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research papers
17 salts of ephedrine: crystal structures and packing analysis
aMolecular Materials Centre, School of Chemical Engineering and Analytical Science, The University of Manchester, PO Box 88, Sackville Street, Manchester M60 1QD, England, bProcess Engineering Group, PR&D, AstraZeneca, Silk Road Business Park, Charter Way, Macclesfield, Cheshire SK10 2NA, England, and cPreformulation and Biopharmaceutics, PAR&D, AstraZeneca, Silk Road Business Park, Charter Way, Macclesfield, Cheshire SK10 2NA, England
*Correspondence e-mail: roger.davey@manchester.ac.uk
The structures of two neutral and 17 salt forms of the base (1R, 2S)-(−)-ephedrine are reported. These structures are discussed in the light of the conformers of the ephedrine moiety, the existence of bilayers and the structure determining role of the counterions. Overall, most of the salt structures are essentially derived from the observed packing of the neutral base and are dominated by the nature of the ephedrine molecular structure. In a few cases the size and hydrophobicity of the counterion disrupts this behaviour.
Keywords: packing analysis; counterion; molecular salts; pharmaceuticals.
1. Introduction
The importance of molecular salts as solid forms in pharmaceutical formulations is well known (Stahl & Wermuth, 2002). For a given active ingredient, the isolation and selection of a salt with the appropriate physicochemical properties involves significant screening activity and has been discussed at some length in the literature (Tong & Whitesell, 1998
; Shanker, 1994
). It is apparent that over 40% of marketed salts are hydrochlorides (Gould, 1986
) and this trend is reflected in the available salt structures in the Cambridge Structural Database (Allen, 2002
): the November 2003 release (Collier, 2004
; Jones et al., 2005
) showed that of 950 salts in which one component is recorded as being active, an agent or a drug, hydrochlorides are the most common occurring as 55% of the entries, with acetates the next most popular at 17%. It is also evident from the CSD records that there have been very few studies in which crystal structures of multiple salt forms of a single active drug have been reported. Recently (Lewis et al., 2005
) the structures of six salts of remacemide have been determined, and the competition between hydrophilic and hydrophobic interactions as drivers for the crystal packings discussed. Our current work seeks to go further using the pharmaceutically active base (1R, 2S)-(−)-ephedrine (I)
as a cation from which salts have been prepared from 17 anions, including carboxylates, sulfonates, phosphonates and inorganic species. The CSD already contains determinations for the hemihydrate (Krebs et al., 2001
), mono- and dihydrogenphosphates (Hearn et al., 1973
; Hearn & Bugg, 1972
) and the hydrochloride (Bergin, 1971
). The entry for the anhydrous free base (Malone & Parvez, 1978
) is incomplete, containing no atomic coordinates: this structure is reported here for the first time. The available hemihydrate structure was solved from powder data at 6 K and so we also report here the results of our single-crystal determination. We have, in addition, redetermined both the hydrochloride and the dihydrogen phosphate since these determinations date from the 1970s. In earlier studies (Leusen et al., 1991
, 1992
) the structures of five pairs of diastereomeric salts of ephedrine with a cyclic phosphoric acid were reported (Zingg et al., 1988
), as well as the structures of the diastereomeric mandelates. These workers were concerned with understanding the structural basis of the chiral resolution process and the relation between solution and crystal structures, respectively, and their studies revealed two conformations of ephedrine in structures based on bilayer packings.
We are concerned with a more general question concerning the process of salt formation. We wanted to explore the relative roles of coulombic and steric factors in directing the packing of molecular salts and, ultimately, to see how crystallographic data might help in providing general guidance for selecting counterions for salt formation. From the previous studies (Leusen et al., 1991, 1992
; Zingg et al., 1988
) we expected that in our new salts ephedrine would adopt either extended or folded conformations and that, in general, the crystal packings would show polar regions where charged moieties are connected by hydrogen bonds, separated by nonpolar sections comprising phenyl rings and alkyl chains.
2. Experimental
Ephedrine base and the inorganic and organic acids were purchased from Sigma–Aldrich and used as supplied. All crystals were grown at room temperature from equimolar aqueous, methanolic or ethanolic solutions of the base and chosen acid. A glass, 10 ml jacketed vessel connected to a circulating water bath was used in these experiments. This allowed components to be dissolved at 323 K in some experiments so that crystallization could be induced by cooling, while in others the vessel was left open so that evaporative crystallization could occur. In a separate series of experiments solutions of the pure base in water were crystallized to yield a hemihydrate which was dehydrated to an anhydrous form in a desiccator. Single-crystal X-ray diffraction data was collected using a Nonius Kappa CCD diffractometer running routinely at 150 K. Graphite-monochromated Mo Kα radiation (λ = 0.71073 Å) was used. Structure solution was performed either with SIR92 (Altomare et al., 1994) or SHELXS97 (Sheldrick, 1997a
), with subsequent achieved using SHELXL97 (Sheldrick, 1997b
). The nomenclature used to describe the salt forms of the is that used widely in the pharmaceutical industry, with besylate representing the counterion benzenesulfonic acid, edisylate (ethanedisulfonic), esylate (ethanesulfonic), mesylate (methanesulfonic) and tosylate (toluenesulfonic), respectively.
3. Results
Table 1 lists the 17 salt systems, together with ephedrine hemihydrate and anhydrous forms, along with summaries of the crystallographic data.1 We note that for some structures (e.g adipate, hemihydrate, malonate) the ellipsoid plots indicate the presence of unresolved disorder. In the discussion below we describe the details of some of the specific structures, while here we make some general observations.
|
Overall it is clear that the molecular packing in many of these solids reflects the et al., 1991, 1992
; Zingg et al., 1988
) and is indeed seen in other systems which have similar molecular features such as remacemide (Lewis et al., 2005
). In the case of the anhydrous solid, the polar functionalities are hydrogen-bonded directly through —OH⋯N— interactions, while in the hemihydrate these interactions are modified by the inclusion of further extensive hydrogen bonding involving the water molecules. In the salts the bilayer expands to incorporate the counterion (and occasionally additional water molecules) through combined coulombic and hydrogen-bonded interactions. In each salt there are two distinct —N—H⋯acceptor distances, one short and one slightly longer. The short distances lie in the range 1.8 (malonate) to 2.2 Å (hydrochloride), while the long distances are in the range 1.9 (dihydrogenphosphate) to 3.0 Å (tartrate trihydrate). In many cases the stability of the bilayer is enhanced through aromatic π–π stacking with distances from the H atom to the closest ring carbon in the range 4.5 (acetate) to 2.8 Å (maleate; Desiraju & Steiner, 1999
). Typical π–π stacks taken from four salts are shown in Fig. 1
, indicating stacking distances between 3.19 and 2.95 Å. The layers are usually interlinked by face-to-edge or methyl-to-face close contacts with dH—π centroid distances between 3.6 (esylate) and 2.8 Å (dihydrogenphosphate). In the case of the adipate, esylate, besylate and tosylate anions, the existence of additional non-polar interactions between the ions destroys the ephedrine bilayer to yield structures with mixed and alternating layers. In the besylate and tosylate this occurs owing to the possibility of additional anion–anion and cation–cation π–π and face-to-edge interactions; in the adipate, its extended non-polar alkyl chain requires that the bilayer is destroyed and in the case of esylate, the ethyl moiety fits between the phenyl rings of the ephedrine.
![]() | Figure 1 π–π stackings of ephedrine from various salt structures. The figures in brackets give the inter-stacking distances in Å. Key: green = ephedrine glycolate (`extended') (3.00, 3.14); blue = ephedrine hydrochloride (`extended') (3.23, 3.10); orange = ephedrine bisulfate (`folded') (3.14, 3.02); red = ephedrine nitrate (`folded') (2.95, 2.92). |
The protonated ephedrine molecule adopts one of two conformations in these structures: `folded' or `extended' owing to the three torsions encompassing the chiral C atoms C7 and C8. Only the `folded' conformation includes an intramolecular hydrogen bond. These conformers are shown in Fig. 2(a), and Table 1
incorporates the measured values (achieved using CERIUS2 (Accelrys Inc., 2003
) of the dihedral angles, τ1, τ2 and τ3, for ephedrine molecules within each Little variation with respect to the dihedral angles involved in either the `extended' or `folded' conformation can be seen. To demonstrate this, individual units of `extended' and `folded' ephedrine were isolated and overlaid from several salt forms, as seen in Fig. 2
(b). This conveys both the similarity in the for units of each conformation and the variation between the two types arising from the torsional flexibility and the intramolecular hydrogen bond. The main difference between the units arises from the variation in τ3 (approximately 100°) from one conformation to the other. Ten structures exhibit the extended form and nine the folded form. In the 12 ephedrine structures examined by Leusen et al. (1991
) they noted that nine exhibited the extended conformer but showed that this could not be rationalized by the difference in internal energy since this was insignificant. We have used a MOPAC conformational search to confirm this result and to show that both conformers represent minima in the overall τ2, τ3 landscape. Our new structures do not appear to support their notion that the extended conformation is associated with face-to-edge aromatic interactions.
![]() | Figure 2 (a) The two conformers of ephedrine. (b) Comparison of ephedrine conformations from selected salt structures. Key: green = ephedrine glycolate (`extended'); blue = ephedrine hydrochloride (`extended'); orange = ephedrine bisulfate (`folded'); red = ephedrine nitrate (`folded'). |
Overall the crystals studied had either needle or plate morphologies. For those that were needles (pure base, acetate, maleate monohydrate, malonate, glycolate, hydrochloride, dihydrogen phosphate, bisulfate, esylate, mesylate), the needle direction always coincided, as expected, with the direction of the strong coulombic interactions and shortest crystallographic axis. These data are included in Table 1. Although we did not perform a dedicated polymorph search, none were found.
4. Ephedrine neutral base and hemihydrate
Fig. 3 (visualized in MERCURY1.4; Bruno et al., 2002
) shows how in the anhydrous neutral base structure, ephedrine molecules are linked along a in hydrogen-bonded chains through alternate —N⋯H—O— interactions between hydroxyl and amino groups, and along b by —C—H⋯ring interactions between methyl groups and phenyl rings on adjacent molecules. The bilayers are then linked along the c axis by T-shaped aromatic —C—H⋯π interactions. The hemihydrate is also based on a bilayer structure, but in this case the inclusion of water molecules into the polar core of the layer enables a different hydrogen-bonding pattern. Our single-crystal structure appears to be essentially similar to that of Krebs et al. (2001
) solved from powder data. The bilayers are created by utilizing hydrogen-bonded dimers linked via hydroxyl–water contacts along a and —C—H⋯π interactions along b. These layers are then further linked along c by face-to-edge contacts between neighbouring phenyl rings. In both of these structures the molecule adopts an extended conformation.
![]() | Figure 3 Projection of ephedrine free base viewed down b. |
5. Inorganic acids
Fig. 4 shows the hydrochloride salt which is essentially the same as in previous structure solutions (Bergin, 1971
). This bilayer structure is held along b by coulombic —N—H2+⋯Cl− interactions and along a by chloride–methyl contacts. The bilayers are then stacked along c by face-to-edge contacts between the interdigitated aromatic rings. The dihydrogenphosphate and bisulfate structures (not shown) follow the same pattern, but here the stereochemistry of the anions allows the bilayer to be held by coulombic interactions, hydrogen bonds and π–π stacking. These layers are then interlinked by aromatic face-to-edge contacts. The planarity of the nitrate ion leads to bilayers in which the expected coulombic interaction and hydrogen bonds between the hydroxyl group and nitrate oxygen are supplemented by weaker —C—H⋯O—N— interactions, as seen in Fig. 5
. The bilayer is further stabilized by π–π stacking between the aromatic rings and the bilayers are again held together by face-to-edge contacts.
![]() | Figure 4 Projection of the hydrochloride salt viewed down a. |
![]() | Figure 5 Projection of the nitrate salt viewed down a. |
6. Carboxylic acids
Structures of the acetate, adipate, maleate, malonate, glycolate, malate and tartrate were solved. In all of these there is, of course, a primary coulombic interaction between the acid anion and the ephedrine cation. Beyond this the actual packing is determined by the nature of the acid involved. The acetate is the simplest comprising (100) bilayers hydrogen bonded as seen in Fig. 6. These layers are interdigitated and held by methyl-to-face and aromatic face-to-edge interactions. In the malonate the dual functionality of the diacid enables the interlinking of bilayers by additional hydrogen bonding along the a axis. In the maleate the increased non-polar nature of the acid, together with the incorporation of water, destroys the bilayer structure totally and creates a three-dimensional hydrogen-bonded network. The acid itself contains an intramolecular hydrogen bond, effectively removing one of its potential hydrogen-bonded functionalities; this is compensated for by the inclusion of water.
![]() | Figure 6 Projection of the acetate salt viewed down b. |
This trend continues in adipate, which again no longer displays the bilayer features. Here the extended non-polar [—(CH2)4—] chain interacts with alternate phenyl rings and the bilayer structure is lost, as seen in Fig. 7. Hydrogen-bonded chains of acid anions run along b. To these chains are bound to ephedrine cations through —C—H⋯aromatic and —O—H⋯O— and —N—H+⋯O— interactions. The case of the glycolate represents a further complication, being a hydroxy acid. Fig. 8
illustrates some features of the structure. Here, the dual functionality of the acid allows the creation of sheets, much in the same ways as the inorganic ions. One hydrogen-bonded chain runs along the c axis connecting molecules via carboxylate–amino and hydroxyl–carboxylate interactions. A second identical chain runs along the b axis, creating hydrogen-bonded (100) sheets. These sheets are stacked along the a axis and held by face-to-edge methyl–phenyl and phenyl–phenyl close contacts. The malate structure is a very similar bilayer structure with the hydrogen bonding creating a (001) sheet. These sheets are held by face-to-edge contacts. The hydrated tartrate salts are similar; the structures (not shown) retain a bilayer form with hydrogen-bonded interactions in the core of the bilayer and the bilayers linked by further hydrogen bonding into sheets. Aromatic face-to-edge ring interactions link the sheets along the c axis. In the case of the monohydrate this involves interdigitation of the phenyl rings, while in the trihydrate the bilayer is translated along the c axis.
![]() | Figure 7 Projection of the adipate salt viewed down a. |
![]() | Figure 8 Projection of the glycolate salt viewed down b. |
7. Sulfonic acids
The mesylate follows a now familiar pattern in which coulombic and hydrogen-bonded interactions from sulfonate O atoms to amino and hydroxyl groups create an (001) layer, with layers interdigitated and held by aromatic face-to-edge contacts. The addition of one methylene group in the esylate changes the nature of the bilayer, which now exposes (Fig. 9) both phenyl rings of the ephedrine and the methyl group of the sulfonic acid. The bilayers have close methyl-aromatic and face-to-edge aromatic contacts. In the case of the disulfonate edysilate, each anion now bridges two ephedrine cations via hydrogen bonds and coulombic interactions which, together with methyl–aromatic close contacts create (010) sheets interdigitated with face-to-edge interactions. The aromatic nature of the besylate totally destroys the ephedrine bilayer and creates (Fig. 10
) a mixed sheet of cations and anions held via coulombic oxygen–amino interactions and oxygen hydroxyl hydrogen bonds. These layers are further stabilized by π–π stacking and methyl-to-face interactions and are held with face-to-edge contacts between phenyl rings of adjacent sulfonic acid anions and ephedrine cations. Finally in the tosylate, the bilayers again comprise both anions and cations. Layers are held together by the usual combination of coulombic, hydrogen bonding and methyl-to-face contacts. Interlayer interactions are face-to-edge on both sides.
![]() | Figure 9 Projection of the esylate salt viewed down a. |
![]() | Figure 10 Projection of the besylate salt viewed down c. |
8. Conclusions
This study has provided the structures of 17 salts of the base ephedrine, enabling for the first time the opportunity to compare and contrast the impact of various factors on the crystal packing of a single
It is clear that the packings observed incorporate, as expected, both bilayer structures of the ions and the two conformations of the ephedrine ion. It is also evident that the crystal structures of ephedrine base and hydrate contain all the essential structural elements which are then transferred over into the salts, with ions fitting within ephedrine bilayers. The bilayers are typically interconnected through aromatic face-to-edge contacts. With increasing size and hydrophobicity of the anion these layers either incorporate the counterion (besylate and tosylate) or can be destroyed altogether (adipate). In the case of the inorganic salts it is clear that crystal packings are determined by the organic moeties rather than the inorganic ions, even though their additional contribution to the lattice energy is presumably quite large.The factors determining the ephedrine conformation are not clear. NMR studies of both neutral (Portoghese, 1967) and protonated (Zingg et al., 1988
) ephedrine in organic solvents have shown the folded conformer with the intramolecular hydrogen bond to be the favoured form. This suggests that in those instances in which the extended conformer exists, it must be imposed by packing and hydrogen-bonding constraints in the crystalline state. Given the previous calculations (Leusen et al., 1991
) showing that the energy barrier between conformers is less than 4.19 kJ mol−1, such a change in conformation could clearly occur during nucleation and crystal growth.
Supporting information
10.1107/S0108768106012018/bk5025sup1.cif
contains datablocks EPHEACET, publication_text, EPHEADIP, EPHEBESY, EPHEEDIS, EPHE, EPHEESYL, EPHEGLYC, EPHEHCL, EPHEHEMI, EPHEMALA, EPHEMALE, EPHEMALO, EPHEMESY, EPHENITR, EPHEPHOS, EPHEBISU, EPHETART1, EPHETART3, EPHETOSY. DOI:Structure factors: contains datablock . DOI: 10.1107/S0108768106012018/bk5025EPHEACETsup2.hkl
Structure factors: contains datablock . DOI: 10.1107/S0108768106012018/bk5025EPHEADIPsup3.hkl
Structure factors: contains datablock . DOI: 10.1107/S0108768106012018/bk5025EPHEBESYsup4.hkl
Structure factors: contains datablock . DOI: 10.1107/S0108768106012018/bk5025EPHEEDISsup5.hkl
Structure factors: contains datablock . DOI: 10.1107/S0108768106012018/bk5025EPHEESYLsup6.hkl
Structure factors: contains datablock . DOI: 10.1107/S0108768106012018/bk5025EPHEGLYCsup7.hkl
Structure factors: contains datablock . DOI: 10.1107/S0108768106012018/bk5025EPHEHCLsup8.hkl
Structure factors: contains datablock . DOI: 10.1107/S0108768106012018/bk5025EPHEHEMIsup9.hkl
Structure factors: contains datablock . DOI: 10.1107/S0108768106012018/bk5025EPHEMALAsup10.hkl
Structure factors: contains datablock . DOI: 10.1107/S0108768106012018/bk5025EPHEMALEsup11.hkl
Structure factors: contains datablock . DOI: 10.1107/S0108768106012018/bk5025EPHEMALOsup12.hkl
Structure factors: contains datablock . DOI: 10.1107/S0108768106012018/bk5025EPHEMESYsup13.hkl
Structure factors: contains datablock . DOI: 10.1107/S0108768106012018/bk5025EPHENITRsup14.hkl
Structure factors: contains datablock . DOI: 10.1107/S0108768106012018/bk5025EPHEPHOSsup15.hkl
Structure factors: contains datablock . DOI: 10.1107/S0108768106012018/bk5025EPHEBISUsup16.hkl
Structure factors: contains datablock . DOI: 10.1107/S0108768106012018/bk5025EPHETART1sup17.hkl
Structure factors: contains datablock . DOI: 10.1107/S0108768106012018/bk5025EPHETART3sup18.hkl
Structure factors: contains datablock . DOI: 10.1107/S0108768106012018/bk5025EPHETOSYsup19.hkl
Structure factors: contains datablock . DOI: 10.1107/S0108768106012018/bk5025EPHEsup20.hkl
Ellipsoid plots. DOI: 10.1107/S0108768106012018/bk5025sup21.pdf
For all compounds, data collection: Collect (Nonius BV, 1997-2000); cell
HKL SCALEPACK (Otwinowski & Minor 1997). Data reduction: HKL DENZO and SCALEPACK (Otwinowski & Minor 1997) for publication_text, EPHEADIP, EPHEBESY, EPHEEDIS, EPHE, EPHEESYL, EPHEGLYC, EPHEHCL, EPHEHEMI, EPHEMALE, EPHEMALO, EPHEMESY, EPHENITR, EPHEPHOS, EPHEBISU, EPHETART1, EPHETART3, EPHETOSY; HKL DENZO and SCALEPACK (Otwinowski & Minor 1 for EPHEMALA. For all compounds, program(s) used to solve structure: SHELXS97 (Sheldrick, 1997). Program(s) used to refine structure: SHELXL97 (sheldrick, 1997) for publication_text; SHELXL97 (Sheldrick, 1997) for EPHEADIP, EPHEBESY, EPHEEDIS, EPHE, EPHEESYL, EPHEGLYC, EPHEHCL, EPHEHEMI, EPHEMALA, EPHEMALE, EPHEMALO, EPHEMESY, EPHENITR, EPHEPHOS, EPHEBISU, EPHETART1, EPHETART3, EPHETOSY. For all compounds, molecular graphics: ORTEP-3 for Windows (Farrugia, 1997); software used to prepare material for publication: WinGX publication routines (Farrugia, 1999).C12H19NO3 | Z = 1 |
Mr = 450.56 | F(000) = 244 |
Triclinic, P1 | Dx = 1.191 Mg m−3 |
Hall symbol: P 1 | Mo Kα radiation, λ = 0.71073 Å |
a = 5.9642 (1) Å | Cell parameters from 7676 reflections |
b = 10.4125 (2) Å | θ = 0–0° |
c = 11.7403 (4) Å | µ = 0.09 mm−1 |
α = 108.175 (1)° | T = 150 K |
β = 104.560 (1)° | Needle, colourless |
γ = 104.087 (2)° | 0.3 × 0.05 × 0.05 mm |
V = 628.08 (3) Å3 |
KappaCCD diffractometer | 3007 independent reflections |
Radiation source: Enraf Nonius FR590 | 2247 reflections with > 2σ(i) |
Graphite monochromator | Rint = 0.062 |
CCD rotation images, thick slices scans | θmax = 28.3°, θmin = 3.5° |
Absorption correction: multi-scan R.H. Blessing, Acta Cryst. (1995), A51, 33-38 | h = −7→7 |
Tmin = 0.927, Tmax = 1.051 | k = −13→13 |
11807 measured reflections | l = −15→15 |
Refinement on f2 | Primary atom site location: structure-invariant direct methods |
Least-squares matrix: full | Secondary atom site location: difference Fourier map |
R[F2 > 2σ(F2)] = 0.043 | Hydrogen site location: inferred from neighbouring sites |
wR(F2) = 0.102 | H atoms treated by a mixture of independent and constrained refinement |
S = 1.03 | w = 1/[σ2(fo2) + (0.0548p)2 + 0.0180p] where p = (fo2 + 2fc2)/3 |
3007 reflections | (Δ/σ)max < 0.001 |
351 parameters | Δρmax = 0.18 e Å−3 |
3 restraints | Δρmin = −0.22 e Å−3 |
C12H19NO3 | γ = 104.087 (2)° |
Mr = 450.56 | V = 628.08 (3) Å3 |
Triclinic, P1 | Z = 1 |
a = 5.9642 (1) Å | Mo Kα radiation |
b = 10.4125 (2) Å | µ = 0.09 mm−1 |
c = 11.7403 (4) Å | T = 150 K |
α = 108.175 (1)° | 0.3 × 0.05 × 0.05 mm |
β = 104.560 (1)° |
KappaCCD diffractometer | 3007 independent reflections |
Absorption correction: multi-scan R.H. Blessing, Acta Cryst. (1995), A51, 33-38 | 2247 reflections with > 2σ(i) |
Tmin = 0.927, Tmax = 1.051 | Rint = 0.062 |
11807 measured reflections |
R[F2 > 2σ(F2)] = 0.043 | 3 restraints |
wR(F2) = 0.102 | H atoms treated by a mixture of independent and constrained refinement |
S = 1.03 | Δρmax = 0.18 e Å−3 |
3007 reflections | Δρmin = −0.22 e Å−3 |
351 parameters |
Geometry. all e.s.d.'s (except the e.s.d. in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. the cell e.s.d.'s are taken into account individually in the estimation of e.s.d.'s in distances, angles and torsion angles; correlations between e.s.d.'s in cell parameters are only used when they are defined by crystal symmetry. an approximate (isotropic) treatment of cell e.s.d.'s is used for estimating e.s.d.'s involving l.s. planes. |
Refinement. Refinement of f2 against all reflections. the weighted r-factor wr and goodness of fit s are based on f2, conventional r-factors r are based on f, with f set to zero for negative f2. the threshold expression of f2 > σ(f2) is used only for calculating r-factors(gt) etc. and is not relevant to the choice of reflections for refinement. r-factors based on f2 are statistically about twice as large as those based on f, and r- factors based on all data will be even larger. |
x | y | z | Uiso*/Ueq | ||
c01 | 0.2211 (5) | 0.9237 (3) | 0.9491 (3) | 0.0399 (7) | |
h01 | 0.333 (7) | 0.890 (4) | 0.915 (3) | 0.048* | |
c02 | 0.2123 (6) | 0.9280 (4) | 1.0662 (4) | 0.0507 (9) | |
h02 | 0.3163 | 0.8947 | 1.1134 | 0.061* | |
c03 | 0.0502 (6) | 0.9815 (3) | 1.1138 (3) | 0.0461 (8) | |
h03 | 0.040 (7) | 0.984 (4) | 1.191 (4) | 0.055* | |
c04 | −0.1086 (6) | 1.0281 (3) | 1.0413 (3) | 0.0437 (8) | |
h04 | −0.230 (7) | 1.061 (4) | 1.073 (3) | 0.052* | |
c05 | −0.1006 (5) | 1.0218 (3) | 0.9233 (3) | 0.0373 (7) | |
h05 | −0.224 (6) | 1.046 (4) | 0.868 (3) | 0.045* | |
c06 | 0.0668 (5) | 0.9715 (3) | 0.8759 (3) | 0.0297 (6) | |
c07 | 0.0800 (5) | 0.9706 (3) | 0.7482 (3) | 0.0298 (6) | |
h07 | −0.091 (6) | 0.922 (3) | 0.680 (3) | 0.036* | |
c08 | 0.1675 (5) | 1.1250 (3) | 0.7551 (3) | 0.0293 (6) | |
h08 | 0.057 (6) | 1.167 (3) | 0.775 (3) | 0.035* | |
c09 | 0.4253 (5) | 1.2176 (3) | 0.8537 (3) | 0.0400 (7) | |
h09a | 0.5458 | 1.1849 | 0.8244 | 0.06* | |
h09b | 0.4356 | 1.2097 | 0.9341 | 0.06* | |
h09c | 0.4568 | 1.3164 | 0.8649 | 0.06* | |
c10 | 0.1881 (6) | 1.2533 (3) | 0.6078 (3) | 0.0360 (7) | |
h12a | 0.155 (6) | 1.231 (3) | 0.519 (4) | 0.043* | |
h12b | 0.355 (6) | 1.329 (4) | 0.671 (3) | 0.043* | |
h12c | 0.058 (6) | 1.286 (4) | 0.624 (3) | 0.043* | |
c11 | 0.5376 (5) | 0.9674 (3) | 0.4752 (3) | 0.0290 (6) | |
c12 | 0.2796 (5) | 0.8617 (3) | 0.3923 (3) | 0.0383 (7) | |
h13a | 0.2295 | 0.7963 | 0.4309 | 0.057* | |
h13b | 0.2779 | 0.8084 | 0.3088 | 0.057* | |
h13c | 0.1673 | 0.9134 | 0.3844 | 0.057* | |
c21 | 0.5902 (5) | 1.6417 (3) | 1.0878 (3) | 0.0353 (7) | |
h21 | 0.763 (6) | 1.697 (4) | 1.151 (3) | 0.042* | |
c22 | 0.5131 (6) | 1.6445 (3) | 0.9669 (3) | 0.0410 (7) | |
h22 | 0.635 (6) | 1.705 (4) | 0.940 (3) | 0.049* | |
c23 | 0.2704 (6) | 1.5715 (3) | 0.8853 (3) | 0.0393 (7) | |
h23 | 0.212 (6) | 1.572 (4) | 0.798 (3) | 0.047* | |
c24 | 0.1053 (6) | 1.4912 (4) | 0.9229 (3) | 0.0403 (7) | |
h24 | −0.066 (7) | 1.440 (4) | 0.869 (3) | 0.048* | |
c25 | 0.1832 (5) | 1.4871 (4) | 1.0432 (3) | 0.0387 (7) | |
h25 | 0.057 (6) | 1.436 (4) | 1.070 (3) | 0.046* | |
c26 | 0.4248 (5) | 1.5627 (3) | 1.1274 (3) | 0.0279 (6) | |
c27 | 0.5043 (4) | 1.5596 (3) | 1.2595 (2) | 0.0271 (6) | |
h27 | 0.3744 | 1.5688 | 1.2953 | 0.033* | |
c28 | 0.5452 (5) | 1.4179 (3) | 1.2544 (3) | 0.0281 (6) | |
h28 | 0.383 (6) | 1.340 (3) | 1.201 (3) | 0.034* | |
c29 | 0.7507 (5) | 1.3977 (3) | 1.2056 (3) | 0.0374 (7) | |
h29a | 0.9047 | 1.4716 | 1.2649 | 0.056* | |
h29b | 0.7173 | 1.4038 | 1.1235 | 0.056* | |
h29c | 0.7607 | 1.3047 | 1.1973 | 0.056* | |
c30 | 0.6195 (6) | 1.2859 (3) | 1.3991 (3) | 0.0361 (7) | |
h32a | 0.637 (6) | 1.298 (3) | 1.496 (3) | 0.043* | |
h32b | 0.472 (7) | 1.211 (4) | 1.339 (3) | 0.043* | |
h32c | 0.762 (7) | 1.270 (3) | 1.381 (3) | 0.043* | |
c31 | 0.2496 (4) | 0.5727 (3) | 0.5515 (2) | 0.0248 (6) | |
c32 | 0.5108 (5) | 0.6702 (3) | 0.6366 (3) | 0.0423 (8) | |
h33a | 0.5899 | 0.6206 | 0.6807 | 0.063* | |
h33b | 0.5084 | 0.7556 | 0.698 | 0.063* | |
h33c | 0.6006 | 0.6966 | 0.5851 | 0.063* | |
n01 | 0.1602 (4) | 1.1171 (2) | 0.6256 (2) | 0.0298 (5) | |
h10 | 0.2813 | 1.0862 | 0.6088 | 0.036* | |
h11 | 0.0152 | 1.0505 | 0.5676 | 0.036* | |
n21 | 0.6061 (4) | 1.4229 (2) | 1.3886 (2) | 0.0258 (5) | |
h30 | 0.7524 | 1.4938 | 1.4387 | 0.031* | |
h31 | 0.4905 | 1.4456 | 1.4192 | 0.031* | |
o01 | 0.2428 (3) | 0.9050 (2) | 0.7081 (2) | 0.0374 (5) | |
h06 | 0.1738 | 0.8171 | 0.6751 | 0.056* | |
o02 | 0.5679 (3) | 1.0778 (2) | 0.5663 (2) | 0.0370 (5) | |
o03 | 0.7149 (3) | 0.9349 (2) | 0.44695 (19) | 0.0384 (5) | |
o21 | 0.7290 (3) | 1.6704 (2) | 1.34584 (18) | 0.0349 (5) | |
h26 | 0.700 (6) | 1.742 (4) | 1.369 (3) | 0.042* | |
o22 | 0.0740 (3) | 0.60889 (19) | 0.57567 (18) | 0.0311 (4) | |
o23 | 0.2199 (3) | 0.45987 (19) | 0.46028 (18) | 0.0298 (4) |
U11 | U22 | U33 | U12 | U13 | U23 | |
c01 | 0.0325 (17) | 0.0408 (17) | 0.051 (2) | 0.0156 (13) | 0.0127 (14) | 0.0242 (15) |
c02 | 0.045 (2) | 0.056 (2) | 0.056 (2) | 0.0178 (16) | 0.0108 (16) | 0.0345 (18) |
c03 | 0.0474 (19) | 0.0429 (18) | 0.0407 (18) | 0.0036 (14) | 0.0136 (15) | 0.0181 (16) |
c04 | 0.0429 (19) | 0.0362 (17) | 0.047 (2) | 0.0105 (14) | 0.0190 (15) | 0.0103 (15) |
c05 | 0.0294 (15) | 0.0325 (16) | 0.0465 (19) | 0.0117 (12) | 0.0097 (13) | 0.0137 (14) |
c06 | 0.0273 (14) | 0.0182 (12) | 0.0374 (15) | 0.0057 (10) | 0.0047 (11) | 0.0104 (11) |
c07 | 0.0235 (14) | 0.0210 (13) | 0.0377 (16) | 0.0062 (10) | 0.0050 (12) | 0.0083 (12) |
c08 | 0.0252 (14) | 0.0192 (13) | 0.0351 (16) | 0.0063 (10) | 0.0048 (11) | 0.0060 (12) |
c09 | 0.0358 (17) | 0.0235 (14) | 0.0448 (18) | 0.0040 (12) | −0.0020 (13) | 0.0113 (13) |
c10 | 0.0363 (18) | 0.0293 (16) | 0.0428 (19) | 0.0124 (14) | 0.0103 (15) | 0.0170 (15) |
c11 | 0.0227 (14) | 0.0289 (15) | 0.0348 (16) | 0.0070 (11) | 0.0069 (12) | 0.0160 (14) |
c12 | 0.0260 (14) | 0.0421 (18) | 0.0405 (17) | 0.0067 (12) | 0.0072 (12) | 0.0160 (15) |
c21 | 0.0339 (16) | 0.0309 (15) | 0.0345 (16) | 0.0034 (12) | 0.0086 (13) | 0.0137 (13) |
c22 | 0.0521 (18) | 0.0328 (16) | 0.0383 (18) | 0.0084 (13) | 0.0161 (14) | 0.0192 (14) |
c23 | 0.0499 (18) | 0.0366 (16) | 0.0325 (17) | 0.0176 (14) | 0.0114 (14) | 0.0157 (14) |
c24 | 0.0286 (16) | 0.052 (2) | 0.0338 (16) | 0.0126 (14) | 0.0051 (13) | 0.0144 (15) |
c25 | 0.0274 (15) | 0.0517 (19) | 0.0354 (17) | 0.0102 (13) | 0.0121 (13) | 0.0173 (15) |
c26 | 0.0288 (14) | 0.0257 (13) | 0.0289 (15) | 0.0106 (11) | 0.0103 (11) | 0.0095 (12) |
c27 | 0.0223 (13) | 0.0281 (14) | 0.0279 (14) | 0.0064 (11) | 0.0090 (11) | 0.0092 (12) |
c28 | 0.0259 (14) | 0.0317 (15) | 0.0243 (14) | 0.0090 (11) | 0.0071 (11) | 0.0103 (12) |
c29 | 0.0392 (16) | 0.0464 (18) | 0.0303 (15) | 0.0215 (14) | 0.0138 (13) | 0.0136 (13) |
c30 | 0.0317 (16) | 0.0282 (16) | 0.0468 (19) | 0.0087 (13) | 0.0105 (14) | 0.0170 (14) |
c31 | 0.0238 (13) | 0.0262 (14) | 0.0249 (14) | 0.0064 (10) | 0.0077 (11) | 0.0133 (12) |
c32 | 0.0269 (15) | 0.0381 (17) | 0.0442 (19) | 0.0046 (12) | 0.0080 (13) | 0.0028 (15) |
n01 | 0.0209 (11) | 0.0242 (11) | 0.0394 (14) | 0.0068 (9) | 0.0072 (10) | 0.0100 (10) |
n21 | 0.0198 (11) | 0.0284 (12) | 0.0294 (13) | 0.0076 (9) | 0.0087 (9) | 0.0123 (10) |
o01 | 0.0381 (11) | 0.0230 (10) | 0.0513 (13) | 0.0126 (8) | 0.0189 (10) | 0.0114 (10) |
o02 | 0.0298 (11) | 0.0285 (11) | 0.0490 (13) | 0.0084 (8) | 0.0161 (9) | 0.0104 (10) |
o03 | 0.0240 (10) | 0.0351 (11) | 0.0434 (12) | 0.0075 (8) | 0.0092 (9) | 0.0039 (10) |
o21 | 0.0333 (11) | 0.0259 (11) | 0.0325 (11) | 0.0050 (9) | 0.0023 (8) | 0.0068 (9) |
o22 | 0.0251 (10) | 0.0296 (10) | 0.0349 (11) | 0.0104 (8) | 0.0080 (8) | 0.0093 (8) |
o23 | 0.0257 (10) | 0.0298 (11) | 0.0306 (10) | 0.0084 (8) | 0.0112 (8) | 0.0080 (9) |
c01—c02 | 1.375 (5) | c22—c23 | 1.380 (5) |
c01—c06 | 1.389 (4) | c22—h22 | 1.02 (4) |
c01—h01 | 0.95 (4) | c23—c24 | 1.383 (5) |
c02—c03 | 1.377 (5) | c23—h23 | 1.00 (3) |
c02—h02 | 0.93 | c24—c25 | 1.389 (4) |
c03—c04 | 1.390 (5) | c24—h24 | 0.96 (4) |
c03—h03 | 0.92 (4) | c25—c26 | 1.385 (4) |
c04—c05 | 1.381 (5) | c25—h25 | 0.99 (4) |
c04—h04 | 0.98 (4) | c26—c27 | 1.517 (4) |
c05—c06 | 1.390 (4) | c27—o21 | 1.411 (3) |
c05—h05 | 0.99 (3) | c27—c28 | 1.539 (4) |
c06—c07 | 1.518 (4) | c27—h27 | 0.98 |
c07—o01 | 1.408 (3) | c28—n21 | 1.506 (3) |
c07—c08 | 1.533 (4) | c28—c29 | 1.509 (4) |
c07—h07 | 1.01 (3) | c28—h28 | 0.99 (3) |
c08—n01 | 1.486 (4) | c29—h29a | 0.96 |
c08—c09 | 1.523 (4) | c29—h29b | 0.96 |
c08—h08 | 0.92 (3) | c29—h29c | 0.96 |
c09—h09a | 0.96 | c30—n21 | 1.489 (3) |
c09—h09b | 0.96 | c30—h32a | 1.07 (3) |
c09—h09c | 0.96 | c30—h32b | 0.94 (4) |
c10—n01 | 1.473 (4) | c30—h32c | 0.97 (4) |
c10—h12a | 0.95 (4) | c31—o23 | 1.256 (3) |
c10—h12b | 1.02 (3) | c31—o22 | 1.263 (3) |
c10—h12c | 0.96 (3) | c31—c32 | 1.507 (4) |
c11—o02 | 1.239 (3) | c32—h33a | 0.96 |
c11—o03 | 1.273 (3) | c32—h33b | 0.96 |
c11—c12 | 1.510 (4) | c32—h33c | 0.96 |
c12—h13a | 0.96 | n01—h10 | 0.9 |
c12—h13b | 0.96 | n01—h11 | 0.9 |
c12—h13c | 0.96 | n21—h30 | 0.9 |
c21—c22 | 1.389 (4) | n21—h31 | 0.9 |
c21—c26 | 1.393 (4) | o01—h06 | 0.82 |
c21—h21 | 1.00 (4) | o21—h26 | 0.78 (4) |
c02—c01—c06 | 121.2 (3) | c22—c23—h23 | 122 (2) |
c02—c01—h01 | 123 (2) | c24—c23—h23 | 119 (2) |
c06—c01—h01 | 116 (2) | c23—c24—c25 | 119.9 (3) |
c01—c02—c03 | 120.4 (3) | c23—c24—h24 | 121 (2) |
c01—c02—h02 | 119.8 | c25—c24—h24 | 119 (2) |
c03—c02—h02 | 119.8 | c26—c25—c24 | 121.2 (3) |
c02—c03—c04 | 119.5 (3) | c26—c25—h25 | 120.8 (19) |
c02—c03—h03 | 122 (2) | c24—c25—h25 | 117.8 (19) |
c04—c03—h03 | 119 (2) | c25—c26—c21 | 118.4 (3) |
c05—c04—c03 | 119.8 (3) | c25—c26—c27 | 120.3 (2) |
c05—c04—h04 | 121 (2) | c21—c26—c27 | 121.3 (2) |
c03—c04—h04 | 119 (2) | o21—c27—c26 | 113.6 (2) |
c04—c05—c06 | 121.2 (3) | o21—c27—c28 | 105.4 (2) |
c04—c05—h05 | 119.7 (19) | c26—c27—c28 | 111.9 (2) |
c06—c05—h05 | 119.0 (19) | o21—c27—h27 | 108.6 |
c01—c06—c05 | 118.0 (3) | c26—c27—h27 | 108.6 |
c01—c06—c07 | 121.5 (3) | c28—c27—h27 | 108.6 |
c05—c06—c07 | 120.5 (2) | n21—c28—c29 | 110.3 (2) |
o01—c07—c06 | 113.7 (2) | n21—c28—c27 | 107.1 (2) |
o01—c07—c08 | 106.9 (2) | c29—c28—c27 | 112.3 (2) |
c06—c07—c08 | 110.6 (2) | n21—c28—h28 | 107.5 (17) |
o01—c07—h07 | 110.2 (17) | c29—c28—h28 | 113.4 (17) |
c06—c07—h07 | 109.9 (18) | c27—c28—h28 | 106.0 (16) |
c08—c07—h07 | 105.1 (18) | c28—c29—h29a | 109.5 |
n01—c08—c09 | 110.1 (2) | c28—c29—h29b | 109.5 |
n01—c08—c07 | 108.3 (2) | h29a—c29—h29b | 109.5 |
c09—c08—c07 | 113.6 (2) | c28—c29—h29c | 109.5 |
n01—c08—h08 | 107.6 (19) | h29a—c29—h29c | 109.5 |
c09—c08—h08 | 109 (2) | h29b—c29—h29c | 109.5 |
c07—c08—h08 | 108 (2) | n21—c30—h32a | 107.0 (18) |
c08—c09—h09a | 109.5 | n21—c30—h32b | 108 (2) |
c08—c09—h09b | 109.5 | h32a—c30—h32b | 111 (3) |
h09a—c09—h09b | 109.5 | n21—c30—h32c | 109 (2) |
c08—c09—h09c | 109.5 | h32a—c30—h32c | 111 (3) |
h09a—c09—h09c | 109.5 | h32b—c30—h32c | 111 (3) |
h09b—c09—h09c | 109.5 | o23—c31—o22 | 123.9 (2) |
n01—c10—h12a | 107 (2) | o23—c31—c32 | 117.7 (2) |
n01—c10—h12b | 109.2 (18) | o22—c31—c32 | 118.4 (2) |
h12a—c10—h12b | 118 (3) | c31—c32—h33a | 109.5 |
n01—c10—h12c | 109 (2) | c31—c32—h33b | 109.5 |
h12a—c10—h12c | 104 (3) | h33a—c32—h33b | 109.5 |
h12b—c10—h12c | 109 (3) | c31—c32—h33c | 109.5 |
o02—c11—o03 | 123.5 (2) | h33a—c32—h33c | 109.5 |
o02—c11—c12 | 119.8 (2) | h33b—c32—h33c | 109.5 |
o03—c11—c12 | 116.6 (3) | c10—n01—c08 | 115.5 (2) |
c11—c12—h13a | 109.5 | c10—n01—h10 | 108.4 |
c11—c12—h13b | 109.5 | c08—n01—h10 | 108.4 |
h13a—c12—h13b | 109.5 | c10—n01—h11 | 108.4 |
c11—c12—h13c | 109.5 | c08—n01—h11 | 108.4 |
h13a—c12—h13c | 109.5 | h10—n01—h11 | 107.5 |
h13b—c12—h13c | 109.5 | c30—n21—c28 | 114.5 (2) |
c22—c21—c26 | 120.5 (3) | c30—n21—h30 | 108.6 |
c22—c21—h21 | 122.6 (19) | c28—n21—h30 | 108.6 |
c26—c21—h21 | 117.0 (19) | c30—n21—h31 | 108.6 |
c23—c22—c21 | 120.5 (3) | c28—n21—h31 | 108.6 |
c23—c22—h22 | 120 (2) | h30—n21—h31 | 107.6 |
c21—c22—h22 | 120 (2) | c07—o01—h06 | 109.5 |
c22—c23—c24 | 119.5 (3) | c27—o21—h26 | 107 (3) |
c06—c01—c02—c03 | −0.5 (5) | c22—c23—c24—c25 | 1.5 (5) |
c01—c02—c03—c04 | 1.5 (5) | c23—c24—c25—c26 | 0.2 (5) |
c02—c03—c04—c05 | −0.7 (5) | c24—c25—c26—c21 | −1.0 (4) |
c03—c04—c05—c06 | −1.0 (4) | c24—c25—c26—c27 | 178.5 (3) |
c02—c01—c06—c05 | −1.1 (4) | c22—c21—c26—c25 | 0.2 (4) |
c02—c01—c06—c07 | 178.4 (3) | c22—c21—c26—c27 | −179.3 (3) |
c04—c05—c06—c01 | 1.9 (4) | c25—c26—c27—o21 | −163.3 (2) |
c04—c05—c06—c07 | −177.7 (3) | c21—c26—c27—o21 | 16.3 (3) |
c01—c06—c07—o01 | 5.8 (3) | c25—c26—c27—c28 | 77.5 (3) |
c05—c06—c07—o01 | −174.7 (2) | c21—c26—c27—c28 | −102.9 (3) |
c01—c06—c07—c08 | −114.5 (3) | o21—c27—c28—n21 | 59.8 (3) |
c05—c06—c07—c08 | 65.0 (3) | c26—c27—c28—n21 | −176.2 (2) |
o01—c07—c08—n01 | 59.6 (3) | o21—c27—c28—c29 | −61.3 (3) |
c06—c07—c08—n01 | −176.1 (2) | c26—c27—c28—c29 | 62.6 (3) |
o01—c07—c08—c09 | −63.0 (3) | c09—c08—n01—c10 | −67.5 (3) |
c06—c07—c08—c09 | 61.3 (3) | c07—c08—n01—c10 | 167.7 (2) |
c26—c21—c22—c23 | 1.4 (5) | c29—c28—n21—c30 | −65.1 (3) |
c21—c22—c23—c24 | −2.2 (5) | c27—c28—n21—c30 | 172.4 (2) |
D—H···A | D—H | H···A | D···A | D—H···A |
n01—h11···o03i | 0.9 | 1.81 | 2.705 (3) | 173 |
n01—h11···o02i | 0.9 | 2.75 | 3.318 (3) | 122 |
n21—h31···o23ii | 0.9 | 1.82 | 2.714 (3) | 170 |
o21—h26···o03ii | 0.78 (4) | 1.90 (4) | 2.669 (3) | 166 (4) |
n21—h30···o23iii | 0.9 | 2.85 | 3.438 (3) | 124 |
Symmetry codes: (i) x−1, y, z; (ii) x, y+1, z+1; (iii) x+1, y+1, z+1. |
C16H25NO5 | F(000) = 672 |
Mr = 311.37 | Dx = 1.207 Mg m−3 |
Orthorhombic, P212121 | Mo Kα radiation, λ = 0.71073 Å |
Hall symbol: P 2ac 2ab | Cell parameters from 2198 reflections |
a = 5.8290 (1) Å | θ = 1.0–27.5° |
b = 13.5440 (4) Å | µ = 0.09 mm−1 |
c = 21.7000 (7) Å | T = 150 K |
V = 1713.17 (8) Å3 | Plate, colourless |
Z = 4 | 0.25 × 0.25 × 0.05 mm |
KappaCCD diffractometer | 1808 reflections with I > 2σ(I) |
Radiation source: Enraf Nonius FR590 | θmax = 27.5°, θmin = 3.2° |
Graphite monochromator | h = −7→7 |
CCD rotation images, thick slices scans | k = −17→17 |
3874 measured reflections | l = −27→28 |
2266 independent reflections |
Refinement on F2 | Primary atom site location: structure-invariant direct methods |
Least-squares matrix: full | Secondary atom site location: difference Fourier map |
R[F2 > 2σ(F2)] = 0.041 | Hydrogen site location: inferred from neighbouring sites |
wR(F2) = 0.094 | H atoms treated by a mixture of independent and constrained refinement |
S = 1.03 | w = 1/[σ2(Fo2) + (0.0506P)2 + 0.0611P] where P = (Fo2 + 2Fc2)/3 |
2266 reflections | (Δ/σ)max < 0.001 |
269 parameters | Δρmax = 0.18 e Å−3 |
0 restraints | Δρmin = −0.24 e Å−3 |
C16H25NO5 | V = 1713.17 (8) Å3 |
Mr = 311.37 | Z = 4 |
Orthorhombic, P212121 | Mo Kα radiation |
a = 5.8290 (1) Å | µ = 0.09 mm−1 |
b = 13.5440 (4) Å | T = 150 K |
c = 21.7000 (7) Å | 0.25 × 0.25 × 0.05 mm |
KappaCCD diffractometer | 2266 independent reflections |
3874 measured reflections | 1808 reflections with I > 2σ(I) |
R[F2 > 2σ(F2)] = 0.041 | 0 restraints |
wR(F2) = 0.094 | H atoms treated by a mixture of independent and constrained refinement |
S = 1.03 | Δρmax = 0.18 e Å−3 |
2266 reflections | Δρmin = −0.24 e Å−3 |
269 parameters |
Geometry. All e.s.d.'s (except the e.s.d. in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell e.s.d.'s are taken into account individually in the estimation of e.s.d.'s in distances, angles and torsion angles; correlations between e.s.d.'s in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell e.s.d.'s is used for estimating e.s.d.'s involving l.s. planes. |
Refinement. Refinement of F2 against ALL reflections. The weighted R-factor wR and goodness of fit S are based on F2, conventional R-factors R are based on F, with F set to zero for negative F2. The threshold expression of F2 > σ(F2) is used only for calculating R-factors(gt) etc. and is not relevant to the choice of reflections for refinement. R-factors based on F2 are statistically about twice as large as those based on F, and R- factors based on ALL data will be even larger. |
x | y | z | Uiso*/Ueq | ||
C1 | 0.8800 (4) | 1.13541 (16) | −0.03860 (10) | 0.0301 (5) | |
H1 | 0.753 (4) | 1.1082 (16) | −0.0118 (10) | 0.036* | |
C2 | 0.8687 (4) | 1.23258 (17) | −0.05869 (11) | 0.0369 (5) | |
H2 | 0.719 (4) | 1.2733 (17) | −0.0469 (11) | 0.044* | |
C3 | 1.0415 (4) | 1.27166 (18) | −0.09512 (11) | 0.0399 (6) | |
H3 | 1.033 (4) | 1.341 (2) | −0.1128 (11) | 0.048* | |
C4 | 1.2274 (4) | 1.21354 (17) | −0.11049 (11) | 0.0381 (6) | |
H4 | 1.353 (5) | 1.2426 (19) | −0.1367 (11) | 0.046* | |
C5 | 1.2402 (4) | 1.11630 (16) | −0.09050 (10) | 0.0319 (5) | |
H5 | 1.380 (4) | 1.0754 (17) | −0.0999 (10) | 0.038* | |
C6 | 1.0656 (3) | 1.07666 (15) | −0.05414 (9) | 0.0243 (4) | |
C7 | 1.0842 (3) | 0.97004 (14) | −0.03315 (9) | 0.0240 (4) | |
H7 | 1.162 (4) | 0.9334 (15) | −0.0674 (9) | 0.029* | |
C8 | 1.2329 (3) | 0.96040 (14) | 0.02480 (9) | 0.0231 (4) | |
H8 | 1.382 (4) | 0.9931 (15) | 0.0167 (9) | 0.028* | |
C9 | 1.1216 (4) | 1.00141 (17) | 0.08211 (10) | 0.0296 (5) | |
H9A | 1.073 (4) | 1.0719 (18) | 0.0754 (10) | 0.036* | |
H9B | 0.987 (4) | 0.9646 (17) | 0.0918 (10) | 0.036* | |
H9C | 1.216 (4) | 0.9979 (17) | 0.1151 (10) | 0.036* | |
C10 | 1.4669 (4) | 0.82970 (18) | 0.07916 (11) | 0.0312 (5) | |
H12A | 1.414 (4) | 0.8557 (17) | 0.1190 (11) | 0.037* | |
H12B | 1.491 (4) | 0.7536 (19) | 0.0795 (10) | 0.037* | |
H12C | 1.605 (4) | 0.8666 (17) | 0.0657 (10) | 0.037* | |
C11 | 1.0124 (3) | 0.67136 (15) | 0.12613 (9) | 0.0250 (4) | |
C12 | 0.8658 (4) | 0.68769 (17) | 0.18247 (10) | 0.0321 (5) | |
H13 | 0.908 (4) | 0.6397 (16) | 0.2136 (11) | 0.039* | |
H14 | 0.710 (5) | 0.6753 (17) | 0.1707 (11) | 0.039* | |
C13 | 0.8842 (4) | 0.79217 (18) | 0.20703 (10) | 0.0327 (5) | |
H15 | 1.035 (5) | 0.8071 (17) | 0.2204 (11) | 0.039* | |
H16 | 0.844 (4) | 0.8431 (17) | 0.1755 (11) | 0.039* | |
C14 | 0.7242 (5) | 0.80945 (19) | 0.26106 (11) | 0.0473 (6) | |
H17 | 0.764 | 0.764 | 0.2939 | 0.057* | |
H18 | 0.5684 | 0.7948 | 0.2483 | 0.057* | |
C15 | 0.7325 (5) | 0.9141 (2) | 0.28594 (12) | 0.0480 (7) | |
H19 | 0.887 (5) | 0.936 (2) | 0.2940 (13) | 0.058* | |
H20 | 0.663 (5) | 0.9199 (19) | 0.3261 (13) | 0.058* | |
C16 | 0.6204 (5) | 0.9895 (2) | 0.24503 (13) | 0.0630 (9) | |
N1 | 1.2860 (3) | 0.85283 (12) | 0.03256 (8) | 0.0233 (4) | |
H10 | 1.163 (4) | 0.8173 (15) | 0.0427 (10) | 0.028* | |
H11 | 1.339 (4) | 0.8239 (15) | −0.0079 (10) | 0.028* | |
O1 | 0.8699 (2) | 0.92552 (11) | −0.01902 (7) | 0.0302 (4) | |
H6 | 0.804 (4) | 0.9125 (17) | −0.0549 (11) | 0.036* | |
O2 | 0.9614 (2) | 0.71905 (10) | 0.07795 (6) | 0.0263 (3) | |
O3 | 1.1767 (3) | 0.61184 (12) | 0.12894 (7) | 0.0435 (5) | |
O4 | 0.5197 (5) | 0.97026 (19) | 0.19809 (12) | 0.1134 (11) | |
O5 | 0.6364 (4) | 1.08406 (16) | 0.26288 (10) | 0.0671 (6) | |
H21 | 0.703 (6) | 1.086 (2) | 0.2997 (16) | 0.08* |
U11 | U22 | U33 | U12 | U13 | U23 | |
C1 | 0.0286 (10) | 0.0328 (12) | 0.0289 (11) | 0.0020 (10) | 0.0000 (9) | 0.0010 (9) |
C2 | 0.0382 (12) | 0.0345 (13) | 0.0380 (12) | 0.0086 (11) | −0.0047 (11) | −0.0016 (10) |
C3 | 0.0515 (14) | 0.0289 (12) | 0.0392 (13) | −0.0018 (12) | −0.0120 (12) | 0.0054 (11) |
C4 | 0.0408 (12) | 0.0374 (13) | 0.0360 (12) | −0.0084 (11) | 0.0002 (11) | 0.0106 (10) |
C5 | 0.0302 (11) | 0.0354 (12) | 0.0301 (11) | 0.0002 (10) | 0.0005 (10) | 0.0039 (10) |
C6 | 0.0248 (9) | 0.0270 (11) | 0.0210 (9) | −0.0017 (9) | −0.0035 (8) | 0.0000 (8) |
C7 | 0.0242 (9) | 0.0257 (10) | 0.0220 (10) | −0.0010 (9) | −0.0015 (8) | 0.0004 (9) |
C8 | 0.0243 (9) | 0.0200 (10) | 0.0251 (10) | −0.0028 (9) | −0.0012 (8) | −0.0006 (8) |
C9 | 0.0368 (11) | 0.0276 (12) | 0.0243 (11) | 0.0016 (10) | −0.0032 (10) | −0.0023 (9) |
C10 | 0.0297 (10) | 0.0334 (13) | 0.0304 (12) | 0.0030 (10) | −0.0075 (10) | 0.0036 (10) |
C11 | 0.0281 (10) | 0.0242 (10) | 0.0225 (10) | −0.0019 (9) | 0.0024 (9) | 0.0006 (9) |
C12 | 0.0380 (12) | 0.0335 (12) | 0.0249 (11) | 0.0033 (11) | 0.0071 (10) | 0.0043 (10) |
C13 | 0.0332 (11) | 0.0406 (13) | 0.0243 (11) | 0.0009 (11) | 0.0034 (9) | −0.0044 (10) |
C14 | 0.0522 (14) | 0.0573 (16) | 0.0324 (12) | −0.0031 (13) | 0.0106 (12) | −0.0153 (12) |
C15 | 0.0490 (15) | 0.0630 (17) | 0.0320 (12) | 0.0028 (15) | 0.0022 (12) | −0.0237 (13) |
C16 | 0.0529 (14) | 0.074 (2) | 0.0616 (17) | 0.0283 (16) | −0.0257 (15) | −0.0455 (16) |
N1 | 0.0236 (8) | 0.0235 (9) | 0.0228 (9) | −0.0011 (8) | −0.0017 (7) | 0.0008 (7) |
O1 | 0.0281 (7) | 0.0358 (8) | 0.0268 (8) | −0.0093 (7) | −0.0051 (6) | 0.0022 (7) |
O2 | 0.0294 (7) | 0.0273 (8) | 0.0224 (7) | −0.0006 (6) | 0.0004 (6) | 0.0033 (6) |
O3 | 0.0473 (10) | 0.0525 (10) | 0.0308 (8) | 0.0246 (9) | 0.0111 (7) | 0.0146 (7) |
O4 | 0.133 (2) | 0.1035 (18) | 0.1035 (17) | 0.0730 (17) | −0.0912 (18) | −0.0781 (15) |
O5 | 0.0744 (13) | 0.0663 (12) | 0.0605 (12) | 0.0330 (12) | −0.0322 (11) | −0.0371 (11) |
C1—C6 | 1.385 (3) | C10—H12B | 1.04 (2) |
C1—C2 | 1.388 (3) | C10—H12C | 0.99 (3) |
C1—H1 | 1.01 (2) | C11—O3 | 1.253 (2) |
C2—C3 | 1.386 (4) | C11—O2 | 1.264 (2) |
C2—H2 | 1.06 (3) | C11—C12 | 1.508 (3) |
C3—C4 | 1.380 (3) | C12—C13 | 1.516 (3) |
C3—H3 | 1.02 (3) | C12—H13 | 0.97 (2) |
C4—C5 | 1.389 (3) | C12—H14 | 0.96 (3) |
C4—H4 | 1.01 (3) | C13—C14 | 1.517 (3) |
C5—C6 | 1.395 (3) | C13—H15 | 0.95 (3) |
C5—H5 | 1.01 (2) | C13—H16 | 1.00 (2) |
C6—C7 | 1.518 (3) | C14—C15 | 1.517 (4) |
C7—O1 | 1.420 (2) | C14—H17 | 0.97 |
C7—C8 | 1.533 (3) | C14—H18 | 0.97 |
C7—H7 | 1.00 (2) | C15—C16 | 1.503 (4) |
C8—N1 | 1.499 (2) | C15—H19 | 0.96 (3) |
C8—C9 | 1.509 (3) | C15—H20 | 0.96 (3) |
C8—H8 | 0.99 (2) | C16—O4 | 1.204 (3) |
C9—H9A | 1.01 (2) | C16—O5 | 1.341 (3) |
C9—H9B | 0.95 (2) | N1—H10 | 0.89 (2) |
C9—H9C | 0.90 (2) | N1—H11 | 1.01 (2) |
C10—N1 | 1.494 (3) | O1—H6 | 0.89 (3) |
C10—H12A | 0.98 (2) | O5—H21 | 0.89 (3) |
C6—C1—C2 | 120.4 (2) | H12A—C10—H12C | 109.4 (19) |
C6—C1—H1 | 120.1 (13) | H12B—C10—H12C | 112.9 (18) |
C2—C1—H1 | 119.5 (13) | O3—C11—O2 | 123.26 (18) |
C3—C2—C1 | 120.4 (2) | O3—C11—C12 | 119.21 (18) |
C3—C2—H2 | 122.3 (13) | O2—C11—C12 | 117.53 (18) |
C1—C2—H2 | 117.1 (13) | C11—C12—C13 | 112.45 (18) |
C4—C3—C2 | 119.4 (2) | C11—C12—H13 | 108.9 (14) |
C4—C3—H3 | 118.5 (15) | C13—C12—H13 | 111.3 (13) |
C2—C3—H3 | 122.1 (15) | C11—C12—H14 | 107.2 (14) |
C3—C4—C5 | 120.5 (2) | C13—C12—H14 | 108.9 (14) |
C3—C4—H4 | 119.0 (14) | H13—C12—H14 | 107.8 (19) |
C5—C4—H4 | 120.5 (15) | C12—C13—C14 | 111.9 (2) |
C4—C5—C6 | 120.2 (2) | C12—C13—H15 | 111.9 (14) |
C4—C5—H5 | 120.2 (13) | C14—C13—H15 | 107.6 (14) |
C6—C5—H5 | 119.5 (13) | C12—C13—H16 | 112.7 (13) |
C1—C6—C5 | 119.10 (19) | C14—C13—H16 | 106.1 (14) |
C1—C6—C7 | 121.97 (18) | H15—C13—H16 | 106 (2) |
C5—C6—C7 | 118.92 (18) | C13—C14—C15 | 113.6 (2) |
O1—C7—C6 | 113.93 (16) | C13—C14—H17 | 108.9 |
O1—C7—C8 | 106.50 (15) | C15—C14—H17 | 108.9 |
C6—C7—C8 | 111.57 (16) | C13—C14—H18 | 108.9 |
O1—C7—H7 | 110.3 (12) | C15—C14—H18 | 108.9 |
C6—C7—H7 | 106.3 (12) | H17—C14—H18 | 107.7 |
C8—C7—H7 | 108.1 (12) | C16—C15—C14 | 114.3 (2) |
N1—C8—C9 | 110.74 (17) | C16—C15—H19 | 107.8 (17) |
N1—C8—C7 | 106.96 (15) | C14—C15—H19 | 112.4 (16) |
C9—C8—C7 | 113.70 (17) | C16—C15—H20 | 107.2 (17) |
N1—C8—H8 | 105.9 (12) | C14—C15—H20 | 112.6 (16) |
C9—C8—H8 | 111.0 (12) | H19—C15—H20 | 102 (2) |
C7—C8—H8 | 108.2 (12) | O4—C16—O5 | 119.0 (3) |
C8—C9—H9A | 110.5 (12) | O4—C16—C15 | 124.4 (3) |
C8—C9—H9B | 110.0 (14) | O5—C16—C15 | 116.6 (2) |
H9A—C9—H9B | 107.3 (18) | C10—N1—C8 | 115.19 (17) |
C8—C9—H9C | 111.8 (15) | C10—N1—H10 | 106.7 (14) |
H9A—C9—H9C | 109.7 (19) | C8—N1—H10 | 112.7 (14) |
H9B—C9—H9C | 107.4 (19) | C10—N1—H11 | 106.9 (12) |
N1—C10—H12A | 107.4 (14) | C8—N1—H11 | 110.0 (12) |
N1—C10—H12B | 108.0 (13) | H10—N1—H11 | 104.7 (18) |
H12A—C10—H12B | 113.0 (19) | C7—O1—H6 | 106.2 (15) |
N1—C10—H12C | 105.6 (13) | C16—O5—H21 | 109 (2) |
C6—C1—C2—C3 | 0.8 (3) | C6—C7—C8—N1 | −166.74 (16) |
C1—C2—C3—C4 | −1.1 (4) | O1—C7—C8—C9 | −54.2 (2) |
C2—C3—C4—C5 | 1.0 (4) | C6—C7—C8—C9 | 70.7 (2) |
C3—C4—C5—C6 | −0.6 (3) | O3—C11—C12—C13 | 115.1 (2) |
C2—C1—C6—C5 | −0.3 (3) | O2—C11—C12—C13 | −65.0 (3) |
C2—C1—C6—C7 | −179.93 (19) | C11—C12—C13—C14 | 176.2 (2) |
C4—C5—C6—C1 | 0.3 (3) | C12—C13—C14—C15 | −178.4 (2) |
C4—C5—C6—C7 | 179.85 (18) | C13—C14—C15—C16 | 72.7 (3) |
C1—C6—C7—O1 | 23.6 (3) | C14—C15—C16—O4 | 4.2 (4) |
C5—C6—C7—O1 | −155.96 (18) | C14—C15—C16—O5 | −175.7 (3) |
C1—C6—C7—C8 | −97.0 (2) | C9—C8—N1—C10 | −67.2 (2) |
C5—C6—C7—C8 | 83.4 (2) | C7—C8—N1—C10 | 168.43 (17) |
O1—C7—C8—N1 | 68.4 (2) |
D—H···A | D—H | H···A | D···A | D—H···A |
O1—H6···O3i | 0.89 (3) | 1.80 (3) | 2.686 (2) | 178 (2) |
N1—H11···O2ii | 1.01 (2) | 1.78 (2) | 2.783 (2) | 173.6 (19) |
O5—H21···O3iii | 0.89 (3) | 1.73 (3) | 2.615 (2) | 170 (3) |
Symmetry codes: (i) x−1/2, −y+3/2, −z; (ii) x+1/2, −y+3/2, −z; (iii) −x+2, y+1/2, −z+1/2. |
C16H20O4S | F(000) = 344 |
Mr = 323.4 | Dx = 1.316 Mg m−3 |
Monoclinic, P21 | Mo Kα radiation, λ = 0.71073 Å |
Hall symbol: P 2yb | Cell parameters from 7649 reflections |
a = 5.7214 (3) Å | θ = 1.0–27.5° |
b = 20.8336 (11) Å | µ = 0.22 mm−1 |
c = 6.9188 (5) Å | T = 150 K |
β = 98.409 (2)° | Plate, brown |
V = 815.84 (8) Å3 | 0.25 × 0.25 × 0.05 mm |
Z = 2 |
KappaCCD diffractometer | 3395 independent reflections |
Radiation source: Enraf Nonius FR590 | 2159 reflections with I > 2σ(I) |
Graphite monochromator | Rint = 0.038 |
CCD rotation images, thick slices scans | θmax = 27.5°, θmin = 3.0° |
Absorption correction: multi-scan R.H. Blessing, Acta Cryst. (1995), A51, 33-38 | h = −7→7 |
Tmin = 0.984, Tmax = 1.024 | k = −24→26 |
5520 measured reflections | l = −7→8 |
Refinement on F2 | Secondary atom site location: difference Fourier map |
Least-squares matrix: full | Hydrogen site location: inferred from neighbouring sites |
R[F2 > 2σ(F2)] = 0.055 | H atoms treated by a mixture of independent and constrained refinement |
wR(F2) = 0.113 | w = 1/[σ2(Fo2) + (0.0302P)2] where P = (Fo2 + 2Fc2)/3 |
S = 1.01 | (Δ/σ)max < 0.001 |
3395 reflections | Δρmax = 0.27 e Å−3 |
260 parameters | Δρmin = −0.42 e Å−3 |
1 restraint | Absolute structure: Flack H D (1983), Acta Cryst. A39, 876-881 |
Primary atom site location: structure-invariant direct methods | Absolute structure parameter: −0.04 (11) |
C16H20O4S | V = 815.84 (8) Å3 |
Mr = 323.4 | Z = 2 |
Monoclinic, P21 | Mo Kα radiation |
a = 5.7214 (3) Å | µ = 0.22 mm−1 |
b = 20.8336 (11) Å | T = 150 K |
c = 6.9188 (5) Å | 0.25 × 0.25 × 0.05 mm |
β = 98.409 (2)° |
KappaCCD diffractometer | 3395 independent reflections |
Absorption correction: multi-scan R.H. Blessing, Acta Cryst. (1995), A51, 33-38 | 2159 reflections with I > 2σ(I) |
Tmin = 0.984, Tmax = 1.024 | Rint = 0.038 |
5520 measured reflections |
R[F2 > 2σ(F2)] = 0.055 | H atoms treated by a mixture of independent and constrained refinement |
wR(F2) = 0.113 | Δρmax = 0.27 e Å−3 |
S = 1.01 | Δρmin = −0.42 e Å−3 |
3395 reflections | Absolute structure: Flack H D (1983), Acta Cryst. A39, 876-881 |
260 parameters | Absolute structure parameter: −0.04 (11) |
1 restraint |
Geometry. All e.s.d.'s (except the e.s.d. in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell e.s.d.'s are taken into account individually in the estimation of e.s.d.'s in distances, angles and torsion angles; correlations between e.s.d.'s in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell e.s.d.'s is used for estimating e.s.d.'s involving l.s. planes. |
Refinement. Refinement of F2 against ALL reflections. The weighted R-factor wR and goodness of fit S are based on F2, conventional R-factors R are based on F, with F set to zero for negative F2. The threshold expression of F2 > σ(F2) is used only for calculating R-factors(gt) etc. and is not relevant to the choice of reflections for refinement. R-factors based on F2 are statistically about twice as large as those based on F, and R- factors based on ALL data will be even larger. |
x | y | z | Uiso*/Ueq | ||
C1 | 1.3882 (8) | 0.85924 (19) | 0.6682 (6) | 0.0302 (10) | |
H1 | 1.232 (9) | 0.8493 (18) | 0.590 (6) | 0.036* | |
C2 | 1.4381 (9) | 0.9179 (2) | 0.7637 (7) | 0.0354 (11) | |
H2 | 1.306 (8) | 0.9518 (19) | 0.736 (6) | 0.042* | |
C3 | 1.6630 (9) | 0.9295 (2) | 0.8638 (6) | 0.0348 (11) | |
H3 | 1.712 (8) | 0.967 (2) | 0.923 (6) | 0.042* | |
C4 | 1.8332 (8) | 0.8831 (2) | 0.8709 (7) | 0.0355 (11) | |
H4 | 1.983 (8) | 0.892 (2) | 0.935 (6) | 0.043* | |
C5 | 1.7846 (8) | 0.8246 (2) | 0.7771 (6) | 0.0292 (10) | |
H5 | 1.911 (7) | 0.7929 (19) | 0.784 (6) | 0.035* | |
C6 | 1.5624 (7) | 0.81220 (17) | 0.6745 (5) | 0.0208 (9) | |
C7 | 1.5112 (8) | 0.74808 (19) | 0.5743 (6) | 0.0265 (10) | |
H7 | 1.598 (7) | 0.717 (2) | 0.648 (6) | 0.032* | |
C8 | 1.6069 (8) | 0.74590 (18) | 0.3781 (6) | 0.0257 (9) | |
H8 | 1.778 (7) | 0.7451 (17) | 0.408 (6) | 0.031* | |
C9 | 1.4924 (11) | 0.7943 (2) | 0.2315 (7) | 0.0358 (12) | |
H9A | 1.539 (8) | 0.7903 (19) | 0.110 (7) | 0.043* | |
H9B | 1.524 (9) | 0.835 (2) | 0.270 (7) | 0.043* | |
H9C | 1.313 (9) | 0.785 (2) | 0.216 (6) | 0.043* | |
C10 | 1.6836 (9) | 0.6260 (2) | 0.4045 (7) | 0.0338 (12) | |
H12A | 1.628 (7) | 0.6208 (19) | 0.524 (7) | 0.041* | |
H12B | 1.851 (8) | 0.631 (2) | 0.421 (6) | 0.041* | |
H12C | 1.633 (8) | 0.584 (2) | 0.321 (7) | 0.041* | |
C11 | 2.2319 (8) | 0.5644 (2) | 0.7256 (6) | 0.0300 (11) | |
H13 | 2.344 (8) | 0.6002 (19) | 0.741 (6) | 0.036* | |
C12 | 2.2484 (8) | 0.5099 (2) | 0.6154 (7) | 0.0377 (12) | |
H14 | 2.393 (8) | 0.504 (2) | 0.543 (6) | 0.045* | |
C13 | 2.0794 (8) | 0.4618 (2) | 0.6064 (7) | 0.0358 (11) | |
H15 | 2.079 (7) | 0.426 (2) | 0.524 (6) | 0.043* | |
C14 | 1.8907 (9) | 0.4692 (2) | 0.7111 (7) | 0.0357 (11) | |
H16 | 1.779 (8) | 0.431 (2) | 0.713 (6) | 0.043* | |
C15 | 1.8736 (8) | 0.52318 (19) | 0.8223 (6) | 0.0291 (10) | |
H17 | 1.749 (8) | 0.5324 (19) | 0.901 (7) | 0.035* | |
C16 | 2.0422 (7) | 0.57102 (17) | 0.8286 (6) | 0.0229 (9) | |
O1 | 1.2687 (5) | 0.73278 (13) | 0.5334 (4) | 0.0291 (7) | |
H6 | 1.2258 | 0.7164 | 0.6301 | 0.044* | |
O2 | 2.1234 (5) | 0.62436 (12) | 1.1704 (4) | 0.0303 (7) | |
O3 | 2.1531 (5) | 0.69075 (12) | 0.8878 (4) | 0.0330 (7) | |
O4 | 1.7664 (5) | 0.65500 (12) | 0.9529 (4) | 0.0293 (7) | |
S1 | 2.01984 (17) | 0.64093 (4) | 0.97080 (13) | 0.0249 (2) | |
N1 | 1.5633 (7) | 0.68021 (15) | 0.2902 (5) | 0.0232 (8) | |
H10 | 1.620 (7) | 0.6774 (18) | 0.184 (6) | 0.028* | |
H11 | 1.397 (8) | 0.6682 (16) | 0.275 (5) | 0.028* |
U11 | U22 | U33 | U12 | U13 | U23 | |
C1 | 0.032 (3) | 0.032 (2) | 0.026 (2) | −0.003 (2) | 0.004 (2) | 0.0010 (18) |
C2 | 0.041 (3) | 0.032 (2) | 0.034 (3) | 0.001 (2) | 0.007 (2) | 0.001 (2) |
C3 | 0.043 (3) | 0.034 (2) | 0.029 (3) | −0.012 (2) | 0.013 (2) | −0.008 (2) |
C4 | 0.028 (3) | 0.048 (3) | 0.030 (3) | −0.009 (2) | 0.002 (2) | −0.010 (2) |
C5 | 0.029 (3) | 0.034 (2) | 0.026 (2) | 0.003 (2) | 0.006 (2) | −0.0031 (19) |
C6 | 0.025 (2) | 0.025 (2) | 0.013 (2) | −0.0022 (17) | 0.0085 (18) | −0.0011 (16) |
C7 | 0.025 (3) | 0.032 (2) | 0.024 (3) | 0.0023 (19) | 0.009 (2) | 0.0005 (18) |
C8 | 0.027 (2) | 0.029 (2) | 0.022 (2) | −0.0024 (19) | 0.0053 (19) | −0.0021 (17) |
C9 | 0.057 (3) | 0.034 (3) | 0.020 (3) | −0.002 (2) | 0.014 (2) | 0.002 (2) |
C10 | 0.038 (3) | 0.041 (3) | 0.026 (2) | 0.008 (2) | 0.015 (2) | 0.005 (2) |
C11 | 0.029 (3) | 0.033 (2) | 0.030 (3) | 0.0004 (19) | 0.013 (2) | −0.0039 (19) |
C12 | 0.035 (3) | 0.041 (3) | 0.039 (3) | 0.005 (2) | 0.011 (2) | −0.009 (2) |
C13 | 0.039 (3) | 0.034 (3) | 0.032 (3) | 0.003 (2) | −0.002 (2) | −0.011 (2) |
C14 | 0.034 (3) | 0.032 (2) | 0.037 (3) | −0.003 (2) | −0.009 (2) | 0.002 (2) |
C15 | 0.025 (3) | 0.035 (2) | 0.026 (3) | −0.001 (2) | 0.001 (2) | 0.0011 (19) |
C16 | 0.023 (2) | 0.027 (2) | 0.019 (2) | 0.0017 (17) | 0.0039 (19) | 0.0027 (16) |
O1 | 0.0272 (18) | 0.0397 (17) | 0.0223 (16) | −0.0100 (13) | 0.0097 (13) | −0.0014 (13) |
O2 | 0.0269 (17) | 0.0444 (18) | 0.0192 (15) | −0.0031 (12) | 0.0023 (13) | −0.0004 (11) |
O3 | 0.0404 (19) | 0.0281 (15) | 0.0350 (18) | −0.0045 (13) | 0.0207 (15) | 0.0024 (13) |
O4 | 0.0209 (16) | 0.0428 (19) | 0.0249 (15) | 0.0065 (12) | 0.0055 (12) | −0.0032 (12) |
S1 | 0.0257 (6) | 0.0300 (5) | 0.0204 (5) | −0.0006 (5) | 0.0083 (4) | 0.0003 (5) |
N1 | 0.022 (2) | 0.0298 (19) | 0.0190 (19) | −0.0037 (15) | 0.0072 (17) | −0.0014 (15) |
C1—C6 | 1.394 (6) | C10—H12A | 0.94 (5) |
C1—C2 | 1.398 (6) | C10—H12B | 0.96 (4) |
C1—H1 | 1.00 (5) | C10—H12C | 1.06 (4) |
C2—C3 | 1.390 (6) | C11—C12 | 1.379 (6) |
C2—H2 | 1.03 (4) | C11—C16 | 1.390 (6) |
C3—C4 | 1.368 (6) | C11—H13 | 0.98 (4) |
C3—H3 | 0.91 (4) | C12—C13 | 1.386 (6) |
C4—C5 | 1.389 (6) | C12—H14 | 1.04 (4) |
C4—H4 | 0.93 (5) | C13—C14 | 1.394 (7) |
C5—C6 | 1.387 (5) | C13—H15 | 0.94 (4) |
C5—H5 | 0.97 (4) | C14—C15 | 1.375 (6) |
C6—C7 | 1.514 (5) | C14—H16 | 1.02 (4) |
C7—O1 | 1.411 (5) | C15—C16 | 1.384 (6) |
C7—C8 | 1.537 (5) | C15—H17 | 0.98 (5) |
C7—H7 | 0.92 (4) | C16—S1 | 1.773 (4) |
C8—N1 | 1.504 (5) | O1—H6 | 0.82 |
C8—C9 | 1.510 (6) | O2—S1 | 1.462 (3) |
C8—H8 | 0.97 (4) | O3—S1 | 1.455 (3) |
C9—H9A | 0.92 (5) | O4—S1 | 1.467 (3) |
C9—H9B | 0.91 (5) | N1—H10 | 0.85 (4) |
C9—H9C | 1.03 (5) | N1—H11 | 0.97 (4) |
C10—N1 | 1.488 (5) | ||
C6—C1—C2 | 120.3 (4) | N1—C10—H12B | 111 (3) |
C6—C1—H1 | 117 (2) | H12A—C10—H12B | 112 (3) |
C2—C1—H1 | 123 (2) | N1—C10—H12C | 105 (3) |
C3—C2—C1 | 119.9 (4) | H12A—C10—H12C | 107 (4) |
C3—C2—H2 | 125 (2) | H12B—C10—H12C | 111 (4) |
C1—C2—H2 | 115 (2) | C12—C11—C16 | 119.1 (4) |
C4—C3—C2 | 119.8 (4) | C12—C11—H13 | 126 (2) |
C4—C3—H3 | 115 (3) | C16—C11—H13 | 115 (2) |
C2—C3—H3 | 125 (3) | C11—C12—C13 | 121.1 (4) |
C3—C4—C5 | 120.7 (4) | C11—C12—H14 | 119 (3) |
C3—C4—H4 | 118 (3) | C13—C12—H14 | 120 (3) |
C5—C4—H4 | 121 (3) | C12—C13—C14 | 119.1 (4) |
C6—C5—C4 | 120.6 (4) | C12—C13—H15 | 123 (3) |
C6—C5—H5 | 121 (2) | C14—C13—H15 | 118 (3) |
C4—C5—H5 | 118 (2) | C15—C14—C13 | 120.3 (4) |
C5—C6—C1 | 118.9 (4) | C15—C14—H16 | 122 (3) |
C5—C6—C7 | 120.0 (4) | C13—C14—H16 | 117 (3) |
C1—C6—C7 | 121.1 (4) | C14—C15—C16 | 120.0 (4) |
O1—C7—C6 | 114.2 (3) | C14—C15—H17 | 126 (2) |
O1—C7—C8 | 106.4 (3) | C16—C15—H17 | 114 (2) |
C6—C7—C8 | 111.1 (3) | C15—C16—C11 | 120.4 (4) |
O1—C7—H7 | 113 (3) | C15—C16—S1 | 120.2 (3) |
C6—C7—H7 | 109 (3) | C11—C16—S1 | 119.4 (3) |
C8—C7—H7 | 103 (3) | C7—O1—H6 | 109.5 |
N1—C8—C9 | 107.9 (3) | O3—S1—O2 | 112.21 (16) |
N1—C8—C7 | 108.9 (3) | O3—S1—O4 | 113.13 (16) |
C9—C8—C7 | 113.4 (4) | O2—S1—O4 | 112.69 (16) |
N1—C8—H8 | 100 (2) | O3—S1—C16 | 106.40 (17) |
C9—C8—H8 | 119 (2) | O2—S1—C16 | 106.15 (17) |
C7—C8—H8 | 107 (2) | O4—S1—C16 | 105.55 (17) |
C8—C9—H9A | 113 (3) | C10—N1—C8 | 116.1 (3) |
C8—C9—H9B | 113 (3) | C10—N1—H10 | 102 (3) |
H9A—C9—H9B | 106 (4) | C8—N1—H10 | 111 (3) |
C8—C9—H9C | 105 (2) | C10—N1—H11 | 103 (2) |
H9A—C9—H9C | 107 (4) | C8—N1—H11 | 112 (2) |
H9B—C9—H9C | 112 (4) | H10—N1—H11 | 112 (4) |
N1—C10—H12A | 112 (2) | ||
C6—C1—C2—C3 | 0.6 (6) | C16—C11—C12—C13 | −0.1 (7) |
C1—C2—C3—C4 | −1.0 (7) | C11—C12—C13—C14 | −0.1 (7) |
C2—C3—C4—C5 | 0.7 (7) | C12—C13—C14—C15 | −0.3 (7) |
C3—C4—C5—C6 | 0.0 (7) | C13—C14—C15—C16 | 0.9 (6) |
C4—C5—C6—C1 | −0.4 (6) | C14—C15—C16—C11 | −1.1 (6) |
C4—C5—C6—C7 | −179.5 (4) | C14—C15—C16—S1 | 179.7 (3) |
C2—C1—C6—C5 | 0.1 (6) | C12—C11—C16—C15 | 0.7 (6) |
C2—C1—C6—C7 | 179.2 (4) | C12—C11—C16—S1 | 179.9 (3) |
C5—C6—C7—O1 | 159.7 (3) | C15—C16—S1—O3 | −156.9 (3) |
C1—C6—C7—O1 | −19.4 (5) | C11—C16—S1—O3 | 23.9 (4) |
C5—C6—C7—C8 | −79.9 (5) | C15—C16—S1—O2 | 83.4 (4) |
C1—C6—C7—C8 | 101.0 (4) | C11—C16—S1—O2 | −95.8 (3) |
O1—C7—C8—N1 | −58.2 (4) | C15—C16—S1—O4 | −36.5 (4) |
C6—C7—C8—N1 | 176.9 (3) | C11—C16—S1—O4 | 144.3 (3) |
O1—C7—C8—C9 | 62.0 (4) | C9—C8—N1—C10 | 174.0 (4) |
C6—C7—C8—C9 | −62.9 (5) | C7—C8—N1—C10 | −62.5 (5) |
D—H···A | D—H | H···A | D···A | D—H···A |
N1—H10···O4i | 0.85 (4) | 1.97 (4) | 2.804 (4) | 170 (4) |
N1—H10···S1i | 0.85 (4) | 3.00 (4) | 3.750 (4) | 149 (3) |
N1—H11···O2ii | 0.97 (4) | 1.87 (4) | 2.787 (5) | 156 (3) |
N1—H11···S1ii | 0.97 (4) | 2.84 (4) | 3.635 (4) | 139 (3) |
O1—H6···O3iii | 0.82 | 1.96 | 2.773 (4) | 169 |
Symmetry codes: (i) x, y, z−1; (ii) x−1, y, z−1; (iii) x−1, y, z. |
C22H36N2O8S2 | F(000) = 556 |
Mr = 520.65 | Dx = 1.335 Mg m−3 |
Monoclinic, P21 | Mo Kα radiation, λ = 0.71073 Å |
Hall symbol: P 2yb | Cell parameters from 13259 reflections |
a = 5.7108 (1) Å | θ = 1.0–27.5° |
b = 34.0651 (7) Å | µ = 0.25 mm−1 |
c = 6.6590 (2) Å | T = 150 K |
β = 90.09° | Plate, white |
V = 1295.43 (5) Å3 | 0.35 × 0.35 × 0.05 mm |
Z = 2 |
KappaCCD diffractometer | 5249 independent reflections |
Radiation source: Enraf Nonius FR590 | 3134 reflections with I > 2σ(I) |
Graphite monochromator | Rint = 0.032 |
CCD rotation images, thick slices scans | θmax = 27.5°, θmin = 2.4° |
Absorption correction: multi-scan R.H. Blessing, Acta Cryst. (1995), A51, 33-38 | h = −4→7 |
Tmin = 0.979, Tmax = 1.027 | k = −41→44 |
10886 measured reflections | l = −7→8 |
Refinement on F2 | Secondary atom site location: difference Fourier map |
Least-squares matrix: full | Hydrogen site location: inferred from neighbouring sites |
R[F2 > 2σ(F2)] = 0.054 | H atoms treated by a mixture of independent and constrained refinement |
wR(F2) = 0.125 | w = 1/[σ2(Fo2) + (0.0481P)2 + 0.2649P] where P = (Fo2 + 2Fc2)/3 |
S = 0.98 | (Δ/σ)max = 0.001 |
5249 reflections | Δρmax = 0.31 e Å−3 |
357 parameters | Δρmin = −0.37 e Å−3 |
1 restraint | Absolute structure: Flack H D (1983), Acta Cryst. A39, 876-881 |
Primary atom site location: structure-invariant direct methods | Absolute structure parameter: −0.03 (11) |
C22H36N2O8S2 | V = 1295.43 (5) Å3 |
Mr = 520.65 | Z = 2 |
Monoclinic, P21 | Mo Kα radiation |
a = 5.7108 (1) Å | µ = 0.25 mm−1 |
b = 34.0651 (7) Å | T = 150 K |
c = 6.6590 (2) Å | 0.35 × 0.35 × 0.05 mm |
β = 90.09° |
KappaCCD diffractometer | 5249 independent reflections |
Absorption correction: multi-scan R.H. Blessing, Acta Cryst. (1995), A51, 33-38 | 3134 reflections with I > 2σ(I) |
Tmin = 0.979, Tmax = 1.027 | Rint = 0.032 |
10886 measured reflections |
R[F2 > 2σ(F2)] = 0.054 | H atoms treated by a mixture of independent and constrained refinement |
wR(F2) = 0.125 | Δρmax = 0.31 e Å−3 |
S = 0.98 | Δρmin = −0.37 e Å−3 |
5249 reflections | Absolute structure: Flack H D (1983), Acta Cryst. A39, 876-881 |
357 parameters | Absolute structure parameter: −0.03 (11) |
1 restraint |
Geometry. All e.s.d.'s (except the e.s.d. in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell e.s.d.'s are taken into account individually in the estimation of e.s.d.'s in distances, angles and torsion angles; correlations between e.s.d.'s in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell e.s.d.'s is used for estimating e.s.d.'s involving l.s. planes. |
Refinement. Refinement of F2 against ALL reflections. The weighted R-factor wR and goodness of fit S are based on F2, conventional R-factors R are based on F, with F set to zero for negative F2. The threshold expression of F2 > σ(F2) is used only for calculating R-factors(gt) etc. and is not relevant to the choice of reflections for refinement. R-factors based on F2 are statistically about twice as large as those based on F, and R- factors based on ALL data will be even larger. |
x | y | z | Uiso*/Ueq | ||
C01 | 0.7038 (8) | 0.90658 (15) | 0.9014 (7) | 0.0391 (12) | |
H01 | 0.5944 | 0.9267 | 0.8921 | 0.047* | |
C02 | 0.6496 (11) | 0.86970 (17) | 0.8240 (8) | 0.0502 (15) | |
H02 | 0.499 (9) | 0.8631 (15) | 0.767 (7) | 0.055 (16)* | |
C03 | 0.8089 (12) | 0.84027 (19) | 0.8410 (9) | 0.0527 (17) | |
H03 | 0.767 (8) | 0.8138 (14) | 0.782 (7) | 0.049 (14)* | |
C04 | 1.0209 (11) | 0.84649 (16) | 0.9342 (9) | 0.0458 (15) | |
H04 | 1.126 (8) | 0.8260 (14) | 0.950 (6) | 0.031 (13)* | |
C05 | 1.0740 (10) | 0.88305 (15) | 1.0101 (8) | 0.0389 (13) | |
H05 | 1.213 (7) | 0.8836 (12) | 1.064 (6) | 0.019 (12)* | |
C06 | 0.9182 (8) | 0.91369 (15) | 0.9922 (7) | 0.0288 (12) | |
C07 | 0.9738 (8) | 0.95497 (15) | 1.0672 (7) | 0.0311 (12) | |
H7 | 0.905 (7) | 0.9785 (13) | 0.970 (6) | 0.036 (13)* | |
C08 | 0.8671 (8) | 0.96273 (14) | 1.2739 (7) | 0.0320 (12) | |
H08 | 0.6961 | 0.9622 | 1.2621 | 0.038* | |
C09 | 0.9419 (12) | 0.93356 (18) | 1.4325 (8) | 0.0589 (18) | |
H09A | 1.1097 | 0.9321 | 1.4362 | 0.088* | |
H09B | 0.8786 | 0.9082 | 1.401 | 0.088* | |
H09C | 0.8849 | 0.9419 | 1.5612 | 0.088* | |
C10 | 0.8845 (8) | 1.03619 (14) | 1.2058 (7) | 0.0398 (13) | |
H12A | 0.9705 | 1.0333 | 1.083 | 0.06* | |
H12B | 0.926 | 1.0606 | 1.2685 | 0.06* | |
H12C | 0.7197 | 1.036 | 1.1773 | 0.06* | |
C11 | 1.1361 (9) | 1.08813 (16) | 0.7161 (8) | 0.0294 (12) | |
H13 | 1.012 (9) | 1.0713 (15) | 0.760 (7) | 0.047 (14)* | |
H14 | 1.137 (7) | 1.0936 (11) | 0.578 (6) | 0.015 (10)* | |
C12 | 1.3726 (8) | 1.07241 (15) | 0.7801 (7) | 0.0277 (12) | |
H15 | 1.3725 | 1.0679 | 0.924 | 0.033* | |
H16 | 1.4924 | 1.0918 | 0.7507 | 0.033* | |
C21 | 1.6242 (8) | 0.76002 (15) | 0.4064 (7) | 0.0392 (12) | |
H21 | 1.7384 | 0.7406 | 0.3982 | 0.047* | |
C22 | 1.6691 (11) | 0.79639 (17) | 0.3293 (8) | 0.0468 (14) | |
H22 | 1.833 (8) | 0.8019 (13) | 0.274 (6) | 0.039 (13)* | |
C23 | 1.5031 (11) | 0.82548 (17) | 0.3433 (8) | 0.0514 (16) | |
H23 | 1.5331 | 0.8502 | 0.2898 | 0.062* | |
C24 | 1.2959 (12) | 0.81820 (17) | 0.4348 (9) | 0.0498 (16) | |
H24 | 1.183 (9) | 0.8370 (15) | 0.441 (7) | 0.039 (14)* | |
C25 | 1.2466 (8) | 0.78152 (14) | 0.5112 (7) | 0.0379 (12) | |
H25 | 1.103 | 0.7769 | 0.5725 | 0.045* | |
C26 | 1.4099 (8) | 0.75136 (15) | 0.4973 (7) | 0.0287 (12) | |
C27 | 1.3662 (8) | 0.70974 (15) | 0.5746 (7) | 0.0289 (12) | |
H27 | 1.454 (6) | 0.6919 (12) | 0.494 (5) | 0.011 (11)* | |
C28 | 1.4679 (9) | 0.70392 (14) | 0.7834 (7) | 0.0311 (12) | |
H28 | 1.619 (7) | 0.7051 (12) | 0.776 (6) | 0.020 (12)* | |
C29 | 1.3654 (11) | 0.73094 (18) | 0.9421 (7) | 0.0580 (18) | |
H29A | 1.1984 | 0.7278 | 0.9454 | 0.087* | |
H29B | 1.4032 | 0.7577 | 0.91 | 0.087* | |
H29C | 1.4299 | 0.7244 | 1.071 | 0.087* | |
C30 | 1.5080 (9) | 0.63087 (15) | 0.7106 (7) | 0.0407 (12) | |
H32A | 1.4063 | 0.6297 | 0.5958 | 0.061* | |
H32B | 1.5052 | 0.6061 | 0.7794 | 0.061* | |
H32C | 1.6648 | 0.6365 | 0.6676 | 0.061* | |
N01 | 0.9421 (6) | 1.00332 (11) | 1.3427 (6) | 0.0304 (10) | |
H10 | 0.8751 | 1.0081 | 1.4625 | 0.036* | |
H11 | 1.0982 | 1.0031 | 1.3618 | 0.036* | |
N21 | 1.4267 (6) | 0.66234 (11) | 0.8487 (5) | 0.0304 (10) | |
H30 | 1.4978 | 0.6588 | 0.9681 | 0.036* | |
H31 | 1.272 | 0.6592 | 0.8683 | 0.036* | |
O02 | 0.8585 (5) | 1.14831 (10) | 0.7290 (5) | 0.0396 (9) | |
O03 | 1.2702 (5) | 1.15841 (9) | 0.8096 (5) | 0.0343 (8) | |
O04 | 1.0147 (6) | 1.12468 (10) | 1.0438 (4) | 0.0364 (9) | |
O05 | 1.4018 (5) | 1.03526 (10) | 0.4410 (4) | 0.0357 (8) | |
O06 | 1.6839 (5) | 1.01977 (10) | 0.7020 (4) | 0.0350 (8) | |
O07 | 1.2764 (6) | 0.99872 (10) | 0.7302 (5) | 0.0414 (9) | |
O21 | 1.1214 (5) | 0.70113 (10) | 0.5869 (5) | 0.0368 (8) | |
H26 | 1.0846 | 0.6863 | 0.4952 | 0.055* | |
S1 | 1.06486 (19) | 1.13367 (3) | 0.83440 (17) | 0.0284 (3) | |
S2 | 1.43963 (19) | 1.02792 (3) | 0.65424 (17) | 0.0281 (3) | |
O01 | 1.2197 (5) | 0.96210 (9) | 1.0871 (5) | 0.0377 (8) | |
H06 | 1.2822 | 0.9432 | 1.141 | 0.057* |
U11 | U22 | U33 | U12 | U13 | U23 | |
C01 | 0.033 (3) | 0.047 (3) | 0.037 (3) | −0.001 (2) | 0.006 (2) | −0.007 (2) |
C02 | 0.041 (3) | 0.063 (4) | 0.047 (3) | −0.014 (3) | 0.009 (3) | −0.022 (3) |
C03 | 0.059 (4) | 0.046 (4) | 0.053 (4) | −0.016 (4) | 0.017 (3) | −0.017 (3) |
C04 | 0.057 (4) | 0.028 (3) | 0.052 (4) | 0.005 (3) | 0.009 (3) | −0.004 (3) |
C05 | 0.035 (3) | 0.042 (3) | 0.040 (3) | 0.003 (3) | 0.000 (3) | 0.003 (3) |
C06 | 0.034 (3) | 0.030 (3) | 0.022 (3) | −0.007 (2) | 0.007 (2) | 0.001 (2) |
C07 | 0.029 (3) | 0.035 (3) | 0.029 (3) | 0.004 (2) | 0.004 (2) | 0.000 (2) |
C08 | 0.034 (3) | 0.030 (3) | 0.033 (3) | −0.009 (2) | 0.008 (2) | −0.005 (2) |
C09 | 0.104 (5) | 0.036 (3) | 0.037 (3) | −0.009 (3) | 0.010 (3) | −0.001 (3) |
C10 | 0.044 (3) | 0.033 (3) | 0.042 (3) | −0.003 (3) | 0.003 (2) | 0.006 (2) |
C11 | 0.030 (3) | 0.031 (3) | 0.027 (3) | −0.005 (2) | 0.001 (2) | −0.001 (3) |
C12 | 0.022 (3) | 0.028 (3) | 0.033 (3) | 0.005 (2) | −0.001 (2) | −0.006 (2) |
C21 | 0.033 (3) | 0.047 (3) | 0.038 (3) | −0.004 (3) | −0.002 (2) | 0.007 (3) |
C22 | 0.040 (3) | 0.055 (4) | 0.046 (3) | −0.016 (3) | −0.007 (3) | 0.016 (3) |
C23 | 0.063 (4) | 0.039 (3) | 0.052 (4) | −0.011 (3) | −0.023 (3) | 0.018 (3) |
C24 | 0.055 (4) | 0.030 (3) | 0.064 (4) | 0.002 (3) | −0.014 (3) | 0.004 (3) |
C25 | 0.031 (3) | 0.040 (3) | 0.043 (3) | 0.002 (2) | −0.003 (2) | −0.003 (2) |
C26 | 0.031 (3) | 0.035 (3) | 0.020 (2) | −0.004 (2) | −0.008 (2) | 0.004 (2) |
C27 | 0.028 (3) | 0.034 (3) | 0.026 (3) | −0.002 (2) | −0.002 (2) | −0.001 (2) |
C28 | 0.031 (3) | 0.030 (3) | 0.032 (3) | −0.002 (3) | −0.006 (2) | 0.004 (2) |
C29 | 0.100 (5) | 0.049 (4) | 0.025 (3) | 0.006 (4) | −0.010 (3) | −0.004 (3) |
C30 | 0.047 (3) | 0.035 (3) | 0.040 (3) | 0.009 (3) | −0.001 (2) | −0.004 (3) |
N01 | 0.029 (2) | 0.035 (3) | 0.027 (2) | 0.001 (2) | 0.0032 (17) | −0.001 (2) |
N21 | 0.028 (2) | 0.033 (3) | 0.030 (2) | −0.0008 (19) | 0.0023 (17) | 0.002 (2) |
O02 | 0.0289 (18) | 0.041 (2) | 0.049 (2) | 0.0090 (16) | −0.0089 (15) | 0.0067 (17) |
O03 | 0.0311 (19) | 0.030 (2) | 0.042 (2) | −0.0059 (15) | 0.0012 (15) | −0.0001 (15) |
O04 | 0.0410 (19) | 0.043 (2) | 0.0250 (18) | 0.0117 (17) | 0.0080 (14) | 0.0037 (15) |
O05 | 0.0338 (18) | 0.047 (2) | 0.0264 (17) | −0.0018 (17) | 0.0010 (14) | −0.0060 (15) |
O06 | 0.0232 (17) | 0.041 (2) | 0.0404 (19) | 0.0058 (15) | −0.0010 (14) | −0.0060 (16) |
O07 | 0.0327 (19) | 0.035 (2) | 0.057 (2) | −0.0085 (16) | 0.0121 (16) | 0.0074 (17) |
O21 | 0.0320 (19) | 0.039 (2) | 0.040 (2) | −0.0056 (15) | 0.0001 (14) | −0.0024 (15) |
S1 | 0.0244 (7) | 0.0293 (7) | 0.0316 (7) | 0.0036 (6) | −0.0001 (5) | 0.0010 (6) |
S2 | 0.0232 (6) | 0.0291 (7) | 0.0319 (7) | −0.0010 (6) | 0.0040 (5) | −0.0019 (6) |
O01 | 0.0238 (18) | 0.042 (2) | 0.048 (2) | −0.0016 (15) | −0.0022 (15) | −0.0038 (17) |
C01—C06 | 1.386 (6) | C22—C23 | 1.375 (8) |
C01—C02 | 1.393 (7) | C22—H22 | 1.02 (5) |
C01—H01 | 0.93 | C23—C24 | 1.355 (8) |
C02—C03 | 1.358 (8) | C23—H23 | 0.93 |
C02—H02 | 0.96 (5) | C24—C25 | 1.378 (7) |
C03—C04 | 1.376 (9) | C24—H24 | 0.91 (5) |
C03—H03 | 1.01 (5) | C25—C26 | 1.391 (7) |
C04—C05 | 1.377 (7) | C25—H25 | 0.93 |
C04—H04 | 0.92 (5) | C26—C27 | 1.529 (7) |
C05—C06 | 1.377 (7) | C27—O21 | 1.431 (5) |
C05—H05 | 0.87 (4) | C27—C28 | 1.519 (6) |
C06—C07 | 1.525 (7) | C27—H27 | 0.95 (4) |
C07—O01 | 1.431 (5) | C28—N21 | 1.500 (6) |
C07—C08 | 1.529 (6) | C28—C29 | 1.519 (7) |
C07—H7 | 1.10 (4) | C28—H28 | 0.87 (4) |
C08—C09 | 1.511 (7) | C29—H29A | 0.96 |
C08—N01 | 1.518 (6) | C29—H29B | 0.96 |
C08—H08 | 0.98 | C29—H29C | 0.96 |
C09—H09A | 0.96 | C30—N21 | 1.487 (6) |
C09—H09B | 0.96 | C30—H32A | 0.96 |
C09—H09C | 0.96 | C30—H32B | 0.96 |
C10—N01 | 1.481 (6) | C30—H32C | 0.96 |
C10—H12A | 0.96 | N01—H10 | 0.9 |
C10—H12B | 0.96 | N01—H11 | 0.9 |
C10—H12C | 0.96 | N21—H30 | 0.9 |
C11—C12 | 1.514 (5) | N21—H31 | 0.9 |
C11—S1 | 1.787 (5) | O02—S1 | 1.458 (3) |
C11—H13 | 0.96 (5) | O03—S1 | 1.454 (3) |
C11—H14 | 0.94 (4) | O04—S1 | 1.456 (3) |
C12—S2 | 1.774 (5) | O05—S2 | 1.457 (3) |
C12—H15 | 0.97 | O06—S2 | 1.457 (3) |
C12—H16 | 0.97 | O07—S2 | 1.454 (3) |
C21—C22 | 1.366 (7) | O21—H26 | 0.82 |
C21—C26 | 1.398 (6) | O01—H06 | 0.82 |
C21—H21 | 0.93 | ||
C06—C01—C02 | 121.0 (5) | C24—C23—H23 | 120 |
C06—C01—H01 | 119.5 | C22—C23—H23 | 120 |
C02—C01—H01 | 119.5 | C23—C24—C25 | 120.7 (6) |
C03—C02—C01 | 119.1 (6) | C23—C24—H24 | 121 (3) |
C03—C02—H02 | 117 (3) | C25—C24—H24 | 119 (3) |
C01—C02—H02 | 124 (3) | C24—C25—C26 | 120.5 (5) |
C02—C03—C04 | 120.8 (6) | C24—C25—H25 | 119.7 |
C02—C03—H03 | 118 (3) | C26—C25—H25 | 119.7 |
C04—C03—H03 | 121 (3) | C25—C26—C21 | 117.4 (5) |
C03—C04—C05 | 119.8 (6) | C25—C26—C27 | 123.6 (4) |
C03—C04—H04 | 120 (3) | C21—C26—C27 | 119.0 (5) |
C05—C04—H04 | 120 (3) | O21—C27—C28 | 107.0 (4) |
C06—C05—C04 | 120.8 (5) | O21—C27—C26 | 111.7 (4) |
C06—C05—H05 | 127 (3) | C28—C27—C26 | 111.5 (4) |
C04—C05—H05 | 112 (3) | O21—C27—H27 | 115 (2) |
C05—C06—C01 | 118.4 (5) | C28—C27—H27 | 103 (2) |
C05—C06—C07 | 122.5 (4) | C26—C27—H27 | 108 (2) |
C01—C06—C07 | 119.2 (5) | N21—C28—C27 | 109.2 (4) |
O01—C07—C06 | 113.0 (4) | N21—C28—C29 | 108.1 (4) |
O01—C07—C08 | 106.2 (4) | C27—C28—C29 | 114.2 (4) |
C06—C07—C08 | 111.8 (4) | N21—C28—H28 | 103 (3) |
O01—C07—H7 | 106 (2) | C27—C28—H28 | 109 (3) |
C06—C07—H7 | 114 (2) | C29—C28—H28 | 113 (3) |
C08—C07—H7 | 105 (2) | C28—C29—H29A | 109.5 |
C09—C08—N01 | 108.0 (4) | C28—C29—H29B | 109.5 |
C09—C08—C07 | 113.8 (4) | H29A—C29—H29B | 109.5 |
N01—C08—C07 | 108.5 (4) | C28—C29—H29C | 109.5 |
C09—C08—H08 | 108.9 | H29A—C29—H29C | 109.5 |
N01—C08—H08 | 108.9 | H29B—C29—H29C | 109.5 |
C07—C08—H08 | 108.9 | N21—C30—H32A | 109.5 |
C08—C09—H09A | 109.5 | N21—C30—H32B | 109.5 |
C08—C09—H09B | 109.5 | H32A—C30—H32B | 109.5 |
H09A—C09—H09B | 109.5 | N21—C30—H32C | 109.5 |
C08—C09—H09C | 109.5 | H32A—C30—H32C | 109.5 |
H09A—C09—H09C | 109.5 | H32B—C30—H32C | 109.5 |
H09B—C09—H09C | 109.5 | C10—N01—C08 | 116.1 (4) |
N01—C10—H12A | 109.5 | C10—N01—H10 | 108.3 |
N01—C10—H12B | 109.5 | C08—N01—H10 | 108.3 |
H12A—C10—H12B | 109.5 | C10—N01—H11 | 108.3 |
N01—C10—H12C | 109.5 | C08—N01—H11 | 108.3 |
H12A—C10—H12C | 109.5 | H10—N01—H11 | 107.4 |
H12B—C10—H12C | 109.5 | C30—N21—C28 | 116.9 (3) |
C12—C11—S1 | 112.7 (3) | C30—N21—H30 | 108.1 |
C12—C11—H13 | 111 (3) | C28—N21—H30 | 108.1 |
S1—C11—H13 | 103 (3) | C30—N21—H31 | 108.1 |
C12—C11—H14 | 110 (2) | C28—N21—H31 | 108.1 |
S1—C11—H14 | 105 (2) | H30—N21—H31 | 107.3 |
H13—C11—H14 | 115 (4) | C27—O21—H26 | 109.5 |
C11—C12—S2 | 111.2 (3) | O03—S1—O04 | 112.99 (19) |
C11—C12—H15 | 109.4 | O03—S1—O02 | 113.5 (2) |
S2—C12—H15 | 109.4 | O04—S1—O02 | 111.9 (2) |
C11—C12—H16 | 109.4 | O03—S1—C11 | 105.6 (2) |
S2—C12—H16 | 109.4 | O04—S1—C11 | 106.5 (2) |
H15—C12—H16 | 108 | O02—S1—C11 | 105.6 (2) |
C22—C21—C26 | 121.3 (5) | O07—S2—O06 | 114.1 (2) |
C22—C21—H21 | 119.3 | O07—S2—O05 | 111.2 (2) |
C26—C21—H21 | 119.3 | O06—S2—O05 | 112.70 (18) |
C21—C22—C23 | 119.9 (6) | O07—S2—C12 | 106.3 (2) |
C21—C22—H22 | 118 (3) | O06—S2—C12 | 105.5 (2) |
C23—C22—H22 | 122 (3) | O05—S2—C12 | 106.4 (2) |
C24—C23—C22 | 120.1 (6) | C07—O01—H06 | 109.5 |
C06—C01—C02—C03 | 1.0 (8) | C24—C25—C26—C27 | −178.8 (5) |
C01—C02—C03—C04 | 0.3 (9) | C22—C21—C26—C25 | −1.7 (7) |
C02—C03—C04—C05 | −0.5 (9) | C22—C21—C26—C27 | 178.0 (4) |
C03—C04—C05—C06 | −0.7 (8) | C25—C26—C27—O21 | 23.2 (6) |
C04—C05—C06—C01 | 1.9 (7) | C21—C26—C27—O21 | −156.5 (4) |
C04—C05—C06—C07 | −177.7 (5) | C25—C26—C27—C28 | −96.5 (6) |
C02—C01—C06—C05 | −2.1 (7) | C21—C26—C27—C28 | 83.8 (6) |
C02—C01—C06—C07 | 177.5 (5) | O21—C27—C28—N21 | 59.4 (5) |
C05—C06—C07—O01 | 21.5 (6) | C26—C27—C28—N21 | −178.2 (4) |
C01—C06—C07—O01 | −158.1 (4) | O21—C27—C28—C29 | −61.7 (5) |
C05—C06—C07—C08 | −98.2 (5) | C26—C27—C28—C29 | 60.7 (6) |
C01—C06—C07—C08 | 82.1 (6) | C09—C08—N01—C10 | 179.8 (4) |
O01—C07—C08—C09 | −67.1 (5) | C07—C08—N01—C10 | 56.1 (5) |
C06—C07—C08—C09 | 56.6 (6) | C27—C28—N21—C30 | 53.5 (5) |
O01—C07—C08—N01 | 53.0 (5) | C29—C28—N21—C30 | 178.2 (4) |
C06—C07—C08—N01 | 176.7 (4) | C12—C11—S1—O03 | 48.7 (4) |
S1—C11—C12—S2 | −178.4 (3) | C12—C11—S1—O04 | −71.7 (4) |
C26—C21—C22—C23 | 1.0 (8) | C12—C11—S1—O02 | 169.2 (3) |
C21—C22—C23—C24 | 0.6 (9) | C11—C12—S2—O07 | −68.1 (3) |
C22—C23—C24—C25 | −1.4 (9) | C11—C12—S2—O06 | 170.5 (3) |
C23—C24—C25—C26 | 0.6 (8) | C11—C12—S2—O05 | 50.6 (3) |
C24—C25—C26—C21 | 0.9 (7) |
D—H···A | D—H | H···A | D···A | D—H···A |
N01—H10···O06i | 0.9 | 1.98 | 2.868 (5) | 171 |
N01—H10···S2i | 0.9 | 2.88 | 3.642 (4) | 144 |
N01—H11···O05ii | 0.9 | 2.12 | 2.915 (5) | 147 |
N01—H11···S2ii | 0.9 | 2.88 | 3.614 (4) | 140 |
N21—H30···O03iii | 0.9 | 1.98 | 2.860 (5) | 164 |
N21—H30···S1iii | 0.9 | 2.95 | 3.717 (4) | 144 |
N21—H31···O04iv | 0.9 | 2.1 | 2.919 (5) | 151 |
N21—H31···S1iv | 0.9 | 2.9 | 3.648 (4) | 142 |
O21—H26···O02v | 0.82 | 2 | 2.771 (4) | 156 |
O21—H26···S1v | 0.82 | 2.96 | 3.778 (3) | 178 |
Symmetry codes: (i) x−1, y, z+1; (ii) x, y, z+1; (iii) −x+3, y−1/2, −z+2; (iv) −x+2, y−1/2, −z+2; (v) −x+2, y−1/2, −z+1. |
C10H16NO | F(000) = 360 |
Mr = 165.23 | Dx = 1.114 Mg m−3 |
Orthorhombic, P212121 | Mo Kα radiation, λ = 0.71073 Å |
Hall symbol: P 2ac 2ab | Cell parameters from 15515 reflections |
a = 5.6851 (4) Å | θ = 1.0–27.5° |
b = 7.7047 (5) Å | µ = 0.07 mm−1 |
c = 22.4819 (17) Å | T = 150 K |
V = 984.75 (12) Å3 | Plate, colourless |
Z = 4 | 0.25 × 0.05 × 0.05 mm |
KappaCCD diffractometer | 1340 independent reflections |
Radiation source: Enraf Nonius FR590 | 617 reflections with I > 2σ(I) |
Graphite monochromator | Rint = 0.076 |
CCD rotation images, thick slices scans | θmax = 27.5°, θmin = 2.8° |
Absorption correction: multi-scan R.H. Blessing, Acta Cryst. (1995), A51, 33-38 | h = −7→7 |
Tmin = 0.975, Tmax = 1.061 | k = −10→7 |
8327 measured reflections | l = −28→29 |
Refinement on F2 | Secondary atom site location: difference Fourier map |
Least-squares matrix: full | Hydrogen site location: inferred from neighbouring sites |
R[F2 > 2σ(F2)] = 0.056 | H atoms treated by a mixture of independent and constrained refinement |
wR(F2) = 0.115 | w = 1/[σ2(Fo2) + (0.0433P)2] where P = (Fo2 + 2Fc2)/3 |
S = 0.96 | (Δ/σ)max < 0.001 |
1340 reflections | Δρmax = 0.23 e Å−3 |
154 parameters | Δρmin = −0.22 e Å−3 |
0 restraints | Extinction correction: SHELXL, Fc*=kFc[1+0.001xFc2λ3/sin(2θ)]-1/4 |
Primary atom site location: structure-invariant direct methods | Extinction coefficient: 0.029 (5) |
C10H16NO | V = 984.75 (12) Å3 |
Mr = 165.23 | Z = 4 |
Orthorhombic, P212121 | Mo Kα radiation |
a = 5.6851 (4) Å | µ = 0.07 mm−1 |
b = 7.7047 (5) Å | T = 150 K |
c = 22.4819 (17) Å | 0.25 × 0.05 × 0.05 mm |
KappaCCD diffractometer | 1340 independent reflections |
Absorption correction: multi-scan R.H. Blessing, Acta Cryst. (1995), A51, 33-38 | 617 reflections with I > 2σ(I) |
Tmin = 0.975, Tmax = 1.061 | Rint = 0.076 |
8327 measured reflections |
R[F2 > 2σ(F2)] = 0.056 | 0 restraints |
wR(F2) = 0.115 | H atoms treated by a mixture of independent and constrained refinement |
S = 0.96 | Δρmax = 0.23 e Å−3 |
1340 reflections | Δρmin = −0.22 e Å−3 |
154 parameters |
Geometry. All e.s.d.'s (except the e.s.d. in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell e.s.d.'s are taken into account individually in the estimation of e.s.d.'s in distances, angles and torsion angles; correlations between e.s.d.'s in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell e.s.d.'s is used for estimating e.s.d.'s involving l.s. planes. |
Refinement. Refinement of F2 against ALL reflections. The weighted R-factor wR and goodness of fit S are based on F2, conventional R-factors R are based on F, with F set to zero for negative F2. The threshold expression of F2 > σ(F2) is used only for calculating R-factors(gt) etc. and is not relevant to the choice of reflections for refinement. R-factors based on F2 are statistically about twice as large as those based on F, and R- factors based on ALL data will be even larger. |
x | y | z | Uiso*/Ueq | ||
C1 | 0.0038 (7) | 0.0288 (5) | 0.35785 (16) | 0.0424 (10) | |
H1 | −0.117 (6) | 0.034 (4) | 0.3892 (14) | 0.051* | |
C2 | −0.0285 (8) | −0.0706 (6) | 0.3072 (2) | 0.0573 (13) | |
H2 | −0.177 (6) | −0.145 (5) | 0.2999 (16) | 0.069* | |
C3 | 0.1436 (10) | −0.0785 (7) | 0.2651 (2) | 0.0697 (16) | |
H3 | 0.126 (7) | −0.161 (6) | 0.2310 (17) | 0.084* | |
C4 | 0.3490 (9) | 0.0151 (8) | 0.27192 (17) | 0.0694 (16) | |
H4 | 0.481 (8) | 0.019 (6) | 0.2419 (17) | 0.083* | |
C5 | 0.3820 (8) | 0.1170 (6) | 0.32321 (15) | 0.0543 (13) | |
H5 | 0.530 (6) | 0.188 (5) | 0.3327 (15) | 0.065* | |
C6 | 0.2098 (6) | 0.1225 (5) | 0.36642 (15) | 0.0380 (10) | |
C7 | 0.2359 (6) | 0.2316 (5) | 0.42236 (14) | 0.0361 (10) | |
H7 | 0.169 (5) | 0.152 (4) | 0.4568 (13) | 0.043* | |
C8 | 0.1075 (7) | 0.4034 (5) | 0.41872 (14) | 0.0375 (10) | |
H8 | −0.068 (6) | 0.389 (5) | 0.4089 (13) | 0.045* | |
C9 | 0.2151 (8) | 0.5247 (6) | 0.37257 (18) | 0.0527 (12) | |
H9A | 0.219 (6) | 0.477 (5) | 0.3329 (15) | 0.063* | |
H9B | 0.395 (7) | 0.555 (5) | 0.3818 (15) | 0.063* | |
H9C | 0.129 (7) | 0.637 (5) | 0.3703 (15) | 0.063* | |
C10 | −0.0643 (8) | 0.6247 (6) | 0.4851 (2) | 0.0532 (12) | |
H11A | −0.057 (6) | 0.663 (5) | 0.5312 (16) | 0.064* | |
H11B | −0.228 (6) | 0.579 (5) | 0.4746 (15) | 0.064* | |
H11C | −0.029 (6) | 0.725 (5) | 0.4629 (17) | 0.064* | |
N1 | 0.0998 (6) | 0.4786 (4) | 0.47910 (13) | 0.0414 (9) | |
H10 | 0.242 (5) | 0.512 (4) | 0.4858 (12) | 0.015 (8)* | |
O1 | 0.4778 (4) | 0.2673 (3) | 0.43595 (9) | 0.0449 (8) | |
H6 | 0.5239 | 0.1995 | 0.4615 | 0.067* |
U11 | U22 | U33 | U12 | U13 | U23 | |
C1 | 0.045 (2) | 0.045 (3) | 0.037 (2) | 0.007 (2) | −0.006 (2) | −0.005 (2) |
C2 | 0.062 (3) | 0.049 (3) | 0.061 (3) | 0.015 (3) | −0.026 (3) | −0.014 (2) |
C3 | 0.082 (4) | 0.074 (4) | 0.053 (3) | 0.035 (3) | −0.029 (3) | −0.026 (3) |
C4 | 0.060 (3) | 0.105 (4) | 0.043 (3) | 0.037 (3) | 0.004 (3) | −0.011 (3) |
C5 | 0.051 (2) | 0.078 (4) | 0.034 (2) | 0.018 (3) | 0.000 (2) | −0.004 (2) |
C6 | 0.036 (2) | 0.044 (3) | 0.0337 (19) | 0.012 (2) | −0.0032 (18) | 0.0008 (19) |
C7 | 0.0308 (19) | 0.045 (3) | 0.0326 (19) | 0.001 (2) | −0.0019 (16) | 0.0036 (19) |
C8 | 0.039 (2) | 0.040 (3) | 0.033 (2) | 0.001 (2) | −0.0026 (19) | 0.0003 (19) |
C9 | 0.063 (3) | 0.053 (3) | 0.042 (2) | 0.002 (3) | 0.002 (2) | 0.007 (2) |
C10 | 0.056 (3) | 0.040 (3) | 0.063 (3) | 0.002 (3) | 0.015 (2) | −0.006 (2) |
N1 | 0.037 (2) | 0.045 (2) | 0.0427 (19) | −0.0042 (19) | 0.0026 (16) | −0.0065 (16) |
O1 | 0.0336 (13) | 0.060 (2) | 0.0414 (15) | −0.0001 (15) | −0.0061 (12) | 0.0052 (12) |
C1—C2 | 1.385 (5) | C7—H7 | 1.06 (3) |
C1—C6 | 1.389 (5) | C8—N1 | 1.477 (4) |
C1—H1 | 0.98 (3) | C8—C9 | 1.524 (5) |
C2—C3 | 1.362 (6) | C8—H8 | 1.03 (3) |
C2—H2 | 1.03 (4) | C9—H9A | 0.97 (3) |
C3—C4 | 1.381 (7) | C9—H9B | 1.07 (4) |
C3—H3 | 1.00 (4) | C9—H9C | 1.00 (4) |
C4—C5 | 1.408 (6) | C10—N1 | 1.469 (5) |
C4—H4 | 1.01 (4) | C10—H11A | 1.08 (4) |
C5—C6 | 1.380 (5) | C10—H11B | 1.02 (4) |
C5—H5 | 1.03 (4) | C10—H11C | 0.94 (4) |
C6—C7 | 1.520 (5) | N1—H10 | 0.86 (3) |
C7—O1 | 1.435 (4) | O1—H6 | 0.82 |
C7—C8 | 1.514 (5) | ||
C2—C1—C6 | 120.9 (4) | C6—C7—H7 | 104.3 (17) |
C2—C1—H1 | 121.4 (19) | N1—C8—C7 | 107.9 (3) |
C6—C1—H1 | 117.7 (19) | N1—C8—C9 | 113.4 (4) |
C3—C2—C1 | 120.0 (5) | C7—C8—C9 | 112.3 (3) |
C3—C2—H2 | 117 (2) | N1—C8—H8 | 102.3 (18) |
C1—C2—H2 | 123 (2) | C7—C8—H8 | 112 (2) |
C2—C3—C4 | 120.5 (4) | C9—C8—H8 | 108.1 (19) |
C2—C3—H3 | 119 (2) | C8—C9—H9A | 114 (2) |
C4—C3—H3 | 120 (2) | C8—C9—H9B | 113 (2) |
C3—C4—C5 | 119.7 (4) | H9A—C9—H9B | 104 (3) |
C3—C4—H4 | 125 (2) | C8—C9—H9C | 112 (2) |
C5—C4—H4 | 116 (2) | H9A—C9—H9C | 107 (3) |
C6—C5—C4 | 119.9 (5) | H9B—C9—H9C | 107 (3) |
C6—C5—H5 | 115 (2) | N1—C10—H11A | 106.1 (19) |
C4—C5—H5 | 125 (2) | N1—C10—H11B | 107 (2) |
C5—C6—C1 | 119.0 (4) | H11A—C10—H11B | 110 (3) |
C5—C6—C7 | 122.0 (4) | N1—C10—H11C | 116 (2) |
C1—C6—C7 | 119.0 (3) | H11A—C10—H11C | 106 (3) |
O1—C7—C8 | 107.8 (3) | H11B—C10—H11C | 111 (3) |
O1—C7—C6 | 112.1 (3) | C10—N1—C8 | 113.8 (3) |
C8—C7—C6 | 113.1 (3) | C10—N1—H10 | 110 (2) |
O1—C7—H7 | 107.3 (17) | C8—N1—H10 | 104.5 (19) |
C8—C7—H7 | 112.1 (17) | C7—O1—H6 | 109.5 |
C6—C1—C2—C3 | 0.6 (6) | C1—C6—C7—O1 | 158.6 (3) |
C1—C2—C3—C4 | −1.5 (7) | C5—C6—C7—C8 | 99.1 (4) |
C2—C3—C4—C5 | 1.1 (8) | C1—C6—C7—C8 | −79.3 (4) |
C3—C4—C5—C6 | 0.2 (7) | O1—C7—C8—N1 | −68.2 (3) |
C4—C5—C6—C1 | −1.1 (6) | C6—C7—C8—N1 | 167.4 (3) |
C4—C5—C6—C7 | −179.5 (4) | O1—C7—C8—C9 | 57.5 (4) |
C2—C1—C6—C5 | 0.7 (6) | C6—C7—C8—C9 | −66.9 (4) |
C2—C1—C6—C7 | 179.2 (3) | C7—C8—N1—C10 | −166.9 (3) |
C5—C6—C7—O1 | −23.0 (5) | C9—C8—N1—C10 | 68.1 (4) |
D—H···A | D—H | H···A | D···A | D—H···A |
O1—H6···N1i | 0.82 | 1.96 | 2.778 (4) | 173 |
Symmetry code: (i) x+1/2, −y+1/2, −z+1. |
C12H21NO4S | F(000) = 592 |
Mr = 275.36 | Dx = 1.237 Mg m−3 |
Orthorhombic, P212121 | Mo Kα radiation, λ = 0.71073 Å |
Hall symbol: P 2ac 2ab | Cell parameters from 1430 reflections |
a = 5.4877 (7) Å | θ = 1.0–27.5° |
b = 11.9057 (17) Å | µ = 0.23 mm−1 |
c = 22.639 (4) Å | T = 150 K |
V = 1479.1 (4) Å3 | Needle, colourless |
Z = 4 | 0.25 × 0.05 × 0.05 mm |
KappaCCD diffractometer | 1073 reflections with I > 2σ(I) |
Radiation source: Enraf Nonius FR590 | θmax = 28.2°, θmin = 3.2° |
Graphite monochromator | h = 0→7 |
CCD rotation images, thick slices scans | k = 0→15 |
1831 measured reflections | l = 0→28 |
1831 independent reflections |
Refinement on F2 | Secondary atom site location: difference Fourier map |
Least-squares matrix: full | Hydrogen site location: inferred from neighbouring sites |
R[F2 > 2σ(F2)] = 0.102 | H atoms treated by a mixture of independent and constrained refinement |
wR(F2) = 0.264 | w = 1/[σ2(Fo2) + (0.0573P)2 + 6.3635P] where P = (Fo2 + 2Fc2)/3 |
S = 1.08 | (Δ/σ)max < 0.001 |
1831 reflections | Δρmax = 0.33 e Å−3 |
169 parameters | Δρmin = −0.31 e Å−3 |
0 restraints | Extinction correction: SHELXL, Fc*=kFc[1+0.001xFc2λ3/sin(2θ)]-1/4 |
Primary atom site location: structure-invariant direct methods | Extinction coefficient: 0.025 (5) |
C12H21NO4S | V = 1479.1 (4) Å3 |
Mr = 275.36 | Z = 4 |
Orthorhombic, P212121 | Mo Kα radiation |
a = 5.4877 (7) Å | µ = 0.23 mm−1 |
b = 11.9057 (17) Å | T = 150 K |
c = 22.639 (4) Å | 0.25 × 0.05 × 0.05 mm |
KappaCCD diffractometer | 1831 independent reflections |
1831 measured reflections | 1073 reflections with I > 2σ(I) |
R[F2 > 2σ(F2)] = 0.102 | 0 restraints |
wR(F2) = 0.264 | H atoms treated by a mixture of independent and constrained refinement |
S = 1.08 | Δρmax = 0.33 e Å−3 |
1831 reflections | Δρmin = −0.31 e Å−3 |
169 parameters |
Geometry. All e.s.d.'s (except the e.s.d. in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell e.s.d.'s are taken into account individually in the estimation of e.s.d.'s in distances, angles and torsion angles; correlations between e.s.d.'s in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell e.s.d.'s is used for estimating e.s.d.'s involving l.s. planes. |
Refinement. Refinement of F2 against ALL reflections. The weighted R-factor wR and goodness of fit S are based on F2, conventional R-factors R are based on F, with F set to zero for negative F2. The threshold expression of F2 > σ(F2) is used only for calculating R-factors(gt) etc. and is not relevant to the choice of reflections for refinement. R-factors based on F2 are statistically about twice as large as those based on F, and R- factors based on ALL data will be even larger. |
x | y | z | Uiso*/Ueq | ||
C1 | 0.674 (2) | 0.2150 (9) | 0.1265 (6) | 0.065 (3) | |
H1C | 0.7966 | 0.2317 | 0.1536 | 0.078* | |
C2 | 0.697 (2) | 0.1248 (9) | 0.0875 (7) | 0.073 (4) | |
H2 | 0.8307 | 0.0776 | 0.0914 | 0.087* | |
C3 | 0.538 (3) | 0.1034 (9) | 0.0456 (7) | 0.083 (4) | |
H3 | 0.5636 | 0.0449 | 0.0191 | 0.1* | |
C4 | 0.327 (3) | 0.1704 (12) | 0.0413 (7) | 0.083 (4) | |
H4 | 0.2102 | 0.1557 | 0.0127 | 0.1* | |
C5 | 0.297 (2) | 0.2580 (9) | 0.0802 (6) | 0.068 (3) | |
H5 | 0.1607 | 0.3039 | 0.0769 | 0.082* | |
C6 | 0.4635 (18) | 0.2787 (8) | 0.1235 (5) | 0.052 (2) | |
C7 | 0.4312 (17) | 0.3764 (7) | 0.1673 (5) | 0.053 (3) | |
H7 | 0.4878 | 0.352 | 0.2063 | 0.064* | |
C8 | 0.5694 (19) | 0.4821 (8) | 0.1499 (5) | 0.053 (3) | |
H8 | 0.7446 | 0.4665 | 0.152 | 0.063* | |
C9 | 0.511 (3) | 0.5260 (9) | 0.0894 (5) | 0.071 (3) | |
H9A | 0.3405 | 0.5428 | 0.087 | 0.106* | |
H9B | 0.5524 | 0.4703 | 0.0604 | 0.106* | |
H9C | 0.6038 | 0.5931 | 0.0822 | 0.106* | |
C10 | 0.570 (2) | 0.5481 (10) | 0.2549 (6) | 0.071 (4) | |
H12A | 0.4657 | 0.4894 | 0.2693 | 0.106* | |
H12B | 0.5459 | 0.6146 | 0.2781 | 0.106* | |
H12C | 0.7368 | 0.5246 | 0.2578 | 0.106* | |
C11 | −0.120 (2) | 0.3574 (9) | 0.3706 (6) | 0.070 (4) | |
H13 | −0.0833 | 0.4359 | 0.3633 | 0.084* | |
H14 | −0.2952 | 0.3481 | 0.3672 | 0.084* | |
C12 | −0.047 (4) | 0.3296 (15) | 0.4311 (7) | 0.116 (6) | |
H15A | −0.0546 | 0.2498 | 0.4366 | 0.173* | |
H15B | −0.1543 | 0.3659 | 0.4585 | 0.173* | |
H15C | 0.1171 | 0.355 | 0.4377 | 0.173* | |
N1 | 0.5102 (16) | 0.5721 (6) | 0.1926 (4) | 0.053 (2) | |
H10 | 0.5901 | 0.6348 | 0.1817 | 0.064* | |
H11 | 0.3496 | 0.5868 | 0.1901 | 0.064* | |
O1 | 0.1779 (12) | 0.4058 (5) | 0.1715 (4) | 0.060 (2) | |
H6 | 0.1577 | 0.4696 | 0.1587 | 0.091* | |
O2 | 0.2829 (12) | 0.2952 (6) | 0.3204 (5) | 0.072 (2) | |
O3 | −0.0346 (14) | 0.1593 (6) | 0.3292 (4) | 0.072 (2) | |
O4 | −0.0808 (14) | 0.3093 (8) | 0.2601 (4) | 0.076 (3) | |
S1 | 0.0218 (5) | 0.2757 (2) | 0.31611 (14) | 0.0563 (8) |
U11 | U22 | U33 | U12 | U13 | U23 | |
C1 | 0.045 (6) | 0.048 (5) | 0.103 (10) | −0.001 (6) | −0.002 (6) | −0.002 (6) |
C2 | 0.051 (7) | 0.046 (6) | 0.122 (12) | 0.013 (6) | 0.003 (8) | −0.004 (7) |
C3 | 0.091 (10) | 0.045 (6) | 0.113 (12) | 0.005 (8) | 0.014 (10) | −0.016 (6) |
C4 | 0.066 (8) | 0.085 (9) | 0.099 (11) | −0.023 (8) | −0.017 (8) | −0.018 (8) |
C5 | 0.068 (7) | 0.063 (7) | 0.074 (9) | 0.001 (6) | −0.010 (7) | −0.020 (6) |
C6 | 0.039 (5) | 0.043 (5) | 0.074 (7) | 0.002 (5) | 0.005 (5) | −0.003 (5) |
C7 | 0.036 (5) | 0.039 (5) | 0.085 (9) | 0.005 (4) | −0.002 (5) | 0.003 (5) |
C8 | 0.043 (5) | 0.045 (5) | 0.070 (7) | 0.007 (5) | 0.001 (5) | −0.003 (5) |
C9 | 0.084 (9) | 0.053 (5) | 0.076 (8) | −0.032 (7) | −0.005 (8) | 0.012 (5) |
C10 | 0.074 (9) | 0.075 (8) | 0.062 (8) | −0.019 (7) | −0.003 (7) | −0.012 (6) |
C11 | 0.055 (7) | 0.050 (6) | 0.105 (12) | 0.012 (6) | −0.003 (7) | −0.005 (6) |
C12 | 0.142 (15) | 0.141 (13) | 0.064 (10) | 0.011 (14) | −0.011 (11) | −0.021 (8) |
N1 | 0.039 (4) | 0.041 (4) | 0.080 (6) | 0.003 (4) | 0.001 (5) | −0.003 (4) |
O1 | 0.041 (4) | 0.039 (3) | 0.102 (7) | 0.007 (3) | 0.002 (4) | 0.006 (4) |
O2 | 0.033 (4) | 0.062 (4) | 0.120 (7) | −0.013 (3) | −0.002 (4) | −0.006 (5) |
O3 | 0.054 (4) | 0.043 (4) | 0.120 (7) | −0.005 (4) | 0.005 (5) | −0.007 (4) |
O4 | 0.057 (5) | 0.105 (7) | 0.067 (6) | −0.001 (5) | −0.005 (4) | 0.004 (5) |
S1 | 0.0447 (14) | 0.0501 (13) | 0.0742 (19) | −0.0012 (13) | 0.0006 (15) | −0.0003 (13) |
C1—C6 | 1.385 (14) | C9—H9B | 0.96 |
C1—C2 | 1.395 (17) | C9—H9C | 0.96 |
C1—H1C | 0.93 | C10—N1 | 1.476 (15) |
C2—C3 | 1.315 (19) | C10—H12A | 0.96 |
C2—H2 | 0.93 | C10—H12B | 0.96 |
C3—C4 | 1.406 (19) | C10—H12C | 0.96 |
C3—H3 | 0.93 | C11—C12 | 1.465 (19) |
C4—C5 | 1.374 (17) | C11—S1 | 1.754 (12) |
C4—H4 | 0.93 | C11—H13 | 0.97 |
C5—C6 | 1.362 (15) | C11—H14 | 0.97 |
C5—H5 | 0.93 | C12—H15A | 0.96 |
C6—C7 | 1.540 (14) | C12—H15B | 0.96 |
C7—O1 | 1.436 (11) | C12—H15C | 0.96 |
C7—C8 | 1.521 (13) | N1—H10 | 0.9 |
C7—H7 | 0.98 | N1—H11 | 0.9 |
C8—N1 | 1.480 (13) | O1—H6 | 0.82 |
C8—C9 | 1.500 (16) | O2—S1 | 1.455 (7) |
C8—H8 | 0.98 | O3—S1 | 1.450 (7) |
C9—H9A | 0.96 | O4—S1 | 1.443 (9) |
C6—C1—C2 | 117.6 (11) | H9A—C9—H9C | 109.5 |
C6—C1—H1C | 121.2 | H9B—C9—H9C | 109.5 |
C2—C1—H1C | 121.2 | N1—C10—H12A | 109.5 |
C3—C2—C1 | 123.2 (11) | N1—C10—H12B | 109.5 |
C3—C2—H2 | 118.4 | H12A—C10—H12B | 109.5 |
C1—C2—H2 | 118.4 | N1—C10—H12C | 109.5 |
C2—C3—C4 | 118.9 (11) | H12A—C10—H12C | 109.5 |
C2—C3—H3 | 120.5 | H12B—C10—H12C | 109.5 |
C4—C3—H3 | 120.5 | C12—C11—S1 | 114.2 (10) |
C5—C4—C3 | 119.1 (13) | C12—C11—H13 | 108.7 |
C5—C4—H4 | 120.5 | S1—C11—H13 | 108.7 |
C3—C4—H4 | 120.5 | C12—C11—H14 | 108.7 |
C6—C5—C4 | 121.1 (12) | S1—C11—H14 | 108.7 |
C6—C5—H5 | 119.4 | H13—C11—H14 | 107.6 |
C4—C5—H5 | 119.4 | C11—C12—H15A | 109.5 |
C5—C6—C1 | 119.8 (10) | C11—C12—H15B | 109.5 |
C5—C6—C7 | 121.5 (9) | H15A—C12—H15B | 109.5 |
C1—C6—C7 | 118.5 (10) | C11—C12—H15C | 109.5 |
O1—C7—C8 | 107.4 (7) | H15A—C12—H15C | 109.5 |
O1—C7—C6 | 109.7 (9) | H15B—C12—H15C | 109.5 |
C8—C7—C6 | 113.6 (9) | C10—N1—C8 | 115.8 (8) |
O1—C7—H7 | 108.7 | C10—N1—H10 | 108.3 |
C8—C7—H7 | 108.7 | C8—N1—H10 | 108.3 |
C6—C7—H7 | 108.7 | C10—N1—H11 | 108.3 |
N1—C8—C9 | 107.3 (8) | C8—N1—H11 | 108.3 |
N1—C8—C7 | 108.7 (8) | H10—N1—H11 | 107.4 |
C9—C8—C7 | 114.8 (9) | C7—O1—H6 | 109.5 |
N1—C8—H8 | 108.7 | O4—S1—O3 | 111.2 (5) |
C9—C8—H8 | 108.7 | O4—S1—O2 | 113.5 (6) |
C7—C8—H8 | 108.7 | O3—S1—O2 | 110.5 (5) |
C8—C9—H9A | 109.5 | O4—S1—C11 | 106.9 (6) |
C8—C9—H9B | 109.5 | O3—S1—C11 | 106.9 (6) |
H9A—C9—H9B | 109.5 | O2—S1—C11 | 107.6 (6) |
C8—C9—H9C | 109.5 |
D—H···A | D—H | H···A | D···A | D—H···A |
N1—H10···O2i | 0.9 | 2.03 | 2.904 (11) | 162 |
N1—H10···O3i | 0.9 | 2.47 | 3.099 (11) | 127 |
N1—H10···S1i | 0.9 | 2.71 | 3.537 (9) | 153 |
N1—H11···O3ii | 0.9 | 1.98 | 2.852 (11) | 162 |
O1—H6···O3ii | 0.82 | 2.37 | 3.119 (9) | 152 |
Symmetry codes: (i) −x+1, y+1/2, −z+1/2; (ii) −x, y+1/2, −z+1/2. |
C12H19NO4 | F(000) = 260 |
Mr = 241.28 | Dx = 1.302 Mg m−3 |
Monoclinic, P21 | Mo Kα radiation, λ = 0.71073 Å |
Hall symbol: P 2yb | Cell parameters from 2930 reflections |
a = 9.5946 (4) Å | θ = 1.0–27.5° |
b = 6.0474 (3) Å | µ = 0.10 mm−1 |
c = 10.8255 (5) Å | T = 150 K |
β = 101.607 (2)° | Needle, colourless |
V = 615.28 (5) Å3 | 0.3 × 0.05 × 0.05 mm |
Z = 2 |
KappaCCD diffractometer | 1513 independent reflections |
Radiation source: Enraf Nonius FR590 | 1200 reflections with I > 2σ(I) |
Graphite monochromator | Rint = 0.035 |
CCD rotation images, thick slices scans | θmax = 27.4°, θmin = 3.2° |
Absorption correction: multi-scan R.H. Blessing, Acta Cryst. (1995), A51, 33-38 | h = −12→11 |
Tmin = 0.938, Tmax = 1.054 | k = −7→6 |
4479 measured reflections | l = −14→12 |
Refinement on F2 | Primary atom site location: structure-invariant direct methods |
Least-squares matrix: full | Secondary atom site location: difference Fourier map |
R[F2 > 2σ(F2)] = 0.045 | Hydrogen site location: inferred from neighbouring sites |
wR(F2) = 0.098 | H atoms treated by a mixture of independent and constrained refinement |
S = 1.08 | w = 1/[σ2(Fo2) + (0.0409P)2 + 0.0943P] where P = (Fo2 + 2Fc2)/3 |
1513 reflections | (Δ/σ)max = 0.008 |
211 parameters | Δρmax = 0.23 e Å−3 |
1 restraint | Δρmin = −0.25 e Å−3 |
C12H19NO4 | V = 615.28 (5) Å3 |
Mr = 241.28 | Z = 2 |
Monoclinic, P21 | Mo Kα radiation |
a = 9.5946 (4) Å | µ = 0.10 mm−1 |
b = 6.0474 (3) Å | T = 150 K |
c = 10.8255 (5) Å | 0.3 × 0.05 × 0.05 mm |
β = 101.607 (2)° |
KappaCCD diffractometer | 1513 independent reflections |
Absorption correction: multi-scan R.H. Blessing, Acta Cryst. (1995), A51, 33-38 | 1200 reflections with I > 2σ(I) |
Tmin = 0.938, Tmax = 1.054 | Rint = 0.035 |
4479 measured reflections |
R[F2 > 2σ(F2)] = 0.045 | 1 restraint |
wR(F2) = 0.098 | H atoms treated by a mixture of independent and constrained refinement |
S = 1.08 | Δρmax = 0.23 e Å−3 |
1513 reflections | Δρmin = −0.25 e Å−3 |
211 parameters |
Geometry. All e.s.d.'s (except the e.s.d. in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell e.s.d.'s are taken into account individually in the estimation of e.s.d.'s in distances, angles and torsion angles; correlations between e.s.d.'s in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell e.s.d.'s is used for estimating e.s.d.'s involving l.s. planes. |
Refinement. Refinement of F2 against ALL reflections. The weighted R-factor wR and goodness of fit S are based on F2, conventional R-factors R are based on F, with F set to zero for negative F2. The threshold expression of F2 > σ(F2) is used only for calculating R-factors(gt) etc. and is not relevant to the choice of reflections for refinement. R-factors based on F2 are statistically about twice as large as those based on F, and R- factors based on ALL data will be even larger. |
x | y | z | Uiso*/Ueq | ||
C1 | −0.0109 (3) | 0.4855 (6) | 0.8559 (3) | 0.0238 (7) | |
H1 | −0.058 (3) | 0.345 (6) | 0.861 (3) | 0.029* | |
C2 | 0.1238 (3) | 0.5263 (6) | 0.9273 (3) | 0.0299 (8) | |
H2 | 0.174 (3) | 0.420 (7) | 0.981 (3) | 0.036* | |
C3 | 0.1865 (3) | 0.7304 (6) | 0.9218 (3) | 0.0305 (8) | |
H3 | 0.282 (3) | 0.757 (6) | 0.971 (3) | 0.037* | |
C4 | 0.1143 (3) | 0.8961 (6) | 0.8468 (3) | 0.0291 (8) | |
H4 | 0.163 (3) | 1.057 (7) | 0.851 (3) | 0.035* | |
C5 | −0.0213 (3) | 0.8552 (5) | 0.7754 (3) | 0.0231 (7) | |
H5 | −0.070 (3) | 0.973 (6) | 0.723 (3) | 0.028* | |
C6 | −0.0839 (3) | 0.6491 (5) | 0.7784 (2) | 0.0187 (6) | |
C7 | −0.2266 (3) | 0.5947 (5) | 0.6942 (3) | 0.0194 (6) | |
H7 | −0.282 (3) | 0.500 (6) | 0.747 (3) | 0.023* | |
C8 | −0.2027 (3) | 0.4557 (5) | 0.5816 (2) | 0.0188 (6) | |
H8 | −0.152 (3) | 0.323 (6) | 0.615 (3) | 0.023* | |
C9 | −0.1232 (3) | 0.5801 (6) | 0.4957 (3) | 0.0238 (7) | |
H9A | −0.037 (4) | 0.621 (6) | 0.538 (3) | 0.029* | |
H9B | −0.179 (3) | 0.703 (6) | 0.454 (3) | 0.029* | |
H9C | −0.108 (3) | 0.497 (6) | 0.423 (3) | 0.029* | |
C10 | −0.3347 (3) | 0.1944 (6) | 0.4189 (3) | 0.0244 (6) | |
H12A | −0.280 (3) | 0.254 (6) | 0.349 (3) | 0.029* | |
H12B | −0.434 (3) | 0.162 (6) | 0.368 (3) | 0.029* | |
H12C | −0.297 (3) | 0.065 (6) | 0.462 (3) | 0.029* | |
C12 | −0.4983 (3) | 0.1423 (5) | 0.7712 (2) | 0.0181 (6) | |
C13 | −0.5625 (3) | 0.2993 (5) | 0.8524 (3) | 0.0213 (7) | |
H13 | −0.507 (3) | 0.440 (7) | 0.857 (3) | 0.026* | |
H14 | −0.659 (3) | 0.335 (5) | 0.809 (3) | 0.026* | |
O1 | −0.3052 (2) | 0.7832 (4) | 0.64316 (19) | 0.0242 (5) | |
H6 | −0.339 (3) | 0.835 (6) | 0.693 (3) | 0.029* | |
O2 | −0.5598 (2) | 0.2123 (4) | 0.97389 (17) | 0.0252 (5) | |
H15 | −0.559 (3) | 0.323 (6) | 1.025 (3) | 0.03* | |
O3 | −0.51542 (19) | 0.1985 (4) | 0.65561 (16) | 0.0207 (5) | |
O4 | −0.4317 (2) | −0.0259 (4) | 0.81707 (17) | 0.0278 (5) | |
N1 | −0.3437 (2) | 0.3799 (4) | 0.5077 (2) | 0.0187 (5) | |
H10 | −0.393 (3) | 0.483 (6) | 0.462 (3) | 0.022* | |
H11 | −0.397 (3) | 0.333 (5) | 0.565 (3) | 0.022* |
U11 | U22 | U33 | U12 | U13 | U23 | |
C1 | 0.0266 (15) | 0.0239 (17) | 0.0217 (14) | 0.0045 (15) | 0.0067 (12) | 0.0011 (14) |
C2 | 0.0262 (16) | 0.042 (2) | 0.0205 (15) | 0.0119 (17) | 0.0022 (12) | 0.0006 (15) |
C3 | 0.0208 (14) | 0.045 (2) | 0.0246 (15) | −0.0012 (16) | 0.0026 (12) | −0.0083 (16) |
C4 | 0.0261 (15) | 0.033 (2) | 0.0287 (16) | −0.0063 (15) | 0.0078 (13) | −0.0068 (15) |
C5 | 0.0261 (14) | 0.0216 (17) | 0.0223 (15) | 0.0009 (14) | 0.0064 (12) | −0.0015 (14) |
C6 | 0.0205 (12) | 0.0225 (17) | 0.0140 (12) | 0.0033 (12) | 0.0057 (11) | 0.0003 (12) |
C7 | 0.0205 (13) | 0.0212 (16) | 0.0175 (13) | 0.0010 (13) | 0.0060 (11) | 0.0016 (13) |
C8 | 0.0171 (12) | 0.0181 (16) | 0.0212 (14) | 0.0022 (13) | 0.0041 (11) | 0.0008 (13) |
C9 | 0.0247 (15) | 0.0254 (18) | 0.0243 (16) | −0.0046 (15) | 0.0121 (12) | −0.0057 (14) |
C10 | 0.0296 (15) | 0.0198 (17) | 0.0239 (14) | 0.0015 (15) | 0.0053 (13) | −0.0033 (14) |
C12 | 0.0184 (12) | 0.0185 (17) | 0.0171 (14) | −0.0021 (12) | 0.0031 (11) | 0.0013 (12) |
C13 | 0.0249 (14) | 0.0216 (17) | 0.0174 (13) | 0.0033 (14) | 0.0044 (11) | 0.0007 (13) |
O1 | 0.0268 (10) | 0.0258 (13) | 0.0202 (10) | 0.0101 (10) | 0.0056 (8) | −0.0012 (10) |
O2 | 0.0378 (11) | 0.0251 (12) | 0.0144 (9) | 0.0042 (11) | 0.0093 (8) | −0.0008 (9) |
O3 | 0.0267 (9) | 0.0203 (11) | 0.0151 (9) | −0.0023 (10) | 0.0043 (8) | −0.0001 (9) |
O4 | 0.0397 (11) | 0.0254 (12) | 0.0208 (10) | 0.0150 (11) | 0.0119 (9) | 0.0030 (10) |
N1 | 0.0197 (11) | 0.0187 (14) | 0.0176 (12) | 0.0002 (12) | 0.0032 (9) | 0.0005 (11) |
C1—C2 | 1.388 (4) | C9—H9A | 0.89 (3) |
C1—C6 | 1.392 (4) | C9—H9B | 0.97 (4) |
C1—H1 | 0.97 (4) | C9—H9C | 0.97 (4) |
C2—C3 | 1.380 (5) | C10—N1 | 1.491 (4) |
C2—H2 | 0.93 (4) | C10—H12A | 1.06 (4) |
C3—C4 | 1.384 (5) | C10—H12B | 1.02 (3) |
C3—H3 | 0.98 (3) | C10—H12C | 0.94 (4) |
C4—C5 | 1.396 (4) | C12—O4 | 1.249 (3) |
C4—H4 | 1.08 (4) | C12—O3 | 1.275 (3) |
C5—C6 | 1.387 (4) | C12—C13 | 1.508 (4) |
C5—H5 | 0.97 (4) | C13—O2 | 1.411 (3) |
C6—C7 | 1.520 (4) | C13—H13 | 1.00 (4) |
C7—O1 | 1.416 (4) | C13—H14 | 0.97 (3) |
C7—C8 | 1.536 (4) | O1—H6 | 0.75 (4) |
C7—H7 | 1.03 (3) | O2—H15 | 0.87 (4) |
C8—N1 | 1.499 (3) | N1—H10 | 0.88 (3) |
C8—C9 | 1.516 (4) | N1—H11 | 0.92 (3) |
C8—H8 | 0.97 (3) | ||
C2—C1—C6 | 120.6 (3) | C8—C9—H9A | 111 (2) |
C2—C1—H1 | 121.0 (19) | C8—C9—H9B | 111.6 (19) |
C6—C1—H1 | 118.4 (19) | H9A—C9—H9B | 113 (3) |
C3—C2—C1 | 120.0 (3) | C8—C9—H9C | 115 (2) |
C3—C2—H2 | 118 (2) | H9A—C9—H9C | 106 (3) |
C1—C2—H2 | 122 (2) | H9B—C9—H9C | 100 (3) |
C2—C3—C4 | 120.1 (3) | N1—C10—H12A | 107.8 (19) |
C2—C3—H3 | 120 (2) | N1—C10—H12B | 109 (2) |
C4—C3—H3 | 120 (2) | H12A—C10—H12B | 103 (2) |
C3—C4—C5 | 119.9 (3) | N1—C10—H12C | 112 (2) |
C3—C4—H4 | 118.1 (18) | H12A—C10—H12C | 116 (3) |
C5—C4—H4 | 121.9 (18) | H12B—C10—H12C | 109 (3) |
C6—C5—C4 | 120.4 (3) | O4—C12—O3 | 124.2 (3) |
C6—C5—H5 | 120.8 (19) | O4—C12—C13 | 121.1 (2) |
C4—C5—H5 | 118.8 (19) | O3—C12—C13 | 114.7 (2) |
C5—C6—C1 | 119.0 (3) | O2—C13—C12 | 112.1 (3) |
C5—C6—C7 | 121.5 (3) | O2—C13—H13 | 111.1 (17) |
C1—C6—C7 | 119.4 (3) | C12—C13—H13 | 106.8 (18) |
O1—C7—C6 | 113.9 (3) | O2—C13—H14 | 111.5 (18) |
O1—C7—C8 | 106.5 (2) | C12—C13—H14 | 108.9 (19) |
C6—C7—C8 | 109.5 (2) | H13—C13—H14 | 106 (2) |
O1—C7—H7 | 111.6 (17) | C7—O1—H6 | 109 (3) |
C6—C7—H7 | 107.1 (15) | C13—O2—H15 | 108 (2) |
C8—C7—H7 | 108.2 (17) | C10—N1—C8 | 114.3 (2) |
N1—C8—C9 | 109.6 (2) | C10—N1—H10 | 106 (2) |
N1—C8—C7 | 109.1 (2) | C8—N1—H10 | 114 (2) |
C9—C8—C7 | 112.9 (3) | C10—N1—H11 | 108 (2) |
N1—C8—H8 | 106.0 (18) | C8—N1—H11 | 107.5 (17) |
C9—C8—H8 | 111.4 (18) | H10—N1—H11 | 106 (3) |
C7—C8—H8 | 107.4 (18) | ||
C6—C1—C2—C3 | −0.1 (4) | C5—C6—C7—C8 | 101.8 (3) |
C1—C2—C3—C4 | 1.1 (5) | C1—C6—C7—C8 | −75.0 (3) |
C2—C3—C4—C5 | −0.9 (5) | O1—C7—C8—N1 | −63.2 (3) |
C3—C4—C5—C6 | −0.5 (5) | C6—C7—C8—N1 | 173.2 (2) |
C4—C5—C6—C1 | 1.5 (4) | O1—C7—C8—C9 | 59.0 (3) |
C4—C5—C6—C7 | −175.3 (3) | C6—C7—C8—C9 | −64.5 (3) |
C2—C1—C6—C5 | −1.2 (4) | O4—C12—C13—O2 | −10.5 (4) |
C2—C1—C6—C7 | 175.6 (3) | O3—C12—C13—O2 | 170.8 (2) |
C5—C6—C7—O1 | −17.3 (4) | C9—C8—N1—C10 | 72.2 (3) |
C1—C6—C7—O1 | 166.0 (2) | C7—C8—N1—C10 | −163.6 (3) |
D—H···A | D—H | H···A | D···A | D—H···A |
O2—H15···O4i | 0.87 (4) | 1.95 (4) | 2.776 (3) | 158 (3) |
O2—H15···O2i | 0.87 (4) | 2.62 (4) | 3.2430 (15) | 130 (3) |
O1—H6···O4ii | 0.75 (4) | 1.94 (4) | 2.696 (3) | 177 (3) |
N1—H10···O3iii | 0.88 (3) | 1.91 (4) | 2.776 (3) | 171 (3) |
Symmetry codes: (i) −x−1, y+1/2, −z+2; (ii) x, y+1, z; (iii) −x−1, y+1/2, −z+1. |
C10H14ClNO | F(000) = 216 |
Mr = 201.69 | Dx = 1.229 Mg m−3 |
Monoclinic, P21 | Mo Kα radiation, λ = 0.71073 Å |
Hall symbol: P 2yb | Cell parameters from 11628 reflections |
a = 7.2557 (3) Å | θ = 1.0–27.5° |
b = 6.1228 (3) Å | µ = 0.31 mm−1 |
c = 12.5486 (6) Å | T = 150 K |
β = 102.223 (2)° | Needle, colourless |
V = 544.84 (4) Å3 | 0.3 × 0.05 × 0.05 mm |
Z = 2 |
KappaCCD diffractometer | 2458 independent reflections |
Radiation source: Enraf Nonius FR590 | 2006 reflections with I > 2σ(I) |
Graphite monochromator | Rint = 0.057 |
CCD rotation images, thick slices scans | θmax = 27.5°, θmin = 3° |
Absorption correction: multi-scan R.H. Blessing, Acta Cryst. (1995), A51, 33-38 | h = −9→9 |
Tmin = 0.926, Tmax = 1.083 | k = −7→7 |
9528 measured reflections | l = −16→16 |
Refinement on F2 | Secondary atom site location: difference Fourier map |
Least-squares matrix: full | Hydrogen site location: inferred from neighbouring sites |
R[F2 > 2σ(F2)] = 0.066 | H atoms treated by a mixture of independent and constrained refinement |
wR(F2) = 0.156 | w = 1/[σ2(Fo2) + (0.0431P)2 + 0.7722P] where P = (Fo2 + 2Fc2)/3 |
S = 1.19 | (Δ/σ)max < 0.001 |
2458 reflections | Δρmax = 0.73 e Å−3 |
148 parameters | Δρmin = −0.37 e Å−3 |
1 restraint | Absolute structure: Flack H D (1983), Acta Cryst. A39, 876-881 |
Primary atom site location: structure-invariant direct methods | Absolute structure parameter: 0.05 (13) |
C10H14ClNO | V = 544.84 (4) Å3 |
Mr = 201.69 | Z = 2 |
Monoclinic, P21 | Mo Kα radiation |
a = 7.2557 (3) Å | µ = 0.31 mm−1 |
b = 6.1228 (3) Å | T = 150 K |
c = 12.5486 (6) Å | 0.3 × 0.05 × 0.05 mm |
β = 102.223 (2)° |
KappaCCD diffractometer | 2458 independent reflections |
Absorption correction: multi-scan R.H. Blessing, Acta Cryst. (1995), A51, 33-38 | 2006 reflections with I > 2σ(I) |
Tmin = 0.926, Tmax = 1.083 | Rint = 0.057 |
9528 measured reflections |
R[F2 > 2σ(F2)] = 0.066 | H atoms treated by a mixture of independent and constrained refinement |
wR(F2) = 0.156 | Δρmax = 0.73 e Å−3 |
S = 1.19 | Δρmin = −0.37 e Å−3 |
2458 reflections | Absolute structure: Flack H D (1983), Acta Cryst. A39, 876-881 |
148 parameters | Absolute structure parameter: 0.05 (13) |
1 restraint |
Geometry. All e.s.d.'s (except the e.s.d. in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell e.s.d.'s are taken into account individually in the estimation of e.s.d.'s in distances, angles and torsion angles; correlations between e.s.d.'s in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell e.s.d.'s is used for estimating e.s.d.'s involving l.s. planes. |
Refinement. Refinement of F2 against ALL reflections. The weighted R-factor wR and goodness of fit S are based on F2, conventional R-factors R are based on F, with F set to zero for negative F2. The threshold expression of F2 > σ(F2) is used only for calculating R-factors(gt) etc. and is not relevant to the choice of reflections for refinement. R-factors based on F2 are statistically about twice as large as those based on F, and R- factors based on ALL data will be even larger. |
x | y | z | Uiso*/Ueq | ||
C1 | 0.8557 (6) | −0.0094 (9) | 0.0753 (4) | 0.0290 (10) | |
H1 | 0.906 (7) | −0.151 (10) | 0.103 (4) | 0.035* | |
C2 | 0.8046 (7) | 0.0174 (9) | −0.0373 (4) | 0.0338 (12) | |
H2 | 0.839 (7) | −0.108 (10) | −0.083 (4) | 0.041* | |
C3 | 0.7084 (6) | 0.2047 (9) | −0.0799 (4) | 0.0335 (13) | |
H3 | 0.685 (7) | 0.224 (9) | −0.154 (4) | 0.04* | |
C4 | 0.6663 (7) | 0.3648 (9) | −0.0110 (4) | 0.0361 (12) | |
H4 | 0.596 (7) | 0.505 (10) | −0.039 (4) | 0.043* | |
C5 | 0.7153 (6) | 0.3370 (8) | 0.1014 (4) | 0.0297 (10) | |
H5 | 0.685 (7) | 0.449 (9) | 0.147 (4) | 0.036* | |
C6 | 0.8108 (5) | 0.1492 (11) | 0.1455 (3) | 0.0247 (8) | |
C7 | 0.8635 (6) | 0.1080 (7) | 0.2672 (3) | 0.0232 (10) | |
H7 | 0.9866 | 0.0354 | 0.2839 | 0.028* | |
C8 | 0.7203 (6) | −0.0402 (8) | 0.3033 (3) | 0.0214 (9) | |
H8 | 0.690 (6) | −0.169 (9) | 0.259 (4) | 0.026* | |
C9 | 0.5321 (6) | 0.0728 (7) | 0.3037 (4) | 0.0259 (10) | |
H10A | 0.4413 | −0.034 | 0.3151 | 0.039* | |
H10B | 0.4876 | 0.1441 | 0.2349 | 0.039* | |
H10C | 0.5494 | 0.179 | 0.3612 | 0.039* | |
C10 | 0.6985 (6) | −0.3065 (8) | 0.4550 (4) | 0.0319 (12) | |
H12A | 0.5758 | −0.2548 | 0.4602 | 0.048* | |
H12B | 0.7653 | −0.355 | 0.5253 | 0.048* | |
H12C | 0.6855 | −0.4258 | 0.4043 | 0.048* | |
N1 | 0.8064 (5) | −0.1248 (7) | 0.4160 (3) | 0.0248 (8) | |
H10 | 0.927 (7) | −0.196 (8) | 0.411 (4) | 0.03* | |
H11 | 0.804 (7) | −0.019 (9) | 0.460 (4) | 0.03* | |
O1 | 0.8740 (5) | 0.2991 (6) | 0.3322 (3) | 0.0315 (8) | |
H6 | 0.956 (8) | 0.404 (10) | 0.325 (4) | 0.038* | |
Cl1 | 1.17971 (13) | −0.34367 (18) | 0.37349 (7) | 0.0267 (3) |
U11 | U22 | U33 | U12 | U13 | U23 | |
C1 | 0.028 (2) | 0.030 (3) | 0.031 (2) | 0.002 (2) | 0.0095 (19) | 0.002 (2) |
C2 | 0.035 (3) | 0.039 (3) | 0.033 (3) | −0.010 (2) | 0.019 (2) | −0.011 (2) |
C3 | 0.029 (2) | 0.049 (4) | 0.024 (2) | −0.009 (2) | 0.0076 (17) | 0.005 (2) |
C4 | 0.029 (2) | 0.038 (3) | 0.041 (3) | 0.006 (2) | 0.009 (2) | 0.012 (2) |
C5 | 0.029 (2) | 0.031 (3) | 0.031 (2) | 0.002 (2) | 0.0106 (19) | 0.002 (2) |
C6 | 0.0205 (16) | 0.028 (2) | 0.027 (2) | −0.001 (2) | 0.0080 (14) | 0.002 (3) |
C7 | 0.0222 (19) | 0.021 (3) | 0.026 (2) | 0.0009 (16) | 0.0039 (15) | −0.0019 (17) |
C8 | 0.018 (2) | 0.025 (2) | 0.020 (2) | 0.0008 (17) | 0.0034 (15) | −0.0046 (18) |
C9 | 0.020 (2) | 0.028 (2) | 0.029 (2) | −0.0002 (17) | 0.0040 (17) | −0.0039 (18) |
C10 | 0.034 (2) | 0.032 (3) | 0.032 (2) | −0.011 (2) | 0.0095 (17) | 0.001 (2) |
N1 | 0.0247 (18) | 0.025 (2) | 0.0259 (19) | −0.0050 (16) | 0.0072 (15) | −0.0020 (16) |
O1 | 0.0358 (17) | 0.0290 (19) | 0.0312 (17) | −0.0162 (15) | 0.0108 (14) | −0.0091 (15) |
Cl1 | 0.0221 (4) | 0.0298 (5) | 0.0289 (5) | −0.0045 (5) | 0.0068 (3) | 0.0017 (6) |
C1—C2 | 1.392 (7) | C7—H7 | 0.98 |
C1—C6 | 1.395 (7) | C8—N1 | 1.512 (5) |
C1—H1 | 0.97 (6) | C8—C9 | 1.532 (6) |
C2—C3 | 1.389 (8) | C8—H8 | 0.96 (5) |
C2—H2 | 1.02 (6) | C9—H10A | 0.96 |
C3—C4 | 1.383 (7) | C9—H10B | 0.96 |
C3—H3 | 0.92 (5) | C9—H10C | 0.96 |
C4—C5 | 1.391 (7) | C10—N1 | 1.500 (6) |
C4—H4 | 1.02 (6) | C10—H12A | 0.96 |
C5—C6 | 1.395 (8) | C10—H12B | 0.96 |
C5—H5 | 0.95 (6) | C10—H12C | 0.96 |
C6—C7 | 1.515 (5) | N1—H10 | 0.99 (5) |
C7—O1 | 1.419 (5) | N1—H11 | 0.85 (5) |
C7—C8 | 1.519 (6) | O1—H6 | 0.89 (6) |
C2—C1—C6 | 120.7 (5) | N1—C8—C9 | 110.1 (3) |
C2—C1—H1 | 118 (3) | C7—C8—C9 | 113.4 (4) |
C6—C1—H1 | 121 (3) | N1—C8—H8 | 105 (3) |
C3—C2—C1 | 119.5 (5) | C7—C8—H8 | 114 (3) |
C3—C2—H2 | 125 (3) | C9—C8—H8 | 106 (3) |
C1—C2—H2 | 116 (3) | C8—C9—H10A | 109.5 |
C4—C3—C2 | 120.2 (4) | C8—C9—H10B | 109.5 |
C4—C3—H3 | 121 (3) | H10A—C9—H10B | 109.5 |
C2—C3—H3 | 118 (3) | C8—C9—H10C | 109.5 |
C3—C4—C5 | 120.3 (5) | H10A—C9—H10C | 109.5 |
C3—C4—H4 | 123 (3) | H10B—C9—H10C | 109.5 |
C5—C4—H4 | 117 (3) | N1—C10—H12A | 109.5 |
C4—C5—C6 | 120.1 (5) | N1—C10—H12B | 109.5 |
C4—C5—H5 | 119 (3) | H12A—C10—H12B | 109.5 |
C6—C5—H5 | 121 (3) | N1—C10—H12C | 109.5 |
C1—C6—C5 | 119.1 (4) | H12A—C10—H12C | 109.5 |
C1—C6—C7 | 118.6 (5) | H12B—C10—H12C | 109.5 |
C5—C6—C7 | 122.3 (4) | C10—N1—C8 | 114.7 (3) |
O1—C7—C6 | 114.4 (4) | C10—N1—H10 | 103 (3) |
O1—C7—C8 | 106.1 (3) | C8—N1—H10 | 107 (3) |
C6—C7—C8 | 111.0 (4) | C10—N1—H11 | 106 (3) |
O1—C7—H7 | 108.4 | C8—N1—H11 | 106 (3) |
C6—C7—H7 | 108.4 | H10—N1—H11 | 121 (4) |
C8—C7—H7 | 108.4 | C7—O1—H6 | 119 (3) |
N1—C8—C7 | 108.1 (3) | ||
C6—C1—C2—C3 | 0.2 (7) | C5—C6—C7—O1 | −22.3 (6) |
C1—C2—C3—C4 | 1.0 (7) | C1—C6—C7—C8 | −80.7 (5) |
C2—C3—C4—C5 | −1.8 (7) | C5—C6—C7—C8 | 97.7 (5) |
C3—C4—C5—C6 | 1.3 (7) | O1—C7—C8—N1 | −70.6 (4) |
C2—C1—C6—C5 | −0.7 (7) | C6—C7—C8—N1 | 164.5 (4) |
C2—C1—C6—C7 | 177.8 (4) | O1—C7—C8—C9 | 51.8 (4) |
C4—C5—C6—C1 | −0.1 (7) | C6—C7—C8—C9 | −73.1 (5) |
C4—C5—C6—C7 | −178.5 (4) | C7—C8—N1—C10 | −168.8 (4) |
C1—C6—C7—O1 | 159.2 (4) | C9—C8—N1—C10 | 66.7 (5) |
D—H···A | D—H | H···A | D···A | D—H···A |
N1—H11···Cl1i | 0.85 (5) | 2.33 (5) | 3.136 (4) | 157 (5) |
O1—H6···Cl1ii | 0.89 (6) | 2.23 (6) | 3.080 (3) | 159 (4) |
Symmetry codes: (i) −x+2, y+1/2, −z+1; (ii) x, y+1, z. |
C10H15NO | F(000) = 760 |
Mr = 174.24 | Dx = 1.157 Mg m−3 |
Orthorhombic, C2221 | Mo Kα radiation, λ = 0.71073 Å |
Hall symbol: C 2c 2 | Cell parameters from 8739 reflections |
a = 7.3639 (4) Å | θ = 1.0–25.0° |
b = 11.2551 (6) Å | µ = 0.08 mm−1 |
c = 24.1442 (16) Å | T = 150 K |
V = 2001.1 (2) Å3 | Plate, colourless |
Z = 8 | 0.25 × 0.25 × 0.05 mm |
KappaCCD diffractometer | 1007 independent reflections |
Radiation source: Enraf Nonius FR590 | 801 reflections with I > 2σ(I) |
Graphite monochromator | Rint = 0.048 |
CCD rotation images, thick slices scans | θmax = 25°, θmin = 3.7° |
Absorption correction: multi-scan R.H. Blessing, Acta Cryst. (1995), A51, 33-38 | h = −8→8 |
Tmin = 0.976, Tmax = 1.02 | k = −13→13 |
5306 measured reflections | l = −28→26 |
Refinement on F2 | Primary atom site location: structure-invariant direct methods |
Least-squares matrix: full | Secondary atom site location: difference Fourier map |
R[F2 > 2σ(F2)] = 0.042 | Hydrogen site location: inferred from neighbouring sites |
wR(F2) = 0.100 | H atoms treated by a mixture of independent and constrained refinement |
S = 1.08 | w = 1/[σ2(Fo2) + (0.0479P)2 + 0.566P] where P = (Fo2 + 2Fc2)/3 |
1007 reflections | (Δ/σ)max = 0.001 |
151 parameters | Δρmax = 0.14 e Å−3 |
0 restraints | Δρmin = −0.16 e Å−3 |
C10H15NO | V = 2001.1 (2) Å3 |
Mr = 174.24 | Z = 8 |
Orthorhombic, C2221 | Mo Kα radiation |
a = 7.3639 (4) Å | µ = 0.08 mm−1 |
b = 11.2551 (6) Å | T = 150 K |
c = 24.1442 (16) Å | 0.25 × 0.25 × 0.05 mm |
KappaCCD diffractometer | 1007 independent reflections |
Absorption correction: multi-scan R.H. Blessing, Acta Cryst. (1995), A51, 33-38 | 801 reflections with I > 2σ(I) |
Tmin = 0.976, Tmax = 1.02 | Rint = 0.048 |
5306 measured reflections |
R[F2 > 2σ(F2)] = 0.042 | 0 restraints |
wR(F2) = 0.100 | H atoms treated by a mixture of independent and constrained refinement |
S = 1.08 | Δρmax = 0.14 e Å−3 |
1007 reflections | Δρmin = −0.16 e Å−3 |
151 parameters |
Geometry. All e.s.d.'s (except the e.s.d. in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell e.s.d.'s are taken into account individually in the estimation of e.s.d.'s in distances, angles and torsion angles; correlations between e.s.d.'s in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell e.s.d.'s is used for estimating e.s.d.'s involving l.s. planes. |
Refinement. Refinement of F2 against ALL reflections. The weighted R-factor wR and goodness of fit S are based on F2, conventional R-factors R are based on F, with F set to zero for negative F2. The threshold expression of F2 > σ(F2) is used only for calculating R-factors(gt) etc. and is not relevant to the choice of reflections for refinement. R-factors based on F2 are statistically about twice as large as those based on F, and R- factors based on ALL data will be even larger. |
x | y | z | Uiso*/Ueq | ||
C1 | 0.3249 (6) | 0.3337 (4) | 0.60488 (13) | 0.0592 (11) | |
H1 | 0.302 (6) | 0.395 (4) | 0.6318 (17) | 0.071* | |
C2 | 0.4242 (7) | 0.3626 (6) | 0.55793 (17) | 0.0883 (18) | |
H2 | 0.458 (8) | 0.438 (5) | 0.553 (2) | 0.106* | |
C3 | 0.4752 (6) | 0.2761 (7) | 0.52123 (17) | 0.0889 (18) | |
H3 | 0.541 | 0.2955 | 0.4896 | 0.107* | |
C4 | 0.4286 (7) | 0.1618 (7) | 0.53154 (16) | 0.0859 (19) | |
H4 | 0.470 (7) | 0.103 (4) | 0.510 (2) | 0.103* | |
C5 | 0.3290 (6) | 0.1322 (4) | 0.57806 (13) | 0.0564 (10) | |
H5 | 0.296 (6) | 0.054 (3) | 0.5870 (16) | 0.068* | |
C6 | 0.2740 (4) | 0.2179 (3) | 0.61511 (12) | 0.0368 (7) | |
C7 | 0.1604 (4) | 0.1856 (3) | 0.66467 (11) | 0.0287 (7) | |
H7 | 0.188 (4) | 0.100 (3) | 0.6764 (11) | 0.034* | |
C8 | −0.0439 (4) | 0.1851 (2) | 0.65060 (11) | 0.0294 (7) | |
H8 | −0.057 (4) | 0.134 (3) | 0.6167 (13) | 0.035* | |
C9 | −0.1189 (5) | 0.3083 (3) | 0.63911 (16) | 0.0429 (8) | |
H9A | −0.252 (5) | 0.303 (3) | 0.6291 (13) | 0.051* | |
H9B | −0.109 (5) | 0.355 (3) | 0.6726 (15) | 0.051* | |
H9C | −0.051 (5) | 0.346 (3) | 0.6083 (15) | 0.051* | |
C10 | −0.3349 (4) | 0.1031 (3) | 0.68479 (12) | 0.0453 (9) | |
H11A | −0.4058 | 0.1741 | 0.689 | 0.068* | |
H11B | −0.3784 | 0.0435 | 0.7099 | 0.068* | |
H11C | −0.3456 | 0.0747 | 0.6474 | 0.068* | |
N1 | −0.1429 (3) | 0.1293 (2) | 0.69701 (9) | 0.0308 (6) | |
H10 | −0.088 (4) | 0.064 (3) | 0.7083 (13) | 0.029 (8)* | |
O1 | 0.1982 (3) | 0.26304 (17) | 0.70953 (7) | 0.0341 (5) | |
H6 | 0.1708 | 0.2304 | 0.7387 | 0.051* | |
O2 | 0.5 | 0.3973 (3) | 0.75 | 0.0435 (8) | |
H13 | 0.417 (4) | 0.349 (3) | 0.7382 (14) | 0.052* |
U11 | U22 | U33 | U12 | U13 | U23 | |
C1 | 0.070 (3) | 0.076 (3) | 0.0313 (17) | −0.039 (2) | 0.0065 (18) | −0.0029 (16) |
C2 | 0.088 (3) | 0.144 (4) | 0.033 (2) | −0.079 (3) | 0.004 (2) | 0.003 (3) |
C3 | 0.037 (2) | 0.196 (6) | 0.033 (2) | −0.013 (3) | 0.0028 (18) | 0.017 (3) |
C4 | 0.071 (3) | 0.152 (5) | 0.035 (2) | 0.064 (4) | 0.012 (2) | 0.002 (3) |
C5 | 0.060 (2) | 0.077 (2) | 0.0315 (17) | 0.035 (2) | 0.0021 (17) | 0.0019 (17) |
C6 | 0.0259 (15) | 0.058 (2) | 0.0264 (14) | 0.0019 (14) | −0.0065 (13) | −0.0008 (14) |
C7 | 0.0291 (15) | 0.0304 (15) | 0.0266 (14) | −0.0008 (14) | −0.0030 (12) | −0.0038 (12) |
C8 | 0.0284 (15) | 0.0363 (16) | 0.0236 (15) | 0.0026 (14) | −0.0026 (12) | 0.0000 (13) |
C9 | 0.0379 (18) | 0.0461 (19) | 0.0447 (19) | 0.0109 (15) | 0.0008 (16) | 0.0122 (16) |
C10 | 0.0358 (18) | 0.063 (2) | 0.0371 (17) | −0.0129 (17) | −0.0036 (16) | −0.0052 (15) |
N1 | 0.0270 (13) | 0.0344 (13) | 0.0309 (12) | −0.0022 (12) | −0.0049 (11) | 0.0028 (11) |
O1 | 0.0349 (11) | 0.0428 (11) | 0.0247 (10) | −0.0095 (9) | −0.0020 (9) | −0.0002 (8) |
O2 | 0.0360 (19) | 0.0310 (16) | 0.063 (2) | 0 | −0.0119 (16) | 0 |
C1—C6 | 1.379 (5) | C7—H7 | 1.03 (3) |
C1—C2 | 1.387 (5) | C8—N1 | 1.477 (4) |
C1—H1 | 0.96 (4) | C8—C9 | 1.518 (4) |
C2—C3 | 1.369 (8) | C8—H8 | 1.01 (3) |
C2—H2 | 0.89 (5) | C9—H9A | 1.01 (4) |
C3—C4 | 1.354 (7) | C9—H9B | 0.97 (4) |
C3—H3 | 0.93 | C9—H9C | 0.99 (3) |
C4—C5 | 1.382 (6) | C10—N1 | 1.474 (4) |
C4—H4 | 0.90 (5) | C10—H11A | 0.96 |
C5—C6 | 1.376 (5) | C10—H11B | 0.96 |
C5—H5 | 0.93 (4) | C10—H11C | 0.96 |
C6—C7 | 1.505 (4) | N1—H10 | 0.88 (3) |
C7—O1 | 1.418 (3) | O1—H6 | 0.82 |
C7—C8 | 1.543 (4) | O2—H13 | 0.86 (3) |
C6—C1—C2 | 120.7 (4) | C8—C7—H7 | 104.6 (19) |
C6—C1—H1 | 121 (2) | N1—C8—C9 | 110.3 (3) |
C2—C1—H1 | 118 (3) | N1—C8—C7 | 108.4 (2) |
C3—C2—C1 | 120.4 (5) | C9—C8—C7 | 113.0 (3) |
C3—C2—H2 | 121 (4) | N1—C8—H8 | 108.8 (17) |
C1—C2—H2 | 119 (4) | C9—C8—H8 | 110.0 (17) |
C4—C3—C2 | 119.1 (4) | C7—C8—H8 | 106.1 (17) |
C4—C3—H3 | 120.4 | C8—C9—H9A | 110 (2) |
C2—C3—H3 | 120.4 | C8—C9—H9B | 108 (2) |
C3—C4—C5 | 120.9 (5) | H9A—C9—H9B | 108 (3) |
C3—C4—H4 | 121 (3) | C8—C9—H9C | 110 (2) |
C5—C4—H4 | 118 (3) | H9A—C9—H9C | 110 (3) |
C6—C5—C4 | 121.0 (4) | H9B—C9—H9C | 111 (3) |
C6—C5—H5 | 115 (3) | N1—C10—H11A | 109.5 |
C4—C5—H5 | 124 (3) | N1—C10—H11B | 109.5 |
C5—C6—C1 | 117.8 (3) | H11A—C10—H11B | 109.5 |
C5—C6—C7 | 120.7 (3) | N1—C10—H11C | 109.5 |
C1—C6—C7 | 121.5 (3) | H11A—C10—H11C | 109.5 |
O1—C7—C6 | 110.5 (2) | H11B—C10—H11C | 109.5 |
O1—C7—C8 | 111.2 (2) | C10—N1—C8 | 114.0 (2) |
C6—C7—C8 | 111.6 (2) | C10—N1—H10 | 109.7 (18) |
O1—C7—H7 | 109.2 (16) | C8—N1—H10 | 111.2 (19) |
C6—C7—H7 | 109.6 (17) | C7—O1—H6 | 109.5 |
C6—C1—C2—C3 | −0.8 (7) | C1—C6—C7—O1 | −31.6 (4) |
C1—C2—C3—C4 | −0.4 (7) | C5—C6—C7—C8 | −86.6 (3) |
C2—C3—C4—C5 | 0.8 (7) | C1—C6—C7—C8 | 92.7 (4) |
C3—C4—C5—C6 | 0.1 (6) | O1—C7—C8—N1 | −67.7 (3) |
C4—C5—C6—C1 | −1.3 (5) | C6—C7—C8—N1 | 168.5 (2) |
C4—C5—C6—C7 | 178.0 (3) | O1—C7—C8—C9 | 55.0 (3) |
C2—C1—C6—C5 | 1.7 (6) | C6—C7—C8—C9 | −68.9 (3) |
C2—C1—C6—C7 | −177.7 (4) | C9—C8—N1—C10 | 66.3 (3) |
C5—C6—C7—O1 | 149.1 (3) | C7—C8—N1—C10 | −169.4 (3) |
D—H···A | D—H | H···A | D···A | D—H···A |
N1—H10···O2i | 0.88 (3) | 2.23 (3) | 3.092 (4) | 167 (3) |
O1—H6···N1ii | 0.82 | 1.93 | 2.743 (3) | 168 |
Symmetry codes: (i) x−1/2, y−1/2, z; (ii) −x, y, −z+3/2. |
C14H21NO6 | F(000) = 320 |
Mr = 299.32 | Dx = 1.31 Mg m−3 |
Monoclinic, P21 | Mo Kα radiation, λ = 0.71073 Å |
Hall symbol: P 2yb | Cell parameters from 17480 reflections |
a = 6.1312 (6) Å | θ = 2.0–25.0° |
b = 9.1719 (10) Å | µ = 0.10 mm−1 |
c = 13.7393 (17) Å | T = 293 K |
β = 100.909 (4)° | Plate, colourless |
V = 758.66 (15) Å3 | 0.25 × 0.25 × 0.1 mm |
Z = 2 |
KappaCCD diffractometer | 1713 independent reflections |
Radiation source: Enraf Nonius FR590 | 1232 reflections with I > 2σ(I) |
Graphite monochromator | Rint = 0.109 |
Detector resolution: 9 pixels mm-1 | θmax = 27.5°, θmin = 2.7° |
CCD rotation images, thick slices scans | h = −7→7 |
Absorption correction: multi-scan R.H. Blessing, Acta Cryst. (1995), A51, 33-38 | k = −10→11 |
Tmin = 0.912, Tmax = 1.134 | l = −15→17 |
6933 measured reflections |
Refinement on F2 | Secondary atom site location: difference Fourier map |
Least-squares matrix: full | Hydrogen site location: inferred from neighbouring sites |
R[F2 > 2σ(F2)] = 0.060 | H atoms treated by a mixture of independent and constrained refinement |
wR(F2) = 0.185 | w = 1/[σ2(Fo2) + (0.0999P)2 + 0.0445P] where P = (Fo2 + 2Fc2)/3 |
S = 1.13 | (Δ/σ)max < 0.001 |
1713 reflections | Δρmax = 0.26 e Å−3 |
213 parameters | Δρmin = −0.30 e Å−3 |
1 restraint | Absolute structure: Flack H D (1983), Acta Cryst. A39, 876-881 |
Primary atom site location: structure-invariant direct methods | Absolute structure parameter: 10 (10) |
C14H21NO6 | V = 758.66 (15) Å3 |
Mr = 299.32 | Z = 2 |
Monoclinic, P21 | Mo Kα radiation |
a = 6.1312 (6) Å | µ = 0.10 mm−1 |
b = 9.1719 (10) Å | T = 293 K |
c = 13.7393 (17) Å | 0.25 × 0.25 × 0.1 mm |
β = 100.909 (4)° |
KappaCCD diffractometer | 1713 independent reflections |
Absorption correction: multi-scan R.H. Blessing, Acta Cryst. (1995), A51, 33-38 | 1232 reflections with I > 2σ(I) |
Tmin = 0.912, Tmax = 1.134 | Rint = 0.109 |
6933 measured reflections |
R[F2 > 2σ(F2)] = 0.060 | H atoms treated by a mixture of independent and constrained refinement |
wR(F2) = 0.185 | Δρmax = 0.26 e Å−3 |
S = 1.13 | Δρmin = −0.30 e Å−3 |
1713 reflections | Absolute structure: Flack H D (1983), Acta Cryst. A39, 876-881 |
213 parameters | Absolute structure parameter: 10 (10) |
1 restraint |
Experimental. Structures of 17 salts of ephedrine: Crystal packing and hydrogen bonding analysis |
Geometry. All e.s.d.'s (except the e.s.d. in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell e.s.d.'s are taken into account individually in the estimation of e.s.d.'s in distances, angles and torsion angles; correlations between e.s.d.'s in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell e.s.d.'s is used for estimating e.s.d.'s involving l.s. planes. |
Refinement. Refinement of F2 against ALL reflections. The weighted R-factor wR and goodness of fit S are based on F2, conventional R-factors R are based on F, with F set to zero for negative F2. The threshold expression of F2 > σ(F2) is used only for calculating R-factors(gt) etc. and is not relevant to the choice of reflections for refinement. R-factors based on F2 are statistically about twice as large as those based on F, and R- factors based on ALL data will be even larger. |
x | y | z | Uiso*/Ueq | ||
C1 | 0.0631 (11) | 0.2120 (7) | 0.3731 (5) | 0.0442 (15) | |
H1 | −0.0393 | 0.1552 | 0.3309 | 0.053* | |
C2 | 0.1200 (12) | 0.1756 (8) | 0.4714 (6) | 0.0544 (18) | |
H2 | 0.0542 | 0.0955 | 0.4957 | 0.065* | |
C3 | 0.2732 (13) | 0.2567 (9) | 0.5337 (5) | 0.0526 (18) | |
H3 | 0.314 (12) | 0.241 (10) | 0.587 (6) | 0.063* | |
C4 | 0.3665 (11) | 0.3788 (9) | 0.4986 (5) | 0.0475 (16) | |
H4 | 0.472 (12) | 0.445 (9) | 0.542 (6) | 0.057* | |
C5 | 0.3078 (9) | 0.4149 (8) | 0.3997 (5) | 0.0396 (14) | |
H5 | 0.384 (10) | 0.512 (8) | 0.388 (5) | 0.047* | |
C6 | 0.1559 (9) | 0.3319 (6) | 0.3361 (5) | 0.0337 (13) | |
C7 | 0.0991 (8) | 0.3755 (6) | 0.2272 (4) | 0.0294 (12) | |
H7 | 0.247 (9) | 0.401 (7) | 0.199 (4) | 0.035* | |
C8 | −0.0623 (8) | 0.5035 (6) | 0.2096 (4) | 0.0272 (11) | |
H8 | 0.001 (9) | 0.585 (8) | 0.240 (4) | 0.033* | |
C9 | −0.2807 (9) | 0.4759 (7) | 0.2413 (5) | 0.0373 (13) | |
H9A | −0.3786 | 0.5568 | 0.2219 | 0.056* | |
H9B | −0.2562 | 0.4646 | 0.312 | 0.056* | |
H9C | −0.3465 | 0.3886 | 0.2101 | 0.056* | |
C10 | 0.0904 (9) | 0.5631 (7) | 0.0559 (5) | 0.0384 (14) | |
H12A | 0.2026 | 0.6165 | 0.0999 | 0.058* | |
H12B | 0.0487 | 0.6159 | −0.0051 | 0.058* | |
H12C | 0.1476 | 0.4692 | 0.0426 | 0.058* | |
C11 | 0.2994 (8) | −0.1015 (6) | 0.2301 (4) | 0.0280 (12) | |
C12 | 0.4963 (8) | 0.0001 (6) | 0.2406 (4) | 0.0297 (12) | |
H13 | 0.6237 | −0.0459 | 0.2817 | 0.036* | |
H14 | 0.4634 | 0.0886 | 0.2737 | 0.036* | |
C13 | 0.5549 (8) | 0.0401 (6) | 0.1398 (4) | 0.0270 (11) | |
H15 | 0.700 (10) | 0.087 (7) | 0.145 (4) | 0.032* | |
C14 | 0.5836 (8) | −0.1006 (6) | 0.0837 (4) | 0.0276 (11) | |
N1 | −0.1073 (7) | 0.5439 (5) | 0.1027 (3) | 0.0289 (10) | |
H10 | −0.1942 | 0.4744 | 0.0691 | 0.035* | |
H11 | −0.1853 | 0.6276 | 0.0958 | 0.035* | |
O1 | −0.0033 (6) | 0.2631 (4) | 0.1639 (3) | 0.0348 (9) | |
H6 | 0.0905 | 0.203 | 0.1557 | 0.052* | |
O2 | 0.3888 (6) | 0.1340 (4) | 0.0873 (3) | 0.0328 (9) | |
H16 | 0.4469 | 0.1946 | 0.0564 | 0.049* | |
O3 | 0.1126 (6) | −0.0354 (4) | 0.1911 (3) | 0.0404 (11) | |
H17 | 0.0127 | −0.0958 | 0.1781 | 0.061* | |
O4 | 0.3119 (6) | −0.2288 (5) | 0.2511 (4) | 0.0445 (11) | |
O5 | 0.4475 (6) | −0.1366 (4) | 0.0085 (3) | 0.0332 (9) | |
O6 | 0.7526 (6) | −0.1770 (4) | 0.1212 (3) | 0.0333 (10) |
U11 | U22 | U33 | U12 | U13 | U23 | |
C1 | 0.056 (3) | 0.029 (3) | 0.045 (4) | −0.003 (3) | 0.000 (3) | 0.001 (3) |
C2 | 0.071 (4) | 0.041 (4) | 0.047 (4) | −0.008 (4) | 0.000 (3) | 0.010 (3) |
C3 | 0.071 (4) | 0.056 (4) | 0.028 (3) | 0.000 (4) | 0.001 (3) | 0.011 (3) |
C4 | 0.047 (3) | 0.055 (4) | 0.036 (4) | −0.008 (3) | −0.003 (3) | −0.004 (3) |
C5 | 0.038 (3) | 0.044 (4) | 0.035 (3) | −0.003 (3) | 0.003 (2) | −0.004 (3) |
C6 | 0.033 (3) | 0.030 (3) | 0.037 (3) | 0.003 (2) | 0.004 (2) | 0.001 (3) |
C7 | 0.023 (2) | 0.027 (3) | 0.036 (3) | 0.001 (2) | 0.002 (2) | −0.002 (2) |
C8 | 0.031 (3) | 0.020 (2) | 0.031 (3) | 0.000 (2) | 0.006 (2) | −0.001 (2) |
C9 | 0.035 (3) | 0.037 (3) | 0.040 (3) | 0.004 (3) | 0.008 (2) | 0.006 (3) |
C10 | 0.030 (3) | 0.048 (4) | 0.039 (3) | 0.001 (3) | 0.012 (2) | 0.003 (3) |
C11 | 0.027 (2) | 0.023 (3) | 0.034 (3) | 0.000 (2) | 0.005 (2) | 0.001 (2) |
C12 | 0.030 (2) | 0.025 (3) | 0.032 (3) | −0.001 (2) | −0.001 (2) | −0.002 (2) |
C13 | 0.025 (2) | 0.021 (2) | 0.033 (3) | 0.003 (2) | 0.001 (2) | 0.005 (2) |
C14 | 0.024 (2) | 0.026 (3) | 0.032 (3) | 0.002 (2) | 0.005 (2) | 0.003 (2) |
N1 | 0.030 (2) | 0.026 (2) | 0.028 (3) | 0.0022 (19) | 0.0007 (18) | 0.001 (2) |
O1 | 0.0373 (19) | 0.0210 (18) | 0.044 (2) | 0.0033 (17) | 0.0014 (17) | −0.0067 (18) |
O2 | 0.0306 (19) | 0.0215 (18) | 0.046 (3) | 0.0024 (15) | 0.0056 (17) | 0.0051 (17) |
O3 | 0.0287 (19) | 0.025 (2) | 0.065 (3) | −0.0012 (16) | 0.0031 (19) | 0.006 (2) |
O4 | 0.036 (2) | 0.028 (2) | 0.065 (3) | −0.0015 (17) | −0.0009 (19) | 0.009 (2) |
O5 | 0.0320 (18) | 0.0259 (19) | 0.040 (2) | 0.0027 (16) | 0.0014 (16) | 0.0013 (17) |
O6 | 0.0307 (18) | 0.0249 (18) | 0.042 (3) | 0.0025 (16) | 0.0022 (16) | 0.0010 (17) |
C1—C2 | 1.371 (9) | C10—N1 | 1.487 (7) |
C1—C6 | 1.378 (9) | C10—H12A | 0.96 |
C1—H1 | 0.93 | C10—H12B | 0.96 |
C2—C3 | 1.365 (11) | C10—H12C | 0.96 |
C2—H2 | 0.93 | C11—O4 | 1.201 (7) |
C3—C4 | 1.385 (11) | C11—O3 | 1.317 (6) |
C3—H3 | 0.74 (8) | C11—C12 | 1.511 (7) |
C4—C5 | 1.379 (9) | C12—C13 | 1.540 (8) |
C4—H4 | 1.00 (8) | C12—H13 | 0.97 |
C5—C6 | 1.379 (8) | C12—H14 | 0.97 |
C5—H5 | 1.03 (7) | C13—O2 | 1.422 (6) |
C6—C7 | 1.525 (8) | C13—C14 | 1.530 (7) |
C7—O1 | 1.416 (6) | C13—H15 | 0.98 (6) |
C7—C8 | 1.525 (7) | C14—O5 | 1.243 (7) |
C7—H7 | 1.08 (6) | C14—O6 | 1.277 (6) |
C8—N1 | 1.488 (7) | N1—H10 | 0.9 |
C8—C9 | 1.506 (7) | N1—H11 | 0.9 |
C8—H8 | 0.91 (7) | O1—H6 | 0.82 |
C9—H9A | 0.96 | O2—H16 | 0.82 |
C9—H9B | 0.96 | O3—H17 | 0.82 |
C9—H9C | 0.96 | ||
C2—C1—C6 | 120.8 (6) | H9B—C9—H9C | 109.5 |
C2—C1—H1 | 119.6 | N1—C10—H12A | 109.5 |
C6—C1—H1 | 119.6 | N1—C10—H12B | 109.5 |
C3—C2—C1 | 120.1 (6) | H12A—C10—H12B | 109.5 |
C3—C2—H2 | 119.9 | N1—C10—H12C | 109.5 |
C1—C2—H2 | 119.9 | H12A—C10—H12C | 109.5 |
C2—C3—C4 | 120.2 (7) | H12B—C10—H12C | 109.5 |
C2—C3—H3 | 125 (7) | O4—C11—O3 | 123.8 (5) |
C4—C3—H3 | 115 (7) | O4—C11—C12 | 124.3 (5) |
C5—C4—C3 | 119.3 (7) | O3—C11—C12 | 111.9 (4) |
C5—C4—H4 | 118 (4) | C11—C12—C13 | 112.3 (4) |
C3—C4—H4 | 123 (4) | C11—C12—H13 | 109.1 |
C6—C5—C4 | 120.7 (6) | C13—C12—H13 | 109.1 |
C6—C5—H5 | 131 (4) | C11—C12—H14 | 109.1 |
C4—C5—H5 | 109 (4) | C13—C12—H14 | 109.1 |
C1—C6—C5 | 118.9 (6) | H13—C12—H14 | 107.9 |
C1—C6—C7 | 122.5 (5) | O2—C13—C14 | 113.2 (4) |
C5—C6—C7 | 118.6 (5) | O2—C13—C12 | 109.5 (4) |
O1—C7—C6 | 113.9 (5) | C14—C13—C12 | 108.7 (4) |
O1—C7—C8 | 105.3 (4) | O2—C13—H15 | 109 (4) |
C6—C7—C8 | 112.2 (5) | C14—C13—H15 | 103 (4) |
O1—C7—H7 | 104 (3) | C12—C13—H15 | 114 (3) |
C6—C7—H7 | 111 (3) | O5—C14—O6 | 123.8 (5) |
C8—C7—H7 | 110 (3) | O5—C14—C13 | 121.3 (4) |
N1—C8—C9 | 108.5 (4) | O6—C14—C13 | 114.9 (4) |
N1—C8—C7 | 110.0 (4) | C10—N1—C8 | 116.2 (4) |
C9—C8—C7 | 114.2 (5) | C10—N1—H10 | 108.2 |
N1—C8—H8 | 104 (4) | C8—N1—H10 | 108.2 |
C9—C8—H8 | 109 (4) | C10—N1—H11 | 108.2 |
C7—C8—H8 | 111 (4) | C8—N1—H11 | 108.2 |
C8—C9—H9A | 109.5 | H10—N1—H11 | 107.4 |
C8—C9—H9B | 109.5 | C7—O1—H6 | 109.5 |
H9A—C9—H9B | 109.5 | C13—O2—H16 | 109.5 |
C8—C9—H9C | 109.5 | C11—O3—H17 | 109.5 |
H9A—C9—H9C | 109.5 | ||
C6—C1—C2—C3 | −1.2 (11) | C6—C7—C8—N1 | 178.6 (4) |
C1—C2—C3—C4 | 2.0 (12) | O1—C7—C8—C9 | 65.2 (6) |
C2—C3—C4—C5 | −1.8 (12) | C6—C7—C8—C9 | −59.2 (6) |
C3—C4—C5—C6 | 0.8 (10) | O4—C11—C12—C13 | 106.6 (6) |
C2—C1—C6—C5 | 0.2 (9) | O3—C11—C12—C13 | −70.7 (6) |
C2—C1—C6—C7 | 179.4 (6) | C11—C12—C13—O2 | 71.0 (5) |
C4—C5—C6—C1 | 0.0 (9) | C11—C12—C13—C14 | −53.2 (5) |
C4—C5—C6—C7 | −179.2 (6) | O2—C13—C14—O5 | −11.5 (7) |
C1—C6—C7—O1 | −17.0 (7) | C12—C13—C14—O5 | 110.5 (6) |
C5—C6—C7—O1 | 162.2 (5) | O2—C13—C14—O6 | 169.9 (4) |
C1—C6—C7—C8 | 102.5 (6) | C12—C13—C14—O6 | −68.2 (6) |
C5—C6—C7—C8 | −78.3 (6) | C9—C8—N1—C10 | −175.0 (5) |
O1—C7—C8—N1 | −57.1 (5) | C7—C8—N1—C10 | −49.4 (6) |
D—H···A | D—H | H···A | D···A | D—H···A |
N1—H10···O5i | 0.9 | 1.99 | 2.867 (6) | 165 |
N1—H11···O6ii | 0.9 | 1.88 | 2.727 (6) | 156 |
O2—H16···O5iii | 0.82 | 1.96 | 2.769 (5) | 170 |
Symmetry codes: (i) −x, y+1/2, −z; (ii) x−1, y+1, z; (iii) −x+1, y+1/2, −z. |
C12H12NO4 | F(000) = 640 |
Mr = 299.32 | Dx = 1.273 Mg m−3 |
Orthorhombic, P212121 | Mo Kα radiation, λ = 0.71073 Å |
Hall symbol: P 2ac 2ab | Cell parameters from 12306 reflections |
a = 5.6370 (2) Å | θ = 4.1–27.5° |
b = 13.4950 (5) Å | µ = 0.1 mm−1 |
c = 20.5250 (5) Å | T = 150 K |
V = 1561.36 (9) Å3 | Needle, colourless |
Z = 4 | 0.25 × 0.05 × 0.05 mm |
KappaCCD diffractometer | 1712 reflections with I > 2σ(I) |
Radiation source: Enraf Nonius FR590 | θmax = 27.5°, θmin = 4.1° |
Graphite monochromator | h = −6→7 |
CCD rotation images, thick slices scans | k = −17→17 |
11592 measured reflections | l = −21→25 |
1996 independent reflections |
Refinement on F2 | Primary atom site location: structure-invariant direct methods |
Least-squares matrix: full | Secondary atom site location: difference Fourier map |
R[F2 > 2σ(F2)] = 0.036 | Hydrogen site location: inferred from neighbouring sites |
wR(F2) = 0.092 | H atoms treated by a mixture of independent and constrained refinement |
S = 1.05 | w = 1/[σ2(Fo2) + (0.0487P)2 + 0.2281P] where P = (Fo2 + 2Fc2)/3 |
1996 reflections | (Δ/σ)max < 0.001 |
208 parameters | Δρmax = 0.19 e Å−3 |
0 restraints | Δρmin = −0.17 e Å−3 |
C12H12NO4 | V = 1561.36 (9) Å3 |
Mr = 299.32 | Z = 4 |
Orthorhombic, P212121 | Mo Kα radiation |
a = 5.6370 (2) Å | µ = 0.1 mm−1 |
b = 13.4950 (5) Å | T = 150 K |
c = 20.5250 (5) Å | 0.25 × 0.05 × 0.05 mm |
KappaCCD diffractometer | 1996 independent reflections |
11592 measured reflections | 1712 reflections with I > 2σ(I) |
R[F2 > 2σ(F2)] = 0.036 | 0 restraints |
wR(F2) = 0.092 | H atoms treated by a mixture of independent and constrained refinement |
S = 1.05 | Δρmax = 0.19 e Å−3 |
1996 reflections | Δρmin = −0.17 e Å−3 |
208 parameters |
Geometry. All e.s.d.'s (except the e.s.d. in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell e.s.d.'s are taken into account individually in the estimation of e.s.d.'s in distances, angles and torsion angles; correlations between e.s.d.'s in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell e.s.d.'s is used for estimating e.s.d.'s involving l.s. planes. |
Refinement. Refinement of F2 against ALL reflections. The weighted R-factor wR and goodness of fit S are based on F2, conventional R-factors R are based on F, with F set to zero for negative F2. The threshold expression of F2 > σ(F2) is used only for calculating R-factors(gt) etc. and is not relevant to the choice of reflections for refinement. R-factors based on F2 are statistically about twice as large as those based on F, and R- factors based on ALL data will be even larger. |
x | y | z | Uiso*/Ueq | ||
C1 | 0.7193 (4) | 0.02778 (16) | 0.10470 (10) | 0.0293 (5) | |
H1 | 0.8515 | −0.0061 | 0.0838 | 0.035* | |
C2 | 0.7626 (4) | 0.07003 (18) | 0.16530 (10) | 0.0352 (5) | |
H2 | 0.9351 | 0.0554 | 0.1826 | 0.042* | |
C3 | 0.5922 (5) | 0.12873 (17) | 0.19428 (11) | 0.0379 (5) | |
H3 | 0.6147 | 0.1584 | 0.2381 | 0.045* | |
C4 | 0.3802 (5) | 0.14626 (17) | 0.16295 (11) | 0.0380 (5) | |
H4 | 0.2472 | 0.186 | 0.1793 | 0.046* | |
C5 | 0.3363 (4) | 0.10395 (17) | 0.10224 (10) | 0.0318 (5) | |
H5 | 0.1832 | 0.1099 | 0.0857 | 0.038* | |
C6 | 0.5055 (4) | 0.04414 (15) | 0.07267 (9) | 0.0251 (4) | |
C7 | 0.4589 (4) | −0.00311 (15) | 0.00663 (9) | 0.0240 (4) | |
H7 | 0.5238 | −0.0742 | 0.0102 | 0.029* | |
C8 | 0.5904 (4) | 0.05299 (15) | −0.04737 (9) | 0.0270 (4) | |
H8 | 0.7683 | 0.0485 | −0.0395 | 0.032* | |
C9 | 0.5209 (6) | 0.16161 (17) | −0.05193 (11) | 0.0442 (6) | |
H9A | 0.6032 | 0.1919 | −0.0877 | 0.066* | |
H9B | 0.5627 | 0.1947 | −0.0122 | 0.066* | |
H9C | 0.3529 | 0.1668 | −0.0588 | 0.066* | |
C10 | 0.5986 (5) | −0.09858 (16) | −0.12049 (11) | 0.0361 (5) | |
H12A | 0.7634 | −0.107 | −0.11 | 0.054* | |
H12B | 0.5716 | −0.1181 | −0.1649 | 0.054* | |
H12C | 0.5041 | −0.139 | −0.092 | 0.054* | |
C11 | 0.4881 (4) | 0.41800 (16) | 0.20953 (10) | 0.0282 (4) | |
C12 | 0.6532 (4) | 0.39022 (17) | 0.26328 (10) | 0.0287 (5) | |
H13 | 0.8124 | 0.4033 | 0.2544 | 0.034* | |
C13 | 0.6134 (4) | 0.34417 (16) | 0.31996 (10) | 0.0280 (4) | |
H14 | 0.7528 | 0.3338 | 0.3445 | 0.034* | |
C14 | 0.3868 (4) | 0.30580 (15) | 0.34815 (9) | 0.0254 (4) | |
O1 | 0.2161 (3) | −0.00389 (13) | −0.01055 (7) | 0.0314 (3) | |
O2 | 0.5673 (3) | 0.46479 (14) | 0.16280 (8) | 0.0422 (4) | |
O3 | 0.2668 (3) | 0.39346 (12) | 0.21329 (7) | 0.0296 (3) | |
O4 | 0.1941 (3) | 0.30615 (12) | 0.31439 (7) | 0.0320 (4) | |
H15 | 0.2228 | 0.3339 | 0.2716 | 0.038* | |
O5 | 0.3894 (3) | 0.27414 (13) | 0.40451 (7) | 0.0358 (4) | |
O6 | −0.0138 (3) | 0.31905 (12) | 0.47903 (8) | 0.0377 (4) | |
H16 | 0.1163 | 0.2981 | 0.4541 | 0.045* | |
N1 | 0.5318 (3) | 0.00672 (13) | −0.11208 (8) | 0.0262 (4) | |
H6 | 0.152 (6) | −0.061 (3) | 0.0027 (13) | 0.064 (10)* | |
H10 | 0.607 (5) | 0.0451 (19) | −0.1476 (11) | 0.031 (6)* | |
H11 | 0.372 (5) | 0.019 (2) | −0.1212 (11) | 0.035 (6)* | |
H17 | 0.012 (6) | 0.287 (2) | 0.5127 (14) | 0.049 (8)* |
U11 | U22 | U33 | U12 | U13 | U23 | |
C1 | 0.0281 (10) | 0.0323 (11) | 0.0273 (10) | −0.0002 (9) | 0.0005 (8) | 0.0000 (8) |
C2 | 0.0351 (12) | 0.0408 (12) | 0.0298 (11) | −0.0035 (11) | −0.0045 (9) | 0.0014 (9) |
C3 | 0.0521 (15) | 0.0331 (12) | 0.0285 (11) | −0.0029 (11) | −0.0022 (11) | −0.0047 (9) |
C4 | 0.0480 (14) | 0.0302 (12) | 0.0358 (12) | 0.0057 (11) | 0.0059 (11) | −0.0038 (9) |
C5 | 0.0343 (12) | 0.0297 (11) | 0.0312 (11) | 0.0031 (9) | 0.0002 (9) | 0.0001 (8) |
C6 | 0.0290 (10) | 0.0240 (9) | 0.0223 (10) | −0.0016 (9) | 0.0023 (8) | 0.0034 (7) |
C7 | 0.0257 (10) | 0.0254 (9) | 0.0209 (9) | −0.0014 (9) | 0.0009 (7) | 0.0028 (7) |
C8 | 0.0300 (11) | 0.0299 (11) | 0.0211 (10) | −0.0067 (9) | 0.0002 (8) | 0.0009 (7) |
C9 | 0.0728 (19) | 0.0275 (11) | 0.0322 (12) | −0.0091 (12) | 0.0089 (12) | 0.0034 (8) |
C10 | 0.0485 (13) | 0.0301 (11) | 0.0296 (11) | −0.0019 (11) | 0.0042 (10) | −0.0013 (8) |
C11 | 0.0256 (10) | 0.0344 (11) | 0.0246 (10) | 0.0041 (9) | 0.0035 (8) | 0.0018 (8) |
C12 | 0.0203 (10) | 0.0377 (12) | 0.0281 (11) | −0.0006 (9) | 0.0014 (8) | 0.0035 (8) |
C13 | 0.0229 (10) | 0.0345 (11) | 0.0268 (10) | 0.0024 (9) | −0.0031 (8) | 0.0008 (8) |
C14 | 0.0254 (10) | 0.0269 (10) | 0.0239 (10) | 0.0034 (9) | 0.0004 (8) | 0.0015 (7) |
O1 | 0.0270 (8) | 0.0395 (8) | 0.0278 (8) | −0.0060 (8) | −0.0012 (6) | 0.0043 (6) |
O2 | 0.0333 (9) | 0.0601 (11) | 0.0331 (9) | 0.0018 (8) | 0.0071 (7) | 0.0172 (8) |
O3 | 0.0247 (8) | 0.0405 (8) | 0.0237 (7) | −0.0008 (7) | −0.0030 (6) | 0.0052 (6) |
O4 | 0.0258 (8) | 0.0435 (9) | 0.0269 (7) | −0.0053 (7) | −0.0021 (6) | 0.0109 (6) |
O5 | 0.0355 (8) | 0.0468 (9) | 0.0252 (8) | 0.0033 (8) | 0.0003 (7) | 0.0124 (6) |
O6 | 0.0395 (9) | 0.0417 (9) | 0.0320 (9) | 0.0101 (8) | 0.0094 (7) | 0.0110 (7) |
N1 | 0.0250 (9) | 0.0321 (9) | 0.0216 (9) | −0.0023 (8) | 0.0001 (7) | 0.0028 (7) |
C1—C2 | 1.390 (3) | C10—N1 | 1.480 (3) |
C1—C6 | 1.391 (3) | C10—H12A | 0.96 |
C1—H1 | 0.9741 | C10—H12B | 0.96 |
C2—C3 | 1.380 (4) | C10—H12C | 0.96 |
C2—H2 | 1.0536 | C11—O2 | 1.232 (3) |
C3—C4 | 1.378 (4) | C11—O3 | 1.293 (3) |
C3—H3 | 0.9928 | C11—C12 | 1.491 (3) |
C4—C5 | 1.393 (3) | C12—C13 | 1.338 (3) |
C4—H4 | 0.9809 | C12—H13 | 0.9323 |
C5—C6 | 1.389 (3) | C13—C14 | 1.494 (3) |
C5—H5 | 0.9305 | C13—H14 | 0.9439 |
C6—C7 | 1.521 (3) | C14—O5 | 1.233 (2) |
C7—O1 | 1.413 (3) | C14—O4 | 1.289 (3) |
C7—C8 | 1.533 (3) | O1—H6 | 0.89 (4) |
C7—H7 | 1.0297 | O3—H15 | 1.4617 |
C8—N1 | 1.504 (3) | O4—H15 | 0.9696 |
C8—C9 | 1.520 (3) | O6—H16 | 0.9374 |
C8—H8 | 1.0172 | O6—H17 | 0.83 (3) |
C9—H9A | 0.96 | N1—H10 | 0.99 (2) |
C9—H9B | 0.96 | N1—H11 | 0.94 (3) |
C9—H9C | 0.96 | ||
C2—C1—C6 | 120.7 (2) | H9A—C9—H9B | 109.5 |
C2—C1—H1 | 117 | C8—C9—H9C | 109.5 |
C6—C1—H1 | 121.9 | H9A—C9—H9C | 109.5 |
C3—C2—C1 | 119.9 (2) | H9B—C9—H9C | 109.5 |
C3—C2—H2 | 127.2 | N1—C10—H12A | 109.5 |
C1—C2—H2 | 112.7 | N1—C10—H12B | 109.5 |
C4—C3—C2 | 120.1 (2) | H12A—C10—H12B | 109.5 |
C4—C3—H3 | 117.7 | N1—C10—H12C | 109.5 |
C2—C3—H3 | 122.2 | H12A—C10—H12C | 109.5 |
C3—C4—C5 | 120.1 (2) | H12B—C10—H12C | 109.5 |
C3—C4—H4 | 126.7 | O2—C11—O3 | 121.8 (2) |
C5—C4—H4 | 113.2 | O2—C11—C12 | 118.6 (2) |
C6—C5—C4 | 120.5 (2) | O3—C11—C12 | 119.57 (18) |
C6—C5—H5 | 121.9 | C13—C12—C11 | 130.9 (2) |
C4—C5—H5 | 117.1 | C13—C12—H13 | 114.8 |
C5—C6—C1 | 118.74 (19) | C11—C12—H13 | 114.1 |
C5—C6—C7 | 120.94 (19) | C12—C13—C14 | 129.9 (2) |
C1—C6—C7 | 120.32 (18) | C12—C13—H14 | 113.1 |
O1—C7—C6 | 113.13 (17) | C14—C13—H14 | 117 |
O1—C7—C8 | 106.96 (16) | O5—C14—O4 | 121.0 (2) |
C6—C7—C8 | 110.71 (16) | O5—C14—C13 | 118.24 (19) |
O1—C7—H7 | 110.8 | O4—C14—C13 | 120.73 (16) |
C6—C7—H7 | 105.4 | C7—O1—H6 | 109 (2) |
C8—C7—H7 | 109.8 | C11—O3—H15 | 110.7 |
N1—C8—C9 | 106.82 (17) | C14—O4—H15 | 110.4 |
N1—C8—C7 | 109.09 (16) | H16—O6—H17 | 99.2 |
C9—C8—C7 | 113.32 (18) | C10—N1—C8 | 116.47 (16) |
N1—C8—H8 | 109.4 | C10—N1—H10 | 108.0 (14) |
C9—C8—H8 | 108.8 | C8—N1—H10 | 109.9 (14) |
C7—C8—H8 | 109.4 | C10—N1—H11 | 113.4 (16) |
C8—C9—H9A | 109.5 | C8—N1—H11 | 108.2 (15) |
C8—C9—H9B | 109.5 | H10—N1—H11 | 100 (2) |
C6—C1—C2—C3 | 0.1 (3) | O1—C7—C8—N1 | −54.0 (2) |
C1—C2—C3—C4 | −0.6 (4) | C6—C7—C8—N1 | −177.67 (16) |
C2—C3—C4—C5 | 0.7 (4) | O1—C7—C8—C9 | 64.9 (2) |
C3—C4—C5—C6 | −0.2 (3) | C6—C7—C8—C9 | −58.8 (2) |
C4—C5—C6—C1 | −0.3 (3) | O2—C11—C12—C13 | 176.7 (2) |
C4—C5—C6—C7 | 179.53 (19) | O3—C11—C12—C13 | −2.6 (4) |
C2—C1—C6—C5 | 0.3 (3) | C11—C12—C13—C14 | −0.4 (4) |
C2—C1—C6—C7 | −179.48 (19) | C12—C13—C14—O5 | −173.1 (2) |
C5—C6—C7—O1 | −17.1 (3) | C12—C13—C14—O4 | 6.7 (4) |
C1—C6—C7—O1 | 162.66 (19) | C9—C8—N1—C10 | 176.4 (2) |
C5—C6—C7—C8 | 102.9 (2) | C7—C8—N1—C10 | −60.8 (2) |
C1—C6—C7—C8 | −77.3 (2) |
D—H···A | D—H | H···A | D···A | D—H···A |
O1—H6···O6i | 0.89 (4) | 1.84 (4) | 2.725 (2) | 174 (3) |
N1—H10···O3ii | 0.99 (2) | 1.82 (3) | 2.808 (2) | 174 (2) |
N1—H10···O2ii | 0.99 (2) | 2.62 (3) | 3.216 (3) | 118.9 (18) |
N1—H11···O2iii | 0.94 (3) | 1.93 (3) | 2.844 (2) | 165 (2) |
O6—H17···O5iv | 0.83 (3) | 2.01 (3) | 2.755 (2) | 149 (3) |
Symmetry codes: (i) −x, y−1/2, −z+1/2; (ii) x+1/2, −y+1/2, −z; (iii) x−1/2, −y+1/2, −z; (iv) x−1/2, −y+1/2, −z+1. |
C11H17NO3 | F(000) = 468 |
Mr = 217.26 | Dx = 1.235 Mg m−3 |
Monoclinic, C2 | Mo Kα radiation, λ = 0.71073 Å |
Hall symbol: C 2y | Cell parameters from 7336 reflections |
a = 15.1190 (14) Å | θ = 1.0–27.5° |
b = 5.7840 (7) Å | µ = 0.09 mm−1 |
c = 13.8788 (15) Å | T = 150 K |
β = 105.765 (7)° | Needle, colourless |
V = 1168.0 (2) Å3 | 0.3 × 0.05 × 0.05 mm |
Z = 4 |
KappaCCD diffractometer | 1448 independent reflections |
Radiation source: Enraf Nonius FR590 | 937 reflections with I > 2σ(I) |
Graphite monochromator | θmax = 27.5°, θmin = 2.8° |
CCD rotation images, thick slices scans | h = −19→19 |
Absorption correction: multi-scan R.H. Blessing, Acta Cryst. (1995), A51, 33-38 | k = −6→7 |
Tmin = 0.987, Tmax = 1.021 | l = −17→14 |
4107 measured reflections |
Refinement on F2 | Primary atom site location: structure-invariant direct methods |
Least-squares matrix: full | Secondary atom site location: difference Fourier map |
R[F2 > 2σ(F2)] = 0.056 | Hydrogen site location: inferred from neighbouring sites |
wR(F2) = 0.129 | H atoms treated by a mixture of independent and constrained refinement |
S = 1.06 | w = 1/[σ2(Fo2) + (0.046P)2 + 0.3178P] where P = (Fo2 + 2Fc2)/3 |
1448 reflections | (Δ/σ)max = 0.001 |
182 parameters | Δρmax = 0.15 e Å−3 |
1 restraint | Δρmin = −0.23 e Å−3 |
C11H17NO3 | V = 1168.0 (2) Å3 |
Mr = 217.26 | Z = 4 |
Monoclinic, C2 | Mo Kα radiation |
a = 15.1190 (14) Å | µ = 0.09 mm−1 |
b = 5.7840 (7) Å | T = 150 K |
c = 13.8788 (15) Å | 0.3 × 0.05 × 0.05 mm |
β = 105.765 (7)° |
KappaCCD diffractometer | 4107 measured reflections |
Absorption correction: multi-scan R.H. Blessing, Acta Cryst. (1995), A51, 33-38 | 1448 independent reflections |
Tmin = 0.987, Tmax = 1.021 | 937 reflections with I > 2σ(I) |
R[F2 > 2σ(F2)] = 0.056 | 1 restraint |
wR(F2) = 0.129 | H atoms treated by a mixture of independent and constrained refinement |
S = 1.06 | Δρmax = 0.15 e Å−3 |
1448 reflections | Δρmin = −0.23 e Å−3 |
182 parameters |
Geometry. All e.s.d.'s (except the e.s.d. in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell e.s.d.'s are taken into account individually in the estimation of e.s.d.'s in distances, angles and torsion angles; correlations between e.s.d.'s in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell e.s.d.'s is used for estimating e.s.d.'s involving l.s. planes. |
Refinement. Refinement of F2 against ALL reflections. The weighted R-factor wR and goodness of fit S are based on F2, conventional R-factors R are based on F, with F set to zero for negative F2. The threshold expression of F2 > σ(F2) is used only for calculating R-factors(gt) etc. and is not relevant to the choice of reflections for refinement. R-factors based on F2 are statistically about twice as large as those based on F, and R- factors based on ALL data will be even larger. |
x | y | z | Uiso*/Ueq | Occ. (<1) | |
C1 | 0.3002 (3) | 0.9664 (8) | 0.1316 (3) | 0.0496 (10) | |
H1 | 0.262 (3) | 0.835 (8) | 0.147 (3) | 0.06* | |
C2 | 0.3336 (3) | 0.9584 (9) | 0.0474 (3) | 0.0569 (11) | |
H2 | 0.318 (3) | 0.823 (9) | 0.004 (3) | 0.068* | |
C3 | 0.3865 (3) | 1.1377 (8) | 0.0280 (3) | 0.0564 (12) | |
H3 | 0.411 (3) | 1.125 (8) | −0.030 (3) | 0.068* | |
C4 | 0.4078 (3) | 1.3199 (8) | 0.0924 (3) | 0.0561 (11) | |
H4 | 0.447 (3) | 1.467 (8) | 0.080 (3) | 0.067* | |
C5 | 0.3747 (3) | 1.3314 (7) | 0.1768 (3) | 0.0479 (10) | |
H5 | 0.389 (3) | 1.459 (8) | 0.224 (3) | 0.057* | |
C6 | 0.3201 (2) | 1.1523 (7) | 0.1964 (3) | 0.0421 (9) | |
C7 | 0.2841 (3) | 1.1662 (6) | 0.2886 (3) | 0.0408 (9) | |
H7 | 0.339 (3) | 1.240 (7) | 0.347 (3) | 0.049* | |
C8 | 0.2022 (3) | 1.3267 (7) | 0.2733 (3) | 0.0433 (9) | |
H8 | 0.217 (2) | 1.480 (8) | 0.253 (3) | 0.052* | |
C9 | 0.1149 (2) | 1.2277 (9) | 0.2038 (3) | 0.0580 (11) | |
H9A | 0.0957 | 1.0953 | 0.2346 | 0.087* | |
H9B | 0.1264 | 1.1825 | 0.1418 | 0.087* | |
H9C | 0.0674 | 1.3428 | 0.191 | 0.087* | |
C10 | 0.1129 (3) | 1.5373 (9) | 0.3772 (4) | 0.0576 (11) | |
H12A | 0.119 (3) | 1.681 (9) | 0.340 (3) | 0.069* | |
H12B | 0.052 (3) | 1.469 (8) | 0.340 (3) | 0.069* | |
H12C | 0.120 (3) | 1.574 (9) | 0.446 (3) | 0.069* | |
C11 | −0.0851 (2) | 1.0927 (7) | 0.4610 (3) | 0.0429 (9) | |
C12 | 0 | 0.9540 (12) | 0.5 | 0.087 (2) | |
H13 | 0.0082 | 0.8549 | 0.4467 | 0.104* | 0.5 |
H14 | −0.0082 | 0.8549 | 0.5533 | 0.104* | 0.5 |
N1 | 0.1890 (2) | 1.3749 (6) | 0.3743 (2) | 0.0432 (8) | |
H10 | 0.243 (3) | 1.436 (7) | 0.414 (3) | 0.052* | |
H11 | 0.175 (3) | 1.240 (8) | 0.404 (3) | 0.052* | |
O1 | 0.25754 (19) | 0.9501 (5) | 0.31847 (19) | 0.0498 (7) | |
H6 | 0.305 (3) | 0.875 (8) | 0.341 (3) | 0.06* | |
O2 | −0.15250 (16) | 1.0494 (5) | 0.49529 (17) | 0.0498 (7) | |
O3 | −0.08517 (19) | 1.2321 (7) | 0.3944 (2) | 0.0739 (10) |
U11 | U22 | U33 | U12 | U13 | U23 | |
C1 | 0.055 (2) | 0.045 (2) | 0.054 (2) | −0.002 (2) | 0.0234 (18) | −0.002 (2) |
C2 | 0.065 (3) | 0.057 (3) | 0.053 (2) | 0.005 (2) | 0.022 (2) | −0.011 (2) |
C3 | 0.047 (2) | 0.077 (3) | 0.053 (2) | 0.000 (2) | 0.0252 (18) | −0.002 (2) |
C4 | 0.045 (2) | 0.070 (3) | 0.060 (2) | −0.011 (2) | 0.0251 (18) | −0.002 (2) |
C5 | 0.047 (2) | 0.053 (3) | 0.046 (2) | −0.0041 (19) | 0.0179 (17) | −0.0036 (19) |
C6 | 0.0364 (19) | 0.047 (2) | 0.0445 (19) | −0.0022 (17) | 0.0143 (15) | 0.0007 (18) |
C7 | 0.043 (2) | 0.040 (2) | 0.0434 (19) | −0.0051 (17) | 0.0182 (16) | −0.0004 (17) |
C8 | 0.042 (2) | 0.046 (2) | 0.0452 (19) | −0.0031 (17) | 0.0172 (15) | 0.0020 (18) |
C9 | 0.042 (2) | 0.080 (3) | 0.052 (2) | 0.000 (2) | 0.0140 (18) | −0.002 (2) |
C10 | 0.051 (2) | 0.052 (3) | 0.078 (3) | 0.005 (2) | 0.032 (2) | −0.002 (2) |
C11 | 0.040 (2) | 0.045 (2) | 0.0436 (18) | 0.0003 (17) | 0.0117 (15) | −0.0077 (18) |
C12 | 0.034 (3) | 0.044 (4) | 0.174 (7) | 0 | 0.012 (4) | 0 |
N1 | 0.0378 (17) | 0.0461 (19) | 0.0502 (18) | −0.0069 (16) | 0.0194 (13) | −0.0019 (16) |
O1 | 0.0497 (16) | 0.0456 (18) | 0.0582 (16) | −0.0010 (13) | 0.0213 (13) | 0.0075 (13) |
O2 | 0.0431 (15) | 0.0563 (16) | 0.0555 (14) | −0.0029 (13) | 0.0225 (12) | −0.0069 (14) |
O3 | 0.0509 (17) | 0.104 (3) | 0.0693 (18) | −0.0005 (19) | 0.0206 (14) | 0.028 (2) |
C1—C6 | 1.382 (5) | C8—H8 | 0.97 (5) |
C1—C2 | 1.395 (5) | C9—H9A | 0.96 |
C1—H1 | 1.01 (4) | C9—H9B | 0.96 |
C2—C3 | 1.380 (6) | C9—H9C | 0.96 |
C2—H2 | 0.98 (5) | C10—N1 | 1.494 (5) |
C3—C4 | 1.363 (6) | C10—H12A | 0.99 (5) |
C3—H3 | 0.98 (4) | C10—H12B | 1.00 (5) |
C4—C5 | 1.394 (5) | C10—H12C | 0.96 (4) |
C4—H4 | 1.08 (5) | C11—O3 | 1.227 (5) |
C5—C6 | 1.397 (5) | C11—O2 | 1.261 (4) |
C5—H5 | 0.97 (4) | C11—C12 | 1.488 (5) |
C6—C7 | 1.522 (5) | C12—C11i | 1.488 (5) |
C7—O1 | 1.409 (4) | C12—H13 | 0.97 |
C7—C8 | 1.516 (5) | C12—H14 | 0.97 |
C7—H7 | 1.08 (4) | N1—H10 | 0.92 (4) |
C8—N1 | 1.496 (5) | N1—H11 | 0.94 (4) |
C8—C9 | 1.519 (5) | O1—H6 | 0.83 (4) |
C6—C1—C2 | 120.5 (4) | C9—C8—H8 | 113 (2) |
C6—C1—H1 | 119 (2) | C8—C9—H9A | 109.5 |
C2—C1—H1 | 121 (2) | C8—C9—H9B | 109.5 |
C3—C2—C1 | 120.0 (4) | H9A—C9—H9B | 109.5 |
C3—C2—H2 | 122 (2) | C8—C9—H9C | 109.5 |
C1—C2—H2 | 118 (2) | H9A—C9—H9C | 109.5 |
C4—C3—C2 | 120.0 (3) | H9B—C9—H9C | 109.5 |
C4—C3—H3 | 122 (3) | N1—C10—H12A | 109 (2) |
C2—C3—H3 | 118 (3) | N1—C10—H12B | 110 (3) |
C3—C4—C5 | 120.9 (4) | H12A—C10—H12B | 105 (4) |
C3—C4—H4 | 123 (2) | N1—C10—H12C | 107 (3) |
C5—C4—H4 | 116 (2) | H12A—C10—H12C | 110 (4) |
C4—C5—C6 | 119.6 (4) | H12B—C10—H12C | 115 (3) |
C4—C5—H5 | 123 (2) | O3—C11—O2 | 125.4 (3) |
C6—C5—H5 | 117 (2) | O3—C11—C12 | 116.8 (3) |
C1—C6—C5 | 119.1 (3) | O2—C11—C12 | 117.6 (3) |
C1—C6—C7 | 121.6 (3) | C11—C12—C11i | 114.8 (6) |
C5—C6—C7 | 119.3 (3) | C11—C12—H13 | 108.6 |
O1—C7—C8 | 107.3 (3) | C11i—C12—H13 | 108.6 |
O1—C7—C6 | 113.3 (3) | C11—C12—H14 | 108.6 |
C8—C7—C6 | 112.3 (3) | C11i—C12—H14 | 108.6 |
O1—C7—H7 | 111 (2) | H13—C12—H14 | 107.6 |
C8—C7—H7 | 107 (2) | C10—N1—C8 | 116.3 (3) |
C6—C7—H7 | 106.1 (18) | C10—N1—H10 | 108 (2) |
N1—C8—C7 | 107.1 (3) | C8—N1—H10 | 108 (2) |
N1—C8—C9 | 110.6 (3) | C10—N1—H11 | 104 (2) |
C7—C8—C9 | 113.2 (4) | C8—N1—H11 | 111 (2) |
N1—C8—H8 | 101 (2) | H10—N1—H11 | 109 (3) |
C7—C8—H8 | 111 (2) | C7—O1—H6 | 107 (3) |
C6—C1—C2—C3 | −0.4 (7) | C1—C6—C7—C8 | −101.8 (4) |
C1—C2—C3—C4 | 1.5 (7) | C5—C6—C7—C8 | 78.4 (4) |
C2—C3—C4—C5 | −1.8 (7) | O1—C7—C8—N1 | 69.5 (4) |
C3—C4—C5—C6 | 0.9 (7) | C6—C7—C8—N1 | −165.3 (3) |
C2—C1—C6—C5 | −0.5 (6) | O1—C7—C8—C9 | −52.6 (4) |
C2—C1—C6—C7 | 179.7 (4) | C6—C7—C8—C9 | 72.5 (4) |
C4—C5—C6—C1 | 0.2 (6) | O3—C11—C12—C11i | 56.6 (3) |
C4—C5—C6—C7 | −180.0 (4) | O2—C11—C12—C11i | −126.9 (3) |
C1—C6—C7—O1 | 19.9 (5) | C7—C8—N1—C10 | 178.1 (3) |
C5—C6—C7—O1 | −159.9 (3) | C9—C8—N1—C10 | −58.1 (5) |
Symmetry code: (i) −x, y, −z+1. |
D—H···A | D—H | H···A | D···A | D—H···A |
N1—H10···O2ii | 0.92 (4) | 1.80 (4) | 2.719 (4) | 178 (3) |
N1—H11···O2i | 0.94 (4) | 1.88 (4) | 2.769 (4) | 158 (4) |
O1—H6···O3iii | 0.83 (4) | 1.82 (5) | 2.645 (4) | 175 (5) |
Symmetry codes: (i) −x, y, −z+1; (ii) x+1/2, y+1/2, z; (iii) x+1/2, y−1/2, z. |
C11H19NO4S | F(000) = 560 |
Mr = 261.33 | Dx = 1.329 Mg m−3 |
Monoclinic, C2 | Mo Kα radiation, λ = 0.71073 Å |
Hall symbol: C 2y | Cell parameters from 32320 reflections |
a = 14.287 (2) Å | θ = 1.0–27.5° |
b = 6.1075 (7) Å | µ = 0.25 mm−1 |
c = 14.993 (2) Å | T = 150 K |
β = 93.211 (6)° | Needle, colourless |
V = 1306.3 (3) Å3 | 0.3 × 0.05 × 0.05 mm |
Z = 4 |
KappaCCD diffractometer | 2236 independent reflections |
Radiation source: Enraf Nonius FR590 | 1751 reflections with I > 2σ(I) |
Graphite monochromator | Rint = 0.029 |
CCD rotation images, thick slices scans | θmax = 27.5°, θmin = 2.7° |
Absorption correction: multi-scan R.H. Blessing, Acta Cryst. (1995), A51, 33-38 | h = −13→14 |
Tmin = 0.984, Tmax = 1.017 | k = −7→7 |
3231 measured reflections | l = −19→13 |
Refinement on F2 | Secondary atom site location: difference Fourier map |
Least-squares matrix: full | Hydrogen site location: inferred from neighbouring sites |
R[F2 > 2σ(F2)] = 0.048 | H atoms treated by a mixture of independent and constrained refinement |
wR(F2) = 0.119 | w = 1/[σ2(Fo2) + (0.0349P)2 + 1.5263P] where P = (Fo2 + 2Fc2)/3 |
S = 1.10 | (Δ/σ)max = 0.002 |
2236 reflections | Δρmax = 0.20 e Å−3 |
179 parameters | Δρmin = −0.33 e Å−3 |
1 restraint | Absolute structure: Flack H D (1983), Acta Cryst. A39, 876-881 |
Primary atom site location: structure-invariant direct methods | Absolute structure parameter: −0.04 (14) |
C11H19NO4S | V = 1306.3 (3) Å3 |
Mr = 261.33 | Z = 4 |
Monoclinic, C2 | Mo Kα radiation |
a = 14.287 (2) Å | µ = 0.25 mm−1 |
b = 6.1075 (7) Å | T = 150 K |
c = 14.993 (2) Å | 0.3 × 0.05 × 0.05 mm |
β = 93.211 (6)° |
KappaCCD diffractometer | 2236 independent reflections |
Absorption correction: multi-scan R.H. Blessing, Acta Cryst. (1995), A51, 33-38 | 1751 reflections with I > 2σ(I) |
Tmin = 0.984, Tmax = 1.017 | Rint = 0.029 |
3231 measured reflections |
R[F2 > 2σ(F2)] = 0.048 | H atoms treated by a mixture of independent and constrained refinement |
wR(F2) = 0.119 | Δρmax = 0.20 e Å−3 |
S = 1.10 | Δρmin = −0.33 e Å−3 |
2236 reflections | Absolute structure: Flack H D (1983), Acta Cryst. A39, 876-881 |
179 parameters | Absolute structure parameter: −0.04 (14) |
1 restraint |
Geometry. All e.s.d.'s (except the e.s.d. in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell e.s.d.'s are taken into account individually in the estimation of e.s.d.'s in distances, angles and torsion angles; correlations between e.s.d.'s in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell e.s.d.'s is used for estimating e.s.d.'s involving l.s. planes. |
Refinement. Refinement of F2 against ALL reflections. The weighted R-factor wR and goodness of fit S are based on F2, conventional R-factors R are based on F, with F set to zero for negative F2. The threshold expression of F2 > σ(F2) is used only for calculating R-factors(gt) etc. and is not relevant to the choice of reflections for refinement. R-factors based on F2 are statistically about twice as large as those based on F, and R- factors based on ALL data will be even larger. |
x | y | z | Uiso*/Ueq | ||
C1 | 0.7331 (3) | 1.1379 (8) | 0.8743 (3) | 0.0452 (11) | |
H1 | 0.779 (3) | 1.260 (8) | 0.859 (3) | 0.054* | |
C2 | 0.6799 (4) | 1.1472 (10) | 0.9496 (3) | 0.0566 (13) | |
H2 | 0.6846 | 1.2684 | 0.9871 | 0.068* | |
C3 | 0.6207 (3) | 0.9779 (13) | 0.9686 (3) | 0.0551 (12) | |
H3 | 0.5864 | 0.9835 | 1.0194 | 0.066* | |
C4 | 0.6122 (4) | 0.8000 (10) | 0.9122 (3) | 0.0546 (13) | |
H4 | 0.569 (3) | 0.663 (9) | 0.932 (3) | 0.066* | |
C5 | 0.6645 (3) | 0.7875 (9) | 0.8372 (3) | 0.0446 (11) | |
H5 | 0.657 (3) | 0.652 (9) | 0.798 (3) | 0.054* | |
C6 | 0.7257 (2) | 0.9583 (9) | 0.8181 (2) | 0.0344 (8) | |
C7 | 0.7853 (3) | 0.9374 (7) | 0.7377 (2) | 0.0322 (9) | |
H7 | 0.743 (3) | 0.883 (6) | 0.681 (2) | 0.039* | |
C8 | 0.8638 (3) | 0.7697 (8) | 0.7542 (3) | 0.0360 (10) | |
H8 | 0.836 (3) | 0.631 (8) | 0.768 (2) | 0.043* | |
C9 | 0.9381 (3) | 0.8471 (9) | 0.8238 (3) | 0.0492 (12) | |
H9A | 0.9828 | 0.7319 | 0.836 | 0.074* | |
H9B | 0.9089 | 0.8851 | 0.8778 | 0.074* | |
H9C | 0.9696 | 0.973 | 0.8016 | 0.074* | |
C10 | 0.9741 (3) | 0.5363 (7) | 0.6674 (3) | 0.0498 (12) | |
H12A | 1.0258 | 0.5606 | 0.71 | 0.075* | |
H12B | 0.9973 | 0.519 | 0.609 | 0.075* | |
H12C | 0.9411 | 0.4063 | 0.6832 | 0.075* | |
C11 | 0.6427 (3) | 0.6881 (8) | 0.5094 (3) | 0.0436 (12) | |
H13A | 0.5879 | 0.6888 | 0.4693 | 0.065* | |
H13B | 0.6976 | 0.6728 | 0.4758 | 0.065* | |
H13C | 0.6461 | 0.823 | 0.5423 | 0.065* | |
N1 | 0.9090 (3) | 0.7283 (6) | 0.6675 (2) | 0.0351 (8) | |
H10 | 0.858 (3) | 0.707 (7) | 0.623 (3) | 0.042* | |
H11 | 0.937 (3) | 0.836 (8) | 0.653 (3) | 0.042* | |
O1 | 0.8263 (2) | 1.1391 (5) | 0.7140 (2) | 0.0445 (7) | |
H6 | 0.8814 | 1.1414 | 0.7324 | 0.067* | |
O2 | 0.72468 (18) | 0.4740 (6) | 0.63878 (15) | 0.0453 (7) | |
O3 | 0.5562 (2) | 0.5129 (5) | 0.63647 (18) | 0.0493 (9) | |
O4 | 0.6274 (2) | 0.2689 (5) | 0.5309 (2) | 0.0465 (8) | |
S1 | 0.63637 (6) | 0.46809 (17) | 0.58403 (5) | 0.0330 (2) |
U11 | U22 | U33 | U12 | U13 | U23 | |
C1 | 0.048 (3) | 0.038 (3) | 0.050 (3) | −0.004 (2) | 0.007 (2) | −0.005 (2) |
C2 | 0.054 (3) | 0.064 (4) | 0.052 (3) | 0.008 (3) | 0.006 (2) | −0.016 (3) |
C3 | 0.037 (3) | 0.085 (4) | 0.045 (2) | −0.002 (3) | 0.0106 (17) | −0.005 (3) |
C4 | 0.044 (3) | 0.069 (4) | 0.052 (3) | −0.015 (3) | 0.011 (2) | −0.001 (3) |
C5 | 0.043 (3) | 0.049 (3) | 0.042 (2) | −0.011 (2) | 0.0063 (19) | −0.003 (2) |
C6 | 0.030 (2) | 0.040 (2) | 0.0338 (17) | 0.005 (2) | 0.0016 (13) | 0.004 (2) |
C7 | 0.029 (2) | 0.032 (3) | 0.0352 (19) | −0.0051 (19) | 0.0013 (14) | −0.0007 (18) |
C8 | 0.035 (3) | 0.036 (3) | 0.038 (2) | −0.002 (2) | 0.0100 (17) | 0.0046 (19) |
C9 | 0.042 (3) | 0.068 (3) | 0.036 (2) | 0.001 (2) | −0.0061 (19) | −0.001 (2) |
C10 | 0.042 (3) | 0.035 (3) | 0.074 (3) | 0.0044 (18) | 0.014 (2) | 0.002 (2) |
C11 | 0.043 (3) | 0.047 (3) | 0.041 (2) | −0.003 (2) | 0.0013 (19) | 0.007 (2) |
N1 | 0.035 (2) | 0.033 (2) | 0.0371 (19) | 0.0018 (15) | 0.0039 (14) | 0.0005 (14) |
O1 | 0.0397 (19) | 0.0435 (19) | 0.0509 (17) | −0.0038 (15) | 0.0072 (14) | 0.0082 (15) |
O2 | 0.0425 (16) | 0.0421 (16) | 0.0494 (15) | 0.0016 (17) | −0.0141 (11) | −0.0024 (17) |
O3 | 0.0441 (19) | 0.053 (3) | 0.0530 (16) | −0.0014 (15) | 0.0249 (13) | −0.0032 (14) |
O4 | 0.047 (2) | 0.0388 (19) | 0.0534 (19) | −0.0064 (15) | 0.0042 (14) | −0.0155 (14) |
S1 | 0.0306 (5) | 0.0317 (5) | 0.0370 (5) | −0.0007 (6) | 0.0047 (3) | −0.0012 (5) |
C1—C6 | 1.384 (6) | C9—H9A | 0.96 |
C1—C2 | 1.398 (6) | C9—H9B | 0.96 |
C1—H1 | 1.02 (5) | C9—H9C | 0.96 |
C2—C3 | 1.376 (8) | C10—N1 | 1.497 (5) |
C2—H2 | 0.93 | C10—H12A | 0.96 |
C3—C4 | 1.378 (8) | C10—H12B | 0.96 |
C3—H3 | 0.93 | C10—H12C | 0.96 |
C4—C5 | 1.386 (6) | C11—S1 | 1.754 (4) |
C4—H4 | 1.09 (5) | C11—H13A | 0.96 |
C5—C6 | 1.402 (7) | C11—H13B | 0.96 |
C5—H5 | 1.02 (5) | C11—H13C | 0.96 |
C6—C7 | 1.519 (5) | N1—H10 | 0.97 (4) |
C7—O1 | 1.418 (5) | N1—H11 | 0.81 (5) |
C7—C8 | 1.528 (6) | O1—H6 | 0.82 |
C7—H7 | 1.07 (4) | O2—S1 | 1.467 (2) |
C8—N1 | 1.505 (5) | O3—S1 | 1.451 (3) |
C8—C9 | 1.522 (6) | O4—S1 | 1.456 (3) |
C8—H8 | 0.97 (5) | ||
C6—C1—C2 | 119.9 (4) | C8—C9—H9B | 109.5 |
C6—C1—H1 | 118 (3) | H9A—C9—H9B | 109.5 |
C2—C1—H1 | 122 (3) | C8—C9—H9C | 109.5 |
C3—C2—C1 | 120.3 (5) | H9A—C9—H9C | 109.5 |
C3—C2—H2 | 119.8 | H9B—C9—H9C | 109.5 |
C1—C2—H2 | 119.8 | N1—C10—H12A | 109.5 |
C2—C3—C4 | 120.0 (4) | N1—C10—H12B | 109.5 |
C2—C3—H3 | 120 | H12A—C10—H12B | 109.5 |
C4—C3—H3 | 120 | N1—C10—H12C | 109.5 |
C3—C4—C5 | 120.6 (5) | H12A—C10—H12C | 109.5 |
C3—C4—H4 | 118 (2) | H12B—C10—H12C | 109.5 |
C5—C4—H4 | 121 (3) | S1—C11—H13A | 109.5 |
C4—C5—C6 | 119.7 (5) | S1—C11—H13B | 109.5 |
C4—C5—H5 | 118 (3) | H13A—C11—H13B | 109.5 |
C6—C5—H5 | 122 (3) | S1—C11—H13C | 109.5 |
C1—C6—C5 | 119.5 (3) | H13A—C11—H13C | 109.5 |
C1—C6—C7 | 121.5 (4) | H13B—C11—H13C | 109.5 |
C5—C6—C7 | 118.9 (4) | C10—N1—C8 | 115.4 (3) |
O1—C7—C6 | 112.5 (4) | C10—N1—H10 | 109 (3) |
O1—C7—C8 | 108.3 (3) | C8—N1—H10 | 106 (2) |
C6—C7—C8 | 111.5 (3) | C10—N1—H11 | 109 (3) |
O1—C7—H7 | 107 (2) | C8—N1—H11 | 110 (3) |
C6—C7—H7 | 110 (2) | H10—N1—H11 | 107 (4) |
C8—C7—H7 | 107 (2) | C7—O1—H6 | 109.5 |
N1—C8—C9 | 109.1 (4) | O3—S1—O4 | 113.94 (19) |
N1—C8—C7 | 108.6 (3) | O3—S1—O2 | 111.87 (16) |
C9—C8—C7 | 112.4 (4) | O4—S1—O2 | 111.9 (2) |
N1—C8—H8 | 104 (2) | O3—S1—C11 | 105.8 (2) |
C9—C8—H8 | 114 (2) | O4—S1—C11 | 107.31 (18) |
C7—C8—H8 | 108 (3) | O2—S1—C11 | 105.3 (2) |
C8—C9—H9A | 109.5 | ||
C6—C1—C2—C3 | 0.5 (8) | C5—C6—C7—O1 | 165.9 (4) |
C1—C2—C3—C4 | −1.3 (8) | C1—C6—C7—C8 | 105.4 (5) |
C2—C3—C4—C5 | 1.4 (9) | C5—C6—C7—C8 | −72.3 (5) |
C3—C4—C5—C6 | −0.7 (8) | O1—C7—C8—N1 | −65.5 (4) |
C2—C1—C6—C5 | 0.2 (7) | C6—C7—C8—N1 | 170.2 (4) |
C2—C1—C6—C7 | −177.4 (4) | O1—C7—C8—C9 | 55.3 (4) |
C4—C5—C6—C1 | −0.1 (7) | C6—C7—C8—C9 | −68.9 (5) |
C4—C5—C6—C7 | 177.6 (4) | C9—C8—N1—C10 | 68.9 (5) |
C1—C6—C7—O1 | −16.4 (5) | C7—C8—N1—C10 | −168.3 (4) |
D—H···A | D—H | H···A | D···A | D—H···A |
N1—H10···O4i | 0.97 (4) | 2.36 (4) | 3.002 (5) | 124 (3) |
N1—H11···O3ii | 0.81 (5) | 2.04 (5) | 2.788 (5) | 153 (5) |
Symmetry codes: (i) −x+3/2, y+1/2, −z+1; (ii) x+1/2, y+1/2, z. |
C10H14N2O4 | F(000) = 244 |
Mr = 228.25 | Dx = 1.285 Mg m−3 |
Monoclinic, P21 | Mo Kα radiation, λ = 0.71073 Å |
Hall symbol: P 2yb | Cell parameters from 4151 reflections |
a = 5.5309 (4) Å | θ = 1.0–27.5° |
b = 6.8501 (6) Å | µ = 0.1 mm−1 |
c = 15.6906 (13) Å | T = 150 K |
β = 97.243 (6)° | Plate, yellow |
V = 589.73 (8) Å3 | 0.2 × 0.2 × 0.05 mm |
Z = 2 |
KappaCCD diffractometer | 1274 independent reflections |
Radiation source: Enraf Nonius FR590 | 991 reflections with I > 2σ(I) |
Graphite monochromator | Rint = 0.032 |
CCD rotation images, thick slices scans | θmax = 27.5°, θmin = 3.3° |
Absorption correction: multi-scan R.H. Blessing, Acta Cryst. (1995), A51, 33-38 | h = −5→7 |
Tmin = 0.951, Tmax = 1.041 | k = −6→8 |
2914 measured reflections | l = −17→17 |
Refinement on F2 | Primary atom site location: structure-invariant direct methods |
Least-squares matrix: full | Secondary atom site location: difference Fourier map |
R[F2 > 2σ(F2)] = 0.044 | Hydrogen site location: inferred from neighbouring sites |
wR(F2) = 0.103 | H atoms treated by a mixture of independent and constrained refinement |
S = 1.07 | w = 1/[σ2(Fo2) + (0.0466P)2] where P = (Fo2 + 2Fc2)/3 |
1274 reflections | (Δ/σ)max < 0.001 |
185 parameters | Δρmax = 0.17 e Å−3 |
1 restraint | Δρmin = −0.23 e Å−3 |
C10H14N2O4 | V = 589.73 (8) Å3 |
Mr = 228.25 | Z = 2 |
Monoclinic, P21 | Mo Kα radiation |
a = 5.5309 (4) Å | µ = 0.1 mm−1 |
b = 6.8501 (6) Å | T = 150 K |
c = 15.6906 (13) Å | 0.2 × 0.2 × 0.05 mm |
β = 97.243 (6)° |
KappaCCD diffractometer | 1274 independent reflections |
Absorption correction: multi-scan R.H. Blessing, Acta Cryst. (1995), A51, 33-38 | 991 reflections with I > 2σ(I) |
Tmin = 0.951, Tmax = 1.041 | Rint = 0.032 |
2914 measured reflections |
R[F2 > 2σ(F2)] = 0.044 | 1 restraint |
wR(F2) = 0.103 | H atoms treated by a mixture of independent and constrained refinement |
S = 1.07 | Δρmax = 0.17 e Å−3 |
1274 reflections | Δρmin = −0.23 e Å−3 |
185 parameters |
Geometry. All e.s.d.'s (except the e.s.d. in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell e.s.d.'s are taken into account individually in the estimation of e.s.d.'s in distances, angles and torsion angles; correlations between e.s.d.'s in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell e.s.d.'s is used for estimating e.s.d.'s involving l.s. planes. |
Refinement. Refinement of F2 against ALL reflections. The weighted R-factor wR and goodness of fit S are based on F2, conventional R-factors R are based on F, with F set to zero for negative F2. The threshold expression of F2 > σ(F2) is used only for calculating R-factors(gt) etc. and is not relevant to the choice of reflections for refinement. R-factors based on F2 are statistically about twice as large as those based on F, and R- factors based on ALL data will be even larger. |
x | y | z | Uiso*/Ueq | ||
C1 | −0.0329 (6) | 0.5459 (5) | 0.3402 (2) | 0.0404 (7) | |
H1 | −0.169 (7) | 0.565 (6) | 0.299 (2) | 0.049* | |
C2 | −0.0436 (7) | 0.6236 (6) | 0.4211 (2) | 0.0498 (8) | |
H2 | −0.185 (7) | 0.693 (7) | 0.435 (2) | 0.06* | |
C3 | 0.1510 (6) | 0.6036 (6) | 0.4847 (2) | 0.0505 (9) | |
H3 | 0.140 (6) | 0.654 (7) | 0.542 (2) | 0.061* | |
C4 | 0.3562 (7) | 0.5038 (6) | 0.4677 (2) | 0.0518 (9) | |
H4 | 0.483 (7) | 0.489 (7) | 0.511 (3) | 0.062* | |
C5 | 0.3679 (6) | 0.4258 (5) | 0.3870 (2) | 0.0432 (8) | |
H5 | 0.516 (6) | 0.353 (7) | 0.3714 (19) | 0.052* | |
C6 | 0.1751 (5) | 0.4460 (4) | 0.32202 (19) | 0.0364 (7) | |
H6 | 0.456 (6) | 0.437 (7) | 0.188 (2) | 0.044* | |
C7 | 0.1859 (5) | 0.3675 (5) | 0.23264 (18) | 0.0332 (6) | |
H7 | 0.100 (5) | 0.462 (6) | 0.196 (2) | 0.04* | |
C8 | 0.0613 (5) | 0.1688 (5) | 0.21980 (18) | 0.0365 (7) | |
H8 | −0.111 (5) | 0.190 (6) | 0.2266 (18) | 0.044* | |
C9 | 0.1802 (8) | 0.0130 (6) | 0.2798 (2) | 0.0510 (9) | |
H9A | 0.360 (7) | 0.018 (7) | 0.280 (2) | 0.061* | |
H9B | 0.108 (6) | −0.114 (7) | 0.268 (2) | 0.061* | |
H9C | 0.136 (6) | 0.038 (7) | 0.343 (2) | 0.061* | |
C10 | −0.0222 (6) | 0.2406 (5) | 0.0604 (2) | 0.0439 (8) | |
H12A | −0.1764 | 0.2913 | 0.0721 | 0.066* | |
H12B | −0.0422 | 0.1754 | 0.0058 | 0.066* | |
H12C | 0.0918 | 0.3459 | 0.0591 | 0.066* | |
N1 | 0.0715 (5) | 0.0995 (4) | 0.12897 (15) | 0.0363 (6) | |
H10 | 0.244 (6) | 0.070 (5) | 0.1250 (19) | 0.044* | |
H11 | −0.016 (6) | 0.002 (7) | 0.121 (2) | 0.044* | |
N2 | 0.5696 (4) | 0.8008 (4) | 0.11488 (15) | 0.0366 (6) | |
O1 | 0.4272 (3) | 0.3458 (4) | 0.21190 (14) | 0.0403 (5) | |
O2 | 0.7798 (4) | 0.7339 (4) | 0.12860 (14) | 0.0479 (6) | |
O3 | 0.3895 (4) | 0.7037 (4) | 0.12808 (14) | 0.0500 (6) | |
O4 | 0.5408 (4) | 0.9729 (4) | 0.08800 (15) | 0.0537 (7) |
U11 | U22 | U33 | U12 | U13 | U23 | |
C1 | 0.0421 (16) | 0.0297 (18) | 0.0500 (18) | −0.0046 (14) | 0.0077 (14) | −0.0037 (14) |
C2 | 0.055 (2) | 0.035 (2) | 0.064 (2) | −0.0082 (16) | 0.0229 (17) | −0.0081 (16) |
C3 | 0.062 (2) | 0.045 (2) | 0.0456 (18) | −0.0174 (18) | 0.0110 (16) | −0.0052 (15) |
C4 | 0.056 (2) | 0.051 (2) | 0.0473 (18) | −0.0136 (18) | 0.0021 (15) | 0.0017 (17) |
C5 | 0.0448 (16) | 0.036 (2) | 0.0488 (18) | −0.0062 (14) | 0.0056 (14) | 0.0030 (14) |
C6 | 0.0400 (15) | 0.0230 (17) | 0.0463 (16) | −0.0087 (12) | 0.0056 (13) | 0.0054 (12) |
C7 | 0.0344 (13) | 0.0215 (15) | 0.0430 (15) | −0.0013 (13) | 0.0025 (11) | 0.0035 (12) |
C8 | 0.0406 (16) | 0.0265 (17) | 0.0427 (17) | −0.0068 (13) | 0.0067 (13) | 0.0023 (13) |
C9 | 0.075 (2) | 0.026 (2) | 0.050 (2) | −0.0067 (17) | 0.0003 (17) | 0.0086 (15) |
C10 | 0.0523 (17) | 0.0343 (19) | 0.0445 (16) | −0.0021 (15) | 0.0036 (13) | 0.0016 (14) |
N1 | 0.0373 (14) | 0.0244 (15) | 0.0468 (15) | −0.0035 (11) | 0.0033 (11) | 0.0027 (11) |
N2 | 0.0384 (13) | 0.0274 (15) | 0.0449 (13) | −0.0016 (11) | 0.0086 (10) | 0.0027 (11) |
O1 | 0.0392 (11) | 0.0291 (14) | 0.0534 (13) | −0.0019 (9) | 0.0089 (9) | 0.0032 (9) |
O2 | 0.0390 (11) | 0.0423 (14) | 0.0616 (13) | 0.0056 (11) | 0.0033 (9) | 0.0008 (11) |
O3 | 0.0453 (11) | 0.0386 (14) | 0.0673 (14) | −0.0071 (11) | 0.0115 (10) | 0.0110 (11) |
O4 | 0.0479 (13) | 0.0296 (14) | 0.0858 (17) | −0.0015 (11) | 0.0162 (12) | 0.0137 (12) |
C1—C2 | 1.385 (5) | C8—C9 | 1.517 (5) |
C1—C6 | 1.399 (4) | C8—H8 | 0.99 (3) |
C1—H1 | 0.94 (4) | C9—H9A | 0.99 (4) |
C2—C3 | 1.379 (5) | C9—H9B | 0.97 (5) |
C2—H2 | 0.96 (4) | C9—H9C | 1.06 (4) |
C3—C4 | 1.379 (6) | C10—N1 | 1.490 (4) |
C3—H3 | 0.97 (4) | C10—H12A | 0.96 |
C4—C5 | 1.383 (5) | C10—H12B | 0.96 |
C4—H4 | 0.91 (4) | C10—H12C | 0.96 |
C5—C6 | 1.387 (4) | N1—H10 | 0.99 (3) |
C5—H5 | 1.01 (4) | N1—H11 | 0.83 (4) |
C6—C7 | 1.510 (4) | N2—O3 | 1.237 (3) |
C7—O1 | 1.421 (3) | N2—O2 | 1.243 (3) |
C7—C8 | 1.527 (4) | N2—O4 | 1.256 (3) |
C7—H7 | 0.95 (4) | O1—H6 | 0.76 (4) |
C8—N1 | 1.510 (4) | ||
C2—C1—C6 | 120.4 (3) | C9—C8—C7 | 113.1 (3) |
C2—C1—H1 | 117 (2) | N1—C8—H8 | 107.4 (17) |
C6—C1—H1 | 123 (2) | C9—C8—H8 | 113 (2) |
C3—C2—C1 | 120.4 (4) | C7—C8—H8 | 107 (2) |
C3—C2—H2 | 118 (2) | C8—C9—H9A | 109 (2) |
C1—C2—H2 | 122 (2) | C8—C9—H9B | 112 (2) |
C2—C3—C4 | 119.7 (4) | H9A—C9—H9B | 115 (4) |
C2—C3—H3 | 120 (2) | C8—C9—H9C | 109 (2) |
C4—C3—H3 | 120 (2) | H9A—C9—H9C | 110 (3) |
C3—C4—C5 | 120.2 (3) | H9B—C9—H9C | 101 (3) |
C3—C4—H4 | 119 (3) | N1—C10—H12A | 109.5 |
C5—C4—H4 | 121 (3) | N1—C10—H12B | 109.5 |
C4—C5—C6 | 121.0 (3) | H12A—C10—H12B | 109.5 |
C4—C5—H5 | 123.0 (17) | N1—C10—H12C | 109.5 |
C6—C5—H5 | 116.1 (17) | H12A—C10—H12C | 109.5 |
C5—C6—C1 | 118.4 (3) | H12B—C10—H12C | 109.5 |
C5—C6—C7 | 122.1 (3) | C10—N1—C8 | 115.3 (3) |
C1—C6—C7 | 119.6 (3) | C10—N1—H10 | 110 (2) |
O1—C7—C6 | 113.5 (2) | C8—N1—H10 | 106.1 (18) |
O1—C7—C8 | 107.3 (2) | C10—N1—H11 | 106 (2) |
C6—C7—C8 | 111.7 (2) | C8—N1—H11 | 108 (2) |
O1—C7—H7 | 110.2 (18) | H10—N1—H11 | 112 (3) |
C6—C7—H7 | 104 (2) | O3—N2—O2 | 121.9 (3) |
C8—C7—H7 | 110 (2) | O3—N2—O4 | 119.4 (2) |
N1—C8—C9 | 107.4 (3) | O2—N2—O4 | 118.7 (2) |
N1—C8—C7 | 109.6 (2) | C7—O1—H6 | 107 (3) |
C6—C1—C2—C3 | 0.1 (5) | C1—C6—C7—O1 | 154.8 (3) |
C1—C2—C3—C4 | −0.7 (5) | C5—C6—C7—C8 | 97.6 (3) |
C2—C3—C4—C5 | 0.7 (5) | C1—C6—C7—C8 | −83.7 (3) |
C3—C4—C5—C6 | −0.1 (5) | O1—C7—C8—N1 | −56.5 (3) |
C4—C5—C6—C1 | −0.5 (5) | C6—C7—C8—N1 | 178.5 (2) |
C4—C5—C6—C7 | 178.2 (3) | O1—C7—C8—C9 | 63.3 (4) |
C2—C1—C6—C5 | 0.5 (4) | C6—C7—C8—C9 | −61.6 (4) |
C2—C1—C6—C7 | −178.2 (3) | C9—C8—N1—C10 | −176.0 (3) |
C5—C6—C7—O1 | −23.9 (4) | C7—C8—N1—C10 | −52.7 (3) |
D—H···A | D—H | H···A | D···A | D—H···A |
N1—H10···O4i | 0.99 (3) | 1.93 (3) | 2.885 (4) | 164 (3) |
N1—H10···N2i | 0.99 (3) | 2.59 (4) | 3.461 (4) | 147 (3) |
N1—H10···O3i | 0.99 (3) | 2.63 (4) | 3.233 (4) | 120 (3) |
N1—H11···O2ii | 0.83 (4) | 2.16 (4) | 2.978 (4) | 168 (3) |
N1—H11···O4ii | 0.83 (4) | 2.45 (3) | 3.051 (3) | 130 (3) |
N1—H11···N2ii | 0.83 (4) | 2.66 (4) | 3.433 (4) | 155 (3) |
Symmetry codes: (i) x, y−1, z; (ii) x−1, y−1, z. |
C10H16NO5P | F(000) = 560 |
Mr = 263.22 | Dx = 1.394 Mg m−3 |
Monoclinic, C2 | Mo Kα radiation, λ = 0.71073 Å |
Hall symbol: C 2y | Cell parameters from 6301 reflections |
a = 14.6992 (10) Å | θ = 1.0–27.5° |
b = 5.6433 (4) Å | µ = 0.23 mm−1 |
c = 15.2432 (14) Å | T = 150 K |
β = 97.333 (3)° | Needle, colourless |
V = 1254.11 (17) Å3 | 0.25 × 0.05 × 0.05 mm |
Z = 4 |
KappaCCD diffractometer | 2497 independent reflections |
Radiation source: Enraf Nonius FR590 | 2110 reflections with I > 2σ(I) |
Graphite monochromator | Rint = 0.033 |
CCD rotation images, thick slices scans | θmax = 27.4°, θmin = 2.8° |
Absorption correction: multi-scan R.H. Blessing, Acta Cryst. (1995), A51, 33-38 | h = −18→14 |
Tmin = 0.954, Tmax = 1.056 | k = −7→7 |
4138 measured reflections | l = −19→19 |
Refinement on F2 | Hydrogen site location: inferred from neighbouring sites |
Least-squares matrix: full | H atoms treated by a mixture of independent and constrained refinement |
R[F2 > 2σ(F2)] = 0.051 | w = 1/[σ2(Fo2) + (0.P)2 + 2.2505P] where P = (Fo2 + 2Fc2)/3 |
wR(F2) = 0.119 | (Δ/σ)max < 0.001 |
S = 1.07 | Δρmax = 0.31 e Å−3 |
2497 reflections | Δρmin = −0.37 e Å−3 |
173 parameters | Extinction correction: SHELXL, Fc*=kFc[1+0.001xFc2λ3/sin(2θ)]-1/4 |
1 restraint | Extinction coefficient: 0.018 (4) |
Primary atom site location: structure-invariant direct methods | Absolute structure: Flack H D (1983), Acta Cryst. A39, 876-881 |
Secondary atom site location: difference Fourier map | Absolute structure parameter: −0.13 (15) |
C10H16NO5P | V = 1254.11 (17) Å3 |
Mr = 263.22 | Z = 4 |
Monoclinic, C2 | Mo Kα radiation |
a = 14.6992 (10) Å | µ = 0.23 mm−1 |
b = 5.6433 (4) Å | T = 150 K |
c = 15.2432 (14) Å | 0.25 × 0.05 × 0.05 mm |
β = 97.333 (3)° |
KappaCCD diffractometer | 2497 independent reflections |
Absorption correction: multi-scan R.H. Blessing, Acta Cryst. (1995), A51, 33-38 | 2110 reflections with I > 2σ(I) |
Tmin = 0.954, Tmax = 1.056 | Rint = 0.033 |
4138 measured reflections |
R[F2 > 2σ(F2)] = 0.051 | H atoms treated by a mixture of independent and constrained refinement |
wR(F2) = 0.119 | Δρmax = 0.31 e Å−3 |
S = 1.07 | Δρmin = −0.37 e Å−3 |
2497 reflections | Absolute structure: Flack H D (1983), Acta Cryst. A39, 876-881 |
173 parameters | Absolute structure parameter: −0.13 (15) |
1 restraint |
Geometry. All e.s.d.'s (except the e.s.d. in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell e.s.d.'s are taken into account individually in the estimation of e.s.d.'s in distances, angles and torsion angles; correlations between e.s.d.'s in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell e.s.d.'s is used for estimating e.s.d.'s involving l.s. planes. |
Refinement. Refinement of F2 against ALL reflections. The weighted R-factor wR and goodness of fit S are based on F2, conventional R-factors R are based on F, with F set to zero for negative F2. The threshold expression of F2 > σ(F2) is used only for calculating R-factors(gt) etc. and is not relevant to the choice of reflections for refinement. R-factors based on F2 are statistically about twice as large as those based on F, and R- factors based on ALL data will be even larger. |
x | y | z | Uiso*/Ueq | ||
C1 | 0.3548 (2) | 0.8180 (7) | 0.6557 (2) | 0.0289 (8) | |
H1 | 0.368 (2) | 0.677 (7) | 0.695 (3) | 0.035* | |
C2 | 0.3993 (2) | 0.8304 (7) | 0.5802 (3) | 0.0348 (9) | |
H2 | 0.443 (3) | 0.695 (7) | 0.567 (3) | 0.042* | |
C3 | 0.3841 (2) | 1.0262 (7) | 0.5237 (3) | 0.0338 (9) | |
H3 | 0.415 (3) | 1.030 (8) | 0.469 (3) | 0.041* | |
C4 | 0.3254 (3) | 1.2054 (8) | 0.5432 (3) | 0.0347 (9) | |
H4 | 0.316 (3) | 1.336 (8) | 0.505 (3) | 0.042* | |
C5 | 0.2811 (3) | 1.1901 (7) | 0.6182 (3) | 0.0324 (9) | |
H5 | 0.245 (3) | 1.314 (8) | 0.634 (3) | 0.039* | |
C6 | 0.2953 (2) | 0.9963 (7) | 0.6750 (2) | 0.0257 (8) | |
C7 | 0.2455 (2) | 0.9729 (7) | 0.7557 (2) | 0.0276 (8) | |
H7 | 0.289 (2) | 0.896 (7) | 0.806 (3) | 0.033* | |
C8 | 0.1622 (2) | 0.8075 (6) | 0.7381 (2) | 0.0276 (8) | |
H8 | 0.178 (2) | 0.651 (7) | 0.710 (3) | 0.033* | |
C9 | 0.0821 (3) | 0.9185 (8) | 0.6795 (3) | 0.0356 (9) | |
H9A | 0.0344 | 0.803 | 0.6664 | 0.053* | |
H9B | 0.1023 | 0.972 | 0.6255 | 0.053* | |
H9C | 0.059 | 1.0506 | 0.7097 | 0.053* | |
C10 | 0.05114 (14) | 0.5858 (4) | 0.8238 (2) | 0.0334 (8) | |
H12A | −0.0016 | 0.6739 | 0.7984 | 0.05* | |
H12B | 0.0434 | 0.54 | 0.8831 | 0.05* | |
H12C | 0.0577 | 0.4467 | 0.7889 | 0.05* | |
O1 | 0.21329 (14) | 1.1954 (4) | 0.78344 (17) | 0.0332 (7) | |
H6 | 0.2443 | 1.2363 | 0.8295 | 0.05* | |
N1 | 0.13475 (18) | 0.7361 (6) | 0.82548 (19) | 0.0271 (7) | |
H10 | 0.182 | 0.6575 | 0.8557 | 0.033* | |
H11 | 0.126 | 0.8688 | 0.8561 | 0.033* | |
P1 | 0.36077 (5) | 0.61493 (17) | 0.95859 (6) | 0.0249 (3) | |
O2 | 0.27240 (15) | 0.4862 (4) | 0.92661 (17) | 0.0286 (6) | |
O3 | 0.40593 (15) | 0.5393 (5) | 1.04823 (16) | 0.0311 (6) | |
O4 | 0.42669 (13) | 0.5879 (3) | 0.88673 (13) | 0.0308 (6) | |
H13 | 0.4794 | 0.6171 | 0.9086 | 0.046* | |
O5 | 0.34129 (14) | 0.8902 (3) | 0.95827 (14) | 0.0314 (6) | |
H14 | 0.3027 | 0.919 | 0.9911 | 0.047* |
U11 | U22 | U33 | U12 | U13 | U23 | |
C1 | 0.0271 (18) | 0.036 (2) | 0.0232 (19) | 0.0031 (15) | 0.0018 (14) | −0.0003 (16) |
C2 | 0.0216 (17) | 0.044 (2) | 0.038 (2) | 0.0020 (16) | 0.0015 (16) | −0.0011 (18) |
C3 | 0.0256 (18) | 0.045 (2) | 0.031 (2) | −0.0013 (16) | 0.0019 (16) | 0.0026 (17) |
C4 | 0.032 (2) | 0.041 (2) | 0.030 (2) | −0.0018 (17) | 0.0010 (16) | 0.0056 (17) |
C5 | 0.035 (2) | 0.032 (2) | 0.029 (2) | 0.0043 (16) | 0.0001 (16) | 0.0014 (15) |
C6 | 0.0198 (16) | 0.0322 (19) | 0.0251 (19) | −0.0011 (14) | 0.0025 (14) | −0.0056 (15) |
C7 | 0.0264 (18) | 0.031 (2) | 0.0242 (19) | 0.0033 (14) | −0.0032 (15) | 0.0000 (15) |
C8 | 0.0314 (18) | 0.031 (2) | 0.0198 (17) | 0.0016 (15) | 0.0014 (14) | −0.0018 (15) |
C9 | 0.035 (2) | 0.045 (2) | 0.024 (2) | 0.0003 (18) | −0.0058 (16) | 0.0007 (17) |
C10 | 0.0246 (16) | 0.036 (2) | 0.039 (2) | −0.0006 (17) | 0.0028 (14) | −0.0023 (18) |
O1 | 0.0382 (15) | 0.0339 (16) | 0.0267 (14) | 0.0014 (11) | 0.0006 (11) | −0.0085 (10) |
N1 | 0.0238 (14) | 0.0313 (16) | 0.0258 (16) | 0.0041 (13) | 0.0021 (12) | 0.0004 (14) |
P1 | 0.0185 (4) | 0.0314 (5) | 0.0241 (5) | 0.0011 (4) | −0.0001 (3) | 0.0011 (4) |
O2 | 0.0214 (12) | 0.0302 (14) | 0.0333 (14) | −0.0010 (10) | −0.0001 (10) | −0.0031 (11) |
O3 | 0.0220 (11) | 0.0445 (17) | 0.0265 (13) | 0.0001 (10) | 0.0009 (10) | 0.0063 (11) |
O4 | 0.0209 (10) | 0.0472 (16) | 0.0245 (12) | 0.0027 (12) | 0.0037 (9) | 0.0008 (12) |
O5 | 0.0318 (14) | 0.0304 (14) | 0.0321 (15) | 0.0012 (11) | 0.0042 (12) | −0.0016 (11) |
C1—C6 | 1.389 (5) | C8—H8 | 1.02 (4) |
C1—C2 | 1.397 (5) | C9—H9A | 0.96 |
C1—H1 | 1.00 (4) | C9—H9B | 0.96 |
C2—C3 | 1.401 (6) | C9—H9C | 0.96 |
C2—H2 | 1.03 (4) | C10—N1 | 1.491 (4) |
C3—C4 | 1.386 (6) | C10—H12A | 0.96 |
C3—H3 | 1.00 (4) | C10—H12B | 0.96 |
C4—C5 | 1.389 (5) | C10—H12C | 0.96 |
C4—H4 | 0.94 (4) | O1—H6 | 0.82 |
C5—C6 | 1.393 (5) | N1—H10 | 0.9 |
C5—H5 | 0.93 (4) | N1—H11 | 0.9 |
C6—C7 | 1.515 (5) | P1—O3 | 1.503 (2) |
C7—O1 | 1.425 (4) | P1—O2 | 1.514 (2) |
C7—C8 | 1.536 (5) | P1—O4 | 1.5597 (18) |
C7—H7 | 1.03 (4) | P1—O5 | 1.580 (2) |
C8—N1 | 1.495 (4) | O4—H13 | 0.82 |
C8—C9 | 1.519 (5) | O5—H14 | 0.82 |
C6—C1—C2 | 120.8 (4) | C7—C8—H8 | 112 (2) |
C6—C1—H1 | 123 (2) | C8—C9—H9A | 109.5 |
C2—C1—H1 | 117 (2) | C8—C9—H9B | 109.5 |
C1—C2—C3 | 119.5 (4) | H9A—C9—H9B | 109.5 |
C1—C2—H2 | 119 (2) | C8—C9—H9C | 109.5 |
C3—C2—H2 | 121 (2) | H9A—C9—H9C | 109.5 |
C4—C3—C2 | 119.9 (4) | H9B—C9—H9C | 109.5 |
C4—C3—H3 | 122 (3) | N1—C10—H12A | 109.5 |
C2—C3—H3 | 118 (3) | N1—C10—H12B | 109.5 |
C3—C4—C5 | 120.1 (4) | H12A—C10—H12B | 109.5 |
C3—C4—H4 | 119 (3) | N1—C10—H12C | 109.5 |
C5—C4—H4 | 121 (3) | H12A—C10—H12C | 109.5 |
C4—C5—C6 | 120.8 (4) | H12B—C10—H12C | 109.5 |
C4—C5—H5 | 121 (3) | C7—O1—H6 | 109.5 |
C6—C5—H5 | 118 (3) | C10—N1—C8 | 117.0 (3) |
C1—C6—C5 | 119.0 (3) | C10—N1—H10 | 108.1 |
C1—C6—C7 | 119.4 (3) | C8—N1—H10 | 108.1 |
C5—C6—C7 | 121.6 (3) | C10—N1—H11 | 108.1 |
O1—C7—C6 | 112.2 (3) | C8—N1—H11 | 108.1 |
O1—C7—C8 | 107.4 (3) | H10—N1—H11 | 107.3 |
C6—C7—C8 | 111.6 (3) | O3—P1—O2 | 114.70 (15) |
O1—C7—H7 | 110 (2) | O3—P1—O4 | 111.65 (13) |
C6—C7—H7 | 109 (2) | O2—P1—O4 | 108.14 (13) |
C8—C7—H7 | 106 (2) | O3—P1—O5 | 109.93 (14) |
N1—C8—C9 | 111.0 (3) | O2—P1—O5 | 108.86 (13) |
N1—C8—C7 | 108.0 (3) | O4—P1—O5 | 102.87 (11) |
C9—C8—C7 | 113.1 (3) | P1—O4—H13 | 109.5 |
N1—C8—H8 | 104 (2) | P1—O5—H14 | 109.4 |
C9—C8—H8 | 108 (2) | ||
C6—C1—C2—C3 | 0.5 (5) | C5—C6—C7—O1 | −21.7 (4) |
C1—C2—C3—C4 | 0.0 (6) | C1—C6—C7—C8 | −79.5 (4) |
C2—C3—C4—C5 | −0.4 (6) | C5—C6—C7—C8 | 98.9 (4) |
C3—C4—C5—C6 | 0.3 (6) | O1—C7—C8—N1 | −73.6 (4) |
C2—C1—C6—C5 | −0.7 (5) | C6—C7—C8—N1 | 163.1 (3) |
C2—C1—C6—C7 | 177.8 (3) | O1—C7—C8—C9 | 49.7 (4) |
C4—C5—C6—C1 | 0.2 (5) | C6—C7—C8—C9 | −73.7 (4) |
C4—C5—C6—C7 | −178.2 (3) | C9—C8—N1—C10 | 51.9 (4) |
C1—C6—C7—O1 | 159.9 (3) | C7—C8—N1—C10 | 176.4 (3) |
D—H···A | D—H | H···A | D···A | D—H···A |
N1—H10···O2 | 0.9 | 1.87 | 2.768 (4) | 174 |
O4—H13···O3i | 0.82 | 1.78 | 2.547 (3) | 154 |
O5—H14···O2ii | 0.82 | 1.81 | 2.630 (3) | 174 |
N1—H11···O3ii | 0.9 | 1.86 | 2.699 (4) | 155 |
O1—H6···O2iii | 0.82 | 2.05 | 2.780 (3) | 148 |
Symmetry codes: (i) −x+1, y, −z+2; (ii) −x+1/2, y+1/2, −z+2; (iii) x, y+1, z. |
C10H18NO5S | F(000) = 560 |
Mr = 263.31 | Dx = 1.44 Mg m−3 |
Monoclinic, C2 | Mo Kα radiation, λ = 0.71073 Å |
Hall symbol: C 2y | Cell parameters from 22048 reflections |
a = 30.9967 (17) Å | θ = 1.0–29.1° |
b = 6.9861 (4) Å | µ = 0.28 mm−1 |
c = 5.6170 (3) Å | T = 150 K |
β = 93.354 (3)° | Needle, colourless |
V = 1214.26 (12) Å3 | 0.35 × 0.15 × 0.05 mm |
Z = 4 |
KappaCCD diffractometer | 3183 independent reflections |
Radiation source: Enraf Nonius FR590 | 1982 reflections with I > 2σ(I) |
Graphite monochromator | Rint = 0.058 |
CCD rotation images, thick slices scans | θmax = 28.9°, θmin = 2.6° |
Absorption correction: multi-scan R.H. Blessing, Acta Cryst. (1995), A51, 33-38 | h = −41→41 |
Tmin = 0.969, Tmax = 1.029 | k = −9→9 |
10680 measured reflections | l = −7→7 |
Refinement on F2 | Secondary atom site location: difference Fourier map |
Least-squares matrix: full | Hydrogen site location: inferred from neighbouring sites |
R[F2 > 2σ(F2)] = 0.074 | H atoms treated by a mixture of independent and constrained refinement |
wR(F2) = 0.125 | w = 1/[σ2(Fo2) + (0.0287P)2 + 1.1389P] where P = (Fo2 + 2Fc2)/3 |
S = 1.12 | (Δ/σ)max < 0.001 |
3183 reflections | Δρmax = 0.31 e Å−3 |
173 parameters | Δρmin = −0.37 e Å−3 |
1 restraint | Absolute structure: Flack H D (1983), Acta Cryst. A39, 876-881 |
Primary atom site location: structure-invariant direct methods | Absolute structure parameter: 0.01 (12) |
C10H18NO5S | V = 1214.26 (12) Å3 |
Mr = 263.31 | Z = 4 |
Monoclinic, C2 | Mo Kα radiation |
a = 30.9967 (17) Å | µ = 0.28 mm−1 |
b = 6.9861 (4) Å | T = 150 K |
c = 5.6170 (3) Å | 0.35 × 0.15 × 0.05 mm |
β = 93.354 (3)° |
KappaCCD diffractometer | 3183 independent reflections |
Absorption correction: multi-scan R.H. Blessing, Acta Cryst. (1995), A51, 33-38 | 1982 reflections with I > 2σ(I) |
Tmin = 0.969, Tmax = 1.029 | Rint = 0.058 |
10680 measured reflections |
R[F2 > 2σ(F2)] = 0.074 | H atoms treated by a mixture of independent and constrained refinement |
wR(F2) = 0.125 | Δρmax = 0.31 e Å−3 |
S = 1.12 | Δρmin = −0.37 e Å−3 |
3183 reflections | Absolute structure: Flack H D (1983), Acta Cryst. A39, 876-881 |
173 parameters | Absolute structure parameter: 0.01 (12) |
1 restraint |
Geometry. All e.s.d.'s (except the e.s.d. in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell e.s.d.'s are taken into account individually in the estimation of e.s.d.'s in distances, angles and torsion angles; correlations between e.s.d.'s in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell e.s.d.'s is used for estimating e.s.d.'s involving l.s. planes. |
Refinement. Refinement of F2 against ALL reflections. The weighted R-factor wR and goodness of fit S are based on F2, conventional R-factors R are based on F, with F set to zero for negative F2. The threshold expression of F2 > σ(F2) is used only for calculating R-factors(gt) etc. and is not relevant to the choice of reflections for refinement. R-factors based on F2 are statistically about twice as large as those based on F, and R- factors based on ALL data will be even larger. |
x | y | z | Uiso*/Ueq | ||
C1 | 0.69736 (14) | 0.5950 (6) | 0.8924 (7) | 0.0284 (10) | |
H1 | 0.6776 (13) | 0.639 (6) | 1.015 (7) | 0.034* | |
C2 | 0.74148 (14) | 0.6077 (6) | 0.9390 (8) | 0.0273 (10) | |
H2 | 0.7516 (14) | 0.667 (6) | 1.073 (7) | 0.033* | |
C3 | 0.76962 (14) | 0.5381 (5) | 0.7768 (7) | 0.0275 (10) | |
H3 | 0.7993 | 0.5448 | 0.8102 | 0.033* | |
C4 | 0.75313 (13) | 0.4582 (5) | 0.5641 (7) | 0.0249 (10) | |
H4 | 0.7720 (12) | 0.428 (6) | 0.442 (6) | 0.03* | |
C5 | 0.70880 (13) | 0.4471 (5) | 0.5176 (7) | 0.0243 (10) | |
H5 | 0.6974 (11) | 0.404 (6) | 0.368 (6) | 0.029* | |
C6 | 0.68042 (13) | 0.5124 (5) | 0.6821 (7) | 0.0236 (9) | |
C7 | 0.63223 (13) | 0.4804 (5) | 0.6424 (7) | 0.0242 (9) | |
H7 | 0.6169 | 0.5885 | 0.7096 | 0.029* | |
C8 | 0.61885 (12) | 0.2950 (5) | 0.7653 (7) | 0.0232 (9) | |
H8 | 0.6223 | 0.3127 | 0.9385 | 0.028* | |
C9 | 0.64371 (13) | 0.1181 (6) | 0.6978 (7) | 0.0300 (10) | |
H9A | 0.6318 | 0.0076 | 0.7714 | 0.045* | |
H9B | 0.6735 | 0.1319 | 0.7517 | 0.045* | |
H9C | 0.6416 | 0.1028 | 0.5277 | 0.045* | |
C10 | 0.54098 (12) | 0.4076 (7) | 0.7644 (6) | 0.0313 (9) | |
H10A | 0.547 | 0.4429 | 0.9281 | 0.047* | |
H10B | 0.512 | 0.3593 | 0.7441 | 0.047* | |
H10C | 0.5439 | 0.5178 | 0.6646 | 0.047* | |
N1 | 0.57185 (10) | 0.2572 (4) | 0.6970 (5) | 0.0246 (8) | |
H11 | 0.569 | 0.2411 | 0.5379 | 0.029* | |
H12 | 0.5643 | 0.1464 | 0.7648 | 0.029* | |
O1 | 0.61847 (10) | 0.4596 (4) | 0.3975 (5) | 0.0288 (7) | |
H6 | 0.6147 (14) | 0.555 (6) | 0.334 (8) | 0.035* | |
O2 | 0.55023 (8) | 0.8906 (4) | 0.8922 (4) | 0.0275 (6) | |
O3 | 0.52720 (9) | 0.7720 (4) | 1.2722 (5) | 0.0323 (7) | |
H13 | 0.5025 | 0.8084 | 1.2358 | 0.048* | |
O4 | 0.55403 (10) | 1.0985 (4) | 1.2305 (5) | 0.0380 (8) | |
O5 | 0.60190 (9) | 0.8243 (4) | 1.2223 (5) | 0.0365 (8) | |
S1 | 0.56039 (3) | 0.90469 (14) | 1.15108 (16) | 0.0264 (3) |
U11 | U22 | U33 | U12 | U13 | U23 | |
C1 | 0.038 (3) | 0.021 (2) | 0.027 (2) | −0.004 (2) | 0.0035 (19) | −0.0013 (18) |
C2 | 0.034 (3) | 0.023 (2) | 0.025 (2) | −0.002 (2) | −0.003 (2) | −0.0041 (19) |
C3 | 0.029 (2) | 0.024 (2) | 0.029 (2) | −0.0036 (18) | 0.0016 (19) | 0.0044 (18) |
C4 | 0.032 (2) | 0.021 (2) | 0.022 (2) | −0.0002 (17) | 0.0053 (18) | 0.0011 (16) |
C5 | 0.031 (2) | 0.022 (2) | 0.0194 (18) | −0.0052 (17) | 0.0006 (17) | −0.0005 (17) |
C6 | 0.029 (2) | 0.0193 (19) | 0.023 (2) | 0.0000 (18) | 0.0024 (18) | 0.0041 (16) |
C7 | 0.027 (2) | 0.023 (2) | 0.023 (2) | −0.0015 (18) | 0.0007 (17) | −0.0011 (17) |
C8 | 0.021 (2) | 0.027 (2) | 0.021 (2) | −0.0040 (18) | −0.0008 (17) | −0.0016 (18) |
C9 | 0.029 (2) | 0.024 (2) | 0.037 (2) | 0.0006 (19) | 0.0008 (18) | 0.0033 (19) |
C10 | 0.030 (2) | 0.029 (2) | 0.036 (2) | 0.004 (2) | 0.0046 (17) | 0.001 (2) |
N1 | 0.030 (2) | 0.0217 (17) | 0.0218 (18) | −0.0017 (15) | −0.0004 (15) | 0.0021 (15) |
O1 | 0.0368 (17) | 0.0261 (18) | 0.0228 (14) | −0.0035 (13) | −0.0040 (12) | 0.0053 (12) |
O2 | 0.0335 (15) | 0.0282 (14) | 0.0211 (13) | −0.0047 (15) | 0.0027 (11) | −0.0005 (15) |
O3 | 0.0273 (17) | 0.0339 (16) | 0.0360 (17) | 0.0002 (14) | 0.0033 (13) | 0.0136 (14) |
O4 | 0.058 (2) | 0.0223 (15) | 0.0327 (17) | 0.0022 (15) | −0.0088 (14) | −0.0038 (13) |
O5 | 0.0279 (18) | 0.0368 (18) | 0.0439 (19) | 0.0031 (13) | −0.0048 (14) | 0.0104 (14) |
S1 | 0.0300 (6) | 0.0228 (5) | 0.0262 (5) | −0.0021 (5) | −0.0016 (4) | 0.0036 (5) |
C1—C2 | 1.380 (6) | C8—H8 | 0.98 |
C1—C6 | 1.390 (5) | C9—H9A | 0.96 |
C1—H1 | 1.00 (4) | C9—H9B | 0.96 |
C2—C3 | 1.386 (6) | C9—H9C | 0.96 |
C2—H2 | 0.90 (4) | C10—N1 | 1.485 (5) |
C3—C4 | 1.389 (5) | C10—H10A | 0.96 |
C3—H3 | 0.93 | C10—H10B | 0.96 |
C4—C5 | 1.386 (5) | C10—H10C | 0.96 |
C4—H4 | 0.95 (4) | N1—H11 | 0.9 |
C5—C6 | 1.390 (5) | N1—H12 | 0.9 |
C5—H5 | 0.94 (4) | O1—H6 | 0.76 (4) |
C6—C7 | 1.514 (6) | O2—S1 | 1.473 (2) |
C7—O1 | 1.424 (4) | O3—S1 | 1.569 (3) |
C7—C8 | 1.536 (5) | O3—H13 | 0.82 |
C7—H7 | 0.98 | O4—S1 | 1.443 (3) |
C8—N1 | 1.508 (5) | O5—S1 | 1.439 (3) |
C8—C9 | 1.516 (5) | ||
C2—C1—C6 | 120.6 (4) | C9—C8—H8 | 108.8 |
C2—C1—H1 | 119 (2) | C7—C8—H8 | 108.8 |
C6—C1—H1 | 120 (2) | C8—C9—H9A | 109.5 |
C1—C2—C3 | 120.5 (4) | C8—C9—H9B | 109.5 |
C1—C2—H2 | 119 (3) | H9A—C9—H9B | 109.5 |
C3—C2—H2 | 121 (3) | C8—C9—H9C | 109.5 |
C2—C3—C4 | 119.5 (4) | H9A—C9—H9C | 109.5 |
C2—C3—H3 | 120.3 | H9B—C9—H9C | 109.5 |
C4—C3—H3 | 120.3 | N1—C10—H10A | 109.5 |
C5—C4—C3 | 119.7 (4) | N1—C10—H10B | 109.5 |
C5—C4—H4 | 120 (2) | H10A—C10—H10B | 109.5 |
C3—C4—H4 | 120 (2) | N1—C10—H10C | 109.5 |
C4—C5—C6 | 121.0 (3) | H10A—C10—H10C | 109.5 |
C4—C5—H5 | 120 (2) | H10B—C10—H10C | 109.5 |
C6—C5—H5 | 119 (2) | C10—N1—C8 | 116.0 (3) |
C1—C6—C5 | 118.6 (4) | C10—N1—H11 | 108.3 |
C1—C6—C7 | 120.5 (4) | C8—N1—H11 | 108.3 |
C5—C6—C7 | 120.7 (3) | C10—N1—H12 | 108.3 |
O1—C7—C6 | 113.3 (3) | C8—N1—H12 | 108.3 |
O1—C7—C8 | 106.0 (3) | H11—N1—H12 | 107.4 |
C6—C7—C8 | 110.4 (3) | C7—O1—H6 | 113 (3) |
O1—C7—H7 | 109 | S1—O3—H13 | 109.5 |
C6—C7—H7 | 109 | O5—S1—O4 | 114.60 (17) |
C8—C7—H7 | 109 | O5—S1—O2 | 112.61 (16) |
N1—C8—C9 | 106.9 (3) | O4—S1—O2 | 110.05 (17) |
N1—C8—C7 | 108.4 (3) | O5—S1—O3 | 104.30 (16) |
C9—C8—C7 | 114.9 (3) | O4—S1—O3 | 108.40 (19) |
N1—C8—H8 | 108.8 | O2—S1—O3 | 106.30 (16) |
C6—C1—C2—C3 | 0.0 (6) | C5—C6—C7—O1 | −25.6 (5) |
C1—C2—C3—C4 | 1.1 (6) | C1—C6—C7—C8 | −82.2 (4) |
C2—C3—C4—C5 | −0.7 (5) | C5—C6—C7—C8 | 93.0 (4) |
C3—C4—C5—C6 | −0.9 (5) | O1—C7—C8—N1 | −50.5 (4) |
C2—C1—C6—C5 | −1.5 (6) | C6—C7—C8—N1 | −173.4 (3) |
C2—C1—C6—C7 | 173.8 (4) | O1—C7—C8—C9 | 69.0 (4) |
C4—C5—C6—C1 | 2.0 (5) | C6—C7—C8—C9 | −54.0 (4) |
C4—C5—C6—C7 | −173.3 (3) | C9—C8—N1—C10 | 175.6 (3) |
C1—C6—C7—O1 | 159.2 (3) | C7—C8—N1—C10 | −60.1 (4) |
D—H···A | D—H | H···A | D···A | D—H···A |
N1—H11···O4i | 0.9 | 2.02 | 2.869 (4) | 156 |
O1—H6···O5ii | 0.76 (4) | 2.01 (4) | 2.768 (4) | 170 (5) |
N1—H12···O2iii | 0.9 | 1.98 | 2.881 (4) | 175 |
N1—H12···S1iii | 0.9 | 2.76 | 3.578 (3) | 152 |
O3—H13···O2iv | 0.82 | 1.84 | 2.653 (4) | 171 |
O3—H13···S1iv | 0.82 | 2.91 | 3.623 (3) | 146 |
Symmetry codes: (i) x, y−1, z−1; (ii) x, y, z−1; (iii) x, y−1, z; (iv) −x+1, y, −z+2. |
C14H23NO8 | F(000) = 712 |
Mr = 333.33 | Dx = 1.349 Mg m−3 |
Orthorhombic, P212121 | Mo Kα radiation, λ = 0.71073 Å |
Hall symbol: P 2ac 2ab | Cell parameters from 1411 reflections |
a = 6.6220 (2) Å | θ = 0–0° |
b = 7.4620 (3) Å | µ = 0.11 mm−1 |
c = 33.2160 (15) Å | T = 150 K |
V = 1641.31 (11) Å3 | Plate, colourless |
Z = 4 | 0.25 × 0.25 × 0.05 mm |
KappaCCD diffractometer | 1789 independent reflections |
Radiation source: Enraf Nonius FR590 | 1362 reflections with I > 2σ(I) |
Graphite monochromator | θmax = 25.7°, θmin = 4.1° |
CCD rotation images, thick slices scans | h = 0→7 |
Absorption correction: multi-scan R.H. Blessing, Acta Cryst. (1995), A51, 33-38 | k = 0→9 |
Tmin = 0.962, Tmax = 1.02 | l = 0→40 |
1789 measured reflections |
Refinement on F2 | Primary atom site location: structure-invariant direct methods |
Least-squares matrix: full | Secondary atom site location: difference Fourier map |
R[F2 > 2σ(F2)] = 0.040 | Hydrogen site location: inferred from neighbouring sites |
wR(F2) = 0.087 | H atoms treated by a mixture of independent and constrained refinement |
S = 1.03 | w = 1/[σ2(Fo2) + (0.0312P)2 + 0.535P] where P = (Fo2 + 2Fc2)/3 |
1789 reflections | (Δ/σ)max < 0.001 |
263 parameters | Δρmax = 0.22 e Å−3 |
0 restraints | Δρmin = −0.21 e Å−3 |
C14H23NO8 | V = 1641.31 (11) Å3 |
Mr = 333.33 | Z = 4 |
Orthorhombic, P212121 | Mo Kα radiation |
a = 6.6220 (2) Å | µ = 0.11 mm−1 |
b = 7.4620 (3) Å | T = 150 K |
c = 33.2160 (15) Å | 0.25 × 0.25 × 0.05 mm |
KappaCCD diffractometer | 1789 measured reflections |
Absorption correction: multi-scan R.H. Blessing, Acta Cryst. (1995), A51, 33-38 | 1789 independent reflections |
Tmin = 0.962, Tmax = 1.02 | 1362 reflections with I > 2σ(I) |
R[F2 > 2σ(F2)] = 0.040 | 0 restraints |
wR(F2) = 0.087 | H atoms treated by a mixture of independent and constrained refinement |
S = 1.03 | Δρmax = 0.22 e Å−3 |
1789 reflections | Δρmin = −0.21 e Å−3 |
263 parameters |
Geometry. All e.s.d.'s (except the e.s.d. in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell e.s.d.'s are taken into account individually in the estimation of e.s.d.'s in distances, angles and torsion angles; correlations between e.s.d.'s in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell e.s.d.'s is used for estimating e.s.d.'s involving l.s. planes. |
Refinement. Refinement of F2 against ALL reflections. The weighted R-factor wR and goodness of fit S are based on F2, conventional R-factors R are based on F, with F set to zero for negative F2. The threshold expression of F2 > σ(F2) is used only for calculating R-factors(gt) etc. and is not relevant to the choice of reflections for refinement. R-factors based on F2 are statistically about twice as large as those based on F, and R- factors based on ALL data will be even larger. |
x | y | z | Uiso*/Ueq | ||
C1 | 0.9589 (7) | 0.7626 (5) | 0.25786 (10) | 0.0282 (9) | |
H1 | 1.087 (6) | 0.707 (5) | 0.2610 (10) | 0.034* | |
C2 | 0.8679 (7) | 0.7652 (5) | 0.21982 (11) | 0.0327 (10) | |
H2 | 0.935 (6) | 0.712 (5) | 0.2000 (10) | 0.039* | |
C3 | 0.6841 (7) | 0.8478 (5) | 0.21453 (11) | 0.0329 (10) | |
H3 | 0.629 (6) | 0.849 (5) | 0.1879 (11) | 0.039* | |
C4 | 0.5886 (6) | 0.9293 (5) | 0.24668 (10) | 0.0336 (10) | |
H4 | 0.445 (6) | 0.995 (5) | 0.2429 (10) | 0.04* | |
C5 | 0.6794 (6) | 0.9271 (5) | 0.28445 (10) | 0.0268 (9) | |
H5 | 0.620 (6) | 0.975 (5) | 0.3046 (10) | 0.032* | |
C6 | 0.8636 (5) | 0.8442 (4) | 0.29030 (9) | 0.0215 (8) | |
C7 | 0.9608 (6) | 0.8340 (5) | 0.33154 (9) | 0.0208 (8) | |
H7 | 1.111 (6) | 0.860 (4) | 0.3284 (9) | 0.025* | |
C8 | 0.9254 (6) | 0.6497 (5) | 0.35107 (9) | 0.0216 (8) | |
H8 | 1.018 (6) | 0.560 (5) | 0.3369 (9) | 0.026* | |
C9 | 0.7066 (6) | 0.5896 (6) | 0.35069 (12) | 0.0300 (9) | |
H9A | 0.657 (6) | 0.577 (5) | 0.3221 (11) | 0.036* | |
H9B | 0.699 (6) | 0.483 (5) | 0.3652 (11) | 0.036* | |
H9C | 0.622 (6) | 0.676 (5) | 0.3643 (10) | 0.036* | |
C10 | 1.2209 (6) | 0.6605 (6) | 0.39925 (12) | 0.0279 (9) | |
H12A | 1.280 (6) | 0.564 (5) | 0.3849 (10) | 0.033* | |
H12B | 1.273 (6) | 0.772 (5) | 0.3893 (10) | 0.033* | |
H12C | 1.247 (5) | 0.650 (4) | 0.4302 (11) | 0.033* | |
C11 | 0.6022 (5) | 0.8044 (4) | 0.47101 (10) | 0.0196 (7) | |
C12 | 0.5932 (5) | 0.9981 (4) | 0.45559 (9) | 0.0174 (7) | |
H13 | 0.482 (6) | 1.063 (4) | 0.4693 (9) | 0.021* | |
C13 | 0.7946 (5) | 1.0856 (4) | 0.46695 (10) | 0.0182 (8) | |
H15 | 0.804 (5) | 1.080 (4) | 0.4962 (10) | 0.022* | |
C14 | 0.7937 (5) | 1.2806 (4) | 0.45358 (9) | 0.0193 (8) | |
O1 | 0.8810 (4) | 0.9684 (3) | 0.35767 (6) | 0.0232 (6) | |
H6 | 0.9729 | 1.0328 | 0.3657 | 0.035* | |
O2 | 0.6298 (3) | 0.6817 (3) | 0.44457 (6) | 0.0220 (5) | |
O3 | 0.5862 (4) | 0.7800 (3) | 0.50762 (6) | 0.0262 (6) | |
O4 | 0.9564 (3) | 0.9938 (3) | 0.44803 (6) | 0.0204 (5) | |
H16 | 1.005 | 0.921 | 0.4638 | 0.031* | |
O5 | 0.5563 (3) | 1.0124 (3) | 0.41350 (6) | 0.0213 (5) | |
H14 | 0.6577 | 0.9821 | 0.4011 | 0.032* | |
O6 | 0.9189 (4) | 1.3369 (3) | 0.42906 (7) | 0.0263 (6) | |
O7 | 0.6541 (4) | 1.3744 (3) | 0.46977 (7) | 0.0278 (6) | |
H17 | 0.6523 | 1.4743 | 0.4595 | 0.042* | |
O8 | 0.7976 (4) | 0.6740 (3) | 0.11874 (7) | 0.0268 (6) | |
H18 | 0.694 (6) | 0.623 (5) | 0.1098 (11) | 0.032* | |
H19 | 0.869 (6) | 0.709 (5) | 0.0974 (11) | 0.032* | |
N1 | 0.9988 (4) | 0.6565 (4) | 0.39388 (7) | 0.0190 (6) | |
H10 | 0.9464 | 0.7546 | 0.4057 | 0.023* | |
H11 | 0.95 | 0.5603 | 0.407 | 0.023* |
U11 | U22 | U33 | U12 | U13 | U23 | |
C1 | 0.035 (2) | 0.025 (2) | 0.0248 (19) | 0.0057 (18) | 0.0021 (19) | 0.0018 (16) |
C2 | 0.054 (3) | 0.026 (2) | 0.0177 (18) | 0.004 (2) | 0.0013 (19) | −0.0023 (16) |
C3 | 0.048 (3) | 0.027 (2) | 0.0237 (19) | −0.002 (2) | −0.0091 (19) | 0.0001 (18) |
C4 | 0.038 (3) | 0.035 (2) | 0.0283 (19) | 0.004 (2) | −0.006 (2) | 0.0051 (18) |
C5 | 0.029 (2) | 0.031 (2) | 0.0204 (18) | 0.0038 (18) | 0.0033 (17) | −0.0014 (17) |
C6 | 0.029 (2) | 0.0197 (17) | 0.0162 (16) | −0.0019 (17) | 0.0029 (15) | 0.0028 (14) |
C7 | 0.020 (2) | 0.0223 (18) | 0.0198 (17) | −0.0013 (17) | 0.0028 (15) | −0.0013 (15) |
C8 | 0.029 (2) | 0.0207 (18) | 0.0147 (17) | −0.0014 (17) | 0.0024 (15) | −0.0017 (15) |
C9 | 0.030 (2) | 0.036 (2) | 0.024 (2) | −0.0112 (19) | −0.0039 (18) | 0.0059 (19) |
C10 | 0.022 (2) | 0.031 (2) | 0.031 (2) | −0.0032 (19) | 0.0014 (17) | 0.0058 (19) |
C11 | 0.0133 (18) | 0.0186 (17) | 0.0268 (18) | −0.0022 (15) | −0.0003 (16) | 0.0026 (15) |
C12 | 0.021 (2) | 0.0138 (17) | 0.0172 (16) | 0.0037 (15) | 0.0032 (15) | −0.0008 (14) |
C13 | 0.0215 (19) | 0.0189 (18) | 0.0142 (16) | 0.0030 (15) | 0.0008 (15) | −0.0004 (15) |
C14 | 0.0214 (19) | 0.0209 (18) | 0.0156 (16) | −0.0016 (16) | −0.0001 (17) | −0.0028 (15) |
O1 | 0.0293 (14) | 0.0203 (12) | 0.0199 (11) | −0.0015 (11) | 0.0004 (11) | −0.0011 (10) |
O2 | 0.0254 (13) | 0.0157 (11) | 0.0250 (12) | 0.0015 (11) | 0.0002 (11) | −0.0024 (10) |
O3 | 0.0393 (16) | 0.0173 (12) | 0.0219 (13) | −0.0047 (11) | 0.0054 (12) | 0.0032 (10) |
O4 | 0.0213 (14) | 0.0181 (12) | 0.0220 (11) | 0.0040 (10) | −0.0004 (11) | 0.0026 (10) |
O5 | 0.0197 (13) | 0.0252 (13) | 0.0190 (11) | 0.0023 (11) | 0.0000 (10) | 0.0000 (10) |
O6 | 0.0292 (15) | 0.0182 (12) | 0.0316 (13) | 0.0014 (12) | 0.0089 (12) | 0.0048 (11) |
O7 | 0.0336 (16) | 0.0122 (12) | 0.0374 (14) | 0.0028 (11) | 0.0135 (13) | 0.0039 (11) |
O8 | 0.0237 (14) | 0.0292 (14) | 0.0275 (14) | −0.0024 (13) | 0.0024 (12) | −0.0009 (12) |
N1 | 0.0208 (16) | 0.0171 (14) | 0.0190 (14) | −0.0014 (13) | 0.0011 (12) | 0.0008 (12) |
C1—C6 | 1.389 (5) | C10—H12A | 0.95 (4) |
C1—C2 | 1.400 (5) | C10—H12B | 0.96 (4) |
C1—H1 | 0.95 (4) | C10—H12C | 1.05 (3) |
C2—C3 | 1.376 (6) | C11—O3 | 1.234 (4) |
C2—H2 | 0.89 (4) | C11—O2 | 1.281 (4) |
C3—C4 | 1.382 (5) | C11—C12 | 1.535 (4) |
C3—H3 | 0.96 (3) | C12—O5 | 1.423 (4) |
C4—C5 | 1.391 (5) | C12—C13 | 1.532 (5) |
C4—H4 | 1.08 (4) | C12—H13 | 0.99 (4) |
C5—C6 | 1.381 (5) | C13—O4 | 1.419 (4) |
C5—H5 | 0.86 (4) | C13—C14 | 1.521 (5) |
C6—C7 | 1.516 (4) | C13—H15 | 0.97 (3) |
C7—O1 | 1.428 (4) | C14—O6 | 1.236 (4) |
C7—C8 | 1.538 (5) | C14—O7 | 1.278 (4) |
C7—H7 | 1.02 (4) | O1—H6 | 0.82 |
C8—N1 | 1.504 (4) | O4—H16 | 0.82 |
C8—C9 | 1.517 (5) | O5—H14 | 0.82 |
C8—H8 | 1.02 (4) | O7—H17 | 0.82 |
C9—H9A | 1.01 (4) | O8—H18 | 0.84 (4) |
C9—H9B | 0.93 (4) | O8—H19 | 0.89 (4) |
C9—H9C | 0.96 (4) | N1—H10 | 0.9 |
C10—N1 | 1.481 (5) | N1—H11 | 0.9 |
C6—C1—C2 | 119.9 (4) | N1—C10—H12A | 109 (2) |
C6—C1—H1 | 121 (2) | N1—C10—H12B | 110 (2) |
C2—C1—H1 | 119 (2) | H12A—C10—H12B | 110 (3) |
C3—C2—C1 | 120.1 (4) | N1—C10—H12C | 106.3 (19) |
C3—C2—H2 | 123 (2) | H12A—C10—H12C | 112 (3) |
C1—C2—H2 | 117 (2) | H12B—C10—H12C | 110 (3) |
C2—C3—C4 | 120.2 (4) | O3—C11—O2 | 125.6 (3) |
C2—C3—H3 | 117 (2) | O3—C11—C12 | 117.7 (3) |
C4—C3—H3 | 122 (2) | O2—C11—C12 | 116.7 (3) |
C3—C4—C5 | 119.6 (4) | O5—C12—C13 | 111.1 (3) |
C3—C4—H4 | 120.9 (18) | O5—C12—C11 | 113.9 (3) |
C5—C4—H4 | 119.5 (19) | C13—C12—C11 | 106.6 (3) |
C6—C5—C4 | 120.9 (4) | O5—C12—H13 | 106.8 (18) |
C6—C5—H5 | 119 (2) | C13—C12—H13 | 108.9 (19) |
C4—C5—H5 | 120 (2) | C11—C12—H13 | 109.5 (18) |
C5—C6—C1 | 119.2 (3) | O4—C13—C14 | 109.6 (3) |
C5—C6—C7 | 121.6 (3) | O4—C13—C12 | 110.0 (2) |
C1—C6—C7 | 119.1 (3) | C14—C13—C12 | 109.4 (3) |
O1—C7—C6 | 110.9 (3) | O4—C13—H15 | 111.9 (19) |
O1—C7—C8 | 108.4 (3) | C14—C13—H15 | 109.2 (18) |
C6—C7—C8 | 111.2 (3) | C12—C13—H15 | 106.6 (19) |
O1—C7—H7 | 107.0 (19) | O6—C14—O7 | 125.2 (3) |
C6—C7—H7 | 108.3 (18) | O6—C14—C13 | 121.0 (3) |
C8—C7—H7 | 111.0 (19) | O7—C14—C13 | 113.8 (3) |
N1—C8—C9 | 109.1 (3) | C7—O1—H6 | 109.5 |
N1—C8—C7 | 108.6 (3) | C13—O4—H16 | 109.5 |
C9—C8—C7 | 114.0 (3) | C12—O5—H14 | 109.5 |
N1—C8—H8 | 105.2 (18) | C14—O7—H17 | 109.5 |
C9—C8—H8 | 112 (2) | H18—O8—H19 | 106 (3) |
C7—C8—H8 | 107.6 (18) | C10—N1—C8 | 115.8 (3) |
C8—C9—H9A | 110 (2) | C10—N1—H10 | 108.3 |
C8—C9—H9B | 108 (2) | C8—N1—H10 | 108.3 |
H9A—C9—H9B | 113 (3) | C10—N1—H11 | 108.3 |
C8—C9—H9C | 111 (2) | C8—N1—H11 | 108.3 |
H9A—C9—H9C | 108 (3) | H10—N1—H11 | 107.4 |
H9B—C9—H9C | 107 (3) | ||
C6—C1—C2—C3 | −0.2 (6) | C6—C7—C8—C9 | −50.2 (4) |
C1—C2—C3—C4 | 0.3 (6) | O3—C11—C12—O5 | −163.4 (3) |
C2—C3—C4—C5 | −0.1 (6) | O2—C11—C12—O5 | 17.9 (4) |
C3—C4—C5—C6 | −0.1 (6) | O3—C11—C12—C13 | 73.7 (4) |
C4—C5—C6—C1 | 0.2 (5) | O2—C11—C12—C13 | −104.9 (3) |
C4—C5—C6—C7 | −177.5 (3) | O5—C12—C13—O4 | −63.4 (3) |
C2—C1—C6—C5 | 0.0 (5) | C11—C12—C13—O4 | 61.2 (3) |
C2—C1—C6—C7 | 177.8 (3) | O5—C12—C13—C14 | 57.1 (3) |
C5—C6—C7—O1 | −20.8 (4) | C11—C12—C13—C14 | −178.4 (3) |
C1—C6—C7—O1 | 161.5 (3) | O4—C13—C14—O6 | 1.4 (4) |
C5—C6—C7—C8 | 99.8 (4) | C12—C13—C14—O6 | −119.3 (3) |
C1—C6—C7—C8 | −77.9 (4) | O4—C13—C14—O7 | −178.9 (3) |
O1—C7—C8—N1 | −49.9 (4) | C12—C13—C14—O7 | 60.4 (3) |
C6—C7—C8—N1 | −172.0 (3) | C9—C8—N1—C10 | 162.8 (3) |
O1—C7—C8—C9 | 71.9 (4) | C7—C8—N1—C10 | −72.4 (4) |
D—H···A | D—H | H···A | D···A | D—H···A |
O4—H16···O3i | 0.82 | 1.86 | 2.661 (3) | 167 |
O1—H6···O8ii | 0.82 | 1.92 | 2.738 (3) | 175 |
N1—H11···O6iii | 0.9 | 1.83 | 2.709 (3) | 164 |
O8—H18···O5iv | 0.84 (4) | 2.01 (4) | 2.845 (3) | 177 (4) |
O8—H19···O6v | 0.89 (4) | 1.91 (4) | 2.743 (3) | 154 (3) |
O8—H19···O4v | 0.89 (4) | 2.49 (3) | 3.063 (3) | 122 (3) |
O7—H17···O2vi | 0.82 | 1.63 | 2.446 (3) | 172 |
Symmetry codes: (i) x+1/2, −y+3/2, −z+1; (ii) −x+2, y+1/2, −z+1/2; (iii) x, y−1, z; (iv) −x+1, y−1/2, −z+1/2; (v) −x+2, y−1/2, −z+1/2; (vi) x, y+1, z. |
C24H42N2O11 | Z = 1 |
Mr = 534.6 | F(000) = 288 |
Triclinic, P1 | Dx = 1.279 Mg m−3 |
Hall symbol: P 1 | Mo Kα radiation, λ = 0.71073 Å |
a = 5.9373 (2) Å | Cell parameters from 25777 reflections |
b = 7.0594 (2) Å | θ = 1.0–25.0° |
c = 18.3791 (8) Å | µ = 0.10 mm−1 |
α = 80.254 (1)° | T = 150 K |
β = 88.527 (2)° | Plate, colourless |
γ = 66.247 (2)° | 0.25 × 0.25 × 0.05 mm |
V = 694.14 (4) Å3 |
KappaCCD diffractometer | 2412 independent reflections |
Radiation source: Enraf Nonius FR590 | 2078 reflections with I > 2σ(I) |
Graphite monochromator | θmax = 25.0°, θmin = 3.2° |
CCD rotation images, thick slices scans | h = −7→7 |
Absorption correction: multi-scan R.H. Blessing, Acta Cryst. (1995), A51, 33-38 | k = −8→8 |
Tmin = 0.879, Tmax = 1.158 | l = −21→19 |
6838 measured reflections |
Refinement on F2 | Secondary atom site location: difference Fourier map |
Least-squares matrix: full | Hydrogen site location: inferred from neighbouring sites |
R[F2 > 2σ(F2)] = 0.098 | H atoms treated by a mixture of independent and constrained refinement |
wR(F2) = 0.295 | w = 1/[σ2(Fo2) + (0.2P)2] where P = (Fo2 + 2Fc2)/3 |
S = 1.31 | (Δ/σ)max = 0.007 |
2412 reflections | Δρmax = 0.59 e Å−3 |
349 parameters | Δρmin = −0.43 e Å−3 |
3 restraints | Extinction correction: SHELXL, Fc*=kFc[1+0.001xFc2λ3/sin(2θ)]-1/4 |
Primary atom site location: structure-invariant direct methods | Extinction coefficient: 0.44 (9) |
C24H42N2O11 | γ = 66.247 (2)° |
Mr = 534.6 | V = 694.14 (4) Å3 |
Triclinic, P1 | Z = 1 |
a = 5.9373 (2) Å | Mo Kα radiation |
b = 7.0594 (2) Å | µ = 0.10 mm−1 |
c = 18.3791 (8) Å | T = 150 K |
α = 80.254 (1)° | 0.25 × 0.25 × 0.05 mm |
β = 88.527 (2)° |
KappaCCD diffractometer | 6838 measured reflections |
Absorption correction: multi-scan R.H. Blessing, Acta Cryst. (1995), A51, 33-38 | 2412 independent reflections |
Tmin = 0.879, Tmax = 1.158 | 2078 reflections with I > 2σ(I) |
R[F2 > 2σ(F2)] = 0.098 | 3 restraints |
wR(F2) = 0.295 | H atoms treated by a mixture of independent and constrained refinement |
S = 1.31 | Δρmax = 0.59 e Å−3 |
2412 reflections | Δρmin = −0.43 e Å−3 |
349 parameters |
Geometry. All e.s.d.'s (except the e.s.d. in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell e.s.d.'s are taken into account individually in the estimation of e.s.d.'s in distances, angles and torsion angles; correlations between e.s.d.'s in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell e.s.d.'s is used for estimating e.s.d.'s involving l.s. planes. |
Refinement. Refinement of F2 against ALL reflections. The weighted R-factor wR and goodness of fit S are based on F2, conventional R-factors R are based on F, with F set to zero for negative F2. The threshold expression of F2 > σ(F2) is used only for calculating R-factors(gt) etc. and is not relevant to the choice of reflections for refinement. R-factors based on F2 are statistically about twice as large as those based on F, and R- factors based on ALL data will be even larger. |
x | y | z | Uiso*/Ueq | ||
C01 | 0.871 (2) | 0.1721 (17) | 1.1790 (6) | 0.057 (3) | |
H01 | 0.7494 | 0.1787 | 1.1464 | 0.069* | |
C02 | 0.925 (2) | 0.033 (2) | 1.2468 (7) | 0.070 (3) | |
H02 | 0.836 | −0.0493 | 1.2595 | 0.084* | |
C03 | 1.109 (2) | 0.0169 (18) | 1.2943 (6) | 0.060 (3) | |
H03 | 1.1454 | −0.0772 | 1.3388 | 0.072* | |
C04 | 1.240 (2) | 0.1419 (15) | 1.2760 (5) | 0.051 (2) | |
H04 | 1.3636 | 0.1324 | 1.3081 | 0.062* | |
C05 | 1.1823 (17) | 0.2839 (14) | 1.2077 (5) | 0.047 (2) | |
H05 | 1.2707 | 0.3665 | 1.1949 | 0.056* | |
C06 | 0.9975 (15) | 0.3001 (12) | 1.1606 (4) | 0.0383 (18) | |
C07 | 0.9281 (15) | 0.4561 (13) | 1.0880 (4) | 0.0370 (17) | |
H07 | 0.9352 | 0.3798 | 1.0476 | 0.044* | |
C08 | 0.6637 (16) | 0.6258 (12) | 1.0890 (5) | 0.0386 (19) | |
C09 | 0.621 (2) | 0.7431 (18) | 1.1535 (6) | 0.067 (3) | |
H09A | 0.7453 | 0.7973 | 1.1555 | 0.1* | |
H09B | 0.6306 | 0.6489 | 1.1987 | 0.1* | |
H09C | 0.4615 | 0.8573 | 1.1471 | 0.1* | |
C10 | 0.3560 (19) | 0.8877 (17) | 0.9919 (6) | 0.053 (2) | |
H12A | 0.3068 | 0.794 | 0.9708 | 0.079* | |
H12B | 0.3367 | 1.0078 | 0.955 | 0.079* | |
H12C | 0.2552 | 0.9329 | 1.0325 | 0.079* | |
C11 | 1.0959 (17) | 0.5183 (13) | 0.8929 (5) | 0.0417 (19) | |
C12 | 1.1825 (16) | 0.4567 (13) | 0.8185 (5) | 0.0421 (19) | |
H13 | 1.2718 | 0.3035 | 0.8268 | 0.051* | |
C13 | 1.3653 (14) | 0.5513 (11) | 0.7876 (5) | 0.0346 (17) | |
H14 | 1.5011 | 0.507 | 0.8245 | 0.042* | |
C14 | 1.4718 (13) | 0.4785 (11) | 0.7163 (5) | 0.0336 (17) | |
C21 | 0.7053 (17) | 0.7605 (13) | 0.4616 (5) | 0.044 (2) | |
H21 | 0.5487 | 0.8442 | 0.4746 | 0.053* | |
C22 | 0.731 (2) | 0.6825 (16) | 0.3962 (5) | 0.053 (2) | |
H22 | 0.5937 | 0.7143 | 0.3658 | 0.063* | |
C23 | 0.963 (2) | 0.5571 (14) | 0.3762 (5) | 0.052 (2) | |
H23 | 0.9808 | 0.503 | 0.3326 | 0.062* | |
C24 | 1.167 (2) | 0.5125 (15) | 0.4204 (6) | 0.054 (2) | |
H24 | 1.3232 | 0.4298 | 0.4065 | 0.064* | |
C25 | 1.1406 (16) | 0.5920 (14) | 0.4868 (5) | 0.0420 (19) | |
H25 | 1.2787 | 0.5617 | 0.5168 | 0.05* | |
C26 | 0.9045 (15) | 0.7175 (12) | 0.5077 (5) | 0.0366 (18) | |
C27 | 0.8824 (14) | 0.8062 (12) | 0.5784 (5) | 0.0372 (18) | |
H27 | 0.986 | 0.6946 | 0.6177 | 0.045* | |
C28 | 0.9715 (15) | 0.9843 (11) | 0.5667 (4) | 0.0324 (16) | |
C29 | 0.809 (2) | 1.1765 (14) | 0.5132 (5) | 0.052 (2) | |
H29A | 0.644 | 1.2267 | 0.5295 | 0.077* | |
H29B | 0.811 | 1.1407 | 0.465 | 0.077* | |
H29C | 0.8704 | 1.2842 | 0.5109 | 0.077* | |
C30 | 1.0894 (16) | 1.1982 (12) | 0.6451 (5) | 0.0413 (19) | |
H32A | 1.2458 | 1.1539 | 0.6225 | 0.062* | |
H32B | 1.112 | 1.2073 | 0.6957 | 0.062* | |
H32C | 0.9808 | 1.3335 | 0.619 | 0.062* | |
O01 | 1.0899 (12) | 0.5557 (11) | 1.0747 (4) | 0.0481 (16) | |
H06 | 1.2322 | 0.4681 | 1.0828 | 0.072* | |
O02 | 0.8714 (11) | 0.6330 (10) | 0.8980 (3) | 0.0460 (15) | |
O03 | 1.2568 (12) | 0.4514 (11) | 0.9439 (4) | 0.0512 (17) | |
O04 | 0.9895 (11) | 0.5091 (11) | 0.7662 (4) | 0.0482 (16) | |
H15 | 0.863 | 0.5201 | 0.7875 | 0.072* | |
O05 | 1.2373 (10) | 0.7757 (8) | 0.7781 (4) | 0.0422 (14) | |
H16 | 1.1227 | 0.8062 | 0.8059 | 0.063* | |
O06 | 1.4444 (12) | 0.6083 (10) | 0.6597 (3) | 0.0474 (15) | |
O07 | 1.5890 (12) | 0.2805 (9) | 0.7206 (4) | 0.0489 (16) | |
O08 | 1.5864 (13) | 0.9141 (11) | 0.7831 (4) | 0.0523 (16) | |
H17A | 1.7169 | 0.8062 | 0.7967 | 0.063* | |
H17B | 1.4963 | 0.8789 | 0.7573 | 0.063* | |
O09 | 0.7162 (12) | 0.1428 (11) | 0.9908 (4) | 0.0505 (16) | |
H18A | 0.8368 | 0.1702 | 0.9732 | 0.061* | |
H18B | 0.5857 | 0.2524 | 0.9787 | 0.061* | |
O10 | 0.9462 (12) | 0.1046 (10) | 0.8566 (4) | 0.0504 (16) | |
H19A | 1.0832 | 0.0315 | 0.8394 | 0.06* | |
H19B | 0.8393 | 0.1534 | 0.8199 | 0.06* | |
O21 | 0.6383 (11) | 0.8885 (10) | 0.6011 (4) | 0.0442 (14) | |
H26 | 0.5443 | 0.9534 | 0.565 | 0.066* | |
N01 | 0.6160 (13) | 0.7781 (11) | 1.0185 (4) | 0.0397 (16) | |
H11 | 0.6732 | 0.8749 | 1.0244 | 0.048* | |
H10A | 0.7028 | 0.7089 | 0.9832 | 0.048* | |
N21 | 0.9799 (12) | 1.0424 (10) | 0.6419 (4) | 0.0355 (15) | |
H30 | 0.8253 | 1.0946 | 0.6574 | 0.043* | |
H31 | 1.067 | 0.9243 | 0.6738 | 0.043* | |
H08 | 0.551 (19) | 0.549 (19) | 1.086 (6) | 0.043* | |
H28 | 1.12 (2) | 0.966 (18) | 0.548 (6) | 0.043* |
U11 | U22 | U33 | U12 | U13 | U23 | |
C01 | 0.066 (6) | 0.051 (6) | 0.050 (5) | −0.025 (5) | −0.007 (4) | 0.011 (4) |
C02 | 0.076 (7) | 0.054 (7) | 0.071 (7) | −0.028 (6) | −0.009 (6) | 0.021 (6) |
C03 | 0.072 (7) | 0.049 (6) | 0.046 (5) | −0.016 (5) | −0.002 (5) | 0.002 (4) |
C04 | 0.069 (6) | 0.034 (5) | 0.038 (4) | −0.005 (4) | −0.008 (4) | −0.009 (4) |
C05 | 0.054 (5) | 0.031 (4) | 0.049 (5) | −0.009 (4) | 0.002 (4) | −0.011 (4) |
C06 | 0.049 (4) | 0.022 (4) | 0.037 (4) | −0.006 (3) | 0.007 (3) | −0.007 (3) |
C07 | 0.047 (4) | 0.030 (4) | 0.031 (4) | −0.010 (3) | 0.004 (3) | −0.009 (3) |
C08 | 0.053 (5) | 0.016 (4) | 0.039 (4) | −0.006 (3) | 0.005 (3) | −0.006 (3) |
C09 | 0.086 (8) | 0.041 (6) | 0.049 (6) | 0.004 (5) | 0.009 (5) | −0.021 (5) |
C10 | 0.051 (5) | 0.043 (5) | 0.056 (6) | −0.016 (4) | −0.007 (4) | 0.006 (4) |
C11 | 0.052 (5) | 0.028 (4) | 0.042 (5) | −0.015 (4) | 0.008 (4) | −0.003 (3) |
C12 | 0.044 (4) | 0.026 (4) | 0.057 (5) | −0.014 (3) | 0.013 (4) | −0.012 (4) |
C13 | 0.038 (4) | 0.013 (3) | 0.048 (5) | −0.007 (3) | −0.004 (3) | −0.001 (3) |
C14 | 0.036 (4) | 0.024 (4) | 0.044 (4) | −0.014 (3) | 0.001 (3) | −0.007 (3) |
C21 | 0.048 (5) | 0.028 (4) | 0.045 (5) | −0.007 (4) | −0.007 (4) | 0.005 (4) |
C22 | 0.078 (7) | 0.050 (6) | 0.027 (4) | −0.024 (5) | −0.012 (4) | 0.001 (4) |
C23 | 0.077 (6) | 0.029 (4) | 0.045 (5) | −0.016 (4) | 0.005 (4) | −0.012 (4) |
C24 | 0.065 (6) | 0.034 (5) | 0.053 (6) | −0.009 (4) | 0.016 (5) | −0.015 (4) |
C25 | 0.043 (4) | 0.028 (4) | 0.044 (4) | −0.005 (3) | 0.001 (3) | −0.003 (3) |
C26 | 0.044 (4) | 0.022 (4) | 0.046 (5) | −0.015 (3) | 0.006 (3) | −0.009 (3) |
C27 | 0.039 (4) | 0.023 (4) | 0.043 (4) | −0.006 (3) | 0.004 (3) | −0.005 (3) |
C28 | 0.040 (4) | 0.022 (4) | 0.034 (4) | −0.011 (3) | 0.006 (3) | −0.005 (3) |
C29 | 0.078 (6) | 0.030 (4) | 0.041 (5) | −0.019 (4) | −0.006 (4) | 0.003 (4) |
C30 | 0.055 (5) | 0.020 (4) | 0.044 (4) | −0.012 (3) | 0.004 (4) | −0.003 (3) |
O01 | 0.045 (3) | 0.060 (4) | 0.041 (3) | −0.025 (3) | 0.002 (2) | −0.003 (3) |
O02 | 0.048 (3) | 0.037 (3) | 0.042 (3) | −0.005 (3) | 0.009 (3) | −0.007 (3) |
O03 | 0.055 (4) | 0.045 (4) | 0.036 (3) | −0.005 (3) | 0.010 (3) | −0.005 (3) |
O04 | 0.047 (3) | 0.058 (4) | 0.049 (4) | −0.026 (3) | 0.014 (3) | −0.026 (3) |
O05 | 0.043 (3) | 0.017 (3) | 0.061 (4) | −0.006 (2) | 0.004 (3) | −0.008 (2) |
O06 | 0.054 (3) | 0.046 (4) | 0.041 (3) | −0.022 (3) | 0.002 (3) | 0.000 (3) |
O07 | 0.059 (4) | 0.024 (3) | 0.060 (4) | −0.012 (3) | 0.022 (3) | −0.013 (3) |
O08 | 0.060 (4) | 0.040 (3) | 0.058 (4) | −0.023 (3) | −0.011 (3) | −0.003 (3) |
O09 | 0.050 (3) | 0.038 (3) | 0.059 (4) | −0.012 (3) | 0.001 (3) | −0.009 (3) |
O10 | 0.056 (3) | 0.034 (3) | 0.051 (4) | −0.007 (3) | −0.001 (3) | −0.006 (3) |
O21 | 0.041 (3) | 0.034 (3) | 0.055 (4) | −0.013 (2) | 0.007 (3) | −0.007 (3) |
N01 | 0.047 (4) | 0.026 (3) | 0.041 (4) | −0.008 (3) | 0.005 (3) | −0.009 (3) |
N21 | 0.042 (3) | 0.029 (3) | 0.032 (3) | −0.011 (3) | 0.004 (3) | −0.005 (3) |
C01—C06 | 1.389 (14) | C21—H21 | 0.93 |
C01—C02 | 1.405 (16) | C22—C23 | 1.384 (16) |
C01—H01 | 0.93 | C22—H22 | 0.93 |
C02—C03 | 1.371 (18) | C23—C24 | 1.373 (16) |
C02—H02 | 0.93 | C23—H23 | 0.93 |
C03—C04 | 1.391 (17) | C24—C25 | 1.407 (14) |
C03—H03 | 0.93 | C24—H24 | 0.93 |
C04—C05 | 1.420 (14) | C25—C26 | 1.410 (12) |
C04—H04 | 0.93 | C25—H25 | 0.93 |
C05—C06 | 1.372 (13) | C26—C27 | 1.514 (11) |
C05—H05 | 0.93 | C27—O21 | 1.409 (10) |
C06—C07 | 1.525 (11) | C27—C28 | 1.531 (11) |
C07—O01 | 1.397 (11) | C27—H27 | 0.98 |
C07—C08 | 1.546 (11) | C28—C29 | 1.510 (12) |
C07—H07 | 0.98 | C28—N21 | 1.514 (10) |
C08—N01 | 1.489 (11) | C28—H28 | 0.93 (12) |
C08—C09 | 1.519 (12) | C29—H29A | 0.96 |
C08—H08 | 1.03 (12) | C29—H29B | 0.96 |
C09—H09A | 0.96 | C29—H29C | 0.96 |
C09—H09B | 0.96 | C30—N21 | 1.496 (11) |
C09—H09C | 0.96 | C30—H32A | 0.96 |
C10—N01 | 1.472 (12) | C30—H32B | 0.96 |
C10—H12A | 0.96 | C30—H32C | 0.96 |
C10—H12B | 0.96 | O01—H06 | 0.82 |
C10—H12C | 0.96 | O04—H15 | 0.82 |
C11—O03 | 1.244 (12) | O05—H16 | 0.82 |
C11—O02 | 1.261 (11) | O08—H17A | 0.8445 |
C11—C12 | 1.519 (12) | O08—H17B | 0.8564 |
C12—O04 | 1.404 (12) | O09—H18A | 0.8562 |
C12—C13 | 1.539 (11) | O09—H18B | 0.8464 |
C12—H13 | 0.98 | O10—H19A | 0.8551 |
C13—O05 | 1.435 (9) | O10—H19B | 0.861 |
C13—C14 | 1.518 (11) | O21—H26 | 0.82 |
C13—H14 | 0.98 | N01—H11 | 0.9 |
C14—O06 | 1.231 (11) | N01—H10A | 0.9 |
C14—O07 | 1.275 (10) | N21—H30 | 0.9 |
C21—C26 | 1.373 (13) | N21—H31 | 0.9 |
C21—C22 | 1.384 (14) | ||
C06—C01—C02 | 120.1 (10) | C26—C21—H21 | 119.1 |
C06—C01—H01 | 119.9 | C22—C21—H21 | 119.1 |
C02—C01—H01 | 119.9 | C23—C22—C21 | 119.8 (9) |
C03—C02—C01 | 120.5 (11) | C23—C22—H22 | 120.1 |
C03—C02—H02 | 119.8 | C21—C22—H22 | 120.1 |
C01—C02—H02 | 119.8 | C24—C23—C22 | 120.2 (9) |
C02—C03—C04 | 119.9 (10) | C24—C23—H23 | 119.9 |
C02—C03—H03 | 120.1 | C22—C23—H23 | 119.9 |
C04—C03—H03 | 120.1 | C23—C24—C25 | 119.9 (8) |
C03—C04—C05 | 119.4 (9) | C23—C24—H24 | 120.1 |
C03—C04—H04 | 120.3 | C25—C24—H24 | 120.1 |
C05—C04—H04 | 120.3 | C24—C25—C26 | 120.0 (8) |
C06—C05—C04 | 120.5 (9) | C24—C25—H25 | 120 |
C06—C05—H05 | 119.8 | C26—C25—H25 | 120 |
C04—C05—H05 | 119.8 | C21—C26—C25 | 118.3 (8) |
C05—C06—C01 | 119.6 (8) | C21—C26—C27 | 122.9 (7) |
C05—C06—C07 | 121.3 (8) | C25—C26—C27 | 118.7 (8) |
C01—C06—C07 | 119.1 (8) | O21—C27—C26 | 112.7 (7) |
O01—C07—C06 | 111.4 (7) | O21—C27—C28 | 107.6 (6) |
O01—C07—C08 | 108.6 (7) | C26—C27—C28 | 109.6 (6) |
C06—C07—C08 | 110.7 (6) | O21—C27—H27 | 108.9 |
O01—C07—H07 | 108.7 | C26—C27—H27 | 108.9 |
C06—C07—H07 | 108.7 | C28—C27—H27 | 108.9 |
C08—C07—H07 | 108.7 | C29—C28—N21 | 109.7 (6) |
N01—C08—C09 | 109.2 (7) | C29—C28—C27 | 114.1 (7) |
N01—C08—C07 | 107.3 (6) | N21—C28—C27 | 106.5 (6) |
C09—C08—C07 | 114.1 (8) | C29—C28—H28 | 99 (7) |
N01—C08—H08 | 106 (6) | N21—C28—H28 | 105 (7) |
C09—C08—H08 | 115 (6) | C27—C28—H28 | 121 (7) |
C07—C08—H08 | 105 (6) | C28—C29—H29A | 109.5 |
C08—C09—H09A | 109.5 | C28—C29—H29B | 109.5 |
C08—C09—H09B | 109.5 | H29A—C29—H29B | 109.5 |
H09A—C09—H09B | 109.5 | C28—C29—H29C | 109.5 |
C08—C09—H09C | 109.5 | H29A—C29—H29C | 109.5 |
H09A—C09—H09C | 109.5 | H29B—C29—H29C | 109.5 |
H09B—C09—H09C | 109.5 | N21—C30—H32A | 109.5 |
N01—C10—H12A | 109.5 | N21—C30—H32B | 109.5 |
N01—C10—H12B | 109.5 | H32A—C30—H32B | 109.5 |
H12A—C10—H12B | 109.5 | N21—C30—H32C | 109.5 |
N01—C10—H12C | 109.5 | H32A—C30—H32C | 109.5 |
H12A—C10—H12C | 109.5 | H32B—C30—H32C | 109.5 |
H12B—C10—H12C | 109.5 | C07—O01—H06 | 109.5 |
O03—C11—O02 | 125.6 (8) | C12—O04—H15 | 109.5 |
O03—C11—C12 | 116.0 (8) | C13—O05—H16 | 109.5 |
O02—C11—C12 | 118.4 (8) | H17A—O08—H17B | 107.6 |
O04—C12—C11 | 113.6 (7) | H18A—O09—H18B | 107.5 |
O04—C12—C13 | 110.3 (7) | H19A—O10—H19B | 106.2 |
C11—C12—C13 | 110.9 (7) | C27—O21—H26 | 109.5 |
O04—C12—H13 | 107.2 | C10—N01—C08 | 115.4 (7) |
C11—C12—H13 | 107.2 | C10—N01—H11 | 108.4 |
C13—C12—H13 | 107.2 | C08—N01—H11 | 108.4 |
O05—C13—C14 | 112.1 (6) | C10—N01—H10A | 108.4 |
O05—C13—C12 | 107.2 (6) | C08—N01—H10A | 108.4 |
C14—C13—C12 | 112.3 (6) | H11—N01—H10A | 107.5 |
O05—C13—H14 | 108.4 | C30—N21—C28 | 115.6 (6) |
C14—C13—H14 | 108.4 | C30—N21—H30 | 108.4 |
C12—C13—H14 | 108.4 | C28—N21—H30 | 108.4 |
O06—C14—O07 | 124.5 (8) | C30—N21—H31 | 108.4 |
O06—C14—C13 | 119.9 (6) | C28—N21—H31 | 108.4 |
O07—C14—C13 | 115.6 (7) | H30—N21—H31 | 107.4 |
C26—C21—C22 | 121.8 (9) | ||
C06—C01—C02—C03 | −2 (2) | O05—C13—C14—O06 | 0.6 (10) |
C01—C02—C03—C04 | 1.0 (19) | C12—C13—C14—O06 | 121.5 (8) |
C02—C03—C04—C05 | −0.4 (16) | O05—C13—C14—O07 | 179.8 (6) |
C03—C04—C05—C06 | 0.8 (13) | C12—C13—C14—O07 | −59.4 (9) |
C04—C05—C06—C01 | −1.8 (12) | C26—C21—C22—C23 | 0.2 (14) |
C04—C05—C06—C07 | 178.3 (8) | C21—C22—C23—C24 | −1.0 (15) |
C02—C01—C06—C05 | 2.4 (15) | C22—C23—C24—C25 | 0.9 (15) |
C02—C01—C06—C07 | −177.6 (10) | C23—C24—C25—C26 | −0.1 (14) |
C05—C06—C07—O01 | 6.1 (10) | C22—C21—C26—C25 | 0.6 (12) |
C01—C06—C07—O01 | −173.8 (8) | C22—C21—C26—C27 | 178.0 (9) |
C05—C06—C07—C08 | −114.8 (8) | C24—C25—C26—C21 | −0.7 (13) |
C01—C06—C07—C08 | 65.2 (10) | C24—C25—C26—C27 | −178.2 (8) |
O01—C07—C08—N01 | 54.1 (8) | C21—C26—C27—O21 | 15.6 (11) |
C06—C07—C08—N01 | 176.7 (7) | C25—C26—C27—O21 | −167.0 (7) |
O01—C07—C08—C09 | −67.1 (10) | C21—C26—C27—C28 | −104.2 (8) |
C06—C07—C08—C09 | 55.5 (10) | C25—C26—C27—C28 | 73.1 (9) |
O03—C11—C12—O04 | 171.0 (8) | O21—C27—C28—C29 | −55.7 (9) |
O02—C11—C12—O04 | −9.8 (11) | C26—C27—C28—C29 | 67.1 (9) |
O03—C11—C12—C13 | −64.0 (10) | O21—C27—C28—N21 | 65.4 (8) |
O02—C11—C12—C13 | 115.2 (8) | C26—C27—C28—N21 | −171.8 (6) |
O04—C12—C13—O05 | 65.7 (8) | C09—C08—N01—C10 | −83.5 (10) |
C11—C12—C13—O05 | −61.1 (9) | C07—C08—N01—C10 | 152.4 (8) |
O04—C12—C13—C14 | −57.9 (8) | C29—C28—N21—C30 | −62.7 (9) |
C11—C12—C13—C14 | 175.3 (7) | C27—C28—N21—C30 | 173.4 (6) |
D—H···A | D—H | H···A | D···A | D—H···A |
O05—H16···O10i | 0.82 | 2.29 | 2.869 (9) | 128 |
N01—H11···O09i | 0.9 | 2 | 2.832 (10) | 153 |
O08—H17A···O02ii | 0.84 | 2.05 | 2.705 (9) | 134 |
O08—H17A···O04ii | 0.84 | 2.22 | 2.958 (10) | 145 |
O09—H18B···O03iii | 0.85 | 1.94 | 2.762 (9) | 165 |
O10—H19B···O07iii | 0.86 | 2.2 | 3.063 (10) | 176 |
O10—H19A···O05iv | 0.86 | 2.16 | 2.869 (9) | 140 |
N21—H30···O07v | 0.9 | 2 | 2.795 (9) | 147 |
Symmetry codes: (i) x, y+1, z; (ii) x+1, y, z; (iii) x−1, y, z; (iv) x, y−1, z; (v) x−1, y+1, z. |
C17H23NO7S | F(000) = 720 |
Mr = 337.42 | Dx = 1.294 Mg m−3 |
Orthorhombic, P212121 | Mo Kα radiation, λ = 0.71073 Å |
Hall symbol: P 2ac 2ab | Cell parameters from 19550 reflections |
a = 5.7491 (2) Å | θ = 1.0–27.5° |
b = 7.1665 (2) Å | µ = 0.21 mm−1 |
c = 42.0343 (9) Å | T = 150 K |
V = 1731.85 (9) Å3 | Plate, white |
Z = 4 | 0.35 × 0.35 × 0.05 mm |
KappaCCD diffractometer | 3446 independent reflections |
Radiation source: Enraf Nonius FR590 | 2839 reflections with I > 2σ(I) |
Graphite monochromator | Rint = 0.018 |
CCD rotation images, thick slices scans | θmax = 27.5°, θmin = 2.9° |
Absorption correction: multi-scan R.H. Blessing, Acta Cryst. (1995), A51, 33-38 | h = −7→6 |
Tmin = 0.976, Tmax = 1.022 | k = −9→9 |
6102 measured reflections | l = −39→54 |
Refinement on F2 | Secondary atom site location: difference Fourier map |
Least-squares matrix: full | Hydrogen site location: inferred from neighbouring sites |
R[F2 > 2σ(F2)] = 0.043 | H atoms treated by a mixture of independent and constrained refinement |
wR(F2) = 0.099 | w = 1/[σ2(Fo2) + (0.0389P)2 + 0.3943P] where P = (Fo2 + 2Fc2)/3 |
S = 1.04 | (Δ/σ)max < 0.001 |
3446 reflections | Δρmax = 0.24 e Å−3 |
263 parameters | Δρmin = −0.29 e Å−3 |
0 restraints | Absolute structure: Flack H D (1983), Acta Cryst. A39, 876-881 |
Primary atom site location: structure-invariant direct methods | Absolute structure parameter: 0.00 (9) |
C17H23NO7S | V = 1731.85 (9) Å3 |
Mr = 337.42 | Z = 4 |
Orthorhombic, P212121 | Mo Kα radiation |
a = 5.7491 (2) Å | µ = 0.21 mm−1 |
b = 7.1665 (2) Å | T = 150 K |
c = 42.0343 (9) Å | 0.35 × 0.35 × 0.05 mm |
KappaCCD diffractometer | 3446 independent reflections |
Absorption correction: multi-scan R.H. Blessing, Acta Cryst. (1995), A51, 33-38 | 2839 reflections with I > 2σ(I) |
Tmin = 0.976, Tmax = 1.022 | Rint = 0.018 |
6102 measured reflections |
R[F2 > 2σ(F2)] = 0.043 | H atoms treated by a mixture of independent and constrained refinement |
wR(F2) = 0.099 | Δρmax = 0.24 e Å−3 |
S = 1.04 | Δρmin = −0.29 e Å−3 |
3446 reflections | Absolute structure: Flack H D (1983), Acta Cryst. A39, 876-881 |
263 parameters | Absolute structure parameter: 0.00 (9) |
0 restraints |
Geometry. All e.s.d.'s (except the e.s.d. in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell e.s.d.'s are taken into account individually in the estimation of e.s.d.'s in distances, angles and torsion angles; correlations between e.s.d.'s in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell e.s.d.'s is used for estimating e.s.d.'s involving l.s. planes. |
Refinement. Refinement of F2 against ALL reflections. The weighted R-factor wR and goodness of fit S are based on F2, conventional R-factors R are based on F, with F set to zero for negative F2. The threshold expression of F2 > σ(F2) is used only for calculating R-factors(gt) etc. and is not relevant to the choice of reflections for refinement. R-factors based on F2 are statistically about twice as large as those based on F, and R- factors based on ALL data will be even larger. |
x | y | z | Uiso*/Ueq | ||
C1 | −0.0136 (5) | 0.8334 (3) | 0.30748 (7) | 0.0388 (6) | |
H1 | 0.115 (5) | 0.827 (4) | 0.3222 (7) | 0.047* | |
C2 | 0.0202 (5) | 0.9236 (4) | 0.27872 (8) | 0.0518 (8) | |
H2 | 0.169 (5) | 0.992 (4) | 0.2735 (7) | 0.062* | |
C3 | −0.1510 (6) | 0.9211 (4) | 0.25576 (8) | 0.0591 (9) | |
H3 | −0.121 (5) | 0.975 (5) | 0.2342 (8) | 0.071* | |
C4 | −0.3549 (5) | 0.8292 (5) | 0.26177 (8) | 0.0562 (8) | |
H4 | −0.475 (6) | 0.819 (4) | 0.2464 (8) | 0.067* | |
C5 | −0.3920 (5) | 0.7377 (4) | 0.29042 (7) | 0.0442 (7) | |
H5 | −0.548 (5) | 0.679 (4) | 0.2963 (7) | 0.053* | |
C6 | −0.2218 (4) | 0.7413 (3) | 0.31369 (6) | 0.0320 (5) | |
C7 | −0.2538 (4) | 0.6446 (3) | 0.34531 (6) | 0.0304 (5) | |
H7 | −0.177 (4) | 0.711 (3) | 0.3607 (6) | 0.036* | |
C8 | −0.1373 (4) | 0.4527 (4) | 0.34526 (6) | 0.0333 (5) | |
H8 | 0.041 (4) | 0.475 (4) | 0.3419 (6) | 0.04* | |
C9 | −0.2427 (6) | 0.3176 (4) | 0.32176 (7) | 0.0500 (8) | |
H9A | −0.217 (5) | 0.350 (4) | 0.3018 (8) | 0.06* | |
H9B | −0.422 (5) | 0.315 (4) | 0.3240 (7) | 0.06* | |
H9C | −0.182 (5) | 0.202 (5) | 0.3240 (7) | 0.06* | |
C10 | −0.0726 (6) | 0.4751 (5) | 0.40487 (7) | 0.0498 (7) | |
H12A | −0.171 (5) | 0.587 (4) | 0.4090 (7) | 0.06* | |
H12B | 0.085 (5) | 0.526 (4) | 0.3995 (7) | 0.06* | |
H12C | −0.061 (5) | 0.394 (4) | 0.4221 (8) | 0.06* | |
C11 | 0.2059 (5) | 1.0550 (3) | 0.49750 (6) | 0.0355 (5) | |
H13 | 0.293 (4) | 1.090 (3) | 0.5165 (7) | 0.043* | |
C12 | 0.2979 (4) | 1.0796 (3) | 0.46741 (6) | 0.0301 (5) | |
H14 | 0.438 (4) | 1.125 (3) | 0.4643 (6) | 0.036* | |
C13 | 0.1744 (3) | 1.0255 (3) | 0.44070 (5) | 0.0267 (5) | |
H15 | −0.149 (4) | 0.920 (3) | 0.4274 (6) | 0.032* | |
C14 | −0.0465 (4) | 0.9489 (3) | 0.44428 (6) | 0.0334 (5) | |
H16 | −0.292 (4) | 0.871 (3) | 0.4783 (6) | 0.04* | |
C15 | −0.1348 (4) | 0.9222 (3) | 0.47470 (7) | 0.0378 (6) | |
C16 | −0.0119 (4) | 0.9739 (3) | 0.50166 (6) | 0.0351 (5) | |
C17 | −0.1153 (5) | 0.9427 (4) | 0.53420 (7) | 0.0519 (7) | |
H17A | −0.2793 | 0.9204 | 0.5322 | 0.078* | |
H17B | −0.0899 | 1.0513 | 0.5471 | 0.078* | |
H17C | −0.0425 | 0.8367 | 0.544 | 0.078* | |
N1 | −0.1613 (3) | 0.3644 (3) | 0.37777 (5) | 0.0349 (5) | |
H10 | −0.3129 | 0.3405 | 0.3812 | 0.042* | |
H11 | −0.0863 | 0.2543 | 0.3775 | 0.042* | |
O1 | −0.4928 (3) | 0.6161 (2) | 0.35346 (4) | 0.0382 (4) | |
H6 | −0.534 (5) | 0.695 (4) | 0.3661 (7) | 0.046* | |
O2 | 0.4535 (3) | 0.8834 (3) | 0.39905 (5) | 0.0478 (5) | |
O3 | 0.4268 (4) | 1.2203 (3) | 0.40278 (5) | 0.0573 (6) | |
O4 | 0.1095 (3) | 1.0419 (3) | 0.37990 (4) | 0.0461 (5) | |
S1 | 0.30178 (10) | 1.04466 (8) | 0.402484 (15) | 0.03374 (16) |
U11 | U22 | U33 | U12 | U13 | U23 | |
C1 | 0.0416 (13) | 0.0321 (13) | 0.0426 (17) | 0.0031 (12) | 0.0055 (13) | 0.0019 (11) |
C2 | 0.0579 (16) | 0.0393 (15) | 0.058 (2) | 0.0061 (15) | 0.0222 (16) | 0.0111 (13) |
C3 | 0.079 (2) | 0.0553 (19) | 0.0435 (18) | 0.0280 (17) | 0.0236 (17) | 0.0177 (15) |
C4 | 0.062 (2) | 0.073 (2) | 0.0341 (19) | 0.0215 (17) | −0.0028 (15) | 0.0088 (15) |
C5 | 0.0445 (14) | 0.0526 (17) | 0.0355 (17) | 0.0096 (13) | −0.0018 (12) | 0.0034 (13) |
C6 | 0.0379 (12) | 0.0260 (11) | 0.0323 (14) | 0.0072 (10) | 0.0035 (11) | −0.0016 (9) |
C7 | 0.0301 (12) | 0.0299 (12) | 0.0313 (14) | 0.0007 (9) | 0.0012 (10) | −0.0037 (10) |
C8 | 0.0382 (12) | 0.0346 (12) | 0.0270 (13) | 0.0076 (11) | 0.0016 (10) | 0.0020 (11) |
C9 | 0.080 (2) | 0.0324 (14) | 0.0375 (18) | 0.0119 (15) | −0.0018 (16) | −0.0062 (12) |
C10 | 0.0728 (19) | 0.0456 (15) | 0.0309 (16) | 0.0020 (15) | −0.0108 (15) | −0.0025 (14) |
C11 | 0.0462 (12) | 0.0275 (11) | 0.0327 (14) | −0.0035 (12) | −0.0027 (11) | −0.0013 (10) |
C12 | 0.0275 (10) | 0.0280 (12) | 0.0347 (13) | −0.0006 (10) | −0.0009 (11) | 0.0004 (9) |
C13 | 0.0284 (10) | 0.0218 (10) | 0.0300 (13) | 0.0027 (10) | 0.0015 (9) | 0.0003 (9) |
C14 | 0.0305 (11) | 0.0272 (12) | 0.0425 (16) | 0.0012 (11) | −0.0070 (10) | −0.0010 (11) |
C15 | 0.0291 (11) | 0.0267 (13) | 0.0576 (19) | −0.0019 (10) | 0.0089 (11) | 0.0031 (11) |
C16 | 0.0456 (12) | 0.0216 (10) | 0.0381 (15) | 0.0072 (11) | 0.0115 (11) | 0.0005 (10) |
C17 | 0.0703 (17) | 0.0332 (13) | 0.0523 (19) | −0.0018 (14) | 0.0284 (15) | 0.0006 (13) |
N1 | 0.0404 (11) | 0.0317 (10) | 0.0326 (12) | 0.0076 (9) | 0.0010 (9) | 0.0025 (9) |
O1 | 0.0350 (8) | 0.0360 (9) | 0.0436 (12) | 0.0049 (8) | 0.0108 (8) | −0.0023 (8) |
O2 | 0.0477 (10) | 0.0600 (11) | 0.0355 (11) | 0.0235 (9) | 0.0003 (9) | −0.0105 (9) |
O3 | 0.0794 (14) | 0.0495 (11) | 0.0431 (13) | −0.0265 (10) | 0.0230 (12) | −0.0051 (10) |
O4 | 0.0562 (10) | 0.0489 (10) | 0.0333 (11) | 0.0124 (10) | −0.0097 (8) | −0.0019 (9) |
S1 | 0.0385 (3) | 0.0334 (3) | 0.0293 (3) | 0.0025 (3) | 0.0023 (3) | −0.0027 (3) |
C1—C2 | 1.385 (4) | C10—H12B | 1.00 (3) |
C1—C6 | 1.392 (3) | C10—H12C | 0.93 (3) |
C1—H1 | 0.96 (3) | C11—C12 | 1.383 (3) |
C2—C3 | 1.379 (5) | C11—C16 | 1.391 (4) |
C2—H2 | 1.01 (3) | C11—H13 | 0.98 (3) |
C3—C4 | 1.368 (4) | C12—C13 | 1.384 (3) |
C3—H3 | 1.00 (3) | C12—H14 | 0.88 (2) |
C4—C5 | 1.388 (4) | C13—C14 | 1.392 (3) |
C4—H4 | 0.95 (3) | C13—S1 | 1.771 (2) |
C5—C6 | 1.383 (4) | C14—C15 | 1.389 (4) |
C5—H5 | 1.02 (3) | C14—H15 | 0.94 (2) |
C6—C7 | 1.510 (3) | C15—C16 | 1.386 (4) |
C7—O1 | 1.430 (3) | C15—H16 | 0.99 (3) |
C7—C8 | 1.530 (3) | C16—C17 | 1.508 (3) |
C7—H7 | 0.92 (3) | C17—H17A | 0.96 |
C8—C9 | 1.510 (4) | C17—H17B | 0.96 |
C8—N1 | 1.512 (3) | C17—H17C | 0.96 |
C8—H8 | 1.05 (2) | N1—H10 | 0.9 |
C9—H9A | 0.89 (3) | N1—H11 | 0.9 |
C9—H9B | 1.03 (3) | O1—H6 | 0.81 (3) |
C9—H9C | 0.91 (3) | O2—S1 | 1.4547 (17) |
C10—N1 | 1.479 (3) | O3—S1 | 1.4496 (19) |
C10—H12A | 1.00 (3) | O4—S1 | 1.4572 (18) |
C2—C1—C6 | 120.4 (3) | H12A—C10—H12C | 114 (3) |
C2—C1—H1 | 118.2 (17) | H12B—C10—H12C | 110 (2) |
C6—C1—H1 | 121.2 (17) | C12—C11—C16 | 120.8 (2) |
C3—C2—C1 | 120.3 (3) | C12—C11—H13 | 121.4 (16) |
C3—C2—H2 | 117.4 (17) | C16—C11—H13 | 117.7 (15) |
C1—C2—H2 | 122.3 (18) | C11—C12—C13 | 120.7 (2) |
C4—C3—C2 | 119.3 (3) | C11—C12—H14 | 122.2 (17) |
C4—C3—H3 | 120.2 (18) | C13—C12—H14 | 117.0 (16) |
C2—C3—H3 | 120.2 (17) | C12—C13—C14 | 119.4 (2) |
C3—C4—C5 | 121.3 (3) | C12—C13—S1 | 120.15 (17) |
C3—C4—H4 | 122 (2) | C14—C13—S1 | 120.41 (18) |
C5—C4—H4 | 116 (2) | C15—C14—C13 | 119.2 (2) |
C6—C5—C4 | 119.7 (3) | C15—C14—H15 | 115.7 (15) |
C6—C5—H5 | 117.3 (16) | C13—C14—H15 | 125.0 (15) |
C4—C5—H5 | 122.6 (16) | C16—C15—C14 | 122.0 (2) |
C5—C6—C1 | 119.0 (2) | C16—C15—H16 | 116.2 (16) |
C5—C6—C7 | 121.8 (2) | C14—C15—H16 | 121.8 (16) |
C1—C6—C7 | 119.2 (2) | C15—C16—C11 | 117.9 (2) |
O1—C7—C6 | 113.15 (19) | C15—C16—C17 | 120.1 (2) |
O1—C7—C8 | 107.02 (19) | C11—C16—C17 | 122.0 (2) |
C6—C7—C8 | 110.97 (19) | C16—C17—H17A | 109.5 |
O1—C7—H7 | 111.6 (16) | C16—C17—H17B | 109.5 |
C6—C7—H7 | 108.8 (16) | H17A—C17—H17B | 109.5 |
C8—C7—H7 | 105.0 (15) | C16—C17—H17C | 109.5 |
C9—C8—N1 | 106.6 (2) | H17A—C17—H17C | 109.5 |
C9—C8—C7 | 113.7 (2) | H17B—C17—H17C | 109.5 |
N1—C8—C7 | 109.55 (19) | C10—N1—C8 | 116.1 (2) |
C9—C8—H8 | 113.6 (15) | C10—N1—H10 | 108.3 |
N1—C8—H8 | 106.0 (15) | C8—N1—H10 | 108.3 |
C7—C8—H8 | 107.1 (15) | C10—N1—H11 | 108.3 |
C8—C9—H9A | 113 (2) | C8—N1—H11 | 108.3 |
C8—C9—H9B | 110.6 (17) | H10—N1—H11 | 107.4 |
H9A—C9—H9B | 105 (3) | C7—O1—H6 | 110 (2) |
C8—C9—H9C | 112 (2) | O3—S1—O2 | 113.17 (12) |
H9A—C9—H9C | 106 (3) | O3—S1—O4 | 113.18 (13) |
H9B—C9—H9C | 111 (3) | O2—S1—O4 | 112.29 (11) |
N1—C10—H12A | 111.5 (17) | O3—S1—C13 | 105.33 (11) |
N1—C10—H12B | 109.5 (18) | O2—S1—C13 | 106.04 (11) |
H12A—C10—H12B | 105 (2) | O4—S1—C13 | 106.03 (11) |
N1—C10—H12C | 106.8 (19) | ||
C6—C1—C2—C3 | −0.8 (4) | C11—C12—C13—C14 | 1.2 (3) |
C1—C2—C3—C4 | 0.3 (5) | C11—C12—C13—S1 | −176.11 (17) |
C2—C3—C4—C5 | −0.4 (5) | C12—C13—C14—C15 | −2.3 (3) |
C3—C4—C5—C6 | 1.0 (5) | S1—C13—C14—C15 | 175.04 (18) |
C4—C5—C6—C1 | −1.5 (4) | C13—C14—C15—C16 | 1.7 (3) |
C4—C5—C6—C7 | 179.8 (2) | C14—C15—C16—C11 | 0.1 (3) |
C2—C1—C6—C5 | 1.4 (4) | C14—C15—C16—C17 | 179.8 (2) |
C2—C1—C6—C7 | −179.8 (2) | C12—C11—C16—C15 | −1.2 (3) |
C5—C6—C7—O1 | −22.8 (3) | C12—C11—C16—C17 | 179.1 (2) |
C1—C6—C7—O1 | 158.5 (2) | C9—C8—N1—C10 | −178.9 (2) |
C5—C6—C7—C8 | 97.5 (3) | C7—C8—N1—C10 | −55.5 (3) |
C1—C6—C7—C8 | −81.2 (3) | C12—C13—S1—O3 | −40.2 (2) |
O1—C7—C8—C9 | 60.0 (3) | C14—C13—S1—O3 | 142.52 (19) |
C6—C7—C8—C9 | −63.9 (3) | C12—C13—S1—O2 | 80.06 (19) |
O1—C7—C8—N1 | −59.2 (2) | C14—C13—S1—O2 | −97.26 (19) |
C6—C7—C8—N1 | 176.94 (18) | C12—C13—S1—O4 | −160.39 (17) |
C16—C11—C12—C13 | 0.5 (3) | C14—C13—S1—O4 | 22.3 (2) |
D—H···A | D—H | H···A | D···A | D—H···A |
N1—H11···O4i | 0.9 | 1.9 | 2.789 (2) | 171 |
N1—H11···S1i | 0.9 | 2.89 | 3.663 (2) | 145 |
N1—H10···O3ii | 0.9 | 1.95 | 2.789 (3) | 154 |
O1—H6···O2iii | 0.81 (3) | 1.94 (3) | 2.727 (2) | 165 (3) |
Symmetry codes: (i) x, y−1, z; (ii) x−1, y−1, z; (iii) x−1, y, z. |
Experimental details
(publication_text) | (EPHEADIP) | (EPHEBESY) | (EPHEEDIS) | |
Crystal data | ||||
Chemical formula | C12H19NO3 | C16H25NO5 | C16H20O4S | C22H36N2O8S2 |
Mr | 450.56 | 311.37 | 323.4 | 520.65 |
Crystal system, space group | Triclinic, P1 | Orthorhombic, P212121 | Monoclinic, P21 | Monoclinic, P21 |
Temperature (K) | 150 | 150 | 150 | 150 |
a, b, c (Å) | 5.9642 (1), 10.4125 (2), 11.7403 (4) | 5.8290 (1), 13.5440 (4), 21.7000 (7) | 5.7214 (3), 20.8336 (11), 6.9188 (5) | 5.7108 (1), 34.0651 (7), 6.6590 (2) |
α, β, γ (°) | 108.175 (1), 104.560 (1), 104.087 (2) | 90, 90, 90 | 90, 98.409 (2), 90 | 90, 90.09, 90 |
V (Å3) | 628.08 (3) | 1713.17 (8) | 815.84 (8) | 1295.43 (5) |
Z | 1 | 4 | 2 | 2 |
Radiation type | Mo Kα | Mo Kα | Mo Kα | Mo Kα |
µ (mm−1) | 0.09 | 0.09 | 0.22 | 0.25 |
Crystal size (mm) | 0.3 × 0.05 × 0.05 | 0.25 × 0.25 × 0.05 | 0.25 × 0.25 × 0.05 | 0.35 × 0.35 × 0.05 |
Data collection | ||||
Diffractometer | KappaCCD diffractometer | KappaCCD diffractometer | KappaCCD diffractometer | KappaCCD diffractometer |
Absorption correction | Multi-scan R.H. Blessing, Acta Cryst. (1995), A51, 33-38 | – | Multi-scan R.H. Blessing, Acta Cryst. (1995), A51, 33-38 | Multi-scan R.H. Blessing, Acta Cryst. (1995), A51, 33-38 |
Tmin, Tmax | 0.927, 1.051 | – | 0.984, 1.024 | 0.979, 1.027 |
No. of measured, independent and observed reflections | 11807, 3007, 2247 [ > 2σ(i)] | 3874, 2266, 1808 [I > 2σ(I)] | 5520, 3395, 2159 [I > 2σ(I)] | 10886, 5249, 3134 [I > 2σ(I)] |
Rint | 0.062 | ? | 0.038 | 0.032 |
(sin θ/λ)max (Å−1) | 0.667 | 0.649 | 0.649 | 0.649 |
Refinement | ||||
R[F2 > 2σ(F2)], wR(F2), S | 0.043, 0.102, 1.03 | 0.041, 0.094, 1.03 | 0.055, 0.113, 1.01 | 0.054, 0.125, 0.98 |
No. of reflections | 3007 | 2266 | 3395 | 5249 |
No. of parameters | 351 | 269 | 260 | 357 |
No. of restraints | 3 | 0 | 1 | 1 |
H-atom treatment | H atoms treated by a mixture of independent and constrained refinement | H atoms treated by a mixture of independent and constrained refinement | H atoms treated by a mixture of independent and constrained refinement | H atoms treated by a mixture of independent and constrained refinement |
Δρmax, Δρmin (e Å−3) | 0.18, −0.22 | 0.18, −0.24 | 0.27, −0.42 | 0.31, −0.37 |
Absolute structure | ? | ? | Flack H D (1983), Acta Cryst. A39, 876-881 | Flack H D (1983), Acta Cryst. A39, 876-881 |
Absolute structure parameter | ? | ? | −0.04 (11) | −0.03 (11) |
(EPHE) | (EPHEESYL) | (EPHEGLYC) | (EPHEHCL) | |
Crystal data | ||||
Chemical formula | C10H16NO | C12H21NO4S | C12H19NO4 | C10H14ClNO |
Mr | 165.23 | 275.36 | 241.28 | 201.69 |
Crystal system, space group | Orthorhombic, P212121 | Orthorhombic, P212121 | Monoclinic, P21 | Monoclinic, P21 |
Temperature (K) | 150 | 150 | 150 | 150 |
a, b, c (Å) | 5.6851 (4), 7.7047 (5), 22.4819 (17) | 5.4877 (7), 11.9057 (17), 22.639 (4) | 9.5946 (4), 6.0474 (3), 10.8255 (5) | 7.2557 (3), 6.1228 (3), 12.5486 (6) |
α, β, γ (°) | 90, 90, 90 | 90, 90, 90 | 90, 101.607 (2), 90 | 90, 102.223 (2), 90 |
V (Å3) | 984.75 (12) | 1479.1 (4) | 615.28 (5) | 544.84 (4) |
Z | 4 | 4 | 2 | 2 |
Radiation type | Mo Kα | Mo Kα | Mo Kα | Mo Kα |
µ (mm−1) | 0.07 | 0.23 | 0.10 | 0.31 |
Crystal size (mm) | 0.25 × 0.05 × 0.05 | 0.25 × 0.05 × 0.05 | 0.3 × 0.05 × 0.05 | 0.3 × 0.05 × 0.05 |
Data collection | ||||
Diffractometer | KappaCCD diffractometer | KappaCCD diffractometer | KappaCCD diffractometer | KappaCCD diffractometer |
Absorption correction | Multi-scan R.H. Blessing, Acta Cryst. (1995), A51, 33-38 | – | Multi-scan R.H. Blessing, Acta Cryst. (1995), A51, 33-38 | Multi-scan R.H. Blessing, Acta Cryst. (1995), A51, 33-38 |
Tmin, Tmax | 0.975, 1.061 | – | 0.938, 1.054 | 0.926, 1.083 |
No. of measured, independent and observed reflections | 8327, 1340, 617 [I > 2σ(I)] | 1831, 1831, 1073 [I > 2σ(I)] | 4479, 1513, 1200 [I > 2σ(I)] | 9528, 2458, 2006 [I > 2σ(I)] |
Rint | 0.076 | ? | 0.035 | 0.057 |
(sin θ/λ)max (Å−1) | 0.649 | 0.664 | 0.648 | 0.650 |
Refinement | ||||
R[F2 > 2σ(F2)], wR(F2), S | 0.056, 0.115, 0.96 | 0.102, 0.264, 1.08 | 0.045, 0.098, 1.08 | 0.066, 0.156, 1.19 |
No. of reflections | 1340 | 1831 | 1513 | 2458 |
No. of parameters | 154 | 169 | 211 | 148 |
No. of restraints | 0 | 0 | 1 | 1 |
H-atom treatment | H atoms treated by a mixture of independent and constrained refinement | H atoms treated by a mixture of independent and constrained refinement | H atoms treated by a mixture of independent and constrained refinement | H atoms treated by a mixture of independent and constrained refinement |
Δρmax, Δρmin (e Å−3) | 0.23, −0.22 | 0.33, −0.31 | 0.23, −0.25 | 0.73, −0.37 |
Absolute structure | ? | ? | ? | Flack H D (1983), Acta Cryst. A39, 876-881 |
Absolute structure parameter | ? | ? | ? | 0.05 (13) |
(EPHEHEMI) | (EPHEMALA) | (EPHEMALE) | (EPHEMALO) | |
Crystal data | ||||
Chemical formula | C10H15NO | C14H21NO6 | C12H12NO4 | C11H17NO3 |
Mr | 174.24 | 299.32 | 299.32 | 217.26 |
Crystal system, space group | Orthorhombic, C2221 | Monoclinic, P21 | Orthorhombic, P212121 | Monoclinic, C2 |
Temperature (K) | 150 | 293 | 150 | 150 |
a, b, c (Å) | 7.3639 (4), 11.2551 (6), 24.1442 (16) | 6.1312 (6), 9.1719 (10), 13.7393 (17) | 5.6370 (2), 13.4950 (5), 20.5250 (5) | 15.1190 (14), 5.7840 (7), 13.8788 (15) |
α, β, γ (°) | 90, 90, 90 | 90, 100.909 (4), 90 | 90, 90, 90 | 90, 105.765 (7), 90 |
V (Å3) | 2001.1 (2) | 758.66 (15) | 1561.36 (9) | 1168.0 (2) |
Z | 8 | 2 | 4 | 4 |
Radiation type | Mo Kα | Mo Kα | Mo Kα | Mo Kα |
µ (mm−1) | 0.08 | 0.10 | 0.1 | 0.09 |
Crystal size (mm) | 0.25 × 0.25 × 0.05 | 0.25 × 0.25 × 0.1 | 0.25 × 0.05 × 0.05 | 0.3 × 0.05 × 0.05 |
Data collection | ||||
Diffractometer | KappaCCD diffractometer | KappaCCD diffractometer | KappaCCD diffractometer | KappaCCD diffractometer |
Absorption correction | Multi-scan R.H. Blessing, Acta Cryst. (1995), A51, 33-38 | Multi-scan R.H. Blessing, Acta Cryst. (1995), A51, 33-38 | – | Multi-scan R.H. Blessing, Acta Cryst. (1995), A51, 33-38 |
Tmin, Tmax | 0.976, 1.02 | 0.912, 1.134 | – | 0.987, 1.021 |
No. of measured, independent and observed reflections | 5306, 1007, 801 [I > 2σ(I)] | 6933, 1713, 1232 [I > 2σ(I)] | 11592, 1996, 1712 [I > 2σ(I)] | 4107, 1448, 937 [I > 2σ(I)] |
Rint | 0.048 | 0.109 | ? | ? |
(sin θ/λ)max (Å−1) | 0.595 | 0.650 | 0.649 | 0.649 |
Refinement | ||||
R[F2 > 2σ(F2)], wR(F2), S | 0.042, 0.100, 1.08 | 0.060, 0.185, 1.13 | 0.036, 0.092, 1.05 | 0.056, 0.129, 1.06 |
No. of reflections | 1007 | 1713 | 1996 | 1448 |
No. of parameters | 151 | 213 | 208 | 182 |
No. of restraints | 0 | 1 | 0 | 1 |
H-atom treatment | H atoms treated by a mixture of independent and constrained refinement | H atoms treated by a mixture of independent and constrained refinement | H atoms treated by a mixture of independent and constrained refinement | H atoms treated by a mixture of independent and constrained refinement |
Δρmax, Δρmin (e Å−3) | 0.14, −0.16 | 0.26, −0.30 | 0.19, −0.17 | 0.15, −0.23 |
Absolute structure | ? | Flack H D (1983), Acta Cryst. A39, 876-881 | ? | ? |
Absolute structure parameter | ? | 10 (10) | ? | ? |
(EPHEMESY) | (EPHENITR) | (EPHEPHOS) | (EPHEBISU) | |
Crystal data | ||||
Chemical formula | C11H19NO4S | C10H14N2O4 | C10H16NO5P | C10H18NO5S |
Mr | 261.33 | 228.25 | 263.22 | 263.31 |
Crystal system, space group | Monoclinic, C2 | Monoclinic, P21 | Monoclinic, C2 | Monoclinic, C2 |
Temperature (K) | 150 | 150 | 150 | 150 |
a, b, c (Å) | 14.287 (2), 6.1075 (7), 14.993 (2) | 5.5309 (4), 6.8501 (6), 15.6906 (13) | 14.6992 (10), 5.6433 (4), 15.2432 (14) | 30.9967 (17), 6.9861 (4), 5.6170 (3) |
α, β, γ (°) | 90, 93.211 (6), 90 | 90, 97.243 (6), 90 | 90, 97.333 (3), 90 | 90, 93.354 (3), 90 |
V (Å3) | 1306.3 (3) | 589.73 (8) | 1254.11 (17) | 1214.26 (12) |
Z | 4 | 2 | 4 | 4 |
Radiation type | Mo Kα | Mo Kα | Mo Kα | Mo Kα |
µ (mm−1) | 0.25 | 0.1 | 0.23 | 0.28 |
Crystal size (mm) | 0.3 × 0.05 × 0.05 | 0.2 × 0.2 × 0.05 | 0.25 × 0.05 × 0.05 | 0.35 × 0.15 × 0.05 |
Data collection | ||||
Diffractometer | KappaCCD diffractometer | KappaCCD diffractometer | KappaCCD diffractometer | KappaCCD diffractometer |
Absorption correction | Multi-scan R.H. Blessing, Acta Cryst. (1995), A51, 33-38 | Multi-scan R.H. Blessing, Acta Cryst. (1995), A51, 33-38 | Multi-scan R.H. Blessing, Acta Cryst. (1995), A51, 33-38 | Multi-scan R.H. Blessing, Acta Cryst. (1995), A51, 33-38 |
Tmin, Tmax | 0.984, 1.017 | 0.951, 1.041 | 0.954, 1.056 | 0.969, 1.029 |
No. of measured, independent and observed reflections | 3231, 2236, 1751 [I > 2σ(I)] | 2914, 1274, 991 [I > 2σ(I)] | 4138, 2497, 2110 [I > 2σ(I)] | 10680, 3183, 1982 [I > 2σ(I)] |
Rint | 0.029 | 0.032 | 0.033 | 0.058 |
(sin θ/λ)max (Å−1) | 0.649 | 0.649 | 0.647 | 0.681 |
Refinement | ||||
R[F2 > 2σ(F2)], wR(F2), S | 0.048, 0.119, 1.10 | 0.044, 0.103, 1.07 | 0.051, 0.119, 1.07 | 0.074, 0.125, 1.12 |
No. of reflections | 2236 | 1274 | 2497 | 3183 |
No. of parameters | 179 | 185 | 173 | 173 |
No. of restraints | 1 | 1 | 1 | 1 |
H-atom treatment | H atoms treated by a mixture of independent and constrained refinement | H atoms treated by a mixture of independent and constrained refinement | H atoms treated by a mixture of independent and constrained refinement | H atoms treated by a mixture of independent and constrained refinement |
Δρmax, Δρmin (e Å−3) | 0.20, −0.33 | 0.17, −0.23 | 0.31, −0.37 | 0.31, −0.37 |
Absolute structure | Flack H D (1983), Acta Cryst. A39, 876-881 | ? | Flack H D (1983), Acta Cryst. A39, 876-881 | Flack H D (1983), Acta Cryst. A39, 876-881 |
Absolute structure parameter | −0.04 (14) | ? | −0.13 (15) | 0.01 (12) |
(EPHETART1) | (EPHETART3) | (EPHETOSY) | |
Crystal data | |||
Chemical formula | C14H23NO8 | C24H42N2O11 | C17H23NO7S |
Mr | 333.33 | 534.6 | 337.42 |
Crystal system, space group | Orthorhombic, P212121 | Triclinic, P1 | Orthorhombic, P212121 |
Temperature (K) | 150 | 150 | 150 |
a, b, c (Å) | 6.6220 (2), 7.4620 (3), 33.2160 (15) | 5.9373 (2), 7.0594 (2), 18.3791 (8) | 5.7491 (2), 7.1665 (2), 42.0343 (9) |
α, β, γ (°) | 90, 90, 90 | 80.254 (1), 88.527 (2), 66.247 (2) | 90, 90, 90 |
V (Å3) | 1641.31 (11) | 694.14 (4) | 1731.85 (9) |
Z | 4 | 1 | 4 |
Radiation type | Mo Kα | Mo Kα | Mo Kα |
µ (mm−1) | 0.11 | 0.10 | 0.21 |
Crystal size (mm) | 0.25 × 0.25 × 0.05 | 0.25 × 0.25 × 0.05 | 0.35 × 0.35 × 0.05 |
Data collection | |||
Diffractometer | KappaCCD diffractometer | KappaCCD diffractometer | KappaCCD diffractometer |
Absorption correction | Multi-scan R.H. Blessing, Acta Cryst. (1995), A51, 33-38 | Multi-scan R.H. Blessing, Acta Cryst. (1995), A51, 33-38 | Multi-scan R.H. Blessing, Acta Cryst. (1995), A51, 33-38 |
Tmin, Tmax | 0.962, 1.02 | 0.879, 1.158 | 0.976, 1.022 |
No. of measured, independent and observed reflections | 1789, 1789, 1362 [I > 2σ(I)] | 6838, 2412, 2078 [I > 2σ(I)] | 6102, 3446, 2839 [I > 2σ(I)] |
Rint | ? | ? | 0.018 |
(sin θ/λ)max (Å−1) | 0.609 | 0.595 | 0.649 |
Refinement | |||
R[F2 > 2σ(F2)], wR(F2), S | 0.040, 0.087, 1.03 | 0.098, 0.295, 1.31 | 0.043, 0.099, 1.04 |
No. of reflections | 1789 | 2412 | 3446 |
No. of parameters | 263 | 349 | 263 |
No. of restraints | 0 | 3 | 0 |
H-atom treatment | H atoms treated by a mixture of independent and constrained refinement | H atoms treated by a mixture of independent and constrained refinement | H atoms treated by a mixture of independent and constrained refinement |
Δρmax, Δρmin (e Å−3) | 0.22, −0.21 | 0.59, −0.43 | 0.24, −0.29 |
Absolute structure | ? | ? | Flack H D (1983), Acta Cryst. A39, 876-881 |
Absolute structure parameter | ? | ? | 0.00 (9) |
Computer programs: Collect (Nonius BV, 1997-2000), HKL SCALEPACK (Otwinowski & Minor 1997), HKL DENZO and SCALEPACK (Otwinowski & Minor 1997), HKL DENZO and SCALEPACK (Otwinowski & Minor 1, SHELXS97 (Sheldrick, 1997), SHELXL97 (sheldrick, 1997), SHELXL97 (Sheldrick, 1997), ORTEP-3 for Windows (Farrugia, 1997), WinGX publication routines (Farrugia, 1999).
D—H···A | D—H | H···A | D···A | D—H···A |
n01—h11···o03i | 0.9 | 1.81 | 2.705 (3) | 172.9 |
n01—h11···o02i | 0.9 | 2.75 | 3.318 (3) | 122.4 |
n21—h31···o23ii | 0.9 | 1.82 | 2.714 (3) | 169.8 |
o21—h26···o03ii | 0.78 (4) | 1.90 (4) | 2.669 (3) | 166 (4) |
n21—h30···o23iii | 0.9 | 2.85 | 3.438 (3) | 123.9 |
Symmetry codes: (i) x−1, y, z; (ii) x, y+1, z+1; (iii) x+1, y+1, z+1. |
D—H···A | D—H | H···A | D···A | D—H···A |
O1—H6···O3i | 0.89 (3) | 1.80 (3) | 2.686 (2) | 178 (2) |
N1—H11···O2ii | 1.01 (2) | 1.78 (2) | 2.783 (2) | 173.6 (19) |
O5—H21···O3iii | 0.89 (3) | 1.73 (3) | 2.615 (2) | 170 (3) |
Symmetry codes: (i) x−1/2, −y+3/2, −z; (ii) x+1/2, −y+3/2, −z; (iii) −x+2, y+1/2, −z+1/2. |
D—H···A | D—H | H···A | D···A | D—H···A |
N1—H10···O4i | 0.85 (4) | 1.97 (4) | 2.804 (4) | 170 (4) |
N1—H10···S1i | 0.85 (4) | 3.00 (4) | 3.750 (4) | 149 (3) |
N1—H11···O2ii | 0.97 (4) | 1.87 (4) | 2.787 (5) | 156 (3) |
N1—H11···S1ii | 0.97 (4) | 2.84 (4) | 3.635 (4) | 139 (3) |
O1—H6···O3iii | 0.82 | 1.96 | 2.773 (4) | 169.3 |
Symmetry codes: (i) x, y, z−1; (ii) x−1, y, z−1; (iii) x−1, y, z. |
D—H···A | D—H | H···A | D···A | D—H···A |
N01—H10···O06i | 0.9 | 1.98 | 2.868 (5) | 171.3 |
N01—H10···S2i | 0.9 | 2.88 | 3.642 (4) | 143.6 |
N01—H11···O05ii | 0.9 | 2.12 | 2.915 (5) | 147.2 |
N01—H11···S2ii | 0.9 | 2.88 | 3.614 (4) | 139.6 |
N21—H30···O03iii | 0.9 | 1.98 | 2.860 (5) | 163.6 |
N21—H30···S1iii | 0.9 | 2.95 | 3.717 (4) | 144.4 |
N21—H31···O04iv | 0.9 | 2.1 | 2.919 (5) | 151 |
N21—H31···S1iv | 0.9 | 2.9 | 3.648 (4) | 142.1 |
O21—H26···O02v | 0.82 | 2 | 2.771 (4) | 155.8 |
O21—H26···S1v | 0.82 | 2.96 | 3.778 (3) | 178.1 |
Symmetry codes: (i) x−1, y, z+1; (ii) x, y, z+1; (iii) −x+3, y−1/2, −z+2; (iv) −x+2, y−1/2, −z+2; (v) −x+2, y−1/2, −z+1. |
D—H···A | D—H | H···A | D···A | D—H···A |
O1—H6···N1i | 0.82 | 1.96 | 2.778 (4) | 173.2 |
Symmetry code: (i) x+1/2, −y+1/2, −z+1. |
D—H···A | D—H | H···A | D···A | D—H···A |
N1—H10···O2i | 0.9 | 2.03 | 2.904 (11) | 162.2 |
N1—H10···O3i | 0.9 | 2.47 | 3.099 (11) | 127.4 |
N1—H10···S1i | 0.9 | 2.71 | 3.537 (9) | 153 |
N1—H11···O3ii | 0.9 | 1.98 | 2.852 (11) | 162.3 |
O1—H6···O3ii | 0.82 | 2.37 | 3.119 (9) | 151.5 |
Symmetry codes: (i) −x+1, y+1/2, −z+1/2; (ii) −x, y+1/2, −z+1/2. |
D—H···A | D—H | H···A | D···A | D—H···A |
O2—H15···O4i | 0.87 (4) | 1.95 (4) | 2.776 (3) | 158 (3) |
O2—H15···O2i | 0.87 (4) | 2.62 (4) | 3.2430 (15) | 130 (3) |
O1—H6···O4ii | 0.75 (4) | 1.94 (4) | 2.696 (3) | 177 (3) |
N1—H10···O3iii | 0.88 (3) | 1.91 (4) | 2.776 (3) | 171 (3) |
Symmetry codes: (i) −x−1, y+1/2, −z+2; (ii) x, y+1, z; (iii) −x−1, y+1/2, −z+1. |
D—H···A | D—H | H···A | D···A | D—H···A |
N1—H11···Cl1i | 0.85 (5) | 2.33 (5) | 3.136 (4) | 157 (5) |
O1—H6···Cl1ii | 0.89 (6) | 2.23 (6) | 3.080 (3) | 159 (4) |
Symmetry codes: (i) −x+2, y+1/2, −z+1; (ii) x, y+1, z. |
D—H···A | D—H | H···A | D···A | D—H···A |
N1—H10···O2i | 0.88 (3) | 2.23 (3) | 3.092 (4) | 167 (3) |
O1—H6···N1ii | 0.82 | 1.93 | 2.743 (3) | 168.1 |
Symmetry codes: (i) x−1/2, y−1/2, z; (ii) −x, y, −z+3/2. |
D—H···A | D—H | H···A | D···A | D—H···A |
N1—H10···O5i | 0.9 | 1.99 | 2.867 (6) | 164.5 |
N1—H11···O6ii | 0.9 | 1.88 | 2.727 (6) | 156.4 |
O2—H16···O5iii | 0.82 | 1.96 | 2.769 (5) | 170.1 |
Symmetry codes: (i) −x, y+1/2, −z; (ii) x−1, y+1, z; (iii) −x+1, y+1/2, −z. |
D—H···A | D—H | H···A | D···A | D—H···A |
O1—H6···O6i | 0.89 (4) | 1.84 (4) | 2.725 (2) | 174 (3) |
N1—H10···O3ii | 0.99 (2) | 1.82 (3) | 2.808 (2) | 174 (2) |
N1—H10···O2ii | 0.99 (2) | 2.62 (3) | 3.216 (3) | 118.9 (18) |
N1—H11···O2iii | 0.94 (3) | 1.93 (3) | 2.844 (2) | 165 (2) |
O6—H17···O5iv | 0.83 (3) | 2.01 (3) | 2.755 (2) | 149 (3) |
Symmetry codes: (i) −x, y−1/2, −z+1/2; (ii) x+1/2, −y+1/2, −z; (iii) x−1/2, −y+1/2, −z; (iv) x−1/2, −y+1/2, −z+1. |
D—H···A | D—H | H···A | D···A | D—H···A |
N1—H10···O2i | 0.92 (4) | 1.80 (4) | 2.719 (4) | 178 (3) |
N1—H11···O2ii | 0.94 (4) | 1.88 (4) | 2.769 (4) | 158 (4) |
O1—H6···O3iii | 0.83 (4) | 1.82 (5) | 2.645 (4) | 175 (5) |
Symmetry codes: (i) x+1/2, y+1/2, z; (ii) −x, y, −z+1; (iii) x+1/2, y−1/2, z. |
D—H···A | D—H | H···A | D···A | D—H···A |
N1—H10···O4i | 0.97 (4) | 2.36 (4) | 3.002 (5) | 124 (3) |
N1—H11···O3ii | 0.81 (5) | 2.04 (5) | 2.788 (5) | 153 (5) |
Symmetry codes: (i) −x+3/2, y+1/2, −z+1; (ii) x+1/2, y+1/2, z. |
D—H···A | D—H | H···A | D···A | D—H···A |
N1—H10···O4i | 0.99 (3) | 1.93 (3) | 2.885 (4) | 164 (3) |
N1—H10···N2i | 0.99 (3) | 2.59 (4) | 3.461 (4) | 147 (3) |
N1—H10···O3i | 0.99 (3) | 2.63 (4) | 3.233 (4) | 120 (3) |
N1—H11···O2ii | 0.83 (4) | 2.16 (4) | 2.978 (4) | 168 (3) |
N1—H11···O4ii | 0.83 (4) | 2.45 (3) | 3.051 (3) | 130 (3) |
N1—H11···N2ii | 0.83 (4) | 2.66 (4) | 3.433 (4) | 155 (3) |
Symmetry codes: (i) x, y−1, z; (ii) x−1, y−1, z. |
D—H···A | D—H | H···A | D···A | D—H···A |
N1—H10···O2 | 0.9 | 1.87 | 2.768 (4) | 174.3 |
O4—H13···O3i | 0.82 | 1.78 | 2.547 (3) | 154.1 |
O5—H14···O2ii | 0.82 | 1.81 | 2.630 (3) | 173.7 |
N1—H11···O3ii | 0.9 | 1.86 | 2.699 (4) | 154.9 |
O1—H6···O2iii | 0.82 | 2.05 | 2.780 (3) | 148.4 |
Symmetry codes: (i) −x+1, y, −z+2; (ii) −x+1/2, y+1/2, −z+2; (iii) x, y+1, z. |
D—H···A | D—H | H···A | D···A | D—H···A |
N1—H11···O4i | 0.9 | 2.02 | 2.869 (4) | 156 |
O1—H6···O5ii | 0.76 (4) | 2.01 (4) | 2.768 (4) | 170 (5) |
N1—H12···O2iii | 0.9 | 1.98 | 2.881 (4) | 175.1 |
N1—H12···S1iii | 0.9 | 2.76 | 3.578 (3) | 152.2 |
O3—H13···O2iv | 0.82 | 1.84 | 2.653 (4) | 171.4 |
O3—H13···S1iv | 0.82 | 2.91 | 3.623 (3) | 146.3 |
Symmetry codes: (i) x, y−1, z−1; (ii) x, y, z−1; (iii) x, y−1, z; (iv) −x+1, y, −z+2. |
D—H···A | D—H | H···A | D···A | D—H···A |
O4—H16···O3i | 0.82 | 1.86 | 2.661 (3) | 167.4 |
O1—H6···O8ii | 0.82 | 1.92 | 2.738 (3) | 175.3 |
N1—H11···O6iii | 0.9 | 1.83 | 2.709 (3) | 163.7 |
O8—H18···O5iv | 0.84 (4) | 2.01 (4) | 2.845 (3) | 177 (4) |
O8—H19···O6v | 0.89 (4) | 1.91 (4) | 2.743 (3) | 154 (3) |
O8—H19···O4v | 0.89 (4) | 2.49 (3) | 3.063 (3) | 122 (3) |
O7—H17···O2vi | 0.82 | 1.63 | 2.446 (3) | 171.8 |
Symmetry codes: (i) x+1/2, −y+3/2, −z+1; (ii) −x+2, y+1/2, −z+1/2; (iii) x, y−1, z; (iv) −x+1, y−1/2, −z+1/2; (v) −x+2, y−1/2, −z+1/2; (vi) x, y+1, z. |
D—H···A | D—H | H···A | D···A | D—H···A |
O05—H16···O10i | 0.82 | 2.29 | 2.869 (9) | 128.2 |
N01—H11···O09i | 0.9 | 2 | 2.832 (10) | 152.6 |
O08—H17A···O02ii | 0.84 | 2.05 | 2.705 (9) | 133.6 |
O08—H17A···O04ii | 0.84 | 2.22 | 2.958 (10) | 145.3 |
O09—H18B···O03iii | 0.85 | 1.94 | 2.762 (9) | 165.1 |
O10—H19B···O07iii | 0.86 | 2.2 | 3.063 (10) | 175.5 |
O10—H19A···O05iv | 0.86 | 2.16 | 2.869 (9) | 139.8 |
N21—H30···O07v | 0.9 | 2 | 2.795 (9) | 147.1 |
Symmetry codes: (i) x, y+1, z; (ii) x+1, y, z; (iii) x−1, y, z; (iv) x, y−1, z; (v) x−1, y+1, z. |
D—H···A | D—H | H···A | D···A | D—H···A |
N1—H11···O4i | 0.9 | 1.9 | 2.789 (2) | 171.4 |
N1—H11···S1i | 0.9 | 2.89 | 3.663 (2) | 145.4 |
N1—H10···O3ii | 0.9 | 1.95 | 2.789 (3) | 154.4 |
O1—H6···O2iii | 0.81 (3) | 1.94 (3) | 2.727 (2) | 165 (3) |
Symmetry codes: (i) x, y−1, z; (ii) x−1, y−1, z; (iii) x−1, y, z. |
Footnotes
‡Current address: TransForm Pharmaceuticals Inc., 29 Hartwell Avenue, Lexington, MA 02139, USA.
1Supplementary data for this paper, including a complete and ellipsoid plots for all structures determined, are available from the IUCr electronic archives (Reference: BK5025 ). Services for accessing these data are described at the back of the journal.
Acknowledgements
The authors would like to thank both Robin G. Pritchard and Amy L. Gillon for their contribution to the crystallographic analysis performed within this work. In addition, Edwin A. Collier would like to thank AstraZeneca for the provision of funding to support this study.
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