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research communications
Crystal structures of four organic salts of trihexyphenidyl at 90 K
aDepartment of Studies in Chemistry, University of Mysore, Manasagangotri, Mysuru-570 006, India, and bDepartment of Chemistry, University of Kentucky, Lexington, KY, 40506-0055, USA
*Correspondence e-mail: ybb2706@gmail.com, yathirajan@hotmail.com
The syntheses and viz., trihexyphenidylium [1-(3-cyclohexyl-3-hydroxy-3-phenylpropyl)piperidin-1-ium] 4-nitrobenzoate, C20H32NO+·C7H4NO4− (I), trihexyphenidylium 4-hydroxybenzoate, C20H32NO+·C7H5O− (II), trihexyphenidylium 4-bromobenzoate, C20H32NO+·C7H4BrO2− (III), and trihexyphenidylium thiophene-2-carboxylate hemihydrate, 2C20H32NO+·2C5H3O2S−·H2O (IV), conducted at 90 K are described. Structures I, II, and III are solvent free with one cation–anion pair per while IV crystallizes as a hemihydrate, having two cation–anion pairs and one water of crystallization in its Structures I and III exhibit of the cation. Structure IV also exhibits disorder, but only of the thiophene-2-carboxylate anions. Structure II is a non-merohedric twin by a twofold rotation about [403]. The main supramolecular motifs in I, II, and III are similar R22(10) rings between cation–anion pairs, although their packing within the crystals is distinct. As a consequence of having two cation–anion pairs and a water molecule in its the packing in IV is by far the most complex of the four structures, its hydrogen-bonding patterns being quite different from I, II, or III. In all the crystals studied, N—H⋯O, O—H⋯O, and C—H⋯O interactions are observed, plus C—H⋯Br close contacts for III.
studies of four organic salts of trihexyphenidyl,1. Chemical context
Trihexyphenidyl, et al., 1994; Seeman & Tallerico, 1998
; Silvestre & Prous, 2005
). In addition, trihexyphenidyl is well established as a treatment for symptomatic relief in cases of Parkinson's disease (Doshay et al., 1954
). Trihexyphenidyl contains a chiral carbon atom, although medicinal formulations are racemates. It is generally administered as the hydrochloride salt, the structure of which was published by Maccaroni et al. (2010
), although structures have also been reported for neutral trihexyphenidyl (Camerman & Camerman, 1972
), and the trihexyphenidylium 3,5-dinitrobenzoate salt (Shaibah et al., 2019
).
In view of the medicinal importance of trihexyphenidyl, this paper reports the crystal structures of some salts of trihexyphenidyl with organic acids, viz., trihexyphenidylium 4-nitrobenzoate, C26H36NO3 (I), trihexyphenidylium 4-hydroxybenzoate, C27H37NO4 (II), trihexyphenidylium 4-bromobenzoate, C27H36NO3Br (III) and trihexyphenidylium thiophene-2-carboxylate, which crystallizes as a hemihydrate, C25H35NO3S·0.5H2O (IV).
2. Structural commentary
Individual neutral trihexyphenidyl molecules contain a chiral carbon atom. In structures I, II, III, IV, each trihexyphenidylium cation also includes a chiral carbon, with atoms C1 (C1A and C1B in IV) being the stereogenic centre. Nevertheless, medicinal formulations are racemic, and all four crystal structures (Figs. 1–4
) determined here are centrosymmetric and therefore also strictly racemic. Structures I, II, and III are solvent free with one cation–anion pair per while IV crystallized as a hemihydrate, having two cation–anion pairs and one water of crystallization in its asymmetric unit.
![]() | Figure 1 An ellipsoid plot (50%) probability of I. Hydrogen bonds are shown as dashed lines. To enhance clarity, only one component of disorder for the cation is shown. |
![]() | Figure 2 An ellipsoid plot (50%) probability of II. Hydrogen bonds are shown as dashed lines. |
![]() | Figure 3 An ellipsoid plot (50%) probability of III. Hydrogen bonds are shown as dashed lines. To enhance clarity, only one component of disorder for the cation is shown. |
![]() | Figure 4 An ellipsoid plot (50%) probability of IV. Hydrogen bonds are shown as dashed lines. To enhance clarity, only one component of disorder for the anions is shown. |
Structures I and III exhibit (see e.g. Parkin et al., 2023; Vinaya et al., 2023
) of the cation. This disorder switches the positions and overlays the phenyl and cyclohexyl rings, thereby superimposing R and S isomers in roughly equal refined proportions [0.503 (4):0.497 (4) in I and 0.508 (5):0.492 (5) in III], as shown for I in Fig. 5
. Structure IV also exhibits disorder, but of the thiophene-2-carboxylate anions [major:minor fractions are 0.795 (2):0.805 (2) and 0.953 (2):0.047 (2) for the inequivalent anion sites]. Structure II is a mon-merohedric twin (see e.g. Sevvana et al., 2019
; Parkin, 2021
) by a twofold rotation about [403], with similar twin-component fractions [0.5298 (9) and 0.4702 (9)]. The treatment of disorder and are described in more detail in section 6 (Refinement).
![]() | Figure 5 Configurational disorder of the trihexyphenidylium cation in I showing the superposition of phenyl and cyclohexyl rings. The disorder in III is similar. Hydrogen atoms are omitted. |
The conformations of the trihexyphenidylium cations are determined, in large part, by torsion angles about the C1—C2, C2—C3, C3—N1, C1—C9, and C1—C15 bonds. These are quantified in Table 1, although for ease of comparison, the variability in cation conformations is better illustrated by an overlay plot, shown in Fig. 6
.
|
![]() | Figure 6 An overlay of five independent trihexyphenidylium cations from structures I, II, III, and IV, showing the conformational variability. |
3. Supramolecular features
The main supramolecular motifs in I, II, and III are R22(10) hydrogen-bonded rings involving N—H and O—H donors from the cations and the carboxylate group of their respective anions. These ring structures are shown in the ellipsoid plots (Figs. 1–3
), while Figs. 7
–9
show how they pack within their unit cells.
![]() | Figure 7 A partial packing plot of I, viewed approximately down the a-axis. Hydrogen bonds are drawn as dotted lines. Hydrogen atoms not involved in hydrogen bonds are omitted. |
![]() | Figure 8 A partial packing plot of II, viewed approximately down the b-axis. Hydrogen bonds are drawn as dotted lines. Hydrogen atoms not involved in hydrogen bonds are omitted. |
![]() | Figure 9 A partial packing plot of III, viewed approximately down the a-axis. Hydrogen bonds are drawn as dotted lines. Hydrogen atoms not involved in hydrogen bonds are omitted. |
For I there are no other strong intermolecular interactions, though there is a weaker C4—H4B⋯O1i [symmetry code: (i) x − 1, y, z] contact between molecules adjacent along the a-axis direction. See Table 2 for details.
|
In II, the 4-hydroxy group of the anion is also involved in hydrogen bonding (Fig. 8). Atom O3 of the carboxylate acts as a bifurcated acceptor for the N1—H1N⋯O3 hydrogen bond within the R22(10) ring and for an O4ii—H4Oii⋯O3 [symmetry code: (ii) x, −y, z −
] hydrogen bond. There are also a few weaker C—H⋯O interactions. All these interactions are quantified in Table 3
.
|
In III, in addition to the aforementioned ring motif, there are short contacts between C3—H3A and Br1 of a screw-related (−x + , y +
, −z +
) anion and between C4—H4A and O3 of a translation-related (x − 1, y, z) anion. Full details are given in Table 4
. A view of the packing is shown in Fig. 9
.
|
As a result of having two cation–anion pairs and a water molecule in the IV is by far the most complex of the four structures. Its hydrogen-bonding patterns are quite different from I, II, or III. In fact the hydrogen-bonding motifs involving the `A–C' and `B–D' cation–anion pairs are themselves distinct. For the `A' cation, the N1A—H1NA group is an asymmetric bifurcated hydrogen-bond donor to O1C and O2C [dD⋯A = 2.7084 (17) and 3.3355 (18) Å, respectively]. The hydroxyl group of cation A forms a hydrogen bond (as donor) to O2C of a translation-related (via x + 1, y, z) anion. These combine to form A–C cation–anion chains that extend parallel to the a-axis (Fig. 10, upper chain). The B–D cation–anion pair plus the water molecule form an R33(12) hydrogen-bonded ring motif that includes N1B—H1NB⋯O1D, O1B—H1OB⋯O1W, and O1W—H2W1⋯O2D within the chosen (Table 5
, Figs. 4
and 10
). The water molecule also forms a hydrogen bond to O1D of a translation-related (x + 1, y, z) anion. The net result of these hydrogen bonds are cation–anion–water chains that also propagate along the a-axis direction (Fig. 10
, lower chain). The only contacts between these two types of chain are weak (Table 5
).
|
![]() | Figure 10 A partial packing plot of IV, viewed approximately down the b-axis. Hydrogen bonds are drawn as dotted lines. Hydrogen atoms not involved in hydrogen bonds are omitted. |
4. Database survey
A search within the Cambridge Structural Database (CSD, v5.43 including all updates through November 2022; Groom et al., 2016) for an unsubstituted trihexyphenidyl structure fragment returned 16 hits, but only five of them bear any similarity to the trihexyphenidylium cation in I, II, III, and IV. CSD entry THEXPL (Camerman & Camerman, 1972
) is a single-crystal structure of neutral trihexyphenidyl. Refcode KUZDIT (Maccaroni et al., 2010
) is trihexyphenidyl hydrochloride, obtained via powder diffraction, and GODJAN (Shaibah et al., 2019
) is a single-crystal study of the trihexyphenidylium 3,5-dinitrobenzoate salt. The remaining two structures are PCYDIN10 (Camerman & Camerman, 1971
) and DODWAU (Tacke et al., 1986
). The former is the anti-psychotic medication procyclidine hydrochloride, which has a pyrrolidinium ring in place of the piperidinium ring in I, II, III, and IV. The latter is (R)-tricyclamol iodide, which has an N-methyl-pyrrolidinium ring.
5. Crystallization
A solution of commercially available trihexyphenidyl (a gift from RL Fine Chem., Bengaluru, India) (150 mg, 0.50 mol) in methanol (10 ml) was mixed with equimolar solutions of the appropriate acids in methanol (10 ml) viz., 4-nitrobenzoic acid (84 mg, 0.50 mol) for I, and in methanol (5 ml) and acetonitrile (5 ml) for 4-hydroxybenzoic acid (69 mg, 0.5 mol) (II), 4-bromobenzoic acid (101 mg, 0.50 mol) (III) and thiophene-2-carboxylic acid (64 mg, 0.50 mol) (IV). The resulting solutions were stirred for 30 minutes at 333 K and allowed to stand at room temperature. X-ray quality crystals were formed on slow evaporation over the course of a week for all of the compounds. The melting points were 409–411 K (I), 425–427 K (II), 395–396 K and (III) 368–369 K (IV).
6. Refinement
Crystal data, data collection, and . For all structures, diffraction data were collected with the crystals at 90 K. Non-disordered hydrogen atoms were located in difference-Fourier maps. Those bound to nitrogen or oxygen were refined freely, but carbon-bound hydrogens were included using riding models with constrained distances of 0.95 Å (Csp2—H), 0.99 Å (R2CH2), and 1.00 Å (R3CH) using Uiso(H) values constrained to 1.2Ueq of the attached carbon atom. Cation disorder in I and III was modelled using similar combinations of restraints (SHELXL commands SADI, SAME, DFIX, FLAT) and constraints (SHELXL command EADP). Disorder of the thiophene-2-carboxylate anions in IV corresponded to a ∼180° flip of the thiophene ring, which is common for thiophene, and was modelled using geometry restraints (SAME and FLAT) and displacement parameter constraints (EADP). Structure II was twinned by non-merohedry, corresponding to a twofold rotation about the real-space direction [403]. Diffraction data were integrated using two orientation matrices and scaled/merged following standard procedures (see e.g. Sevvana et al., 2019
), and the model refined against both twin components in the usual manner (SHELXL-format HKLF 5 datafile and a BASF parameter to define their relative volume fractions).
|
Supporting information
https://doi.org/10.1107/S2056989023005960/vm2286sup1.cif
contains datablocks I, II, III, IV, global. DOI:Structure factors: contains datablock I. DOI: https://doi.org/10.1107/S2056989023005960/vm2286Isup2.hkl
Structure factors: contains datablock II. DOI: https://doi.org/10.1107/S2056989023005960/vm2286IIsup3.hkl
Structure factors: contains datablock III. DOI: https://doi.org/10.1107/S2056989023005960/vm2286IIIsup4.hkl
Structure factors: contains datablock IV. DOI: https://doi.org/10.1107/S2056989023005960/vm2286IVsup5.hkl
Supporting information file. DOI: https://doi.org/10.1107/S2056989023005960/vm2286Isup6.cml
Supporting information file. DOI: https://doi.org/10.1107/S2056989023005960/vm2286IIsup7.cml
Supporting information file. DOI: https://doi.org/10.1107/S2056989023005960/vm2286IIIsup8.cml
Supporting information file. DOI: https://doi.org/10.1107/S2056989023005960/vm2286IVsup9.cml
For all structures, data collection: APEX3 (Bruker, 2016); cell
APEX3 (Bruker, 2016); data reduction: APEX3 (Bruker, 2016); program(s) used to solve structure: SHELXT (Sheldrick, 2015a); program(s) used to refine structure: SHELXL2019/2 (Sheldrick, 2015b); molecular graphics: XP in SHELXTL (Sheldrick, 2008) and Mercury (Macrae et al., 2020); software used to prepare material for publication: SHELX (Sheldrick, 2008) and publCIF (Westrip, 2010).C20H32NO+·C7H4NO4− | Z = 2 |
Mr = 468.58 | F(000) = 504 |
Triclinic, P1 | Dx = 1.277 Mg m−3 |
a = 6.2568 (5) Å | Mo Kα radiation, λ = 0.71073 Å |
b = 11.7542 (14) Å | Cell parameters from 9957 reflections |
c = 16.9162 (19) Å | θ = 2.2–27.5° |
α = 85.329 (3)° | µ = 0.09 mm−1 |
β = 79.534 (4)° | T = 90 K |
γ = 87.785 (3)° | Plate, colourless |
V = 1219.0 (2) Å3 | 0.30 × 0.21 × 0.04 mm |
Bruker D8 Venture dual source diffractometer | 5590 independent reflections |
Radiation source: microsource | 4825 reflections with I > 2σ(I) |
Detector resolution: 7.41 pixels mm-1 | Rint = 0.041 |
φ and ω scans | θmax = 27.6°, θmin = 2.1° |
Absorption correction: multi-scan (SADABS; Krause et al., 2015) | h = −8→7 |
Tmin = 0.907, Tmax = 0.959 | k = −15→15 |
35646 measured reflections | l = −21→21 |
Refinement on F2 | Secondary atom site location: difference Fourier map |
Least-squares matrix: full | Hydrogen site location: mixed |
R[F2 > 2σ(F2)] = 0.047 | H atoms treated by a mixture of independent and constrained refinement |
wR(F2) = 0.107 | w = 1/[σ2(Fo2) + (0.0274P)2 + 0.7788P] where P = (Fo2 + 2Fc2)/3 |
S = 1.11 | (Δ/σ)max < 0.001 |
5590 reflections | Δρmax = 0.30 e Å−3 |
355 parameters | Δρmin = −0.19 e Å−3 |
68 restraints | Extinction correction: SHELXL-2019/2 (Sheldrick 2008), Fc*=kFc[1+0.001xFc2λ3/sin(2θ)]-1/4 |
Primary atom site location: structure-invariant direct methods | Extinction coefficient: 0.0101 (18) |
Experimental. The crystal was mounted using polyisobutene oil on the tip of a fine glass fibre, which was fastened in a copper mounting pin with electrical solder. It was placed directly into the cold gas stream of a liquid-nitrogen based cryostat (Hope, 1994; Parkin & Hope, 1998). Diffraction data were collected with the crystal at 90K, which is standard practice in this laboratory for the majority of flash-cooled crystals. |
Geometry. All esds (except the esd in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell esds are taken into account individually in the estimation of esds in distances, angles and torsion angles; correlations between esds in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell esds is used for estimating esds involving l.s. planes. |
Refinement. Refinement progress was checked using Platon (Spek, 2020) and by an R-tensor (Parkin, 2000). The final model was further checked with the IUCr utility checkCIF. |
x | y | z | Uiso*/Ueq | Occ. (<1) | |
O1 | 0.82422 (17) | 0.32282 (9) | 0.66770 (6) | 0.0204 (2) | |
H1O | 0.781 (3) | 0.3907 (18) | 0.6831 (12) | 0.037 (5)* | |
N1 | 0.28880 (18) | 0.3218 (1) | 0.83935 (7) | 0.0149 (2) | |
H1N | 0.343 (3) | 0.4029 (18) | 0.8331 (12) | 0.040 (5)* | |
C2 | 0.4351 (2) | 0.30509 (12) | 0.69168 (8) | 0.0173 (3) | |
H2A | 0.415565 | 0.389099 | 0.691340 | 0.021* | |
H2B | 0.312841 | 0.274844 | 0.670545 | 0.021* | |
C3 | 0.4311 (2) | 0.25491 (12) | 0.77785 (8) | 0.0185 (3) | |
H3A | 0.379240 | 0.175688 | 0.782916 | 0.022* | |
H3B | 0.581117 | 0.251798 | 0.789138 | 0.022* | |
C4 | 0.0570 (2) | 0.33002 (12) | 0.82710 (9) | 0.0191 (3) | |
H4A | −0.000299 | 0.252326 | 0.828888 | 0.023* | |
H4B | 0.049986 | 0.368697 | 0.773374 | 0.023* | |
C5 | −0.0824 (2) | 0.39645 (12) | 0.89201 (9) | 0.0223 (3) | |
H5A | −0.235727 | 0.397598 | 0.884423 | 0.027* | |
H5B | −0.033901 | 0.476326 | 0.886619 | 0.027* | |
C6 | −0.0675 (3) | 0.34350 (13) | 0.97607 (9) | 0.0260 (3) | |
H6A | −0.153718 | 0.390390 | 1.017119 | 0.031* | |
H6B | −0.127707 | 0.265915 | 0.983520 | 0.031* | |
C7 | 0.1686 (3) | 0.33709 (13) | 0.98665 (8) | 0.0233 (3) | |
H7A | 0.224705 | 0.415231 | 0.983490 | 0.028* | |
H7B | 0.179046 | 0.299809 | 1.040486 | 0.028* | |
C8 | 0.3055 (2) | 0.26997 (12) | 0.92196 (8) | 0.0187 (3) | |
H8A | 0.459291 | 0.268557 | 0.928976 | 0.022* | |
H8B | 0.256145 | 0.190218 | 0.927814 | 0.022* | |
C1 | 0.6509 (2) | 0.27540 (12) | 0.63673 (8) | 0.0164 (3) | |
C9 | 0.6913 (11) | 0.1497 (8) | 0.6352 (4) | 0.0153 (7) | 0.503 (4) |
C10 | 0.9061 (5) | 0.1091 (3) | 0.6302 (2) | 0.0200 (6) | 0.503 (4) |
H10 | 1.017442 | 0.161637 | 0.630723 | 0.024* | 0.503 (4) |
C11 | 0.9611 (8) | −0.0066 (3) | 0.6246 (3) | 0.0202 (8) | 0.503 (4) |
H11 | 1.107859 | −0.032621 | 0.621441 | 0.024* | 0.503 (4) |
C12 | 0.7960 (9) | −0.0841 (6) | 0.6235 (3) | 0.0200 (8) | 0.503 (4) |
H12 | 0.830948 | −0.163027 | 0.619228 | 0.024* | 0.503 (4) |
C13 | 0.5802 (7) | −0.0449 (4) | 0.6288 (3) | 0.0217 (8) | 0.503 (4) |
H13 | 0.468533 | −0.097386 | 0.628653 | 0.026* | 0.503 (4) |
C14 | 0.5286 (14) | 0.0713 (6) | 0.6344 (5) | 0.0185 (6) | 0.503 (4) |
H14 | 0.381829 | 0.097303 | 0.637796 | 0.022* | 0.503 (4) |
C15 | 0.639 (2) | 0.3364 (10) | 0.5511 (7) | 0.0156 (12) | 0.503 (4) |
H15 | 0.595441 | 0.417765 | 0.559790 | 0.019* | 0.503 (4) |
C16 | 0.863 (2) | 0.3384 (9) | 0.4978 (8) | 0.0172 (13) | 0.503 (4) |
H16A | 0.914545 | 0.259178 | 0.488027 | 0.021* | 0.503 (4) |
H16B | 0.967116 | 0.373263 | 0.525847 | 0.021* | 0.503 (4) |
C17 | 0.858 (2) | 0.4059 (9) | 0.4174 (7) | 0.0191 (5) | 0.503 (4) |
H17A | 0.818716 | 0.486717 | 0.426845 | 0.023* | 0.503 (4) |
H17B | 1.004414 | 0.403480 | 0.383390 | 0.023* | 0.503 (4) |
C18 | 0.695 (2) | 0.3579 (7) | 0.3737 (6) | 0.0202 (12) | 0.503 (4) |
H18A | 0.740979 | 0.279132 | 0.360210 | 0.024* | 0.503 (4) |
H18B | 0.690913 | 0.404932 | 0.322736 | 0.024* | 0.503 (4) |
C19 | 0.471 (2) | 0.3569 (10) | 0.4260 (8) | 0.0188 (12) | 0.503 (4) |
H19A | 0.368218 | 0.321764 | 0.397780 | 0.023* | 0.503 (4) |
H19B | 0.420477 | 0.436353 | 0.435100 | 0.023* | 0.503 (4) |
C20 | 0.475 (2) | 0.2905 (11) | 0.5065 (8) | 0.0191 (10) | 0.503 (4) |
H20A | 0.511136 | 0.209320 | 0.497424 | 0.023* | 0.503 (4) |
H20B | 0.328551 | 0.294531 | 0.540256 | 0.023* | 0.503 (4) |
C9' | 0.662 (2) | 0.3164 (9) | 0.5487 (7) | 0.0156 (12) | 0.497 (4) |
C10' | 0.851 (2) | 0.3635 (8) | 0.5021 (8) | 0.0172 (13) | 0.497 (4) |
H10' | 0.973969 | 0.372373 | 0.526510 | 0.021* | 0.497 (4) |
C11' | 0.862 (2) | 0.3977 (9) | 0.4201 (7) | 0.0191 (5) | 0.497 (4) |
H11' | 0.991624 | 0.429451 | 0.389556 | 0.023* | 0.497 (4) |
C12' | 0.682 (2) | 0.3850 (7) | 0.3834 (6) | 0.0202 (12) | 0.497 (4) |
H12' | 0.688241 | 0.407963 | 0.327914 | 0.024* | 0.497 (4) |
C13' | 0.492 (2) | 0.3382 (10) | 0.4292 (8) | 0.0188 (12) | 0.497 (4) |
H13' | 0.369144 | 0.329390 | 0.404641 | 0.023* | 0.497 (4) |
C14' | 0.482 (2) | 0.3043 (11) | 0.5110 (8) | 0.0191 (10) | 0.497 (4) |
H14' | 0.352773 | 0.272635 | 0.541527 | 0.023* | 0.497 (4) |
C15' | 0.7100 (12) | 0.1425 (8) | 0.6432 (4) | 0.0153 (7) | 0.497 (4) |
H15' | 0.730895 | 0.122954 | 0.699947 | 0.018* | 0.497 (4) |
C16' | 0.5296 (15) | 0.0665 (6) | 0.6297 (6) | 0.0200 (6) | 0.497 (4) |
H16C | 0.391453 | 0.087722 | 0.664630 | 0.024* | 0.497 (4) |
H16D | 0.509202 | 0.078531 | 0.572899 | 0.024* | 0.497 (4) |
C17' | 0.5852 (7) | −0.0584 (4) | 0.6487 (3) | 0.0202 (8) | 0.497 (4) |
H17C | 0.467720 | −0.106094 | 0.638287 | 0.024* | 0.497 (4) |
H17D | 0.594430 | −0.071330 | 0.706574 | 0.024* | 0.497 (4) |
C18' | 0.7999 (9) | −0.0947 (6) | 0.5981 (3) | 0.0200 (8) | 0.497 (4) |
H18C | 0.838653 | −0.173790 | 0.616098 | 0.024* | 0.497 (4) |
H18D | 0.783465 | −0.093545 | 0.540911 | 0.024* | 0.497 (4) |
C19' | 0.9794 (8) | −0.0169 (4) | 0.6051 (4) | 0.0217 (8) | 0.497 (4) |
H19C | 1.110868 | −0.036668 | 0.566067 | 0.026* | 0.497 (4) |
H19D | 1.014763 | −0.029729 | 0.659896 | 0.026* | 0.497 (4) |
C20' | 0.9217 (5) | 0.1084 (2) | 0.5897 (3) | 0.0185 (6) | 0.497 (4) |
H20C | 0.907689 | 0.124037 | 0.532398 | 0.022* | 0.497 (4) |
H20D | 1.040472 | 0.155317 | 0.599858 | 0.022* | 0.497 (4) |
O2 | 0.40809 (17) | 0.53766 (9) | 0.83371 (6) | 0.0228 (2) | |
O3 | 0.71358 (18) | 0.52200 (9) | 0.74198 (6) | 0.0271 (3) | |
O4 | 1.0546 (2) | 1.02209 (11) | 0.85879 (11) | 0.0526 (4) | |
O5 | 0.7218 (2) | 1.07163 (11) | 0.90394 (11) | 0.0524 (4) | |
N2 | 0.8591 (2) | 1.00387 (12) | 0.87272 (10) | 0.0365 (4) | |
C21 | 0.5869 (2) | 0.57318 (12) | 0.79342 (8) | 0.0179 (3) | |
C22 | 0.6545 (2) | 0.68961 (11) | 0.81174 (8) | 0.0170 (3) | |
C23 | 0.8706 (2) | 0.72132 (12) | 0.78779 (8) | 0.0191 (3) | |
H23 | 0.972057 | 0.671709 | 0.757832 | 0.023* | |
C24 | 0.9384 (2) | 0.82466 (12) | 0.80738 (9) | 0.0214 (3) | |
H24 | 1.085757 | 0.846162 | 0.791836 | 0.026* | |
C25 | 0.7863 (3) | 0.89562 (12) | 0.85005 (10) | 0.0246 (3) | |
C26 | 0.5694 (3) | 0.86797 (13) | 0.87355 (11) | 0.0287 (4) | |
H26 | 0.467630 | 0.918967 | 0.901992 | 0.034* | |
C27 | 0.5057 (2) | 0.76343 (12) | 0.85422 (9) | 0.0223 (3) | |
H27 | 0.358403 | 0.742036 | 0.870235 | 0.027* |
U11 | U22 | U33 | U12 | U13 | U23 | |
O1 | 0.0231 (5) | 0.0180 (5) | 0.0231 (5) | −0.0037 (4) | −0.0100 (4) | −0.0046 (4) |
N1 | 0.0161 (6) | 0.0155 (6) | 0.0135 (5) | −0.0013 (4) | −0.0030 (4) | −0.0018 (4) |
C2 | 0.0211 (7) | 0.0168 (7) | 0.0149 (6) | 0.0012 (5) | −0.0049 (5) | −0.0026 (5) |
C3 | 0.0202 (7) | 0.0192 (7) | 0.0157 (7) | 0.0044 (5) | −0.0022 (5) | −0.0031 (5) |
C4 | 0.0171 (7) | 0.0188 (7) | 0.0229 (7) | −0.0018 (5) | −0.0063 (5) | −0.0035 (5) |
C5 | 0.0186 (7) | 0.0185 (7) | 0.0281 (8) | 0.0008 (5) | 0.0001 (6) | −0.0006 (6) |
C6 | 0.0306 (8) | 0.0181 (7) | 0.0240 (8) | 0.0012 (6) | 0.0080 (6) | 0.0008 (6) |
C7 | 0.0370 (9) | 0.0178 (7) | 0.0137 (7) | −0.0004 (6) | −0.0010 (6) | 0.0003 (5) |
C8 | 0.0233 (7) | 0.0183 (7) | 0.0145 (6) | −0.0008 (5) | −0.0043 (5) | 0.0009 (5) |
C1 | 0.0177 (6) | 0.0171 (7) | 0.0155 (6) | −0.0039 (5) | −0.0045 (5) | −0.0028 (5) |
C9 | 0.0155 (11) | 0.0162 (11) | 0.0147 (12) | −0.0003 (9) | −0.0040 (9) | −0.0019 (9) |
C10 | 0.0188 (13) | 0.0194 (14) | 0.0221 (14) | −0.0033 (10) | −0.0039 (9) | −0.0018 (9) |
C11 | 0.0217 (15) | 0.0168 (13) | 0.024 (2) | −0.0003 (10) | −0.0081 (11) | −0.0012 (9) |
C12 | 0.0237 (9) | 0.0163 (13) | 0.020 (3) | 0.0006 (8) | −0.0031 (17) | −0.0017 (19) |
C13 | 0.0210 (15) | 0.0209 (14) | 0.025 (2) | −0.0009 (10) | −0.0069 (11) | −0.0045 (10) |
C14 | 0.0134 (12) | 0.0168 (13) | 0.0243 (15) | 0.0006 (9) | 0.0004 (9) | −0.0043 (9) |
C15 | 0.017 (2) | 0.013 (3) | 0.0174 (8) | −0.001 (2) | −0.0035 (11) | −0.0007 (16) |
C16 | 0.0158 (13) | 0.018 (4) | 0.0177 (12) | −0.002 (2) | −0.0027 (10) | −0.004 (2) |
C17 | 0.0177 (8) | 0.0186 (12) | 0.0192 (9) | −0.0011 (8) | 0.0009 (6) | −0.0005 (9) |
C18 | 0.0247 (15) | 0.019 (4) | 0.015 (2) | 0.001 (3) | −0.0024 (15) | 0.001 (2) |
C19 | 0.0205 (19) | 0.018 (3) | 0.0185 (10) | 0.0010 (18) | −0.0055 (11) | −0.0008 (18) |
C20 | 0.0167 (9) | 0.024 (2) | 0.0173 (13) | −0.0028 (13) | −0.0033 (8) | −0.0019 (15) |
C9' | 0.017 (2) | 0.013 (3) | 0.0174 (8) | −0.001 (2) | −0.0035 (11) | −0.0007 (16) |
C10' | 0.0158 (13) | 0.018 (4) | 0.0177 (12) | −0.002 (2) | −0.0027 (10) | −0.004 (2) |
C11' | 0.0177 (8) | 0.0186 (12) | 0.0192 (9) | −0.0011 (8) | 0.0009 (6) | −0.0005 (9) |
C12' | 0.0247 (15) | 0.019 (4) | 0.015 (2) | 0.001 (3) | −0.0024 (15) | 0.001 (2) |
C13' | 0.0205 (19) | 0.018 (3) | 0.0185 (10) | 0.0010 (18) | −0.0055 (11) | −0.0008 (18) |
C14' | 0.0167 (9) | 0.024 (2) | 0.0173 (13) | −0.0028 (13) | −0.0033 (8) | −0.0019 (15) |
C15' | 0.0155 (11) | 0.0162 (11) | 0.0147 (12) | −0.0003 (9) | −0.0040 (9) | −0.0019 (9) |
C16' | 0.0188 (13) | 0.0194 (14) | 0.0221 (14) | −0.0033 (10) | −0.0039 (9) | −0.0018 (9) |
C17' | 0.0217 (15) | 0.0168 (13) | 0.024 (2) | −0.0003 (10) | −0.0081 (11) | −0.0012 (9) |
C18' | 0.0237 (9) | 0.0163 (13) | 0.020 (3) | 0.0006 (8) | −0.0031 (17) | −0.0017 (19) |
C19' | 0.0210 (15) | 0.0209 (14) | 0.025 (2) | −0.0009 (10) | −0.0069 (11) | −0.0045 (10) |
C20' | 0.0134 (12) | 0.0168 (13) | 0.0243 (15) | 0.0006 (9) | 0.0004 (9) | −0.0043 (9) |
O2 | 0.0253 (5) | 0.0184 (5) | 0.0243 (5) | −0.0074 (4) | −0.0022 (4) | −0.0011 (4) |
O3 | 0.0324 (6) | 0.0253 (6) | 0.0235 (6) | −0.0079 (5) | 0.0002 (5) | −0.0103 (4) |
O4 | 0.0333 (7) | 0.0273 (7) | 0.1028 (13) | −0.0086 (6) | −0.0199 (8) | −0.0171 (7) |
O5 | 0.0425 (8) | 0.0214 (6) | 0.0975 (12) | 0.0029 (6) | −0.0154 (8) | −0.0250 (7) |
N2 | 0.0337 (8) | 0.0158 (7) | 0.0639 (11) | −0.0020 (6) | −0.0171 (7) | −0.0070 (7) |
C21 | 0.0240 (7) | 0.0163 (7) | 0.0146 (6) | −0.0039 (5) | −0.0069 (5) | 0.0007 (5) |
C22 | 0.0223 (7) | 0.0151 (6) | 0.0145 (6) | −0.0039 (5) | −0.0065 (5) | 0.0022 (5) |
C23 | 0.0219 (7) | 0.0192 (7) | 0.0158 (6) | −0.0026 (5) | −0.0024 (5) | −0.0005 (5) |
C24 | 0.0216 (7) | 0.0195 (7) | 0.0238 (7) | −0.0057 (6) | −0.0071 (6) | 0.0034 (6) |
C25 | 0.0277 (8) | 0.0118 (7) | 0.0368 (9) | −0.0027 (6) | −0.0127 (7) | −0.0006 (6) |
C26 | 0.0240 (8) | 0.0161 (7) | 0.0473 (10) | 0.0039 (6) | −0.0087 (7) | −0.0067 (7) |
C27 | 0.0178 (7) | 0.0182 (7) | 0.0317 (8) | −0.0009 (5) | −0.0068 (6) | 0.0000 (6) |
O1—C1 | 1.4358 (16) | C18—H18A | 0.9900 |
O1—H1O | 0.88 (2) | C18—H18B | 0.9900 |
N1—C3 | 1.4953 (17) | C19—C20 | 1.516 (7) |
N1—C8 | 1.4982 (17) | C19—H19A | 0.9900 |
N1—C4 | 1.5004 (17) | C19—H19B | 0.9900 |
N1—H1N | 1.01 (2) | C20—H20A | 0.9900 |
C2—C3 | 1.5235 (18) | C20—H20B | 0.9900 |
C2—C1 | 1.5396 (19) | C9'—C10' | 1.404 (7) |
C2—H2A | 0.9900 | C9'—C14' | 1.405 (7) |
C2—H2B | 0.9900 | C10'—C11' | 1.401 (6) |
C3—H3A | 0.9900 | C10'—H10' | 0.9500 |
C3—H3B | 0.9900 | C11'—C12' | 1.402 (7) |
C4—C5 | 1.522 (2) | C11'—H11' | 0.9500 |
C4—H4A | 0.9900 | C12'—C13' | 1.400 (7) |
C4—H4B | 0.9900 | C12'—H12' | 0.9500 |
C5—C6 | 1.522 (2) | C13'—C14' | 1.401 (7) |
C5—H5A | 0.9900 | C13'—H13' | 0.9500 |
C5—H5B | 0.9900 | C14'—H14' | 0.9500 |
C6—C7 | 1.518 (2) | C15'—C20' | 1.522 (7) |
C6—H6A | 0.9900 | C15'—C16' | 1.526 (7) |
C6—H6B | 0.9900 | C15'—H15' | 1.0000 |
C7—C8 | 1.517 (2) | C16'—C17' | 1.518 (7) |
C7—H7A | 0.9900 | C16'—H16C | 0.9900 |
C7—H7B | 0.9900 | C16'—H16D | 0.9900 |
C8—H8A | 0.9900 | C17'—C18' | 1.522 (6) |
C8—H8B | 0.9900 | C17'—H17C | 0.9900 |
C1—C9 | 1.490 (9) | C17'—H17D | 0.9900 |
C1—C9' | 1.517 (11) | C18'—C19' | 1.502 (6) |
C1—C15 | 1.576 (11) | C18'—H18C | 0.9900 |
C1—C15' | 1.592 (10) | C18'—H18D | 0.9900 |
C9—C10 | 1.399 (7) | C19'—C20' | 1.516 (5) |
C9—C14 | 1.402 (7) | C19'—H19C | 0.9900 |
C10—C11 | 1.397 (5) | C19'—H19D | 0.9900 |
C10—H10 | 0.9500 | C20'—H20C | 0.9900 |
C11—C12 | 1.407 (6) | C20'—H20D | 0.9900 |
C11—H11 | 0.9500 | O2—C21 | 1.2661 (17) |
C12—C13 | 1.399 (6) | O3—C21 | 1.2431 (18) |
C12—H12 | 0.9500 | O4—N2 | 1.227 (2) |
C13—C14 | 1.398 (6) | O5—N2 | 1.226 (2) |
C13—H13 | 0.9500 | N2—C25 | 1.4698 (19) |
C14—H14 | 0.9500 | C21—C22 | 1.5197 (19) |
C15—C20 | 1.519 (7) | C22—C27 | 1.390 (2) |
C15—C16 | 1.521 (7) | C22—C23 | 1.395 (2) |
C15—H15 | 1.0000 | C23—C24 | 1.386 (2) |
C16—C17 | 1.523 (7) | C23—H23 | 0.9500 |
C16—H16A | 0.9900 | C24—C25 | 1.382 (2) |
C16—H16B | 0.9900 | C24—H24 | 0.9500 |
C17—C18 | 1.512 (7) | C25—C26 | 1.387 (2) |
C17—H17A | 0.9900 | C26—C27 | 1.388 (2) |
C17—H17B | 0.9900 | C26—H26 | 0.9500 |
C18—C19 | 1.515 (7) | C27—H27 | 0.9500 |
C1—O1—H1O | 107.8 (13) | C17—C18—C19 | 110.3 (6) |
C3—N1—C8 | 109.22 (10) | C17—C18—H18A | 109.6 |
C3—N1—C4 | 112.50 (11) | C19—C18—H18A | 109.6 |
C8—N1—C4 | 111.30 (11) | C17—C18—H18B | 109.6 |
C3—N1—H1N | 108.1 (11) | C19—C18—H18B | 109.6 |
C8—N1—H1N | 109.2 (11) | H18A—C18—H18B | 108.1 |
C4—N1—H1N | 106.4 (11) | C18—C19—C20 | 111.0 (6) |
C3—C2—C1 | 111.20 (11) | C18—C19—H19A | 109.4 |
C3—C2—H2A | 109.4 | C20—C19—H19A | 109.4 |
C1—C2—H2A | 109.4 | C18—C19—H19B | 109.4 |
C3—C2—H2B | 109.4 | C20—C19—H19B | 109.4 |
C1—C2—H2B | 109.4 | H19A—C19—H19B | 108.0 |
H2A—C2—H2B | 108.0 | C19—C20—C15 | 112.1 (7) |
N1—C3—C2 | 113.20 (11) | C19—C20—H20A | 109.2 |
N1—C3—H3A | 108.9 | C15—C20—H20A | 109.2 |
C2—C3—H3A | 108.9 | C19—C20—H20B | 109.2 |
N1—C3—H3B | 108.9 | C15—C20—H20B | 109.2 |
C2—C3—H3B | 108.9 | H20A—C20—H20B | 107.9 |
H3A—C3—H3B | 107.8 | C10'—C9'—C14' | 118.1 (7) |
N1—C4—C5 | 110.64 (11) | C10'—C9'—C1 | 121.7 (10) |
N1—C4—H4A | 109.5 | C14'—C9'—C1 | 120.1 (10) |
C5—C4—H4A | 109.5 | C11'—C10'—C9' | 121.3 (7) |
N1—C4—H4B | 109.5 | C11'—C10'—H10' | 119.3 |
C5—C4—H4B | 109.5 | C9'—C10'—H10' | 119.3 |
H4A—C4—H4B | 108.1 | C10'—C11'—C12' | 119.8 (7) |
C4—C5—C6 | 111.42 (12) | C10'—C11'—H11' | 120.1 |
C4—C5—H5A | 109.3 | C12'—C11'—H11' | 120.1 |
C6—C5—H5A | 109.3 | C13'—C12'—C11' | 119.5 (7) |
C4—C5—H5B | 109.3 | C13'—C12'—H12' | 120.2 |
C6—C5—H5B | 109.3 | C11'—C12'—H12' | 120.2 |
H5A—C5—H5B | 108.0 | C12'—C13'—C14' | 120.2 (7) |
C7—C6—C5 | 109.47 (12) | C12'—C13'—H13' | 119.9 |
C7—C6—H6A | 109.8 | C14'—C13'—H13' | 119.9 |
C5—C6—H6A | 109.8 | C13'—C14'—C9' | 121.0 (7) |
C7—C6—H6B | 109.8 | C13'—C14'—H14' | 119.5 |
C5—C6—H6B | 109.8 | C9'—C14'—H14' | 119.5 |
H6A—C6—H6B | 108.2 | C20'—C15'—C16' | 109.0 (6) |
C8—C7—C6 | 110.62 (12) | C20'—C15'—C1 | 114.6 (5) |
C8—C7—H7A | 109.5 | C16'—C15'—C1 | 114.1 (5) |
C6—C7—H7A | 109.5 | C20'—C15'—H15' | 106.1 |
C8—C7—H7B | 109.5 | C16'—C15'—H15' | 106.1 |
C6—C7—H7B | 109.5 | C1—C15'—H15' | 106.1 |
H7A—C7—H7B | 108.1 | C17'—C16'—C15' | 110.7 (6) |
N1—C8—C7 | 111.18 (11) | C17'—C16'—H16C | 109.5 |
N1—C8—H8A | 109.4 | C15'—C16'—H16C | 109.5 |
C7—C8—H8A | 109.4 | C17'—C16'—H16D | 109.5 |
N1—C8—H8B | 109.4 | C15'—C16'—H16D | 109.5 |
C7—C8—H8B | 109.4 | H16C—C16'—H16D | 108.1 |
H8A—C8—H8B | 108.0 | C16'—C17'—C18' | 111.6 (5) |
O1—C1—C9 | 108.1 (3) | C16'—C17'—H17C | 109.3 |
O1—C1—C9' | 110.1 (6) | C18'—C17'—H17C | 109.3 |
O1—C1—C2 | 108.07 (11) | C16'—C17'—H17D | 109.3 |
C9—C1—C2 | 112.1 (3) | C18'—C17'—H17D | 109.3 |
C9'—C1—C2 | 114.3 (5) | H17C—C17'—H17D | 108.0 |
O1—C1—C15 | 109.0 (5) | C19'—C18'—C17' | 111.4 (4) |
C9—C1—C15 | 113.1 (5) | C19'—C18'—H18C | 109.4 |
C2—C1—C15 | 106.3 (5) | C17'—C18'—H18C | 109.4 |
O1—C1—C15' | 102.0 (3) | C19'—C18'—H18D | 109.4 |
C9'—C1—C15' | 109.1 (5) | C17'—C18'—H18D | 109.4 |
C2—C1—C15' | 112.5 (3) | H18C—C18'—H18D | 108.0 |
C10—C9—C14 | 118.5 (6) | C18'—C19'—C20' | 113.1 (4) |
C10—C9—C1 | 117.6 (5) | C18'—C19'—H19C | 109.0 |
C14—C9—C1 | 123.8 (5) | C20'—C19'—H19C | 109.0 |
C11—C10—C9 | 121.7 (5) | C18'—C19'—H19D | 109.0 |
C11—C10—H10 | 119.1 | C20'—C19'—H19D | 109.0 |
C9—C10—H10 | 119.1 | H19C—C19'—H19D | 107.8 |
C10—C11—C12 | 119.0 (4) | C19'—C20'—C15' | 111.7 (4) |
C10—C11—H11 | 120.5 | C19'—C20'—H20C | 109.3 |
C12—C11—H11 | 120.5 | C15'—C20'—H20C | 109.3 |
C13—C12—C11 | 119.9 (5) | C19'—C20'—H20D | 109.3 |
C13—C12—H12 | 120.0 | C15'—C20'—H20D | 109.3 |
C11—C12—H12 | 120.0 | H20C—C20'—H20D | 107.9 |
C14—C13—C12 | 120.1 (5) | O5—N2—O4 | 123.33 (14) |
C14—C13—H13 | 119.9 | O5—N2—C25 | 118.52 (14) |
C12—C13—H13 | 119.9 | O4—N2—C25 | 118.15 (14) |
C13—C14—C9 | 120.7 (6) | O3—C21—O2 | 126.87 (13) |
C13—C14—H14 | 119.7 | O3—C21—C22 | 117.08 (12) |
C9—C14—H14 | 119.7 | O2—C21—C22 | 116.04 (12) |
C20—C15—C16 | 109.9 (6) | C27—C22—C23 | 119.55 (13) |
C20—C15—C1 | 116.1 (9) | C27—C22—C21 | 120.94 (13) |
C16—C15—C1 | 110.7 (8) | C23—C22—C21 | 119.48 (13) |
C20—C15—H15 | 106.5 | C24—C23—C22 | 120.50 (14) |
C16—C15—H15 | 106.5 | C24—C23—H23 | 119.8 |
C1—C15—H15 | 106.5 | C22—C23—H23 | 119.7 |
C15—C16—C17 | 111.3 (6) | C25—C24—C23 | 118.38 (14) |
C15—C16—H16A | 109.4 | C25—C24—H24 | 120.8 |
C17—C16—H16A | 109.4 | C23—C24—H24 | 120.8 |
C15—C16—H16B | 109.4 | C24—C25—C26 | 122.75 (14) |
C17—C16—H16B | 109.4 | C24—C25—N2 | 118.45 (14) |
H16A—C16—H16B | 108.0 | C26—C25—N2 | 118.80 (14) |
C18—C17—C16 | 111.1 (6) | C25—C26—C27 | 117.89 (15) |
C18—C17—H17A | 109.4 | C25—C26—H26 | 121.1 |
C16—C17—H17A | 109.4 | C27—C26—H26 | 121.1 |
C18—C17—H17B | 109.4 | C26—C27—C22 | 120.92 (14) |
C16—C17—H17B | 109.4 | C26—C27—H27 | 119.5 |
H17A—C17—H17B | 108.0 | C22—C27—H27 | 119.5 |
C8—N1—C3—C2 | −176.78 (11) | C2—C1—C9'—C10' | 139.3 (6) |
C4—N1—C3—C2 | 59.11 (15) | C15'—C1—C9'—C10' | −93.7 (7) |
C1—C2—C3—N1 | 152.29 (11) | O1—C1—C9'—C14' | −164.6 (5) |
C3—N1—C4—C5 | 178.76 (11) | C2—C1—C9'—C14' | −42.8 (7) |
C8—N1—C4—C5 | 55.81 (14) | C15'—C1—C9'—C14' | 84.1 (7) |
N1—C4—C5—C6 | −56.25 (16) | C14'—C9'—C10'—C11' | 0.0 (3) |
C4—C5—C6—C7 | 56.67 (16) | C1—C9'—C10'—C11' | 177.9 (8) |
C5—C6—C7—C8 | −56.90 (16) | C9'—C10'—C11'—C12' | 0.0 (3) |
C3—N1—C8—C7 | 178.38 (12) | C10'—C11'—C12'—C13' | 0.0 (6) |
C4—N1—C8—C7 | −56.81 (15) | C11'—C12'—C13'—C14' | 0.0 (8) |
C6—C7—C8—N1 | 57.53 (15) | C12'—C13'—C14'—C9' | 0.0 (8) |
C3—C2—C1—O1 | −60.52 (14) | C10'—C9'—C14'—C13' | 0.0 (6) |
C3—C2—C1—C9 | 58.5 (3) | C1—C9'—C14'—C13' | −177.9 (9) |
C3—C2—C1—C9' | 176.5 (5) | O1—C1—C15'—C20' | −64.7 (6) |
C3—C2—C1—C15 | −177.4 (5) | C9'—C1—C15'—C20' | 51.8 (8) |
C3—C2—C1—C15' | 51.3 (3) | C2—C1—C15'—C20' | 179.7 (4) |
O1—C1—C9—C10 | −25.0 (5) | O1—C1—C15'—C16' | 168.6 (4) |
C2—C1—C9—C10 | −144.1 (3) | C9'—C1—C15'—C16' | −74.9 (7) |
C15—C1—C9—C10 | 95.7 (7) | C2—C1—C15'—C16' | 53.1 (5) |
O1—C1—C9—C14 | 158.2 (4) | C20'—C15'—C16'—C17' | 58.7 (7) |
C2—C1—C9—C14 | 39.1 (5) | C1—C15'—C16'—C17' | −171.8 (5) |
C15—C1—C9—C14 | −81.1 (7) | C15'—C16'—C17'—C18' | −57.6 (7) |
C14—C9—C10—C11 | 0.1 (3) | C16'—C17'—C18'—C19' | 53.0 (6) |
C1—C9—C10—C11 | −176.9 (5) | C17'—C18'—C19'—C20' | −51.2 (6) |
C9—C10—C11—C12 | 0.2 (2) | C18'—C19'—C20'—C15' | 54.0 (6) |
C10—C11—C12—C13 | −0.5 (5) | C16'—C15'—C20'—C19' | −56.6 (6) |
C11—C12—C13—C14 | 0.6 (6) | C1—C15'—C20'—C19' | 174.1 (5) |
C12—C13—C14—C9 | −0.3 (7) | O3—C21—C22—C27 | 165.70 (13) |
C10—C9—C14—C13 | 0.0 (6) | O2—C21—C22—C27 | −15.63 (19) |
C1—C9—C14—C13 | 176.7 (6) | O3—C21—C22—C23 | −16.34 (19) |
O1—C1—C15—C20 | 175.6 (5) | O2—C21—C22—C23 | 162.33 (13) |
C9—C1—C15—C20 | 55.4 (8) | C27—C22—C23—C24 | 1.2 (2) |
C2—C1—C15—C20 | −68.1 (6) | C21—C22—C23—C24 | −176.75 (13) |
O1—C1—C15—C16 | 49.4 (7) | C22—C23—C24—C25 | −0.9 (2) |
C9—C1—C15—C16 | −70.9 (7) | C23—C24—C25—C26 | −0.4 (2) |
C2—C1—C15—C16 | 165.6 (5) | C23—C24—C25—N2 | 178.42 (14) |
C20—C15—C16—C17 | 55.2 (7) | O5—N2—C25—C24 | 173.37 (16) |
C1—C15—C16—C17 | −175.1 (8) | O4—N2—C25—C24 | −6.1 (2) |
C15—C16—C17—C18 | −57.1 (6) | O5—N2—C25—C26 | −7.8 (2) |
C16—C17—C18—C19 | 57.1 (7) | O4—N2—C25—C26 | 172.74 (17) |
C17—C18—C19—C20 | −56.3 (8) | C24—C25—C26—C27 | 1.2 (2) |
C18—C19—C20—C15 | 56.1 (8) | N2—C25—C26—C27 | −177.59 (15) |
C16—C15—C20—C19 | −55.1 (7) | C25—C26—C27—C22 | −0.8 (2) |
C1—C15—C20—C19 | 178.3 (8) | C23—C22—C27—C26 | −0.4 (2) |
O1—C1—C9'—C10' | 17.5 (8) | C21—C22—C27—C26 | 177.57 (14) |
D—H···A | D—H | H···A | D···A | D—H···A |
O1—H1O···O3 | 0.88 (2) | 1.90 (2) | 2.7527 (15) | 164.5 (19) |
N1—H1N···O2 | 1.01 (2) | 1.65 (2) | 2.6618 (15) | 172.6 (18) |
C4—H4B···O1i | 0.99 | 2.57 | 3.2972 (17) | 130 |
Symmetry code: (i) x−1, y, z. |
C20H32NO+·C7H5O− | F(000) = 1904 |
Mr = 439.57 | Dx = 1.255 Mg m−3 |
Monoclinic, C2/c | Mo Kα radiation, λ = 0.71073 Å |
a = 45.098 (2) Å | Cell parameters from 9845 reflections |
b = 8.5314 (5) Å | θ = 2.4–27.5° |
c = 12.3516 (6) Å | µ = 0.08 mm−1 |
β = 101.789 (2)° | T = 90 K |
V = 4652.0 (4) Å3 | Plate, colourless |
Z = 8 | 0.25 × 0.20 × 0.04 mm |
Bruker D8 Venture dual source diffractometer | 5327 independent reflections |
Radiation source: microsource | 4543 reflections with I > 2σ(I) |
Detector resolution: 7.41 pixels mm-1 | Rint = 0.062 |
φ and ω scans | θmax = 27.5°, θmin = 2.4° |
Absorption correction: multi-scan (TWINABS; Sheldrick, 2012) | h = −58→57 |
Tmin = 0.706, Tmax = 0.959 | k = 0→11 |
5327 measured reflections | l = 0→16 |
Refinement on F2 | Secondary atom site location: difference Fourier map |
Least-squares matrix: full | Hydrogen site location: mixed |
R[F2 > 2σ(F2)] = 0.041 | H atoms treated by a mixture of independent and constrained refinement |
wR(F2) = 0.090 | w = 1/[σ2(Fo2) + (0.0332P)2 + 1.3379P] where P = (Fo2 + 2Fc2)/3 |
S = 1.03 | (Δ/σ)max = 0.001 |
5327 reflections | Δρmax = 0.28 e Å−3 |
303 parameters | Δρmin = −0.28 e Å−3 |
0 restraints | Extinction correction: SHELXL-2019/2 (Sheldrick 2008), Fc*=kFc[1+0.001xFc2λ3/sin(2θ)]-1/4 |
Primary atom site location: structure-invariant direct methods | Extinction coefficient: 0.0030 (5) |
Experimental. The crystal was mounted using polyisobutene oil on the tip of a fine glass fibre, which was fastened in a copper mounting pin with electrical solder. It was placed directly into the cold gas stream of a liquid-nitrogen based cryostat (Hope, 1994; Parkin & Hope, 1998). Diffraction data were collected with the crystal at 90K, which is standard practice in this laboratory for the majority of flash-cooled crystals. |
Geometry. All esds (except the esd in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell esds are taken into account individually in the estimation of esds in distances, angles and torsion angles; correlations between esds in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell esds is used for estimating esds involving l.s. planes. |
Refinement. Refined as a two-component twin. |
x | y | z | Uiso*/Ueq | ||
O1 | 0.64503 (3) | 0.47657 (16) | 0.23197 (10) | 0.0197 (3) | |
H1O | 0.6394 (5) | 0.395 (3) | 0.267 (2) | 0.037 (6)* | |
N1 | 0.58510 (3) | 0.60731 (17) | 0.40624 (11) | 0.0145 (3) | |
H1N | 0.5832 (4) | 0.499 (3) | 0.3955 (17) | 0.023 (5)* | |
C1 | 0.66057 (4) | 0.5819 (2) | 0.31582 (14) | 0.0168 (3) | |
C2 | 0.64073 (3) | 0.5992 (2) | 0.40316 (14) | 0.0166 (3) | |
H2A | 0.638047 | 0.495231 | 0.435376 | 0.020* | |
H2B | 0.651117 | 0.668315 | 0.463538 | 0.020* | |
C3 | 0.60976 (3) | 0.6679 (2) | 0.35289 (14) | 0.0185 (4) | |
H3A | 0.610726 | 0.783437 | 0.360334 | 0.022* | |
H3B | 0.604764 | 0.642710 | 0.272994 | 0.022* | |
C4 | 0.59104 (4) | 0.6392 (2) | 0.52798 (13) | 0.0170 (4) | |
H4A | 0.592245 | 0.753753 | 0.541102 | 0.020* | |
H4B | 0.610672 | 0.592309 | 0.563876 | 0.020* | |
C5 | 0.56583 (4) | 0.5702 (2) | 0.57793 (14) | 0.0185 (4) | |
H5A | 0.569629 | 0.595026 | 0.657884 | 0.022* | |
H5B | 0.565790 | 0.454786 | 0.569906 | 0.022* | |
C6 | 0.53495 (4) | 0.6349 (2) | 0.52184 (14) | 0.0215 (4) | |
H6A | 0.518871 | 0.581952 | 0.552046 | 0.026* | |
H6B | 0.534062 | 0.748444 | 0.537538 | 0.026* | |
C7 | 0.52948 (4) | 0.6091 (2) | 0.39728 (15) | 0.0194 (4) | |
H7A | 0.527524 | 0.495443 | 0.381295 | 0.023* | |
H7B | 0.510274 | 0.660366 | 0.361565 | 0.023* | |
C8 | 0.55528 (3) | 0.6755 (2) | 0.34958 (14) | 0.0183 (4) | |
H8A | 0.551751 | 0.651862 | 0.269500 | 0.022* | |
H8B | 0.555856 | 0.790859 | 0.358541 | 0.022* | |
C9 | 0.66395 (3) | 0.7379 (2) | 0.25866 (14) | 0.0161 (4) | |
C10 | 0.65862 (4) | 0.7484 (2) | 0.14377 (15) | 0.0203 (4) | |
H10 | 0.652558 | 0.657720 | 0.100257 | 0.024* | |
C11 | 0.66205 (4) | 0.8899 (2) | 0.09203 (16) | 0.0240 (4) | |
H11 | 0.658087 | 0.895399 | 0.013573 | 0.029* | |
C12 | 0.67121 (4) | 1.0227 (2) | 0.15405 (16) | 0.0251 (4) | |
H12 | 0.673865 | 1.118945 | 0.118511 | 0.030* | |
C13 | 0.67646 (4) | 1.0144 (2) | 0.26827 (16) | 0.0222 (4) | |
H13 | 0.682632 | 1.105283 | 0.311469 | 0.027* | |
C14 | 0.67272 (4) | 0.8732 (2) | 0.31970 (15) | 0.0192 (4) | |
H14 | 0.676227 | 0.868889 | 0.398139 | 0.023* | |
C15 | 0.69159 (4) | 0.5071 (2) | 0.36817 (14) | 0.0176 (4) | |
H15 | 0.686969 | 0.402152 | 0.396860 | 0.021* | |
C16 | 0.71081 (4) | 0.4760 (2) | 0.28197 (16) | 0.0244 (4) | |
H16A | 0.716442 | 0.577069 | 0.252371 | 0.029* | |
H16B | 0.698755 | 0.415569 | 0.219800 | 0.029* | |
C17 | 0.73957 (4) | 0.3845 (3) | 0.33156 (16) | 0.0281 (4) | |
H17A | 0.733941 | 0.278419 | 0.352781 | 0.034* | |
H17B | 0.752121 | 0.372668 | 0.274999 | 0.034* | |
C18 | 0.75806 (4) | 0.4665 (3) | 0.43271 (17) | 0.0276 (4) | |
H18A | 0.775308 | 0.398936 | 0.466766 | 0.033* | |
H18B | 0.766361 | 0.565645 | 0.409679 | 0.033* | |
C19 | 0.73880 (4) | 0.5015 (2) | 0.51730 (16) | 0.0254 (4) | |
H19A | 0.750942 | 0.561859 | 0.579318 | 0.030* | |
H19B | 0.732701 | 0.401767 | 0.547398 | 0.030* | |
C20 | 0.71056 (4) | 0.5949 (2) | 0.46637 (15) | 0.0210 (4) | |
H20A | 0.716603 | 0.698106 | 0.441359 | 0.025* | |
H20B | 0.698238 | 0.613178 | 0.522950 | 0.025* | |
O2 | 0.61716 (3) | 0.24225 (15) | 0.33577 (10) | 0.0223 (3) | |
O3 | 0.57253 (2) | 0.30007 (14) | 0.37676 (10) | 0.0182 (3) | |
O4 | 0.53273 (3) | −0.20004 (15) | −0.00636 (10) | 0.0197 (3) | |
H4O | 0.5455 (5) | −0.227 (3) | −0.042 (2) | 0.042 (7)* | |
C21 | 0.58953 (4) | 0.2187 (2) | 0.32616 (14) | 0.0166 (3) | |
C22 | 0.57456 (3) | 0.0946 (2) | 0.24782 (13) | 0.0145 (3) | |
C23 | 0.54314 (4) | 0.0716 (2) | 0.22493 (14) | 0.0164 (3) | |
H23 | 0.531016 | 0.126006 | 0.267150 | 0.020* | |
C24 | 0.52947 (4) | −0.0294 (2) | 0.14147 (15) | 0.0170 (4) | |
H24 | 0.508153 | −0.044621 | 0.127228 | 0.020* | |
C25 | 0.54707 (4) | −0.10839 (19) | 0.07870 (14) | 0.0150 (3) | |
C26 | 0.57859 (4) | −0.0913 (2) | 0.10326 (14) | 0.0165 (3) | |
H26 | 0.590788 | −0.148204 | 0.062676 | 0.020* | |
C27 | 0.59185 (3) | 0.0093 (2) | 0.18711 (14) | 0.0158 (3) | |
H27 | 0.613258 | 0.020403 | 0.203686 | 0.019* |
U11 | U22 | U33 | U12 | U13 | U23 | |
O1 | 0.0239 (6) | 0.0189 (7) | 0.0149 (6) | −0.0060 (5) | 0.0005 (5) | −0.0013 (5) |
N1 | 0.0151 (6) | 0.0127 (8) | 0.0153 (7) | 0.0001 (5) | 0.0023 (5) | 0.0009 (6) |
C1 | 0.0168 (7) | 0.0178 (9) | 0.0152 (8) | −0.0029 (7) | 0.0021 (6) | −0.0023 (7) |
C2 | 0.0160 (8) | 0.0182 (9) | 0.0152 (8) | −0.0016 (7) | 0.0022 (6) | 0.0005 (7) |
C3 | 0.0177 (8) | 0.0195 (10) | 0.0182 (8) | −0.0018 (7) | 0.0037 (6) | 0.0046 (7) |
C4 | 0.0200 (8) | 0.0175 (9) | 0.0129 (8) | −0.0006 (7) | 0.0018 (6) | −0.0014 (7) |
C5 | 0.0247 (8) | 0.0157 (9) | 0.0156 (8) | −0.0018 (7) | 0.0051 (7) | −0.0011 (7) |
C6 | 0.0193 (8) | 0.0247 (10) | 0.0220 (9) | 0.0003 (7) | 0.0082 (7) | −0.0045 (8) |
C7 | 0.0161 (7) | 0.0187 (10) | 0.0230 (9) | 0.0023 (7) | 0.0028 (7) | −0.0011 (7) |
C8 | 0.0175 (8) | 0.0183 (9) | 0.0180 (8) | 0.0045 (7) | 0.0009 (7) | 0.0024 (7) |
C9 | 0.0110 (7) | 0.0187 (9) | 0.0189 (8) | 0.0002 (6) | 0.0037 (6) | 0.0007 (7) |
C10 | 0.0197 (8) | 0.0219 (10) | 0.0197 (9) | −0.0018 (7) | 0.0054 (7) | −0.0009 (8) |
C11 | 0.0242 (9) | 0.0310 (11) | 0.0180 (9) | 0.0001 (8) | 0.0074 (7) | 0.0053 (8) |
C12 | 0.0218 (8) | 0.0236 (11) | 0.0314 (11) | 0.0000 (7) | 0.0090 (8) | 0.0094 (8) |
C13 | 0.0190 (8) | 0.0189 (10) | 0.0285 (10) | −0.0016 (7) | 0.0048 (7) | 0.0000 (8) |
C14 | 0.0183 (8) | 0.0208 (10) | 0.0188 (9) | 0.0002 (7) | 0.0042 (7) | 0.0002 (7) |
C15 | 0.0181 (7) | 0.0179 (9) | 0.0172 (9) | −0.0001 (7) | 0.0043 (7) | 0.0005 (7) |
C16 | 0.0245 (9) | 0.0300 (11) | 0.0190 (9) | 0.0056 (8) | 0.0053 (7) | 0.0007 (8) |
C17 | 0.0251 (9) | 0.0336 (12) | 0.0269 (10) | 0.0092 (8) | 0.0085 (8) | 0.0006 (9) |
C18 | 0.0185 (8) | 0.0301 (12) | 0.0340 (11) | 0.0035 (7) | 0.0049 (8) | 0.0031 (9) |
C19 | 0.0199 (8) | 0.0295 (11) | 0.0241 (10) | 0.0007 (8) | −0.0018 (7) | −0.0005 (8) |
C20 | 0.0181 (8) | 0.0242 (10) | 0.0193 (9) | 0.0012 (7) | 0.0009 (7) | −0.0019 (7) |
O2 | 0.0210 (6) | 0.0204 (7) | 0.0252 (7) | −0.0035 (5) | 0.0042 (5) | −0.0029 (6) |
O3 | 0.0241 (6) | 0.0147 (6) | 0.0172 (6) | 0.0005 (5) | 0.0074 (5) | −0.0018 (5) |
O4 | 0.0187 (6) | 0.0197 (7) | 0.0202 (6) | −0.0009 (5) | 0.0028 (5) | −0.0051 (5) |
C21 | 0.0243 (8) | 0.0114 (9) | 0.0146 (8) | 0.0013 (7) | 0.0047 (7) | 0.0063 (7) |
C22 | 0.0184 (8) | 0.0118 (8) | 0.0136 (8) | 0.0006 (6) | 0.0038 (6) | 0.0034 (6) |
C23 | 0.0202 (8) | 0.0130 (9) | 0.0175 (8) | 0.0022 (7) | 0.0071 (7) | 0.0024 (7) |
C24 | 0.0154 (7) | 0.0159 (9) | 0.0201 (9) | 0.0002 (6) | 0.0046 (7) | 0.0021 (7) |
C25 | 0.0194 (8) | 0.0104 (8) | 0.0141 (8) | −0.0003 (6) | 0.0010 (6) | 0.0025 (6) |
C26 | 0.0191 (8) | 0.0148 (9) | 0.0163 (8) | 0.0037 (6) | 0.0052 (7) | 0.0015 (7) |
C27 | 0.0170 (7) | 0.0146 (9) | 0.0151 (8) | 0.0008 (7) | 0.0014 (7) | 0.0040 (7) |
O1—C1 | 1.440 (2) | C13—C14 | 1.388 (3) |
O1—H1O | 0.88 (3) | C13—H13 | 0.9500 |
N1—C3 | 1.496 (2) | C14—H14 | 0.9500 |
N1—C4 | 1.497 (2) | C15—C16 | 1.527 (2) |
N1—C8 | 1.501 (2) | C15—C20 | 1.530 (2) |
N1—H1N | 0.94 (2) | C15—H15 | 1.0000 |
C1—C9 | 1.529 (2) | C16—C17 | 1.530 (2) |
C1—C2 | 1.543 (2) | C16—H16A | 0.9900 |
C1—C15 | 1.553 (2) | C16—H16B | 0.9900 |
C2—C3 | 1.525 (2) | C17—C18 | 1.523 (3) |
C2—H2A | 0.9900 | C17—H17A | 0.9900 |
C2—H2B | 0.9900 | C17—H17B | 0.9900 |
C3—H3A | 0.9900 | C18—C19 | 1.519 (3) |
C3—H3B | 0.9900 | C18—H18A | 0.9900 |
C4—C5 | 1.519 (2) | C18—H18B | 0.9900 |
C4—H4A | 0.9900 | C19—C20 | 1.525 (2) |
C4—H4B | 0.9900 | C19—H19A | 0.9900 |
C5—C6 | 1.526 (2) | C19—H19B | 0.9900 |
C5—H5A | 0.9900 | C20—H20A | 0.9900 |
C5—H5B | 0.9900 | C20—H20B | 0.9900 |
C6—C7 | 1.524 (2) | O2—C21 | 1.244 (2) |
C6—H6A | 0.9900 | O3—C21 | 1.287 (2) |
C6—H6B | 0.9900 | O4—C25 | 1.362 (2) |
C7—C8 | 1.517 (2) | O4—H4O | 0.82 (2) |
C7—H7A | 0.9900 | C21—C22 | 1.499 (2) |
C7—H7B | 0.9900 | C22—C27 | 1.392 (2) |
C8—H8A | 0.9900 | C22—C23 | 1.401 (2) |
C8—H8B | 0.9900 | C23—C24 | 1.388 (2) |
C9—C14 | 1.391 (2) | C23—H23 | 0.9500 |
C9—C10 | 1.393 (2) | C24—C25 | 1.392 (2) |
C10—C11 | 1.389 (3) | C24—H24 | 0.9500 |
C10—H10 | 0.9500 | C25—C26 | 1.400 (2) |
C11—C12 | 1.383 (3) | C26—C27 | 1.383 (2) |
C11—H11 | 0.9500 | C26—H26 | 0.9500 |
C12—C13 | 1.384 (3) | C27—H27 | 0.9500 |
C12—H12 | 0.9500 | ||
C1—O1—H1O | 106.6 (15) | C13—C12—H12 | 120.3 |
C3—N1—C4 | 112.50 (13) | C12—C13—C14 | 119.97 (18) |
C3—N1—C8 | 109.68 (13) | C12—C13—H13 | 120.0 |
C4—N1—C8 | 110.94 (13) | C14—C13—H13 | 120.0 |
C3—N1—H1N | 109.6 (12) | C13—C14—C9 | 121.31 (16) |
C4—N1—H1N | 108.3 (13) | C13—C14—H14 | 119.3 |
C8—N1—H1N | 105.6 (12) | C9—C14—H14 | 119.3 |
O1—C1—C9 | 106.91 (13) | C16—C15—C20 | 109.43 (14) |
O1—C1—C2 | 107.21 (13) | C16—C15—C1 | 111.85 (14) |
C9—C1—C2 | 111.47 (14) | C20—C15—C1 | 116.04 (15) |
O1—C1—C15 | 107.90 (14) | C16—C15—H15 | 106.3 |
C9—C1—C15 | 112.59 (13) | C20—C15—H15 | 106.3 |
C2—C1—C15 | 110.48 (14) | C1—C15—H15 | 106.3 |
C3—C2—C1 | 111.46 (14) | C15—C16—C17 | 111.40 (15) |
C3—C2—H2A | 109.3 | C15—C16—H16A | 109.3 |
C1—C2—H2A | 109.3 | C17—C16—H16A | 109.3 |
C3—C2—H2B | 109.3 | C15—C16—H16B | 109.3 |
C1—C2—H2B | 109.3 | C17—C16—H16B | 109.3 |
H2A—C2—H2B | 108.0 | H16A—C16—H16B | 108.0 |
N1—C3—C2 | 112.92 (14) | C18—C17—C16 | 111.82 (17) |
N1—C3—H3A | 109.0 | C18—C17—H17A | 109.3 |
C2—C3—H3A | 109.0 | C16—C17—H17A | 109.3 |
N1—C3—H3B | 109.0 | C18—C17—H17B | 109.3 |
C2—C3—H3B | 109.0 | C16—C17—H17B | 109.3 |
H3A—C3—H3B | 107.8 | H17A—C17—H17B | 107.9 |
N1—C4—C5 | 110.01 (13) | C19—C18—C17 | 111.13 (14) |
N1—C4—H4A | 109.7 | C19—C18—H18A | 109.4 |
C5—C4—H4A | 109.7 | C17—C18—H18A | 109.4 |
N1—C4—H4B | 109.7 | C19—C18—H18B | 109.4 |
C5—C4—H4B | 109.7 | C17—C18—H18B | 109.4 |
H4A—C4—H4B | 108.2 | H18A—C18—H18B | 108.0 |
C4—C5—C6 | 111.40 (14) | C18—C19—C20 | 111.47 (16) |
C4—C5—H5A | 109.3 | C18—C19—H19A | 109.3 |
C6—C5—H5A | 109.3 | C20—C19—H19A | 109.3 |
C4—C5—H5B | 109.3 | C18—C19—H19B | 109.3 |
C6—C5—H5B | 109.3 | C20—C19—H19B | 109.3 |
H5A—C5—H5B | 108.0 | H19A—C19—H19B | 108.0 |
C7—C6—C5 | 110.52 (14) | C19—C20—C15 | 110.86 (15) |
C7—C6—H6A | 109.5 | C19—C20—H20A | 109.5 |
C5—C6—H6A | 109.5 | C15—C20—H20A | 109.5 |
C7—C6—H6B | 109.5 | C19—C20—H20B | 109.5 |
C5—C6—H6B | 109.5 | C15—C20—H20B | 109.5 |
H6A—C6—H6B | 108.1 | H20A—C20—H20B | 108.1 |
C8—C7—C6 | 111.06 (14) | C25—O4—H4O | 107.3 (17) |
C8—C7—H7A | 109.4 | O2—C21—O3 | 123.43 (16) |
C6—C7—H7A | 109.4 | O2—C21—C22 | 119.08 (15) |
C8—C7—H7B | 109.4 | O3—C21—C22 | 117.42 (14) |
C6—C7—H7B | 109.4 | C27—C22—C23 | 118.22 (15) |
H7A—C7—H7B | 108.0 | C27—C22—C21 | 119.29 (14) |
N1—C8—C7 | 111.06 (14) | C23—C22—C21 | 122.17 (15) |
N1—C8—H8A | 109.4 | C24—C23—C22 | 120.95 (15) |
C7—C8—H8A | 109.4 | C24—C23—H23 | 119.5 |
N1—C8—H8B | 109.4 | C22—C23—H23 | 119.5 |
C7—C8—H8B | 109.4 | C23—C24—C25 | 119.81 (15) |
H8A—C8—H8B | 108.0 | C23—C24—H24 | 120.1 |
C14—C9—C10 | 118.00 (16) | C25—C24—H24 | 120.1 |
C14—C9—C1 | 121.08 (15) | O4—C25—C24 | 118.21 (14) |
C10—C9—C1 | 120.92 (16) | O4—C25—C26 | 121.89 (15) |
C11—C10—C9 | 120.83 (17) | C24—C25—C26 | 119.90 (15) |
C11—C10—H10 | 119.6 | C27—C26—C25 | 119.45 (16) |
C9—C10—H10 | 119.6 | C27—C26—H26 | 120.3 |
C12—C11—C10 | 120.39 (17) | C25—C26—H26 | 120.3 |
C12—C11—H11 | 119.8 | C26—C27—C22 | 121.58 (15) |
C10—C11—H11 | 119.8 | C26—C27—H27 | 119.2 |
C11—C12—C13 | 119.49 (18) | C22—C27—H27 | 119.2 |
C11—C12—H12 | 120.3 | ||
O1—C1—C2—C3 | −60.92 (18) | O1—C1—C15—C16 | 58.47 (19) |
C9—C1—C2—C3 | 55.77 (18) | C9—C1—C15—C16 | −59.3 (2) |
C15—C1—C2—C3 | −178.26 (14) | C2—C1—C15—C16 | 175.39 (15) |
C4—N1—C3—C2 | 58.13 (19) | O1—C1—C15—C20 | −175.03 (14) |
C8—N1—C3—C2 | −177.89 (14) | C9—C1—C15—C20 | 67.2 (2) |
C1—C2—C3—N1 | 147.37 (15) | C2—C1—C15—C20 | −58.1 (2) |
C3—N1—C4—C5 | −178.06 (14) | C20—C15—C16—C17 | 56.8 (2) |
C8—N1—C4—C5 | 58.66 (18) | C1—C15—C16—C17 | −173.14 (16) |
N1—C4—C5—C6 | −57.16 (18) | C15—C16—C17—C18 | −55.2 (2) |
C4—C5—C6—C7 | 54.9 (2) | C16—C17—C18—C19 | 53.4 (2) |
C5—C6—C7—C8 | −53.8 (2) | C17—C18—C19—C20 | −54.7 (2) |
C3—N1—C8—C7 | 176.68 (14) | C18—C19—C20—C15 | 57.6 (2) |
C4—N1—C8—C7 | −58.44 (18) | C16—C15—C20—C19 | −58.0 (2) |
C6—C7—C8—N1 | 55.9 (2) | C1—C15—C20—C19 | 174.29 (16) |
O1—C1—C9—C14 | 167.46 (14) | O2—C21—C22—C27 | −0.4 (2) |
C2—C1—C9—C14 | 50.6 (2) | O3—C21—C22—C27 | 176.72 (15) |
C15—C1—C9—C14 | −74.2 (2) | O2—C21—C22—C23 | −173.83 (16) |
O1—C1—C9—C10 | −13.2 (2) | O3—C21—C22—C23 | 3.3 (2) |
C2—C1—C9—C10 | −130.08 (16) | C27—C22—C23—C24 | −2.1 (2) |
C15—C1—C9—C10 | 105.11 (17) | C21—C22—C23—C24 | 171.35 (16) |
C14—C9—C10—C11 | 0.1 (2) | C22—C23—C24—C25 | −0.6 (3) |
C1—C9—C10—C11 | −179.21 (15) | C23—C24—C25—O4 | −176.52 (15) |
C9—C10—C11—C12 | 0.8 (3) | C23—C24—C25—C26 | 2.9 (3) |
C10—C11—C12—C13 | −1.0 (3) | O4—C25—C26—C27 | 176.85 (15) |
C11—C12—C13—C14 | 0.4 (3) | C24—C25—C26—C27 | −2.6 (2) |
C12—C13—C14—C9 | 0.5 (3) | C25—C26—C27—C22 | −0.2 (3) |
C10—C9—C14—C13 | −0.8 (2) | C23—C22—C27—C26 | 2.5 (3) |
C1—C9—C14—C13 | 178.57 (15) | C21—C22—C27—C26 | −171.18 (15) |
D—H···A | D—H | H···A | D···A | D—H···A |
O1—H1O···O2 | 0.88 (3) | 1.94 (3) | 2.8068 (18) | 165 (2) |
N1—H1N···O3 | 0.94 (2) | 1.76 (2) | 2.6908 (19) | 169.4 (17) |
C2—H2A···O2 | 0.99 | 2.57 | 3.277 (2) | 129 |
C4—H4B···O1i | 0.99 | 2.40 | 3.278 (2) | 148 |
C7—H7A···O3 | 0.99 | 2.64 | 3.314 (2) | 126 |
O4—H4O···O3ii | 0.82 (2) | 1.84 (3) | 2.6633 (18) | 176 (3) |
C26—H26···O3ii | 0.95 | 2.62 | 3.281 (2) | 127 |
Symmetry codes: (i) x, −y+1, z+1/2; (ii) x, −y, z−1/2. |
C20H32NO+·C7H4BrO2− | F(000) = 1056 |
Mr = 502.48 | Dx = 1.376 Mg m−3 |
Monoclinic, P21/n | Mo Kα radiation, λ = 0.71073 Å |
a = 6.2422 (4) Å | Cell parameters from 9837 reflections |
b = 17.8126 (14) Å | θ = 2.2–27.5° |
c = 21.9938 (19) Å | µ = 1.72 mm−1 |
β = 97.345 (3)° | T = 90 K |
V = 2425.4 (3) Å3 | Rod, colourless |
Z = 4 | 0.20 × 0.08 × 0.07 mm |
Bruker D8 Venture dual source diffractometer | 5566 independent reflections |
Radiation source: microsource | 4634 reflections with I > 2σ(I) |
Detector resolution: 7.41 pixels mm-1 | Rint = 0.049 |
φ and ω scans | θmax = 27.5°, θmin = 1.9° |
Absorption correction: multi-scan (SADABS; Krause et al., 2015) | h = −8→8 |
Tmin = 0.740, Tmax = 0.862 | k = −21→23 |
40844 measured reflections | l = −28→28 |
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)] = 0.037 | Hydrogen site location: mixed |
wR(F2) = 0.074 | H atoms treated by a mixture of independent and constrained refinement |
S = 1.13 | w = 1/[σ2(Fo2) + (0.0033P)2 + 2.553P] where P = (Fo2 + 2Fc2)/3 |
5566 reflections | (Δ/σ)max = 0.001 |
334 parameters | Δρmax = 0.33 e Å−3 |
68 restraints | Δρmin = −0.38 e Å−3 |
Experimental. The crystal was mounted using polyisobutene oil on the tip of a fine glass fibre, which was fastened in a copper mounting pin with electrical solder. It was placed directly into the cold gas stream of a liquid-nitrogen based cryostat (Hope, 1994; Parkin & Hope, 1998). Diffraction data were collected with the crystal at 90K, which is standard practice in this laboratory for the majority of flash-cooled crystals. |
Geometry. All esds (except the esd in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell esds are taken into account individually in the estimation of esds in distances, angles and torsion angles; correlations between esds in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell esds is used for estimating esds involving l.s. planes. |
Refinement. Refinement progress was checked using Platon (Spek, 2020) and by an R-tensor (Parkin, 2000). The final model was further checked with the IUCr utility checkCIF. |
x | y | z | Uiso*/Ueq | Occ. (<1) | |
N1 | −0.0077 (3) | 0.73580 (11) | 0.72464 (8) | 0.0168 (4) | |
H1N | 0.057 (4) | 0.6878 (14) | 0.7274 (11) | 0.020* | |
O1 | 0.2444 (2) | 0.71420 (9) | 0.56823 (7) | 0.0167 (3) | |
H1O | 0.277 (4) | 0.6811 (15) | 0.5928 (12) | 0.025* | |
C1 | 0.0138 (3) | 0.71331 (12) | 0.55325 (9) | 0.0159 (4) | |
C2 | −0.0881 (3) | 0.70260 (12) | 0.61312 (9) | 0.0158 (4) | |
H2A | −0.247256 | 0.706091 | 0.604115 | 0.019* | |
H2B | −0.051482 | 0.652058 | 0.630093 | 0.019* | |
C3 | −0.0063 (4) | 0.76191 (13) | 0.66025 (10) | 0.0182 (5) | |
H3A | 0.142919 | 0.776098 | 0.654261 | 0.022* | |
H3B | −0.097808 | 0.807276 | 0.653383 | 0.022* | |
C4 | −0.2313 (3) | 0.72756 (13) | 0.74133 (10) | 0.0170 (5) | |
H4A | −0.313965 | 0.692199 | 0.712543 | 0.020* | |
H4B | −0.305374 | 0.776800 | 0.737427 | 0.020* | |
C5 | −0.2278 (4) | 0.69889 (14) | 0.80611 (10) | 0.0229 (5) | |
H5A | −0.165578 | 0.647694 | 0.809116 | 0.027* | |
H5B | −0.377383 | 0.695961 | 0.816399 | 0.027* | |
C6 | −0.0946 (4) | 0.75021 (18) | 0.85167 (11) | 0.0359 (7) | |
H6A | −0.163886 | 0.800210 | 0.851709 | 0.043* | |
H6B | −0.086857 | 0.728925 | 0.893473 | 0.043* | |
C7 | 0.1317 (4) | 0.7579 (2) | 0.83370 (12) | 0.0497 (9) | |
H7A | 0.216628 | 0.793139 | 0.862134 | 0.060* | |
H7B | 0.204808 | 0.708516 | 0.837223 | 0.060* | |
C8 | 0.1239 (4) | 0.78670 (18) | 0.76852 (11) | 0.0351 (7) | |
H8A | 0.060303 | 0.837693 | 0.765682 | 0.042* | |
H8B | 0.272461 | 0.790033 | 0.757489 | 0.042* | |
C9 | −0.0707 (13) | 0.6559 (4) | 0.5074 (3) | 0.0136 (11) | 0.508 (5) |
C10 | 0.0709 (11) | 0.6299 (3) | 0.4673 (3) | 0.0173 (14) | 0.508 (5) |
H10 | 0.213821 | 0.649190 | 0.470634 | 0.021* | 0.508 (5) |
C11 | 0.0044 (10) | 0.5755 (4) | 0.4219 (3) | 0.0235 (14) | 0.508 (5) |
H11 | 0.101919 | 0.558842 | 0.394960 | 0.028* | 0.508 (5) |
C12 | −0.2045 (12) | 0.5462 (5) | 0.4169 (4) | 0.0273 (17) | 0.508 (5) |
H12 | −0.249979 | 0.509381 | 0.386694 | 0.033* | 0.508 (5) |
C13 | −0.3456 (12) | 0.5716 (3) | 0.4567 (3) | 0.0207 (13) | 0.508 (5) |
H13 | −0.487721 | 0.551647 | 0.453643 | 0.025* | 0.508 (5) |
C14 | −0.2813 (14) | 0.6259 (4) | 0.5010 (3) | 0.0136 (12) | 0.508 (5) |
H14 | −0.380815 | 0.642943 | 0.527248 | 0.016* | 0.508 (5) |
C15 | −0.039 (2) | 0.7975 (6) | 0.5267 (4) | 0.0138 (11) | 0.508 (5) |
H15 | 0.015215 | 0.833325 | 0.560196 | 0.017* | 0.508 (5) |
C16 | 0.0816 (18) | 0.8153 (6) | 0.4728 (4) | 0.0180 (14) | 0.508 (5) |
H16A | 0.237713 | 0.805671 | 0.484359 | 0.022* | 0.508 (5) |
H16B | 0.029602 | 0.781937 | 0.438020 | 0.022* | 0.508 (5) |
C17 | 0.049 (2) | 0.8963 (7) | 0.4531 (5) | 0.0236 (9) | 0.508 (5) |
H17A | 0.114029 | 0.929526 | 0.486503 | 0.028* | 0.508 (5) |
H17B | 0.123234 | 0.905569 | 0.416712 | 0.028* | 0.508 (5) |
C18 | −0.188 (2) | 0.9152 (6) | 0.4378 (4) | 0.0220 (15) | 0.508 (5) |
H18A | −0.203745 | 0.969529 | 0.428832 | 0.026* | 0.508 (5) |
H18B | −0.248717 | 0.887262 | 0.400652 | 0.026* | 0.508 (5) |
C19 | −0.313 (2) | 0.8955 (8) | 0.4901 (6) | 0.0214 (18) | 0.508 (5) |
H19A | −0.468747 | 0.904270 | 0.477411 | 0.026* | 0.508 (5) |
H19B | −0.265974 | 0.928465 | 0.525560 | 0.026* | 0.508 (5) |
C20 | −0.277 (2) | 0.8140 (7) | 0.5091 (6) | 0.0169 (11) | 0.508 (5) |
H20A | −0.335805 | 0.780907 | 0.474794 | 0.020* | 0.508 (5) |
H20B | −0.356185 | 0.803143 | 0.544407 | 0.020* | 0.508 (5) |
C9' | −0.049 (2) | 0.7826 (6) | 0.5209 (3) | 0.0138 (11) | 0.492 (5) |
C10' | 0.1019 (19) | 0.8232 (7) | 0.4919 (4) | 0.0180 (14) | 0.492 (5) |
H10' | 0.245495 | 0.804915 | 0.493673 | 0.022* | 0.492 (5) |
C11' | 0.045 (2) | 0.8903 (7) | 0.4604 (5) | 0.0236 (9) | 0.492 (5) |
H11' | 0.149052 | 0.916842 | 0.440915 | 0.028* | 0.492 (5) |
C12' | −0.166 (2) | 0.9180 (6) | 0.4577 (4) | 0.0220 (15) | 0.492 (5) |
H12' | −0.204684 | 0.963546 | 0.436680 | 0.026* | 0.492 (5) |
C13' | −0.318 (2) | 0.8781 (8) | 0.4861 (6) | 0.0214 (18) | 0.492 (5) |
H13' | −0.461470 | 0.896431 | 0.484072 | 0.026* | 0.492 (5) |
C14' | −0.261 (2) | 0.8112 (8) | 0.5175 (5) | 0.0169 (11) | 0.492 (5) |
H14' | −0.365777 | 0.784779 | 0.536804 | 0.020* | 0.492 (5) |
C15' | −0.0302 (14) | 0.6403 (5) | 0.5099 (4) | 0.0136 (11) | 0.492 (5) |
H15' | 0.024398 | 0.595835 | 0.534938 | 0.016* | 0.492 (5) |
C16' | −0.2696 (15) | 0.6269 (4) | 0.4891 (4) | 0.0173 (14) | 0.492 (5) |
H16C | −0.329759 | 0.669833 | 0.463868 | 0.021* | 0.492 (5) |
H16D | −0.347887 | 0.623333 | 0.525389 | 0.021* | 0.492 (5) |
C17' | −0.3021 (13) | 0.5547 (4) | 0.4518 (3) | 0.0235 (14) | 0.492 (5) |
H17C | −0.257359 | 0.511378 | 0.478574 | 0.028* | 0.492 (5) |
H17D | −0.457395 | 0.548808 | 0.436556 | 0.028* | 0.492 (5) |
C18' | −0.1755 (13) | 0.5547 (6) | 0.3986 (4) | 0.0273 (17) | 0.492 (5) |
H18C | −0.235017 | 0.593147 | 0.368608 | 0.033* | 0.492 (5) |
H18D | −0.190455 | 0.505129 | 0.378042 | 0.033* | 0.492 (5) |
C19' | 0.0624 (11) | 0.5707 (4) | 0.4184 (4) | 0.0207 (13) | 0.492 (5) |
H19C | 0.127161 | 0.528577 | 0.443714 | 0.025* | 0.492 (5) |
H19D | 0.138378 | 0.574622 | 0.381633 | 0.025* | 0.492 (5) |
C20' | 0.0923 (11) | 0.6428 (3) | 0.4547 (3) | 0.0136 (12) | 0.492 (5) |
H20C | 0.040000 | 0.685599 | 0.428151 | 0.016* | 0.492 (5) |
H20D | 0.247886 | 0.650653 | 0.468583 | 0.016* | 0.492 (5) |
Br1 | 1.04489 (4) | 0.39057 (2) | 0.85717 (2) | 0.02363 (7) | |
O2 | 0.1997 (3) | 0.60868 (11) | 0.73749 (8) | 0.0373 (5) | |
O3 | 0.3993 (2) | 0.61835 (10) | 0.66054 (7) | 0.0260 (4) | |
C21 | 0.3598 (3) | 0.59223 (12) | 0.71036 (11) | 0.0194 (5) | |
C22 | 0.5195 (3) | 0.53769 (12) | 0.74351 (10) | 0.0167 (4) | |
C23 | 0.4884 (3) | 0.51112 (12) | 0.80118 (10) | 0.0179 (5) | |
H23 | 0.359419 | 0.523381 | 0.817674 | 0.022* | |
C24 | 0.6430 (3) | 0.46708 (12) | 0.8348 (1) | 0.0194 (5) | |
H24 | 0.622186 | 0.449348 | 0.874355 | 0.023* | |
C25 | 0.8289 (3) | 0.44938 (12) | 0.80955 (10) | 0.0177 (5) | |
C26 | 0.8621 (4) | 0.47302 (13) | 0.75203 (10) | 0.0203 (5) | |
H26 | 0.989445 | 0.459348 | 0.735240 | 0.024* | |
C27 | 0.7050 (4) | 0.51743 (13) | 0.71895 (10) | 0.0198 (5) | |
H27 | 0.724997 | 0.534080 | 0.679027 | 0.024* |
U11 | U22 | U33 | U12 | U13 | U23 | |
N1 | 0.0140 (9) | 0.0254 (11) | 0.0109 (9) | −0.0013 (8) | 0.0013 (7) | −0.0019 (8) |
O1 | 0.0117 (7) | 0.0229 (8) | 0.0150 (8) | −0.0010 (6) | −0.0003 (6) | 0.0023 (7) |
C1 | 0.0122 (10) | 0.0235 (12) | 0.0118 (10) | −0.0025 (9) | 0.0003 (8) | −0.0001 (9) |
C2 | 0.0151 (10) | 0.0199 (11) | 0.0125 (10) | −0.0023 (8) | 0.0023 (8) | 0.0008 (9) |
C3 | 0.0206 (11) | 0.0214 (12) | 0.0131 (11) | −0.0044 (9) | 0.0039 (9) | −0.0015 (9) |
C4 | 0.0121 (10) | 0.0224 (12) | 0.0166 (11) | −0.0006 (9) | 0.0024 (8) | −0.0020 (9) |
C5 | 0.0185 (11) | 0.0355 (14) | 0.0153 (11) | −0.0019 (10) | 0.0050 (9) | −0.0003 (10) |
C6 | 0.0314 (14) | 0.066 (2) | 0.0111 (12) | −0.0133 (13) | 0.0044 (10) | −0.0086 (12) |
C7 | 0.0289 (14) | 0.106 (3) | 0.0136 (13) | −0.0268 (16) | −0.0004 (11) | −0.0079 (15) |
C8 | 0.0240 (13) | 0.066 (2) | 0.0152 (12) | −0.0213 (13) | 0.0032 (10) | −0.0122 (13) |
C9 | 0.010 (3) | 0.016 (3) | 0.0147 (13) | 0.005 (2) | 0.0003 (15) | −0.0024 (15) |
C10 | 0.018 (2) | 0.021 (2) | 0.015 (3) | −0.0014 (17) | 0.007 (2) | 0.0028 (17) |
C11 | 0.014 (3) | 0.031 (2) | 0.026 (3) | 0.003 (2) | 0.002 (2) | −0.0068 (19) |
C12 | 0.031 (2) | 0.018 (2) | 0.033 (5) | −0.0048 (18) | 0.005 (3) | −0.006 (3) |
C13 | 0.012 (3) | 0.027 (2) | 0.023 (2) | 0.0010 (19) | 0.0031 (18) | −0.0044 (19) |
C14 | 0.018 (2) | 0.015 (2) | 0.009 (2) | −0.0039 (16) | 0.0064 (18) | 0.0009 (16) |
C15 | 0.0178 (16) | 0.011 (4) | 0.0123 (15) | −0.002 (2) | 0.0011 (14) | −0.0014 (13) |
C16 | 0.017 (2) | 0.021 (2) | 0.016 (5) | 0.0001 (17) | 0.002 (3) | 0.002 (3) |
C17 | 0.0258 (12) | 0.0229 (19) | 0.023 (2) | −0.0011 (13) | 0.0057 (15) | 0.0057 (17) |
C18 | 0.031 (3) | 0.0148 (14) | 0.020 (5) | 0.0005 (15) | 0.000 (4) | −0.003 (3) |
C19 | 0.0196 (12) | 0.023 (6) | 0.0208 (17) | 0.002 (3) | 0.0011 (12) | −0.003 (3) |
C20 | 0.020 (2) | 0.0185 (13) | 0.013 (3) | −0.0013 (13) | 0.0026 (19) | 0.0011 (16) |
C9' | 0.0178 (16) | 0.011 (4) | 0.0123 (15) | −0.002 (2) | 0.0011 (14) | −0.0014 (13) |
C10' | 0.017 (2) | 0.021 (2) | 0.016 (5) | 0.0001 (17) | 0.002 (3) | 0.002 (3) |
C11' | 0.0258 (12) | 0.0229 (19) | 0.023 (2) | −0.0011 (13) | 0.0057 (15) | 0.0057 (17) |
C12' | 0.031 (3) | 0.0148 (14) | 0.020 (5) | 0.0005 (15) | 0.000 (4) | −0.003 (3) |
C13' | 0.0196 (12) | 0.023 (6) | 0.0208 (17) | 0.002 (3) | 0.0011 (12) | −0.003 (3) |
C14' | 0.020 (2) | 0.0185 (13) | 0.013 (3) | −0.0013 (13) | 0.0026 (19) | 0.0011 (16) |
C15' | 0.010 (3) | 0.016 (3) | 0.0147 (13) | 0.005 (2) | 0.0003 (15) | −0.0024 (15) |
C16' | 0.018 (2) | 0.021 (2) | 0.015 (3) | −0.0014 (17) | 0.007 (2) | 0.0028 (17) |
C17' | 0.014 (3) | 0.031 (2) | 0.026 (3) | 0.003 (2) | 0.002 (2) | −0.0068 (19) |
C18' | 0.031 (2) | 0.018 (2) | 0.033 (5) | −0.0048 (18) | 0.005 (3) | −0.006 (3) |
C19' | 0.012 (3) | 0.027 (2) | 0.023 (2) | 0.0010 (19) | 0.0031 (18) | −0.0044 (19) |
C20' | 0.018 (2) | 0.015 (2) | 0.009 (2) | −0.0039 (16) | 0.0064 (18) | 0.0009 (16) |
Br1 | 0.01870 (11) | 0.02277 (12) | 0.02920 (13) | 0.00452 (10) | 0.00219 (9) | 0.00522 (11) |
O2 | 0.0284 (9) | 0.0486 (12) | 0.0368 (11) | 0.0198 (9) | 0.0115 (8) | 0.0151 (10) |
O3 | 0.0226 (8) | 0.0305 (10) | 0.0236 (9) | 0.0012 (7) | −0.0021 (7) | 0.0081 (8) |
C21 | 0.0183 (11) | 0.0159 (11) | 0.0225 (12) | −0.0012 (8) | −0.0035 (9) | −0.0023 (9) |
C22 | 0.0182 (10) | 0.0134 (10) | 0.0179 (11) | −0.0007 (8) | −0.0003 (9) | −0.0033 (9) |
C23 | 0.017 (1) | 0.0150 (11) | 0.0227 (12) | 0.0003 (8) | 0.0060 (9) | −0.0023 (9) |
C24 | 0.0216 (11) | 0.0171 (11) | 0.0204 (12) | 0.0005 (9) | 0.0056 (9) | 0.0011 (9) |
C25 | 0.0179 (10) | 0.0107 (10) | 0.0237 (12) | 0.0019 (8) | −0.0006 (9) | −0.0001 (9) |
C26 | 0.0183 (11) | 0.0197 (12) | 0.0237 (12) | 0.0027 (9) | 0.0059 (9) | −0.0017 (10) |
C27 | 0.0228 (11) | 0.0203 (12) | 0.0168 (11) | 0.0009 (9) | 0.0044 (9) | −0.0002 (9) |
N1—C3 | 1.492 (3) | C18—C19 | 1.511 (8) |
N1—C8 | 1.492 (3) | C18—H18A | 0.9900 |
N1—C4 | 1.495 (3) | C18—H18B | 0.9900 |
N1—H1N | 0.95 (2) | C19—C20 | 1.519 (8) |
O1—C1 | 1.436 (2) | C19—H19A | 0.9900 |
O1—H1O | 0.81 (3) | C19—H19B | 0.9900 |
C1—C9' | 1.454 (13) | C20—H20A | 0.9900 |
C1—C9 | 1.485 (10) | C20—H20B | 0.9900 |
C1—C2 | 1.546 (3) | C9'—C10' | 1.404 (7) |
C1—C15' | 1.615 (11) | C9'—C14' | 1.408 (7) |
C1—C15 | 1.628 (13) | C10'—C11' | 1.405 (7) |
C2—C3 | 1.522 (3) | C10'—H10' | 0.9500 |
C2—H2A | 0.9900 | C11'—C12' | 1.396 (7) |
C2—H2B | 0.9900 | C11'—H11' | 0.9500 |
C3—H3A | 0.9900 | C12'—C13' | 1.398 (7) |
C3—H3B | 0.9900 | C12'—H12' | 0.9500 |
C4—C5 | 1.511 (3) | C13'—C14' | 1.401 (7) |
C4—H4A | 0.9900 | C13'—H13' | 0.9500 |
C4—H4B | 0.9900 | C14'—H14' | 0.9500 |
C5—C6 | 1.522 (3) | C15'—C20' | 1.516 (7) |
C5—H5A | 0.9900 | C15'—C16' | 1.525 (8) |
C5—H5B | 0.9900 | C15'—H15' | 1.0000 |
C6—C7 | 1.521 (4) | C16'—C17' | 1.525 (7) |
C6—H6A | 0.9900 | C16'—H16C | 0.9900 |
C6—H6B | 0.9900 | C16'—H16D | 0.9900 |
C7—C8 | 1.517 (4) | C17'—C18' | 1.493 (7) |
C7—H7A | 0.9900 | C17'—H17C | 0.9900 |
C7—H7B | 0.9900 | C17'—H17D | 0.9900 |
C8—H8A | 0.9900 | C18'—C19' | 1.520 (7) |
C8—H8B | 0.9900 | C18'—H18C | 0.9900 |
C9—C10 | 1.405 (7) | C18'—H18D | 0.9900 |
C9—C14 | 1.409 (7) | C19'—C20' | 1.512 (7) |
C10—C11 | 1.414 (6) | C19'—H19C | 0.9900 |
C10—H10 | 0.9500 | C19'—H19D | 0.9900 |
C11—C12 | 1.396 (7) | C20'—H20C | 0.9900 |
C11—H11 | 0.9500 | C20'—H20D | 0.9900 |
C12—C13 | 1.395 (7) | Br1—C25 | 1.911 (2) |
C12—H12 | 0.9500 | O2—C21 | 1.262 (3) |
C13—C14 | 1.395 (6) | O3—C21 | 1.244 (3) |
C13—H13 | 0.9500 | C21—C22 | 1.511 (3) |
C14—H14 | 0.9500 | C22—C27 | 1.387 (3) |
C15—C16 | 1.515 (8) | C22—C23 | 1.390 (3) |
C15—C20 | 1.520 (8) | C23—C24 | 1.382 (3) |
C15—H15 | 1.0000 | C23—H23 | 0.9500 |
C16—C17 | 1.512 (8) | C24—C25 | 1.385 (3) |
C16—H16A | 0.9900 | C24—H24 | 0.9500 |
C16—H16B | 0.9900 | C25—C26 | 1.374 (3) |
C17—C18 | 1.511 (8) | C26—C27 | 1.391 (3) |
C17—H17A | 0.9900 | C26—H26 | 0.9500 |
C17—H17B | 0.9900 | C27—H27 | 0.9500 |
C3—N1—C8 | 110.79 (18) | H17A—C17—H17B | 107.9 |
C3—N1—C4 | 112.51 (16) | C19—C18—C17 | 111.3 (7) |
C8—N1—C4 | 110.80 (18) | C19—C18—H18A | 109.4 |
C3—N1—H1N | 106.7 (15) | C17—C18—H18A | 109.4 |
C8—N1—H1N | 108.3 (14) | C19—C18—H18B | 109.4 |
C4—N1—H1N | 107.5 (15) | C17—C18—H18B | 109.4 |
C1—O1—H1O | 107.7 (18) | H18A—C18—H18B | 108.0 |
O1—C1—C9' | 107.6 (6) | C18—C19—C20 | 111.1 (7) |
O1—C1—C9 | 115.0 (3) | C18—C19—H19A | 109.4 |
O1—C1—C2 | 108.39 (16) | C20—C19—H19A | 109.4 |
C9'—C1—C2 | 114.0 (5) | C18—C19—H19B | 109.4 |
C9—C1—C2 | 110.2 (3) | C20—C19—H19B | 109.4 |
O1—C1—C15' | 103.5 (3) | H19A—C19—H19B | 108.0 |
C9'—C1—C15' | 112.3 (3) | C19—C20—C15 | 111.0 (7) |
C2—C1—C15' | 110.3 (3) | C19—C20—H20A | 109.4 |
O1—C1—C15 | 102.8 (5) | C15—C20—H20A | 109.4 |
C9—C1—C15 | 110.7 (3) | C19—C20—H20B | 109.4 |
C2—C1—C15 | 109.5 (4) | C15—C20—H20B | 109.4 |
C3—C2—C1 | 110.85 (17) | H20A—C20—H20B | 108.0 |
C3—C2—H2A | 109.5 | C10'—C9'—C14' | 118.0 (7) |
C1—C2—H2A | 109.5 | C10'—C9'—C1 | 120.3 (11) |
C3—C2—H2B | 109.5 | C14'—C9'—C1 | 121.7 (10) |
C1—C2—H2B | 109.5 | C9'—C10'—C11' | 121.3 (7) |
H2A—C2—H2B | 108.1 | C9'—C10'—H10' | 119.4 |
N1—C3—C2 | 112.83 (18) | C11'—C10'—H10' | 119.4 |
N1—C3—H3A | 109.0 | C12'—C11'—C10' | 120.0 (7) |
C2—C3—H3A | 109.0 | C12'—C11'—H11' | 120.0 |
N1—C3—H3B | 109.0 | C10'—C11'—H11' | 120.0 |
C2—C3—H3B | 109.0 | C11'—C12'—C13' | 119.4 (7) |
H3A—C3—H3B | 107.8 | C11'—C12'—H12' | 120.3 |
N1—C4—C5 | 111.28 (17) | C13'—C12'—H12' | 120.3 |
N1—C4—H4A | 109.4 | C12'—C13'—C14' | 120.6 (8) |
C5—C4—H4A | 109.4 | C12'—C13'—H13' | 119.7 |
N1—C4—H4B | 109.4 | C14'—C13'—H13' | 119.7 |
C5—C4—H4B | 109.4 | C13'—C14'—C9' | 120.8 (8) |
H4A—C4—H4B | 108.0 | C13'—C14'—H14' | 119.6 |
C4—C5—C6 | 111.0 (2) | C9'—C14'—H14' | 119.6 |
C4—C5—H5A | 109.4 | C20'—C15'—C16' | 109.9 (6) |
C6—C5—H5A | 109.4 | C20'—C15'—C1 | 112.6 (6) |
C4—C5—H5B | 109.4 | C16'—C15'—C1 | 112.9 (5) |
C6—C5—H5B | 109.4 | C20'—C15'—H15' | 107.0 |
H5A—C5—H5B | 108.0 | C16'—C15'—H15' | 107.0 |
C7—C6—C5 | 109.3 (2) | C1—C15'—H15' | 107.0 |
C7—C6—H6A | 109.8 | C15'—C16'—C17' | 110.6 (6) |
C5—C6—H6A | 109.8 | C15'—C16'—H16C | 109.5 |
C7—C6—H6B | 109.8 | C17'—C16'—H16C | 109.5 |
C5—C6—H6B | 109.8 | C15'—C16'—H16D | 109.5 |
H6A—C6—H6B | 108.3 | C17'—C16'—H16D | 109.5 |
C8—C7—C6 | 110.9 (2) | H16C—C16'—H16D | 108.1 |
C8—C7—H7A | 109.5 | C18'—C17'—C16' | 112.0 (6) |
C6—C7—H7A | 109.5 | C18'—C17'—H17C | 109.2 |
C8—C7—H7B | 109.5 | C16'—C17'—H17C | 109.2 |
C6—C7—H7B | 109.5 | C18'—C17'—H17D | 109.2 |
H7A—C7—H7B | 108.0 | C16'—C17'—H17D | 109.2 |
N1—C8—C7 | 110.8 (2) | H17C—C17'—H17D | 107.9 |
N1—C8—H8A | 109.5 | C17'—C18'—C19' | 111.8 (6) |
C7—C8—H8A | 109.5 | C17'—C18'—H18C | 109.3 |
N1—C8—H8B | 109.5 | C19'—C18'—H18C | 109.3 |
C7—C8—H8B | 109.5 | C17'—C18'—H18D | 109.3 |
H8A—C8—H8B | 108.1 | C19'—C18'—H18D | 109.3 |
C10—C9—C14 | 117.8 (6) | H18C—C18'—H18D | 107.9 |
C10—C9—C1 | 117.2 (6) | C20'—C19'—C18' | 111.2 (6) |
C14—C9—C1 | 125.0 (5) | C20'—C19'—H19C | 109.4 |
C9—C10—C11 | 121.2 (5) | C18'—C19'—H19C | 109.4 |
C9—C10—H10 | 119.4 | C20'—C19'—H19D | 109.4 |
C11—C10—H10 | 119.4 | C18'—C19'—H19D | 109.4 |
C12—C11—C10 | 120.0 (5) | H19C—C19'—H19D | 108.0 |
C12—C11—H11 | 120.0 | C19'—C20'—C15' | 111.0 (5) |
C10—C11—H11 | 120.0 | C19'—C20'—H20C | 109.4 |
C13—C12—C11 | 119.1 (6) | C15'—C20'—H20C | 109.4 |
C13—C12—H12 | 120.4 | C19'—C20'—H20D | 109.4 |
C11—C12—H12 | 120.4 | C15'—C20'—H20D | 109.4 |
C14—C13—C12 | 121.0 (6) | H20C—C20'—H20D | 108.0 |
C14—C13—H13 | 119.5 | O3—C21—O2 | 126.0 (2) |
C12—C13—H13 | 119.5 | O3—C21—C22 | 118.2 (2) |
C13—C14—C9 | 120.9 (6) | O2—C21—C22 | 115.7 (2) |
C13—C14—H14 | 119.5 | C27—C22—C23 | 119.2 (2) |
C9—C14—H14 | 119.5 | C27—C22—C21 | 120.8 (2) |
C16—C15—C20 | 109.2 (6) | C23—C22—C21 | 119.9 (2) |
C16—C15—C1 | 112.1 (8) | C24—C23—C22 | 120.8 (2) |
C20—C15—C1 | 114.5 (9) | C24—C23—H23 | 119.6 |
C16—C15—H15 | 106.9 | C22—C23—H23 | 119.6 |
C20—C15—H15 | 106.9 | C23—C24—C25 | 118.6 (2) |
C1—C15—H15 | 106.9 | C23—C24—H24 | 120.7 |
C17—C16—C15 | 111.1 (7) | C25—C24—H24 | 120.7 |
C17—C16—H16A | 109.4 | C26—C25—C24 | 122.1 (2) |
C15—C16—H16A | 109.4 | C26—C25—Br1 | 119.58 (17) |
C17—C16—H16B | 109.4 | C24—C25—Br1 | 118.28 (17) |
C15—C16—H16B | 109.4 | C25—C26—C27 | 118.5 (2) |
H16A—C16—H16B | 108.0 | C25—C26—H26 | 120.8 |
C18—C17—C16 | 111.7 (7) | C27—C26—H26 | 120.8 |
C18—C17—H17A | 109.3 | C22—C27—C26 | 120.8 (2) |
C16—C17—H17A | 109.3 | C22—C27—H27 | 119.6 |
C18—C17—H17B | 109.3 | C26—C27—H27 | 119.6 |
C16—C17—H17B | 109.3 | ||
O1—C1—C2—C3 | 54.4 (2) | C1—C15—C20—C19 | 175.0 (6) |
C9'—C1—C2—C3 | −65.4 (5) | O1—C1—C9'—C10' | 21.4 (4) |
C9—C1—C2—C3 | −179.0 (2) | C2—C1—C9'—C10' | 141.6 (4) |
C15'—C1—C2—C3 | 167.1 (3) | C15'—C1—C9'—C10' | −92.0 (5) |
C15—C1—C2—C3 | −57.0 (5) | O1—C1—C9'—C14' | −158.7 (5) |
C8—N1—C3—C2 | 165.40 (19) | C2—C1—C9'—C14' | −38.4 (5) |
C4—N1—C3—C2 | −70.0 (2) | C15'—C1—C9'—C14' | 88.0 (6) |
C1—C2—C3—N1 | −152.27 (17) | C14'—C9'—C10'—C11' | 0.0 (4) |
C3—N1—C4—C5 | 178.32 (18) | C1—C9'—C10'—C11' | 180.0 (3) |
C8—N1—C4—C5 | −57.0 (3) | C9'—C10'—C11'—C12' | 0.3 (6) |
N1—C4—C5—C6 | 56.8 (3) | C10'—C11'—C12'—C13' | −0.5 (8) |
C4—C5—C6—C7 | −56.1 (3) | C11'—C12'—C13'—C14' | 0.5 (8) |
C5—C6—C7—C8 | 56.5 (4) | C12'—C13'—C14'—C9' | −0.3 (8) |
C3—N1—C8—C7 | −177.1 (2) | C10'—C9'—C14'—C13' | 0.0 (6) |
C4—N1—C8—C7 | 57.3 (3) | C1—C9'—C14'—C13' | −179.9 (4) |
C6—C7—C8—N1 | −57.7 (4) | O1—C1—C15'—C20' | −56.1 (5) |
O1—C1—C9—C10 | −23.8 (2) | C9'—C1—C15'—C20' | 59.8 (8) |
C2—C1—C9—C10 | −146.6 (2) | C2—C1—C15'—C20' | −171.9 (4) |
C15—C1—C9—C10 | 92.1 (6) | O1—C1—C15'—C16' | 178.7 (4) |
O1—C1—C9—C14 | 156.4 (3) | C9'—C1—C15'—C16' | −65.4 (8) |
C2—C1—C9—C14 | 33.6 (3) | C2—C1—C15'—C16' | 63.0 (6) |
C15—C1—C9—C14 | −87.7 (6) | C20'—C15'—C16'—C17' | 56.9 (8) |
C14—C9—C10—C11 | 0.0 (3) | C1—C15'—C16'—C17' | −176.4 (5) |
C1—C9—C10—C11 | −179.7 (2) | C15'—C16'—C17'—C18' | −55.4 (9) |
C9—C10—C11—C12 | −0.6 (5) | C16'—C17'—C18'—C19' | 53.7 (9) |
C10—C11—C12—C13 | 0.4 (7) | C17'—C18'—C19'—C20' | −54.1 (9) |
C11—C12—C13—C14 | 0.4 (7) | C18'—C19'—C20'—C15' | 56.5 (8) |
C12—C13—C14—C9 | −0.9 (7) | C16'—C15'—C20'—C19' | −58.1 (8) |
C10—C9—C14—C13 | 0.7 (5) | C1—C15'—C20'—C19' | 175.1 (5) |
C1—C9—C14—C13 | −179.5 (3) | O3—C21—C22—C27 | 0.0 (3) |
O1—C1—C15—C16 | 57.2 (6) | O2—C21—C22—C27 | −177.9 (2) |
C9—C1—C15—C16 | −66.0 (7) | O3—C21—C22—C23 | 175.7 (2) |
C2—C1—C15—C16 | 172.3 (5) | O2—C21—C22—C23 | −2.2 (3) |
O1—C1—C15—C20 | −177.7 (5) | C27—C22—C23—C24 | 2.1 (3) |
C9—C1—C15—C20 | 59.1 (8) | C21—C22—C23—C24 | −173.6 (2) |
C2—C1—C15—C20 | −62.6 (6) | C22—C23—C24—C25 | −0.6 (3) |
C20—C15—C16—C17 | 57.9 (9) | C23—C24—C25—C26 | −1.2 (3) |
C1—C15—C16—C17 | −174.1 (7) | C23—C24—C25—Br1 | 178.47 (16) |
C15—C16—C17—C18 | −56.3 (9) | C24—C25—C26—C27 | 1.3 (3) |
C16—C17—C18—C19 | 53.9 (9) | Br1—C25—C26—C27 | −178.31 (17) |
C17—C18—C19—C20 | −54.1 (9) | C23—C22—C27—C26 | −2.0 (3) |
C18—C19—C20—C15 | 56.9 (9) | C21—C22—C27—C26 | 173.8 (2) |
C16—C15—C20—C19 | −58.3 (8) | C25—C26—C27—C22 | 0.3 (3) |
D—H···A | D—H | H···A | D···A | D—H···A |
N1—H1N···O2 | 0.95 (2) | 1.67 (3) | 2.606 (3) | 172 (2) |
O1—H1O···O3 | 0.81 (3) | 1.94 (3) | 2.733 (2) | 167 (3) |
C3—H3A···Br1i | 0.99 | 2.85 | 3.739 (2) | 149 |
C4—H4A···O3ii | 0.99 | 2.39 | 3.348 (3) | 162 |
Symmetry codes: (i) −x+3/2, y+1/2, −z+3/2; (ii) x−1, y, z. |
2C20H32NO+·2C5H3O2S−·H2O | Z = 2 |
Mr = 877.21 | F(000) = 948 |
Triclinic, P1 | Dx = 1.226 Mg m−3 |
a = 6.2765 (3) Å | Mo Kα radiation, λ = 0.71073 Å |
b = 18.5390 (13) Å | Cell parameters from 9857 reflections |
c = 20.6383 (14) Å | θ = 2.2–27.5° |
α = 89.710 (2)° | µ = 0.16 mm−1 |
β = 81.600 (2)° | T = 90 K |
γ = 88.977 (2)° | Cut block, colourless |
V = 2375.3 (3) Å3 | 0.16 × 0.12 × 0.11 mm |
Bruker D8 Venture dual source diffractometer | 10922 independent reflections |
Radiation source: microsource | 8540 reflections with I > 2σ(I) |
Detector resolution: 7.41 pixels mm-1 | Rint = 0.049 |
φ and ω scans | θmax = 27.5°, θmin = 2.0° |
Absorption correction: multi-scan (SADABS; Krause et al., 2015) | h = −8→7 |
Tmin = 0.908, Tmax = 0.959 | k = −24→24 |
78578 measured reflections | l = −26→26 |
Refinement on F2 | Secondary atom site location: difference Fourier map |
Least-squares matrix: full | Hydrogen site location: mixed |
R[F2 > 2σ(F2)] = 0.042 | H atoms treated by a mixture of independent and constrained refinement |
wR(F2) = 0.101 | w = 1/[σ2(Fo2) + (0.0315P)2 + 1.4676P] where P = (Fo2 + 2Fc2)/3 |
S = 1.03 | (Δ/σ)max < 0.001 |
10922 reflections | Δρmax = 0.71 e Å−3 |
603 parameters | Δρmin = −0.30 e Å−3 |
168 restraints | Extinction correction: SHELXL-2019/2 (Sheldrick 2008), Fc*=kFc[1+0.001xFc2λ3/sin(2θ)]-1/4 |
Primary atom site location: structure-invariant direct methods | Extinction coefficient: 0.0025 (5) |
Experimental. The crystal was mounted using polyisobutene oil on the tip of a fine glass fibre, which was fastened in a copper mounting pin with electrical solder. It was placed directly into the cold gas stream of a liquid-nitrogen based cryostat (Hope, 1994; Parkin & Hope, 1998). Diffraction data were collected with the crystal at 90K, which is standard practice in this laboratory for the majority of flash-cooled crystals. |
Geometry. All esds (except the esd in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell esds are taken into account individually in the estimation of esds in distances, angles and torsion angles; correlations between esds in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell esds is used for estimating esds involving l.s. planes. |
Refinement. Refinement progress was checked using Platon (Spek, 2020) and by an R-tensor (Parkin, 2000). The final model was further checked with the IUCr utility checkCIF. |
x | y | z | Uiso*/Ueq | Occ. (<1) | |
O1A | 1.01018 (18) | 0.31684 (6) | 0.70649 (6) | 0.0285 (3) | |
H1OA | 1.023 (3) | 0.2634 (12) | 0.7113 (10) | 0.043* | |
N1A | 0.5203 (2) | 0.23400 (7) | 0.63156 (6) | 0.0206 (3) | |
H1NA | 0.453 (3) | 0.2036 (10) | 0.6642 (9) | 0.025* | |
C1A | 0.8139 (3) | 0.34315 (8) | 0.74407 (8) | 0.0246 (3) | |
C2A | 0.6310 (3) | 0.29422 (8) | 0.73028 (8) | 0.0253 (3) | |
H2AA | 0.675790 | 0.243307 | 0.735486 | 0.030* | |
H2AB | 0.502954 | 0.303999 | 0.763355 | 0.030* | |
C3A | 0.5673 (3) | 0.30407 (8) | 0.66211 (8) | 0.0256 (3) | |
H3AA | 0.438076 | 0.335988 | 0.665222 | 0.031* | |
H3AB | 0.685613 | 0.328097 | 0.633470 | 0.031* | |
C4A | 0.3690 (3) | 0.24531 (8) | 0.58264 (8) | 0.0239 (3) | |
H4AA | 0.433679 | 0.278891 | 0.548123 | 0.029* | |
H4AB | 0.233164 | 0.267659 | 0.604615 | 0.029* | |
C5A | 0.3196 (3) | 0.17482 (9) | 0.55142 (8) | 0.0267 (3) | |
H5AA | 0.225973 | 0.184592 | 0.517602 | 0.032* | |
H5AB | 0.240637 | 0.143179 | 0.585165 | 0.032* | |
C6A | 0.5257 (3) | 0.13633 (9) | 0.52014 (8) | 0.0301 (4) | |
H6AA | 0.490413 | 0.088829 | 0.503153 | 0.036* | |
H6AB | 0.596577 | 0.165251 | 0.482910 | 0.036* | |
C7A | 0.6776 (3) | 0.12594 (9) | 0.57060 (8) | 0.0291 (4) | |
H7AA | 0.611910 | 0.092930 | 0.605468 | 0.035* | |
H7AB | 0.814144 | 0.103430 | 0.549390 | 0.035* | |
C8A | 0.7247 (2) | 0.19724 (9) | 0.60084 (8) | 0.0249 (3) | |
H8AA | 0.819660 | 0.188632 | 0.634514 | 0.030* | |
H8AB | 0.801136 | 0.228876 | 0.566611 | 0.030* | |
C9A | 0.7819 (3) | 0.42050 (8) | 0.72132 (8) | 0.0237 (3) | |
C10A | 0.9541 (3) | 0.45935 (9) | 0.68973 (8) | 0.0273 (4) | |
H10A | 1.092921 | 0.437141 | 0.681494 | 0.033* | |
C11A | 0.9262 (3) | 0.52997 (9) | 0.67009 (8) | 0.0321 (4) | |
H11A | 1.046247 | 0.555952 | 0.649098 | 0.038* | |
C12A | 0.7251 (3) | 0.56292 (9) | 0.68080 (9) | 0.0326 (4) | |
H12A | 0.706126 | 0.611106 | 0.666536 | 0.039* | |
C13A | 0.5516 (3) | 0.52542 (9) | 0.71237 (9) | 0.0309 (4) | |
H13A | 0.412744 | 0.547731 | 0.719791 | 0.037* | |
C14A | 0.5804 (3) | 0.45499 (9) | 0.73325 (8) | 0.0280 (4) | |
H14A | 0.461284 | 0.429938 | 0.755983 | 0.034* | |
C15A | 0.8340 (3) | 0.34294 (9) | 0.81871 (8) | 0.0266 (3) | |
H15A | 0.705784 | 0.370056 | 0.841580 | 0.032* | |
C16A | 0.8318 (3) | 0.26799 (10) | 0.84952 (9) | 0.0354 (4) | |
H16A | 0.954228 | 0.238918 | 0.827028 | 0.042* | |
H16B | 0.697018 | 0.243715 | 0.843341 | 0.042* | |
C17A | 0.8478 (4) | 0.27140 (12) | 0.92268 (10) | 0.0500 (6) | |
H17A | 0.718855 | 0.296857 | 0.945739 | 0.060* | |
H17B | 0.850162 | 0.221762 | 0.940516 | 0.060* | |
C18A | 1.0476 (4) | 0.30993 (11) | 0.9355 (1) | 0.0495 (5) | |
H18A | 1.177279 | 0.282055 | 0.916199 | 0.059* | |
H18B | 1.048795 | 0.313333 | 0.983302 | 0.059* | |
C19A | 1.0534 (4) | 0.38502 (11) | 0.90591 (10) | 0.0434 (5) | |
H19A | 1.190434 | 0.408055 | 0.911702 | 0.052* | |
H19B | 0.933691 | 0.414674 | 0.929198 | 0.052* | |
C20A | 1.0334 (3) | 0.38268 (10) | 0.83260 (9) | 0.0333 (4) | |
H20A | 1.027564 | 0.432667 | 0.815760 | 0.040* | |
H20B | 1.163368 | 0.358562 | 0.808711 | 0.040* | |
O1B | 0.62051 (16) | 0.22169 (6) | 0.18905 (5) | 0.0210 (2) | |
H1OB | 0.612 (3) | 0.2411 (10) | 0.2281 (10) | 0.032* | |
N1B | 0.10474 (19) | 0.12468 (7) | 0.30623 (6) | 0.0181 (3) | |
H1NB | 0.047 (3) | 0.1674 (9) | 0.3283 (8) | 0.022* | |
C1B | 0.4188 (2) | 0.23678 (8) | 0.16663 (7) | 0.0189 (3) | |
C2B | 0.2339 (2) | 0.21738 (8) | 0.22165 (7) | 0.0193 (3) | |
H2BA | 0.216467 | 0.255748 | 0.255292 | 0.023* | |
H2BB | 0.097312 | 0.214315 | 0.203195 | 0.023* | |
C3B | 0.2815 (2) | 0.14581 (8) | 0.25303 (8) | 0.0211 (3) | |
H3BA | 0.301071 | 0.107825 | 0.219030 | 0.025* | |
H3BB | 0.417797 | 0.149268 | 0.271543 | 0.025* | |
C4B | −0.0739 (2) | 0.08888 (9) | 0.27877 (8) | 0.0245 (3) | |
H4BA | −0.015542 | 0.046408 | 0.252701 | 0.029* | |
H4BB | −0.136153 | 0.122889 | 0.249186 | 0.029* | |
C5B | −0.2491 (3) | 0.06503 (9) | 0.33256 (9) | 0.0319 (4) | |
H5BA | −0.359215 | 0.038520 | 0.312913 | 0.038* | |
H5BB | −0.319904 | 0.108110 | 0.354948 | 0.038* | |
C6B | −0.1609 (3) | 0.01707 (10) | 0.38237 (10) | 0.0374 (4) | |
H6BA | −0.277625 | 0.005040 | 0.418224 | 0.045* | |
H6BB | −0.102964 | −0.028468 | 0.361313 | 0.045* | |
C7B | 0.0161 (3) | 0.05594 (10) | 0.40982 (9) | 0.0336 (4) | |
H7BA | −0.044944 | 0.099505 | 0.433733 | 0.040* | |
H7BB | 0.077591 | 0.024010 | 0.441205 | 0.040* | |
C8B | 0.1921 (3) | 0.07761 (9) | 0.35551 (8) | 0.0252 (3) | |
H8BA | 0.304572 | 0.103759 | 0.374417 | 0.030* | |
H8BB | 0.259651 | 0.033774 | 0.333591 | 0.030* | |
C9B | 0.4125 (2) | 0.18947 (8) | 0.10659 (7) | 0.0201 (3) | |
C10B | 0.5955 (3) | 0.15091 (9) | 0.07854 (8) | 0.0273 (4) | |
H10B | 0.723935 | 0.153051 | 0.097723 | 0.033* | |
C11B | 0.5920 (3) | 0.10937 (10) | 0.02280 (9) | 0.0330 (4) | |
H11B | 0.717322 | 0.082911 | 0.004555 | 0.040* | |
C12B | 0.4076 (3) | 0.10633 (10) | −0.00619 (8) | 0.0321 (4) | |
H12B | 0.406621 | 0.078639 | −0.044746 | 0.038* | |
C13B | 0.2245 (3) | 0.14378 (9) | 0.02120 (8) | 0.0268 (4) | |
H13B | 0.097227 | 0.141749 | 0.001444 | 0.032* | |
C14B | 0.2258 (3) | 0.18437 (9) | 0.07746 (8) | 0.0235 (3) | |
H14B | 0.098002 | 0.209034 | 0.096422 | 0.028* | |
C15B | 0.4105 (2) | 0.31884 (8) | 0.15073 (7) | 0.0204 (3) | |
H15B | 0.439976 | 0.344282 | 0.191012 | 0.025* | |
C16B | 0.5900 (3) | 0.34017 (9) | 0.09634 (8) | 0.0277 (4) | |
H16C | 0.565023 | 0.317958 | 0.054636 | 0.033* | |
H16D | 0.729811 | 0.321623 | 0.106890 | 0.033* | |
C17B | 0.5992 (3) | 0.42217 (9) | 0.08811 (9) | 0.0321 (4) | |
H17C | 0.638612 | 0.443979 | 0.128317 | 0.039* | |
H17D | 0.712094 | 0.434314 | 0.051163 | 0.039* | |
C18B | 0.3841 (3) | 0.4536 (1) | 0.07513 (9) | 0.0352 (4) | |
H18C | 0.353857 | 0.436755 | 0.032005 | 0.042* | |
H18D | 0.391733 | 0.506885 | 0.073601 | 0.042* | |
C19B | 0.2018 (3) | 0.43126 (9) | 0.12812 (9) | 0.0294 (4) | |
H19C | 0.062788 | 0.449334 | 0.116573 | 0.035* | |
H19D | 0.222369 | 0.453327 | 0.170305 | 0.035* | |
C20B | 0.1949 (2) | 0.34916 (9) | 0.13579 (8) | 0.0247 (3) | |
H20C | 0.079550 | 0.336296 | 0.171769 | 0.030* | |
H20D | 0.160938 | 0.327335 | 0.094916 | 0.030* | |
O1C | 0.38536 (19) | 0.13539 (7) | 0.72520 (6) | 0.0311 (3) | |
O2C | 0.05586 (19) | 0.17101 (6) | 0.70831 (6) | 0.0303 (3) | |
C1C | 0.1829 (3) | 0.13457 (8) | 0.73747 (8) | 0.0232 (3) | |
C2C | 0.0836 (10) | 0.0857 (2) | 0.79077 (18) | 0.0235 (3) | 0.795 (2) |
C3C | −0.1309 (7) | 0.0756 (3) | 0.8116 (3) | 0.0320 (6) | 0.795 (2) |
H3C | −0.242434 | 0.101251 | 0.794336 | 0.038* | 0.795 (2) |
C4C | −0.1696 (6) | 0.0221 (2) | 0.86233 (17) | 0.0270 (6) | 0.795 (2) |
H4C | −0.308005 | 0.005622 | 0.880602 | 0.032* | 0.795 (2) |
C5C | 0.0185 (4) | −0.0016 (2) | 0.88055 (17) | 0.0257 (5) | 0.795 (2) |
H5C | 0.026038 | −0.034526 | 0.915589 | 0.031* | 0.795 (2) |
S1C | 0.24428 (13) | 0.03415 (5) | 0.83360 (4) | 0.0289 (2) | 0.795 (2) |
C2C' | 0.092 (4) | 0.0854 (8) | 0.7908 (6) | 0.0235 (3) | 0.205 (2) |
S1C' | −0.1819 (7) | 0.0762 (3) | 0.8081 (3) | 0.0320 (6) | 0.205 (2) |
C4C' | −0.134 (3) | 0.0206 (9) | 0.8727 (7) | 0.0270 (6) | 0.205 (2) |
H4C' | −0.248531 | 0.004734 | 0.904501 | 0.032* | 0.205 (2) |
C5C' | 0.071 (2) | 0.0010 (9) | 0.8759 (7) | 0.0257 (5) | 0.205 (2) |
H5C' | 0.117994 | −0.033274 | 0.905439 | 0.031* | 0.205 (2) |
C3C' | 0.213 (2) | 0.0421 (10) | 0.8252 (8) | 0.0289 (2) | 0.205 (2) |
H3C' | 0.365342 | 0.038728 | 0.817909 | 0.035* | 0.205 (2) |
O1D | −0.07797 (17) | 0.23654 (6) | 0.37347 (5) | 0.0263 (3) | |
O2D | 0.22275 (18) | 0.26032 (7) | 0.41459 (6) | 0.0305 (3) | |
C1D | 0.0291 (2) | 0.27138 (8) | 0.41029 (7) | 0.0210 (3) | |
C2D | −0.0919 (3) | 0.32908 (9) | 0.45097 (9) | 0.0194 (3) | 0.953 (2) |
C3D | −0.2973 (8) | 0.3526 (4) | 0.4525 (3) | 0.0249 (7) | 0.953 (2) |
H3D | −0.393171 | 0.332453 | 0.426189 | 0.030* | 0.953 (2) |
C4D | −0.3574 (3) | 0.40997 (11) | 0.49666 (11) | 0.0248 (4) | 0.953 (2) |
H4D | −0.496068 | 0.432443 | 0.503224 | 0.030* | 0.953 (2) |
C5D | −0.1924 (3) | 0.42896 (11) | 0.52857 (10) | 0.0274 (4) | 0.953 (2) |
H5D | −0.201924 | 0.466275 | 0.560292 | 0.033* | 0.953 (2) |
S1D | 0.03497 (9) | 0.37763 (3) | 0.50481 (3) | 0.02668 (15) | 0.953 (2) |
C2D' | −0.065 (5) | 0.3297 (10) | 0.4521 (11) | 0.0194 (3) | 0.047 (2) |
S1D' | −0.327 (5) | 0.353 (2) | 0.4487 (19) | 0.0249 (7) | 0.047 (2) |
C4D' | −0.315 (6) | 0.417 (2) | 0.508 (2) | 0.0248 (4) | 0.047 (2) |
H4D' | −0.433809 | 0.447017 | 0.525319 | 0.030* | 0.047 (2) |
C5D' | −0.118 (6) | 0.421 (2) | 0.526 (2) | 0.0274 (4) | 0.047 (2) |
H5D' | −0.080477 | 0.454562 | 0.556402 | 0.033* | 0.047 (2) |
C3D' | 0.027 (6) | 0.369 (2) | 0.494 (2) | 0.02668 (15) | 0.047 (2) |
H3D' | 0.172860 | 0.363239 | 0.500762 | 0.032* | 0.047 (2) |
O1W | 0.5732 (3) | 0.26595 (10) | 0.31580 (7) | 0.0497 (4) | |
H1W1 | 0.679 (4) | 0.2610 (13) | 0.3359 (12) | 0.059 (7)* | |
H2W1 | 0.469 (4) | 0.2601 (14) | 0.3429 (13) | 0.063 (8)* |
U11 | U22 | U33 | U12 | U13 | U23 | |
O1A | 0.0283 (6) | 0.0233 (6) | 0.0313 (6) | 0.0017 (5) | 0.0045 (5) | 0.0018 (5) |
N1A | 0.0209 (6) | 0.0177 (6) | 0.0221 (7) | −0.0006 (5) | 0.0004 (5) | 0.0043 (5) |
C1A | 0.0255 (8) | 0.0209 (8) | 0.0261 (8) | 0.0008 (6) | 0.0004 (6) | 0.0029 (6) |
C2A | 0.0307 (9) | 0.0189 (8) | 0.0257 (8) | −0.0027 (6) | −0.0018 (7) | 0.0040 (6) |
C3A | 0.0299 (8) | 0.0163 (7) | 0.0307 (9) | −0.0028 (6) | −0.0043 (7) | 0.0032 (6) |
C4A | 0.0229 (8) | 0.0241 (8) | 0.0243 (8) | 0.0020 (6) | −0.0023 (6) | 0.0070 (6) |
C5A | 0.0275 (8) | 0.0311 (9) | 0.0215 (8) | −0.0028 (7) | −0.0039 (6) | 0.0037 (7) |
C6A | 0.037 (1) | 0.0282 (9) | 0.0239 (8) | 0.0000 (7) | 0.0000 (7) | −0.0010 (7) |
C7A | 0.0325 (9) | 0.0256 (9) | 0.0274 (9) | 0.0063 (7) | 0.0015 (7) | 0.0002 (7) |
C8A | 0.0200 (8) | 0.0279 (8) | 0.0255 (8) | 0.0031 (6) | 0.0007 (6) | 0.0044 (7) |
C9A | 0.0304 (8) | 0.0190 (8) | 0.0228 (8) | −0.0005 (6) | −0.0071 (6) | −0.0002 (6) |
C10A | 0.0293 (9) | 0.0258 (8) | 0.0274 (8) | −0.0015 (7) | −0.0065 (7) | −0.0002 (7) |
C11A | 0.0437 (10) | 0.0266 (9) | 0.0269 (9) | −0.0098 (8) | −0.0076 (8) | 0.0038 (7) |
C12A | 0.0499 (11) | 0.0197 (8) | 0.0306 (9) | −0.0013 (7) | −0.0142 (8) | 0.0030 (7) |
C13A | 0.0369 (10) | 0.0237 (9) | 0.0337 (9) | 0.0064 (7) | −0.0118 (8) | −0.0022 (7) |
C14A | 0.0306 (9) | 0.0235 (8) | 0.0301 (9) | −0.0022 (7) | −0.0046 (7) | 0.0009 (7) |
C15A | 0.0307 (9) | 0.0247 (8) | 0.0232 (8) | −0.0011 (7) | −0.0006 (7) | 0.0038 (6) |
C16A | 0.0495 (11) | 0.0306 (9) | 0.0255 (9) | −0.0034 (8) | −0.0034 (8) | 0.0048 (7) |
C17A | 0.0773 (16) | 0.0443 (12) | 0.0286 (10) | −0.0043 (11) | −0.008 (1) | 0.0103 (9) |
C18A | 0.0757 (16) | 0.0418 (12) | 0.0351 (11) | 0.0015 (11) | −0.0222 (11) | 0.0042 (9) |
C19A | 0.0621 (13) | 0.0368 (11) | 0.0354 (11) | 0.0009 (9) | −0.0211 (10) | −0.0001 (8) |
C20A | 0.0373 (10) | 0.0298 (9) | 0.0343 (10) | −0.0011 (7) | −0.0108 (8) | 0.0044 (7) |
O1B | 0.0169 (5) | 0.0262 (6) | 0.0203 (5) | 0.0011 (4) | −0.0043 (4) | −0.0025 (4) |
N1B | 0.0163 (6) | 0.0170 (6) | 0.0206 (6) | −0.0003 (5) | −0.0013 (5) | 0.0009 (5) |
C1B | 0.0153 (7) | 0.0222 (8) | 0.0194 (7) | 0.0001 (6) | −0.0029 (6) | 0.0010 (6) |
C2B | 0.0181 (7) | 0.0203 (7) | 0.0193 (7) | 0.0000 (6) | −0.0019 (6) | 0.0011 (6) |
C3B | 0.0171 (7) | 0.0217 (8) | 0.0230 (8) | −0.0001 (6) | 0.0022 (6) | 0.0023 (6) |
C4B | 0.0207 (8) | 0.0236 (8) | 0.0296 (9) | −0.0031 (6) | −0.0047 (6) | −0.0039 (7) |
C5B | 0.0203 (8) | 0.0258 (9) | 0.0474 (11) | −0.0043 (7) | 0.0029 (7) | −0.0057 (8) |
C6B | 0.0362 (10) | 0.0265 (9) | 0.0429 (11) | −0.0036 (7) | 0.0167 (8) | 0.0047 (8) |
C7B | 0.038 (1) | 0.0311 (9) | 0.0284 (9) | 0.0075 (8) | 0.0051 (8) | 0.0100 (7) |
C8B | 0.0230 (8) | 0.0258 (8) | 0.0262 (8) | 0.0048 (6) | −0.0021 (6) | 0.0061 (7) |
C9B | 0.0214 (7) | 0.0203 (7) | 0.0180 (7) | −0.0038 (6) | −0.0009 (6) | 0.0012 (6) |
C10B | 0.0224 (8) | 0.0339 (9) | 0.0254 (8) | −0.0036 (7) | −0.0017 (6) | −0.0050 (7) |
C11B | 0.0287 (9) | 0.0384 (10) | 0.0304 (9) | −0.0012 (7) | 0.0018 (7) | −0.0112 (8) |
C12B | 0.039 (1) | 0.0349 (10) | 0.0220 (8) | −0.0084 (8) | −0.0022 (7) | −0.0063 (7) |
C13B | 0.0307 (9) | 0.0271 (9) | 0.0246 (8) | −0.0078 (7) | −0.0094 (7) | 0.0020 (7) |
C14B | 0.0241 (8) | 0.0229 (8) | 0.0239 (8) | −0.0026 (6) | −0.0044 (6) | 0.0011 (6) |
C15B | 0.0198 (7) | 0.0217 (8) | 0.0201 (7) | −0.0021 (6) | −0.0035 (6) | 0.0001 (6) |
C16B | 0.0242 (8) | 0.0294 (9) | 0.0285 (9) | −0.0031 (7) | −0.0005 (7) | 0.0042 (7) |
C17B | 0.0304 (9) | 0.0309 (9) | 0.0343 (10) | −0.0084 (7) | −0.0017 (7) | 0.0074 (7) |
C18B | 0.0392 (10) | 0.0279 (9) | 0.039 (1) | −0.0046 (8) | −0.0071 (8) | 0.0099 (8) |
C19B | 0.0276 (9) | 0.0258 (9) | 0.0354 (9) | 0.0012 (7) | −0.0071 (7) | 0.0039 (7) |
C20B | 0.0230 (8) | 0.0256 (8) | 0.0258 (8) | −0.0018 (6) | −0.0046 (6) | 0.0021 (6) |
O1C | 0.0290 (6) | 0.0341 (7) | 0.0305 (6) | −0.0095 (5) | −0.0043 (5) | 0.0120 (5) |
O2C | 0.0370 (7) | 0.0230 (6) | 0.0301 (6) | 0.0053 (5) | −0.0033 (5) | 0.0039 (5) |
C1C | 0.0312 (8) | 0.0177 (7) | 0.0205 (7) | −0.0035 (6) | −0.0020 (6) | −0.0003 (6) |
C2C | 0.0316 (8) | 0.0195 (7) | 0.0189 (7) | −0.0046 (6) | −0.0018 (5) | −0.0006 (5) |
C3C | 0.0344 (15) | 0.0275 (6) | 0.0326 (8) | −0.0049 (11) | 0.0006 (10) | −0.0001 (5) |
C4C | 0.0274 (13) | 0.0286 (8) | 0.0242 (12) | −0.0052 (8) | −0.0009 (8) | −0.0036 (9) |
C5C | 0.0285 (14) | 0.0274 (9) | 0.0204 (9) | −0.0103 (10) | −0.0005 (9) | 0.0062 (7) |
S1C | 0.0347 (4) | 0.0309 (4) | 0.0241 (4) | −0.0118 (3) | −0.0131 (2) | 0.0109 (2) |
C2C' | 0.0316 (8) | 0.0195 (7) | 0.0189 (7) | −0.0046 (6) | −0.0018 (5) | −0.0006 (5) |
S1C' | 0.0344 (15) | 0.0275 (6) | 0.0326 (8) | −0.0049 (11) | 0.0006 (10) | −0.0001 (5) |
C4C' | 0.0274 (13) | 0.0286 (8) | 0.0242 (12) | −0.0052 (8) | −0.0009 (8) | −0.0036 (9) |
C5C' | 0.0285 (14) | 0.0274 (9) | 0.0204 (9) | −0.0103 (10) | −0.0005 (9) | 0.0062 (7) |
C3C' | 0.0347 (4) | 0.0309 (4) | 0.0241 (4) | −0.0118 (3) | −0.0131 (2) | 0.0109 (2) |
O1D | 0.0236 (6) | 0.0275 (6) | 0.0282 (6) | 0.0051 (5) | −0.0051 (5) | −0.0084 (5) |
O2D | 0.0196 (6) | 0.0374 (7) | 0.0347 (7) | 0.0048 (5) | −0.0053 (5) | 0.0029 (5) |
C1D | 0.0210 (7) | 0.0221 (8) | 0.0194 (7) | −0.0005 (6) | −0.0017 (6) | 0.0052 (6) |
C2D | 0.0225 (9) | 0.0177 (7) | 0.0182 (7) | −0.0036 (6) | −0.0029 (6) | 0.0042 (6) |
C3D | 0.0237 (18) | 0.0233 (8) | 0.0274 (12) | −0.0019 (12) | −0.0026 (12) | −0.0010 (7) |
C4D | 0.0273 (10) | 0.0185 (9) | 0.0272 (11) | −0.0013 (7) | 0.0013 (7) | −0.0007 (7) |
C5D | 0.0366 (12) | 0.0192 (9) | 0.0255 (9) | −0.0041 (8) | −0.0016 (9) | −0.0015 (7) |
S1D | 0.0310 (2) | 0.0244 (3) | 0.0271 (3) | −0.00499 (18) | −0.01186 (19) | −0.00035 (18) |
C2D' | 0.0225 (9) | 0.0177 (7) | 0.0182 (7) | −0.0036 (6) | −0.0029 (6) | 0.0042 (6) |
S1D' | 0.0237 (18) | 0.0233 (8) | 0.0274 (12) | −0.0019 (12) | −0.0026 (12) | −0.0010 (7) |
C4D' | 0.0273 (10) | 0.0185 (9) | 0.0272 (11) | −0.0013 (7) | 0.0013 (7) | −0.0007 (7) |
C5D' | 0.0366 (12) | 0.0192 (9) | 0.0255 (9) | −0.0041 (8) | −0.0016 (9) | −0.0015 (7) |
C3D' | 0.0310 (2) | 0.0244 (3) | 0.0271 (3) | −0.00499 (18) | −0.01186 (19) | −0.00035 (18) |
O1W | 0.0265 (7) | 0.0958 (13) | 0.0285 (7) | 0.0131 (8) | −0.0105 (6) | −0.0212 (8) |
O1A—C1A | 1.4356 (19) | C6B—H6BA | 0.9900 |
O1A—H1OA | 1.00 (2) | C6B—H6BB | 0.9900 |
N1A—C4A | 1.496 (2) | C7B—C8B | 1.513 (2) |
N1A—C8A | 1.4989 (19) | C7B—H7BA | 0.9900 |
N1A—C3A | 1.499 (2) | C7B—H7BB | 0.9900 |
N1A—H1NA | 0.933 (18) | C8B—H8BA | 0.9900 |
C1A—C9A | 1.526 (2) | C8B—H8BB | 0.9900 |
C1A—C2A | 1.535 (2) | C9B—C10B | 1.395 (2) |
C1A—C15A | 1.564 (2) | C9B—C14B | 1.398 (2) |
C2A—C3A | 1.527 (2) | C10B—C11B | 1.391 (2) |
C2A—H2AA | 0.9900 | C10B—H10B | 0.9500 |
C2A—H2AB | 0.9900 | C11B—C12B | 1.381 (3) |
C3A—H3AA | 0.9900 | C11B—H11B | 0.9500 |
C3A—H3AB | 0.9900 | C12B—C13B | 1.381 (2) |
C4A—C5A | 1.517 (2) | C12B—H12B | 0.9500 |
C4A—H4AA | 0.9900 | C13B—C14B | 1.388 (2) |
C4A—H4AB | 0.9900 | C13B—H13B | 0.9500 |
C5A—C6A | 1.526 (2) | C14B—H14B | 0.9500 |
C5A—H5AA | 0.9900 | C15B—C16B | 1.526 (2) |
C5A—H5AB | 0.9900 | C15B—C20B | 1.528 (2) |
C6A—C7A | 1.520 (2) | C15B—H15B | 1.0000 |
C6A—H6AA | 0.9900 | C16B—C17B | 1.530 (2) |
C6A—H6AB | 0.9900 | C16B—H16C | 0.9900 |
C7A—C8A | 1.517 (2) | C16B—H16D | 0.9900 |
C7A—H7AA | 0.9900 | C17B—C18B | 1.520 (3) |
C7A—H7AB | 0.9900 | C17B—H17C | 0.9900 |
C8A—H8AA | 0.9900 | C17B—H17D | 0.9900 |
C8A—H8AB | 0.9900 | C18B—C19B | 1.524 (2) |
C9A—C10A | 1.389 (2) | C18B—H18C | 0.9900 |
C9A—C14A | 1.396 (2) | C18B—H18D | 0.9900 |
C10A—C11A | 1.384 (2) | C19B—C20B | 1.530 (2) |
C10A—H10A | 0.9500 | C19B—H19C | 0.9900 |
C11A—C12A | 1.381 (3) | C19B—H19D | 0.9900 |
C11A—H11A | 0.9500 | C20B—H20C | 0.9900 |
C12A—C13A | 1.382 (3) | C20B—H20D | 0.9900 |
C12A—H12A | 0.9500 | O1C—C1C | 1.2596 (19) |
C13A—C14A | 1.390 (2) | O2C—C1C | 1.2533 (19) |
C13A—H13A | 0.9500 | C1C—C2C' | 1.482 (12) |
C14A—H14A | 0.9500 | C1C—C2C | 1.493 (4) |
C15A—C16A | 1.525 (2) | C2C—C3C | 1.368 (7) |
C15A—C20A | 1.527 (2) | C2C—S1C | 1.712 (6) |
C15A—H15A | 1.0000 | C3C—C4C | 1.436 (6) |
C16A—C17A | 1.529 (3) | C3C—H3C | 0.9500 |
C16A—H16A | 0.9900 | C4C—C5C | 1.356 (3) |
C16A—H16B | 0.9900 | C4C—H4C | 0.9500 |
C17A—C18A | 1.512 (3) | C5C—S1C | 1.735 (2) |
C17A—H17A | 0.9900 | C5C—H5C | 0.9500 |
C17A—H17B | 0.9900 | C2C'—C3C' | 1.36 (2) |
C18A—C19A | 1.516 (3) | C2C'—S1C' | 1.71 (2) |
C18A—H18A | 0.9900 | S1C'—C4C' | 1.738 (13) |
C18A—H18B | 0.9900 | C4C'—C5C' | 1.343 (12) |
C19A—C20A | 1.537 (3) | C4C'—H4C' | 0.9500 |
C19A—H19A | 0.9900 | C5C'—C3C' | 1.485 (15) |
C19A—H19B | 0.9900 | C5C'—H5C' | 0.9500 |
C20A—H20A | 0.9900 | C3C'—H3C' | 0.9500 |
C20A—H20B | 0.9900 | O1D—C1D | 1.2710 (19) |
O1B—C1B | 1.4327 (17) | O2D—C1D | 1.2451 (18) |
O1B—H1OB | 0.88 (2) | C1D—C2D' | 1.449 (17) |
N1B—C8B | 1.4947 (19) | C1D—C2D | 1.490 (2) |
N1B—C4B | 1.4948 (19) | C2D—C3D | 1.350 (4) |
N1B—C3B | 1.4981 (18) | C2D—S1D | 1.724 (2) |
N1B—H1NB | 0.955 (18) | C3D—C4D | 1.413 (5) |
C1B—C9B | 1.527 (2) | C3D—H3D | 0.9500 |
C1B—C2B | 1.546 (2) | C4D—C5D | 1.358 (3) |
C1B—C15B | 1.556 (2) | C4D—H4D | 0.9500 |
C2B—C3B | 1.518 (2) | C5D—S1D | 1.713 (2) |
C2B—H2BA | 0.9900 | C5D—H5D | 0.9500 |
C2B—H2BB | 0.9900 | C2D'—C3D' | 1.331 (18) |
C3B—H3BA | 0.9900 | C2D'—S1D' | 1.706 (19) |
C3B—H3BB | 0.9900 | S1D'—C4D' | 1.715 (19) |
C4B—C5B | 1.514 (2) | C4D'—C5D' | 1.347 (19) |
C4B—H4BA | 0.9900 | C4D'—H4D' | 0.9500 |
C4B—H4BB | 0.9900 | C5D'—C3D' | 1.408 (19) |
C5B—C6B | 1.514 (3) | C5D'—H5D' | 0.9500 |
C5B—H5BA | 0.9900 | C3D'—H3D' | 0.9500 |
C5B—H5BB | 0.9900 | O1W—H1W1 | 0.84 (3) |
C6B—C7B | 1.513 (3) | O1W—H2W1 | 0.81 (3) |
C1A—O1A—H1OA | 110.2 (12) | C4B—C5B—H5BA | 109.2 |
C4A—N1A—C8A | 111.01 (12) | C6B—C5B—H5BA | 109.2 |
C4A—N1A—C3A | 110.95 (12) | C4B—C5B—H5BB | 109.2 |
C8A—N1A—C3A | 110.75 (12) | C6B—C5B—H5BB | 109.2 |
C4A—N1A—H1NA | 107.3 (11) | H5BA—C5B—H5BB | 107.9 |
C8A—N1A—H1NA | 107.9 (11) | C7B—C6B—C5B | 109.36 (14) |
C3A—N1A—H1NA | 108.8 (11) | C7B—C6B—H6BA | 109.8 |
O1A—C1A—C9A | 106.32 (12) | C5B—C6B—H6BA | 109.8 |
O1A—C1A—C2A | 107.92 (13) | C7B—C6B—H6BB | 109.8 |
C9A—C1A—C2A | 111.94 (13) | C5B—C6B—H6BB | 109.8 |
O1A—C1A—C15A | 110.31 (13) | H6BA—C6B—H6BB | 108.3 |
C9A—C1A—C15A | 109.43 (13) | C8B—C7B—C6B | 110.73 (15) |
C2A—C1A—C15A | 110.80 (13) | C8B—C7B—H7BA | 109.5 |
C3A—C2A—C1A | 114.04 (13) | C6B—C7B—H7BA | 109.5 |
C3A—C2A—H2AA | 108.7 | C8B—C7B—H7BB | 109.5 |
C1A—C2A—H2AA | 108.7 | C6B—C7B—H7BB | 109.5 |
C3A—C2A—H2AB | 108.7 | H7BA—C7B—H7BB | 108.1 |
C1A—C2A—H2AB | 108.7 | N1B—C8B—C7B | 111.17 (13) |
H2AA—C2A—H2AB | 107.6 | N1B—C8B—H8BA | 109.4 |
N1A—C3A—C2A | 112.66 (12) | C7B—C8B—H8BA | 109.4 |
N1A—C3A—H3AA | 109.1 | N1B—C8B—H8BB | 109.4 |
C2A—C3A—H3AA | 109.1 | C7B—C8B—H8BB | 109.4 |
N1A—C3A—H3AB | 109.1 | H8BA—C8B—H8BB | 108.0 |
C2A—C3A—H3AB | 109.1 | C10B—C9B—C14B | 118.04 (14) |
H3AA—C3A—H3AB | 107.8 | C10B—C9B—C1B | 120.56 (14) |
N1A—C4A—C5A | 111.54 (13) | C14B—C9B—C1B | 121.39 (13) |
N1A—C4A—H4AA | 109.3 | C11B—C10B—C9B | 120.71 (15) |
C5A—C4A—H4AA | 109.3 | C11B—C10B—H10B | 119.6 |
N1A—C4A—H4AB | 109.3 | C9B—C10B—H10B | 119.6 |
C5A—C4A—H4AB | 109.3 | C12B—C11B—C10B | 120.42 (16) |
H4AA—C4A—H4AB | 108.0 | C12B—C11B—H11B | 119.8 |
C4A—C5A—C6A | 111.17 (14) | C10B—C11B—H11B | 119.8 |
C4A—C5A—H5AA | 109.4 | C11B—C12B—C13B | 119.61 (16) |
C6A—C5A—H5AA | 109.4 | C11B—C12B—H12B | 120.2 |
C4A—C5A—H5AB | 109.4 | C13B—C12B—H12B | 120.2 |
C6A—C5A—H5AB | 109.4 | C12B—C13B—C14B | 120.28 (15) |
H5AA—C5A—H5AB | 108.0 | C12B—C13B—H13B | 119.9 |
C7A—C6A—C5A | 109.78 (14) | C14B—C13B—H13B | 119.9 |
C7A—C6A—H6AA | 109.7 | C13B—C14B—C9B | 120.91 (15) |
C5A—C6A—H6AA | 109.7 | C13B—C14B—H14B | 119.5 |
C7A—C6A—H6AB | 109.7 | C9B—C14B—H14B | 119.5 |
C5A—C6A—H6AB | 109.7 | C16B—C15B—C20B | 109.72 (13) |
H6AA—C6A—H6AB | 108.2 | C16B—C15B—C1B | 111.92 (12) |
C8A—C7A—C6A | 111.29 (14) | C20B—C15B—C1B | 116.31 (12) |
C8A—C7A—H7AA | 109.4 | C16B—C15B—H15B | 106.0 |
C6A—C7A—H7AA | 109.4 | C20B—C15B—H15B | 106.0 |
C8A—C7A—H7AB | 109.4 | C1B—C15B—H15B | 106.0 |
C6A—C7A—H7AB | 109.4 | C15B—C16B—C17B | 111.13 (14) |
H7AA—C7A—H7AB | 108.0 | C15B—C16B—H16C | 109.4 |
N1A—C8A—C7A | 110.79 (13) | C17B—C16B—H16C | 109.4 |
N1A—C8A—H8AA | 109.5 | C15B—C16B—H16D | 109.4 |
C7A—C8A—H8AA | 109.5 | C17B—C16B—H16D | 109.4 |
N1A—C8A—H8AB | 109.5 | H16C—C16B—H16D | 108.0 |
C7A—C8A—H8AB | 109.5 | C18B—C17B—C16B | 111.32 (14) |
H8AA—C8A—H8AB | 108.1 | C18B—C17B—H17C | 109.4 |
C10A—C9A—C14A | 118.07 (15) | C16B—C17B—H17C | 109.4 |
C10A—C9A—C1A | 120.81 (14) | C18B—C17B—H17D | 109.4 |
C14A—C9A—C1A | 121.10 (14) | C16B—C17B—H17D | 109.4 |
C11A—C10A—C9A | 120.93 (16) | H17C—C17B—H17D | 108.0 |
C11A—C10A—H10A | 119.5 | C17B—C18B—C19B | 111.30 (14) |
C9A—C10A—H10A | 119.5 | C17B—C18B—H18C | 109.4 |
C12A—C11A—C10A | 120.43 (17) | C19B—C18B—H18C | 109.4 |
C12A—C11A—H11A | 119.8 | C17B—C18B—H18D | 109.4 |
C10A—C11A—H11A | 119.8 | C19B—C18B—H18D | 109.4 |
C11A—C12A—C13A | 119.64 (16) | H18C—C18B—H18D | 108.0 |
C11A—C12A—H12A | 120.2 | C18B—C19B—C20B | 111.16 (14) |
C13A—C12A—H12A | 120.2 | C18B—C19B—H19C | 109.4 |
C12A—C13A—C14A | 119.90 (16) | C20B—C19B—H19C | 109.4 |
C12A—C13A—H13A | 120.0 | C18B—C19B—H19D | 109.4 |
C14A—C13A—H13A | 120.0 | C20B—C19B—H19D | 109.4 |
C13A—C14A—C9A | 120.99 (16) | H19C—C19B—H19D | 108.0 |
C13A—C14A—H14A | 119.5 | C15B—C20B—C19B | 110.96 (13) |
C9A—C14A—H14A | 119.5 | C15B—C20B—H20C | 109.4 |
C16A—C15A—C20A | 109.41 (15) | C19B—C20B—H20C | 109.4 |
C16A—C15A—C1A | 114.22 (14) | C15B—C20B—H20D | 109.4 |
C20A—C15A—C1A | 111.91 (13) | C19B—C20B—H20D | 109.4 |
C16A—C15A—H15A | 107.0 | H20C—C20B—H20D | 108.0 |
C20A—C15A—H15A | 107.0 | O2C—C1C—O1C | 125.58 (15) |
C1A—C15A—H15A | 107.0 | O2C—C1C—C2C' | 118.5 (9) |
C15A—C16A—C17A | 111.76 (16) | O1C—C1C—C2C' | 115.9 (9) |
C15A—C16A—H16A | 109.3 | O2C—C1C—C2C | 116.6 (3) |
C17A—C16A—H16A | 109.3 | O1C—C1C—C2C | 117.8 (3) |
C15A—C16A—H16B | 109.3 | C3C—C2C—C1C | 127.6 (5) |
C17A—C16A—H16B | 109.3 | C3C—C2C—S1C | 112.4 (3) |
H16A—C16A—H16B | 107.9 | C1C—C2C—S1C | 120.0 (4) |
C18A—C17A—C16A | 111.81 (18) | C2C—C3C—C4C | 112.9 (5) |
C18A—C17A—H17A | 109.3 | C2C—C3C—H3C | 123.6 |
C16A—C17A—H17A | 109.3 | C4C—C3C—H3C | 123.6 |
C18A—C17A—H17B | 109.3 | C5C—C4C—C3C | 110.6 (4) |
C16A—C17A—H17B | 109.3 | C5C—C4C—H4C | 124.7 |
H17A—C17A—H17B | 107.9 | C3C—C4C—H4C | 124.7 |
C17A—C18A—C19A | 110.40 (18) | C4C—C5C—S1C | 113.4 (3) |
C17A—C18A—H18A | 109.6 | C4C—C5C—H5C | 123.3 |
C19A—C18A—H18A | 109.6 | S1C—C5C—H5C | 123.3 |
C17A—C18A—H18B | 109.6 | C2C—S1C—C5C | 90.48 (19) |
C19A—C18A—H18B | 109.6 | C3C'—C2C'—C1C | 124.0 (16) |
H18A—C18A—H18B | 108.1 | C3C'—C2C'—S1C' | 116.2 (10) |
C18A—C19A—C20A | 111.35 (16) | C1C—C2C'—S1C' | 119.6 (14) |
C18A—C19A—H19A | 109.4 | C2C'—S1C'—C4C' | 87.0 (8) |
C20A—C19A—H19A | 109.4 | C5C'—C4C'—S1C' | 117.5 (12) |
C18A—C19A—H19B | 109.4 | C5C'—C4C'—H4C' | 121.3 |
C20A—C19A—H19B | 109.4 | S1C'—C4C'—H4C' | 121.3 |
H19A—C19A—H19B | 108.0 | C4C'—C5C'—C3C' | 108.1 (13) |
C15A—C20A—C19A | 112.89 (16) | C4C'—C5C'—H5C' | 125.9 |
C15A—C20A—H20A | 109.0 | C3C'—C5C'—H5C' | 125.9 |
C19A—C20A—H20A | 109.0 | C2C'—C3C'—C5C' | 110.3 (13) |
C15A—C20A—H20B | 109.0 | C2C'—C3C'—H3C' | 124.9 |
C19A—C20A—H20B | 109.0 | C5C'—C3C'—H3C' | 124.9 |
H20A—C20A—H20B | 107.8 | O2D—C1D—O1D | 124.94 (15) |
C1B—O1B—H1OB | 106.6 (12) | O2D—C1D—C2D' | 112.5 (14) |
C8B—N1B—C4B | 111.36 (12) | O1D—C1D—C2D' | 122.5 (14) |
C8B—N1B—C3B | 110.39 (11) | O2D—C1D—C2D | 119.14 (15) |
C4B—N1B—C3B | 111.26 (12) | O1D—C1D—C2D | 115.92 (14) |
C8B—N1B—H1NB | 107.5 (10) | C3D—C2D—C1D | 129.6 (3) |
C4B—N1B—H1NB | 107.8 (10) | C3D—C2D—S1D | 110.5 (2) |
C3B—N1B—H1NB | 108.4 (10) | C1D—C2D—S1D | 119.83 (14) |
O1B—C1B—C9B | 106.73 (12) | C2D—C3D—C4D | 114.2 (3) |
O1B—C1B—C2B | 108.88 (12) | C2D—C3D—H3D | 122.9 |
C9B—C1B—C2B | 110.47 (12) | C4D—C3D—H3D | 122.9 |
O1B—C1B—C15B | 107.46 (12) | C5D—C4D—C3D | 111.6 (2) |
C9B—C1B—C15B | 112.84 (12) | C5D—C4D—H4D | 124.2 |
C2B—C1B—C15B | 110.27 (12) | C3D—C4D—H4D | 124.2 |
C3B—C2B—C1B | 110.51 (12) | C4D—C5D—S1D | 111.97 (14) |
C3B—C2B—H2BA | 109.5 | C4D—C5D—H5D | 124.0 |
C1B—C2B—H2BA | 109.5 | S1D—C5D—H5D | 124.0 |
C3B—C2B—H2BB | 109.5 | C5D—S1D—C2D | 91.72 (9) |
C1B—C2B—H2BB | 109.5 | C3D'—C2D'—C1D | 128 (2) |
H2BA—C2B—H2BB | 108.1 | C3D'—C2D'—S1D' | 114.0 (15) |
N1B—C3B—C2B | 112.17 (12) | C1D—C2D'—S1D' | 118 (2) |
N1B—C3B—H3BA | 109.2 | C2D'—S1D'—C4D' | 89.6 (13) |
C2B—C3B—H3BA | 109.2 | C5D'—C4D'—S1D' | 112.4 (18) |
N1B—C3B—H3BB | 109.2 | C5D'—C4D'—H4D' | 123.8 |
C2B—C3B—H3BB | 109.2 | S1D'—C4D'—H4D' | 123.8 |
H3BA—C3B—H3BB | 107.9 | C4D'—C5D'—C3D' | 113 (2) |
N1B—C4B—C5B | 111.40 (13) | C4D'—C5D'—H5D' | 123.7 |
N1B—C4B—H4BA | 109.3 | C3D'—C5D'—H5D' | 123.7 |
C5B—C4B—H4BA | 109.3 | C2D'—C3D'—C5D' | 111.4 (19) |
N1B—C4B—H4BB | 109.3 | C2D'—C3D'—H3D' | 124.3 |
C5B—C4B—H4BB | 109.3 | C5D'—C3D'—H3D' | 124.3 |
H4BA—C4B—H4BB | 108.0 | H1W1—O1W—H2W1 | 105 (2) |
C4B—C5B—C6B | 111.93 (14) | ||
O1A—C1A—C2A—C3A | −72.04 (17) | C9B—C10B—C11B—C12B | 0.8 (3) |
C9A—C1A—C2A—C3A | 44.62 (18) | C10B—C11B—C12B—C13B | −1.2 (3) |
C15A—C1A—C2A—C3A | 167.08 (13) | C11B—C12B—C13B—C14B | 0.1 (3) |
C4A—N1A—C3A—C2A | 154.13 (13) | C12B—C13B—C14B—C9B | 1.4 (2) |
C8A—N1A—C3A—C2A | −82.12 (16) | C10B—C9B—C14B—C13B | −1.8 (2) |
C1A—C2A—C3A—N1A | 140.13 (14) | C1B—C9B—C14B—C13B | 177.10 (14) |
C8A—N1A—C4A—C5A | 56.52 (16) | O1B—C1B—C15B—C16B | 61.74 (16) |
C3A—N1A—C4A—C5A | −179.88 (12) | C9B—C1B—C15B—C16B | −55.65 (16) |
N1A—C4A—C5A—C6A | −55.86 (17) | C2B—C1B—C15B—C16B | −179.72 (12) |
C4A—C5A—C6A—C7A | 54.99 (18) | O1B—C1B—C15B—C20B | −171.04 (12) |
C5A—C6A—C7A—C8A | −55.89 (18) | C9B—C1B—C15B—C20B | 71.57 (16) |
C4A—N1A—C8A—C7A | −56.93 (16) | C2B—C1B—C15B—C20B | −52.50 (17) |
C3A—N1A—C8A—C7A | 179.36 (13) | C20B—C15B—C16B—C17B | 57.42 (18) |
C6A—C7A—C8A—N1A | 57.21 (17) | C1B—C15B—C16B—C17B | −171.89 (13) |
O1A—C1A—C9A—C10A | −20.6 (2) | C15B—C16B—C17B—C18B | −56.28 (19) |
C2A—C1A—C9A—C10A | −138.19 (15) | C16B—C17B—C18B—C19B | 54.5 (2) |
C15A—C1A—C9A—C10A | 98.57 (17) | C17B—C18B—C19B—C20B | −54.7 (2) |
O1A—C1A—C9A—C14A | 161.28 (15) | C16B—C15B—C20B—C19B | −57.63 (17) |
C2A—C1A—C9A—C14A | 43.7 (2) | C1B—C15B—C20B—C19B | 174.07 (13) |
C15A—C1A—C9A—C14A | −79.58 (19) | C18B—C19B—C20B—C15B | 56.61 (18) |
C14A—C9A—C10A—C11A | −0.6 (2) | O2C—C1C—C2C—C3C | 0.3 (6) |
C1A—C9A—C10A—C11A | −178.83 (15) | O1C—C1C—C2C—C3C | −179.1 (4) |
C9A—C10A—C11A—C12A | −0.9 (3) | O2C—C1C—C2C—S1C | −179.70 (18) |
C10A—C11A—C12A—C13A | 1.1 (3) | O1C—C1C—C2C—S1C | 0.9 (4) |
C11A—C12A—C13A—C14A | 0.1 (3) | C1C—C2C—C3C—C4C | 177.5 (4) |
C12A—C13A—C14A—C9A | −1.7 (3) | S1C—C2C—C3C—C4C | −2.5 (7) |
C10A—C9A—C14A—C13A | 1.9 (2) | C2C—C3C—C4C—C5C | 4.5 (7) |
C1A—C9A—C14A—C13A | −179.88 (15) | C3C—C4C—C5C—S1C | −4.6 (5) |
O1A—C1A—C15A—C16A | −72.32 (18) | C3C—C2C—S1C—C5C | −0.1 (4) |
C9A—C1A—C15A—C16A | 171.04 (14) | C1C—C2C—S1C—C5C | 179.9 (3) |
C2A—C1A—C15A—C16A | 47.13 (19) | C4C—C5C—S1C—C2C | 2.8 (3) |
O1A—C1A—C15A—C20A | 52.69 (18) | O2C—C1C—C2C'—C3C' | 178.7 (11) |
C9A—C1A—C15A—C20A | −63.95 (17) | O1C—C1C—C2C'—C3C' | −0.8 (13) |
C2A—C1A—C15A—C20A | 172.14 (14) | O2C—C1C—C2C'—S1C' | 3.4 (11) |
C20A—C15A—C16A—C17A | 54.7 (2) | O1C—C1C—C2C'—S1C' | −176.1 (6) |
C1A—C15A—C16A—C17A | −178.95 (16) | C3C'—C2C'—S1C'—C4C' | 8.2 (13) |
C15A—C16A—C17A—C18A | −57.3 (2) | C1C—C2C'—S1C'—C4C' | −176.1 (10) |
C16A—C17A—C18A—C19A | 56.3 (2) | C2C'—S1C'—C4C'—C5C' | −9.2 (14) |
C17A—C18A—C19A—C20A | −54.6 (2) | S1C'—C4C'—C5C'—C3C' | 7.6 (18) |
C16A—C15A—C20A—C19A | −54.0 (2) | C1C—C2C'—C3C'—C5C' | 178.8 (12) |
C1A—C15A—C20A—C19A | 178.42 (14) | S1C'—C2C'—C3C'—C5C' | −5.7 (17) |
C18A—C19A—C20A—C15A | 54.8 (2) | C4C'—C5C'—C3C'—C2C' | −1.2 (18) |
O1B—C1B—C2B—C3B | −43.39 (16) | O2D—C1D—C2D—C3D | 176.8 (5) |
C9B—C1B—C2B—C3B | 73.51 (15) | O1D—C1D—C2D—C3D | −3.6 (5) |
C15B—C1B—C2B—C3B | −161.07 (12) | O2D—C1D—C2D—S1D | −1.9 (2) |
C8B—N1B—C3B—C2B | −152.81 (13) | O1D—C1D—C2D—S1D | 177.75 (11) |
C4B—N1B—C3B—C2B | 83.03 (15) | C1D—C2D—C3D—C4D | −178.7 (3) |
C1B—C2B—C3B—N1B | −179.42 (12) | S1D—C2D—C3D—C4D | 0.0 (7) |
C8B—N1B—C4B—C5B | 54.34 (17) | C2D—C3D—C4D—C5D | −0.2 (7) |
C3B—N1B—C4B—C5B | 177.94 (13) | C3D—C4D—C5D—S1D | 0.2 (4) |
N1B—C4B—C5B—C6B | −54.87 (18) | C4D—C5D—S1D—C2D | −0.17 (17) |
C4B—C5B—C6B—C7B | 55.87 (19) | C3D—C2D—S1D—C5D | 0.1 (4) |
C5B—C6B—C7B—C8B | −57.11 (18) | C1D—C2D—S1D—C5D | 178.98 (14) |
C4B—N1B—C8B—C7B | −56.14 (17) | O2D—C1D—C2D'—C3D' | −2 (2) |
C3B—N1B—C8B—C7B | 179.76 (13) | O1D—C1D—C2D'—C3D' | 179 (3) |
C6B—C7B—C8B—N1B | 57.95 (18) | O2D—C1D—C2D'—S1D' | 177.5 (19) |
O1B—C1B—C9B—C10B | −9.16 (19) | O1D—C1D—C2D'—S1D' | −2 (2) |
C2B—C1B—C9B—C10B | −127.39 (15) | C3D'—C2D'—S1D'—C4D' | −2 (3) |
C15B—C1B—C9B—C10B | 108.65 (16) | C1D—C2D'—S1D'—C4D' | 178.9 (19) |
O1B—C1B—C9B—C14B | 171.96 (13) | C2D'—S1D'—C4D'—C5D' | 2 (4) |
C2B—C1B—C9B—C14B | 53.74 (18) | S1D'—C4D'—C5D'—C3D' | −2 (6) |
C15B—C1B—C9B—C14B | −70.22 (18) | C1D—C2D'—C3D'—C5D' | −180 (3) |
C14B—C9B—C10B—C11B | 0.7 (2) | S1D'—C2D'—C3D'—C5D' | 1 (3) |
C1B—C9B—C10B—C11B | −178.20 (15) | C4D'—C5D'—C3D'—C2D' | 1 (5) |
D—H···A | D—H | H···A | D···A | D—H···A |
O1A—H1OA···O2Ci | 1.00 (2) | 1.72 (2) | 2.7143 (16) | 172.3 (18) |
N1A—H1NA···O1C | 0.933 (18) | 1.793 (18) | 2.7084 (17) | 166.4 (16) |
N1A—H1NA···O2C | 0.933 (18) | 2.606 (18) | 3.3355 (18) | 135.4 (14) |
C4A—H4AB···O1Aii | 0.99 | 2.51 | 3.407 (2) | 150 |
C5A—H5AA···O2D | 0.99 | 2.54 | 3.358 (2) | 139 |
C8A—H8AA···O2Ci | 0.99 | 2.29 | 3.283 (2) | 177 |
O1B—H1OB···O1W | 0.88 (2) | 1.85 (2) | 2.7186 (18) | 169.5 (18) |
N1B—H1NB···O1D | 0.955 (18) | 1.700 (18) | 2.6497 (17) | 172.8 (16) |
C3B—H3BB···O1W | 0.99 | 2.61 | 3.295 (2) | 126 |
O1W—H1W1···O1Di | 0.84 (3) | 1.86 (3) | 2.6873 (18) | 171 (2) |
O1W—H2W1···O2D | 0.81 (3) | 1.98 (3) | 2.775 (2) | 171 (3) |
Symmetry codes: (i) x+1, y, z; (ii) x−1, y, z. |
The primed (') atoms in I are III are for the second disorder component. |
Torsion | I | II | III | IVa | IVb |
O1—C1—C2—C3 | -60.52 (14) | -60.92 (18) | 54.5 (2) | -72.04 (17) | -43.38 (16) |
C1—C2—C3—N1 | 152.29 (11) | 147.37 (15) | -152.27 (17) | 140.13 (14) | -179.42 (12) |
C2—C3—N1—C4 | 59.11 (15) | 58.13 (19) | -70.0 (2) | 154.13 (13) | 83.03 (15) |
O1—C1—C9—C10 | -25.1 (5) | -13.2 (2) | -23.8 (2) | -20.6 (2) | -9.16 (19) |
O1—C1—C15—C16 | 49.4 (7) | 58.47 (19) | 57.2 (6) | -72.32 (18) | 61.74 (16) |
O1—C1—C9'—C10' | 17.5 (8) | - | 21.4 (4) | - | - |
O1—C1—C15'—C16' | 168.6 (4) | - | 178.8 (5) | - | - |
Acknowledgements
One of the authors (V) is grateful to the DST–PURSE Project, Vijnana Bhavana, UOM for providing research facilities. HSY thanks UGC for a BSR Faculty fellowship for three years.
Funding information
Funding for this research was provided by: National Science Foundation, Directorate for Mathematical and Physical Sciences (award No. MRI CHE1625732 to SP).
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