research communications
Syntheses, crystal structures and Hirshfeld surface analyses of four molecular salts of amitriptynol
aDepartment of Studies in Chemistry, University of Mysore, Manasagangotri, Mysuru-570 006, India, bDepartment of Science and Humanities, PES University, BSK III Stage, Bengaluru-560 085, India, cDepartment of Chemistry, Amrita School of Engineering, Amrita Vishwa Vidyapeetham, Bengaluru-560 035, India, and dDepartment of Chemistry, University of Kentucky, Lexington, KY, 40506-0055, USA
*Correspondence e-mail: ybb2706@gmail.com, yathirajan@hotmail.com
The syntheses and crystal structures of four salts of amitriptynol (C20H25NO) with different carboxylic acids are described. The salts formed directly from solutions of amitriptyline (which first hydrolysed to amitriptynol) and the corresponding acid in acetonitrile to form amitriptynolium [systematic name: (3-{2-hydroxytricyclo[9.4.0.03,8]pentadeca-1(11),3,5,7,12,14-hexaen-2-yl}propyl)dimethylazanium] 4-methoxybenzoate monohydrate, C20H26NO+·C8H7O3−·H2O, (I), amitriptynolium 3,4-dimethoxybenzoate trihydrate, C20H26NO+·C9H9O4−·3H2O, (II), amitriptynolium 2-chlorobenzoate, C20H26NO+·C7H4ClO2−, (III), and amitriptynolium thiophene-2-carboxylate monohydrate, C20H26NO+·C5H3O2S−·H2O, (IV). Compound (III) crystallizes with two cations, two anions and six water molecules in the The different conformations of the amitriptynolium cations are determined by the torsion angles in the dimethylamino-propyl chains and the –CH2–CH2- bridge between the benzene rings in the tricyclic ring system, and are complicated by disorder of the bridging unit in II and III. The packing in all four salts is dominated by N—H⋯O and O—H⋯O hydrogen bonds. Hirshfeld surface analyses show that the amitriptynolium cations make similar inter-species contacts, despite the distinctly different packing in each salt.
1. Chemical context
Amitriptynol, C20H25NO, 5-[3-(dimethylamino)propyl]-10,11-dihydro-5H-dibenzo[a,d][7]annulen-5-ol, is a derivative and common impurity (designated `amitriptyline impurity B′) of amitriptyline, C20H23N. Amitriptyline is a tricyclic antidepressant agent, which also has analgesic properties with sedative effects. Amitriptyline affects certain chemical messengers (neurotransmitters) that communicate between brain cells and help regulate mood. It is used in the treatment of depression, neuropathic pain, and migraine.
A review of the pharmacological properties and therapeutic use for chronic pain of amitriptyline was published by Bryson & Wilde (1996). A comprehensive review of amitriptyline for the treatment of fibromyalgia was given by Rico-Villademoros et al. (2015). In a systematic review, Thompson & Brooks (2015) discussed the use of topical amitriptyline for the treatment of neuropathic pain. A brief review of the pharmacology of amitriptyline and clinical outcomes in treating fibromyalgia was given by Lawson (2017). Analytical methods for the determination of amitriptyline and its metabolite nortriptyline were reviewed by Khatoon et al. (2013). Molecular insights from single-crystal X-ray diffraction and DFT calculations of β-cyclodextrin encapsulation of nortriptyline HCl and amitriptyline HCl were published by Aree (2020a).
Our goal was to prepare molecular salts of amitriptyline, but the amitriptyline free base is susceptible to hydrolysis, owing to its aliphatic double bond attached to the central seven-membered ring (Henwood, 1967). Consequently, the amitriptyline hydrolysed to amitriptynol, which then formed salts with the organic acids. Perhaps surprisingly, any such salts have thus far been absent from the crystallographic literature. This paper reports the crystal structures of four amitriptynolium (C20H26NO+) salts: 4-methoxybenzoate monohydrate (I), 3,4-dimethoxybenzoate trihydrate, (II), 2-chlorobenzoate (III) and thiophene-2-carboxylate monohydrate (IV).
2. Structural commentary
Salts I and IV crystallized as monohydrates, and II as a trihydrate; only salt III is anhydrous (see Figs. 1–4). In spite of their chemical similarity (i.e., the same cation and similar sized aromatic carboxylate anions), the crystal structures of I–IV are notably distinct, each having different space-group symmetries (Pn for I, Cc for II, P21/n for III, and P212121 for IV). Although only IV has a Sohncke its structure was twinned by inversion, with major:minor twin fractions of 0.70 (7):0.30 (7), so any discussion of is moot.
The conformations of the amitriptynolium cations are determined by the torsion angles in the dimethylamino-propyl chains and by the C6—C7—C8—C9 torsion angles in the long bridge between the benzene rings of the tricyclic ring system, and are complicated by cation disorder in II and III. All conformation-defining torsion angles are given in Table 1, but further description is limited to the major disorder components. From Table 1 and Figs. 1–4, it is evident that the cation geometries in I, III, and IV are broadly similar. The two independent cations in II, however, are self-similar, but different from I, III, and IV, primarily evidenced by the C16—C17—C18—N1 torsion angle, which is anti in both cations of II, but gauche in I, III, and IV. In each case, the tricyclic unit of the cation adopts a `butterfly' conformation with dihedral angles between the pendant benzene rings of 62.01 (9) (I), 69.30 (16) and 71.06 (13) (II), 57.21 (10) (III) and 50.51 (8)° (IV). In every case, the –OH group attached to C15 is in an equatorial orientation and the pendant alkyl chain is axial.
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The 4-methoxybenzoate anion in I is largely planar, with maximum deviation from planarity of 0.1216 (15) Å, caused by a C24—C25—O4—C28 torsion angle of −7.5 (2)° for the methoxy group. In II, the 3,4-dimethoxybenzoate anions are also close to planar. In the `A' anion, C29A is offset by 0.229 (2) Å from the mean plane, for a C26A—C25A—O5A—C29A methoxy torsion of 13.6 (3)°, while for the `B' anion, the largest deviation is 0.2264 (16) Å for O2B, due to the dihedral angle between the benzene ring and the carboxylate group of 10.43 (15)°. The 2-chlorobenzoate anion in III is disordered by a ∼180° flip, giving major:minor component occupancies of 0.9600 (15):0.0400 (15). The two components are, however, far from planar as a result of by the chlorine substituent; the dihedral angles between the chlorobenzene and carboxylate groups being 57.82 (11)° and 56.4 (5)° for the major and minor parts, respectively. In IV, the thiophene-2-carboxylate anion is also disordered, with major:minor occupancies of 0.899 (3):0.101 (3), but the components are again largely planar; the maximum deviations being for O3 in each, at 0.167 (3) Å (major) and 0.14 (2) Å (minor), resulting from dihedral angles between the thiophene rings and carboxylate groups of 12.3 (6)° (major) and 11 (5)° (minor).
3. Supramolecular features
The dominant supramolecular features in all four salts are N—H⋯O hydrogen bonds between the cationic [R3N—H]+ moiety and the anion carboxylate groups, plus O—H⋯O hydrogen bonds involving the amitriptynolium cation O—H group as donor to a carboxylate acceptor in III and to water molecules in I, II, and IV. These hydroxyl groups are effectively shielded from accepting strong hydrogen bonds by the adjacent benzene rings of the amitriptynolium fused ring systems in each case. The strong hydrogen bonds are augmented in all four structures by a few weaker C—H⋯O contacts.
In I, the main packing motifs are infinite chains of N—H⋯O and O—H⋯O hydrogen-bonded cations, anions, and water molecules that extend parallel to the a-axis direction. These are shown in Fig. 5 and quantified in Table 2, along with their attendant symmetry operations.
Owing to the presence of two copies each of cation and anion, plus six water molecules in the Z′ = 2), the packing in II is the most complex of the four salts. However, the most obvious supramolecular feature, an R44(8) ring of water molecules, is evident in the ellipsoid plot of its (Fig. 2). These rings of four water molecules are hydrogen bonded to the anion carboxylate groups (via O1W and O4W to O3A and O2B, respectively), and via O2W and O3W to (−1 + x, y, z) and (1 + x, y, z) translation-related anion carboxylate groups (Table 3). The anions in turn act as hydrogen-bond acceptors to the cations (via O2A to N1A and O2B to N1B). The remaining water molecules accept hydrogen bonds from the cation hydroxyl groups (O1A to O5W and O1B to O6W), also shown in Fig. 2. In addition to the hydrogen-bonded motifs shown in Fig. 2, water molecule O5W takes part in bifurcated O—H⋯(O,O) hydrogen bonding to both methoxy groups of a translation-related (x, y, −1 + z) anion, and similar bifurcated hydrogen bonding occurs between water molecule O6W and a translation-related (−1 + x, y, 1 + z) anion. The net result gives layers of cations and layers of anions parallel to the ac plane interspersed with and separated by the water molecules (Fig. 6). These layers stack along the b-axis direction to build an intricate three-dimensional framework. Given its complexity and the size of the [the b-axis is 55.2061 (19) Å], the specific interactions are largely obscured, and are best viewed using a molecular graphics program such as Mercury (Macrae et al., 2020).
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The hydrogen bonding in III is the simplest of the four salts because there are no water molecules involved. N—H⋯O hydrogen bonds connect cation to anion within the (chosen) and O—H⋯O hydrogen bonds connect cations to anions in adjacent unit cells, to form chains that extend parallel to the a-axis, as shown in Fig. 7 and Table 4. The main supramolecular constructs in IV are hydrogen-bonded chains that propagate parallel to its a-axis, broadly similar to those in I (Fig. 8, Table 5).
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Although structures I–IV are quite different, atom-to-atom contacts involving just the amitriptynolium cations expressed in Hirshfeld-surface two-dimensional fingerprint plots (Spackman et al., 2021) in each are remarkably similar, as shown in Fig. 9. The most abundant contacts are between hydrogen atoms, ranging from 56.4% in III to 64.3% in I. The next most abundant contacts are H⋯C/C⋯H, which range between 22.8% coverage in I to 27.2% in II. The only other double-digit percentage coverages are for H⋯O/O⋯H contacts, which range from 11.2% in IV to 12.9% in III. All other types of contact involving the cations are negligible.
4. Database survey
A search of the Cambridge Structural Database (CSD v5.43 plus updates to Nov. 2022; Groom et al., 2016) for a search fragment consisting of the three fused rings with a propyl-1-amine chain attached to the seven-membered ring returned nine hits. CSD refcode CHSBHA (Wägner, 1980) has a spiro-2-cyclohexene-4-N,N-dimethylamine group in place of the propyl-1-amine chain. Entries CIKVEX and CIKVIB (Horsburgh et al., 1984) are racaemic (S,S and R,R) and meso (S,R) pentacyclic analogues of amitryptyline. Structures KOGXIP (Kise et al., 2014), QUKDEH (Kise et al., 2015), IQALUJ, IQAPEX, and IQAPIB (Kise et al., 2016) carry a variety of ring-containing groups in place of the propyl-1-amine chain. Lastly, entry YEYTUS (Portalone et al., 2007) is the free-base amitriptynol, from which salts I–IV were prepared. Other related structures, not returned in the above CSD search, include nortriptyline hydrochloride (JINGIW; Klein et al., 1991), three tricyclic neuroleptics (MEAPOT11, YOVYUD, and YOVZEO; Klein et al., 1994), amitriptylinium picrate (DIKWEA; Bindya et al., 2007), desipraminium chloride (PUKGEI; Jasinski et al., 2010), desipraminium picrate (HISHEX; Swamy et al., 2007), imipramine hydrochloride and desipramine hydrochloride (PAJTON and PALBOX; Aree, 2020b).
5. Synthesis and crystallization
Solutions of commercially available (RL Fine Chem, Bengaluru, India) amitriptyline (100 mg, 0.360 mol) in methanol (10 ml) were mixed with equimolar solutions of the appropriate acid in acetonitrile (10 ml) viz., 4-methoxybenzoic acid (55 mg, 0.360 mol) for I, 3,4-dimethoxybenzoic acid (67 mg, 0.483 mol) for II, 2-chlorobenzoic acid (57 mg, 0.360 mol) for III and thiophene 2-carboxylic acid (46 mg, 0.360 mol) for IV. The resulting solutions were stirred for 30 minutes at 333 K and allowed to stand at room temperature. X-ray quality crystals formed on slow evaporation of solutions in ethanol:acetonitrile (1:1) after a week for all four compounds. The melting points are 367–369 K (I), 359–361 K (II), 410–412 K (III) and 373–376 K (IV).
6. Refinement
Crystal data, data collection, and . Crystals of III shattered on cooling to 90 K, but remained intact at 180 K. Non-disordered hydrogen atoms were located in difference-Fourier maps. Those bound to nitrogen or oxygen atoms were refined, but carbon-bound hydrogen atoms were included using riding models with constrained distances of 0.95 Å (Csp2H), 0.99 Å (R2CH2), and 0.98 Å (RCH3) using Uiso(H) values constrained to 1.2Ueq or 1.5Ueq (methyl group only) of the attached carbon atom. Structure IV was twinned by inversion, which was included using the standard TWIN/BASF treatment in SHELXL. Two-component disorder in the amitriptynolium cations of II and III and the anions of III and IV was handled using separate PART instructions and occupancies set via FVAR parameters in SHELXL.
are given in Table 6
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Supporting information
https://doi.org/10.1107/S2056989023003225/hb8061sup1.cif
contains datablocks I, II, III, IV, global. DOI:Structure factors: contains datablock I. DOI: https://doi.org/10.1107/S2056989023003225/hb8061Isup2.hkl
Structure factors: contains datablock II. DOI: https://doi.org/10.1107/S2056989023003225/hb8061IIsup3.hkl
Structure factors: contains datablock III. DOI: https://doi.org/10.1107/S2056989023003225/hb8061IIIsup4.hkl
Structure factors: contains datablock IV. DOI: https://doi.org/10.1107/S2056989023003225/hb8061IVsup5.hkl
Supporting information file. DOI: https://doi.org/10.1107/S2056989023003225/hb8061Isup6.cml
Supporting information file. DOI: https://doi.org/10.1107/S2056989023003225/hb8061IIIsup7.cml
Supporting information file. DOI: https://doi.org/10.1107/S2056989023003225/hb8061IVsup8.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) for (I), (III), (IV); XP in SHELXTL (Sheldrick, 2008) and Mercury (Macrae et al., 2020) for (II). For all structures, software used to prepare material for publication: SHELX (Sheldrick, 2008) and publCIF (Westrip, 2010).C20H26NO+·C8H7O3−·H2O | F(000) = 500 |
Mr = 465.57 | Dx = 1.247 Mg m−3 |
Monoclinic, Pn | Cu Kα radiation, λ = 1.54178 Å |
a = 6.2398 (2) Å | Cell parameters from 9880 reflections |
b = 14.7216 (4) Å | θ = 3.0–74.4° |
c = 13.5383 (4) Å | µ = 0.68 mm−1 |
β = 94.229 (1)° | T = 90 K |
V = 1240.24 (6) Å3 | Cut block, colourless |
Z = 2 | 0.30 × 0.24 × 0.18 mm |
Bruker D8 Venture dual source diffractometer | 4078 independent reflections |
Radiation source: microsource | 3995 reflections with I > 2σ(I) |
Detector resolution: 7.41 pixels mm-1 | Rint = 0.022 |
φ and ω scans | θmax = 74.4°, θmin = 3.0° |
Absorption correction: multi-scan (SADABS; Krause et al., 2015) | h = −6→7 |
Tmin = 0.893, Tmax = 0.971 | k = −18→18 |
15326 measured reflections | l = −16→16 |
Refinement on F2 | Hydrogen site location: mixed |
Least-squares matrix: full | H atoms treated by a mixture of independent and constrained refinement |
R[F2 > 2σ(F2)] = 0.024 | w = 1/[σ2(Fo2) + (0.032P)2 + 0.2099P] where P = (Fo2 + 2Fc2)/3 |
wR(F2) = 0.064 | (Δ/σ)max = 0.001 |
S = 1.02 | Δρmax = 0.16 e Å−3 |
4078 reflections | Δρmin = −0.14 e Å−3 |
327 parameters | Extinction correction: SHELXL2019/2 (Sheldrick, 2015b), Fc*=kFc[1+0.001xFc2λ3/sin(2θ)]-1/4 |
3 restraints | Extinction coefficient: 0.0035 (6) |
Primary atom site location: structure-invariant direct methods | Absolute structure: Flack x obtained from 1479 quotients [(I+)-(I-)]/[(I+)+(I-)] (Parsons et al., 2013) |
Secondary atom site location: difference Fourier map | Absolute structure parameter: 0.08 (7) |
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 | ||
O1 | 0.05552 (19) | 0.72439 (8) | 0.57107 (10) | 0.0207 (3) | |
H1O | 0.053 (4) | 0.6672 (19) | 0.561 (2) | 0.039 (7)* | |
N1 | 0.5936 (2) | 0.54909 (9) | 0.72662 (11) | 0.0169 (3) | |
H1N | 0.537 (3) | 0.5239 (15) | 0.6666 (18) | 0.021 (5)* | |
C1 | 0.2571 (3) | 0.85982 (11) | 0.57192 (12) | 0.0169 (3) | |
C2 | 0.0971 (3) | 0.89257 (12) | 0.62852 (13) | 0.0195 (3) | |
H2 | −0.017827 | 0.853518 | 0.642767 | 0.023* | |
C3 | 0.1005 (3) | 0.98071 (12) | 0.66482 (13) | 0.0224 (4) | |
H3 | −0.012447 | 1.001724 | 0.702307 | 0.027* | |
C4 | 0.2695 (3) | 1.03815 (12) | 0.64621 (13) | 0.0240 (4) | |
H4 | 0.273384 | 1.098709 | 0.670526 | 0.029* | |
C5 | 0.4316 (3) | 1.00568 (12) | 0.59177 (14) | 0.0231 (4) | |
H5 | 0.548457 | 1.044559 | 0.579907 | 0.028* | |
C6 | 0.4294 (3) | 0.91754 (12) | 0.55353 (13) | 0.0197 (3) | |
C7 | 0.6095 (3) | 0.88649 (12) | 0.49423 (14) | 0.0220 (4) | |
H7A | 0.670947 | 0.829778 | 0.523644 | 0.026* | |
H7B | 0.724160 | 0.933119 | 0.498402 | 0.026* | |
C8 | 0.5390 (3) | 0.86947 (13) | 0.38562 (14) | 0.0242 (4) | |
H8A | 0.511844 | 0.929638 | 0.354531 | 0.029* | |
H8B | 0.663866 | 0.843058 | 0.354795 | 0.029* | |
C9 | 0.3461 (3) | 0.81008 (11) | 0.35504 (13) | 0.0207 (4) | |
C10 | 0.3015 (4) | 0.80517 (12) | 0.25206 (14) | 0.0279 (4) | |
H10 | 0.399634 | 0.832237 | 0.210388 | 0.033* | |
C11 | 0.1211 (4) | 0.76264 (12) | 0.20880 (14) | 0.0318 (5) | |
H11 | 0.095222 | 0.761135 | 0.138778 | 0.038* | |
C12 | −0.0207 (3) | 0.72250 (12) | 0.26846 (16) | 0.0299 (5) | |
H12 | −0.147085 | 0.693966 | 0.239991 | 0.036* | |
C13 | 0.0220 (3) | 0.72390 (11) | 0.37074 (15) | 0.0238 (4) | |
H13 | −0.076086 | 0.695359 | 0.411320 | 0.029* | |
C14 | 0.2061 (3) | 0.7663 (1) | 0.41590 (13) | 0.0181 (3) | |
C15 | 0.2394 (3) | 0.76263 (11) | 0.53007 (13) | 0.0170 (3) | |
C16 | 0.4325 (3) | 0.70040 (11) | 0.56309 (12) | 0.0165 (3) | |
H16B | 0.391728 | 0.636220 | 0.550513 | 0.020* | |
H16A | 0.554670 | 0.714706 | 0.523040 | 0.020* | |
C17 | 0.5035 (3) | 0.71235 (11) | 0.67311 (12) | 0.0196 (4) | |
H17A | 0.561491 | 0.774523 | 0.683229 | 0.024* | |
H17B | 0.375332 | 0.707074 | 0.711697 | 0.024* | |
C18 | 0.6713 (3) | 0.64510 (11) | 0.71430 (13) | 0.0197 (3) | |
H18A | 0.790325 | 0.644083 | 0.669854 | 0.024* | |
H18B | 0.730746 | 0.667431 | 0.779651 | 0.024* | |
C19 | 0.4136 (3) | 0.54363 (13) | 0.79194 (15) | 0.0274 (4) | |
H19A | 0.376582 | 0.479798 | 0.802175 | 0.041* | |
H19B | 0.288444 | 0.575669 | 0.760923 | 0.041* | |
H19C | 0.456773 | 0.571815 | 0.855914 | 0.041* | |
C20 | 0.7769 (3) | 0.49130 (12) | 0.76608 (15) | 0.0259 (4) | |
H20A | 0.728457 | 0.428261 | 0.771203 | 0.039* | |
H20B | 0.829547 | 0.513304 | 0.831755 | 0.039* | |
H20C | 0.892900 | 0.494386 | 0.721206 | 0.039* | |
O2 | 0.4034 (2) | 0.45194 (8) | 0.5783 (1) | 0.0234 (3) | |
O3 | 0.6984 (2) | 0.43518 (11) | 0.49734 (13) | 0.0426 (4) | |
O4 | 0.2349 (2) | 0.07544 (8) | 0.35022 (10) | 0.0245 (3) | |
C21 | 0.5175 (3) | 0.41034 (11) | 0.51922 (13) | 0.0198 (3) | |
C22 | 0.4306 (3) | 0.32348 (11) | 0.47354 (12) | 0.0169 (3) | |
C23 | 0.2284 (3) | 0.28982 (11) | 0.49120 (12) | 0.0180 (3) | |
H23 | 0.138870 | 0.323687 | 0.531451 | 0.022* | |
C24 | 0.1549 (3) | 0.20751 (11) | 0.45102 (13) | 0.0186 (3) | |
H24 | 0.015986 | 0.185752 | 0.463216 | 0.022* | |
C25 | 0.2868 (3) | 0.15731 (11) | 0.39276 (13) | 0.0184 (3) | |
C26 | 0.4889 (3) | 0.19091 (11) | 0.37383 (13) | 0.0204 (4) | |
H26 | 0.578018 | 0.157350 | 0.333126 | 0.024* | |
C27 | 0.5595 (3) | 0.27239 (11) | 0.41385 (13) | 0.0189 (3) | |
H27 | 0.697803 | 0.294343 | 0.400821 | 0.023* | |
C28 | 0.0414 (3) | 0.03267 (12) | 0.37610 (16) | 0.0271 (4) | |
H28A | 0.028544 | −0.027200 | 0.344564 | 0.041* | |
H28B | −0.082092 | 0.070258 | 0.353305 | 0.041* | |
H28C | 0.045039 | 0.025594 | 0.448178 | 0.041* | |
O1W | 1.0235 (3) | 0.54257 (9) | 0.55570 (14) | 0.0366 (4) | |
H1W1 | 0.913 (5) | 0.511 (2) | 0.539 (2) | 0.052 (8)* | |
H2W1 | 1.141 (5) | 0.508 (2) | 0.553 (2) | 0.051 (8)* |
U11 | U22 | U33 | U12 | U13 | U23 | |
O1 | 0.0184 (6) | 0.0168 (6) | 0.0275 (7) | −0.0032 (5) | 0.0055 (5) | −0.0024 (5) |
N1 | 0.0190 (7) | 0.0155 (6) | 0.0160 (7) | −0.0029 (5) | −0.0002 (6) | 0.0004 (5) |
C1 | 0.0180 (8) | 0.0181 (8) | 0.0140 (7) | 0.0007 (6) | −0.0024 (6) | 0.0014 (6) |
C2 | 0.0221 (9) | 0.0200 (8) | 0.0162 (8) | −0.0006 (7) | 0.0005 (6) | 0.0016 (6) |
C3 | 0.0290 (9) | 0.0226 (8) | 0.0159 (8) | 0.0028 (7) | 0.0027 (7) | −0.0016 (6) |
C4 | 0.0368 (11) | 0.0164 (7) | 0.0182 (8) | −0.0004 (7) | −0.0015 (7) | −0.0030 (6) |
C5 | 0.0274 (10) | 0.0206 (8) | 0.0207 (9) | −0.0054 (7) | −0.0015 (7) | 0.0005 (6) |
C6 | 0.0207 (8) | 0.0197 (8) | 0.0184 (8) | −0.0021 (7) | −0.0011 (6) | 0.0010 (6) |
C7 | 0.0201 (8) | 0.0211 (8) | 0.0246 (9) | −0.0043 (7) | 0.0004 (7) | 0.0036 (7) |
C8 | 0.0256 (9) | 0.0273 (9) | 0.0202 (9) | −0.0011 (8) | 0.0063 (7) | 0.0028 (7) |
C9 | 0.0274 (9) | 0.0174 (8) | 0.0170 (9) | 0.0054 (7) | 0.0006 (7) | −0.0002 (6) |
C10 | 0.0431 (12) | 0.0209 (8) | 0.0193 (9) | 0.0032 (8) | 0.0008 (8) | 0.0016 (7) |
C11 | 0.0550 (14) | 0.0202 (8) | 0.0182 (9) | 0.0059 (9) | −0.0107 (9) | −0.0026 (7) |
C12 | 0.0351 (11) | 0.0207 (8) | 0.0312 (10) | 0.0034 (8) | −0.0148 (8) | −0.0066 (7) |
C13 | 0.0241 (9) | 0.0188 (8) | 0.0274 (9) | 0.0026 (7) | −0.0063 (7) | −0.0038 (7) |
C14 | 0.0207 (8) | 0.0139 (7) | 0.0190 (8) | 0.0045 (6) | −0.0030 (6) | −0.0015 (6) |
C15 | 0.0161 (8) | 0.0165 (8) | 0.0186 (8) | −0.0018 (6) | 0.0016 (6) | 0.0000 (6) |
C16 | 0.0183 (8) | 0.0159 (7) | 0.0153 (8) | −0.0010 (6) | 0.0009 (6) | 0.0009 (6) |
C17 | 0.0265 (9) | 0.0170 (8) | 0.0150 (8) | −0.0011 (7) | 0.0000 (7) | 0.0008 (6) |
C18 | 0.0226 (8) | 0.0164 (8) | 0.0193 (8) | −0.0047 (7) | −0.0037 (6) | 0.0015 (6) |
C19 | 0.0325 (11) | 0.0230 (9) | 0.0284 (10) | −0.0040 (7) | 0.0135 (8) | 0.0004 (7) |
C20 | 0.0284 (9) | 0.0196 (8) | 0.0284 (10) | 0.0000 (7) | −0.0063 (8) | 0.0029 (7) |
O2 | 0.0246 (7) | 0.0201 (6) | 0.0247 (7) | 0.0006 (5) | −0.0032 (5) | −0.0066 (5) |
O3 | 0.0331 (8) | 0.0486 (9) | 0.0481 (10) | −0.0244 (7) | 0.0155 (7) | −0.0238 (8) |
O4 | 0.0283 (7) | 0.0177 (6) | 0.0275 (7) | −0.0019 (5) | 0.0024 (5) | −0.0047 (5) |
C21 | 0.0213 (8) | 0.0209 (8) | 0.0166 (8) | −0.0017 (7) | −0.0031 (6) | 0.0000 (6) |
C22 | 0.0189 (8) | 0.0170 (7) | 0.0143 (7) | 0.0011 (6) | −0.0026 (6) | 0.0025 (6) |
C23 | 0.0188 (8) | 0.0187 (8) | 0.0164 (8) | 0.0022 (6) | 0.0006 (6) | −0.0012 (6) |
C24 | 0.0168 (8) | 0.0186 (8) | 0.0201 (8) | −0.0013 (7) | −0.0005 (6) | 0.0010 (6) |
C25 | 0.0221 (8) | 0.0154 (7) | 0.0172 (8) | 0.0015 (7) | −0.0023 (6) | 0.0010 (6) |
C26 | 0.0220 (9) | 0.0211 (8) | 0.0183 (8) | 0.0051 (7) | 0.0027 (7) | −0.0011 (6) |
C27 | 0.0170 (8) | 0.0228 (8) | 0.0167 (8) | 0.0012 (7) | 0.0007 (6) | 0.0034 (6) |
C28 | 0.0256 (9) | 0.0198 (8) | 0.0347 (10) | −0.0028 (8) | −0.0049 (8) | −0.0046 (7) |
O1W | 0.0214 (7) | 0.0192 (6) | 0.0687 (11) | −0.0040 (6) | −0.0012 (7) | −0.0097 (6) |
O1—C15 | 1.427 (2) | C15—C16 | 1.553 (2) |
O1—H1O | 0.85 (3) | C16—C17 | 1.532 (2) |
N1—C19 | 1.482 (2) | C16—H16B | 0.9900 |
N1—C20 | 1.492 (2) | C16—H16A | 0.9900 |
N1—C18 | 1.507 (2) | C17—C18 | 1.517 (2) |
N1—H1N | 0.94 (2) | C17—H17A | 0.9900 |
C1—C2 | 1.389 (2) | C17—H17B | 0.9900 |
C1—C6 | 1.407 (2) | C18—H18A | 0.9900 |
C1—C15 | 1.540 (2) | C18—H18B | 0.9900 |
C2—C3 | 1.387 (2) | C19—H19A | 0.9800 |
C2—H2 | 0.9500 | C19—H19B | 0.9800 |
C3—C4 | 1.389 (3) | C19—H19C | 0.9800 |
C3—H3 | 0.9500 | C20—H20A | 0.9800 |
C4—C5 | 1.380 (3) | C20—H20B | 0.9800 |
C4—H4 | 0.9500 | C20—H20C | 0.9800 |
C5—C6 | 1.397 (2) | O2—C21 | 1.267 (2) |
C5—H5 | 0.9500 | O3—C21 | 1.243 (2) |
C6—C7 | 1.500 (3) | O4—C25 | 1.364 (2) |
C7—C8 | 1.524 (3) | O4—C28 | 1.428 (2) |
C7—H7A | 0.9900 | C21—C22 | 1.504 (2) |
C7—H7B | 0.9900 | C22—C23 | 1.392 (2) |
C8—C9 | 1.521 (3) | C22—C27 | 1.401 (2) |
C8—H8A | 0.9900 | C23—C24 | 1.392 (2) |
C8—H8B | 0.9900 | C23—H23 | 0.9500 |
C9—C14 | 1.401 (3) | C24—C25 | 1.393 (2) |
C9—C10 | 1.403 (3) | C24—H24 | 0.9500 |
C10—C11 | 1.381 (3) | C25—C26 | 1.396 (3) |
C10—H10 | 0.9500 | C26—C27 | 1.375 (2) |
C11—C12 | 1.374 (3) | C26—H26 | 0.9500 |
C11—H11 | 0.9500 | C27—H27 | 0.9500 |
C12—C13 | 1.391 (3) | C28—H28A | 0.9800 |
C12—H12 | 0.9500 | C28—H28B | 0.9800 |
C13—C14 | 1.407 (2) | C28—H28C | 0.9800 |
C13—H13 | 0.9500 | O1W—H1W1 | 0.84 (3) |
C14—C15 | 1.545 (2) | O1W—H2W1 | 0.90 (3) |
C15—O1—H1O | 109.4 (18) | C14—C15—C16 | 110.67 (13) |
C19—N1—C20 | 110.48 (14) | C17—C16—C15 | 111.99 (14) |
C19—N1—C18 | 112.39 (14) | C17—C16—H16B | 109.2 |
C20—N1—C18 | 109.28 (13) | C15—C16—H16B | 109.2 |
C19—N1—H1N | 104.0 (13) | C17—C16—H16A | 109.2 |
C20—N1—H1N | 108.3 (13) | C15—C16—H16A | 109.2 |
C18—N1—H1N | 112.2 (13) | H16B—C16—H16A | 107.9 |
C2—C1—C6 | 118.54 (15) | C18—C17—C16 | 115.12 (14) |
C2—C1—C15 | 119.39 (15) | C18—C17—H17A | 108.5 |
C6—C1—C15 | 122.07 (15) | C16—C17—H17A | 108.5 |
C3—C2—C1 | 121.84 (16) | C18—C17—H17B | 108.5 |
C3—C2—H2 | 119.1 | C16—C17—H17B | 108.5 |
C1—C2—H2 | 119.1 | H17A—C17—H17B | 107.5 |
C2—C3—C4 | 119.81 (17) | N1—C18—C17 | 115.72 (14) |
C2—C3—H3 | 120.1 | N1—C18—H18A | 108.4 |
C4—C3—H3 | 120.1 | C17—C18—H18A | 108.4 |
C5—C4—C3 | 118.82 (16) | N1—C18—H18B | 108.4 |
C5—C4—H4 | 120.6 | C17—C18—H18B | 108.4 |
C3—C4—H4 | 120.6 | H18A—C18—H18B | 107.4 |
C4—C5—C6 | 122.16 (17) | N1—C19—H19A | 109.5 |
C4—C5—H5 | 118.9 | N1—C19—H19B | 109.5 |
C6—C5—H5 | 118.9 | H19A—C19—H19B | 109.5 |
C5—C6—C1 | 118.81 (16) | N1—C19—H19C | 109.5 |
C5—C6—C7 | 119.64 (15) | H19A—C19—H19C | 109.5 |
C1—C6—C7 | 121.55 (15) | H19B—C19—H19C | 109.5 |
C6—C7—C8 | 113.10 (15) | N1—C20—H20A | 109.5 |
C6—C7—H7A | 109.0 | N1—C20—H20B | 109.5 |
C8—C7—H7A | 109.0 | H20A—C20—H20B | 109.5 |
C6—C7—H7B | 109.0 | N1—C20—H20C | 109.5 |
C8—C7—H7B | 109.0 | H20A—C20—H20C | 109.5 |
H7A—C7—H7B | 107.8 | H20B—C20—H20C | 109.5 |
C9—C8—C7 | 121.58 (15) | C25—O4—C28 | 117.67 (14) |
C9—C8—H8A | 106.9 | O3—C21—O2 | 124.79 (16) |
C7—C8—H8A | 106.9 | O3—C21—C22 | 117.31 (16) |
C9—C8—H8B | 106.9 | O2—C21—C22 | 117.89 (15) |
C7—C8—H8B | 106.9 | C23—C22—C27 | 118.31 (15) |
H8A—C8—H8B | 106.7 | C23—C22—C21 | 122.41 (15) |
C14—C9—C10 | 118.31 (17) | C27—C22—C21 | 119.23 (15) |
C14—C9—C8 | 128.30 (16) | C24—C23—C22 | 121.28 (16) |
C10—C9—C8 | 113.26 (16) | C24—C23—H23 | 119.4 |
C11—C10—C9 | 122.71 (19) | C22—C23—H23 | 119.4 |
C11—C10—H10 | 118.6 | C23—C24—C25 | 119.45 (15) |
C9—C10—H10 | 118.6 | C23—C24—H24 | 120.3 |
C12—C11—C10 | 119.06 (18) | C25—C24—H24 | 120.3 |
C12—C11—H11 | 120.5 | O4—C25—C24 | 125.17 (15) |
C10—C11—H11 | 120.5 | O4—C25—C26 | 115.15 (15) |
C11—C12—C13 | 119.64 (18) | C24—C25—C26 | 119.69 (15) |
C11—C12—H12 | 120.2 | C27—C26—C25 | 120.30 (16) |
C13—C12—H12 | 120.2 | C27—C26—H26 | 119.9 |
C12—C13—C14 | 121.97 (19) | C25—C26—H26 | 119.9 |
C12—C13—H13 | 119.0 | C26—C27—C22 | 120.96 (16) |
C14—C13—H13 | 119.0 | C26—C27—H27 | 119.5 |
C9—C14—C13 | 118.22 (16) | C22—C27—H27 | 119.5 |
C9—C14—C15 | 124.09 (15) | O4—C28—H28A | 109.5 |
C13—C14—C15 | 117.69 (16) | O4—C28—H28B | 109.5 |
O1—C15—C1 | 105.14 (13) | H28A—C28—H28B | 109.5 |
O1—C15—C14 | 110.50 (13) | O4—C28—H28C | 109.5 |
C1—C15—C14 | 109.65 (13) | H28A—C28—H28C | 109.5 |
O1—C15—C16 | 106.53 (13) | H28B—C28—H28C | 109.5 |
C1—C15—C16 | 114.15 (13) | H1W1—O1W—H2W1 | 109 (3) |
C6—C1—C2—C3 | 1.7 (2) | C2—C1—C15—C16 | −121.82 (16) |
C15—C1—C2—C3 | −177.45 (15) | C6—C1—C15—C16 | 59.1 (2) |
C1—C2—C3—C4 | −1.2 (3) | C9—C14—C15—O1 | 171.96 (14) |
C2—C3—C4—C5 | −0.2 (3) | C13—C14—C15—O1 | −7.22 (19) |
C3—C4—C5—C6 | 1.0 (3) | C9—C14—C15—C1 | 56.5 (2) |
C4—C5—C6—C1 | −0.5 (3) | C13—C14—C15—C1 | −122.66 (16) |
C4—C5—C6—C7 | 179.51 (17) | C9—C14—C15—C16 | −70.29 (19) |
C2—C1—C6—C5 | −0.8 (2) | C13—C14—C15—C16 | 110.54 (16) |
C15—C1—C6—C5 | 178.29 (15) | O1—C15—C16—C17 | −73.23 (16) |
C2—C1—C6—C7 | 179.15 (15) | C1—C15—C16—C17 | 42.34 (19) |
C15—C1—C6—C7 | −1.8 (2) | C14—C15—C16—C17 | 166.61 (13) |
C5—C6—C7—C8 | −112.86 (18) | C15—C16—C17—C18 | 172.16 (14) |
C1—C6—C7—C8 | 67.2 (2) | C19—N1—C18—C17 | −57.8 (2) |
C6—C7—C8—C9 | −50.9 (2) | C20—N1—C18—C17 | 179.13 (15) |
C7—C8—C9—C14 | 2.0 (3) | C16—C17—C18—N1 | −71.7 (2) |
C7—C8—C9—C10 | 177.79 (17) | O3—C21—C22—C23 | −178.82 (18) |
C14—C9—C10—C11 | 3.0 (3) | O2—C21—C22—C23 | 2.4 (2) |
C8—C9—C10—C11 | −173.25 (17) | O3—C21—C22—C27 | 3.6 (2) |
C9—C10—C11—C12 | −0.6 (3) | O2—C21—C22—C27 | −175.24 (15) |
C10—C11—C12—C13 | −1.2 (3) | C27—C22—C23—C24 | 0.1 (2) |
C11—C12—C13—C14 | 0.7 (3) | C21—C22—C23—C24 | −177.54 (16) |
C10—C9—C14—C13 | −3.4 (2) | C22—C23—C24—C25 | 0.6 (2) |
C8—C9—C14—C13 | 172.22 (17) | C28—O4—C25—C24 | −7.5 (2) |
C10—C9—C14—C15 | 177.46 (16) | C28—O4—C25—C26 | 172.93 (15) |
C8—C9—C14—C15 | −6.9 (3) | C23—C24—C25—O4 | 179.18 (16) |
C12—C13—C14—C9 | 1.6 (2) | C23—C24—C25—C26 | −1.2 (2) |
C12—C13—C14—C15 | −179.15 (16) | O4—C25—C26—C27 | −179.22 (15) |
C2—C1—C15—O1 | −5.43 (19) | C24—C25—C26—C27 | 1.2 (3) |
C6—C1—C15—O1 | 175.48 (15) | C25—C26—C27—C22 | −0.4 (3) |
C2—C1—C15—C14 | 113.37 (16) | C23—C22—C27—C26 | −0.2 (2) |
C6—C1—C15—C14 | −65.71 (19) | C21—C22—C27—C26 | 177.53 (15) |
D—H···A | D—H | H···A | D···A | D—H···A |
O1—H1O···O1Wi | 0.85 (3) | 1.84 (3) | 2.6911 (18) | 171 (3) |
N1—H1N···O2 | 0.94 (2) | 1.76 (2) | 2.6711 (18) | 163 (2) |
C18—H18A···O1ii | 0.99 | 2.50 | 3.400 (2) | 151 |
C18—H18A···O1W | 0.99 | 2.66 | 3.523 (3) | 146 |
C19—H19C···O3iii | 0.98 | 2.59 | 3.191 (3) | 119 |
C20—H20C···O1W | 0.98 | 2.54 | 3.420 (3) | 149 |
O1W—H1W1···O3 | 0.84 (3) | 1.81 (3) | 2.646 (2) | 173 (3) |
O1W—H2W1···O2ii | 0.90 (3) | 1.84 (3) | 2.718 (2) | 165 (3) |
Symmetry codes: (i) x−1, y, z; (ii) x+1, y, z; (iii) x−1/2, −y+1, z+1/2. |
C20H26NO+·C9H9O4−·3H2O | F(000) = 2288 |
Mr = 531.63 | Dx = 1.252 Mg m−3 |
Monoclinic, Cc | Cu Kα radiation, λ = 1.54178 Å |
a = 8.6750 (3) Å | Cell parameters from 9909 reflections |
b = 55.2061 (19) Å | θ = 3.2–74.4° |
c = 12.3988 (4) Å | µ = 0.74 mm−1 |
β = 108.238 (2)° | T = 90 K |
V = 5639.7 (3) Å3 | Cut block, colourless |
Z = 8 | 0.30 × 0.24 × 0.18 mm |
Bruker D8 Venture dual source diffractometer | 9069 independent reflections |
Radiation source: microsource | 8333 reflections with I > 2σ(I) |
Detector resolution: 7.41 pixels mm-1 | Rint = 0.034 |
φ and ω scans | θmax = 74.5°, θmin = 1.6° |
Absorption correction: multi-scan (SADABS; Krause et al., 2015) | h = −10→10 |
Tmin = 0.858, Tmax = 0.982 | k = −67→68 |
22593 measured reflections | l = −14→15 |
Refinement on F2 | Hydrogen site location: mixed |
Least-squares matrix: full | H atoms treated by a mixture of independent and constrained refinement |
R[F2 > 2σ(F2)] = 0.031 | w = 1/[σ2(Fo2) + (0.0311P)2 + 1.2839P] where P = (Fo2 + 2Fc2)/3 |
wR(F2) = 0.074 | (Δ/σ)max = 0.002 |
S = 1.02 | Δρmax = 0.17 e Å−3 |
9069 reflections | Δρmin = −0.20 e Å−3 |
773 parameters | Extinction correction: SHELXL2019/2 (Sheldrick, 2015b), Fc*=kFc[1+0.001xFc2λ3/sin(2θ)]-1/4 |
160 restraints | Extinction coefficient: 0.00036 (6) |
Primary atom site location: structure-invariant direct methods | Absolute structure: Flack x obtained from 2935 quotients [(I+)-(I-)]/[(I+)+(I-)] (Parsons et al., 2013) |
Secondary atom site location: difference Fourier map | Absolute structure parameter: 0.00 (7) |
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 | 0.8097 (2) | 0.47166 (3) | 0.10132 (14) | 0.0261 (4) | |
H1OA | 0.728 (5) | 0.4647 (6) | 0.104 (3) | 0.050 (11)* | |
N1A | 0.9739 (2) | 0.42601 (4) | 0.47205 (16) | 0.0223 (4) | |
H1NA | 0.944 (4) | 0.4156 (5) | 0.404 (3) | 0.034 (8)* | |
C1A | 0.7195 (3) | 0.51236 (4) | 0.1267 (2) | 0.0254 (5) | |
C2A | 0.6083 (3) | 0.50919 (5) | 0.0187 (2) | 0.0338 (6) | |
H2A | 0.601812 | 0.493898 | −0.017580 | 0.041* | |
C3A | 0.5074 (4) | 0.52770 (6) | −0.0370 (3) | 0.0478 (8) | |
H3A | 0.431704 | 0.525070 | −0.110150 | 0.057* | |
C4A | 0.5177 (4) | 0.55017 (6) | 0.0150 (3) | 0.0520 (9) | |
H4A | 0.452519 | 0.563268 | −0.023627 | 0.062* | |
C5A | 0.6226 (4) | 0.55328 (5) | 0.1225 (3) | 0.0453 (8) | |
H5A | 0.625477 | 0.568544 | 0.158415 | 0.054* | |
C6A | 0.7258 (4) | 0.53489 (5) | 0.1815 (3) | 0.0343 (6) | |
C7A | 0.8349 (7) | 0.5406 (2) | 0.3010 (6) | 0.0430 (7) | 0.723 (8) |
H7AA | 0.774332 | 0.535915 | 0.353525 | 0.052* | 0.723 (8) |
H7AB | 0.847683 | 0.558391 | 0.306159 | 0.052* | 0.723 (8) |
C8A | 1.0040 (6) | 0.52974 (10) | 0.3483 (4) | 0.0412 (10) | 0.723 (8) |
H8AA | 1.076644 | 0.542410 | 0.393608 | 0.049* | 0.723 (8) |
H8AB | 0.998948 | 0.516568 | 0.401305 | 0.049* | 0.723 (8) |
C9A | 1.0821 (3) | 0.51966 (5) | 0.2649 (2) | 0.0328 (6) | |
C7A' | 0.8294 (15) | 0.5414 (5) | 0.3009 (13) | 0.0430 (7) | 0.277 (8) |
H7AC | 0.801921 | 0.558060 | 0.317951 | 0.052* | 0.277 (8) |
H7AD | 0.801849 | 0.530334 | 0.354952 | 0.052* | 0.277 (8) |
C8A' | 1.0098 (13) | 0.5400 (2) | 0.3200 (11) | 0.0412 (10) | 0.277 (8) |
H8AC | 1.063586 | 0.539017 | 0.403067 | 0.049* | 0.277 (8) |
H8AD | 1.042800 | 0.555628 | 0.294696 | 0.049* | 0.277 (8) |
C10A | 1.2396 (4) | 0.52680 (5) | 0.2704 (3) | 0.0436 (8) | |
H10A | 1.289198 | 0.539784 | 0.319256 | 0.052* | |
C11A | 1.3237 (4) | 0.51577 (6) | 0.2081 (4) | 0.0577 (10) | |
H11A | 1.430100 | 0.521015 | 0.213257 | 0.069* | |
C12A | 1.2531 (4) | 0.49711 (7) | 0.1383 (4) | 0.0615 (10) | |
H12A | 1.309878 | 0.489321 | 0.093825 | 0.074* | |
C13A | 1.0992 (4) | 0.48948 (5) | 0.1322 (3) | 0.0406 (7) | |
H13A | 1.052750 | 0.476225 | 0.084158 | 0.049* | |
C14A | 1.0105 (3) | 0.50042 (4) | 0.1933 (2) | 0.0245 (5) | |
C15A | 0.8373 (3) | 0.49146 (4) | 0.17906 (19) | 0.0223 (5) | |
C16A | 0.8133 (3) | 0.48197 (4) | 0.2894 (2) | 0.0237 (5) | |
H16A | 0.828234 | 0.495479 | 0.344260 | 0.028* | |
H16B | 0.700971 | 0.475870 | 0.272840 | 0.028* | |
C17A | 0.9323 (3) | 0.46170 (4) | 0.3429 (2) | 0.0265 (5) | |
H17A | 0.928203 | 0.449175 | 0.284873 | 0.032* | |
H17B | 1.043917 | 0.468334 | 0.369343 | 0.032* | |
C18A | 0.8928 (3) | 0.45018 (4) | 0.44236 (19) | 0.0238 (5) | |
H18A | 0.929122 | 0.461037 | 0.509095 | 0.029* | |
H18B | 0.773833 | 0.448128 | 0.422774 | 0.029* | |
C19A | 0.9150 (3) | 0.41316 (5) | 0.5565 (2) | 0.0318 (6) | |
H19A | 0.796673 | 0.411542 | 0.527029 | 0.048* | |
H19B | 0.944868 | 0.422393 | 0.627505 | 0.048* | |
H19C | 0.964507 | 0.397033 | 0.570658 | 0.048* | |
C20A | 1.1528 (3) | 0.42766 (5) | 0.5104 (2) | 0.0364 (6) | |
H20A | 1.189226 | 0.433926 | 0.448517 | 0.055* | |
H20B | 1.199354 | 0.411546 | 0.532492 | 0.055* | |
H20C | 1.188559 | 0.438616 | 0.575741 | 0.055* | |
O2A | 0.9079 (2) | 0.39435 (3) | 0.29857 (14) | 0.0288 (4) | |
O3A | 0.6631 (2) | 0.40818 (3) | 0.28617 (14) | 0.0253 (4) | |
O4A | 0.8017 (2) | 0.32516 (3) | 0.01210 (14) | 0.0276 (4) | |
O5A | 0.4946 (2) | 0.32461 (3) | −0.08854 (13) | 0.0251 (4) | |
C21A | 0.7548 (3) | 0.39383 (4) | 0.25680 (19) | 0.0220 (5) | |
C22A | 0.6805 (3) | 0.37502 (4) | 0.16730 (19) | 0.0201 (5) | |
C23A | 0.7816 (3) | 0.35872 (4) | 0.13490 (19) | 0.0216 (5) | |
H23A | 0.895721 | 0.359291 | 0.170702 | 0.026* | |
C24A | 0.7158 (3) | 0.34177 (4) | 0.05087 (19) | 0.0221 (5) | |
C25A | 0.5467 (3) | 0.34135 (4) | −0.00328 (19) | 0.0214 (5) | |
C26A | 0.4471 (3) | 0.35703 (4) | 0.0312 (2) | 0.0234 (5) | |
H26A | 0.332757 | 0.356322 | −0.003274 | 0.028* | |
C27A | 0.5145 (3) | 0.37388 (4) | 0.1167 (2) | 0.0230 (5) | |
H27A | 0.445821 | 0.384642 | 0.140285 | 0.028* | |
C28A | 0.9746 (3) | 0.32550 (5) | 0.0603 (2) | 0.0296 (6) | |
H28A | 1.021890 | 0.313054 | 0.023889 | 0.044* | |
H28B | 1.004536 | 0.322238 | 0.141968 | 0.044* | |
H28C | 1.015872 | 0.341455 | 0.048111 | 0.044* | |
C29A | 0.3318 (3) | 0.32681 (5) | −0.1622 (2) | 0.0328 (6) | |
H29A | 0.311686 | 0.343562 | −0.189141 | 0.049* | |
H29B | 0.256278 | 0.322455 | −0.120829 | 0.049* | |
H29C | 0.315510 | 0.315935 | −0.227306 | 0.049* | |
O2B | 0.0055 (2) | 0.35198 (3) | 0.65098 (13) | 0.0255 (4) | |
O3B | −0.2199 (2) | 0.35121 (3) | 0.69922 (14) | 0.0276 (4) | |
O4B | 0.2120 (2) | 0.42401 (3) | 1.06985 (13) | 0.0252 (4) | |
O5B | 0.35057 (19) | 0.41657 (3) | 0.91879 (13) | 0.0240 (4) | |
C21B | −0.0785 (3) | 0.35866 (4) | 0.71262 (19) | 0.0221 (5) | |
C22B | −0.0065 (3) | 0.37649 (4) | 0.80631 (18) | 0.0203 (5) | |
C23B | 0.1409 (3) | 0.38828 (4) | 0.81467 (19) | 0.0204 (5) | |
H23B | 0.193726 | 0.385270 | 0.759468 | 0.024* | |
C24B | 0.2089 (3) | 0.40417 (4) | 0.90259 (19) | 0.0192 (5) | |
C25B | 0.1319 (3) | 0.40846 (4) | 0.98534 (19) | 0.0218 (5) | |
C26B | −0.0135 (3) | 0.39715 (4) | 0.9766 (2) | 0.0241 (5) | |
H26B | −0.066450 | 0.400164 | 1.031777 | 0.029* | |
C27B | −0.0826 (3) | 0.38130 (4) | 0.8868 (2) | 0.0240 (5) | |
H27B | −0.183243 | 0.373717 | 0.880850 | 0.029* | |
C28B | 0.4461 (3) | 0.41039 (5) | 0.8472 (2) | 0.0284 (5) | |
H28D | 0.386712 | 0.414694 | 0.768475 | 0.043* | |
H28E | 0.468079 | 0.392938 | 0.852269 | 0.043* | |
H28F | 0.548977 | 0.419289 | 0.871932 | 0.043* | |
C29B | 0.1497 (4) | 0.42658 (5) | 1.1636 (2) | 0.0327 (6) | |
H29D | 0.040051 | 0.433412 | 1.136581 | 0.049* | |
H29E | 0.220504 | 0.437408 | 1.220407 | 0.049* | |
H29F | 0.146086 | 0.410670 | 1.197751 | 0.049* | |
O1B | −0.0088 (2) | 0.27936 (3) | 0.84148 (14) | 0.0249 (4) | |
H1OB | −0.099 (5) | 0.2875 (6) | 0.828 (3) | 0.049 (10)* | |
N1B | −0.1886 (2) | 0.32466 (4) | 0.47886 (16) | 0.0226 (4) | |
H1NB | −0.124 (3) | 0.3328 (5) | 0.550 (2) | 0.021 (6)* | |
C1B | −0.0970 (3) | 0.23739 (4) | 0.8230 (2) | 0.0226 (5) | |
C2B | −0.1097 (3) | 0.24038 (5) | 0.9320 (2) | 0.0280 (5) | |
H2B | −0.087797 | 0.255825 | 0.967240 | 0.034* | |
C3B | −0.1532 (3) | 0.22148 (5) | 0.9899 (2) | 0.0353 (6) | |
H3B | −0.161545 | 0.224032 | 1.063669 | 0.042* | |
C4B | −0.1845 (3) | 0.19891 (5) | 0.9399 (3) | 0.0364 (7) | |
H4B | −0.212209 | 0.185725 | 0.979475 | 0.044* | |
C5B | −0.1751 (3) | 0.19572 (5) | 0.8317 (2) | 0.0343 (6) | |
H5B | −0.198988 | 0.180227 | 0.797139 | 0.041* | |
C6B | −0.1315 (3) | 0.21454 (4) | 0.7710 (2) | 0.0271 (5) | |
C7B | −0.1254 (7) | 0.20877 (14) | 0.6523 (4) | 0.0334 (6) | 0.794 (10) |
H7BA | −0.234262 | 0.212447 | 0.598930 | 0.040* | 0.794 (10) |
H7BB | −0.110401 | 0.191034 | 0.649269 | 0.040* | 0.794 (10) |
C8B | −0.0001 (4) | 0.22072 (10) | 0.6031 (3) | 0.0308 (9) | 0.794 (10) |
H8BA | 0.039106 | 0.208199 | 0.560842 | 0.037* | 0.794 (10) |
H8BB | −0.057133 | 0.233197 | 0.547578 | 0.037* | 0.794 (10) |
C9B | 0.1457 (3) | 0.23241 (5) | 0.6868 (2) | 0.0273 (5) | |
C7B' | −0.136 (2) | 0.2077 (5) | 0.6516 (14) | 0.0334 (6) | 0.206 (10) |
H7BC | −0.218932 | 0.217595 | 0.596256 | 0.040* | 0.206 (10) |
H7BD | −0.167884 | 0.190459 | 0.637791 | 0.040* | 0.206 (10) |
C8B' | 0.0286 (17) | 0.2115 (3) | 0.6328 (14) | 0.0308 (9) | 0.206 (10) |
H8BC | 0.006565 | 0.212792 | 0.549693 | 0.037* | 0.206 (10) |
H8BD | 0.090553 | 0.196284 | 0.656675 | 0.037* | 0.206 (10) |
C10B | 0.2992 (3) | 0.22630 (5) | 0.6836 (2) | 0.0302 (6) | |
H10B | 0.310033 | 0.213517 | 0.635197 | 0.036* | |
C11B | 0.4373 (3) | 0.23822 (5) | 0.7488 (3) | 0.0372 (7) | |
H11B | 0.541280 | 0.233658 | 0.745478 | 0.045* | |
C12B | 0.4212 (3) | 0.25691 (5) | 0.8188 (3) | 0.0401 (7) | |
H12B | 0.514461 | 0.265297 | 0.864353 | 0.048* | |
C13B | 0.2683 (3) | 0.26334 (5) | 0.8221 (2) | 0.0302 (6) | |
H13B | 0.258570 | 0.276233 | 0.870363 | 0.036* | |
C14B | 0.1286 (3) | 0.25148 (4) | 0.75701 (19) | 0.0217 (5) | |
C15B | −0.0369 (3) | 0.25886 (4) | 0.76773 (19) | 0.0213 (5) | |
C16B | −0.1633 (3) | 0.26664 (4) | 0.65459 (19) | 0.0218 (5) | |
H16C | −0.190054 | 0.252546 | 0.602651 | 0.026* | |
H16D | −0.264023 | 0.271806 | 0.669456 | 0.026* | |
C17B | −0.1019 (3) | 0.28741 (4) | 0.5966 (2) | 0.0235 (5) | |
H17C | −0.034510 | 0.298558 | 0.655019 | 0.028* | |
H17D | −0.033210 | 0.280764 | 0.553196 | 0.028* | |
C18B | −0.2434 (3) | 0.30135 (4) | 0.51667 (19) | 0.0218 (5) | |
H18C | −0.296440 | 0.291225 | 0.449361 | 0.026* | |
H18D | −0.324476 | 0.304823 | 0.555782 | 0.026* | |
C19B | −0.3287 (3) | 0.34098 (5) | 0.4246 (2) | 0.0295 (5) | |
H19D | −0.288277 | 0.356619 | 0.407438 | 0.044* | |
H19E | −0.392125 | 0.343457 | 0.476692 | 0.044* | |
H19F | −0.397610 | 0.333581 | 0.354196 | 0.044* | |
C20B | −0.0901 (3) | 0.32096 (5) | 0.4014 (2) | 0.0323 (6) | |
H20D | −0.157237 | 0.313348 | 0.330950 | 0.048* | |
H20E | 0.002483 | 0.310452 | 0.438230 | 0.048* | |
H20F | −0.050527 | 0.336639 | 0.383928 | 0.048* | |
O1W | 0.4417 (3) | 0.39328 (4) | 0.39210 (18) | 0.0413 (5) | |
H1W1 | 0.504 (4) | 0.3966 (6) | 0.357 (2) | 0.052 (9)* | |
H2W1 | 0.489 (4) | 0.3906 (7) | 0.4585 (16) | 0.074 (11)* | |
O2W | 0.1734 (2) | 0.36400 (3) | 0.33118 (17) | 0.0338 (4) | |
H1W2 | 0.096 (3) | 0.3738 (5) | 0.315 (3) | 0.058 (10)* | |
H2W2 | 0.255 (3) | 0.3723 (6) | 0.338 (4) | 0.081 (11)* | |
O3W | 0.5334 (3) | 0.38545 (4) | 0.62643 (19) | 0.0413 (5) | |
H1W3 | 0.609 (4) | 0.3755 (7) | 0.649 (4) | 0.091 (13)* | |
H2W3 | 0.451 (3) | 0.3769 (7) | 0.608 (4) | 0.103 (14)* | |
O4W | 0.2519 (3) | 0.36026 (7) | 0.5651 (2) | 0.0731 (9) | |
H1W4 | 0.185 (4) | 0.3580 (9) | 0.598 (3) | 0.086 (13)* | |
H2W4 | 0.209 (5) | 0.3598 (9) | 0.4968 (15) | 0.103 (14)* | |
O5W | 0.5522 (2) | 0.44426 (4) | 0.11870 (17) | 0.0382 (5) | |
H1W5 | 0.467 (3) | 0.4390 (6) | 0.072 (2) | 0.059 (10)* | |
H2W5 | 0.576 (4) | 0.4335 (5) | 0.168 (2) | 0.066 (10)* | |
O6W | −0.2896 (2) | 0.30734 (3) | 0.78184 (16) | 0.0319 (4) | |
H1W6 | −0.320 (4) | 0.3101 (6) | 0.838 (2) | 0.053 (9)* | |
H2W6 | −0.258 (4) | 0.3206 (4) | 0.765 (3) | 0.048 (9)* |
U11 | U22 | U33 | U12 | U13 | U23 | |
O1A | 0.0294 (10) | 0.0231 (9) | 0.0283 (9) | −0.0036 (7) | 0.0129 (8) | −0.0060 (7) |
N1A | 0.0234 (10) | 0.0216 (10) | 0.0208 (9) | 0.0012 (8) | 0.0053 (8) | −0.0004 (8) |
C1A | 0.0234 (12) | 0.0263 (13) | 0.0328 (13) | 0.0007 (9) | 0.0178 (11) | 0.0054 (10) |
C2A | 0.0224 (13) | 0.0410 (16) | 0.0399 (15) | −0.0023 (11) | 0.0124 (12) | 0.0121 (12) |
C3A | 0.0215 (14) | 0.062 (2) | 0.061 (2) | 0.0021 (13) | 0.0142 (14) | 0.0290 (17) |
C4A | 0.0303 (16) | 0.048 (2) | 0.089 (3) | 0.0166 (13) | 0.0340 (18) | 0.0377 (18) |
C5A | 0.0459 (18) | 0.0313 (16) | 0.076 (2) | 0.0125 (13) | 0.0449 (18) | 0.0159 (15) |
C6A | 0.0405 (15) | 0.0232 (13) | 0.0515 (16) | 0.0027 (11) | 0.0324 (13) | 0.0074 (11) |
C7A | 0.073 (2) | 0.0212 (15) | 0.0458 (16) | −0.0028 (13) | 0.0346 (16) | −0.0045 (12) |
C8A | 0.062 (2) | 0.026 (2) | 0.039 (2) | −0.0220 (19) | 0.0205 (18) | −0.0088 (17) |
C9A | 0.0352 (14) | 0.0308 (14) | 0.0304 (13) | −0.0069 (11) | 0.0073 (12) | 0.0043 (11) |
C7A' | 0.073 (2) | 0.0212 (15) | 0.0458 (16) | −0.0028 (13) | 0.0346 (16) | −0.0045 (12) |
C8A' | 0.062 (2) | 0.026 (2) | 0.039 (2) | −0.0220 (19) | 0.0205 (18) | −0.0088 (17) |
C10A | 0.0396 (17) | 0.0304 (16) | 0.0526 (18) | −0.0114 (12) | 0.0026 (14) | 0.0101 (13) |
C11A | 0.0316 (17) | 0.045 (2) | 0.101 (3) | −0.0067 (14) | 0.0282 (19) | 0.0127 (19) |
C12A | 0.045 (2) | 0.048 (2) | 0.110 (3) | −0.0027 (16) | 0.052 (2) | −0.007 (2) |
C13A | 0.0372 (16) | 0.0290 (15) | 0.066 (2) | −0.0019 (12) | 0.0315 (15) | −0.0049 (14) |
C14A | 0.0243 (12) | 0.0210 (12) | 0.0308 (12) | −0.0014 (9) | 0.0124 (10) | 0.0072 (9) |
C15A | 0.0249 (12) | 0.0202 (12) | 0.0248 (11) | −0.0008 (9) | 0.0119 (10) | −0.0027 (9) |
C16A | 0.0274 (13) | 0.0192 (12) | 0.0279 (12) | −0.0025 (9) | 0.0135 (10) | −0.0020 (9) |
C17A | 0.0238 (12) | 0.0269 (13) | 0.0306 (13) | −0.0003 (10) | 0.0112 (11) | 0.004 (1) |
C18A | 0.0261 (13) | 0.0224 (12) | 0.0242 (12) | 0.0019 (9) | 0.0096 (10) | −0.0023 (9) |
C19A | 0.0391 (15) | 0.0285 (14) | 0.0306 (13) | 0.0075 (11) | 0.0150 (12) | 0.0077 (10) |
C20A | 0.0238 (13) | 0.0389 (16) | 0.0398 (15) | 0.0006 (11) | 0.0006 (12) | −0.0020 (12) |
O2A | 0.0218 (9) | 0.0309 (10) | 0.0308 (9) | −0.0011 (7) | 0.0040 (7) | −0.0070 (7) |
O3A | 0.0235 (8) | 0.0270 (9) | 0.0270 (8) | 0.0010 (7) | 0.0100 (7) | −0.0021 (7) |
O4A | 0.0221 (9) | 0.0293 (10) | 0.0282 (9) | 0.0045 (7) | 0.0033 (7) | −0.0058 (7) |
O5A | 0.0232 (9) | 0.0253 (9) | 0.0224 (8) | 0.0020 (7) | 0.0007 (7) | −0.0019 (7) |
C21A | 0.0229 (12) | 0.0225 (12) | 0.0210 (11) | −0.0020 (9) | 0.0073 (9) | 0.0029 (9) |
C22A | 0.0205 (11) | 0.0214 (11) | 0.0182 (10) | −0.0010 (9) | 0.0060 (9) | 0.0020 (9) |
C23A | 0.0184 (11) | 0.0226 (12) | 0.0221 (11) | −0.0001 (9) | 0.0040 (9) | 0.0038 (9) |
C24A | 0.0236 (12) | 0.0216 (12) | 0.0208 (11) | 0.0025 (9) | 0.0065 (9) | 0.0037 (9) |
C25A | 0.0238 (11) | 0.0196 (11) | 0.0192 (11) | −0.0002 (9) | 0.0043 (9) | 0.0020 (9) |
C26A | 0.0201 (11) | 0.0231 (12) | 0.0247 (11) | 0.0008 (9) | 0.0038 (9) | 0.0032 (9) |
C27A | 0.0233 (12) | 0.0226 (12) | 0.0240 (11) | 0.0015 (9) | 0.0087 (10) | 0.0039 (9) |
C28A | 0.0213 (12) | 0.0321 (14) | 0.0321 (13) | 0.0053 (10) | 0.0035 (11) | −0.0033 (11) |
C29A | 0.0254 (13) | 0.0301 (14) | 0.0329 (14) | 0.0036 (10) | −0.0054 (11) | −0.0059 (11) |
O2B | 0.0239 (9) | 0.0282 (9) | 0.0243 (8) | −0.0038 (7) | 0.0071 (7) | −0.0052 (7) |
O3B | 0.0238 (9) | 0.0286 (9) | 0.0296 (9) | −0.0066 (7) | 0.0071 (7) | −0.0025 (7) |
O4B | 0.0299 (9) | 0.0251 (9) | 0.0215 (8) | −0.0023 (7) | 0.0094 (7) | −0.0056 (7) |
O5B | 0.0215 (8) | 0.0264 (9) | 0.0256 (8) | −0.0055 (7) | 0.0097 (7) | −0.0051 (7) |
C21B | 0.0233 (12) | 0.0189 (11) | 0.0219 (11) | −0.0004 (9) | 0.0041 (9) | 0.0049 (9) |
C22B | 0.0209 (12) | 0.0196 (11) | 0.0201 (11) | 0.0010 (9) | 0.0059 (9) | 0.0034 (9) |
C23B | 0.0211 (11) | 0.0216 (12) | 0.0187 (11) | 0.0014 (9) | 0.0066 (9) | 0.0028 (9) |
C24B | 0.0188 (11) | 0.0182 (11) | 0.0201 (11) | 0.0015 (8) | 0.0055 (9) | 0.0037 (8) |
C25B | 0.0232 (12) | 0.0208 (12) | 0.0202 (11) | 0.0017 (9) | 0.0048 (9) | 0.0010 (9) |
C26B | 0.0278 (12) | 0.0254 (13) | 0.0230 (11) | 0.0022 (10) | 0.0137 (10) | 0.0025 (9) |
C27B | 0.0211 (12) | 0.0248 (12) | 0.0275 (12) | −0.0025 (9) | 0.0095 (10) | 0.0038 (9) |
C28B | 0.0249 (12) | 0.0338 (14) | 0.0308 (13) | −0.0058 (10) | 0.0147 (11) | −0.0050 (11) |
C29B | 0.0407 (15) | 0.0350 (15) | 0.0255 (13) | −0.0041 (12) | 0.0150 (12) | −0.0069 (11) |
O1B | 0.0236 (9) | 0.0210 (9) | 0.0278 (9) | 0.0013 (7) | 0.0047 (7) | −0.0052 (7) |
N1B | 0.0233 (10) | 0.0219 (10) | 0.0208 (10) | −0.0021 (8) | 0.0045 (8) | 0.0003 (8) |
C1B | 0.0144 (10) | 0.0210 (12) | 0.0288 (12) | 0.0024 (8) | 0.0014 (9) | 0.0036 (9) |
C2B | 0.0221 (12) | 0.0286 (13) | 0.0325 (13) | 0.0024 (10) | 0.0074 (11) | 0.0014 (10) |
C3B | 0.0258 (13) | 0.0440 (17) | 0.0370 (15) | 0.0043 (11) | 0.0113 (12) | 0.0118 (12) |
C4B | 0.0205 (13) | 0.0354 (16) | 0.0524 (17) | 0.0003 (10) | 0.0102 (12) | 0.0161 (13) |
C5B | 0.0194 (12) | 0.0239 (13) | 0.0510 (17) | −0.002 (1) | −0.0013 (12) | 0.0039 (12) |
C6B | 0.0183 (11) | 0.0237 (12) | 0.0320 (12) | 0.0013 (9) | −0.0026 (10) | 0.0008 (10) |
C7B | 0.0363 (16) | 0.0203 (14) | 0.0350 (14) | −0.0037 (11) | −0.0013 (12) | −0.0060 (11) |
C8B | 0.0253 (16) | 0.032 (2) | 0.0303 (18) | 0.0102 (14) | 0.0013 (14) | −0.0078 (15) |
C9B | 0.0256 (12) | 0.0295 (13) | 0.0257 (12) | 0.0045 (10) | 0.0063 (10) | 0.0013 (10) |
C7B' | 0.0363 (16) | 0.0203 (14) | 0.0350 (14) | −0.0037 (11) | −0.0013 (12) | −0.0060 (11) |
C8B' | 0.0253 (16) | 0.032 (2) | 0.0303 (18) | 0.0102 (14) | 0.0013 (14) | −0.0078 (15) |
C10B | 0.0289 (13) | 0.0293 (14) | 0.0342 (13) | 0.0075 (10) | 0.0123 (11) | 0.0045 (11) |
C11B | 0.0255 (14) | 0.0353 (16) | 0.0552 (18) | 0.0043 (11) | 0.0190 (13) | 0.0074 (13) |
C12B | 0.0226 (13) | 0.0377 (16) | 0.0569 (18) | −0.0090 (11) | 0.0078 (13) | −0.0028 (13) |
C13B | 0.0247 (13) | 0.0253 (14) | 0.0387 (14) | −0.0015 (10) | 0.0071 (11) | −0.0012 (11) |
C14B | 0.0198 (11) | 0.0223 (12) | 0.0214 (11) | 0.0027 (9) | 0.0040 (9) | 0.0051 (9) |
C15B | 0.0218 (11) | 0.0195 (11) | 0.0203 (11) | 0.0002 (9) | 0.0034 (9) | −0.0029 (9) |
C16B | 0.0195 (11) | 0.0182 (11) | 0.0250 (11) | 0.0013 (8) | 0.0030 (9) | −0.0001 (9) |
C17B | 0.0217 (12) | 0.0234 (12) | 0.0244 (12) | 0.0012 (9) | 0.0059 (10) | 0.0015 (9) |
C18B | 0.0201 (11) | 0.0213 (12) | 0.0230 (11) | −0.0021 (9) | 0.0054 (9) | 0.0000 (9) |
C19B | 0.0293 (13) | 0.0246 (13) | 0.0283 (12) | 0.001 (1) | 0.0000 (11) | 0.0034 (10) |
C20B | 0.0341 (15) | 0.0372 (15) | 0.0266 (13) | −0.0058 (11) | 0.0110 (11) | −0.0007 (11) |
O1W | 0.0361 (11) | 0.0495 (13) | 0.0433 (12) | −0.0045 (9) | 0.0198 (10) | 0.0081 (10) |
O2W | 0.0261 (10) | 0.0304 (10) | 0.0406 (11) | 0.0033 (8) | 0.0044 (9) | −0.0038 (8) |
O3W | 0.0401 (12) | 0.0330 (11) | 0.0427 (12) | 0.0035 (9) | 0.0011 (10) | −0.0047 (9) |
O4W | 0.0344 (13) | 0.142 (3) | 0.0407 (14) | −0.0144 (15) | 0.0091 (11) | 0.0307 (16) |
O5W | 0.0339 (11) | 0.0308 (11) | 0.0405 (11) | −0.0124 (8) | −0.0021 (9) | 0.0065 (9) |
O6W | 0.0372 (10) | 0.0275 (10) | 0.0364 (10) | 0.0034 (8) | 0.0194 (9) | −0.0023 (8) |
O1A—C15A | 1.427 (3) | C21B—C22B | 1.501 (3) |
O1A—H1OA | 0.82 (4) | C22B—C27B | 1.384 (3) |
N1A—C20A | 1.477 (3) | C22B—C23B | 1.409 (3) |
N1A—C19A | 1.481 (3) | C23B—C24B | 1.380 (3) |
N1A—C18A | 1.500 (3) | C23B—H23B | 0.9500 |
N1A—H1NA | 0.99 (3) | C24B—C25B | 1.408 (3) |
C1A—C2A | 1.395 (4) | C25B—C26B | 1.381 (3) |
C1A—C6A | 1.410 (4) | C26B—C27B | 1.396 (3) |
C1A—C15A | 1.543 (3) | C26B—H26B | 0.9500 |
C2A—C3A | 1.381 (4) | C27B—H27B | 0.9500 |
C2A—H2A | 0.9500 | C28B—H28D | 0.9800 |
C3A—C4A | 1.388 (5) | C28B—H28E | 0.9800 |
C3A—H3A | 0.9500 | C28B—H28F | 0.9800 |
C4A—C5A | 1.369 (5) | C29B—H29D | 0.9800 |
C4A—H4A | 0.9500 | C29B—H29E | 0.9800 |
C5A—C6A | 1.399 (4) | C29B—H29F | 0.9800 |
C5A—H5A | 0.9500 | O1B—C15B | 1.427 (3) |
C6A—C7A' | 1.514 (11) | O1B—H1OB | 0.87 (4) |
C6A—C7A | 1.520 (6) | N1B—C20B | 1.486 (3) |
C7A—C8A | 1.522 (7) | N1B—C19B | 1.493 (3) |
C7A—H7AA | 0.9900 | N1B—C18B | 1.497 (3) |
C7A—H7AB | 0.9900 | N1B—H1NB | 0.99 (3) |
C8A—C9A | 1.509 (5) | C1B—C2B | 1.399 (3) |
C8A—H8AA | 0.9900 | C1B—C6B | 1.406 (3) |
C8A—H8AB | 0.9900 | C1B—C15B | 1.540 (3) |
C9A—C14A | 1.399 (4) | C2B—C3B | 1.385 (4) |
C9A—C10A | 1.403 (4) | C2B—H2B | 0.9500 |
C9A—C8A' | 1.546 (9) | C3B—C4B | 1.380 (4) |
C7A'—C8A' | 1.509 (12) | C3B—H3B | 0.9500 |
C7A'—H7AC | 0.9900 | C4B—C5B | 1.380 (4) |
C7A'—H7AD | 0.9900 | C4B—H4B | 0.9500 |
C8A'—H8AC | 0.9900 | C5B—C6B | 1.403 (4) |
C8A'—H8AD | 0.9900 | C5B—H5B | 0.9500 |
C10A—C11A | 1.361 (5) | C6B—C7B' | 1.517 (11) |
C10A—H10A | 0.9500 | C6B—C7B | 1.523 (5) |
C11A—C12A | 1.362 (5) | C7B—C8B | 1.551 (5) |
C11A—H11A | 0.9500 | C7B—H7BA | 0.9900 |
C12A—C13A | 1.379 (4) | C7B—H7BB | 0.9900 |
C12A—H12A | 0.9500 | C8B—C9B | 1.506 (4) |
C13A—C14A | 1.376 (4) | C8B—H8BA | 0.9900 |
C13A—H13A | 0.9500 | C8B—H8BB | 0.9900 |
C14A—C15A | 1.539 (3) | C9B—C10B | 1.387 (4) |
C15A—C16A | 1.539 (3) | C9B—C14B | 1.404 (3) |
C16A—C17A | 1.526 (3) | C9B—C8B' | 1.545 (10) |
C16A—H16A | 0.9900 | C7B'—C8B' | 1.531 (12) |
C16A—H16B | 0.9900 | C7B'—H7BC | 0.9900 |
C17A—C18A | 1.520 (3) | C7B'—H7BD | 0.9900 |
C17A—H17A | 0.9900 | C8B'—H8BC | 0.9900 |
C17A—H17B | 0.9900 | C8B'—H8BD | 0.9900 |
C18A—H18A | 0.9900 | C10B—C11B | 1.384 (4) |
C18A—H18B | 0.9900 | C10B—H10B | 0.9500 |
C19A—H19A | 0.9800 | C11B—C12B | 1.383 (4) |
C19A—H19B | 0.9800 | C11B—H11B | 0.9500 |
C19A—H19C | 0.9800 | C12B—C13B | 1.386 (4) |
C20A—H20A | 0.9800 | C12B—H12B | 0.9500 |
C20A—H20B | 0.9800 | C13B—C14B | 1.392 (3) |
C20A—H20C | 0.9800 | C13B—H13B | 0.9500 |
O2A—C21A | 1.266 (3) | C14B—C15B | 1.538 (3) |
O3A—C21A | 1.254 (3) | C15B—C16B | 1.546 (3) |
O4A—C24A | 1.361 (3) | C16B—C17B | 1.535 (3) |
O4A—C28A | 1.430 (3) | C16B—H16C | 0.9900 |
O5A—C25A | 1.370 (3) | C16B—H16D | 0.9900 |
O5A—C29A | 1.427 (3) | C17B—C18B | 1.523 (3) |
C21A—C22A | 1.509 (3) | C17B—H17C | 0.9900 |
C22A—C27A | 1.381 (3) | C17B—H17D | 0.9900 |
C22A—C23A | 1.401 (3) | C18B—H18C | 0.9900 |
C23A—C24A | 1.383 (3) | C18B—H18D | 0.9900 |
C23A—H23A | 0.9500 | C19B—H19D | 0.9800 |
C24A—C25A | 1.409 (3) | C19B—H19E | 0.9800 |
C25A—C26A | 1.382 (3) | C19B—H19F | 0.9800 |
C26A—C27A | 1.394 (3) | C20B—H20D | 0.9800 |
C26A—H26A | 0.9500 | C20B—H20E | 0.9800 |
C27A—H27A | 0.9500 | C20B—H20F | 0.9800 |
C28A—H28A | 0.9800 | O1W—H1W1 | 0.815 (16) |
C28A—H28B | 0.9800 | O1W—H2W1 | 0.810 (16) |
C28A—H28C | 0.9800 | O2W—H1W2 | 0.833 (16) |
C29A—H29A | 0.9800 | O2W—H2W2 | 0.826 (17) |
C29A—H29B | 0.9800 | O3W—H1W3 | 0.831 (17) |
C29A—H29C | 0.9800 | O3W—H2W3 | 0.825 (17) |
O2B—C21B | 1.265 (3) | O4W—H1W4 | 0.823 (17) |
O3B—C21B | 1.255 (3) | O4W—H2W4 | 0.812 (17) |
O4B—C25B | 1.364 (3) | O5W—H1W5 | 0.834 (16) |
O4B—C29B | 1.433 (3) | O5W—H2W5 | 0.829 (16) |
O5B—C24B | 1.366 (3) | O6W—H1W6 | 0.835 (16) |
O5B—C28B | 1.432 (3) | O6W—H2W6 | 0.832 (16) |
C15A—O1A—H1OA | 107 (3) | O3B—C21B—C22B | 118.1 (2) |
C20A—N1A—C19A | 111.2 (2) | O2B—C21B—C22B | 118.7 (2) |
C20A—N1A—C18A | 112.9 (2) | C27B—C22B—C23B | 119.0 (2) |
C19A—N1A—C18A | 111.13 (19) | C27B—C22B—C21B | 120.5 (2) |
C20A—N1A—H1NA | 106.2 (18) | C23B—C22B—C21B | 120.5 (2) |
C19A—N1A—H1NA | 105.8 (17) | C24B—C23B—C22B | 120.4 (2) |
C18A—N1A—H1NA | 109.2 (17) | C24B—C23B—H23B | 119.8 |
C2A—C1A—C6A | 118.9 (2) | C22B—C23B—H23B | 119.8 |
C2A—C1A—C15A | 118.5 (2) | O5B—C24B—C23B | 125.3 (2) |
C6A—C1A—C15A | 122.4 (2) | O5B—C24B—C25B | 114.74 (19) |
C3A—C2A—C1A | 121.8 (3) | C23B—C24B—C25B | 120.0 (2) |
C3A—C2A—H2A | 119.1 | O4B—C25B—C26B | 125.3 (2) |
C1A—C2A—H2A | 119.1 | O4B—C25B—C24B | 115.0 (2) |
C2A—C3A—C4A | 119.4 (3) | C26B—C25B—C24B | 119.8 (2) |
C2A—C3A—H3A | 120.3 | C25B—C26B—C27B | 120.0 (2) |
C4A—C3A—H3A | 120.3 | C25B—C26B—H26B | 120.0 |
C5A—C4A—C3A | 119.4 (3) | C27B—C26B—H26B | 120.0 |
C5A—C4A—H4A | 120.3 | C22B—C27B—C26B | 120.9 (2) |
C3A—C4A—H4A | 120.3 | C22B—C27B—H27B | 119.6 |
C4A—C5A—C6A | 122.7 (3) | C26B—C27B—H27B | 119.6 |
C4A—C5A—H5A | 118.7 | O5B—C28B—H28D | 109.5 |
C6A—C5A—H5A | 118.7 | O5B—C28B—H28E | 109.5 |
C5A—C6A—C1A | 117.8 (3) | H28D—C28B—H28E | 109.5 |
C5A—C6A—C7A' | 115.2 (9) | O5B—C28B—H28F | 109.5 |
C1A—C6A—C7A' | 127.0 (9) | H28D—C28B—H28F | 109.5 |
C5A—C6A—C7A | 117.5 (4) | H28E—C28B—H28F | 109.5 |
C1A—C6A—C7A | 124.7 (4) | O4B—C29B—H29D | 109.5 |
C6A—C7A—C8A | 121.7 (4) | O4B—C29B—H29E | 109.5 |
C6A—C7A—H7AA | 106.9 | H29D—C29B—H29E | 109.5 |
C8A—C7A—H7AA | 106.9 | O4B—C29B—H29F | 109.5 |
C6A—C7A—H7AB | 106.9 | H29D—C29B—H29F | 109.5 |
C8A—C7A—H7AB | 106.9 | H29E—C29B—H29F | 109.5 |
H7AA—C7A—H7AB | 106.7 | C15B—O1B—H1OB | 109 (2) |
C9A—C8A—C7A | 117.8 (4) | C20B—N1B—C19B | 110.10 (19) |
C9A—C8A—H8AA | 107.9 | C20B—N1B—C18B | 112.79 (19) |
C7A—C8A—H8AA | 107.9 | C19B—N1B—C18B | 111.48 (19) |
C9A—C8A—H8AB | 107.9 | C20B—N1B—H1NB | 110.7 (15) |
C7A—C8A—H8AB | 107.9 | C19B—N1B—H1NB | 106.4 (15) |
H8AA—C8A—H8AB | 107.2 | C18B—N1B—H1NB | 105.1 (15) |
C14A—C9A—C10A | 118.5 (3) | C2B—C1B—C6B | 118.6 (2) |
C14A—C9A—C8A | 120.6 (3) | C2B—C1B—C15B | 118.6 (2) |
C10A—C9A—C8A | 120.2 (3) | C6B—C1B—C15B | 122.7 (2) |
C14A—C9A—C8A' | 132.1 (5) | C3B—C2B—C1B | 121.9 (3) |
C10A—C9A—C8A' | 107.3 (5) | C3B—C2B—H2B | 119.0 |
C8A'—C7A'—C6A | 114.3 (10) | C1B—C2B—H2B | 119.0 |
C8A'—C7A'—H7AC | 108.7 | C4B—C3B—C2B | 119.6 (3) |
C6A—C7A'—H7AC | 108.7 | C4B—C3B—H3B | 120.2 |
C8A'—C7A'—H7AD | 108.7 | C2B—C3B—H3B | 120.2 |
C6A—C7A'—H7AD | 108.7 | C3B—C4B—C5B | 119.3 (3) |
H7AC—C7A'—H7AD | 107.6 | C3B—C4B—H4B | 120.4 |
C7A'—C8A'—C9A | 120.7 (9) | C5B—C4B—H4B | 120.4 |
C7A'—C8A'—H8AC | 107.1 | C4B—C5B—C6B | 122.3 (3) |
C9A—C8A'—H8AC | 107.1 | C4B—C5B—H5B | 118.8 |
C7A'—C8A'—H8AD | 107.1 | C6B—C5B—H5B | 118.8 |
C9A—C8A'—H8AD | 107.1 | C5B—C6B—C1B | 118.3 (2) |
H8AC—C8A'—H8AD | 106.8 | C5B—C6B—C7B' | 114.2 (9) |
C11A—C10A—C9A | 122.3 (3) | C1B—C6B—C7B' | 127.5 (10) |
C11A—C10A—H10A | 118.9 | C5B—C6B—C7B | 117.4 (3) |
C9A—C10A—H10A | 118.9 | C1B—C6B—C7B | 124.4 (3) |
C10A—C11A—C12A | 119.0 (3) | C6B—C7B—C8B | 122.1 (3) |
C10A—C11A—H11A | 120.5 | C6B—C7B—H7BA | 106.8 |
C12A—C11A—H11A | 120.5 | C8B—C7B—H7BA | 106.8 |
C11A—C12A—C13A | 120.1 (3) | C6B—C7B—H7BB | 106.8 |
C11A—C12A—H12A | 119.9 | C8B—C7B—H7BB | 106.8 |
C13A—C12A—H12A | 119.9 | H7BA—C7B—H7BB | 106.6 |
C14A—C13A—C12A | 122.3 (3) | C9B—C8B—C7B | 116.9 (3) |
C14A—C13A—H13A | 118.9 | C9B—C8B—H8BA | 108.1 |
C12A—C13A—H13A | 118.9 | C7B—C8B—H8BA | 108.1 |
C13A—C14A—C9A | 117.9 (2) | C9B—C8B—H8BB | 108.1 |
C13A—C14A—C15A | 119.3 (2) | C7B—C8B—H8BB | 108.1 |
C9A—C14A—C15A | 122.7 (2) | H8BA—C8B—H8BB | 107.3 |
O1A—C15A—C14A | 105.94 (19) | C10B—C9B—C14B | 119.3 (2) |
O1A—C15A—C16A | 107.40 (19) | C10B—C9B—C8B | 118.9 (3) |
C14A—C15A—C16A | 114.0 (2) | C14B—C9B—C8B | 121.3 (3) |
O1A—C15A—C1A | 109.87 (19) | C10B—C9B—C8B' | 108.2 (6) |
C14A—C15A—C1A | 107.60 (19) | C14B—C9B—C8B' | 130.3 (5) |
C16A—C15A—C1A | 111.86 (19) | C6B—C7B'—C8B' | 112.0 (11) |
C17A—C16A—C15A | 111.99 (19) | C6B—C7B'—H7BC | 109.2 |
C17A—C16A—H16A | 109.2 | C8B'—C7B'—H7BC | 109.2 |
C15A—C16A—H16A | 109.2 | C6B—C7B'—H7BD | 109.2 |
C17A—C16A—H16B | 109.2 | C8B'—C7B'—H7BD | 109.2 |
C15A—C16A—H16B | 109.2 | H7BC—C7B'—H7BD | 107.9 |
H16A—C16A—H16B | 107.9 | C7B'—C8B'—C9B | 123.6 (10) |
C18A—C17A—C16A | 111.4 (2) | C7B'—C8B'—H8BC | 106.4 |
C18A—C17A—H17A | 109.3 | C9B—C8B'—H8BC | 106.4 |
C16A—C17A—H17A | 109.3 | C7B'—C8B'—H8BD | 106.4 |
C18A—C17A—H17B | 109.3 | C9B—C8B'—H8BD | 106.4 |
C16A—C17A—H17B | 109.3 | H8BC—C8B'—H8BD | 106.5 |
H17A—C17A—H17B | 108.0 | C11B—C10B—C9B | 122.1 (3) |
N1A—C18A—C17A | 111.35 (19) | C11B—C10B—H10B | 118.9 |
N1A—C18A—H18A | 109.4 | C9B—C10B—H10B | 118.9 |
C17A—C18A—H18A | 109.4 | C12B—C11B—C10B | 118.8 (3) |
N1A—C18A—H18B | 109.4 | C12B—C11B—H11B | 120.6 |
C17A—C18A—H18B | 109.4 | C10B—C11B—H11B | 120.6 |
H18A—C18A—H18B | 108.0 | C11B—C12B—C13B | 119.7 (3) |
N1A—C19A—H19A | 109.5 | C11B—C12B—H12B | 120.2 |
N1A—C19A—H19B | 109.5 | C13B—C12B—H12B | 120.2 |
H19A—C19A—H19B | 109.5 | C12B—C13B—C14B | 122.0 (3) |
N1A—C19A—H19C | 109.5 | C12B—C13B—H13B | 119.0 |
H19A—C19A—H19C | 109.5 | C14B—C13B—H13B | 119.0 |
H19B—C19A—H19C | 109.5 | C13B—C14B—C9B | 118.1 (2) |
N1A—C20A—H20A | 109.5 | C13B—C14B—C15B | 119.5 (2) |
N1A—C20A—H20B | 109.5 | C9B—C14B—C15B | 122.4 (2) |
H20A—C20A—H20B | 109.5 | O1B—C15B—C14B | 106.77 (19) |
N1A—C20A—H20C | 109.5 | O1B—C15B—C1B | 109.81 (19) |
H20A—C20A—H20C | 109.5 | C14B—C15B—C1B | 106.86 (18) |
H20B—C20A—H20C | 109.5 | O1B—C15B—C16B | 106.96 (18) |
C24A—O4A—C28A | 117.51 (19) | C14B—C15B—C16B | 114.27 (19) |
C25A—O5A—C29A | 117.25 (19) | C1B—C15B—C16B | 112.01 (19) |
O3A—C21A—O2A | 123.1 (2) | C17B—C16B—C15B | 112.40 (19) |
O3A—C21A—C22A | 119.0 (2) | C17B—C16B—H16C | 109.1 |
O2A—C21A—C22A | 117.9 (2) | C15B—C16B—H16C | 109.1 |
C27A—C22A—C23A | 119.9 (2) | C17B—C16B—H16D | 109.1 |
C27A—C22A—C21A | 120.7 (2) | C15B—C16B—H16D | 109.1 |
C23A—C22A—C21A | 119.4 (2) | H16C—C16B—H16D | 107.9 |
C24A—C23A—C22A | 120.2 (2) | C18B—C17B—C16B | 110.81 (19) |
C24A—C23A—H23A | 119.9 | C18B—C17B—H17C | 109.5 |
C22A—C23A—H23A | 119.9 | C16B—C17B—H17C | 109.5 |
O4A—C24A—C23A | 125.4 (2) | C18B—C17B—H17D | 109.5 |
O4A—C24A—C25A | 115.1 (2) | C16B—C17B—H17D | 109.5 |
C23A—C24A—C25A | 119.5 (2) | H17C—C17B—H17D | 108.1 |
O5A—C25A—C26A | 125.0 (2) | N1B—C18B—C17B | 111.57 (19) |
O5A—C25A—C24A | 115.0 (2) | N1B—C18B—H18C | 109.3 |
C26A—C25A—C24A | 120.0 (2) | C17B—C18B—H18C | 109.3 |
C25A—C26A—C27A | 119.9 (2) | N1B—C18B—H18D | 109.3 |
C25A—C26A—H26A | 120.0 | C17B—C18B—H18D | 109.3 |
C27A—C26A—H26A | 120.0 | H18C—C18B—H18D | 108.0 |
C22A—C27A—C26A | 120.4 (2) | N1B—C19B—H19D | 109.5 |
C22A—C27A—H27A | 119.8 | N1B—C19B—H19E | 109.5 |
C26A—C27A—H27A | 119.8 | H19D—C19B—H19E | 109.5 |
O4A—C28A—H28A | 109.5 | N1B—C19B—H19F | 109.5 |
O4A—C28A—H28B | 109.5 | H19D—C19B—H19F | 109.5 |
H28A—C28A—H28B | 109.5 | H19E—C19B—H19F | 109.5 |
O4A—C28A—H28C | 109.5 | N1B—C20B—H20D | 109.5 |
H28A—C28A—H28C | 109.5 | N1B—C20B—H20E | 109.5 |
H28B—C28A—H28C | 109.5 | H20D—C20B—H20E | 109.5 |
O5A—C29A—H29A | 109.5 | N1B—C20B—H20F | 109.5 |
O5A—C29A—H29B | 109.5 | H20D—C20B—H20F | 109.5 |
H29A—C29A—H29B | 109.5 | H20E—C20B—H20F | 109.5 |
O5A—C29A—H29C | 109.5 | H1W1—O1W—H2W1 | 112 (3) |
H29A—C29A—H29C | 109.5 | H1W2—O2W—H2W2 | 105 (3) |
H29B—C29A—H29C | 109.5 | H1W3—O3W—H2W3 | 104 (3) |
C25B—O4B—C29B | 117.04 (19) | H1W4—O4W—H2W4 | 111 (3) |
C24B—O5B—C28B | 117.26 (18) | H1W5—O5W—H2W5 | 103 (3) |
O3B—C21B—O2B | 123.3 (2) | H1W6—O6W—H2W6 | 106 (2) |
C6A—C1A—C2A—C3A | 1.6 (4) | O3B—C21B—C22B—C27B | 10.7 (3) |
C15A—C1A—C2A—C3A | −175.1 (2) | O2B—C21B—C22B—C27B | −169.5 (2) |
C1A—C2A—C3A—C4A | 0.8 (4) | O3B—C21B—C22B—C23B | −170.3 (2) |
C2A—C3A—C4A—C5A | −2.8 (4) | O2B—C21B—C22B—C23B | 9.5 (3) |
C3A—C4A—C5A—C6A | 2.5 (4) | C27B—C22B—C23B—C24B | 0.7 (3) |
C4A—C5A—C6A—C1A | −0.1 (4) | C21B—C22B—C23B—C24B | −178.3 (2) |
C4A—C5A—C6A—C7A' | −178.1 (10) | C28B—O5B—C24B—C23B | −8.1 (3) |
C4A—C5A—C6A—C7A | −179.2 (5) | C28B—O5B—C24B—C25B | 171.3 (2) |
C2A—C1A—C6A—C5A | −1.9 (4) | C22B—C23B—C24B—O5B | −179.9 (2) |
C15A—C1A—C6A—C5A | 174.7 (2) | C22B—C23B—C24B—C25B | 0.7 (3) |
C2A—C1A—C6A—C7A' | 175.8 (11) | C29B—O4B—C25B—C26B | 7.6 (3) |
C15A—C1A—C6A—C7A' | −7.6 (12) | C29B—O4B—C25B—C24B | −172.3 (2) |
C2A—C1A—C6A—C7A | 177.1 (5) | O5B—C24B—C25B—O4B | −1.0 (3) |
C15A—C1A—C6A—C7A | −6.3 (6) | C23B—C24B—C25B—O4B | 178.4 (2) |
C5A—C6A—C7A—C8A | −146.0 (7) | O5B—C24B—C25B—C26B | 179.1 (2) |
C1A—C6A—C7A—C8A | 35.0 (12) | C23B—C24B—C25B—C26B | −1.5 (3) |
C6A—C7A—C8A—C9A | 18.7 (12) | O4B—C25B—C26B—C27B | −179.1 (2) |
C7A—C8A—C9A—C14A | −61.2 (7) | C24B—C25B—C26B—C27B | 0.8 (3) |
C7A—C8A—C9A—C10A | 128.9 (6) | C23B—C22B—C27B—C26B | −1.4 (3) |
C5A—C6A—C7A'—C8A' | −119.5 (15) | C21B—C22B—C27B—C26B | 177.6 (2) |
C1A—C6A—C7A'—C8A' | 63 (2) | C25B—C26B—C27B—C22B | 0.7 (4) |
C6A—C7A'—C8A'—C9A | −38 (3) | C6B—C1B—C2B—C3B | 0.7 (4) |
C14A—C9A—C8A'—C7A' | 1 (2) | C15B—C1B—C2B—C3B | −176.0 (2) |
C10A—C9A—C8A'—C7A' | 163.6 (15) | C1B—C2B—C3B—C4B | 0.4 (4) |
C14A—C9A—C10A—C11A | 0.4 (4) | C2B—C3B—C4B—C5B | −1.4 (4) |
C8A—C9A—C10A—C11A | 170.5 (4) | C3B—C4B—C5B—C6B | 1.3 (4) |
C8A'—C9A—C10A—C11A | −165.2 (6) | C4B—C5B—C6B—C1B | −0.2 (4) |
C9A—C10A—C11A—C12A | −0.2 (5) | C4B—C5B—C6B—C7B' | −177.3 (11) |
C10A—C11A—C12A—C13A | −0.6 (6) | C4B—C5B—C6B—C7B | 180.0 (4) |
C11A—C12A—C13A—C14A | 1.2 (6) | C2B—C1B—C6B—C5B | −0.8 (3) |
C12A—C13A—C14A—C9A | −1.0 (5) | C15B—C1B—C6B—C5B | 175.8 (2) |
C12A—C13A—C14A—C15A | 178.0 (3) | C2B—C1B—C6B—C7B' | 175.8 (12) |
C10A—C9A—C14A—C13A | 0.2 (4) | C15B—C1B—C6B—C7B' | −7.6 (12) |
C8A—C9A—C14A—C13A | −169.9 (3) | C2B—C1B—C6B—C7B | 179.0 (4) |
C8A'—C9A—C14A—C13A | 161.6 (8) | C15B—C1B—C6B—C7B | −4.5 (5) |
C10A—C9A—C14A—C15A | −178.8 (2) | C5B—C6B—C7B—C8B | −145.8 (5) |
C8A—C9A—C14A—C15A | 11.2 (4) | C1B—C6B—C7B—C8B | 34.5 (9) |
C8A'—C9A—C14A—C15A | −17.4 (9) | C6B—C7B—C8B—C9B | 17.7 (9) |
C13A—C14A—C15A—O1A | 1.9 (3) | C7B—C8B—C9B—C10B | 128.6 (5) |
C9A—C14A—C15A—O1A | −179.2 (2) | C7B—C8B—C9B—C14B | −59.8 (6) |
C13A—C14A—C15A—C16A | 119.7 (3) | C5B—C6B—C7B'—C8B' | −122.2 (16) |
C9A—C14A—C15A—C16A | −61.3 (3) | C1B—C6B—C7B'—C8B' | 61 (2) |
C13A—C14A—C15A—C1A | −115.6 (3) | C6B—C7B'—C8B'—C9B | −35 (3) |
C9A—C14A—C15A—C1A | 63.3 (3) | C10B—C9B—C8B'—C7B' | 160.9 (18) |
C2A—C1A—C15A—O1A | 0.7 (3) | C14B—C9B—C8B'—C7B' | −2 (3) |
C6A—C1A—C15A—O1A | −175.9 (2) | C14B—C9B—C10B—C11B | 0.8 (4) |
C2A—C1A—C15A—C14A | 115.6 (2) | C8B—C9B—C10B—C11B | 172.6 (3) |
C6A—C1A—C15A—C14A | −61.0 (3) | C8B'—C9B—C10B—C11B | −164.0 (8) |
C2A—C1A—C15A—C16A | −118.4 (2) | C9B—C10B—C11B—C12B | −0.3 (4) |
C6A—C1A—C15A—C16A | 64.9 (3) | C10B—C11B—C12B—C13B | −0.2 (4) |
O1A—C15A—C16A—C17A | 60.7 (3) | C11B—C12B—C13B—C14B | 0.2 (5) |
C14A—C15A—C16A—C17A | −56.3 (3) | C12B—C13B—C14B—C9B | 0.3 (4) |
C1A—C15A—C16A—C17A | −178.7 (2) | C12B—C13B—C14B—C15B | 177.8 (3) |
C15A—C16A—C17A—C18A | −172.24 (19) | C10B—C9B—C14B—C13B | −0.8 (4) |
C20A—N1A—C18A—C17A | 63.2 (3) | C8B—C9B—C14B—C13B | −172.3 (3) |
C19A—N1A—C18A—C17A | −171.1 (2) | C8B'—C9B—C14B—C13B | 160.2 (10) |
C16A—C17A—C18A—N1A | 162.68 (19) | C10B—C9B—C14B—C15B | −178.2 (2) |
O3A—C21A—C22A—C27A | 1.3 (3) | C8B—C9B—C14B—C15B | 10.2 (4) |
O2A—C21A—C22A—C27A | −178.6 (2) | C8B'—C9B—C14B—C15B | −17.2 (11) |
O3A—C21A—C22A—C23A | −179.2 (2) | C13B—C14B—C15B—O1B | 5.2 (3) |
O2A—C21A—C22A—C23A | 0.9 (3) | C9B—C14B—C15B—O1B | −177.4 (2) |
C27A—C22A—C23A—C24A | 1.2 (3) | C13B—C14B—C15B—C1B | −112.3 (2) |
C21A—C22A—C23A—C24A | −178.3 (2) | C9B—C14B—C15B—C1B | 65.1 (3) |
C28A—O4A—C24A—C23A | −1.4 (3) | C13B—C14B—C15B—C16B | 123.2 (2) |
C28A—O4A—C24A—C25A | 177.2 (2) | C9B—C14B—C15B—C16B | −59.4 (3) |
C22A—C23A—C24A—O4A | 179.7 (2) | C2B—C1B—C15B—O1B | −2.1 (3) |
C22A—C23A—C24A—C25A | 1.2 (3) | C6B—C1B—C15B—O1B | −178.6 (2) |
C29A—O5A—C25A—C26A | 13.6 (3) | C2B—C1B—C15B—C14B | 113.4 (2) |
C29A—O5A—C25A—C24A | −166.7 (2) | C6B—C1B—C15B—C14B | −63.2 (3) |
O4A—C24A—C25A—O5A | −1.3 (3) | C2B—C1B—C15B—C16B | −120.8 (2) |
C23A—C24A—C25A—O5A | 177.3 (2) | C6B—C1B—C15B—C16B | 62.7 (3) |
O4A—C24A—C25A—C26A | 178.4 (2) | O1B—C15B—C16B—C17B | 61.8 (3) |
C23A—C24A—C25A—C26A | −3.0 (3) | C14B—C15B—C16B—C17B | −56.2 (3) |
O5A—C25A—C26A—C27A | −177.9 (2) | C1B—C15B—C16B—C17B | −177.87 (19) |
C24A—C25A—C26A—C27A | 2.4 (3) | C15B—C16B—C17B—C18B | −156.6 (2) |
C23A—C22A—C27A—C26A | −1.8 (3) | C20B—N1B—C18B—C17B | 69.5 (2) |
C21A—C22A—C27A—C26A | 177.7 (2) | C19B—N1B—C18B—C17B | −166.07 (19) |
C25A—C26A—C27A—C22A | 0.0 (3) | C16B—C17B—C18B—N1B | 167.64 (19) |
D—H···A | D—H | H···A | D···A | D—H···A |
O1A—H1OA···O5W | 0.82 (4) | 1.95 (4) | 2.762 (3) | 172 (4) |
N1A—H1NA···O2A | 0.99 (3) | 1.71 (3) | 2.690 (3) | 172 (3) |
N1A—H1NA···O3A | 0.99 (3) | 2.45 (3) | 3.108 (3) | 124 (2) |
C16A—H16B···O5W | 0.99 | 2.61 | 3.308 (3) | 128 |
C23A—H23A···O2Wi | 0.95 | 2.61 | 3.519 (3) | 159 |
O1B—H1OB···O6W | 0.87 (4) | 1.91 (4) | 2.781 (3) | 173 (3) |
N1B—H1NB···O2B | 0.99 (3) | 1.75 (3) | 2.723 (3) | 165 (2) |
N1B—H1NB···O3B | 0.99 (3) | 2.48 (3) | 3.186 (3) | 128 (2) |
C16B—H16D···O6W | 0.99 | 2.46 | 3.134 (3) | 125 |
O1W—H1W1···O3A | 0.82 (2) | 1.96 (2) | 2.770 (3) | 172 (4) |
O1W—H2W1···O3W | 0.81 (2) | 2.02 (2) | 2.795 (3) | 161 (4) |
O2W—H1W2···O2Aii | 0.83 (2) | 1.95 (2) | 2.773 (3) | 170 (4) |
O2W—H2W2···O1W | 0.83 (2) | 1.93 (2) | 2.738 (3) | 166 (4) |
O3W—H1W3···O3Bi | 0.83 (2) | 1.96 (2) | 2.785 (3) | 178 (5) |
O3W—H2W3···O4W | 0.83 (2) | 1.88 (2) | 2.705 (4) | 174 (5) |
O4W—H1W4···O2B | 0.82 (2) | 1.89 (2) | 2.708 (3) | 171 (4) |
O4W—H2W4···O2W | 0.81 (2) | 1.99 (2) | 2.771 (3) | 160 (4) |
O5W—H1W5···O4Biii | 0.83 (2) | 2.36 (3) | 3.035 (3) | 138 (3) |
O5W—H1W5···O5Biii | 0.83 (2) | 2.23 (2) | 2.971 (2) | 149 (3) |
O5W—H2W5···O3A | 0.83 (2) | 2.00 (2) | 2.820 (3) | 173 (4) |
O6W—H1W6···O4Aiv | 0.84 (2) | 2.24 (3) | 2.886 (2) | 134 (3) |
O6W—H1W6···O5Aiv | 0.84 (2) | 2.23 (2) | 2.980 (3) | 150 (3) |
O6W—H2W6···O3B | 0.83 (2) | 1.95 (2) | 2.769 (3) | 169 (3) |
Symmetry codes: (i) x+1, y, z; (ii) x−1, y, z; (iii) x, y, z−1; (iv) x−1, y, z+1. |
C20H26NO+·C7H4ClO2− | F(000) = 960 |
Mr = 451.97 | Dx = 1.303 Mg m−3 |
Monoclinic, P21/n | Mo Kα radiation, λ = 0.71073 Å |
a = 6.7576 (2) Å | Cell parameters from 9897 reflections |
b = 22.9081 (6) Å | θ = 2.9–27.5° |
c = 14.9477 (3) Å | µ = 0.20 mm−1 |
β = 95.359 (1)° | T = 180 K |
V = 2303.85 (10) Å3 | Block, colourless |
Z = 4 | 0.22 × 0.16 × 0.12 mm |
Bruker D8 Venture dual source diffractometer | 5279 independent reflections |
Radiation source: microsource | 4188 reflections with I > 2σ(I) |
Detector resolution: 7.41 pixels mm-1 | Rint = 0.039 |
φ and ω scans | θmax = 27.5°, θmin = 2.2° |
Absorption correction: multi-scan (SADABS; Krause et al., 2015) | h = −8→8 |
Tmin = 0.848, Tmax = 0.959 | k = −29→29 |
35872 measured reflections | l = −19→19 |
Refinement on F2 | Secondary atom site location: difference Fourier map |
Least-squares matrix: full | Hydrogen site location: mixed |
R[F2 > 2σ(F2)] = 0.045 | H atoms treated by a mixture of independent and constrained refinement |
wR(F2) = 0.110 | w = 1/[σ2(Fo2) + (0.0344P)2 + 1.4657P] where P = (Fo2 + 2Fc2)/3 |
S = 1.03 | (Δ/σ)max = 0.001 |
5279 reflections | Δρmax = 0.63 e Å−3 |
380 parameters | Δρmin = −0.61 e Å−3 |
404 restraints | Extinction correction: SHELXL2019/2 (Sheldrick, 2015b), Fc*=kFc[1+0.001xFc2λ3/sin(2θ)]-1/4 |
Primary atom site location: structure-invariant direct methods | Extinction coefficient: 0.0055 (11) |
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). The crystals appeared to undergo a destructive phase transition when cooled to 90K. Visual inspection of crystal integrity and diffraction quality vs temperature established a safe temperature for data collection of -93° C. |
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 | 1.08766 (18) | 0.71374 (6) | 0.68005 (9) | 0.0388 (3) | |
H1O | 1.105 (3) | 0.6787 (11) | 0.6624 (15) | 0.054 (7)* | |
N1 | 0.6010 (2) | 0.61029 (6) | 0.46779 (9) | 0.0297 (3) | |
H1N | 0.560 (3) | 0.5931 (9) | 0.5248 (14) | 0.048 (6)* | |
C1 | 0.8566 (3) | 0.79026 (7) | 0.68891 (11) | 0.0340 (4) | |
C2 | 1.0026 (3) | 0.82305 (8) | 0.65383 (12) | 0.0452 (5) | |
H2 | 1.119208 | 0.804054 | 0.637893 | 0.054* | |
C3 | 0.9839 (4) | 0.88324 (9) | 0.64107 (14) | 0.0583 (6) | |
H3 | 1.087910 | 0.904653 | 0.617711 | 0.070* | |
C4 | 0.8163 (4) | 0.91134 (9) | 0.66215 (13) | 0.0519 (6) | |
H4 | 0.802576 | 0.952324 | 0.654118 | 0.062* | |
C5 | 0.6703 (3) | 0.87968 (9) | 0.69468 (15) | 0.0523 (5) | |
H5 | 0.552625 | 0.899131 | 0.708215 | 0.063* | |
C6 | 0.6852 (3) | 0.81968 (8) | 0.70920 (17) | 0.0521 (5) | |
C7 | 0.5037 (4) | 0.78841 (14) | 0.7261 (2) | 0.0413 (6) | 0.585 (3) |
H7A | 0.479064 | 0.755636 | 0.683309 | 0.050* | 0.585 (3) |
H7B | 0.387589 | 0.814958 | 0.719918 | 0.050* | 0.585 (3) |
C8 | 0.5401 (5) | 0.76585 (19) | 0.8220 (2) | 0.0460 (7) | 0.585 (3) |
H8A | 0.413604 | 0.748711 | 0.837966 | 0.055* | 0.585 (3) |
H8B | 0.567508 | 0.800205 | 0.861352 | 0.055* | 0.585 (3) |
C9 | 0.7129 (3) | 0.71860 (11) | 0.84866 (13) | 0.0536 (6) | |
C7' | 0.5369 (7) | 0.7976 (2) | 0.7851 (4) | 0.0413 (6) | 0.415 (3) |
H7'A | 0.584189 | 0.816270 | 0.842941 | 0.050* | 0.415 (3) |
H7'B | 0.402748 | 0.813447 | 0.767179 | 0.050* | 0.415 (3) |
C8' | 0.5133 (6) | 0.7327 (2) | 0.8032 (4) | 0.0460 (7) | 0.415 (3) |
H8'A | 0.406685 | 0.725218 | 0.842848 | 0.055* | 0.415 (3) |
H8'B | 0.485756 | 0.710332 | 0.746685 | 0.055* | 0.415 (3) |
C10 | 0.7166 (4) | 0.70071 (12) | 0.93794 (14) | 0.0628 (7) | |
H10 | 0.604666 | 0.708795 | 0.969898 | 0.075* | |
C11 | 0.8748 (4) | 0.67204 (10) | 0.98133 (14) | 0.0553 (6) | |
H11 | 0.872768 | 0.660390 | 1.042233 | 0.066* | |
C12 | 1.0359 (4) | 0.66044 (9) | 0.93555 (14) | 0.0543 (6) | |
H12 | 1.148164 | 0.640996 | 0.964731 | 0.065* | |
C13 | 1.0353 (3) | 0.67713 (8) | 0.84621 (13) | 0.0427 (4) | |
H13 | 1.147668 | 0.668280 | 0.814937 | 0.051* | |
C14 | 0.8757 (2) | 0.70636 (7) | 0.80106 (11) | 0.0328 (4) | |
C15 | 0.8907 (2) | 0.72385 (7) | 0.70189 (11) | 0.0306 (4) | |
C16 | 0.7494 (2) | 0.68667 (7) | 0.63750 (11) | 0.0302 (3) | |
H16A | 0.781845 | 0.644864 | 0.647117 | 0.036* | |
H16B | 0.610943 | 0.692780 | 0.652065 | 0.036* | |
C17 | 0.7636 (3) | 0.70177 (8) | 0.53891 (11) | 0.0376 (4) | |
H17A | 0.758925 | 0.744767 | 0.532353 | 0.045* | |
H17B | 0.894424 | 0.688522 | 0.521902 | 0.045* | |
C18 | 0.6024 (3) | 0.67544 (7) | 0.47353 (11) | 0.0373 (4) | |
H18A | 0.471694 | 0.688457 | 0.490970 | 0.045* | |
H18B | 0.617271 | 0.691320 | 0.412923 | 0.045* | |
C19 | 0.7946 (3) | 0.58483 (9) | 0.44969 (13) | 0.0428 (4) | |
H19A | 0.782727 | 0.542242 | 0.446047 | 0.064* | |
H19B | 0.895551 | 0.595334 | 0.498382 | 0.064* | |
H19C | 0.833659 | 0.600058 | 0.392648 | 0.064* | |
C20 | 0.4418 (3) | 0.59129 (9) | 0.39854 (13) | 0.0467 (5) | |
H20A | 0.466060 | 0.608124 | 0.340281 | 0.070* | |
H20B | 0.312640 | 0.604628 | 0.415442 | 0.070* | |
H20C | 0.441801 | 0.548605 | 0.394234 | 0.070* | |
Cl1 | −0.05707 (7) | 0.52215 (2) | 0.69053 (3) | 0.04297 (16) | 0.9600 (15) |
O2 | 0.4875 (4) | 0.55670 (15) | 0.60797 (16) | 0.0359 (6) | 0.9600 (15) |
O3 | 0.2218 (4) | 0.61482 (13) | 0.60465 (13) | 0.0406 (4) | 0.9600 (15) |
C21 | 0.3407 (3) | 0.57905 (8) | 0.64190 (12) | 0.0294 (4) | 0.9600 (15) |
C22 | 0.3192 (3) | 0.56105 (7) | 0.73778 (11) | 0.0303 (4) | 0.9600 (15) |
C23 | 0.1495 (3) | 0.53554 (7) | 0.76610 (12) | 0.0325 (4) | 0.9600 (15) |
C24 | 0.1385 (3) | 0.52015 (9) | 0.85523 (13) | 0.0425 (5) | 0.9600 (15) |
H24 | 0.022568 | 0.501828 | 0.873292 | 0.051* | 0.9600 (15) |
C25 | 0.2976 (4) | 0.53169 (9) | 0.91742 (13) | 0.0499 (5) | 0.9600 (15) |
H25 | 0.290500 | 0.521547 | 0.978665 | 0.060* | 0.9600 (15) |
C26 | 0.4667 (4) | 0.55782 (9) | 0.89141 (14) | 0.0491 (5) | 0.9600 (15) |
H26 | 0.575063 | 0.566423 | 0.934541 | 0.059* | 0.9600 (15) |
C27 | 0.4770 (4) | 0.57139 (12) | 0.80175 (17) | 0.0417 (5) | 0.9600 (15) |
H27 | 0.595325 | 0.588246 | 0.783629 | 0.050* | 0.9600 (15) |
Cl1' | 0.564 (2) | 0.5767 (8) | 0.8173 (12) | 0.053 (4) | 0.0400 (15) |
O2' | 0.488 (9) | 0.561 (4) | 0.622 (5) | 0.0359 (6) | 0.0400 (15) |
O3' | 0.225 (10) | 0.618 (3) | 0.586 (4) | 0.0406 (4) | 0.0400 (15) |
C21' | 0.317 (5) | 0.5805 (11) | 0.6330 (19) | 0.0294 (4) | 0.0400 (15) |
C22' | 0.226 (3) | 0.5557 (6) | 0.7133 (13) | 0.035 (3) | 0.0400 (15) |
C23' | 0.322 (2) | 0.5517 (6) | 0.7991 (13) | 0.042 (2) | 0.0400 (15) |
C24' | 0.230 (3) | 0.5285 (10) | 0.8706 (14) | 0.042 (3) | 0.0400 (15) |
H24' | 0.299591 | 0.526275 | 0.928789 | 0.051* | 0.0400 (15) |
C25' | 0.037 (4) | 0.5087 (11) | 0.8556 (17) | 0.041 (3) | 0.0400 (15) |
H25' | −0.026900 | 0.492706 | 0.903833 | 0.049* | 0.0400 (15) |
C26' | −0.063 (3) | 0.5119 (11) | 0.7711 (18) | 0.039 (3) | 0.0400 (15) |
H26' | −0.198774 | 0.501143 | 0.761498 | 0.047* | 0.0400 (15) |
C27' | 0.039 (4) | 0.531 (2) | 0.7004 (16) | 0.040 (3) | 0.0400 (15) |
H27' | −0.022587 | 0.527469 | 0.640815 | 0.048* | 0.0400 (15) |
U11 | U22 | U33 | U12 | U13 | U23 | |
O1 | 0.0272 (6) | 0.0374 (7) | 0.0526 (8) | −0.0017 (5) | 0.0073 (5) | −0.0064 (6) |
N1 | 0.0364 (7) | 0.0252 (7) | 0.0272 (7) | −0.0008 (6) | 0.0006 (6) | −0.0023 (5) |
C1 | 0.0378 (9) | 0.0294 (8) | 0.0326 (8) | −0.0031 (7) | −0.0077 (7) | −0.0076 (7) |
C2 | 0.0652 (13) | 0.0391 (10) | 0.0330 (9) | −0.0016 (9) | 0.0144 (9) | −0.0006 (8) |
C3 | 0.0934 (18) | 0.0407 (11) | 0.0437 (11) | −0.0089 (12) | 0.0217 (11) | 0.0096 (9) |
C4 | 0.0881 (17) | 0.0306 (10) | 0.0352 (10) | 0.0043 (10) | −0.0035 (10) | −0.0006 (8) |
C5 | 0.0570 (13) | 0.0329 (10) | 0.0637 (13) | 0.0093 (9) | −0.0126 (10) | −0.0106 (9) |
C6 | 0.0381 (10) | 0.0302 (9) | 0.0863 (16) | −0.0002 (8) | −0.004 (1) | −0.0095 (10) |
C7 | 0.0304 (12) | 0.0422 (14) | 0.0501 (15) | 0.0058 (10) | −0.0025 (12) | −0.0013 (13) |
C8 | 0.0282 (12) | 0.063 (2) | 0.0472 (16) | 0.0013 (16) | 0.0083 (11) | −0.0021 (16) |
C9 | 0.0333 (10) | 0.0894 (16) | 0.0375 (10) | 0.003 (1) | 0.0004 (8) | −0.0034 (10) |
C7' | 0.0304 (12) | 0.0422 (14) | 0.0501 (15) | 0.0058 (10) | −0.0025 (12) | −0.0013 (13) |
C8' | 0.0282 (12) | 0.063 (2) | 0.0472 (16) | 0.0013 (16) | 0.0083 (11) | −0.0021 (16) |
C10 | 0.0507 (13) | 0.100 (2) | 0.0389 (11) | 0.0042 (13) | 0.0082 (9) | −0.0066 (12) |
C11 | 0.0745 (15) | 0.0563 (13) | 0.0349 (10) | 0.0040 (11) | 0.0031 (10) | −0.0071 (9) |
C12 | 0.0716 (15) | 0.0438 (11) | 0.0456 (11) | 0.0219 (10) | −0.0053 (10) | −0.0012 (9) |
C13 | 0.0511 (11) | 0.0340 (9) | 0.043 (1) | 0.0139 (8) | 0.0038 (8) | −0.0046 (8) |
C14 | 0.0331 (9) | 0.0300 (8) | 0.0345 (8) | −0.0054 (7) | −0.0013 (7) | −0.0097 (7) |
C15 | 0.0251 (8) | 0.0284 (8) | 0.0377 (9) | −0.0008 (6) | 0.0005 (6) | −0.0050 (7) |
C16 | 0.0318 (8) | 0.0249 (8) | 0.0337 (8) | −0.0024 (6) | 0.0021 (7) | −0.0041 (6) |
C17 | 0.0509 (11) | 0.0283 (8) | 0.0335 (9) | −0.0088 (8) | 0.0032 (8) | −0.0039 (7) |
C18 | 0.0543 (11) | 0.0248 (8) | 0.0315 (8) | 0.0009 (8) | −0.0031 (8) | −0.0010 (6) |
C19 | 0.0442 (10) | 0.042 (1) | 0.0441 (10) | 0.0038 (8) | 0.0145 (8) | −0.0055 (8) |
C20 | 0.0562 (12) | 0.0408 (10) | 0.0394 (10) | −0.0063 (9) | −0.0146 (9) | −0.0058 (8) |
Cl1 | 0.0367 (3) | 0.0428 (3) | 0.0493 (3) | −0.0071 (2) | 0.0036 (2) | 0.0053 (2) |
O2 | 0.0367 (7) | 0.0329 (9) | 0.0401 (12) | 0.0059 (6) | 0.0139 (7) | 0.0008 (10) |
O3 | 0.0401 (7) | 0.0446 (8) | 0.0377 (12) | 0.0127 (6) | 0.0075 (8) | 0.0074 (8) |
C21 | 0.0290 (9) | 0.0262 (8) | 0.0333 (8) | −0.0014 (6) | 0.0047 (7) | −0.0028 (6) |
C22 | 0.0326 (9) | 0.0264 (8) | 0.0323 (9) | 0.0067 (7) | 0.0052 (7) | −0.0017 (7) |
C23 | 0.0391 (9) | 0.0258 (8) | 0.0334 (8) | 0.0049 (7) | 0.0070 (7) | −0.0007 (7) |
C24 | 0.0569 (12) | 0.0332 (10) | 0.0398 (10) | 0.0022 (9) | 0.0167 (9) | 0.0022 (8) |
C25 | 0.0778 (15) | 0.0420 (11) | 0.0302 (9) | 0.0102 (10) | 0.0059 (10) | 0.0026 (8) |
C26 | 0.0595 (13) | 0.0473 (12) | 0.0382 (10) | 0.0089 (10) | −0.0078 (9) | −0.0039 (9) |
C27 | 0.0390 (13) | 0.0429 (12) | 0.0423 (12) | 0.0051 (11) | −0.0003 (11) | −0.0012 (9) |
Cl1' | 0.059 (8) | 0.051 (7) | 0.050 (7) | 0.004 (7) | 0.006 (7) | 0.003 (6) |
O2' | 0.0367 (7) | 0.0329 (9) | 0.0401 (12) | 0.0059 (6) | 0.0139 (7) | 0.0008 (10) |
O3' | 0.0401 (7) | 0.0446 (8) | 0.0377 (12) | 0.0127 (6) | 0.0075 (8) | 0.0074 (8) |
C21' | 0.0290 (9) | 0.0262 (8) | 0.0333 (8) | −0.0014 (6) | 0.0047 (7) | −0.0028 (6) |
C22' | 0.038 (4) | 0.030 (4) | 0.038 (4) | 0.004 (4) | 0.005 (4) | −0.003 (4) |
C23' | 0.051 (4) | 0.037 (4) | 0.038 (4) | 0.005 (4) | 0.004 (4) | 0.000 (4) |
C24' | 0.056 (4) | 0.037 (4) | 0.035 (4) | 0.005 (4) | 0.006 (4) | 0.002 (4) |
C25' | 0.056 (5) | 0.033 (5) | 0.034 (5) | 0.004 (5) | 0.009 (5) | 0.003 (5) |
C26' | 0.049 (5) | 0.033 (5) | 0.036 (5) | 0.002 (5) | 0.010 (5) | 0.002 (5) |
C27' | 0.043 (6) | 0.035 (6) | 0.042 (6) | 0.003 (6) | 0.006 (6) | −0.001 (6) |
O1—C15 | 1.418 (2) | C16—C17 | 1.525 (2) |
O1—H1O | 0.86 (2) | C16—H16A | 0.9900 |
N1—C19 | 1.480 (2) | C16—H16B | 0.9900 |
N1—C20 | 1.487 (2) | C17—C18 | 1.519 (2) |
N1—C18 | 1.495 (2) | C17—H17A | 0.9900 |
N1—H1N | 1.00 (2) | C17—H17B | 0.9900 |
C1—C2 | 1.382 (3) | C18—H18A | 0.9900 |
C1—C6 | 1.398 (3) | C18—H18B | 0.9900 |
C1—C15 | 1.548 (2) | C19—H19A | 0.9800 |
C2—C3 | 1.396 (3) | C19—H19B | 0.9800 |
C2—H2 | 0.9500 | C19—H19C | 0.9800 |
C3—C4 | 1.365 (3) | C20—H20A | 0.9800 |
C3—H3 | 0.9500 | C20—H20B | 0.9800 |
C4—C5 | 1.351 (3) | C20—H20C | 0.9800 |
C4—H4 | 0.9500 | Cl1—C23 | 1.7388 (19) |
C5—C6 | 1.394 (3) | O2—C21 | 1.264 (2) |
C5—H5 | 0.9500 | O3—C21 | 1.243 (2) |
C6—C7 | 1.463 (4) | C21—C22 | 1.511 (2) |
C6—C7' | 1.662 (5) | C22—C27 | 1.384 (3) |
C7—C8 | 1.522 (4) | C22—C23 | 1.388 (2) |
C7—H7A | 0.9900 | C23—C24 | 1.387 (3) |
C7—H7B | 0.9900 | C24—C25 | 1.380 (3) |
C8—C9 | 1.615 (4) | C24—H24 | 0.9500 |
C8—H8A | 0.9900 | C25—C26 | 1.378 (3) |
C8—H8B | 0.9900 | C25—H25 | 0.9500 |
C9—C14 | 1.394 (3) | C26—C27 | 1.384 (3) |
C9—C10 | 1.394 (3) | C26—H26 | 0.9500 |
C9—C8' | 1.488 (5) | C27—H27 | 0.9500 |
C7'—C8' | 1.523 (6) | Cl1'—C23' | 1.729 (9) |
C7'—H7'A | 0.9900 | O2'—C21' | 1.264 (9) |
C7'—H7'B | 0.9900 | O3'—C21' | 1.243 (9) |
C8'—H8'A | 0.9900 | C21'—C22' | 1.510 (9) |
C8'—H8'B | 0.9900 | C22'—C27' | 1.38 (1) |
C10—C11 | 1.366 (3) | C22'—C23' | 1.385 (9) |
C10—H10 | 0.9500 | C23'—C24' | 1.389 (9) |
C11—C12 | 1.365 (3) | C24'—C25' | 1.379 (10) |
C11—H11 | 0.9500 | C24'—H24' | 0.9500 |
C12—C13 | 1.389 (3) | C25'—C26' | 1.378 (10) |
C12—H12 | 0.9500 | C25'—H25' | 0.9500 |
C13—C14 | 1.389 (2) | C26'—C27' | 1.385 (10) |
C13—H13 | 0.9500 | C26'—H26' | 0.9500 |
C14—C15 | 1.548 (2) | C27'—H27' | 0.9500 |
C15—C16 | 1.547 (2) | ||
C15—O1—H1O | 112.3 (15) | C16—C15—C1 | 112.76 (13) |
C19—N1—C20 | 110.60 (14) | C14—C15—C1 | 110.61 (13) |
C19—N1—C18 | 113.77 (14) | C17—C16—C15 | 112.66 (14) |
C20—N1—C18 | 109.41 (13) | C17—C16—H16A | 109.1 |
C19—N1—H1N | 108.8 (12) | C15—C16—H16A | 109.1 |
C20—N1—H1N | 103.6 (12) | C17—C16—H16B | 109.1 |
C18—N1—H1N | 110.2 (12) | C15—C16—H16B | 109.1 |
C2—C1—C6 | 117.12 (17) | H16A—C16—H16B | 107.8 |
C2—C1—C15 | 118.58 (16) | C18—C17—C16 | 115.17 (15) |
C6—C1—C15 | 124.29 (16) | C18—C17—H17A | 108.5 |
C1—C2—C3 | 122.0 (2) | C16—C17—H17A | 108.5 |
C1—C2—H2 | 119.0 | C18—C17—H17B | 108.5 |
C3—C2—H2 | 119.0 | C16—C17—H17B | 108.5 |
C4—C3—C2 | 120.0 (2) | H17A—C17—H17B | 107.5 |
C4—C3—H3 | 120.0 | N1—C18—C17 | 115.70 (14) |
C2—C3—H3 | 120.0 | N1—C18—H18A | 108.4 |
C5—C4—C3 | 118.64 (19) | C17—C18—H18A | 108.4 |
C5—C4—H4 | 120.7 | N1—C18—H18B | 108.4 |
C3—C4—H4 | 120.7 | C17—C18—H18B | 108.4 |
C4—C5—C6 | 122.8 (2) | H18A—C18—H18B | 107.4 |
C4—C5—H5 | 118.6 | N1—C19—H19A | 109.5 |
C6—C5—H5 | 118.6 | N1—C19—H19B | 109.5 |
C5—C6—C1 | 119.4 (2) | H19A—C19—H19B | 109.5 |
C5—C6—C7 | 117.4 (2) | N1—C19—H19C | 109.5 |
C1—C6—C7 | 121.8 (2) | H19A—C19—H19C | 109.5 |
C5—C6—C7' | 111.6 (2) | H19B—C19—H19C | 109.5 |
C1—C6—C7' | 124.5 (2) | N1—C20—H20A | 109.5 |
C6—C7—C8 | 105.3 (3) | N1—C20—H20B | 109.5 |
C6—C7—H7A | 110.7 | H20A—C20—H20B | 109.5 |
C8—C7—H7A | 110.7 | N1—C20—H20C | 109.5 |
C6—C7—H7B | 110.7 | H20A—C20—H20C | 109.5 |
C8—C7—H7B | 110.7 | H20B—C20—H20C | 109.5 |
H7A—C7—H7B | 108.8 | O3—C21—O2 | 125.90 (17) |
C7—C8—C9 | 120.7 (3) | O3—C21—C22 | 119.30 (15) |
C7—C8—H8A | 107.2 | O2—C21—C22 | 114.76 (15) |
C9—C8—H8A | 107.2 | C27—C22—C23 | 117.80 (18) |
C7—C8—H8B | 107.2 | C27—C22—C21 | 118.17 (18) |
C9—C8—H8B | 107.2 | C23—C22—C21 | 124.02 (16) |
H8A—C8—H8B | 106.8 | C24—C23—C22 | 121.31 (18) |
C14—C9—C10 | 119.00 (19) | C24—C23—Cl1 | 117.88 (15) |
C14—C9—C8' | 122.4 (3) | C22—C23—Cl1 | 120.80 (13) |
C10—C9—C8' | 115.9 (3) | C25—C24—C23 | 119.4 (2) |
C14—C9—C8 | 126.6 (2) | C25—C24—H24 | 120.3 |
C10—C9—C8 | 112.5 (2) | C23—C24—H24 | 120.3 |
C8'—C7'—C6 | 119.9 (4) | C26—C25—C24 | 120.51 (19) |
C8'—C7'—H7'A | 107.4 | C26—C25—H25 | 119.7 |
C6—C7'—H7'A | 107.4 | C24—C25—H25 | 119.7 |
C8'—C7'—H7'B | 107.4 | C25—C26—C27 | 119.3 (2) |
C6—C7'—H7'B | 107.4 | C25—C26—H26 | 120.4 |
H7'A—C7'—H7'B | 106.9 | C27—C26—H26 | 120.4 |
C9—C8'—C7' | 100.8 (4) | C26—C27—C22 | 121.7 (2) |
C9—C8'—H8'A | 111.6 | C26—C27—H27 | 119.2 |
C7'—C8'—H8'A | 111.6 | C22—C27—H27 | 119.2 |
C9—C8'—H8'B | 111.6 | O3'—C21'—O2' | 125.6 (16) |
C7'—C8'—H8'B | 111.6 | O3'—C21'—C22' | 119.5 (15) |
H8'A—C8'—H8'B | 109.4 | O2'—C21'—C22' | 114.8 (14) |
C11—C10—C9 | 122.7 (2) | C27'—C22'—C23' | 116.5 (10) |
C11—C10—H10 | 118.7 | C27'—C22'—C21' | 118.5 (13) |
C9—C10—H10 | 118.7 | C23'—C22'—C21' | 124.8 (13) |
C12—C11—C10 | 118.7 (2) | C22'—C23'—C24' | 122.3 (11) |
C12—C11—H11 | 120.6 | C22'—C23'—Cl1' | 118.6 (11) |
C10—C11—H11 | 120.6 | C24'—C23'—Cl1' | 119.2 (11) |
C11—C12—C13 | 119.8 (2) | C25'—C24'—C23' | 118.9 (12) |
C11—C12—H12 | 120.1 | C25'—C24'—H24' | 120.6 |
C13—C12—H12 | 120.1 | C23'—C24'—H24' | 120.6 |
C12—C13—C14 | 122.15 (19) | C26'—C25'—C24' | 120.5 (12) |
C12—C13—H13 | 118.9 | C26'—C25'—H25' | 119.8 |
C14—C13—H13 | 118.9 | C24'—C25'—H25' | 119.8 |
C13—C14—C9 | 117.59 (17) | C25'—C26'—C27' | 118.7 (12) |
C13—C14—C15 | 118.19 (15) | C25'—C26'—H26' | 120.6 |
C9—C14—C15 | 124.22 (16) | C27'—C26'—H26' | 120.6 |
O1—C15—C16 | 107.76 (13) | C22'—C27'—C26' | 122.4 (13) |
O1—C15—C14 | 108.96 (13) | C22'—C27'—H27' | 118.8 |
C16—C15—C14 | 111.19 (13) | C26'—C27'—H27' | 118.8 |
O1—C15—C1 | 105.28 (13) | ||
C6—C1—C2—C3 | 1.7 (3) | C2—C1—C15—O1 | 5.5 (2) |
C15—C1—C2—C3 | −179.25 (17) | C6—C1—C15—O1 | −175.44 (17) |
C1—C2—C3—C4 | −1.0 (3) | C2—C1—C15—C16 | −111.70 (17) |
C2—C3—C4—C5 | −0.4 (3) | C6—C1—C15—C16 | 67.3 (2) |
C3—C4—C5—C6 | 1.2 (3) | C2—C1—C15—C14 | 123.10 (17) |
C4—C5—C6—C1 | −0.6 (3) | C6—C1—C15—C14 | −57.9 (2) |
C4—C5—C6—C7 | −167.3 (2) | O1—C15—C16—C17 | −59.35 (18) |
C4—C5—C6—C7' | 156.6 (3) | C14—C15—C16—C17 | −178.70 (14) |
C2—C1—C6—C5 | −0.9 (3) | C1—C15—C16—C17 | 56.41 (19) |
C15—C1—C6—C5 | −179.91 (18) | C15—C16—C17—C18 | −168.84 (14) |
C2—C1—C6—C7 | 165.2 (2) | C19—N1—C18—C17 | −53.2 (2) |
C15—C1—C6—C7 | −13.8 (3) | C20—N1—C18—C17 | −177.48 (16) |
C2—C1—C6—C7' | −154.9 (3) | C16—C17—C18—N1 | −64.1 (2) |
C15—C1—C6—C7' | 26.1 (3) | O3—C21—C22—C27 | −120.5 (3) |
C5—C6—C7—C8 | −115.1 (3) | O2—C21—C22—C27 | 57.2 (3) |
C1—C6—C7—C8 | 78.5 (3) | O3—C21—C22—C23 | 58.5 (3) |
C6—C7—C8—C9 | −64.1 (4) | O2—C21—C22—C23 | −123.9 (3) |
C7—C8—C9—C14 | 19.6 (5) | C27—C22—C23—C24 | −0.8 (3) |
C7—C8—C9—C10 | −176.6 (3) | C21—C22—C23—C24 | −179.78 (17) |
C5—C6—C7'—C8' | 173.2 (3) | C27—C22—C23—Cl1 | 178.91 (16) |
C1—C6—C7'—C8' | −31.1 (5) | C21—C22—C23—Cl1 | 0.0 (2) |
C14—C9—C8'—C7' | −83.4 (4) | C22—C23—C24—C25 | 1.6 (3) |
C10—C9—C8'—C7' | 115.6 (3) | Cl1—C23—C24—C25 | −178.16 (15) |
C6—C7'—C8'—C9 | 69.8 (5) | C23—C24—C25—C26 | −0.5 (3) |
C14—C9—C10—C11 | 0.7 (4) | C24—C25—C26—C27 | −1.2 (3) |
C8'—C9—C10—C11 | 162.3 (3) | C25—C26—C27—C22 | 2.0 (4) |
C8—C9—C10—C11 | −164.4 (3) | C23—C22—C27—C26 | −1.0 (3) |
C9—C10—C11—C12 | 0.1 (4) | C21—C22—C27—C26 | 178.0 (2) |
C10—C11—C12—C13 | −0.8 (3) | O3'—C21'—C22'—C27' | 55 (6) |
C11—C12—C13—C14 | 0.9 (3) | O2'—C21'—C22'—C27' | −127 (7) |
C12—C13—C14—C9 | −0.2 (3) | O3'—C21'—C22'—C23' | −130 (6) |
C12—C13—C14—C15 | 179.15 (18) | O2'—C21'—C22'—C23' | 49 (7) |
C10—C9—C14—C13 | −0.6 (3) | C27'—C22'—C23'—C24' | −5 (3) |
C8'—C9—C14—C13 | −161.0 (3) | C21'—C22'—C23'—C24' | 180.00 (17) |
C8—C9—C14—C13 | 162.2 (2) | C27'—C22'—C23'—Cl1' | 175 (2) |
C10—C9—C14—C15 | −179.9 (2) | C21'—C22'—C23'—Cl1' | 0.0 (2) |
C8'—C9—C14—C15 | 19.8 (4) | C22'—C23'—C24'—C25' | 0.0 (4) |
C8—C9—C14—C15 | −17.1 (3) | Cl1'—C23'—C24'—C25' | 180.0 (2) |
C13—C14—C15—O1 | −9.3 (2) | C23'—C24'—C25'—C26' | 0.0 (4) |
C9—C14—C15—O1 | 169.98 (17) | C24'—C25'—C26'—C27' | 5 (3) |
C13—C14—C15—C16 | 109.36 (17) | C23'—C22'—C27'—C26' | 10 (5) |
C9—C14—C15—C16 | −71.4 (2) | C21'—C22'—C27'—C26' | −174 (3) |
C13—C14—C15—C1 | −124.55 (16) | C25'—C26'—C27'—C22' | −10 (5) |
C9—C14—C15—C1 | 54.7 (2) |
D—H···A | D—H | H···A | D···A | D—H···A |
O1—H1O···O3i | 0.86 (2) | 1.91 (2) | 2.724 (3) | 159 (2) |
O1—H1O···O3′i | 0.86 (2) | 2.02 (8) | 2.81 (8) | 153 (3) |
N1—H1N···O2 | 1.00 (2) | 1.61 (2) | 2.605 (2) | 171.5 (19) |
N1—H1N···O2′ | 1.00 (2) | 1.73 (4) | 2.73 (4) | 178 (4) |
N1—H1N···O3′ | 1.00 (2) | 2.58 (5) | 3.23 (5) | 122.4 (16) |
C19—H19B···O3i | 0.98 | 2.63 | 3.595 (4) | 167 |
C19—H19B···O3′i | 0.98 | 2.52 | 3.47 (9) | 162 |
C20—H20C···O2ii | 0.98 | 2.46 | 3.426 (4) | 169 |
C20—H20C···O2′ii | 0.98 | 2.57 | 3.54 (10) | 169 |
Symmetry codes: (i) x+1, y, z; (ii) −x+1, −y+1, −z+1. |
C20H26NO+·C5H3O2S−·H2O | Dx = 1.308 Mg m−3 |
Mr = 441.57 | Mo Kα radiation, λ = 0.71073 Å |
Orthorhombic, P212121 | Cell parameters from 9921 reflections |
a = 6.1659 (5) Å | θ = 2.7–27.5° |
b = 13.1299 (12) Å | µ = 0.18 mm−1 |
c = 27.698 (2) Å | T = 90 K |
V = 2242.3 (3) Å3 | Tablet, colourless |
Z = 4 | 0.27 × 0.13 × 0.04 mm |
F(000) = 944 |
Bruker D8 Venture dual source diffractometer | 5133 independent reflections |
Radiation source: microsource | 4772 reflections with I > 2σ(I) |
Detector resolution: 7.41 pixels mm-1 | Rint = 0.042 |
φ and ω scans | θmax = 27.5°, θmin = 2.1° |
Absorption correction: multi-scan (SADABS; Krause et al., 2015) | h = −8→7 |
Tmin = 0.852, Tmax = 0.959 | k = −17→17 |
43123 measured reflections | l = −36→36 |
Refinement on F2 | Secondary atom site location: difference Fourier map |
Least-squares matrix: full | Hydrogen site location: mixed |
R[F2 > 2σ(F2)] = 0.028 | H atoms treated by a mixture of independent and constrained refinement |
wR(F2) = 0.062 | w = 1/[σ2(Fo2) + (0.0234P)2 + 0.459P] where P = (Fo2 + 2Fc2)/3 |
S = 1.06 | (Δ/σ)max = 0.001 |
5133 reflections | Δρmax = 0.19 e Å−3 |
315 parameters | Δρmin = −0.19 e Å−3 |
10 restraints | Absolute structure: Twinned by inversion. |
Primary atom site location: structure-invariant direct methods | Absolute structure parameter: 0.30 (7) |
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 2-component inversion twin. |
x | y | z | Uiso*/Ueq | Occ. (<1) | |
O1 | 0.0126 (2) | 0.58778 (10) | 0.63942 (4) | 0.0166 (3) | |
H1O | 0.004 (4) | 0.6031 (17) | 0.6681 (8) | 0.029 (6)* | |
N1 | 0.4459 (3) | 0.42400 (12) | 0.73556 (5) | 0.0181 (3) | |
H1N | 0.414 (3) | 0.4876 (19) | 0.7500 (7) | 0.028 (6)* | |
C1 | 0.1911 (3) | 0.74788 (14) | 0.61758 (6) | 0.0145 (4) | |
C2 | 0.0149 (3) | 0.79475 (14) | 0.64074 (6) | 0.0181 (4) | |
H2 | −0.091994 | 0.753200 | 0.655643 | 0.022* | |
C3 | −0.0081 (3) | 0.89955 (15) | 0.64259 (6) | 0.0215 (4) | |
H3 | −0.131587 | 0.928973 | 0.657624 | 0.026* | |
C4 | 0.1494 (3) | 0.96115 (15) | 0.62245 (6) | 0.0219 (4) | |
H4 | 0.138751 | 1.033189 | 0.624603 | 0.026* | |
C5 | 0.3224 (3) | 0.91624 (15) | 0.59916 (6) | 0.0199 (4) | |
H5 | 0.430753 | 0.958886 | 0.585524 | 0.024* | |
C6 | 0.3454 (3) | 0.81054 (14) | 0.59471 (6) | 0.0166 (4) | |
C7 | 0.5327 (3) | 0.77912 (15) | 0.56226 (6) | 0.0193 (4) | |
H7A | 0.661250 | 0.818537 | 0.572726 | 0.023* | |
H7B | 0.496813 | 0.802372 | 0.529210 | 0.023* | |
C8 | 0.6028 (3) | 0.66828 (15) | 0.55839 (6) | 0.0181 (4) | |
H8A | 0.723454 | 0.663333 | 0.534937 | 0.022* | |
H8B | 0.658328 | 0.645680 | 0.590169 | 0.022* | |
C9 | 0.4243 (3) | 0.59754 (14) | 0.54289 (6) | 0.0171 (4) | |
C10 | 0.4468 (3) | 0.54576 (15) | 0.49902 (6) | 0.0212 (4) | |
H10 | 0.573560 | 0.556479 | 0.480189 | 0.025* | |
C11 | 0.2895 (3) | 0.47934 (15) | 0.48231 (6) | 0.0229 (4) | |
H11 | 0.308467 | 0.444647 | 0.452511 | 0.027* | |
C12 | 0.1043 (3) | 0.46409 (15) | 0.50952 (6) | 0.0204 (4) | |
H12 | −0.005380 | 0.418995 | 0.498405 | 0.025* | |
C13 | 0.0789 (3) | 0.51493 (14) | 0.55318 (6) | 0.0170 (4) | |
H13 | −0.048939 | 0.504153 | 0.571617 | 0.020* | |
C14 | 0.2371 (3) | 0.58134 (14) | 0.57047 (6) | 0.0148 (4) | |
C15 | 0.2083 (3) | 0.63035 (14) | 0.62048 (6) | 0.0141 (3) | |
C16 | 0.3924 (3) | 0.59993 (14) | 0.65624 (6) | 0.0153 (4) | |
H16A | 0.518832 | 0.645177 | 0.651203 | 0.018* | |
H16B | 0.340931 | 0.609543 | 0.689787 | 0.018* | |
C17 | 0.4623 (3) | 0.48945 (14) | 0.64929 (6) | 0.0176 (4) | |
H17A | 0.331425 | 0.448170 | 0.642543 | 0.021* | |
H17B | 0.556508 | 0.485789 | 0.620391 | 0.021* | |
C18 | 0.5823 (3) | 0.44131 (15) | 0.69130 (6) | 0.0177 (4) | |
H18A | 0.642223 | 0.375076 | 0.680643 | 0.021* | |
H18B | 0.705992 | 0.485638 | 0.700092 | 0.021* | |
C19 | 0.2363 (3) | 0.37253 (17) | 0.72515 (7) | 0.0252 (4) | |
H19A | 0.143055 | 0.418364 | 0.706473 | 0.038* | |
H19B | 0.164428 | 0.354959 | 0.755588 | 0.038* | |
H19C | 0.263284 | 0.310346 | 0.706529 | 0.038* | |
C20 | 0.5736 (4) | 0.36513 (18) | 0.77156 (7) | 0.0337 (5) | |
H20A | 0.489898 | 0.358568 | 0.801467 | 0.051* | |
H20B | 0.709976 | 0.400774 | 0.778277 | 0.051* | |
H20C | 0.605215 | 0.297237 | 0.758641 | 0.051* | |
O2 | 0.3116 (2) | 0.58314 (11) | 0.78720 (5) | 0.0226 (3) | |
O3 | 0.6468 (2) | 0.63027 (12) | 0.80797 (5) | 0.0242 (3) | |
C21 | 0.4471 (3) | 0.62759 (14) | 0.81440 (6) | 0.0170 (4) | |
C22 | 0.3557 (6) | 0.6824 (7) | 0.8572 (3) | 0.0153 (5) | 0.899 (3) |
S1 | 0.53403 (11) | 0.72881 (9) | 0.89993 (2) | 0.01932 (17) | 0.899 (3) |
C23 | 0.3261 (4) | 0.7847 (2) | 0.93133 (10) | 0.0216 (6) | 0.899 (3) |
H23 | 0.345230 | 0.822272 | 0.960340 | 0.026* | 0.899 (3) |
C24 | 0.1299 (4) | 0.7691 (4) | 0.90976 (12) | 0.0214 (6) | 0.899 (3) |
H24 | −0.003283 | 0.795199 | 0.921778 | 0.026* | 0.899 (3) |
C25 | 0.1477 (15) | 0.7099 (11) | 0.8678 (4) | 0.0232 (11) | 0.899 (3) |
H25 | 0.026638 | 0.690741 | 0.848600 | 0.028* | 0.899 (3) |
C22' | 0.388 (5) | 0.678 (7) | 0.857 (2) | 0.0153 (5) | 0.101 (3) |
S1' | 0.118 (4) | 0.707 (3) | 0.8642 (10) | 0.0232 (11) | 0.101 (3) |
C23' | 0.171 (4) | 0.770 (4) | 0.9170 (13) | 0.0214 (6) | 0.101 (3) |
H23' | 0.062801 | 0.799212 | 0.937142 | 0.026* | 0.101 (3) |
C24' | 0.387 (4) | 0.775 (3) | 0.9266 (10) | 0.0216 (6) | 0.101 (3) |
H24' | 0.447583 | 0.807427 | 0.954137 | 0.026* | 0.101 (3) |
C25' | 0.511 (4) | 0.726 (4) | 0.8910 (12) | 0.01932 (17) | 0.101 (3) |
H25' | 0.664620 | 0.725448 | 0.890806 | 0.023* | 0.101 (3) |
O1W | 0.9441 (3) | 0.62270 (13) | 0.73651 (5) | 0.0304 (4) | |
H1W | 0.834 (5) | 0.619 (2) | 0.7559 (10) | 0.058 (9)* | |
H2W | 1.053 (5) | 0.614 (2) | 0.7533 (11) | 0.056 (9)* |
U11 | U22 | U33 | U12 | U13 | U23 | |
O1 | 0.0163 (6) | 0.0188 (7) | 0.0148 (6) | −0.0031 (5) | 0.0036 (5) | −0.0023 (5) |
N1 | 0.0268 (8) | 0.0129 (8) | 0.0147 (7) | 0.0034 (7) | −0.0032 (6) | −0.0009 (6) |
C1 | 0.0163 (8) | 0.0145 (10) | 0.0128 (7) | 0.0022 (7) | −0.0036 (6) | −0.0008 (6) |
C2 | 0.0196 (9) | 0.0187 (10) | 0.0158 (8) | 0.0019 (7) | −0.0009 (7) | −0.0015 (6) |
C3 | 0.025 (1) | 0.0214 (10) | 0.0180 (8) | 0.0085 (8) | −0.0037 (7) | −0.0040 (7) |
C4 | 0.0352 (11) | 0.0126 (10) | 0.0178 (8) | 0.0028 (8) | −0.0073 (8) | −0.0015 (7) |
C5 | 0.0262 (9) | 0.0163 (10) | 0.0172 (8) | −0.0039 (8) | −0.0056 (8) | 0.0017 (7) |
C6 | 0.0189 (9) | 0.0162 (9) | 0.0147 (8) | 0.0010 (7) | −0.0055 (7) | 0.0001 (7) |
C7 | 0.0175 (8) | 0.0204 (10) | 0.0198 (8) | −0.0030 (8) | −0.0001 (7) | 0.0037 (7) |
C8 | 0.0163 (9) | 0.0211 (11) | 0.0169 (8) | 0.0004 (7) | 0.0032 (7) | 0.0019 (7) |
C9 | 0.0192 (9) | 0.0164 (10) | 0.0158 (8) | 0.0041 (7) | 0.0012 (7) | 0.0018 (7) |
C10 | 0.0265 (10) | 0.022 (1) | 0.0150 (8) | 0.0043 (9) | 0.0038 (8) | 0.0017 (7) |
C11 | 0.0358 (11) | 0.0184 (10) | 0.0145 (8) | 0.0037 (8) | 0.0014 (8) | −0.0030 (7) |
C12 | 0.0278 (10) | 0.0157 (10) | 0.0178 (8) | −0.0024 (8) | −0.0036 (7) | −0.0003 (7) |
C13 | 0.0205 (9) | 0.0142 (9) | 0.0164 (8) | 0.0007 (7) | 0.0011 (7) | 0.0018 (7) |
C14 | 0.0179 (8) | 0.0125 (9) | 0.0140 (8) | 0.0045 (7) | 0.0007 (7) | 0.0007 (6) |
C15 | 0.0141 (8) | 0.0148 (9) | 0.0135 (7) | −0.0007 (7) | 0.0012 (6) | 0.0002 (7) |
C16 | 0.0167 (8) | 0.0138 (9) | 0.0152 (8) | −0.0003 (7) | 0.0009 (6) | 0.0005 (7) |
C17 | 0.0228 (9) | 0.0156 (9) | 0.0142 (7) | 0.0028 (8) | 0.0017 (7) | −0.0004 (7) |
C18 | 0.0171 (9) | 0.0152 (9) | 0.0208 (8) | 0.0029 (7) | −0.0006 (7) | −0.0009 (7) |
C19 | 0.0296 (11) | 0.0199 (11) | 0.0262 (9) | −0.0055 (9) | 0.0056 (8) | −0.0005 (8) |
C20 | 0.0543 (15) | 0.0287 (12) | 0.0182 (9) | 0.0143 (11) | −0.0105 (10) | 0.0025 (8) |
O2 | 0.0240 (7) | 0.0234 (8) | 0.0206 (6) | 0.0040 (6) | −0.0017 (5) | −0.0063 (6) |
O3 | 0.0198 (7) | 0.0296 (8) | 0.0230 (7) | 0.0025 (6) | 0.0058 (5) | 0.0011 (6) |
C21 | 0.0212 (9) | 0.0131 (9) | 0.0167 (8) | 0.0030 (8) | 0.0032 (7) | 0.0034 (7) |
C22 | 0.0175 (14) | 0.0110 (14) | 0.0175 (8) | −0.0007 (18) | 0.0022 (14) | 0.0020 (7) |
S1 | 0.0196 (3) | 0.0193 (3) | 0.0191 (4) | −0.0007 (3) | −0.0014 (2) | −0.0019 (3) |
C23 | 0.0241 (15) | 0.0193 (13) | 0.0213 (10) | −0.0003 (12) | 0.0057 (11) | −0.0066 (8) |
C24 | 0.0202 (13) | 0.019 (1) | 0.0252 (15) | 0.0006 (14) | 0.0037 (10) | −0.0035 (12) |
C25 | 0.028 (3) | 0.0164 (12) | 0.0247 (19) | −0.002 (2) | 0.0019 (17) | −0.0015 (12) |
C22' | 0.0175 (14) | 0.0110 (14) | 0.0175 (8) | −0.0007 (18) | 0.0022 (14) | 0.0020 (7) |
S1' | 0.028 (3) | 0.0164 (12) | 0.0247 (19) | −0.002 (2) | 0.0019 (17) | −0.0015 (12) |
C23' | 0.0202 (13) | 0.019 (1) | 0.0252 (15) | 0.0006 (14) | 0.0037 (10) | −0.0035 (12) |
C24' | 0.0241 (15) | 0.0193 (13) | 0.0213 (10) | −0.0003 (12) | 0.0057 (11) | −0.0066 (8) |
C25' | 0.0196 (3) | 0.0193 (3) | 0.0191 (4) | −0.0007 (3) | −0.0014 (2) | −0.0019 (3) |
O1W | 0.0197 (7) | 0.0532 (11) | 0.0182 (6) | 0.0024 (8) | 0.0029 (6) | −0.0039 (7) |
O1—C15 | 1.430 (2) | C16—C17 | 1.525 (2) |
O1—H1O | 0.82 (2) | C16—H16A | 0.9900 |
N1—C19 | 1.487 (3) | C16—H16B | 0.9900 |
N1—C20 | 1.487 (2) | C17—C18 | 1.517 (2) |
N1—C18 | 1.504 (2) | C17—H17A | 0.9900 |
N1—H1N | 0.95 (2) | C17—H17B | 0.9900 |
C1—C2 | 1.404 (2) | C18—H18A | 0.9900 |
C1—C6 | 1.408 (3) | C18—H18B | 0.9900 |
C1—C15 | 1.549 (2) | C19—H19A | 0.9800 |
C2—C3 | 1.384 (3) | C19—H19B | 0.9800 |
C2—H2 | 0.9500 | C19—H19C | 0.9800 |
C3—C4 | 1.382 (3) | C20—H20A | 0.9800 |
C3—H3 | 0.9500 | C20—H20B | 0.9800 |
C4—C5 | 1.379 (3) | C20—H20C | 0.9800 |
C4—H4 | 0.9500 | O2—C21 | 1.267 (2) |
C5—C6 | 1.401 (3) | O3—C21 | 1.245 (2) |
C5—H5 | 0.9500 | C21—C22' | 1.40 (3) |
C6—C7 | 1.521 (3) | C21—C22 | 1.496 (3) |
C7—C8 | 1.522 (3) | C22—C25 | 1.364 (9) |
C7—H7A | 0.9900 | C22—S1 | 1.727 (3) |
C7—H7B | 0.9900 | S1—C23 | 1.714 (2) |
C8—C9 | 1.502 (3) | C23—C24 | 1.365 (3) |
C8—H8A | 0.9900 | C23—H23 | 0.9500 |
C8—H8B | 0.9900 | C24—C25 | 1.403 (10) |
C9—C10 | 1.399 (2) | C24—H24 | 0.9500 |
C9—C14 | 1.401 (2) | C25—H25 | 0.9500 |
C10—C11 | 1.384 (3) | C22'—C25' | 1.367 (16) |
C10—H10 | 0.9500 | C22'—S1' | 1.720 (14) |
C11—C12 | 1.383 (3) | S1'—C23' | 1.716 (13) |
C11—H11 | 0.9500 | C23'—C24' | 1.359 (13) |
C12—C13 | 1.390 (2) | C23'—H23' | 0.9500 |
C12—H12 | 0.9500 | C24'—C25' | 1.402 (16) |
C13—C14 | 1.393 (3) | C24'—H24' | 0.9500 |
C13—H13 | 0.9500 | C25'—H25' | 0.9500 |
C14—C15 | 1.538 (2) | O1W—H1W | 0.87 (3) |
C15—C16 | 1.559 (2) | O1W—H2W | 0.83 (3) |
C15—O1—H1O | 108.3 (17) | C17—C16—H16A | 109.3 |
C19—N1—C20 | 110.74 (17) | C15—C16—H16A | 109.3 |
C19—N1—C18 | 113.36 (14) | C17—C16—H16B | 109.3 |
C20—N1—C18 | 109.20 (15) | C15—C16—H16B | 109.3 |
C19—N1—H1N | 107.6 (13) | H16A—C16—H16B | 107.9 |
C20—N1—H1N | 106.5 (13) | C18—C17—C16 | 115.93 (14) |
C18—N1—H1N | 109.1 (13) | C18—C17—H17A | 108.3 |
C2—C1—C6 | 118.18 (17) | C16—C17—H17A | 108.3 |
C2—C1—C15 | 117.77 (16) | C18—C17—H17B | 108.3 |
C6—C1—C15 | 124.00 (15) | C16—C17—H17B | 108.3 |
C3—C2—C1 | 122.14 (17) | H17A—C17—H17B | 107.4 |
C3—C2—H2 | 118.9 | N1—C18—C17 | 114.57 (15) |
C1—C2—H2 | 118.9 | N1—C18—H18A | 108.6 |
C4—C3—C2 | 119.67 (18) | C17—C18—H18A | 108.6 |
C4—C3—H3 | 120.2 | N1—C18—H18B | 108.6 |
C2—C3—H3 | 120.2 | C17—C18—H18B | 108.6 |
C5—C4—C3 | 118.84 (19) | H18A—C18—H18B | 107.6 |
C5—C4—H4 | 120.6 | N1—C19—H19A | 109.5 |
C3—C4—H4 | 120.6 | N1—C19—H19B | 109.5 |
C4—C5—C6 | 122.90 (18) | H19A—C19—H19B | 109.5 |
C4—C5—H5 | 118.5 | N1—C19—H19C | 109.5 |
C6—C5—H5 | 118.5 | H19A—C19—H19C | 109.5 |
C5—C6—C1 | 118.10 (17) | H19B—C19—H19C | 109.5 |
C5—C6—C7 | 113.43 (16) | N1—C20—H20A | 109.5 |
C1—C6—C7 | 128.36 (17) | N1—C20—H20B | 109.5 |
C6—C7—C8 | 121.10 (15) | H20A—C20—H20B | 109.5 |
C6—C7—H7A | 107.1 | N1—C20—H20C | 109.5 |
C8—C7—H7A | 107.1 | H20A—C20—H20C | 109.5 |
C6—C7—H7B | 107.1 | H20B—C20—H20C | 109.5 |
C8—C7—H7B | 107.1 | O3—C21—O2 | 125.44 (17) |
H7A—C7—H7B | 106.8 | O3—C21—C22' | 111.5 (15) |
C9—C8—C7 | 113.79 (15) | O2—C21—C22' | 123.0 (16) |
C9—C8—H8A | 108.8 | O3—C21—C22 | 118.2 (2) |
C7—C8—H8A | 108.8 | O2—C21—C22 | 116.4 (2) |
C9—C8—H8B | 108.8 | C25—C22—C21 | 130.7 (5) |
C7—C8—H8B | 108.8 | C25—C22—S1 | 111.0 (4) |
H8A—C8—H8B | 107.7 | C21—C22—S1 | 118.2 (2) |
C10—C9—C14 | 118.78 (18) | C23—S1—C22 | 91.31 (12) |
C10—C9—C8 | 118.43 (17) | C24—C23—S1 | 112.10 (19) |
C14—C9—C8 | 122.79 (15) | C24—C23—H23 | 123.9 |
C11—C10—C9 | 121.80 (18) | S1—C23—H23 | 123.9 |
C11—C10—H10 | 119.1 | C23—C24—C25 | 112.1 (4) |
C9—C10—H10 | 119.1 | C23—C24—H24 | 123.9 |
C12—C11—C10 | 119.20 (17) | C25—C24—H24 | 123.9 |
C12—C11—H11 | 120.4 | C22—C25—C24 | 113.5 (5) |
C10—C11—H11 | 120.4 | C22—C25—H25 | 123.3 |
C11—C12—C13 | 119.83 (18) | C24—C25—H25 | 123.3 |
C11—C12—H12 | 120.1 | C25'—C22'—C21 | 131 (3) |
C13—C12—H12 | 120.1 | C25'—C22'—S1' | 110.6 (12) |
C12—C13—C14 | 121.39 (17) | C21—C22'—S1' | 117 (2) |
C12—C13—H13 | 119.3 | C23'—S1'—C22' | 91.3 (9) |
C14—C13—H13 | 119.3 | C24'—C23'—S1' | 112.1 (13) |
C13—C14—C9 | 118.99 (15) | C24'—C23'—H23' | 123.9 |
C13—C14—C15 | 119.39 (15) | S1'—C23'—H23' | 123.9 |
C9—C14—C15 | 121.54 (16) | C23'—C24'—C25' | 111.9 (14) |
O1—C15—C14 | 105.33 (14) | C23'—C24'—H24' | 124.0 |
O1—C15—C1 | 110.54 (14) | C25'—C24'—H24' | 124.0 |
C14—C15—C1 | 112.21 (14) | C22'—C25'—C24' | 113.5 (15) |
O1—C15—C16 | 106.35 (13) | C22'—C25'—H25' | 123.2 |
C14—C15—C16 | 112.40 (14) | C24'—C25'—H25' | 123.2 |
C1—C15—C16 | 109.76 (14) | H1W—O1W—H2W | 106 (2) |
C17—C16—C15 | 111.67 (14) | ||
C6—C1—C2—C3 | −1.5 (2) | C6—C1—C15—O1 | −171.35 (15) |
C15—C1—C2—C3 | 176.23 (16) | C2—C1—C15—C14 | 128.37 (16) |
C1—C2—C3—C4 | −2.1 (3) | C6—C1—C15—C14 | −54.1 (2) |
C2—C3—C4—C5 | 2.6 (3) | C2—C1—C15—C16 | −105.89 (17) |
C3—C4—C5—C6 | 0.4 (3) | C6—C1—C15—C16 | 71.6 (2) |
C4—C5—C6—C1 | −3.8 (3) | O1—C15—C16—C17 | 77.64 (17) |
C4—C5—C6—C7 | 172.66 (16) | C14—C15—C16—C17 | −37.1 (2) |
C2—C1—C6—C5 | 4.2 (2) | C1—C15—C16—C17 | −162.76 (14) |
C15—C1—C6—C5 | −173.28 (15) | C15—C16—C17—C18 | −160.52 (15) |
C2—C1—C6—C7 | −171.65 (16) | C19—N1—C18—C17 | 49.0 (2) |
C15—C1—C6—C7 | 10.8 (3) | C20—N1—C18—C17 | 172.95 (16) |
C5—C6—C7—C8 | 171.58 (16) | C16—C17—C18—N1 | 68.6 (2) |
C1—C6—C7—C8 | −12.4 (3) | O3—C21—C22—C25 | 164.9 (11) |
C6—C7—C8—C9 | 56.9 (2) | O2—C21—C22—C25 | −14.1 (14) |
C7—C8—C9—C10 | 116.72 (18) | O3—C21—C22—S1 | −9.9 (9) |
C7—C8—C9—C14 | −63.3 (2) | O2—C21—C22—S1 | 171.0 (5) |
C14—C9—C10—C11 | 0.0 (3) | C25—C22—S1—C23 | −0.2 (9) |
C8—C9—C10—C11 | 180.00 (18) | C21—C22—S1—C23 | 175.7 (7) |
C9—C10—C11—C12 | 0.4 (3) | C22—S1—C23—C24 | −0.4 (5) |
C10—C11—C12—C13 | −0.3 (3) | S1—C23—C24—C25 | 0.9 (8) |
C11—C12—C13—C14 | −0.1 (3) | C21—C22—C25—C24 | −174.5 (9) |
C12—C13—C14—C9 | 0.6 (3) | S1—C22—C25—C24 | 0.7 (14) |
C12—C13—C14—C15 | −176.05 (16) | C23—C24—C25—C22 | −1.0 (13) |
C10—C9—C14—C13 | −0.5 (3) | O3—C21—C22'—C25' | −2 (12) |
C8—C9—C14—C13 | 179.54 (17) | O2—C21—C22'—C25' | 177 (8) |
C10—C9—C14—C15 | 176.04 (16) | O3—C21—C22'—S1' | 165 (5) |
C8—C9—C14—C15 | −3.9 (3) | O2—C21—C22'—S1' | −16 (10) |
C13—C14—C15—O1 | 2.8 (2) | C25'—C22'—S1'—C23' | −6 (7) |
C9—C14—C15—O1 | −173.68 (15) | C21—C22'—S1'—C23' | −176 (7) |
C13—C14—C15—C1 | −117.49 (18) | C22'—S1'—C23'—C24' | 4 (6) |
C9—C14—C15—C1 | 66.0 (2) | S1'—C23'—C24'—C25' | 0 (6) |
C13—C14—C15—C16 | 118.22 (18) | C21—C22'—C25'—C24' | 175 (8) |
C9—C14—C15—C16 | −58.3 (2) | S1'—C22'—C25'—C24' | 7 (9) |
C2—C1—C15—O1 | 11.1 (2) | C23'—C24'—C25'—C22' | −5 (8) |
D—H···A | D—H | H···A | D···A | D—H···A |
O1—H1O···O1Wi | 0.82 (2) | 1.95 (2) | 2.7607 (18) | 170 (2) |
N1—H1N···O2 | 0.95 (2) | 1.74 (2) | 2.664 (2) | 164 (2) |
C18—H18A···S1′bii | 0.99 | 2.93 | 3.90 (3) | 167 |
C18—H18B···O1W | 0.99 | 2.53 | 3.495 (3) | 164 |
C19—H19C···O3ii | 0.98 | 2.46 | 3.388 (3) | 158 |
C25′b—H25′b···S1′biii | 0.95 | 2.90 | 3.82 (3) | 165 |
O1W—H1W···O3 | 0.87 (3) | 1.85 (3) | 2.6993 (19) | 165 (3) |
O1W—H2W···O2iii | 0.83 (3) | 1.89 (3) | 2.716 (2) | 174 (3) |
Symmetry codes: (i) x−1, y, z; (ii) −x+1, y−1/2, −z+3/2; (iii) x+1, y, z. |
atoms | torsion angle | geometry |
I | ||
C6—C7—C8—C9 | -50.9 (2) | gauche |
C15—C16—C17—C18 | 172.16 (14) | anti |
C16—C17—C18—N1 | -71.7 (2) | gauche |
II | ||
C6A—C7A—C8A—C9A | 18.7 (12) | syn |
C6A—C7A'—C8A'—C9A | -38 (3) | gauche |
C6B—C7B—C8B—C9B | 17.7 (9) | syn |
C6B—C7B'—C8B'—C9B | -35 (3) | gauche |
C15A—C16A—C17A—C18A | -172.24 (19) | anti |
C16A—C17A—C18A—N1A | 162.68 (19) | anti |
C15B—C16B—C17B—C18B | -156.6 (2) | anti |
C16B—C17B—C18B—N1B | 167.64 (19) | anti |
III | ||
C6—C7—C8—C9 | -64.1 (4) | gauche |
C6—C7'—C8'—C9 | 69.8 (5) | gauche |
C15—C16—C17—C18 | -168.84 (14) | anti |
C16—C17—C18—N1 | -64.1 (2) | gauche |
IV | ||
C6—C7—C8—C9 | 56.9 (2) | gauche |
C15—C16—C17—C18 | -160.52 (15) | anti |
C16—C17—C18—N1 | 68.6 (2) | gauche |
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.
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