organic compounds
4-tert-Butylpyridinium chloride–4,4′-(propane-2,2-diyl)bis(2,6-dimethylphenol)–toluene (2/2/1)
aChemistry, Institute of Natural and Mathematical Sciences, Massey University at Albany, PO Box 102904, North Shore Mail Centre, Auckland, New Zealand
*Correspondence e-mail: a.j.nielson@massey.ac.nz
In the title solvated salt, C9H14N+·Cl−·C19H24O2·0.5C7H7, two molecules of 4,4′-(propane-2,2-diyl)bis(2,6-dimethylphenol) are linked via O—H⋯Cl hydrogen bonds to two chloride ions, each of which is also engaged in N—H⋯Cl hydrogen bonding to a 4-tert-butylpyridinium cation, giving a cyclic hydrogen-bonded entity centred at 1/2, 1/2, 1/2. The toluene solvent molecule resides in the lattice and resides on an inversion centre; the disorder of the methyl group requires it to have a site-occupancy factor of 0.5. No crystal packing channels are observed.
CCDC reference: 989768
Related literature
For general background to hydrogen-bond structural information, see: Hamilton & Ibers (1968). For hydrogen bonding between and nitrogen bases, see: Coupar et al. (1997); Steiner et al. (2000). For hydrogen bonding in phenol molecules, see: Prout et al. (1988); Ziemer & Surygina, (2000). For the structure of a related bis-phenol molecule, see: Okada (1996). For hydrogen bonds between pyridinium hydrochloride and OH-containing molecules, see: Sykora & Cioffi (2007); Hossain et al. (1988). For structural data pertaining to pyridinium hydrohalides, see: Faber et al. (1999); Hensen et al. (1988); Mootz & Hocken (1989); van de Streek et al. (2010).
Experimental
Crystal data
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Data collection: SMART (Siemens, 1995); cell SAINT (Siemens, 1995); data reduction: SAINT; program(s) used to solve structure: SHELXS97 (Sheldrick, 2008); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008); molecular graphics: ORTEP-3 for Windows (Farrugia, 2012); software used to prepare material for publication: SHELXL97.
Supporting information
CCDC reference: 989768
10.1107/S1600536814004942/gg2132sup1.cif
contains datablocks I, global. DOI:Structure factors: contains datablock I. DOI: 10.1107/S1600536814004942/gg2132Isup2.hkl
The title compound crystallized from toluene as very thin colourless plates from the reaction between TiCl4 and 4,4'-(propane-2,2-diyl)bis(2,6-dimethylphenol) in the presence of 4-tert-butylpyridine.
Crystal data, data collection and structure
details are summarized in Table 1. All H atoms (except H1 and H2) were placed in calculated positions and in the allowed to ride on the C atoms to which they were attached. H1 and H2 were located from a difference map and their positions were then allowed to ride on their oxygen atoms. All H atoms were assigned fixed isotropic thermal parameters. Disorder was associated with tert-butyl substituent on the pyridinium ion and two alternative positions were found for this group with site occupancy factors of 0.62 and 0.38. Both were refined as a rigid group. A half-weighted molecule of toluene disordered across a centre of symmetry was identified in the The numbering system used for the diphenol and pyridinium moieties is indicated in figure 1, where the linking of the moities via the chloride ion is shown.As part of a study into the reactions of TiCl4 with various
in the presence of pyridines, crystals of the title compound were isolated from a toluene solution. X-ray structural analysis revealed two molecules of (CH3)2C(C6H2Me2OH)2 linked together by hydrogen bonds to 2 chloride ions which in turn are further linked to two 4-tert-butyl pyridinium-H ions about a centre of symmetry to form a ring of atoms (Figure 1). No Ti atom was present. Distances of 3.118 (2) and 3.079 (2) Å were observed for Cl···O1 and Cl···O2 respectively. The H contact distances and O–H···Cl angles observed were 2.27 (4) Å, 157 (3) ° and 2.30 (3) Å, 153 (3) ° for H1 and H2, respectively. The Cl is also H-bound to H20 of the pyridinium-H ion with Cl···N20 and Cl···H20 approaches of 3.035 (3) and 1.98 (4) Å respectively. The angle N20–H20···Cl is 173 (3) °. These distances are typical of such H-bonded distances as described elsewhere (Hamilton & Ibers, 1968). H-bonds between N bases and phenolic moieties are not uncommon (Coupar et al. 1997) and the interaction is often strong (Steiner et al. 2000). However a Cl ion linking a phenol and an ammine hydrocloride as occurs in the title compound has apparently not been observed before. A single link between pyridinium hydrochloride and the OH hydrogen of triphenylmethanol has been observed (Sykora & Cioffi, 2007) as has a similar link with the OH group of 1,1,3,3-tetraphenyl-1,3-disiloxanediol (Hossain et al. 1988).The N20 to Cl separation for the 4-tert-butylpyridinium hydrochloride in the present compound [3.035 (3) Å] compares with that found for 4-methylpyridinium hydrochloride itself at 2.999 (2) Å, 2.981 (4) Å in 3-methylpyridinium hydrochloride and 3.162 (2) Å in 4-methylpyridinium hydrobromide (Faber et al. 1999). Taking into account the imprecise positioning of hydrogen atoms in X-ray crystal structures, in the latter three compounds the N—H···Cl bond angles are 180 °, 177 (5)° [and 165 (5) °] and 173 (3) ° whereas in the present compound this angle is 173 (3) °. For (C6H5)3COH·C5H6N+·Cl- the N to Cl separation is 3.008 (2) Å and the N—H···Cl bond angle is 169 ° (Sykora & Cioffi, 2007). It is noted here that for pyridinium hydrochloride itself two polymorphs found by crystallography (Hensen et al. 1988; Mootz & Hocken, 1989) have been substantiated by dispersion-corrected density functional theory calculations (van de Streek et al. 2010).
The O to Cl separations in the title compound are 3.079 (2) and 3.118 (2) Å and these compare with 3.134 (1) Å in (C6H5)3COH·C5H6N+·Cl- (Sykora & Cioffi, 2007). The C1–O1 bond length in the present compound [1.382 (3) Å] is not significantly different from the C15–O2 bond length [1.378 (3) Å] at the opposite end of the bis-phenol. In comparison, 2,4,6-trimethylphenol which is structurally similar to the phenolic portion of the present molecule but contains a hydrogen bonded O—H···OH system, has a C–O bond length of 1.386 (2) Å (Ziemer & Surygina, 2000). 2,6-Diisopropylphenol which also has a hydrogen bonded O—H···OH system has C–O bond lengths of 1.480 (7) Å (C—O—H···O section) and 1.382 (8) Å (C—O···H section) (Prout et al. 1988).
The chlorines in the present lattice form a pyramidal structure in the interactions with their 3 H-bonded neighbours (Figure 2). Angles are 118, 79 and 69 ° for O1···Cl···O2, O1···Cl···N20 and O2···Cl···N20 respectively and 117, 82 and 76 ° for H1···Cl···H2, H1···Cl···H20 and H2···Cl···H20 respectively. Within the phenolic moiety and the pyrdinium-H ion bond distances and angles are unremarkable. The two phenyl rings of the former (C1—C6 and C12—C17) are inclined to one another at an angle of 84.78 (8) °, a value which is similar to the values reported [86.9 (2), 83.6 (2) and 79.2 (2) °] for the three independent molecules in the
of (CH3)2C(C6H4OH)2 (bisphenol A) (Okada, 1996). Two disordered sites were found for the terminal tertiary butyl substitiuent on the pyridinium-H group. Toluene solvent molecules occupy space between the H-bound units in the crystal lying across centres of symmetry. No close approaches of this solvent to the other molecules are observed. The crystal packing shows that no channels are developed in the overall structure.Data collection: SMART (Siemens, 1995); cell
SAINT (Siemens, 1995); data reduction: SAINT (Siemens, 1995); program(s) used to solve structure: SHELXS97 (Sheldrick, 2008); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008); molecular graphics: ORTEP-3 for Windows (Farrugia, 2012); software used to prepare material for publication: SHELXL97 (Sheldrick, 2008).C9H14N+·Cl−·C19H24O2·0.5C7H7 | F(000) = 1082 |
Mr = 501.60 | Dx = 1.173 Mg m−3 |
Monoclinic, P21/n | Mo Kα radiation, λ = 0.71073 Å |
Hall symbol: -P 2yn | Cell parameters from 7233 reflections |
a = 13.5656 (9) Å | θ = 2.0–25.1° |
b = 14.3215 (9) Å | µ = 0.16 mm−1 |
c = 15.787 (1) Å | T = 150 K |
β = 112.186 (1)° | Thin plate, colourless |
V = 2840.0 (3) Å3 | 0.39 × 0.28 × 0.02 mm |
Z = 4 |
Siemens SMART diffractometer | 4989 independent reflections |
Radiation source: fine-focus sealed tube | 3253 reflections with I > 2σ(I) |
Graphite monochromator | Rint = 0.053 |
area–detector ω scan | θmax = 25.1°, θmin = 2.0° |
Absorption correction: multi-scan (Blessing, 1995) | h = −16→10 |
Tmin = 0.700, Tmax = 0.821 | k = −17→15 |
14535 measured reflections | l = −18→18 |
Refinement on F2 | Secondary atom site location: difference Fourier map |
Least-squares matrix: full | Hydrogen site location: inferred from neighbouring sites |
R[F2 > 2σ(F2)] = 0.052 | H atoms treated by a mixture of independent and constrained refinement |
wR(F2) = 0.114 | w = 1/[σ2(Fo2) + (0.0296P)2 + 1.4177P] where P = (Fo2 + 2Fc2)/3 |
S = 1.08 | (Δ/σ)max = 0.009 |
4989 reflections | Δρmax = 0.22 e Å−3 |
379 parameters | Δρmin = −0.20 e Å−3 |
0 restraints | Extinction correction: SHELXL97 (Sheldrick, 2008), Fc*=kFc[1+0.001xFc2λ3/sin(2θ)]-1/4 |
Primary atom site location: structure-invariant direct methods | Extinction coefficient: 0.0025 (5) |
C9H14N+·Cl−·C19H24O2·0.5C7H7 | V = 2840.0 (3) Å3 |
Mr = 501.60 | Z = 4 |
Monoclinic, P21/n | Mo Kα radiation |
a = 13.5656 (9) Å | µ = 0.16 mm−1 |
b = 14.3215 (9) Å | T = 150 K |
c = 15.787 (1) Å | 0.39 × 0.28 × 0.02 mm |
β = 112.186 (1)° |
Siemens SMART diffractometer | 4989 independent reflections |
Absorption correction: multi-scan (Blessing, 1995) | 3253 reflections with I > 2σ(I) |
Tmin = 0.700, Tmax = 0.821 | Rint = 0.053 |
14535 measured reflections |
R[F2 > 2σ(F2)] = 0.052 | 0 restraints |
wR(F2) = 0.114 | H atoms treated by a mixture of independent and constrained refinement |
S = 1.08 | Δρmax = 0.22 e Å−3 |
4989 reflections | Δρmin = −0.20 e Å−3 |
379 parameters |
Geometry. All e.s.d.'s (except the e.s.d. in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell e.s.d.'s are taken into account individually in the estimation of e.s.d.'s in distances, angles and torsion angles; correlations between e.s.d.'s in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell e.s.d.'s is used for estimating e.s.d.'s involving l.s. planes. |
Refinement. Refinement of F2 against ALL reflections. The weighted R-factor wR and goodness of fit S are based on F2, conventional R-factors R are based on F, with F set to zero for negative F2. The threshold expression of F2 > σ(F2) is used only for calculating R-factors(gt) etc. and is not relevant to the choice of reflections for refinement. R-factors based on F2 are statistically about twice as large as those based on F, and R- factors based on ALL data will be even larger. |
x | y | z | Uiso*/Ueq | Occ. (<1) | |
N20 | 0.5777 (2) | 0.96003 (16) | 0.67143 (17) | 0.0415 (6) | |
Cl | 0.37477 (6) | 0.87567 (5) | 0.53461 (4) | 0.0384 (2) | |
O1 | 0.52861 (16) | 0.85019 (13) | 0.43127 (13) | 0.0406 (5) | |
C1 | 0.5296 (2) | 0.78792 (17) | 0.36475 (17) | 0.0305 (6) | |
C2 | 0.4550 (2) | 0.71593 (17) | 0.33306 (17) | 0.0306 (6) | |
C3 | 0.4654 (2) | 0.65504 (17) | 0.26836 (17) | 0.0305 (6) | |
H3 | 0.4158 | 0.6053 | 0.2469 | 0.037* | |
C4 | 0.5451 (2) | 0.66375 (17) | 0.23373 (17) | 0.0299 (6) | |
C5 | 0.6164 (2) | 0.73712 (17) | 0.26655 (17) | 0.0339 (6) | |
H5 | 0.6712 | 0.7449 | 0.2435 | 0.041* | |
C6 | 0.6106 (2) | 0.79978 (17) | 0.33215 (18) | 0.0329 (6) | |
C7 | 0.3669 (2) | 0.70383 (19) | 0.36795 (19) | 0.0400 (7) | |
H7A | 0.3209 | 0.6520 | 0.3355 | 0.060* | |
H7B | 0.3249 | 0.7614 | 0.3575 | 0.060* | |
H7C | 0.3975 | 0.6902 | 0.4336 | 0.060* | |
C8 | 0.6908 (2) | 0.8769 (2) | 0.3682 (2) | 0.0464 (8) | |
H8A | 0.7396 | 0.8766 | 0.3355 | 0.070* | |
H8B | 0.7313 | 0.8674 | 0.4337 | 0.070* | |
H8C | 0.6539 | 0.9371 | 0.3588 | 0.070* | |
C9 | 0.5473 (2) | 0.59489 (17) | 0.15972 (17) | 0.0331 (6) | |
C10 | 0.4500 (2) | 0.61622 (19) | 0.07168 (17) | 0.0428 (7) | |
H10A | 0.4526 | 0.6815 | 0.0542 | 0.064* | |
H10B | 0.3845 | 0.6054 | 0.0827 | 0.064* | |
H10C | 0.4511 | 0.5753 | 0.0223 | 0.064* | |
C11 | 0.6480 (2) | 0.60593 (19) | 0.13774 (19) | 0.0430 (7) | |
H11A | 0.7112 | 0.5997 | 0.1941 | 0.064* | |
H11B | 0.6478 | 0.6676 | 0.1109 | 0.064* | |
H11C | 0.6490 | 0.5575 | 0.0942 | 0.064* | |
C12 | 0.5458 (2) | 0.49417 (17) | 0.19209 (16) | 0.0271 (6) | |
C13 | 0.6213 (2) | 0.46605 (17) | 0.27644 (17) | 0.0289 (6) | |
H13 | 0.6688 | 0.5114 | 0.3141 | 0.035* | |
C14 | 0.62964 (19) | 0.37446 (17) | 0.30749 (16) | 0.0275 (6) | |
C15 | 0.5596 (2) | 0.30877 (17) | 0.25142 (17) | 0.0289 (6) | |
C16 | 0.4806 (2) | 0.33380 (17) | 0.16800 (17) | 0.0284 (6) | |
C17 | 0.4755 (2) | 0.42643 (17) | 0.14003 (16) | 0.0276 (6) | |
H17 | 0.4220 | 0.4441 | 0.0833 | 0.033* | |
C18 | 0.7107 (2) | 0.34792 (18) | 0.40014 (17) | 0.0355 (7) | |
H18A | 0.7588 | 0.3004 | 0.3927 | 0.053* | |
H18B | 0.6742 | 0.3229 | 0.4382 | 0.053* | |
H18C | 0.7519 | 0.4033 | 0.4297 | 0.053* | |
C19 | 0.4016 (2) | 0.26264 (18) | 0.11083 (18) | 0.0381 (7) | |
H19A | 0.3731 | 0.2274 | 0.1497 | 0.057* | |
H19B | 0.4370 | 0.2197 | 0.0831 | 0.057* | |
H19C | 0.3432 | 0.2945 | 0.0626 | 0.057* | |
O2 | 0.56282 (16) | 0.21611 (12) | 0.27588 (14) | 0.0407 (5) | |
C21 | 0.5685 (2) | 0.9709 (2) | 0.7521 (2) | 0.0462 (8) | |
H21 | 0.5092 | 0.9447 | 0.7618 | 0.055* | |
C22 | 0.6438 (2) | 1.01925 (19) | 0.8208 (2) | 0.0420 (7) | |
H22 | 0.6367 | 1.0258 | 0.8781 | 0.050* | |
C23 | 0.7310 (2) | 1.05919 (17) | 0.80820 (18) | 0.0324 (6) | |
C24 | 0.7377 (2) | 1.04480 (18) | 0.72336 (19) | 0.0374 (7) | |
H24 | 0.7967 | 1.0691 | 0.7120 | 0.045* | |
C25 | 0.6597 (2) | 0.99569 (19) | 0.65561 (19) | 0.0424 (7) | |
H25 | 0.6646 | 0.9873 | 0.5976 | 0.051* | |
C26 | 0.8127 (2) | 1.11584 (19) | 0.88468 (19) | 0.0408 (7) | |
C27 | 0.8489 (7) | 1.0589 (5) | 0.9743 (5) | 0.067 (3) | 0.619 (7) |
H27A | 0.7867 | 1.0424 | 0.9885 | 0.100* | 0.619 (7) |
H27B | 0.8982 | 1.0964 | 1.0243 | 0.100* | 0.619 (7) |
H27C | 0.8847 | 1.0018 | 0.9670 | 0.100* | 0.619 (7) |
C28 | 0.7510 (4) | 1.2038 (3) | 0.9005 (4) | 0.0549 (19) | 0.619 (7) |
H28A | 0.7999 | 1.2425 | 0.9495 | 0.082* | 0.619 (7) |
H28B | 0.6923 | 1.1828 | 0.9177 | 0.082* | 0.619 (7) |
H28C | 0.7224 | 1.2404 | 0.8440 | 0.082* | 0.619 (7) |
C29 | 0.9038 (5) | 1.1479 (5) | 0.8648 (4) | 0.070 (2) | 0.619 (7) |
H29A | 0.9496 | 1.1870 | 0.9153 | 0.105* | 0.619 (7) |
H29B | 0.8787 | 1.1843 | 0.8081 | 0.105* | 0.619 (7) |
H29C | 0.9444 | 1.0938 | 0.8578 | 0.105* | 0.619 (7) |
C30 | 0.8223 (8) | 1.2143 (6) | 0.8482 (7) | 0.069 (4) | 0.381 (7) |
H30A | 0.8707 | 1.2524 | 0.8981 | 0.104* | 0.381 (7) |
H30B | 0.7520 | 1.2438 | 0.8237 | 0.104* | 0.381 (7) |
H30C | 0.8504 | 1.2089 | 0.7995 | 0.104* | 0.381 (7) |
C31 | 0.8037 (13) | 1.1145 (11) | 0.9700 (8) | 0.104 (7) | 0.381 (7) |
H31A | 0.8624 | 1.1501 | 1.0141 | 0.156* | 0.381 (7) |
H31B | 0.8065 | 1.0498 | 0.9910 | 0.156* | 0.381 (7) |
H31C | 0.7357 | 1.1426 | 0.9647 | 0.156* | 0.381 (7) |
C32 | 0.9270 (7) | 1.0667 (8) | 0.8952 (7) | 0.073 (4) | 0.381 (7) |
H32A | 0.9270 | 1.0013 | 0.9134 | 0.109* | 0.381 (7) |
H32B | 0.9857 | 1.0999 | 0.9420 | 0.109* | 0.381 (7) |
H32C | 0.9361 | 1.0698 | 0.8366 | 0.109* | 0.381 (7) |
C41 | 0.3686 (5) | 0.8541 (4) | 0.9056 (4) | 0.0463 (15) | 0.50 |
H41A | 0.2966 | 0.8651 | 0.9039 | 0.069* | 0.50 |
H41B | 0.3958 | 0.7950 | 0.9372 | 0.069* | 0.50 |
H41C | 0.3667 | 0.8508 | 0.8430 | 0.069* | 0.50 |
C42 | 0.4352 (3) | 0.9272 (3) | 0.9523 (3) | 0.0648 (11) | |
C43 | 0.4328 (3) | 1.0136 (3) | 0.9105 (3) | 0.0702 (11) | |
H43 | 0.3863 | 1.0227 | 0.8486 | 0.084* | |
C44 | 0.5031 (3) | 0.9144 (3) | 1.0423 (3) | 0.0699 (11) | |
H44 | 0.5054 | 0.8559 | 1.0714 | 0.084* | |
H20 | 0.511 (3) | 0.927 (2) | 0.622 (2) | 0.092 (12)* | |
H2 | 0.593 (3) | 0.208 (2) | 0.333 (2) | 0.078 (12)* | |
H1 | 0.477 (3) | 0.842 (3) | 0.453 (3) | 0.099 (15)* |
U11 | U22 | U33 | U12 | U13 | U23 | |
N20 | 0.0395 (15) | 0.0352 (14) | 0.0404 (15) | −0.0018 (12) | 0.0044 (13) | −0.0008 (11) |
Cl | 0.0462 (4) | 0.0377 (4) | 0.0290 (4) | −0.0071 (3) | 0.0116 (3) | −0.0025 (3) |
O1 | 0.0424 (12) | 0.0351 (11) | 0.0439 (12) | −0.0056 (9) | 0.0160 (10) | −0.0110 (9) |
C1 | 0.0322 (15) | 0.0251 (14) | 0.0295 (15) | 0.0055 (12) | 0.0064 (12) | 0.0006 (12) |
C2 | 0.0269 (14) | 0.0276 (14) | 0.0339 (15) | 0.0018 (12) | 0.0077 (12) | 0.0022 (12) |
C3 | 0.0317 (15) | 0.0253 (14) | 0.0302 (14) | −0.0028 (12) | 0.0068 (12) | 0.0008 (11) |
C4 | 0.0343 (15) | 0.0258 (14) | 0.0281 (14) | 0.0027 (12) | 0.0103 (12) | 0.0048 (11) |
C5 | 0.0360 (16) | 0.0313 (15) | 0.0348 (16) | 0.0003 (13) | 0.0139 (13) | 0.0028 (13) |
C6 | 0.0321 (15) | 0.0275 (14) | 0.0342 (15) | 0.0002 (12) | 0.0069 (13) | 0.0015 (12) |
C7 | 0.0374 (17) | 0.0352 (16) | 0.0476 (18) | −0.0033 (13) | 0.0163 (14) | −0.0082 (13) |
C8 | 0.0418 (18) | 0.0444 (18) | 0.0527 (19) | −0.0125 (15) | 0.0174 (15) | −0.0088 (15) |
C9 | 0.0410 (16) | 0.0316 (15) | 0.0288 (14) | −0.0016 (13) | 0.0154 (13) | −0.0004 (12) |
C10 | 0.059 (2) | 0.0350 (16) | 0.0285 (15) | 0.0023 (15) | 0.0094 (14) | 0.0037 (13) |
C11 | 0.059 (2) | 0.0370 (17) | 0.0422 (17) | −0.0069 (14) | 0.0301 (15) | 0.0006 (13) |
C12 | 0.0317 (14) | 0.0270 (14) | 0.0266 (14) | 0.0015 (12) | 0.0154 (12) | −0.0001 (11) |
C13 | 0.0254 (14) | 0.0324 (15) | 0.0275 (14) | −0.0024 (12) | 0.0085 (12) | −0.0045 (12) |
C14 | 0.0266 (14) | 0.0306 (14) | 0.0251 (13) | 0.0009 (12) | 0.0097 (11) | −0.0002 (12) |
C15 | 0.0320 (15) | 0.0267 (14) | 0.0288 (14) | −0.0008 (12) | 0.0122 (12) | 0.0009 (11) |
C16 | 0.0283 (14) | 0.0285 (14) | 0.0285 (14) | −0.0017 (12) | 0.0108 (12) | −0.0037 (11) |
C17 | 0.0280 (14) | 0.0324 (15) | 0.0218 (13) | 0.0024 (12) | 0.0089 (11) | 0.0015 (11) |
C18 | 0.0333 (15) | 0.0319 (15) | 0.0341 (15) | 0.0006 (12) | 0.0046 (12) | 0.0006 (12) |
C19 | 0.0379 (16) | 0.0365 (16) | 0.0341 (16) | −0.0034 (13) | 0.0069 (13) | −0.0035 (13) |
O2 | 0.0527 (13) | 0.0278 (11) | 0.0323 (12) | −0.0025 (9) | 0.0053 (10) | 0.0012 (9) |
C21 | 0.0412 (18) | 0.0473 (19) | 0.052 (2) | −0.0104 (15) | 0.0204 (16) | −0.0086 (16) |
C22 | 0.0415 (17) | 0.0466 (18) | 0.0400 (17) | −0.0110 (15) | 0.0177 (14) | −0.0086 (14) |
C23 | 0.0287 (15) | 0.0292 (14) | 0.0366 (16) | 0.0022 (12) | 0.0093 (13) | 0.0041 (12) |
C24 | 0.0367 (16) | 0.0351 (16) | 0.0416 (17) | 0.0004 (13) | 0.0160 (14) | 0.0060 (13) |
C25 | 0.054 (2) | 0.0356 (17) | 0.0353 (17) | 0.0034 (15) | 0.0147 (15) | 0.0055 (13) |
C26 | 0.0346 (16) | 0.0393 (17) | 0.0404 (17) | −0.0090 (14) | 0.0051 (13) | −0.0003 (14) |
C27 | 0.074 (6) | 0.055 (4) | 0.040 (4) | −0.011 (3) | −0.014 (3) | 0.004 (3) |
C28 | 0.049 (3) | 0.041 (3) | 0.060 (4) | −0.002 (3) | 0.004 (3) | −0.016 (3) |
C29 | 0.052 (4) | 0.093 (6) | 0.068 (4) | −0.038 (4) | 0.025 (3) | −0.024 (4) |
C30 | 0.062 (7) | 0.044 (6) | 0.073 (7) | −0.004 (5) | −0.007 (6) | −0.003 (5) |
C31 | 0.115 (14) | 0.155 (17) | 0.045 (7) | −0.097 (13) | 0.032 (9) | −0.043 (11) |
C32 | 0.042 (6) | 0.060 (7) | 0.086 (8) | −0.008 (5) | −0.009 (5) | −0.008 (6) |
C41 | 0.040 (4) | 0.054 (4) | 0.046 (4) | 0.009 (3) | 0.017 (3) | 0.002 (3) |
C42 | 0.047 (2) | 0.058 (2) | 0.105 (3) | −0.0047 (18) | 0.047 (2) | −0.027 (2) |
C43 | 0.053 (2) | 0.080 (3) | 0.093 (3) | 0.005 (2) | 0.044 (2) | −0.017 (2) |
C44 | 0.054 (2) | 0.070 (3) | 0.099 (3) | 0.004 (2) | 0.045 (2) | −0.012 (2) |
N20—C25 | 1.331 (4) | C19—H19A | 0.9800 |
N20—C21 | 1.335 (4) | C19—H19B | 0.9800 |
N20—Cl | 3.035 (3) | C19—H19C | 0.9800 |
N20—H20 | 1.06 (4) | O2—H2 | 0.85 (3) |
Cl—H20 | 1.98 (4) | C21—C22 | 1.365 (4) |
Cl—H1 | 2.27 (4) | C21—H21 | 0.9500 |
O1—C1 | 1.382 (3) | C22—C23 | 1.394 (4) |
O1—H1 | 0.90 (4) | C22—H22 | 0.9500 |
C1—C6 | 1.389 (4) | C23—C24 | 1.392 (4) |
C1—C2 | 1.398 (3) | C23—C26 | 1.528 (4) |
C2—C3 | 1.390 (3) | C24—C25 | 1.379 (4) |
C2—C7 | 1.502 (4) | C24—H24 | 0.9500 |
C3—C4 | 1.389 (4) | C25—H25 | 0.9500 |
C3—H3 | 0.9500 | C26—C31 | 1.398 (12) |
C4—C5 | 1.389 (3) | C26—C29 | 1.459 (6) |
C4—C9 | 1.538 (3) | C26—C27 | 1.544 (8) |
C5—C6 | 1.395 (4) | C26—C30 | 1.547 (9) |
C5—H5 | 0.9500 | C26—C28 | 1.584 (6) |
C6—C8 | 1.504 (3) | C26—C32 | 1.653 (10) |
C7—H7A | 0.9800 | C27—H27A | 0.9800 |
C7—H7B | 0.9800 | C27—H27B | 0.9800 |
C7—H7C | 0.9800 | C27—H27C | 0.9800 |
C8—H8A | 0.9800 | C28—H28A | 0.9800 |
C8—H8B | 0.9800 | C28—H28B | 0.9800 |
C8—H8C | 0.9800 | C28—H28C | 0.9800 |
C9—C12 | 1.533 (3) | C29—H29A | 0.9800 |
C9—C11 | 1.539 (4) | C29—H29B | 0.9800 |
C9—C10 | 1.543 (4) | C29—H29C | 0.9800 |
C10—H10A | 0.9800 | C30—H30A | 0.9800 |
C10—H10B | 0.9800 | C30—H30B | 0.9800 |
C10—H10C | 0.9800 | C30—H30C | 0.9800 |
C11—H11A | 0.9800 | C31—H31A | 0.9800 |
C11—H11B | 0.9800 | C31—H31B | 0.9800 |
C11—H11C | 0.9800 | C31—H31C | 0.9800 |
C12—C17 | 1.391 (3) | C32—H32A | 0.9800 |
C12—C13 | 1.398 (3) | C32—H32B | 0.9800 |
C13—C14 | 1.390 (3) | C32—H32C | 0.9800 |
C13—H13 | 0.9500 | C41—C42 | 1.398 (6) |
C14—C15 | 1.391 (3) | C41—H41A | 0.9800 |
C14—C18 | 1.510 (3) | C41—H41B | 0.9800 |
C15—O2 | 1.378 (3) | C41—H41C | 0.9800 |
C15—C16 | 1.395 (3) | C42—C44 | 1.383 (5) |
C16—C17 | 1.392 (3) | C42—C43 | 1.398 (5) |
C16—C19 | 1.507 (3) | C43—C44i | 1.373 (5) |
C17—H17 | 0.9500 | C43—H43 | 0.9500 |
C18—H18A | 0.9800 | C44—C43i | 1.373 (5) |
C18—H18B | 0.9800 | C44—H44 | 0.9500 |
C18—H18C | 0.9800 | ||
C25—N20—C21 | 121.4 (3) | C16—C19—H19C | 109.5 |
C25—N20—Cl | 128.1 (2) | H19A—C19—H19C | 109.5 |
C21—N20—Cl | 109.82 (19) | H19B—C19—H19C | 109.5 |
C25—N20—H20 | 125 (2) | C15—O2—H2 | 113 (2) |
C21—N20—H20 | 113 (2) | N20—C21—C22 | 120.4 (3) |
H20—Cl—H1 | 82.2 (14) | N20—C21—H21 | 119.8 |
C1—O1—H1 | 116 (2) | C22—C21—H21 | 119.8 |
O1—C1—C6 | 116.0 (2) | C21—C22—C23 | 121.0 (3) |
O1—C1—C2 | 122.3 (2) | C21—C22—H22 | 119.5 |
C6—C1—C2 | 121.6 (2) | C23—C22—H22 | 119.5 |
C3—C2—C1 | 117.7 (2) | C24—C23—C22 | 116.4 (2) |
C3—C2—C7 | 120.8 (2) | C24—C23—C26 | 123.2 (2) |
C1—C2—C7 | 121.5 (2) | C22—C23—C26 | 120.5 (2) |
C4—C3—C2 | 122.9 (2) | C25—C24—C23 | 120.8 (3) |
C4—C3—H3 | 118.6 | C25—C24—H24 | 119.6 |
C2—C3—H3 | 118.6 | C23—C24—H24 | 119.6 |
C5—C4—C3 | 117.2 (2) | N20—C25—C24 | 120.0 (3) |
C5—C4—C9 | 123.9 (2) | N20—C25—H25 | 120.0 |
C3—C4—C9 | 118.9 (2) | C24—C25—H25 | 120.0 |
C4—C5—C6 | 122.5 (3) | C31—C26—C29 | 126.9 (6) |
C4—C5—H5 | 118.8 | C31—C26—C23 | 116.9 (5) |
C6—C5—H5 | 118.8 | C29—C26—C23 | 114.7 (3) |
C1—C6—C5 | 118.1 (2) | C29—C26—C27 | 111.2 (5) |
C1—C6—C8 | 120.7 (2) | C23—C26—C27 | 109.2 (3) |
C5—C6—C8 | 121.2 (3) | C31—C26—C30 | 115.0 (8) |
C2—C7—H7A | 109.5 | C29—C26—C30 | 55.7 (5) |
C2—C7—H7B | 109.5 | C23—C26—C30 | 109.1 (4) |
H7A—C7—H7B | 109.5 | C27—C26—C30 | 141.3 (5) |
C2—C7—H7C | 109.5 | C31—C26—C28 | 67.4 (8) |
H7A—C7—H7C | 109.5 | C29—C26—C28 | 109.0 (4) |
H7B—C7—H7C | 109.5 | C23—C26—C28 | 106.1 (3) |
C6—C8—H8A | 109.5 | C27—C26—C28 | 106.2 (4) |
C6—C8—H8B | 109.5 | C30—C26—C28 | 57.2 (5) |
H8A—C8—H8B | 109.5 | C31—C26—C32 | 108.5 (8) |
C6—C8—H8C | 109.5 | C29—C26—C32 | 46.9 (4) |
H8A—C8—H8C | 109.5 | C23—C26—C32 | 103.1 (4) |
H8B—C8—H8C | 109.5 | C27—C26—C32 | 73.8 (5) |
C12—C9—C4 | 110.1 (2) | C30—C26—C32 | 102.6 (6) |
C12—C9—C11 | 107.2 (2) | C28—C26—C32 | 148.7 (4) |
C4—C9—C11 | 112.3 (2) | C26—C27—H27A | 109.5 |
C12—C9—C10 | 111.8 (2) | C26—C27—H27B | 109.5 |
C4—C9—C10 | 107.6 (2) | C26—C27—H27C | 109.5 |
C11—C9—C10 | 107.9 (2) | C26—C28—H28A | 109.5 |
C9—C10—H10A | 109.5 | C26—C28—H28B | 109.5 |
C9—C10—H10B | 109.5 | C26—C28—H28C | 109.5 |
H10A—C10—H10B | 109.5 | C26—C29—H29A | 109.5 |
C9—C10—H10C | 109.5 | C26—C29—H29B | 109.5 |
H10A—C10—H10C | 109.5 | C26—C29—H29C | 109.5 |
H10B—C10—H10C | 109.5 | C26—C30—H30A | 109.5 |
C9—C11—H11A | 109.5 | C26—C30—H30B | 109.5 |
C9—C11—H11B | 109.5 | H30A—C30—H30B | 109.5 |
H11A—C11—H11B | 109.5 | C26—C30—H30C | 109.5 |
C9—C11—H11C | 109.5 | H30A—C30—H30C | 109.5 |
H11A—C11—H11C | 109.5 | H30B—C30—H30C | 109.5 |
H11B—C11—H11C | 109.5 | C26—C31—H31A | 109.5 |
C17—C12—C13 | 117.0 (2) | C26—C31—H31B | 109.5 |
C17—C12—C9 | 123.5 (2) | H31A—C31—H31B | 109.5 |
C13—C12—C9 | 119.4 (2) | C26—C31—H31C | 109.5 |
C14—C13—C12 | 122.7 (2) | H31A—C31—H31C | 109.5 |
C14—C13—H13 | 118.6 | H31B—C31—H31C | 109.5 |
C12—C13—H13 | 118.6 | C26—C32—H32A | 109.5 |
C13—C14—C15 | 117.9 (2) | C26—C32—H32B | 109.5 |
C13—C14—C18 | 120.8 (2) | H32A—C32—H32B | 109.5 |
C15—C14—C18 | 121.3 (2) | C26—C32—H32C | 109.5 |
O2—C15—C14 | 122.1 (2) | H32A—C32—H32C | 109.5 |
O2—C15—C16 | 116.3 (2) | H32B—C32—H32C | 109.5 |
C14—C15—C16 | 121.6 (2) | C42—C41—H41A | 109.5 |
C17—C16—C15 | 118.2 (2) | C42—C41—H41B | 109.5 |
C17—C16—C19 | 121.0 (2) | H41A—C41—H41B | 109.5 |
C15—C16—C19 | 120.7 (2) | C42—C41—H41C | 109.5 |
C12—C17—C16 | 122.4 (2) | H41A—C41—H41C | 109.5 |
C12—C17—H17 | 118.8 | H41B—C41—H41C | 109.5 |
C16—C17—H17 | 118.8 | C44—C42—C41 | 119.3 (4) |
C14—C18—H18A | 109.5 | C44—C42—C43 | 119.4 (4) |
C14—C18—H18B | 109.5 | C41—C42—C43 | 121.3 (5) |
H18A—C18—H18B | 109.5 | C44i—C43—C42 | 120.8 (4) |
C14—C18—H18C | 109.5 | C44i—C43—H43 | 119.6 |
H18A—C18—H18C | 109.5 | C42—C43—H43 | 119.6 |
H18B—C18—H18C | 109.5 | C43i—C44—C42 | 119.9 (4) |
C16—C19—H19A | 109.5 | C43i—C44—H44 | 120.1 |
C16—C19—H19B | 109.5 | C42—C44—H44 | 120.1 |
H19A—C19—H19B | 109.5 |
Symmetry code: (i) −x+1, −y+2, −z+2. |
D—H···A | D—H | H···A | D···A | D—H···A |
N20—H20···Cl | 1.06 (4) | 1.98 (4) | 3.035 (3) | 173 (3) |
O2—H2···Clii | 0.85 (3) | 2.30 (3) | 3.079 (2) | 153 (3) |
O1—H1···Cl | 0.90 (4) | 2.27 (4) | 3.118 (2) | 157 (3) |
Symmetry code: (ii) −x+1, −y+1, −z+1. |
D—H···A | D—H | H···A | D···A | D—H···A |
N20—H20···Cl | 1.06 (4) | 1.98 (4) | 3.035 (3) | 173 (3) |
O2—H2···Cli | 0.85 (3) | 2.30 (3) | 3.079 (2) | 153 (3) |
O1—H1···Cl | 0.90 (4) | 2.27 (4) | 3.118 (2) | 157 (3) |
Symmetry code: (i) −x+1, −y+1, −z+1. |
Acknowledgements
We are grateful to Ms Tanya Groutso of the University of Auckland for the data collection.
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