Supporting information
Crystallographic Information File (CIF) https://doi.org/10.1107/S1600536807052245/zl2073sup1.cif | |
Structure factor file (CIF format) https://doi.org/10.1107/S1600536807052245/zl2073Isup2.hkl |
CCDC reference: 667437
The title compound was prepared following the procedure of Baliah et al. (1978). Crystals suitable for X-ray diffraction were grown by slow evaporation of an ethanolic solution.
The solvate water molecule is disordered over two positions with an occupancy rate of 0.905 (3) to 0.095 (3). The ADPs of both oxygen atoms were set to be identical. The water hydrogen atoms were located in difference density Fourier maps and the O—H distances were restrained to be 0.84 (2) Å. To allow for a stable and meaningful refinement of the H atoms of the less occupied water molecule the hydrogen bonding distances to both chlorine atoms were restrained to be each the same in both moieties, as were the H···H distances in both water molecules. The remaining H atoms were positioned geometrically and allowed to ride on their parent atoms with N—H = 0.90 Å, C—H = 0.93–0.98 Å, O—H = 0.82 Å and Uiso = 1.2–1.5 Ueq(parent atom). Hydroxyl H atoms were allowed to rotate, but not to tip, to best fit the experimental electron density. A damping factor (damp 400 15 in the final refinement cycles) was applied to avoid large and erratic displacements of the hydrogen atoms of the less occupied water molecule.
The title compound has been analysed as part of our crystallographic studies on substituted decahydroquinolines. Thiruvalluvar et al. (1995) have reported a crystal structure of N-benzoyl-2-phenyldecahydroquinolin-4-one, wherein the piperidine ring adopts a flexible twist conformation. The title compound, Fig. 1., crystallizes with two molecules per asymmetric unit. Both molecules are essentially identical, the r.m.s. deviation of an overlay of all non-hydrogen atoms is only 0.086 Å. The torsion angles (C8—C9—C10—C4 = -179.5 (1)° for molecule A and -178.1 (1)° for molecule B) confirm the trans fusion of the piperidine and cyclohexane rings in both independent molecules. It is evident from the ring torsion angles that the piperidine and cyclohexane rings are both in a chair conformation. The oxime moieties are essentially planar with r.m.s. deviations of only 0.024 (1) Å. The phenyl rings at C2 are equatorially oriented with respect to the piperidine rings. The crystal structure is stabilized by intramolecular N—H···Cl, C—H···Cl, and C—H···O and by intermolecular N—H···N, N—H···Cl, and O—H···Cl hydrogen bonds., see Fig. 2 and the hydrogen bonding table. A water molecule that bridges via hydrogen bonds the two crystallographically independent chlorine anions is disordered over two chemically equivalent sites. Its occupancy ratio refined to 0.905:0.095.
For a related crystal structure, see Thiruvalluvar et al., 1995. For preparation of the title compound, see Baliah et al., 1978.
Data collection: APEX2 (Bruker, 2004); cell refinement: APEX2 (Bruker, 2004; data reduction: SAINT-NT (Bruker, 2004); program(s) used to solve structure: DIRDIF99 (Beurskens et al., 1999); program(s) used to refine structure: SHELXL97 (Sheldrick, 1997); molecular graphics: ORTEP-3 (Farrugia, 1997); software used to prepare material for publication: PLATON (Spek, 2003).
C15H21N2O+·Cl−·0.5H2O | Dx = 1.262 Mg m−3 |
Mr = 289.81 | Melting point: 521.5 K |
Orthorhombic, Pna21 | Mo Kα radiation, λ = 0.71073 Å |
Hall symbol: P 2c -2n | Cell parameters from 7599 reflections |
a = 13.1733 (4) Å | θ = 1.9–25.0° |
b = 18.2824 (5) Å | µ = 0.25 mm−1 |
c = 12.6656 (4) Å | T = 293 K |
V = 3050.38 (16) Å3 | Block, colourless |
Z = 8 | 0.28 × 0.18 × 0.18 mm |
F(000) = 1240 |
Bruker APEXII diffractometer | 4758 independent reflections |
Radiation source: fine-focus sealed tube | 4335 reflections with I > 2σ(I) |
Graphite monochromator | Rint = 0.020 |
φ and ω scans | θmax = 25.0°, θmin = 1.9° |
Absorption correction: multi-scan (SADABS; Bruker, 2004) | h = −11→15 |
Tmin = 0.743, Tmax = 0.956 | k = −21→21 |
15501 measured reflections | l = −13→15 |
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)] = 0.028 | H atoms treated by a mixture of independent and constrained refinement |
wR(F2) = 0.075 | w = 1/[σ2(Fo2) + (0.0401P)2 + 0.4811P] where P = (Fo2 + 2Fc2)/3 |
S = 1.04 | (Δ/σ)max = 0.021 |
4758 reflections | Δρmax = 0.16 e Å−3 |
370 parameters | Δρmin = −0.14 e Å−3 |
8 restraints | Absolute structure: Flack (1983), 1936 Friedel pairs |
Primary atom site location: structure-invariant direct methods | Absolute structure parameter: −0.02 (5) |
C15H21N2O+·Cl−·0.5H2O | V = 3050.38 (16) Å3 |
Mr = 289.81 | Z = 8 |
Orthorhombic, Pna21 | Mo Kα radiation |
a = 13.1733 (4) Å | µ = 0.25 mm−1 |
b = 18.2824 (5) Å | T = 293 K |
c = 12.6656 (4) Å | 0.28 × 0.18 × 0.18 mm |
Bruker APEXII diffractometer | 4758 independent reflections |
Absorption correction: multi-scan (SADABS; Bruker, 2004) | 4335 reflections with I > 2σ(I) |
Tmin = 0.743, Tmax = 0.956 | Rint = 0.020 |
15501 measured reflections |
R[F2 > 2σ(F2)] = 0.028 | H atoms treated by a mixture of independent and constrained refinement |
wR(F2) = 0.075 | Δρmax = 0.16 e Å−3 |
S = 1.04 | Δρmin = −0.14 e Å−3 |
4758 reflections | Absolute structure: Flack (1983), 1936 Friedel pairs |
370 parameters | Absolute structure parameter: −0.02 (5) |
8 restraints |
Geometry. Bond distances, angles etc. have been calculated using the rounded fractional coordinates. All su's are estimated from the variances of the (full) variance-covariance matrix. The cell e.s.d.'s are taken into account in the estimation of distances, angles and torsion angles |
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) | |
O4A | −0.08852 (9) | 0.14775 (6) | 0.14251 (11) | 0.0470 (4) | |
N1A | 0.23310 (8) | 0.22848 (7) | 0.26652 (10) | 0.0261 (4) | |
N4A | −0.06632 (9) | 0.20708 (7) | 0.20969 (11) | 0.0327 (4) | |
C2A | 0.19797 (11) | 0.17058 (8) | 0.19004 (13) | 0.0287 (4) | |
C3A | 0.09632 (11) | 0.14114 (8) | 0.22857 (15) | 0.0356 (5) | |
C4A | 0.02224 (11) | 0.20168 (8) | 0.24970 (13) | 0.0299 (5) | |
C5A | −0.01349 (12) | 0.32273 (10) | 0.34549 (15) | 0.0415 (6) | |
C6A | 0.03391 (14) | 0.38036 (11) | 0.41681 (17) | 0.0511 (6) | |
C7A | 0.12985 (14) | 0.41068 (10) | 0.36777 (17) | 0.0525 (6) | |
C8A | 0.20610 (13) | 0.35007 (9) | 0.34488 (15) | 0.0393 (5) | |
C9A | 0.15959 (11) | 0.29081 (8) | 0.27758 (13) | 0.0293 (4) | |
C10A | 0.06029 (11) | 0.26051 (9) | 0.32326 (13) | 0.0302 (5) | |
C21A | 0.27973 (11) | 0.11392 (8) | 0.17575 (13) | 0.0309 (5) | |
C22A | 0.34608 (13) | 0.12016 (11) | 0.09173 (15) | 0.0450 (6) | |
C23A | 0.42413 (15) | 0.07005 (13) | 0.07871 (17) | 0.0614 (7) | |
C24A | 0.43615 (15) | 0.01465 (11) | 0.1498 (2) | 0.0583 (7) | |
C25A | 0.37243 (15) | 0.00811 (10) | 0.23380 (18) | 0.0521 (7) | |
C26A | 0.29358 (13) | 0.05739 (9) | 0.24692 (15) | 0.0396 (5) | |
O4B | 0.55407 (9) | 0.14436 (6) | 0.85979 (11) | 0.0467 (4) | |
N1B | 0.23888 (9) | 0.22615 (7) | 0.72882 (11) | 0.0293 (4) | |
N4B | 0.53580 (10) | 0.20112 (7) | 0.78713 (12) | 0.0348 (4) | |
C2B | 0.27362 (11) | 0.16966 (9) | 0.80739 (13) | 0.0305 (5) | |
C3B | 0.37217 (11) | 0.13598 (9) | 0.76778 (15) | 0.0367 (5) | |
C4B | 0.44839 (11) | 0.19465 (8) | 0.74485 (13) | 0.0314 (5) | |
C5B | 0.48912 (13) | 0.31285 (10) | 0.64300 (16) | 0.0457 (6) | |
C6B | 0.44378 (14) | 0.36985 (12) | 0.56901 (18) | 0.0570 (7) | |
C7B | 0.34831 (14) | 0.40309 (10) | 0.61570 (18) | 0.0533 (7) | |
C8B | 0.27053 (12) | 0.34430 (10) | 0.64105 (16) | 0.0417 (6) | |
C9B | 0.31512 (11) | 0.28649 (8) | 0.71339 (13) | 0.0305 (5) | |
C10B | 0.41304 (11) | 0.25273 (9) | 0.66891 (13) | 0.0328 (5) | |
C21B | 0.18782 (12) | 0.11607 (9) | 0.82825 (14) | 0.0342 (5) | |
C22B | 0.11709 (14) | 0.13335 (11) | 0.90508 (15) | 0.0465 (6) | |
C23B | 0.03521 (16) | 0.08800 (13) | 0.92400 (18) | 0.0630 (8) | |
C24B | 0.02430 (16) | 0.02501 (12) | 0.8665 (2) | 0.0629 (8) | |
C25B | 0.09344 (15) | 0.00736 (10) | 0.7902 (2) | 0.0619 (8) | |
C26B | 0.17489 (14) | 0.05274 (10) | 0.77065 (18) | 0.0496 (6) | |
O1 | 0.17392 (18) | 0.49339 (11) | 0.0517 (2) | 0.1090 (9) | 0.906 (3) |
O2 | 0.3144 (15) | 0.4868 (8) | −0.0019 (18) | 0.1090 (9) | 0.095 (3) |
Cl1 | 0.23093 (3) | 0.15663 (2) | 0.49699 (4) | 0.0410 (1) | |
Cl2 | 0.23808 (3) | 0.31712 (2) | 0.99444 (5) | 0.0463 (1) | |
H1A1 | 0.29328 | 0.24616 | 0.24460 | 0.0314* | |
H1A2 | 0.24260 | 0.20783 | 0.33025 | 0.0314* | |
H2A | 0.18667 | 0.19420 | 0.12159 | 0.0344* | |
H3A1 | 0.10671 | 0.11322 | 0.29280 | 0.0427* | |
H3A2 | 0.06834 | 0.10846 | 0.17572 | 0.0427* | |
H4A | −0.14310 | 0.15490 | 0.11314 | 0.0705* | |
H5A1 | −0.07396 | 0.30328 | 0.37898 | 0.0498* | |
H5A2 | −0.03359 | 0.34522 | 0.27935 | 0.0498* | |
H6A1 | 0.04972 | 0.35881 | 0.48483 | 0.0613* | |
H6A2 | −0.01417 | 0.41976 | 0.42815 | 0.0613* | |
H7A1 | 0.11304 | 0.43574 | 0.30256 | 0.0631* | |
H9A | 0.14576 | 0.31090 | 0.20730 | 0.0352* | |
H7A2 | 0.16012 | 0.44602 | 0.41542 | 0.0631* | |
H10A | 0.07643 | 0.23720 | 0.39088 | 0.0362* | |
H8A1 | 0.22939 | 0.32910 | 0.41092 | 0.0472* | |
H8A2 | 0.26445 | 0.37053 | 0.30870 | 0.0472* | |
H22A | 0.33836 | 0.15819 | 0.04363 | 0.0540* | |
H23A | 0.46817 | 0.07419 | 0.02163 | 0.0737* | |
H24A | 0.48844 | −0.01896 | 0.14081 | 0.0699* | |
H25A | 0.38179 | −0.02944 | 0.28237 | 0.0625* | |
H26A | 0.24965 | 0.05244 | 0.30395 | 0.0475* | |
H2B | 0.28847 | 0.19499 | 0.87381 | 0.0366* | |
H4B | 0.60021 | 0.15630 | 0.89968 | 0.0700* | |
H9B | 0.33005 | 0.30878 | 0.78202 | 0.0366* | |
H10B | 0.39548 | 0.22829 | 0.60251 | 0.0393* | |
H1B1 | 0.22727 | 0.20419 | 0.66639 | 0.0351* | |
H1B2 | 0.17993 | 0.24564 | 0.75114 | 0.0351* | |
H3B1 | 0.39906 | 0.10292 | 0.82075 | 0.0440* | |
H3B2 | 0.35908 | 0.10802 | 0.70413 | 0.0440* | |
H5B1 | 0.54857 | 0.29132 | 0.61019 | 0.0548* | |
H5B2 | 0.51057 | 0.33648 | 0.70785 | 0.0548* | |
H6B1 | 0.49324 | 0.40815 | 0.55628 | 0.0684* | |
H6B2 | 0.42772 | 0.34716 | 0.50183 | 0.0684* | |
H7B1 | 0.31940 | 0.43761 | 0.56592 | 0.0640* | |
H7B2 | 0.36541 | 0.42954 | 0.67966 | 0.0640* | |
H22B | 0.12475 | 0.17595 | 0.94440 | 0.0558* | |
H8B1 | 0.21207 | 0.36650 | 0.67482 | 0.0500* | |
H23B | −0.01222 | 0.10015 | 0.97548 | 0.0756* | |
H8B2 | 0.24784 | 0.32150 | 0.57605 | 0.0500* | |
H24B | −0.03042 | −0.00586 | 0.87938 | 0.0755* | |
H25B | 0.08553 | −0.03542 | 0.75134 | 0.0743* | |
H26B | 0.22140 | 0.04056 | 0.71828 | 0.0595* | |
H1A | 0.2045 (6) | 0.45366 (7) | 0.0351 (11) | 0.1635* | 0.906 (3) |
H1B | 0.2120 (4) | 0.53110 (13) | 0.0474 (8) | 0.1635* | 0.906 (3) |
H2C | 0.2816 (10) | 0.4531 (3) | 0.028 (2) | 0.1635* | 0.095 (3) |
H2D | 0.3179 (9) | 0.52669 (19) | 0.031 (2) | 0.1635* | 0.095 (3) |
U11 | U22 | U33 | U12 | U13 | U23 | |
O4A | 0.0355 (6) | 0.0516 (7) | 0.0538 (8) | 0.0033 (5) | −0.0179 (6) | −0.0147 (6) |
N1A | 0.0186 (6) | 0.0324 (6) | 0.0274 (8) | 0.0001 (5) | −0.0009 (5) | 0.0013 (6) |
N4A | 0.0242 (6) | 0.0399 (7) | 0.0339 (8) | 0.0007 (5) | −0.0042 (5) | −0.0050 (6) |
C2A | 0.0239 (7) | 0.0359 (8) | 0.0262 (8) | 0.0033 (6) | −0.0043 (6) | 0.0004 (7) |
C3A | 0.0255 (7) | 0.0362 (8) | 0.0450 (10) | 0.0008 (6) | −0.0062 (7) | −0.0016 (8) |
C4A | 0.0203 (7) | 0.0363 (8) | 0.0332 (9) | −0.0004 (6) | 0.0005 (6) | 0.0031 (7) |
C5A | 0.0256 (8) | 0.0575 (10) | 0.0415 (11) | 0.0081 (7) | −0.0021 (7) | −0.0120 (9) |
C6A | 0.0384 (9) | 0.0608 (11) | 0.0542 (12) | 0.0112 (9) | −0.0038 (8) | −0.0261 (10) |
C7A | 0.0465 (10) | 0.0474 (9) | 0.0637 (14) | 0.0037 (8) | −0.0067 (9) | −0.0226 (10) |
C8A | 0.0306 (8) | 0.0416 (9) | 0.0457 (11) | −0.0029 (7) | −0.0016 (8) | −0.0074 (8) |
C9A | 0.0256 (7) | 0.0346 (7) | 0.0278 (9) | 0.0032 (6) | −0.0012 (6) | 0.0007 (7) |
C10A | 0.0211 (7) | 0.0417 (8) | 0.0279 (9) | 0.0035 (6) | −0.0025 (6) | 0.0001 (7) |
C21A | 0.0241 (7) | 0.0368 (8) | 0.0318 (9) | 0.0017 (6) | −0.0054 (6) | −0.0069 (7) |
C22A | 0.0390 (9) | 0.0620 (11) | 0.0341 (10) | 0.0121 (8) | −0.0010 (8) | 0.0035 (9) |
C23A | 0.0460 (11) | 0.0932 (15) | 0.0451 (12) | 0.0246 (11) | 0.0080 (9) | −0.0125 (12) |
C24A | 0.0480 (11) | 0.0550 (11) | 0.0718 (16) | 0.0248 (9) | −0.0108 (10) | −0.0183 (11) |
C25A | 0.0503 (10) | 0.0370 (9) | 0.0689 (15) | 0.0079 (8) | −0.0126 (10) | −0.0021 (9) |
C26A | 0.0365 (8) | 0.0344 (8) | 0.0479 (11) | 0.0013 (7) | −0.0017 (8) | 0.0042 (8) |
O4B | 0.0383 (6) | 0.0441 (6) | 0.0576 (9) | −0.0002 (5) | −0.0225 (6) | 0.0093 (6) |
N1B | 0.0232 (6) | 0.0370 (7) | 0.0276 (8) | 0.0031 (5) | 0.0002 (5) | −0.0026 (6) |
N4B | 0.0253 (7) | 0.0411 (7) | 0.0379 (9) | 0.0031 (5) | −0.0056 (6) | 0.0014 (6) |
C2B | 0.0300 (8) | 0.0367 (8) | 0.0247 (9) | −0.0012 (6) | −0.0042 (6) | −0.0005 (7) |
C3B | 0.0273 (8) | 0.0372 (8) | 0.0455 (11) | 0.0020 (7) | −0.0085 (7) | 0.0012 (8) |
C4B | 0.0237 (7) | 0.0404 (8) | 0.0301 (9) | 0.0033 (6) | −0.0016 (6) | −0.0041 (7) |
C5B | 0.0283 (8) | 0.0634 (11) | 0.0454 (12) | −0.0020 (8) | −0.0012 (8) | 0.0157 (10) |
C6B | 0.0388 (10) | 0.0727 (13) | 0.0595 (14) | −0.0056 (9) | −0.0002 (9) | 0.0284 (11) |
C7B | 0.0487 (11) | 0.0512 (10) | 0.0601 (13) | 0.0000 (9) | −0.0026 (10) | 0.0225 (10) |
C8B | 0.0320 (9) | 0.0459 (10) | 0.0471 (12) | 0.0074 (7) | 0.0007 (8) | 0.0107 (9) |
C9B | 0.0274 (7) | 0.0360 (8) | 0.0281 (9) | −0.0001 (6) | −0.0008 (6) | 0.0023 (7) |
C10B | 0.0217 (7) | 0.0485 (9) | 0.0281 (9) | 0.0005 (7) | −0.0017 (6) | 0.0007 (8) |
C21B | 0.0325 (8) | 0.0363 (8) | 0.0338 (10) | −0.0013 (7) | −0.0067 (7) | 0.0014 (7) |
C22B | 0.0465 (10) | 0.0593 (11) | 0.0337 (10) | −0.0138 (9) | 0.0015 (8) | −0.0067 (9) |
C23B | 0.0536 (12) | 0.0916 (15) | 0.0438 (13) | −0.0259 (11) | 0.0113 (9) | −0.0024 (12) |
C24B | 0.0530 (12) | 0.0615 (12) | 0.0743 (17) | −0.0231 (10) | −0.0007 (11) | 0.0099 (12) |
C25B | 0.0480 (11) | 0.0406 (10) | 0.0971 (19) | −0.0071 (9) | −0.0065 (12) | −0.0136 (12) |
C26B | 0.0357 (9) | 0.0444 (10) | 0.0687 (14) | −0.0009 (8) | 0.0009 (9) | −0.0152 (10) |
O1 | 0.1029 (16) | 0.0790 (12) | 0.145 (2) | −0.0179 (12) | 0.0326 (15) | −0.0115 (13) |
O2 | 0.1029 (16) | 0.0790 (12) | 0.145 (2) | −0.0179 (12) | 0.0326 (15) | −0.0115 (13) |
Cl1 | 0.0443 (2) | 0.0488 (2) | 0.0298 (2) | 0.0058 (2) | −0.0018 (2) | −0.0005 (2) |
Cl2 | 0.0433 (2) | 0.0545 (2) | 0.0410 (2) | 0.0002 (2) | −0.0150 (2) | −0.0034 (3) |
O4A—N4A | 1.4093 (18) | C8A—H8A1 | 0.9700 |
O4A—H4A | 0.8200 | C8A—H8A2 | 0.9700 |
O4B—N4B | 1.4077 (19) | C9A—H9A | 0.9800 |
O4B—H4B | 0.8200 | C10A—H10A | 0.9800 |
O1—H1A | 0.857 (6) | C22A—H22A | 0.9300 |
O1—H1B | 0.854 (4) | C23A—H23A | 0.9300 |
O2—H2C | 0.84 (2) | C24A—H24A | 0.9300 |
O2—H2D | 0.84 (2) | C25A—H25A | 0.9300 |
N1A—C9A | 1.5020 (19) | C26A—H26A | 0.9300 |
N1A—C2A | 1.508 (2) | C2B—C3B | 1.522 (2) |
N4A—C4A | 1.2758 (19) | C2B—C21B | 1.519 (2) |
N1A—H1A1 | 0.9000 | C3B—C4B | 1.498 (2) |
N1A—H1A2 | 0.9000 | C4B—C10B | 1.507 (2) |
N1B—C2B | 1.505 (2) | C5B—C10B | 1.523 (2) |
N1B—C9B | 1.5046 (19) | C5B—C6B | 1.524 (3) |
N4B—C4B | 1.275 (2) | C6B—C7B | 1.517 (3) |
N1B—H1B2 | 0.9000 | C7B—C8B | 1.519 (3) |
N1B—H1B1 | 0.9000 | C8B—C9B | 1.517 (2) |
C2A—C21A | 1.505 (2) | C9B—C10B | 1.537 (2) |
C2A—C3A | 1.524 (2) | C21B—C22B | 1.384 (3) |
C3A—C4A | 1.500 (2) | C21B—C26B | 1.379 (3) |
C4A—C10A | 1.509 (2) | C22B—C23B | 1.381 (3) |
C5A—C6A | 1.522 (3) | C23B—C24B | 1.370 (3) |
C5A—C10A | 1.523 (2) | C24B—C25B | 1.367 (3) |
C6A—C7A | 1.513 (3) | C25B—C26B | 1.379 (3) |
C7A—C8A | 1.523 (3) | C2B—H2B | 0.9800 |
C8A—C9A | 1.509 (2) | C3B—H3B1 | 0.9700 |
C9A—C10A | 1.534 (2) | C3B—H3B2 | 0.9700 |
C21A—C26A | 1.384 (2) | C5B—H5B1 | 0.9700 |
C21A—C22A | 1.382 (2) | C5B—H5B2 | 0.9700 |
C22A—C23A | 1.387 (3) | C6B—H6B2 | 0.9700 |
C23A—C24A | 1.364 (3) | C6B—H6B1 | 0.9700 |
C24A—C25A | 1.360 (3) | C7B—H7B2 | 0.9700 |
C25A—C26A | 1.385 (3) | C7B—H7B1 | 0.9700 |
C2A—H2A | 0.9800 | C8B—H8B1 | 0.9700 |
C3A—H3A2 | 0.9700 | C8B—H8B2 | 0.9700 |
C3A—H3A1 | 0.9700 | C9B—H9B | 0.9800 |
C5A—H5A1 | 0.9700 | C10B—H10B | 0.9800 |
C5A—H5A2 | 0.9700 | C22B—H22B | 0.9300 |
C6A—H6A1 | 0.9700 | C23B—H23B | 0.9300 |
C6A—H6A2 | 0.9700 | C24B—H24B | 0.9300 |
C7A—H7A2 | 0.9700 | C25B—H25B | 0.9300 |
C7A—H7A1 | 0.9700 | C26B—H26B | 0.9300 |
Cl1···N1A | 3.2011 (14) | H1A2···Cl1 | 2.3200 |
Cl1···N1B | 3.2013 (15) | H2A···H22A | 2.3200 |
Cl1···O2i | 3.162 (15) | H2A···H22Bv | 2.4100 |
Cl1···O1i | 3.310 (2) | H2A···Cl2v | 2.8500 |
Cl2···O1ii | 3.410 (2) | H2A···H9A | 2.4500 |
Cl2···O2ii | 3.261 (15) | H2A···C22Bv | 3.1000 |
Cl2···O4Biii | 3.0464 (13) | H2B···H22Aii | 2.3500 |
Cl2···C2B | 3.6194 (17) | H2B···H9B | 2.4500 |
Cl1···H10A | 2.8500 | H2B···Cl2 | 2.7900 |
Cl1···H10B | 2.8600 | H2B···H22B | 2.3600 |
Cl1···H1A2 | 2.3200 | H2C···O4Aiv | 2.904 (15) |
Cl1···H2Di | 2.499 (6) | H2C···H4Aiv | 2.4600 |
Cl1···H5B1iii | 2.9600 | H2C···Cl2v | 2.587 (7) |
Cl1···H26A | 3.1100 | H2D···H26Bvi | 2.4400 |
Cl1···H5A1iv | 3.0600 | H2D···Cl1vi | 2.499 (6) |
Cl1···H1Bi | 2.498 (4) | H2D···C26Bvi | 3.07 (3) |
Cl1···H1B1 | 2.3200 | H3A1···H1A2 | 2.5300 |
Cl2···H2B | 2.7900 | H3A1···C26A | 2.7300 |
Cl2···H9B | 2.9500 | H3A1···H26A | 2.1900 |
Cl2···H22B | 3.0500 | H3A1···H24Bviii | 2.4600 |
Cl2···H9Aii | 2.9600 | H3A2···O4A | 2.2300 |
Cl2···H2Cii | 2.587 (7) | H4A···H2Ciii | 2.4600 |
Cl2···H2Aii | 2.8500 | H4A···Cl2ix | 2.2300 |
Cl2···H4Biii | 2.2300 | H4A···H1A1iii | 2.6000 |
Cl2···H1Aii | 2.587 (3) | H4B···Cl2iv | 2.2300 |
O1···Cl2v | 3.410 (2) | H5A1···Cl1iii | 3.0600 |
O1···C24Aiii | 3.373 (3) | H5A1···N4A | 2.7800 |
O1···Cl1vi | 3.310 (2) | H5A1···H1A2iii | 2.5000 |
O2···Cl1vi | 3.162 (15) | H5A2···H7A1 | 2.5600 |
O2···C24Bvii | 3.24 (2) | H5A2···C21Aiii | 2.8900 |
O2···C23Bvii | 3.348 (19) | H5A2···C22Aiii | 2.9300 |
O2···Cl2v | 3.261 (15) | H5A2···C23Aiii | 3.0300 |
O4A···C25Bviii | 3.398 (2) | H5A2···C24Aiii | 3.0700 |
O4A···Cl2ix | 3.0245 (14) | H5A2···C25Aiii | 3.0100 |
O4A···C23Bv | 3.393 (3) | H5A2···C26Aiii | 2.9200 |
O4B···C25Ax | 3.355 (2) | H5A2···N4A | 2.7100 |
O4B···Cl2iv | 3.0464 (13) | H6A1···H10A | 2.5500 |
O1···H26Bvi | 2.6600 | H7A1···H5A2 | 2.5600 |
O1···H24Aiii | 2.7300 | H9A···H2A | 2.4500 |
O1···H3B2vi | 2.8800 | H9A···Cl2v | 2.9600 |
O2···H26Avi | 2.8600 | H9B···H2B | 2.4500 |
O2···H23Bvii | 2.8000 | H9B···Cl2 | 2.9500 |
O2···H24Bvii | 2.5600 | H10A···H1A2 | 2.3800 |
O4A···H1A1iii | 2.8000 | H10A···H6A1 | 2.5500 |
O4A···H2Ciii | 2.904 (15) | H10A···Cl1 | 2.8500 |
O4A···H8A2iii | 2.8800 | H10B···H3B2 | 2.5900 |
O4A···H23Bv | 2.5000 | H10B···Cl1 | 2.8600 |
O4A···H25Bviii | 2.4700 | H10B···H1B1 | 2.4000 |
O4A···H3A2 | 2.2300 | H10B···H6B2 | 2.5600 |
O4B···H23Aii | 2.6700 | H8A1···C8B | 2.9800 |
O4B···H3B1 | 2.2300 | H8A1···H1A2 | 2.4500 |
O4B···H25Ax | 2.4700 | H8A1···H8B2 | 2.1100 |
N1A···Cl1 | 3.2011 (14) | H8A2···H1A1 | 2.4400 |
N1A···N4Aiv | 2.9812 (16) | H8A2···O4Aiv | 2.8800 |
N1B···N4Biii | 3.0774 (18) | H8A2···N4Aiv | 2.9300 |
N1B···Cl1 | 3.2013 (15) | H1B1···C4B | 3.0800 |
N4A···N1Aiii | 2.9812 (16) | H1B1···H3B2 | 2.5200 |
N4B···N1Biv | 3.0774 (18) | H1B1···Cl1 | 2.3200 |
N1B···H5B1iii | 2.9400 | H1B1···H5B1iii | 2.4600 |
N4A···H1A1iii | 2.0800 | H1B1···H8B2 | 2.4500 |
N4A···H5A1 | 2.7800 | H1B1···H10B | 2.4000 |
N4A···H5A2 | 2.7100 | H1B2···H8B1 | 2.4500 |
N4A···H8A2iii | 2.9300 | H1B2···N4Biii | 2.1800 |
N4B···H5B1 | 2.7900 | H1B2···C5Biii | 3.0600 |
N4B···H1B2iv | 2.1800 | H1B2···C22B | 2.9500 |
N4B···H5B2 | 2.6900 | H1B2···H5B1iii | 2.5800 |
C2B···Cl2 | 3.6194 (17) | H3B1···O4B | 2.2300 |
C5A···C26Aiii | 3.581 (2) | H3B2···O1i | 2.8800 |
C23B···O2xi | 3.348 (19) | H3B2···H1B1 | 2.5200 |
C23B···O4Aii | 3.393 (3) | H3B2···C26B | 2.7600 |
C24A···O1iv | 3.373 (3) | H3B2···H10B | 2.5900 |
C24B···O2xi | 3.24 (2) | H3B2···H26B | 2.2000 |
C25A···O4Bxii | 3.355 (2) | H5B1···Cl1iv | 2.9600 |
C25B···O4Axiii | 3.398 (2) | H5B1···N1Biv | 2.9400 |
C26A···C5Aiv | 3.581 (2) | H5B1···N4B | 2.7900 |
C3A···H25Bviii | 3.0900 | H5B1···H1B1iv | 2.4600 |
C3A···H26A | 2.7600 | H5B1···H1B2iv | 2.5800 |
C3B···H26B | 2.7200 | H5B2···N4B | 2.6900 |
C4A···H1A2 | 3.0800 | H5B2···H7B2 | 2.5800 |
C4B···H1B1 | 3.0800 | H5B2···C21Biv | 2.9200 |
C5B···H1B2iv | 3.0600 | H5B2···C22Biv | 2.9200 |
C8A···H8B2 | 3.0200 | H5B2···C23Biv | 3.0800 |
C8B···H8A1 | 2.9800 | H5B2···C26Biv | 3.0700 |
C21A···H5A2iv | 2.8900 | H6B2···H10B | 2.5600 |
C21B···H5B2iii | 2.9200 | H6B2···H8B2 | 2.5900 |
C22A···H5A2iv | 2.9300 | H7B2···H5B2 | 2.5800 |
C22A···H1A1 | 3.0900 | H22A···H2Bv | 2.3500 |
C22B···H5B2iii | 2.9200 | H22A···H2A | 2.3200 |
C22B···H1B2 | 2.9500 | H22B···Cl2 | 3.0500 |
C22B···H2Aii | 3.1000 | H22B···H2Aii | 2.4100 |
C23A···H5A2iv | 3.0300 | H22B···H2B | 2.3600 |
C23B···H5B2iii | 3.0800 | H8B1···H1B2 | 2.4500 |
C24A···H5A2iv | 3.0700 | H8B1···C25Axv | 2.9200 |
C25A···H8B1xiv | 2.9200 | H23A···O4Bv | 2.6700 |
C25A···H5A2iv | 3.0100 | H23B···O2xi | 2.8000 |
C26A···H1A2 | 3.0200 | H23B···O4Aii | 2.5000 |
C26A···H5A2iv | 2.9200 | H8B2···H8A1 | 2.1100 |
C26A···H3A1 | 2.7300 | H8B2···H6B2 | 2.5900 |
C26B···H5B2iii | 3.0700 | H8B2···H1B1 | 2.4500 |
C26B···H2Di | 3.07 (3) | H8B2···C8A | 3.0200 |
C26B···H3B2 | 2.7600 | H24A···O1iv | 2.7300 |
H1A1···C22A | 3.0900 | H24B···O2xi | 2.5600 |
H1A1···H4Aiv | 2.6000 | H24B···H3A1xiii | 2.4600 |
H1A1···N4Aiv | 2.0800 | H25A···O4Bxii | 2.4700 |
H1A1···H8A2 | 2.4400 | H25B···C3Axiii | 3.0900 |
H1A1···O4Aiv | 2.8000 | H25B···O4Axiii | 2.4700 |
H1A···Cl2v | 2.587 (3) | H26A···H3A1 | 2.1900 |
H1B···H26Bvi | 2.3400 | H26A···O2i | 2.8600 |
H1B···Cl1vi | 2.498 (4) | H26A···C3A | 2.7600 |
H1A2···H8A1 | 2.4500 | H26A···Cl1 | 3.1100 |
H1A2···H5A1iv | 2.5000 | H26B···C3B | 2.7200 |
H1A2···H3A1 | 2.5300 | H26B···H3B2 | 2.2000 |
H1A2···H10A | 2.3800 | H26B···H1Bi | 2.3400 |
H1A2···C4A | 3.0800 | H26B···H2Di | 2.4400 |
H1A2···C26A | 3.0200 | H26B···O1i | 2.6600 |
N4A—O4A—H4A | 109.00 | C23A—C22A—H22A | 120.00 |
N4B—O4B—H4B | 109.00 | C22A—C23A—H23A | 120.00 |
H1A—O1—H1B | 113.1 (6) | C24A—C23A—H23A | 120.00 |
H2C—O2—H2D | 116 (3) | C25A—C24A—H24A | 120.00 |
C2A—N1A—C9A | 113.25 (11) | C23A—C24A—H24A | 120.00 |
O4A—N4A—C4A | 111.72 (12) | C26A—C25A—H25A | 120.00 |
H1A1—N1A—H1A2 | 108.00 | C24A—C25A—H25A | 120.00 |
C2A—N1A—H1A1 | 109.00 | C25A—C26A—H26A | 120.00 |
C9A—N1A—H1A1 | 109.00 | C21A—C26A—H26A | 120.00 |
C9A—N1A—H1A2 | 109.00 | C3B—C2B—C21B | 115.54 (14) |
C2A—N1A—H1A2 | 109.00 | N1B—C2B—C21B | 109.35 (12) |
C2B—N1B—C9B | 112.70 (11) | N1B—C2B—C3B | 108.60 (13) |
O4B—N4B—C4B | 111.13 (12) | C2B—C3B—C4B | 110.25 (13) |
C2B—N1B—H1B1 | 109.00 | N4B—C4B—C10B | 118.80 (13) |
H1B1—N1B—H1B2 | 108.00 | N4B—C4B—C3B | 126.18 (15) |
C9B—N1B—H1B2 | 109.00 | C3B—C4B—C10B | 114.92 (13) |
C2B—N1B—H1B2 | 109.00 | C6B—C5B—C10B | 111.60 (14) |
C9B—N1B—H1B1 | 109.00 | C5B—C6B—C7B | 111.06 (17) |
N1A—C2A—C21A | 109.93 (12) | C6B—C7B—C8B | 110.99 (16) |
C3A—C2A—C21A | 115.11 (12) | C7B—C8B—C9B | 111.06 (14) |
N1A—C2A—C3A | 108.18 (12) | N1B—C9B—C10B | 108.26 (12) |
C2A—C3A—C4A | 111.62 (12) | N1B—C9B—C8B | 109.32 (12) |
N4A—C4A—C3A | 125.54 (14) | C8B—C9B—C10B | 112.54 (14) |
N4A—C4A—C10A | 119.60 (13) | C4B—C10B—C5B | 116.28 (13) |
C3A—C4A—C10A | 114.85 (13) | C5B—C10B—C9B | 109.96 (13) |
C6A—C5A—C10A | 111.42 (14) | C4B—C10B—C9B | 107.97 (13) |
C5A—C6A—C7A | 110.65 (16) | C2B—C21B—C26B | 122.78 (16) |
C6A—C7A—C8A | 111.24 (15) | C22B—C21B—C26B | 118.72 (16) |
C7A—C8A—C9A | 111.23 (14) | C2B—C21B—C22B | 118.43 (15) |
N1A—C9A—C8A | 109.62 (12) | C21B—C22B—C23B | 120.71 (18) |
C8A—C9A—C10A | 113.12 (14) | C22B—C23B—C24B | 119.6 (2) |
N1A—C9A—C10A | 108.12 (12) | C23B—C24B—C25B | 120.3 (2) |
C4A—C10A—C5A | 115.77 (13) | C24B—C25B—C26B | 120.24 (19) |
C4A—C10A—C9A | 107.93 (13) | C21B—C26B—C25B | 120.42 (19) |
C5A—C10A—C9A | 110.14 (13) | C3B—C2B—H2B | 108.00 |
C2A—C21A—C26A | 122.01 (14) | C21B—C2B—H2B | 108.00 |
C22A—C21A—C26A | 118.69 (15) | N1B—C2B—H2B | 108.00 |
C2A—C21A—C22A | 119.23 (15) | C4B—C3B—H3B1 | 110.00 |
C21A—C22A—C23A | 120.39 (18) | C2B—C3B—H3B1 | 110.00 |
C22A—C23A—C24A | 119.86 (19) | C2B—C3B—H3B2 | 110.00 |
C23A—C24A—C25A | 120.65 (19) | H3B1—C3B—H3B2 | 108.00 |
C24A—C25A—C26A | 119.96 (19) | C4B—C3B—H3B2 | 110.00 |
C21A—C26A—C25A | 120.44 (17) | C6B—C5B—H5B2 | 109.00 |
C21A—C2A—H2A | 108.00 | C6B—C5B—H5B1 | 109.00 |
N1A—C2A—H2A | 108.00 | H5B1—C5B—H5B2 | 108.00 |
C3A—C2A—H2A | 108.00 | C10B—C5B—H5B1 | 109.00 |
C2A—C3A—H3A1 | 109.00 | C10B—C5B—H5B2 | 109.00 |
C2A—C3A—H3A2 | 109.00 | C7B—C6B—H6B1 | 109.00 |
C4A—C3A—H3A1 | 109.00 | C7B—C6B—H6B2 | 109.00 |
C4A—C3A—H3A2 | 109.00 | H6B1—C6B—H6B2 | 108.00 |
H3A1—C3A—H3A2 | 108.00 | C5B—C6B—H6B1 | 109.00 |
C6A—C5A—H5A2 | 109.00 | C5B—C6B—H6B2 | 109.00 |
H5A1—C5A—H5A2 | 108.00 | C6B—C7B—H7B1 | 109.00 |
C10A—C5A—H5A2 | 109.00 | C8B—C7B—H7B2 | 109.00 |
C6A—C5A—H5A1 | 109.00 | C6B—C7B—H7B2 | 109.00 |
C10A—C5A—H5A1 | 109.00 | C8B—C7B—H7B1 | 109.00 |
H6A1—C6A—H6A2 | 108.00 | H7B1—C7B—H7B2 | 108.00 |
C5A—C6A—H6A1 | 110.00 | C7B—C8B—H8B2 | 109.00 |
C7A—C6A—H6A2 | 110.00 | C9B—C8B—H8B1 | 109.00 |
C7A—C6A—H6A1 | 110.00 | H8B1—C8B—H8B2 | 108.00 |
C5A—C6A—H6A2 | 110.00 | C9B—C8B—H8B2 | 109.00 |
C8A—C7A—H7A1 | 109.00 | C7B—C8B—H8B1 | 109.00 |
C6A—C7A—H7A2 | 109.00 | N1B—C9B—H9B | 109.00 |
H7A1—C7A—H7A2 | 108.00 | C10B—C9B—H9B | 109.00 |
C6A—C7A—H7A1 | 109.00 | C8B—C9B—H9B | 109.00 |
C8A—C7A—H7A2 | 109.00 | C5B—C10B—H10B | 107.00 |
C7A—C8A—H8A1 | 109.00 | C9B—C10B—H10B | 107.00 |
C9A—C8A—H8A2 | 109.00 | C4B—C10B—H10B | 107.00 |
C7A—C8A—H8A2 | 109.00 | C21B—C22B—H22B | 120.00 |
C9A—C8A—H8A1 | 109.00 | C23B—C22B—H22B | 120.00 |
H8A1—C8A—H8A2 | 108.00 | C22B—C23B—H23B | 120.00 |
C10A—C9A—H9A | 109.00 | C24B—C23B—H23B | 120.00 |
N1A—C9A—H9A | 109.00 | C25B—C24B—H24B | 120.00 |
C8A—C9A—H9A | 109.00 | C23B—C24B—H24B | 120.00 |
C9A—C10A—H10A | 108.00 | C24B—C25B—H25B | 120.00 |
C5A—C10A—H10A | 108.00 | C26B—C25B—H25B | 120.00 |
C4A—C10A—H10A | 108.00 | C25B—C26B—H26B | 120.00 |
C21A—C22A—H22A | 120.00 | C21B—C26B—H26B | 120.00 |
C9A—N1A—C2A—C3A | −58.84 (16) | C26A—C21A—C22A—C23A | 0.8 (3) |
C9A—N1A—C2A—C21A | 174.71 (12) | C2A—C21A—C26A—C25A | −177.11 (16) |
C2A—N1A—C9A—C8A | −173.23 (13) | C21A—C22A—C23A—C24A | −0.6 (3) |
C2A—N1A—C9A—C10A | 63.05 (16) | C22A—C23A—C24A—C25A | −0.2 (3) |
O4A—N4A—C4A—C3A | 0.9 (2) | C23A—C24A—C25A—C26A | 0.9 (3) |
O4A—N4A—C4A—C10A | 179.48 (13) | C24A—C25A—C26A—C21A | −0.8 (3) |
C9B—N1B—C2B—C3B | −59.89 (16) | N1B—C2B—C3B—C4B | 53.73 (17) |
C9B—N1B—C2B—C21B | 173.23 (13) | C21B—C2B—C3B—C4B | 176.97 (14) |
C2B—N1B—C9B—C8B | −174.93 (13) | N1B—C2B—C21B—C22B | −86.26 (19) |
C2B—N1B—C9B—C10B | 62.15 (16) | N1B—C2B—C21B—C26B | 90.68 (19) |
O4B—N4B—C4B—C3B | 0.7 (2) | C3B—C2B—C21B—C22B | 150.90 (16) |
O4B—N4B—C4B—C10B | 176.86 (13) | C3B—C2B—C21B—C26B | −32.2 (2) |
C3A—C2A—C21A—C26A | −40.8 (2) | C2B—C3B—C4B—N4B | 120.99 (18) |
C21A—C2A—C3A—C4A | 175.02 (14) | C2B—C3B—C4B—C10B | −55.31 (19) |
N1A—C2A—C21A—C22A | −95.33 (17) | N4B—C4B—C10B—C5B | 4.0 (2) |
N1A—C2A—C3A—C4A | 51.65 (17) | N4B—C4B—C10B—C9B | −120.09 (16) |
C3A—C2A—C21A—C22A | 142.23 (16) | C3B—C4B—C10B—C5B | −179.41 (15) |
N1A—C2A—C21A—C26A | 81.69 (18) | C3B—C4B—C10B—C9B | 56.50 (18) |
C2A—C3A—C4A—N4A | 125.11 (17) | C10B—C5B—C6B—C7B | 57.0 (2) |
C2A—C3A—C4A—C10A | −53.58 (19) | C6B—C5B—C10B—C4B | −177.83 (15) |
N4A—C4A—C10A—C5A | 1.0 (2) | C6B—C5B—C10B—C9B | −54.8 (2) |
C3A—C4A—C10A—C9A | 55.82 (18) | C5B—C6B—C7B—C8B | −56.7 (2) |
N4A—C4A—C10A—C9A | −122.96 (15) | C6B—C7B—C8B—C9B | 55.5 (2) |
C3A—C4A—C10A—C5A | 179.74 (14) | C7B—C8B—C9B—N1B | −175.11 (14) |
C6A—C5A—C10A—C9A | −54.96 (19) | C7B—C8B—C9B—C10B | −54.77 (19) |
C10A—C5A—C6A—C7A | 57.8 (2) | N1B—C9B—C10B—C4B | −57.15 (16) |
C6A—C5A—C10A—C4A | −177.73 (15) | N1B—C9B—C10B—C5B | 175.05 (13) |
C5A—C6A—C7A—C8A | −57.1 (2) | C8B—C9B—C10B—C4B | −178.09 (13) |
C6A—C7A—C8A—C9A | 54.7 (2) | C8B—C9B—C10B—C5B | 54.11 (18) |
C7A—C8A—C9A—N1A | −173.94 (14) | C2B—C21B—C22B—C23B | 177.23 (17) |
C7A—C8A—C9A—C10A | −53.20 (19) | C26B—C21B—C22B—C23B | 0.2 (3) |
C8A—C9A—C10A—C5A | 53.22 (18) | C2B—C21B—C26B—C25B | −177.51 (18) |
C8A—C9A—C10A—C4A | −179.52 (13) | C22B—C21B—C26B—C25B | −0.6 (3) |
N1A—C9A—C10A—C4A | −57.94 (16) | C21B—C22B—C23B—C24B | 0.4 (3) |
N1A—C9A—C10A—C5A | 174.81 (13) | C22B—C23B—C24B—C25B | −0.6 (3) |
C2A—C21A—C22A—C23A | 177.89 (17) | C23B—C24B—C25B—C26B | 0.2 (3) |
C22A—C21A—C26A—C25A | −0.1 (3) | C24B—C25B—C26B—C21B | 0.4 (3) |
Symmetry codes: (i) −x+1/2, y−1/2, z+1/2; (ii) x, y, z+1; (iii) x−1/2, −y+1/2, z; (iv) x+1/2, −y+1/2, z; (v) x, y, z−1; (vi) −x+1/2, y+1/2, z−1/2; (vii) x+1/2, −y+1/2, z−1; (viii) −x, −y, z−1/2; (ix) x−1/2, −y+1/2, z−1; (x) −x+1, −y, z+1/2; (xi) x−1/2, −y+1/2, z+1; (xii) −x+1, −y, z−1/2; (xiii) −x, −y, z+1/2; (xiv) −x+1/2, y−1/2, z−1/2; (xv) −x+1/2, y+1/2, z+1/2. |
D—H···A | D—H | H···A | D···A | D—H···A |
N1A—H1A1···N4Aiv | 0.90 | 2.08 | 2.9812 (16) | 174 |
O1—H1A···Cl2v | 0.857 (6) | 2.587 (3) | 3.410 (2) | 161.3 (7) |
O1—H1B···Cl1vi | 0.854 (4) | 2.498 (4) | 3.310 (2) | 159.1 (6) |
N1A—H1A2···Cl1 | 0.90 | 2.32 | 3.2011 (14) | 168 |
O4A—H4A···Cl2ix | 0.82 | 2.23 | 3.0245 (14) | 163 |
O4B—H4B···Cl2iv | 0.82 | 2.23 | 3.0464 (13) | 173 |
N1B—H1B1···Cl1 | 0.90 | 2.32 | 3.2013 (15) | 168 |
N1B—H1B2···N4Biii | 0.90 | 2.18 | 3.0774 (18) | 173 |
C2B—H2B···Cl2 | 0.98 | 2.79 | 3.6194 (17) | 143 |
C3A—H3A2···O4A | 0.97 | 2.23 | 2.671 (2) | 107 |
C3B—H3B1···O4B | 0.97 | 2.23 | 2.669 (2) | 106 |
C23B—H23B···O4Aii | 0.93 | 2.50 | 3.393 (3) | 161 |
C25A—H25A···O4Bxii | 0.93 | 2.47 | 3.355 (2) | 160 |
C25B—H25B···O4Axiii | 0.93 | 2.47 | 3.398 (2) | 172 |
O2—H2C···Cl2v | 0.842 (6) | 2.587 (3) | 3.261 (2) | 137.9 (7) |
O2—H2D···Cl1vi | 0.840 (4) | 2.498 (4) | 3.162 (2) | 136.6 (6) |
Symmetry codes: (ii) x, y, z+1; (iii) x−1/2, −y+1/2, z; (iv) x+1/2, −y+1/2, z; (v) x, y, z−1; (vi) −x+1/2, y+1/2, z−1/2; (ix) x−1/2, −y+1/2, z−1; (xii) −x+1, −y, z−1/2; (xiii) −x, −y, z+1/2. |
Experimental details
Crystal data | |
Chemical formula | C15H21N2O+·Cl−·0.5H2O |
Mr | 289.81 |
Crystal system, space group | Orthorhombic, Pna21 |
Temperature (K) | 293 |
a, b, c (Å) | 13.1733 (4), 18.2824 (5), 12.6656 (4) |
V (Å3) | 3050.38 (16) |
Z | 8 |
Radiation type | Mo Kα |
µ (mm−1) | 0.25 |
Crystal size (mm) | 0.28 × 0.18 × 0.18 |
Data collection | |
Diffractometer | Bruker APEXII |
Absorption correction | Multi-scan (SADABS; Bruker, 2004) |
Tmin, Tmax | 0.743, 0.956 |
No. of measured, independent and observed [I > 2σ(I)] reflections | 15501, 4758, 4335 |
Rint | 0.020 |
(sin θ/λ)max (Å−1) | 0.595 |
Refinement | |
R[F2 > 2σ(F2)], wR(F2), S | 0.028, 0.075, 1.04 |
No. of reflections | 4758 |
No. of parameters | 370 |
No. of restraints | 8 |
H-atom treatment | H atoms treated by a mixture of independent and constrained refinement |
Δρmax, Δρmin (e Å−3) | 0.16, −0.14 |
Absolute structure | Flack (1983), 1936 Friedel pairs |
Absolute structure parameter | −0.02 (5) |
Computer programs: APEX2 (Bruker, 2004), APEX2 (Bruker, 2004, SAINT-NT (Bruker, 2004), DIRDIF99 (Beurskens et al., 1999), SHELXL97 (Sheldrick, 1997), ORTEP-3 (Farrugia, 1997), PLATON (Spek, 2003).
D—H···A | D—H | H···A | D···A | D—H···A |
N1A—H1A1···N4Ai | 0.90 | 2.08 | 2.9812 (16) | 174 |
O1—H1A···Cl2ii | 0.857 (6) | 2.587 (3) | 3.410 (2) | 161.3 (7) |
O1—H1B···Cl1iii | 0.854 (4) | 2.498 (4) | 3.310 (2) | 159.1 (6) |
N1A—H1A2···Cl1 | 0.90 | 2.32 | 3.2011 (14) | 168 |
O4A—H4A···Cl2iv | 0.82 | 2.23 | 3.0245 (14) | 163 |
O4B—H4B···Cl2i | 0.82 | 2.23 | 3.0464 (13) | 173 |
N1B—H1B1···Cl1 | 0.90 | 2.32 | 3.2013 (15) | 168 |
N1B—H1B2···N4Bv | 0.90 | 2.18 | 3.0774 (18) | 173 |
C2B—H2B···Cl2 | 0.98 | 2.79 | 3.6194 (17) | 143 |
C3A—H3A2···O4A | 0.97 | 2.23 | 2.671 (2) | 107 |
C3B—H3B1···O4B | 0.97 | 2.23 | 2.669 (2) | 106 |
C23B—H23B···O4Avi | 0.93 | 2.50 | 3.393 (3) | 161 |
C25A—H25A···O4Bvii | 0.93 | 2.47 | 3.355 (2) | 160 |
C25B—H25B···O4Aviii | 0.93 | 2.47 | 3.398 (2) | 172 |
O2—H2C···Cl2ii | 0.842 (6) | 2.587 (3) | 3.261 (2) | 137.9 (7) |
O2—H2D···Cl1iii | 0.840 (4) | 2.498 (4) | 3.162 (2) | 136.6 (6) |
Symmetry codes: (i) x+1/2, −y+1/2, z; (ii) x, y, z−1; (iii) −x+1/2, y+1/2, z−1/2; (iv) x−1/2, −y+1/2, z−1; (v) x−1/2, −y+1/2, z; (vi) x, y, z+1; (vii) −x+1, −y, z−1/2; (viii) −x, −y, z+1/2. |
The title compound has been analysed as part of our crystallographic studies on substituted decahydroquinolines. Thiruvalluvar et al. (1995) have reported a crystal structure of N-benzoyl-2-phenyldecahydroquinolin-4-one, wherein the piperidine ring adopts a flexible twist conformation. The title compound, Fig. 1., crystallizes with two molecules per asymmetric unit. Both molecules are essentially identical, the r.m.s. deviation of an overlay of all non-hydrogen atoms is only 0.086 Å. The torsion angles (C8—C9—C10—C4 = -179.5 (1)° for molecule A and -178.1 (1)° for molecule B) confirm the trans fusion of the piperidine and cyclohexane rings in both independent molecules. It is evident from the ring torsion angles that the piperidine and cyclohexane rings are both in a chair conformation. The oxime moieties are essentially planar with r.m.s. deviations of only 0.024 (1) Å. The phenyl rings at C2 are equatorially oriented with respect to the piperidine rings. The crystal structure is stabilized by intramolecular N—H···Cl, C—H···Cl, and C—H···O and by intermolecular N—H···N, N—H···Cl, and O—H···Cl hydrogen bonds., see Fig. 2 and the hydrogen bonding table. A water molecule that bridges via hydrogen bonds the two crystallographically independent chlorine anions is disordered over two chemically equivalent sites. Its occupancy ratio refined to 0.905:0.095.