




Supporting information
![]() | Crystallographic Information File (CIF) https://doi.org/10.1107/S1600536812003091/lx2225sup1.cif |
![]() | Structure factor file (CIF format) https://doi.org/10.1107/S1600536812003091/lx2225Isup2.hkl |
![]() | Chemical Markup Language (CML) file https://doi.org/10.1107/S1600536812003091/lx2225Isup3.cml |
CCDC reference: 868239
Key indicators
- Single-crystal X-ray study
- T = 170 K
- Mean
(C-C) = 0.002 Å
- R factor = 0.044
- wR factor = 0.107
- Data-to-parameter ratio = 18.9
checkCIF/PLATON results
No syntax errors found
Alert level C PLAT910_ALERT_3_C Missing # of FCF Reflections Below Th(Min) ..... 9
Alert level G PLAT002_ALERT_2_G Number of Distance or Angle Restraints on AtSite 5 PLAT005_ALERT_5_G No _iucr_refine_instructions_details in CIF .... ? PLAT860_ALERT_3_G Note: Number of Least-Squares Restraints ....... 4
0 ALERT level A = Most likely a serious problem - resolve or explain 0 ALERT level B = A potentially serious problem, consider carefully 1 ALERT level C = Check. Ensure it is not caused by an omission or oversight 3 ALERT level G = General information/check it is not something unexpected 0 ALERT type 1 CIF construction/syntax error, inconsistent or missing data 1 ALERT type 2 Indicator that the structure model may be wrong or deficient 2 ALERT type 3 Indicator that the structure quality may be low 0 ALERT type 4 Improvement, methodology, query or suggestion 1 ALERT type 5 Informative message, check
The title compound was obtained as a gift sample from R. L. Fine Chem, Bangalore. X–ray quality crystals were obtained by slow evaporation of dimethylformamide solution (m.p.: 403-407 K).
H1w, H2w and H2O were located by a difference map and refined isotropically. Ow1 with H1w and H2w were set to DFIX = 0.85 (2)Å, while Hw1 and Hw2 were set to 1.35 (2)Å. H20 with O2 was set to 0.82 (2)Å. All of the remaining H atoms were placed in their calculated positions and then refined using the riding model with Atom—H lengths of 0.93Å (CH), 0.96Å (CH2) or 0.97Å (CH3). Isotropic displacement parameters for these atoms were set to 1.18–1.21 (CH, CH2) or 1.49–1.50 (CH3) times Ueq of the parent atom.
Data collection: CrysAlis PRO (Oxford Diffraction, 2010); cell refinement: CrysAlis PRO (Oxford Diffraction, 2010); data reduction: CrysAlis RED (Oxford Diffraction, 2010); program(s) used to solve structure: SHELXS97 (Sheldrick, 2008); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008); molecular graphics: SHELXTL (Sheldrick, 2008) and DIAMOND (Brandenburg, 1998); software used to prepare material for publication: SHELXTL (Sheldrick, 2008).
C29H33ClN2O2·H2O | F(000) = 2112 |
Mr = 495.04 | Dx = 1.251 Mg m−3 |
Orthorhombic, Pbca | Mo Kα radiation, λ = 0.71073 Å |
Hall symbol: -P 2ac 2ab | Cell parameters from 15584 reflections |
a = 16.7869 (4) Å | θ = 3.1–32.3° |
b = 15.1506 (6) Å | µ = 0.18 mm−1 |
c = 20.6617 (6) Å | T = 170 K |
V = 5254.9 (3) Å3 | Chunk, colorless |
Z = 8 | 0.45 × 0.30 × 0.20 mm |
Oxford Diffraction Xcalibur Eos Gemini diffractometer | 6247 independent reflections |
Radiation source: Enhance (Mo) X-ray Source | 5231 reflections with I > 2σ(I) |
Graphite monochromator | Rint = 0.033 |
Detector resolution: 16.1500 pixels mm-1 | θmax = 27.9°, θmin = 3.1° |
ω scans | h = −22→22 |
Absorption correction: multi-scan (CrysAlis RED; Oxford Diffraction, 2010) | k = −19→19 |
Tmin = 0.989, Tmax = 1.000 | l = −27→27 |
48373 measured reflections |
Refinement on F2 | Primary atom site location: structure-invariant direct methods |
Least-squares matrix: full | Secondary atom site location: difference Fourier map |
R[F2 > 2σ(F2)] = 0.044 | Hydrogen site location: difference Fourier map |
wR(F2) = 0.107 | H atoms treated by a mixture of independent and constrained refinement |
S = 1.04 | w = 1/[σ2(Fo2) + (0.0415P)2 + 2.2656P] where P = (Fo2 + 2Fc2)/3 |
6247 reflections | (Δ/σ)max = 0.001 |
330 parameters | Δρmax = 0.27 e Å−3 |
4 restraints | Δρmin = −0.29 e Å−3 |
C29H33ClN2O2·H2O | V = 5254.9 (3) Å3 |
Mr = 495.04 | Z = 8 |
Orthorhombic, Pbca | Mo Kα radiation |
a = 16.7869 (4) Å | µ = 0.18 mm−1 |
b = 15.1506 (6) Å | T = 170 K |
c = 20.6617 (6) Å | 0.45 × 0.30 × 0.20 mm |
Oxford Diffraction Xcalibur Eos Gemini diffractometer | 6247 independent reflections |
Absorption correction: multi-scan (CrysAlis RED; Oxford Diffraction, 2010) | 5231 reflections with I > 2σ(I) |
Tmin = 0.989, Tmax = 1.000 | Rint = 0.033 |
48373 measured reflections |
R[F2 > 2σ(F2)] = 0.044 | 4 restraints |
wR(F2) = 0.107 | H atoms treated by a mixture of independent and constrained refinement |
S = 1.04 | Δρmax = 0.27 e Å−3 |
6247 reflections | Δρmin = −0.29 e Å−3 |
330 parameters |
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 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 > 2sigma(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 | ||
Cl1 | 1.17722 (2) | 0.58038 (4) | 0.26920 (2) | 0.06055 (15) | |
N1 | 0.47942 (7) | 0.28878 (9) | 0.58732 (6) | 0.0379 (3) | |
N2 | 0.74378 (6) | 0.48771 (7) | 0.48602 (5) | 0.0261 (2) | |
O1 | 0.56971 (7) | 0.30669 (7) | 0.50943 (5) | 0.0394 (3) | |
O2 | 0.85002 (6) | 0.68017 (7) | 0.44131 (5) | 0.0367 (2) | |
H2O | 0.8828 (11) | 0.7037 (13) | 0.4658 (9) | 0.059 (6)* | |
O1W | 0.75307 (10) | 0.33121 (10) | 0.40445 (7) | 0.0636 (4) | |
H1W | 0.7543 (17) | 0.3701 (14) | 0.4371 (11) | 0.101 (9)* | |
H2W | 0.7248 (16) | 0.2875 (14) | 0.4215 (13) | 0.114 (11)* | |
C1 | 1.09073 (8) | 0.58308 (12) | 0.31591 (7) | 0.0390 (4) | |
C2 | 1.06820 (9) | 0.66035 (11) | 0.34473 (8) | 0.0435 (4) | |
H2 | 1.0998 | 0.7104 | 0.3408 | 0.052* | |
C3 | 0.99766 (9) | 0.66366 (10) | 0.37999 (8) | 0.0369 (3) | |
H3 | 0.9822 | 0.7165 | 0.3992 | 0.044* | |
C4 | 0.95013 (8) | 0.58960 (9) | 0.38694 (6) | 0.0288 (3) | |
C5 | 0.97593 (9) | 0.51173 (11) | 0.35815 (8) | 0.0417 (4) | |
H5 | 0.9455 | 0.4609 | 0.3630 | 0.050* | |
C6 | 1.04572 (10) | 0.50782 (12) | 0.32247 (8) | 0.0454 (4) | |
H6 | 1.0618 | 0.4552 | 0.3033 | 0.054* | |
C7 | 0.87288 (8) | 0.59170 (9) | 0.42628 (6) | 0.0269 (3) | |
C8 | 0.80218 (8) | 0.55421 (10) | 0.38837 (6) | 0.0303 (3) | |
H8A | 0.7906 | 0.5926 | 0.3520 | 0.036* | |
H8B | 0.8163 | 0.4966 | 0.3714 | 0.036* | |
C9 | 0.72810 (8) | 0.54558 (10) | 0.43032 (6) | 0.0305 (3) | |
H9A | 0.7120 | 0.6035 | 0.4456 | 0.037* | |
H9B | 0.6848 | 0.5214 | 0.4048 | 0.037* | |
C10 | 0.80641 (9) | 0.52790 (11) | 0.52601 (6) | 0.0335 (3) | |
H10A | 0.8157 | 0.4914 | 0.5638 | 0.040* | |
H10B | 0.7888 | 0.5854 | 0.5408 | 0.040* | |
C11 | 0.88357 (8) | 0.53792 (10) | 0.48847 (6) | 0.0326 (3) | |
H11A | 0.9038 | 0.4798 | 0.4775 | 0.039* | |
H11B | 0.9228 | 0.5667 | 0.5157 | 0.039* | |
C12 | 0.67039 (8) | 0.47411 (9) | 0.52392 (7) | 0.0298 (3) | |
H12A | 0.6268 | 0.4596 | 0.4950 | 0.036* | |
H12B | 0.6568 | 0.5282 | 0.5465 | 0.036* | |
C13 | 0.68173 (8) | 0.39967 (9) | 0.57288 (6) | 0.0287 (3) | |
H13A | 0.7225 | 0.4176 | 0.6035 | 0.034* | |
H13B | 0.7017 | 0.3483 | 0.5500 | 0.034* | |
C14 | 0.60632 (7) | 0.37140 (8) | 0.61187 (6) | 0.0246 (3) | |
C15 | 0.57026 (8) | 0.45613 (8) | 0.63995 (6) | 0.0256 (3) | |
C16 | 0.49950 (9) | 0.49212 (10) | 0.61733 (7) | 0.0354 (3) | |
H16 | 0.4701 | 0.4617 | 0.5863 | 0.042* | |
C17 | 0.47176 (10) | 0.57271 (11) | 0.64016 (8) | 0.0428 (4) | |
H17 | 0.4241 | 0.5956 | 0.6246 | 0.051* | |
C18 | 0.51458 (10) | 0.61866 (10) | 0.68566 (8) | 0.0403 (4) | |
H18 | 0.4953 | 0.6718 | 0.7018 | 0.048* | |
C19 | 0.58649 (9) | 0.58545 (10) | 0.70730 (8) | 0.0371 (3) | |
H19 | 0.6165 | 0.6172 | 0.7371 | 0.044* | |
C20 | 0.61395 (8) | 0.50510 (9) | 0.68474 (7) | 0.0307 (3) | |
H20 | 0.6624 | 0.4833 | 0.6997 | 0.037* | |
C21 | 0.63539 (8) | 0.30328 (9) | 0.66256 (6) | 0.0260 (3) | |
C22 | 0.67485 (10) | 0.22848 (10) | 0.63995 (7) | 0.0363 (3) | |
H22 | 0.6805 | 0.2201 | 0.5956 | 0.044* | |
C23 | 0.70578 (11) | 0.16645 (11) | 0.68201 (8) | 0.0437 (4) | |
H23 | 0.7320 | 0.1171 | 0.6658 | 0.052* | |
C24 | 0.69791 (10) | 0.17757 (10) | 0.74803 (8) | 0.0394 (3) | |
H24 | 0.7197 | 0.1367 | 0.7765 | 0.047* | |
C25 | 0.65740 (9) | 0.24984 (10) | 0.77106 (7) | 0.0345 (3) | |
H25 | 0.6511 | 0.2572 | 0.8155 | 0.041* | |
C26 | 0.62582 (8) | 0.31198 (9) | 0.72898 (6) | 0.0300 (3) | |
H26 | 0.5979 | 0.3600 | 0.7454 | 0.036* | |
C27 | 0.54922 (8) | 0.32055 (9) | 0.56588 (6) | 0.0289 (3) | |
C28 | 0.43120 (11) | 0.23911 (14) | 0.54098 (10) | 0.0598 (5) | |
H28A | 0.4215 | 0.2748 | 0.5034 | 0.090* | |
H28B | 0.3813 | 0.2234 | 0.5606 | 0.090* | |
H28C | 0.4591 | 0.1865 | 0.5285 | 0.090* | |
C29 | 0.44931 (10) | 0.29174 (13) | 0.65343 (9) | 0.0502 (4) | |
H29A | 0.4573 | 0.2354 | 0.6737 | 0.075* | |
H29B | 0.3935 | 0.3053 | 0.6528 | 0.075* | |
H29C | 0.4773 | 0.3364 | 0.6773 | 0.075* |
U11 | U22 | U33 | U12 | U13 | U23 | |
Cl1 | 0.0316 (2) | 0.0921 (4) | 0.0580 (3) | 0.0086 (2) | 0.01224 (18) | 0.0166 (2) |
N1 | 0.0325 (6) | 0.0378 (7) | 0.0433 (7) | −0.0056 (5) | 0.0020 (5) | −0.0085 (6) |
N2 | 0.0259 (5) | 0.0302 (6) | 0.0222 (5) | −0.0031 (4) | 0.0004 (4) | 0.0026 (4) |
O1 | 0.0500 (6) | 0.0377 (6) | 0.0304 (5) | −0.0004 (5) | 0.0027 (5) | −0.0083 (4) |
O2 | 0.0356 (5) | 0.0290 (5) | 0.0454 (6) | −0.0024 (4) | 0.0008 (5) | −0.0055 (5) |
O1W | 0.0782 (10) | 0.0581 (9) | 0.0545 (8) | −0.0109 (8) | 0.0067 (7) | −0.0136 (7) |
C1 | 0.0258 (7) | 0.0588 (10) | 0.0326 (7) | 0.0022 (7) | 0.0012 (6) | 0.0100 (7) |
C2 | 0.0328 (8) | 0.0425 (9) | 0.0551 (10) | −0.0067 (7) | 0.0044 (7) | 0.0118 (7) |
C3 | 0.0348 (7) | 0.0325 (8) | 0.0433 (8) | −0.0040 (6) | 0.0021 (6) | 0.0036 (6) |
C4 | 0.0292 (6) | 0.0325 (7) | 0.0247 (6) | −0.0029 (5) | −0.0019 (5) | 0.0021 (5) |
C5 | 0.0376 (8) | 0.0384 (8) | 0.0491 (9) | −0.0082 (7) | 0.0070 (7) | −0.0096 (7) |
C6 | 0.0379 (8) | 0.0505 (10) | 0.0478 (9) | 0.0008 (7) | 0.0060 (7) | −0.0130 (8) |
C7 | 0.0281 (6) | 0.0262 (6) | 0.0264 (6) | −0.0038 (5) | 0.0007 (5) | −0.0002 (5) |
C8 | 0.0325 (7) | 0.0359 (7) | 0.0226 (6) | −0.0066 (6) | −0.0026 (5) | 0.0036 (5) |
C9 | 0.0287 (7) | 0.0345 (7) | 0.0282 (6) | −0.0031 (6) | −0.0035 (5) | 0.0058 (6) |
C10 | 0.0352 (7) | 0.0433 (8) | 0.0221 (6) | −0.0091 (6) | −0.0025 (5) | 0.0014 (6) |
C11 | 0.0293 (7) | 0.0406 (8) | 0.0280 (6) | −0.0061 (6) | −0.0050 (5) | 0.0047 (6) |
C12 | 0.0272 (6) | 0.0314 (7) | 0.0309 (7) | 0.0015 (5) | 0.0046 (5) | 0.0038 (5) |
C13 | 0.0269 (6) | 0.0313 (7) | 0.0280 (6) | 0.0026 (5) | 0.0060 (5) | 0.0035 (5) |
C14 | 0.0252 (6) | 0.0237 (6) | 0.0249 (6) | 0.0019 (5) | 0.0032 (5) | 0.0000 (5) |
C15 | 0.0260 (6) | 0.0238 (6) | 0.0269 (6) | 0.0008 (5) | 0.0048 (5) | 0.0014 (5) |
C16 | 0.0337 (7) | 0.0324 (7) | 0.0400 (8) | 0.0046 (6) | −0.0053 (6) | −0.0037 (6) |
C17 | 0.0365 (8) | 0.0348 (8) | 0.0571 (10) | 0.0116 (7) | −0.0044 (7) | −0.0015 (7) |
C18 | 0.0440 (8) | 0.0253 (7) | 0.0515 (9) | 0.0068 (6) | 0.0079 (7) | −0.0037 (6) |
C19 | 0.0392 (8) | 0.0293 (7) | 0.0427 (8) | −0.0036 (6) | 0.0002 (6) | −0.0069 (6) |
C20 | 0.0275 (6) | 0.0283 (7) | 0.0363 (7) | 0.0003 (5) | 0.0008 (5) | −0.0009 (6) |
C21 | 0.0261 (6) | 0.0241 (6) | 0.0277 (6) | −0.0002 (5) | 0.0018 (5) | 0.0005 (5) |
C22 | 0.0482 (8) | 0.0329 (8) | 0.0280 (7) | 0.0101 (6) | 0.0012 (6) | −0.0027 (6) |
C23 | 0.0559 (10) | 0.0341 (8) | 0.0411 (8) | 0.0172 (7) | −0.0005 (7) | −0.0005 (7) |
C24 | 0.0463 (8) | 0.0352 (8) | 0.0369 (7) | 0.0051 (7) | −0.0063 (7) | 0.0078 (6) |
C25 | 0.0403 (8) | 0.0370 (8) | 0.0263 (6) | −0.0042 (6) | 0.0009 (6) | 0.0034 (6) |
C26 | 0.0335 (7) | 0.0266 (7) | 0.0299 (7) | −0.0005 (6) | 0.0066 (5) | −0.0011 (5) |
C27 | 0.0326 (7) | 0.0238 (6) | 0.0302 (7) | 0.0043 (5) | −0.0001 (5) | −0.0019 (5) |
C28 | 0.0468 (10) | 0.0601 (12) | 0.0723 (12) | −0.0139 (9) | −0.0054 (9) | −0.0236 (10) |
C29 | 0.0404 (9) | 0.0603 (11) | 0.0500 (10) | −0.0135 (8) | 0.0127 (7) | −0.0020 (8) |
Cl1—C1 | 1.7440 (15) | C12—H12A | 0.9700 |
N1—C27 | 1.3419 (18) | C12—H12B | 0.9700 |
N1—C29 | 1.457 (2) | C13—C14 | 1.5606 (17) |
N1—C28 | 1.462 (2) | C13—H13A | 0.9700 |
N2—C10 | 1.4693 (17) | C13—H13B | 0.9700 |
N2—C9 | 1.4705 (16) | C14—C15 | 1.5332 (17) |
N2—C12 | 1.4743 (16) | C14—C21 | 1.5493 (18) |
O1—C27 | 1.2340 (16) | C14—C27 | 1.5542 (18) |
O2—C7 | 1.4284 (17) | C15—C16 | 1.3880 (19) |
O2—H2O | 0.827 (15) | C15—C20 | 1.3946 (19) |
O1W—H1W | 0.896 (16) | C16—C17 | 1.389 (2) |
O1W—H2W | 0.888 (16) | C16—H16 | 0.9300 |
C1—C2 | 1.367 (2) | C17—C18 | 1.373 (2) |
C1—C6 | 1.375 (2) | C17—H17 | 0.9300 |
C2—C3 | 1.391 (2) | C18—C19 | 1.382 (2) |
C2—H2 | 0.9300 | C18—H18 | 0.9300 |
C3—C4 | 1.384 (2) | C19—C20 | 1.383 (2) |
C3—H3 | 0.9300 | C19—H19 | 0.9300 |
C4—C5 | 1.390 (2) | C20—H20 | 0.9300 |
C4—C7 | 1.5307 (18) | C21—C26 | 1.3879 (18) |
C5—C6 | 1.386 (2) | C21—C22 | 1.3934 (19) |
C5—H5 | 0.9300 | C22—C23 | 1.381 (2) |
C6—H6 | 0.9300 | C22—H22 | 0.9300 |
C7—C8 | 1.5312 (18) | C23—C24 | 1.381 (2) |
C7—C11 | 1.5321 (18) | C23—H23 | 0.9300 |
C8—C9 | 1.5214 (19) | C24—C25 | 1.374 (2) |
C8—H8A | 0.9700 | C24—H24 | 0.9300 |
C8—H8B | 0.9700 | C25—C26 | 1.387 (2) |
C9—H9A | 0.9700 | C25—H25 | 0.9300 |
C9—H9B | 0.9700 | C26—H26 | 0.9300 |
C10—C11 | 1.5174 (19) | C28—H28A | 0.9600 |
C10—H10A | 0.9700 | C28—H28B | 0.9600 |
C10—H10B | 0.9700 | C28—H28C | 0.9600 |
C11—H11A | 0.9700 | C29—H29A | 0.9600 |
C11—H11B | 0.9700 | C29—H29B | 0.9600 |
C12—C13 | 1.5269 (18) | C29—H29C | 0.9600 |
C27—N1—C29 | 126.97 (13) | C12—C13—H13A | 108.2 |
C27—N1—C28 | 116.86 (13) | C14—C13—H13A | 108.2 |
C29—N1—C28 | 115.94 (14) | C12—C13—H13B | 108.2 |
C10—N2—C9 | 108.73 (11) | C14—C13—H13B | 108.2 |
C10—N2—C12 | 110.93 (10) | H13A—C13—H13B | 107.4 |
C9—N2—C12 | 110.46 (10) | C15—C14—C21 | 115.23 (10) |
C7—O2—H2O | 111.0 (15) | C15—C14—C27 | 113.76 (10) |
H1W—O1W—H2W | 101.9 (19) | C21—C14—C27 | 106.10 (10) |
C2—C1—C6 | 121.03 (14) | C15—C14—C13 | 106.61 (10) |
C2—C1—Cl1 | 119.44 (13) | C21—C14—C13 | 106.04 (10) |
C6—C1—Cl1 | 119.52 (13) | C27—C14—C13 | 108.71 (10) |
C1—C2—C3 | 119.64 (15) | C16—C15—C20 | 117.68 (12) |
C1—C2—H2 | 120.2 | C16—C15—C14 | 122.64 (12) |
C3—C2—H2 | 120.2 | C20—C15—C14 | 119.27 (11) |
C4—C3—C2 | 121.05 (15) | C15—C16—C17 | 121.18 (14) |
C4—C3—H3 | 119.5 | C15—C16—H16 | 119.4 |
C2—C3—H3 | 119.5 | C17—C16—H16 | 119.4 |
C3—C4—C5 | 117.63 (13) | C18—C17—C16 | 120.17 (14) |
C3—C4—C7 | 121.77 (13) | C18—C17—H17 | 119.9 |
C5—C4—C7 | 120.58 (12) | C16—C17—H17 | 119.9 |
C6—C5—C4 | 121.82 (15) | C17—C18—C19 | 119.61 (14) |
C6—C5—H5 | 119.1 | C17—C18—H18 | 120.2 |
C4—C5—H5 | 119.1 | C19—C18—H18 | 120.2 |
C1—C6—C5 | 118.80 (16) | C18—C19—C20 | 120.19 (14) |
C1—C6—H6 | 120.6 | C18—C19—H19 | 119.9 |
C5—C6—H6 | 120.6 | C20—C19—H19 | 119.9 |
O2—C7—C4 | 111.26 (11) | C19—C20—C15 | 121.11 (13) |
O2—C7—C8 | 104.54 (11) | C19—C20—H20 | 119.4 |
C4—C7—C8 | 112.17 (11) | C15—C20—H20 | 119.4 |
O2—C7—C11 | 110.37 (11) | C26—C21—C22 | 117.64 (12) |
C4—C7—C11 | 109.57 (11) | C26—C21—C14 | 124.66 (12) |
C8—C7—C11 | 108.81 (11) | C22—C21—C14 | 117.70 (11) |
C9—C8—C7 | 111.97 (11) | C23—C22—C21 | 121.41 (13) |
C9—C8—H8A | 109.2 | C23—C22—H22 | 119.3 |
C7—C8—H8A | 109.2 | C21—C22—H22 | 119.3 |
C9—C8—H8B | 109.2 | C24—C23—C22 | 120.18 (14) |
C7—C8—H8B | 109.2 | C24—C23—H23 | 119.9 |
H8A—C8—H8B | 107.9 | C22—C23—H23 | 119.9 |
N2—C9—C8 | 110.54 (11) | C25—C24—C23 | 119.12 (14) |
N2—C9—H9A | 109.5 | C25—C24—H24 | 120.4 |
C8—C9—H9A | 109.5 | C23—C24—H24 | 120.4 |
N2—C9—H9B | 109.5 | C24—C25—C26 | 120.86 (13) |
C8—C9—H9B | 109.5 | C24—C25—H25 | 119.6 |
H9A—C9—H9B | 108.1 | C26—C25—H25 | 119.6 |
N2—C10—C11 | 111.40 (11) | C25—C26—C21 | 120.74 (13) |
N2—C10—H10A | 109.3 | C25—C26—H26 | 119.6 |
C11—C10—H10A | 109.3 | C21—C26—H26 | 119.6 |
N2—C10—H10B | 109.3 | O1—C27—N1 | 119.63 (13) |
C11—C10—H10B | 109.3 | O1—C27—C14 | 119.36 (12) |
H10A—C10—H10B | 108.0 | N1—C27—C14 | 120.96 (12) |
C10—C11—C7 | 112.46 (11) | N1—C28—H28A | 109.5 |
C10—C11—H11A | 109.1 | N1—C28—H28B | 109.5 |
C7—C11—H11A | 109.1 | H28A—C28—H28B | 109.5 |
C10—C11—H11B | 109.1 | N1—C28—H28C | 109.5 |
C7—C11—H11B | 109.1 | H28A—C28—H28C | 109.5 |
H11A—C11—H11B | 107.8 | H28B—C28—H28C | 109.5 |
N2—C12—C13 | 110.54 (11) | N1—C29—H29A | 109.5 |
N2—C12—H12A | 109.5 | N1—C29—H29B | 109.5 |
C13—C12—H12A | 109.5 | H29A—C29—H29B | 109.5 |
N2—C12—H12B | 109.5 | N1—C29—H29C | 109.5 |
C13—C12—H12B | 109.5 | H29A—C29—H29C | 109.5 |
H12A—C12—H12B | 108.1 | H29B—C29—H29C | 109.5 |
C12—C13—C14 | 116.33 (11) | ||
C6—C1—C2—C3 | −1.6 (2) | C13—C14—C15—C16 | 108.68 (14) |
Cl1—C1—C2—C3 | 177.56 (12) | C21—C14—C15—C20 | 53.60 (16) |
C1—C2—C3—C4 | 0.6 (2) | C27—C14—C15—C20 | 176.46 (12) |
C2—C3—C4—C5 | 0.8 (2) | C13—C14—C15—C20 | −63.74 (15) |
C2—C3—C4—C7 | 179.21 (13) | C20—C15—C16—C17 | −2.2 (2) |
C3—C4—C5—C6 | −1.3 (2) | C14—C15—C16—C17 | −174.70 (14) |
C7—C4—C5—C6 | −179.78 (14) | C15—C16—C17—C18 | 0.3 (3) |
C2—C1—C6—C5 | 1.0 (3) | C16—C17—C18—C19 | 1.8 (3) |
Cl1—C1—C6—C5 | −178.10 (13) | C17—C18—C19—C20 | −2.0 (2) |
C4—C5—C6—C1 | 0.5 (3) | C18—C19—C20—C15 | 0.1 (2) |
C3—C4—C7—O2 | 12.31 (18) | C16—C15—C20—C19 | 1.9 (2) |
C5—C4—C7—O2 | −169.32 (13) | C14—C15—C20—C19 | 174.73 (13) |
C3—C4—C7—C8 | 129.02 (14) | C15—C14—C21—C26 | 4.52 (18) |
C5—C4—C7—C8 | −52.61 (17) | C27—C14—C21—C26 | −122.32 (14) |
C3—C4—C7—C11 | −110.02 (15) | C13—C14—C21—C26 | 122.19 (14) |
C5—C4—C7—C11 | 68.35 (16) | C15—C14—C21—C22 | −174.61 (12) |
O2—C7—C8—C9 | −66.58 (14) | C27—C14—C21—C22 | 58.54 (15) |
C4—C7—C8—C9 | 172.74 (11) | C13—C14—C21—C22 | −56.95 (15) |
C11—C7—C8—C9 | 51.34 (15) | C26—C21—C22—C23 | −2.1 (2) |
C10—N2—C9—C8 | 62.26 (14) | C14—C21—C22—C23 | 177.10 (15) |
C12—N2—C9—C8 | −175.80 (11) | C21—C22—C23—C24 | 0.1 (3) |
C7—C8—C9—N2 | −58.86 (15) | C22—C23—C24—C25 | 1.5 (3) |
C9—N2—C10—C11 | −61.25 (15) | C23—C24—C25—C26 | −1.1 (2) |
C12—N2—C10—C11 | 177.10 (12) | C24—C25—C26—C21 | −0.9 (2) |
N2—C10—C11—C7 | 56.54 (17) | C22—C21—C26—C25 | 2.5 (2) |
O2—C7—C11—C10 | 64.01 (15) | C14—C21—C26—C25 | −176.64 (13) |
C4—C7—C11—C10 | −173.13 (12) | C29—N1—C27—O1 | 173.93 (16) |
C8—C7—C11—C10 | −50.16 (16) | C28—N1—C27—O1 | −0.3 (2) |
C10—N2—C12—C13 | −71.26 (15) | C29—N1—C27—C14 | −3.6 (2) |
C9—N2—C12—C13 | 168.11 (11) | C28—N1—C27—C14 | −177.83 (14) |
N2—C12—C13—C14 | −174.15 (11) | C15—C14—C27—O1 | 121.16 (13) |
C12—C13—C14—C15 | −50.72 (15) | C21—C14—C27—O1 | −111.12 (13) |
C12—C13—C14—C21 | −173.99 (11) | C13—C14—C27—O1 | 2.55 (17) |
C12—C13—C14—C27 | 72.30 (15) | C15—C14—C27—N1 | −61.33 (16) |
C21—C14—C15—C16 | −133.97 (13) | C21—C14—C27—N1 | 66.39 (15) |
C27—C14—C15—C16 | −11.12 (18) | C13—C14—C27—N1 | −179.94 (12) |
D—H···A | D—H | H···A | D···A | D—H···A |
O1W—H2W···O2i | 0.89 (2) | 2.10 (2) | 2.9684 (19) | 168 (3) |
O1W—H1W···N2 | 0.90 (2) | 2.06 (2) | 2.9132 (18) | 160 (2) |
O2—H2O···O1ii | 0.83 (2) | 1.97 (2) | 2.7333 (15) | 153 (2) |
C28—H28B···O1Wiii | 0.96 | 2.42 | 3.369 (3) | 171 |
Symmetry codes: (i) −x+3/2, y−1/2, z; (ii) −x+3/2, y+1/2, z; (iii) x−1/2, −y+1/2, −z+1. |
Experimental details
Crystal data | |
Chemical formula | C29H33ClN2O2·H2O |
Mr | 495.04 |
Crystal system, space group | Orthorhombic, Pbca |
Temperature (K) | 170 |
a, b, c (Å) | 16.7869 (4), 15.1506 (6), 20.6617 (6) |
V (Å3) | 5254.9 (3) |
Z | 8 |
Radiation type | Mo Kα |
µ (mm−1) | 0.18 |
Crystal size (mm) | 0.45 × 0.30 × 0.20 |
Data collection | |
Diffractometer | Oxford Diffraction Xcalibur Eos Gemini diffractometer |
Absorption correction | Multi-scan (CrysAlis RED; Oxford Diffraction, 2010) |
Tmin, Tmax | 0.989, 1.000 |
No. of measured, independent and observed [I > 2σ(I)] reflections | 48373, 6247, 5231 |
Rint | 0.033 |
(sin θ/λ)max (Å−1) | 0.658 |
Refinement | |
R[F2 > 2σ(F2)], wR(F2), S | 0.044, 0.107, 1.04 |
No. of reflections | 6247 |
No. of parameters | 330 |
No. of restraints | 4 |
H-atom treatment | H atoms treated by a mixture of independent and constrained refinement |
Δρmax, Δρmin (e Å−3) | 0.27, −0.29 |
Computer programs: CrysAlis PRO (Oxford Diffraction, 2010), CrysAlis RED (Oxford Diffraction, 2010), SHELXS97 (Sheldrick, 2008), SHELXL97 (Sheldrick, 2008), SHELXTL (Sheldrick, 2008) and DIAMOND (Brandenburg, 1998), SHELXTL (Sheldrick, 2008).
D—H···A | D—H | H···A | D···A | D—H···A |
O1W—H2W···O2i | 0.888 (16) | 2.095 (17) | 2.9684 (19) | 168 (3) |
O1W—H1W···N2 | 0.896 (16) | 2.056 (17) | 2.9132 (18) | 160 (2) |
O2—H2O···O1ii | 0.827 (15) | 1.971 (17) | 2.7333 (15) | 153 (2) |
C28—H28B···O1Wiii | 0.96 | 2.42 | 3.369 (3) | 171.0 |
Symmetry codes: (i) −x+3/2, y−1/2, z; (ii) −x+3/2, y+1/2, z; (iii) x−1/2, −y+1/2, −z+1. |
Loperamide, a butyramide derivative is a new agent for use in symptomatic control of acute non-specific diarrhoea and chronic diarrhoea. Loperamide is a synthetic piperidine derivative, an opioid drug effective against diarrhea resulting from gastroenteritis or inflammatory bowel disease. Loperamide is an opioid-receptor agonist and acts on the µ-opioid receptors in the myenteric plexus of the large intestine; by itself it does not affect the central nervous system like other opioids. A review of its pharmacological properties and therapeutic efficacy in diarrhoea is reported (Heel et al., 1978). The crystal structures of loperamide hydrochloride tetrahydrate (Caira et al., 1995) and loperamide N-oxide hydrate (Peeters et al., 1996) have been reported. The crystal structure of the title compound was first reported [Germain, et al. (1977) Acta Cryst. B33, 942–944] with an R value of 9% at room temperature. The present paper is a redetermination of the title compound, C29H33ClN2O2Cl . H2O, at 170 (2) K with a high accuracy, hydrogen atom coordinates and an R value of 4.39%.
The title compound, is a synthetic piperidine derivative, an opioid drug effective against diarrhea resulting from gastroenteritis or inflammatory bowel disease. It consists of a piperidin–1–yl ring (distorted chair conformation with (Cremer & Pople, 1975) puckering parameters Q, θ and ϕ of 0.5771 (4)Å, 173.87 (14)° and 195.2 (14)°), with N,N-dimethyl-α,α-diphenylbutyramide and p-chlorophenyl and hydroxy groups bonded in para positions and an external water molecule within the asymmetric unit (Fig. 1). The dihedral angles between the mean planes of the piperidin–1–yl ring, chlorophenyl and two benzene rings are 83.4 (5)°, 76.4 (2)° and 85.9 (2)°, respectively. The two benzene rings are separated by 50.8 (6)°. Crystal packing (fig. 2) is stabilized by O2—H2O···O1 hydrogen bonds from the molecule along with O1w—H2w···O2 and O1w—H1w···N2 hydrogen bonds and weak C28—H28B···O1w intermolecular interactions between the monohydrate water molecule and the title compound (Table 1) forming an infinite 2–D network along [110].