


Supporting information
![]() | Crystallographic Information File (CIF) https://doi.org/10.1107/S1600536810013309/nc2178sup1.cif |
![]() | Structure factor file (CIF format) https://doi.org/10.1107/S1600536810013309/nc2178Isup2.hkl |
CCDC reference: 685375
Key indicators
- Single-crystal X-ray study
- T = 298 K
- Mean
(C-C) = 0.003 Å
- R factor = 0.048
- wR factor = 0.146
- Data-to-parameter ratio = 29.8
checkCIF/PLATON results
No syntax errors found
Alert level C PLAT601_ALERT_2_C Structure Contains Solvent Accessible VOIDS of . 33.00 A 3 PLAT911_ALERT_3_C Missing # FCF Refl Between THmin & STh/L= 0.600 7 PLAT913_ALERT_3_C Missing # of Very Strong Reflections in FCF .... 1 PLAT912_ALERT_4_C Missing # of FCF Reflections Above STh/L= 0.600 93 PLAT927_ALERT_1_C Reported and Calculated wR2 * 100.0 Differ by . -0.18
Alert level G PLAT793_ALERT_4_G The Model has Chirality at C3A (Verify) .... S PLAT793_ALERT_4_G The Model has Chirality at C7A (Verify) .... R PLAT793_ALERT_4_G The Model has Chirality at C8 (Verify) .... R
0 ALERT level A = In general: serious problem 0 ALERT level B = Potentially serious problem 5 ALERT level C = Check and explain 3 ALERT level G = General alerts; check 1 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 4 ALERT type 4 Improvement, methodology, query or suggestion 0 ALERT type 5 Informative message, check
2-Methyl-11-(2-chlorophenyl)-4-[(E)-(2-chlorophenyl)methylidene]- 1,2,3,4,11,11a-hexahydro-pyrido[3,4-c][1,5]benzothiazepines (1 mmol) and 4-chloro-N-hydroxybenzenecarboximidoyl chloride (1 mmol) were dissolved in benzene (15 ml). Triethylamine (1 mmol) was added to the mixture and refluxed for 20 to 30 min. After completion of the reaction as evident from thin layer chromatography the triethylamine hydrochloride was filtered off, solvent evaporated, product was purified by column chromatography using petroleum ether:ethyl acetate (90:10 v/v) mixture and finally recrystallized from ethyl acetate to obtain pure 1-(4-chlorophenyl)-8-(2-chlorophenyl) -4-[(E)-(2-chlorophenyl)methylidene]-6-methyl-4,5,6,7,7a,8- hexahydro[1,2,4]oxa-diazolo[5,4-d]pyrido[3,4-c][1,5] benzothiazepine as colorless crystals.
H atoms were positioned geometrically and refined using a riding model with C—H = 0.95–0.99 Å and with Uiso(H) = 1.2 (1.5 for methyl groups) times Ueq(C).
The title compound, C33H26N3OCl3 S, belongs to an important class of heterocycles which exhibit antihypertensive properties. The compound consists of a benzothiazepine, a oxadiazole and a methyl piperidine ring. Benziothiazepines are regarded as a class of calcium channel blockers (Budriesi et al., 2007), oxadiazol derivatives are established as micobicides (Sahin et al., 2002) and piperidines are established as key components of anti-Parkinson's drugs. Accurate description of the molecular geometry of such molecules are indispensable to proceed with the pharmacological investigations which may prove useful in the design of drugs with a wide range of activities. Also, the role of non-conventional hydrogen bonds viz. C—H···X (X= N, O, Cl, F, etc.) in influencing the geometry of the molecular packing can be unambiguously assessed. Recently, an anlogue of the title compound namely, the crystal structure of 1-(4-chlorophenyl)- 8-(4-fluorophenyl)-4-[(E)-(4-fluorophenyl)methylidene]-6-methyl-4,5,6,7,7a, 8-hexahydro[1,2,4]oxadiazolo[5,4-d]pyrido [3,4-c][1,5] benzothiazepine (Srinivasan et al., 2007) was elucidated.
A least-squares plane calculations show that the 2-chlorophenyl attached to thiazepine, 2-chlorophenyl attached to piperidine and 4-chlorophenyl ring of the oxadiazole ring make a dihedral angle of 34.8 (1) °, 51.3 (1) ° and 73.9 (1) °, respectively, with respect to the benzene fused to the thiazepine ring. The torsion angles about the methylidene bond C4—C40—C41—C42 = 39.8 (2) ° and C4—C40—C41—C46 = -141.8 (2) ° indicates a significant twist of the 2-chlorophenyl ring which may be attributed to steric factors. These values that describe the molecular geometry slightly differ from those observed in the 4-fluoro-4-fluoro- 4-chloro analogue (Srinivasan et al., 2007). The oxadiazole, piperidine and benzothiapezine rings adopt the usually expected envelope, chair and twist-boat conformations, respectively. The molecular aggreagation is characterized by linear chains of centrosymmetrically related pairs extending parallel to the (202) plane and connected through Cl···Cl interactions [Cl1···Cl2(-x+1,-y,-z+2) = 3.533 (2) Å. Other Cl···Cl distances observed are Cl2···Cl2(-x+1,-y+1,-z+1) = 3.826 (2) Å and Cl1···Cl3(x,+y-1,+z+1) = 3.952 (2) Å.
For the biological importance of benziothiazepines and oxadiazol derivatives, see: Budriesi et al. (2007); Sahin et al. (2002).For ring geometry, see: Boeyens (1978); Cremer & Pople (1975). For a related structure, see: Srinivasan et al. (2007).
Data collection: APEX2 (Bruker, 2004); cell refinement: SAINT-Plus (Bruker, 2004); data reduction: SAINT-Plus (Bruker, 2004); program(s) used to solve structure: SHELXS97 (Sheldrick, 2008); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008); molecular graphics: PLATON (Spek, 2009); software used to prepare material for publication: SHELXL97 (Sheldrick, 2008).
C33H26Cl3N3OS | Z = 2 |
Mr = 618.98 | F(000) = 640 |
Triclinic, P1 | Dx = 1.378 Mg m−3 |
Hall symbol: -P 1 | Mo Kα radiation, λ = 0.71073 Å |
a = 11.015 (3) Å | Cell parameters from 4125 reflections |
b = 11.758 (4) Å | θ = 2.0–30.0° |
c = 11.988 (4) Å | µ = 0.41 mm−1 |
α = 78.87 (2)° | T = 298 K |
β = 86.89 (3)° | Needle, colourless |
γ = 78.29 (2)° | 0.30 × 0.15 × 0.15 mm |
V = 1491.5 (8) Å3 |
Bruker Kappa APEXII CCD diffractometer | 11096 independent reflections |
Radiation source: fine-focus sealed tube | 7867 reflections with I > 2σ(I) |
Graphite monochromator | Rint = 0.023 |
ω and φ scan | θmax = 33.0°, θmin = 1.7° |
Absorption correction: multi-scan (SADABS; Sheldrick, 2004) | h = −16→16 |
Tmin = 0.90, Tmax = 0.94 | k = −17→17 |
42055 measured reflections | l = −18→18 |
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)] = 0.048 | Hydrogen site location: inferred from neighbouring sites |
wR(F2) = 0.146 | H-atom parameters constrained |
S = 1.03 | w = 1/[σ2(Fo2) + (0.0605P)2 + 0.6302P] where P = (Fo2 + 2Fc2)/3 |
11096 reflections | (Δ/σ)max = 0.001 |
372 parameters | Δρmax = 0.64 e Å−3 |
0 restraints | Δρmin = −0.62 e Å−3 |
C33H26Cl3N3OS | γ = 78.29 (2)° |
Mr = 618.98 | V = 1491.5 (8) Å3 |
Triclinic, P1 | Z = 2 |
a = 11.015 (3) Å | Mo Kα radiation |
b = 11.758 (4) Å | µ = 0.41 mm−1 |
c = 11.988 (4) Å | T = 298 K |
α = 78.87 (2)° | 0.30 × 0.15 × 0.15 mm |
β = 86.89 (3)° |
Bruker Kappa APEXII CCD diffractometer | 11096 independent reflections |
Absorption correction: multi-scan (SADABS; Sheldrick, 2004) | 7867 reflections with I > 2σ(I) |
Tmin = 0.90, Tmax = 0.94 | Rint = 0.023 |
42055 measured reflections |
R[F2 > 2σ(F2)] = 0.048 | 0 restraints |
wR(F2) = 0.146 | H-atom parameters constrained |
S = 1.03 | Δρmax = 0.64 e Å−3 |
11096 reflections | Δρmin = −0.62 e Å−3 |
372 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 > 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 | ||
Cl1 | 0.57470 (7) | −0.12556 (6) | 1.22882 (7) | 0.0878 (2) | |
Cl2 | 0.55422 (5) | 0.34566 (6) | 0.58843 (6) | 0.07294 (17) | |
Cl3 | 0.71901 (7) | 0.77874 (5) | 0.53545 (4) | 0.0769 (2) | |
C1 | 0.85278 (14) | 0.22540 (11) | 0.96401 (12) | 0.0336 (3) | |
N2 | 0.97082 (12) | 0.20144 (11) | 0.95229 (12) | 0.0404 (3) | |
O3 | 1.00715 (9) | 0.30577 (9) | 0.89247 (9) | 0.0378 (2) | |
C3A | 0.89581 (12) | 0.37735 (11) | 0.83332 (11) | 0.0300 (2) | |
C4 | 0.89945 (13) | 0.33994 (11) | 0.71870 (12) | 0.0320 (3) | |
C5 | 1.01522 (14) | 0.36089 (13) | 0.65093 (13) | 0.0368 (3) | |
H5A | 1.0857 | 0.3030 | 0.6843 | 0.044* | |
H5B | 1.0069 | 0.3495 | 0.5739 | 0.044* | |
N6 | 1.03901 (12) | 0.48001 (11) | 0.64726 (10) | 0.0353 (2) | |
C7 | 1.03493 (13) | 0.51369 (13) | 0.75868 (13) | 0.0355 (3) | |
H7A | 1.0489 | 0.5938 | 0.7497 | 0.043* | |
H7B | 1.1005 | 0.4617 | 0.8053 | 0.043* | |
C7A | 0.90965 (12) | 0.50621 (11) | 0.81809 (12) | 0.0307 (2) | |
H71A | 0.9104 | 0.5276 | 0.8931 | 0.037* | |
C8 | 0.80644 (13) | 0.59400 (11) | 0.74674 (12) | 0.0315 (2) | |
H8 | 0.8252 | 0.5869 | 0.6672 | 0.038* | |
S9 | 0.65096 (3) | 0.56089 (3) | 0.77852 (3) | 0.03747 (9) | |
C9A | 0.65984 (13) | 0.52634 (12) | 0.92758 (13) | 0.0333 (3) | |
C10 | 0.59577 (15) | 0.60462 (13) | 0.99383 (16) | 0.0439 (3) | |
H10 | 0.5521 | 0.6780 | 0.9589 | 0.053* | |
C11 | 0.59637 (17) | 0.57444 (16) | 1.11118 (17) | 0.0484 (4) | |
H11 | 0.5521 | 0.6266 | 1.1549 | 0.058* | |
C12 | 0.66289 (16) | 0.46670 (16) | 1.16287 (14) | 0.0437 (3) | |
H12 | 0.6613 | 0.4453 | 1.2417 | 0.052* | |
C13 | 0.73233 (14) | 0.38968 (13) | 1.09826 (13) | 0.0368 (3) | |
H13 | 0.7803 | 0.3188 | 1.1340 | 0.044* | |
C13A | 0.73021 (12) | 0.41847 (11) | 0.98022 (12) | 0.0303 (2) | |
N14 | 0.79641 (11) | 0.34047 (9) | 0.91010 (10) | 0.0300 (2) | |
C61 | 1.15951 (16) | 0.48759 (16) | 0.59264 (15) | 0.0462 (4) | |
H61A | 1.1759 | 0.5652 | 0.5899 | 0.069* | |
H61B | 1.1591 | 0.4726 | 0.5168 | 0.069* | |
H61C | 1.2229 | 0.4299 | 0.6354 | 0.069* | |
C1E | 0.78313 (14) | 0.13884 (11) | 1.02695 (12) | 0.0350 (3) | |
C2E | 0.65779 (16) | 0.15047 (14) | 1.01121 (16) | 0.0458 (4) | |
H2E | 0.6168 | 0.2127 | 0.9579 | 0.055* | |
C3E | 0.59237 (19) | 0.07021 (16) | 1.07412 (19) | 0.0555 (5) | |
H3E | 0.5074 | 0.0796 | 1.0650 | 0.067* | |
C4E | 0.6548 (2) | −0.02356 (15) | 1.15020 (17) | 0.0527 (4) | |
C5E | 0.7800 (2) | −0.03845 (15) | 1.16498 (16) | 0.0529 (4) | |
H5E | 0.8211 | −0.1032 | 1.2156 | 0.063* | |
C6E | 0.84464 (17) | 0.04309 (13) | 1.10441 (14) | 0.0443 (3) | |
H6E | 0.9293 | 0.0341 | 1.1153 | 0.053* | |
C40 | 0.80948 (15) | 0.29252 (12) | 0.68793 (12) | 0.0364 (3) | |
H40 | 0.7441 | 0.2867 | 0.7398 | 0.044* | |
C41 | 0.79968 (17) | 0.24807 (13) | 0.58271 (13) | 0.0419 (3) | |
C42 | 0.9013 (2) | 0.18426 (17) | 0.53161 (17) | 0.0557 (5) | |
H42 | 0.9788 | 0.1682 | 0.5647 | 0.067* | |
C43 | 0.8879 (3) | 0.1446 (2) | 0.4319 (2) | 0.0757 (7) | |
H43 | 0.9568 | 0.1037 | 0.3980 | 0.091* | |
C44 | 0.7738 (3) | 0.1654 (2) | 0.38322 (19) | 0.0815 (8) | |
H44 | 0.7656 | 0.1387 | 0.3164 | 0.098* | |
C45 | 0.6718 (3) | 0.2253 (2) | 0.43257 (18) | 0.0690 (6) | |
H45 | 0.5942 | 0.2383 | 0.4002 | 0.083* | |
C46 | 0.68514 (19) | 0.26646 (16) | 0.53113 (15) | 0.0503 (4) | |
C81 | 0.80119 (13) | 0.72208 (12) | 0.75331 (12) | 0.0336 (3) | |
C82 | 0.82787 (18) | 0.75779 (14) | 0.85131 (15) | 0.0460 (4) | |
H82 | 0.8572 | 0.7006 | 0.9140 | 0.055* | |
C83 | 0.8122 (2) | 0.87629 (16) | 0.85885 (19) | 0.0585 (5) | |
H83 | 0.8297 | 0.8974 | 0.9262 | 0.070* | |
C84 | 0.7708 (2) | 0.96217 (16) | 0.7669 (2) | 0.0635 (5) | |
H84 | 0.7607 | 1.0416 | 0.7717 | 0.076* | |
C85 | 0.7445 (2) | 0.93064 (15) | 0.66774 (18) | 0.0598 (5) | |
H85 | 0.7168 | 0.9885 | 0.6050 | 0.072* | |
C86 | 0.75923 (17) | 0.81224 (14) | 0.66168 (14) | 0.0436 (3) |
U11 | U22 | U33 | U12 | U13 | U23 | |
Cl1 | 0.1016 (5) | 0.0606 (3) | 0.0984 (5) | −0.0388 (3) | 0.0198 (4) | 0.0104 (3) |
Cl2 | 0.0590 (3) | 0.0861 (4) | 0.0774 (4) | −0.0188 (3) | −0.0099 (3) | −0.0169 (3) |
Cl3 | 0.1281 (5) | 0.0532 (3) | 0.0411 (2) | 0.0047 (3) | −0.0262 (3) | −0.0051 (2) |
C1 | 0.0396 (7) | 0.0255 (5) | 0.0314 (6) | 0.0003 (5) | 0.0013 (5) | −0.0025 (5) |
N2 | 0.0403 (6) | 0.0324 (6) | 0.0411 (7) | 0.0011 (5) | 0.0000 (5) | 0.0022 (5) |
O3 | 0.0318 (5) | 0.0364 (5) | 0.0399 (5) | −0.0018 (4) | −0.0024 (4) | 0.0015 (4) |
C3A | 0.0312 (6) | 0.0271 (5) | 0.0302 (6) | −0.0029 (4) | −0.0011 (5) | −0.0043 (4) |
C4 | 0.0377 (7) | 0.0256 (5) | 0.0318 (6) | −0.0046 (5) | 0.0018 (5) | −0.0054 (4) |
C5 | 0.0399 (7) | 0.0343 (6) | 0.0366 (7) | −0.0070 (5) | 0.0049 (6) | −0.0091 (5) |
N6 | 0.0375 (6) | 0.0350 (6) | 0.0335 (6) | −0.0097 (5) | 0.0018 (5) | −0.0044 (4) |
C7 | 0.0357 (7) | 0.0349 (6) | 0.0371 (7) | −0.0096 (5) | −0.0016 (5) | −0.0067 (5) |
C7A | 0.0334 (6) | 0.0278 (5) | 0.0314 (6) | −0.0065 (5) | −0.0025 (5) | −0.0055 (5) |
C8 | 0.0366 (6) | 0.0276 (5) | 0.0303 (6) | −0.0060 (5) | −0.0027 (5) | −0.0048 (4) |
S9 | 0.03504 (17) | 0.03241 (16) | 0.0429 (2) | −0.00581 (13) | −0.00816 (14) | −0.00064 (13) |
C9A | 0.0302 (6) | 0.0275 (6) | 0.0415 (7) | −0.0045 (5) | 0.0010 (5) | −0.0063 (5) |
C10 | 0.0401 (8) | 0.0306 (6) | 0.0599 (10) | −0.0017 (6) | 0.0067 (7) | −0.0133 (6) |
C11 | 0.0483 (9) | 0.0447 (8) | 0.0581 (10) | −0.0099 (7) | 0.0122 (8) | −0.0266 (8) |
C12 | 0.0472 (8) | 0.0509 (9) | 0.0387 (8) | −0.0146 (7) | 0.0045 (6) | −0.0187 (7) |
C13 | 0.0387 (7) | 0.0368 (7) | 0.0357 (7) | −0.0069 (5) | −0.0009 (5) | −0.0092 (5) |
C13A | 0.0294 (6) | 0.0271 (5) | 0.0349 (6) | −0.0046 (4) | 0.0007 (5) | −0.0080 (5) |
N14 | 0.0330 (5) | 0.0231 (4) | 0.0310 (5) | −0.0016 (4) | 0.0021 (4) | −0.0031 (4) |
C61 | 0.0456 (8) | 0.0512 (9) | 0.0429 (8) | −0.0179 (7) | 0.0091 (7) | −0.0052 (7) |
C1E | 0.0426 (7) | 0.0238 (5) | 0.0351 (7) | −0.0006 (5) | 0.0046 (5) | −0.0046 (5) |
C2E | 0.0457 (8) | 0.0315 (7) | 0.0553 (10) | −0.0037 (6) | −0.0005 (7) | −0.0006 (6) |
C3E | 0.0514 (10) | 0.0409 (8) | 0.0724 (13) | −0.0125 (7) | 0.0056 (9) | −0.0042 (8) |
C4E | 0.0684 (12) | 0.0340 (7) | 0.0553 (10) | −0.0164 (7) | 0.0136 (9) | −0.0042 (7) |
C5E | 0.0704 (12) | 0.0319 (7) | 0.0474 (9) | −0.0029 (7) | 0.0042 (8) | 0.0057 (6) |
C6E | 0.0503 (9) | 0.0322 (7) | 0.0434 (8) | 0.0006 (6) | 0.0012 (7) | 0.0006 (6) |
C40 | 0.0456 (8) | 0.0308 (6) | 0.0342 (7) | −0.0119 (5) | 0.0033 (6) | −0.0062 (5) |
C41 | 0.0631 (10) | 0.0334 (7) | 0.0341 (7) | −0.0221 (7) | 0.0032 (7) | −0.0061 (5) |
C42 | 0.0753 (13) | 0.0449 (9) | 0.0521 (10) | −0.0158 (9) | 0.0077 (9) | −0.0201 (8) |
C43 | 0.118 (2) | 0.0592 (12) | 0.0582 (13) | −0.0252 (13) | 0.0204 (14) | −0.0288 (10) |
C44 | 0.141 (3) | 0.0757 (15) | 0.0429 (11) | −0.0470 (17) | 0.0015 (14) | −0.0220 (10) |
C45 | 0.1051 (18) | 0.0694 (13) | 0.0436 (10) | −0.0437 (13) | −0.0145 (11) | −0.0061 (9) |
C46 | 0.0713 (12) | 0.0456 (8) | 0.0402 (8) | −0.0299 (8) | −0.0033 (8) | −0.0028 (7) |
C81 | 0.0385 (7) | 0.0273 (5) | 0.0346 (7) | −0.0064 (5) | −0.0007 (5) | −0.0051 (5) |
C82 | 0.0612 (10) | 0.0329 (7) | 0.0447 (8) | −0.0057 (7) | −0.0120 (7) | −0.0100 (6) |
C83 | 0.0764 (13) | 0.0389 (8) | 0.0653 (12) | −0.0070 (8) | −0.0167 (10) | −0.0223 (8) |
C84 | 0.0848 (15) | 0.0293 (7) | 0.0776 (14) | −0.0098 (8) | −0.0056 (11) | −0.0131 (8) |
C85 | 0.0850 (14) | 0.0296 (7) | 0.0580 (11) | −0.0053 (8) | −0.0037 (10) | 0.0032 (7) |
C86 | 0.0584 (10) | 0.0328 (7) | 0.0365 (7) | −0.0057 (6) | −0.0010 (7) | −0.0022 (5) |
Cl1—C4E | 1.7345 (19) | C13A—N14 | 1.4279 (17) |
Cl2—C46 | 1.736 (2) | C61—H61A | 0.9600 |
Cl3—C86 | 1.7364 (19) | C61—H61B | 0.9600 |
C1—N2 | 1.279 (2) | C61—H61C | 0.9600 |
C1—N14 | 1.4138 (17) | C1E—C2E | 1.379 (2) |
C1—C1E | 1.467 (2) | C1E—C6E | 1.394 (2) |
N2—O3 | 1.4169 (17) | C2E—C3E | 1.386 (3) |
O3—C3A | 1.4698 (17) | C2E—H2E | 0.9300 |
C3A—N14 | 1.4708 (18) | C3E—C4E | 1.376 (3) |
C3A—C4 | 1.518 (2) | C3E—H3E | 0.9300 |
C3A—C7A | 1.5285 (19) | C4E—C5E | 1.371 (3) |
C4—C40 | 1.331 (2) | C5E—C6E | 1.381 (2) |
C4—C5 | 1.511 (2) | C5E—H5E | 0.9300 |
C5—N6 | 1.4684 (19) | C6E—H6E | 0.9300 |
C5—H5A | 0.9700 | C40—C41 | 1.472 (2) |
C5—H5B | 0.9700 | C40—H40 | 0.9300 |
N6—C61 | 1.459 (2) | C41—C46 | 1.394 (3) |
N6—C7 | 1.461 (2) | C41—C42 | 1.398 (3) |
C7—C7A | 1.529 (2) | C42—C43 | 1.389 (3) |
C7—H7A | 0.9700 | C42—H42 | 0.9300 |
C7—H7B | 0.9700 | C43—C44 | 1.372 (4) |
C7A—C8 | 1.5420 (19) | C43—H43 | 0.9300 |
C7A—H71A | 0.9800 | C44—C45 | 1.370 (4) |
C8—C81 | 1.5124 (19) | C44—H44 | 0.9300 |
C8—S9 | 1.8364 (16) | C45—C46 | 1.386 (3) |
C8—H8 | 0.9800 | C45—H45 | 0.9300 |
S9—C9A | 1.7580 (17) | C81—C82 | 1.386 (2) |
C9A—C10 | 1.391 (2) | C81—C86 | 1.397 (2) |
C9A—C13A | 1.3974 (19) | C82—C83 | 1.389 (2) |
C10—C11 | 1.383 (3) | C82—H82 | 0.9300 |
C10—H10 | 0.9300 | C83—C84 | 1.371 (3) |
C11—C12 | 1.377 (3) | C83—H83 | 0.9300 |
C11—H11 | 0.9300 | C84—C85 | 1.373 (3) |
C12—C13 | 1.389 (2) | C84—H84 | 0.9300 |
C12—H12 | 0.9300 | C85—C86 | 1.384 (2) |
C13—C13A | 1.390 (2) | C85—H85 | 0.9300 |
C13—H13 | 0.9300 | ||
N2—C1—N14 | 114.41 (13) | N6—C61—H61A | 109.5 |
N2—C1—C1E | 122.05 (12) | N6—C61—H61B | 109.5 |
N14—C1—C1E | 123.53 (13) | H61A—C61—H61B | 109.5 |
C1—N2—O3 | 106.95 (11) | N6—C61—H61C | 109.5 |
N2—O3—C3A | 105.63 (10) | H61A—C61—H61C | 109.5 |
O3—C3A—N14 | 101.63 (10) | H61B—C61—H61C | 109.5 |
O3—C3A—C4 | 105.55 (10) | C2E—C1E—C6E | 119.32 (15) |
N14—C3A—C4 | 113.86 (11) | C2E—C1E—C1 | 121.26 (13) |
O3—C3A—C7A | 106.44 (11) | C6E—C1E—C1 | 119.43 (15) |
N14—C3A—C7A | 117.54 (11) | C1E—C2E—C3E | 120.60 (16) |
C4—C3A—C7A | 110.41 (11) | C1E—C2E—H2E | 119.7 |
C40—C4—C5 | 126.87 (13) | C3E—C2E—H2E | 119.7 |
C40—C4—C3A | 121.26 (13) | C4E—C3E—C2E | 119.13 (19) |
C5—C4—C3A | 111.85 (12) | C4E—C3E—H3E | 120.4 |
N6—C5—C4 | 112.64 (11) | C2E—C3E—H3E | 120.4 |
N6—C5—H5A | 109.1 | C5E—C4E—C3E | 121.18 (16) |
C4—C5—H5A | 109.1 | C5E—C4E—Cl1 | 119.05 (15) |
N6—C5—H5B | 109.1 | C3E—C4E—Cl1 | 119.77 (17) |
C4—C5—H5B | 109.1 | C4E—C5E—C6E | 119.72 (16) |
H5A—C5—H5B | 107.8 | C4E—C5E—H5E | 120.1 |
C61—N6—C7 | 109.80 (12) | C6E—C5E—H5E | 120.1 |
C61—N6—C5 | 108.88 (12) | C5E—C6E—C1E | 120.02 (17) |
C7—N6—C5 | 113.90 (11) | C5E—C6E—H6E | 120.0 |
N6—C7—C7A | 110.94 (12) | C1E—C6E—H6E | 120.0 |
N6—C7—H7A | 109.5 | C4—C40—C41 | 128.64 (14) |
C7A—C7—H7A | 109.5 | C4—C40—H40 | 115.7 |
N6—C7—H7B | 109.5 | C41—C40—H40 | 115.7 |
C7A—C7—H7B | 109.5 | C46—C41—C42 | 117.06 (16) |
H7A—C7—H7B | 108.0 | C46—C41—C40 | 120.18 (16) |
C3A—C7A—C7 | 106.66 (11) | C42—C41—C40 | 122.74 (17) |
C3A—C7A—C8 | 113.68 (11) | C43—C42—C41 | 120.8 (2) |
C7—C7A—C8 | 109.23 (12) | C43—C42—H42 | 119.6 |
C3A—C7A—H71A | 109.1 | C41—C42—H42 | 119.6 |
C7—C7A—H71A | 109.1 | C44—C43—C42 | 120.4 (2) |
C8—C7A—H71A | 109.1 | C44—C43—H43 | 119.8 |
C81—C8—C7A | 114.25 (11) | C42—C43—H43 | 119.8 |
C81—C8—S9 | 108.47 (10) | C45—C44—C43 | 120.3 (2) |
C7A—C8—S9 | 113.89 (10) | C45—C44—H44 | 119.9 |
C81—C8—H8 | 106.6 | C43—C44—H44 | 119.9 |
C7A—C8—H8 | 106.6 | C44—C45—C46 | 119.5 (2) |
S9—C8—H8 | 106.6 | C44—C45—H45 | 120.3 |
C9A—S9—C8 | 98.49 (6) | C46—C45—H45 | 120.3 |
C10—C9A—C13A | 119.60 (14) | C45—C46—C41 | 122.0 (2) |
C10—C9A—S9 | 120.58 (12) | C45—C46—Cl2 | 117.89 (18) |
C13A—C9A—S9 | 119.82 (11) | C41—C46—Cl2 | 120.09 (14) |
C11—C10—C9A | 120.63 (15) | C82—C81—C86 | 116.15 (14) |
C11—C10—H10 | 119.7 | C82—C81—C8 | 122.89 (13) |
C9A—C10—H10 | 119.7 | C86—C81—C8 | 120.79 (13) |
C12—C11—C10 | 119.64 (15) | C81—C82—C83 | 122.09 (16) |
C12—C11—H11 | 120.2 | C81—C82—H82 | 119.0 |
C10—C11—H11 | 120.2 | C83—C82—H82 | 119.0 |
C11—C12—C13 | 120.55 (16) | C84—C83—C82 | 119.96 (18) |
C11—C12—H12 | 119.7 | C84—C83—H83 | 120.0 |
C13—C12—H12 | 119.7 | C82—C83—H83 | 120.0 |
C12—C13—C13A | 120.05 (14) | C83—C84—C85 | 119.84 (17) |
C12—C13—H13 | 120.0 | C83—C84—H84 | 120.1 |
C13A—C13—H13 | 120.0 | C85—C84—H84 | 120.1 |
C13—C13A—C9A | 119.41 (13) | C84—C85—C86 | 119.65 (17) |
C13—C13A—N14 | 122.17 (12) | C84—C85—H85 | 120.2 |
C9A—C13A—N14 | 118.41 (13) | C86—C85—H85 | 120.2 |
C1—N14—C13A | 117.65 (11) | C85—C86—C81 | 122.31 (16) |
C1—N14—C3A | 102.39 (10) | C85—C86—Cl3 | 117.21 (14) |
C13A—N14—C3A | 119.70 (11) | C81—C86—Cl3 | 120.46 (12) |
N14—C1—N2—O3 | 3.72 (17) | C9A—C13A—N14—C3A | 63.38 (17) |
C1E—C1—N2—O3 | −177.20 (13) | O3—C3A—N14—C1 | −26.29 (12) |
C1—N2—O3—C3A | −21.41 (15) | C4—C3A—N14—C1 | 86.69 (13) |
N2—O3—C3A—N14 | 29.51 (12) | C7A—C3A—N14—C1 | −141.96 (12) |
N2—O3—C3A—C4 | −89.57 (12) | O3—C3A—N14—C13A | 105.95 (12) |
N2—O3—C3A—C7A | 153.08 (11) | C4—C3A—N14—C13A | −141.07 (12) |
O3—C3A—C4—C40 | 119.11 (14) | C7A—C3A—N14—C13A | −9.72 (17) |
N14—C3A—C4—C40 | 8.51 (18) | N2—C1—C1E—C2E | −160.17 (16) |
C7A—C3A—C4—C40 | −126.24 (14) | N14—C1—C1E—C2E | 18.8 (2) |
O3—C3A—C4—C5 | −59.56 (14) | N2—C1—C1E—C6E | 20.0 (2) |
N14—C3A—C4—C5 | −170.17 (11) | N14—C1—C1E—C6E | −161.01 (14) |
C7A—C3A—C4—C5 | 55.08 (14) | C6E—C1E—C2E—C3E | 2.1 (3) |
C40—C4—C5—N6 | 132.87 (15) | C1—C1E—C2E—C3E | −177.78 (16) |
C3A—C4—C5—N6 | −48.55 (16) | C1E—C2E—C3E—C4E | −2.0 (3) |
C4—C5—N6—C61 | 173.08 (13) | C2E—C3E—C4E—C5E | 0.3 (3) |
C4—C5—N6—C7 | 50.17 (17) | C2E—C3E—C4E—Cl1 | −179.47 (16) |
C61—N6—C7—C7A | −179.84 (12) | C3E—C4E—C5E—C6E | 1.3 (3) |
C5—N6—C7—C7A | −57.44 (16) | Cl1—C4E—C5E—C6E | −178.92 (15) |
O3—C3A—C7A—C7 | 53.94 (13) | C4E—C5E—C6E—C1E | −1.2 (3) |
N14—C3A—C7A—C7 | 166.95 (11) | C2E—C1E—C6E—C5E | −0.4 (2) |
C4—C3A—C7A—C7 | −60.14 (14) | C1—C1E—C6E—C5E | 179.41 (15) |
O3—C3A—C7A—C8 | 174.39 (11) | C5—C4—C40—C41 | 0.6 (3) |
N14—C3A—C7A—C8 | −72.60 (15) | C3A—C4—C40—C41 | −177.89 (14) |
C4—C3A—C7A—C8 | 60.30 (15) | C4—C40—C41—C46 | −141.76 (17) |
N6—C7—C7A—C3A | 61.13 (14) | C4—C40—C41—C42 | 39.8 (2) |
N6—C7—C7A—C8 | −62.13 (14) | C46—C41—C42—C43 | 1.9 (3) |
C3A—C7A—C8—C81 | 166.54 (12) | C40—C41—C42—C43 | −179.61 (17) |
C7—C7A—C8—C81 | −74.47 (14) | C41—C42—C43—C44 | −1.4 (3) |
C3A—C7A—C8—S9 | 41.12 (14) | C42—C43—C44—C45 | −0.1 (4) |
C7—C7A—C8—S9 | 160.11 (9) | C43—C44—C45—C46 | 1.0 (4) |
C81—C8—S9—C9A | −85.63 (10) | C44—C45—C46—C41 | −0.5 (3) |
C7A—C8—S9—C9A | 42.81 (11) | C44—C45—C46—Cl2 | 178.16 (17) |
C8—S9—C9A—C10 | 106.47 (13) | C42—C41—C46—C45 | −1.0 (2) |
C8—S9—C9A—C13A | −74.58 (12) | C40—C41—C46—C45 | −179.52 (16) |
C13A—C9A—C10—C11 | −3.0 (2) | C42—C41—C46—Cl2 | −179.57 (13) |
S9—C9A—C10—C11 | 175.92 (13) | C40—C41—C46—Cl2 | 1.9 (2) |
C9A—C10—C11—C12 | 1.2 (3) | C7A—C8—C81—C82 | −35.1 (2) |
C10—C11—C12—C13 | 2.0 (3) | S9—C8—C81—C82 | 93.14 (16) |
C11—C12—C13—C13A | −3.2 (2) | C7A—C8—C81—C86 | 149.96 (14) |
C12—C13—C13A—C9A | 1.3 (2) | S9—C8—C81—C86 | −81.81 (16) |
C12—C13—C13A—N14 | −177.72 (13) | C86—C81—C82—C83 | 0.9 (3) |
C10—C9A—C13A—C13 | 1.8 (2) | C8—C81—C82—C83 | −174.28 (18) |
S9—C9A—C13A—C13 | −177.20 (11) | C81—C82—C83—C84 | −1.0 (3) |
C10—C9A—C13A—N14 | −179.17 (13) | C82—C83—C84—C85 | 0.3 (4) |
S9—C9A—C13A—N14 | 1.87 (17) | C83—C84—C85—C86 | 0.3 (4) |
N2—C1—N14—C13A | −118.19 (14) | C84—C85—C86—C81 | −0.4 (3) |
C1E—C1—N14—C13A | 62.74 (18) | C84—C85—C86—Cl3 | 177.80 (18) |
N2—C1—N14—C3A | 15.27 (16) | C82—C81—C86—C85 | −0.2 (3) |
C1E—C1—N14—C3A | −163.80 (13) | C8—C81—C86—C85 | 175.07 (17) |
C13—C13A—N14—C1 | 7.71 (19) | C82—C81—C86—Cl3 | −178.35 (14) |
C9A—C13A—N14—C1 | −171.33 (12) | C8—C81—C86—Cl3 | −3.1 (2) |
C13—C13A—N14—C3A | −117.57 (15) |
Experimental details
Crystal data | |
Chemical formula | C33H26Cl3N3OS |
Mr | 618.98 |
Crystal system, space group | Triclinic, P1 |
Temperature (K) | 298 |
a, b, c (Å) | 11.015 (3), 11.758 (4), 11.988 (4) |
α, β, γ (°) | 78.87 (2), 86.89 (3), 78.29 (2) |
V (Å3) | 1491.5 (8) |
Z | 2 |
Radiation type | Mo Kα |
µ (mm−1) | 0.41 |
Crystal size (mm) | 0.30 × 0.15 × 0.15 |
Data collection | |
Diffractometer | Bruker Kappa APEXII CCD diffractometer |
Absorption correction | Multi-scan (SADABS; Sheldrick, 2004) |
Tmin, Tmax | 0.90, 0.94 |
No. of measured, independent and observed [I > 2σ(I)] reflections | 42055, 11096, 7867 |
Rint | 0.023 |
(sin θ/λ)max (Å−1) | 0.766 |
Refinement | |
R[F2 > 2σ(F2)], wR(F2), S | 0.048, 0.146, 1.03 |
No. of reflections | 11096 |
No. of parameters | 372 |
H-atom treatment | H-atom parameters constrained |
Δρmax, Δρmin (e Å−3) | 0.64, −0.62 |
Computer programs: APEX2 (Bruker, 2004), SAINT-Plus (Bruker, 2004), SHELXS97 (Sheldrick, 2008), SHELXL97 (Sheldrick, 2008), PLATON (Spek, 2009).
The title compound, C33H26N3OCl3 S, belongs to an important class of heterocycles which exhibit antihypertensive properties. The compound consists of a benzothiazepine, a oxadiazole and a methyl piperidine ring. Benziothiazepines are regarded as a class of calcium channel blockers (Budriesi et al., 2007), oxadiazol derivatives are established as micobicides (Sahin et al., 2002) and piperidines are established as key components of anti-Parkinson's drugs. Accurate description of the molecular geometry of such molecules are indispensable to proceed with the pharmacological investigations which may prove useful in the design of drugs with a wide range of activities. Also, the role of non-conventional hydrogen bonds viz. C—H···X (X= N, O, Cl, F, etc.) in influencing the geometry of the molecular packing can be unambiguously assessed. Recently, an anlogue of the title compound namely, the crystal structure of 1-(4-chlorophenyl)- 8-(4-fluorophenyl)-4-[(E)-(4-fluorophenyl)methylidene]-6-methyl-4,5,6,7,7a, 8-hexahydro[1,2,4]oxadiazolo[5,4-d]pyrido [3,4-c][1,5] benzothiazepine (Srinivasan et al., 2007) was elucidated.
A least-squares plane calculations show that the 2-chlorophenyl attached to thiazepine, 2-chlorophenyl attached to piperidine and 4-chlorophenyl ring of the oxadiazole ring make a dihedral angle of 34.8 (1) °, 51.3 (1) ° and 73.9 (1) °, respectively, with respect to the benzene fused to the thiazepine ring. The torsion angles about the methylidene bond C4—C40—C41—C42 = 39.8 (2) ° and C4—C40—C41—C46 = -141.8 (2) ° indicates a significant twist of the 2-chlorophenyl ring which may be attributed to steric factors. These values that describe the molecular geometry slightly differ from those observed in the 4-fluoro-4-fluoro- 4-chloro analogue (Srinivasan et al., 2007). The oxadiazole, piperidine and benzothiapezine rings adopt the usually expected envelope, chair and twist-boat conformations, respectively. The molecular aggreagation is characterized by linear chains of centrosymmetrically related pairs extending parallel to the (202) plane and connected through Cl···Cl interactions [Cl1···Cl2(-x+1,-y,-z+2) = 3.533 (2) Å. Other Cl···Cl distances observed are Cl2···Cl2(-x+1,-y+1,-z+1) = 3.826 (2) Å and Cl1···Cl3(x,+y-1,+z+1) = 3.952 (2) Å.