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In the title compound, C33H26Cl3N3OS, the oxadiazole, piperidine and benzothia­pezine rings adopt envelope, chair and twist-boat conformations, respectively. In the crystal, the mol­ecular aggregation is characterized by chains of centrosymmetrically related pairs connected through Cl...Cl inter­actions [3.533 (2) Å], extending parallel to (202).

Supporting information

cif

Crystallographic Information File (CIF) https://doi.org/10.1107/S1600536810013309/nc2178sup1.cif
Contains datablocks I, global

hkl

Structure factor file (CIF format) https://doi.org/10.1107/S1600536810013309/nc2178Isup2.hkl
Contains datablock I

CCDC reference: 685375

Key indicators

  • Single-crystal X-ray study
  • T = 298 K
  • Mean [sigma](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

Comment top

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.

Related literature top

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).

Experimental top

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.

Refinement top

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).

Structure description top

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).

Computing details top

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).

Figures top
[Figure 1] Fig. 1. The molecular structure of (I), with atom labels and 50% probability displacement ellipsoids for non-H atoms. H atoms have been omitted for clarity.
[Figure 2] Fig. 2. A view of the molecular aggregation down the a--axis. H atoms have been omitted and Cl···Cl interactions are indicated by dashed lines.
8-(2-Chlorophenyl)-1-(4-chlorophenyl)-4-[(E)-(2- chlorophenyl)methylidene]-6-methyl-4,5,6,7,7a,8-hexahydro- 1,2,4-oxadiazolo[5,4-d]pyrido[3,4-c][1,5]benzothiazepine top
Crystal data top
C33H26Cl3N3OSZ = 2
Mr = 618.98F(000) = 640
Triclinic, P1Dx = 1.378 Mg m3
Hall symbol: -P 1Mo Kα radiation, λ = 0.71073 Å
a = 11.015 (3) ÅCell parameters from 4125 reflections
b = 11.758 (4) Åθ = 2.0–30.0°
c = 11.988 (4) ŵ = 0.41 mm1
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
Data collection top
Bruker Kappa APEXII CCD
diffractometer
11096 independent reflections
Radiation source: fine-focus sealed tube7867 reflections with I > 2σ(I)
Graphite monochromatorRint = 0.023
ω and φ scanθmax = 33.0°, θmin = 1.7°
Absorption correction: multi-scan
(SADABS; Sheldrick, 2004)
h = 1616
Tmin = 0.90, Tmax = 0.94k = 1717
42055 measured reflectionsl = 1818
Refinement top
Refinement on F2Primary atom site location: structure-invariant direct methods
Least-squares matrix: fullSecondary atom site location: difference Fourier map
R[F2 > 2σ(F2)] = 0.048Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.146H-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 parametersΔρmax = 0.64 e Å3
0 restraintsΔρmin = 0.62 e Å3
Crystal data top
C33H26Cl3N3OSγ = 78.29 (2)°
Mr = 618.98V = 1491.5 (8) Å3
Triclinic, P1Z = 2
a = 11.015 (3) ÅMo Kα radiation
b = 11.758 (4) ŵ = 0.41 mm1
c = 11.988 (4) ÅT = 298 K
α = 78.87 (2)°0.30 × 0.15 × 0.15 mm
β = 86.89 (3)°
Data collection top
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 = 0.94Rint = 0.023
42055 measured reflections
Refinement top
R[F2 > 2σ(F2)] = 0.0480 restraints
wR(F2) = 0.146H-atom parameters constrained
S = 1.03Δρmax = 0.64 e Å3
11096 reflectionsΔρmin = 0.62 e Å3
372 parameters
Special details top

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.

Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Å2) top
xyzUiso*/Ueq
Cl10.57470 (7)0.12556 (6)1.22882 (7)0.0878 (2)
Cl20.55422 (5)0.34566 (6)0.58843 (6)0.07294 (17)
Cl30.71901 (7)0.77874 (5)0.53545 (4)0.0769 (2)
C10.85278 (14)0.22540 (11)0.96401 (12)0.0336 (3)
N20.97082 (12)0.20144 (11)0.95229 (12)0.0404 (3)
O31.00715 (9)0.30577 (9)0.89247 (9)0.0378 (2)
C3A0.89581 (12)0.37735 (11)0.83332 (11)0.0300 (2)
C40.89945 (13)0.33994 (11)0.71870 (12)0.0320 (3)
C51.01522 (14)0.36089 (13)0.65093 (13)0.0368 (3)
H5A1.08570.30300.68430.044*
H5B1.00690.34950.57390.044*
N61.03901 (12)0.48001 (11)0.64726 (10)0.0353 (2)
C71.03493 (13)0.51369 (13)0.75868 (13)0.0355 (3)
H7A1.04890.59380.74970.043*
H7B1.10050.46170.80530.043*
C7A0.90965 (12)0.50621 (11)0.81809 (12)0.0307 (2)
H71A0.91040.52760.89310.037*
C80.80644 (13)0.59400 (11)0.74674 (12)0.0315 (2)
H80.82520.58690.66720.038*
S90.65096 (3)0.56089 (3)0.77852 (3)0.03747 (9)
C9A0.65984 (13)0.52634 (12)0.92758 (13)0.0333 (3)
C100.59577 (15)0.60462 (13)0.99383 (16)0.0439 (3)
H100.55210.67800.95890.053*
C110.59637 (17)0.57444 (16)1.11118 (17)0.0484 (4)
H110.55210.62661.15490.058*
C120.66289 (16)0.46670 (16)1.16287 (14)0.0437 (3)
H120.66130.44531.24170.052*
C130.73233 (14)0.38968 (13)1.09826 (13)0.0368 (3)
H130.78030.31881.13400.044*
C13A0.73021 (12)0.41847 (11)0.98022 (12)0.0303 (2)
N140.79641 (11)0.34047 (9)0.91010 (10)0.0300 (2)
C611.15951 (16)0.48759 (16)0.59264 (15)0.0462 (4)
H61A1.17590.56520.58990.069*
H61B1.15910.47260.51680.069*
H61C1.22290.42990.63540.069*
C1E0.78313 (14)0.13884 (11)1.02695 (12)0.0350 (3)
C2E0.65779 (16)0.15047 (14)1.01121 (16)0.0458 (4)
H2E0.61680.21270.95790.055*
C3E0.59237 (19)0.07021 (16)1.07412 (19)0.0555 (5)
H3E0.50740.07961.06500.067*
C4E0.6548 (2)0.02356 (15)1.15020 (17)0.0527 (4)
C5E0.7800 (2)0.03845 (15)1.16498 (16)0.0529 (4)
H5E0.82110.10321.21560.063*
C6E0.84464 (17)0.04309 (13)1.10441 (14)0.0443 (3)
H6E0.92930.03411.11530.053*
C400.80948 (15)0.29252 (12)0.68793 (12)0.0364 (3)
H400.74410.28670.73980.044*
C410.79968 (17)0.24807 (13)0.58271 (13)0.0419 (3)
C420.9013 (2)0.18426 (17)0.53161 (17)0.0557 (5)
H420.97880.16820.56470.067*
C430.8879 (3)0.1446 (2)0.4319 (2)0.0757 (7)
H430.95680.10370.39800.091*
C440.7738 (3)0.1654 (2)0.38322 (19)0.0815 (8)
H440.76560.13870.31640.098*
C450.6718 (3)0.2253 (2)0.43257 (18)0.0690 (6)
H450.59420.23830.40020.083*
C460.68514 (19)0.26646 (16)0.53113 (15)0.0503 (4)
C810.80119 (13)0.72208 (12)0.75331 (12)0.0336 (3)
C820.82787 (18)0.75779 (14)0.85131 (15)0.0460 (4)
H820.85720.70060.91400.055*
C830.8122 (2)0.87629 (16)0.85885 (19)0.0585 (5)
H830.82970.89740.92620.070*
C840.7708 (2)0.96217 (16)0.7669 (2)0.0635 (5)
H840.76071.04160.77170.076*
C850.7445 (2)0.93064 (15)0.66774 (18)0.0598 (5)
H850.71680.98850.60500.072*
C860.75923 (17)0.81224 (14)0.66168 (14)0.0436 (3)
Atomic displacement parameters (Å2) top
U11U22U33U12U13U23
Cl10.1016 (5)0.0606 (3)0.0984 (5)0.0388 (3)0.0198 (4)0.0104 (3)
Cl20.0590 (3)0.0861 (4)0.0774 (4)0.0188 (3)0.0099 (3)0.0169 (3)
Cl30.1281 (5)0.0532 (3)0.0411 (2)0.0047 (3)0.0262 (3)0.0051 (2)
C10.0396 (7)0.0255 (5)0.0314 (6)0.0003 (5)0.0013 (5)0.0025 (5)
N20.0403 (6)0.0324 (6)0.0411 (7)0.0011 (5)0.0000 (5)0.0022 (5)
O30.0318 (5)0.0364 (5)0.0399 (5)0.0018 (4)0.0024 (4)0.0015 (4)
C3A0.0312 (6)0.0271 (5)0.0302 (6)0.0029 (4)0.0011 (5)0.0043 (4)
C40.0377 (7)0.0256 (5)0.0318 (6)0.0046 (5)0.0018 (5)0.0054 (4)
C50.0399 (7)0.0343 (6)0.0366 (7)0.0070 (5)0.0049 (6)0.0091 (5)
N60.0375 (6)0.0350 (6)0.0335 (6)0.0097 (5)0.0018 (5)0.0044 (4)
C70.0357 (7)0.0349 (6)0.0371 (7)0.0096 (5)0.0016 (5)0.0067 (5)
C7A0.0334 (6)0.0278 (5)0.0314 (6)0.0065 (5)0.0025 (5)0.0055 (5)
C80.0366 (6)0.0276 (5)0.0303 (6)0.0060 (5)0.0027 (5)0.0048 (4)
S90.03504 (17)0.03241 (16)0.0429 (2)0.00581 (13)0.00816 (14)0.00064 (13)
C9A0.0302 (6)0.0275 (6)0.0415 (7)0.0045 (5)0.0010 (5)0.0063 (5)
C100.0401 (8)0.0306 (6)0.0599 (10)0.0017 (6)0.0067 (7)0.0133 (6)
C110.0483 (9)0.0447 (8)0.0581 (10)0.0099 (7)0.0122 (8)0.0266 (8)
C120.0472 (8)0.0509 (9)0.0387 (8)0.0146 (7)0.0045 (6)0.0187 (7)
C130.0387 (7)0.0368 (7)0.0357 (7)0.0069 (5)0.0009 (5)0.0092 (5)
C13A0.0294 (6)0.0271 (5)0.0349 (6)0.0046 (4)0.0007 (5)0.0080 (5)
N140.0330 (5)0.0231 (4)0.0310 (5)0.0016 (4)0.0021 (4)0.0031 (4)
C610.0456 (8)0.0512 (9)0.0429 (8)0.0179 (7)0.0091 (7)0.0052 (7)
C1E0.0426 (7)0.0238 (5)0.0351 (7)0.0006 (5)0.0046 (5)0.0046 (5)
C2E0.0457 (8)0.0315 (7)0.0553 (10)0.0037 (6)0.0005 (7)0.0006 (6)
C3E0.0514 (10)0.0409 (8)0.0724 (13)0.0125 (7)0.0056 (9)0.0042 (8)
C4E0.0684 (12)0.0340 (7)0.0553 (10)0.0164 (7)0.0136 (9)0.0042 (7)
C5E0.0704 (12)0.0319 (7)0.0474 (9)0.0029 (7)0.0042 (8)0.0057 (6)
C6E0.0503 (9)0.0322 (7)0.0434 (8)0.0006 (6)0.0012 (7)0.0006 (6)
C400.0456 (8)0.0308 (6)0.0342 (7)0.0119 (5)0.0033 (6)0.0062 (5)
C410.0631 (10)0.0334 (7)0.0341 (7)0.0221 (7)0.0032 (7)0.0061 (5)
C420.0753 (13)0.0449 (9)0.0521 (10)0.0158 (9)0.0077 (9)0.0201 (8)
C430.118 (2)0.0592 (12)0.0582 (13)0.0252 (13)0.0204 (14)0.0288 (10)
C440.141 (3)0.0757 (15)0.0429 (11)0.0470 (17)0.0015 (14)0.0220 (10)
C450.1051 (18)0.0694 (13)0.0436 (10)0.0437 (13)0.0145 (11)0.0061 (9)
C460.0713 (12)0.0456 (8)0.0402 (8)0.0299 (8)0.0033 (8)0.0028 (7)
C810.0385 (7)0.0273 (5)0.0346 (7)0.0064 (5)0.0007 (5)0.0051 (5)
C820.0612 (10)0.0329 (7)0.0447 (8)0.0057 (7)0.0120 (7)0.0100 (6)
C830.0764 (13)0.0389 (8)0.0653 (12)0.0070 (8)0.0167 (10)0.0223 (8)
C840.0848 (15)0.0293 (7)0.0776 (14)0.0098 (8)0.0056 (11)0.0131 (8)
C850.0850 (14)0.0296 (7)0.0580 (11)0.0053 (8)0.0037 (10)0.0032 (7)
C860.0584 (10)0.0328 (7)0.0365 (7)0.0057 (6)0.0010 (7)0.0022 (5)
Geometric parameters (Å, º) top
Cl1—C4E1.7345 (19)C13A—N141.4279 (17)
Cl2—C461.736 (2)C61—H61A0.9600
Cl3—C861.7364 (19)C61—H61B0.9600
C1—N21.279 (2)C61—H61C0.9600
C1—N141.4138 (17)C1E—C2E1.379 (2)
C1—C1E1.467 (2)C1E—C6E1.394 (2)
N2—O31.4169 (17)C2E—C3E1.386 (3)
O3—C3A1.4698 (17)C2E—H2E0.9300
C3A—N141.4708 (18)C3E—C4E1.376 (3)
C3A—C41.518 (2)C3E—H3E0.9300
C3A—C7A1.5285 (19)C4E—C5E1.371 (3)
C4—C401.331 (2)C5E—C6E1.381 (2)
C4—C51.511 (2)C5E—H5E0.9300
C5—N61.4684 (19)C6E—H6E0.9300
C5—H5A0.9700C40—C411.472 (2)
C5—H5B0.9700C40—H400.9300
N6—C611.459 (2)C41—C461.394 (3)
N6—C71.461 (2)C41—C421.398 (3)
C7—C7A1.529 (2)C42—C431.389 (3)
C7—H7A0.9700C42—H420.9300
C7—H7B0.9700C43—C441.372 (4)
C7A—C81.5420 (19)C43—H430.9300
C7A—H71A0.9800C44—C451.370 (4)
C8—C811.5124 (19)C44—H440.9300
C8—S91.8364 (16)C45—C461.386 (3)
C8—H80.9800C45—H450.9300
S9—C9A1.7580 (17)C81—C821.386 (2)
C9A—C101.391 (2)C81—C861.397 (2)
C9A—C13A1.3974 (19)C82—C831.389 (2)
C10—C111.383 (3)C82—H820.9300
C10—H100.9300C83—C841.371 (3)
C11—C121.377 (3)C83—H830.9300
C11—H110.9300C84—C851.373 (3)
C12—C131.389 (2)C84—H840.9300
C12—H120.9300C85—C861.384 (2)
C13—C13A1.390 (2)C85—H850.9300
C13—H130.9300
N2—C1—N14114.41 (13)N6—C61—H61A109.5
N2—C1—C1E122.05 (12)N6—C61—H61B109.5
N14—C1—C1E123.53 (13)H61A—C61—H61B109.5
C1—N2—O3106.95 (11)N6—C61—H61C109.5
N2—O3—C3A105.63 (10)H61A—C61—H61C109.5
O3—C3A—N14101.63 (10)H61B—C61—H61C109.5
O3—C3A—C4105.55 (10)C2E—C1E—C6E119.32 (15)
N14—C3A—C4113.86 (11)C2E—C1E—C1121.26 (13)
O3—C3A—C7A106.44 (11)C6E—C1E—C1119.43 (15)
N14—C3A—C7A117.54 (11)C1E—C2E—C3E120.60 (16)
C4—C3A—C7A110.41 (11)C1E—C2E—H2E119.7
C40—C4—C5126.87 (13)C3E—C2E—H2E119.7
C40—C4—C3A121.26 (13)C4E—C3E—C2E119.13 (19)
C5—C4—C3A111.85 (12)C4E—C3E—H3E120.4
N6—C5—C4112.64 (11)C2E—C3E—H3E120.4
N6—C5—H5A109.1C5E—C4E—C3E121.18 (16)
C4—C5—H5A109.1C5E—C4E—Cl1119.05 (15)
N6—C5—H5B109.1C3E—C4E—Cl1119.77 (17)
C4—C5—H5B109.1C4E—C5E—C6E119.72 (16)
H5A—C5—H5B107.8C4E—C5E—H5E120.1
C61—N6—C7109.80 (12)C6E—C5E—H5E120.1
C61—N6—C5108.88 (12)C5E—C6E—C1E120.02 (17)
C7—N6—C5113.90 (11)C5E—C6E—H6E120.0
N6—C7—C7A110.94 (12)C1E—C6E—H6E120.0
N6—C7—H7A109.5C4—C40—C41128.64 (14)
C7A—C7—H7A109.5C4—C40—H40115.7
N6—C7—H7B109.5C41—C40—H40115.7
C7A—C7—H7B109.5C46—C41—C42117.06 (16)
H7A—C7—H7B108.0C46—C41—C40120.18 (16)
C3A—C7A—C7106.66 (11)C42—C41—C40122.74 (17)
C3A—C7A—C8113.68 (11)C43—C42—C41120.8 (2)
C7—C7A—C8109.23 (12)C43—C42—H42119.6
C3A—C7A—H71A109.1C41—C42—H42119.6
C7—C7A—H71A109.1C44—C43—C42120.4 (2)
C8—C7A—H71A109.1C44—C43—H43119.8
C81—C8—C7A114.25 (11)C42—C43—H43119.8
C81—C8—S9108.47 (10)C45—C44—C43120.3 (2)
C7A—C8—S9113.89 (10)C45—C44—H44119.9
C81—C8—H8106.6C43—C44—H44119.9
C7A—C8—H8106.6C44—C45—C46119.5 (2)
S9—C8—H8106.6C44—C45—H45120.3
C9A—S9—C898.49 (6)C46—C45—H45120.3
C10—C9A—C13A119.60 (14)C45—C46—C41122.0 (2)
C10—C9A—S9120.58 (12)C45—C46—Cl2117.89 (18)
C13A—C9A—S9119.82 (11)C41—C46—Cl2120.09 (14)
C11—C10—C9A120.63 (15)C82—C81—C86116.15 (14)
C11—C10—H10119.7C82—C81—C8122.89 (13)
C9A—C10—H10119.7C86—C81—C8120.79 (13)
C12—C11—C10119.64 (15)C81—C82—C83122.09 (16)
C12—C11—H11120.2C81—C82—H82119.0
C10—C11—H11120.2C83—C82—H82119.0
C11—C12—C13120.55 (16)C84—C83—C82119.96 (18)
C11—C12—H12119.7C84—C83—H83120.0
C13—C12—H12119.7C82—C83—H83120.0
C12—C13—C13A120.05 (14)C83—C84—C85119.84 (17)
C12—C13—H13120.0C83—C84—H84120.1
C13A—C13—H13120.0C85—C84—H84120.1
C13—C13A—C9A119.41 (13)C84—C85—C86119.65 (17)
C13—C13A—N14122.17 (12)C84—C85—H85120.2
C9A—C13A—N14118.41 (13)C86—C85—H85120.2
C1—N14—C13A117.65 (11)C85—C86—C81122.31 (16)
C1—N14—C3A102.39 (10)C85—C86—Cl3117.21 (14)
C13A—N14—C3A119.70 (11)C81—C86—Cl3120.46 (12)
N14—C1—N2—O33.72 (17)C9A—C13A—N14—C3A63.38 (17)
C1E—C1—N2—O3177.20 (13)O3—C3A—N14—C126.29 (12)
C1—N2—O3—C3A21.41 (15)C4—C3A—N14—C186.69 (13)
N2—O3—C3A—N1429.51 (12)C7A—C3A—N14—C1141.96 (12)
N2—O3—C3A—C489.57 (12)O3—C3A—N14—C13A105.95 (12)
N2—O3—C3A—C7A153.08 (11)C4—C3A—N14—C13A141.07 (12)
O3—C3A—C4—C40119.11 (14)C7A—C3A—N14—C13A9.72 (17)
N14—C3A—C4—C408.51 (18)N2—C1—C1E—C2E160.17 (16)
C7A—C3A—C4—C40126.24 (14)N14—C1—C1E—C2E18.8 (2)
O3—C3A—C4—C559.56 (14)N2—C1—C1E—C6E20.0 (2)
N14—C3A—C4—C5170.17 (11)N14—C1—C1E—C6E161.01 (14)
C7A—C3A—C4—C555.08 (14)C6E—C1E—C2E—C3E2.1 (3)
C40—C4—C5—N6132.87 (15)C1—C1E—C2E—C3E177.78 (16)
C3A—C4—C5—N648.55 (16)C1E—C2E—C3E—C4E2.0 (3)
C4—C5—N6—C61173.08 (13)C2E—C3E—C4E—C5E0.3 (3)
C4—C5—N6—C750.17 (17)C2E—C3E—C4E—Cl1179.47 (16)
C61—N6—C7—C7A179.84 (12)C3E—C4E—C5E—C6E1.3 (3)
C5—N6—C7—C7A57.44 (16)Cl1—C4E—C5E—C6E178.92 (15)
O3—C3A—C7A—C753.94 (13)C4E—C5E—C6E—C1E1.2 (3)
N14—C3A—C7A—C7166.95 (11)C2E—C1E—C6E—C5E0.4 (2)
C4—C3A—C7A—C760.14 (14)C1—C1E—C6E—C5E179.41 (15)
O3—C3A—C7A—C8174.39 (11)C5—C4—C40—C410.6 (3)
N14—C3A—C7A—C872.60 (15)C3A—C4—C40—C41177.89 (14)
C4—C3A—C7A—C860.30 (15)C4—C40—C41—C46141.76 (17)
N6—C7—C7A—C3A61.13 (14)C4—C40—C41—C4239.8 (2)
N6—C7—C7A—C862.13 (14)C46—C41—C42—C431.9 (3)
C3A—C7A—C8—C81166.54 (12)C40—C41—C42—C43179.61 (17)
C7—C7A—C8—C8174.47 (14)C41—C42—C43—C441.4 (3)
C3A—C7A—C8—S941.12 (14)C42—C43—C44—C450.1 (4)
C7—C7A—C8—S9160.11 (9)C43—C44—C45—C461.0 (4)
C81—C8—S9—C9A85.63 (10)C44—C45—C46—C410.5 (3)
C7A—C8—S9—C9A42.81 (11)C44—C45—C46—Cl2178.16 (17)
C8—S9—C9A—C10106.47 (13)C42—C41—C46—C451.0 (2)
C8—S9—C9A—C13A74.58 (12)C40—C41—C46—C45179.52 (16)
C13A—C9A—C10—C113.0 (2)C42—C41—C46—Cl2179.57 (13)
S9—C9A—C10—C11175.92 (13)C40—C41—C46—Cl21.9 (2)
C9A—C10—C11—C121.2 (3)C7A—C8—C81—C8235.1 (2)
C10—C11—C12—C132.0 (3)S9—C8—C81—C8293.14 (16)
C11—C12—C13—C13A3.2 (2)C7A—C8—C81—C86149.96 (14)
C12—C13—C13A—C9A1.3 (2)S9—C8—C81—C8681.81 (16)
C12—C13—C13A—N14177.72 (13)C86—C81—C82—C830.9 (3)
C10—C9A—C13A—C131.8 (2)C8—C81—C82—C83174.28 (18)
S9—C9A—C13A—C13177.20 (11)C81—C82—C83—C841.0 (3)
C10—C9A—C13A—N14179.17 (13)C82—C83—C84—C850.3 (4)
S9—C9A—C13A—N141.87 (17)C83—C84—C85—C860.3 (4)
N2—C1—N14—C13A118.19 (14)C84—C85—C86—C810.4 (3)
C1E—C1—N14—C13A62.74 (18)C84—C85—C86—Cl3177.80 (18)
N2—C1—N14—C3A15.27 (16)C82—C81—C86—C850.2 (3)
C1E—C1—N14—C3A163.80 (13)C8—C81—C86—C85175.07 (17)
C13—C13A—N14—C17.71 (19)C82—C81—C86—Cl3178.35 (14)
C9A—C13A—N14—C1171.33 (12)C8—C81—C86—Cl33.1 (2)
C13—C13A—N14—C3A117.57 (15)

Experimental details

Crystal data
Chemical formulaC33H26Cl3N3OS
Mr618.98
Crystal system, space groupTriclinic, 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)
V3)1491.5 (8)
Z2
Radiation typeMo Kα
µ (mm1)0.41
Crystal size (mm)0.30 × 0.15 × 0.15
Data collection
DiffractometerBruker Kappa APEXII CCD
diffractometer
Absorption correctionMulti-scan
(SADABS; Sheldrick, 2004)
Tmin, Tmax0.90, 0.94
No. of measured, independent and
observed [I > 2σ(I)] reflections
42055, 11096, 7867
Rint0.023
(sin θ/λ)max1)0.766
Refinement
R[F2 > 2σ(F2)], wR(F2), S 0.048, 0.146, 1.03
No. of reflections11096
No. of parameters372
H-atom treatmentH-atom parameters constrained
Δρmax, Δρmin (e Å3)0.64, 0.62

Computer programs: APEX2 (Bruker, 2004), SAINT-Plus (Bruker, 2004), SHELXS97 (Sheldrick, 2008), SHELXL97 (Sheldrick, 2008), PLATON (Spek, 2009).

 

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