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, N.; Sribala, R.; Ranjith Kumar, R.; Perumal, S.; Krishnakumar, R.V.

doi:10.1107/S1600536807048465

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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

N. Srinivasan, R. Sribala, R. Ranjith Kumar, S. Perumal and R. V. Krishnakumar

In the title compound, C₃₃H₂₆ClF₂N₃OS, the oxadiazole, piperidine and benzothiazepine rings adopt envelope, chair and twist-boat conformations, respectively. The molecular aggregation in the crystal is characterized by linear chains of centrosymmetrically related pairs of molecules connected through C—H

F and C—H

N hydrogen bonds.

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Supporting information

	Crystallographic Information File (CIF) https://doi.org/10.1107/S1600536807048465/bh2135sup1.cif Contains datablocks I, global
	Structure factor file (CIF format) https://doi.org/10.1107/S1600536807048465/bh2135Isup2.hkl Contains datablock I

CCDC reference: 667316

checkCIF report

Key indicators

Single-crystal X-ray study
T = 298 K
Mean (C-C) = 0.003 Å
R factor = 0.045
wR factor = 0.128
Data-to-parameter ratio = 22.7

checkCIF/PLATON results

No syntax errors found



Alert level G
PLAT793_ALERT_1_G Check the Absolute Configuration of C3A    = ...          S
PLAT793_ALERT_1_G Check the Absolute Configuration of C7A    = ...          R
PLAT793_ALERT_1_G Check the Absolute Configuration of C8     = ...          R

   0 ALERT level A = In general: serious problem
   0 ALERT level B = Potentially serious problem
   0 ALERT level C = Check and explain
   3 ALERT level G = General alerts; check

   3 ALERT type 1 CIF construction/syntax error, inconsistent or missing data
   0 ALERT type 2 Indicator that the structure model may be wrong or deficient
   0 ALERT type 3 Indicator that the structure quality may be low
   0 ALERT type 4 Improvement, methodology, query or suggestion
   0 ALERT type 5 Informative message, check

Comment top

The title compound, C₃₃H₂₆N₃OF₂SCl, belongs to an important class of heterocycles which are expected to possess antihypertensive properties, and is made of three fused ring systems viz. a benzothiazepine, an oxadiazole and a methyl piperidine ring. Interestingly, benzothiazepines have been established as a class of calcium channel blockers (Budriesi et al., 2007), oxadiazole derivatives have been found to possess antimicrobial activity (Şahin et al., 2002) and piperidine ring occurs in many natural alkaloids and are constituents of a number of pharmaceutical drugs. Also, the role of non-conventional hydrogen bonds viz. C—H···X (X= N, O, Cl, F, etc.) can be accurately assessed through precise single-crystal structure determinations of these compounds which, in turn, may provide insights into design of drugs with a wide range of biological activities.

Least-squares plane calculations show that the 4-fluorophenyl attached to thiazepine, 4-flurophenyl attached to piperidine and 4-chlorophenyl rings make dihedral angles of 40.0 (1), 67.6 (1) and 71.5 (1)°, respectively, with respect to the benzene fused to the thiazepine ring. The torsion angles about the methylidene bond C4—C40—C41—C42 = -39.7 (3)° and C4—C40—C41—C46 = 144.01 (19)° indicate a significant twist of the 4-fluorophenyl ring which may be attributed to steric factors. The oxadiazole, piperidine and benzothiazepine rings adopt the envelope [Q = 0.299 (2) Å, φ = 150.5 (3)°] (Cremer & Pople, 1975), chair [Q = 0.597 (2) Å, θ = 1.6 (2)°, φ = 251 (5)°] (Boeyens, 1978) and twist-boat conformations, respectively. The molecular aggregation is characterized by linear chains of centrosymmetrically related pairs extending along the [010] axis, connected through a C—H···F and a C—H···N bonds (Table 1). The interactions between these linear chains are purely van der Waal's in nature. No significant π···π and C—H···π interactions were found in the crystal structure.

Related literature top

For biological properties of related compounds, see: Budriesi et al., 2007; Şahin et al., 2002. For conformational analysis of ring systems, see: Cremer & Pople, 1975; Boeyens, 1978.

Experimental top

2-Methyl-11-(4-fluorophenyl)-4-[(E)-(4-fluorophenyl)methylidene]- 1,2,3,4,11,11a-hexahydro-pyrido[3,4-c][1,5]benzothiazepine (1 mmol) and 4-chloro-N-hydroxybenzenecarboxymidoyl chloride (1 mmol) were dissolved in benzene (15 ml). Triethylamine (1 mmol) was added to the above mixture and refluxed for 30 min. After completion of the reaction the triethylamine hydrochloride was filtered off, solvent evaporated, and the 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-(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 as colourless crystals.

Structure description top

For biological properties of related compounds, see: Budriesi et al., 2007; Şahin et al., 2002. For conformational analysis of ring systems, see: Cremer & Pople, 1975; Boeyens, 1978.

Computing details top

Data collection: APEXII (Bruker–Nonius, 2004); cell refinement: SAINT (Bruker–Nonius, 2004); data reduction: SAINT (Bruker–Nonius, 2004); program(s) used to solve structure: SHELXS97 (Sheldrick, 1997); program(s) used to refine structure: SHELXL97 (Sheldrick, 1997); molecular graphics: PLUTON (Spek, 2003); software used to prepare material for publication: SHELXL97 (Sheldrick, 1997).

Figures top

	Fig. 1. The molecular structure of (I), with atom labels and 50% probability displacement ellipsoids. H atoms have been omitted for clarity.
	Fig. 2. A view of the molecular aggregation down the [100] axis. Ring systems and H atoms that are not involved in hydrogen bonding have been omitted for clarity.

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 top

Crystal data top

C₃₃H₂₆ClF₂N₃OS	F(000) = 1216
M_r = 586.08	D_x = 1.370 Mg m⁻³
Monoclinic, P2₁/n	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: -P 2yn	Cell parameters from 5122 reflections
a = 10.836 (5) Å	θ = 2.0–30.0°
b = 11.366 (4) Å	µ = 0.25 mm⁻¹
c = 23.100 (3) Å	T = 298 K
β = 92.63 (1)°	Plate, colourless
V = 2842.0 (17) Å³	0.30 × 0.20 × 0.20 mm
Z = 4

Data collection top

Bruker Kappa-APEX2 CCD diffractometer	8394 independent reflections
Radiation source: fine-focus sealed tube	5384 reflections with I > 2σ(I)
Graphite monochromator	R_int = 0.029
ω and φ scans	θ_max = 30.2°, θ_min = 2.1°
Absorption correction: multi-scan (SADABS; Sheldrick, 2004)	h = −14→15
T_min = 0.93, T_max = 0.96	k = −16→15
36502 measured reflections	l = −32→30

Refinement top

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)] = 0.045	Hydrogen site location: inferred from neighbouring sites
wR(F²) = 0.128	H-atom parameters constrained
S = 1.01	w = 1/[σ²(F_o²) + (0.0498P)² + 0.8797P] where P = (F_o² + 2F_c²)/3
8394 reflections	(Δ/σ)_max = 0.001
370 parameters	Δρ_max = 0.32 e Å⁻³
0 restraints	Δρ_min = −0.34 e Å⁻³

Crystal data top

C₃₃H₂₆ClF₂N₃OS	V = 2842.0 (17) Å³
M_r = 586.08	Z = 4
Monoclinic, P2₁/n	Mo Kα radiation
a = 10.836 (5) Å	µ = 0.25 mm⁻¹
b = 11.366 (4) Å	T = 298 K
c = 23.100 (3) Å	0.30 × 0.20 × 0.20 mm
β = 92.63 (1)°

Data collection top

Bruker Kappa-APEX2 CCD diffractometer	8394 independent reflections
Absorption correction: multi-scan (SADABS; Sheldrick, 2004)	5384 reflections with I > 2σ(I)
T_min = 0.93, T_max = 0.96	R_int = 0.029
36502 measured reflections

Refinement top

R[F² > 2σ(F²)] = 0.045	0 restraints
wR(F²) = 0.128	H-atom parameters constrained
S = 1.01	Δρ_max = 0.32 e Å⁻³
8394 reflections	Δρ_min = −0.34 e Å⁻³
370 parameters

Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Å²) top

	x	y	z	U_iso*/U_eq
C1	0.26565 (15)	−0.17757 (14)	0.62165 (7)	0.0415 (3)
N2	0.18066 (13)	−0.16509 (12)	0.65790 (6)	0.0463 (3)
O3	0.13128 (10)	−0.04971 (10)	0.64893 (5)	0.0464 (3)
C3A	0.22839 (14)	0.01637 (13)	0.62121 (6)	0.0391 (3)
C4	0.31070 (15)	0.06934 (13)	0.66958 (6)	0.0399 (3)
C5	0.23745 (16)	0.14586 (15)	0.70822 (7)	0.0458 (4)
H5A	0.1761	0.0986	0.7268	0.055*
H5B	0.2920	0.1797	0.7383	0.055*
N6	0.17576 (14)	0.24050 (13)	0.67469 (6)	0.0491 (3)
C7	0.09347 (16)	0.19098 (16)	0.62914 (7)	0.0481 (4)
H7A	0.0515	0.2543	0.6081	0.058*
H7B	0.0313	0.1427	0.6466	0.058*
C7A	0.16481 (14)	0.11610 (13)	0.58675 (6)	0.0390 (3)
H71A	0.1059	0.0818	0.5580	0.047*
C8	0.25323 (15)	0.19818 (13)	0.55535 (7)	0.0406 (3)
H8	0.2868	0.2524	0.5851	0.049*
S9	0.38729 (4)	0.12699 (4)	0.525049 (19)	0.04702 (12)
C9A	0.31578 (15)	0.00373 (15)	0.49202 (7)	0.0429 (4)
C10	0.30426 (17)	−0.00698 (17)	0.43211 (7)	0.0517 (4)
H10	0.3324	0.0532	0.4088	0.062*
C11	0.25179 (19)	−0.10530 (18)	0.40693 (8)	0.0582 (5)
H11	0.2471	−0.1128	0.3668	0.070*
C12	0.20602 (17)	−0.19283 (17)	0.44107 (8)	0.0544 (4)
H12	0.1700	−0.2592	0.4239	0.065*
C13	0.21341 (16)	−0.18245 (15)	0.50082 (7)	0.0469 (4)
H13	0.1800	−0.2407	0.5236	0.056*
C13A	0.27046 (14)	−0.08553 (14)	0.52684 (7)	0.0404 (3)
N14	0.28845 (12)	−0.07636 (11)	0.58843 (5)	0.0396 (3)
C1E	0.47422 (19)	−0.48916 (16)	0.60873 (8)	0.0560 (5)
C2E	0.36580 (19)	−0.49215 (15)	0.63745 (8)	0.0535 (4)
H2E	0.3392	−0.5617	0.6541	0.064*
C3E	0.29710 (17)	−0.39048 (14)	0.64122 (7)	0.0470 (4)
H3E	0.2230	−0.3917	0.6600	0.056*
C4E	0.33800 (16)	−0.28603 (14)	0.61706 (7)	0.0426 (4)
C5E	0.44779 (17)	−0.28544 (16)	0.58912 (8)	0.0546 (4)
H5E	0.4760	−0.2157	0.5733	0.066*
C6E	0.51637 (19)	−0.38703 (17)	0.58441 (9)	0.0611 (5)
H6E	0.5898	−0.3865	0.5651	0.073*
C40	0.43178 (15)	0.04950 (14)	0.67434 (7)	0.0438 (4)
H40	0.4622	−0.0044	0.6483	0.053*
C41	0.52401 (16)	0.10201 (17)	0.71562 (7)	0.0492 (4)
C42	0.5219 (2)	0.21982 (18)	0.73168 (9)	0.0641 (5)
H42	0.4578	0.2676	0.7174	0.077*
C43	0.6129 (2)	0.2676 (2)	0.76843 (11)	0.0807 (7)
H43	0.6101	0.3463	0.7792	0.097*
C44	0.7058 (2)	0.1977 (3)	0.78831 (11)	0.0828 (7)
C45	0.7134 (2)	0.0817 (3)	0.77427 (10)	0.0809 (7)
H45	0.7784	0.0356	0.7890	0.097*
C46	0.62175 (17)	0.0339 (2)	0.73741 (9)	0.0619 (5)
H46	0.6260	−0.0451	0.7272	0.074*
C61	0.1071 (2)	0.3164 (2)	0.71289 (9)	0.0737 (6)
H61A	0.1624	0.3477	0.7427	0.111*
H61B	0.0436	0.2714	0.7303	0.111*
H61C	0.0702	0.3798	0.6908	0.111*
C81	0.18678 (15)	0.27456 (14)	0.51049 (7)	0.0405 (3)
C82	0.11326 (16)	0.22881 (16)	0.46533 (7)	0.0507 (4)
H82	0.1009	0.1479	0.4630	0.061*
C83	0.05769 (18)	0.3015 (2)	0.42351 (8)	0.0603 (5)
H83	0.0090	0.2702	0.3931	0.072*
C84	0.0760 (2)	0.4192 (2)	0.42803 (9)	0.0670 (6)
C85	0.1463 (2)	0.46790 (19)	0.47118 (11)	0.0792 (7)
H85	0.1573	0.5490	0.4731	0.095*
C86	0.2018 (2)	0.39493 (16)	0.51271 (9)	0.0622 (5)
H86	0.2504	0.4279	0.5428	0.075*
F1	0.79600 (16)	0.24504 (19)	0.82413 (8)	0.1296 (7)
F2	0.02109 (15)	0.49074 (14)	0.38734 (6)	0.1075 (5)
CL1	0.55743 (6)	−0.61865 (5)	0.60066 (3)	0.0882 (2)

Atomic displacement parameters (Å²) top

	U¹¹	U²²	U³³	U¹²	U¹³	U²³
C1	0.0473 (9)	0.0431 (8)	0.0338 (8)	−0.0042 (7)	−0.0001 (7)	0.0055 (6)
N2	0.0513 (8)	0.0449 (7)	0.0429 (8)	−0.0018 (6)	0.0041 (6)	0.0078 (6)
O3	0.0455 (6)	0.0478 (6)	0.0465 (6)	−0.0002 (5)	0.0097 (5)	0.0072 (5)
C3A	0.0404 (8)	0.0430 (8)	0.0341 (8)	0.0006 (6)	0.0042 (6)	0.0043 (6)
C4	0.0457 (9)	0.0423 (8)	0.0315 (7)	0.0019 (6)	0.0007 (6)	0.0066 (6)
C5	0.0497 (9)	0.0533 (9)	0.0342 (8)	0.0067 (7)	0.0008 (7)	0.0020 (7)
N6	0.0583 (9)	0.0519 (8)	0.0370 (7)	0.0130 (7)	0.0009 (6)	−0.0011 (6)
C7	0.0459 (9)	0.0579 (10)	0.0407 (9)	0.0104 (7)	0.0027 (7)	0.0055 (7)
C7A	0.0385 (8)	0.0455 (8)	0.0326 (8)	0.0007 (6)	−0.0020 (6)	0.0033 (6)
C8	0.0441 (9)	0.0414 (8)	0.0362 (8)	0.0009 (6)	−0.0013 (7)	0.0018 (6)
S9	0.0408 (2)	0.0489 (2)	0.0518 (3)	−0.00048 (17)	0.00653 (18)	0.01041 (18)
C9A	0.0408 (8)	0.0493 (9)	0.0392 (8)	0.0071 (7)	0.0081 (7)	0.0073 (7)
C10	0.0529 (10)	0.0627 (11)	0.0402 (9)	0.0078 (8)	0.0111 (8)	0.0107 (8)
C11	0.0636 (12)	0.0768 (13)	0.0341 (9)	0.0095 (10)	0.0024 (8)	0.0012 (8)
C12	0.0583 (11)	0.0605 (11)	0.0438 (10)	0.0031 (8)	−0.0054 (8)	−0.0053 (8)
C13	0.0494 (10)	0.0504 (9)	0.0408 (9)	−0.0002 (7)	0.0011 (7)	0.0026 (7)
C13A	0.0411 (8)	0.0464 (8)	0.0338 (8)	0.0055 (6)	0.0036 (6)	0.0034 (6)
N14	0.0473 (7)	0.0382 (6)	0.0332 (7)	0.0015 (5)	0.0028 (5)	0.0048 (5)
C1E	0.0650 (12)	0.0476 (9)	0.0547 (11)	0.0095 (8)	−0.0054 (9)	0.0014 (8)
C2E	0.0753 (13)	0.0404 (8)	0.0445 (9)	−0.0027 (8)	−0.0010 (9)	0.0055 (7)
C3E	0.0601 (10)	0.0447 (9)	0.0363 (8)	−0.0046 (7)	0.0046 (7)	0.0032 (6)
C4E	0.0518 (9)	0.0417 (8)	0.0339 (8)	−0.0013 (7)	−0.0016 (7)	0.0042 (6)
C5E	0.0556 (11)	0.0474 (9)	0.0611 (11)	−0.0006 (8)	0.0065 (9)	0.0116 (8)
C6E	0.0558 (11)	0.0600 (11)	0.0682 (13)	0.0070 (9)	0.0092 (10)	0.0086 (9)
C40	0.0447 (9)	0.0484 (9)	0.0383 (8)	0.0022 (7)	0.0012 (7)	0.0066 (7)
C41	0.0446 (9)	0.0627 (11)	0.0400 (9)	−0.0014 (8)	−0.0004 (7)	0.0105 (7)
C42	0.0634 (12)	0.0601 (12)	0.0675 (13)	−0.0060 (9)	−0.0096 (10)	0.0087 (10)
C43	0.0832 (16)	0.0760 (15)	0.0812 (16)	−0.0228 (13)	−0.0137 (13)	−0.0014 (12)
C44	0.0693 (15)	0.110 (2)	0.0672 (14)	−0.0264 (14)	−0.0187 (12)	0.0072 (14)
C45	0.0529 (12)	0.116 (2)	0.0717 (15)	0.0024 (13)	−0.0179 (11)	0.0199 (14)
C46	0.0501 (11)	0.0755 (13)	0.0597 (12)	0.0049 (9)	−0.0027 (9)	0.0105 (10)
C61	0.0951 (17)	0.0759 (14)	0.0501 (11)	0.0348 (12)	0.0032 (11)	−0.0070 (10)
C81	0.0426 (8)	0.0442 (8)	0.0350 (8)	0.0034 (6)	0.0040 (7)	0.0042 (6)
C82	0.0543 (10)	0.0515 (10)	0.0455 (10)	−0.0002 (8)	−0.0044 (8)	0.0032 (7)
C83	0.0560 (11)	0.0831 (14)	0.0412 (10)	0.0075 (10)	−0.0055 (8)	0.0089 (9)
C84	0.0723 (14)	0.0732 (13)	0.0556 (12)	0.0189 (11)	0.0033 (10)	0.0271 (10)
C85	0.1073 (19)	0.0467 (11)	0.0828 (16)	0.0116 (11)	−0.0055 (14)	0.0163 (10)
C86	0.0826 (14)	0.0457 (10)	0.0573 (12)	−0.0001 (9)	−0.0093 (10)	0.0019 (8)
F1	0.1032 (12)	0.1675 (18)	0.1129 (13)	−0.0444 (12)	−0.0530 (10)	−0.0030 (12)
F2	0.1228 (12)	0.1098 (11)	0.0883 (10)	0.0369 (10)	−0.0117 (9)	0.0513 (9)
CL1	0.0964 (4)	0.0586 (3)	0.1103 (5)	0.0258 (3)	0.0137 (4)	0.0067 (3)

Geometric parameters (Å, º) top

C1—N2	1.281 (2)	C1E—CL1	1.740 (2)
C1—N14	1.4108 (19)	C2E—C3E	1.380 (3)
C1—C4E	1.467 (2)	C2E—H2E	0.9300
N2—O3	1.4279 (18)	C3E—C4E	1.393 (2)
O3—C3A	1.4639 (19)	C3E—H3E	0.9300
C3A—N14	1.467 (2)	C4E—C5E	1.379 (3)
C3A—C4	1.521 (2)	C5E—C6E	1.380 (3)
C3A—C7A	1.531 (2)	C5E—H5E	0.9300
C4—C40	1.331 (2)	C6E—H6E	0.9300
C4—C5	1.499 (2)	C40—C41	1.475 (2)
C5—N6	1.468 (2)	C40—H40	0.9300
C5—H5A	0.9700	C41—C46	1.388 (3)
C5—H5B	0.9700	C41—C42	1.390 (3)
N6—C7	1.461 (2)	C42—C43	1.383 (3)
N6—C61	1.461 (2)	C42—H42	0.9300
C7—C7A	1.533 (2)	C43—C44	1.346 (4)
C7—H7A	0.9700	C43—H43	0.9300
C7—H7B	0.9700	C44—C45	1.361 (4)
C7A—C8	1.542 (2)	C44—F1	1.362 (3)
C7A—H71A	0.9800	C45—C46	1.389 (3)
C8—C81	1.509 (2)	C45—H45	0.9300
C8—S9	1.8298 (17)	C46—H46	0.9300
C8—H8	0.9800	C61—H61A	0.9600
S9—C9A	1.7582 (19)	C61—H61B	0.9600
C9A—C10	1.389 (2)	C61—H61C	0.9600
C9A—C13A	1.398 (2)	C81—C86	1.379 (2)
C10—C11	1.371 (3)	C81—C82	1.385 (2)
C10—H10	0.9300	C82—C83	1.388 (2)
C11—C12	1.376 (3)	C82—H82	0.9300
C11—H11	0.9300	C83—C84	1.356 (3)
C12—C13	1.384 (2)	C83—H83	0.9300
C12—H12	0.9300	C84—C85	1.345 (3)
C13—C13A	1.387 (2)	C84—F2	1.359 (2)
C13—H13	0.9300	C85—C86	1.385 (3)
C13A—N14	1.431 (2)	C85—H85	0.9300
C1E—C2E	1.376 (3)	C86—H86	0.9300
C1E—C6E	1.377 (3)

N2—C1—N14	114.48 (14)	C2E—C1E—C6E	121.62 (17)
N2—C1—C4E	122.87 (14)	C2E—C1E—CL1	119.26 (15)
N14—C1—C4E	122.57 (14)	C6E—C1E—CL1	119.08 (16)
C1—N2—O3	106.42 (12)	C1E—C2E—C3E	119.01 (16)
N2—O3—C3A	105.22 (11)	C1E—C2E—H2E	120.5
O3—C3A—N14	101.65 (12)	C3E—C2E—H2E	120.5
O3—C3A—C4	106.91 (12)	C2E—C3E—C4E	120.40 (17)
N14—C3A—C4	113.85 (13)	C2E—C3E—H3E	119.8
O3—C3A—C7A	106.98 (12)	C4E—C3E—H3E	119.8
N14—C3A—C7A	117.59 (12)	C5E—C4E—C3E	119.26 (16)
C4—C3A—C7A	108.88 (13)	C5E—C4E—C1	120.32 (15)
C40—C4—C5	126.58 (15)	C3E—C4E—C1	120.42 (16)
C40—C4—C3A	122.42 (15)	C4E—C5E—C6E	120.79 (17)
C5—C4—C3A	110.99 (14)	C4E—C5E—H5E	119.6
N6—C5—C4	110.59 (13)	C6E—C5E—H5E	119.6
N6—C5—H5A	109.5	C1E—C6E—C5E	118.91 (19)
C4—C5—H5A	109.5	C1E—C6E—H6E	120.5
N6—C5—H5B	109.5	C5E—C6E—H6E	120.5
C4—C5—H5B	109.5	C4—C40—C41	128.37 (16)
H5A—C5—H5B	108.1	C4—C40—H40	115.8
C7—N6—C61	110.58 (15)	C41—C40—H40	115.8
C7—N6—C5	110.23 (14)	C46—C41—C42	117.55 (18)
C61—N6—C5	110.24 (14)	C46—C41—C40	119.45 (18)
N6—C7—C7A	111.41 (14)	C42—C41—C40	122.90 (16)
N6—C7—H7A	109.3	C43—C42—C41	121.5 (2)
C7A—C7—H7A	109.3	C43—C42—H42	119.3
N6—C7—H7B	109.3	C41—C42—H42	119.3
C7A—C7—H7B	109.3	C44—C43—C42	118.6 (2)
H7A—C7—H7B	108.0	C44—C43—H43	120.7
C3A—C7A—C7	107.88 (12)	C42—C43—H43	120.7
C3A—C7A—C8	114.71 (13)	C43—C44—C45	122.8 (2)
C7—C7A—C8	107.87 (13)	C43—C44—F1	118.6 (3)
C3A—C7A—H71A	108.7	C45—C44—F1	118.5 (2)
C7—C7A—H71A	108.7	C44—C45—C46	118.4 (2)
C8—C7A—H71A	108.7	C44—C45—H45	120.8
C81—C8—C7A	112.57 (13)	C46—C45—H45	120.8
C81—C8—S9	110.72 (11)	C41—C46—C45	121.1 (2)
C7A—C8—S9	115.70 (11)	C41—C46—H46	119.5
C81—C8—H8	105.7	C45—C46—H46	119.5
C7A—C8—H8	105.7	N6—C61—H61A	109.5
S9—C8—H8	105.7	N6—C61—H61B	109.5
C9A—S9—C8	100.17 (8)	H61A—C61—H61B	109.5
C10—C9A—C13A	119.46 (16)	N6—C61—H61C	109.5
C10—C9A—S9	121.32 (13)	H61A—C61—H61C	109.5
C13A—C9A—S9	119.22 (12)	H61B—C61—H61C	109.5
C11—C10—C9A	120.71 (17)	C86—C81—C82	117.63 (16)
C11—C10—H10	119.6	C86—C81—C8	119.57 (15)
C9A—C10—H10	119.6	C82—C81—C8	122.77 (15)
C10—C11—C12	119.95 (17)	C81—C82—C83	121.15 (18)
C10—C11—H11	120.0	C81—C82—H82	119.4
C12—C11—H11	120.0	C83—C82—H82	119.4
C11—C12—C13	120.28 (18)	C84—C83—C82	118.47 (19)
C11—C12—H12	119.9	C84—C83—H83	120.8
C13—C12—H12	119.9	C82—C83—H83	120.8
C12—C13—C13A	120.28 (16)	C85—C84—C83	122.59 (18)
C12—C13—H13	119.9	C85—C84—F2	118.8 (2)
C13A—C13—H13	119.9	C83—C84—F2	118.6 (2)
C13—C13A—C9A	119.24 (15)	C84—C85—C86	118.7 (2)
C13—C13A—N14	121.77 (14)	C84—C85—H85	120.6
C9A—C13A—N14	118.94 (14)	C86—C85—H85	120.6
C1—N14—C13A	117.52 (13)	C81—C86—C85	121.44 (19)
C1—N14—C3A	102.24 (12)	C81—C86—H86	119.3
C13A—N14—C3A	121.47 (12)	C85—C86—H86	119.3

N14—C1—N2—O3	3.69 (18)	C13—C13A—N14—C3A	−116.19 (17)
C4E—C1—N2—O3	−179.38 (14)	C9A—C13A—N14—C3A	66.2 (2)
C1—N2—O3—C3A	−22.32 (15)	O3—C3A—N14—C1	−27.85 (14)
N2—O3—C3A—N14	31.02 (13)	C4—C3A—N14—C1	86.72 (15)
N2—O3—C3A—C4	−88.59 (14)	C7A—C3A—N14—C1	−144.21 (14)
N2—O3—C3A—C7A	154.89 (12)	O3—C3A—N14—C13A	105.57 (14)
O3—C3A—C4—C40	123.58 (16)	C4—C3A—N14—C13A	−139.87 (14)
N14—C3A—C4—C40	12.2 (2)	C7A—C3A—N14—C13A	−10.8 (2)
C7A—C3A—C4—C40	−121.17 (16)	C6E—C1E—C2E—C3E	0.9 (3)
O3—C3A—C4—C5	−57.68 (16)	CL1—C1E—C2E—C3E	−176.81 (14)
N14—C3A—C4—C5	−169.09 (12)	C1E—C2E—C3E—C4E	−1.0 (3)
C7A—C3A—C4—C5	57.57 (16)	C2E—C3E—C4E—C5E	0.2 (3)
C40—C4—C5—N6	120.48 (18)	C2E—C3E—C4E—C1	−179.30 (15)
C3A—C4—C5—N6	−58.19 (18)	N2—C1—C4E—C5E	−162.90 (17)
C4—C5—N6—C7	59.06 (18)	N14—C1—C4E—C5E	13.8 (2)
C4—C5—N6—C61	−178.59 (17)	N2—C1—C4E—C3E	16.6 (2)
C61—N6—C7—C7A	177.10 (15)	N14—C1—C4E—C3E	−166.68 (15)
C5—N6—C7—C7A	−60.75 (17)	C3E—C4E—C5E—C6E	0.7 (3)
O3—C3A—C7A—C7	58.34 (16)	C1—C4E—C5E—C6E	−179.80 (17)
N14—C3A—C7A—C7	171.77 (13)	C2E—C1E—C6E—C5E	0.0 (3)
C4—C3A—C7A—C7	−56.86 (16)	CL1—C1E—C6E—C5E	177.70 (16)
O3—C3A—C7A—C8	178.57 (12)	C4E—C5E—C6E—C1E	−0.8 (3)
N14—C3A—C7A—C8	−67.99 (18)	C5—C4—C40—C41	−4.0 (3)
C4—C3A—C7A—C8	63.37 (16)	C3A—C4—C40—C41	174.52 (15)
N6—C7—C7A—C3A	59.72 (17)	C4—C40—C41—C46	144.01 (19)
N6—C7—C7A—C8	−64.73 (16)	C4—C40—C41—C42	−39.7 (3)
C3A—C7A—C8—C81	165.43 (13)	C46—C41—C42—C43	−0.6 (3)
C7—C7A—C8—C81	−74.34 (16)	C40—C41—C42—C43	−176.99 (19)
C3A—C7A—C8—S9	36.72 (17)	C41—C42—C43—C44	0.7 (4)
C7—C7A—C8—S9	156.96 (11)	C42—C43—C44—C45	−0.7 (4)
C81—C8—S9—C9A	−84.45 (12)	C42—C43—C44—F1	179.5 (2)
C7A—C8—S9—C9A	45.15 (12)	C43—C44—C45—C46	0.6 (4)
C8—S9—C9A—C10	110.28 (14)	F1—C44—C45—C46	−179.6 (2)
C8—S9—C9A—C13A	−70.17 (14)	C42—C41—C46—C45	0.5 (3)
C13A—C9A—C10—C11	−1.6 (3)	C40—C41—C46—C45	177.01 (19)
S9—C9A—C10—C11	177.92 (14)	C44—C45—C46—C41	−0.5 (3)
C9A—C10—C11—C12	2.3 (3)	C7A—C8—C81—C86	125.69 (18)
C10—C11—C12—C13	−0.4 (3)	S9—C8—C81—C86	−103.06 (17)
C11—C12—C13—C13A	−2.0 (3)	C7A—C8—C81—C82	−56.5 (2)
C12—C13—C13A—C9A	2.6 (2)	S9—C8—C81—C82	74.79 (18)
C12—C13—C13A—N14	−174.97 (16)	C86—C81—C82—C83	0.6 (3)
C10—C9A—C13A—C13	−0.8 (2)	C8—C81—C82—C83	−177.30 (16)
S9—C9A—C13A—C13	179.63 (12)	C81—C82—C83—C84	−0.6 (3)
C10—C9A—C13A—N14	176.86 (14)	C82—C83—C84—C85	0.4 (3)
S9—C9A—C13A—N14	−2.7 (2)	C82—C83—C84—F2	−179.60 (18)
N2—C1—N14—C13A	−119.50 (16)	C83—C84—C85—C86	−0.2 (4)
C4E—C1—N14—C13A	63.6 (2)	F2—C84—C85—C86	179.8 (2)
N2—C1—N14—C3A	16.18 (17)	C82—C81—C86—C85	−0.4 (3)
C4E—C1—N14—C3A	−160.76 (14)	C8—C81—C86—C85	177.58 (19)
C13—C13A—N14—C1	10.6 (2)	C84—C85—C86—C81	0.2 (4)
C9A—C13A—N14—C1	−166.97 (15)

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
C61—H61C···F2ⁱ	0.96	2.50	3.435 (3)	166
C83—H83···N2ⁱⁱ	0.93	2.61	3.488 (3)	157

Symmetry codes: (i) −x, −y+1, −z+1; (ii) −x, −y, −z+1.

Experimental details

Crystal data
Chemical formula	C₃₃H₂₆ClF₂N₃OS
M_r	586.08
Crystal system, space group	Monoclinic, P2₁/n
Temperature (K)	298
a, b, c (Å)	10.836 (5), 11.366 (4), 23.100 (3)
β (°)	92.63 (1)
V (Å³)	2842.0 (17)
Z	4
Radiation type	Mo Kα
µ (mm⁻¹)	0.25
Crystal size (mm)	0.30 × 0.20 × 0.20

Data collection
Diffractometer	Bruker Kappa-APEX2 CCD
Absorption correction	Multi-scan (SADABS; Sheldrick, 2004)
T_min, T_max	0.93, 0.96
No. of measured, independent and observed [I > 2σ(I)] reflections	36502, 8394, 5384
R_int	0.029
(sin θ/λ)_max (Å⁻¹)	0.707

Refinement
R[F² > 2σ(F²)], wR(F²), S	0.045, 0.128, 1.01
No. of reflections	8394
No. of parameters	370
H-atom treatment	H-atom parameters constrained
Δρ_max, Δρ_min (e Å⁻³)	0.32, −0.34

Computer programs: APEXII (Bruker–Nonius, 2004), SAINT (Bruker–Nonius, 2004), SHELXS97 (Sheldrick, 1997), SHELXL97 (Sheldrick, 1997), PLUTON (Spek, 2003).

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
C61—H61C···F2ⁱ	0.96	2.50	3.435 (3)	165.5
C83—H83···N2ⁱⁱ	0.93	2.61	3.488 (3)	157.4

Symmetry codes: (i) −x, −y+1, −z+1; (ii) −x, −y, −z+1.

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