{2-[(1,3-Benzo-thia-zol-2-yl)meth-oxy]-5-fluoro-phen-yl}(4-chloro-phen-yl)methanone.

The asymmetric unit of the title compound, C21H13ClFNO2S, contains two independent mol-ecules with similar conformations. In the mol-ecules, the thia-zole ring is essentially planar [maximum atomic deviations = 0.014 (4) and 0.023 (5) Å] and is oriented with respect to the fluoro-phenyl ring and chloro-phenyl rings at 9.96 (18) and 70.39 (18)° in one mol-ecule and at 7.50 (18) and 68.43 (18)° in the other; the dihedral angles between the fluoro-phenyl and chloro-phenyl rings are 64.9 (2) and 64.6 (2)°, respectively. Inter-molecular C-H⋯O and C-H⋯F hydrogen bonds stabilize the three-dimensional supra-molecular architecture. Weak C-H⋯π and π-π inter-actions [centroid-centroid distance = 3.877 (3) Å] lead to a criss-cross mol-ecular packing along the c axis.

Related literature

For background to the applications of benzo­thia­zole derivatives, see: Rana et al. (2007 ▶); Saeed et al. (2010 ▶); Telvekar et al. (2012 ▶); Kelarev et al. (2003 ▶). For crystal structures of related benzo­thia­zoles, see: Nayak et al. (2013 ▶); Venugopala et al. (2012 ▶).

Experimental

Crystal data

C21H13ClFNO2S

M = 397.84

Orthorhombic,

a = 19.7280 (6) Å

b = 7.4755 (3) Å

c = 24.4847 (7) Å

V = 3611.0 (2) Å3

Z = 8

Mo Kα radiation

μ = 0.35 mm−1

T = 292 K

0.18 × 0.12 × 0.08 mm

Data collection

Oxford Diffraction Xcalibur (Eos, Nova) diffractometer

Absorption correction: multi-scan (CrysAlis PRO; Oxford Diffraction, 2009 ▶) T min = 0.939, T max = 0.972

36561 measured reflections

7100 independent reflections

4182 reflections with I > 2σ(I)

R int = 0.076

Refinement

R[F 2 > 2σ(F 2)] = 0.053

wR(F 2) = 0.118

S = 0.99

7100 reflections

488 parameters

1 restraint

H-atom parameters constrained

Δρmax = 0.31 e Å−3

Δρmin = −0.21 e Å−3

Absolute structure: Flack (1983 ▶)

Flack parameter: −0.05 (8), ???? Friedel pairs

Data collection: CrysAlis PRO (Oxford Diffraction, 2009 ▶); cell refinement: CrysAlis PRO; data reduction: CrysAlis PRO; program(s) used to solve structure: SHELXS97 (Sheldrick, 2008 ▶); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008 ▶); molecular graphics: ORTEP-3 for Windows (Farrugia, 2012 ▶) and Mercury (Macrae et al., 2008 ▶); software used to prepare material for publication: PLATON (Spek, 2009 ▶) and PARST (Nardelli, 1995 ▶).

Crystal structure: contains datablock(s) global, I. DOI: 10.1107/S1600536813014621/xu5707sup1.cif

Structure factors: contains datablock(s) I. DOI: 10.1107/S1600536813014621/xu5707Isup2.hkl

Click here for additional data file.

Supplementary material file. DOI: 10.1107/S1600536813014621/xu5707Isup3.cml

Additional supplementary materials: crystallographic information; 3D view; checkCIF report

C21H13ClFNO2S	Dx = 1.464 Mg m−3
Mr = 397.84	Melting point: 419(2) K
Orthorhombic, Pna21	Mo Kα radiation, λ = 0.7107 Å
Hall symbol: P 2c -2n	Cell parameters from 340 reflections
a = 19.7280 (6) Å	θ = 2.7–27.0°
b = 7.4755 (3) Å	µ = 0.35 mm−1
c = 24.4847 (7) Å	T = 292 K
V = 3611.0 (2) Å3	Block, colorless
Z = 8	0.18 × 0.12 × 0.08 mm
F(000) = 1632

Oxford Diffraction Xcalibur (Eos, Nova) diffractometer	7100 independent reflections
Radiation source: Mova (Mo) X-ray Source	4182 reflections with I > 2σ(I)
Mirror monochromator	Rint = 0.076
Detector resolution: 16.0839 pixels mm-1	θmax = 26.0°, θmin = 2.7°
ω scans	h = −24→24
Absorption correction: multi-scan (CrysAlis PRO; Oxford Diffraction, 2009)	k = −9→9
Tmin = 0.939, Tmax = 0.972	l = −30→30
36561 measured reflections

Refinement on F2	Hydrogen site location: inferred from neighbouring sites
Least-squares matrix: full	H-atom parameters constrained
R[F2 > 2σ(F2)] = 0.053	w = 1/[σ2(Fo2) + (0.037P)2] where P = (Fo2 + 2Fc2)/3
wR(F2) = 0.118	(Δ/σ)max < 0.001
S = 0.99	Δρmax = 0.31 e Å−3
7100 reflections	Δρmin = −0.21 e Å−3
488 parameters	Extinction correction: SHELXL97 (Sheldrick, 2008), Fc*=kFc[1+0.001xFc2λ3/sin(2θ)]-1/4
1 restraint	Extinction coefficient: 0.0012 (2)
Primary atom site location: structure-invariant direct methods	Absolute structure: Flack (1983)
Secondary atom site location: difference Fourier map	Flack parameter: −0.05 (8)

Geometry. All s.u.'s (except the s.u. in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell s.u.'s are taken into account individually in the estimation of s.u.'s in distances, angles and torsion angles; correlations between s.u.'s in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell s.u.'s is used for estimating s.u.'s 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 > 2σ(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
S2	0.06104 (6)	0.33720 (18)	0.47599 (5)	0.0583 (4)
S1	0.17610 (6)	0.63708 (17)	0.25881 (5)	0.0595 (4)
Cl2	0.06464 (8)	0.7998 (2)	0.57593 (6)	0.1029 (6)
Cl1	0.18806 (8)	0.1307 (2)	0.15892 (6)	0.1061 (6)
O1	0.22799 (14)	0.5887 (4)	0.36472 (11)	0.0561 (8)
N1	0.08765 (16)	0.8291 (5)	0.31021 (13)	0.0426 (9)
O2	0.41192 (16)	0.4498 (5)	0.33659 (13)	0.0686 (10)
O3	0.00885 (14)	0.3921 (4)	0.37068 (11)	0.0537 (8)
N2	0.14867 (17)	0.1432 (5)	0.42445 (14)	0.0442 (9)
F1	0.37852 (17)	0.3630 (5)	0.53847 (12)	0.1056 (12)
F2	−0.14027 (16)	0.6181 (5)	0.19584 (12)	0.0965 (11)
C35	−0.0842 (2)	0.5483 (6)	0.33474 (16)	0.0444 (11)
C6	0.06876 (18)	0.8298 (5)	0.25537 (18)	0.0420 (10)
C27	0.1675 (2)	0.1403 (6)	0.47895 (18)	0.0427 (10)
C28	0.0952 (2)	0.2386 (5)	0.41793 (18)	0.0406 (10)
C16	0.3100 (2)	0.3434 (5)	0.29917 (17)	0.0397 (10)
C37	−0.0700 (2)	0.6470 (6)	0.43582 (17)	0.0443 (11)
C24	0.1953 (2)	0.1670 (7)	0.5891 (2)	0.0622 (14)
H24	0.2059	0.1769	0.6260	0.075*
C18	0.2180 (2)	0.1664 (6)	0.26527 (19)	0.0530 (12)
H18	0.1816	0.0900	0.2717	0.064*
C26	0.2223 (2)	0.0503 (6)	0.50034 (18)	0.0532 (12)
H26	0.2501	−0.0184	0.4779	0.064*
C34	−0.1231 (2)	0.6039 (6)	0.29010 (19)	0.0553 (13)
H34	−0.1627	0.6688	0.2955	0.066*
C9	0.2631 (2)	0.5326 (6)	0.40965 (16)	0.0446 (11)
C1	0.1111 (2)	0.7311 (6)	0.22139 (19)	0.0492 (12)
C19	0.2358 (3)	0.2103 (7)	0.21246 (19)	0.0571 (13)
C38	−0.0117 (2)	0.7485 (5)	0.4272 (2)	0.0473 (12)
H38	0.0004	0.7809	0.3918	0.057*
C15	0.3522 (2)	0.4139 (6)	0.34429 (18)	0.0472 (11)
C21	0.3291 (2)	0.3796 (6)	0.24532 (17)	0.0500 (12)
H21	0.3673	0.4487	0.2384	0.060*
O4	−0.17413 (16)	0.5686 (5)	0.39716 (13)	0.0701 (10)
C17	0.2540 (2)	0.2356 (6)	0.30809 (19)	0.0461 (12)
H17	0.2406	0.2100	0.3437	0.055*
C40	0.0101 (3)	0.7524 (7)	0.5223 (2)	0.0609 (14)
C2	0.0976 (2)	0.7182 (7)	0.1656 (2)	0.0652 (14)
H2	0.1258	0.6527	0.1427	0.078*
C10	0.2421 (2)	0.5674 (6)	0.46288 (17)	0.0515 (12)
H10	0.2019	0.6291	0.4693	0.062*
C41	−0.0482 (2)	0.6569 (7)	0.53269 (19)	0.0623 (14)
H41	−0.0604	0.6271	0.5682	0.075*
C32	−0.0457 (3)	0.4639 (7)	0.22913 (18)	0.0631 (14)
H32	−0.0333	0.4358	0.1935	0.076*
C29	0.0633 (2)	0.2694 (6)	0.36384 (19)	0.0507 (12)
H29A	0.0964	0.3179	0.3385	0.061*
H29B	0.0465	0.1574	0.3491	0.061*
C14	0.3237 (2)	0.4423 (6)	0.39979 (17)	0.0426 (11)
C5	0.0125 (2)	0.9163 (6)	0.23477 (18)	0.0535 (12)
H5	−0.0158	0.9825	0.2575	0.064*
C31	−0.0069 (2)	0.4062 (6)	0.27210 (17)	0.0546 (13)
H31	0.0321	0.3393	0.2658	0.066*
C22	0.1258 (2)	0.2402 (6)	0.51368 (18)	0.0453 (12)
C42	−0.0883 (2)	0.6062 (7)	0.48870 (19)	0.0585 (13)
H42	−0.1282	0.5435	0.4950	0.070*
C11	0.2812 (3)	0.5095 (6)	0.50601 (18)	0.0633 (14)
H11	0.2674	0.5295	0.5418	0.076*
C36	−0.1134 (2)	0.5866 (6)	0.39001 (17)	0.0488 (11)
C33	−0.1023 (3)	0.5621 (7)	0.2386 (2)	0.0635 (14)
C39	0.0280 (2)	0.8013 (6)	0.4703 (2)	0.0546 (12)
H39	0.0667	0.8696	0.4644	0.066*
C8	0.1729 (2)	0.7062 (6)	0.37194 (18)	0.0504 (12)
H8A	0.1884	0.8193	0.3868	0.061*
H8B	0.1401	0.6548	0.3969	0.061*
C30	−0.0263 (2)	0.4483 (6)	0.32504 (18)	0.0458 (11)
C4	−0.0004 (2)	0.9022 (7)	0.1803 (2)	0.0667 (15)
H4	−0.0384	0.9592	0.1659	0.080*
C7	0.1416 (2)	0.7339 (6)	0.31678 (18)	0.0444 (11)
C25	0.2354 (2)	0.0638 (7)	0.55564 (19)	0.0610 (13)
H25	0.2720	0.0021	0.5705	0.073*
C20	0.2919 (2)	0.3138 (6)	0.20268 (19)	0.0574 (13)
H20	0.3046	0.3394	0.1670	0.069*
C12	0.3407 (3)	0.4220 (7)	0.49521 (19)	0.0641 (14)
C13	0.3629 (2)	0.3886 (6)	0.4435 (2)	0.0575 (13)
H13	0.4039	0.3304	0.4378	0.069*
C23	0.1399 (2)	0.2553 (6)	0.5689 (2)	0.0595 (13)
H23	0.1124	0.3236	0.5917	0.071*
C3	0.0414 (2)	0.8049 (8)	0.1455 (2)	0.0702 (16)
H3	0.0314	0.7985	0.1085	0.084*

	U11	U22	U33	U12	U13	U23
S2	0.0601 (8)	0.0648 (8)	0.0499 (7)	0.0205 (7)	0.0044 (6)	−0.0056 (7)
S1	0.0573 (7)	0.0733 (9)	0.0478 (7)	0.0237 (6)	0.0023 (6)	−0.0068 (7)
Cl2	0.1140 (12)	0.1242 (14)	0.0707 (10)	−0.0212 (11)	−0.0177 (9)	−0.0367 (10)
Cl1	0.1281 (13)	0.1298 (15)	0.0602 (10)	−0.0478 (11)	−0.0180 (9)	−0.0170 (10)
O1	0.0629 (19)	0.067 (2)	0.0387 (17)	0.0271 (17)	−0.0047 (15)	−0.0040 (16)
N1	0.0363 (19)	0.045 (2)	0.047 (2)	0.0055 (17)	0.0011 (16)	−0.0016 (17)
O2	0.045 (2)	0.088 (3)	0.072 (2)	−0.0047 (19)	0.0011 (18)	−0.006 (2)
O3	0.0607 (19)	0.060 (2)	0.0403 (17)	0.0167 (17)	−0.0029 (15)	−0.0032 (16)
N2	0.0402 (19)	0.048 (2)	0.044 (2)	0.0019 (18)	0.0020 (17)	−0.0069 (18)
F1	0.113 (2)	0.145 (3)	0.0588 (19)	0.009 (2)	−0.0385 (18)	0.025 (2)
F2	0.102 (2)	0.122 (3)	0.065 (2)	−0.007 (2)	−0.0297 (17)	0.033 (2)
C35	0.045 (3)	0.047 (3)	0.041 (3)	−0.011 (2)	−0.004 (2)	0.006 (2)
C6	0.041 (2)	0.043 (3)	0.043 (3)	−0.001 (2)	0.001 (2)	0.003 (2)
C27	0.044 (2)	0.043 (3)	0.041 (3)	0.000 (2)	0.008 (2)	−0.007 (2)
C28	0.043 (2)	0.041 (3)	0.038 (3)	0.000 (2)	0.003 (2)	−0.0030 (19)
C16	0.039 (2)	0.036 (2)	0.044 (2)	0.004 (2)	0.001 (2)	0.000 (2)
C37	0.050 (3)	0.041 (3)	0.042 (3)	0.007 (2)	0.003 (2)	−0.003 (2)
C24	0.071 (3)	0.071 (4)	0.044 (3)	0.001 (3)	−0.004 (3)	0.003 (3)
C18	0.061 (3)	0.043 (3)	0.055 (3)	−0.013 (2)	0.002 (2)	−0.004 (2)
C26	0.044 (3)	0.061 (3)	0.055 (3)	0.007 (2)	0.003 (2)	−0.005 (2)
C34	0.052 (3)	0.054 (3)	0.060 (3)	−0.007 (2)	−0.010 (2)	0.011 (3)
C9	0.047 (3)	0.046 (3)	0.041 (3)	0.002 (2)	−0.004 (2)	−0.001 (2)
C1	0.043 (2)	0.058 (3)	0.046 (3)	0.010 (2)	0.001 (2)	0.004 (2)
C19	0.073 (3)	0.051 (3)	0.047 (3)	−0.007 (3)	−0.006 (3)	−0.012 (2)
C38	0.051 (3)	0.039 (3)	0.052 (3)	−0.002 (2)	0.006 (2)	−0.002 (2)
C15	0.046 (3)	0.041 (3)	0.054 (3)	0.004 (2)	−0.006 (2)	0.001 (2)
C21	0.042 (2)	0.059 (3)	0.049 (3)	−0.001 (2)	0.009 (2)	0.000 (2)
O4	0.046 (2)	0.095 (3)	0.069 (2)	−0.002 (2)	0.0001 (17)	−0.003 (2)
C17	0.050 (3)	0.042 (3)	0.046 (3)	0.001 (2)	0.008 (2)	−0.003 (2)
C40	0.068 (3)	0.062 (3)	0.053 (3)	−0.003 (3)	0.004 (3)	−0.022 (3)
C2	0.053 (3)	0.096 (4)	0.046 (3)	0.002 (3)	0.005 (3)	−0.001 (3)
C10	0.062 (3)	0.054 (3)	0.038 (3)	−0.002 (3)	−0.001 (2)	−0.005 (2)
C41	0.067 (3)	0.074 (4)	0.045 (3)	0.006 (3)	0.013 (3)	−0.008 (3)
C32	0.079 (4)	0.070 (4)	0.040 (3)	−0.021 (3)	−0.005 (3)	0.004 (3)
C29	0.049 (3)	0.054 (3)	0.050 (3)	0.007 (2)	0.006 (2)	−0.011 (2)
C14	0.047 (3)	0.043 (3)	0.038 (2)	0.002 (2)	−0.010 (2)	−0.001 (2)
C5	0.046 (3)	0.063 (3)	0.052 (3)	0.005 (2)	−0.002 (2)	0.007 (2)
C31	0.060 (3)	0.056 (3)	0.048 (3)	−0.003 (2)	0.002 (2)	−0.001 (2)
C22	0.048 (2)	0.046 (3)	0.042 (3)	0.001 (2)	0.001 (2)	0.002 (2)
C42	0.052 (3)	0.066 (3)	0.058 (3)	0.000 (3)	0.009 (2)	0.005 (3)
C11	0.084 (4)	0.067 (4)	0.039 (3)	−0.019 (3)	−0.008 (3)	0.005 (3)
C36	0.046 (3)	0.044 (3)	0.056 (3)	0.005 (2)	−0.002 (2)	0.006 (2)
C33	0.068 (3)	0.068 (4)	0.055 (3)	−0.011 (3)	−0.018 (3)	0.015 (3)
C39	0.053 (3)	0.048 (3)	0.063 (3)	−0.007 (2)	0.006 (3)	−0.008 (3)
C8	0.056 (3)	0.052 (3)	0.043 (3)	0.020 (2)	0.000 (2)	0.002 (2)
C30	0.057 (3)	0.040 (3)	0.041 (3)	−0.003 (2)	−0.008 (2)	0.003 (2)
C4	0.052 (3)	0.085 (4)	0.063 (3)	0.007 (3)	−0.003 (3)	0.020 (3)
C7	0.046 (2)	0.046 (3)	0.041 (3)	0.003 (2)	0.003 (2)	0.001 (2)
C25	0.056 (3)	0.069 (4)	0.058 (3)	0.009 (3)	−0.007 (2)	−0.001 (3)
C20	0.067 (3)	0.064 (4)	0.041 (3)	0.005 (3)	0.003 (2)	0.001 (2)
C12	0.075 (4)	0.072 (4)	0.045 (3)	−0.002 (3)	−0.025 (3)	0.018 (3)
C13	0.057 (3)	0.060 (3)	0.056 (3)	0.004 (3)	−0.013 (2)	0.010 (3)
C23	0.067 (3)	0.067 (4)	0.044 (3)	0.009 (3)	0.008 (3)	−0.004 (3)
C3	0.059 (3)	0.107 (5)	0.045 (3)	−0.005 (3)	−0.007 (3)	0.014 (3)

S2—C22	1.735 (4)	C1—C2	1.395 (6)
S2—C28	1.737 (4)	C19—C20	1.371 (6)
S1—C1	1.726 (4)	C38—C39	1.373 (6)
S1—C7	1.733 (4)	C38—H38	0.9300
Cl2—C40	1.734 (5)	C15—C14	1.486 (6)
Cl1—C19	1.721 (5)	C21—C20	1.368 (6)
O1—C9	1.366 (5)	C21—H21	0.9300
O1—C8	1.408 (4)	O4—C36	1.218 (5)
N1—C7	1.291 (5)	C17—H17	0.9300
N1—C6	1.393 (5)	C40—C39	1.369 (7)
O2—C15	1.224 (5)	C40—C41	1.378 (6)
O3—C30	1.380 (5)	C2—C3	1.374 (6)
O3—C29	1.422 (5)	C2—H2	0.9300
N2—C28	1.283 (5)	C10—C11	1.378 (6)
N2—C27	1.386 (5)	C10—H10	0.9300
F1—C12	1.369 (5)	C41—C42	1.389 (6)
F2—C33	1.354 (5)	C41—H41	0.9300
C35—C30	1.387 (6)	C32—C33	1.356 (7)
C35—C34	1.398 (5)	C32—C31	1.371 (6)
C35—C36	1.498 (6)	C32—H32	0.9300
C6—C5	1.380 (5)	C29—H29A	0.9700
C6—C1	1.391 (6)	C29—H29B	0.9700
C27—C26	1.376 (5)	C14—C13	1.381 (5)
C27—C22	1.399 (5)	C5—C4	1.363 (6)
C28—C29	1.485 (6)	C5—H5	0.9300
C16—C17	1.385 (5)	C31—C30	1.388 (5)
C16—C21	1.398 (6)	C31—H31	0.9300
C16—C15	1.480 (6)	C22—C23	1.386 (6)
C37—C42	1.378 (6)	C42—H42	0.9300
C37—C38	1.394 (5)	C11—C12	1.369 (7)
C37—C36	1.481 (6)	C11—H11	0.9300
C24—C23	1.369 (6)	C39—H39	0.9300
C24—C25	1.376 (6)	C8—C7	1.500 (6)
C24—H24	0.9300	C8—H8A	0.9700
C18—C17	1.368 (6)	C8—H8B	0.9700
C18—C19	1.380 (6)	C4—C3	1.391 (6)
C18—H18	0.9300	C4—H4	0.9300
C26—C25	1.382 (6)	C25—H25	0.9300
C26—H26	0.9300	C20—H20	0.9300
C34—C33	1.362 (7)	C12—C13	1.362 (6)
C34—H34	0.9300	C13—H13	0.9300
C9—C10	1.392 (5)	C23—H23	0.9300
C9—C14	1.394 (6)	C3—H3	0.9300
C22—S2—C28	88.4 (2)	C33—C32—C31	119.9 (4)
C1—S1—C7	88.4 (2)	C33—C32—H32	120.0
C9—O1—C8	118.8 (3)	C31—C32—H32	120.0
C7—N1—C6	110.0 (3)	O3—C29—C28	108.4 (4)
C30—O3—C29	118.7 (3)	O3—C29—H29A	110.0
C28—N2—C27	110.4 (3)	C28—C29—H29A	110.0
C30—C35—C34	118.6 (4)	O3—C29—H29B	110.0
C30—C35—C36	125.0 (4)	C28—C29—H29B	110.0
C34—C35—C36	116.1 (4)	H29A—C29—H29B	108.4
C5—C6—N1	124.7 (4)	C13—C14—C9	119.2 (4)
C5—C6—C1	120.9 (4)	C13—C14—C15	117.1 (4)
N1—C6—C1	114.5 (4)	C9—C14—C15	123.5 (4)
C26—C27—N2	125.8 (4)	C4—C5—C6	118.2 (5)
C26—C27—C22	119.4 (4)	C4—C5—H5	120.9
N2—C27—C22	114.8 (4)	C6—C5—H5	120.9
N2—C28—C29	123.1 (4)	C32—C31—C30	119.5 (4)
N2—C28—S2	116.9 (3)	C32—C31—H31	120.3
C29—C28—S2	120.0 (3)	C30—C31—H31	120.3
C17—C16—C21	118.5 (4)	C23—C22—C27	121.3 (4)
C17—C16—C15	122.5 (4)	C23—C22—S2	129.2 (4)
C21—C16—C15	118.9 (4)	C27—C22—S2	109.5 (3)
C42—C37—C38	118.6 (4)	C37—C42—C41	121.3 (4)
C42—C37—C36	119.5 (4)	C37—C42—H42	119.4
C38—C37—C36	121.9 (4)	C41—C42—H42	119.4
C23—C24—C25	121.1 (5)	C12—C11—C10	118.8 (4)
C23—C24—H24	119.5	C12—C11—H11	120.6
C25—C24—H24	119.5	C10—C11—H11	120.6
C17—C18—C19	119.7 (4)	O4—C36—C37	119.6 (4)
C17—C18—H18	120.1	O4—C36—C35	119.1 (4)
C19—C18—H18	120.1	C37—C36—C35	121.4 (4)
C27—C26—C25	119.0 (4)	F2—C33—C32	119.4 (5)
C27—C26—H26	120.5	F2—C33—C34	118.6 (5)
C25—C26—H26	120.5	C32—C33—C34	122.0 (4)
C33—C34—C35	119.4 (4)	C40—C39—C38	119.4 (4)
C33—C34—H34	120.3	C40—C39—H39	120.3
C35—C34—H34	120.3	C38—C39—H39	120.3
O1—C9—C10	123.1 (4)	O1—C8—C7	106.9 (3)
O1—C9—C14	116.4 (4)	O1—C8—H8A	110.3
C10—C9—C14	120.5 (4)	C7—C8—H8A	110.3
C2—C1—C6	120.5 (4)	O1—C8—H8B	110.3
C2—C1—S1	129.3 (4)	C7—C8—H8B	110.3
C6—C1—S1	110.2 (3)	H8A—C8—H8B	108.6
C20—C19—C18	120.3 (4)	O3—C30—C31	123.3 (4)
C20—C19—Cl1	120.3 (4)	O3—C30—C35	116.1 (4)
C18—C19—Cl1	119.5 (4)	C31—C30—C35	120.6 (4)
C39—C38—C37	120.7 (5)	C5—C4—C3	121.9 (5)
C39—C38—H38	119.7	C5—C4—H4	119.0
C37—C38—H38	119.7	C3—C4—H4	119.0
O2—C15—C16	120.3 (4)	N1—C7—C8	121.9 (4)
O2—C15—C14	118.3 (4)	N1—C7—S1	116.9 (3)
C16—C15—C14	121.4 (4)	C8—C7—S1	121.2 (3)
C20—C21—C16	120.4 (4)	C24—C25—C26	121.0 (4)
C20—C21—H21	119.8	C24—C25—H25	119.5
C16—C21—H21	119.8	C26—C25—H25	119.5
C18—C17—C16	120.9 (4)	C21—C20—C19	120.2 (4)
C18—C17—H17	119.6	C21—C20—H20	119.9
C16—C17—H17	119.6	C19—C20—H20	119.9
C39—C40—C41	121.7 (5)	C13—C12—F1	119.0 (5)
C39—C40—Cl2	119.3 (4)	C13—C12—C11	122.9 (4)
C41—C40—Cl2	118.9 (4)	F1—C12—C11	118.2 (5)
C3—C2—C1	118.2 (5)	C12—C13—C14	119.1 (4)
C3—C2—H2	120.9	C12—C13—H13	120.4
C1—C2—H2	120.9	C14—C13—H13	120.4
C11—C10—C9	119.5 (4)	C24—C23—C22	118.1 (4)
C11—C10—H10	120.3	C24—C23—H23	120.9
C9—C10—H10	120.3	C22—C23—H23	120.9
C40—C41—C42	118.2 (4)	C2—C3—C4	120.4 (5)
C40—C41—H41	120.9	C2—C3—H3	119.8
C42—C41—H41	120.9	C4—C3—H3	119.8
C7—N1—C6—C5	178.7 (4)	C26—C27—C22—S2	−179.7 (3)
C7—N1—C6—C1	−0.1 (5)	N2—C27—C22—S2	0.6 (5)
C28—N2—C27—C26	179.8 (4)	C28—S2—C22—C23	177.5 (5)
C28—N2—C27—C22	−0.5 (5)	C28—S2—C22—C27	−0.4 (3)
C27—N2—C28—C29	179.1 (4)	C38—C37—C42—C41	−3.1 (7)
C27—N2—C28—S2	0.2 (5)	C36—C37—C42—C41	178.5 (4)
C22—S2—C28—N2	0.1 (3)	C40—C41—C42—C37	1.2 (7)
C22—S2—C28—C29	−178.8 (4)	C9—C10—C11—C12	1.2 (7)
N2—C27—C26—C25	178.5 (4)	C42—C37—C36—O4	29.3 (6)
C22—C27—C26—C25	−1.2 (6)	C38—C37—C36—O4	−148.9 (4)
C30—C35—C34—C33	−1.4 (7)	C42—C37—C36—C35	−151.1 (4)
C36—C35—C34—C33	−175.2 (4)	C38—C37—C36—C35	30.6 (6)
C8—O1—C9—C10	8.4 (6)	C30—C35—C36—O4	−134.0 (5)
C8—O1—C9—C14	−169.3 (4)	C34—C35—C36—O4	39.3 (6)
C5—C6—C1—C2	0.2 (7)	C30—C35—C36—C37	46.5 (7)
N1—C6—C1—C2	179.1 (4)	C34—C35—C36—C37	−140.2 (4)
C5—C6—C1—S1	−179.3 (3)	C31—C32—C33—F2	−179.9 (4)
N1—C6—C1—S1	−0.4 (5)	C31—C32—C33—C34	−1.1 (8)
C7—S1—C1—C2	−178.8 (5)	C35—C34—C33—F2	−179.5 (4)
C7—S1—C1—C6	0.6 (3)	C35—C34—C33—C32	1.7 (8)
C17—C18—C19—C20	4.0 (7)	C41—C40—C39—C38	−2.4 (7)
C17—C18—C19—Cl1	−177.1 (4)	Cl2—C40—C39—C38	173.6 (3)
C42—C37—C38—C39	2.3 (6)	C37—C38—C39—C40	0.4 (7)
C36—C37—C38—C39	−179.4 (4)	C9—O1—C8—C7	−176.1 (4)
C17—C16—C15—O2	153.1 (4)	C29—O3—C30—C31	−6.9 (6)
C21—C16—C15—O2	−23.8 (6)	C29—O3—C30—C35	171.6 (4)
C17—C16—C15—C14	−26.6 (6)	C32—C31—C30—O3	178.4 (4)
C21—C16—C15—C14	156.5 (4)	C32—C31—C30—C35	−0.1 (7)
C17—C16—C21—C20	1.9 (6)	C34—C35—C30—O3	−177.9 (4)
C15—C16—C21—C20	178.9 (4)	C36—C35—C30—O3	−4.8 (6)
C19—C18—C17—C16	−2.8 (7)	C34—C35—C30—C31	0.7 (6)
C21—C16—C17—C18	−0.1 (6)	C36—C35—C30—C31	173.9 (4)
C15—C16—C17—C18	−177.1 (4)	C6—C5—C4—C3	−0.4 (7)
C6—C1—C2—C3	−0.2 (7)	C6—N1—C7—C8	−178.8 (4)
S1—C1—C2—C3	179.2 (4)	C6—N1—C7—S1	0.6 (5)
O1—C9—C10—C11	−178.5 (4)	O1—C8—C7—N1	176.7 (4)
C14—C9—C10—C11	−0.9 (7)	O1—C8—C7—S1	−2.7 (5)
C39—C40—C41—C42	1.7 (7)	C1—S1—C7—N1	−0.8 (4)
Cl2—C40—C41—C42	−174.4 (4)	C1—S1—C7—C8	178.7 (4)
C30—O3—C29—C28	176.6 (3)	C23—C24—C25—C26	2.0 (8)
N2—C28—C29—O3	−175.2 (4)	C27—C26—C25—C24	−0.9 (7)
S2—C28—C29—O3	3.6 (5)	C16—C21—C20—C19	−0.7 (7)
O1—C9—C14—C13	177.4 (4)	C18—C19—C20—C21	−2.3 (7)
C10—C9—C14—C13	−0.4 (7)	Cl1—C19—C20—C21	178.9 (4)
O1—C9—C14—C15	3.1 (6)	C10—C11—C12—C13	−0.3 (8)
C10—C9—C14—C15	−174.7 (4)	C10—C11—C12—F1	−179.1 (4)
O2—C15—C14—C13	−43.0 (6)	F1—C12—C13—C14	177.7 (4)
C16—C15—C14—C13	136.7 (4)	C11—C12—C13—C14	−1.0 (8)
O2—C15—C14—C9	131.3 (5)	C9—C14—C13—C12	1.4 (7)
C16—C15—C14—C9	−49.0 (6)	C15—C14—C13—C12	176.0 (4)
N1—C6—C5—C4	−178.7 (4)	C25—C24—C23—C22	−0.9 (7)
C1—C6—C5—C4	0.1 (7)	C27—C22—C23—C24	−1.1 (7)
C33—C32—C31—C30	0.3 (7)	S2—C22—C23—C24	−178.9 (4)
C26—C27—C22—C23	2.2 (6)	C1—C2—C3—C4	−0.1 (8)
N2—C27—C22—C23	−177.5 (4)	C5—C4—C3—C2	0.4 (8)

D—H···A	D—H	H···A	D···A	D—H···A
C3—H3···F1i	0.93	2.52	3.091 (6)	120
C5—H5···O2ii	0.93	2.46	3.340 (5)	158
C26—H26···O4iii	0.93	2.51	3.369 (5)	154
C18—H18···Cg1iv	0.93	2.83	3.686 (5)	154
C39—H39···Cg2v	0.93	2.82	3.619 (5)	145

Table 1

Hydrogen-bond geometry (Å, °)

Cg1 and Cg2 are the centroids of the thia­zole rings S1/C1/C6/N1/C7 and S2/C22/C27/N2/C28, respectively.

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
C3—H3⋯F1i	0.93	2.52	3.091 (6)	120
C5—H5⋯O2ii	0.93	2.46	3.340 (5)	158
C26—H26⋯O4iii	0.93	2.51	3.369 (5)	154
C18—H18⋯Cg1iv	0.93	2.83	3.686 (5)	154
C39—H39⋯Cg2v	0.93	2.82	3.619 (5)	145

Symmetry codes: (i) ; (ii) ; (iii) ; (iv) ; (v) .