6-Fluoro-2-(4-meth-oxy-phen-yl)imidazo[2,1-b][1,3]benzothia-zole.

The asymmetric unit of the title compound, C(16)H(11)FN(2)OS, comprises two independent mol-ecules in which the benzothia-zole rings are essentially planar, with maximum deviations of 0.038 (2) and 0.045 (3) Å. The central benzothia-zole ring makes dihedral angles of 4.87 (13) and 0.64 (12)° and 4.04 (12) and 3.67 (12)° with the two terminal phenyl rings in the two independent mol-ecules. In the crystal, mol-ecules are connected via weak inter-molecular C-H⋯O hydrogen bonds forming supra-molecular chains along the c axis.

Related literature

For details and applications of benzothia­zoles, see: Yaseen et al. (2006 ▶); Kini et al. (2007 ▶); Munirajasekhar et al. (2011 ▶); Gurupadayya et al. (2008 ▶); Mittal et al. (2007 ▶); Bowyer et al. (2007 ▶); Pozas et al. (2005 ▶); Rana et al. (2008 ▶); Saha et al. (2000 ▶); Katritzky & Rees (1984 ▶). For bond-length data, see: Allen et al. (1987 ▶). For a related structure, see: Fun et al. (2011 ▶).

Experimental

Crystal data

C16H11FN2OS

M = 298.33

Monoclinic,

a = 7.6120 (13) Å

b = 13.883 (2) Å

c = 13.049 (2) Å

β = 105.117 (3)°

V = 1331.3 (4) Å3

Z = 4

Mo Kα radiation

μ = 0.25 mm−1

T = 296 K

0.31 × 0.30 × 0.13 mm

Data collection

Bruker APEXII DUO CCD area-detector diffractometer

Absorption correction: multi-scan (SADABS; Bruker, 2009 ▶) T min = 0.926, T max = 0.967

20506 measured reflections

7656 independent reflections

4268 reflections with I > 2σ(I)

R int = 0.051

Refinement

R[F 2 > 2σ(F 2)] = 0.051

wR(F 2) = 0.116

S = 1.00

7656 reflections

381 parameters

1 restraint

H-atom parameters constrained

Δρmax = 0.24 e Å−3

Δρmin = −0.25 e Å−3

Absolute structure: Flack (1983 ▶), 3649 Friedel pairs

Flack parameter: 0.00 (8)

Data collection: APEX2 (Bruker, 2009 ▶); cell refinement: SAINT (Bruker, 2009 ▶); data reduction: SAINT; program(s) used to solve structure: SHELXTL (Sheldrick, 2008 ▶); program(s) used to refine structure: SHELXTL; molecular graphics: SHELXTL; software used to prepare material for publication: SHELXTL and PLATON (Spek, 2009 ▶).

Crystal structure: contains datablock(s) global, I. DOI: 10.1107/S1600536811046666/bq2315sup1.cif

Structure factors: contains datablock(s) I. DOI: 10.1107/S1600536811046666/bq2315Isup2.hkl

Supplementary material file. DOI: 10.1107/S1600536811046666/bq2315Isup3.cml

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

C16H11FN2OS	F(000) = 616
Mr = 298.33	Dx = 1.488 Mg m−3
Monoclinic, P21	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: P 2yb	Cell parameters from 3518 reflections
a = 7.6120 (13) Å	θ = 2.2–23.5°
b = 13.883 (2) Å	µ = 0.25 mm−1
c = 13.049 (2) Å	T = 296 K
β = 105.117 (3)°	Block, colourless
V = 1331.3 (4) Å3	0.31 × 0.30 × 0.13 mm
Z = 4

Bruker APEXII DUO CCD area-detector diffractometer	7656 independent reflections
Radiation source: fine-focus sealed tube	4268 reflections with I > 2σ(I)
graphite	Rint = 0.051
φ and ω scans	θmax = 30.0°, θmin = 2.2°
Absorption correction: multi-scan (SADABS; Bruker, 2009)	h = −8→10
Tmin = 0.926, Tmax = 0.967	k = −19→19
20506 measured reflections	l = −18→18

Refinement on F2	Secondary atom site location: difference Fourier map
Least-squares matrix: full	Hydrogen site location: inferred from neighbouring sites
R[F2 > 2σ(F2)] = 0.051	H-atom parameters constrained
wR(F2) = 0.116	w = 1/[σ2(Fo2) + (0.0433P)2 + 0.0628P] where P = (Fo2 + 2Fc2)/3
S = 1.00	(Δ/σ)max = 0.001
7656 reflections	Δρmax = 0.24 e Å−3
381 parameters	Δρmin = −0.25 e Å−3
1 restraint	Absolute structure: Flack (1983), 3649 Friedel pairs
Primary atom site location: structure-invariant direct methods	Flack parameter: 0.00 (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
S1A	0.85944 (11)	1.02159 (6)	0.83180 (6)	0.0574 (2)
F1A	1.5287 (3)	0.92386 (17)	0.98451 (18)	0.0787 (7)
O1A	0.1100 (4)	0.95521 (17)	0.15032 (18)	0.0642 (7)
N1A	0.9233 (4)	0.96545 (17)	0.65606 (19)	0.0406 (6)
N2A	0.6279 (4)	1.00305 (19)	0.62596 (19)	0.0499 (7)
C1A	0.8431 (5)	0.9457 (2)	0.5494 (2)	0.0447 (8)
H1AA	0.8999	0.9213	0.4999	0.054*
C2A	1.0919 (5)	0.9560 (2)	0.7307 (3)	0.0416 (8)
C3A	1.2520 (5)	0.9211 (2)	0.7145 (3)	0.0462 (8)
H3AA	1.2599	0.9045	0.6468	0.055*
C4A	1.4000 (5)	0.9111 (2)	0.8010 (3)	0.0517 (9)
H4AA	1.5099	0.8876	0.7927	0.062*
C5A	1.3830 (5)	0.9365 (2)	0.9004 (3)	0.0529 (9)
C6A	1.2256 (5)	0.9728 (3)	0.9189 (3)	0.0513 (9)
H6AA	1.2195	0.9902	0.9867	0.062*
C7A	1.0774 (5)	0.9822 (2)	0.8322 (2)	0.0448 (7)
C8A	0.7857 (5)	0.9987 (2)	0.6965 (3)	0.0475 (8)
C9A	0.6656 (5)	0.9695 (2)	0.5327 (3)	0.0442 (8)
C10A	0.5183 (4)	0.9645 (2)	0.4339 (2)	0.0419 (7)
C11A	0.5515 (5)	0.9338 (2)	0.3389 (3)	0.0512 (9)
H11A	0.6680	0.9147	0.3376	0.061*
C12A	0.4119 (5)	0.9315 (2)	0.2468 (3)	0.0535 (9)
H12A	0.4354	0.9107	0.1840	0.064*
C13A	0.2379 (5)	0.9599 (2)	0.2466 (2)	0.0469 (8)
C14A	0.2027 (5)	0.9902 (2)	0.3400 (2)	0.0489 (8)
H14A	0.0862	1.0094	0.3410	0.059*
C15A	0.3434 (5)	0.9915 (2)	0.4323 (2)	0.0485 (8)
H15A	0.3189	1.0113	0.4952	0.058*
C16A	−0.0712 (5)	0.9810 (3)	0.1471 (3)	0.0736 (11)
H16A	−0.1439	0.9797	0.0749	0.110*
H16B	−0.0730	1.0446	0.1755	0.110*
H16C	−0.1196	0.9361	0.1886	0.110*
S1B	0.44615 (11)	0.65085 (6)	0.87504 (6)	0.0551 (2)
F1B	1.1185 (3)	0.74352 (15)	1.02571 (15)	0.0727 (6)
O1B	−0.3004 (4)	0.72079 (18)	0.19408 (19)	0.0642 (7)
N1B	0.5109 (4)	0.70099 (17)	0.6977 (2)	0.0420 (7)
N2B	0.2174 (4)	0.6637 (2)	0.6678 (2)	0.0471 (7)
C1B	0.4345 (5)	0.7183 (2)	0.5919 (2)	0.0449 (8)
H1BA	0.4932	0.7411	0.5425	0.054*
C2B	0.6794 (4)	0.71310 (19)	0.7725 (2)	0.0379 (7)
C3B	0.8426 (5)	0.7428 (2)	0.7558 (3)	0.0450 (8)
H3BA	0.8528	0.7565	0.6878	0.054*
C4B	0.9899 (5)	0.7517 (2)	0.8425 (3)	0.0496 (8)
H4BA	1.1021	0.7708	0.8336	0.060*
C5B	0.9712 (5)	0.7326 (2)	0.9415 (3)	0.0500 (9)
C6B	0.8146 (5)	0.7013 (2)	0.9615 (2)	0.0496 (8)
H6BA	0.8072	0.6879	1.0301	0.060*
C7B	0.6651 (4)	0.6903 (2)	0.8739 (2)	0.0427 (8)
C8B	0.3730 (4)	0.6691 (2)	0.7379 (2)	0.0444 (7)
C9B	0.2543 (5)	0.6953 (2)	0.5740 (2)	0.0417 (8)
C10B	0.1091 (5)	0.7020 (2)	0.4758 (3)	0.0423 (8)
C11B	0.1394 (5)	0.7359 (2)	0.3813 (2)	0.0506 (8)
H11B	0.2560	0.7550	0.3802	0.061*
C12B	0.0013 (5)	0.7417 (3)	0.2897 (3)	0.0554 (9)
H12B	0.0248	0.7652	0.2279	0.066*
C13B	−0.1737 (5)	0.7124 (2)	0.2892 (2)	0.0472 (8)
C14B	−0.2083 (5)	0.6788 (2)	0.3807 (3)	0.0505 (9)
H14B	−0.3251	0.6595	0.3811	0.061*
C15B	−0.0671 (5)	0.6739 (2)	0.4732 (2)	0.0489 (8)
H15B	−0.0915	0.6512	0.5351	0.059*
C16B	−0.4794 (5)	0.6850 (3)	0.1868 (3)	0.0671 (10)
H16D	−0.5526	0.6914	0.1151	0.101*
H16E	−0.5333	0.7213	0.2334	0.101*
H16F	−0.4724	0.6184	0.2071	0.101*

	U11	U22	U33	U12	U13	U23
S1A	0.0490 (6)	0.0787 (6)	0.0442 (5)	0.0094 (4)	0.0113 (4)	−0.0105 (4)
F1A	0.0579 (17)	0.1000 (16)	0.0651 (15)	0.0116 (13)	−0.0074 (12)	−0.0116 (12)
O1A	0.0589 (18)	0.0840 (17)	0.0428 (13)	0.0008 (14)	0.0007 (12)	−0.0052 (12)
N1A	0.0385 (18)	0.0436 (14)	0.0396 (15)	0.0029 (12)	0.0104 (12)	0.0004 (12)
N2A	0.0422 (17)	0.0633 (18)	0.0431 (14)	0.0056 (14)	0.0093 (12)	−0.0042 (12)
C1A	0.053 (2)	0.0441 (17)	0.0376 (17)	−0.0003 (14)	0.0128 (15)	0.0002 (12)
C2A	0.045 (2)	0.0360 (16)	0.0452 (18)	0.0008 (15)	0.0144 (15)	0.0016 (13)
C3A	0.050 (2)	0.0409 (16)	0.0503 (19)	0.0022 (15)	0.0175 (17)	−0.0004 (14)
C4A	0.041 (2)	0.0457 (18)	0.068 (3)	0.0004 (16)	0.0143 (19)	−0.0006 (16)
C5A	0.047 (2)	0.053 (2)	0.053 (2)	−0.0049 (16)	0.0036 (17)	−0.0041 (15)
C6A	0.052 (2)	0.055 (2)	0.0446 (19)	−0.0062 (17)	0.0102 (16)	−0.0063 (16)
C7A	0.049 (2)	0.0423 (16)	0.0439 (18)	−0.0001 (15)	0.0130 (15)	−0.0045 (14)
C8A	0.043 (2)	0.054 (2)	0.0478 (19)	0.0048 (16)	0.0155 (15)	−0.0044 (15)
C9A	0.047 (2)	0.0408 (16)	0.0464 (19)	−0.0011 (15)	0.0158 (17)	0.0000 (14)
C10A	0.046 (2)	0.0383 (15)	0.0397 (17)	−0.0018 (14)	0.0077 (14)	0.0010 (13)
C11A	0.050 (2)	0.056 (2)	0.048 (2)	0.0050 (16)	0.0141 (17)	0.0003 (16)
C12A	0.058 (3)	0.064 (2)	0.0387 (18)	0.0004 (17)	0.0125 (17)	−0.0032 (15)
C13A	0.049 (2)	0.0462 (16)	0.0408 (18)	−0.0026 (16)	0.0035 (16)	0.0037 (14)
C14A	0.045 (2)	0.0543 (19)	0.0470 (18)	0.0061 (15)	0.0106 (15)	−0.0025 (14)
C15A	0.052 (2)	0.0525 (19)	0.0405 (18)	−0.0007 (15)	0.0112 (16)	−0.0036 (14)
C16A	0.052 (3)	0.094 (3)	0.064 (2)	0.005 (2)	−0.0045 (18)	0.001 (2)
S1B	0.0432 (5)	0.0785 (6)	0.0425 (4)	−0.0067 (4)	0.0093 (4)	0.0115 (4)
F1B	0.0498 (13)	0.0932 (14)	0.0636 (13)	−0.0094 (11)	−0.0058 (10)	0.0097 (12)
O1B	0.0554 (18)	0.0845 (18)	0.0456 (13)	−0.0021 (14)	0.0009 (12)	0.0108 (13)
N1B	0.0400 (18)	0.0464 (15)	0.0398 (15)	−0.0022 (12)	0.0106 (13)	−0.0020 (12)
N2B	0.0417 (17)	0.0549 (16)	0.0433 (14)	−0.0053 (14)	0.0085 (12)	0.0012 (13)
C1B	0.051 (2)	0.0484 (18)	0.0355 (16)	−0.0038 (15)	0.0121 (15)	0.0004 (13)
C2B	0.0339 (19)	0.0384 (15)	0.0403 (16)	0.0028 (13)	0.0077 (13)	−0.0004 (12)
C3B	0.044 (2)	0.0478 (17)	0.0433 (18)	0.0049 (15)	0.0117 (16)	0.0020 (15)
C4B	0.045 (2)	0.0444 (17)	0.062 (2)	−0.0003 (14)	0.0171 (17)	0.0073 (15)
C5B	0.041 (2)	0.0504 (18)	0.051 (2)	0.0024 (16)	−0.0016 (16)	0.0024 (16)
C6B	0.047 (2)	0.0557 (18)	0.0439 (17)	0.0006 (15)	0.0078 (15)	0.0057 (14)
C7B	0.038 (2)	0.0452 (17)	0.0450 (18)	0.0004 (14)	0.0106 (15)	0.0011 (14)
C8B	0.045 (2)	0.0483 (17)	0.0424 (17)	−0.0028 (15)	0.0157 (15)	0.0026 (14)
C9B	0.045 (2)	0.0432 (16)	0.0373 (17)	−0.0023 (14)	0.0109 (15)	−0.0033 (13)
C10B	0.044 (2)	0.0404 (16)	0.0413 (17)	−0.0024 (14)	0.0083 (15)	−0.0021 (13)
C11B	0.046 (2)	0.0609 (19)	0.0445 (18)	−0.0049 (16)	0.0112 (16)	0.0048 (16)
C12B	0.059 (3)	0.065 (2)	0.0424 (19)	−0.0071 (19)	0.0131 (17)	0.0091 (18)
C13B	0.052 (2)	0.0453 (17)	0.0399 (17)	0.0036 (15)	0.0037 (15)	0.0005 (13)
C14B	0.041 (2)	0.061 (2)	0.049 (2)	−0.0031 (16)	0.0096 (16)	−0.0005 (16)
C15B	0.051 (2)	0.0530 (18)	0.0424 (17)	−0.0059 (15)	0.0106 (15)	0.0026 (14)
C16B	0.048 (2)	0.081 (3)	0.060 (2)	0.0003 (19)	−0.0078 (17)	−0.0053 (18)

S1A—C8A	1.737 (4)	S1B—C8B	1.748 (3)
S1A—C7A	1.746 (3)	S1B—C7B	1.758 (3)
F1A—C5A	1.353 (4)	F1B—C5B	1.359 (3)
O1A—C13A	1.376 (4)	O1B—C13B	1.364 (3)
O1A—C16A	1.415 (4)	O1B—C16B	1.430 (4)
N1A—C8A	1.369 (4)	N1B—C8B	1.364 (4)
N1A—C1A	1.394 (4)	N1B—C1B	1.373 (4)
N1A—C2A	1.400 (4)	N1B—C2B	1.405 (3)
N2A—C8A	1.311 (4)	N2B—C8B	1.296 (4)
N2A—C9A	1.401 (4)	N2B—C9B	1.396 (4)
C1A—C9A	1.352 (5)	C1B—C9B	1.368 (4)
C1A—H1AA	0.9300	C1B—H1BA	0.9300
C2A—C3A	1.378 (5)	C2B—C3B	1.379 (4)
C2A—C7A	1.405 (4)	C2B—C7B	1.392 (4)
C3A—C4A	1.379 (4)	C3B—C4B	1.375 (4)
C3A—H3AA	0.9300	C3B—H3BA	0.9300
C4A—C5A	1.382 (5)	C4B—C5B	1.362 (5)
C4A—H4AA	0.9300	C4B—H4BA	0.9300
C5A—C6A	1.378 (5)	C5B—C6B	1.357 (5)
C6A—C7A	1.380 (4)	C6B—C7B	1.396 (4)
C6A—H6AA	0.9300	C6B—H6BA	0.9300
C9A—C10A	1.473 (4)	C9B—C10B	1.461 (4)
C10A—C15A	1.378 (4)	C10B—C15B	1.389 (5)
C10A—C11A	1.394 (4)	C10B—C11B	1.394 (4)
C11A—C12A	1.382 (4)	C11B—C12B	1.372 (4)
C11A—H11A	0.9300	C11B—H11B	0.9300
C12A—C13A	1.381 (5)	C12B—C13B	1.391 (5)
C12A—H12A	0.9300	C12B—H12B	0.9300
C13A—C14A	1.379 (4)	C13B—C14B	1.370 (4)
C14A—C15A	1.388 (4)	C14B—C15B	1.393 (4)
C14A—H14A	0.9300	C14B—H14B	0.9300
C15A—H15A	0.9300	C15B—H15B	0.9300
C16A—H16A	0.9600	C16B—H16D	0.9600
C16A—H16B	0.9600	C16B—H16E	0.9600
C16A—H16C	0.9600	C16B—H16F	0.9600
C8A—S1A—C7A	90.01 (16)	C8B—S1B—C7B	89.75 (16)
C13A—O1A—C16A	117.9 (3)	C13B—O1B—C16B	117.8 (3)
C8A—N1A—C1A	105.7 (3)	C8B—N1B—C1B	106.1 (3)
C8A—N1A—C2A	114.7 (3)	C8B—N1B—C2B	115.2 (2)
C1A—N1A—C2A	139.4 (3)	C1B—N1B—C2B	138.4 (3)
C8A—N2A—C9A	103.7 (3)	C8B—N2B—C9B	104.2 (3)
C9A—C1A—N1A	105.8 (3)	C9B—C1B—N1B	105.9 (3)
C9A—C1A—H1AA	127.1	C9B—C1B—H1BA	127.1
N1A—C1A—H1AA	127.1	N1B—C1B—H1BA	127.1
C3A—C2A—N1A	127.8 (3)	C3B—C2B—C7B	121.0 (3)
C3A—C2A—C7A	121.7 (3)	C3B—C2B—N1B	128.5 (3)
N1A—C2A—C7A	110.4 (3)	C7B—C2B—N1B	110.4 (3)
C2A—C3A—C4A	118.5 (3)	C4B—C3B—C2B	118.1 (3)
C2A—C3A—H3AA	120.8	C4B—C3B—H3BA	120.9
C4A—C3A—H3AA	120.8	C2B—C3B—H3BA	120.9
C3A—C4A—C5A	119.1 (3)	C5B—C4B—C3B	119.9 (3)
C3A—C4A—H4AA	120.5	C5B—C4B—H4BA	120.1
C5A—C4A—H4AA	120.5	C3B—C4B—H4BA	120.1
F1A—C5A—C6A	118.2 (3)	C6B—C5B—F1B	117.5 (3)
F1A—C5A—C4A	118.0 (3)	C6B—C5B—C4B	124.0 (3)
C6A—C5A—C4A	123.8 (3)	F1B—C5B—C4B	118.5 (3)
C5A—C6A—C7A	117.0 (3)	C5B—C6B—C7B	116.5 (3)
C5A—C6A—H6AA	121.5	C5B—C6B—H6BA	121.7
C7A—C6A—H6AA	121.5	C7B—C6B—H6BA	121.7
C6A—C7A—C2A	120.0 (3)	C2B—C7B—C6B	120.3 (3)
C6A—C7A—S1A	127.2 (2)	C2B—C7B—S1B	112.9 (2)
C2A—C7A—S1A	112.7 (2)	C6B—C7B—S1B	126.8 (2)
N2A—C8A—N1A	113.5 (3)	N2B—C8B—N1B	113.6 (3)
N2A—C8A—S1A	134.4 (2)	N2B—C8B—S1B	134.6 (2)
N1A—C8A—S1A	112.1 (3)	N1B—C8B—S1B	111.7 (2)
C1A—C9A—N2A	111.3 (3)	C1B—C9B—N2B	110.2 (3)
C1A—C9A—C10A	129.0 (3)	C1B—C9B—C10B	129.1 (3)
N2A—C9A—C10A	119.6 (3)	N2B—C9B—C10B	120.7 (3)
C15A—C10A—C11A	117.9 (3)	C15B—C10B—C11B	117.1 (3)
C15A—C10A—C9A	120.8 (3)	C15B—C10B—C9B	120.5 (3)
C11A—C10A—C9A	121.3 (3)	C11B—C10B—C9B	122.4 (3)
C12A—C11A—C10A	120.2 (3)	C12B—C11B—C10B	121.6 (3)
C12A—C11A—H11A	119.9	C12B—C11B—H11B	119.2
C10A—C11A—H11A	119.9	C10B—C11B—H11B	119.2
C13A—C12A—C11A	121.0 (3)	C11B—C12B—C13B	120.2 (3)
C13A—C12A—H12A	119.5	C11B—C12B—H12B	119.9
C11A—C12A—H12A	119.5	C13B—C12B—H12B	119.9
O1A—C13A—C14A	124.5 (3)	O1B—C13B—C14B	124.8 (3)
O1A—C13A—C12A	116.0 (3)	O1B—C13B—C12B	115.4 (3)
C14A—C13A—C12A	119.5 (3)	C14B—C13B—C12B	119.8 (3)
C13A—C14A—C15A	119.1 (3)	C13B—C14B—C15B	119.4 (3)
C13A—C14A—H14A	120.4	C13B—C14B—H14B	120.3
C15A—C14A—H14A	120.4	C15B—C14B—H14B	120.3
C10A—C15A—C14A	122.2 (3)	C10B—C15B—C14B	122.0 (3)
C10A—C15A—H15A	118.9	C10B—C15B—H15B	119.0
C14A—C15A—H15A	118.9	C14B—C15B—H15B	119.0
O1A—C16A—H16A	109.5	O1B—C16B—H16D	109.5
O1A—C16A—H16B	109.5	O1B—C16B—H16E	109.5
H16A—C16A—H16B	109.5	H16D—C16B—H16E	109.5
O1A—C16A—H16C	109.5	O1B—C16B—H16F	109.5
H16A—C16A—H16C	109.5	H16D—C16B—H16F	109.5
H16B—C16A—H16C	109.5	H16E—C16B—H16F	109.5
C8A—N1A—C1A—C9A	0.9 (3)	C8B—N1B—C1B—C9B	−0.4 (3)
C2A—N1A—C1A—C9A	176.0 (3)	C2B—N1B—C1B—C9B	−174.7 (3)
C8A—N1A—C2A—C3A	177.2 (3)	C8B—N1B—C2B—C3B	179.1 (3)
C1A—N1A—C2A—C3A	2.4 (5)	C1B—N1B—C2B—C3B	−6.9 (5)
C8A—N1A—C2A—C7A	1.0 (3)	C8B—N1B—C2B—C7B	−0.9 (3)
C1A—N1A—C2A—C7A	−173.8 (3)	C1B—N1B—C2B—C7B	173.1 (3)
N1A—C2A—C3A—C4A	−175.2 (3)	C7B—C2B—C3B—C4B	−1.6 (4)
C7A—C2A—C3A—C4A	0.6 (4)	N1B—C2B—C3B—C4B	178.4 (3)
C2A—C3A—C4A—C5A	−0.1 (4)	C2B—C3B—C4B—C5B	−0.9 (4)
C3A—C4A—C5A—F1A	178.4 (3)	C3B—C4B—C5B—C6B	2.3 (5)
C3A—C4A—C5A—C6A	−0.8 (5)	C3B—C4B—C5B—F1B	−179.0 (3)
F1A—C5A—C6A—C7A	−178.1 (3)	F1B—C5B—C6B—C7B	−179.8 (3)
C4A—C5A—C6A—C7A	1.1 (5)	C4B—C5B—C6B—C7B	−1.1 (5)
C5A—C6A—C7A—C2A	−0.6 (4)	C3B—C2B—C7B—C6B	2.8 (4)
C5A—C6A—C7A—S1A	177.5 (3)	N1B—C2B—C7B—C6B	−177.2 (2)
C3A—C2A—C7A—C6A	−0.3 (4)	C3B—C2B—C7B—S1B	−178.2 (2)
N1A—C2A—C7A—C6A	176.2 (3)	N1B—C2B—C7B—S1B	1.8 (3)
C3A—C2A—C7A—S1A	−178.6 (2)	C5B—C6B—C7B—C2B	−1.4 (4)
N1A—C2A—C7A—S1A	−2.1 (3)	C5B—C6B—C7B—S1B	179.7 (3)
C8A—S1A—C7A—C6A	−176.1 (3)	C8B—S1B—C7B—C2B	−1.7 (2)
C8A—S1A—C7A—C2A	2.1 (2)	C8B—S1B—C7B—C6B	177.1 (3)
C9A—N2A—C8A—N1A	0.4 (3)	C9B—N2B—C8B—N1B	−0.7 (3)
C9A—N2A—C8A—S1A	−176.8 (3)	C9B—N2B—C8B—S1B	175.4 (3)
C1A—N1A—C8A—N2A	−0.8 (3)	C1B—N1B—C8B—N2B	0.7 (3)
C2A—N1A—C8A—N2A	−177.3 (2)	C2B—N1B—C8B—N2B	176.5 (2)
C1A—N1A—C8A—S1A	177.0 (2)	C1B—N1B—C8B—S1B	−176.3 (2)
C2A—N1A—C8A—S1A	0.5 (3)	C2B—N1B—C8B—S1B	−0.4 (3)
C7A—S1A—C8A—N2A	175.8 (3)	C7B—S1B—C8B—N2B	−174.9 (3)
C7A—S1A—C8A—N1A	−1.4 (2)	C7B—S1B—C8B—N1B	1.2 (2)
N1A—C1A—C9A—N2A	−0.7 (3)	N1B—C1B—C9B—N2B	0.0 (3)
N1A—C1A—C9A—C10A	179.1 (3)	N1B—C1B—C9B—C10B	178.6 (3)
C8A—N2A—C9A—C1A	0.2 (3)	C8B—N2B—C9B—C1B	0.4 (3)
C8A—N2A—C9A—C10A	−179.6 (3)	C8B—N2B—C9B—C10B	−178.3 (2)
C1A—C9A—C10A—C15A	179.6 (3)	C1B—C9B—C10B—C15B	179.4 (3)
N2A—C9A—C10A—C15A	−0.6 (4)	N2B—C9B—C10B—C15B	−2.2 (4)
C1A—C9A—C10A—C11A	−1.4 (5)	C1B—C9B—C10B—C11B	−0.4 (5)
N2A—C9A—C10A—C11A	178.4 (3)	N2B—C9B—C10B—C11B	178.1 (3)
C15A—C10A—C11A—C12A	0.4 (4)	C15B—C10B—C11B—C12B	0.3 (5)
C9A—C10A—C11A—C12A	−178.7 (3)	C9B—C10B—C11B—C12B	180.0 (3)
C10A—C11A—C12A—C13A	0.3 (5)	C10B—C11B—C12B—C13B	−0.7 (5)
C16A—O1A—C13A—C14A	−1.6 (5)	C16B—O1B—C13B—C14B	−5.1 (4)
C16A—O1A—C13A—C12A	178.3 (3)	C16B—O1B—C13B—C12B	175.4 (3)
C11A—C12A—C13A—O1A	179.6 (3)	C11B—C12B—C13B—O1B	−179.7 (3)
C11A—C12A—C13A—C14A	−0.5 (5)	C11B—C12B—C13B—C14B	0.7 (5)
O1A—C13A—C14A—C15A	179.9 (3)	O1B—C13B—C14B—C15B	−179.8 (3)
C12A—C13A—C14A—C15A	0.0 (5)	C12B—C13B—C14B—C15B	−0.3 (5)
C11A—C10A—C15A—C14A	−0.9 (4)	C11B—C10B—C15B—C14B	0.2 (4)
C9A—C10A—C15A—C14A	178.2 (3)	C9B—C10B—C15B—C14B	−179.6 (3)
C13A—C14A—C15A—C10A	0.7 (4)	C13B—C14B—C15B—C10B	−0.1 (5)

D—H···A	D—H	H···A	D···A	D—H···A
C6A—H6AA···O1Ai	0.93	2.53	3.367 (5)	149.
C6B—H6BA···O1Bi	0.93	2.52	3.382 (4)	153.

Table 1

Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
C6A—H6AA⋯O1Ai	0.93	2.53	3.367 (5)	149
C6B—H6BA⋯O1Bi	0.93	2.52	3.382 (4)	153

Symmetry code: (i) .