1-(6-Fluoro-1,3-benzothia-zol-2-yl)-2-(1-phenyl-ethyl-idene)hydrazine.

The asymmetric unit of the title compound, C(15)H(12)FN(3)S, consists of two independent mol-ecules with comparable geometries. In one mol-ecule, the 1,3-benzothia-zole ring system (r.m.s. deviation = 0.011 Å) forms a dihedral angle of 19.86 (6)° with the phenyl ring. The corresponding r.m.s. deviation and dihedral angle for the other mol-ecule are 0.014 Å and 22.32 (6)°, respectively. In the crystal, mol-ecules are linked via N-H⋯N, C-H⋯F and C-H⋯N hydrogen bonds into a three-dimensional network. The crystal studied was a non-merohedral twin with a refined BASF value of 0.301 (2).

Related literature

For general background to and the biological activities of benzothia­zoles derivatives, see: Al-Soud et al. (2006 ▶); Kini et al. (2007 ▶); Munirajasekhar et al. (2011 ▶); Gurupadayya et al. (2008 ▶); Bowyer et al. (2007 ▶); Mittal et al. (2007 ▶); Pozas et al. (2005 ▶); Rana et al. (2008 ▶). For standard bond-length data, see: Allen et al. (1987 ▶). For the stability of the temperature controller used for the data collection, see: Cosier & Glazer (1986 ▶).

Experimental

Crystal data

C15H12FN3S

M = 285.34

Monoclinic,

a = 28.312 (3) Å

b = 7.2952 (7) Å

c = 13.0626 (13) Å

β = 103.151 (2)°

V = 2627.2 (5) Å3

Z = 8

Mo Kα radiation

μ = 0.25 mm−1

T = 100 K

0.46 × 0.21 × 0.14 mm

Data collection

Bruker SMART APEXII DUO CCD area-detector diffractometer

Absorption correction: multi-scan (SADABS; Bruker, 2009 ▶) T min = 0.894, T max = 0.965

52781 measured reflections

7411 independent reflections

7049 reflections with I > 2σ(I)

R int = 0.036

Refinement

R[F 2 > 2σ(F 2)] = 0.033

wR(F 2) = 0.080

S = 1.06

7411 reflections

364 parameters

H-atom parameters constrained

Δρmax = 0.46 e Å−3

Δρmin = −0.43 e Å−3

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/S1600536812030851/rz2786sup1.cif

Structure factors: contains datablock(s) I. DOI: 10.1107/S1600536812030851/rz2786Isup2.hkl

Supplementary material file. DOI: 10.1107/S1600536812030851/rz2786Isup3.cml

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

C15H12FN3S	F(000) = 1184
Mr = 285.34	Dx = 1.443 Mg m−3
Monoclinic, P2/c	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: -P 2yc	Cell parameters from 9959 reflections
a = 28.312 (3) Å	θ = 2.9–29.6°
b = 7.2952 (7) Å	µ = 0.25 mm−1
c = 13.0626 (13) Å	T = 100 K
β = 103.151 (2)°	Block, yellow
V = 2627.2 (5) Å3	0.46 × 0.21 × 0.14 mm
Z = 8

Bruker SMART APEXII DUO CCD area-detector diffractometer	7411 independent reflections
Radiation source: fine-focus sealed tube	7049 reflections with I > 2σ(I)
Graphite monochromator	Rint = 0.036
φ and ω scans	θmax = 29.7°, θmin = 0.7°
Absorption correction: multi-scan (SADABS; Bruker, 2009)	h = −39→39
Tmin = 0.894, Tmax = 0.965	k = −10→10
52781 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)] = 0.033	Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.080	H-atom parameters constrained
S = 1.06	w = 1/[σ2(Fo2) + (0.0333P)2 + 1.4375P] where P = (Fo2 + 2Fc2)/3
7411 reflections	(Δ/σ)max = 0.002
364 parameters	Δρmax = 0.46 e Å−3
0 restraints	Δρmin = −0.43 e Å−3

Experimental. The crystal was placed in the cold stream of an Oxford Cryosystems Cobra open-flow nitrogen cryostat (Cosier & Glazer, 1986) operating at 100.0 (1) K.

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 > 2sigma(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	0.972160 (13)	0.76932 (5)	1.01810 (3)	0.01518 (8)
F1A	1.12593 (4)	0.52213 (16)	1.27187 (9)	0.0279 (2)
N1A	1.02856 (5)	0.76694 (18)	0.88368 (11)	0.0153 (2)
N2A	0.94918 (4)	0.86931 (19)	0.81485 (11)	0.0164 (3)
H1NA	0.9510	0.8461	0.7457	0.020*
N3A	0.90434 (4)	0.88095 (18)	0.83979 (11)	0.0156 (2)
C1A	1.03203 (5)	0.6981 (2)	1.06242 (13)	0.0157 (3)
C2A	1.05463 (6)	0.6359 (2)	1.16183 (13)	0.0185 (3)
H2AA	1.0381	0.6291	1.2174	0.022*
C3A	1.10265 (6)	0.5845 (2)	1.17516 (13)	0.0197 (3)
C4A	1.12836 (6)	0.5918 (2)	1.09697 (14)	0.0197 (3)
H4AA	1.1615	0.5562	1.1112	0.024*
C5A	1.10515 (5)	0.6519 (2)	0.99766 (13)	0.0176 (3)
H5AA	1.1220	0.6561	0.9425	0.021*
C6A	1.05651 (5)	0.7064 (2)	0.97977 (13)	0.0142 (3)
C7A	0.98479 (5)	0.8033 (2)	0.89425 (12)	0.0141 (3)
C8A	0.86838 (5)	0.9481 (2)	0.77176 (12)	0.0151 (3)
C9A	0.82091 (5)	0.9398 (2)	0.80292 (13)	0.0154 (3)
C10A	0.77909 (5)	1.0154 (2)	0.73955 (13)	0.0190 (3)
H10B	0.7811	1.0814	0.6780	0.023*
C11A	0.73430 (5)	0.9950 (2)	0.76586 (14)	0.0224 (3)
H11B	0.7061	1.0482	0.7224	0.027*
C12A	0.73052 (6)	0.8977 (2)	0.85482 (15)	0.0222 (3)
H12B	0.6999	0.8819	0.8716	0.027*
C13A	0.77206 (6)	0.8236 (2)	0.91916 (15)	0.0219 (3)
H13B	0.7699	0.7578	0.9807	0.026*
C14A	0.81679 (5)	0.8455 (2)	0.89382 (13)	0.0180 (3)
H14B	0.8450	0.7957	0.9388	0.022*
C15A	0.87077 (6)	1.0251 (2)	0.66642 (14)	0.0212 (3)
H15D	0.9046	1.0273	0.6600	0.032*
H15E	0.8577	1.1500	0.6599	0.032*
H15F	0.8516	0.9481	0.6107	0.032*
S1B	0.530131 (12)	0.72187 (5)	1.04747 (3)	0.01352 (8)
F1B	0.37853 (3)	0.96714 (15)	1.16254 (8)	0.0242 (2)
N1B	0.47380 (4)	0.75091 (17)	0.85933 (10)	0.0135 (2)
N2B	0.55248 (4)	0.64677 (18)	0.86209 (10)	0.0154 (2)
H1NB	0.5496	0.6729	0.8024	0.018*
N3B	0.59655 (4)	0.60724 (17)	0.92759 (10)	0.0139 (2)
C1B	0.47084 (5)	0.7988 (2)	1.03672 (12)	0.0125 (3)
C2B	0.44856 (5)	0.8532 (2)	1.11663 (13)	0.0164 (3)
H2BA	0.4652	0.8500	1.1885	0.020*
C3B	0.40115 (5)	0.9118 (2)	1.08580 (13)	0.0161 (3)
C4B	0.37534 (5)	0.9174 (2)	0.98252 (13)	0.0160 (3)
H4BA	0.3425	0.9572	0.9656	0.019*
C5B	0.39812 (5)	0.8640 (2)	0.90372 (13)	0.0154 (3)
H5BA	0.3811	0.8676	0.8321	0.019*
C6B	0.44636 (5)	0.80470 (19)	0.93059 (12)	0.0125 (3)
C7B	0.51744 (5)	0.7067 (2)	0.91009 (12)	0.0131 (3)
C8B	0.62998 (5)	0.5364 (2)	0.88735 (12)	0.0143 (3)
C9B	0.67655 (5)	0.4959 (2)	0.96244 (12)	0.0133 (3)
C10B	0.71024 (5)	0.3762 (2)	0.93491 (13)	0.0181 (3)
H10A	0.7037	0.3245	0.8664	0.022*
C11B	0.75312 (5)	0.3316 (2)	1.00643 (15)	0.0222 (3)
H11A	0.7754	0.2487	0.9870	0.027*
C12B	0.76319 (5)	0.4081 (2)	1.10577 (15)	0.0223 (3)
H12A	0.7924	0.3780	1.1548	0.027*
C13B	0.73027 (6)	0.5300 (2)	1.13402 (13)	0.0208 (3)
H13A	0.7373	0.5832	1.2022	0.025*
C14B	0.68728 (5)	0.5737 (2)	1.06267 (13)	0.0173 (3)
H14A	0.6651	0.6570	1.0823	0.021*
C15B	0.62514 (6)	0.4894 (2)	0.77311 (13)	0.0192 (3)
H15A	0.5936	0.5318	0.7323	0.029*
H15B	0.6276	0.3563	0.7655	0.029*
H15C	0.6511	0.5496	0.7472	0.029*

	U11	U22	U33	U12	U13	U23
S1A	0.01302 (15)	0.01712 (18)	0.01631 (19)	0.00009 (13)	0.00523 (13)	−0.00027 (13)
F1A	0.0272 (5)	0.0317 (6)	0.0211 (5)	0.0061 (4)	−0.0024 (4)	0.0071 (5)
N1A	0.0138 (5)	0.0159 (6)	0.0158 (6)	0.0004 (5)	0.0027 (5)	0.0006 (5)
N2A	0.0130 (5)	0.0205 (6)	0.0160 (6)	0.0019 (5)	0.0040 (5)	0.0003 (5)
N3A	0.0135 (5)	0.0169 (6)	0.0166 (6)	0.0009 (4)	0.0039 (5)	−0.0002 (5)
C1A	0.0142 (6)	0.0144 (7)	0.0184 (7)	−0.0004 (5)	0.0038 (5)	0.0001 (6)
C2A	0.0204 (7)	0.0180 (7)	0.0173 (7)	−0.0005 (6)	0.0050 (6)	0.0018 (6)
C3A	0.0204 (7)	0.0177 (7)	0.0183 (8)	0.0017 (6)	−0.0012 (6)	0.0020 (6)
C4A	0.0156 (6)	0.0172 (7)	0.0248 (8)	0.0021 (5)	0.0020 (6)	−0.0002 (6)
C5A	0.0143 (6)	0.0160 (7)	0.0228 (8)	0.0007 (5)	0.0051 (6)	0.0003 (6)
C6A	0.0138 (6)	0.0122 (6)	0.0168 (7)	0.0000 (5)	0.0041 (5)	−0.0005 (5)
C7A	0.0148 (6)	0.0131 (6)	0.0148 (7)	−0.0014 (5)	0.0045 (5)	−0.0008 (5)
C8A	0.0150 (6)	0.0136 (7)	0.0167 (7)	0.0010 (5)	0.0033 (5)	−0.0021 (6)
C9A	0.0134 (6)	0.0130 (6)	0.0192 (7)	0.0010 (5)	0.0025 (5)	−0.0023 (6)
C10A	0.0177 (6)	0.0190 (7)	0.0192 (7)	0.0031 (6)	0.0017 (6)	−0.0005 (6)
C11A	0.0137 (6)	0.0231 (8)	0.0284 (9)	0.0046 (6)	0.0008 (6)	−0.0029 (7)
C12A	0.0151 (6)	0.0216 (8)	0.0310 (9)	0.0010 (6)	0.0073 (6)	−0.0037 (7)
C13A	0.0191 (7)	0.0200 (7)	0.0282 (9)	0.0011 (6)	0.0085 (6)	0.0008 (7)
C14A	0.0145 (6)	0.0176 (7)	0.0217 (8)	0.0022 (5)	0.0035 (6)	−0.0001 (6)
C15A	0.0192 (7)	0.0245 (8)	0.0204 (8)	0.0045 (6)	0.0056 (6)	0.0025 (6)
S1B	0.01062 (15)	0.01609 (17)	0.01314 (17)	0.00098 (12)	0.00124 (13)	0.00005 (13)
F1B	0.0191 (4)	0.0361 (6)	0.0192 (5)	0.0064 (4)	0.0078 (4)	−0.0052 (4)
N1B	0.0113 (5)	0.0168 (6)	0.0123 (6)	0.0002 (4)	0.0025 (4)	0.0001 (5)
N2B	0.0122 (5)	0.0198 (6)	0.0143 (6)	0.0038 (5)	0.0034 (5)	0.0009 (5)
N3B	0.0119 (5)	0.0146 (6)	0.0146 (6)	0.0007 (4)	0.0018 (4)	0.0011 (5)
C1B	0.0108 (5)	0.0133 (6)	0.0129 (6)	−0.0003 (5)	0.0016 (5)	−0.0014 (5)
C2B	0.0156 (6)	0.0201 (7)	0.0131 (7)	0.0000 (5)	0.0026 (5)	−0.0015 (6)
C3B	0.0158 (6)	0.0181 (7)	0.0161 (7)	0.0009 (5)	0.0069 (5)	−0.0027 (6)
C4B	0.0115 (6)	0.0163 (7)	0.0206 (7)	0.0016 (5)	0.0043 (5)	0.0008 (6)
C5B	0.0129 (6)	0.0165 (7)	0.0164 (7)	0.0008 (5)	0.0024 (5)	0.0012 (6)
C6B	0.0126 (6)	0.0125 (6)	0.0127 (6)	−0.0007 (5)	0.0036 (5)	0.0011 (5)
C7B	0.0130 (6)	0.0130 (6)	0.0127 (7)	−0.0006 (5)	0.0016 (5)	0.0000 (5)
C8B	0.0128 (6)	0.0146 (7)	0.0157 (7)	0.0005 (5)	0.0036 (5)	0.0016 (6)
C9B	0.0120 (6)	0.0139 (6)	0.0139 (7)	0.0003 (5)	0.0030 (5)	0.0028 (5)
C10B	0.0154 (6)	0.0175 (7)	0.0211 (8)	0.0019 (5)	0.0036 (6)	−0.0006 (6)
C11B	0.0153 (6)	0.0191 (7)	0.0313 (9)	0.0035 (5)	0.0032 (6)	0.0025 (7)
C12B	0.0154 (6)	0.0212 (8)	0.0275 (9)	−0.0008 (6)	−0.0009 (6)	0.0056 (7)
C13B	0.0189 (7)	0.0252 (8)	0.0167 (7)	−0.0023 (6)	0.0004 (6)	0.0021 (6)
C14B	0.0159 (6)	0.0200 (7)	0.0166 (7)	−0.0002 (5)	0.0047 (5)	0.0011 (6)
C15B	0.0190 (6)	0.0244 (8)	0.0140 (7)	0.0069 (6)	0.0032 (6)	−0.0016 (6)

S1A—C1A	1.7414 (15)	S1B—C1B	1.7451 (15)
S1A—C7A	1.7521 (16)	S1B—C7B	1.7518 (16)
F1A—C3A	1.3632 (19)	F1B—C3B	1.3674 (17)
N1A—C7A	1.3051 (19)	N1B—C7B	1.3029 (18)
N1A—C6A	1.395 (2)	N1B—C6B	1.3976 (19)
N2A—C7A	1.3594 (19)	N2B—C7B	1.3608 (18)
N2A—N3A	1.3831 (17)	N2B—N3B	1.3735 (17)
N2A—H1NA	0.9319	N2B—H1NB	0.7882
N3A—C8A	1.2862 (19)	N3B—C8B	1.2906 (19)
C1A—C2A	1.387 (2)	C1B—C2B	1.394 (2)
C1A—C6A	1.411 (2)	C1B—C6B	1.403 (2)
C2A—C3A	1.383 (2)	C2B—C3B	1.379 (2)
C2A—H2AA	0.9500	C2B—H2BA	0.9500
C3A—C4A	1.384 (2)	C3B—C4B	1.381 (2)
C4A—C5A	1.385 (2)	C4B—C5B	1.389 (2)
C4A—H4AA	0.9500	C4B—H4BA	0.9500
C5A—C6A	1.401 (2)	C5B—C6B	1.3989 (19)
C5A—H5AA	0.9500	C5B—H5BA	0.9500
C8A—C9A	1.492 (2)	C8B—C9B	1.4831 (19)
C8A—C15A	1.502 (2)	C8B—C15B	1.507 (2)
C9A—C10A	1.395 (2)	C9B—C14B	1.396 (2)
C9A—C14A	1.400 (2)	C9B—C10B	1.399 (2)
C10A—C11A	1.395 (2)	C10B—C11B	1.391 (2)
C10A—H10B	0.9500	C10B—H10A	0.9500
C11A—C12A	1.386 (3)	C11B—C12B	1.381 (3)
C11A—H11B	0.9500	C11B—H11A	0.9500
C12A—C13A	1.390 (2)	C12B—C13B	1.397 (2)
C12A—H12B	0.9500	C12B—H12A	0.9500
C13A—C14A	1.389 (2)	C13B—C14B	1.391 (2)
C13A—H13B	0.9500	C13B—H13A	0.9500
C14A—H14B	0.9500	C14B—H14A	0.9500
C15A—H15D	0.9800	C15B—H15A	0.9800
C15A—H15E	0.9800	C15B—H15B	0.9800
C15A—H15F	0.9800	C15B—H15C	0.9800
C1A—S1A—C7A	87.80 (7)	C1B—S1B—C7B	88.19 (7)
C7A—N1A—C6A	109.10 (13)	C7B—N1B—C6B	109.69 (13)
C7A—N2A—N3A	113.78 (13)	C7B—N2B—N3B	115.76 (12)
C7A—N2A—H1NA	118.6	C7B—N2B—H1NB	117.1
N3A—N2A—H1NA	119.8	N3B—N2B—H1NB	122.8
C8A—N3A—N2A	119.03 (13)	C8B—N3B—N2B	118.47 (13)
C2A—C1A—C6A	121.90 (14)	C2B—C1B—C6B	121.68 (13)
C2A—C1A—S1A	128.01 (12)	C2B—C1B—S1B	128.46 (12)
C6A—C1A—S1A	110.08 (12)	C6B—C1B—S1B	109.84 (11)
C3A—C2A—C1A	115.95 (15)	C3B—C2B—C1B	116.47 (14)
C3A—C2A—H2AA	122.0	C3B—C2B—H2BA	121.8
C1A—C2A—H2AA	122.0	C1B—C2B—H2BA	121.8
F1A—C3A—C2A	117.48 (15)	F1B—C3B—C2B	117.68 (14)
F1A—C3A—C4A	118.20 (14)	F1B—C3B—C4B	118.38 (13)
C2A—C3A—C4A	124.32 (15)	C2B—C3B—C4B	123.93 (14)
C3A—C4A—C5A	119.11 (14)	C3B—C4B—C5B	118.94 (13)
C3A—C4A—H4AA	120.4	C3B—C4B—H4BA	120.5
C5A—C4A—H4AA	120.4	C5B—C4B—H4BA	120.5
C4A—C5A—C6A	119.00 (15)	C4B—C5B—C6B	119.48 (14)
C4A—C5A—H5AA	120.5	C4B—C5B—H5BA	120.3
C6A—C5A—H5AA	120.5	C6B—C5B—H5BA	120.3
N1A—C6A—C5A	125.09 (14)	N1B—C6B—C5B	125.34 (14)
N1A—C6A—C1A	115.19 (13)	N1B—C6B—C1B	115.16 (12)
C5A—C6A—C1A	119.71 (15)	C5B—C6B—C1B	119.49 (14)
N1A—C7A—N2A	123.27 (14)	N1B—C7B—N2B	123.47 (14)
N1A—C7A—S1A	117.84 (12)	N1B—C7B—S1B	117.10 (11)
N2A—C7A—S1A	118.87 (11)	N2B—C7B—S1B	119.42 (11)
N3A—C8A—C9A	114.63 (14)	N3B—C8B—C9B	115.75 (13)
N3A—C8A—C15A	125.59 (14)	N3B—C8B—C15B	125.78 (14)
C9A—C8A—C15A	119.75 (13)	C9B—C8B—C15B	118.47 (13)
C10A—C9A—C14A	118.33 (14)	C14B—C9B—C10B	118.65 (13)
C10A—C9A—C8A	121.20 (15)	C14B—C9B—C8B	120.69 (13)
C14A—C9A—C8A	120.36 (13)	C10B—C9B—C8B	120.65 (14)
C9A—C10A—C11A	120.53 (15)	C11B—C10B—C9B	120.98 (15)
C9A—C10A—H10B	119.7	C11B—C10B—H10A	119.5
C11A—C10A—H10B	119.7	C9B—C10B—H10A	119.5
C12A—C11A—C10A	120.59 (15)	C12B—C11B—C10B	119.90 (15)
C12A—C11A—H11B	119.7	C12B—C11B—H11A	120.0
C10A—C11A—H11B	119.7	C10B—C11B—H11A	120.0
C11A—C12A—C13A	119.33 (15)	C11B—C12B—C13B	119.84 (15)
C11A—C12A—H12B	120.3	C11B—C12B—H12A	120.1
C13A—C12A—H12B	120.3	C13B—C12B—H12A	120.1
C14A—C13A—C12A	120.21 (16)	C14B—C13B—C12B	120.24 (16)
C14A—C13A—H13B	119.9	C14B—C13B—H13A	119.9
C12A—C13A—H13B	119.9	C12B—C13B—H13A	119.9
C13A—C14A—C9A	120.99 (15)	C13B—C14B—C9B	120.37 (14)
C13A—C14A—H14B	119.5	C13B—C14B—H14A	119.8
C9A—C14A—H14B	119.5	C9B—C14B—H14A	119.8
C8A—C15A—H15D	109.5	C8B—C15B—H15A	109.5
C8A—C15A—H15E	109.5	C8B—C15B—H15B	109.5
H15D—C15A—H15E	109.5	H15A—C15B—H15B	109.5
C8A—C15A—H15F	109.5	C8B—C15B—H15C	109.5
H15D—C15A—H15F	109.5	H15A—C15B—H15C	109.5
H15E—C15A—H15F	109.5	H15B—C15B—H15C	109.5
C7A—N2A—N3A—C8A	177.41 (14)	C7B—N2B—N3B—C8B	174.69 (14)
C7A—S1A—C1A—C2A	−178.25 (16)	C7B—S1B—C1B—C2B	−177.91 (15)
C7A—S1A—C1A—C6A	0.09 (12)	C7B—S1B—C1B—C6B	0.62 (11)
C6A—C1A—C2A—C3A	0.6 (2)	C6B—C1B—C2B—C3B	0.4 (2)
S1A—C1A—C2A—C3A	178.81 (13)	S1B—C1B—C2B—C3B	178.78 (12)
C1A—C2A—C3A—F1A	−179.81 (14)	C1B—C2B—C3B—F1B	−179.57 (13)
C1A—C2A—C3A—C4A	0.0 (2)	C1B—C2B—C3B—C4B	0.6 (2)
F1A—C3A—C4A—C5A	178.95 (14)	F1B—C3B—C4B—C5B	179.14 (14)
C2A—C3A—C4A—C5A	−0.9 (3)	C2B—C3B—C4B—C5B	−1.0 (2)
C3A—C4A—C5A—C6A	1.0 (2)	C3B—C4B—C5B—C6B	0.4 (2)
C7A—N1A—C6A—C5A	178.88 (15)	C7B—N1B—C6B—C5B	178.95 (14)
C7A—N1A—C6A—C1A	0.23 (19)	C7B—N1B—C6B—C1B	−0.19 (18)
C4A—C5A—C6A—N1A	−178.99 (14)	C4B—C5B—C6B—N1B	−178.61 (14)
C4A—C5A—C6A—C1A	−0.4 (2)	C4B—C5B—C6B—C1B	0.5 (2)
C2A—C1A—C6A—N1A	178.25 (14)	C2B—C1B—C6B—N1B	178.26 (13)
S1A—C1A—C6A—N1A	−0.20 (17)	S1B—C1B—C6B—N1B	−0.39 (16)
C2A—C1A—C6A—C5A	−0.5 (2)	C2B—C1B—C6B—C5B	−0.9 (2)
S1A—C1A—C6A—C5A	−178.93 (12)	S1B—C1B—C6B—C5B	−179.59 (11)
C6A—N1A—C7A—N2A	178.47 (14)	C6B—N1B—C7B—N2B	179.28 (14)
C6A—N1A—C7A—S1A	−0.16 (17)	C6B—N1B—C7B—S1B	0.72 (16)
N3A—N2A—C7A—N1A	173.87 (14)	N3B—N2B—C7B—N1B	179.62 (14)
N3A—N2A—C7A—S1A	−7.51 (18)	N3B—N2B—C7B—S1B	−1.86 (18)
C1A—S1A—C7A—N1A	0.05 (13)	C1B—S1B—C7B—N1B	−0.81 (13)
C1A—S1A—C7A—N2A	−178.65 (13)	C1B—S1B—C7B—N2B	−179.43 (13)
N2A—N3A—C8A—C9A	175.07 (13)	N2B—N3B—C8B—C9B	−179.60 (13)
N2A—N3A—C8A—C15A	−2.9 (2)	N2B—N3B—C8B—C15B	−0.8 (2)
N3A—C8A—C9A—C10A	176.81 (14)	N3B—C8B—C9B—C14B	−16.3 (2)
C15A—C8A—C9A—C10A	−5.1 (2)	C15B—C8B—C9B—C14B	164.85 (14)
N3A—C8A—C9A—C14A	−7.2 (2)	N3B—C8B—C9B—C10B	162.52 (14)
C15A—C8A—C9A—C14A	170.95 (14)	C15B—C8B—C9B—C10B	−16.3 (2)
C14A—C9A—C10A—C11A	−0.8 (2)	C14B—C9B—C10B—C11B	1.5 (2)
C8A—C9A—C10A—C11A	175.31 (15)	C8B—C9B—C10B—C11B	−177.34 (15)
C9A—C10A—C11A—C12A	−0.6 (3)	C9B—C10B—C11B—C12B	−0.9 (2)
C10A—C11A—C12A—C13A	1.4 (3)	C10B—C11B—C12B—C13B	0.0 (3)
C11A—C12A—C13A—C14A	−0.6 (3)	C11B—C12B—C13B—C14B	0.3 (2)
C12A—C13A—C14A—C9A	−0.8 (3)	C12B—C13B—C14B—C9B	0.2 (2)
C10A—C9A—C14A—C13A	1.5 (2)	C10B—C9B—C14B—C13B	−1.1 (2)
C8A—C9A—C14A—C13A	−174.61 (15)	C8B—C9B—C14B—C13B	177.69 (14)

D—H···A	D—H	H···A	D···A	D—H···A
N2A—H1NA···N1Ai	0.93	1.99	2.902 (2)	165
N2B—H1NB···N1Bii	0.79	2.14	2.9184 (18)	168
C5B—H5BA···F1Biii	0.95	2.51	3.310 (2)	142
C12B—H12A···F1Aiv	0.95	2.52	3.289 (2)	138
C12A—H12B···F1Bv	0.95	2.43	3.200 (2)	138
C15B—H15A···N1Bii	0.98	2.57	3.503 (2)	160

Table 1

Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
N2A—H1NA⋯N1A i	0.93	1.99	2.902 (2)	165
N2B—H1NB⋯N1B ii	0.79	2.14	2.9184 (18)	168
C5B—H5BA⋯F1B iii	0.95	2.51	3.310 (2)	142
C12B—H12A⋯F1A iv	0.95	2.52	3.289 (2)	138
C12A—H12B⋯F1B v	0.95	2.43	3.200 (2)	138
C15B—H15A⋯N1B ii	0.98	2.57	3.503 (2)	160

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