4-{2-[5-(4-Chloro-phen-yl)-1-(4-fluoro-phen-yl)-1H-pyrazol-3-yl]thia-zol-4-yl}benzonitrile.

The asymmetric unit of the title compound, C(25)H(14)ClFN(4)S, contains two independent mol-ecules (A and B). Each mol-ecule consists of five rings, namely chloro-phenyl, fluoro-phenyl, 1H-pyrazole, thia-zole and benzonitrile. In mol-ecule A, the 1H-pyrazole ring makes dihedral angles of 52.54 (8), 35.96 (8) and 15.43 (8)° with respect to the attached chloro-phenyl, fluoro-phenyl and thia-zole rings. The corresponding values in mol-ecule B are 51.65 (8), 37.26 (8) and 8.32 (8)°. In the crystal, mol-ecules are linked into dimers by C-H⋯N hydrogen bonds, generating R(2) (2)(10) ring motifs. These dimers are further linked into two-dimensional arrays parallel to the ab plane via inter-molecular weak C-H⋯N and C-H⋯F hydrogen bonds. The crystal structure is further stabilized by weak π-π inter-actions [with centroid-centroid distances of 3.4303 (9) and 3.6826 (9) Å] and weak C-H⋯π inter-actions.

Related literature

For background and the microbial activity of pyrazole derivatives, see: Ragavan et al. (2009 ▶, 2010 ▶). For related structures, see: Shahani et al. (2009 ▶, 2010a ▶,b ▶). For hydrogen-bond motifs, see: Bernstein et al. (1995 ▶). For standard bond-length data, see: Allen et al. (1987 ▶). For the stability of the temperature controller used in the data collection, see: Cosier & Glazer (1986 ▶).

Experimental

Crystal data

C25H14ClFN4S

M = 456.91

Triclinic,

a = 10.1412 (9) Å

b = 15.0496 (14) Å

c = 15.8890 (14) Å

α = 105.518 (2)°

β = 107.869 (2)°

γ = 99.253 (2)°

V = 2144.5 (3) Å3

Z = 4

Mo Kα radiation

μ = 0.31 mm−1

T = 100 K

0.32 × 0.26 × 0.08 mm

Data collection

Bruker APEXII DUO CCD area-detector diffractometer

Absorption correction: multi-scan (SADABS; Bruker, 2009 ▶) T min = 0.909, T max = 0.977

44680 measured reflections

12570 independent reflections

9300 reflections with I > 2σ(I)

R int = 0.047

Refinement

R[F 2 > 2σ(F 2)] = 0.042

wR(F 2) = 0.107

S = 1.01

12570 reflections

577 parameters

H-atom parameters constrained

Δρmax = 0.45 e Å−3

Δρmin = −0.50 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 datablocks global, I. DOI: 10.1107/S1600536810031405/lh5111sup1.cif

Structure factors: contains datablocks I. DOI: 10.1107/S1600536810031405/lh5111Isup2.hkl

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

C25H14ClFN4S	Z = 4
Mr = 456.91	F(000) = 936
Triclinic, P1	Dx = 1.415 Mg m−3
Hall symbol: -P 1	Mo Kα radiation, λ = 0.71073 Å
a = 10.1412 (9) Å	Cell parameters from 8583 reflections
b = 15.0496 (14) Å	θ = 2.7–30.0°
c = 15.8890 (14) Å	µ = 0.31 mm−1
α = 105.518 (2)°	T = 100 K
β = 107.869 (2)°	Plate, yellow
γ = 99.253 (2)°	0.32 × 0.26 × 0.08 mm
V = 2144.5 (3) Å3

Bruker APEXII DUO CCD area-detector diffractometer	12570 independent reflections
Radiation source: fine-focus sealed tube	9300 reflections with I > 2σ(I)
graphite	Rint = 0.047
φ and ω scans	θmax = 30.2°, θmin = 1.7°
Absorption correction: multi-scan (SADABS; Bruker, 2009)	h = −14→14
Tmin = 0.909, Tmax = 0.977	k = −21→21
44680 measured reflections	l = −22→22

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)] = 0.042	Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.107	H-atom parameters constrained
S = 1.01	w = 1/[σ2(Fo2) + (0.044P)2 + 0.5673P] where P = (Fo2 + 2Fc2)/3
12570 reflections	(Δ/σ)max < 0.001
577 parameters	Δρmax = 0.45 e Å−3
0 restraints	Δρmin = −0.50 e Å−3

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

Geometry. All e.s.d.'s (except the e.s.d. in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell e.s.d.'s are taken into account individually in the estimation of e.s.d.'s in distances, angles and torsion angles; correlations between e.s.d.'s in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell e.s.d.'s is used for estimating e.s.d.'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 > 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.

	x	y	z	Uiso*/Ueq
Cl1A	0.65750 (6)	0.27225 (3)	0.07240 (3)	0.04616 (13)
S1A	1.13306 (4)	1.04182 (3)	0.40859 (3)	0.02482 (8)
F1A	1.42149 (12)	0.59713 (9)	0.08545 (7)	0.0464 (3)
N1A	1.06028 (13)	0.73997 (8)	0.25101 (9)	0.0217 (2)
N2A	1.09248 (13)	0.83652 (8)	0.29256 (9)	0.0229 (3)
N3A	0.86452 (14)	0.97158 (9)	0.37237 (9)	0.0233 (3)
N4A	0.37277 (16)	1.24996 (10)	0.53307 (12)	0.0402 (4)
C1A	0.95272 (17)	0.52359 (11)	0.21546 (11)	0.0248 (3)
H1AA	1.0519	0.5452	0.2463	0.030*
C2A	0.88712 (18)	0.42599 (11)	0.17403 (11)	0.0284 (3)
H2AA	0.9423	0.3823	0.1763	0.034*
C3A	0.73902 (19)	0.39404 (11)	0.12930 (11)	0.0312 (4)
C4A	0.65433 (18)	0.45760 (12)	0.12679 (12)	0.0324 (4)
H4AA	0.5548	0.4354	0.0986	0.039*
C5A	0.72013 (17)	0.55472 (12)	0.16696 (11)	0.0290 (3)
H5AA	0.6640	0.5979	0.1648	0.035*
C6A	0.87003 (16)	0.58924 (10)	0.21090 (10)	0.0229 (3)
C7A	0.93212 (15)	0.69361 (10)	0.25151 (10)	0.0220 (3)
C8A	0.88014 (16)	0.76421 (11)	0.29533 (11)	0.0242 (3)
H8AA	0.7953	0.7563	0.3069	0.029*
C9A	0.98191 (16)	0.85051 (10)	0.31872 (10)	0.0222 (3)
C10A	0.97933 (16)	0.94805 (10)	0.36358 (10)	0.0225 (3)
C11A	1.03671 (16)	1.11797 (11)	0.44212 (10)	0.0241 (3)
H11A	1.0741	1.1836	0.4728	0.029*
C12A	0.89653 (16)	1.06938 (10)	0.41774 (10)	0.0227 (3)
C13A	0.78227 (16)	1.11019 (10)	0.43729 (10)	0.0231 (3)
C14A	0.64515 (18)	1.05103 (12)	0.41109 (12)	0.0331 (4)
H14B	0.6257	0.9860	0.3792	0.040*
C15A	0.53762 (18)	1.08749 (12)	0.43178 (13)	0.0357 (4)
H15B	0.4465	1.0473	0.4135	0.043*
C16A	0.56653 (17)	1.18491 (11)	0.48025 (11)	0.0275 (3)
C17A	0.70275 (18)	1.24542 (11)	0.50599 (11)	0.0283 (3)
H17B	0.7219	1.3105	0.5376	0.034*
C18A	0.80874 (18)	1.20810 (11)	0.48427 (11)	0.0276 (3)
H18B	0.8990	1.2486	0.5011	0.033*
C19A	0.45761 (17)	1.22203 (11)	0.50766 (12)	0.0311 (4)
C20A	1.15274 (15)	0.70276 (10)	0.20723 (10)	0.0211 (3)
C21A	1.29851 (17)	0.72700 (12)	0.25942 (11)	0.0282 (3)
H21B	1.3348	0.7669	0.3218	0.034*
C22A	1.39029 (18)	0.69147 (13)	0.21811 (12)	0.0333 (4)
H22B	1.4884	0.7068	0.2521	0.040*
C23A	1.33238 (18)	0.63320 (13)	0.12600 (12)	0.0310 (4)
C24A	1.18802 (18)	0.60842 (12)	0.07246 (11)	0.0294 (3)
H24B	1.1524	0.5684	0.0102	0.035*
C25A	1.09718 (16)	0.64470 (11)	0.11382 (10)	0.0243 (3)
H25B	0.9995	0.6302	0.0790	0.029*
Cl1B	0.76527 (5)	−0.39437 (3)	−0.11384 (3)	0.04333 (12)
S1B	1.14106 (4)	0.33994 (3)	0.36702 (3)	0.02914 (9)
F1B	1.57725 (11)	−0.05590 (8)	0.10753 (9)	0.0484 (3)
N1B	1.13119 (13)	0.06398 (8)	0.18871 (9)	0.0212 (2)
N2B	1.14761 (13)	0.15432 (8)	0.24368 (9)	0.0224 (2)
N3B	0.86803 (13)	0.25950 (8)	0.29038 (8)	0.0216 (2)
N4B	0.31537 (16)	0.53818 (10)	0.35928 (12)	0.0417 (4)
C1B	0.99178 (17)	−0.12120 (11)	0.01556 (10)	0.0251 (3)
H1BA	1.0637	−0.0792	0.0097	0.030*
C2B	0.93788 (18)	−0.21482 (11)	−0.04635 (11)	0.0286 (3)
H2BA	0.9740	−0.2358	−0.0931	0.034*
C3B	0.82978 (18)	−0.27638 (11)	−0.03761 (11)	0.0287 (3)
C4B	0.77397 (17)	−0.24687 (11)	0.03145 (12)	0.0284 (3)
H4BA	0.7011	−0.2890	0.0363	0.034*
C5B	0.82882 (16)	−0.15338 (10)	0.09319 (11)	0.0246 (3)
H5BA	0.7920	−0.1328	0.1397	0.029*
C6B	0.93883 (16)	−0.08956 (10)	0.08655 (10)	0.0220 (3)
C7B	0.99122 (16)	0.00952 (10)	0.15263 (10)	0.0212 (3)
C8B	0.91412 (16)	0.06778 (10)	0.18710 (10)	0.0230 (3)
H8BA	0.8164	0.0520	0.1760	0.028*
C9B	1.01516 (16)	0.15581 (10)	0.24242 (10)	0.0219 (3)
C10B	0.99350 (16)	0.24426 (10)	0.29498 (10)	0.0218 (3)
C11B	1.02670 (17)	0.40573 (11)	0.39097 (11)	0.0267 (3)
H11B	1.0558	0.4691	0.4303	0.032*
C12B	0.88655 (16)	0.35308 (10)	0.34484 (10)	0.0220 (3)
C13B	0.76062 (16)	0.38949 (10)	0.34638 (10)	0.0217 (3)
C14B	0.62431 (17)	0.32800 (10)	0.31896 (11)	0.0255 (3)
H14A	0.6121	0.2622	0.2988	0.031*
C15B	0.50724 (17)	0.36374 (11)	0.32137 (12)	0.0289 (3)
H15A	0.4171	0.3223	0.3030	0.035*
C16B	0.52600 (17)	0.46296 (11)	0.35171 (11)	0.0258 (3)
C17B	0.66100 (17)	0.52504 (10)	0.37804 (11)	0.0262 (3)
H17A	0.6732	0.5908	0.3977	0.031*
C18B	0.77587 (17)	0.48827 (10)	0.37473 (11)	0.0252 (3)
H18A	0.8654	0.5298	0.3916	0.030*
C19B	0.40724 (18)	0.50352 (11)	0.35543 (12)	0.0314 (4)
C20B	1.25363 (15)	0.03680 (10)	0.17432 (10)	0.0216 (3)
C21B	1.33796 (17)	0.09201 (11)	0.14291 (12)	0.0284 (3)
H21A	1.3194	0.1487	0.1358	0.034*
C22B	1.45039 (18)	0.06178 (12)	0.12222 (14)	0.0355 (4)
H22A	1.5097	0.0982	0.1023	0.043*
C23B	1.47150 (17)	−0.02352 (12)	0.13207 (13)	0.0321 (4)
C24B	1.39172 (17)	−0.07789 (11)	0.16568 (12)	0.0303 (3)
H24A	1.4112	−0.1342	0.1731	0.036*
C25B	1.28151 (16)	−0.04656 (11)	0.18819 (11)	0.0258 (3)
H25A	1.2270	−0.0810	0.2123	0.031*

	U11	U22	U33	U12	U13	U23
Cl1A	0.0592 (3)	0.0278 (2)	0.0379 (2)	−0.0061 (2)	0.0127 (2)	0.00634 (18)
S1A	0.02376 (18)	0.02641 (18)	0.02893 (19)	0.00997 (14)	0.01377 (15)	0.00987 (15)
F1A	0.0419 (6)	0.0755 (8)	0.0383 (6)	0.0401 (6)	0.0251 (5)	0.0185 (6)
N1A	0.0211 (6)	0.0218 (6)	0.0257 (6)	0.0092 (5)	0.0124 (5)	0.0070 (5)
N2A	0.0248 (6)	0.0218 (6)	0.0264 (6)	0.0097 (5)	0.0134 (5)	0.0082 (5)
N3A	0.0255 (6)	0.0244 (6)	0.0252 (6)	0.0113 (5)	0.0133 (5)	0.0092 (5)
N4A	0.0261 (7)	0.0277 (7)	0.0547 (10)	0.0079 (6)	0.0127 (7)	−0.0027 (7)
C1A	0.0226 (7)	0.0267 (7)	0.0274 (8)	0.0066 (6)	0.0109 (6)	0.0108 (6)
C2A	0.0348 (9)	0.0271 (7)	0.0290 (8)	0.0113 (7)	0.0162 (7)	0.0115 (6)
C3A	0.0383 (9)	0.0254 (7)	0.0253 (8)	−0.0012 (7)	0.0126 (7)	0.0063 (6)
C4A	0.0247 (8)	0.0376 (9)	0.0286 (8)	0.0005 (7)	0.0082 (7)	0.0080 (7)
C5A	0.0220 (7)	0.0341 (8)	0.0304 (8)	0.0084 (6)	0.0099 (6)	0.0093 (7)
C6A	0.0206 (7)	0.0264 (7)	0.0235 (7)	0.0067 (6)	0.0104 (6)	0.0082 (6)
C7A	0.0184 (7)	0.0269 (7)	0.0242 (7)	0.0089 (6)	0.0104 (6)	0.0096 (6)
C8A	0.0200 (7)	0.0291 (7)	0.0280 (8)	0.0102 (6)	0.0126 (6)	0.0100 (6)
C9A	0.0223 (7)	0.0258 (7)	0.0231 (7)	0.0114 (6)	0.0113 (6)	0.0092 (6)
C10A	0.0246 (7)	0.0249 (7)	0.0232 (7)	0.0105 (6)	0.0122 (6)	0.0099 (6)
C11A	0.0274 (8)	0.0240 (7)	0.0254 (7)	0.0104 (6)	0.0138 (6)	0.0086 (6)
C12A	0.0268 (7)	0.0253 (7)	0.0215 (7)	0.0125 (6)	0.0116 (6)	0.0097 (6)
C13A	0.0264 (7)	0.0261 (7)	0.0213 (7)	0.0132 (6)	0.0114 (6)	0.0083 (6)
C14A	0.0268 (8)	0.0263 (8)	0.0400 (9)	0.0114 (6)	0.0116 (7)	−0.0005 (7)
C15A	0.0231 (8)	0.0308 (8)	0.0427 (10)	0.0090 (7)	0.0099 (7)	−0.0020 (7)
C16A	0.0273 (8)	0.0290 (8)	0.0263 (8)	0.0155 (6)	0.0089 (6)	0.0058 (6)
C17A	0.0347 (9)	0.0233 (7)	0.0306 (8)	0.0135 (6)	0.0152 (7)	0.0079 (6)
C18A	0.0294 (8)	0.0246 (7)	0.0333 (8)	0.0096 (6)	0.0155 (7)	0.0106 (6)
C19A	0.0248 (8)	0.0251 (7)	0.0344 (9)	0.0091 (6)	0.0059 (7)	0.0001 (6)
C20A	0.0208 (7)	0.0236 (7)	0.0251 (7)	0.0104 (5)	0.0124 (6)	0.0104 (6)
C21A	0.0240 (8)	0.0363 (8)	0.0241 (8)	0.0106 (6)	0.0099 (6)	0.0071 (6)
C22A	0.0216 (8)	0.0509 (10)	0.0327 (9)	0.0183 (7)	0.0119 (7)	0.0153 (8)
C23A	0.0320 (9)	0.0443 (9)	0.0317 (9)	0.0253 (8)	0.0206 (7)	0.0170 (7)
C24A	0.0334 (9)	0.0349 (8)	0.0245 (8)	0.0169 (7)	0.0136 (7)	0.0092 (6)
C25A	0.0219 (7)	0.0289 (7)	0.0248 (7)	0.0108 (6)	0.0091 (6)	0.0100 (6)
Cl1B	0.0461 (3)	0.0250 (2)	0.0414 (2)	0.00970 (18)	0.0042 (2)	−0.00243 (17)
S1B	0.02187 (18)	0.02330 (18)	0.0385 (2)	0.00744 (14)	0.00972 (16)	0.00539 (16)
F1B	0.0310 (6)	0.0397 (6)	0.0831 (9)	0.0154 (5)	0.0356 (6)	0.0135 (6)
N1B	0.0209 (6)	0.0196 (5)	0.0251 (6)	0.0076 (5)	0.0106 (5)	0.0067 (5)
N2B	0.0247 (6)	0.0195 (6)	0.0252 (6)	0.0084 (5)	0.0119 (5)	0.0064 (5)
N3B	0.0237 (6)	0.0209 (6)	0.0221 (6)	0.0089 (5)	0.0104 (5)	0.0060 (5)
N4B	0.0287 (8)	0.0238 (7)	0.0653 (11)	0.0086 (6)	0.0160 (8)	0.0040 (7)
C1B	0.0272 (8)	0.0258 (7)	0.0251 (7)	0.0105 (6)	0.0100 (6)	0.0101 (6)
C2B	0.0352 (9)	0.0292 (8)	0.0226 (7)	0.0165 (7)	0.0093 (7)	0.0074 (6)
C3B	0.0327 (8)	0.0202 (7)	0.0257 (8)	0.0121 (6)	0.0019 (6)	0.0036 (6)
C4B	0.0230 (7)	0.0252 (7)	0.0340 (8)	0.0068 (6)	0.0064 (6)	0.0098 (6)
C5B	0.0216 (7)	0.0255 (7)	0.0268 (8)	0.0095 (6)	0.0085 (6)	0.0076 (6)
C6B	0.0211 (7)	0.0235 (7)	0.0215 (7)	0.0103 (6)	0.0059 (6)	0.0076 (5)
C7B	0.0215 (7)	0.0224 (7)	0.0223 (7)	0.0080 (5)	0.0097 (6)	0.0083 (5)
C8B	0.0210 (7)	0.0242 (7)	0.0256 (7)	0.0083 (6)	0.0104 (6)	0.0076 (6)
C9B	0.0239 (7)	0.0224 (7)	0.0231 (7)	0.0101 (6)	0.0107 (6)	0.0087 (6)
C10B	0.0241 (7)	0.0201 (6)	0.0232 (7)	0.0076 (5)	0.0099 (6)	0.0081 (5)
C11B	0.0267 (8)	0.0208 (7)	0.0306 (8)	0.0088 (6)	0.0102 (6)	0.0044 (6)
C12B	0.0252 (7)	0.0213 (7)	0.0221 (7)	0.0095 (6)	0.0105 (6)	0.0075 (5)
C13B	0.0247 (7)	0.0229 (7)	0.0188 (7)	0.0090 (6)	0.0095 (6)	0.0055 (5)
C14B	0.0271 (8)	0.0199 (7)	0.0281 (8)	0.0084 (6)	0.0105 (6)	0.0045 (6)
C15B	0.0251 (8)	0.0231 (7)	0.0364 (9)	0.0071 (6)	0.0120 (7)	0.0058 (6)
C16B	0.0251 (8)	0.0244 (7)	0.0280 (8)	0.0112 (6)	0.0109 (6)	0.0053 (6)
C17B	0.0304 (8)	0.0194 (7)	0.0280 (8)	0.0091 (6)	0.0124 (7)	0.0033 (6)
C18B	0.0250 (7)	0.0218 (7)	0.0269 (8)	0.0062 (6)	0.0105 (6)	0.0044 (6)
C19B	0.0275 (8)	0.0212 (7)	0.0408 (9)	0.0061 (6)	0.0122 (7)	0.0035 (7)
C20B	0.0183 (7)	0.0229 (7)	0.0244 (7)	0.0073 (5)	0.0093 (6)	0.0063 (6)
C21B	0.0261 (8)	0.0227 (7)	0.0408 (9)	0.0075 (6)	0.0168 (7)	0.0119 (6)
C22B	0.0294 (9)	0.0306 (8)	0.0555 (11)	0.0076 (7)	0.0270 (8)	0.0154 (8)
C23B	0.0203 (7)	0.0299 (8)	0.0472 (10)	0.0095 (6)	0.0176 (7)	0.0067 (7)
C24B	0.0258 (8)	0.0259 (7)	0.0416 (9)	0.0126 (6)	0.0128 (7)	0.0111 (7)
C25B	0.0236 (7)	0.0268 (7)	0.0321 (8)	0.0100 (6)	0.0132 (6)	0.0126 (6)

Cl1A—C3A	1.7401 (16)	Cl1B—C3B	1.7428 (15)
S1A—C11A	1.7044 (15)	S1B—C11B	1.7055 (15)
S1A—C10A	1.7325 (16)	S1B—C10B	1.7312 (15)
F1A—C23A	1.3617 (17)	F1B—C23B	1.3647 (17)
N1A—N2A	1.3622 (16)	N1B—N2B	1.3570 (16)
N1A—C7A	1.3761 (18)	N1B—C7B	1.3749 (18)
N1A—C20A	1.4273 (17)	N1B—C20B	1.4314 (18)
N2A—C9A	1.3377 (18)	N2B—C9B	1.3411 (18)
N3A—C10A	1.3063 (18)	N3B—C10B	1.3124 (19)
N3A—C12A	1.3879 (18)	N3B—C12B	1.3895 (18)
N4A—C19A	1.148 (2)	N4B—C19B	1.148 (2)
C1A—C2A	1.390 (2)	C1B—C2B	1.390 (2)
C1A—C6A	1.397 (2)	C1B—C6B	1.398 (2)
C1A—H1AA	0.9300	C1B—H1BA	0.9300
C2A—C3A	1.386 (2)	C2B—C3B	1.384 (2)
C2A—H2AA	0.9300	C2B—H2BA	0.9300
C3A—C4A	1.385 (2)	C3B—C4B	1.387 (2)
C4A—C5A	1.384 (2)	C4B—C5B	1.388 (2)
C4A—H4AA	0.9300	C4B—H4BA	0.9300
C5A—C6A	1.403 (2)	C5B—C6B	1.400 (2)
C5A—H5AA	0.9300	C5B—H5BA	0.9300
C6A—C7A	1.473 (2)	C6B—C7B	1.474 (2)
C7A—C8A	1.379 (2)	C7B—C8B	1.3808 (19)
C8A—C9A	1.402 (2)	C8B—C9B	1.402 (2)
C8A—H8AA	0.9300	C8B—H8BA	0.9300
C9A—C10A	1.459 (2)	C9B—C10B	1.459 (2)
C11A—C12A	1.372 (2)	C11B—C12B	1.369 (2)
C11A—H11A	0.9300	C11B—H11B	0.9300
C12A—C13A	1.471 (2)	C12B—C13B	1.473 (2)
C13A—C14A	1.396 (2)	C13B—C14B	1.400 (2)
C13A—C18A	1.401 (2)	C13B—C18B	1.401 (2)
C14A—C15A	1.384 (2)	C14B—C15B	1.387 (2)
C14A—H14B	0.9300	C14B—H14A	0.9300
C15A—C16A	1.396 (2)	C15B—C16B	1.402 (2)
C15A—H15B	0.9300	C15B—H15A	0.9300
C16A—C17A	1.398 (2)	C16B—C17B	1.397 (2)
C16A—C19A	1.444 (2)	C16B—C19B	1.445 (2)
C17A—C18A	1.381 (2)	C17B—C18B	1.377 (2)
C17A—H17B	0.9300	C17B—H17A	0.9300
C18A—H18B	0.9300	C18B—H18A	0.9300
C20A—C25A	1.385 (2)	C20B—C25B	1.388 (2)
C20A—C21A	1.385 (2)	C20B—C21B	1.388 (2)
C21A—C22A	1.389 (2)	C21B—C22B	1.390 (2)
C21A—H21B	0.9300	C21B—H21A	0.9300
C22A—C23A	1.370 (2)	C22B—C23B	1.376 (2)
C22A—H22B	0.9300	C22B—H22A	0.9300
C23A—C24A	1.377 (2)	C23B—C24B	1.377 (2)
C24A—C25A	1.386 (2)	C24B—C25B	1.387 (2)
C24A—H24B	0.9300	C24B—H24A	0.9300
C25A—H25B	0.9300	C25B—H25A	0.9300
C11A—S1A—C10A	89.00 (7)	C11B—S1B—C10B	88.81 (7)
N2A—N1A—C7A	112.26 (11)	N2B—N1B—C7B	112.35 (11)
N2A—N1A—C20A	117.81 (11)	N2B—N1B—C20B	119.34 (12)
C7A—N1A—C20A	129.66 (12)	C7B—N1B—C20B	128.31 (12)
C9A—N2A—N1A	104.36 (12)	C9B—N2B—N1B	104.17 (12)
C10A—N3A—C12A	110.04 (13)	C10B—N3B—C12B	109.82 (12)
C2A—C1A—C6A	120.19 (15)	C2B—C1B—C6B	120.61 (14)
C2A—C1A—H1AA	119.9	C2B—C1B—H1BA	119.7
C6A—C1A—H1AA	119.9	C6B—C1B—H1BA	119.7
C3A—C2A—C1A	119.69 (15)	C3B—C2B—C1B	119.22 (15)
C3A—C2A—H2AA	120.2	C3B—C2B—H2BA	120.4
C1A—C2A—H2AA	120.2	C1B—C2B—H2BA	120.4
C4A—C3A—C2A	121.18 (15)	C2B—C3B—C4B	121.55 (14)
C4A—C3A—Cl1A	119.05 (13)	C2B—C3B—Cl1B	119.01 (13)
C2A—C3A—Cl1A	119.75 (14)	C4B—C3B—Cl1B	119.42 (13)
C5A—C4A—C3A	118.95 (15)	C3B—C4B—C5B	118.84 (15)
C5A—C4A—H4AA	120.5	C3B—C4B—H4BA	120.6
C3A—C4A—H4AA	120.5	C5B—C4B—H4BA	120.6
C4A—C5A—C6A	121.13 (15)	C4B—C5B—C6B	120.98 (14)
C4A—C5A—H5AA	119.4	C4B—C5B—H5BA	119.5
C6A—C5A—H5AA	119.4	C6B—C5B—H5BA	119.5
C1A—C6A—C5A	118.80 (14)	C1B—C6B—C5B	118.80 (13)
C1A—C6A—C7A	123.26 (13)	C1B—C6B—C7B	122.35 (13)
C5A—C6A—C7A	117.93 (14)	C5B—C6B—C7B	118.81 (13)
N1A—C7A—C8A	105.87 (13)	N1B—C7B—C8B	106.21 (12)
N1A—C7A—C6A	124.12 (13)	N1B—C7B—C6B	124.85 (13)
C8A—C7A—C6A	130.00 (13)	C8B—C7B—C6B	128.87 (13)
C7A—C8A—C9A	105.62 (13)	C7B—C8B—C9B	105.04 (13)
C7A—C8A—H8AA	127.2	C7B—C8B—H8BA	127.5
C9A—C8A—H8AA	127.2	C9B—C8B—H8BA	127.5
N2A—C9A—C8A	111.89 (13)	N2B—C9B—C8B	112.23 (13)
N2A—C9A—C10A	118.99 (13)	N2B—C9B—C10B	118.76 (13)
C8A—C9A—C10A	129.10 (13)	C8B—C9B—C10B	129.00 (14)
N3A—C10A—C9A	123.79 (14)	N3B—C10B—C9B	125.06 (13)
N3A—C10A—S1A	115.43 (11)	N3B—C10B—S1B	115.54 (11)
C9A—C10A—S1A	120.78 (11)	C9B—C10B—S1B	119.37 (11)
C12A—C11A—S1A	110.82 (11)	C12B—C11B—S1B	111.18 (11)
C12A—C11A—H11A	124.6	C12B—C11B—H11B	124.4
S1A—C11A—H11A	124.6	S1B—C11B—H11B	124.4
C11A—C12A—N3A	114.71 (13)	C11B—C12B—N3B	114.62 (13)
C11A—C12A—C13A	126.63 (14)	C11B—C12B—C13B	125.19 (13)
N3A—C12A—C13A	118.64 (13)	N3B—C12B—C13B	120.14 (13)
C14A—C13A—C18A	118.52 (14)	C14B—C13B—C18B	118.50 (13)
C14A—C13A—C12A	120.22 (13)	C14B—C13B—C12B	121.88 (13)
C18A—C13A—C12A	121.24 (14)	C18B—C13B—C12B	119.61 (13)
C15A—C14A—C13A	121.12 (15)	C15B—C14B—C13B	120.98 (14)
C15A—C14A—H14B	119.4	C15B—C14B—H14A	119.5
C13A—C14A—H14B	119.4	C13B—C14B—H14A	119.5
C14A—C15A—C16A	119.65 (16)	C14B—C15B—C16B	119.36 (14)
C14A—C15A—H15B	120.2	C14B—C15B—H15A	120.3
C16A—C15A—H15B	120.2	C16B—C15B—H15A	120.3
C15A—C16A—C17A	119.99 (14)	C17B—C16B—C15B	120.22 (14)
C15A—C16A—C19A	119.77 (15)	C17B—C16B—C19B	118.43 (13)
C17A—C16A—C19A	120.17 (14)	C15B—C16B—C19B	121.34 (14)
C18A—C17A—C16A	119.70 (14)	C18B—C17B—C16B	119.62 (14)
C18A—C17A—H17B	120.2	C18B—C17B—H17A	120.2
C16A—C17A—H17B	120.2	C16B—C17B—H17A	120.2
C17A—C18A—C13A	121.01 (15)	C17B—C18B—C13B	121.30 (14)
C17A—C18A—H18B	119.5	C17B—C18B—H18A	119.3
C13A—C18A—H18B	119.5	C13B—C18B—H18A	119.3
N4A—C19A—C16A	176.7 (2)	N4B—C19B—C16B	178.14 (17)
C25A—C20A—C21A	120.93 (14)	C25B—C20B—C21B	121.52 (13)
C25A—C20A—N1A	120.26 (13)	C25B—C20B—N1B	119.10 (13)
C21A—C20A—N1A	118.80 (13)	C21B—C20B—N1B	119.32 (13)
C20A—C21A—C22A	119.68 (15)	C20B—C21B—C22B	119.32 (14)
C20A—C21A—H21B	120.2	C20B—C21B—H21A	120.3
C22A—C21A—H21B	120.2	C22B—C21B—H21A	120.3
C23A—C22A—C21A	118.22 (15)	C23B—C22B—C21B	118.09 (15)
C23A—C22A—H22B	120.9	C23B—C22B—H22A	121.0
C21A—C22A—H22B	120.9	C21B—C22B—H22A	121.0
F1A—C23A—C22A	118.52 (15)	F1B—C23B—C22B	118.39 (15)
F1A—C23A—C24A	118.24 (15)	F1B—C23B—C24B	118.19 (14)
C22A—C23A—C24A	123.24 (15)	C22B—C23B—C24B	123.42 (14)
C23A—C24A—C25A	118.27 (15)	C23B—C24B—C25B	118.34 (14)
C23A—C24A—H24B	120.9	C23B—C24B—H24A	120.8
C25A—C24A—H24B	120.9	C25B—C24B—H24A	120.8
C20A—C25A—C24A	119.63 (14)	C24B—C25B—C20B	119.20 (14)
C20A—C25A—H25B	120.2	C24B—C25B—H25A	120.4
C24A—C25A—H25B	120.2	C20B—C25B—H25A	120.4
C7A—N1A—N2A—C9A	−0.46 (16)	C7B—N1B—N2B—C9B	0.54 (16)
C20A—N1A—N2A—C9A	174.20 (12)	C20B—N1B—N2B—C9B	−179.95 (12)
C6A—C1A—C2A—C3A	−0.9 (2)	C6B—C1B—C2B—C3B	0.7 (2)
C1A—C2A—C3A—C4A	−1.4 (2)	C1B—C2B—C3B—C4B	0.0 (2)
C1A—C2A—C3A—Cl1A	176.82 (12)	C1B—C2B—C3B—Cl1B	−178.65 (12)
C2A—C3A—C4A—C5A	2.3 (2)	C2B—C3B—C4B—C5B	−0.3 (2)
Cl1A—C3A—C4A—C5A	−175.97 (12)	Cl1B—C3B—C4B—C5B	178.40 (12)
C3A—C4A—C5A—C6A	−0.9 (2)	C3B—C4B—C5B—C6B	−0.2 (2)
C2A—C1A—C6A—C5A	2.3 (2)	C2B—C1B—C6B—C5B	−1.1 (2)
C2A—C1A—C6A—C7A	−178.81 (14)	C2B—C1B—C6B—C7B	−178.93 (14)
C4A—C5A—C6A—C1A	−1.4 (2)	C4B—C5B—C6B—C1B	0.8 (2)
C4A—C5A—C6A—C7A	179.62 (14)	C4B—C5B—C6B—C7B	178.76 (14)
N2A—N1A—C7A—C8A	0.16 (17)	N2B—N1B—C7B—C8B	−0.64 (16)
C20A—N1A—C7A—C8A	−173.70 (14)	C20B—N1B—C7B—C8B	179.92 (13)
N2A—N1A—C7A—C6A	179.59 (13)	N2B—N1B—C7B—C6B	176.52 (13)
C20A—N1A—C7A—C6A	5.7 (2)	C20B—N1B—C7B—C6B	−2.9 (2)
C1A—C6A—C7A—N1A	37.1 (2)	C1B—C6B—C7B—N1B	−36.7 (2)
C5A—C6A—C7A—N1A	−143.99 (15)	C5B—C6B—C7B—N1B	145.41 (14)
C1A—C6A—C7A—C8A	−143.60 (17)	C1B—C6B—C7B—C8B	139.76 (16)
C5A—C6A—C7A—C8A	35.3 (2)	C5B—C6B—C7B—C8B	−38.1 (2)
N1A—C7A—C8A—C9A	0.20 (16)	N1B—C7B—C8B—C9B	0.44 (16)
C6A—C7A—C8A—C9A	−179.19 (15)	C6B—C7B—C8B—C9B	−176.56 (14)
N1A—N2A—C9A—C8A	0.59 (17)	N1B—N2B—C9B—C8B	−0.24 (16)
N1A—N2A—C9A—C10A	−178.03 (12)	N1B—N2B—C9B—C10B	−179.58 (12)
C7A—C8A—C9A—N2A	−0.51 (18)	C7B—C8B—C9B—N2B	−0.13 (17)
C7A—C8A—C9A—C10A	177.94 (15)	C7B—C8B—C9B—C10B	179.12 (14)
C12A—N3A—C10A—C9A	−179.85 (13)	C12B—N3B—C10B—C9B	−176.26 (13)
C12A—N3A—C10A—S1A	−0.36 (16)	C12B—N3B—C10B—S1B	1.59 (16)
N2A—C9A—C10A—N3A	163.76 (14)	N2B—C9B—C10B—N3B	170.87 (14)
C8A—C9A—C10A—N3A	−14.6 (3)	C8B—C9B—C10B—N3B	−8.3 (2)
N2A—C9A—C10A—S1A	−15.70 (19)	N2B—C9B—C10B—S1B	−6.90 (18)
C8A—C9A—C10A—S1A	165.95 (13)	C8B—C9B—C10B—S1B	173.89 (12)
C11A—S1A—C10A—N3A	0.31 (12)	C11B—S1B—C10B—N3B	−1.16 (12)
C11A—S1A—C10A—C9A	179.81 (13)	C11B—S1B—C10B—C9B	176.82 (12)
C10A—S1A—C11A—C12A	−0.15 (12)	C10B—S1B—C11B—C12B	0.34 (12)
S1A—C11A—C12A—N3A	−0.01 (17)	S1B—C11B—C12B—N3B	0.48 (17)
S1A—C11A—C12A—C13A	178.17 (12)	S1B—C11B—C12B—C13B	−176.84 (11)
C10A—N3A—C12A—C11A	0.24 (18)	C10B—N3B—C12B—C11B	−1.32 (18)
C10A—N3A—C12A—C13A	−178.10 (13)	C10B—N3B—C12B—C13B	176.15 (12)
C11A—C12A—C13A—C14A	−177.63 (16)	C11B—C12B—C13B—C14B	−163.03 (15)
N3A—C12A—C13A—C14A	0.5 (2)	N3B—C12B—C13B—C14B	19.8 (2)
C11A—C12A—C13A—C18A	0.8 (2)	C11B—C12B—C13B—C18B	17.9 (2)
N3A—C12A—C13A—C18A	178.91 (14)	N3B—C12B—C13B—C18B	−159.31 (13)
C18A—C13A—C14A—C15A	−0.8 (3)	C18B—C13B—C14B—C15B	−1.2 (2)
C12A—C13A—C14A—C15A	177.70 (16)	C12B—C13B—C14B—C15B	179.68 (14)
C13A—C14A—C15A—C16A	−0.5 (3)	C13B—C14B—C15B—C16B	0.0 (2)
C14A—C15A—C16A—C17A	1.3 (3)	C14B—C15B—C16B—C17B	0.8 (2)
C14A—C15A—C16A—C19A	−175.72 (17)	C14B—C15B—C16B—C19B	−179.99 (15)
C15A—C16A—C17A—C18A	−0.8 (2)	C15B—C16B—C17B—C18B	−0.5 (2)
C19A—C16A—C17A—C18A	176.16 (15)	C19B—C16B—C17B—C18B	−179.70 (15)
C16A—C17A—C18A—C13A	−0.4 (2)	C16B—C17B—C18B—C13B	−0.7 (2)
C14A—C13A—C18A—C17A	1.2 (2)	C14B—C13B—C18B—C17B	1.6 (2)
C12A—C13A—C18A—C17A	−177.22 (14)	C12B—C13B—C18B—C17B	−179.31 (14)
N2A—N1A—C20A—C25A	−124.58 (15)	N2B—N1B—C20B—C25B	129.87 (15)
C7A—N1A—C20A—C25A	49.0 (2)	C7B—N1B—C20B—C25B	−50.7 (2)
N2A—N1A—C20A—C21A	54.44 (18)	N2B—N1B—C20B—C21B	−52.93 (19)
C7A—N1A—C20A—C21A	−131.98 (16)	C7B—N1B—C20B—C21B	126.48 (16)
C25A—C20A—C21A—C22A	−1.0 (2)	C25B—C20B—C21B—C22B	1.9 (3)
N1A—C20A—C21A—C22A	179.96 (14)	N1B—C20B—C21B—C22B	−175.22 (15)
C20A—C21A—C22A—C23A	0.2 (3)	C20B—C21B—C22B—C23B	1.3 (3)
C21A—C22A—C23A—F1A	−179.16 (15)	C21B—C22B—C23B—F1B	176.88 (16)
C21A—C22A—C23A—C24A	0.2 (3)	C21B—C22B—C23B—C24B	−3.3 (3)
F1A—C23A—C24A—C25A	179.68 (14)	F1B—C23B—C24B—C25B	−178.21 (15)
C22A—C23A—C24A—C25A	0.3 (3)	C22B—C23B—C24B—C25B	2.0 (3)
C21A—C20A—C25A—C24A	1.6 (2)	C23B—C24B—C25B—C20B	1.3 (2)
N1A—C20A—C25A—C24A	−179.45 (13)	C21B—C20B—C25B—C24B	−3.3 (2)
C23A—C24A—C25A—C20A	−1.2 (2)	N1B—C20B—C25B—C24B	173.87 (14)

Cg1 and Cg2 are the centroids of the C1A–C6A and C1B–C6B rings, respectively.

D—H···A	D—H	H···A	D···A	D—H···A
C5A—H5AA···F1Ai	0.93	2.39	3.149 (2)	138
C8B—H8BA···F1Bi	0.93	2.42	3.283 (2)	154
C17B—H17A···N4Aii	0.93	2.54	3.419 (2)	159
C17A—H17B···N4Bii	0.93	2.58	3.453 (2)	156
C25B—H25A···N2Aiii	0.93	2.53	3.457 (2)	175
C24A—H24B···Cg1iv	0.93	2.96	3.7811 (18)	148
C21B—H21A···Cg2v	0.93	2.97	3.6423 (19)	131

Table 1

Hydrogen-bond geometry (Å, °)

Cg1 and Cg2 are the centroids of the C1A–C6A and C1B–C6B rings, respectively.

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
C5A—H5AA⋯F1Ai	0.93	2.39	3.149 (2)	138
C8B—H8BA⋯F1Bi	0.93	2.42	3.283 (2)	154
C17B—H17A⋯N4Aii	0.93	2.54	3.419 (2)	159
C17A—H17B⋯N4Bii	0.93	2.58	3.453 (2)	156
C25B—H25A⋯N2Aiii	0.93	2.53	3.457 (2)	175
C24A—H24B⋯Cg1iv	0.93	2.96	3.7811 (18)	148
C21B—H21A⋯Cg2v	0.93	2.97	3.6423 (19)	131

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