2-[5-(2-Methyl-phen-yl)-3-(2-methyl-styryl)-4,5-di-hydro-1H-pyrazol-1-yl]-6-(thio-phen-2-yl)-4-(tri-fluoro-meth-yl)pyrimidine chloro-form monosolvate.

In the crystal structure of the title compound, C28H23F3N4S·CHCl3, the chloro-form solvate mol-ecules connect the pyrimidine mol-ecules into chains along [101] through weak C-H⋯N and C-H⋯Cl hydrogen-bond inter-actions. There are further connections between adjacent chains through F⋯Cl halogen contacts of 3.185 (3) Å, with the -CF3 group presenting a significant short F⋯F inter-chain distance of 2.712 (4) Å. The five-membered pyrazole ring is approximately planar (r.m.s. deviation = 0.050 Å). The pyrimidine ring makes dihedral angles of 84.15 (8) and 4.56 (8)° with the benzene rings.

Related literature

For the synthesis of the title compound and similar crystal structures, see: Flores et al. (2006 ▶). For biological properties of 4-tri­fluoro­methyl-2-(5-aryl-3-styryl-1H-pyrazol-1­yl)-pyrim­idines, see: Gressler et al. (2010 ▶). For halogen contacts, see: Baker et al. (2012 ▶); Metrangolo et al. (2008 ▶). For van der Waals radii, see: Batsanov (2001 ▶). For a related structure, see: Fabiani Claro Flores et al. (2014 ▶).

Experimental

Crystal data

C28H23F3N4S·CHCl3

M = 623.93

Triclinic,

a = 10.6606 (3) Å

b = 11.0902 (3) Å

c = 13.4230 (4) Å

α = 100.518 (2)°

β = 105.863 (2)°

γ = 100.848 (2)°

V = 1452.55 (7) Å3

Z = 2

Mo Kα radiation

μ = 0.43 mm−1

T = 273 K

0.31 × 0.28 × 0.16 mm

Data collection

Bruker APEXII CCD diffractometer

Absorption correction: gaussian (XPREP; Bruker, 2009 ▶) T min = 0.902, T max = 1

45041 measured reflections

6974 independent reflections

4777 reflections with I > 2σ(I)

R int = 0.024

Refinement

R[F 2 > 2σ(F 2)] = 0.068

wR(F 2) = 0.242

S = 1.11

6974 reflections

361 parameters

H-atom parameters constrained

Δρmax = 1.24 e Å−3

Δρmin = −0.93 e Å−3

Data collection: APEX2 (Bruker, 2009 ▶); cell refinement: SAINT (Bruker, 2009 ▶); data reduction: SAINT; program(s) used to solve structure: SHELXS97 (Sheldrick, 2008 ▶); program(s) used to refine structure: SHELXL2013 (Sheldrick, 2008 ▶); molecular graphics: DIAMOND (Brandenburg, 2006 ▶); software used to prepare material for publication: publCIF (Westrip, 2010 ▶).

Crystal structure: contains datablock(s) I. DOI: 10.1107/S160053681401321X/zq2224sup1.cif

Structure factors: contains datablock(s) I. DOI: 10.1107/S160053681401321X/zq2224Isup2.hkl

Click here for additional data file.

Supporting information file. DOI: 10.1107/S160053681401321X/zq2224Isup3.cml

CCDC reference: 1007013

Additional supporting information: crystallographic information; 3D view; checkCIF report

C28H23F3N4S·CHCl3	Z = 2
Mr = 623.93	F(000) = 640
Triclinic, P1	Dx = 1.427 Mg m−3
Hall symbol: -P 1	Mo Kα radiation, λ = 0.71073 Å
a = 10.6606 (3) Å	Cell parameters from 6263 reflections
b = 11.0902 (3) Å	θ = 2.8–25.1°
c = 13.4230 (4) Å	µ = 0.43 mm−1
α = 100.518 (2)°	T = 273 K
β = 105.863 (2)°	Prismatic, colourless
γ = 100.848 (2)°	0.31 × 0.28 × 0.16 mm
V = 1452.55 (7) Å3

Bruker APEXII CCD diffractometer	6974 independent reflections
Radiation source: fine-focus sealed tube	4777 reflections with I > 2σ(I)
Graphite monochromator	Rint = 0.024
φ and ω scans	θmax = 28.0°, θmin = 2.4°
Absorption correction: gaussian (XPREP; Bruker, 2009)	h = −14→14
Tmin = 0.902, Tmax = 1	k = −14→14
45041 measured reflections	l = −17→16

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)] = 0.068	Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.242	H-atom parameters constrained
S = 1.11	w = 1/[σ2(Fo2) + (0.1398P)2 + 0.5025P] where P = (Fo2 + 2Fc2)/3
6974 reflections	(Δ/σ)max < 0.001
361 parameters	Δρmax = 1.24 e Å−3
0 restraints	Δρmin = −0.93 e Å−3

Experimental. Absorption correction: XPREP (Bruker, 2009) was used to perform the Gaussian absorption correction based on the face-indexed crystal size.

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
S1	−0.01728 (9)	0.76442 (8)	0.50222 (7)	0.0682 (3)
C11	0.4130 (2)	0.8288 (2)	0.65685 (19)	0.0438 (6)
C17	0.4753 (3)	0.7295 (3)	0.6497 (3)	0.0572 (7)
H17	0.5028	0.6966	0.7087	0.069*
C12	0.3698 (3)	0.8789 (3)	0.5683 (2)	0.0595 (8)
C16	0.4966 (4)	0.6790 (4)	0.5550 (3)	0.0776 (11)
H16	0.5410	0.6145	0.5511	0.093*
C15	0.4518 (5)	0.7249 (5)	0.4671 (4)	0.0985 (16)
H15	0.4633	0.6896	0.4029	0.118*
C14	0.3895 (5)	0.8234 (4)	0.4737 (3)	0.0860 (12)
H14	0.3600	0.8535	0.4134	0.103*
Cl1	0.44264 (9)	0.26973 (10)	0.81760 (8)	0.0848 (3)
Cl3	0.5764 (2)	0.52932 (12)	0.88980 (12)	0.1361 (7)
Cl2	0.72237 (12)	0.3306 (2)	0.85929 (13)	0.1408 (7)
C29	0.5949 (3)	0.3790 (3)	0.8970 (3)	0.0664 (8)
H29	0.6084	0.3740	0.9712	0.080*
C23	1.0217 (3)	1.1438 (2)	1.1310 (2)	0.0462 (6)
C22	0.9161 (2)	1.0415 (2)	1.12276 (19)	0.0435 (6)
C28	0.9355 (3)	0.9708 (3)	1.1992 (2)	0.0593 (8)
H28	0.8649	0.9046	1.1954	0.071*
C25	1.1422 (3)	1.1681 (3)	1.2150 (3)	0.0618 (8)
H25	1.2126	1.2360	1.2215	0.074*
C26	1.1608 (3)	1.0965 (3)	1.2874 (3)	0.0679 (9)
H26	1.2428	1.1143	1.3414	0.081*
C27	1.0552 (4)	0.9959 (3)	1.2795 (3)	0.0699 (9)
H27	1.0659	0.9462	1.3285	0.084*
N2	0.22412 (19)	0.6049 (2)	0.83093 (15)	0.0411 (5)
N1	0.15480 (19)	0.71151 (19)	0.69225 (15)	0.0395 (4)
C9	0.2431 (2)	0.6973 (2)	0.78029 (18)	0.0377 (5)
C6	0.0076 (2)	0.5238 (3)	0.6959 (2)	0.0467 (6)
H6	−0.0739	0.4625	0.6668	0.056*
C5	0.0375 (2)	0.6247 (2)	0.65126 (18)	0.0409 (5)
C7	0.1059 (2)	0.5198 (2)	0.78595 (19)	0.0413 (5)
N4	0.4644 (2)	0.7868 (2)	0.90721 (15)	0.0431 (5)
N3	0.3620 (2)	0.7876 (2)	0.81858 (15)	0.0423 (5)
C10	0.3995 (2)	0.8858 (2)	0.76382 (18)	0.0401 (5)
H10	0.3334	0.9369	0.7545	0.048*
C19	0.5630 (2)	0.8833 (2)	0.92339 (18)	0.0404 (5)
C21	0.7875 (2)	1.0104 (2)	1.03551 (19)	0.0454 (6)
H21	0.7757	1.0682	0.9936	0.055*
C18	0.5347 (3)	0.9649 (2)	0.84646 (19)	0.0448 (6)
H18B	0.6048	0.9786	0.8134	0.054*
H18A	0.5266	1.0463	0.8816	0.054*
C20	0.6865 (2)	0.9077 (3)	1.0108 (2)	0.0463 (6)
H20	0.6959	0.8488	1.0517	0.056*
C3	−0.1863 (3)	0.5594 (3)	0.4960 (2)	0.0534 (7)
H3	−0.2261	0.4863	0.5118	0.064*
C4	−0.0573 (2)	0.6396 (3)	0.5552 (2)	0.0447 (6)
C1	−0.1672 (3)	0.7167 (4)	0.4033 (3)	0.0666 (8)
H1	−0.1924	0.7605	0.3513	0.080*
C2	−0.2467 (3)	0.6086 (4)	0.4072 (2)	0.0654 (9)
H2	−0.3315	0.5699	0.3578	0.078*
C8	0.0840 (3)	0.4152 (3)	0.8404 (2)	0.0531 (7)
F1	−0.0216 (2)	0.32016 (19)	0.78234 (18)	0.0835 (6)
F3	0.1888 (2)	0.3649 (2)	0.8628 (2)	0.0819 (6)
F2	0.0635 (3)	0.4554 (2)	0.93190 (18)	0.0898 (7)
C24	1.0106 (3)	1.2256 (3)	1.0535 (3)	0.0641 (8)
H24C	0.9226	1.1971	1.0010	0.096*
H24B	1.0777	1.2202	1.0186	0.096*
H24A	1.0244	1.3118	1.0910	0.096*
C13	0.3074 (4)	0.9893 (4)	0.5745 (3)	0.0785 (10)
H13A	0.3042	1.0170	0.6456	0.118*
H13C	0.2176	0.9642	0.5248	0.118*
H13B	0.3603	1.0574	0.5570	0.118*

	U11	U22	U33	U12	U13	U23
S1	0.0641 (5)	0.0673 (5)	0.0585 (5)	0.0090 (4)	−0.0020 (3)	0.0201 (4)
C11	0.0383 (11)	0.0434 (13)	0.0392 (12)	−0.0038 (10)	0.0074 (9)	0.0071 (10)
C17	0.0474 (14)	0.0498 (16)	0.0626 (17)	0.0020 (12)	0.0155 (12)	−0.0011 (13)
C12	0.0619 (16)	0.0635 (18)	0.0427 (14)	−0.0045 (14)	0.0108 (12)	0.0174 (12)
C16	0.067 (2)	0.067 (2)	0.088 (3)	0.0004 (16)	0.0387 (19)	−0.0115 (19)
C15	0.109 (3)	0.100 (3)	0.069 (3)	−0.018 (3)	0.053 (2)	−0.015 (2)
C14	0.107 (3)	0.093 (3)	0.0460 (18)	−0.004 (2)	0.0272 (19)	0.0144 (18)
Cl1	0.0610 (5)	0.0950 (7)	0.0881 (6)	0.0108 (4)	0.0046 (4)	0.0360 (5)
Cl3	0.1896 (16)	0.0734 (7)	0.1109 (10)	0.0221 (8)	−0.0054 (10)	0.0323 (7)
Cl2	0.0650 (7)	0.235 (2)	0.1214 (11)	0.0516 (9)	0.0312 (7)	0.0244 (11)
C29	0.0627 (18)	0.077 (2)	0.0523 (16)	0.0201 (16)	0.0041 (13)	0.0185 (15)
C23	0.0416 (12)	0.0459 (14)	0.0461 (13)	0.0052 (10)	0.0116 (10)	0.0092 (11)
C22	0.0417 (12)	0.0403 (13)	0.0386 (12)	0.0052 (10)	0.0040 (9)	0.0043 (10)
C28	0.0522 (15)	0.0561 (17)	0.0515 (15)	−0.0062 (12)	−0.0020 (12)	0.0184 (13)
C25	0.0411 (13)	0.0646 (19)	0.0643 (18)	−0.0034 (12)	0.0054 (12)	0.0129 (14)
C26	0.0485 (15)	0.078 (2)	0.0551 (16)	0.0014 (14)	−0.0072 (12)	0.0148 (15)
C27	0.0674 (19)	0.072 (2)	0.0509 (16)	0.0020 (16)	−0.0063 (14)	0.0232 (15)
N2	0.0359 (9)	0.0469 (11)	0.0386 (10)	0.0062 (8)	0.0106 (8)	0.0127 (8)
N1	0.0350 (9)	0.0444 (11)	0.0359 (10)	0.0091 (8)	0.0074 (7)	0.0091 (8)
C9	0.0331 (10)	0.0429 (13)	0.0353 (11)	0.0082 (9)	0.0094 (8)	0.0090 (9)
C6	0.0347 (11)	0.0500 (15)	0.0501 (14)	0.0048 (10)	0.0108 (10)	0.0100 (11)
C5	0.0334 (10)	0.0484 (14)	0.0386 (12)	0.0121 (10)	0.0095 (9)	0.0061 (10)
C7	0.0385 (11)	0.0435 (13)	0.0427 (12)	0.0082 (10)	0.0163 (9)	0.0098 (10)
N4	0.0362 (9)	0.0495 (12)	0.0373 (10)	0.0053 (8)	0.0027 (8)	0.0145 (9)
N3	0.0380 (10)	0.0461 (12)	0.0369 (10)	0.0039 (8)	0.0035 (8)	0.0157 (8)
C10	0.0388 (11)	0.0372 (12)	0.0397 (12)	0.0055 (9)	0.0069 (9)	0.0110 (9)
C19	0.0390 (11)	0.0403 (12)	0.0356 (11)	0.0060 (9)	0.0061 (9)	0.0069 (9)
C21	0.0434 (12)	0.0440 (13)	0.0399 (12)	0.0053 (10)	0.0039 (10)	0.0085 (10)
C18	0.0475 (13)	0.0388 (13)	0.0379 (12)	0.0027 (10)	0.0033 (10)	0.0087 (10)
C20	0.0408 (12)	0.0474 (14)	0.0424 (12)	0.0048 (10)	0.0031 (10)	0.0123 (10)
C3	0.0343 (12)	0.0724 (19)	0.0447 (13)	0.0144 (12)	0.0015 (10)	0.0088 (12)
C4	0.0360 (11)	0.0522 (15)	0.0420 (12)	0.0133 (10)	0.0070 (9)	0.0078 (11)
C1	0.0600 (17)	0.082 (2)	0.0528 (16)	0.0280 (17)	0.0008 (13)	0.0196 (15)
C2	0.0439 (14)	0.089 (2)	0.0522 (16)	0.0213 (15)	−0.0012 (12)	0.0114 (15)
C8	0.0473 (14)	0.0529 (16)	0.0582 (16)	0.0045 (12)	0.0189 (12)	0.0168 (13)
F1	0.0741 (13)	0.0630 (12)	0.0957 (15)	−0.0129 (10)	0.0130 (11)	0.0288 (11)
F3	0.0684 (12)	0.0774 (13)	0.1198 (17)	0.0293 (10)	0.0324 (12)	0.0574 (12)
F2	0.139 (2)	0.0786 (14)	0.0794 (14)	0.0263 (14)	0.0685 (14)	0.0346 (11)
C24	0.0557 (16)	0.0616 (18)	0.0724 (19)	0.0038 (14)	0.0174 (14)	0.0262 (15)
C13	0.093 (3)	0.077 (2)	0.0596 (19)	0.0149 (19)	0.0050 (17)	0.0383 (17)

S1—C1	1.692 (3)	C9—N3	1.361 (3)
S1—C4	1.705 (3)	C6—C7	1.381 (3)
C11—C17	1.391 (4)	C6—C5	1.388 (4)
C11—C12	1.403 (4)	C6—H6	0.9300
C11—C10	1.516 (4)	C5—C4	1.463 (3)
C17—C16	1.388 (5)	C7—C8	1.494 (4)
C17—H17	0.9300	N4—C19	1.289 (3)
C12—C14	1.395 (5)	N4—N3	1.380 (3)
C12—C13	1.500 (5)	N3—C10	1.475 (3)
C16—C15	1.371 (7)	C10—C18	1.541 (3)
C16—H16	0.9300	C10—H10	0.9800
C15—C14	1.383 (7)	C19—C20	1.445 (3)
C15—H15	0.9300	C19—C18	1.500 (3)
C14—H14	0.9300	C21—C20	1.331 (4)
Cl1—C29	1.755 (4)	C21—H21	0.9300
Cl3—C29	1.732 (4)	C18—H18B	0.9700
Cl2—C29	1.716 (4)	C18—H18A	0.9700
C29—H29	0.9800	C20—H20	0.9300
C23—C25	1.401 (4)	C3—C4	1.413 (4)
C23—C22	1.405 (4)	C3—C2	1.444 (4)
C23—C24	1.495 (4)	C3—H3	0.9300
C22—C28	1.396 (4)	C1—C2	1.350 (5)
C22—C21	1.472 (3)	C1—H1	0.9300
C28—C27	1.368 (4)	C2—H2	0.9300
C28—H28	0.9300	C8—F2	1.319 (4)
C25—C26	1.361 (5)	C8—F3	1.327 (4)
C25—H25	0.9300	C8—F1	1.327 (3)
C26—C27	1.393 (5)	C24—H24C	0.9600
C26—H26	0.9300	C24—H24B	0.9600
C27—H27	0.9300	C24—H24A	0.9600
N2—C7	1.331 (3)	C13—H13A	0.9600
N2—C9	1.343 (3)	C13—H13C	0.9600
N1—C5	1.330 (3)	C13—H13B	0.9600
N1—C9	1.350 (3)
C1—S1—C4	91.99 (16)	C6—C7—C8	120.5 (2)
C17—C11—C12	120.6 (3)	C19—N4—N3	107.67 (19)
C17—C11—C10	118.4 (2)	C9—N3—N4	122.22 (19)
C12—C11—C10	120.9 (3)	C9—N3—C10	123.73 (18)
C16—C17—C11	120.5 (3)	N4—N3—C10	113.73 (18)
C16—C17—H17	119.8	N3—C10—C11	111.8 (2)
C11—C17—H17	119.8	N3—C10—C18	100.66 (18)
C14—C12—C11	117.3 (4)	C11—C10—C18	113.0 (2)
C14—C12—C13	120.6 (3)	N3—C10—H10	110.4
C11—C12—C13	122.0 (3)	C11—C10—H10	110.4
C15—C16—C17	119.5 (4)	C18—C10—H10	110.4
C15—C16—H16	120.2	N4—C19—C20	120.8 (2)
C17—C16—H16	120.2	N4—C19—C18	114.1 (2)
C16—C15—C14	120.3 (3)	C20—C19—C18	125.1 (2)
C16—C15—H15	119.9	C20—C21—C22	126.3 (2)
C14—C15—H15	119.9	C20—C21—H21	116.9
C15—C14—C12	121.8 (4)	C22—C21—H21	116.9
C15—C14—H14	119.1	C19—C18—C10	102.5 (2)
C12—C14—H14	119.1	C19—C18—H18B	111.3
Cl2—C29—Cl3	118.3 (2)	C10—C18—H18B	111.3
Cl2—C29—Cl1	107.7 (2)	C19—C18—H18A	111.3
Cl3—C29—Cl1	107.82 (18)	C10—C18—H18A	111.3
Cl2—C29—H29	107.6	H18B—C18—H18A	109.2
Cl3—C29—H29	107.6	C21—C20—C19	123.2 (2)
Cl1—C29—H29	107.6	C21—C20—H20	118.4
C25—C23—C22	117.9 (3)	C19—C20—H20	118.4
C25—C23—C24	119.4 (3)	C4—C3—C2	109.4 (3)
C22—C23—C24	122.7 (2)	C4—C3—H3	125.3
C28—C22—C23	118.7 (2)	C2—C3—H3	125.3
C28—C22—C21	120.9 (2)	C3—C4—C5	127.3 (3)
C23—C22—C21	120.4 (2)	C3—C4—S1	112.3 (2)
C27—C28—C22	122.0 (3)	C5—C4—S1	120.49 (19)
C27—C28—H28	119.0	C2—C1—S1	113.3 (2)
C22—C28—H28	119.0	C2—C1—H1	123.4
C26—C25—C23	122.8 (3)	S1—C1—H1	123.4
C26—C25—H25	118.6	C1—C2—C3	113.0 (3)
C23—C25—H25	118.6	C1—C2—H2	123.5
C25—C26—C27	119.0 (3)	C3—C2—H2	123.5
C25—C26—H26	120.5	F2—C8—F3	106.5 (3)
C27—C26—H26	120.5	F2—C8—F1	106.5 (2)
C28—C27—C26	119.6 (3)	F3—C8—F1	106.3 (2)
C28—C27—H27	120.2	F2—C8—C7	111.6 (2)
C26—C27—H27	120.2	F3—C8—C7	112.5 (2)
C7—N2—C9	114.4 (2)	F1—C8—C7	113.0 (2)
C5—N1—C9	116.6 (2)	C23—C24—H24C	109.5
N2—C9—N1	126.6 (2)	C23—C24—H24B	109.5
N2—C9—N3	119.0 (2)	H24C—C24—H24B	109.5
N1—C9—N3	114.4 (2)	C23—C24—H24A	109.5
C7—C6—C5	116.1 (2)	H24C—C24—H24A	109.5
C7—C6—H6	122.0	H24B—C24—H24A	109.5
C5—C6—H6	122.0	C12—C13—H13A	109.5
N1—C5—C6	121.9 (2)	C12—C13—H13C	109.5
N1—C5—C4	116.5 (2)	H13A—C13—H13C	109.5
C6—C5—C4	121.7 (2)	C12—C13—H13B	109.5
N2—C7—C6	124.5 (2)	H13A—C13—H13B	109.5
N2—C7—C8	115.1 (2)	H13C—C13—H13B	109.5
C12—C11—C17—C16	0.6 (4)	C19—N4—N3—C9	179.9 (2)
C10—C11—C17—C16	−176.4 (3)	C19—N4—N3—C10	6.2 (3)
C17—C11—C12—C14	1.2 (4)	C9—N3—C10—C11	−64.4 (3)
C10—C11—C12—C14	178.1 (3)	N4—N3—C10—C11	109.2 (2)
C17—C11—C12—C13	−177.5 (3)	C9—N3—C10—C18	175.5 (2)
C10—C11—C12—C13	−0.6 (4)	N4—N3—C10—C18	−10.9 (3)
C11—C17—C16—C15	−2.2 (5)	C17—C11—C10—N3	−41.0 (3)
C17—C16—C15—C14	2.0 (6)	C12—C11—C10—N3	142.0 (2)
C16—C15—C14—C12	−0.2 (6)	C17—C11—C10—C18	71.7 (3)
C11—C12—C14—C15	−1.4 (5)	C12—C11—C10—C18	−105.3 (3)
C13—C12—C14—C15	177.3 (4)	N3—N4—C19—C20	−179.4 (2)
C25—C23—C22—C28	1.1 (4)	N3—N4—C19—C18	1.9 (3)
C24—C23—C22—C28	−179.7 (3)	C28—C22—C21—C20	−9.4 (5)
C25—C23—C22—C21	−179.3 (3)	C23—C22—C21—C20	171.0 (3)
C24—C23—C22—C21	−0.1 (4)	N4—C19—C18—C10	−8.5 (3)
C23—C22—C28—C27	−2.0 (5)	C20—C19—C18—C10	172.9 (2)
C21—C22—C28—C27	178.4 (3)	N3—C10—C18—C19	10.6 (2)
C22—C23—C25—C26	0.5 (5)	C11—C10—C18—C19	−108.7 (2)
C24—C23—C25—C26	−178.7 (3)	C22—C21—C20—C19	−179.7 (2)
C23—C25—C26—C27	−1.2 (6)	N4—C19—C20—C21	−175.2 (3)
C22—C28—C27—C26	1.3 (6)	C18—C19—C20—C21	3.3 (4)
C25—C26—C27—C28	0.3 (6)	C2—C3—C4—C5	179.8 (3)
C7—N2—C9—N1	1.2 (4)	C2—C3—C4—S1	−0.3 (3)
C7—N2—C9—N3	−178.6 (2)	N1—C5—C4—C3	178.8 (2)
C5—N1—C9—N2	−0.4 (4)	C6—C5—C4—C3	0.1 (4)
C5—N1—C9—N3	179.3 (2)	N1—C5—C4—S1	−1.1 (3)
C9—N1—C5—C6	−0.6 (3)	C6—C5—C4—S1	−179.9 (2)
C9—N1—C5—C4	−179.3 (2)	C1—S1—C4—C3	0.6 (2)
C7—C6—C5—N1	0.8 (4)	C1—S1—C4—C5	−179.4 (2)
C7—C6—C5—C4	179.4 (2)	C4—S1—C1—C2	−0.9 (3)
C9—N2—C7—C6	−1.0 (4)	S1—C1—C2—C3	0.9 (4)
C9—N2—C7—C8	179.1 (2)	C4—C3—C2—C1	−0.4 (4)
C5—C6—C7—N2	0.1 (4)	N2—C7—C8—F2	72.4 (3)
C5—C6—C7—C8	180.0 (2)	C6—C7—C8—F2	−107.5 (3)
N2—C9—N3—N4	0.6 (4)	N2—C7—C8—F3	−47.2 (3)
N1—C9—N3—N4	−179.2 (2)	C6—C7—C8—F3	132.9 (3)
N2—C9—N3—C10	173.7 (2)	N2—C7—C8—F1	−167.5 (2)
N1—C9—N3—C10	−6.1 (3)	C6—C7—C8—F1	12.6 (4)

D—H···A	D—H	H···A	D···A	D—H···A
C20—H20···Cl1i	0.93	2.92	3.667 (3)	139
C29—H29···N2i	0.98	2.71	3.588 (4)	150
C1—H1···Cl1ii	0.93	2.91	3.606 (3)	133

Table 1

Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
C20—H20⋯Cl1i	0.93	2.92	3.667 (3)	139
C29—H29⋯N2i	0.98	2.71	3.588 (4)	150
C1—H1⋯Cl1ii	0.93	2.91	3.606 (3)	133

Symmetry codes: (i) ; (ii) .