2-[5-(2-Methyl­phen­yl)-3-(2-methyl­styryl)-4,5-di­hydro-1H-pyrazol-1-yl]-6-(thio­phen-2-yl)-4-(tri­fluoro­meth­yl)pyrimidine chloro­form monosolvate

In the crystal structure of the title compound, C₂₈H₂₃F₃N₄S·CHCl₃, the chloro­form solvate mol­ecules connect the pyrimidine mol­ecules into chains along [101] through weak C—H...N and C—H...Cl hydrogen-bond inter­actions. 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 inter­chain 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.

Key indicators

• Single-crystal X-ray study
• T = 273 K
• Mean [sigma](C-C) = 0.004 Å
• R factor = 0.068
• wR factor = 0.242
• Data-to-parameter ratio = 19.3

checkCIF/PLATON results

No syntax errors found



Alert level C
PLAT230_ALERT_2_C Hirshfeld Test Diff for    S1     --  C4      ..        5.1 su
PLAT241_ALERT_2_C High      Ueq as Compared to Neighbors for .....        C15 Check
PLAT244_ALERT_4_C Low   'Solvent' Ueq as Compared to Neighbors of         C29 Check
PLAT340_ALERT_3_C Low Bond Precision on  C-C Bonds ...............     0.0044 Ang.
PLAT412_ALERT_2_C Short Intra XH3 .. XHn     H10    ..  H13A    ..       1.83 Ang.
PLAT412_ALERT_2_C Short Intra XH3 .. XHn     H21    ..  H24C    ..       1.88 Ang.
PLAT480_ALERT_4_C Long H...A H-Bond Reported H20    ..  CL1     ..       2.92 Ang.
PLAT480_ALERT_4_C Long H...A H-Bond Reported H29    ..  N2      ..       2.71 Ang.
PLAT480_ALERT_4_C Long H...A H-Bond Reported H1     ..  CL1     ..       2.91 Ang.
PLAT910_ALERT_3_C Missing # of FCF Reflections Below Th(Min) .....          5 Why ?
PLAT911_ALERT_3_C Missing # FCF Refl Between THmin & STh/L=  0.600         15 Why ?
PLAT918_ALERT_3_C Reflection(s) with I(obs) much smaller I(calc) .          2 Check

Alert level G
PLAT005_ALERT_5_G No _iucr_refine_instructions_details  in the CIF     Please Do !
PLAT072_ALERT_2_G SHELXL First  Parameter in WGHT Unusually Large.       0.14 Why ?
PLAT154_ALERT_1_G The su's on the Cell Angles are Equal ..........    0.00200 Degree
PLAT199_ALERT_1_G Reported _cell_measurement_temperature ..... (K)        273 Check
PLAT200_ALERT_1_G Reported   _diffrn_ambient_temperature ..... (K)        273 Check
PLAT242_ALERT_2_G Low       Ueq as Compared to Neighbors for .....         C8 Check
PLAT380_ALERT_4_G Incorrectly? Oriented X(sp2)-Methyl Moiety .....        C24 Check
PLAT434_ALERT_2_G Short Inter HL..HL Contact  F2     ..  F2      .       2.71 Ang.
PLAT793_ALERT_4_G The Model has Chirality at C10     .............          S Verify
PLAT912_ALERT_4_G Missing # of FCF Reflections Above STh/L=  0.600         18 Note

   0 ALERT level A = Most likely a serious problem - resolve or explain
   0 ALERT level B = A potentially serious problem, consider carefully
  12 ALERT level C = Check. Ensure it is not caused by an omission or oversight
  10 ALERT level G = General information/check it is not something unexpected

   3 ALERT type 1 CIF construction/syntax error, inconsistent or missing data
   7 ALERT type 2 Indicator that the structure model may be wrong or deficient
   4 ALERT type 3 Indicator that the structure quality may be low
   7 ALERT type 4 Improvement, methodology, query or suggestion
   1 ALERT type 5 Informative message, check

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S1. Comment

The 4-trifluoromethyl-2-(5-aryl-3-styryl-1H-pyrazol-1yl)-pyrimidines are biologically active compounds (Gressler et al., 2010) obtained from a sequential two steps process involving [3 + 2] and [3 + 3] cyclocondensation starting from aminoguanidine (Flores et al., 2006). In the crystal structure of the title compound, the asymmetric unit is composed by the whole organic molecule, including an additional chloroform solvate (Fig. 1) and displaying some interesting conformational features (Fabiani Claro Flores et al., 2014). The styrene fragment is planar with r.m.s. deviation from the mean plane of 0.0456 Å and the least-squares plane angle between the 4,5-dihydropyrazole ring and the styrene fragment of 3.27 (19)°. Five-membered pyrazole and six-membered pyrimidine rings are also planar, with r.m.s. deviations from the plane of 0.0504 Å and 0.0044 Å, respectively. The torsion angle N4/N3/C9/N2 is 0.6 (4)°, showing that the pyrazole and pyrimidine rings are almost coplanar. The planarity can be confirmed by the pyrazole ring deviation from the least-squares plane by 1.87 (18)° from the pyrimidine ring. Additionally, the five-membered thien-2-yl ring is planar with r.m.s. deviation from the plane of 0.0040 Å and the least square plane angle between the pyrimidine ring and the thien-2-yl ring was 0.68 (18)°. This planarity observed is probably due to the π-resonance involving all system. The phenyl groupment C11/C12/C14/C15/C16/C17 deviates from the least-squares plane by 83.42 (9)° of 4,5-dihydropyrazole ring, indicating an orientation perpendicular between the rings. The geometry of the heterocyclic system is similar to that reported in the literature (Flores et al., 2006). The chloroform solvate molecule plays an important role in the crystal structure packing, connecting molecules into polymer-like chains through the following weak hydrogen bond interactions (Fig. 2): C29—H29···N2ⁱ (2.7056 (18) Å); C20ⁱ—H20ⁱ···Cl1 (2.9182 (12) Å); C1ⁱⁱ—H1ⁱⁱ···Cl1 (2.9072 (9) Å). The chloroform solvate also promotes further connections with adjacent chains through halogen long range contacts F1ⁱⁱⁱ···Cl2 (3.1854 (29) Å). The CF₃ group present a considerably short F2ⁱⁱⁱ···F2ⁱ distance of 2.712 (4) Å (Baker et al., 2012), which may contribute to the arrangement observed in the solid state (symmetry codes: (i) –x + 1, –y + 1, –z + 2; (ii) –x, –y + 1, –z + 1; (iii) x + 1, y, z). All these interactions presented distances lesser than the sum of the van der Waals radii of the atoms involved (Batsanov, 2001). Besides, F···F contacts are quite similar to that described for larger halogen atoms, such as bromine and iodine (Metrangolo et al., 2008).

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, Correia Flores, Rosa de Menezes Vicenti, Pizzuti & Teixeira Campos (2014).

S2. Experimental

To a mixture of 1-carboxamidino-3-(2'-methylstyryl)-5-(2-methylphenyl)-4,5-dihydro-1H-pyrazole hydrochloride (1.2 mmol) (Flores et al., 2006) and 1,1,1-trifluoro-4-methoxy-4-(tien-2-yl)-3-buten-2-one (1 mmol) in dry EtOH (3 ml) it was added three drops of BF₃·OEt₂, the mixture was stirred for 15 minutes. A yellow precipitated was isolated by filtration, washed with cold EtOH and recrystallized from CHCl₃, affording the title compound.

S3. Refinement

All H atoms attached to C atoms were positioned with idealized geometry and were refined isotropic with U_eq(H) set to 1.5 times of the U_eq(C) for CH₃ groups and 1.2 otherwise. It was used a riding model with C—H = 0.96 Å for CH₃, 0.97 Å for CH₂, 0.98 Å for CH and 0.93 Å for aromatic CH. The following set of reflections was omitted due to the large difference observed between F_o² and Fc²: -1 -2 2; 0 0 1; 0 1 0; 1 0 0; -2 -3 4; -3 -3 1; -2 -3 3; -4 5 0; -6 -2 2; -2 -4 4; 2 -9 1; -2 8 0; 1 1 6; 1 1 4; 3 3 1.

Computing details

Data collection: APEX2 (Bruker, 2009); cell refinement: SAINT (Bruker, 2009); data reduction: SAINT (Bruker, 2009); 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).

Figures

	Fig. 1. Asymmetric unit of the title compound. Ellipsoid probability: 50%.
	Fig. 2. Packing diagram of the title compound showing polymer-like chains interacting through Cl3C—H···F, Cl2HC—Cl···F and F···F weak contacts represented as dashed lines. Most of the hydrogen atoms were omitted for clarity. Darker colors were used to emphasize front molecules. Symmetry codes: (i) –x + 1, –y + 1, –z + 2; (ii) –x, –y + 1, –z + 1; (iii) x + 1, y, z.

2-[5-(2-Methylphenyl)-3-(2-methylstyryl)-4,5-dihydro-1H-pyrazol-1-yl]-6-(thiophen-2-yl)-4-(trifluoromethyl)pyrimidine chloroform monosolvate

Crystal data

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) Å^3

Data collection

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

Refinement on F^2	Primary atom site location: structure-invariant direct methods
Least-squares matrix: full	Secondary atom site location: difference Fourier map
R[F^2 > 2σ(F^2)] = 0.068	Hydrogen site location: inferred from neighbouring sites
wR(F^2) = 0.242	H-atom parameters constrained
S = 1.11	w = 1/[σ^2(Fo^2) + (0.1398P)^2 + 0.5025P] where P = (Fo^2 + 2Fc^2)/3
6974 reflections	(Δ/σ)max < 0.001
361 parameters	Δρmax = 1.24 e Å^−3
0 restraints	Δρmin = −0.93 e Å^−3

Special details

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.

Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Ų)

	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*

Atomic displacement parameters (Ų)

	U^11	U^22	U^33	U^12	U^13	U^23
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)

Geometric parameters (Å, º)

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)

Hydrogen-bond geometry (Å, º)

D—H···A	D—H	H···A	D···A	D—H···A
C20—H20···Cl1^i	0.93	2.92	3.667 (3)	139
C29—H29···N2^i	0.98	2.71	3.588 (4)	150
C1—H1···Cl1^ii	0.93	2.91	3.606 (3)	133

Symmetry codes: (i) −x+1, −y+1, −z+2; (ii) −x, −y+1, −z+1.