5-Amino-1-[2,6-dichloro-4-(trifluoro­meth­yl)phen­yl]-4-(trifluoro­methyl­sulfan­yl)-1H-pyrazole-3-carbonitrile

The mol­ecule of the title compound, C₁₂H₄Cl₂F₆N₄S, exhibits disorder of both trifluoro­methyl groups. Crystal packing is realised by N—H...N hydrogen bonds.

Key indicators

• Single-crystal X-ray study
• T = 298 K
• Mean [sigma](C-C) = 0.003 Å
• Disorder in main residue
• R factor = 0.047
• wR factor = 0.113
• Data-to-parameter ratio = 10.7

checkCIF/PLATON results

No syntax errors found



Alert level A
PLAT241_ALERT_2_A Check High      Ueq as Compared to Neighbors for        F4'
PLAT241_ALERT_2_A Check High      Ueq as Compared to Neighbors for        F6'
PLAT242_ALERT_2_A Check Low       Ueq as Compared to Neighbors for        C12

Author Response: see _publ_section_exptl_refinement

Alert level B
PLAT241_ALERT_2_B Check High      Ueq as Compared to Neighbors for         F2
PLAT241_ALERT_2_B Check High      Ueq as Compared to Neighbors for         F5
PLAT242_ALERT_2_B Check Low       Ueq as Compared to Neighbors for         C1

Author Response: see _publ_section_exptl_refinement

Alert level C
PLAT215_ALERT_3_C Disordered F4'     has ADP max/min Ratio .......       3.50
PLAT241_ALERT_2_C Check High      Ueq as Compared to Neighbors for         F3
PLAT241_ALERT_2_C Check High      Ueq as Compared to Neighbors for        F3'
PLAT242_ALERT_2_C Check Low       Ueq as Compared to Neighbors for         F6

Author Response: see _publ_section_exptl_refinement

PLAT301_ALERT_3_C Main Residue  Disorder .........................      17.00 Perc.
PLAT371_ALERT_2_C Long   C(sp2)-C(sp1) Bond  C3     -   C5     ...       1.44 Ang.
PLAT420_ALERT_2_C D-H Without Acceptor       N4     -   H4B    ...          ?
PLAT431_ALERT_2_C Short Inter HL..A Contact  F4'    ..  N1      ..       2.97 Ang.
PLAT710_ALERT_4_C Delete 1-2-3 or 2-3-4 Linear Torsion Angle ... #         50
            N2  -C3  -C5  -N1      9.00  0.00   1.555   1.555   1.555   1.555
PLAT710_ALERT_4_C Delete 1-2-3 or 2-3-4 Linear Torsion Angle ... #         51
            C2  -C3  -C5  -N1      9.00  0.00   1.555   1.555   1.555   1.555
PLAT779_ALERT_2_C Suspect or Irrelevant (Bond) Angle in CIF ......      22.00 Deg.
              F2   -C1   -F2'     1.555   1.555   1.555
PLAT779_ALERT_2_C Suspect or Irrelevant (Bond) Angle in CIF ......      11.50 Deg.
              F3   -C1   -F3'     1.555   1.555   1.555
PLAT779_ALERT_2_C Suspect or Irrelevant (Bond) Angle in CIF ......      40.00 Deg.
              F5'  -C12  -F5      1.555   1.555   1.555
PLAT779_ALERT_2_C Suspect or Irrelevant (Bond) Angle in CIF ......      39.60 Deg.
              F4'  -C12  -F4      1.555   1.555   1.555

   3 ALERT level A = In general: serious problem
   3 ALERT level B = Potentially serious problem
  14 ALERT level C = Check and explain
   0 ALERT level G = General alerts; check

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

---

Computing details

Data collection: SMART (Bruker, 2002); cell refinement: SAINT (Bruker, 2002); data reduction: SAINT; program(s) used to solve structure: SHELXS97 (Sheldrick, 1997); program(s) used to refine structure: SHELXL97 (Sheldrick, 1997); molecular graphics: SHELXTL (Bruker, 2002); software used to prepare material for publication: SHELXL97.

5-Amino-1-[2,6-dichloro-4-(trifluoromethyl)phenyl]- 4-(trifluoromethylsulfanyl)-1H-pyrazole-3-carbonitrile

Crystal data

C12H4Cl2F6N4S	F(000) = 832
Mr = 421.16	Dx = 1.701 Mg m^−3
Monoclinic, P21/n	Melting point: 434(1) K
Hall symbol: -P 2yn	Mo Kα radiation, λ = 0.71073 Å
a = 10.7801 (8) Å	Cell parameters from 3781 reflections
b = 12.7006 (9) Å	θ = 2.3–25.0°
c = 12.1039 (9) Å	µ = 0.59 mm^−1
β = 96.973 (1)°	T = 298 K
V = 1644.9 (2) Å^3	Prism, colourless
Z = 4	0.42 × 0.29 × 0.21 mm

Data collection

Bruker APEX area-detector diffractometer	2953 independent reflections
Radiation source: fine-focus sealed tube	2636 reflections with I > 2σ(I)
Graphite monochromator	Rint = 0.018
φ and ω scans	θmax = 25.2°, θmin = 2.3°
Absorption correction: multi-scan (SADABS; Bruker, 2002)	h = −12→12
Tmin = 0.791, Tmax = 0.887	k = −12→15
8518 measured reflections	l = −14→12

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)] = 0.047	Hydrogen site location: inferred from neighbouring sites
wR(F^2) = 0.114	H atoms treated by a mixture of independent and constrained refinement
S = 1.10	w = 1/[σ^2(Fo^2) + (0.059P)^2 + 0.9497P] where P = (Fo^2 + 2Fc^2)/3
2953 reflections	(Δ/σ)max = 0.001
277 parameters	Δρmax = 0.21 e Å^−3
2 restraints	Δρmin = −0.26 e Å^−3

Special details

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	Occ. (<1)
Cl1	1.17081 (7)	0.08140 (6)	0.57001 (6)	0.0642 (2)
Cl2	0.77652 (7)	0.31669 (7)	0.40429 (7)	0.0773 (3)
S1	1.05416 (7)	0.41352 (7)	0.84033 (6)	0.0664 (2)
F1	1.0052 (3)	0.60601 (19)	0.8706 (2)	0.1317 (10)
F2	0.852 (2)	0.516 (2)	0.830 (2)	0.128 (7)	0.50
F2'	0.841 (2)	0.5160 (19)	0.788 (2)	0.116 (6)	0.50
F3	0.9607 (13)	0.5570 (11)	0.7024 (10)	0.119 (4)	0.50
F3'	0.9846 (13)	0.5642 (12)	0.7017 (12)	0.116 (5)	0.50
F4	1.0293 (15)	0.1466 (7)	0.0813 (8)	0.120 (4)	0.50
F4'	0.9506 (19)	0.1303 (13)	0.0777 (5)	0.166 (7)	0.50
F5	1.1159 (10)	0.0611 (16)	0.1334 (9)	0.147 (6)	0.50
F5'	1.0824 (13)	0.0015 (11)	0.1475 (7)	0.121 (5)	0.50
F6	0.8933 (7)	0.0364 (11)	0.1036 (7)	0.105 (2)	0.50
F6'	0.9570 (19)	−0.0224 (10)	0.1410 (9)	0.157 (4)	0.50
N1	0.7652 (3)	0.2128 (2)	0.8963 (2)	0.0742 (8)
N2	0.8823 (2)	0.19271 (17)	0.64758 (18)	0.0528 (5)
N3	0.96566 (19)	0.23574 (17)	0.58307 (16)	0.0476 (5)
N4	1.1189 (2)	0.3691 (2)	0.5841 (2)	0.0665 (7)
C1	0.9642 (3)	0.5287 (3)	0.8031 (3)	0.0764 (9)
C2	0.9915 (2)	0.3283 (2)	0.73624 (19)	0.0473 (6)
C3	0.8993 (2)	0.2506 (2)	0.7390 (2)	0.0483 (6)
C4	1.0329 (2)	0.3159 (2)	0.63280 (19)	0.0461 (6)
C5	0.8250 (3)	0.2289 (2)	0.8273 (2)	0.0559 (7)
C6	0.9741 (2)	0.19387 (19)	0.47544 (19)	0.0433 (5)
C7	1.0653 (2)	0.1209 (2)	0.45895 (19)	0.0439 (5)
C8	1.0749 (2)	0.0802 (2)	0.3545 (2)	0.0474 (6)
H8	1.1357	0.0305	0.3440	0.057*
C9	0.9923 (2)	0.1149 (2)	0.2663 (2)	0.0491 (6)
C10	0.9004 (2)	0.1872 (2)	0.2804 (2)	0.0527 (6)
H10	0.8452	0.2096	0.2200	0.063*
C11	0.8914 (2)	0.2260 (2)	0.3853 (2)	0.0493 (6)
C12	1.0025 (4)	0.0728 (3)	0.1517 (3)	0.0709 (9)
H4A	1.145 (3)	0.347 (3)	0.525 (2)	0.085*
H4B	1.144 (3)	0.4243 (19)	0.615 (3)	0.085*

Atomic displacement parameters (Ų)

	U^11	U^22	U^33	U^12	U^13	U^23
Cl1	0.0571 (4)	0.0807 (5)	0.0530 (4)	0.0067 (3)	0.0000 (3)	0.0074 (3)
Cl2	0.0658 (5)	0.0778 (5)	0.0892 (6)	0.0270 (4)	0.0127 (4)	−0.0132 (4)
S1	0.0674 (5)	0.0828 (5)	0.0486 (4)	−0.0024 (4)	0.0062 (3)	−0.0208 (4)
F1	0.164 (2)	0.0879 (16)	0.147 (2)	−0.0156 (16)	0.0340 (19)	−0.0584 (16)
F2	0.062 (6)	0.117 (8)	0.22 (2)	0.007 (5)	0.064 (9)	−0.017 (10)
F2'	0.079 (5)	0.091 (7)	0.185 (15)	0.009 (4)	0.040 (7)	0.024 (8)
F3	0.162 (9)	0.092 (7)	0.094 (8)	0.037 (6)	−0.016 (6)	0.003 (5)
F3'	0.143 (7)	0.086 (6)	0.135 (9)	−0.013 (5)	0.086 (7)	0.020 (5)
F4	0.206 (11)	0.092 (4)	0.078 (5)	−0.009 (7)	0.080 (7)	−0.002 (3)
F4'	0.237 (13)	0.228 (16)	0.030 (3)	0.134 (12)	0.001 (5)	−0.006 (5)
F5	0.113 (5)	0.255 (16)	0.083 (6)	−0.007 (10)	0.050 (5)	−0.068 (9)
F5'	0.170 (12)	0.133 (7)	0.056 (3)	0.099 (8)	0.002 (6)	−0.030 (4)
F6	0.094 (4)	0.141 (7)	0.078 (4)	−0.011 (4)	−0.003 (3)	−0.057 (5)
F6'	0.237 (13)	0.134 (7)	0.107 (6)	−0.077 (7)	0.051 (7)	−0.076 (6)
N1	0.0890 (18)	0.0733 (17)	0.0697 (16)	0.0114 (14)	0.0484 (15)	0.0084 (13)
N2	0.0556 (12)	0.0536 (13)	0.0540 (13)	−0.0067 (10)	0.0266 (10)	−0.0054 (10)
N3	0.0487 (11)	0.0548 (12)	0.0430 (11)	−0.0079 (10)	0.0203 (9)	−0.0098 (9)
N4	0.0661 (15)	0.0786 (18)	0.0612 (15)	−0.0287 (13)	0.0338 (12)	−0.0250 (13)
C1	0.075 (2)	0.068 (2)	0.092 (3)	−0.0118 (17)	0.032 (2)	−0.0232 (19)
C2	0.0475 (13)	0.0557 (15)	0.0405 (12)	0.0021 (11)	0.0122 (10)	−0.0056 (11)
C3	0.0523 (14)	0.0505 (14)	0.0457 (13)	0.0047 (11)	0.0207 (11)	0.0007 (11)
C4	0.0425 (13)	0.0558 (15)	0.0418 (13)	−0.0032 (11)	0.0128 (10)	−0.0064 (11)
C5	0.0644 (16)	0.0525 (15)	0.0558 (16)	0.0085 (13)	0.0268 (13)	0.0006 (12)
C6	0.0434 (12)	0.0468 (13)	0.0418 (13)	−0.0065 (10)	0.0140 (10)	−0.0070 (10)
C7	0.0402 (12)	0.0517 (14)	0.0407 (12)	−0.0041 (10)	0.0083 (10)	0.0005 (10)
C8	0.0455 (13)	0.0492 (14)	0.0500 (14)	0.0041 (11)	0.0158 (11)	−0.0063 (11)
C9	0.0546 (14)	0.0509 (15)	0.0435 (13)	−0.0044 (11)	0.0124 (11)	−0.0078 (11)
C10	0.0548 (15)	0.0562 (15)	0.0458 (14)	0.0043 (12)	0.0008 (11)	−0.0022 (12)
C11	0.0432 (13)	0.0490 (14)	0.0566 (15)	0.0028 (11)	0.0101 (11)	−0.0071 (11)
C12	0.085 (2)	0.078 (2)	0.0496 (17)	0.0031 (19)	0.0113 (17)	−0.0163 (16)

Geometric parameters (Å, º)

Cl1—C7	1.726 (2)	F6'—C12	1.306 (8)
Cl2—C11	1.727 (3)	N1—C5	1.135 (3)
S1—C2	1.735 (3)	N2—C3	1.323 (3)
S1—C1	1.783 (4)	N2—N3	1.374 (3)
F1—C1	1.319 (4)	N3—C4	1.349 (3)
F2—F2'	0.51 (5)	N3—C6	1.420 (3)
F2—C1	1.30 (2)	N4—C4	1.340 (3)
F2'—C1	1.33 (2)	N4—H4A	0.848 (18)
F3—C1	1.266 (11)	N4—H4B	0.828 (18)
F3'—C1	1.350 (12)	C2—C4	1.388 (3)
F4—F4'	0.869 (16)	C2—C3	1.403 (4)
F4—C12	1.321 (8)	C3—C5	1.438 (3)
F4—F5	1.517 (15)	C6—C11	1.383 (4)
F4'—C12	1.235 (9)	C6—C7	1.384 (3)
F4'—F6	1.396 (16)	C7—C8	1.381 (3)
F5—F5'	0.866 (12)	C8—C9	1.377 (4)
F5—C12	1.277 (10)	C8—H8	0.9300
F5'—C12	1.255 (8)	C9—C10	1.377 (4)
F5'—F6'	1.378 (13)	C9—C12	1.503 (4)
F6—F6'	1.077 (13)	C10—C11	1.376 (4)
F6—C12	1.331 (7)	C10—H10	0.9300
C2—S1—C1	100.16 (15)	N2—C3—C2	113.4 (2)
F2'—F2—C1	81 (5)	N2—C3—C5	118.8 (2)
F2—F2'—C1	76 (5)	C2—C3—C5	127.8 (2)
F4'—F4—C12	64.8 (9)	N4—C4—N3	123.2 (2)
F4'—F4—F5	113.5 (13)	N4—C4—C2	130.9 (2)
C12—F4—F5	52.9 (5)	N3—C4—C2	105.9 (2)
F4—F4'—C12	75.6 (10)	N1—C5—C3	179.0 (3)
F4—F4'—F6	130.4 (14)	C11—C6—C7	119.0 (2)
C12—F4'—F6	60.4 (6)	C11—C6—N3	120.4 (2)
F5'—F5—C12	68.6 (10)	C7—C6—N3	120.6 (2)
F5'—F5—F4	117.2 (14)	C8—C7—C6	121.1 (2)
C12—F5—F4	55.6 (5)	C8—C7—Cl1	119.27 (19)
F5—F5'—C12	71.4 (9)	C6—C7—Cl1	119.66 (18)
F5—F5'—F6'	127.7 (14)	C9—C8—C7	118.5 (2)
C12—F5'—F6'	59.2 (6)	C9—C8—H8	120.7
F6'—F6—C12	64.7 (6)	C7—C8—H8	120.7
F6'—F6—F4'	114.2 (9)	C10—C9—C8	121.6 (2)
C12—F6—F4'	53.8 (5)	C10—C9—C12	119.1 (3)
F6—F6'—C12	67.1 (8)	C8—C9—C12	119.3 (2)
F6—F6'—F5'	116.3 (10)	C11—C10—C9	119.1 (2)
C12—F6'—F5'	55.7 (5)	C11—C10—H10	120.5
C3—N2—N3	102.7 (2)	C9—C10—H10	120.5
C4—N3—N2	113.58 (19)	C10—C11—C6	120.7 (2)
C4—N3—C6	126.99 (19)	C10—C11—Cl2	119.6 (2)
N2—N3—C6	119.44 (19)	C6—C11—Cl2	119.70 (19)
C4—N4—H4A	122 (2)	F4'—C12—F5'	130.6 (6)
C4—N4—H4B	116 (3)	F4'—C12—F5	107.5 (8)
H4A—N4—H4B	123 (3)	F5'—C12—F5	40.0 (6)
F3—C1—F2	111.0 (13)	F4'—C12—F6'	110.1 (8)
F3—C1—F1	110.7 (7)	F5'—C12—F6'	65.1 (7)
F2—C1—F1	100.7 (13)	F5—C12—F6'	103.4 (7)
F3—C1—F2'	89.4 (13)	F4'—C12—F4	39.6 (8)
F2—C1—F2'	22 (2)	F5'—C12—F4	106.3 (7)
F1—C1—F2'	115.4 (12)	F5—C12—F4	71.4 (7)
F3—C1—F3'	11.5 (11)	F6'—C12—F4	134.6 (6)
F2—C1—F3'	122.0 (13)	F4'—C12—F6	65.8 (8)
F1—C1—F3'	103.6 (8)	F5'—C12—F6	107.8 (6)
F2'—C1—F3'	100.7 (12)	F5—C12—F6	134.2 (6)
F3—C1—S1	115.4 (7)	F6'—C12—F6	48.2 (6)
F2—C1—S1	109.2 (11)	F4—C12—F6	102.5 (6)
F1—C1—S1	108.8 (3)	F4'—C12—C9	112.4 (5)
F2'—C1—S1	116.1 (10)	F5'—C12—C9	114.9 (4)
F3'—C1—S1	111.1 (7)	F5—C12—C9	112.3 (6)
C4—C2—C3	104.4 (2)	F6'—C12—C9	110.7 (4)
C4—C2—S1	125.86 (19)	F4—C12—C9	112.9 (5)
C3—C2—S1	129.47 (18)	F6—C12—C9	111.6 (4)
F5—F4—F4'—C12	21.6 (10)	F6—F4'—C12—F5'	93.3 (10)
C12—F4—F4'—F6	−27.4 (11)	F4—F4'—C12—F5	−24.9 (13)
F5—F4—F4'—F6	−6 (2)	F6—F4'—C12—F5	131.3 (6)
F4'—F4—F5—F5'	7 (2)	F4—F4'—C12—F6'	−136.9 (11)
C12—F4—F5—F5'	32.0 (12)	F6—F4'—C12—F6'	19.4 (7)
F4'—F4—F5—C12	−24.7 (11)	F6—F4'—C12—F4	156.2 (12)
F4—F5—F5'—C12	−28.0 (10)	F4—F4'—C12—F6	−156.2 (12)
C12—F5—F5'—F6'	19.6 (13)	F4—F4'—C12—C9	99.2 (10)
F4—F5—F5'—F6'	−8 (2)	F6—F4'—C12—C9	−104.5 (6)
F4—F4'—F6—F6'	6.4 (18)	F5—F5'—C12—F4'	66.2 (17)
C12—F4'—F6—F6'	−24.5 (7)	F6'—F5'—C12—F4'	−95.8 (11)
F4—F4'—F6—C12	30.8 (13)	F6'—F5'—C12—F5	−162.0 (14)
F4'—F6—F6'—C12	21.7 (6)	F5—F5'—C12—F6'	162.0 (14)
C12—F6—F6'—F5'	−27.1 (6)	F5—F5'—C12—F4	30.0 (13)
F4'—F6—F6'—F5'	−5.4 (11)	F6'—F5'—C12—F4	−132.1 (7)
F5—F5'—F6'—F6	9 (2)	F5—F5'—C12—F6	139.2 (11)
C12—F5'—F6'—F6	30.6 (7)	F6'—F5'—C12—F6	−22.8 (7)
F5—F5'—F6'—C12	−21.7 (15)	F5—F5'—C12—C9	−95.6 (12)
C3—N2—N3—C4	0.8 (3)	F6'—F5'—C12—C9	102.3 (5)
C3—N2—N3—C6	−179.5 (2)	F5'—F5—C12—F4'	−133.2 (12)
F2'—F2—C1—F3	16 (6)	F4—F5—C12—F4'	16.5 (9)
F2'—F2—C1—F1	134 (5)	F4—F5—C12—F5'	149.6 (13)
F2'—F2—C1—F3'	20 (6)	F5'—F5—C12—F6'	−16.7 (13)
F2'—F2—C1—S1	−112 (5)	F4—F5—C12—F6'	132.9 (6)
F2—F2'—C1—F3	−165 (5)	F5'—F5—C12—F4	−149.6 (13)
F2—F2'—C1—F1	−52 (6)	F5'—F5—C12—F6	−60.2 (16)
F2—F2'—C1—F3'	−163 (5)	F4—F5—C12—F6	89.4 (10)
F2—F2'—C1—S1	77 (6)	F5'—F5—C12—C9	102.6 (11)
C2—S1—C1—F3	−50.9 (8)	F4—F5—C12—C9	−107.8 (6)
C2—S1—C1—F2	74.9 (13)	F6—F6'—C12—F4'	−23.9 (8)
C2—S1—C1—F1	−176.0 (2)	F5'—F6'—C12—F4'	126.4 (7)
C2—S1—C1—F2'	51.7 (13)	F6—F6'—C12—F5'	−150.3 (8)
C2—S1—C1—F3'	−62.6 (7)	F6—F6'—C12—F5	−138.6 (8)
C1—S1—C2—C4	89.0 (3)	F5'—F6'—C12—F5	11.7 (9)
C1—S1—C2—C3	−98.0 (3)	F6—F6'—C12—F4	−61.6 (12)
N3—N2—C3—C2	−0.7 (3)	F5'—F6'—C12—F4	88.7 (11)
N3—N2—C3—C5	179.2 (2)	F5'—F6'—C12—F6	150.3 (8)
C4—C2—C3—N2	0.4 (3)	F6—F6'—C12—C9	101.0 (6)
S1—C2—C3—N2	−173.8 (2)	F5'—F6'—C12—C9	−108.7 (5)
C4—C2—C3—C5	−179.5 (3)	F5—F4—C12—F4'	−154.9 (13)
S1—C2—C3—C5	6.3 (4)	F4'—F4—C12—F5'	135.1 (11)
N2—N3—C4—N4	−179.7 (3)	F5—F4—C12—F5'	−19.8 (8)
C6—N3—C4—N4	0.7 (4)	F4'—F4—C12—F5	154.9 (13)
N2—N3—C4—C2	−0.6 (3)	F4'—F4—C12—F6'	64.3 (15)
C6—N3—C4—C2	179.8 (2)	F5—F4—C12—F6'	−90.6 (11)
C3—C2—C4—N4	179.1 (3)	F4'—F4—C12—F6	22.1 (11)
S1—C2—C4—N4	−6.4 (4)	F5—F4—C12—F6	−132.8 (6)
C3—C2—C4—N3	0.1 (3)	F4'—F4—C12—C9	−98.0 (11)
S1—C2—C4—N3	174.58 (19)	F5—F4—C12—C9	107.1 (6)
N2—C3—C5—N1	−91 (21)	F6'—F6—C12—F4'	155.3 (8)
C2—C3—C5—N1	89 (21)	F6'—F6—C12—F5'	28.1 (8)
C4—N3—C6—C11	−97.0 (3)	F4'—F6—C12—F5'	−127.2 (7)
N2—N3—C6—C11	83.4 (3)	F6'—F6—C12—F5	64.0 (12)
C4—N3—C6—C7	82.6 (3)	F4'—F6—C12—F5	−91.3 (11)
N2—N3—C6—C7	−97.0 (3)	F4'—F6—C12—F6'	−155.3 (8)
C11—C6—C7—C8	0.1 (4)	F6'—F6—C12—F4	140.1 (7)
N3—C6—C7—C8	−179.5 (2)	F4'—F6—C12—F4	−15.2 (7)
C11—C6—C7—Cl1	179.00 (19)	F6'—F6—C12—C9	−98.9 (6)
N3—C6—C7—Cl1	−0.7 (3)	F4'—F6—C12—C9	105.8 (5)
C6—C7—C8—C9	0.8 (4)	C10—C9—C12—F4'	20.1 (13)
Cl1—C7—C8—C9	−178.04 (19)	C8—C9—C12—F4'	−160.1 (13)
C7—C8—C9—C10	−1.1 (4)	C10—C9—C12—F5'	−174.8 (10)
C7—C8—C9—C12	179.1 (3)	C8—C9—C12—F5'	5.1 (11)
C8—C9—C10—C11	0.3 (4)	C10—C9—C12—F5	141.5 (10)
C12—C9—C10—C11	−179.8 (3)	C8—C9—C12—F5	−38.6 (11)
C9—C10—C11—C6	0.7 (4)	C10—C9—C12—F6'	−103.5 (12)
C9—C10—C11—Cl2	180.0 (2)	C8—C9—C12—F6'	76.3 (12)
C7—C6—C11—C10	−0.9 (4)	C10—C9—C12—F4	63.1 (9)
N3—C6—C11—C10	178.8 (2)	C8—C9—C12—F4	−117.1 (8)
C7—C6—C11—Cl2	179.78 (19)	C10—C9—C12—F6	−51.6 (8)
N3—C6—C11—Cl2	−0.6 (3)	C8—C9—C12—F6	128.2 (8)
F4—F4'—C12—F5'	−63.0 (16)

Hydrogen-bond geometry (Å, º)

D—H···A	D—H	H···A	D···A	D—H···A
N4—H4A···N1^i	0.85 (2)	2.27 (2)	3.099 (3)	164 (3)

Symmetry code: (i) x+1/2, −y+1/2, z−1/2.