1-(3,5-Dichloro­phen­yl)-3-trifluoro­methyl-1H-pyrazol-5-yl 2-chloro­benzoate

In the title compound, C₁₇H₈Cl₃F₃N₂O₂, the asymmetric unit contains two mol­ecules, which are stacked by π–π inter­actions, and the asymmetric units are linked by inter­molecular C—H...O hydrogen bonds oriented along the [010] axis.

Key indicators

• Single-crystal X-ray study
• T = 294 K
• Mean [sigma](C-C) = 0.004 Å
• R factor = 0.044
• wR factor = 0.124
• Data-to-parameter ratio = 14.6

checkCIF/PLATON results

No syntax errors found



Alert level C
PLAT241_ALERT_2_C Check High      Ueq as Compared to Neighbors for         O1
PLAT242_ALERT_2_C Check Low       Ueq as Compared to Neighbors for        C11
PLAT242_ALERT_2_C Check Low       Ueq as Compared to Neighbors for        C28
PLAT431_ALERT_2_C Short Inter HL..A Contact  Cl2    ..  F1      ..       3.19 Ang.

   0 ALERT level A = In general: serious problem
   0 ALERT level B = Potentially serious problem
   4 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
   4 ALERT type 2 Indicator that the structure model may be wrong or deficient
   0 ALERT type 3 Indicator that the structure quality may be low
   0 ALERT type 4 Improvement, methodology, query or suggestion

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Computing details

Data collection: SMART (Bruker, 1997); cell refinement: SAINT (Bruker, 1997); 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, 1997); software used to prepare material for publication: SHELXTL.

1-(3,5-Dichlorophenyl)-3-trifluoromethyl-1H-pyrazol-5-yl 2-chlorobenzoate

Crystal data

C17H8Cl3F3N2O2	F(000) = 1744
Mr = 435.60	Dx = 1.681 Mg m^−3
Monoclinic, P21/n	Melting point = 386–387 K
Hall symbol: -P 2yn	Mo Kα radiation, λ = 0.71073 Å
a = 8.060 (3) Å	Cell parameters from 3881 reflections
b = 19.531 (6) Å	θ = 2.3–24.5°
c = 21.868 (7) Å	µ = 0.58 mm^−1
β = 90.512 (6)°	T = 294 K
V = 3442.2 (19) Å^3	Block, colourless
Z = 8	0.30 × 0.24 × 0.12 mm

Data collection

Bruker SMART CCD area-detector diffractometer	7086 independent reflections
Radiation source: fine-focus sealed tube	3882 reflections with I > 2σ(I)
Graphite monochromator	Rint = 0.044
φ and ω scans	θmax = 26.6°, θmin = 1.4°
Absorption correction: multi-scan (SADABS; Sheldrick, 1996)	h = −9→10
Tmin = 0.845, Tmax = 0.934	k = −24→24
19365 measured reflections	l = −27→15

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)] = 0.044	Hydrogen site location: inferred from neighbouring sites
wR(F^2) = 0.125	H-atom parameters constrained
S = 0.99	w = 1/[σ^2(Fo^2) + (0.051P)^2 + 0.9811P] where P = (Fo^2 + 2Fc^2)/3
7086 reflections	(Δ/σ)max = 0.003
487 parameters	Δρmax = 0.31 e Å^−3
0 restraints	Δρmin = −0.34 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
Cl1	0.45551 (11)	0.92530 (4)	0.05386 (4)	0.0601 (2)
Cl2	0.73482 (13)	0.92458 (4)	0.27754 (4)	0.0690 (3)
Cl3	0.22845 (11)	0.58763 (4)	0.41628 (4)	0.0581 (2)
Cl4	−0.03536 (12)	0.93718 (4)	0.05524 (4)	0.0621 (3)
Cl5	0.23780 (12)	0.93183 (4)	0.28075 (4)	0.0651 (3)
Cl6	−0.26573 (12)	0.58193 (4)	0.40496 (4)	0.0641 (3)
F1	0.7891 (2)	0.51439 (9)	0.10078 (9)	0.0682 (6)
F2	0.5312 (3)	0.49407 (9)	0.09213 (9)	0.0687 (6)
F3	0.6484 (3)	0.56378 (9)	0.02970 (8)	0.0661 (6)
F4	0.1475 (2)	0.50349 (8)	0.08472 (8)	0.0615 (5)
F5	0.0303 (3)	0.57322 (9)	0.02236 (8)	0.0656 (6)
F6	0.2905 (2)	0.57988 (9)	0.03748 (8)	0.0666 (6)
O1	0.4982 (3)	0.69090 (9)	0.26418 (9)	0.0564 (6)
O2	0.3672 (4)	0.59846 (12)	0.29714 (10)	0.0898 (10)
O3	0.0123 (3)	0.69211 (9)	0.25796 (8)	0.0515 (6)
O4	−0.0993 (4)	0.59434 (12)	0.28945 (10)	0.0863 (9)
N1	0.5951 (3)	0.70229 (11)	0.16554 (10)	0.0389 (6)
N2	0.6352 (3)	0.66579 (11)	0.11445 (10)	0.0415 (6)
N3	0.1063 (3)	0.71308 (10)	0.16073 (9)	0.0382 (6)
N4	0.1448 (3)	0.68250 (11)	0.10681 (10)	0.0416 (6)
C1	0.5988 (3)	0.77537 (13)	0.16503 (12)	0.0359 (7)
C2	0.5338 (3)	0.81008 (13)	0.11474 (12)	0.0380 (7)
H2	0.4908	0.7865	0.0812	0.046*
C3	0.5352 (4)	0.88087 (14)	0.11620 (13)	0.0410 (7)
C4	0.5963 (4)	0.91755 (14)	0.16559 (13)	0.0439 (7)
H4	0.5947	0.9652	0.1659	0.053*
C5	0.6595 (4)	0.88092 (15)	0.21421 (13)	0.0434 (7)
C6	0.6644 (3)	0.81001 (14)	0.21449 (13)	0.0397 (7)
H6	0.7109	0.7864	0.2473	0.048*
C7	0.6428 (4)	0.54435 (16)	0.08729 (14)	0.0481 (8)
C8	0.6068 (4)	0.60152 (14)	0.13039 (12)	0.0390 (7)
C9	0.5482 (4)	0.59419 (14)	0.18966 (13)	0.0476 (8)
H9	0.5200	0.5541	0.2101	0.057*
C10	0.5419 (4)	0.65987 (14)	0.21064 (12)	0.0410 (7)
C11	0.4090 (4)	0.65556 (14)	0.30686 (12)	0.0396 (7)
C12	0.3779 (3)	0.69832 (14)	0.36131 (12)	0.0356 (7)
C13	0.4259 (4)	0.76696 (14)	0.36304 (13)	0.0444 (7)
H13	0.4787	0.7858	0.3294	0.053*
C14	0.3968 (4)	0.80742 (17)	0.41340 (14)	0.0569 (9)
H14	0.4277	0.8533	0.4134	0.068*
C15	0.3210 (4)	0.77899 (18)	0.46396 (15)	0.0612 (10)
H15	0.3034	0.8057	0.4985	0.073*
C16	0.2719 (4)	0.71209 (17)	0.46349 (13)	0.0530 (9)
H16	0.2198	0.6938	0.4976	0.064*
C17	0.2988 (4)	0.67130 (14)	0.41288 (12)	0.0411 (7)
C18	0.1059 (3)	0.78619 (13)	0.16427 (12)	0.0350 (7)
C19	0.0421 (3)	0.82187 (13)	0.11500 (12)	0.0384 (7)
H19	0.0000	0.7989	0.0810	0.046*
C20	0.0425 (4)	0.89256 (14)	0.11746 (13)	0.0407 (7)
C21	0.1022 (4)	0.92803 (14)	0.16785 (13)	0.0439 (7)
H21	0.1012	0.9756	0.1690	0.053*
C22	0.1632 (4)	0.89022 (14)	0.21611 (13)	0.0404 (7)
C23	0.1688 (3)	0.81908 (14)	0.21511 (12)	0.0372 (7)
H23	0.2136	0.7945	0.2477	0.045*
C24	0.1466 (4)	0.56796 (15)	0.06585 (13)	0.0453 (8)
C25	0.1187 (4)	0.61677 (13)	0.11701 (12)	0.0374 (7)
C26	0.0627 (4)	0.60304 (14)	0.17585 (12)	0.0415 (7)
H26	0.0364	0.5609	0.1930	0.050*
C27	0.0558 (4)	0.66600 (14)	0.20209 (12)	0.0385 (7)
C28	−0.0717 (4)	0.65274 (15)	0.29952 (12)	0.0409 (7)
C29	−0.1112 (3)	0.69367 (14)	0.35424 (12)	0.0352 (7)
C30	−0.0650 (4)	0.76276 (14)	0.35862 (13)	0.0454 (7)
H30	−0.0099	0.7830	0.3261	0.055*
C31	−0.0989 (4)	0.80165 (16)	0.40968 (14)	0.0554 (9)
H31	−0.0670	0.8474	0.4115	0.066*
C32	−0.1806 (4)	0.77176 (17)	0.45793 (14)	0.0583 (9)
H32	−0.2025	0.7973	0.4928	0.070*
C33	−0.2296 (4)	0.70488 (17)	0.45493 (13)	0.0528 (9)
H33	−0.2862	0.6856	0.4875	0.063*
C34	−0.1958 (4)	0.66559 (14)	0.40388 (13)	0.0414 (7)

Atomic displacement parameters (Ų)

	U^11	U^22	U^33	U^12	U^13	U^23
Cl1	0.0841 (7)	0.0519 (5)	0.0443 (4)	0.0114 (4)	0.0015 (4)	0.0111 (4)
Cl2	0.0978 (7)	0.0531 (5)	0.0557 (5)	−0.0163 (5)	−0.0147 (5)	−0.0145 (4)
Cl3	0.0723 (6)	0.0560 (5)	0.0463 (4)	−0.0100 (4)	0.0143 (4)	0.0075 (4)
Cl4	0.0927 (7)	0.0470 (5)	0.0465 (5)	0.0150 (5)	−0.0045 (4)	0.0114 (4)
Cl5	0.0921 (7)	0.0492 (5)	0.0538 (5)	−0.0076 (5)	−0.0148 (5)	−0.0160 (4)
Cl6	0.0821 (7)	0.0527 (5)	0.0579 (5)	−0.0162 (5)	0.0224 (5)	0.0031 (4)
F1	0.0739 (14)	0.0635 (12)	0.0674 (13)	0.0183 (11)	0.0035 (11)	−0.0138 (10)
F2	0.0880 (15)	0.0455 (11)	0.0729 (13)	−0.0134 (10)	0.0107 (11)	−0.0179 (10)
F3	0.1044 (17)	0.0593 (12)	0.0350 (10)	0.0075 (11)	0.0089 (10)	−0.0091 (9)
F4	0.0975 (15)	0.0325 (10)	0.0547 (11)	0.0054 (10)	0.0087 (10)	−0.0041 (8)
F5	0.0926 (16)	0.0626 (12)	0.0413 (10)	0.0073 (11)	−0.0154 (10)	−0.0127 (9)
F6	0.0803 (14)	0.0580 (12)	0.0619 (12)	0.0043 (10)	0.0283 (11)	−0.0127 (10)
O1	0.0985 (18)	0.0339 (11)	0.0374 (11)	−0.0114 (11)	0.0291 (12)	−0.0055 (9)
O2	0.158 (3)	0.0598 (16)	0.0518 (15)	−0.0460 (17)	0.0449 (16)	−0.0187 (13)
O3	0.0910 (17)	0.0305 (10)	0.0334 (11)	−0.0090 (11)	0.0218 (11)	−0.0040 (9)
O4	0.150 (3)	0.0545 (15)	0.0546 (15)	−0.0400 (16)	0.0424 (16)	−0.0172 (12)
N1	0.0537 (16)	0.0309 (12)	0.0323 (12)	−0.0036 (11)	0.0109 (11)	0.0008 (11)
N2	0.0552 (16)	0.0376 (14)	0.0320 (13)	−0.0013 (12)	0.0086 (12)	−0.0063 (11)
N3	0.0604 (17)	0.0268 (12)	0.0276 (12)	−0.0009 (11)	0.0086 (11)	−0.0023 (10)
N4	0.0635 (17)	0.0316 (13)	0.0298 (12)	0.0012 (12)	0.0100 (12)	−0.0033 (10)
C1	0.0431 (18)	0.0321 (14)	0.0326 (15)	−0.0028 (13)	0.0120 (13)	−0.0003 (13)
C2	0.0455 (19)	0.0367 (16)	0.0318 (15)	−0.0027 (13)	0.0072 (13)	−0.0016 (13)
C3	0.0492 (19)	0.0385 (17)	0.0354 (16)	0.0029 (14)	0.0092 (14)	0.0063 (13)
C4	0.056 (2)	0.0304 (15)	0.0457 (17)	−0.0064 (14)	0.0113 (15)	−0.0012 (14)
C5	0.052 (2)	0.0383 (17)	0.0397 (16)	−0.0070 (14)	0.0035 (15)	−0.0045 (13)
C6	0.0441 (19)	0.0380 (17)	0.0371 (16)	−0.0030 (14)	0.0039 (14)	0.0032 (13)
C7	0.060 (2)	0.0420 (18)	0.0424 (18)	0.0054 (17)	0.0037 (16)	−0.0059 (15)
C8	0.0459 (19)	0.0352 (16)	0.0360 (16)	−0.0036 (14)	0.0037 (14)	−0.0044 (13)
C9	0.071 (2)	0.0307 (16)	0.0415 (17)	−0.0025 (15)	0.0152 (16)	−0.0022 (13)
C10	0.058 (2)	0.0337 (16)	0.0317 (15)	−0.0011 (14)	0.0106 (14)	−0.0022 (12)
C11	0.055 (2)	0.0346 (16)	0.0297 (15)	−0.0028 (14)	0.0028 (14)	0.0022 (13)
C12	0.0394 (18)	0.0391 (16)	0.0281 (14)	0.0048 (13)	−0.0024 (12)	0.0012 (12)
C13	0.058 (2)	0.0403 (17)	0.0351 (16)	0.0001 (15)	0.0027 (14)	−0.0010 (14)
C14	0.077 (3)	0.0449 (19)	0.049 (2)	0.0038 (17)	0.0003 (18)	−0.0084 (16)
C15	0.077 (3)	0.065 (2)	0.0415 (19)	0.017 (2)	0.0017 (18)	−0.0154 (17)
C16	0.060 (2)	0.066 (2)	0.0330 (16)	0.0116 (18)	0.0087 (15)	−0.0021 (16)
C17	0.0459 (19)	0.0446 (17)	0.0327 (15)	0.0056 (14)	0.0018 (14)	0.0015 (13)
C18	0.0439 (18)	0.0289 (14)	0.0325 (15)	−0.0012 (13)	0.0123 (13)	0.0006 (12)
C19	0.0508 (19)	0.0330 (16)	0.0316 (14)	−0.0001 (13)	0.0066 (14)	−0.0018 (12)
C20	0.0495 (19)	0.0362 (16)	0.0365 (16)	0.0059 (14)	0.0067 (14)	0.0056 (13)
C21	0.060 (2)	0.0251 (14)	0.0463 (17)	−0.0003 (14)	0.0106 (16)	0.0005 (14)
C22	0.0480 (19)	0.0355 (16)	0.0377 (16)	−0.0063 (14)	0.0031 (14)	−0.0090 (13)
C23	0.0455 (19)	0.0351 (16)	0.0312 (14)	0.0003 (13)	0.0056 (13)	0.0007 (12)
C24	0.062 (2)	0.0364 (17)	0.0373 (17)	0.0033 (15)	0.0064 (16)	−0.0015 (14)
C25	0.0504 (19)	0.0303 (15)	0.0313 (15)	0.0022 (13)	0.0009 (13)	−0.0012 (12)
C26	0.063 (2)	0.0292 (15)	0.0321 (15)	0.0009 (14)	0.0056 (14)	0.0009 (12)
C27	0.055 (2)	0.0329 (15)	0.0275 (14)	0.0004 (14)	0.0042 (13)	0.0004 (12)
C28	0.052 (2)	0.0357 (17)	0.0347 (16)	−0.0071 (14)	0.0045 (14)	0.0002 (13)
C29	0.0390 (18)	0.0369 (15)	0.0296 (14)	0.0019 (13)	−0.0024 (13)	0.0008 (12)
C30	0.062 (2)	0.0388 (17)	0.0356 (16)	−0.0010 (15)	0.0030 (15)	−0.0001 (14)
C31	0.075 (3)	0.0429 (18)	0.0479 (19)	0.0044 (17)	−0.0008 (18)	−0.0083 (15)
C32	0.081 (3)	0.056 (2)	0.0380 (18)	0.0212 (19)	0.0080 (17)	−0.0115 (16)
C33	0.062 (2)	0.061 (2)	0.0352 (17)	0.0081 (17)	0.0138 (15)	0.0011 (15)
C34	0.0446 (19)	0.0407 (17)	0.0391 (16)	0.0053 (14)	0.0021 (14)	0.0040 (13)

Geometric parameters (Å, º)

Cl1—C3	1.735 (3)	C9—C10	1.363 (4)
Cl2—C5	1.732 (3)	C9—H9	0.9300
Cl3—C17	1.732 (3)	C11—C12	1.478 (4)
Cl4—C20	1.729 (3)	C12—C13	1.396 (4)
Cl5—C22	1.734 (3)	C12—C17	1.404 (4)
Cl6—C34	1.729 (3)	C13—C14	1.377 (4)
F1—C7	1.347 (4)	C13—H13	0.9300
F2—C7	1.337 (3)	C14—C15	1.384 (4)
F3—C7	1.316 (3)	C14—H14	0.9300
F4—C24	1.325 (3)	C15—C16	1.365 (4)
F5—C24	1.334 (3)	C15—H15	0.9300
F6—C24	1.340 (3)	C16—C17	1.382 (4)
O1—C10	1.367 (3)	C16—H16	0.9300
O1—C11	1.370 (3)	C18—C23	1.377 (4)
O2—C11	1.183 (3)	C18—C19	1.379 (4)
O3—C27	1.372 (3)	C19—C20	1.382 (4)
O3—C28	1.373 (3)	C19—H19	0.9300
O4—C28	1.182 (3)	C20—C21	1.384 (4)
N1—C10	1.361 (3)	C21—C22	1.375 (4)
N1—N2	1.367 (3)	C21—H21	0.9300
N1—C1	1.428 (3)	C22—C23	1.390 (4)
N2—C8	1.323 (3)	C23—H23	0.9300
N3—C27	1.355 (3)	C24—C25	1.488 (4)
N3—N4	1.360 (3)	C25—C26	1.393 (4)
N3—C18	1.430 (3)	C26—C27	1.358 (4)
N4—C25	1.320 (3)	C26—H26	0.9300
C1—C6	1.377 (4)	C28—C29	1.476 (4)
C1—C2	1.390 (4)	C29—C34	1.399 (4)
C2—C3	1.383 (4)	C29—C30	1.403 (4)
C2—H2	0.9300	C30—C31	1.380 (4)
C3—C4	1.383 (4)	C30—H30	0.9300
C4—C5	1.376 (4)	C31—C32	1.378 (4)
C4—H4	0.9300	C31—H31	0.9300
C5—C6	1.385 (4)	C32—C33	1.366 (4)
C6—H6	0.9300	C32—H32	0.9300
C7—C8	1.491 (4)	C33—C34	1.384 (4)
C8—C9	1.391 (4)	C33—H33	0.9300
C10—O1—C11	120.0 (2)	C15—C16—H16	119.7
C27—O3—C28	120.8 (2)	C17—C16—H16	119.7
C10—N1—N2	110.7 (2)	C16—C17—C12	120.2 (3)
C10—N1—C1	128.4 (2)	C16—C17—Cl3	117.1 (2)
N2—N1—C1	120.7 (2)	C12—C17—Cl3	122.7 (2)
C8—N2—N1	103.7 (2)	C23—C18—C19	121.8 (2)
C27—N3—N4	110.7 (2)	C23—C18—N3	120.6 (2)
C27—N3—C18	129.9 (2)	C19—C18—N3	117.6 (2)
N4—N3—C18	119.1 (2)	C18—C19—C20	118.3 (3)
C25—N4—N3	104.0 (2)	C18—C19—H19	120.8
C6—C1—C2	121.4 (2)	C20—C19—H19	120.8
C6—C1—N1	119.5 (3)	C19—C20—C21	122.1 (3)
C2—C1—N1	119.1 (2)	C19—C20—Cl4	118.2 (2)
C3—C2—C1	117.8 (3)	C21—C20—Cl4	119.7 (2)
C3—C2—H2	121.1	C22—C21—C20	117.5 (2)
C1—C2—H2	121.1	C22—C21—H21	121.3
C4—C3—C2	122.6 (3)	C20—C21—H21	121.3
C4—C3—Cl1	118.8 (2)	C21—C22—C23	122.4 (3)
C2—C3—Cl1	118.6 (2)	C21—C22—Cl5	119.5 (2)
C5—C4—C3	117.4 (3)	C23—C22—Cl5	118.0 (2)
C5—C4—H4	121.3	C18—C23—C22	117.8 (3)
C3—C4—H4	121.3	C18—C23—H23	121.1
C4—C5—C6	122.3 (3)	C22—C23—H23	121.1
C4—C5—Cl2	119.1 (2)	F4—C24—F5	107.3 (2)
C6—C5—Cl2	118.6 (2)	F4—C24—F6	107.9 (2)
C1—C6—C5	118.5 (3)	F5—C24—F6	105.2 (2)
C1—C6—H6	120.8	F4—C24—C25	112.0 (2)
C5—C6—H6	120.8	F5—C24—C25	112.1 (2)
F3—C7—F2	108.4 (3)	F6—C24—C25	111.9 (3)
F3—C7—F1	107.3 (2)	N4—C25—C26	113.4 (2)
F2—C7—F1	104.6 (2)	N4—C25—C24	118.1 (2)
F3—C7—C8	113.4 (3)	C26—C25—C24	128.5 (3)
F2—C7—C8	111.4 (2)	C27—C26—C25	103.3 (2)
F1—C7—C8	111.2 (3)	C27—C26—H26	128.3
N2—C8—C9	113.8 (2)	C25—C26—H26	128.3
N2—C8—C7	120.6 (2)	N3—C27—C26	108.6 (2)
C9—C8—C7	125.6 (3)	N3—C27—O3	115.0 (2)
C10—C9—C8	103.3 (2)	C26—C27—O3	136.4 (2)
C10—C9—H9	128.3	O4—C28—O3	120.7 (3)
C8—C9—H9	128.3	O4—C28—C29	129.2 (3)
N1—C10—C9	108.4 (2)	O3—C28—C29	110.1 (2)
N1—C10—O1	115.9 (2)	C34—C29—C30	117.1 (2)
C9—C10—O1	135.7 (3)	C34—C29—C28	121.8 (2)
O2—C11—O1	120.2 (3)	C30—C29—C28	121.1 (2)
O2—C11—C12	128.9 (3)	C31—C30—C29	122.0 (3)
O1—C11—C12	111.0 (2)	C31—C30—H30	119.0
C13—C12—C17	117.8 (2)	C29—C30—H30	119.0
C13—C12—C11	121.1 (2)	C32—C31—C30	119.1 (3)
C17—C12—C11	121.1 (3)	C32—C31—H31	120.5
C14—C13—C12	121.6 (3)	C30—C31—H31	120.5
C14—C13—H13	119.2	C33—C32—C31	120.5 (3)
C12—C13—H13	119.2	C33—C32—H32	119.7
C13—C14—C15	119.2 (3)	C31—C32—H32	119.7
C13—C14—H14	120.4	C32—C33—C34	120.7 (3)
C15—C14—H14	120.4	C32—C33—H33	119.7
C16—C15—C14	120.5 (3)	C34—C33—H33	119.7
C16—C15—H15	119.7	C33—C34—C29	120.6 (3)
C14—C15—H15	119.7	C33—C34—Cl6	116.5 (2)
C15—C16—C17	120.7 (3)	C29—C34—Cl6	122.8 (2)
C10—N1—N2—C8	−0.7 (3)	C13—C12—C17—Cl3	178.4 (2)
C1—N1—N2—C8	−175.7 (3)	C11—C12—C17—Cl3	−1.3 (4)
C27—N3—N4—C25	−0.9 (3)	C27—N3—C18—C23	48.5 (4)
C18—N3—N4—C25	−174.2 (2)	N4—N3—C18—C23	−139.6 (3)
C10—N1—C1—C6	48.2 (4)	C27—N3—C18—C19	−132.0 (3)
N2—N1—C1—C6	−137.9 (3)	N4—N3—C18—C19	39.9 (4)
C10—N1—C1—C2	−131.0 (3)	C23—C18—C19—C20	0.1 (4)
N2—N1—C1—C2	43.0 (4)	N3—C18—C19—C20	−179.3 (2)
C6—C1—C2—C3	−0.8 (4)	C18—C19—C20—C21	−0.9 (4)
N1—C1—C2—C3	178.4 (2)	C18—C19—C20—Cl4	179.3 (2)
C1—C2—C3—C4	−0.8 (4)	C19—C20—C21—C22	0.3 (4)
C1—C2—C3—Cl1	179.8 (2)	Cl4—C20—C21—C22	−179.9 (2)
C2—C3—C4—C5	0.9 (4)	C20—C21—C22—C23	1.2 (4)
Cl1—C3—C4—C5	−179.7 (2)	C20—C21—C22—Cl5	−179.4 (2)
C3—C4—C5—C6	0.5 (4)	C19—C18—C23—C22	1.3 (4)
C3—C4—C5—Cl2	−179.1 (2)	N3—C18—C23—C22	−179.3 (2)
C2—C1—C6—C5	2.1 (4)	C21—C22—C23—C18	−2.0 (4)
N1—C1—C6—C5	−177.0 (2)	Cl5—C22—C23—C18	178.6 (2)
C4—C5—C6—C1	−2.1 (4)	N3—N4—C25—C26	0.6 (3)
Cl2—C5—C6—C1	177.6 (2)	N3—N4—C25—C24	178.8 (3)
N1—N2—C8—C9	0.5 (3)	F4—C24—C25—N4	167.9 (3)
N1—N2—C8—C7	−177.4 (3)	F5—C24—C25—N4	−71.4 (4)
F3—C7—C8—N2	−21.6 (4)	F6—C24—C25—N4	46.6 (4)
F2—C7—C8—N2	−144.2 (3)	F4—C24—C25—C26	−14.1 (5)
F1—C7—C8—N2	99.5 (3)	F5—C24—C25—C26	106.6 (3)
F3—C7—C8—C9	160.8 (3)	F6—C24—C25—C26	−135.4 (3)
F2—C7—C8—C9	38.1 (4)	N4—C25—C26—C27	−0.1 (4)
F1—C7—C8—C9	−78.2 (4)	C24—C25—C26—C27	−178.1 (3)
N2—C8—C9—C10	−0.2 (4)	N4—N3—C27—C26	0.8 (3)
C7—C8—C9—C10	177.6 (3)	C18—N3—C27—C26	173.3 (3)
N2—N1—C10—C9	0.6 (3)	N4—N3—C27—O3	−179.3 (2)
C1—N1—C10—C9	175.1 (3)	C18—N3—C27—O3	−6.9 (4)
N2—N1—C10—O1	180.0 (2)	C25—C26—C27—N3	−0.5 (3)
C1—N1—C10—O1	−5.6 (4)	C25—C26—C27—O3	179.8 (3)
C8—C9—C10—N1	−0.3 (3)	C28—O3—C27—N3	166.8 (3)
C8—C9—C10—O1	−179.4 (3)	C28—O3—C27—C26	−13.4 (5)
C11—O1—C10—N1	165.3 (3)	C27—O3—C28—O4	4.6 (5)
C11—O1—C10—C9	−15.7 (5)	C27—O3—C28—C29	−177.0 (2)
C10—O1—C11—O2	−1.2 (5)	O4—C28—C29—C34	−1.4 (5)
C10—O1—C11—C12	179.1 (2)	O3—C28—C29—C34	−179.6 (3)
O2—C11—C12—C13	−175.0 (4)	O4—C28—C29—C30	178.6 (4)
O1—C11—C12—C13	4.7 (4)	O3—C28—C29—C30	0.4 (4)
O2—C11—C12—C17	4.8 (5)	C34—C29—C30—C31	0.8 (4)
O1—C11—C12—C17	−175.5 (3)	C28—C29—C30—C31	−179.1 (3)
C17—C12—C13—C14	−0.1 (4)	C29—C30—C31—C32	0.0 (5)
C11—C12—C13—C14	179.6 (3)	C30—C31—C32—C33	−1.0 (5)
C12—C13—C14—C15	1.2 (5)	C31—C32—C33—C34	1.1 (5)
C13—C14—C15—C16	−1.6 (5)	C32—C33—C34—C29	−0.2 (5)
C14—C15—C16—C17	0.8 (5)	C32—C33—C34—Cl6	−179.4 (3)
C15—C16—C17—C12	0.3 (5)	C30—C29—C34—C33	−0.7 (4)
C15—C16—C17—Cl3	−178.8 (3)	C28—C29—C34—C33	179.2 (3)
C13—C12—C17—C16	−0.6 (4)	C30—C29—C34—Cl6	178.4 (2)
C11—C12—C17—C16	179.6 (3)	C28—C29—C34—Cl6	−1.7 (4)

Hydrogen-bond geometry (Å, º)

D—H···A	D—H	H···A	D···A	D—H···A
C6—H6···O1	0.93	2.56	2.901 (3)	102
C9—H9···O2	0.93	2.44	2.779 (4)	102
C13—H13···O1	0.93	2.34	2.691 (4)	102
C21—H21···O2^i	0.93	2.52	3.424 (4)	163
C23—H23···O3	0.93	2.59	2.939 (3)	103
C26—H26···O4	0.93	2.47	2.822 (4)	102
C30—H30···O3	0.93	2.33	2.676 (4)	102

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