1-(4-Chloro­phenyl)-3-(4-tri­fluoro­methyl­benzoyl­hydrazino)­-2-propenone

The title compound, C₁₇H₁₂ClF₃N₂O₂, contains two independent mol­ecules in the asymmetric unit. The dihedral angles between the two benzene rings in each mol­ecule are 53.9 (2) and 23.1 (2)°. The crystal packing is stabilized by intermolecular hydrogen bonds, which link the mol­ecules into two-dimensional layers.

Key indicators

• Single-crystal X-ray study
• T = 293 K
• Mean [sigma](C-C) = 0.005 Å
• R factor = 0.061
• wR factor = 0.189
• Data-to-parameter ratio = 11.6

checkCIF/PLATON results

No syntax errors found



Alert level B
PLAT242_ALERT_2_B Check Low    U(eq) as Compared to Neighbors  for         C8
PLAT242_ALERT_2_B Check Low    U(eq) as Compared to Neighbors  for        C25

Alert level C
PLAT066_ALERT_1_C Predicted and Reported Transmissions Identical .          ?
PLAT125_ALERT_4_C No _symmetry_space_group_name_Hall Given .......          ?
PLAT213_ALERT_2_C Atom F3      has ADP max/min Ratio .............       3.10 prolat
PLAT242_ALERT_2_C Check Low    U(eq) as Compared to Neighbors  for        C15
PLAT242_ALERT_2_C Check Low    U(eq) as Compared to Neighbors  for        C32
PLAT250_ALERT_2_C Large U3/U1 Ratio for Average U(i,j) Tensor ....       2.31
PLAT301_ALERT_3_C Main Residue  Disorder .........................       6.00 Perc.
PLAT309_ALERT_2_C Single Bonded Oxygen (C-O .GT. 1.3 Ang) ........         O4
PLAT340_ALERT_3_C Low Bond Precision on C-C bonds (x 1000) Ang ...          6
PLAT431_ALERT_2_C Short Inter HL..A Contact  Cl1    ..  Cl1     ..       3.23 Ang.
PLAT480_ALERT_4_C Long H...A H-Bond Reported H9     ..  CG2     ..       2.99 Ang.
PLAT480_ALERT_4_C Long H...A H-Bond Reported H31    ..  CG1     ..       2.95 Ang.
PLAT731_ALERT_1_C Bond    Calc     0.86(3), Rep   0.862(10) ......       3.00 su-Rat
              N1   -H1A     1.555   1.555
PLAT731_ALERT_1_C Bond    Calc     0.86(3), Rep   0.857(10) ......       3.00 su-Rat
              N2   -H2A     1.555   1.555
PLAT779_ALERT_2_C Suspect or Irrelevant (Bond) Angle in CIF ......      44.50 Deg.
              F3   -C8   -F2'     1.555   1.555   1.555

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

   3 ALERT type 1 CIF construction/syntax error, inconsistent or missing data
   9 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
   3 ALERT type 4 Improvement, methodology, query or suggestion

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Computing details

Data collection: SMART (Siemens, 1996); cell refinement: SAINT (Siemens, 1996); data reduction: SAINT; program(s) used to solve structure: SHELXTL (Sheldrick, 1997); program(s) used to refine structure: SHELXTL; molecular graphics: SHELXTL; software used to prepare material for publication: SHELXTL, PARST (Nardelli, 1995) and PLATON (Spek, 1990).

1-(4-Chlorophenyl)3-(4-trifluoromethylbenzoylhydrazino)prop-2-en-1-one

Crystal data

C17H12ClF3N2O2	Z = 4
Mr = 368.74	F(000) = 752
Triclinic, P1	Dx = 1.504 Mg m^−3
a = 7.6851 (14) Å	Mo Kα radiation, λ = 0.71073 Å
b = 8.8523 (16) Å	Cell parameters from 8493 reflections
c = 25.104 (4) Å	θ = 0.8–25.0°
α = 86.897 (3)°	µ = 0.28 mm^−1
β = 88.293 (3)°	T = 293 K
γ = 72.739 (3)°	Colomn, colorless
V = 1628.4 (5) Å^3	0.32 × 0.24 × 0.16 mm

Data collection

Siemens SMART 1000 CCD area-detector diffractometer	5711 independent reflections
Radiation source: fine-focus sealed tube	3546 reflections with I > 2σ(I)
Graphite monochromator	Rint = 0.021
Detector resolution: 8.33 pixels mm^-1	θmax = 25.0°, θmin = 0.8°
ω scans	h = −4→9
Absorption correction: empirical (using intensity measurements) (SADABS; Sheldrick, 1996)	k = −10→10
Tmin = 0.916, Tmax = 0.957	l = −29→29
8493 measured reflections

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)] = 0.061	Hydrogen site location: inferred from neighbouring sites
wR(F^2) = 0.189	H-atom parameters constrained
S = 1.09	w = 1/[σ^2(Fo^2) + (0.0816P)^2 + 0.8468P] where P = (Fo^2 + 2Fc^2)/3
5711 reflections	(Δ/σ)max < 0.001
494 parameters	Δρmax = 0.28 e Å^−3
49 restraints	Δρmin = −0.30 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	0.8424 (2)	0.4699 (2)	0.03928 (7)	0.1271 (7)
Cl2	1.33450 (17)	0.94732 (16)	0.04182 (5)	0.0848 (4)
C1	−0.2238 (4)	−0.0125 (4)	0.33451 (13)	0.0368 (8)
C2	−0.1729 (5)	−0.1187 (4)	0.37820 (15)	0.0518 (10)
H2	−0.0501	−0.1633	0.3859	0.062*
C3	−0.3023 (5)	−0.1580 (5)	0.40992 (16)	0.0553 (10)
H3	−0.2670	−0.2291	0.4390	0.066*
C4	−0.4843 (5)	−0.0929 (4)	0.39900 (15)	0.0459 (9)
C5	−0.5362 (5)	0.0116 (4)	0.35542 (15)	0.0496 (9)
H5	−0.6590	0.0542	0.3475	0.060*
C6	−0.4071 (5)	0.0530 (4)	0.32377 (15)	0.0466 (9)
H6	−0.4430	0.1254	0.2950	0.056*
C7	−0.0769 (5)	0.0271 (4)	0.30191 (14)	0.0416 (9)
C8	−0.6226 (5)	−0.1357 (5)	0.43422 (16)	0.0606 (11)
C9	0.0364 (5)	0.1953 (4)	0.20086 (15)	0.0503 (10)
H9	−0.0387	0.1436	0.1862	0.060*
C10	0.1646 (5)	0.2289 (4)	0.16783 (15)	0.0493 (9)
H10	0.1688	0.2035	0.1323	0.059*
C11	0.2923 (5)	0.3016 (4)	0.18579 (14)	0.0422 (9)
C12	0.4283 (5)	0.3419 (4)	0.14809 (14)	0.0409 (9)
C13	0.5598 (5)	0.4001 (4)	0.16784 (16)	0.0491 (9)
H13	0.5633	0.4118	0.2043	0.059*
C14	0.6862 (5)	0.4412 (5)	0.13471 (18)	0.0609 (11)
H14	0.7736	0.4813	0.1485	0.073*
C15	0.6804 (6)	0.4216 (5)	0.08068 (19)	0.0692 (13)
C16	0.5524 (7)	0.3652 (5)	0.05971 (17)	0.0682 (13)
H16	0.5510	0.3528	0.0232	0.082*
C17	0.4247 (6)	0.3264 (4)	0.09304 (14)	0.0543 (10)
H17	0.3354	0.2896	0.0788	0.065*
C18	0.3010 (4)	0.4821 (4)	0.34887 (13)	0.0346 (8)
C19	0.3547 (5)	0.3948 (4)	0.39604 (14)	0.0453 (9)
H19	0.4757	0.3678	0.4063	0.054*
C20	0.2293 (5)	0.3477 (4)	0.42781 (15)	0.0501 (10)
H20	0.2659	0.2903	0.4597	0.060*
C21	0.0508 (5)	0.3850 (4)	0.41271 (14)	0.0438 (9)
C22	−0.0037 (5)	0.4712 (4)	0.36513 (14)	0.0458 (9)
H22	−0.1242	0.4957	0.3545	0.055*
C23	0.1214 (4)	0.5205 (4)	0.33367 (14)	0.0415 (8)
H23	0.0845	0.5799	0.3021	0.050*
C24	0.4430 (4)	0.5277 (4)	0.31598 (13)	0.0365 (8)
C25	−0.0863 (5)	0.3332 (5)	0.44644 (16)	0.0567 (11)
C26	0.4689 (5)	0.8397 (4)	0.22702 (15)	0.0494 (10)
H26	0.3497	0.9057	0.2286	0.059*
C27	0.5978 (5)	0.8821 (4)	0.19227 (15)	0.0494 (10)
H27	0.5585	0.9744	0.1708	0.059*
C28	0.7752 (5)	0.7951 (4)	0.18878 (14)	0.0418 (8)
C29	0.9104 (5)	0.8319 (4)	0.15144 (14)	0.0418 (8)
C30	1.0932 (5)	0.7445 (5)	0.15475 (17)	0.0572 (11)
H30	1.1291	0.6622	0.1805	0.069*
C31	1.2219 (5)	0.7779 (5)	0.12061 (18)	0.0640 (12)
H31	1.3435	0.7179	0.1230	0.077*
C32	1.1693 (6)	0.9006 (5)	0.08293 (16)	0.0535 (10)
C33	0.9908 (6)	0.9873 (5)	0.07811 (16)	0.0595 (11)
H33	0.9564	1.0687	0.0520	0.071*
C34	0.8622 (5)	0.9535 (5)	0.11205 (15)	0.0554 (10)
H34	0.7407	1.0130	0.1087	0.067*
F1	−0.643 (2)	−0.067 (2)	0.4786 (4)	0.103 (6)	0.53 (3)
F2	−0.581 (2)	−0.2885 (7)	0.4471 (9)	0.136 (10)	0.53 (3)
F3	−0.7844 (14)	−0.096 (3)	0.4139 (5)	0.140 (11)	0.53 (3)
F1'	−0.5669 (19)	−0.184 (3)	0.4831 (4)	0.124 (11)	0.47 (3)
F2'	−0.7740 (17)	−0.0195 (10)	0.4400 (9)	0.122 (11)	0.47 (3)
F3'	−0.679 (2)	−0.2470 (19)	0.4159 (5)	0.093 (6)	0.47 (3)
F4	−0.0272 (4)	0.2748 (4)	0.49371 (11)	0.1149 (13)
F5	−0.2376 (4)	0.4504 (3)	0.45445 (13)	0.1033 (11)
F6	−0.1437 (4)	0.2259 (3)	0.42392 (12)	0.0973 (10)
N1	−0.1192 (4)	0.1771 (3)	0.28163 (13)	0.0482 (8)
H1A	−0.217 (3)	0.248 (3)	0.2910 (14)	0.057 (11)*
N2	0.0078 (4)	0.2283 (4)	0.25126 (14)	0.0479 (8)
H2A	0.084 (3)	0.271 (3)	0.2636 (12)	0.033 (10)*
N3	0.3889 (4)	0.6672 (3)	0.28807 (12)	0.0420 (7)
H3A	0.278 (2)	0.727 (3)	0.2904 (14)	0.049 (11)*
N4	0.5151 (4)	0.7119 (3)	0.25614 (12)	0.0433 (7)
H4A	0.6294 (18)	0.663 (4)	0.2530 (14)	0.052*
O1	0.0703 (3)	−0.0689 (3)	0.29300 (11)	0.0624 (8)
O2	0.2971 (4)	0.3320 (4)	0.23354 (11)	0.0649 (8)
O3	0.6024 (3)	0.4438 (3)	0.31433 (10)	0.0473 (6)
O4	0.8406 (3)	0.6641 (3)	0.21963 (11)	0.0581 (8)

Atomic displacement parameters (Ų)

	U^11	U^22	U^33	U^12	U^13	U^23
Cl1	0.0928 (11)	0.1763 (17)	0.1190 (13)	−0.0622 (11)	0.0407 (9)	0.0392 (12)
Cl2	0.0827 (9)	0.1040 (10)	0.0805 (8)	−0.0496 (8)	0.0396 (7)	−0.0141 (7)
C1	0.0314 (18)	0.0316 (17)	0.046 (2)	−0.0080 (15)	0.0059 (15)	−0.0050 (15)
C2	0.034 (2)	0.049 (2)	0.066 (3)	−0.0052 (17)	0.0034 (18)	0.0092 (19)
C3	0.048 (2)	0.058 (2)	0.058 (2)	−0.017 (2)	0.0031 (19)	0.0116 (19)
C4	0.043 (2)	0.047 (2)	0.052 (2)	−0.0204 (18)	0.0081 (17)	−0.0066 (17)
C5	0.0307 (19)	0.052 (2)	0.068 (3)	−0.0147 (17)	0.0013 (17)	−0.0027 (19)
C6	0.035 (2)	0.045 (2)	0.059 (2)	−0.0123 (17)	−0.0001 (17)	0.0073 (17)
C7	0.0326 (19)	0.0384 (18)	0.049 (2)	−0.0044 (16)	0.0069 (16)	−0.0019 (16)
C8	0.054 (3)	0.069 (3)	0.069 (3)	−0.033 (2)	0.015 (2)	−0.008 (2)
C9	0.044 (2)	0.049 (2)	0.060 (3)	−0.0168 (18)	0.0025 (18)	−0.0007 (18)
C10	0.051 (2)	0.058 (2)	0.044 (2)	−0.023 (2)	0.0047 (17)	−0.0036 (17)
C11	0.040 (2)	0.0387 (19)	0.041 (2)	−0.0028 (16)	0.0050 (16)	0.0024 (16)
C12	0.0374 (19)	0.0320 (17)	0.049 (2)	−0.0046 (16)	0.0071 (16)	0.0006 (15)
C13	0.045 (2)	0.048 (2)	0.054 (2)	−0.0148 (18)	0.0056 (18)	−0.0010 (17)
C14	0.042 (2)	0.059 (2)	0.084 (3)	−0.020 (2)	0.004 (2)	0.008 (2)
C15	0.052 (3)	0.075 (3)	0.077 (3)	−0.019 (2)	0.024 (2)	0.019 (2)
C16	0.082 (3)	0.077 (3)	0.049 (3)	−0.031 (3)	0.019 (2)	0.001 (2)
C17	0.066 (3)	0.059 (2)	0.044 (2)	−0.029 (2)	0.0062 (19)	0.0003 (18)
C18	0.0279 (17)	0.0318 (17)	0.0434 (19)	−0.0075 (14)	0.0031 (14)	−0.0041 (14)
C19	0.0315 (19)	0.052 (2)	0.053 (2)	−0.0136 (17)	−0.0018 (16)	0.0013 (17)
C20	0.046 (2)	0.059 (2)	0.046 (2)	−0.0188 (19)	−0.0017 (17)	0.0063 (18)
C21	0.038 (2)	0.050 (2)	0.046 (2)	−0.0177 (17)	0.0056 (16)	−0.0071 (17)
C22	0.0299 (19)	0.053 (2)	0.056 (2)	−0.0155 (17)	0.0009 (16)	−0.0062 (18)
C23	0.0340 (19)	0.0440 (19)	0.045 (2)	−0.0101 (16)	0.0014 (15)	0.0015 (16)
C24	0.0312 (18)	0.0325 (17)	0.046 (2)	−0.0091 (15)	0.0048 (15)	−0.0077 (15)
C25	0.053 (3)	0.063 (3)	0.061 (3)	−0.028 (2)	0.013 (2)	−0.002 (2)
C26	0.035 (2)	0.041 (2)	0.065 (2)	−0.0011 (16)	0.0101 (17)	0.0036 (18)
C27	0.040 (2)	0.0389 (19)	0.062 (2)	−0.0039 (17)	0.0110 (18)	0.0106 (17)
C28	0.041 (2)	0.0357 (18)	0.050 (2)	−0.0138 (16)	0.0035 (16)	−0.0006 (16)
C29	0.039 (2)	0.0392 (18)	0.049 (2)	−0.0146 (16)	0.0039 (16)	−0.0053 (16)
C30	0.044 (2)	0.052 (2)	0.071 (3)	−0.0100 (19)	0.0105 (19)	0.004 (2)
C31	0.040 (2)	0.062 (3)	0.088 (3)	−0.012 (2)	0.019 (2)	−0.006 (2)
C32	0.053 (2)	0.060 (2)	0.054 (2)	−0.027 (2)	0.0185 (19)	−0.0132 (19)
C33	0.061 (3)	0.065 (3)	0.052 (2)	−0.021 (2)	0.008 (2)	0.009 (2)
C34	0.044 (2)	0.062 (2)	0.057 (2)	−0.013 (2)	0.0055 (18)	0.007 (2)
F1	0.121 (13)	0.144 (9)	0.075 (7)	−0.086 (9)	0.058 (7)	−0.045 (6)
F2	0.130 (11)	0.067 (5)	0.21 (2)	−0.047 (5)	0.089 (13)	0.011 (7)
F3	0.079 (9)	0.27 (3)	0.108 (8)	−0.115 (15)	−0.001 (5)	0.033 (10)
F1'	0.094 (9)	0.24 (3)	0.065 (6)	−0.092 (13)	0.000 (5)	0.041 (10)
F2'	0.070 (11)	0.064 (5)	0.22 (2)	−0.006 (5)	0.086 (14)	−0.002 (7)
F3'	0.125 (12)	0.092 (10)	0.096 (8)	−0.083 (9)	0.041 (7)	−0.033 (6)
F4	0.084 (2)	0.203 (4)	0.0725 (19)	−0.075 (2)	0.0001 (15)	0.049 (2)
F5	0.0704 (18)	0.092 (2)	0.141 (3)	−0.0208 (16)	0.0594 (18)	−0.0047 (18)
F6	0.103 (2)	0.101 (2)	0.117 (2)	−0.0751 (19)	0.0314 (18)	−0.0192 (18)
N1	0.0321 (17)	0.0346 (16)	0.071 (2)	−0.0026 (14)	0.0191 (15)	0.0052 (15)
N2	0.0403 (18)	0.0466 (18)	0.060 (2)	−0.0195 (15)	0.0138 (15)	−0.0013 (15)
N3	0.0271 (16)	0.0348 (15)	0.0580 (19)	−0.0020 (13)	0.0117 (13)	0.0034 (13)
N4	0.0297 (15)	0.0382 (16)	0.0595 (19)	−0.0077 (13)	0.0106 (14)	0.0010 (14)
O1	0.0393 (15)	0.0442 (14)	0.088 (2)	0.0068 (12)	0.0230 (14)	0.0100 (14)
O2	0.0651 (18)	0.096 (2)	0.0465 (17)	−0.0431 (17)	0.0137 (13)	−0.0143 (15)
O3	0.0264 (13)	0.0410 (13)	0.0690 (17)	−0.0028 (11)	0.0075 (11)	0.0016 (12)
O4	0.0398 (15)	0.0520 (15)	0.0740 (18)	−0.0049 (12)	0.0039 (13)	0.0195 (14)

Geometric parameters (Å, º)

Cl1—C15	1.733 (4)	C18—C19	1.383 (5)
Cl2—C32	1.742 (4)	C18—C24	1.486 (4)
C1—C6	1.383 (5)	C19—C20	1.376 (5)
C1—C2	1.391 (5)	C19—H19	0.9300
C1—C7	1.488 (4)	C20—C21	1.373 (5)
C2—C3	1.368 (5)	C20—H20	0.9300
C2—H2	0.9300	C21—C22	1.388 (5)
C3—C4	1.375 (5)	C21—C25	1.493 (5)
C3—H3	0.9300	C22—C23	1.381 (5)
C4—C5	1.382 (5)	C22—H22	0.9300
C4—C8	1.484 (5)	C23—H23	0.9300
C5—C6	1.374 (5)	C24—O3	1.231 (4)
C5—H5	0.9300	C24—N3	1.345 (4)
C6—H6	0.9300	C25—F4	1.307 (4)
C7—O1	1.220 (4)	C25—F6	1.318 (4)
C7—N1	1.345 (4)	C25—F5	1.327 (4)
C8—F1	1.280 (7)	C26—N4	1.276 (4)
C8—F3	1.300 (7)	C26—C27	1.420 (5)
C8—F3'	1.300 (7)	C26—H26	0.9300
C8—F2'	1.315 (7)	C27—C28	1.355 (5)
C8—F1'	1.319 (7)	C27—H27	0.9300
C8—F2	1.319 (7)	C28—O4	1.333 (4)
C9—N2	1.312 (5)	C28—C29	1.474 (5)
C9—C10	1.359 (5)	C29—C30	1.390 (5)
C9—H9	0.9300	C29—C34	1.394 (5)
C10—C11	1.418 (5)	C30—C31	1.377 (5)
C10—H10	0.9300	C30—H30	0.9300
C11—O2	1.247 (4)	C31—C32	1.374 (6)
C11—C12	1.497 (5)	C31—H31	0.9300
C12—C13	1.378 (5)	C32—C33	1.364 (6)
C12—C17	1.398 (5)	C33—C34	1.375 (5)
C13—C14	1.377 (5)	C33—H33	0.9300
C13—H13	0.9300	C34—H34	0.9300
C14—C15	1.380 (6)	N1—N2	1.385 (4)
C14—H14	0.9300	N1—H1A	0.862 (10)
C15—C16	1.358 (7)	N2—H2A	0.857 (10)
C16—C17	1.379 (5)	N3—N4	1.374 (4)
C16—H16	0.9300	N3—H3A	0.864 (10)
C17—H17	0.9300	N4—H4A	0.860 (10)
C18—C23	1.380 (5)
C6—C1—C2	119.0 (3)	C12—C17—H17	119.7
C6—C1—C7	123.1 (3)	C23—C18—C19	119.6 (3)
C2—C1—C7	117.9 (3)	C23—C18—C24	122.8 (3)
C3—C2—C1	120.4 (3)	C19—C18—C24	117.6 (3)
C3—C2—H2	119.8	C20—C19—C18	120.1 (3)
C1—C2—H2	119.8	C20—C19—H19	119.9
C2—C3—C4	120.4 (3)	C18—C19—H19	119.9
C2—C3—H3	119.8	C21—C20—C19	120.5 (3)
C4—C3—H3	119.8	C21—C20—H20	119.7
C3—C4—C5	119.6 (3)	C19—C20—H20	119.7
C3—C4—C8	119.6 (3)	C20—C21—C22	119.7 (3)
C5—C4—C8	120.8 (3)	C20—C21—C25	121.1 (3)
C6—C5—C4	120.3 (3)	C22—C21—C25	119.2 (3)
C6—C5—H5	119.8	C23—C22—C21	119.8 (3)
C4—C5—H5	119.8	C23—C22—H22	120.1
C5—C6—C1	120.2 (3)	C21—C22—H22	120.1
C5—C6—H6	119.9	C18—C23—C22	120.3 (3)
C1—C6—H6	119.9	C18—C23—H23	119.8
O1—C7—N1	121.7 (3)	C22—C23—H23	119.8
O1—C7—C1	123.2 (3)	O3—C24—N3	121.2 (3)
N1—C7—C1	115.1 (3)	O3—C24—C18	122.4 (3)
F1—C8—F3	105.3 (7)	N3—C24—C18	116.5 (3)
F1—C8—F3'	134.4 (6)	F4—C25—F6	107.2 (4)
F3—C8—F3'	62.0 (6)	F4—C25—F5	106.2 (4)
F1—C8—F2'	64.1 (6)	F6—C25—F5	103.9 (3)
F3—C8—F2'	44.5 (6)	F4—C25—C21	113.7 (3)
F3'—C8—F2'	103.0 (6)	F6—C25—C21	112.6 (3)
F1—C8—F1'	46.4 (6)	F5—C25—C21	112.5 (3)
F3—C8—F1'	131.0 (6)	N4—C26—C27	120.6 (3)
F3'—C8—F1'	106.3 (7)	N4—C26—H26	119.7
F2'—C8—F1'	105.2 (7)	C27—C26—H26	119.7
F1—C8—F2	105.6 (7)	C28—C27—C26	123.4 (3)
F3—C8—F2	106.2 (7)	C28—C27—H27	118.3
F3'—C8—F2	48.6 (6)	C26—C27—H27	118.3
F2'—C8—F2	131.7 (6)	O4—C28—C27	121.0 (3)
F1'—C8—F2	62.1 (6)	O4—C28—C29	114.3 (3)
F1—C8—C4	112.0 (5)	C27—C28—C29	124.8 (3)
F3—C8—C4	113.8 (5)	C30—C29—C34	117.6 (3)
F3'—C8—C4	113.1 (5)	C30—C29—C28	120.2 (3)
F2'—C8—C4	114.0 (5)	C34—C29—C28	122.2 (3)
F1'—C8—C4	114.3 (5)	C31—C30—C29	121.1 (4)
F2—C8—C4	113.3 (5)	C31—C30—H30	119.4
N2—C9—C10	126.6 (4)	C29—C30—H30	119.4
N2—C9—H9	116.7	C32—C31—C30	119.5 (4)
C10—C9—H9	116.7	C32—C31—H31	120.2
C9—C10—C11	122.2 (4)	C30—C31—H31	120.2
C9—C10—H10	118.9	C33—C32—C31	120.9 (3)
C11—C10—H10	118.9	C33—C32—Cl2	119.9 (3)
O2—C11—C10	121.3 (3)	C31—C32—Cl2	119.2 (3)
O2—C11—C12	117.7 (3)	C32—C33—C34	119.6 (4)
C10—C11—C12	121.0 (3)	C32—C33—H33	120.2
C13—C12—C17	118.3 (3)	C34—C33—H33	120.2
C13—C12—C11	119.2 (3)	C33—C34—C29	121.3 (4)
C17—C12—C11	122.4 (4)	C33—C34—H34	119.3
C14—C13—C12	121.5 (4)	C29—C34—H34	119.3
C14—C13—H13	119.3	C7—N1—N2	120.3 (3)
C12—C13—H13	119.3	C7—N1—H1A	122 (2)
C13—C14—C15	118.6 (4)	N2—N1—H1A	117 (2)
C13—C14—H14	120.7	C9—N2—N1	120.8 (4)
C15—C14—H14	120.7	C9—N2—H2A	114 (2)
C16—C15—C14	121.7 (4)	N1—N2—H2A	125 (2)
C16—C15—Cl1	119.9 (4)	C24—N3—N4	118.3 (3)
C14—C15—Cl1	118.5 (4)	C24—N3—H3A	120 (2)
C15—C16—C17	119.4 (4)	N4—N3—H3A	121 (2)
C15—C16—H16	120.3	C26—N4—N3	120.7 (3)
C17—C16—H16	120.3	C26—N4—H4A	112 (2)
C16—C17—C12	120.6 (4)	N3—N4—H4A	127 (2)
C16—C17—H17	119.7
C6—C1—C2—C3	0.2 (6)	C24—C18—C19—C20	−179.2 (3)
C7—C1—C2—C3	179.2 (4)	C18—C19—C20—C21	0.9 (6)
C1—C2—C3—C4	0.0 (6)	C19—C20—C21—C22	−0.2 (6)
C2—C3—C4—C5	0.5 (6)	C19—C20—C21—C25	179.3 (4)
C2—C3—C4—C8	−179.3 (4)	C20—C21—C22—C23	−0.8 (6)
C3—C4—C5—C6	−1.3 (6)	C25—C21—C22—C23	179.7 (3)
C8—C4—C5—C6	178.6 (4)	C19—C18—C23—C22	−0.5 (5)
C4—C5—C6—C1	1.5 (6)	C24—C18—C23—C22	178.2 (3)
C2—C1—C6—C5	−1.0 (6)	C21—C22—C23—C18	1.1 (5)
C7—C1—C6—C5	−180.0 (3)	C23—C18—C24—O3	−146.4 (3)
C6—C1—C7—O1	−144.8 (4)	C19—C18—C24—O3	32.2 (5)
C2—C1—C7—O1	36.2 (5)	C23—C18—C24—N3	34.1 (5)
C6—C1—C7—N1	33.8 (5)	C19—C18—C24—N3	−147.3 (3)
C2—C1—C7—N1	−145.2 (3)	C20—C21—C25—F4	10.5 (6)
C3—C4—C8—F1	75.2 (11)	C22—C21—C25—F4	−170.0 (4)
C5—C4—C8—F1	−104.7 (11)	C20—C21—C25—F6	−111.7 (4)
C3—C4—C8—F3	−165.6 (13)	C22—C21—C25—F6	67.8 (5)
C5—C4—C8—F3	14.6 (14)	C20—C21—C25—F5	131.3 (4)
C3—C4—C8—F3'	−97.3 (12)	C22—C21—C25—F5	−49.2 (5)
C5—C4—C8—F3'	82.8 (12)	N4—C26—C27—C28	−2.0 (6)
C3—C4—C8—F2'	145.5 (13)	C26—C27—C28—O4	−1.9 (6)
C5—C4—C8—F2'	−34.4 (14)	C26—C27—C28—C29	177.1 (4)
C3—C4—C8—F1'	24.5 (15)	O4—C28—C29—C30	−7.6 (5)
C5—C4—C8—F1'	−155.4 (14)	C27—C28—C29—C30	173.3 (4)
C3—C4—C8—F2	−44.1 (14)	O4—C28—C29—C34	172.5 (3)
C5—C4—C8—F2	136.0 (14)	C27—C28—C29—C34	−6.5 (6)
N2—C9—C10—C11	2.6 (6)	C34—C29—C30—C31	0.5 (6)
C9—C10—C11—O2	3.0 (5)	C28—C29—C30—C31	−179.4 (4)
C9—C10—C11—C12	−178.1 (3)	C29—C30—C31—C32	0.6 (7)
O2—C11—C12—C13	4.4 (5)	C30—C31—C32—C33	−1.5 (7)
C10—C11—C12—C13	−174.6 (3)	C30—C31—C32—Cl2	177.3 (3)
O2—C11—C12—C17	−174.0 (3)	C31—C32—C33—C34	1.2 (6)
C10—C11—C12—C17	7.0 (5)	Cl2—C32—C33—C34	−177.5 (3)
C17—C12—C13—C14	−0.5 (5)	C32—C33—C34—C29	−0.1 (7)
C11—C12—C13—C14	−179.0 (3)	C30—C29—C34—C33	−0.8 (6)
C12—C13—C14—C15	−0.6 (6)	C28—C29—C34—C33	179.1 (4)
C13—C14—C15—C16	0.8 (6)	O1—C7—N1—N2	−2.3 (6)
C13—C14—C15—Cl1	−178.8 (3)	C1—C7—N1—N2	179.1 (3)
C14—C15—C16—C17	0.1 (7)	C10—C9—N2—N1	−175.3 (3)
Cl1—C15—C16—C17	179.7 (3)	C7—N1—N2—C9	79.9 (5)
C15—C16—C17—C12	−1.2 (6)	O3—C24—N3—N4	2.0 (5)
C13—C12—C17—C16	1.4 (5)	C18—C24—N3—N4	−178.5 (3)
C11—C12—C17—C16	179.9 (4)	C27—C26—N4—N3	−177.2 (4)
C23—C18—C19—C20	−0.6 (5)	C24—N3—N4—C26	176.8 (3)

Hydrogen-bond geometry (Å, º)

D—H···A	D—H	H···A	D···A	D—H···A
N1—H1A···O3^i	0.86 (3)	1.98 (3)	2.817 (4)	165 (2)
N2—H2A···O2	0.86 (3)	1.99 (3)	2.663 (5)	135 (3)
N3—H3A···O1^ii	0.86 (2)	2.03 (2)	2.844 (4)	158 (2)
N4—H4A···O4	0.86 (2)	1.81 (2)	2.560 (4)	145 (3)
C2—H2···F3^iii	0.93	2.42	3.218 (1)	142
C22—H22···O3^i	0.93	2.53	3.398 (5)	156
C9—H9···Cg2^iv	0.93	2.99	3.69	132
C31—H31···Cg1^iii	0.93	2.95	3.68	137

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