2-(4-Chloro­phen­yl)-N-{3-cyano-1-[2,6-dichloro-4-(trifluoro­meth­yl)phen­yl]-1H-pyrazol-5-yl}-3-methyl­butanamide ethanol solvate

In the title compound, C₂₂H₁₆Cl₃F₃N₄O·C₂H₆O, the asymmetric unit consists of one mol­ecule of C₂₂H₁₆Cl₃F₃N₄O and one ethanol solvent mol­ecule which are connected through an N—H...O hydrogen bond. The H atom of the hydroxyl group of the solvent mol­ecule is hydrogen bonded to the N atom of the cyano group. These hydrogen-bond inter­actions result in the formation of zigzag chains parallel to the a axis.

Key indicators

• Single-crystal X-ray study
• T = 243 K
• Mean [sigma](C-C) = 0.004 Å
• Disorder in main residue
• R factor = 0.053
• wR factor = 0.188
• Data-to-parameter ratio = 16.7

checkCIF/PLATON results

No syntax errors found



Alert level C
PLAT029_ALERT_3_C _diffrn_measured_fraction_theta_full Low .......       0.97
PLAT213_ALERT_2_C Atom F21     has ADP max/min Ratio .............       3.30 prolat
PLAT213_ALERT_2_C Atom F12     has ADP max/min Ratio .............       3.80 prolat
PLAT213_ALERT_2_C Atom F32     has ADP max/min Ratio .............       3.90 prolat
PLAT220_ALERT_2_C Large Non-Solvent    C     Ueq(max)/Ueq(min) ...       2.83 Ratio
PLAT242_ALERT_2_C Check Low       Ueq as Compared to Neighbors for        C10
PLAT242_ALERT_2_C Check Low       Ueq as Compared to Neighbors for        C13
PLAT301_ALERT_3_C Main Residue  Disorder .........................       8.00 Perc.
PLAT371_ALERT_2_C Long   C(sp2)-C(sp1) Bond  C5     -   C6     ...       1.43 Ang.
PLAT432_ALERT_2_C Short Inter X...Y Contact  C24    ..  F12     ..       2.94 Ang.
PLAT764_ALERT_4_C Overcomplete CIF Bond List Detected (Rep/Expd) .       1.15 Ratio
PLAT779_ALERT_2_C Suspect or Irrelevant (Bond) Angle in CIF ......      43.40 Deg.
              F21  -C13  -F22     1.555   1.555   1.555
PLAT779_ALERT_2_C Suspect or Irrelevant (Bond) Angle in CIF ......      35.30 Deg.
              F31  -C13  -F32     1.555   1.555   1.555

   0 ALERT level A = In general: serious problem
   0 ALERT level B = Potentially serious problem
  13 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
  10 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
   1 ALERT type 4 Improvement, methodology, query or suggestion

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Computing details

Data collection: PROCESS-AUTO (Rigaku, 1998); cell refinement: PROCESS-AUTO (Rigaku, 1998); data reduction: CrystalStructure (Rigaku/MSC & Rigaku, 2004); program(s) used to solve structure: SIR97 (Altomare et al., 1993); program(s) used to refine structure: CRYSTALS (Betteridge et al., 2003); molecular graphics: ORTEP-3 for Windows (Farrugia,1997); PLATON (Spek, 2003); software used to prepare material for publication: CrystalStructure (Rigaku/MSC & Rigaku, 2004).

2-(4-chlorophenyl)-N-{3-cyano-1-[2,6-dichloro-4- (trifluoromethyl)phenyl]-1H-pyrazol-5-yl}-3-methylbutanamide ethanol solvate

Crystal data

C22H16Cl3F3N4O·C2H6O	Z = 2
Mr = 561.82	F(000) = 576.00
Triclinic, P1	Dx = 1.416 Mg m^−3
Hall symbol: -P 1	Mo Kα radiation, λ = 0.71075 Å
a = 10.139 (4) Å	Cell parameters from 10553 reflections
b = 10.652 (5) Å	θ = 3.1–27.6°
c = 12.827 (7) Å	µ = 0.40 mm^−1
α = 73.255 (18)°	T = 243 K
β = 83.517 (19)°	Chunk, colorless
γ = 89.185 (15)°	0.33 × 0.28 × 0.27 mm
V = 1317.9 (11) Å^3

Data collection

Rigaku RAXIS-RAPID diffractometer	4011 reflections with F^2 > 2.0σ(F^2)
Detector resolution: 10.00 pixels mm^-1	Rint = 0.026
ω scans	θmax = 27.5°
Absorption correction: multi-scan ABSCOR (Higashi, 1995)	h = −12→13
Tmin = 0.874, Tmax = 0.898	k = −13→13
12934 measured reflections	l = −16→16
5889 independent reflections

Refinement

Refinement on F^2	w = 1/[0.0038Fo^2 + 1.0000σ(Fo^2)]/(4Fo^2)
R[F^2 > 2σ(F^2)] = 0.053	(Δ/σ)max < 0.001
wR(F^2) = 0.188	Δρmax = 0.68 e Å^−3
S = 1.01	Δρmin = −0.39 e Å^−3
5889 reflections	Extinction correction: Larson (1970) eq. 22
353 parameters	Extinction coefficient: 53 (31)
H-atom parameters constrained

Special details

Refinement. Refinement using all reflections. The weighted R-factor (wR) and goodness of fit (S) are based on F². R-factor (gt) are based on F. The threshold expression of F² > 2.0 σ(F²) is used only for calculating R-factor (gt).

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

	x	y	z	Uiso*/Ueq	Occ. (<1)
Cl1	0.65691 (6)	0.46618 (6)	0.60751 (6)	0.04682 (18)
Cl2	0.31046 (6)	0.86043 (6)	0.58592 (6)	0.0556 (2)
Cl3	1.08516 (12)	0.75635 (12)	0.32400 (9)	0.0927 (3)
F11	0.5542 (5)	0.9117 (12)	0.1961 (4)	0.126 (2)	0.60
F12	0.6007 (15)	0.7985 (14)	0.1939 (6)	0.143 (3)	0.40
F21	0.7049 (15)	0.7780 (5)	0.2077 (6)	0.131 (3)	0.60
F22	0.7795 (7)	0.8136 (12)	0.2341 (7)	0.119 (3)	0.40
F31	0.7303 (7)	0.9478 (6)	0.2456 (5)	0.119 (2)	0.60
F32	0.663 (2)	0.9720 (9)	0.2304 (11)	0.158 (7)	0.40
O1	0.59450 (19)	0.8346 (2)	0.71835 (19)	0.0559 (5)
O2	0.7557 (2)	0.3988 (2)	0.9094 (2)	0.0638 (6)
N1	0.60967 (19)	0.6159 (2)	0.79787 (18)	0.0411 (5)
N2	0.0421 (2)	0.4153 (3)	0.8966 (2)	0.0749 (9)
N3	0.30053 (18)	0.5610 (2)	0.70663 (18)	0.0403 (5)
N4	0.42740 (18)	0.60374 (19)	0.69319 (16)	0.0343 (4)
C1	0.8094 (2)	0.7483 (2)	0.7663 (2)	0.0445 (6)
C2	0.6607 (2)	0.7415 (2)	0.7591 (2)	0.0418 (6)
C3	0.4789 (2)	0.5846 (2)	0.7910 (2)	0.0376 (6)
C4	0.3814 (2)	0.5212 (2)	0.8707 (2)	0.0454 (6)
C5	0.2747 (2)	0.5115 (2)	0.8145 (2)	0.0436 (6)
C6	0.1454 (2)	0.4570 (2)	0.8600 (2)	0.0505 (7)
C7	0.4875 (2)	0.6694 (2)	0.5859 (2)	0.0364 (5)
C8	0.5944 (2)	0.6147 (2)	0.5371 (2)	0.0374 (6)
C9	0.6488 (2)	0.6748 (2)	0.4315 (2)	0.0427 (6)
C10	0.5959 (2)	0.7905 (2)	0.3736 (2)	0.0464 (7)
C11	0.4913 (2)	0.8490 (2)	0.4204 (2)	0.0469 (7)
C12	0.4384 (2)	0.7874 (2)	0.5262 (2)	0.0414 (6)
C13	0.6503 (3)	0.8537 (3)	0.2561 (2)	0.103 (10)
C14	0.8453 (3)	0.8655 (2)	0.8070 (2)	0.0548 (8)
C15	0.9921 (3)	0.8622 (4)	0.8205 (3)	0.0738 (11)
C16	0.7614 (3)	0.8620 (4)	0.9134 (3)	0.0770 (12)
C17	0.8803 (2)	0.7533 (2)	0.6553 (2)	0.0441 (6)
C18	0.9586 (2)	0.6502 (3)	0.6419 (2)	0.0602 (8)
C19	1.0228 (3)	0.6506 (3)	0.5421 (2)	0.0636 (9)
C20	1.0063 (2)	0.7552 (3)	0.4521 (2)	0.0546 (8)
C21	0.9291 (3)	0.8582 (2)	0.4618 (2)	0.0540 (8)
C22	0.8663 (2)	0.8564 (2)	0.5630 (2)	0.0547 (8)
C23	0.7399 (8)	0.2580 (4)	0.9667 (11)	0.101 (3)
C24	0.6004 (11)	0.2233 (13)	0.9485 (18)	0.146 (5)
H1	0.8332	0.6699	0.8176	0.053*
H4	0.3858	0.4908	0.9475	0.054*
H9	0.7219	0.6372	0.3989	0.051*
H11	0.4570	0.9297	0.3803	0.056*
H14	0.8283	0.9445	0.7532	0.066*
H18	0.9680	0.5772	0.7038	0.072*
H19	1.0779	0.5800	0.5350	0.076*
H21	0.9189	0.9302	0.3994	0.065*
H22	0.8119	0.9277	0.5697	0.066*
H151	1.0154	0.9357	0.8430	0.089*
H152	1.0423	0.8651	0.7527	0.089*
H153	1.0106	0.7838	0.8744	0.089*
H161	0.7905	0.9297	0.9405	0.092*
H162	0.7702	0.7794	0.9657	0.092*
H163	0.6710	0.8745	0.9006	0.092*
H231	0.7475	0.2412	1.0442	0.121*
H232	0.8059	0.2081	0.9355	0.121*
H241	0.5378	0.2349	1.0068	0.175*
H242	0.5784	0.2795	0.8798	0.175*
H243	0.5973	0.1336	0.9475	0.175*
H101	0.6637	0.5529	0.8233	0.048*
H201	0.8386	0.4064	0.9116	0.071*

Atomic displacement parameters (Ų)

	U^11	U^22	U^33	U^12	U^13	U^23
Cl1	0.0430 (3)	0.0477 (3)	0.0515 (4)	0.0129 (2)	−0.0068 (2)	−0.0170 (2)
Cl2	0.0516 (4)	0.0482 (3)	0.0603 (4)	0.0174 (2)	0.0005 (3)	−0.0086 (3)
Cl3	0.1048 (7)	0.0950 (7)	0.0645 (6)	0.0377 (5)	0.0149 (5)	−0.0119 (5)
F11	0.122 (3)	0.179 (7)	0.046 (2)	−0.018 (4)	−0.020 (2)	0.022 (4)
F12	0.168 (8)	0.232 (11)	0.030 (2)	−0.122 (8)	0.022 (4)	−0.046 (4)
F21	0.265 (11)	0.046 (2)	0.067 (4)	−0.033 (5)	0.080 (7)	−0.030 (2)
F22	0.111 (4)	0.142 (11)	0.083 (4)	−0.008 (5)	0.043 (3)	−0.018 (5)
F31	0.148 (4)	0.137 (4)	0.057 (2)	−0.102 (4)	0.021 (3)	−0.013 (3)
F32	0.34 (2)	0.030 (4)	0.072 (9)	−0.016 (10)	0.102 (13)	−0.008 (4)
O1	0.0461 (10)	0.0512 (11)	0.0685 (14)	0.0062 (8)	−0.0149 (9)	−0.0115 (10)
O2	0.0443 (10)	0.0537 (11)	0.0791 (16)	−0.0026 (9)	−0.0004 (10)	0.0010 (11)
N1	0.0321 (9)	0.0486 (11)	0.0396 (11)	0.0024 (8)	−0.0064 (8)	−0.0075 (9)
N2	0.0430 (13)	0.098 (2)	0.0620 (18)	−0.0073 (13)	0.0044 (12)	0.0072 (16)
N3	0.0295 (9)	0.0470 (11)	0.0399 (12)	0.0026 (8)	−0.0018 (8)	−0.0063 (9)
N4	0.0291 (8)	0.0388 (10)	0.0336 (10)	0.0030 (7)	−0.0021 (7)	−0.0088 (8)
C1	0.0403 (12)	0.0425 (13)	0.0479 (15)	−0.0018 (10)	−0.0110 (11)	−0.0059 (11)
C2	0.0411 (12)	0.0441 (13)	0.0414 (14)	0.0014 (10)	−0.0065 (10)	−0.0139 (11)
C3	0.0337 (10)	0.0438 (12)	0.0348 (13)	0.0054 (9)	−0.0039 (9)	−0.0107 (10)
C4	0.0419 (12)	0.0566 (15)	0.0338 (13)	0.0022 (11)	−0.0026 (10)	−0.0078 (11)
C5	0.0320 (11)	0.0534 (14)	0.0394 (14)	0.0038 (10)	0.0011 (9)	−0.0058 (11)
C6	0.0410 (13)	0.0565 (16)	0.0458 (16)	−0.0012 (12)	−0.0006 (11)	−0.0033 (12)
C7	0.0329 (10)	0.0437 (12)	0.0310 (12)	0.0006 (9)	−0.0019 (9)	−0.0090 (10)
C8	0.0347 (11)	0.0397 (11)	0.0404 (13)	0.0003 (9)	−0.0039 (9)	−0.0159 (10)
C9	0.0463 (13)	0.0439 (13)	0.0421 (14)	−0.0071 (11)	0.0036 (10)	−0.0217 (11)
C10	0.0600 (15)	0.0429 (13)	0.0365 (14)	−0.0146 (11)	0.0009 (11)	−0.0134 (11)
C11	0.0549 (14)	0.0426 (13)	0.0394 (14)	−0.0027 (11)	−0.0065 (11)	−0.0050 (11)
C12	0.0371 (11)	0.0459 (13)	0.0386 (14)	0.0026 (10)	−0.0027 (10)	−0.0087 (11)
C13	0.068 (5)	0.108 (8)	0.113 (9)	−0.008 (4)	−0.017 (5)	0.003 (7)
C14	0.0624 (16)	0.0485 (15)	0.0547 (18)	−0.0095 (13)	−0.0158 (13)	−0.0130 (13)
C15	0.0644 (19)	0.089 (2)	0.064 (2)	−0.0247 (18)	−0.0227 (17)	−0.0100 (19)
C16	0.080 (2)	0.095 (2)	0.063 (2)	−0.009 (2)	−0.0095 (18)	−0.032 (2)
C17	0.0328 (11)	0.0461 (13)	0.0492 (15)	−0.0013 (10)	−0.0104 (10)	−0.0048 (11)
C18	0.0515 (15)	0.0591 (17)	0.0565 (18)	0.0136 (13)	−0.0063 (13)	0.0041 (14)
C19	0.0601 (17)	0.0493 (16)	0.075 (2)	0.0195 (14)	−0.0018 (15)	−0.0104 (15)
C20	0.0472 (14)	0.0593 (16)	0.0527 (17)	0.0072 (13)	−0.0008 (12)	−0.0107 (13)
C21	0.0632 (17)	0.0429 (14)	0.0492 (17)	0.0098 (12)	−0.0065 (13)	−0.0032 (12)
C22	0.0540 (16)	0.0520 (15)	0.0533 (18)	0.0165 (12)	−0.0077 (13)	−0.0074 (13)
C23	0.066 (5)	0.107 (8)	0.111 (9)	−0.009 (4)	−0.015 (5)	0.001 (7)
C24	0.100 (7)	0.091 (7)	0.227 (19)	−0.027 (6)	−0.064 (9)	0.004 (10)

Geometric parameters (Å, º)

Cl1—C8	1.731 (2)	C10—C11	1.388 (4)
Cl2—C12	1.722 (2)	C10—C13	1.506 (3)
Cl3—C20	1.741 (3)	C11—C12	1.375 (3)
F11—F12	1.30 (2)	C14—C15	1.517 (4)
F11—F32	1.45 (2)	C14—C16	1.515 (5)
F11—C13	1.342 (7)	C17—C18	1.385 (4)
F12—F21	1.10 (2)	C17—C22	1.382 (3)
F12—C13	1.267 (14)	C18—C19	1.368 (5)
F21—F22	0.985 (17)	C19—C20	1.379 (4)
F21—C13	1.240 (9)	C20—C21	1.365 (4)
F22—F31	1.549 (15)	C21—C22	1.376 (4)
F22—C13	1.395 (9)	C23—C24	1.526 (16)
F31—F32	0.75 (2)	O2—H201	0.850
F31—C13	1.266 (8)	N1—H101	0.873
F32—C13	1.212 (10)	C1—H1	0.950
O1—C2	1.212 (3)	C4—H4	0.950
O2—C23	1.470 (5)	C9—H9	0.950
N1—C2	1.372 (3)	C11—H11	0.950
N1—C3	1.390 (3)	C14—H14	0.950
N2—C6	1.139 (3)	C15—H151	0.960
N3—N4	1.346 (2)	C15—H152	0.960
N3—C5	1.328 (3)	C15—H153	0.960
N4—C3	1.373 (3)	C16—H161	0.960
N4—C7	1.422 (2)	C16—H162	0.960
C1—C2	1.524 (3)	C16—H163	0.960
C1—C14	1.548 (4)	C18—H18	0.950
C1—C17	1.508 (4)	C19—H19	0.950
C3—C4	1.368 (3)	C21—H21	0.950
C4—C5	1.388 (3)	C22—H22	0.950
C5—C6	1.431 (3)	C23—H232	0.970
C7—C8	1.395 (3)	C23—H231	0.970
C7—C12	1.388 (3)	C24—H241	0.960
C8—C9	1.375 (3)	C24—H243	0.960
C9—C10	1.380 (3)	C24—H242	0.960
Cl1···Cl3	3.5174 (13)	H231···C5	3.595
Cl1···C8	3.567 (2)	H231···C15	3.324
Cl2···F31	3.366 (7)	H231···H4	3.166
Cl2···F32	3.375 (15)	H231···H151	3.242
Cl3···Cl1	3.5174 (13)	H231···H152	3.479
F11···O1	3.465 (12)	H231···H153	2.753
F11···C24	3.20 (2)	H4···O2	2.723
F12···C5	3.545 (15)	H4···N1	3.139
F12···C24	2.94 (2)	H4···C4	3.476
F21···N3	3.458 (5)	H4···C23	3.360
F21···C5	3.179 (7)	H4···C24	3.558
F21···C6	3.189 (9)	H4···H1	3.545
F22···C6	3.476 (13)	H4···H231	3.166
F31···Cl2	3.366 (7)	H4···H4	2.843
F31···C15	3.372 (8)	H4···H241	3.055
F32···Cl2	3.375 (15)	H4···H241	3.261
F32···O1	3.43 (2)	H4···H242	3.201
O1···F11	3.465 (12)	H4···H101	2.828
O1···F32	3.43 (2)	H4···H162	3.148
O1···C11	3.478 (3)	H4···H201	3.128
O2···N1	2.839 (2)	H241···F12	3.176
O2···N2	2.895 (3)	H241···O1	3.497
O2···C4	3.329 (3)	H241···N1	3.524
N1···O2	2.839 (2)	H241···C2	3.491
N2···O2	2.895 (3)	H241···C4	3.505
N2···C23	3.415 (7)	H241···C4	3.547
N3···F21	3.458 (5)	H241···C16	3.177
N3···C9	3.470 (4)	H241···H4	3.055
C4···O2	3.329 (3)	H241···H4	3.261
C5···F12	3.545 (15)	H241···H162	3.104
C5···F21	3.179 (7)	H241···H163	2.441
C6···F21	3.189 (9)	H243···F11	3.364
C6···F22	3.476 (13)	H243···F11	2.676
C8···Cl1	3.567 (2)	H243···F12	2.805
C8···C8	3.525 (3)	H243···C16	3.430
C9···N3	3.470 (4)	H243···H243	3.341
C11···O1	3.478 (3)	H243···H161	2.918
C15···F31	3.372 (8)	H243···H163	3.055
C23···N2	3.415 (7)	H243···H163	3.148
C24···F11	3.20 (2)	H242···Cl1	3.493
C24···F12	2.94 (2)	H242···F11	2.902
Cl1···H242	3.493	H242···F12	2.401
Cl1···H19	3.191	H242···F21	3.326
Cl2···H11	3.418	H242···N1	3.440
Cl2···H21	3.227	H242···C3	3.303
Cl2···H22	2.916	H242···C4	3.220
Cl2···H152	3.273	H242···C13	3.586
Cl3···H232	3.301	H242···H4	3.201
Cl3···H14	3.158	H242···H101	2.910
Cl3···H151	3.569	H242···H163	3.587
F11···H243	3.364	H9···N3	2.842
F11···H243	2.676	H9···N4	3.541
F11···H242	2.902	H9···C5	3.533
F11···H163	3.287	H9···H19	3.052
F12···H241	3.176	H11···Cl2	3.418
F12···H243	2.805	H11···O1	2.541
F12···H242	2.401	H11···H14	3.574
F12···H161	3.502	H11···H22	3.194
F12···H162	3.280	H14···Cl3	3.158
F21···H242	3.326	H14···H11	3.574
F21···H161	3.360	H14···H21	3.105
F21···H162	3.096	H18···O2	3.338
F22···H151	3.256	H18···N2	2.753
F22···H161	3.599	H18···N3	3.378
F22···H162	3.577	H18···C5	3.541
F31···H231	3.425	H18···C6	2.856
F31···H151	2.845	H18···H201	2.936
F31···H152	3.074	H19···Cl1	3.191
F32···H231	3.213	H19···N3	3.292
F32···H151	3.369	H19···C19	3.123
F32···H152	3.535	H19···H9	3.052
O1···H241	3.497	H19···H19	2.735
O1···H11	2.541	H21···Cl2	3.227
O2···H1	2.870	H21···C14	3.586
O2···H4	2.723	H21···C15	3.090
O2···H18	3.338	H21···C22	3.339
O2···H101	1.982	H21···H14	3.105
N1···H4	3.139	H21···H22	3.256
N1···H241	3.524	H21···H151	3.025
N1···H242	3.440	H21···H152	2.472
N1···H201	3.352	H22···Cl2	2.916
N2···H1	3.407	H22···C21	3.414
N2···H232	3.179	H22···H11	3.194
N2···H231	3.578	H22···H21	3.256
N2···H18	2.753	H101···O2	1.982
N2···H153	3.082	H101···C23	3.282
N2···H162	3.095	H101···C24	3.450
N2···H201	2.051	H101···H4	2.828
N3···H9	2.842	H101···H242	2.910
N3···H18	3.378	H101···H201	2.493
N3···H19	3.292	H151···Cl3	3.569
N4···H9	3.541	H151···F22	3.256
C2···H241	3.491	H151···F31	2.845
C3···H242	3.303	H151···F32	3.369
C4···H231	3.237	H151···H232	3.504
C4···H4	3.476	H151···H231	3.242
C4···H241	3.505	H151···H21	3.025
C4···H241	3.547	H152···Cl2	3.273
C4···H242	3.220	H152···F31	3.074
C4···H162	3.544	H152···F32	3.535
C5···H231	3.595	H152···C21	3.392
C5···H9	3.533	H152···H231	3.479
C5···H18	3.541	H152···H21	2.472
C5···H162	3.532	H153···N2	3.082
C6···H18	2.856	H153···C23	3.372
C6···H162	3.034	H153···H232	3.251
C6···H201	3.128	H153···H231	2.753
C13···H242	3.586	H153···H201	3.411
C14···H21	3.586	H161···F12	3.502
C15···H231	3.324	H161···F21	3.360
C15···H21	3.090	H161···F22	3.599
C16···H241	3.177	H161···H232	2.953
C16···H243	3.430	H161···H243	2.918
C19···H19	3.123	H162···F12	3.280
C21···H22	3.414	H162···F21	3.096
C21···H152	3.392	H162···F22	3.577
C22···H21	3.339	H162···N2	3.095
C23···H4	3.360	H162···C4	3.544
C23···H101	3.282	H162···C5	3.532
C23···H153	3.372	H162···C6	3.034
C24···H4	3.558	H162···H4	3.148
C24···H101	3.450	H162···H241	3.104
C24···H163	3.181	H163···F11	3.287
H1···O2	2.870	H163···C24	3.181
H1···N2	3.407	H163···H241	2.441
H1···H4	3.545	H163···H243	3.055
H1···H201	2.719	H163···H243	3.148
H232···Cl3	3.301	H163···H242	3.587
H232···N2	3.179	H201···N1	3.352
H232···H151	3.504	H201···N2	2.051
H232···H153	3.251	H201···C6	3.128
H232···H161	2.953	H201···H1	2.719
H231···F31	3.425	H201···H4	3.128
H231···F32	3.213	H201···H18	2.936
H231···N2	3.578	H201···H101	2.493
H231···C4	3.237	H201···H153	3.411
F12—F11—F32	102.9 (10)	F22—C13—F31	71.0 (6)
F12—F11—C13	57.4 (7)	F22—C13—F32	102.6 (13)
F32—F11—C13	51.2 (5)	F22—C13—C10	111.2 (4)
F11—F12—F21	118.6 (13)	F31—C13—F32	35.3 (13)
F11—F12—C13	63.2 (7)	F31—C13—C10	112.6 (4)
F21—F12—C13	62.8 (8)	F32—C13—C10	115.0 (7)
F12—F21—F22	140.3 (13)	C1—C14—C15	109.1 (2)
F12—F21—C13	65.2 (9)	C1—C14—C16	110.8 (2)
F22—F21—C13	76.7 (8)	C15—C14—C16	111.2 (3)
F21—F22—F31	104.3 (9)	C1—C17—C18	120.2 (2)
F21—F22—C13	59.9 (7)	C1—C17—C22	122.2 (2)
F31—F22—C13	50.6 (5)	C18—C17—C22	117.5 (2)
F22—F31—F32	120.7 (13)	C17—C18—C19	121.8 (2)
F22—F31—C13	58.4 (4)	C18—C19—C20	118.9 (3)
F32—F31—C13	68.5 (11)	Cl3—C20—C19	119.6 (2)
F11—F32—F31	132.3 (14)	Cl3—C20—C21	119.4 (2)
F11—F32—C13	59.6 (9)	C19—C20—C21	121.0 (3)
F31—F32—C13	76.3 (10)	C20—C21—C22	119.2 (2)
C2—N1—C3	122.8 (2)	C17—C22—C21	121.6 (2)
N4—N3—C5	103.4 (2)	O2—C23—C24	104.2 (7)
N3—N4—C3	112.55 (18)	C23—O2—H201	98.3
N3—N4—C7	119.0 (2)	C2—N1—H101	117.9
C3—N4—C7	128.25 (19)	C3—N1—H101	119.1
C2—C1—C14	111.2 (2)	C2—C1—H1	108.2
C2—C1—C17	107.6 (2)	C14—C1—H1	108.2
C14—C1—C17	113.3 (2)	C17—C1—H1	108.2
O1—C2—N1	122.6 (2)	C3—C4—H4	127.7
O1—C2—C1	124.6 (2)	C5—C4—H4	127.7
N1—C2—C1	112.7 (2)	C8—C9—H9	120.4
N1—C3—N4	123.1 (2)	C10—C9—H9	120.4
N1—C3—C4	130.6 (2)	C10—C11—H11	120.7
N4—C3—C4	106.0 (2)	C12—C11—H11	120.7
C3—C4—C5	104.6 (2)	C1—C14—H14	108.6
N3—C5—C4	113.4 (2)	C15—C14—H14	108.6
N3—C5—C6	119.2 (2)	C16—C14—H14	108.6
C4—C5—C6	127.4 (2)	C14—C15—H151	109.5
N2—C6—C5	179.0 (3)	C14—C15—H152	109.5
N4—C7—C8	120.7 (2)	C14—C15—H153	109.5
N4—C7—C12	120.7 (2)	H151—C15—H152	109.5
C8—C7—C12	118.6 (2)	H151—C15—H153	109.5
Cl1—C8—C7	120.16 (17)	H152—C15—H153	109.5
Cl1—C8—C9	118.91 (19)	C14—C16—H161	109.5
C7—C8—C9	120.9 (2)	C14—C16—H162	109.5
C8—C9—C10	119.1 (2)	C14—C16—H163	109.5
C9—C10—C11	121.5 (2)	H161—C16—H162	109.5
C9—C10—C13	119.5 (2)	H161—C16—H163	109.5
C11—C10—C13	119.0 (2)	H162—C16—H163	109.5
C10—C11—C12	118.5 (2)	C17—C18—H18	119.1
Cl2—C12—C7	119.64 (18)	C19—C18—H18	119.1
Cl2—C12—C11	118.9 (2)	C18—C19—H19	120.5
C7—C12—C11	121.4 (2)	C20—C19—H19	120.5
F11—C13—F12	59.5 (8)	C20—C21—H21	120.4
F11—C13—F21	105.9 (7)	C22—C21—H21	120.4
F11—C13—F22	135.9 (5)	C17—C22—H22	119.2
F11—C13—F31	102.8 (6)	C21—C22—H22	119.2
F11—C13—F32	69.2 (13)	O2—C23—H232	110.8
F11—C13—C10	111.3 (3)	O2—C23—H231	110.8
F12—C13—F21	52.0 (9)	C24—C23—H232	110.8
F12—C13—F22	94.8 (8)	C24—C23—H231	110.8
F12—C13—F31	137.3 (6)	H232—C23—H231	109.5
F12—C13—F32	120.5 (10)	C23—C24—H241	109.5
F12—C13—C10	110.1 (5)	C23—C24—H243	109.5
F21—C13—F22	43.4 (8)	C23—C24—H242	109.5
F21—C13—F31	108.2 (7)	H241—C24—H243	109.5
F21—C13—F32	127.3 (10)	H241—C24—H242	109.5
F21—C13—C10	115.2 (3)	H243—C24—H242	109.5
F12—F11—F32—F31	−1.6 (19)	F31—F32—C13—F12	−130.0 (12)
F12—F11—F32—C13	−26.6 (8)	F31—F32—C13—F21	−66.7 (17)
F32—F11—F12—F21	−6.2 (11)	F31—F32—C13—F22	−26.6 (13)
F32—F11—F12—C13	24.5 (7)	F31—F32—C13—C10	94.2 (13)
F12—F11—C13—F21	24.4 (8)	C2—N1—C3—N4	62.2 (3)
F12—F11—C13—F22	62.0 (12)	C2—N1—C3—C4	−124.5 (3)
F12—F11—C13—F31	137.8 (7)	C3—N1—C2—O1	1.8 (4)
F12—F11—C13—F32	148.8 (11)	C3—N1—C2—C1	−174.5 (2)
F12—F11—C13—C10	−101.5 (6)	N4—N3—C5—C4	0.0 (2)
C13—F11—F12—F21	−30.6 (7)	N4—N3—C5—C6	179.3 (2)
F32—F11—C13—F12	−148.8 (11)	C5—N3—N4—C3	−1.6 (2)
F32—F11—C13—F21	−124.4 (10)	C5—N3—N4—C7	−177.1 (2)
F32—F11—C13—F22	−86.7 (14)	N3—N4—C3—N1	177.3 (2)
F32—F11—C13—F31	−11.0 (9)	N3—N4—C3—C4	2.6 (3)
F32—F11—C13—C10	109.7 (9)	N3—N4—C7—C8	−115.3 (2)
C13—F11—F32—F31	25.0 (16)	N3—N4—C7—C12	62.7 (3)
F11—F12—F21—F22	13.1 (18)	C3—N4—C7—C8	70.0 (3)
F11—F12—F21—C13	30.8 (6)	C3—N4—C7—C12	−111.9 (3)
F11—F12—C13—F21	−149.8 (7)	C7—N4—C3—N1	−7.7 (4)
F11—F12—C13—F22	−141.9 (6)	C7—N4—C3—C4	177.6 (2)
F11—F12—C13—F31	−74.9 (11)	C2—C1—C14—C15	176.0 (2)
F11—F12—C13—F32	−34.2 (15)	C2—C1—C14—C16	53.2 (3)
F11—F12—C13—C10	103.4 (4)	C14—C1—C2—O1	46.2 (3)
F21—F12—C13—F11	149.8 (7)	C14—C1—C2—N1	−137.7 (2)
F21—F12—C13—F22	7.9 (6)	C2—C1—C17—C18	−113.8 (2)
F21—F12—C13—F31	74.9 (11)	C2—C1—C17—C22	63.5 (3)
F21—F12—C13—F32	115.6 (15)	C17—C1—C2—O1	−78.4 (3)
F21—F12—C13—C10	−106.8 (5)	C17—C1—C2—N1	97.7 (2)
C13—F12—F21—F22	−17.7 (14)	C14—C1—C17—C18	122.9 (3)
F12—F21—F22—F31	−8.7 (17)	C14—C1—C17—C22	−59.8 (3)
F12—F21—F22—C13	16.5 (13)	C17—C1—C14—C15	−62.7 (3)
F12—F21—C13—F11	−26.8 (8)	C17—C1—C14—C16	174.5 (2)
F12—F21—C13—F22	−168.5 (9)	N1—C3—C4—C5	−176.5 (2)
F12—F21—C13—F31	−136.4 (7)	N4—C3—C4—C5	−2.4 (3)
F12—F21—C13—F32	−102.5 (17)	C3—C4—C5—N3	1.5 (3)
F12—F21—C13—C10	96.6 (7)	C3—C4—C5—C6	−177.7 (3)
F22—F21—C13—F11	141.7 (7)	N4—C7—C8—Cl1	−0.7 (3)
F22—F21—C13—F12	168.5 (9)	N4—C7—C8—C9	177.0 (2)
F22—F21—C13—F31	32.1 (7)	N4—C7—C12—Cl2	4.3 (3)
F22—F21—C13—F32	66.0 (17)	N4—C7—C12—C11	−176.9 (2)
F22—F21—C13—C10	−94.9 (7)	C8—C7—C12—Cl2	−177.6 (2)
C13—F21—F22—F31	−25.2 (5)	C8—C7—C12—C11	1.2 (4)
F21—F22—F31—F32	−1.6 (17)	C12—C7—C8—Cl1	−178.8 (2)
F21—F22—F31—C13	28.5 (6)	C12—C7—C8—C9	−1.1 (4)
F21—F22—C13—F11	−58.8 (12)	Cl1—C8—C9—C10	177.4 (2)
F21—F22—C13—F12	−9.1 (7)	C7—C8—C9—C10	−0.3 (4)
F21—F22—C13—F31	−147.7 (7)	C8—C9—C10—C11	1.6 (4)
F21—F22—C13—F32	−131.8 (10)	C8—C9—C10—C13	−177.0 (2)
F21—F22—C13—C10	104.7 (6)	C9—C10—C11—C12	−1.5 (4)
F31—F22—C13—F11	88.9 (11)	C9—C10—C13—F11	144.8 (6)
F31—F22—C13—F12	138.7 (6)	C9—C10—C13—F12	80.8 (8)
F31—F22—C13—F21	147.7 (7)	C9—C10—C13—F21	24.3 (8)
F31—F22—C13—F32	15.9 (8)	C9—C10—C13—F22	−23.0 (7)
F31—F22—C13—C10	−107.6 (4)	C9—C10—C13—F31	−100.4 (5)
C13—F22—F31—F32	−30.0 (14)	C9—C10—C13—F32	−139.0 (14)
F22—F31—F32—F11	5 (2)	C11—C10—C13—F11	−33.8 (7)
F22—F31—F32—C13	27.3 (12)	C11—C10—C13—F12	−97.8 (8)
F22—F31—C13—F11	−134.4 (5)	C11—C10—C13—F21	−154.3 (8)
F22—F31—C13—F12	−76.0 (12)	C11—C10—C13—F22	158.4 (6)
F22—F31—C13—F21	−22.7 (6)	C11—C10—C13—F31	80.9 (5)
F22—F31—C13—F32	−152.4 (14)	C11—C10—C13—F32	42.4 (14)
F22—F31—C13—C10	105.7 (5)	C13—C10—C11—C12	177.1 (3)
F32—F31—C13—F11	18.0 (13)	C10—C11—C12—Cl2	178.9 (2)
F32—F31—C13—F12	76.5 (17)	C10—C11—C12—C7	0.0 (3)
F32—F31—C13—F21	129.7 (14)	C1—C17—C18—C19	179.1 (3)
F32—F31—C13—F22	152.4 (14)	C1—C17—C22—C21	−178.5 (2)
F32—F31—C13—C10	−101.8 (13)	C18—C17—C22—C21	−1.0 (4)
C13—F31—F32—F11	−22.1 (15)	C22—C17—C18—C19	1.6 (4)
F11—F32—C13—F12	31.2 (12)	C17—C18—C19—C20	−1.6 (5)
F11—F32—C13—F21	94.5 (13)	C18—C19—C20—Cl3	−179.0 (2)
F11—F32—C13—F22	134.6 (6)	C18—C19—C20—C21	1.1 (5)
F11—F32—C13—F31	161.2 (14)	Cl3—C20—C21—C22	179.6 (2)
F11—F32—C13—C10	−104.5 (6)	C19—C20—C21—C22	−0.6 (5)
F31—F32—C13—F11	−161.2 (14)	C20—C21—C22—C17	0.5 (5)

Hydrogen-bond geometry (Å, º)

D—H···A	D—H	H···A	D···A	D—H···A
O(2)—H(201)···N(2)^i	0.85	2.05	2.895 (3)	172
N(1)—H(101)···O(2)	0.87	1.98	2.839 (2)	167

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