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

Zhang, X.-H.; Zhong, P.; Yang, Z.-P.; Hu, M.-L.; Xiao, H.-P.

doi:10.1107/S1600536805005763

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

X.-H. Zhang, P. Zhong, Z.-P. Yang, M.-L. Hu and H.-P. Xiao

The molecule of the title compound, C₁₈H₈Cl₃F₃N₄O, is a tricyclic amide with an overall U-shape. Intermolecular N—H

N hydrogen bonds, with an N(amide)

N(cyano) separation of 3.051 (4) Å, link the molecules into linear chains along the c axis.

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Supporting information

	Crystallographic Information File (CIF) https://doi.org/10.1107/S1600536805005763/cv6454sup1.cif Contains datablocks I, global
	Structure factor file (CIF format) https://doi.org/10.1107/S1600536805005763/cv6454Isup2.hkl Contains datablock I

CCDC reference: 270281

checkCIF report

Key indicators

Single-crystal X-ray study
T = 298 K
Mean (C-C) = 0.005 Å
R factor = 0.054
wR factor = 0.125
Data-to-parameter ratio = 13.2

checkCIF/PLATON results

No syntax errors found



Alert level B
PLAT431_ALERT_2_B Short Inter HL..A Contact  Cl1    ..  O1      ..       2.92 Ang.

Alert level C
PLAT340_ALERT_3_C Low Bond Precision on C-C bonds (x 1000) Ang ...          5
PLAT371_ALERT_2_C Long   C(sp2)-C(sp1) Bond  C8     -   C11    ...       1.44 Ang.
PLAT431_ALERT_2_C Short Inter HL..A Contact  Cl2    ..  Cl3     ..       3.25 Ang.
PLAT731_ALERT_1_C Bond    Calc     0.85(3), Rep   0.857(10) ......       3.00 su-Rat
              N3   -H3A     1.555   1.555

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

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

Computing details top

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: XP (Bruker, 2002); software used to prepare material for publication: SHELXL97.

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

Crystal data top

C₁₈H₈Cl₃F₃N₄O	F(000) = 920
M_r = 459.63	D_x = 1.579 Mg m⁻³
Monoclinic, P2₁/c	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: -P2ybc	Cell parameters from 3120 reflections
a = 10.3133 (8) Å	θ = 2.2–24.1°
b = 22.7193 (18) Å	µ = 0.52 mm⁻¹
c = 8.5237 (7) Å	T = 298 K
β = 104.580 (1)°	Block, colorless
V = 1932.9 (3) Å³	0.42 × 0.24 × 0.14 mm
Z = 4

Data collection top

Bruker APEX area-detector diffractometer	3509 independent reflections
Radiation source: fine-focus sealed tube	3069 reflections with I > 2σ(I)
Graphite monochromator	R_int = 0.026
φ and ω scans	θ_max = 25.3°, θ_min = 1.8°
Absorption correction: multi-scan (SADABS; Bruker, 2002)	h = −10→12
T_min = 0.811, T_max = 0.931	k = −27→20
10250 measured reflections	l = −10→10

Refinement top

Refinement on F²	Primary atom site location: structure-invariant direct methods
Least-squares matrix: full	Secondary atom site location: difference Fourier map
R[F² > 2σ(F²)] = 0.054	Hydrogen site location: inferred from neighbouring sites
wR(F²) = 0.125	H atoms treated by a mixture of independent and constrained refinement
S = 1.11	w = 1/[σ²(F_o²) + (0.0486P)² + 1.4918P] where P = (F_o² + 2F_c²)/3
3509 reflections	(Δ/σ)_max = 0.001
265 parameters	Δρ_max = 0.46 e Å⁻³
1 restraint	Δρ_min = −0.27 e Å⁻³

Special details top

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 (Å²) top

	x	y	z	U_iso*/U_eq
N2	0.6709 (2)	0.62003 (12)	0.7445 (3)	0.0452 (6)
Cl1	0.82479 (8)	0.53678 (3)	0.51354 (10)	0.0510 (2)
Cl2	0.56977 (8)	0.74420 (4)	0.47483 (11)	0.0579 (3)
Cl3	0.33463 (10)	0.69804 (4)	0.11645 (12)	0.0693 (3)
F1	1.1122 (2)	0.71333 (12)	0.3508 (3)	0.0847 (8)
F2	0.9690 (2)	0.77421 (10)	0.2168 (3)	0.0757 (6)
F3	0.9926 (3)	0.69021 (12)	0.1167 (3)	0.0891 (8)
O1	0.22736 (19)	0.58346 (10)	0.3973 (2)	0.0485 (5)
C10	0.5020 (3)	0.59477 (13)	0.5304 (3)	0.0377 (6)
C9	0.4645 (3)	0.57822 (15)	0.6661 (4)	0.0468 (8)
H9	0.3854	0.5599	0.6723	0.056*
N3	0.4381 (2)	0.59115 (13)	0.3662 (3)	0.0442 (6)
N4	0.5849 (3)	0.58347 (17)	1.0977 (3)	0.0698 (9)
C1	0.9902 (3)	0.71745 (17)	0.2530 (4)	0.0575 (9)
C2	0.8866 (3)	0.69149 (14)	0.3298 (3)	0.0410 (7)
C3	0.9015 (3)	0.63338 (14)	0.3778 (3)	0.0399 (7)
H3	0.9710	0.6107	0.3584	0.048*
C4	0.8115 (3)	0.60954 (13)	0.4549 (3)	0.0361 (6)
C5	0.7096 (3)	0.64364 (13)	0.4875 (3)	0.0353 (6)
C6	0.6955 (3)	0.70129 (13)	0.4343 (3)	0.0392 (7)
C7	0.7841 (3)	0.72561 (14)	0.3551 (3)	0.0435 (7)
H7	0.7744	0.7644	0.3195	0.052*
C8	0.5715 (3)	0.59495 (15)	0.7935 (3)	0.0434 (7)
N1	0.6250 (2)	0.61982 (11)	0.5807 (3)	0.0376 (5)
C11	0.5817 (3)	0.58840 (17)	0.9647 (4)	0.0528 (8)
C12	0.3025 (3)	0.58745 (13)	0.3094 (3)	0.0386 (6)
C13	0.2528 (3)	0.58571 (15)	0.1286 (3)	0.0433 (7)
C14	0.2630 (3)	0.63328 (16)	0.0307 (4)	0.0510 (8)
C15	0.2125 (4)	0.6303 (2)	−0.1362 (4)	0.0645 (10)
H15	0.2190	0.6624	−0.2014	0.077*
C16	0.1532 (4)	0.5793 (2)	−0.2031 (5)	0.0718 (12)
H16	0.1204	0.5768	−0.3150	0.086*
C17	0.1409 (4)	0.5318 (2)	−0.1094 (5)	0.0754 (12)
H17	0.0999	0.4976	−0.1578	0.090*
C18	0.1892 (3)	0.53448 (18)	0.0563 (4)	0.0612 (9)
H18	0.1795	0.5024	0.1201	0.073*
H3A	0.488 (3)	0.5921 (17)	0.300 (4)	0.073*

Atomic displacement parameters (Å²) top

	U¹¹	U²²	U³³	U¹²	U¹³	U²³
N2	0.0407 (13)	0.0664 (17)	0.0302 (13)	−0.0011 (12)	0.0119 (10)	−0.0025 (11)
Cl1	0.0550 (5)	0.0438 (4)	0.0576 (5)	0.0021 (4)	0.0204 (4)	0.0067 (4)
Cl2	0.0521 (5)	0.0615 (5)	0.0652 (6)	0.0157 (4)	0.0242 (4)	−0.0022 (4)
Cl3	0.0683 (6)	0.0700 (6)	0.0730 (6)	−0.0126 (5)	0.0242 (5)	0.0145 (5)
F1	0.0413 (11)	0.114 (2)	0.0977 (17)	−0.0126 (12)	0.0155 (11)	0.0344 (15)
F2	0.0728 (14)	0.0735 (15)	0.0870 (16)	−0.0115 (11)	0.0315 (12)	0.0290 (12)
F3	0.1038 (18)	0.1107 (19)	0.0741 (15)	−0.0184 (15)	0.0622 (14)	−0.0053 (14)
O1	0.0374 (11)	0.0676 (15)	0.0455 (12)	−0.0038 (10)	0.0195 (10)	0.0079 (10)
C10	0.0330 (14)	0.0530 (18)	0.0295 (14)	0.0019 (13)	0.0125 (11)	0.0011 (12)
C9	0.0384 (16)	0.069 (2)	0.0366 (16)	−0.0063 (15)	0.0170 (13)	0.0024 (15)
N3	0.0342 (13)	0.0726 (18)	0.0288 (13)	−0.0064 (12)	0.0135 (10)	0.0013 (12)
N4	0.0592 (18)	0.124 (3)	0.0304 (15)	0.0024 (18)	0.0194 (13)	0.0053 (16)
C1	0.050 (2)	0.071 (2)	0.055 (2)	−0.0078 (18)	0.0195 (16)	0.0123 (18)
C2	0.0372 (15)	0.0549 (19)	0.0316 (15)	−0.0059 (14)	0.0100 (12)	0.0020 (13)
C3	0.0324 (14)	0.0536 (18)	0.0365 (15)	0.0017 (13)	0.0141 (12)	−0.0004 (13)
C4	0.0342 (14)	0.0437 (16)	0.0295 (14)	−0.0008 (12)	0.0063 (11)	0.0004 (12)
C5	0.0289 (13)	0.0501 (17)	0.0276 (13)	−0.0047 (12)	0.0083 (11)	−0.0021 (12)
C6	0.0351 (15)	0.0503 (18)	0.0340 (15)	0.0035 (13)	0.0119 (12)	−0.0010 (13)
C7	0.0443 (17)	0.0459 (17)	0.0405 (16)	0.0004 (14)	0.0111 (13)	0.0057 (13)
C8	0.0402 (16)	0.065 (2)	0.0285 (15)	0.0032 (15)	0.0149 (12)	0.0016 (14)
N1	0.0339 (12)	0.0558 (15)	0.0249 (11)	−0.0034 (11)	0.0106 (9)	0.0004 (10)
C11	0.0436 (17)	0.082 (2)	0.0364 (18)	0.0037 (17)	0.0162 (14)	0.0026 (16)
C12	0.0363 (15)	0.0426 (16)	0.0387 (16)	−0.0024 (13)	0.0129 (13)	0.0033 (12)
C13	0.0302 (14)	0.065 (2)	0.0351 (16)	0.0030 (14)	0.0083 (12)	0.0011 (14)
C14	0.0375 (16)	0.076 (2)	0.0425 (18)	0.0067 (16)	0.0157 (13)	0.0102 (16)
C15	0.052 (2)	0.096 (3)	0.047 (2)	0.018 (2)	0.0171 (16)	0.018 (2)
C16	0.054 (2)	0.117 (4)	0.040 (2)	0.010 (2)	0.0041 (16)	−0.004 (2)
C17	0.062 (2)	0.098 (3)	0.060 (2)	−0.004 (2)	0.0044 (19)	−0.023 (2)
C18	0.0510 (19)	0.082 (3)	0.049 (2)	−0.0021 (18)	0.0086 (16)	−0.0094 (18)

Geometric parameters (Å, º) top

N2—C8	1.330 (4)	C3—C4	1.377 (4)
N2—N1	1.356 (3)	C3—H3	0.9300
Cl1—C4	1.722 (3)	C4—C5	1.388 (4)
Cl2—C6	1.725 (3)	C5—C6	1.382 (4)
Cl3—C14	1.724 (4)	C5—N1	1.427 (3)
F1—C1	1.325 (4)	C6—C7	1.381 (4)
F2—C1	1.331 (4)	C7—H7	0.9300
F3—C1	1.323 (4)	C8—C11	1.444 (4)
O1—C12	1.209 (3)	C12—C13	1.497 (4)
C10—N1	1.358 (4)	C13—C14	1.386 (4)
C10—C9	1.362 (4)	C13—C18	1.401 (5)
C10—N3	1.391 (4)	C14—C15	1.388 (5)
C9—C8	1.392 (4)	C15—C16	1.366 (6)
C9—H9	0.9300	C15—H15	0.9300
N3—C12	1.363 (4)	C16—C17	1.367 (6)
N3—H3A	0.857 (10)	C16—H16	0.9300
N4—C11	1.132 (4)	C17—C18	1.376 (5)
C1—C2	1.507 (4)	C17—H17	0.9300
C2—C7	1.371 (4)	C18—H18	0.9300
C2—C3	1.379 (4)

C8—N2—N1	103.0 (2)	C2—C7—C6	118.8 (3)
N1—C10—C9	106.9 (2)	C2—C7—H7	120.6
N1—C10—N3	120.7 (2)	C6—C7—H7	120.6
C9—C10—N3	132.4 (3)	N2—C8—C9	113.2 (2)
C10—C9—C8	104.4 (3)	N2—C8—C11	119.7 (3)
C10—C9—H9	127.8	C9—C8—C11	127.0 (3)
C8—C9—H9	127.8	N2—N1—C10	112.5 (2)
C12—N3—C10	123.0 (2)	N2—N1—C5	117.9 (2)
C12—N3—H3A	120 (3)	C10—N1—C5	129.6 (2)
C10—N3—H3A	117 (3)	N4—C11—C8	177.5 (3)
F3—C1—F1	107.2 (3)	O1—C12—N3	123.0 (3)
F3—C1—F2	106.7 (3)	O1—C12—C13	121.9 (3)
F1—C1—F2	106.8 (3)	N3—C12—C13	115.0 (2)
F3—C1—C2	111.8 (3)	C14—C13—C18	118.8 (3)
F1—C1—C2	111.3 (3)	C14—C13—C12	122.8 (3)
F2—C1—C2	112.8 (3)	C18—C13—C12	118.4 (3)
C7—C2—C3	121.8 (3)	C13—C14—C15	120.9 (4)
C7—C2—C1	120.4 (3)	C13—C14—Cl3	120.0 (2)
C3—C2—C1	117.7 (3)	C15—C14—Cl3	119.1 (3)
C4—C3—C2	118.7 (3)	C16—C15—C14	118.9 (4)
C4—C3—H3	120.6	C16—C15—H15	120.6
C2—C3—H3	120.6	C14—C15—H15	120.6
C3—C4—C5	120.7 (3)	C15—C16—C17	121.5 (4)
C3—C4—Cl1	120.1 (2)	C15—C16—H16	119.2
C5—C4—Cl1	119.1 (2)	C17—C16—H16	119.2
C6—C5—C4	119.1 (2)	C16—C17—C18	120.1 (4)
C6—C5—N1	120.9 (2)	C16—C17—H17	119.9
C4—C5—N1	120.0 (3)	C18—C17—H17	119.9
C7—C6—C5	120.8 (3)	C17—C18—C13	119.8 (4)
C7—C6—Cl2	119.7 (2)	C17—C18—H18	120.1
C5—C6—Cl2	119.5 (2)	C13—C18—H18	120.1

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
N3—H3A···N4ⁱ	0.85 (3)	2.21 (3)	3.051 (4)	168 (4)

Symmetry code: (i) x, y, z−1.

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

Supporting information

Key indicators

checkCIF/PLATON results

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