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

The title compound, C₁₈H₈Cl₂F₃N₅O₃·C₂H₆O, is an ethanol solvate of a tricyclic imide with an overall U-shape, each of the the three rings being planar. These include a benzene ring with two chloro and one tri­fluoro­methyl substituent, a central pyrazole ring with a cyano substituent, and a benzene ring with one nitro substituent. In the crystal packing, weak intermolecular hydrogen-bond contacts result in the formation of zigzag chains running parallel to the b axis

Key indicators

• Single-crystal X-ray study
• T = 298 K
• Mean [sigma](C-C) = 0.005 Å
• R factor = 0.055
• wR factor = 0.167
• Data-to-parameter ratio = 12.4

checkCIF/PLATON results

No syntax errors found



Alert level A
PLAT242_ALERT_2_A Check Low       Ueq as Compared to Neighbors for        C18

Author Response: see _publ_section_exptl_refinement

Alert level B
PLAT417_ALERT_2_B Short Inter D-H..H-D       H2B    ..  H4A     ..       1.96 Ang.
PLAT420_ALERT_2_B D-H Without Acceptor       O4     -   H4A    ...          ?

Alert level C
PLAT242_ALERT_2_C Check Low       Ueq as Compared to Neighbors for         N1

Author Response: see _publ_section_exptl_refinement

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  C10    -   C11    ...       1.44 Ang.
PLAT480_ALERT_4_C Long H...A H-Bond Reported H4A    ..  CL2     ..       2.86 Ang.
PLAT480_ALERT_4_C Long H...A H-Bond Reported H19B   ..  O2      ..       2.63 Ang.

   1 ALERT level A = In general: serious problem
   2 ALERT level B = Potentially serious problem
   5 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
   5 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
   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: XP (Bruker, 2002); software used to prepare material for publication: SHELXL97.

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

Crystal data

C18H8Cl2F3N5O3·C2H6O	F(000) = 1048
Mr = 516.26	Dx = 1.509 Mg m^−3
Monoclinic, P21/n	Melting point = 483–485 K
Hall symbol: -P 2yn	Mo Kα radiation, λ = 0.71073 Å
a = 10.630 (19) Å	Cell parameters from 5801 reflections
b = 18.00 (3) Å	θ = 2.1–25.2°
c = 12.54 (2) Å	µ = 0.35 mm^−1
β = 108.75 (3)°	T = 298 K
V = 2272 (7) Å^3	Block, colourless
Z = 4	0.25 × 0.22 × 0.18 mm

Data collection

Bruker APEX area-detector diffractometer	4099 independent reflections
Radiation source: fine-focus sealed tube	2643 reflections with I > 2σ(I)
Graphite monochromator	Rint = 0.030
φ and ω scans	θmax = 25.2°, θmin = 2.1°
Absorption correction: multi-scan (SADABS; Bruker, 2002)	h = −11→12
Tmin = 0.916, Tmax = 0.937	k = −21→21
10256 measured reflections	l = −15→11

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)] = 0.055	Hydrogen site location: inferred from neighbouring sites
wR(F^2) = 0.167	H-atom parameters constrained
S = 1.07	w = 1/[σ^2(Fo^2) + (0.0929P)^2 + 0.0142P] where P = (Fo^2 + 2Fc^2)/3
4099 reflections	(Δ/σ)max < 0.001
307 parameters	Δρmax = 0.36 e Å^−3
0 restraints	Δρmin = −0.32 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	0.11194 (9)	0.25044 (5)	−0.08647 (7)	0.0775 (3)
Cl2	0.25638 (8)	0.18918 (4)	0.35552 (7)	0.0623 (3)
F1	−0.1109 (3)	−0.00225 (17)	0.1375 (4)	0.1668 (17)
F2	−0.2468 (2)	0.08081 (15)	0.0842 (3)	0.1322 (12)
F3	−0.1766 (3)	0.02639 (19)	−0.0301 (3)	0.1518 (16)
O1	−0.4312 (3)	0.5531 (2)	0.0937 (3)	0.1086 (10)
O2	−0.3282 (3)	0.65092 (16)	0.1719 (3)	0.1006 (10)
O3	0.2640 (2)	0.49195 (11)	0.1871 (2)	0.0662 (6)
O4	−0.0202 (2)	0.31018 (11)	0.2492 (2)	0.0634 (6)
H4A	0.0251	0.2748	0.2425	0.095*
N1	−0.3296 (3)	0.58785 (19)	0.1374 (3)	0.0701 (8)
N2	0.1731 (2)	0.37578 (12)	0.1702 (2)	0.0478 (6)
H2B	0.1053	0.3502	0.1716	0.057*
N3	0.2825 (2)	0.26307 (12)	0.14905 (19)	0.0406 (5)
N4	0.3957 (2)	0.23655 (13)	0.1334 (2)	0.0485 (6)
N5	0.7015 (3)	0.28832 (18)	0.1215 (3)	0.0806 (9)
C1	−0.2016 (3)	0.55106 (17)	0.1504 (3)	0.0540 (8)
C2	−0.2019 (3)	0.48856 (17)	0.0855 (3)	0.0577 (8)
H2A	−0.2805	0.4697	0.0361	0.069*
C3	−0.0806 (3)	0.45540 (16)	0.0971 (3)	0.0530 (7)
H3A	−0.0775	0.4132	0.0553	0.064*
C4	0.0353 (3)	0.48400 (14)	0.1696 (3)	0.0463 (7)
C5	0.0317 (3)	0.54766 (16)	0.2322 (3)	0.0534 (7)
H5A	0.1103	0.5674	0.2805	0.064*
C6	−0.0879 (3)	0.58143 (16)	0.2225 (3)	0.0590 (9)
H6A	−0.0913	0.6238	0.2639	0.071*
C7	0.1684 (3)	0.45225 (16)	0.1779 (2)	0.0475 (7)
C8	0.2833 (2)	0.33876 (15)	0.1603 (2)	0.0424 (6)
C9	0.4033 (3)	0.36383 (17)	0.1553 (3)	0.0499 (7)
H9A	0.4349	0.4123	0.1618	0.060*
C10	0.4666 (3)	0.29873 (16)	0.1383 (2)	0.0469 (7)
C11	0.5979 (3)	0.29243 (18)	0.1287 (3)	0.0574 (8)
C12	0.1732 (2)	0.21240 (14)	0.1313 (2)	0.0407 (6)
C13	0.0876 (3)	0.20064 (15)	0.0236 (2)	0.0467 (7)
C14	−0.0150 (3)	0.15042 (17)	0.0018 (3)	0.0550 (7)
H14A	−0.0723	0.1434	−0.0711	0.066*
C15	−0.0309 (3)	0.11031 (15)	0.0915 (3)	0.0483 (7)
C16	0.0522 (3)	0.12135 (14)	0.2002 (2)	0.0464 (7)
H16A	0.0400	0.0945	0.2594	0.056*
C17	0.1547 (3)	0.17312 (14)	0.2203 (2)	0.0414 (6)
C18	−0.1410 (3)	0.0541 (2)	0.0690 (3)	0.0669 (9)
C19	−0.0078 (5)	0.3196 (2)	0.3642 (4)	0.0885 (12)
H19A	0.0852	0.3274	0.4064	0.106*
H19B	−0.0356	0.2741	0.3915	0.106*
C20	−0.0860 (6)	0.3823 (3)	0.3876 (4)	0.1062 (15)
H20A	−0.0718	0.3851	0.4671	0.159*
H20B	−0.1787	0.3745	0.3483	0.159*
H20C	−0.0581	0.4280	0.3625	0.159*

Atomic displacement parameters (Ų)

	U^11	U^22	U^33	U^12	U^13	U^23
Cl1	0.0893 (7)	0.0944 (7)	0.0451 (5)	−0.0187 (5)	0.0166 (5)	0.0179 (4)
Cl2	0.0695 (5)	0.0690 (6)	0.0418 (5)	−0.0043 (4)	0.0088 (4)	0.0045 (4)
F1	0.130 (2)	0.108 (2)	0.211 (4)	−0.0668 (17)	−0.018 (2)	0.072 (2)
F2	0.0716 (15)	0.137 (2)	0.204 (4)	−0.0361 (14)	0.067 (2)	−0.045 (2)
F3	0.171 (3)	0.176 (3)	0.128 (3)	−0.123 (3)	0.077 (3)	−0.083 (2)
O1	0.0678 (18)	0.149 (3)	0.110 (3)	0.0199 (19)	0.0302 (18)	−0.024 (2)
O2	0.104 (2)	0.0685 (18)	0.154 (3)	0.0312 (15)	0.076 (2)	0.0201 (18)
O3	0.0556 (12)	0.0500 (12)	0.097 (2)	−0.0115 (10)	0.0293 (13)	−0.0071 (12)
O4	0.0525 (12)	0.0602 (13)	0.0847 (18)	0.0019 (9)	0.0320 (13)	0.0058 (11)
N1	0.074 (2)	0.076 (2)	0.072 (2)	0.0206 (16)	0.0394 (19)	0.0158 (16)
N2	0.0443 (12)	0.0380 (13)	0.0667 (17)	−0.0035 (9)	0.0256 (13)	0.0004 (11)
N3	0.0376 (11)	0.0395 (13)	0.0458 (14)	−0.0002 (9)	0.0149 (11)	0.0004 (10)
N4	0.0426 (12)	0.0550 (15)	0.0486 (15)	0.0050 (10)	0.0158 (12)	0.0005 (11)
N5	0.0454 (16)	0.119 (3)	0.081 (2)	−0.0020 (15)	0.0254 (17)	−0.0057 (19)
C1	0.0594 (18)	0.0517 (18)	0.059 (2)	0.0100 (15)	0.0295 (17)	0.0109 (15)
C2	0.0568 (18)	0.066 (2)	0.0501 (19)	0.0072 (15)	0.0172 (16)	0.0047 (16)
C3	0.0611 (18)	0.0456 (16)	0.054 (2)	−0.0003 (14)	0.0212 (16)	−0.0056 (14)
C4	0.0544 (16)	0.0356 (15)	0.0529 (18)	0.0012 (12)	0.0228 (15)	0.0050 (13)
C5	0.0590 (17)	0.0415 (16)	0.062 (2)	−0.0074 (13)	0.0230 (16)	−0.0041 (14)
C6	0.078 (2)	0.0387 (16)	0.072 (2)	0.0007 (15)	0.041 (2)	−0.0012 (15)
C7	0.0490 (15)	0.0446 (16)	0.0499 (18)	−0.0033 (13)	0.0174 (14)	0.0013 (13)
C8	0.0423 (14)	0.0449 (16)	0.0408 (16)	0.0014 (12)	0.0143 (13)	0.0027 (12)
C9	0.0457 (15)	0.0508 (17)	0.0542 (19)	−0.0087 (12)	0.0176 (14)	−0.0010 (14)
C10	0.0388 (14)	0.0586 (18)	0.0440 (17)	−0.0004 (13)	0.0141 (13)	−0.0009 (13)
C11	0.0456 (17)	0.075 (2)	0.0502 (19)	−0.0043 (14)	0.0137 (15)	−0.0022 (16)
C12	0.0454 (15)	0.0347 (14)	0.0447 (17)	0.0057 (11)	0.0183 (14)	0.0026 (12)
C13	0.0512 (15)	0.0480 (16)	0.0421 (16)	0.0020 (12)	0.0166 (14)	0.0092 (13)
C14	0.0539 (16)	0.0589 (19)	0.0460 (18)	−0.0024 (14)	0.0073 (15)	−0.0021 (14)
C15	0.0446 (14)	0.0433 (16)	0.059 (2)	−0.0020 (12)	0.0189 (15)	−0.0030 (14)
C16	0.0519 (16)	0.0393 (15)	0.0546 (19)	0.0035 (12)	0.0264 (15)	0.0066 (13)
C17	0.0437 (13)	0.0405 (15)	0.0413 (16)	0.0045 (11)	0.0156 (13)	0.0005 (12)
C18	0.062 (2)	0.064 (2)	0.078 (3)	−0.0151 (17)	0.027 (2)	−0.006 (2)
C19	0.096 (3)	0.079 (3)	0.089 (3)	−0.003 (2)	0.028 (3)	0.008 (2)
C20	0.137 (4)	0.104 (3)	0.095 (3)	0.009 (3)	0.062 (3)	0.007 (3)

Geometric parameters (Å, º)

Cl1—C13	1.734 (3)	C3—H3A	0.9300
Cl2—C17	1.717 (4)	C4—C5	1.396 (4)
F1—C18	1.301 (5)	C4—C7	1.498 (5)
F2—C18	1.292 (4)	C5—C6	1.380 (5)
F3—C18	1.278 (5)	C5—H5A	0.9300
O1—N1	1.215 (4)	C6—H6A	0.9300
O2—N1	1.213 (4)	C8—C9	1.373 (4)
O3—C7	1.217 (4)	C9—C10	1.401 (4)
O4—C19	1.415 (5)	C9—H9A	0.9300
O4—N2	2.812 (4)	C10—C11	1.444 (5)
O4—N5^i	2.903 (6)	C12—C13	1.381 (4)
O4—H4A	0.8200	C12—C17	1.387 (4)
N1—C1	1.474 (5)	C13—C14	1.374 (4)
N2—C7	1.382 (4)	C14—C15	1.393 (4)
N2—C8	1.387 (4)	C14—H14A	0.9300
N2—H2B	0.8600	C15—C16	1.379 (5)
N3—N4	1.365 (3)	C15—C18	1.504 (5)
N3—C8	1.369 (4)	C16—C17	1.394 (4)
N3—C12	1.437 (4)	C16—H16A	0.9300
N4—C10	1.340 (4)	C19—C20	1.487 (6)
N5—C11	1.136 (4)	C19—H19A	0.9700
C1—C6	1.369 (5)	C19—H19B	0.9700
C1—C2	1.388 (5)	C20—H20A	0.9600
C2—C3	1.386 (5)	C20—H20B	0.9600
C2—H2A	0.9300	C20—H20C	0.9600
C3—C4	1.374 (5)
C19—O4—N2	118.0 (2)	C10—C9—H9A	128.3
C19—O4—N5^i	108.9 (2)	N4—C10—C9	114.5 (3)
N2—O4—N5^i	126.37 (16)	N4—C10—C11	118.4 (3)
C19—O4—H4A	109.5	C9—C10—C11	127.1 (3)
N2—O4—H4A	76.7	N5—C11—C10	179.2 (4)
N5^i—O4—H4A	111.5	C13—C12—C17	119.3 (3)
O1—N1—O2	123.3 (3)	C13—C12—N3	119.7 (2)
O2—N1—C1	118.4 (3)	C17—C12—N3	121.0 (3)
O1—N1—C1	118.3 (3)	C14—C13—C12	121.8 (3)
C7—N2—C8	122.4 (2)	C14—C13—Cl1	119.6 (2)
C7—N2—H2B	118.8	C12—C13—Cl1	118.6 (2)
C8—N2—H2B	118.8	C13—C14—C15	118.3 (3)
N4—N3—C8	112.73 (19)	C13—C14—H14A	120.8
N4—N3—C12	117.5 (2)	C15—C14—H14A	120.8
C8—N3—C12	128.7 (2)	C16—C15—C14	121.2 (3)
N3—N4—C10	102.1 (2)	C16—C15—C18	119.7 (3)
C6—C1—C2	123.1 (3)	C14—C15—C18	119.1 (3)
C6—C1—N1	118.7 (3)	C15—C16—C17	119.4 (2)
C2—C1—N1	118.1 (3)	C15—C16—H16A	120.3
C3—C2—C1	117.4 (3)	C17—C16—H16A	120.3
C3—C2—H2A	121.3	C12—C17—C16	120.0 (3)
C1—C2—H2A	121.3	C12—C17—Cl2	120.1 (2)
C4—C3—C2	121.0 (3)	C16—C17—Cl2	119.9 (2)
C4—C3—H3A	119.5	F3—C18—F2	106.8 (4)
C2—C3—H3A	119.5	F3—C18—F1	105.7 (4)
C3—C4—C5	119.9 (3)	F2—C18—F1	103.5 (3)
C3—C4—C7	121.9 (3)	F3—C18—C15	114.5 (3)
C5—C4—C7	118.0 (3)	F2—C18—C15	112.6 (3)
C6—C5—C4	120.2 (3)	F1—C18—C15	112.9 (3)
C6—C5—H5A	119.9	O4—C19—C20	114.7 (4)
C4—C5—H5A	119.9	O4—C19—H19A	108.6
C1—C6—C5	118.4 (3)	C20—C19—H19A	108.6
C1—C6—H6A	120.8	O4—C19—H19B	108.6
C5—C6—H6A	120.8	C20—C19—H19B	108.6
O3—C7—N2	122.9 (2)	H19A—C19—H19B	107.6
O3—C7—C4	121.6 (3)	C19—C20—H20A	109.5
N2—C7—C4	115.4 (2)	C19—C20—H20B	109.5
N3—C8—C9	107.3 (2)	H20A—C20—H20B	109.5
N3—C8—N2	120.7 (2)	C19—C20—H20C	109.5
C9—C8—N2	132.0 (3)	H20A—C20—H20C	109.5
C8—C9—C10	103.3 (3)	H20B—C20—H20C	109.5
C8—C9—H9A	128.3
C19—O4—N2—C7	−64.2 (3)	N3—C8—C9—C10	1.3 (3)
N5^i—O4—N2—C7	83.5 (2)	N2—C8—C9—C10	−176.4 (3)
C19—O4—N2—C8	96.3 (3)	N3—N4—C10—C9	−0.6 (3)
N5^i—O4—N2—C8	−116.0 (2)	N3—N4—C10—C11	178.0 (3)
C8—N3—N4—C10	1.4 (3)	C8—C9—C10—N4	−0.5 (4)
C12—N3—N4—C10	170.5 (2)	C8—C9—C10—C11	−178.9 (3)
O2—N1—C1—C6	14.9 (4)	N4—N3—C12—C13	−83.4 (3)
O1—N1—C1—C6	−164.3 (3)	C8—N3—C12—C13	83.6 (3)
O2—N1—C1—C2	−162.7 (3)	N4—N3—C12—C17	94.4 (3)
O1—N1—C1—C2	18.1 (4)	C8—N3—C12—C17	−98.6 (3)
C6—C1—C2—C3	1.3 (4)	C17—C12—C13—C14	−0.7 (4)
N1—C1—C2—C3	178.8 (3)	N3—C12—C13—C14	177.2 (2)
C1—C2—C3—C4	−0.6 (4)	C17—C12—C13—Cl1	179.82 (19)
C2—C3—C4—C5	−0.5 (4)	N3—C12—C13—Cl1	−2.3 (3)
C2—C3—C4—C7	−175.8 (3)	C12—C13—C14—C15	−0.5 (4)
C3—C4—C5—C6	0.8 (4)	Cl1—C13—C14—C15	178.9 (2)
C7—C4—C5—C6	176.3 (3)	C13—C14—C15—C16	1.2 (4)
C2—C1—C6—C5	−1.0 (5)	C13—C14—C15—C18	−178.9 (3)
N1—C1—C6—C5	−178.5 (3)	C14—C15—C16—C17	−0.6 (4)
C4—C5—C6—C1	−0.1 (4)	C18—C15—C16—C17	179.5 (3)
C8—N2—C7—O3	−7.0 (4)	C13—C12—C17—C16	1.3 (4)
C8—N2—C7—C4	170.6 (3)	N3—C12—C17—C16	−176.5 (2)
C3—C4—C7—O3	139.4 (3)	C13—C12—C17—Cl2	−177.72 (19)
C5—C4—C7—O3	−36.0 (4)	N3—C12—C17—Cl2	4.4 (3)
C3—C4—C7—N2	−38.3 (4)	C15—C16—C17—C12	−0.7 (4)
C5—C4—C7—N2	146.3 (3)	C15—C16—C17—Cl2	178.36 (19)
N4—N3—C8—C9	−1.8 (3)	C16—C15—C18—F3	−153.4 (4)
C12—N3—C8—C9	−169.3 (3)	C14—C15—C18—F3	26.7 (5)
N4—N3—C8—N2	176.2 (2)	C16—C15—C18—F2	84.4 (4)
C12—N3—C8—N2	8.7 (4)	C14—C15—C18—F2	−95.5 (4)
C7—N2—C8—N3	−177.8 (3)	C16—C15—C18—F1	−32.3 (5)
C7—N2—C8—C9	−0.3 (5)	C14—C15—C18—F1	147.8 (4)

Symmetry code: (i) x−1, y, z.

Hydrogen-bond geometry (Å, º)

D—H···A	D—H	H···A	D···A	D—H···A
N2—H2B···O4	0.86	2.02	2.812 (5)	153
O4—H4A···Cl2	0.82	2.86	3.556 (5)	144
C16—H16A···O1^ii	0.93	2.58	3.461 (6)	159
C19—H19B···O2^ii	0.97	2.63	3.458 (7)	144

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