3,5-Bis(4-fluoro-phen-yl)-1-(4-nitro-phen-yl)-4,5-dihydro-1H-pyrazole.

In the title compound, C(21)H(15)F(2)N(3)O(2), a pyrazole derivative bearing three aromatic substituents, the central five-membered heterocyclic ring makes dihedral angles of 1.77 (14), 3.68 (13) and 72.15 (14)° with the three benzene rings. In the crystal, C-H⋯O and C-H⋯F inter-actions connect the mol-ecules into double layers parallel to the bc plane.

Related literature

For general information about the pharmacological properties and medical applications of pyrazole derivatives, see: Kumar et al. (2009 ▶); Sarojini et al. (2010 ▶); Samshuddin et al. (2012 ▶). For the crystal structures of other pyrazole derivatives, see: Baktır et al. (2011 ▶); Jasinski et al. (2012 ▶). For the puckering analysis of cyclic motifs, see: Cremer & Pople (1975 ▶). For graph-set analysis of hydrogen bonds, see: Etter et al. (1990 ▶); Bernstein et al. (1995 ▶).

Experimental

Crystal data

C21H15F2N3O2

M = 379.36

Monoclinic,

a = 13.2884 (13) Å

b = 12.7364 (10) Å

c = 11.4656 (9) Å

β = 115.324 (3)°

V = 1754.0 (3) Å3

Z = 4

Mo Kα radiation

μ = 0.11 mm−1

T = 200 K

0.57 × 0.33 × 0.27 mm

Data collection

Bruker APEXII CCD diffractometer

Absorption correction: multi-scan (SADABS; Bruker, 2008 ▶) T min = 0.692, T max = 0.971

15973 measured reflections

4301 independent reflections

3066 reflections with I > 2σ(I)

R int = 0.052

Refinement

R[F 2 > 2σ(F 2)] = 0.067

wR(F 2) = 0.221

S = 1.06

4301 reflections

253 parameters

H-atom parameters constrained

Δρmax = 0.41 e Å−3

Δρmin = −0.39 e Å−3

Data collection: APEX2 (Bruker, 2010 ▶); cell refinement: SAINT (Bruker, 2010 ▶); data reduction: SAINT; program(s) used to solve structure: SHELXS97 (Sheldrick, 2008 ▶); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008 ▶); molecular graphics: ORTEP-3 (Farrugia, 1997 ▶) and Mercury (Macrae et al., 2008 ▶); software used to prepare material for publication: SHELXL97 and PLATON (Spek, 2009 ▶).

Click here for additional data file.

Crystal structure: contains datablock(s) I, global. DOI: 10.1107/S160053681204370X/is5210sup1.cif

Click here for additional data file.

Supplementary material file. DOI: 10.1107/S160053681204370X/is5210Isup2.cdx

Click here for additional data file.

Structure factors: contains datablock(s) I. DOI: 10.1107/S160053681204370X/is5210Isup3.hkl

Click here for additional data file.

Supplementary material file. DOI: 10.1107/S160053681204370X/is5210Isup4.cml

Additional supplementary materials: crystallographic information; 3D view; checkCIF report

C21H15F2N3O2	F(000) = 784
Mr = 379.36	Dx = 1.437 Mg m−3
Monoclinic, P21/c	Melting point: 443 K
Hall symbol: -P 2ybc	Mo Kα radiation, λ = 0.71073 Å
a = 13.2884 (13) Å	Cell parameters from 6702 reflections
b = 12.7364 (10) Å	θ = 2.3–27.9°
c = 11.4656 (9) Å	µ = 0.11 mm−1
β = 115.324 (3)°	T = 200 K
V = 1754.0 (3) Å3	Block, orange
Z = 4	0.57 × 0.33 × 0.27 mm

Bruker APEXII CCD diffractometer	4301 independent reflections
Radiation source: fine-focus sealed tube	3066 reflections with I > 2σ(I)
Graphite monochromator	Rint = 0.052
φ and ω scans	θmax = 28.3°, θmin = 2.3°
Absorption correction: multi-scan (SADABS; Bruker, 2008)	h = −17→17
Tmin = 0.692, Tmax = 0.971	k = −15→16
15973 measured reflections	l = −15→14

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)] = 0.067	Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.221	H-atom parameters constrained
S = 1.06	w = 1/[σ2(Fo2) + (0.1331P)2 + 0.5062P] where P = (Fo2 + 2Fc2)/3
4301 reflections	(Δ/σ)max < 0.001
253 parameters	Δρmax = 0.41 e Å−3
0 restraints	Δρmin = −0.39 e Å−3

	x	y	z	Uiso*/Ueq
F1	0.11689 (15)	−0.42461 (13)	−0.04507 (17)	0.0638 (5)
F2	0.01460 (13)	0.43563 (13)	0.35591 (18)	0.0611 (5)
O1	0.61528 (16)	0.02802 (17)	1.00769 (16)	0.0536 (5)
O2	0.57223 (18)	0.19339 (18)	0.98021 (18)	0.0663 (6)
N1	0.30617 (15)	−0.05788 (13)	0.36124 (16)	0.0305 (4)
N2	0.32892 (15)	0.04326 (14)	0.40815 (16)	0.0327 (4)
N3	0.56940 (16)	0.10368 (18)	0.93869 (18)	0.0428 (5)
C1	0.25491 (17)	−0.05414 (16)	0.23711 (18)	0.0297 (4)
C2	0.2351 (2)	0.05569 (17)	0.1837 (2)	0.0368 (5)
H2A	0.1545	0.0717	0.1396	0.044*
H2B	0.2688	0.0663	0.1225	0.044*
C3	0.29364 (18)	0.12390 (17)	0.30617 (19)	0.0322 (5)
H3	0.3607	0.1583	0.3047	0.039*
C11	0.21963 (17)	−0.15094 (17)	0.16168 (18)	0.0298 (4)
C12	0.24429 (19)	−0.24829 (18)	0.2240 (2)	0.0354 (5)
H12	0.2849	−0.2511	0.3151	0.042*
C13	0.2103 (2)	−0.34014 (19)	0.1545 (3)	0.0426 (5)
H13	0.2270	−0.4063	0.1968	0.051*
C14	0.1515 (2)	−0.3339 (2)	0.0222 (2)	0.0431 (6)
C15	0.1269 (2)	−0.2404 (2)	−0.0425 (2)	0.0437 (6)
H15	0.0871	−0.2385	−0.1338	0.052*
C16	0.16125 (19)	−0.14838 (19)	0.0279 (2)	0.0375 (5)
H16	0.1448	−0.0827	−0.0156	0.045*
C21	0.21828 (17)	0.20653 (17)	0.32160 (18)	0.0303 (4)
C22	0.2177 (2)	0.30641 (19)	0.2750 (3)	0.0495 (6)
H22	0.2653	0.3225	0.2350	0.059*
C23	0.1486 (3)	0.3840 (2)	0.2857 (3)	0.0570 (7)
H23	0.1479	0.4525	0.2528	0.068*
C24	0.08164 (19)	0.35925 (19)	0.3447 (3)	0.0422 (6)
C25	0.0790 (2)	0.2616 (2)	0.3912 (2)	0.0431 (6)
H25	0.0308	0.2464	0.4309	0.052*
C26	0.14779 (19)	0.18489 (19)	0.3796 (2)	0.0390 (5)
H26	0.1468	0.1163	0.4117	0.047*
C31	0.39135 (16)	0.05788 (16)	0.53770 (18)	0.0289 (4)
C32	0.42036 (18)	−0.02827 (17)	0.62266 (19)	0.0321 (4)
H32	0.3995	−0.0972	0.5896	0.039*
C33	0.47889 (18)	−0.01300 (18)	0.7534 (2)	0.0344 (5)
H33	0.4983	−0.0711	0.8108	0.041*
C34	0.50939 (17)	0.08796 (18)	0.80077 (19)	0.0331 (5)
C35	0.48391 (18)	0.17349 (18)	0.7191 (2)	0.0348 (5)
H35	0.5063	0.2419	0.7534	0.042*
C36	0.42597 (18)	0.15954 (18)	0.5877 (2)	0.0346 (5)
H36	0.4095	0.2181	0.5311	0.042*

	U11	U22	U33	U12	U13	U23
F1	0.0698 (11)	0.0542 (10)	0.0696 (11)	−0.0138 (8)	0.0319 (9)	−0.0309 (8)
F2	0.0490 (9)	0.0516 (10)	0.0853 (12)	0.0049 (7)	0.0312 (9)	−0.0195 (8)
O1	0.0509 (10)	0.0741 (14)	0.0274 (8)	0.0024 (9)	0.0089 (7)	−0.0019 (8)
O2	0.0681 (13)	0.0731 (14)	0.0428 (10)	0.0056 (11)	0.0096 (9)	−0.0301 (10)
N1	0.0346 (9)	0.0314 (9)	0.0248 (8)	0.0006 (7)	0.0119 (7)	−0.0021 (7)
N2	0.0425 (10)	0.0293 (9)	0.0234 (8)	0.0018 (7)	0.0113 (7)	0.0009 (7)
N3	0.0354 (10)	0.0617 (14)	0.0292 (9)	−0.0014 (9)	0.0117 (8)	−0.0124 (9)
C1	0.0316 (10)	0.0352 (11)	0.0239 (9)	0.0015 (8)	0.0133 (8)	−0.0014 (8)
C2	0.0474 (13)	0.0379 (12)	0.0248 (9)	0.0063 (10)	0.0151 (9)	0.0025 (8)
C3	0.0356 (11)	0.0350 (11)	0.0267 (9)	0.0027 (8)	0.0139 (8)	0.0035 (8)
C11	0.0301 (10)	0.0366 (11)	0.0233 (9)	0.0008 (8)	0.0121 (8)	−0.0025 (8)
C12	0.0364 (11)	0.0373 (11)	0.0308 (10)	0.0015 (9)	0.0127 (9)	0.0014 (9)
C13	0.0449 (13)	0.0362 (12)	0.0505 (14)	0.0009 (10)	0.0240 (11)	−0.0002 (10)
C14	0.0418 (13)	0.0435 (13)	0.0490 (13)	−0.0072 (10)	0.0243 (11)	−0.0179 (11)
C15	0.0465 (14)	0.0559 (15)	0.0288 (10)	−0.0052 (11)	0.0162 (10)	−0.0114 (10)
C16	0.0428 (12)	0.0456 (13)	0.0233 (9)	0.0011 (10)	0.0132 (9)	−0.0011 (9)
C21	0.0319 (10)	0.0334 (11)	0.0261 (9)	−0.0009 (8)	0.0128 (8)	−0.0010 (8)
C22	0.0518 (15)	0.0375 (13)	0.0737 (18)	0.0024 (11)	0.0408 (14)	0.0105 (12)
C23	0.0619 (17)	0.0300 (13)	0.091 (2)	0.0033 (12)	0.0439 (16)	0.0080 (13)
C24	0.0311 (11)	0.0396 (13)	0.0511 (14)	0.0004 (9)	0.0132 (10)	−0.0151 (10)
C25	0.0375 (12)	0.0548 (15)	0.0420 (12)	0.0000 (10)	0.0217 (10)	−0.0030 (11)
C26	0.0415 (12)	0.0412 (12)	0.0392 (11)	−0.0023 (10)	0.0221 (10)	0.0042 (9)
C31	0.0287 (10)	0.0344 (11)	0.0251 (9)	0.0009 (8)	0.0128 (8)	−0.0020 (8)
C32	0.0363 (11)	0.0330 (11)	0.0255 (9)	−0.0020 (8)	0.0118 (8)	−0.0023 (8)
C33	0.0369 (11)	0.0404 (12)	0.0256 (9)	−0.0004 (9)	0.0132 (8)	0.0004 (8)
C34	0.0273 (10)	0.0460 (12)	0.0244 (9)	0.0007 (9)	0.0094 (8)	−0.0073 (9)
C35	0.0317 (11)	0.0355 (11)	0.0376 (11)	−0.0023 (9)	0.0151 (9)	−0.0097 (9)
C36	0.0332 (11)	0.0354 (11)	0.0355 (11)	−0.0003 (9)	0.0150 (9)	−0.0007 (9)

F1—C14	1.356 (3)	C15—C16	1.385 (3)
F2—C24	1.362 (3)	C15—H15	0.9500
O1—N3	1.230 (3)	C16—H16	0.9500
O2—N3	1.232 (3)	C21—C22	1.378 (3)
N1—C1	1.289 (2)	C21—C26	1.388 (3)
N1—N2	1.379 (2)	C22—C23	1.389 (4)
N2—C31	1.369 (2)	C22—H22	0.9500
N2—C3	1.474 (3)	C23—C24	1.364 (4)
N3—C34	1.448 (3)	C23—H23	0.9500
C1—C11	1.463 (3)	C24—C25	1.360 (4)
C1—C2	1.504 (3)	C25—C26	1.383 (3)
C2—C3	1.548 (3)	C25—H25	0.9500
C2—H2A	0.9900	C26—H26	0.9500
C2—H2B	0.9900	C31—C32	1.407 (3)
C3—C21	1.514 (3)	C31—C36	1.411 (3)
C3—H3	1.0000	C32—C33	1.376 (3)
C11—C16	1.392 (3)	C32—H32	0.9500
C11—C12	1.398 (3)	C33—C34	1.387 (3)
C12—C13	1.378 (3)	C33—H33	0.9500
C12—H12	0.9500	C34—C35	1.381 (3)
C13—C14	1.380 (4)	C35—C36	1.379 (3)
C13—H13	0.9500	C35—H35	0.9500
C14—C15	1.367 (4)	C36—H36	0.9500
C1—N1—N2	108.68 (16)	C15—C16—H16	119.6
C31—N2—N1	118.70 (16)	C11—C16—H16	119.6
C31—N2—C3	127.24 (18)	C22—C21—C26	118.4 (2)
N1—N2—C3	113.53 (16)	C22—C21—C3	119.40 (18)
O1—N3—O2	123.6 (2)	C26—C21—C3	122.22 (19)
O1—N3—C34	118.9 (2)	C21—C22—C23	121.1 (2)
O2—N3—C34	117.5 (2)	C21—C22—H22	119.4
N1—C1—C11	120.38 (18)	C23—C22—H22	119.4
N1—C1—C2	113.68 (18)	C24—C23—C22	118.4 (2)
C11—C1—C2	125.93 (17)	C24—C23—H23	120.8
C1—C2—C3	102.70 (16)	C22—C23—H23	120.8
C1—C2—H2A	111.2	C25—C24—F2	119.2 (2)
C3—C2—H2A	111.2	C25—C24—C23	122.5 (2)
C1—C2—H2B	111.2	F2—C24—C23	118.3 (2)
C3—C2—H2B	111.2	C24—C25—C26	118.6 (2)
H2A—C2—H2B	109.1	C24—C25—H25	120.7
N2—C3—C21	113.17 (16)	C26—C25—H25	120.7
N2—C3—C2	101.21 (16)	C25—C26—C21	121.0 (2)
C21—C3—C2	113.27 (18)	C25—C26—H26	119.5
N2—C3—H3	109.6	C21—C26—H26	119.5
C21—C3—H3	109.6	N2—C31—C32	120.28 (18)
C2—C3—H3	109.6	N2—C31—C36	120.42 (19)
C16—C11—C12	118.82 (19)	C32—C31—C36	119.30 (19)
C16—C11—C1	121.22 (19)	C33—C32—C31	120.3 (2)
C12—C11—C1	119.97 (18)	C33—C32—H32	119.9
C13—C12—C11	120.7 (2)	C31—C32—H32	119.9
C13—C12—H12	119.7	C32—C33—C34	119.5 (2)
C11—C12—H12	119.7	C32—C33—H33	120.3
C12—C13—C14	118.5 (2)	C34—C33—H33	120.3
C12—C13—H13	120.7	C35—C34—C33	121.33 (19)
C14—C13—H13	120.7	C35—C34—N3	119.5 (2)
F1—C14—C15	119.3 (2)	C33—C34—N3	119.2 (2)
F1—C14—C13	118.1 (2)	C36—C35—C34	120.0 (2)
C15—C14—C13	122.6 (2)	C36—C35—H35	120.0
C14—C15—C16	118.6 (2)	C34—C35—H35	120.0
C14—C15—H15	120.7	C35—C36—C31	119.6 (2)
C16—C15—H15	120.7	C35—C36—H36	120.2
C15—C16—C11	120.8 (2)	C31—C36—H36	120.2
C1—N1—N2—C31	−174.73 (17)	C2—C3—C21—C26	85.0 (2)
C1—N1—N2—C3	−2.4 (2)	C26—C21—C22—C23	0.1 (4)
N2—N1—C1—C11	−179.48 (17)	C3—C21—C22—C23	179.1 (3)
N2—N1—C1—C2	−0.7 (2)	C21—C22—C23—C24	0.6 (5)
N1—C1—C2—C3	3.2 (2)	C22—C23—C24—C25	−1.0 (4)
C11—C1—C2—C3	−178.07 (19)	C22—C23—C24—F2	179.5 (3)
C31—N2—C3—C21	−62.7 (3)	F2—C24—C25—C26	−179.8 (2)
N1—N2—C3—C21	125.73 (19)	C23—C24—C25—C26	0.8 (4)
C31—N2—C3—C2	175.7 (2)	C24—C25—C26—C21	0.0 (4)
N1—N2—C3—C2	4.2 (2)	C22—C21—C26—C25	−0.4 (3)
C1—C2—C3—N2	−4.1 (2)	C3—C21—C26—C25	−179.3 (2)
C1—C2—C3—C21	−125.55 (18)	N1—N2—C31—C32	−7.3 (3)
N1—C1—C11—C16	178.05 (19)	C3—N2—C31—C32	−178.48 (19)
C2—C1—C11—C16	−0.6 (3)	N1—N2—C31—C36	173.54 (18)
N1—C1—C11—C12	−1.8 (3)	C3—N2—C31—C36	2.4 (3)
C2—C1—C11—C12	179.6 (2)	N2—C31—C32—C33	−177.13 (19)
C16—C11—C12—C13	−0.8 (3)	C36—C31—C32—C33	2.0 (3)
C1—C11—C12—C13	179.1 (2)	C31—C32—C33—C34	−0.2 (3)
C11—C12—C13—C14	0.0 (3)	C32—C33—C34—C35	−1.2 (3)
C12—C13—C14—F1	−179.0 (2)	C32—C33—C34—N3	178.99 (18)
C12—C13—C14—C15	0.8 (4)	O1—N3—C34—C35	−162.4 (2)
F1—C14—C15—C16	178.9 (2)	O2—N3—C34—C35	17.0 (3)
C13—C14—C15—C16	−0.9 (4)	O1—N3—C34—C33	17.4 (3)
C14—C15—C16—C11	0.1 (3)	O2—N3—C34—C33	−163.2 (2)
C12—C11—C16—C15	0.7 (3)	C33—C34—C35—C36	0.7 (3)
C1—C11—C16—C15	−179.1 (2)	N3—C34—C35—C36	−179.45 (18)
N2—C3—C21—C22	151.6 (2)	C34—C35—C36—C31	1.1 (3)
C2—C3—C21—C22	−94.0 (3)	N2—C31—C36—C35	176.68 (18)
N2—C3—C21—C26	−29.5 (3)	C32—C31—C36—C35	−2.4 (3)

D—H···A	D—H	H···A	D···A	D—H···A
C12—H12···O2i	0.95	2.41	3.305 (3)	157
C16—H16···F2ii	0.95	2.55	3.427 (3)	154
C26—H26···F1iii	0.95	2.56	3.494 (3)	169

Table 1

Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
C12—H12⋯O2i	0.95	2.41	3.305 (3)	157
C16—H16⋯F2ii	0.95	2.55	3.427 (3)	154
C26—H26⋯F1iii	0.95	2.56	3.494 (3)	169

Symmetry codes: (i) ; (ii) ; (iii) .