Crystal structure of 1-(2,4-di-nitro-phen-yl)-3,5-diphenyl-1H-pyrazole.

In the title mol-ecule, C21H14N4O4, the phenyl rings make dihedral angles of 39.61 (8) and 9.4 (1)°, respectively, with the central pyrazole ring. The dihedral angle between the pyrazole and di-nitro-phenyl rings is 46.95 (5)°. In the crystal, mol-ecules pack in helical stacks parallel to the a axis aided by weak C-H⋯O inter-actions.

Related literature

For the synthesis and pharmaceutical activities of pyrazole-containing compounds, see: Szabó et al. (2008 ▸); Tanitame et al. (2005 ▸); Cottineau et al. (2002 ▸); Mokhtar & El-Khawass (1988 ▸); Rida et al. (2009 ▸); Abadi et al. (2003 ▸); Sharma et al. (2014 ▸); Mykhailiuk (2015 ▸).

Experimental

Crystal data

C21H14N4O4

M = 386.36

Orthorhombic,

a = 7.2170 (5) Å

b = 12.9467 (10) Å

c = 19.3006 (14) Å

V = 1803.4 (2) Å3

Z = 4

Mo Kα radiation

μ = 0.10 mm−1

T = 150 K

0.18 × 0.18 × 0.17 mm

Data collection

Bruker SMART APEX CCD diffractometer

Absorption correction: multi-scan (SADABS; Bruker, 2015 ▸) T min = 0.78, T max = 0.98

17283 measured reflections

4635 independent reflections

3401 reflections with I > 2σ(I)

R int = 0.045

Refinement

R[F 2 > 2σ(F 2)] = 0.042

wR(F 2) = 0.096

S = 1.03

4635 reflections

262 parameters

H-atom parameters constrained

Δρmax = 0.21 e Å−3

Δρmin = −0.17 e Å−3

Absolute structure: Flack x determined using 1193 quotients [(I +)−(I −)]/[(I +)+(I −)] (Parsons et al., 2013 ▸)

Absolute structure parameter: −0.3 (8)

Data collection: APEX2 (Bruker, 2015 ▸); cell refinement: SAINT (Bruker, 2015 ▸); data reduction: SAINT; program(s) used to solve structure: SHELXT (Sheldrick, 2015a ▸); program(s) used to refine structure: SHELXL2014 (Sheldrick, 2015b ▸); molecular graphics: DIAMOND (Brandenburg & Putz, 2012 ▸); software used to prepare material for publication: SHELXTL (Sheldrick, 2008 ▸).

Crystal structure: contains datablock(s) global, I. DOI: 10.1107/S2056989015021350/qm2114sup1.cif

Structure factors: contains datablock(s) I. DOI: 10.1107/S2056989015021350/qm2114Isup2.hkl

Click here for additional data file.

Supporting information file. DOI: 10.1107/S2056989015021350/qm2114Isup3.cml

Click here for additional data file.

. DOI: 10.1107/S2056989015021350/qm2114fig1.tif

The title mol­ecule with the labeling scheme and 50% probability ellipsoids.

Click here for additional data file.

a . DOI: 10.1107/S2056989015021350/qm2114fig2.tif

Packing viewed down the a axis with weak C—H⋯O inter­actions depicted as dotted lines.

Click here for additional data file.

b . DOI: 10.1107/S2056989015021350/qm2114fig3.tif

Packing viewed down the b axis with weak C—H⋯O inter­actions depicted as dotted lines.

CCDC reference: 1436135

Additional supporting information: crystallographic information; 3D view; checkCIF report

C21H14N4O4	Dx = 1.423 Mg m−3
Mr = 386.36	Mo Kα radiation, λ = 0.71073 Å
Orthorhombic, P212121	Cell parameters from 4944 reflections
a = 7.2170 (5) Å	θ = 2.6–24.1°
b = 12.9467 (10) Å	µ = 0.10 mm−1
c = 19.3006 (14) Å	T = 150 K
V = 1803.4 (2) Å3	Block, yellow-orange
Z = 4	0.18 × 0.18 × 0.17 mm
F(000) = 800

Bruker SMART APEX CCD diffractometer	4635 independent reflections
Radiation source: fine-focus sealed tube	3401 reflections with I > 2σ(I)
Graphite monochromator	Rint = 0.045
Detector resolution: 8.3333 pixels mm-1	θmax = 29.1°, θmin = 1.9°
φ and ω scans	h = −9→9
Absorption correction: multi-scan (SADABS; Bruker, 2015)	k = −17→16
Tmin = 0.78, Tmax = 0.98	l = −26→26
17283 measured reflections

Refinement on F2	Secondary atom site location: difference Fourier map
Least-squares matrix: full	Hydrogen site location: inferred from neighbouring sites
R[F2 > 2σ(F2)] = 0.042	H-atom parameters constrained
wR(F2) = 0.096	w = 1/[σ2(Fo2) + (0.0375P)2] where P = (Fo2 + 2Fc2)/3
S = 1.03	(Δ/σ)max < 0.001
4635 reflections	Δρmax = 0.21 e Å−3
262 parameters	Δρmin = −0.17 e Å−3
0 restraints	Absolute structure: Flack x determined using 1193 quotients [(I+)-(I-)]/[(I+)+(I-)] (Parsons et al., 2013)
Primary atom site location: structure-invariant direct methods	Absolute structure parameter: −0.3 (8)

Experimental. The diffraction data were collected in three sets of 363 frames (0.5° width in ω) at φ = 0, 120 and 240°. A scan time of 40 sec/frame was used.

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. H-atoms attached to carbon were placed in calculated positions (C—H = 0.95 Å). All were included as riding contributions with isotropic displacement parameters 1.2 times those of the attached atoms.

	x	y	z	Uiso*/Ueq
O1	0.0335 (2)	0.48865 (13)	0.50537 (9)	0.0369 (4)
O2	0.1081 (3)	0.56459 (13)	0.40944 (10)	0.0466 (5)
O3	0.1707 (3)	0.33782 (17)	0.21292 (9)	0.0617 (6)
O4	0.2274 (3)	0.17545 (18)	0.22859 (9)	0.0625 (6)
N1	0.2445 (3)	0.26495 (13)	0.58248 (9)	0.0280 (4)
N2	0.3024 (2)	0.33719 (12)	0.53522 (9)	0.0261 (4)
N3	0.1040 (2)	0.48950 (14)	0.44764 (10)	0.0319 (4)
N4	0.2043 (3)	0.2633 (2)	0.24971 (11)	0.0464 (6)
C1	0.3782 (3)	0.42265 (15)	0.56610 (11)	0.0268 (5)
C2	0.3640 (3)	0.40575 (17)	0.63603 (11)	0.0284 (5)
H2	0.4021	0.4511	0.6720	0.034*
C3	0.2814 (3)	0.30750 (17)	0.64398 (11)	0.0279 (5)
C4	0.4636 (3)	0.50690 (16)	0.52632 (11)	0.0260 (5)
C5	0.5697 (3)	0.48621 (18)	0.46740 (12)	0.0305 (5)
H5	0.5917	0.4167	0.4539	0.037*
C6	0.6430 (3)	0.56641 (17)	0.42857 (12)	0.0334 (5)
H6	0.7123	0.5519	0.3879	0.040*
C7	0.6152 (3)	0.66760 (18)	0.44903 (13)	0.0377 (6)
H7	0.6639	0.7226	0.4220	0.045*
C8	0.5167 (4)	0.68884 (19)	0.50876 (13)	0.0379 (6)
H8	0.5010	0.7583	0.5235	0.045*
C9	0.4406 (3)	0.60891 (17)	0.54720 (12)	0.0338 (5)
H9	0.3723	0.6239	0.5881	0.041*
C10	0.2384 (3)	0.24957 (17)	0.70755 (11)	0.0297 (5)
C11	0.2507 (3)	0.29519 (19)	0.77262 (12)	0.0377 (6)
H11	0.2866	0.3656	0.7764	0.045*
C12	0.2113 (4)	0.2394 (2)	0.83180 (13)	0.0456 (7)
H12	0.2220	0.2715	0.8759	0.055*
C13	0.1569 (4)	0.1382 (2)	0.82749 (13)	0.0459 (7)
H13	0.1295	0.1004	0.8684	0.055*
C14	0.1421 (4)	0.0917 (2)	0.76378 (14)	0.0491 (7)
H14	0.1038	0.0217	0.7605	0.059*
C15	0.1830 (4)	0.14687 (18)	0.70429 (13)	0.0413 (6)
H15	0.1731	0.1139	0.6605	0.050*
C16	0.2618 (3)	0.31836 (16)	0.46461 (10)	0.0254 (4)
C17	0.1820 (3)	0.39223 (16)	0.42117 (11)	0.0277 (5)
C18	0.1647 (3)	0.37515 (18)	0.35076 (12)	0.0329 (5)
H18	0.1168	0.4271	0.3210	0.040*
C19	0.2188 (3)	0.28098 (18)	0.32499 (11)	0.0328 (5)
C20	0.2869 (3)	0.20328 (18)	0.36702 (12)	0.0332 (5)
H20	0.3171	0.1376	0.3482	0.040*
C21	0.3104 (3)	0.22280 (16)	0.43688 (11)	0.0293 (5)
H21	0.3600	0.1707	0.4662	0.035*

	U11	U22	U33	U12	U13	U23
O1	0.0335 (9)	0.0348 (10)	0.0423 (10)	0.0026 (7)	0.0025 (8)	0.0002 (8)
O2	0.0523 (11)	0.0286 (9)	0.0588 (11)	0.0032 (8)	−0.0003 (10)	0.0159 (9)
O3	0.0703 (13)	0.0840 (15)	0.0308 (10)	−0.0060 (12)	−0.0092 (9)	0.0152 (10)
O4	0.0708 (14)	0.0772 (15)	0.0394 (11)	0.0100 (12)	−0.0055 (10)	−0.0219 (10)
N1	0.0297 (10)	0.0279 (10)	0.0264 (9)	−0.0008 (8)	−0.0002 (8)	0.0051 (8)
N2	0.0293 (9)	0.0228 (9)	0.0261 (9)	−0.0012 (8)	−0.0007 (7)	0.0017 (7)
N3	0.0264 (9)	0.0276 (10)	0.0418 (12)	−0.0005 (8)	−0.0052 (9)	0.0052 (9)
N4	0.0402 (12)	0.0702 (17)	0.0289 (12)	−0.0053 (12)	−0.0022 (9)	−0.0018 (12)
C1	0.0261 (11)	0.0231 (11)	0.0313 (12)	0.0014 (9)	−0.0008 (9)	−0.0022 (9)
C2	0.0300 (11)	0.0255 (11)	0.0297 (11)	−0.0004 (9)	−0.0019 (10)	−0.0021 (9)
C3	0.0276 (11)	0.0303 (12)	0.0256 (11)	0.0037 (9)	−0.0006 (9)	−0.0009 (9)
C4	0.0235 (11)	0.0260 (12)	0.0286 (11)	−0.0011 (9)	−0.0032 (9)	−0.0004 (9)
C5	0.0279 (12)	0.0264 (12)	0.0372 (13)	0.0003 (9)	−0.0004 (10)	−0.0019 (10)
C6	0.0280 (12)	0.0363 (13)	0.0360 (13)	−0.0027 (10)	0.0023 (10)	0.0017 (11)
C7	0.0347 (12)	0.0318 (13)	0.0467 (14)	−0.0085 (10)	−0.0016 (12)	0.0058 (11)
C8	0.0421 (14)	0.0253 (13)	0.0462 (15)	−0.0045 (11)	−0.0027 (11)	−0.0031 (11)
C9	0.0396 (13)	0.0282 (12)	0.0335 (12)	−0.0011 (10)	0.0005 (11)	−0.0059 (11)
C10	0.0274 (11)	0.0340 (13)	0.0278 (11)	0.0006 (10)	−0.0014 (10)	0.0005 (10)
C11	0.0420 (14)	0.0382 (14)	0.0329 (13)	−0.0083 (11)	0.0034 (11)	−0.0026 (10)
C12	0.0544 (17)	0.0531 (16)	0.0293 (13)	−0.0042 (14)	0.0032 (12)	−0.0003 (12)
C13	0.0553 (17)	0.0519 (17)	0.0304 (14)	−0.0078 (14)	0.0004 (12)	0.0116 (12)
C14	0.0721 (19)	0.0360 (15)	0.0394 (14)	−0.0103 (14)	−0.0031 (14)	0.0091 (12)
C15	0.0616 (16)	0.0329 (13)	0.0293 (12)	−0.0054 (12)	−0.0031 (12)	0.0015 (10)
C16	0.0234 (10)	0.0264 (11)	0.0265 (11)	−0.0034 (9)	−0.0013 (9)	0.0024 (9)
C17	0.0257 (11)	0.0255 (11)	0.0320 (12)	−0.0043 (9)	−0.0007 (9)	0.0029 (10)
C18	0.0300 (12)	0.0364 (13)	0.0324 (12)	−0.0055 (10)	−0.0040 (10)	0.0092 (10)
C19	0.0315 (12)	0.0430 (14)	0.0240 (11)	−0.0077 (11)	−0.0020 (10)	0.0011 (10)
C20	0.0321 (12)	0.0335 (13)	0.0340 (13)	−0.0033 (10)	0.0014 (10)	−0.0056 (10)
C21	0.0294 (12)	0.0288 (12)	0.0296 (12)	−0.0015 (9)	−0.0025 (9)	0.0022 (9)

O1—N3	1.225 (2)	C8—C9	1.387 (3)
O2—N3	1.220 (2)	C8—H8	0.9500
O3—N4	1.222 (3)	C9—H9	0.9500
O4—N4	1.220 (3)	C10—C15	1.390 (3)
N1—C3	1.335 (3)	C10—C11	1.391 (3)
N1—N2	1.372 (2)	C11—C12	1.381 (3)
N2—C1	1.371 (3)	C11—H11	0.9500
N2—C16	1.415 (3)	C12—C13	1.371 (4)
N3—C17	1.471 (3)	C12—H12	0.9500
N4—C19	1.475 (3)	C13—C14	1.373 (4)
C1—C2	1.371 (3)	C13—H13	0.9500
C1—C4	1.469 (3)	C14—C15	1.384 (3)
C2—C3	1.413 (3)	C14—H14	0.9500
C2—H2	0.9500	C15—H15	0.9500
C3—C10	1.471 (3)	C16—C21	1.393 (3)
C4—C9	1.391 (3)	C16—C17	1.396 (3)
C4—C5	1.397 (3)	C17—C18	1.382 (3)
C5—C6	1.385 (3)	C18—C19	1.373 (3)
C5—H5	0.9500	C18—H18	0.9500
C6—C7	1.383 (3)	C19—C20	1.383 (3)
C6—H6	0.9500	C20—C21	1.382 (3)
C7—C8	1.382 (3)	C20—H20	0.9500
C7—H7	0.9500	C21—H21	0.9500
C3—N1—N2	104.42 (17)	C15—C10—C11	117.7 (2)
C1—N2—N1	112.51 (17)	C15—C10—C3	120.71 (19)
C1—N2—C16	129.82 (17)	C11—C10—C3	121.5 (2)
N1—N2—C16	117.39 (16)	C12—C11—C10	120.8 (2)
O2—N3—O1	124.5 (2)	C12—C11—H11	119.6
O2—N3—C17	117.58 (19)	C10—C11—H11	119.6
O1—N3—C17	117.85 (17)	C13—C12—C11	120.6 (2)
O4—N4—O3	124.7 (2)	C13—C12—H12	119.7
O4—N4—C19	117.7 (2)	C11—C12—H12	119.7
O3—N4—C19	117.6 (2)	C12—C13—C14	119.7 (2)
N2—C1—C2	105.63 (19)	C12—C13—H13	120.1
N2—C1—C4	122.64 (19)	C14—C13—H13	120.1
C2—C1—C4	131.6 (2)	C13—C14—C15	120.0 (2)
C1—C2—C3	106.38 (19)	C13—C14—H14	120.0
C1—C2—H2	126.8	C15—C14—H14	120.0
C3—C2—H2	126.8	C14—C15—C10	121.2 (2)
N1—C3—C2	111.04 (18)	C14—C15—H15	119.4
N1—C3—C10	119.27 (18)	C10—C15—H15	119.4
C2—C3—C10	129.68 (19)	C21—C16—C17	118.79 (19)
C9—C4—C5	118.9 (2)	C21—C16—N2	118.11 (18)
C9—C4—C1	120.2 (2)	C17—C16—N2	123.06 (18)
C5—C4—C1	120.87 (19)	C18—C17—C16	121.2 (2)
C6—C5—C4	120.4 (2)	C18—C17—N3	116.36 (19)
C6—C5—H5	119.8	C16—C17—N3	122.39 (18)
C4—C5—H5	119.8	C19—C18—C17	118.2 (2)
C7—C6—C5	120.0 (2)	C19—C18—H18	120.9
C7—C6—H6	120.0	C17—C18—H18	120.9
C5—C6—H6	120.0	C18—C19—C20	122.3 (2)
C8—C7—C6	120.1 (2)	C18—C19—N4	118.3 (2)
C8—C7—H7	120.0	C20—C19—N4	119.4 (2)
C6—C7—H7	120.0	C21—C20—C19	118.9 (2)
C7—C8—C9	120.1 (2)	C21—C20—H20	120.6
C7—C8—H8	120.0	C19—C20—H20	120.6
C9—C8—H8	120.0	C20—C21—C16	120.4 (2)
C8—C9—C4	120.4 (2)	C20—C21—H21	119.8
C8—C9—H9	119.8	C16—C21—H21	119.8
C4—C9—H9	119.8
C3—N1—N2—C1	1.4 (2)	C11—C12—C13—C14	0.3 (4)
C3—N1—N2—C16	−173.15 (17)	C12—C13—C14—C15	0.3 (5)
N1—N2—C1—C2	−1.6 (2)	C13—C14—C15—C10	−0.3 (4)
C16—N2—C1—C2	172.1 (2)	C11—C10—C15—C14	−0.2 (4)
N1—N2—C1—C4	174.98 (19)	C3—C10—C15—C14	−179.9 (3)
C16—N2—C1—C4	−11.4 (3)	C1—N2—C16—C21	135.4 (2)
N2—C1—C2—C3	1.1 (2)	N1—N2—C16—C21	−51.2 (3)
C4—C1—C2—C3	−175.0 (2)	C1—N2—C16—C17	−42.3 (3)
N2—N1—C3—C2	−0.6 (2)	N1—N2—C16—C17	131.2 (2)
N2—N1—C3—C10	−179.24 (18)	C21—C16—C17—C18	−5.3 (3)
C1—C2—C3—N1	−0.3 (2)	N2—C16—C17—C18	172.3 (2)
C1—C2—C3—C10	178.1 (2)	C21—C16—C17—N3	171.68 (19)
N2—C1—C4—C9	142.0 (2)	N2—C16—C17—N3	−10.7 (3)
C2—C1—C4—C9	−42.4 (4)	O2—N3—C17—C18	−32.5 (3)
N2—C1—C4—C5	−38.4 (3)	O1—N3—C17—C18	144.9 (2)
C2—C1—C4—C5	137.2 (3)	O2—N3—C17—C16	150.3 (2)
C9—C4—C5—C6	−3.2 (3)	O1—N3—C17—C16	−32.3 (3)
C1—C4—C5—C6	177.2 (2)	C16—C17—C18—C19	3.6 (3)
C4—C5—C6—C7	1.6 (3)	N3—C17—C18—C19	−173.60 (19)
C5—C6—C7—C8	1.0 (4)	C17—C18—C19—C20	0.8 (3)
C6—C7—C8—C9	−2.0 (4)	C17—C18—C19—N4	−178.7 (2)
C7—C8—C9—C4	0.4 (4)	O4—N4—C19—C18	−169.8 (2)
C5—C4—C9—C8	2.2 (3)	O3—N4—C19—C18	10.5 (3)
C1—C4—C9—C8	−178.2 (2)	O4—N4—C19—C20	10.6 (3)
N1—C3—C10—C15	8.4 (3)	O3—N4—C19—C20	−169.1 (2)
C2—C3—C10—C15	−169.9 (2)	C18—C19—C20—C21	−3.4 (3)
N1—C3—C10—C11	−171.3 (2)	N4—C19—C20—C21	176.2 (2)
C2—C3—C10—C11	10.4 (4)	C19—C20—C21—C16	1.6 (3)
C15—C10—C11—C12	0.8 (4)	C17—C16—C21—C20	2.7 (3)
C3—C10—C11—C12	−179.5 (2)	N2—C16—C21—C20	−175.03 (19)
C10—C11—C12—C13	−0.8 (4)

D—H···A	D—H	H···A	D···A	D—H···A
C21—H21···O1i	0.95	2.48	3.366 (3)	156

Table 1

Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
C21—H21⋯O1i	0.95	2.48	3.366 (3)	156

Symmetry code: (i) .