1-(2,4-Dinitro-phen-yl)-3-phenyl-4-phenyl-sulfanyl-1H-pyrazole.

In the title mol-ecule, C(21)H(14)N(4)O(4)S, the pyrazole ring forms dihedral angles of 45.6 (1), 87.7 (1) and 27.4 (1)° with the phenyl, sulfur-substituted benzene and nitro-substituted benzene rings, respectively. In the crystal, mol-ecules are connected by weak C-H⋯O and C-H⋯N hydrogen bonds into layers parallel to (010).

Related literature

For the pharmacological and medicinal properties of pyrazole compounds, see: Baraldi et al. (1998 ▶); Bruno et al. (1990 ▶); Chen & Li (1998 ▶); Cottineau et al. (2002 ▶); Londershausen (1996 ▶); Mishra et al. (1998 ▶); Smith et al. (2001 ▶).

Experimental

Crystal data

C21H14N4O4S

M = 418.42

Monoclinic,

a = 7.3062 (4) Å

b = 26.5212 (13) Å

c = 10.3361 (5) Å

β = 104.012 (1)°

V = 1943.22 (17) Å3

Z = 4

Mo Kα radiation

μ = 0.20 mm−1

T = 293 K

0.24 × 0.21 × 0.18 mm

Data collection

Bruker SMART APEX CCD diffractometer

18559 measured reflections

3426 independent reflections

3128 reflections with I > 2σ(I)

R int = 0.021

Refinement

R[F 2 > 2σ(F 2)] = 0.035

wR(F 2) = 0.091

S = 1.04

3426 reflections

271 parameters

H-atom parameters constrained

Δρmax = 0.27 e Å−3

Δρmin = −0.14 e Å−3

Data collection: SMART (Bruker, 2001 ▶); cell refinement: SAINT (Bruker, 2001 ▶); data reduction: SAINT; program(s) used to solve structure: SHELXTL (Sheldrick, 2008 ▶); program(s) used to refine structure: SHELXTL; molecular graphics: PLATON (Spek, 2009 ▶); software used to prepare material for publication: SHELXTL.

Crystal structure: contains datablock(s) global, I. DOI: 10.1107/S1600536812036914/lh5484sup1.cif

Structure factors: contains datablock(s) I. DOI: 10.1107/S1600536812036914/lh5484Isup2.hkl

Supplementary material file. DOI: 10.1107/S1600536812036914/lh5484Isup3.cml

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

C21H14N4O4S	F(000) = 864
Mr = 418.42	Dx = 1.430 Mg m−3
Monoclinic, P21/n	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: -P 2yn	Cell parameters from 4527 reflections
a = 7.3062 (4) Å	θ = 2.1–24.4°
b = 26.5212 (13) Å	µ = 0.20 mm−1
c = 10.3361 (5) Å	T = 293 K
β = 104.012 (1)°	Block, colourless
V = 1943.22 (17) Å3	0.24 × 0.21 × 0.18 mm
Z = 4

Bruker SMART APEX CCD diffractometer	3128 reflections with I > 2σ(I)
Radiation source: fine-focus sealed tube	Rint = 0.021
Graphite monochromator	θmax = 25.0°, θmin = 1.5°
ω scans	h = −8→8
18559 measured reflections	k = −31→31
3426 independent reflections	l = −12→12

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)] = 0.035	Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.091	H-atom parameters constrained
S = 1.04	w = 1/[σ2(Fo2) + (0.0451P)2 + 0.5673P] where P = (Fo2 + 2Fc2)/3
3426 reflections	(Δ/σ)max < 0.001
271 parameters	Δρmax = 0.27 e Å−3
0 restraints	Δρmin = −0.14 e Å−3

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.

	x	y	z	Uiso*/Ueq
N1	0.41540 (17)	0.26466 (4)	0.02430 (12)	0.0380 (3)
C11	0.4691 (2)	0.31285 (5)	−0.01058 (15)	0.0379 (3)
C12	0.5120 (2)	0.34984 (6)	0.08788 (16)	0.0466 (4)
H12	0.5059	0.3421	0.1745	0.056*
C13	0.5635 (3)	0.39766 (6)	0.05891 (17)	0.0510 (4)
H13	0.5969	0.4217	0.1259	0.061*
C14	0.5647 (2)	0.40930 (6)	−0.07041 (17)	0.0458 (4)
C15	0.5206 (2)	0.37446 (6)	−0.17104 (16)	0.0453 (4)
H15	0.5197	0.3832	−0.2583	0.054*
C16	0.4775 (2)	0.32614 (6)	−0.13962 (15)	0.0407 (3)
N3	0.6219 (2)	0.46010 (6)	−0.10176 (19)	0.0597 (4)
O31	0.5928 (2)	0.47181 (5)	−0.21916 (17)	0.0820 (5)
O32	0.6962 (2)	0.48746 (5)	−0.00956 (17)	0.0849 (5)
N4	0.4608 (2)	0.28911 (6)	−0.24824 (15)	0.0546 (4)
O41	0.3765 (2)	0.30239 (6)	−0.35976 (13)	0.0816 (5)
O42	0.5384 (2)	0.24840 (5)	−0.22055 (15)	0.0727 (4)
N2	0.48161 (17)	0.24827 (4)	0.15338 (12)	0.0385 (3)
C3	0.4084 (2)	0.20278 (5)	0.15590 (14)	0.0363 (3)
C31	0.4517 (2)	0.17255 (5)	0.27946 (14)	0.0379 (3)
C32	0.4992 (2)	0.12194 (6)	0.27580 (16)	0.0447 (4)
H32	0.5016	0.1070	0.1948	0.054*
C33	0.5428 (3)	0.09357 (6)	0.39095 (17)	0.0518 (4)
H33	0.5753	0.0598	0.3875	0.062*
C34	0.5382 (3)	0.11532 (7)	0.51093 (17)	0.0565 (5)
H34	0.5673	0.0962	0.5886	0.068*
C35	0.4907 (2)	0.16534 (7)	0.51629 (16)	0.0536 (4)
H35	0.4879	0.1799	0.5977	0.064*
C36	0.4472 (2)	0.19411 (6)	0.40134 (15)	0.0439 (4)
H36	0.4149	0.2279	0.4055	0.053*
C4	0.2922 (2)	0.18993 (5)	0.02874 (14)	0.0380 (3)
S1	0.15552 (6)	0.135789 (14)	−0.01962 (4)	0.04436 (13)
C41	0.3132 (2)	0.09507 (6)	−0.07662 (15)	0.0454 (4)
C42	0.4896 (3)	0.10892 (7)	−0.08882 (18)	0.0576 (4)
H42	0.5346	0.1413	−0.0656	0.069*
C43	0.5999 (3)	0.07424 (9)	−0.1360 (2)	0.0716 (6)
H43	0.7196	0.0834	−0.1437	0.086*
C44	0.5341 (4)	0.02652 (9)	−0.1715 (2)	0.0768 (6)
H44	0.6087	0.0035	−0.2034	0.092*
C45	0.3590 (4)	0.01295 (8)	−0.1596 (2)	0.0745 (6)
H45	0.3141	−0.0193	−0.1841	0.089*
C46	0.2477 (3)	0.04661 (6)	−0.11152 (18)	0.0588 (5)
H46	0.1291	0.0369	−0.1025	0.071*
C5	0.2996 (2)	0.23037 (5)	−0.05062 (15)	0.0387 (3)
H5	0.2367	0.2338	−0.1399	0.046*

	U11	U22	U33	U12	U13	U23
N1	0.0427 (7)	0.0330 (6)	0.0352 (6)	−0.0002 (5)	0.0035 (5)	−0.0003 (5)
C11	0.0379 (8)	0.0341 (7)	0.0398 (8)	0.0013 (6)	0.0060 (6)	−0.0006 (6)
C12	0.0599 (10)	0.0391 (8)	0.0402 (9)	−0.0022 (7)	0.0109 (7)	−0.0027 (7)
C13	0.0608 (10)	0.0377 (8)	0.0527 (10)	−0.0039 (7)	0.0099 (8)	−0.0083 (7)
C14	0.0438 (9)	0.0337 (8)	0.0589 (10)	−0.0004 (6)	0.0107 (7)	0.0027 (7)
C15	0.0428 (8)	0.0487 (9)	0.0446 (9)	−0.0008 (7)	0.0108 (7)	0.0065 (7)
C16	0.0396 (8)	0.0420 (8)	0.0397 (8)	−0.0025 (6)	0.0082 (6)	−0.0050 (6)
N3	0.0548 (9)	0.0419 (8)	0.0835 (12)	0.0016 (7)	0.0189 (8)	0.0118 (8)
O31	0.0934 (11)	0.0606 (9)	0.0907 (11)	−0.0049 (8)	0.0199 (9)	0.0289 (8)
O32	0.1012 (12)	0.0454 (8)	0.1062 (12)	−0.0240 (8)	0.0213 (9)	−0.0121 (8)
N4	0.0597 (9)	0.0609 (10)	0.0481 (9)	−0.0199 (7)	0.0225 (7)	−0.0143 (7)
O41	0.1011 (11)	0.1023 (12)	0.0392 (7)	−0.0322 (9)	0.0129 (7)	−0.0093 (7)
O42	0.0884 (10)	0.0552 (8)	0.0825 (10)	−0.0049 (7)	0.0366 (8)	−0.0259 (7)
N2	0.0425 (7)	0.0372 (7)	0.0334 (6)	−0.0002 (5)	0.0043 (5)	−0.0010 (5)
C3	0.0366 (7)	0.0344 (7)	0.0371 (8)	0.0020 (6)	0.0074 (6)	−0.0021 (6)
C31	0.0361 (7)	0.0401 (8)	0.0359 (8)	−0.0031 (6)	0.0056 (6)	−0.0009 (6)
C32	0.0518 (9)	0.0427 (8)	0.0379 (8)	0.0027 (7)	0.0076 (7)	−0.0020 (6)
C33	0.0608 (10)	0.0427 (9)	0.0481 (10)	0.0021 (8)	0.0057 (8)	0.0061 (7)
C34	0.0648 (11)	0.0596 (11)	0.0404 (9)	−0.0086 (9)	0.0032 (8)	0.0107 (8)
C35	0.0606 (10)	0.0646 (11)	0.0345 (8)	−0.0125 (9)	0.0097 (7)	−0.0057 (7)
C36	0.0448 (9)	0.0433 (8)	0.0422 (8)	−0.0065 (7)	0.0078 (7)	−0.0064 (7)
C4	0.0390 (8)	0.0343 (7)	0.0384 (8)	−0.0003 (6)	0.0052 (6)	−0.0029 (6)
S1	0.0456 (2)	0.0389 (2)	0.0466 (2)	−0.00736 (16)	0.00724 (17)	−0.00609 (16)
C41	0.0594 (10)	0.0408 (8)	0.0329 (8)	0.0021 (7)	0.0050 (7)	−0.0023 (6)
C42	0.0671 (12)	0.0552 (10)	0.0534 (10)	−0.0013 (9)	0.0199 (9)	−0.0060 (8)
C43	0.0754 (13)	0.0867 (15)	0.0574 (12)	0.0130 (11)	0.0250 (10)	−0.0043 (11)
C44	0.1021 (18)	0.0722 (14)	0.0556 (12)	0.0298 (13)	0.0180 (11)	−0.0104 (10)
C45	0.1061 (18)	0.0479 (11)	0.0631 (12)	0.0123 (11)	0.0081 (12)	−0.0130 (9)
C46	0.0742 (12)	0.0433 (9)	0.0542 (10)	−0.0012 (8)	0.0061 (9)	−0.0061 (8)
C5	0.0406 (8)	0.0367 (7)	0.0353 (8)	0.0014 (6)	0.0025 (6)	−0.0025 (6)

N1—C5	1.3508 (18)	C32—H32	0.9300
N1—N2	1.3749 (17)	C33—C34	1.375 (3)
N1—C11	1.4093 (18)	C33—H33	0.9300
C11—C12	1.393 (2)	C34—C35	1.376 (3)
C11—C16	1.395 (2)	C34—H34	0.9300
C12—C13	1.376 (2)	C35—C36	1.383 (2)
C12—H12	0.9300	C35—H35	0.9300
C13—C14	1.374 (2)	C36—H36	0.9300
C13—H13	0.9300	C4—C5	1.359 (2)
C14—C15	1.370 (2)	C4—S1	1.7515 (14)
C14—N3	1.470 (2)	S1—C41	1.7805 (17)
C15—C16	1.377 (2)	C41—C42	1.375 (2)
C15—H15	0.9300	C41—C46	1.388 (2)
C16—N4	1.474 (2)	C42—C43	1.387 (3)
N3—O32	1.216 (2)	C42—H42	0.9300
N3—O31	1.220 (2)	C43—C44	1.372 (3)
N4—O41	1.220 (2)	C43—H43	0.9300
N4—O42	1.221 (2)	C44—C45	1.363 (3)
N2—C3	1.3226 (18)	C44—H44	0.9300
C3—C4	1.423 (2)	C45—C46	1.378 (3)
C3—C31	1.476 (2)	C45—H45	0.9300
C31—C32	1.389 (2)	C46—H46	0.9300
C31—C36	1.391 (2)	C5—H5	0.9300
C32—C33	1.379 (2)
C5—N1—N2	111.59 (11)	C34—C33—C32	119.89 (16)
C5—N1—C11	129.66 (12)	C34—C33—H33	120.1
N2—N1—C11	118.72 (11)	C32—C33—H33	120.1
C12—C11—C16	117.79 (14)	C33—C34—C35	120.16 (16)
C12—C11—N1	118.62 (13)	C33—C34—H34	119.9
C16—C11—N1	123.57 (13)	C35—C34—H34	119.9
C13—C12—C11	120.99 (15)	C34—C35—C36	120.34 (15)
C13—C12—H12	119.5	C34—C35—H35	119.8
C11—C12—H12	119.5	C36—C35—H35	119.8
C14—C13—C12	119.03 (15)	C35—C36—C31	120.03 (15)
C14—C13—H13	120.5	C35—C36—H36	120.0
C12—C13—H13	120.5	C31—C36—H36	120.0
C15—C14—C13	122.07 (15)	C5—C4—C3	105.46 (12)
C15—C14—N3	118.56 (15)	C5—C4—S1	125.31 (11)
C13—C14—N3	119.32 (15)	C3—C4—S1	129.16 (11)
C14—C15—C16	118.29 (15)	C4—S1—C41	102.81 (7)
C14—C15—H15	120.9	C42—C41—C46	119.70 (17)
C16—C15—H15	120.9	C42—C41—S1	124.36 (13)
C15—C16—C11	121.73 (14)	C46—C41—S1	115.94 (14)
C15—C16—N4	114.95 (14)	C41—C42—C43	119.49 (18)
C11—C16—N4	123.04 (14)	C41—C42—H42	120.3
O32—N3—O31	124.40 (16)	C43—C42—H42	120.3
O32—N3—C14	118.10 (16)	C44—C43—C42	120.7 (2)
O31—N3—C14	117.51 (16)	C44—C43—H43	119.7
O41—N4—O42	125.20 (16)	C42—C43—H43	119.7
O41—N4—C16	117.19 (16)	C45—C44—C43	119.7 (2)
O42—N4—C16	117.54 (15)	C45—C44—H44	120.2
C3—N2—N1	104.98 (11)	C43—C44—H44	120.2
N2—C3—C4	110.73 (12)	C44—C45—C46	120.7 (2)
N2—C3—C31	120.64 (12)	C44—C45—H45	119.7
C4—C3—C31	128.63 (13)	C46—C45—H45	119.7
C32—C31—C36	118.85 (14)	C45—C46—C41	119.8 (2)
C32—C31—C3	120.26 (13)	C45—C46—H46	120.1
C36—C31—C3	120.89 (13)	C41—C46—H46	120.1
C33—C32—C31	120.73 (15)	N1—C5—C4	107.22 (13)
C33—C32—H32	119.6	N1—C5—H5	126.4
C31—C32—H32	119.6	C4—C5—H5	126.4
C5—N1—C11—C12	150.11 (15)	N2—C3—C31—C36	45.2 (2)
N2—N1—C11—C12	−27.9 (2)	C4—C3—C31—C36	−135.11 (16)
C5—N1—C11—C16	−28.3 (2)	C36—C31—C32—C33	−0.6 (2)
N2—N1—C11—C16	153.72 (14)	C3—C31—C32—C33	178.96 (15)
C16—C11—C12—C13	−0.9 (2)	C31—C32—C33—C34	0.4 (3)
N1—C11—C12—C13	−179.36 (15)	C32—C33—C34—C35	−0.2 (3)
C11—C12—C13—C14	2.6 (3)	C33—C34—C35—C36	0.0 (3)
C12—C13—C14—C15	−1.5 (3)	C34—C35—C36—C31	−0.2 (2)
C12—C13—C14—N3	−179.20 (15)	C32—C31—C36—C35	0.4 (2)
C13—C14—C15—C16	−1.3 (2)	C3—C31—C36—C35	−179.10 (14)
N3—C14—C15—C16	176.38 (14)	N2—C3—C4—C5	−0.01 (17)
C14—C15—C16—C11	3.1 (2)	C31—C3—C4—C5	−179.74 (14)
C14—C15—C16—N4	−170.88 (14)	N2—C3—C4—S1	−176.96 (11)
C12—C11—C16—C15	−2.1 (2)	C31—C3—C4—S1	3.3 (2)
N1—C11—C16—C15	176.35 (14)	C5—C4—S1—C41	91.96 (14)
C12—C11—C16—N4	171.45 (14)	C3—C4—S1—C41	−91.65 (15)
N1—C11—C16—N4	−10.1 (2)	C4—S1—C41—C42	−6.10 (16)
C15—C14—N3—O32	−165.63 (16)	C4—S1—C41—C46	174.66 (13)
C13—C14—N3—O32	12.1 (2)	C46—C41—C42—C43	0.0 (3)
C15—C14—N3—O31	13.8 (2)	S1—C41—C42—C43	−179.18 (14)
C13—C14—N3—O31	−168.44 (17)	C41—C42—C43—C44	0.5 (3)
C15—C16—N4—O41	−42.7 (2)	C42—C43—C44—C45	−0.3 (3)
C11—C16—N4—O41	143.32 (16)	C43—C44—C45—C46	−0.4 (3)
C15—C16—N4—O42	134.48 (16)	C44—C45—C46—C41	0.9 (3)
C11—C16—N4—O42	−39.4 (2)	C42—C41—C46—C45	−0.7 (3)
C5—N1—N2—C3	1.50 (16)	S1—C41—C46—C45	178.53 (15)
C11—N1—N2—C3	179.83 (12)	N2—N1—C5—C4	−1.54 (17)
N1—N2—C3—C4	−0.88 (16)	C11—N1—C5—C4	−179.63 (14)
N1—N2—C3—C31	178.87 (12)	C3—C4—C5—N1	0.92 (16)
N2—C3—C31—C32	−134.32 (15)	S1—C4—C5—N1	178.02 (11)
C4—C3—C31—C32	45.4 (2)

D—H···A	D—H	H···A	D···A	D—H···A
C35—H35···O42i	0.93	2.58	3.452 (2)	157
C5—H5···N2ii	0.93	2.52	3.411 (2)	161

Table 1

Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
C35—H35⋯O42i	0.93	2.58	3.452 (2)	157
C5—H5⋯N2ii	0.93	2.52	3.411 (2)	161

Symmetry codes: (i) ; (ii) .