3-Oxo-N',2-diphenyl-2,3-di-hydro-1H-pyrazole-4-carbohydrazide.

In the title compound, C16H14N4O2, the pyrazole ring makes a dihedral angle of 10.49 (8)° with its N-bound phenyl group, while it is nearly perpendicular to the other phenyl ring [dihedral angle = 88.47 (5)°]. The mol-ecular conformation is stabilized by intra-molecular C-H⋯O and N-H⋯O hydrogen bonds. In the crystal, the packing involves sheets of mol-ecules parallel to (100) linked by N-H⋯O hydrogen bonds. A C-H⋯O interaction is also observed.

Related literature

For the diverse biological activities of pyrazolone compounds, see: Guckian et al. (2010 ▶); Fan et al. (2006 ▶); Castagnolo et al. (2008 ▶); Idrees et al. (2009 ▶); Abdel-Aziz et al. (2009 ▶); Manojkumar et al. (2009 ▶); Shete et al. (2011 ▶); Sujatha et al. (2009 ▶); El-Hawash et al. (2006 ▶); Kawai et al. (1997 ▶); Wu et al. (2002 ▶6). For industrial applications of pyrazolo­nes, see: Basaif et al. (2007 ▶); Ho (2005 ▶); Kirschke et al. (1984 ▶); Chande et al. (1993 ▶); El-Saraf & El-Sayed (2003 ▶). For graph-set motif notation, see: Bernstein et al. (1995 ▶).

Experimental

Crystal data

C16H14N4O2

M = 294.31

Monoclinic,

a = 8.4488 (12) Å

b = 11.5605 (17) Å

c = 14.642 (2) Å

β = 91.565 (2)°

V = 1429.6 (4) Å3

Z = 4

Mo Kα radiation

μ = 0.09 mm−1

T = 150 K

0.26 × 0.20 × 0.07 mm

Data collection

Bruker SMART APEX CCD diffractometer

Absorption correction: multi-scan (SADABS; Bruker, 2013 ▶) T min = 0.85, T max = 0.99

25571 measured reflections

3674 independent reflections

2895 reflections with I > 2σ(I)

R int = 0.049

Refinement

R[F 2 > 2σ(F 2)] = 0.043

wR(F 2) = 0.112

S = 1.03

3674 reflections

199 parameters

H-atom parameters constrained

Δρmax = 0.25 e Å−3

Δρmin = −0.21 e Å−3

Data collection: APEX2 (Bruker, 2013 ▶); cell refinement: SAINT (Bruker, 2013 ▶); data reduction: SAINT; program(s) used to solve structure: SHELXTL (Sheldrick, 2008 ▶); program(s) used to refine structure: SHELXL2014 (Sheldrick, 2008 ▶); molecular graphics: DIAMOND (Brandenburg & Putz, 2012 ▶); software used to prepare material for publication: SHELXTL.

Crystal structure: contains datablock(s) global, I. DOI: 10.1107/S1600536814012392/bt6982sup1.cif

Structure factors: contains datablock(s) I. DOI: 10.1107/S1600536814012392/bt6982Isup2.hkl

Click here for additional data file.

Supporting information file. DOI: 10.1107/S1600536814012392/bt6982Isup3.cml

CCDC reference: 1005600

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

C16H14N4O2	F(000) = 616
Mr = 294.31	Dx = 1.367 Mg m−3
Monoclinic, P21/c	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: -P 2ybc	Cell parameters from 9891 reflections
a = 8.4488 (12) Å	θ = 2.2–28.6°
b = 11.5605 (17) Å	µ = 0.09 mm−1
c = 14.642 (2) Å	T = 150 K
β = 91.565 (2)°	Plate, colourless
V = 1429.6 (4) Å3	0.26 × 0.20 × 0.07 mm
Z = 4

Bruker SMART APEX CCD diffractometer	3674 independent reflections
Radiation source: fine-focus sealed tube	2895 reflections with I > 2σ(I)
Graphite monochromator	Rint = 0.049
Detector resolution: 8.3660 pixels mm-1	θmax = 28.7°, θmin = 2.2°
φ and ω scans	h = −11→11
Absorption correction: multi-scan (SADABS; Bruker, 2013)	k = −15→15
Tmin = 0.85, Tmax = 0.99	l = −19→19
25571 measured reflections

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)] = 0.043	Hydrogen site location: mixed
wR(F2) = 0.112	H-atom parameters constrained
S = 1.03	w = 1/[σ2(Fo2) + (0.0439P)2 + 0.5339P] where P = (Fo2 + 2Fc2)/3
3674 reflections	(Δ/σ)max < 0.001
199 parameters	Δρmax = 0.25 e Å−3
0 restraints	Δρmin = −0.21 e Å−3

Geometry. Bond distances, angles etc. have been calculated using the rounded fractional coordinates. All su's are estimated from the variances of the (full) variance-covariance matrix. The cell e.s.d.'s are taken into account in the estimation of distances, angles and torsion angles

Refinement. Refinement on F2 for ALL reflections except those flagged by the user for potential systematic errors. Weighted R-factors wR and all goodnesses of fit S are based on F2, conventional R-factors R are based on F, with F set to zero for negative F2. The observed criterion of F2 > σ(F2) is used only for calculating -R-factor-obs 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
O1	0.63625 (12)	0.59121 (8)	0.76051 (6)	0.0326 (3)
O2	0.48112 (11)	0.70165 (8)	0.48802 (6)	0.0318 (3)
N1	0.72819 (12)	0.44304 (9)	0.62602 (7)	0.0271 (3)
N2	0.64406 (12)	0.54510 (9)	0.60905 (7)	0.0271 (3)
N3	0.38524 (14)	0.88161 (10)	0.66714 (7)	0.0304 (3)
N4	0.38879 (13)	0.85733 (9)	0.57481 (7)	0.0280 (3)
C1	0.89573 (15)	0.45011 (12)	0.62204 (8)	0.0284 (3)
C2	0.98148 (18)	0.34748 (14)	0.62651 (10)	0.0394 (4)
C3	1.14618 (19)	0.35060 (17)	0.62340 (11)	0.0501 (5)
C4	1.22455 (18)	0.45435 (18)	0.61602 (10)	0.0506 (6)
C5	1.13945 (18)	0.55579 (17)	0.61308 (10)	0.0468 (5)
C6	0.97471 (16)	0.55477 (13)	0.61649 (9)	0.0357 (4)
C7	0.60259 (15)	0.61338 (10)	0.67917 (8)	0.0259 (3)
C8	0.51543 (15)	0.71675 (11)	0.65311 (8)	0.0263 (3)
C9	0.46389 (16)	0.79948 (11)	0.71259 (8)	0.0285 (4)
C10	0.46608 (15)	0.75198 (11)	0.56291 (8)	0.0264 (3)
C11	0.31419 (16)	0.93191 (11)	0.50934 (8)	0.0294 (3)
C12	0.3405 (2)	0.91486 (13)	0.41745 (9)	0.0401 (5)
C13	0.2658 (2)	0.98677 (15)	0.35349 (10)	0.0470 (5)
C14	0.1706 (2)	1.07633 (15)	0.37982 (11)	0.0456 (5)
C15	0.1489 (2)	1.09488 (16)	0.47180 (11)	0.0507 (6)
C16	0.21914 (19)	1.02231 (14)	0.53697 (10)	0.0429 (5)
H1A	0.68570	0.38480	0.59150	0.0320*
H2	0.92800	0.27560	0.63170	0.0470*
H2A	0.62470	0.57050	0.55100	0.0320*
H3	1.20480	0.28050	0.62640	0.0600*
H3A	0.36760	0.95490	0.68710	0.0360*
H4	1.33670	0.45590	0.61300	0.0610*
H5	1.19360	0.62750	0.60870	0.0560*
H6	0.91710	0.62530	0.61500	0.0430*
H9	0.48190	0.79820	0.77690	0.0340*
H12	0.40880	0.85480	0.39830	0.0480*
H13	0.28090	0.97360	0.29030	0.0560*
H14	0.12040	1.12490	0.33540	0.0550*
H15	0.08530	1.15780	0.49080	0.0610*
H16	0.20200	1.03470	0.60010	0.0520*

	U11	U22	U33	U12	U13	U23
O1	0.0487 (6)	0.0260 (5)	0.0230 (4)	−0.0009 (4)	0.0018 (4)	−0.0005 (3)
O2	0.0371 (5)	0.0345 (5)	0.0239 (4)	−0.0022 (4)	0.0012 (4)	−0.0072 (4)
N1	0.0270 (5)	0.0257 (5)	0.0286 (5)	−0.0012 (4)	0.0029 (4)	−0.0043 (4)
N2	0.0299 (5)	0.0286 (5)	0.0229 (5)	0.0003 (4)	0.0018 (4)	−0.0019 (4)
N3	0.0432 (6)	0.0268 (5)	0.0212 (5)	0.0004 (5)	0.0013 (4)	−0.0033 (4)
N4	0.0355 (6)	0.0275 (5)	0.0209 (5)	−0.0029 (4)	0.0012 (4)	−0.0026 (4)
C1	0.0268 (6)	0.0398 (7)	0.0186 (5)	−0.0005 (5)	0.0015 (4)	−0.0041 (5)
C2	0.0369 (7)	0.0458 (8)	0.0354 (7)	0.0058 (6)	−0.0009 (6)	−0.0100 (6)
C3	0.0378 (8)	0.0735 (12)	0.0386 (8)	0.0187 (8)	−0.0043 (6)	−0.0178 (8)
C4	0.0271 (7)	0.0945 (14)	0.0300 (7)	−0.0009 (8)	−0.0005 (6)	−0.0155 (8)
C5	0.0343 (8)	0.0735 (12)	0.0326 (7)	−0.0175 (8)	−0.0005 (6)	−0.0012 (7)
C6	0.0314 (7)	0.0462 (8)	0.0294 (6)	−0.0083 (6)	−0.0002 (5)	0.0010 (6)
C7	0.0286 (6)	0.0248 (6)	0.0243 (6)	−0.0078 (5)	0.0027 (5)	−0.0024 (5)
C8	0.0301 (6)	0.0249 (6)	0.0239 (6)	−0.0053 (5)	0.0027 (5)	−0.0020 (4)
C9	0.0371 (7)	0.0258 (6)	0.0227 (6)	−0.0027 (5)	0.0013 (5)	−0.0007 (5)
C10	0.0278 (6)	0.0269 (6)	0.0246 (6)	−0.0065 (5)	0.0028 (5)	−0.0034 (5)
C11	0.0323 (6)	0.0303 (6)	0.0254 (6)	−0.0079 (5)	−0.0029 (5)	0.0012 (5)
C12	0.0551 (9)	0.0380 (8)	0.0274 (7)	−0.0010 (7)	0.0031 (6)	0.0003 (6)
C13	0.0633 (10)	0.0502 (9)	0.0272 (7)	−0.0051 (8)	−0.0014 (7)	0.0052 (6)
C14	0.0510 (9)	0.0471 (9)	0.0378 (8)	−0.0043 (7)	−0.0130 (7)	0.0098 (7)
C15	0.0572 (10)	0.0515 (10)	0.0427 (9)	0.0147 (8)	−0.0115 (7)	−0.0006 (7)
C16	0.0503 (9)	0.0473 (9)	0.0307 (7)	0.0106 (7)	−0.0064 (6)	−0.0034 (6)

O1—C7	1.2436 (15)	C8—C9	1.3724 (18)
O2—C10	1.2509 (15)	C8—C10	1.4332 (17)
N1—N2	1.3962 (15)	C11—C16	1.385 (2)
N1—C1	1.4207 (16)	C11—C12	1.3838 (18)
N2—C7	1.3489 (16)	C12—C13	1.391 (2)
N3—N4	1.3819 (15)	C13—C14	1.373 (2)
N3—C9	1.3273 (17)	C14—C15	1.381 (2)
N4—C10	1.3951 (17)	C15—C16	1.391 (2)
N4—C11	1.4236 (16)	C2—H2	0.9500
N1—H1A	0.9100	C3—H3	0.9500
N2—H2A	0.9100	C4—H4	0.9500
N3—H3A	0.9100	C5—H5	0.9500
C1—C6	1.385 (2)	C6—H6	0.9500
C1—C2	1.391 (2)	C9—H9	0.9500
C2—C3	1.394 (2)	C12—H12	0.9500
C3—C4	1.376 (3)	C13—H13	0.9500
C4—C5	1.376 (3)	C14—H14	0.9500
C5—C6	1.394 (2)	C15—H15	0.9500
C7—C8	1.4493 (17)	C16—H16	0.9500
N2—N1—C1	116.56 (10)	N4—C11—C12	119.25 (12)
N1—N2—C7	120.04 (10)	N4—C11—C16	120.65 (11)
N4—N3—C9	108.74 (10)	C12—C11—C16	120.09 (13)
N3—N4—C10	108.80 (10)	C11—C12—C13	119.18 (14)
N3—N4—C11	120.98 (10)	C12—C13—C14	121.35 (14)
C10—N4—C11	130.15 (10)	C13—C14—C15	119.04 (15)
N2—N1—H1A	110.00	C14—C15—C16	120.65 (16)
C1—N1—H1A	113.00	C11—C16—C15	119.64 (14)
C7—N2—H2A	119.00	C1—C2—H2	120.00
N1—N2—H2A	121.00	C3—C2—H2	120.00
N4—N3—H3A	121.00	C2—C3—H3	120.00
C9—N3—H3A	126.00	C4—C3—H3	120.00
C2—C1—C6	119.79 (12)	C3—C4—H4	120.00
N1—C1—C2	117.86 (12)	C5—C4—H4	120.00
N1—C1—C6	122.33 (12)	C4—C5—H5	120.00
C1—C2—C3	119.71 (15)	C6—C5—H5	120.00
C2—C3—C4	120.54 (17)	C1—C6—H6	120.00
C3—C4—C5	119.57 (15)	C5—C6—H6	120.00
C4—C5—C6	120.87 (16)	N3—C9—H9	125.00
C1—C6—C5	119.50 (14)	C8—C9—H9	125.00
N2—C7—C8	115.01 (10)	C11—C12—H12	120.00
O1—C7—N2	123.43 (11)	C13—C12—H12	120.00
O1—C7—C8	121.56 (11)	C12—C13—H13	119.00
C7—C8—C10	127.58 (11)	C14—C13—H13	119.00
C9—C8—C10	107.30 (11)	C13—C14—H14	120.00
C7—C8—C9	125.12 (11)	C15—C14—H14	120.00
N3—C9—C8	110.09 (11)	C14—C15—H15	120.00
N4—C10—C8	104.97 (10)	C16—C15—H15	120.00
O2—C10—C8	129.92 (12)	C11—C16—H16	120.00
O2—C10—N4	125.08 (11)	C15—C16—H16	120.00
C1—N1—N2—C7	−93.97 (13)	C2—C3—C4—C5	1.0 (2)
N2—N1—C1—C2	−171.62 (11)	C3—C4—C5—C6	−0.7 (2)
N2—N1—C1—C6	10.19 (17)	C4—C5—C6—C1	−0.6 (2)
N1—N2—C7—O1	0.51 (18)	O1—C7—C8—C9	0.9 (2)
N1—N2—C7—C8	−179.89 (10)	O1—C7—C8—C10	−178.68 (13)
C9—N3—N4—C10	3.27 (14)	N2—C7—C8—C9	−178.74 (12)
C9—N3—N4—C11	−179.56 (11)	N2—C7—C8—C10	1.71 (19)
N4—N3—C9—C8	−2.57 (15)	C7—C8—C9—N3	−178.73 (12)
N3—N4—C10—O2	175.50 (12)	C10—C8—C9—N3	0.90 (15)
N3—N4—C10—C8	−2.61 (13)	C7—C8—C10—O2	2.7 (2)
C11—N4—C10—O2	−1.3 (2)	C7—C8—C10—N4	−179.30 (12)
C11—N4—C10—C8	−179.44 (12)	C9—C8—C10—O2	−176.90 (13)
N3—N4—C11—C12	170.15 (13)	C9—C8—C10—N4	1.08 (14)
N3—N4—C11—C16	−8.37 (19)	N4—C11—C12—C13	179.11 (14)
C10—N4—C11—C12	−13.3 (2)	C16—C11—C12—C13	−2.4 (2)
C10—N4—C11—C16	168.14 (13)	N4—C11—C16—C15	179.27 (14)
N1—C1—C2—C3	−179.61 (13)	C12—C11—C16—C15	0.8 (2)
C6—C1—C2—C3	−1.4 (2)	C11—C12—C13—C14	2.0 (2)
N1—C1—C6—C5	179.80 (12)	C12—C13—C14—C15	−0.1 (3)
C2—C1—C6—C5	1.64 (19)	C13—C14—C15—C16	−1.6 (3)
C1—C2—C3—C4	0.1 (2)	C14—C15—C16—C11	1.2 (3)

D—H···A	D—H	H···A	D···A	D—H···A
N1—H1A···O2i	0.91	2.06	2.9244 (14)	158
N2—H2A···O2	0.91	2.14	2.8597 (14)	136
N3—H3A···O1ii	0.91	1.75	2.6527 (15)	169
C12—H12···O2	0.95	2.28	2.9133 (18)	124
C16—H16···O1ii	0.95	2.51	3.2745 (18)	137

Table 1

Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
N1—H1A⋯O2i	0.91	2.06	2.9244 (14)	158
N2—H2A⋯O2	0.91	2.14	2.8597 (14)	136
N3—H3A⋯O1ii	0.91	1.75	2.6527 (15)	169
C12—H12⋯O2	0.95	2.28	2.9133 (18)	124
C16—H16⋯O1ii	0.95	2.51	3.2745 (18)	137

Symmetry codes: (i) ; (ii) .