Crystal structure of N'-di-phenyl-methyl-idene-5-methyl-1H-pyrazole-3-carbo-hydrazide.

In the title compound, C18H16N4O, the planes of the phenyl rings are approximately perpendicular to each other [dihedral angle = 78.07 (8)°] and form dihedral angles of 56.43 (8) and 24.59 (8)° with the pyrazole ring. In the crystal, mol-ecules are linked by N-H⋯O hydrogen bonds to form one-dimensional chains parallel to the [010] direction.

Related literature

For the biological activities of pyrazole derivatives, see: Zhang et al. (2015 ▸); Özdemir et al. (2015 ▸); El-Sabbagh et al. (2009 ▸); Farag et al. (2010 ▸); Karrouchi et al. (2014 ▸); Mert et al. (2014 ▸); Alegaon et al. (2014 ▸). For the applications in agrochemical and pharmaceutical industries of pyrazole derivatives, see: Patel et al. (2004 ▸). For the structure of a related compound, see: Karrouchi et al. (2013 ▸).

Experimental

Crystal data

C18H16N4O

M = 304.35

Orthorhombic

a = 11.0299 (2) Å

b = 14.1131 (2) Å

c = 20.2211 (3) Å

V = 3147.74 (9) Å3

Z = 8

Mo Kα radiation

μ = 0.08 mm−1

T = 296 K

0.40 × 0.32 × 0.25 mm

Data collection

Bruker X8 APEX diffractometer

31259 measured reflections

3766 independent reflections

3117 reflections with I > 2σ(I)

R int = 0.029

Refinement

R[F 2 > 2σ(F 2)] = 0.047

wR(F 2) = 0.136

S = 1.04

3766 reflections

208 parameters

H-atom parameters constrained

Δρmax = 0.33 e Å−3

Δρmin = −0.26 e Å−3

Data collection: APEX2 (Bruker, 2009 ▸); cell refinement: SAINT-Plus (Bruker, 2009 ▸); data reduction: SAINT-Plus; program(s) used to solve structure: SHELXS97 (Sheldrick, 2008 ▸); program(s) used to refine structure: SHELXL2014 (Sheldrick, 2015 ▸); molecular graphics: ORTEP-3 for Windows (Farrugia, 2012 ▸); software used to prepare material for publication: PLATON (Spek, 2009 ▸) and publCIF (Westrip, 2010 ▸).

Crystal structure: contains datablock(s) I. DOI: 10.1107/S2056989015020071/rz5174sup1.cif

Structure factors: contains datablock(s) I. DOI: 10.1107/S2056989015020071/rz5174Isup2.hkl

Click here for additional data file.

Supporting information file. DOI: 10.1107/S2056989015020071/rz5174Isup3.cml

Click here for additional data file.

. DOI: 10.1107/S2056989015020071/rz5174fig1.tif

The mol­ecular structure of the title compound with displacement ellipsoids drawn at the 50% probability level. H atoms are represented as small circles.

Click here for additional data file.

b . DOI: 10.1107/S2056989015020071/rz5174fig2.tif

Partial crystal packing of the title compound, showing mol­ecules linked by N–H⋯O hydrogen bonds (dashed lines) into a chain parallel to the b axis.

CCDC reference: 1432912

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

C18H16N4O	F(000) = 1280
Mr = 304.35	Dx = 1.284 Mg m−3
Orthorhombic, Pbca	Melting point: 595 K
a = 11.0299 (2) Å	Mo Kα radiation, λ = 0.71073 Å
b = 14.1131 (2) Å	µ = 0.08 mm−1
c = 20.2211 (3) Å	T = 296 K
V = 3147.74 (9) Å3	Block, colourless
Z = 8	0.40 × 0.32 × 0.25 mm

Bruker X8 APEX diffractometer	3117 reflections with I > 2σ(I)
Radiation source: fine-focus sealed tube	Rint = 0.029
Graphite monochromator	θmax = 27.9°, θmin = 2.6°
φ and ω scans	h = −14→13
31259 measured reflections	k = −18→17
3766 independent reflections	l = −26→26

Refinement on F2	0 restraints
Least-squares matrix: full	Hydrogen site location: inferred from neighbouring sites
R[F2 > 2σ(F2)] = 0.047	H-atom parameters constrained
wR(F2) = 0.136	w = 1/[σ2(Fo2) + (0.0655P)2 + 1.2766P] where P = (Fo2 + 2Fc2)/3
S = 1.04	(Δ/σ)max < 0.001
3766 reflections	Δρmax = 0.33 e Å−3
208 parameters	Δρmin = −0.26 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.

	x	y	z	Uiso*/Ueq
C1	0.95160 (17)	0.23308 (11)	0.22978 (11)	0.0559 (5)
H1A	1.0236	0.2614	0.2119	0.084*
H1B	0.9735	0.1873	0.2628	0.084*
H1C	0.9073	0.2024	0.1950	0.084*
C2	0.87443 (13)	0.30798 (9)	0.26034 (8)	0.0351 (3)
C3	0.88909 (13)	0.40388 (9)	0.26613 (7)	0.0349 (3)
H3	0.9538	0.4403	0.2512	0.042*
C4	0.78552 (12)	0.43513 (8)	0.29934 (7)	0.0292 (3)
C5	0.75426 (13)	0.53261 (9)	0.31897 (7)	0.0304 (3)
C6	0.50855 (13)	0.62906 (9)	0.40692 (7)	0.0320 (3)
C7	0.40970 (13)	0.55750 (9)	0.40017 (7)	0.0338 (3)
C8	0.42278 (16)	0.46563 (11)	0.42431 (8)	0.0444 (4)
H8	0.4945	0.4480	0.4451	0.053*
C9	0.33011 (19)	0.40042 (13)	0.41756 (10)	0.0567 (5)
H9	0.3398	0.3393	0.4339	0.068*
C10	0.22390 (18)	0.42554 (14)	0.38688 (10)	0.0576 (5)
H10	0.1616	0.3816	0.3825	0.069*
C11	0.20965 (16)	0.51595 (14)	0.36252 (10)	0.0537 (4)
H11	0.1379	0.5327	0.3414	0.064*
C12	0.30150 (15)	0.58207 (12)	0.36924 (8)	0.0439 (4)
H12	0.2908	0.6432	0.3530	0.053*
C13	0.48843 (13)	0.71522 (9)	0.44807 (7)	0.0332 (3)
C14	0.56815 (15)	0.79196 (10)	0.44439 (8)	0.0413 (4)
H14	0.6288	0.7925	0.4124	0.050*
C15	0.55768 (17)	0.86695 (11)	0.48774 (10)	0.0505 (4)
H15	0.6118	0.9174	0.4852	0.061*
C16	0.46712 (17)	0.86744 (12)	0.53494 (9)	0.0514 (4)
H16	0.4611	0.9176	0.5646	0.062*
C17	0.38608 (17)	0.79383 (13)	0.53797 (9)	0.0498 (4)
H17	0.3243	0.7948	0.5692	0.060*
C18	0.39577 (14)	0.71784 (11)	0.49463 (8)	0.0414 (3)
H18	0.3400	0.6685	0.4968	0.050*
N1	0.76763 (11)	0.28765 (8)	0.28919 (7)	0.0368 (3)
H1N	0.7385	0.2312	0.2914	0.044*
N2	0.71101 (11)	0.36377 (8)	0.31412 (7)	0.0355 (3)
N3	0.64218 (11)	0.54067 (8)	0.34657 (7)	0.0366 (3)
HN3	0.5896	0.4961	0.3424	0.044*
N4	0.61501 (11)	0.62165 (8)	0.38121 (6)	0.0346 (3)
O1	0.82345 (10)	0.59943 (7)	0.31103 (6)	0.0420 (3)

	U11	U22	U33	U12	U13	U23
C1	0.0517 (10)	0.0332 (8)	0.0829 (13)	0.0055 (7)	0.0233 (9)	−0.0125 (8)
C2	0.0336 (7)	0.0267 (6)	0.0450 (8)	0.0025 (5)	0.0051 (6)	−0.0028 (5)
C3	0.0334 (7)	0.0265 (6)	0.0447 (8)	−0.0014 (5)	0.0091 (6)	−0.0007 (5)
C4	0.0298 (6)	0.0212 (6)	0.0367 (7)	0.0000 (5)	0.0014 (5)	−0.0006 (5)
C5	0.0323 (7)	0.0209 (6)	0.0381 (7)	0.0011 (5)	0.0014 (5)	−0.0014 (5)
C6	0.0332 (7)	0.0264 (6)	0.0364 (7)	0.0032 (5)	0.0001 (5)	−0.0003 (5)
C7	0.0340 (7)	0.0313 (6)	0.0362 (7)	0.0004 (5)	0.0043 (6)	−0.0032 (5)
C8	0.0480 (9)	0.0376 (8)	0.0475 (9)	−0.0026 (7)	0.0017 (7)	0.0059 (6)
C9	0.0650 (12)	0.0432 (9)	0.0618 (11)	−0.0147 (8)	0.0084 (9)	0.0086 (8)
C10	0.0510 (11)	0.0598 (11)	0.0621 (11)	−0.0240 (9)	0.0113 (9)	−0.0067 (9)
C11	0.0384 (9)	0.0655 (11)	0.0573 (10)	−0.0062 (8)	−0.0015 (8)	−0.0080 (9)
C12	0.0398 (8)	0.0410 (8)	0.0510 (9)	0.0025 (6)	−0.0023 (7)	−0.0015 (7)
C13	0.0332 (7)	0.0274 (6)	0.0391 (7)	0.0062 (5)	−0.0015 (6)	−0.0017 (5)
C14	0.0401 (8)	0.0320 (7)	0.0519 (9)	0.0034 (6)	0.0059 (7)	−0.0040 (6)
C15	0.0500 (10)	0.0332 (7)	0.0682 (11)	−0.0008 (7)	−0.0002 (8)	−0.0120 (7)
C16	0.0571 (10)	0.0424 (9)	0.0549 (10)	0.0092 (8)	−0.0010 (8)	−0.0187 (7)
C17	0.0507 (10)	0.0510 (9)	0.0477 (9)	0.0078 (7)	0.0097 (8)	−0.0103 (7)
C18	0.0391 (8)	0.0378 (7)	0.0473 (8)	0.0017 (6)	0.0065 (7)	−0.0044 (6)
N1	0.0342 (6)	0.0183 (5)	0.0580 (8)	−0.0004 (4)	0.0070 (6)	−0.0042 (5)
N2	0.0318 (6)	0.0208 (5)	0.0540 (7)	−0.0002 (4)	0.0077 (5)	−0.0035 (5)
N3	0.0325 (6)	0.0226 (5)	0.0547 (7)	−0.0017 (4)	0.0064 (5)	−0.0095 (5)
N4	0.0341 (6)	0.0237 (5)	0.0459 (7)	0.0029 (4)	0.0022 (5)	−0.0067 (5)
O1	0.0402 (6)	0.0216 (5)	0.0643 (7)	−0.0040 (4)	0.0108 (5)	−0.0039 (4)

C1—C2	1.491 (2)	C10—C11	1.377 (3)
C1—H1A	0.9600	C10—H10	0.9300
C1—H1B	0.9600	C11—C12	1.384 (2)
C1—H1C	0.9600	C11—H11	0.9300
C2—N1	1.3455 (19)	C12—H12	0.9300
C2—C3	1.3681 (18)	C13—C18	1.390 (2)
C3—C4	1.3966 (19)	C13—C14	1.397 (2)
C3—H3	0.9300	C14—C15	1.379 (2)
C4—N2	1.3339 (16)	C14—H14	0.9300
C4—C5	1.4727 (17)	C15—C16	1.382 (3)
C5—O1	1.2238 (16)	C15—H15	0.9300
C5—N3	1.3611 (18)	C16—C17	1.372 (3)
C6—N4	1.2883 (19)	C16—H16	0.9300
C6—C13	1.4901 (18)	C17—C18	1.389 (2)
C6—C7	1.4924 (19)	C17—H17	0.9300
C7—C12	1.391 (2)	C18—H18	0.9300
C7—C8	1.393 (2)	N1—N2	1.3411 (15)
C8—C9	1.382 (2)	N1—H1N	0.8600
C8—H8	0.9300	N3—N4	1.3736 (15)
C9—C10	1.372 (3)	N3—HN3	0.8600
C9—H9	0.9300
C2—C1—H1A	109.5	C10—C11—C12	120.42 (17)
C2—C1—H1B	109.5	C10—C11—H11	119.8
H1A—C1—H1B	109.5	C12—C11—H11	119.8
C2—C1—H1C	109.5	C11—C12—C7	120.26 (16)
H1A—C1—H1C	109.5	C11—C12—H12	119.9
H1B—C1—H1C	109.5	C7—C12—H12	119.9
N1—C2—C3	106.10 (12)	C18—C13—C14	118.57 (13)
N1—C2—C1	121.89 (13)	C18—C13—C6	120.63 (13)
C3—C2—C1	132.01 (14)	C14—C13—C6	120.61 (13)
C2—C3—C4	104.89 (12)	C15—C14—C13	120.56 (15)
C2—C3—H3	127.6	C15—C14—H14	119.7
C4—C3—H3	127.6	C13—C14—H14	119.7
N2—C4—C3	111.92 (11)	C14—C15—C16	120.23 (16)
N2—C4—C5	120.04 (12)	C14—C15—H15	119.9
C3—C4—C5	128.03 (12)	C16—C15—H15	119.9
O1—C5—N3	123.76 (12)	C17—C16—C15	119.89 (15)
O1—C5—C4	122.58 (12)	C17—C16—H16	120.1
N3—C5—C4	113.66 (11)	C15—C16—H16	120.1
N4—C6—C13	115.30 (12)	C16—C17—C18	120.41 (16)
N4—C6—C7	125.03 (12)	C16—C17—H17	119.8
C13—C6—C7	119.64 (12)	C18—C17—H17	119.8
C12—C7—C8	118.58 (14)	C17—C18—C13	120.29 (15)
C12—C7—C6	119.94 (13)	C17—C18—H18	119.9
C8—C7—C6	121.48 (14)	C13—C18—H18	119.9
C9—C8—C7	120.57 (16)	N2—N1—C2	113.57 (11)
C9—C8—H8	119.7	N2—N1—H1N	123.2
C7—C8—H8	119.7	C2—N1—H1N	123.2
C10—C9—C8	120.26 (17)	C4—N2—N1	103.52 (11)
C10—C9—H9	119.9	C5—N3—N4	118.48 (11)
C8—C9—H9	119.9	C5—N3—HN3	120.8
C9—C10—C11	119.91 (16)	N4—N3—HN3	120.8
C9—C10—H10	120.0	C6—N4—N3	118.18 (12)
C11—C10—H10	120.0

D—H···A	D—H	H···A	D···A	D—H···A
N1—H1N···O1i	0.86	2.02	2.8740 (15)	172

Table 1

Hydrogen-bond geometry (, )

DHA	DH	HA	D A	DHA
N1H1NO1i	0.86	2.02	2.8740(15)	172

Symmetry code: (i) .