(2E)-2-Benzyl-idene-N-phenyl-hydrazinecarboxamide.

The mol-ecule of the title compound, C14H13N3O, adopts an E conformation with respect to the azomethine C=N bond, and is roughly planar, with an r.m.s. deviation of the non-H atoms from the least-squares plane of 0.100 (2) Å and a dihedral angle between the terminal benzene rings of 5.74 (12)°. An intramolecular N-H⋯N hydrogen bond closes an S(6) ring. In the crystal, mol-ecules are linked by the pairs of N-H⋯O hydrogen bonds into centrosymmetric dimers. Dimers related by translation along [010] form slanted stacks, the shortest C⋯C inter-molecular distance within the stack being 3.283 (3) Å. Weak C-H⋯π inter-actions link the stacks into a three-dimensional structure.

Related literature

For the synthesis of related compounds, see: Siji et al. (2010 ▶). For biological applications of hydrazinecarboxamide and its derivatives, see: Rivadeneira et al. (2009 ▶); Shalini et al. (2009 ▶). For related structures, see: Annie et al. (2012 ▶); Aravindakshan et al. (2013 ▶).

Experimental

Crystal data

C14H13N3O

M = 239.27

Monoclinic,

a = 13.6308 (14) Å

b = 5.4023 (5) Å

c = 17.5751 (19) Å

β = 93.065 (4)°

V = 1292.3 (2) Å3

Z = 4

Mo Kα radiation

μ = 0.08 mm−1

T = 296 K

0.29 × 0.24 × 0.21 mm

Data collection

Bruker APEXII CCD area-detector diffractometer

Absorption correction: multi-scan (SADABS; Bruker, 2004 ▶) T min = 0.977, T max = 0.983

9857 measured reflections

2302 independent reflections

1655 reflections with I > 2σ(I)

R int = 0.023

Refinement

R[F 2 > 2σ(F 2)] = 0.044

wR(F 2) = 0.146

S = 1.04

2300 reflections

171 parameters

2 restraints

H atoms treated by a mixture of independent and constrained refinement

Δρmax = 0.19 e Å−3

Δρmin = −0.14 e Å−3

Data collection: APEX2 (Bruker, 2004 ▶); cell refinement: SAINT (Bruker, 2004 ▶); 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 for Windows (Farrugia, 2012 ▶) and Mercury (Macrae et al., 2008 ▶); software used to prepare material for publication: SHELXL97 and publCIF (Westrip, 2010 ▶).

Crystal structure: contains datablock(s) I, global. DOI: 10.1107/S1600536814008344/yk2104sup1.cif

Structure factors: contains datablock(s) I. DOI: 10.1107/S1600536814008344/yk2104Isup2.hkl

Click here for additional data file.

Supporting information file. DOI: 10.1107/S1600536814008344/yk2104Isup3.cml

CCDC reference: 997059

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

C14H13N3O	F(000) = 504
Mr = 239.27	Dx = 1.230 Mg m−3
Monoclinic, P2/c	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: -P 2yc	Cell parameters from 3449 reflections
a = 13.6308 (14) Å	θ = 2.7–25.1°
b = 5.4023 (5) Å	µ = 0.08 mm−1
c = 17.5751 (19) Å	T = 296 K
β = 93.065 (4)°	Block, colourless
V = 1292.3 (2) Å3	0.29 × 0.24 × 0.21 mm
Z = 4

Bruker APEXII CCD area-detector diffractometer	2302 independent reflections
Radiation source: fine-focus sealed tube	1655 reflections with I > 2σ(I)
Graphite monochromator	Rint = 0.023
Detector resolution: 8.33 pixels mm-1	θmax = 25.1°, θmin = 2.3°
φ and ω scans	h = −16→16
Absorption correction: multi-scan (SADABS; Bruker, 2004)	k = −6→6
Tmin = 0.977, Tmax = 0.983	l = −20→20
9857 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)] = 0.044	Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.146	H atoms treated by a mixture of independent and constrained refinement
S = 1.04	w = 1/[σ2(Fo2) + (0.0686P)2 + 0.3096P] where P = (Fo2 + 2Fc2)/3
2300 reflections	(Δ/σ)max < 0.001
171 parameters	Δρmax = 0.19 e Å−3
2 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
O1	0.12555 (9)	−0.4737 (3)	0.03527 (9)	0.0743 (4)
N1	−0.03540 (11)	−0.0322 (3)	0.10278 (9)	0.0613 (4)
N2	−0.00160 (11)	−0.2374 (3)	0.06671 (10)	0.0678 (5)
N3	0.15497 (11)	−0.1014 (3)	0.09396 (10)	0.0642 (4)
C1	−0.12124 (15)	0.3641 (4)	0.18518 (12)	0.0718 (6)
H1	−0.0535	0.3456	0.1924	0.086*
C2	−0.1678 (2)	0.5526 (4)	0.22135 (14)	0.0879 (7)
H2	−0.1315	0.6601	0.2532	0.105*
C3	−0.2675 (2)	0.5831 (5)	0.21077 (16)	0.0924 (8)
H3	−0.2989	0.7108	0.2353	0.111*
C4	−0.32004 (18)	0.4260 (5)	0.16432 (16)	0.0885 (7)
H4	−0.3875	0.4474	0.1567	0.106*
C5	−0.27437 (14)	0.2354 (4)	0.12843 (12)	0.0735 (6)
H5	−0.3114	0.1278	0.0972	0.088*
C6	−0.17410 (13)	0.2018 (3)	0.13822 (10)	0.0585 (5)
C7	−0.12822 (13)	−0.0028 (4)	0.09942 (11)	0.0605 (5)
H7	−0.1677	−0.1145	0.0715	0.073*
C8	0.09629 (13)	−0.2821 (4)	0.06361 (11)	0.0596 (5)
C9	0.25809 (13)	−0.0996 (3)	0.10287 (11)	0.0593 (5)
C10	0.29986 (15)	0.0908 (4)	0.14580 (15)	0.0811 (7)
H10	0.2601	0.2115	0.1659	0.097*
C11	0.40000 (17)	0.1028 (5)	0.15888 (18)	0.0985 (8)
H11	0.4275	0.2300	0.1886	0.118*
C12	0.45930 (17)	−0.0700 (5)	0.12867 (19)	0.1017 (9)
H12	0.5271	−0.0598	0.1370	0.122*
C13	0.41822 (16)	−0.2588 (5)	0.08601 (17)	0.0977 (8)
H13	0.4587	−0.3768	0.0653	0.117*
C14	0.31741 (14)	−0.2772 (4)	0.07315 (13)	0.0773 (6)
H14	0.2901	−0.4079	0.0448	0.093*
H2'	−0.0434 (12)	−0.336 (3)	0.0420 (11)	0.075 (6)*
H3'	0.1243 (14)	0.026 (3)	0.1121 (12)	0.078 (7)*

	U11	U22	U33	U12	U13	U23
O1	0.0593 (8)	0.0682 (9)	0.0949 (11)	0.0025 (6)	−0.0021 (7)	−0.0228 (7)
N1	0.0535 (9)	0.0662 (10)	0.0646 (10)	−0.0012 (7)	0.0064 (7)	−0.0066 (7)
N2	0.0501 (9)	0.0714 (11)	0.0820 (11)	−0.0038 (8)	0.0036 (8)	−0.0216 (9)
N3	0.0520 (9)	0.0623 (10)	0.0776 (11)	0.0030 (7)	−0.0022 (7)	−0.0141 (8)
C1	0.0687 (12)	0.0747 (14)	0.0718 (13)	0.0010 (10)	0.0009 (10)	−0.0056 (10)
C2	0.112 (2)	0.0756 (15)	0.0759 (15)	−0.0007 (13)	0.0062 (13)	−0.0110 (12)
C3	0.112 (2)	0.0763 (15)	0.0919 (18)	0.0256 (14)	0.0291 (15)	0.0068 (13)
C4	0.0737 (14)	0.0932 (17)	0.0995 (18)	0.0234 (13)	0.0137 (13)	0.0107 (14)
C5	0.0582 (11)	0.0841 (15)	0.0783 (14)	0.0038 (10)	0.0046 (10)	0.0023 (11)
C6	0.0564 (10)	0.0630 (11)	0.0566 (11)	−0.0001 (8)	0.0072 (8)	0.0048 (9)
C7	0.0528 (10)	0.0684 (12)	0.0603 (11)	−0.0057 (8)	0.0018 (8)	−0.0053 (9)
C8	0.0532 (10)	0.0630 (11)	0.0623 (11)	−0.0005 (9)	0.0009 (8)	−0.0040 (9)
C9	0.0517 (10)	0.0605 (11)	0.0651 (11)	0.0007 (8)	−0.0017 (8)	0.0039 (9)
C10	0.0625 (12)	0.0685 (13)	0.1114 (18)	−0.0038 (10)	−0.0036 (11)	−0.0131 (12)
C11	0.0678 (14)	0.0837 (16)	0.142 (2)	−0.0114 (12)	−0.0128 (14)	−0.0153 (15)
C12	0.0534 (12)	0.0997 (19)	0.151 (3)	−0.0060 (13)	−0.0056 (14)	−0.0021 (17)
C13	0.0603 (13)	0.1020 (19)	0.131 (2)	0.0146 (13)	0.0054 (13)	−0.0146 (16)
C14	0.0589 (11)	0.0817 (14)	0.0909 (15)	0.0045 (10)	0.0001 (10)	−0.0161 (12)

O1—C8	1.225 (2)	C4—H4	0.9300
N1—C7	1.273 (2)	C5—C6	1.380 (3)
N1—N2	1.369 (2)	C5—H5	0.9300
N2—C8	1.360 (2)	C6—C7	1.457 (3)
N2—H2'	0.877 (9)	C7—H7	0.9300
N3—C8	1.353 (2)	C9—C14	1.376 (3)
N3—C9	1.406 (2)	C9—C10	1.380 (3)
N3—H3'	0.876 (9)	C10—C11	1.373 (3)
C1—C2	1.374 (3)	C10—H10	0.9300
C1—C6	1.380 (3)	C11—C12	1.361 (4)
C1—H1	0.9300	C11—H11	0.9300
C2—C3	1.373 (4)	C12—C13	1.368 (4)
C2—H2	0.9300	C12—H12	0.9300
C3—C4	1.355 (4)	C13—C14	1.384 (3)
C3—H3	0.9300	C13—H13	0.9300
C4—C5	1.374 (3)	C14—H14	0.9300
C7—N1—N2	115.97 (15)	N1—C7—C6	121.55 (17)
C8—N2—N1	121.18 (15)	N1—C7—H7	119.2
C8—N2—H2'	119.0 (13)	C6—C7—H7	119.2
N1—N2—H2'	119.7 (13)	O1—C8—N3	124.84 (16)
C8—N3—C9	127.98 (16)	O1—C8—N2	120.54 (16)
C8—N3—H3'	115.4 (14)	N3—C8—N2	114.62 (17)
C9—N3—H3'	116.6 (14)	C14—C9—C10	119.58 (18)
C2—C1—C6	120.6 (2)	C14—C9—N3	123.85 (17)
C2—C1—H1	119.7	C10—C9—N3	116.54 (17)
C6—C1—H1	119.7	C11—C10—C9	120.2 (2)
C3—C2—C1	120.3 (2)	C11—C10—H10	119.9
C3—C2—H2	119.8	C9—C10—H10	119.9
C1—C2—H2	119.8	C12—C11—C10	120.5 (2)
C4—C3—C2	119.6 (2)	C12—C11—H11	119.7
C4—C3—H3	120.2	C10—C11—H11	119.7
C2—C3—H3	120.2	C11—C12—C13	119.4 (2)
C3—C4—C5	120.6 (2)	C11—C12—H12	120.3
C3—C4—H4	119.7	C13—C12—H12	120.3
C5—C4—H4	119.7	C12—C13—C14	121.1 (2)
C4—C5—C6	120.7 (2)	C12—C13—H13	119.4
C4—C5—H5	119.6	C14—C13—H13	119.4
C6—C5—H5	119.6	C9—C14—C13	119.1 (2)
C1—C6—C5	118.23 (19)	C9—C14—H14	120.4
C1—C6—C7	122.55 (17)	C13—C14—H14	120.4
C5—C6—C7	119.22 (18)
C7—N1—N2—C8	177.05 (17)	C9—N3—C8—N2	176.29 (18)
C6—C1—C2—C3	−0.5 (3)	N1—N2—C8—O1	175.52 (17)
C1—C2—C3—C4	−0.1 (4)	N1—N2—C8—N3	−4.3 (3)
C2—C3—C4—C5	0.7 (4)	C8—N3—C9—C14	7.8 (3)
C3—C4—C5—C6	−0.8 (3)	C8—N3—C9—C10	−170.6 (2)
C2—C1—C6—C5	0.4 (3)	C14—C9—C10—C11	−0.1 (4)
C2—C1—C6—C7	−179.21 (19)	N3—C9—C10—C11	178.4 (2)
C4—C5—C6—C1	0.2 (3)	C9—C10—C11—C12	1.2 (4)
C4—C5—C6—C7	179.83 (18)	C10—C11—C12—C13	−1.1 (5)
N2—N1—C7—C6	177.24 (16)	C11—C12—C13—C14	−0.1 (4)
C1—C6—C7—N1	−4.9 (3)	C10—C9—C14—C13	−1.0 (3)
C5—C6—C7—N1	175.51 (18)	N3—C9—C14—C13	−179.4 (2)
C9—N3—C8—O1	−3.5 (3)	C12—C13—C14—C9	1.1 (4)

D—H···A	D—H	H···A	D···A	D—H···A
N3—H3′···N1	0.88 (1)	2.20 (2)	2.634 (2)	110 (2)
N2—H2′···O1i	0.88 (1)	2.00 (1)	2.860 (2)	167 (2)
C3—H3···Cg1ii	0.93	2.99	3.800 (3)	146

Table 1

Hydrogen-bond geometry (Å, °)

Cg1 is the centroid of the C9–C14 ring.

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
N3—H3′⋯N1	0.88 (1)	2.20 (2)	2.634 (2)	110 (2)
N2—H2′⋯O1i	0.88 (1)	2.00 (1)	2.860 (2)	167 (2)
C3—H3⋯Cg1ii	0.93	2.99	3.800 (3)	146

Symmetry codes: (i) ; (ii) .