N-Phenyl-2-(propan-2-yl-idene)-hydrazine-carboxamide.

In the title compound, C(10)H(13)N(3)O, the hydrazinecarboxamide N-N-C(=O)-N unit is nearly planar [maximum deviation = 0.018 (2) Å] and is inclined at a dihedral angle of 8.45 (10)° with respect to the plane of the phenyl ring. The mol-ecular structure is stabilized by an intra-molecular C-H⋯O hydrogen bond which generates an S(6) ring motif. In the crystal, mol-ecules are linked into an inversion dimer by pairs of N-H⋯O and C-H⋯O hydrogen bonds.

Related literature

For general background to and the pharmacological activities of the title compound, see: Sander & Shorvon (1987 ▶); Dimmock et al. (1993 ▶). For the preparation of the starting material of the title compound, see: Aboul-Enein et al. (2012 ▶). For standard bond-length data, see: Allen et al. (1987 ▶). For hydrogen-bond motifs, see: Bernstein et al. (1995 ▶). For a related compound, see: Thirumurugan et al. (2006 ▶).

Experimental

Crystal data

C10H13N3O

M = 191.23

Monoclinic,

a = 6.2225 (3) Å

b = 15.3429 (7) Å

c = 11.8897 (5) Å

β = 112.283 (4)°

V = 1050.35 (8) Å3

Z = 4

Cu Kα radiation

μ = 0.66 mm−1

T = 296 K

0.50 × 0.11 × 0.08 mm

Data collection

Bruker SMART APEXII CCD area-detector diffractometer

Absorption correction: multi-scan (SADABS; Bruker, 2009 ▶) T min = 0.438, T max = 0.949

7990 measured reflections

1657 independent reflections

938 reflections with I > 2σ(I)

R int = 0.135

Refinement

R[F 2 > 2σ(F 2)] = 0.048

wR(F 2) = 0.142

S = 0.95

1657 reflections

130 parameters

H-atom parameters constrained

Δρmax = 0.18 e Å−3

Δρmin = −0.13 e Å−3

Data collection: APEX2 (Bruker, 2009 ▶); cell refinement: SAINT (Bruker, 2009 ▶); data reduction: SAINT; program(s) used to solve structure: SHELXTL (Sheldrick, 2008 ▶); program(s) used to refine structure: SHELXTL; molecular graphics: SHELXTL; software used to prepare material for publication: SHELXTL and PLATON (Spek, 2009 ▶).

Crystal structure: contains datablock(s) global, I. DOI: 10.1107/S1600536812004904/is5068sup1.cif

Structure factors: contains datablock(s) I. DOI: 10.1107/S1600536812004904/is5068Isup2.hkl

Supplementary material file. DOI: 10.1107/S1600536812004904/is5068Isup3.cml

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

C10H13N3O	F(000) = 408
Mr = 191.23	Dx = 1.209 Mg m−3
Monoclinic, P21/c	Cu Kα radiation, λ = 1.54178 Å
Hall symbol: -P 2ybc	Cell parameters from 751 reflections
a = 6.2225 (3) Å	θ = 5.0–67.2°
b = 15.3429 (7) Å	µ = 0.66 mm−1
c = 11.8897 (5) Å	T = 296 K
β = 112.283 (4)°	Needel, colourless
V = 1050.35 (8) Å3	0.50 × 0.11 × 0.08 mm
Z = 4

Bruker SMART APEXII CCD area-detector diffractometer	1657 independent reflections
Radiation source: fine-focus sealed tube	938 reflections with I > 2σ(I)
Graphite monochromator	Rint = 0.135
φ and ω scans	θmax = 63.0°, θmin = 5.0°
Absorption correction: multi-scan (SADABS; Bruker, 2009)	h = −5→6
Tmin = 0.438, Tmax = 0.949	k = −17→17
7990 measured reflections	l = −13→13

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)] = 0.048	H-atom parameters constrained
wR(F2) = 0.142	w = 1/[σ2(Fo2) + (0.0676P)2] where P = (Fo2 + 2Fc2)/3
S = 0.95	(Δ/σ)max = 0.002
1657 reflections	Δρmax = 0.18 e Å−3
130 parameters	Δρmin = −0.13 e Å−3
0 restraints	Extinction correction: SHELXTL (Sheldrick, 2008), Fc*=kFc[1+0.001xFc2λ3/sin(2θ)]-1/4
Primary atom site location: structure-invariant direct methods	Extinction coefficient: 0.0093 (12)

Geometry. All esds (except the esd in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell esds are taken into account individually in the estimation of esds in distances, angles and torsion angles; correlations between esds in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell esds is used for estimating esds 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 > 2sigma(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	0.8269 (3)	0.06411 (10)	0.88218 (14)	0.0795 (5)
N1	0.5175 (3)	0.12926 (11)	0.90676 (16)	0.0686 (6)
H1	0.4585	0.1299	0.9605	0.082*
N2	0.7965 (3)	0.05943 (12)	1.06500 (16)	0.0691 (6)
H2	0.9184	0.0260	1.0912	0.083*
N3	0.6658 (3)	0.08137 (11)	1.13237 (17)	0.0671 (5)
C1	0.4742 (4)	0.16254 (14)	0.6968 (2)	0.0740 (7)
H1A	0.6202	0.1402	0.7087	0.089*
C2	0.3356 (5)	0.19777 (16)	0.5857 (2)	0.0844 (7)
H2A	0.3905	0.1989	0.5230	0.101*
C3	0.1202 (4)	0.23094 (16)	0.5654 (2)	0.0855 (8)
H3A	0.0301	0.2543	0.4900	0.103*
C4	0.0386 (4)	0.22947 (15)	0.6575 (2)	0.0800 (7)
H4A	−0.1074	0.2521	0.6450	0.096*
C5	0.1727 (4)	0.19460 (13)	0.7679 (2)	0.0715 (7)
H5A	0.1154	0.1933	0.8296	0.086*
C6	0.3922 (4)	0.16118 (12)	0.78967 (19)	0.0602 (6)
C7	0.7190 (4)	0.08280 (14)	0.9466 (2)	0.0640 (6)
C8	0.7504 (4)	0.06860 (13)	1.2464 (2)	0.0669 (6)
C9	0.9849 (4)	0.03171 (16)	1.3183 (2)	0.0873 (8)
H9A	1.0181	−0.0148	1.2733	0.131*
H9B	0.9871	0.0097	1.3943	0.131*
H9C	1.1001	0.0765	1.3333	0.131*
C10	0.6029 (4)	0.09321 (16)	1.3149 (2)	0.0883 (8)
H10A	0.4583	0.1166	1.2596	0.132*
H10B	0.6818	0.1364	1.3748	0.132*
H10C	0.5735	0.0426	1.3543	0.132*

	U11	U22	U33	U12	U13	U23
O1	0.0855 (11)	0.0935 (11)	0.0727 (11)	0.0206 (8)	0.0449 (9)	0.0105 (9)
N1	0.0766 (12)	0.0733 (11)	0.0652 (11)	0.0133 (10)	0.0374 (9)	0.0071 (10)
N2	0.0719 (12)	0.0784 (12)	0.0636 (12)	0.0100 (9)	0.0331 (9)	0.0026 (10)
N3	0.0725 (13)	0.0741 (11)	0.0650 (12)	0.0015 (9)	0.0375 (9)	−0.0009 (10)
C1	0.0778 (16)	0.0797 (14)	0.0764 (16)	0.0085 (11)	0.0427 (12)	0.0103 (13)
C2	0.0960 (19)	0.0941 (16)	0.0774 (18)	0.0090 (15)	0.0490 (13)	0.0165 (14)
C3	0.0818 (18)	0.0957 (17)	0.0816 (18)	0.0115 (14)	0.0338 (13)	0.0227 (15)
C4	0.0774 (17)	0.0878 (16)	0.0817 (18)	0.0106 (12)	0.0379 (13)	0.0125 (15)
C5	0.0796 (16)	0.0728 (13)	0.0733 (16)	0.0049 (12)	0.0415 (12)	0.0028 (12)
C6	0.0688 (15)	0.0544 (11)	0.0658 (14)	0.0002 (10)	0.0351 (10)	−0.0015 (11)
C7	0.0725 (16)	0.0627 (12)	0.0636 (16)	0.0014 (11)	0.0333 (11)	−0.0006 (12)
C8	0.0744 (16)	0.0662 (11)	0.0662 (16)	−0.0066 (11)	0.0335 (12)	−0.0052 (12)
C9	0.0894 (17)	0.0979 (16)	0.0719 (15)	0.0069 (13)	0.0275 (13)	−0.0016 (14)
C10	0.0961 (19)	0.1029 (17)	0.0802 (17)	0.0004 (15)	0.0496 (14)	−0.0007 (15)

O1—C7	1.229 (3)	C3—H3A	0.9300
N1—C7	1.362 (3)	C4—C5	1.369 (3)
N1—C6	1.401 (2)	C4—H4A	0.9300
N1—H1	0.8488	C5—C6	1.388 (3)
N2—C7	1.352 (3)	C5—H5A	0.9300
N2—N3	1.382 (2)	C8—C10	1.487 (3)
N2—H2	0.8694	C8—C9	1.495 (3)
N3—C8	1.270 (2)	C9—H9A	0.9600
C1—C6	1.381 (3)	C9—H9B	0.9600
C1—C2	1.385 (3)	C9—H9C	0.9600
C1—H1A	0.9300	C10—H10A	0.9600
C2—C3	1.367 (3)	C10—H10B	0.9600
C2—H2A	0.9300	C10—H10C	0.9600
C3—C4	1.371 (3)
C7—N1—C6	128.38 (18)	C1—C6—C5	118.7 (2)
C7—N1—H1	110.4	C1—C6—N1	124.4 (2)
C6—N1—H1	120.5	C5—C6—N1	116.88 (18)
C7—N2—N3	118.88 (18)	O1—C7—N2	121.6 (2)
C7—N2—H2	116.6	O1—C7—N1	123.6 (2)
N3—N2—H2	124.1	N2—C7—N1	114.8 (2)
C8—N3—N2	118.99 (18)	N3—C8—C10	117.0 (2)
C6—C1—C2	118.9 (2)	N3—C8—C9	126.0 (2)
C6—C1—H1A	120.6	C10—C8—C9	117.0 (2)
C2—C1—H1A	120.6	C8—C9—H9A	109.5
C3—C2—C1	121.9 (2)	C8—C9—H9B	109.5
C3—C2—H2A	119.1	H9A—C9—H9B	109.5
C1—C2—H2A	119.1	C8—C9—H9C	109.5
C2—C3—C4	119.3 (2)	H9A—C9—H9C	109.5
C2—C3—H3A	120.4	H9B—C9—H9C	109.5
C4—C3—H3A	120.4	C8—C10—H10A	109.5
C5—C4—C3	119.7 (2)	C8—C10—H10B	109.5
C5—C4—H4A	120.1	H10A—C10—H10B	109.5
C3—C4—H4A	120.1	C8—C10—H10C	109.5
C4—C5—C6	121.5 (2)	H10A—C10—H10C	109.5
C4—C5—H5A	119.3	H10B—C10—H10C	109.5
C6—C5—H5A	119.3
C7—N2—N3—C8	−171.93 (18)	C7—N1—C6—C1	−11.0 (3)
C6—C1—C2—C3	−0.1 (4)	C7—N1—C6—C5	169.99 (19)
C1—C2—C3—C4	0.0 (4)	N3—N2—C7—O1	−179.16 (18)
C2—C3—C4—C5	−0.3 (4)	N3—N2—C7—N1	2.0 (3)
C3—C4—C5—C6	0.7 (3)	C6—N1—C7—O1	2.5 (3)
C2—C1—C6—C5	0.5 (3)	C6—N1—C7—N2	−178.70 (18)
C2—C1—C6—N1	−178.47 (19)	N2—N3—C8—C10	−179.96 (18)
C4—C5—C6—C1	−0.8 (3)	N2—N3—C8—C9	0.5 (3)
C4—C5—C6—N1	178.26 (18)

D—H···A	D—H	H···A	D···A	D—H···A
N2—H2···O1i	0.87	2.04	2.892 (3)	168
C1—H1A···O1	0.93	2.29	2.879 (3)	120
C9—H9A···O1i	0.96	2.50	3.366 (3)	149

Table 1

Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
N2—H2⋯O1i	0.87	2.04	2.892 (3)	168
C1—H1A⋯O1	0.93	2.29	2.879 (3)	120
C9—H9A⋯O1i	0.96	2.50	3.366 (3)	149

Symmetry code: (i) .