1-(1-Phenyl-ethyl-idene)carbonohydrazide.

The title compound, C(9)H(12)N(4)O, crystallizes with two independent mol-ecules in the asymmetric unit. In the crystal, inter-molecular N-H⋯O and N-H⋯N hydrogen bonds link the mol-ecules into paired ribbons propagated in [100]. The crystal studied was a twin (twin law 00/00/001) with a minor component of 25%.

Related literature

For applications of carbonohydrazide derivatives, see: Esmail & Kurzer (1977 ▶); Loncle et al. (2004 ▶). For a related structure, see: Meyers et al. (1995 ▶).

Experimental

Crystal data

C9H12N4O

M = 192.23

Monoclinic,

a = 9.7744 (8) Å

b = 7.3163 (7) Å

c = 28.2761 (3) Å

β = 90.796 (1)°

V = 2021.9 (3) Å3

Z = 8

Mo Kα radiation

μ = 0.09 mm−1

T = 293 K

0.43 × 0.17 × 0.15 mm

Data collection

Bruker SMART APEX CCD area-detector diffractometer

Absorption correction: multi-scan (SADABS; Sheldrick, 2007 ▶) T min = 0.963, T max = 0.987

9568 measured reflections

3568 independent reflections

1412 reflections with I > 2σ(I)

R int = 0.111

Refinement

R[F 2 > 2σ(F 2)] = 0.062

wR(F 2) = 0.186

S = 0.84

3568 reflections

256 parameters

H-atom parameters constrained

Δρmax = 0.26 e Å−3

Δρmin = −0.24 e Å−3

Data collection: SMART (Bruker, 2007 ▶); cell refinement: SAINT (Bruker, 2007 ▶); data reduction: SAINT; program(s) used to solve structure: SHELXS97 (Sheldrick, 2008 ▶); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008 ▶); molecular graphics: SHELXTL (Sheldrick, 2008 ▶); software used to prepare material for publication: SHELXTL.

Crystal structure: contains datablocks I, global. DOI: 10.1107/S1600536810038353/cv2761sup1.cif

Structure factors: contains datablocks I. DOI: 10.1107/S1600536810038353/cv2761Isup2.hkl

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

C9H12N4O	F(000) = 816
Mr = 192.23	Dx = 1.263 Mg m−3
Monoclinic, P21/c	Mo Kα radiation, λ = 0.71073 Å
a = 9.7744 (8) Å	Cell parameters from 839 reflections
b = 7.3163 (7) Å	θ = 2.5–26.2°
c = 28.2761 (3) Å	µ = 0.09 mm−1
β = 90.796 (1)°	T = 293 K
V = 2021.9 (3) Å3	Block, colourless
Z = 8	0.43 × 0.17 × 0.15 mm

Bruker SMART APEX CCD area-detector diffractometer	3568 independent reflections
Radiation source: fine-focus sealed tube	1412 reflections with I > 2σ(I)
graphite	Rint = 0.111
phi and ω scans	θmax = 25.0°, θmin = 1.4°
Absorption correction: multi-scan (SADABS; Sheldrick, 2007)	h = −10→11
Tmin = 0.963, Tmax = 0.987	k = −8→8
9568 measured reflections	l = −33→23

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)] = 0.062	Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.186	H-atom parameters constrained
S = 0.84	w = 1/[σ2(Fo2) + (0.0777P)2] where P = (Fo2 + 2Fc2)/3
3568 reflections	(Δ/σ)max < 0.001
256 parameters	Δρmax = 0.26 e Å−3
0 restraints	Δρmin = −0.24 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	0.8472 (3)	0.1813 (5)	0.45497 (9)	0.0877 (10)
O2	0.3489 (2)	0.2384 (4)	0.50884 (9)	0.0731 (9)
N1	0.6814 (3)	0.3386 (5)	0.55616 (12)	0.0627 (9)
N2	0.7850 (3)	0.3042 (5)	0.52501 (12)	0.0655 (10)
H2	0.8681	0.3330	0.5320	0.079*
N3	0.6226 (3)	0.1926 (5)	0.47282 (11)	0.0746 (11)
H3	0.5607	0.2305	0.4918	0.089*
N4	0.5831 (3)	0.0984 (6)	0.43144 (11)	0.0793 (11)
H4A	0.6347	0.1350	0.4075	0.119*
H4C	0.5948	−0.0210	0.4360	0.119*
N5	0.1757 (3)	0.0963 (5)	0.40633 (11)	0.0578 (9)
N6	0.2815 (3)	0.1455 (5)	0.43539 (11)	0.0610 (9)
H6A	0.3642	0.1413	0.4254	0.073*
N7	0.1225 (3)	0.2228 (5)	0.49114 (11)	0.0762 (11)
H7A	0.0802	0.1160	0.4849	0.091*
N8	0.0871 (3)	0.2698 (6)	0.53820 (12)	0.0931 (13)
H8A	0.1197	0.1869	0.5584	0.140*
H8C	0.1239	0.3782	0.5448	0.140*
C1	0.2557 (4)	0.2014 (6)	0.48027 (15)	0.0612 (11)
C2	0.2023 (4)	0.0482 (5)	0.36361 (14)	0.0559 (10)
C3	0.0833 (4)	−0.0052 (6)	0.33345 (14)	0.0583 (11)
C4	0.0951 (5)	−0.0984 (6)	0.29212 (15)	0.0735 (12)
H4	0.1824	−0.1264	0.2817	0.088*
C5	−0.0154 (6)	−0.1537 (7)	0.26486 (17)	0.0882 (15)
H5	−0.0020	−0.2153	0.2365	0.106*
C6	−0.1446 (6)	−0.1168 (8)	0.27995 (18)	0.0965 (17)
H6	−0.2203	−0.1574	0.2626	0.116*
C7	−0.1616 (5)	−0.0192 (8)	0.32097 (18)	0.1011 (17)
H7	−0.2494	0.0110	0.3306	0.121*
C8	−0.0505 (5)	0.0345 (7)	0.34802 (15)	0.0789 (14)
H8	−0.0639	0.0976	0.3761	0.095*
C9	0.3434 (4)	0.0465 (6)	0.34318 (14)	0.0776 (13)
H9A	0.3935	0.1513	0.3543	0.116*
H9B	0.3368	0.0498	0.3093	0.116*
H9C	0.3903	−0.0629	0.3529	0.116*
C10	0.7539 (4)	0.2242 (6)	0.48324 (16)	0.0670 (12)
C11	0.7111 (4)	0.4054 (6)	0.59662 (15)	0.0609 (11)
C12	0.5943 (5)	0.4406 (6)	0.62839 (16)	0.0696 (12)
C13	0.4626 (5)	0.4533 (7)	0.60913 (17)	0.0916 (16)
H13	0.4496	0.4393	0.5767	0.110*
C14	0.3502 (6)	0.4868 (8)	0.6376 (2)	0.119 (2)
H14	0.2631	0.4944	0.6241	0.143*
C15	0.3676 (7)	0.5084 (9)	0.6855 (2)	0.126 (2)
H15	0.2926	0.5326	0.7045	0.151*
C16	0.4968 (8)	0.4940 (8)	0.7055 (2)	0.116 (2)
H16	0.5093	0.5049	0.7381	0.139*
C17	0.6091 (6)	0.4628 (6)	0.67616 (17)	0.0891 (15)
H17	0.6963	0.4571	0.6897	0.107*
C18	0.8554 (4)	0.4505 (6)	0.61330 (15)	0.0754 (13)
H18A	0.9043	0.3393	0.6198	0.113*
H18B	0.8517	0.5230	0.6416	0.113*
H18C	0.9015	0.5178	0.5891	0.113*

	U11	U22	U33	U12	U13	U23
O1	0.0453 (16)	0.145 (3)	0.073 (2)	0.0036 (17)	0.0070 (15)	−0.0160 (19)
O2	0.0450 (15)	0.106 (2)	0.0682 (19)	0.0043 (15)	−0.0040 (14)	−0.0133 (17)
N1	0.062 (2)	0.070 (3)	0.057 (2)	0.0059 (18)	0.0080 (18)	−0.0016 (19)
N2	0.0499 (19)	0.088 (3)	0.058 (2)	−0.0044 (18)	0.0016 (17)	−0.012 (2)
N3	0.044 (2)	0.114 (3)	0.066 (2)	0.0049 (19)	0.0020 (16)	−0.025 (2)
N4	0.055 (2)	0.115 (3)	0.068 (2)	0.002 (2)	−0.0024 (17)	−0.015 (2)
N5	0.055 (2)	0.062 (2)	0.056 (2)	0.0020 (17)	−0.0064 (17)	−0.0019 (18)
N6	0.0501 (19)	0.080 (3)	0.054 (2)	−0.0011 (17)	0.0018 (16)	−0.0103 (19)
N7	0.054 (2)	0.111 (3)	0.064 (2)	−0.011 (2)	0.0074 (17)	−0.020 (2)
N8	0.056 (2)	0.152 (4)	0.072 (3)	0.002 (2)	0.0065 (18)	−0.015 (3)
C1	0.041 (2)	0.079 (3)	0.064 (3)	−0.003 (2)	−0.003 (2)	−0.002 (2)
C2	0.061 (3)	0.049 (3)	0.057 (3)	0.000 (2)	−0.004 (2)	0.001 (2)
C3	0.071 (3)	0.054 (3)	0.050 (2)	0.002 (2)	−0.003 (2)	0.006 (2)
C4	0.087 (3)	0.066 (3)	0.068 (3)	0.004 (3)	−0.005 (3)	−0.006 (3)
C5	0.116 (4)	0.078 (4)	0.069 (3)	−0.006 (3)	−0.016 (3)	−0.010 (3)
C6	0.105 (4)	0.104 (5)	0.079 (4)	−0.031 (4)	−0.027 (3)	0.003 (3)
C7	0.078 (4)	0.146 (5)	0.079 (4)	−0.013 (3)	−0.011 (3)	−0.004 (4)
C8	0.071 (3)	0.104 (4)	0.062 (3)	−0.011 (3)	−0.009 (2)	−0.009 (3)
C9	0.074 (3)	0.092 (4)	0.067 (3)	−0.001 (3)	0.011 (2)	−0.009 (3)
C10	0.050 (3)	0.089 (3)	0.062 (3)	0.009 (2)	−0.001 (2)	−0.006 (3)
C11	0.071 (3)	0.055 (3)	0.057 (3)	0.005 (2)	0.000 (2)	−0.001 (2)
C12	0.079 (3)	0.063 (3)	0.067 (3)	0.002 (2)	0.006 (2)	−0.002 (2)
C13	0.086 (4)	0.102 (4)	0.088 (4)	0.006 (3)	0.029 (3)	−0.021 (3)
C14	0.098 (4)	0.153 (6)	0.106 (4)	0.001 (4)	0.031 (4)	−0.032 (4)
C15	0.114 (5)	0.156 (6)	0.109 (5)	−0.011 (4)	0.052 (4)	−0.028 (4)
C16	0.153 (6)	0.122 (5)	0.074 (4)	−0.010 (5)	0.034 (4)	−0.016 (3)
C17	0.119 (4)	0.083 (4)	0.067 (3)	0.009 (3)	0.012 (3)	−0.005 (3)
C18	0.078 (3)	0.067 (3)	0.080 (3)	0.007 (2)	−0.009 (2)	−0.005 (2)

O1—C10	1.260 (4)	C5—C6	1.365 (6)
O2—C1	1.239 (4)	C5—H5	0.9300
N1—C11	1.274 (4)	C6—C7	1.374 (7)
N1—N2	1.374 (4)	C6—H6	0.9300
N2—C10	1.349 (5)	C7—C8	1.377 (6)
N2—H2	0.8600	C7—H7	0.9300
N3—C10	1.333 (5)	C8—H8	0.9300
N3—N4	1.407 (4)	C9—H9A	0.9600
N3—H3	0.8600	C9—H9B	0.9600
N4—H4A	0.8900	C9—H9C	0.9600
N4—H4C	0.8900	C11—C12	1.485 (5)
N5—C2	1.288 (4)	C11—C18	1.518 (5)
N5—N6	1.361 (4)	C12—C17	1.366 (5)
N6—C1	1.360 (5)	C12—C13	1.393 (6)
N6—H6A	0.8600	C13—C14	1.393 (6)
N7—C1	1.351 (4)	C13—H13	0.9300
N7—N8	1.422 (4)	C14—C15	1.373 (7)
N7—H7A	0.9000	C14—H14	0.9300
N8—H8A	0.8900	C15—C16	1.380 (8)
N8—H8C	0.8900	C15—H15	0.9300
C2—C3	1.485 (5)	C16—C17	1.404 (7)
C2—C9	1.503 (5)	C16—H16	0.9300
C3—C4	1.359 (5)	C17—H17	0.9300
C3—C8	1.407 (5)	C18—H18A	0.9600
C4—C5	1.378 (6)	C18—H18B	0.9600
C4—H4	0.9300	C18—H18C	0.9600
C11—N1—N2	119.1 (3)	C8—C7—H7	119.6
C10—N2—N1	118.8 (3)	C7—C8—C3	120.5 (4)
C10—N2—H2	120.6	C7—C8—H8	119.8
N1—N2—H2	120.6	C3—C8—H8	119.8
C10—N3—N4	121.4 (3)	C2—C9—H9A	109.5
C10—N3—H3	119.3	C2—C9—H9B	109.5
N4—N3—H3	119.3	H9A—C9—H9B	109.5
N3—N4—H4A	109.4	C2—C9—H9C	109.5
N3—N4—H4C	109.1	H9A—C9—H9C	109.5
H4A—N4—H4C	109.5	H9B—C9—H9C	109.5
C2—N5—N6	118.5 (3)	O1—C10—N3	121.3 (4)
C1—N6—N5	119.6 (3)	O1—C10—N2	120.5 (4)
C1—N6—H6A	120.2	N3—C10—N2	118.2 (4)
N5—N6—H6A	120.2	N1—C11—C12	116.3 (4)
C1—N7—N8	119.3 (3)	N1—C11—C18	124.2 (4)
C1—N7—H7A	107.2	C12—C11—C18	119.6 (4)
N8—N7—H7A	106.0	C17—C12—C13	117.6 (4)
N7—N8—H8A	110.3	C17—C12—C11	123.1 (4)
N7—N8—H8C	107.9	C13—C12—C11	119.3 (4)
H8A—N8—H8C	109.5	C14—C13—C12	121.2 (5)
O2—C1—N7	121.9 (4)	C14—C13—H13	119.4
O2—C1—N6	122.0 (3)	C12—C13—H13	119.4
N7—C1—N6	116.0 (3)	C15—C14—C13	120.2 (6)
N5—C2—C3	116.4 (4)	C15—C14—H14	119.9
N5—C2—C9	124.1 (3)	C13—C14—H14	119.9
C3—C2—C9	119.5 (4)	C14—C15—C16	119.7 (5)
C4—C3—C8	116.5 (4)	C14—C15—H15	120.2
C4—C3—C2	123.4 (4)	C16—C15—H15	120.2
C8—C3—C2	120.1 (4)	C15—C16—C17	119.3 (5)
C3—C4—C5	123.6 (5)	C15—C16—H16	120.4
C3—C4—H4	118.2	C17—C16—H16	120.4
C5—C4—H4	118.2	C12—C17—C16	122.0 (5)
C6—C5—C4	119.2 (5)	C12—C17—H17	119.0
C6—C5—H5	120.4	C16—C17—H17	119.0
C4—C5—H5	120.4	C11—C18—H18A	109.5
C5—C6—C7	119.3 (5)	C11—C18—H18B	109.5
C5—C6—H6	120.3	H18A—C18—H18B	109.5
C7—C6—H6	120.3	C11—C18—H18C	109.5
C6—C7—C8	120.9 (5)	H18A—C18—H18C	109.5
C6—C7—H7	119.6	H18B—C18—H18C	109.5

D—H···A	D—H	H···A	D···A	D—H···A
N2—H2···N8i	0.86	2.19	2.982 (4)	152
N4—H4C···O2ii	0.89	2.29	3.055 (5)	144
N3—H3···O2	0.86	2.13	2.895 (4)	148
N6—H6A···N4	0.86	2.17	2.972 (4)	156

Table 1

Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
N2—H2⋯N8i	0.86	2.19	2.982 (4)	152
N4—H4C⋯O2ii	0.89	2.29	3.055 (5)	144
N3—H3⋯O2	0.86	2.13	2.895 (4)	148
N6—H6A⋯N4	0.86	2.17	2.972 (4)	156

Symmetry codes: (i) ; (ii) .