1-(1-Phenyl­ethyl­idene)carbonohydrazide

Qiao, Y.; Ju, X.; Gao, Z.; Kong, L.

doi:10.1107/S1600536810038353

organic compounds

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ISSN: 2056-9890

Volume 66| Part 10| October 2010| Page o2691

doi:10.1107/S1600536810038353

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1-(1-Phenylethylidene)carbonohydrazide

Yan Qiao,^a Xiuping Ju,^a Zhiqing Gao ^a and Lingqian Kong ^a ^*

^aDongchang College, Liaocheng University, Liaocheng 250059, People's Republic of China
^*Correspondence e-mail: konglingqian08@163.com

(Received 2 September 2010; accepted 25 September 2010; online 30 September 2010)

The title compound, C₉H₁₂N₄O, crystallizes with two independent molecules in the asymmetric unit. In the crystal, intermolecular N—H⋯O and N—H⋯N hydrogen bonds link the molecules into paired ribbons propagated in [100]. The crystal studied was a twin (twin law $[\overline{1}]$ 00/0 $[\overline{1}]$ 0/001) 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_r = 192.23
Monoclinic, P 2₁ /c
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[F² > 2σ(F²)] = 0.062
wR(F²) = 0.186
S = 0.84
3568 reflections
256 parameters
H-atom parameters constrained
Δρ_max = 0.26 e Å⁻³
Δρ_min = −0.24 e Å⁻³

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) x+1, y, z; (ii) -x+1, -y, -z+1.

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.

Supporting information

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

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

checkCIF report

Comment top

Carbonohydrazide derivatives are popular ligands in coordination chemistry due to the strong coordinative ability (Esmail et al., 1977). Meanwhile, they have also attracted much attention due to interesting bioactivity such as antibacteriale antifungal, anticonvulsant, anticancer activities (Loncle et al., 2004). Herewith we present the crystal structure of the title compound, (I), which is a carbonohydrazide derivative.

In (I) (Fig. 1), the bond lengths and angles are normal and comparable to those observed in the reported compound (Meyers et al., 1995). The C=N bond lengths in the molecule are 1.282 (5) °, 1.272 (5)° (C2=N5, C1=N11), respectively, showing the double-bond character. The dihedral angle between the benzene ring (C12—C17) and the plane of C11/N1/N2 is 19.17 (27) °, while the dihedral angle between the benzene ring (C3—C8) and the plane of C2/N5/N6 is 14.87 (31) °.

Intermolecular N—H···O and N—H···N hydrogen bonds (Table 1) link the molecules into paired ribbons propagated in direction [100].

Related literature top

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

Experimental top

Acetophenone (10.0 mmol) and carbohydrazide (10.0 mmol) were mixed in 50 ml flash under sovlent-free condtions. After stirring 2 h at 373 K, the resulting mixture was cooled to room temperature, and recrystalized from ethanol, and afforded the title compound as a crystalline solid. Elemental analysis: calculated for C₉H₁₂N₄O: C 56.24, H 6.29, N 29.15%; found: C 56.13, H 6.24, N 29.31%.

Computing details top

Data collection: SMART (Bruker, 2007); cell refinement: SAINT (Bruker, 2007); data reduction: SAINT (Bruker, 2007); 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 (Sheldrick, 2008).

Figures top

Fig. 1. A view of (I) showing the atomic numbering scheme and 30% probability displacement ellipsoids.

1-(1-Phenylethylidene)carbonohydrazide top

Crystal data top

C₉H₁₂N₄O	F(000) = 816
M_r = 192.23	D_x = 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

Data collection top

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

Refinement top

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(F_o²) + (0.0777P)²] where P = (F_o² + 2F_c²)/3
3568 reflections	(Δ/σ)_max < 0.001
256 parameters	Δρ_max = 0.26 e Å⁻³
0 restraints	Δρ_min = −0.24 e Å⁻³

Crystal data top

C₉H₁₂N₄O	V = 2021.9 (3) Å³
M_r = 192.23	Z = 8
Monoclinic, P2₁/c	Mo Kα radiation
a = 9.7744 (8) Å	µ = 0.09 mm⁻¹
b = 7.3163 (7) Å	T = 293 K
c = 28.2761 (3) Å	0.43 × 0.17 × 0.15 mm
β = 90.796 (1)°

Data collection top

Bruker SMART APEX CCD area-detector diffractometer	3568 independent reflections
Absorption correction: multi-scan (SADABS; Sheldrick, 2007)	1412 reflections with I > 2σ(I)
T_min = 0.963, T_max = 0.987	R_int = 0.111
9568 measured reflections

Refinement top

R[F² > 2σ(F²)] = 0.062	0 restraints
wR(F²) = 0.186	H-atom parameters constrained
S = 0.84	Δρ_max = 0.26 e Å⁻³
3568 reflections	Δρ_min = −0.24 e Å⁻³
256 parameters

Special details top

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.

Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Å²) top

	x	y	z	U_iso*/U_eq
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*

Atomic displacement parameters (Å²) top

	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)

Geometric parameters (Å, º) top

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

Hydrogen-bond geometry (Å, º) top

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) x+1, y, z; (ii) −x+1, −y, −z+1.

Experimental details

Crystal data
Chemical formula	C₉H₁₂N₄O
M_r	192.23
Crystal system, space group	Monoclinic, P2₁/c
Temperature (K)	293
a, b, c (Å)	9.7744 (8), 7.3163 (7), 28.2761 (3)
β (°)	90.796 (1)
V (Å³)	2021.9 (3)
Z	8
Radiation type	Mo Kα
µ (mm⁻¹)	0.09
Crystal size (mm)	0.43 × 0.17 × 0.15

Data collection
Diffractometer	Bruker SMART APEX CCD area-detector diffractometer
Absorption correction	Multi-scan (SADABS; Sheldrick, 2007)
T_min, T_max	0.963, 0.987
No. of measured, independent and observed [I > 2σ(I)] reflections	9568, 3568, 1412
R_int	0.111
(sin θ/λ)_max (Å⁻¹)	0.595

Refinement
R[F² > 2σ(F²)], wR(F²), S	0.062, 0.186, 0.84
No. of reflections	3568
No. of parameters	256
H-atom treatment	H-atom parameters constrained
Δρ_max, Δρ_min (e Å⁻³)	0.26, −0.24

Computer programs: SMART (Bruker, 2007), SAINT (Bruker, 2007), SHELXS97 (Sheldrick, 2008), SHELXL97 (Sheldrick, 2008), SHELXTL (Sheldrick, 2008).

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
N2—H2···N8ⁱ	0.86	2.19	2.982 (4)	152.1
N4—H4C···O2ⁱⁱ	0.89	2.29	3.055 (5)	144.1
N3—H3···O2	0.86	2.13	2.895 (4)	147.5
N6—H6A···N4	0.86	2.17	2.972 (4)	155.7

Symmetry codes: (i) x+1, y, z; (ii) −x+1, −y, −z+1.

Acknowledgements

This project was supported by the Foundation of Dongchang College, Liaocheng University (grant No. LG0801).

References

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