(E)-1-Phenyl-ethanone semicarbazone.

In the title compound, C(9)H(11)N(3)O, the benzene ring is disordered over two positions with refined occupancies of 0.922 (5) and 0.078 (5). The program PLATON [Spek (2009 ▶). Acta Cryst. D65, 148-155] recommends the solution in the space group C2/m with a = 7.3050 (3), b = 6.6745 (2), c = 18.3853 (6) Å and β = 96.986 (2)°. However, the large number of non-extinct reflections needed to be ignored if C2/m is chosen suggested that the space group is incorrect, even though the R values are lower than that for P2(1)/c. The semicarbazone group is essentially planar, with a maximum deviation of 0.046 (1) Å for one of the N atoms. The mean plane of the semicarbazone group forms dihedral angles of 33.61 (8) and 39.1 (9)° with the benzene ring of the major and minor components, respectively. In the crystal structure, mol-ecules are linked by inter-molecular N-H⋯O hydrogen bonds into extended chains along the c axis. The crystal structure is further stabilized by weak inter-molucular C-H⋯π inter-actions.

Related literature

For hydrogen-bond motifs, see: Bernstein et al. (1995 ▶). For applications of semicarbazone derivatives, see: Chandra & Gupta (2005 ▶); Jain et al. (2002 ▶); Pilgram (1978 ▶); Warren et al. (1977 ▶); Yogeeswari et al. (2004 ▶). For the preparation of the title compound, see: Furniss et al. (1978 ▶). For related structures, see: Fun et al. (2009a ▶,b ▶,c ▶). For the stability of the temperature controller used for the data collection, see: Cosier & Glazer (1986 ▶).

Experimental

Crystal data

C9H11N3O

M = 177.21

Monoclinic,

a = 18.3853 (6) Å

b = 6.6745 (2) Å

c = 7.3050 (3) Å

β = 96.986 (2)°

V = 889.76 (5) Å3

Z = 4

Mo Kα radiation

μ = 0.09 mm−1

T = 100 K

0.32 × 0.13 × 0.03 mm

Data collection

Bruker SMART APEXII CCD area-detector diffractometer

Absorption correction: multi-scan (; Bruker, 2005 ▶) T min = 0.881, T max = 0.997

9294 measured reflections

2034 independent reflections

1449 reflections with I > 2σ(I)

R int = 0.043

Refinement

R[F 2 > 2σ(F 2)] = 0.056

wR(F 2) = 0.181

S = 1.08

2034 reflections

148 parameters

H atoms treated by a mixture of independent and constrained refinement

Δρmax = 0.43 e Å−3

Δρmin = −0.46 e Å−3

Data collection: APEX2 (Bruker, 2005 ▶); cell refinement: SAINT (Bruker, 2005 ▶); 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 datablocks global, I. DOI: 10.1107/S1600536809025847/lh2857sup1.cif

Structure factors: contains datablocks I. DOI: 10.1107/S1600536809025847/lh2857Isup2.hkl

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

C9H11N3O	F(000) = 376
Mr = 177.21	Dx = 1.323 Mg m−3
Monoclinic, P21/c	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: -P 2ybc	Cell parameters from 2113 reflections
a = 18.3853 (6) Å	θ = 3.4–29.6°
b = 6.6745 (2) Å	µ = 0.09 mm−1
c = 7.3050 (3) Å	T = 100 K
β = 96.986 (2)°	Plate, colourless
V = 889.76 (5) Å3	0.32 × 0.13 × 0.03 mm
Z = 4

Bruker SMART APEXII CCD area-detector diffractometer	2034 independent reflections
Radiation source: fine-focus sealed tube	1449 reflections with I > 2σ(I)
graphite	Rint = 0.043
φ and ω scans	θmax = 27.5°, θmin = 1.1°
Absorption correction: multi-scan (SADABS; Bruker, 2005)	h = −23→23
Tmin = 0.881, Tmax = 0.997	k = −8→8
9294 measured reflections	l = −5→9

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)] = 0.056	Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.181	H atoms treated by a mixture of independent and constrained refinement
S = 1.08	w = 1/[σ2(Fo2) + (0.0993P)2 + 0.2822P] where P = (Fo2 + 2Fc2)/3
2034 reflections	(Δ/σ)max < 0.001
148 parameters	Δρmax = 0.43 e Å−3
0 restraints	Δρmin = −0.46 e Å−3

Experimental. The crystal was placed in the cold stream of an Oxford Cyrosystems Cobra open-flow nitrogen cryostat (Cosier & Glazer, 1986) operating at 100.0 (1)K.

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	Occ. (<1)
O1	0.51345 (7)	0.4963 (2)	0.7657 (2)	0.0165 (4)
N1	0.32789 (9)	0.4925 (2)	0.8239 (3)	0.0130 (4)
N2	0.40259 (9)	0.4938 (2)	0.8715 (3)	0.0142 (4)
N3	0.41052 (10)	0.4917 (3)	0.5585 (3)	0.0174 (5)
C3	0.05611 (11)	0.5011 (3)	0.7581 (3)	0.0169 (5)
H3A	0.0064	0.5007	0.7151	0.020*
C6	0.20605 (10)	0.5016 (3)	0.8879 (3)	0.0114 (4)
C7	0.28592 (11)	0.5045 (3)	0.9528 (3)	0.0119 (5)
C8	0.44581 (11)	0.4942 (3)	0.7296 (3)	0.0135 (5)
C9	0.31370 (11)	0.5196 (3)	1.1541 (3)	0.0149 (5)
H9A	0.3444	0.6357	1.1750	0.022*
H9B	0.3415	0.4018	1.1920	0.022*
H9C	0.2730	0.5311	1.2242	0.022*
C1A	0.17941 (11)	0.3969 (3)	0.7290 (3)	0.0144 (5)	0.922 (5)
H1AA	0.2120	0.3267	0.6649	0.017*	0.922 (5)
C2A	0.10550 (12)	0.3954 (3)	0.6644 (3)	0.0176 (5)	0.922 (5)
H2AA	0.0888	0.3238	0.5584	0.021*	0.922 (5)
C4A	0.08190 (11)	0.6070 (3)	0.9162 (3)	0.0164 (5)	0.922 (5)
H4AA	0.0492	0.6784	0.9789	0.020*	0.922 (5)
C5A	0.15600 (11)	0.6073 (3)	0.9816 (3)	0.0142 (5)	0.922 (5)
H5AA	0.1726	0.6781	1.0883	0.017*	0.922 (5)
C1B	0.1548 (15)	0.395 (4)	0.979 (4)	0.022 (7)*	0.078 (5)
H1BA	0.1725	0.3268	1.0861	0.026*	0.078 (5)
C2B	0.0822 (18)	0.385 (5)	0.923 (5)	0.032 (8)*	0.078 (5)
H2BA	0.0506	0.3096	0.9861	0.039*	0.078 (5)
C4B	0.1048 (17)	0.607 (5)	0.664 (5)	0.032 (8)*	0.078 (5)
H4BA	0.0876	0.6756	0.5570	0.038*	0.078 (5)
C5B	0.1785 (16)	0.612 (5)	0.728 (4)	0.025 (7)*	0.078 (5)
H5BA	0.2103	0.6871	0.6662	0.030*	0.078 (5)
H1N2	0.4271 (15)	0.500 (3)	0.983 (4)	0.025 (7)*
H1N3	0.3627 (14)	0.495 (3)	0.543 (4)	0.019 (6)*
H2N3	0.4366 (14)	0.496 (3)	0.469 (4)	0.020 (6)*

	U11	U22	U33	U12	U13	U23
O1	0.0110 (7)	0.0241 (8)	0.0143 (8)	−0.0017 (6)	0.0015 (6)	−0.0005 (6)
N1	0.0088 (8)	0.0142 (8)	0.0159 (9)	0.0007 (6)	0.0010 (6)	−0.0003 (7)
N2	0.0094 (8)	0.0207 (9)	0.0121 (9)	−0.0008 (7)	−0.0002 (7)	0.0002 (8)
N3	0.0102 (9)	0.0303 (11)	0.0118 (9)	−0.0010 (8)	0.0020 (7)	0.0001 (8)
C3	0.0101 (9)	0.0172 (10)	0.0227 (12)	0.0015 (8)	−0.0007 (8)	0.0033 (9)
C6	0.0110 (9)	0.0101 (9)	0.0131 (10)	0.0001 (7)	0.0008 (7)	0.0028 (8)
C7	0.0131 (9)	0.0088 (9)	0.0135 (10)	0.0005 (7)	0.0006 (8)	0.0005 (8)
C8	0.0121 (9)	0.0133 (9)	0.0152 (10)	0.0000 (7)	0.0024 (7)	−0.0005 (8)
C9	0.0118 (9)	0.0243 (11)	0.0086 (10)	−0.0009 (8)	0.0016 (7)	−0.0015 (8)
C1A	0.0135 (10)	0.0140 (11)	0.0155 (12)	0.0018 (8)	0.0015 (9)	−0.0016 (9)
C2A	0.0158 (11)	0.0169 (11)	0.0189 (12)	−0.0007 (9)	−0.0028 (9)	−0.0009 (9)
C4A	0.0127 (11)	0.0186 (12)	0.0185 (12)	0.0018 (9)	0.0045 (9)	−0.0008 (9)
C5A	0.0160 (11)	0.0143 (11)	0.0120 (11)	0.0012 (9)	0.0011 (8)	−0.0008 (9)

O1—C8	1.240 (2)	C6—C7	1.487 (3)
N1—C7	1.290 (3)	C7—C9	1.500 (3)
N1—N2	1.375 (2)	C9—H9A	0.9600
N2—C8	1.380 (3)	C9—H9B	0.9600
N2—H1N2	0.88 (3)	C9—H9C	0.9600
N3—C8	1.336 (3)	C1A—C2A	1.383 (3)
N3—H1N3	0.87 (3)	C1A—H1AA	0.9300
N3—H2N3	0.85 (3)	C2A—H2AA	0.9300
C3—C4B	1.39 (3)	C4A—C5A	1.388 (3)
C3—C4A	1.387 (3)	C4A—H4AA	0.9300
C3—C2A	1.394 (3)	C5A—H5AA	0.9300
C3—C2B	1.46 (3)	C1B—C2B	1.35 (4)
C3—H3A	0.9300	C1B—H1BA	0.9300
C6—C1A	1.392 (3)	C2B—H2BA	0.9300
C6—C5A	1.402 (3)	C4B—C5B	1.38 (4)
C6—C1B	1.41 (3)	C4B—H4BA	0.9300
C6—C5B	1.42 (3)	C5B—H5BA	0.9300
C7—N1—N2	118.86 (18)	N3—C8—N2	116.34 (18)
N1—N2—C8	117.31 (18)	C7—C9—H9A	109.5
N1—N2—H1N2	128.1 (18)	C7—C9—H9B	109.5
C8—N2—H1N2	114.6 (18)	H9A—C9—H9B	109.5
C8—N3—H1N3	119.0 (17)	C7—C9—H9C	109.5
C8—N3—H2N3	117.3 (18)	H9A—C9—H9C	109.5
H1N3—N3—H2N3	124 (2)	H9B—C9—H9C	109.5
C4B—C3—C4A	88.6 (14)	C2A—C1A—C6	121.3 (2)
C4B—C3—C2A	61.1 (13)	C2A—C1A—H1AA	119.4
C4A—C3—C2A	119.32 (19)	C6—C1A—H1AA	119.4
C4B—C3—C2B	120.7 (19)	C1A—C2A—C3	120.0 (2)
C4A—C3—C2B	62.5 (13)	C1A—C2A—H2AA	120.0
C2A—C3—C2B	88.3 (13)	C3—C2A—H2AA	120.0
C4B—C3—H3A	120.2	C3—C4A—C5A	120.6 (2)
C4A—C3—H3A	120.3	C3—C4A—H4AA	119.7
C2A—C3—H3A	120.3	C5A—C4A—H4AA	119.7
C2B—C3—H3A	119.1	C4A—C5A—C6	120.4 (2)
C1A—C6—C5A	118.32 (18)	C4A—C5A—H5AA	119.8
C1A—C6—C1B	87.4 (12)	C6—C5A—H5AA	119.8
C5A—C6—C1B	60.4 (11)	C2B—C1B—C6	125 (3)
C1A—C6—C5B	61.3 (12)	C2B—C1B—H1BA	117.4
C5A—C6—C5B	87.2 (12)	C6—C1B—H1BA	117.4
C1B—C6—C5B	117.2 (17)	C1B—C2B—C3	116 (3)
C1A—C6—C7	120.39 (17)	C1B—C2B—H2BA	122.1
C5A—C6—C7	121.27 (19)	C3—C2B—H2BA	122.1
C1B—C6—C7	123.1 (12)	C5B—C4B—C3	121 (3)
C5B—C6—C7	119.7 (12)	C5B—C4B—H4BA	119.6
N1—C7—C6	114.93 (18)	C3—C4B—H4BA	119.6
N1—C7—C9	123.85 (18)	C4B—C5B—C6	120 (3)
C6—C7—C9	121.22 (17)	C4B—C5B—H5BA	119.9
O1—C8—N3	124.04 (19)	C6—C5B—H5BA	119.9
O1—C8—N2	119.63 (19)
C7—N1—N2—C8	−175.79 (18)	C2B—C3—C4A—C5A	70.3 (14)
N2—N1—C7—C6	−179.91 (16)	C3—C4A—C5A—C6	0.5 (3)
N2—N1—C7—C9	−0.2 (3)	C1A—C6—C5A—C4A	−0.1 (3)
C1A—C6—C7—N1	30.7 (3)	C1B—C6—C5A—C4A	−68.7 (14)
C5A—C6—C7—N1	−147.66 (19)	C5B—C6—C5A—C4A	54.9 (12)
C1B—C6—C7—N1	139.4 (14)	C7—C6—C5A—C4A	178.31 (19)
C5B—C6—C7—N1	−41.4 (14)	C1A—C6—C1B—C2B	−54 (3)
C1A—C6—C7—C9	−149.0 (2)	C5A—C6—C1B—C2B	71 (3)
C5A—C6—C7—C9	32.6 (3)	C5B—C6—C1B—C2B	2(4)
C1B—C6—C7—C9	−40.4 (14)	C7—C6—C1B—C2B	−179 (2)
C5B—C6—C7—C9	138.9 (14)	C6—C1B—C2B—C3	−2(4)
N1—N2—C8—O1	179.65 (17)	C4B—C3—C2B—C1B	2(4)
N1—N2—C8—N3	−0.5 (3)	C4A—C3—C2B—C1B	−68 (2)
C5A—C6—C1A—C2A	−0.3 (3)	C2A—C3—C2B—C1B	57 (3)
C1B—C6—C1A—C2A	53.8 (12)	C4A—C3—C4B—C5B	54 (3)
C5B—C6—C1A—C2A	−69.3 (13)	C2A—C3—C4B—C5B	−71 (3)
C7—C6—C1A—C2A	−178.78 (19)	C2B—C3—C4B—C5B	−2(4)
C6—C1A—C2A—C3	0.4 (3)	C3—C4B—C5B—C6	2(4)
C4B—C3—C2A—C1A	69.9 (17)	C1A—C6—C5B—C4B	68 (3)
C4A—C3—C2A—C1A	−0.1 (3)	C5A—C6—C5B—C4B	−57 (3)
C2B—C3—C2A—C1A	−57.0 (13)	C1B—C6—C5B—C4B	−2(3)
C4B—C3—C4A—C5A	−55.7 (14)	C7—C6—C5B—C4B	179 (2)
C2A—C3—C4A—C5A	−0.4 (3)

D—H···A	D—H	H···A	D···A	D—H···A
N2—H1N2···O1i	0.88 (3)	2.02 (3)	2.901 (3)	177.2 (19)
N3—H2N3···O1ii	0.86 (3)	2.04 (3)	2.894 (3)	173 (3)
C2A—H2AA···Cgiii	0.93	2.93	3.707 (2)	142
C5A—H5AA···Cgiv	0.93	2.90	3.678 (2)	142

Table 1

Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
N2—H1N2⋯O1i	0.88 (3)	2.02 (3)	2.901 (3)	177.2 (19)
N3—H2N3⋯O1ii	0.86 (3)	2.04 (3)	2.894 (3)	173 (3)
C2A—H2AA⋯Cgiii	0.93	2.93	3.707 (2)	142
C5A—H5AA⋯Cgiv	0.93	2.90	3.678 (2)	142

Symmetry codes: (i) ; (ii) ; (iii) ; (iv) . Cg is the centroid of the C1A,C2A,C3,C4A,C5A,C6 benzene ring.