4-Phenyl-semicarbazide.

The title compound, C(7)H(9)N(3)O, crystallizes with two independent mol-ecules per asymmetric unit. The structure is stabilized by four distinct inter-molecular N-H⋯O hydrogen bonds. Four intra-molecular inter-actions of the N-H⋯N and C-H⋯O types are also observed.

Related literature

For related structures see: Ashiq, Jamal et al. (2008 ▶, 2009 ▶); Jamal et al. (2008 ▶ ▶, 2009 ▶); Kallel et al. (1992 ▶); Saraogi et al. (2002 ▶); For the biological activity of hydrazides, see: Ara et al. (2007 ▶); Ashiq, Ara et al. (2008 ▶).

Experimental

Crystal data

C7H9N3O

M = 151.17

Monoclinic,

a = 16.5984 (10) Å

b = 8.8862 (4) Å

c = 10.3518 (6) Å

β = 91.359 (3)°

V = 1526.43 (14) Å3

Z = 8

Mo Kα radiation

μ = 0.09 mm−1

T = 296 K

0.43 × 0.15 × 0.12 mm

Data collection

Bruker Kappa APEXII CCD diffractometer

Absorption correction: multi-scan (SADABS; Bruker, 2005 ▶) T min = 0.979, T max = 0.990

15394 measured reflections

3500 independent reflections

2258 reflections with I > 2σ(I)

R int = 0.030

Refinement

R[F 2 > 2σ(F 2)] = 0.039

wR(F 2) = 0.107

S = 1.03

3500 reflections

223 parameters

H atoms treated by a mixture of independent and constrained refinement

Δρmax = 0.16 e Å−3

Δρmin = −0.15 e Å−3

Data collection: APEX2 (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: ORTEP-3 for Windows (Farrugia, 1997 ▶) and Mercury (Macrae et al., 2006 ▶); software used to prepare material for publication: SHELXL97.

Crystal structure: contains datablocks I, global. DOI: 10.1107/S1600536809035284/pk2182sup1.cif

Structure factors: contains datablocks I. DOI: 10.1107/S1600536809035284/pk2182Isup2.hkl

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

C7H9N3O	F(000) = 640
Mr = 151.17	Dx = 1.316 Mg m−3
Monoclinic, P21/c	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: -P 2ybc	Cell parameters from 3838 reflections
a = 16.5984 (10) Å	θ = 2.5–24.4°
b = 8.8862 (4) Å	µ = 0.09 mm−1
c = 10.3518 (6) Å	T = 296 K
β = 91.359 (3)°	Needle, colourless
V = 1526.43 (14) Å3	0.43 × 0.15 × 0.12 mm
Z = 8

Bruker Kappa APEXII CCD diffractometer	3500 independent reflections
Radiation source: fine-focus sealed tube	2258 reflections with I > 2σ(I)
graphite	Rint = 0.030
ω scans	θmax = 27.5°, θmin = 2.5°
Absorption correction: multi-scan (SADABS; Bruker, 2005)	h = −21→20
Tmin = 0.979, Tmax = 0.990	k = −6→11
15394 measured reflections	l = −13→13

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)] = 0.039	Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.107	H atoms treated by a mixture of independent and constrained refinement
S = 1.03	w = 1/[σ2(Fo2) + (0.0459P)2 + 0.1614P] where P = (Fo2 + 2Fc2)/3
3500 reflections	(Δ/σ)max < 0.001
223 parameters	Δρmax = 0.16 e Å−3
0 restraints	Δρmin = −0.15 e Å−3

Geometry. Bond distances, angles etc. have been calculated using the rounded fractional coordinates. All su's are estimated from the variances of the (full) variance-covariance matrix. The cell e.s.d.'s are taken into account in the estimation of distances, angles and torsion angles

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
O11	0.01604 (6)	0.79747 (12)	0.48141 (10)	0.0553 (4)
N11	0.09359 (7)	0.58992 (13)	0.44101 (12)	0.0427 (4)
N12	−0.01754 (7)	0.64373 (13)	0.31698 (11)	0.0438 (4)
N13	−0.00041 (8)	0.51513 (16)	0.24513 (14)	0.0506 (5)
C11	0.15892 (8)	0.60879 (14)	0.52831 (12)	0.0354 (4)
C12	0.16095 (9)	0.71248 (16)	0.62779 (13)	0.0439 (5)
C13	0.22909 (10)	0.72368 (18)	0.70707 (15)	0.0508 (5)
C14	0.29449 (9)	0.63342 (19)	0.68932 (15)	0.0554 (6)
C15	0.29205 (10)	0.52914 (19)	0.59133 (16)	0.0572 (6)
C16	0.22502 (9)	0.51619 (17)	0.51125 (14)	0.0462 (5)
C17	0.03011 (8)	0.68266 (15)	0.41816 (13)	0.0378 (5)
O21	0.17516 (6)	0.28317 (12)	0.23819 (10)	0.0529 (4)
N21	0.28009 (7)	0.40092 (15)	0.13966 (13)	0.0500 (5)
N22	0.15623 (8)	0.38933 (15)	0.04272 (12)	0.0488 (4)
N23	0.18846 (8)	0.47117 (17)	−0.05959 (13)	0.0514 (5)
C21	0.34464 (8)	0.38042 (16)	0.22790 (14)	0.0433 (5)
C22	0.34917 (9)	0.26384 (18)	0.31535 (15)	0.0509 (5)
C23	0.41651 (9)	0.2490 (2)	0.39537 (16)	0.0593 (6)
C24	0.47943 (10)	0.3476 (2)	0.38889 (17)	0.0643 (6)
C25	0.47515 (10)	0.4626 (2)	0.30239 (18)	0.0707 (7)
C26	0.40834 (9)	0.48014 (19)	0.22223 (17)	0.0596 (6)
C27	0.20285 (8)	0.35311 (15)	0.14604 (14)	0.0405 (5)
H11N	0.0960 (9)	0.5210 (18)	0.3845 (15)	0.0510*
H12	0.11680	0.77440	0.64140	0.0530*
H12N	−0.0624 (9)	0.6927 (17)	0.3025 (14)	0.0530*
H13	0.23030	0.79400	0.77360	0.0610*
H13N	−0.0413 (10)	0.4498 (19)	0.2569 (15)	0.0610*
H14	0.34000	0.64240	0.74280	0.0660*
H14N	0.0017 (10)	0.5393 (19)	0.1621 (17)	0.0610*
H15	0.33610	0.46660	0.57900	0.0690*
H16	0.22410	0.44500	0.44540	0.0550*
H21N	0.2880 (10)	0.4551 (18)	0.0733 (16)	0.0600*
H22	0.30700	0.19530	0.32060	0.0610*
H22N	0.1043 (10)	0.3598 (17)	0.0395 (15)	0.0590*
H23	0.41900	0.17040	0.45470	0.0710*
H23N	0.1844 (10)	0.4143 (19)	−0.1336 (16)	0.0620*
H24	0.52460	0.33620	0.44290	0.0770*
H24N	0.1591 (10)	0.5550 (19)	−0.0679 (15)	0.0620*
H25	0.51780	0.53010	0.29720	0.0850*
H26	0.40610	0.55970	0.16390	0.0720*

	U11	U22	U33	U12	U13	U23
O11	0.0570 (7)	0.0548 (7)	0.0534 (7)	0.0192 (5)	−0.0156 (5)	−0.0142 (5)
N11	0.0424 (7)	0.0419 (7)	0.0434 (7)	0.0079 (6)	−0.0090 (6)	−0.0063 (5)
N12	0.0394 (7)	0.0465 (7)	0.0449 (7)	0.0100 (6)	−0.0088 (6)	−0.0061 (6)
N13	0.0484 (8)	0.0510 (8)	0.0519 (8)	0.0034 (6)	−0.0074 (7)	−0.0105 (7)
C11	0.0355 (7)	0.0362 (7)	0.0345 (7)	−0.0003 (6)	0.0002 (6)	0.0061 (6)
C12	0.0433 (8)	0.0468 (8)	0.0416 (8)	0.0066 (7)	−0.0014 (6)	−0.0018 (7)
C13	0.0546 (10)	0.0539 (9)	0.0435 (9)	−0.0006 (8)	−0.0050 (7)	−0.0052 (7)
C14	0.0438 (9)	0.0679 (11)	0.0537 (10)	0.0002 (8)	−0.0136 (7)	0.0009 (8)
C15	0.0435 (9)	0.0658 (11)	0.0619 (10)	0.0155 (8)	−0.0063 (8)	−0.0005 (8)
C16	0.0438 (8)	0.0480 (9)	0.0464 (9)	0.0087 (7)	−0.0042 (7)	−0.0025 (7)
C17	0.0372 (8)	0.0392 (8)	0.0370 (8)	0.0024 (6)	−0.0014 (6)	0.0032 (6)
O21	0.0386 (6)	0.0680 (7)	0.0520 (7)	−0.0068 (5)	−0.0024 (5)	0.0135 (5)
N21	0.0380 (7)	0.0630 (9)	0.0488 (8)	−0.0090 (6)	−0.0040 (6)	0.0102 (6)
N22	0.0372 (7)	0.0595 (8)	0.0495 (8)	−0.0050 (6)	−0.0050 (6)	0.0095 (6)
N23	0.0517 (8)	0.0591 (9)	0.0432 (8)	0.0001 (6)	−0.0026 (6)	0.0044 (7)
C21	0.0340 (8)	0.0526 (9)	0.0433 (8)	−0.0017 (6)	0.0008 (6)	−0.0063 (7)
C22	0.0384 (8)	0.0566 (10)	0.0578 (10)	−0.0019 (7)	0.0009 (7)	0.0013 (8)
C23	0.0455 (10)	0.0743 (12)	0.0579 (10)	0.0094 (8)	−0.0022 (8)	0.0068 (9)
C24	0.0405 (9)	0.0906 (13)	0.0612 (11)	0.0034 (9)	−0.0121 (8)	−0.0091 (10)
C25	0.0445 (10)	0.0823 (13)	0.0846 (13)	−0.0177 (9)	−0.0116 (9)	−0.0025 (11)
C26	0.0488 (10)	0.0628 (11)	0.0669 (11)	−0.0135 (8)	−0.0044 (8)	0.0043 (8)
C27	0.0355 (8)	0.0419 (8)	0.0440 (8)	−0.0013 (6)	−0.0016 (6)	−0.0033 (7)

O11—C17	1.2375 (17)	C12—C13	1.385 (2)
O21—C27	1.2362 (17)	C13—C14	1.366 (2)
N11—C11	1.4051 (18)	C14—C15	1.374 (2)
N11—C17	1.3541 (18)	C15—C16	1.376 (2)
N12—N13	1.3964 (18)	C12—H12	0.9300
N12—C17	1.3427 (18)	C13—H13	0.9300
N11—H11N	0.849 (16)	C14—H14	0.9300
N12—H12N	0.872 (15)	C15—H15	0.9300
N13—H14N	0.887 (18)	C16—H16	0.9300
N13—H13N	0.904 (17)	C21—C22	1.377 (2)
N21—C21	1.4032 (19)	C21—C26	1.382 (2)
N21—C27	1.3537 (18)	C22—C23	1.382 (2)
N22—C27	1.3443 (19)	C23—C24	1.366 (2)
N22—N23	1.4013 (19)	C24—C25	1.360 (3)
N21—H21N	0.852 (16)	C25—C26	1.378 (2)
N22—H22N	0.901 (16)	C22—H22	0.9300
N23—H23N	0.919 (17)	C23—H23	0.9300
N23—H24N	0.893 (17)	C24—H24	0.9300
C11—C12	1.3817 (19)	C25—H25	0.9300
C11—C16	1.386 (2)	C26—H26	0.9300
C11—N11—C17	128.70 (12)	C13—C12—H12	120.00
N13—N12—C17	120.18 (12)	C14—C13—H13	119.00
C11—N11—H11N	118.8 (10)	C12—C13—H13	119.00
C17—N11—H11N	111.6 (10)	C15—C14—H14	120.00
C17—N12—H12N	119.4 (10)	C13—C14—H14	120.00
N13—N12—H12N	120.0 (10)	C16—C15—H15	120.00
N12—N13—H14N	109.3 (11)	C14—C15—H15	120.00
H13N—N13—H14N	109.5 (15)	C15—C16—H16	120.00
N12—N13—H13N	106.9 (11)	C11—C16—H16	120.00
C21—N21—C27	129.56 (13)	C22—C21—C26	118.72 (14)
N23—N22—C27	120.18 (12)	N21—C21—C22	123.69 (13)
C21—N21—H21N	117.9 (11)	N21—C21—C26	117.53 (13)
C27—N21—H21N	112.4 (11)	C21—C22—C23	119.79 (14)
C27—N22—H22N	119.5 (10)	C22—C23—C24	121.19 (16)
N23—N22—H22N	120.4 (10)	C23—C24—C25	119.10 (16)
H23N—N23—H24N	110.4 (15)	C24—C25—C26	120.69 (16)
N22—N23—H24N	106.8 (10)	C21—C26—C25	120.50 (16)
N22—N23—H23N	108.8 (11)	O21—C27—N21	124.42 (13)
C12—C11—C16	119.04 (13)	O21—C27—N22	121.12 (13)
N11—C11—C16	116.64 (12)	N21—C27—N22	114.46 (13)
N11—C11—C12	124.32 (12)	C21—C22—H22	120.00
C11—C12—C13	119.65 (14)	C23—C22—H22	120.00
C12—C13—C14	121.24 (14)	C22—C23—H23	119.00
C13—C14—C15	119.07 (15)	C24—C23—H23	119.00
C14—C15—C16	120.69 (15)	C23—C24—H24	120.00
C11—C16—C15	120.30 (14)	C25—C24—H24	120.00
N11—C17—N12	114.90 (12)	C24—C25—H25	120.00
O11—C17—N11	124.42 (13)	C26—C25—H25	120.00
O11—C17—N12	120.67 (12)	C21—C26—H26	120.00
C11—C12—H12	120.00	C25—C26—H26	120.00
C17—N11—C11—C12	14.9 (2)	C16—C11—C12—C13	1.0 (2)
C17—N11—C11—C16	−164.97 (14)	N11—C11—C16—C15	178.94 (13)
C11—N11—C17—O11	−6.6 (2)	C11—C12—C13—C14	−0.3 (2)
C11—N11—C17—N12	171.74 (13)	C12—C13—C14—C15	−0.4 (2)
N13—N12—C17—O11	179.06 (13)	C13—C14—C15—C16	0.5 (2)
N13—N12—C17—N11	0.66 (18)	C14—C15—C16—C11	0.2 (2)
C21—N21—C27—O21	2.2 (2)	N21—C21—C22—C23	177.50 (14)
C27—N21—C21—C22	24.3 (2)	C26—C21—C22—C23	0.2 (2)
C27—N21—C21—C26	−158.35 (15)	N21—C21—C26—C25	−177.24 (15)
C21—N21—C27—N22	−178.53 (14)	C22—C21—C26—C25	0.2 (2)
N23—N22—C27—N21	−0.5 (2)	C21—C22—C23—C24	−0.5 (2)
N23—N22—C27—O21	178.77 (13)	C22—C23—C24—C25	0.3 (3)
N11—C11—C12—C13	−178.84 (13)	C23—C24—C25—C26	0.1 (3)
C12—C11—C16—C15	−0.9 (2)	C24—C25—C26—C21	−0.4 (3)

D—H···A	D—H	H···A	D···A	D—H···A
N11—H11N···N13	0.849 (16)	2.130 (15)	2.6149 (19)	116.0 (13)
N12—H12N···O21i	0.872 (15)	2.071 (15)	2.9386 (15)	172.8 (14)
N13—H14N···O11ii	0.887 (18)	2.383 (17)	3.2149 (18)	156.1 (15)
N21—H21N···N23	0.852 (16)	2.130 (17)	2.6093 (19)	115.3 (14)
N22—H22N···O11iii	0.901 (16)	2.079 (17)	2.9784 (17)	175.9 (14)
N23—H23N···O21iv	0.919 (17)	2.203 (17)	3.0850 (18)	160.5 (15)
C12—H12···O11	0.93	2.33	2.9119 (18)	120
C22—H22···O21	0.93	2.46	2.9833 (18)	116

Table 1

Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
N11—H11N⋯N13	0.849 (16)	2.130 (15)	2.6149 (19)	116.0 (13)
N12—H12N⋯O21i	0.872 (15)	2.071 (15)	2.9386 (15)	172.8 (14)
N13—H14N⋯O11ii	0.887 (18)	2.383 (17)	3.2149 (18)	156.1 (15)
N21—H21N⋯N23	0.852 (16)	2.130 (17)	2.6093 (19)	115.3 (14)
N22—H22N⋯O11iii	0.901 (16)	2.079 (17)	2.9784 (17)	175.9 (14)
N23—H23N⋯O21iv	0.919 (17)	2.203 (17)	3.0850 (18)	160.5 (15)
C12—H12⋯O11	0.93	2.33	2.9119 (18)	120
C22—H22⋯O21	0.93	2.46	2.9833 (18)	116

Symmetry codes: (i) ; (ii) ; (iii) ; (iv) .