Benzamide oxime.

In the crystal structure of the title compound, C(7)H(8)N(2)O, mol-ecules are connected via inter-molecular N-H⋯O and O-H⋯N hydrogen bonds to form a two-dimensional supra-molecular structure. The oxime group has an E configuration and the dihedral angle between the mean planes of the benzene ring and the amidoxime grouping is 20.2 (3)°.

Related literature

For related literature, see: Bruton et al. (2003 ▶); Kang et al. (2007 ▶); Li et al. (2007 ▶); Srivastava et al. (1997 ▶); Wang et al. (2006 ▶, 2007 ▶); Bertolasi et al. (1982 ▶); Chertanova et al. (1994 ▶); Goel et al. (1981 ▶); Xing, Ding et al. (2007 ▶); Xing, Wang et al. (2007 ▶).

Experimental

Crystal data

C7H8N2O

M = 136.15

Monoclinic,

a = 12.579 (2) Å

b = 5.053 (1) Å

c = 10.908 (2) Å

β = 90.380 (7)°

V = 693.3 (2) Å3

Z = 4

Mo Kα radiation

μ = 0.09 mm−1

T = 273 (2) K

0.28 × 0.22 × 0.18 mm

Data collection

Bruker SMART CCD area-detector diffractometer

Absorption correction: multi-scan (SADABS; Sheldrick, 1996 ▶) T min = 0.975, T max = 0.984

4489 measured reflections

1216 independent reflections

967 reflections with I > 2σ(I)

R int = 0.028

Refinement

R[F 2 > 2σ(F 2)] = 0.050

wR(F 2) = 0.145

S = 1.04

1216 reflections

92 parameters

H-atom parameters constrained

Δρmax = 0.21 e Å−3

Δρmin = −0.22 e Å−3

Data collection: SMART (Bruker, 2003 ▶); cell refinement: SAINT (Bruker, 2003 ▶); 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 global, I. DOI: 10.1107/S1600536808020813/ez2131sup1.cif

Structure factors: contains datablocks I. DOI: 10.1107/S1600536808020813/ez2131Isup2.hkl

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

C7H8N2O	F000 = 288
Mr = 136.15	Dx = 1.304 Mg m−3
Monoclinic, P21/c	Mo Kα radiation λ = 0.71073 Å
Hall symbol: -P 2ybc	Cell parameters from 1198 reflections
a = 12.579 (2) Å	θ = 2.5–27.7º
b = 5.053 (1) Å	µ = 0.09 mm−1
c = 10.908 (2) Å	T = 273 (2) K
β = 90.380 (7)º	Block, colorless
V = 693.3 (2) Å3	0.28 × 0.22 × 0.18 mm
Z = 4

Bruker SMART CCD area-detector diffractometer	1216 independent reflections
Radiation source: fine-focus sealed tube	967 reflections with I > 2σ(I)
Monochromator: graphite	Rint = 0.028
T = 273(2) K	θmax = 25.0º
φ and ω scans	θmin = 1.6º
Absorption correction: multi-scan(SADABS; Sheldrick, 1996)	h = −14→14
Tmin = 0.975, Tmax = 0.984	k = −6→6
4489 measured reflections	l = −12→12

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)] = 0.050	H-atom parameters constrained
wR(F2) = 0.145	w = 1/[σ2(Fo2) + (0.0753P)2 + 0.2452P] where P = (Fo2 + 2Fc2)/3
S = 1.05	(Δ/σ)max < 0.001
1216 reflections	Δρmax = 0.21 e Å−3
92 parameters	Δρmin = −0.22 e Å−3
Primary atom site location: structure-invariant direct methods	Extinction correction: none

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	0.50237 (11)	0.1813 (3)	1.12339 (12)	0.0523 (4)
H1	0.4578	0.0750	1.0990	0.078*
N2	0.58736 (13)	0.1959 (3)	1.03730 (14)	0.0453 (5)
C7	0.63885 (14)	0.4152 (4)	1.05147 (16)	0.0391 (5)
N1	0.61721 (14)	0.5943 (3)	1.13971 (15)	0.0508 (5)
H1A	0.5666	0.5653	1.1906	0.061*
H1B	0.6540	0.7373	1.1450	0.061*
C1	0.72942 (14)	0.4640 (4)	0.96838 (17)	0.0411 (5)
C5	0.8218 (2)	0.3813 (6)	0.7814 (2)	0.0710 (7)
H5	0.8256	0.2908	0.7073	0.085*
C6	0.73762 (19)	0.3377 (5)	0.8576 (2)	0.0643 (7)
H6	0.6847	0.2195	0.8337	0.077*
C2	0.8089 (2)	0.6386 (6)	0.9997 (3)	0.0781 (8)
H2	0.8062	0.7276	1.0742	0.094*
C4	0.89920 (19)	0.5537 (5)	0.8122 (2)	0.0674 (7)
H4	0.9560	0.5839	0.7599	0.081*
C3	0.8926 (2)	0.6829 (7)	0.9215 (3)	0.0962 (11)
H3	0.9455	0.8027	0.9437	0.115*

	U11	U22	U33	U12	U13	U23
O1	0.0545 (9)	0.0537 (9)	0.0488 (8)	−0.0083 (6)	0.0195 (7)	0.0020 (6)
N2	0.0477 (9)	0.0438 (10)	0.0445 (9)	−0.0035 (7)	0.0130 (7)	0.0000 (7)
C7	0.0435 (10)	0.0375 (10)	0.0364 (9)	0.0027 (8)	0.0008 (7)	0.0041 (7)
N1	0.0609 (11)	0.0444 (10)	0.0471 (9)	−0.0028 (8)	0.0116 (8)	−0.0054 (8)
C1	0.0427 (10)	0.0376 (10)	0.0429 (10)	0.0011 (8)	0.0024 (8)	0.0036 (8)
C5	0.0705 (15)	0.0845 (18)	0.0583 (13)	−0.0135 (13)	0.0222 (12)	−0.0124 (13)
C6	0.0606 (13)	0.0763 (16)	0.0562 (13)	−0.0226 (12)	0.0151 (10)	−0.0164 (12)
C2	0.0739 (16)	0.0848 (19)	0.0757 (16)	−0.0334 (14)	0.0208 (13)	−0.0281 (14)
C4	0.0543 (13)	0.0735 (16)	0.0747 (16)	−0.0065 (12)	0.0226 (11)	0.0063 (13)
C3	0.0763 (18)	0.108 (2)	0.105 (2)	−0.0503 (18)	0.0278 (16)	−0.0271 (19)

O1—N2	1.430 (2)	C5—C4	1.348 (4)
O1—H1	0.8200	C5—C6	1.368 (3)
N2—C7	1.292 (2)	C5—H5	0.9300
C7—N1	1.350 (2)	C6—H6	0.9300
C7—C1	1.481 (3)	C2—C3	1.378 (4)
N1—H1A	0.8600	C2—H2	0.9300
N1—H1B	0.8600	C4—C3	1.362 (4)
C1—C6	1.371 (3)	C4—H4	0.9300
C1—C2	1.375 (3)	C3—H3	0.9300
N2—O1—H1	109.5	C6—C5—H5	119.6
C7—N2—O1	109.99 (15)	C5—C6—C1	121.6 (2)
N2—C7—N1	123.82 (17)	C5—C6—H6	119.2
N2—C7—C1	117.16 (16)	C1—C6—H6	119.2
N1—C7—C1	118.97 (17)	C1—C2—C3	120.5 (2)
C7—N1—H1A	120.0	C1—C2—H2	119.7
C7—N1—H1B	120.0	C3—C2—H2	119.7
H1A—N1—H1B	120.0	C5—C4—C3	118.7 (2)
C6—C1—C2	117.3 (2)	C5—C4—H4	120.7
C6—C1—C7	121.63 (18)	C3—C4—H4	120.7
C2—C1—C7	121.06 (18)	C4—C3—C2	121.0 (2)
C4—C5—C6	120.9 (2)	C4—C3—H3	119.5
C4—C5—H5	119.6	C2—C3—H3	119.5
O1—N2—C7—N1	3.2 (2)	C2—C1—C6—C5	0.5 (4)
O1—N2—C7—C1	−179.43 (14)	C7—C1—C6—C5	−179.5 (2)
N2—C7—C1—C6	21.8 (3)	C6—C1—C2—C3	0.2 (4)
N1—C7—C1—C6	−160.7 (2)	C7—C1—C2—C3	−179.8 (3)
N2—C7—C1—C2	−158.2 (2)	C6—C5—C4—C3	0.5 (5)
N1—C7—C1—C2	19.3 (3)	C5—C4—C3—C2	0.2 (5)
C4—C5—C6—C1	−0.9 (4)	C1—C2—C3—C4	−0.5 (5)

D—H···A	D—H	H···A	D···A	D—H···A
O1—H1···N2i	0.82	2.10	2.820 (2)	147
N1—H1A···O1ii	0.86	2.29	3.031 (2)	145

Table 1

Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
O1—H1⋯N2i	0.82	2.10	2.820 (2)	147
N1—H1A⋯O1ii	0.86	2.29	3.031 (2)	145

Symmetry codes: (i) ; (ii) .