Benzamide oxime

Xu, S.-Q.; Li, J.-M.

doi:10.1107/S1600536808020813

organic compounds

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ISSN: 2056-9890

Volume 64| Part 8| August 2008| Page o1469

doi:10.1107/S1600536808020813

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Benzamide oxime

Shu-Qing Xu ^a and Jia-Ming Li ^a ^*

^aLaboratory of Beibu Gulf Marine Protection and Exploitation, Department of Chemistry and Biology, Qinzhou University, Qinzhou, Guangxi 535000, People's Republic of China
^*Correspondence e-mail: ljmmarise@163.com

(Received 22 May 2008; accepted 5 July 2008; online 12 July 2008)

In the crystal structure of the title compound, C₇H₈N₂O, molecules are connected via intermolecular N—H⋯O and O—H⋯N hydrogen bonds to form a two-dimensional supramolecular 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_r = 136.15
Monoclinic, P 2₁ /c
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[F² > 2σ(F²)] = 0.050
wR(F²) = 0.145
S = 1.04
1216 reflections
92 parameters
H-atom parameters constrained
Δρ_max = 0.21 e Å⁻³
Δρ_min = −0.22 e Å⁻³

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) -x+1, -y, -z+2; (ii) $[-x+1, y+{\script{1\over 2}}, -z+{\script{5\over 2}}]$ .

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.

Supporting information

Crystal structure: contains datablocks global, I. DOI: 10.1107/S1600536808020813/ez2131sup1.cif

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

checkCIF report

Comment top

The synthesis of Schiff base complexes containing oxime (–C═N—OH) functional groups has attracted great interest due to their antiviral, anticancer and antibacterial activities (Srivastava et al., 1997; Goel et al., 1981; Li et al., 2007; Wang et al., 2007; Xing, Ding et al. (2007), Xing, Wang et al. (2007). Also, the interesting hydrogen-bond systems in the crystal structures of oximes have been analysed and a correlation between the pattern of hydrogen bonding and N—O bond lengths has been suggested (Bertolasi et al., 1982; Bruton et al., 2003). Herein, we report the synthesis and crystal structure of the title compound, (I). In the crystal structure of the title compound, molecules are connected via intermolecular N—H···O and O—H···N hydrogen bonds (see Table 1 and Fig. 2) to form a two-dimensional supramolecular structure. The oxime group has an E configuration [C4—C9—N1—O3 = -179.43 (14) °, Chertanova et al., 1994] and the dihedral angle between the mean planes of the benzene ring and the C7/N1/N2/O grouping is 20.2 (3) °, which is less than that reported for similar structures by Kang et al. (2007) and Xing, Ding et al. (2007), Xing, Wang et al. (2007).

Related literature top

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), Xing et al. (2007a,b); Bertolasi et al. (1982); Chertanova et al. (1994); Goel et al. (1981); Xing, Ding, Wang, Jun & Han (2007); Xing, Wang, Jun, Wu & Feng (2007).

Experimental top

Reagents and solvents used were of commercially available quality. The Schiff base ligand benzamidoxime was synthesized according to the method of Kang et al. (2007). A mixture of benzonitrile (0.33 mol) and hydroxylamine hydrochloride (0.33 mol) in ethanol (231 ml) and potassium carbonate (0.33 mol) in water (66 ml) was refluxed for 12 h. After cooling and filtering, compound (I) was obtained. Crystals of (I) suitable for X-ray diffraction were obtained by slow evaporation of an ethanol solution.

Computing details top

Data collection: SMART (Bruker, 2003); cell refinement: SAINT (Bruker, 2003); data reduction: SAINT (Bruker, 2003); 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. The molecular structure of I showing the atom numbering scheme with displacement ellipsoids at the 30% probability level.
	Fig. 2. Part of the crystal structure showing hydrogen bonds as dashed lines. H atoms, except for those involved in hydrogen bonds, are not included.

Benzamide oxime top

Crystal data top

C₇H₈N₂O	F(000) = 288
M_r = 136.15	D_x = 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 = 2.5–27.7°
b = 5.053 (1) Å	µ = 0.09 mm⁻¹
c = 10.908 (2) Å	T = 273 K
β = 90.380 (7)°	Block, colorless
V = 693.3 (2) Å³	0.28 × 0.22 × 0.18 mm
Z = 4

Data collection top

Bruker SMART CCD area-detector diffractometer	1216 independent reflections
Radiation source: fine-focus sealed tube	967 reflections with I > 2σ(I)
Graphite monochromator	R_int = 0.028
ϕ and ω scans	θ_max = 25.0°, θ_min = 1.6°
Absorption correction: multi-scan (SADABS; Sheldrick, 1996)	h = −14→14
T_min = 0.975, T_max = 0.984	k = −6→6
4489 measured reflections	l = −12→12

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)] = 0.050	Hydrogen site location: inferred from neighbouring sites
wR(F²) = 0.145	H-atom parameters constrained
S = 1.05	w = 1/[σ²(F_o²) + (0.0753P)² + 0.2452P] where P = (F_o² + 2F_c²)/3
1216 reflections	(Δ/σ)_max < 0.001
92 parameters	Δρ_max = 0.21 e Å⁻³
0 restraints	Δρ_min = −0.22 e Å⁻³

Crystal data top

C₇H₈N₂O	V = 693.3 (2) Å³
M_r = 136.15	Z = 4
Monoclinic, P2₁/c	Mo Kα radiation
a = 12.579 (2) Å	µ = 0.09 mm⁻¹
b = 5.053 (1) Å	T = 273 K
c = 10.908 (2) Å	0.28 × 0.22 × 0.18 mm
β = 90.380 (7)°

Data collection top

Bruker SMART CCD area-detector diffractometer	1216 independent reflections
Absorption correction: multi-scan (SADABS; Sheldrick, 1996)	967 reflections with I > 2σ(I)
T_min = 0.975, T_max = 0.984	R_int = 0.028
4489 measured reflections

Refinement top

R[F² > 2σ(F²)] = 0.050	0 restraints
wR(F²) = 0.145	H-atom parameters constrained
S = 1.05	Δρ_max = 0.21 e Å⁻³
1216 reflections	Δρ_min = −0.22 e Å⁻³
92 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	0.50237 (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*

Atomic displacement parameters (Å²) top

	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)

Geometric parameters (Å, º) top

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)

Hydrogen-bond geometry (Å, º) top

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) −x+1, −y, −z+2; (ii) −x+1, y+1/2, −z+5/2.

Experimental details

Crystal data
Chemical formula	C₇H₈N₂O
M_r	136.15
Crystal system, space group	Monoclinic, P2₁/c
Temperature (K)	273
a, b, c (Å)	12.579 (2), 5.053 (1), 10.908 (2)
β (°)	90.380 (7)
V (Å³)	693.3 (2)
Z	4
Radiation type	Mo Kα
µ (mm⁻¹)	0.09
Crystal size (mm)	0.28 × 0.22 × 0.18

Data collection
Diffractometer	Bruker SMART CCD area-detector diffractometer
Absorption correction	Multi-scan (SADABS; Sheldrick, 1996)
T_min, T_max	0.975, 0.984
No. of measured, independent and observed [I > 2σ(I)] reflections	4489, 1216, 967
R_int	0.028
(sin θ/λ)_max (Å⁻¹)	0.596

Refinement
R[F² > 2σ(F²)], wR(F²), S	0.050, 0.145, 1.05
No. of reflections	1216
No. of parameters	92
H-atom treatment	H-atom parameters constrained
Δρ_max, Δρ_min (e Å⁻³)	0.21, −0.22

Computer programs: SMART (Bruker, 2003), SAINT (Bruker, 2003), SHELXS97 (Sheldrick, 2008), SHELXL97 (Sheldrick, 2008), SHELXTL (Sheldrick, 2008).

Selected bond lengths (Å) top

O1—N2	1.430 (2)	C7—N1	1.350 (2)
N2—C7	1.292 (2)	C7—C1	1.481 (3)

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
O1—H1···N2ⁱ	0.82	2.10	2.820 (2)	147.1
N1—H1A···O1ⁱⁱ	0.86	2.29	3.031 (2)	144.6

Symmetry codes: (i) −x+1, −y, −z+2; (ii) −x+1, y+1/2, −z+5/2.

Acknowledgements

This work was supported by a grant from the Qinzhou University Foundation of Guangxi Zhuang Autonomous Region of the People's Republic of China (grant No. 2007XJ15).

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