4-Bromo-N-phenyl-benzamidoxime.

The title compound, C(13)H(11)BrN(2)O, a hydroxy-amidine derivative (an amidoxime), was obtained by addition of the corresponding imidoyl chloride to hydroxy-lamine. The benzene and phenyl rings are twisted from the mean plane of the hydroxy-amidine group by 34.4 (1) and 59.2 (1)°, respectively. In the crystal structure, inter-molecular O-H⋯N hydrogen bonds link pairs of mol-ecules, forming centrosymmetric dimers.

Related literature

For the synthesis, properties and applications of N-substituted hydroxy­amidines/amidoximes see: Krajete et al. (2004 ▶), Srivastava et al. (1997 ▶); Dondoni et al. (1975 ▶, 1977 ▶); Dürüst et al. (2000 ▶, 2008 ▶); Exner et al. (1974 ▶); Briggs et al. (1976 ▶); Deb et al. (1991 ▶). For a description of the Cambridge Structural Database, see: Allen et al. (1987 ▶).

Experimental

Crystal data

C13H11BrN2O

M = 291.15

Monoclinic,

a = 6.1752 (1) Å

b = 15.2628 (3) Å

c = 13.1312 (2) Å

β = 103.415 (1)°

V = 1203.86 (4) Å3

Z = 4

Cu Kα radiation

μ = 4.53 mm−1

T = 200 K

0.18 × 0.15 × 0.09 mm

Data collection

Bruker APEXII diffractometer

Absorption correction: multi-scan (SADABS; Sheldrick, 1996 ▶) T min = 0.532, T max = 0.665

15615 measured reflections

2356 independent reflections

2273 reflections with I > 2σ(I)

R int = 0.033

Refinement

R[F 2 > 2σ(F 2)] = 0.037

wR(F 2) = 0.090

S = 1.11

2356 reflections

155 parameters

H-atom parameters constrained

Δρmax = 0.39 e Å−3

Δρmin = −0.68 e Å−3

Data collection: APEX2 (Bruker, 2009 ▶); cell refinement: SAINT (Bruker, 2009 ▶); 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: UdMX (Maris, 2004 ▶).

Crystal structure: contains datablocks I, global. DOI: 10.1107/S1600536809040057/lh2914sup1.cif

Structure factors: contains datablocks I. DOI: 10.1107/S1600536809040057/lh2914Isup2.hkl

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

C13H11BrN2O	F(000) = 584
Mr = 291.15	Dx = 1.606 Mg m−3
Monoclinic, P21/n	Cu Kα radiation, λ = 1.54178 Å
Hall symbol: -P 2yn	Cell parameters from 11676 reflections
a = 6.1752 (1) Å	θ = 2.9–71.9°
b = 15.2628 (3) Å	µ = 4.53 mm−1
c = 13.1312 (2) Å	T = 200 K
β = 103.415 (1)°	Block, yellow
V = 1203.86 (4) Å3	0.18 × 0.15 × 0.09 mm
Z = 4

Bruker APEXII diffractometer	2356 independent reflections
Radiation source: Rotating Anode	2273 reflections with I > 2σ(I)
Montel 200 optics	Rint = 0.033
Detector resolution: 5.5 pixels mm-1	θmax = 72.5°, θmin = 4.5°
ω scans	h = −7→7
Absorption correction: multi-scan (SADABS; Sheldrick, 1996)	k = −18→18
Tmin = 0.532, Tmax = 0.665	l = −15→16
15615 measured reflections

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)] = 0.037	H-atom parameters constrained
wR(F2) = 0.090	w = 1/[σ2(Fo2) + (0.0601P)2 + 0.3484P] where P = (Fo2 + 2Fc2)/3
S = 1.11	(Δ/σ)max = 0.001
2356 reflections	Δρmax = 0.39 e Å−3
155 parameters	Δρmin = −0.68 e Å−3
0 restraints	Extinction correction: SHELXL97 (Sheldrick, 2008), Fc*=kFc[1+0.001xFc2λ3/sin(2θ)]-1/4
Primary atom site location: structure-invariant direct methods	Extinction coefficient: 0.0212 (8)

Experimental. X-ray crystallographic data for (I) were collected from a single-crystal sample, which was mounted on a loop fiber. Data were collected using a Bruker Platform diffractometer, equipped with a Bruker SMART 4 K Charged-Coupled Device (CCD) Area Detector using the program APEX2 and a Nonius FR591 rotating anode equiped with a Montel 200 optics The crystal-to-detector distance was 5.0 cm, and the data collection was carried out in 512 x 512 pixel mode. The initial unit-cell parameters were determined by a least-squares fit of the angular setting of strong reflections, collected by a 10.0 degree scan in 33 frames over four different parts of the reciprocal space (133 frames total). One complete sphere of data was collected, to better than 0.80Å resolution.

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
Br	1.22913 (4)	0.643427 (14)	0.618702 (18)	0.04819 (16)
O1	0.4208 (2)	0.40817 (9)	0.94989 (11)	0.0393 (3)
H1	0.3752	0.4375	0.9949	0.059*
N1	0.5789 (3)	0.45874 (10)	0.91086 (12)	0.0340 (3)
N2	0.4624 (3)	0.36287 (11)	0.77216 (14)	0.0410 (4)
H2	0.3431	0.3517	0.7958	0.049*
C1	0.5957 (3)	0.42884 (11)	0.82101 (14)	0.0313 (4)
C2	0.7549 (3)	0.47517 (11)	0.77017 (13)	0.0299 (4)
C3	0.9510 (3)	0.50983 (12)	0.83173 (14)	0.0346 (4)
H3	0.9873	0.4994	0.9051	0.041*
C4	1.0932 (3)	0.55912 (13)	0.78747 (15)	0.0368 (4)
H4	1.2261	0.5828	0.8299	0.044*
C5	1.0391 (3)	0.57343 (12)	0.68075 (15)	0.0353 (4)
C6	0.8484 (4)	0.53857 (14)	0.61731 (15)	0.0408 (4)
H6	0.8153	0.5479	0.5438	0.049*
C7	0.7060 (3)	0.48970 (13)	0.66248 (15)	0.0381 (4)
H7	0.5738	0.4659	0.6196	0.046*
C8	0.4934 (3)	0.31015 (12)	0.68770 (14)	0.0337 (4)
C9	0.3113 (3)	0.29434 (13)	0.60544 (16)	0.0386 (4)
H9	0.1703	0.3189	0.6062	0.046*
C10	0.3362 (4)	0.24228 (13)	0.52181 (16)	0.0417 (4)
H10	0.2117	0.2309	0.4656	0.050*
C11	0.5407 (4)	0.20724 (13)	0.52029 (16)	0.0414 (4)
H11	0.5577	0.1726	0.4626	0.050*
C12	0.7220 (3)	0.22247 (14)	0.60292 (17)	0.0418 (5)
H12	0.8629	0.1980	0.6017	0.050*
C13	0.6989 (3)	0.27319 (13)	0.68740 (15)	0.0384 (4)
H13	0.8226	0.2826	0.7446	0.046*

	U11	U22	U33	U12	U13	U23
Br	0.0483 (2)	0.0459 (2)	0.0568 (2)	−0.00414 (8)	0.02515 (13)	0.00910 (8)
O1	0.0486 (8)	0.0365 (7)	0.0400 (7)	−0.0037 (6)	0.0248 (6)	−0.0008 (5)
N1	0.0401 (8)	0.0326 (8)	0.0336 (7)	0.0003 (6)	0.0173 (6)	0.0020 (6)
N2	0.0419 (9)	0.0438 (9)	0.0439 (10)	−0.0102 (7)	0.0235 (8)	−0.0114 (7)
C1	0.0353 (8)	0.0289 (8)	0.0315 (8)	0.0025 (7)	0.0113 (7)	−0.0001 (6)
C2	0.0346 (8)	0.0272 (8)	0.0300 (8)	0.0029 (6)	0.0118 (7)	0.0004 (6)
C3	0.0399 (9)	0.0362 (9)	0.0280 (8)	0.0020 (7)	0.0088 (7)	0.0005 (7)
C4	0.0353 (9)	0.0370 (9)	0.0380 (9)	−0.0008 (7)	0.0086 (7)	−0.0007 (7)
C5	0.0383 (9)	0.0304 (8)	0.0409 (10)	0.0017 (7)	0.0170 (7)	0.0038 (7)
C6	0.0492 (11)	0.0437 (10)	0.0298 (9)	−0.0029 (9)	0.0101 (8)	0.0063 (8)
C7	0.0422 (10)	0.0403 (10)	0.0306 (9)	−0.0052 (8)	0.0061 (7)	0.0018 (7)
C8	0.0394 (9)	0.0307 (8)	0.0344 (9)	−0.0060 (7)	0.0156 (7)	−0.0028 (7)
C9	0.0377 (9)	0.0352 (9)	0.0439 (10)	−0.0029 (7)	0.0113 (8)	−0.0017 (8)
C10	0.0479 (11)	0.0383 (10)	0.0373 (10)	−0.0075 (8)	0.0065 (8)	−0.0035 (8)
C11	0.0565 (12)	0.0332 (9)	0.0389 (10)	−0.0079 (8)	0.0199 (9)	−0.0072 (7)
C12	0.0410 (10)	0.0356 (10)	0.0534 (11)	−0.0016 (7)	0.0203 (9)	−0.0058 (8)
C13	0.0374 (9)	0.0372 (9)	0.0409 (10)	−0.0031 (7)	0.0099 (8)	−0.0046 (8)

Br—C5	1.9040 (18)	C6—C7	1.387 (3)
O1—N1	1.430 (2)	C6—H6	0.9500
O1—H1	0.8400	C7—H7	0.9500
N1—C1	1.292 (2)	C8—C9	1.388 (3)
N2—C1	1.363 (2)	C8—C13	1.390 (3)
N2—C8	1.419 (2)	C9—C10	1.393 (3)
N2—H2	0.8800	C9—H9	0.9500
C1—C2	1.489 (2)	C10—C11	1.376 (3)
C2—C7	1.394 (2)	C10—H10	0.9500
C2—C3	1.394 (3)	C11—C12	1.386 (3)
C3—C4	1.383 (3)	C11—H11	0.9500
C3—H3	0.9500	C12—C13	1.387 (3)
C4—C5	1.381 (3)	C12—H12	0.9500
C4—H4	0.9500	C13—H13	0.9500
C5—C6	1.382 (3)
N1—O1—H1	109.5	C7—C6—H6	120.5
C1—N1—O1	110.06 (15)	C6—C7—C2	120.66 (17)
C1—N2—C8	127.65 (17)	C6—C7—H7	119.7
C1—N2—H2	116.2	C2—C7—H7	119.7
C8—N2—H2	116.2	C9—C8—C13	120.19 (17)
N1—C1—N2	121.56 (17)	C9—C8—N2	118.38 (18)
N1—C1—C2	116.31 (16)	C13—C8—N2	121.42 (17)
N2—C1—C2	121.95 (16)	C8—C9—C10	119.66 (19)
C7—C2—C3	118.85 (16)	C8—C9—H9	120.2
C7—C2—C1	121.35 (16)	C10—C9—H9	120.2
C3—C2—C1	119.67 (15)	C11—C10—C9	120.21 (19)
C4—C3—C2	120.89 (17)	C11—C10—H10	119.9
C4—C3—H3	119.6	C9—C10—H10	119.9
C2—C3—H3	119.6	C10—C11—C12	120.06 (18)
C5—C4—C3	119.02 (17)	C10—C11—H11	120.0
C5—C4—H4	120.5	C12—C11—H11	120.0
C3—C4—H4	120.5	C11—C12—C13	120.36 (19)
C4—C5—C6	121.51 (17)	C11—C12—H12	119.8
C4—C5—Br	119.69 (15)	C13—C12—H12	119.8
C6—C5—Br	118.80 (14)	C12—C13—C8	119.50 (18)
C5—C6—C7	119.05 (17)	C12—C13—H13	120.3
C5—C6—H6	120.5	C8—C13—H13	120.3
O1—N1—C1—N2	4.8 (2)	Br—C5—C6—C7	−178.10 (16)
O1—N1—C1—C2	179.94 (14)	C5—C6—C7—C2	−0.5 (3)
C8—N2—C1—N1	−164.13 (19)	C3—C2—C7—C6	−0.7 (3)
C8—N2—C1—C2	21.0 (3)	C1—C2—C7—C6	175.18 (18)
N1—C1—C2—C7	−141.09 (18)	C1—N2—C8—C9	−135.4 (2)
N2—C1—C2—C7	34.0 (3)	C1—N2—C8—C13	46.0 (3)
N1—C1—C2—C3	34.7 (2)	C13—C8—C9—C10	−0.9 (3)
N2—C1—C2—C3	−150.13 (18)	N2—C8—C9—C10	−179.53 (17)
C7—C2—C3—C4	1.1 (3)	C8—C9—C10—C11	−0.5 (3)
C1—C2—C3—C4	−174.82 (16)	C9—C10—C11—C12	1.1 (3)
C2—C3—C4—C5	−0.3 (3)	C10—C11—C12—C13	−0.2 (3)
C3—C4—C5—C6	−1.0 (3)	C11—C12—C13—C8	−1.3 (3)
C3—C4—C5—Br	178.52 (14)	C9—C8—C13—C12	1.8 (3)
C4—C5—C6—C7	1.4 (3)	N2—C8—C13—C12	−179.64 (18)

D—H···A	D—H	H···A	D···A	D—H···A
O1—H1···N1i	0.84	1.99	2.733 (2)	147

Table 1

Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
O1—H1⋯N1i	0.84	1.99	2.733 (2)	147

Symmetry code: (i) .