6-Bromo-4-[(3-chloro-4-methyl-phenyl)-imino-meth-yl]-2-meth-oxy-3-nitro-phenol.

In the title compound, C(15)H(12)BrClN(2)O(4), the configuration of the C=N double bond can be described as trans. The two aromatic rings in this Schiff base are nearly coplanar with a dihedral angle between their mean planes of 15.4 (2)°. In the crystal, molecules are linked via O-H⋯N and C-H⋯O interactions.

Related literature

For Schiff bases in coordination chemistry, see: Shao et al. (2004 ▶) and for their biological activity, see: Desai et al. (2001 ▶); Venugopal & Jayashree (2008 ▶). For standard bond lengths, see: Allen et al. (1987 ▶).

Experimental

Crystal data

C15H12BrClN2O4

M = 399.62

Orthorhombic,

a = 18.288 (2) Å

b = 8.713 (3) Å

c = 19.018 (2) Å

V = 3030.4 (11) Å3

Z = 8

Mo Kα radiation

μ = 2.91 mm−1

T = 296 K

0.26 × 0.22 × 0.20 mm

Data collection

Bruker SMART APEX CCD diffractometer

Absorption correction: multi-scan (SADABS; Bruker, 2000 ▶) T min = 0.518, T max = 0.594

17176 measured reflections

2973 independent reflections

1713 reflections with I > 2σ(I)

R int = 0.088

Refinement

R[F 2 > 2σ(F 2)] = 0.050

wR(F 2) = 0.149

S = 1.06

2973 reflections

210 parameters

H-atom parameters constrained

Δρmax = 0.43 e Å−3

Δρmin = −0.49 e Å−3

Data collection: SMART (Bruker, 2000 ▶); cell refinement: SAINT (Bruker, 2000 ▶); 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 datablock(s) global, I. DOI: 10.1107/S1600536812023859/vm2167sup1.cif

Structure factors: contains datablock(s) I. DOI: 10.1107/S1600536812023859/vm2167Isup2.hkl

Supplementary material file. DOI: 10.1107/S1600536812023859/vm2167Isup3.cml

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

C15H12BrClN2O4	F(000) = 1600
Mr = 399.62	Dx = 1.752 Mg m−3
Orthorhombic, Pbca	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: -P 2ac 2ab	Cell parameters from 2396 reflections
a = 18.288 (2) Å	θ = 2.4–25.2°
b = 8.713 (3) Å	µ = 2.91 mm−1
c = 19.018 (2) Å	T = 296 K
V = 3030.4 (11) Å3	Block, orange
Z = 8	0.26 × 0.22 × 0.20 mm

Bruker SMART APEX CCD diffractometer	2973 independent reflections
Radiation source: fine-focus sealed tube	1713 reflections with I > 2σ(I)
Graphite monochromator	Rint = 0.088
phi and ω scans	θmax = 26.0°, θmin = 2.4°
Absorption correction: multi-scan (SADABS; Bruker, 2000)	h = −17→22
Tmin = 0.518, Tmax = 0.594	k = −10→10
17176 measured reflections	l = −23→22

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) = 0.149	H-atom parameters constrained
S = 1.06	w = 1/[σ2(Fo2) + (0.0664P)2] where P = (Fo2 + 2Fc2)/3
2973 reflections	(Δ/σ)max = 0.001
210 parameters	Δρmax = 0.43 e Å−3
0 restraints	Δρmin = −0.49 e Å−3

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
Cl1	0.55428 (7)	0.89623 (17)	0.11025 (7)	0.0552 (4)
Br1	1.09270 (3)	0.59794 (7)	0.22933 (3)	0.0560 (3)
N1	0.7871 (2)	0.5746 (5)	0.3498 (2)	0.0453 (11)
N2	0.8252 (2)	0.8332 (4)	0.17064 (18)	0.0337 (9)
O1	0.8983 (2)	0.4633 (5)	0.4246 (2)	0.0673 (12)
O2	1.03988 (18)	0.4585 (4)	0.36915 (17)	0.0490 (9)
H2	1.0785	0.4695	0.3478	0.074*
O3	0.7666 (3)	0.6579 (6)	0.3947 (3)	0.1000 (18)
O4	0.7493 (3)	0.4810 (7)	0.3247 (3)	0.0949 (16)
C1	0.9994 (2)	0.6004 (5)	0.2709 (3)	0.0364 (11)
C2	0.9893 (2)	0.5226 (5)	0.3358 (2)	0.0346 (11)
C3	0.9157 (3)	0.5221 (6)	0.3611 (2)	0.0370 (12)
C4	0.8613 (2)	0.5872 (5)	0.3237 (2)	0.0336 (11)
C5	0.8729 (3)	0.6696 (5)	0.2597 (2)	0.0311 (10)
C6	0.9444 (2)	0.6715 (5)	0.2356 (2)	0.0348 (11)
H6	0.9550	0.7230	0.1940	0.042*
C7	0.8157 (2)	0.7392 (5)	0.2234 (2)	0.0340 (11)
H7	0.7681	0.7177	0.2375	0.041*
C8	0.7679 (2)	0.9012 (5)	0.1301 (2)	0.0321 (11)
C9	0.6953 (2)	0.8724 (5)	0.1399 (2)	0.0338 (11)
H9	0.6798	0.8078	0.1758	0.041*
C10	0.6461 (3)	0.9398 (5)	0.0962 (3)	0.0376 (12)
C11	0.6652 (3)	1.0380 (6)	0.0428 (3)	0.0446 (13)
C12	0.7383 (3)	1.0638 (6)	0.0349 (3)	0.0505 (14)
H12	0.7538	1.1292	−0.0007	0.061*
C13	0.7898 (3)	0.9972 (6)	0.0774 (3)	0.0434 (13)
H13	0.8392	1.0172	0.0704	0.052*
C14	0.6107 (3)	1.1121 (7)	−0.0045 (3)	0.071 (2)
H14A	0.5802	1.1796	0.0225	0.106*
H14B	0.5811	1.0346	−0.0263	0.106*
H14C	0.6358	1.1700	−0.0400	0.106*
C15	0.9170 (4)	0.3327 (8)	0.4458 (3)	0.083 (2)
H15A	0.9309	0.2704	0.4064	0.124*
H15B	0.8767	0.2854	0.4698	0.124*
H15C	0.9576	0.3423	0.4774	0.124*

	U11	U22	U33	U12	U13	U23
Cl1	0.0268 (7)	0.0794 (10)	0.0594 (9)	0.0022 (7)	−0.0050 (6)	−0.0039 (7)
Br1	0.0303 (3)	0.0724 (5)	0.0653 (4)	0.0062 (3)	0.0014 (3)	0.0108 (3)
N1	0.036 (2)	0.057 (3)	0.044 (3)	0.003 (2)	0.000 (2)	0.007 (2)
N2	0.032 (2)	0.035 (2)	0.034 (2)	0.0007 (18)	−0.0099 (17)	−0.0005 (19)
O1	0.053 (3)	0.091 (3)	0.059 (3)	0.021 (2)	0.004 (2)	0.024 (2)
O2	0.0296 (18)	0.070 (2)	0.047 (2)	0.0113 (18)	−0.0033 (16)	0.0053 (18)
O3	0.072 (3)	0.112 (4)	0.116 (4)	−0.001 (3)	0.046 (3)	−0.039 (3)
O4	0.050 (3)	0.112 (4)	0.122 (4)	−0.034 (3)	0.011 (3)	−0.027 (4)
C1	0.022 (2)	0.042 (3)	0.046 (3)	0.000 (2)	−0.002 (2)	−0.005 (2)
C2	0.031 (3)	0.036 (3)	0.036 (3)	0.009 (2)	−0.007 (2)	−0.005 (2)
C3	0.038 (3)	0.044 (3)	0.029 (3)	0.001 (2)	−0.003 (2)	−0.001 (2)
C4	0.024 (2)	0.035 (3)	0.042 (3)	0.004 (2)	−0.003 (2)	−0.009 (2)
C5	0.027 (2)	0.029 (2)	0.037 (3)	0.001 (2)	−0.004 (2)	0.001 (2)
C6	0.030 (3)	0.039 (3)	0.035 (3)	0.003 (2)	−0.002 (2)	0.000 (2)
C7	0.025 (2)	0.036 (3)	0.041 (3)	0.004 (2)	−0.004 (2)	−0.007 (2)
C8	0.026 (2)	0.032 (3)	0.037 (3)	0.004 (2)	−0.004 (2)	−0.004 (2)
C9	0.034 (3)	0.036 (3)	0.031 (2)	0.001 (2)	−0.001 (2)	0.001 (2)
C10	0.025 (2)	0.044 (3)	0.044 (3)	0.003 (2)	−0.005 (2)	−0.009 (2)
C11	0.037 (3)	0.050 (3)	0.047 (3)	0.007 (3)	−0.009 (2)	−0.001 (3)
C12	0.042 (3)	0.053 (4)	0.056 (3)	−0.005 (3)	−0.008 (3)	0.020 (3)
C13	0.036 (3)	0.049 (3)	0.045 (3)	−0.005 (3)	−0.007 (2)	0.005 (3)
C14	0.048 (4)	0.083 (5)	0.080 (5)	0.006 (3)	−0.016 (3)	0.030 (4)
C15	0.111 (6)	0.082 (5)	0.055 (4)	0.013 (4)	0.036 (4)	0.032 (4)

Cl1—C10	1.743 (5)	C6—H6	0.9300
Br1—C1	1.880 (5)	C7—H7	0.9300
N1—O4	1.171 (5)	C8—C9	1.365 (6)
N1—O3	1.182 (6)	C8—C13	1.365 (6)
N1—C4	1.448 (6)	C9—C10	1.358 (6)
N2—C7	1.307 (5)	C9—H9	0.9300
N2—C8	1.429 (5)	C10—C11	1.374 (7)
O1—C15	1.255 (7)	C11—C12	1.362 (7)
O1—C3	1.350 (6)	C11—C14	1.489 (7)
O2—C2	1.253 (5)	C12—C13	1.370 (7)
O2—H2	0.8200	C12—H12	0.9300
C1—C6	1.360 (6)	C13—H13	0.9300
C1—C2	1.420 (7)	C14—H14A	0.9600
C2—C3	1.429 (6)	C14—H14B	0.9600
C3—C4	1.348 (6)	C14—H14C	0.9600
C4—C5	1.429 (6)	C15—H15A	0.9600
C5—C6	1.386 (6)	C15—H15B	0.9600
C5—C7	1.392 (6)	C15—H15C	0.9600
O4—N1—O3	122.3 (5)	C13—C8—N2	115.9 (4)
O4—N1—C4	117.9 (5)	C10—C9—C8	118.8 (4)
O3—N1—C4	119.9 (5)	C10—C9—H9	120.6
C7—N2—C8	125.3 (4)	C8—C9—H9	120.6
C15—O1—C3	124.6 (5)	C9—C10—C11	123.6 (5)
C2—O2—H2	109.5	C9—C10—Cl1	116.8 (4)
C6—C1—C2	123.4 (4)	C11—C10—Cl1	119.6 (4)
C6—C1—Br1	118.0 (4)	C12—C11—C10	115.6 (5)
C2—C1—Br1	118.6 (3)	C12—C11—C14	121.2 (5)
O2—C2—C1	123.8 (4)	C10—C11—C14	123.1 (5)
O2—C2—C3	121.6 (4)	C11—C12—C13	122.7 (5)
C1—C2—C3	114.6 (4)	C11—C12—H12	118.7
O1—C3—C4	117.1 (4)	C13—C12—H12	118.7
O1—C3—C2	121.7 (4)	C8—C13—C12	119.4 (5)
C4—C3—C2	121.1 (4)	C8—C13—H13	120.3
C3—C4—C5	123.4 (4)	C12—C13—H13	120.3
C3—C4—N1	118.7 (4)	C11—C14—H14A	109.5
C5—C4—N1	117.9 (4)	C11—C14—H14B	109.5
C6—C5—C7	122.6 (4)	H14A—C14—H14B	109.5
C6—C5—C4	115.4 (4)	C11—C14—H14C	109.5
C7—C5—C4	122.0 (4)	H14A—C14—H14C	109.5
C1—C6—C5	122.0 (4)	H14B—C14—H14C	109.5
C1—C6—H6	119.0	O1—C15—H15A	109.5
C5—C6—H6	119.0	O1—C15—H15B	109.5
N2—C7—C5	123.7 (4)	H15A—C15—H15B	109.5
N2—C7—H7	118.2	O1—C15—H15C	109.5
C5—C7—H7	118.2	H15A—C15—H15C	109.5
C9—C8—C13	119.8 (4)	H15B—C15—H15C	109.5
C9—C8—N2	124.2 (4)

D—H···A	D—H	H···A	D···A	D—H···A
O2—H2···N2i	0.82	2.15	2.803 (5)	136
C6—H6···O2ii	0.93	2.38	3.210 (6)	149
C13—H13···O2ii	0.93	2.54	3.295 (6)	138

Table 1

Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
O2—H2⋯N2i	0.82	2.15	2.803 (5)	136
C6—H6⋯O2ii	0.93	2.38	3.210 (6)	149
C13—H13⋯O2ii	0.93	2.54	3.295 (6)	138

Symmetry codes: (i) ; (ii) .