(E)-4-[(4-Bromo-phen-yl)imino-meth-yl]-2-meth-oxy-phenol.

In the crystal structure of the title compound, C(14)H(12)BrNO(2), the dihedral angle between the rings is 37.87 (10)° and the mol-ecule has an E conformation about the central C=N bond. In the crystal, mol-ecules are connected by inter-molecular O-H⋯N hydrogen bonds into zigzag chains running parallel to the b axis. The packing also features C-H⋯O inter-actions.

Related literature

For Schiff base derivatives and related structures, see: Fejfarová et al. (2010a ▶,b ▶); Özek et al. (2009 ▶, 2010 ▶); Akkurt et al. (2008 ▶); Khalaji et al. (2007 ▶, 2009 ▶). For applications and properties of Schiff base compounds, see: da Silva et al. (2011 ▶); Dalapati et al. (2011 ▶); Sun et al. (2012 ▶).

Experimental

Crystal data

C14H12BrNO2

M = 306.2

Monoclinic,

a = 6.5692 (3) Å

b = 11.4323 (4) Å

c = 17.5552 (9) Å

β = 97.798 (4)°

V = 1306.22 (10) Å3

Z = 4

Cu Kα radiation

μ = 4.24 mm−1

T = 120 K

0.33 × 0.13 × 0.04 mm

Data collection

Agilent Xcalibur diffractometer with an Atlas (Gemini ultra Cu) detector

Absorption correction: multi-scan (CrysAlis PRO; Agilent, 2011 ▶) T min = 0.432, T max = 1

12474 measured reflections

2320 independent reflections

1991 reflections with I > 3σ(I)

R int = 0.044

Refinement

R[F 2 > 3σ(F 2)] = 0.028

wR(F 2) = 0.067

S = 1.65

2320 reflections

166 parameters

1 restraint

H atoms treated by a mixture of independent and constrained refinement

Δρmax = 0.27 e Å−3

Δρmin = −0.37 e Å−3

Data collection: CrysAlis PRO (Agilent, 2011 ▶); cell refinement: CrysAlis PRO; data reduction: CrysAlis PRO; program(s) used to solve structure: SIR2002 (Burla et al., 2003 ▶); program(s) used to refine structure: JANA2006 (Petříček et al., 2006 ▶); molecular graphics: DIAMOND (Brandenburg & Putz, 2005 ▶); software used to prepare material for publication: JANA2006.

Crystal structure: contains datablock(s) global, I. DOI: 10.1107/S1600536812031704/pk2433sup1.cif

Structure factors: contains datablock(s) I. DOI: 10.1107/S1600536812031704/pk2433Isup2.hkl

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

C14H12BrNO2	F(000) = 616
Mr = 306.2	Dx = 1.556 Mg m−3
Monoclinic, P21/c	Cu Kα radiation, λ = 1.5418 Å
Hall symbol: -P 2ybc	Cell parameters from 6414 reflections
a = 6.5692 (3) Å	θ = 3.9–66.9°
b = 11.4323 (4) Å	µ = 4.24 mm−1
c = 17.5552 (9) Å	T = 120 K
β = 97.798 (4)°	Plate, colourless
V = 1306.22 (10) Å3	0.33 × 0.13 × 0.04 mm
Z = 4

Agilent Xcalibur diffractometer with an Atlas (Gemini ultra Cu) detector	2320 independent reflections
Radiation source: Enhance Ultra (Cu) X-ray Source	1991 reflections with I > 3σ(I)
Mirror monochromator	Rint = 0.044
Detector resolution: 10.3784 pixels mm-1	θmax = 67.0°, θmin = 4.6°
Rotation method data acquisition using ω scans	h = −7→7
Absorption correction: multi-scan (CrysAlis PRO; Agilent, 2011)	k = −13→13
Tmin = 0.432, Tmax = 1	l = −19→20
12474 measured reflections

Refinement on F2	45 constraints
R[F2 > 2σ(F2)] = 0.028	H atoms treated by a mixture of independent and constrained refinement
wR(F2) = 0.067	Weighting scheme based on measured s.u.'s w = 1/(σ2(I) + 0.0004I2)
S = 1.65	(Δ/σ)max = 0.0003
2320 reflections	Δρmax = 0.27 e Å−3
166 parameters	Δρmin = −0.37 e Å−3
1 restraint

Experimental. Absorption correction: CrysAlis PRO (Agilent, 2011) Empirical absorption correction using spherical harmonics, implemented in SCALE3 ABSPACK scaling algorithm.

Refinement. The refinement was carried out against all reflections. The conventional R-factor is always based on F. The goodness of fit as well as the weighted R-factor are based on F and F2 for refinement carried out on F and F2, respectively. The threshold expression is used only for calculating R-factors etc. and it is not relevant to the choice of reflections for refinement.The program used for refinement, Jana2006, uses the weighting scheme based on the experimental expectations, see _refine_ls_weighting_details, that does not force S to be one. Therefore the values of S are usually larger than the ones from the SHELX program.

	x	y	z	Uiso*/Ueq
Br1	0.68807 (4)	0.03813 (2)	0.611307 (17)	0.04255 (10)
O1	1.0904 (2)	0.70826 (13)	0.18744 (10)	0.0341 (5)
O2	0.8114 (2)	0.88161 (13)	0.17128 (9)	0.0283 (5)
N1	0.8397 (3)	0.43584 (16)	0.39607 (10)	0.0260 (6)
C1	0.7469 (3)	0.61449 (19)	0.32641 (12)	0.0268 (6)
C2	0.9135 (3)	0.61379 (19)	0.28390 (13)	0.0278 (7)
C3	0.9362 (3)	0.70156 (18)	0.23240 (13)	0.0260 (6)
C4	0.7941 (3)	0.79425 (18)	0.22238 (13)	0.0252 (6)
C5	0.6294 (3)	0.79520 (19)	0.26391 (13)	0.0292 (7)
C6	0.6055 (3)	0.70607 (19)	0.31557 (13)	0.0296 (7)
C7	1.2114 (4)	0.6054 (2)	0.18148 (15)	0.0342 (8)
C8	0.7179 (3)	0.52315 (19)	0.38158 (12)	0.0278 (7)
C9	0.7943 (3)	0.34873 (18)	0.44886 (12)	0.0263 (6)
C10	0.9598 (3)	0.29543 (19)	0.49366 (13)	0.0304 (7)
C11	0.9292 (4)	0.2049 (2)	0.54324 (13)	0.0326 (7)
C12	0.7312 (4)	0.16602 (19)	0.54612 (13)	0.0308 (7)
C13	0.5637 (3)	0.21731 (19)	0.50239 (13)	0.0312 (7)
C14	0.5954 (3)	0.30931 (19)	0.45378 (13)	0.0281 (7)
H2	1.012127	0.551422	0.290947	0.0333*
H5	0.531306	0.857837	0.256922	0.035*
H6	0.490709	0.70739	0.344094	0.0355*
H7a	1.305933	0.618817	0.14521	0.0513*
H7b	1.286592	0.587401	0.230856	0.0513*
H7c	1.12292	0.541111	0.164378	0.0513*
H8	0.600817	0.52848	0.408718	0.0334*
H10	1.096928	0.321827	0.490106	0.0365*
H11	1.043401	0.169756	0.575023	0.0391*
H13	0.42723	0.189582	0.505637	0.0374*
H14	0.480191	0.345928	0.423465	0.0337*
H2o	0.930 (2)	0.882 (2)	0.1576 (16)	0.0424*

	U11	U22	U33	U12	U13	U23
Br1	0.04436 (17)	0.03681 (16)	0.05028 (18)	0.00744 (11)	0.02019 (12)	0.01743 (12)
O1	0.0363 (9)	0.0270 (8)	0.0426 (9)	0.0074 (6)	0.0190 (7)	0.0074 (7)
O2	0.0264 (8)	0.0245 (8)	0.0347 (9)	0.0004 (6)	0.0066 (6)	0.0055 (6)
N1	0.0294 (9)	0.0254 (9)	0.0235 (9)	−0.0014 (7)	0.0044 (8)	0.0003 (7)
C1	0.0314 (11)	0.0256 (11)	0.0237 (11)	0.0006 (9)	0.0050 (9)	−0.0045 (9)
C2	0.0310 (11)	0.0240 (11)	0.0287 (11)	0.0035 (9)	0.0054 (9)	−0.0003 (9)
C3	0.0275 (10)	0.0251 (11)	0.0261 (11)	−0.0003 (8)	0.0063 (9)	−0.0029 (9)
C4	0.0264 (10)	0.0216 (10)	0.0271 (11)	−0.0035 (8)	0.0014 (9)	−0.0031 (9)
C5	0.0294 (11)	0.0259 (11)	0.0327 (12)	0.0030 (9)	0.0062 (9)	−0.0012 (9)
C6	0.0306 (11)	0.0297 (11)	0.0299 (12)	0.0018 (9)	0.0093 (9)	−0.0022 (9)
C7	0.0317 (12)	0.0276 (12)	0.0459 (14)	0.0044 (9)	0.0146 (11)	0.0005 (10)
C8	0.0315 (11)	0.0288 (12)	0.0243 (11)	−0.0001 (9)	0.0075 (9)	−0.0043 (9)
C9	0.0321 (11)	0.0237 (11)	0.0237 (11)	0.0004 (8)	0.0066 (9)	−0.0037 (9)
C10	0.0255 (11)	0.0327 (12)	0.0331 (12)	−0.0009 (9)	0.0043 (9)	0.0011 (10)
C11	0.0317 (12)	0.0339 (13)	0.0317 (12)	0.0057 (9)	0.0025 (10)	0.0053 (10)
C12	0.0349 (12)	0.0271 (11)	0.0318 (12)	0.0024 (9)	0.0101 (10)	0.0035 (9)
C13	0.0276 (11)	0.0321 (12)	0.0356 (13)	−0.0005 (9)	0.0108 (10)	−0.0005 (10)
C14	0.0275 (11)	0.0302 (12)	0.0273 (11)	0.0032 (9)	0.0060 (9)	0.0010 (9)

Br1—C12	1.901 (2)	C6—H6	0.96
O1—C3	1.368 (3)	C7—H7a	0.96
O1—C7	1.431 (3)	C7—H7b	0.96
O2—C4	1.358 (3)	C7—H7c	0.96
O2—H2o	0.846 (19)	C8—H8	0.96
N1—C8	1.283 (3)	C9—C10	1.393 (3)
N1—C9	1.419 (3)	C9—C14	1.396 (3)
C1—C2	1.406 (3)	C10—C11	1.385 (3)
C1—C6	1.396 (3)	C10—H10	0.96
C1—C8	1.454 (3)	C11—C12	1.382 (3)
C2—C3	1.372 (3)	C11—H11	0.96
C2—H2	0.96	C12—C13	1.384 (3)
C3—C4	1.407 (3)	C13—C14	1.388 (3)
C4—C5	1.384 (3)	C13—H13	0.96
C5—C6	1.387 (3)	C14—H14	0.96
C5—H5	0.96
C3—O1—C7	117.28 (17)	H7a—C7—H7b	109.4709
C4—O2—H2o	111.1 (19)	H7a—C7—H7c	109.4715
C8—N1—C9	119.6 (2)	H7b—C7—H7c	109.4709
C2—C1—C6	118.9 (2)	N1—C8—C1	123.8 (2)
C2—C1—C8	122.1 (2)	N1—C8—H8	118.1105
C6—C1—C8	119.0 (2)	C1—C8—H8	118.1102
C1—C2—C3	120.5 (2)	N1—C9—C10	117.3 (2)
C1—C2—H2	119.7453	N1—C9—C14	123.25 (18)
C3—C2—H2	119.747	C10—C9—C14	119.3 (2)
O1—C3—C2	125.18 (19)	C9—C10—C11	120.9 (2)
O1—C3—C4	114.60 (19)	C9—C10—H10	119.5592
C2—C3—C4	120.2 (2)	C11—C10—H10	119.5589
O2—C4—C3	121.5 (2)	C10—C11—C12	118.7 (2)
O2—C4—C5	118.94 (19)	C10—C11—H11	120.6272
C3—C4—C5	119.5 (2)	C12—C11—H11	120.6256
C4—C5—C6	120.3 (2)	Br1—C12—C11	119.14 (17)
C4—C5—H5	119.8487	Br1—C12—C13	119.19 (18)
C6—C5—H5	119.849	C11—C12—C13	121.7 (2)
C1—C6—C5	120.5 (2)	C12—C13—C14	119.2 (2)
C1—C6—H6	119.7435	C12—C13—H13	120.3851
C5—C6—H6	119.7433	C14—C13—H13	120.3861
O1—C7—H7a	109.4713	C9—C14—C13	120.15 (19)
O1—C7—H7b	109.4714	C9—C14—H14	119.9259
O1—C7—H7c	109.4714	C13—C14—H14	119.925
C2—C3—O1—C7	13.8 (3)

D—H···A	D—H	H···A	D···A	D—H···A
C2—H2···O2i	0.96	2.31	3.247 (3)	165
C14—H14···O2ii	0.96	2.40	3.325 (3)	163
O2—H2o···N1iii	0.85 (2)	1.98 (2)	2.787 (2)	158 (3)

Table 1

Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
C2—H2⋯O2i	0.96	2.31	3.247 (3)	165
C14—H14⋯O2ii	0.96	2.40	3.325 (3)	163
O2—H2o⋯N1iii	0.85 (2)	1.98 (2)	2.787 (2)	158 (3)

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