4-Bromo-2-[(E)-(2-fluoro-5-nitro-phenyl)iminometh-yl]phenol.

The mol-ecular conformation of the title compound, C13H8BrFN2O3, is essentially planar, with maximum deviations of 0.076 (1) and -0.080 (2) Å for the O atoms of the NO2 group. The mol-ecular conformation is stabilized by an intra-molecular O-H⋯N hydrogen bond, forming an S(6) ring motif. In the crystal, pairs of mol-ecules are linked via two pairs of C-H⋯O hydrogen bonds, forming inversion dimers that enclose R(2)2(7)R(2)2(10)R(2)2(7) ring motifs.

Related literature

For the synthesis and biological activity of azomethines, see: Przybylski et al. (2009 ▶); Kalaivani et al. (2012 ▶); Blair et al. (2000 ▶). For the synthesis of fluorinated azomethines, see: Mohamed et al. (2012 ▶). For hydrogen-bond motifs, see: Bernstein et al. (1995 ▶). For standard bond lengths, see: Allen et al. (1987 ▶).

Experimental

Crystal data

C13H8BrFN2O3

M = 339.11

Monoclinic,

a = 4.5082 (9) Å

b = 19.815 (4) Å

c = 13.853 (3) Å

β = 95.484 (5)°

V = 1231.8 (4) Å3

Z = 4

Mo Kα radiation

μ = 3.36 mm−1

T = 100 K

0.24 × 0.04 × 0.03 mm

Data collection

Rigaku AFC12 (Right) diffractometer

Absorption correction: multi-scan (CrystalClear-SM Expert; Rigaku, 2012 ▶) T min = 0.500, T max = 0.906

8107 measured reflections

2811 independent reflections

2633 reflections with I > 2σ(I)

R int = 0.023

Refinement

R[F 2 > 2σ(F 2)] = 0.025

wR(F 2) = 0.059

S = 1.05

2811 reflections

182 parameters

H-atom parameters constrained

Δρmax = 0.52 e Å−3

Δρmin = −0.54 e Å−3

Data collection: CrystalClear-SM Expert (Rigaku, 2012 ▶); cell refinement: CrystalClear-SM Expert; data reduction: CrystalClear-SM Expert; program(s) used to solve structure: SHELXS97 (Sheldrick, 2008 ▶); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008 ▶); molecular graphics: ORTEP-3 for Windows (Farrugia, 2012 ▶); software used to prepare material for publication: WinGX (Farrugia, 2012 ▶) and PLATON (Spek, 2009 ▶).

Click here for additional data file.

Crystal structure: contains datablock(s) global, I. DOI: 10.1107/S1600536812050696/xu5665sup1.cif

Click here for additional data file.

Structure factors: contains datablock(s) I. DOI: 10.1107/S1600536812050696/xu5665Isup2.hkl

Click here for additional data file.

Supplementary material file. DOI: 10.1107/S1600536812050696/xu5665Isup3.cml

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

C13H8BrFN2O3	F(000) = 672
Mr = 339.11	Dx = 1.829 Mg m−3
Monoclinic, P21/n	Mo Kα radiation, λ = 0.71075 Å
Hall symbol: -P 2yn	Cell parameters from 4566 reflections
a = 4.5082 (9) Å	θ = 2.5–31.2°
b = 19.815 (4) Å	µ = 3.36 mm−1
c = 13.853 (3) Å	T = 100 K
β = 95.484 (5)°	Rod, yellow
V = 1231.8 (4) Å3	0.24 × 0.04 × 0.03 mm
Z = 4

Rigaku AFC12 (Right) diffractometer	2811 independent reflections
Radiation source: Rotating Anode	2633 reflections with I > 2σ(I)
Detector resolution: 28.5714 pixels mm-1	Rint = 0.023
profile data from ω–scans	θmax = 27.5°, θmin = 3.0°
Absorption correction: multi-scan (CrystalClear-SM Expert; Rigaku, 2012)	h = −5→5
Tmin = 0.500, Tmax = 0.906	k = −25→24
8107 measured reflections	l = −17→14

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)] = 0.025	Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.059	H-atom parameters constrained
S = 1.05	w = 1/[σ2(Fo2) + (0.0255P)2 + 1.1447P] where P = (Fo2 + 2Fc2)/3
2811 reflections	(Δ/σ)max = 0.001
182 parameters	Δρmax = 0.52 e Å−3
0 restraints	Δρmin = −0.54 e Å−3

Geometry. Bond distances, angles etc. have been calculated using the rounded fractional coordinates. All su's are estimated from the variances of the (full) variance-covariance matrix. The cell e.s.d.'s are taken into account in the estimation of distances, angles and torsion angles

Refinement. Refinement on F2 for ALL reflections except those flagged by the user for potential systematic errors. Weighted R-factors wR and all goodnesses of fit S are based on F2, conventional R-factors R are based on F, with F set to zero for negative F2. The observed criterion of F2 > σ(F2) is used only for calculating -R-factor-obs 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
Br1	−0.15532 (4)	0.22619 (1)	0.43736 (1)	0.0188 (1)
F1	0.7510 (2)	0.50903 (6)	0.05672 (7)	0.0202 (3)
O1	0.2171 (3)	0.37891 (7)	0.09274 (9)	0.0171 (4)
O2	1.5039 (3)	0.63282 (8)	0.41030 (11)	0.0290 (4)
O3	1.2227 (5)	0.56614 (11)	0.48212 (12)	0.0614 (8)
N1	0.5847 (3)	0.44689 (7)	0.21201 (11)	0.0140 (4)
N2	1.3057 (4)	0.59101 (9)	0.40914 (12)	0.0227 (5)
C1	0.2662 (4)	0.36222 (8)	0.26646 (12)	0.0123 (5)
C2	0.1398 (4)	0.34652 (9)	0.17204 (12)	0.0135 (5)
C3	−0.0742 (4)	0.29535 (9)	0.15895 (13)	0.0157 (5)
C4	−0.1635 (4)	0.26099 (9)	0.23746 (13)	0.0159 (5)
C5	−0.0389 (4)	0.27669 (9)	0.33084 (12)	0.0140 (5)
C6	0.1728 (4)	0.32683 (9)	0.34603 (12)	0.0145 (5)
C7	0.4936 (4)	0.41399 (9)	0.28338 (13)	0.0138 (5)
C8	0.8050 (4)	0.49730 (9)	0.22592 (13)	0.0136 (5)
C9	0.8877 (4)	0.52873 (9)	0.14215 (12)	0.0150 (5)
C10	1.0992 (4)	0.57931 (9)	0.14290 (13)	0.0165 (5)
C11	1.2365 (4)	0.60049 (9)	0.23159 (13)	0.0157 (5)
C12	1.1566 (4)	0.56969 (9)	0.31484 (13)	0.0156 (5)
C13	0.9451 (4)	0.51880 (9)	0.31435 (13)	0.0154 (5)
H1	0.34830	0.40790	0.10930	0.0260*
H3	−0.15830	0.28430	0.09540	0.0190*
H4	−0.31010	0.22660	0.22810	0.0190*
H6	0.25500	0.33730	0.41000	0.0170*
H7	0.57530	0.42350	0.34770	0.0170*
H10	1.14920	0.59910	0.08410	0.0200*
H11	1.38190	0.63530	0.23510	0.0190*
H13	0.89690	0.49900	0.37330	0.0180*

	U11	U22	U33	U12	U13	U23
Br1	0.0189 (1)	0.0213 (1)	0.0161 (1)	−0.0045 (1)	0.0003 (1)	0.0053 (1)
F1	0.0209 (6)	0.0273 (6)	0.0115 (5)	−0.0064 (5)	−0.0028 (4)	0.0011 (4)
O1	0.0208 (7)	0.0184 (6)	0.0119 (6)	−0.0042 (5)	0.0007 (5)	0.0008 (5)
O2	0.0326 (8)	0.0292 (8)	0.0243 (7)	−0.0159 (7)	−0.0022 (6)	−0.0043 (6)
O3	0.0880 (16)	0.0804 (15)	0.0135 (8)	−0.0628 (13)	−0.0074 (9)	0.0082 (8)
N1	0.0128 (7)	0.0141 (7)	0.0150 (7)	0.0001 (6)	0.0013 (6)	−0.0005 (5)
N2	0.0290 (9)	0.0228 (8)	0.0156 (8)	−0.0085 (7)	−0.0011 (7)	−0.0008 (6)
C1	0.0110 (8)	0.0124 (8)	0.0136 (8)	0.0021 (6)	0.0011 (6)	−0.0003 (6)
C2	0.0137 (8)	0.0135 (8)	0.0133 (8)	0.0026 (6)	0.0015 (6)	0.0004 (6)
C3	0.0156 (9)	0.0171 (8)	0.0140 (8)	0.0000 (7)	−0.0011 (6)	−0.0047 (7)
C4	0.0145 (8)	0.0144 (8)	0.0186 (9)	−0.0005 (7)	0.0001 (7)	−0.0018 (7)
C5	0.0144 (8)	0.0148 (8)	0.0127 (8)	0.0009 (7)	0.0015 (6)	0.0021 (6)
C6	0.0147 (8)	0.0160 (8)	0.0125 (8)	0.0014 (7)	0.0000 (6)	0.0002 (6)
C7	0.0123 (8)	0.0151 (8)	0.0137 (8)	0.0012 (7)	−0.0005 (6)	−0.0014 (6)
C8	0.0129 (8)	0.0129 (8)	0.0151 (8)	0.0007 (6)	0.0016 (7)	−0.0003 (6)
C9	0.0139 (8)	0.0179 (8)	0.0125 (8)	0.0022 (7)	−0.0023 (6)	−0.0014 (6)
C10	0.0164 (9)	0.0166 (8)	0.0167 (9)	0.0011 (7)	0.0022 (7)	0.0036 (7)
C11	0.0155 (8)	0.0126 (8)	0.0191 (9)	−0.0009 (7)	0.0017 (7)	0.0007 (7)
C12	0.0163 (9)	0.0155 (8)	0.0145 (8)	−0.0004 (7)	−0.0010 (7)	−0.0021 (6)
C13	0.0160 (9)	0.0159 (8)	0.0143 (8)	−0.0009 (7)	0.0012 (7)	0.0007 (6)

Br1—C5	1.8980 (18)	C5—C6	1.380 (3)
F1—C9	1.339 (2)	C8—C13	1.390 (3)
O1—C2	1.347 (2)	C8—C9	1.399 (2)
O2—N2	1.218 (2)	C9—C10	1.383 (3)
O3—N2	1.215 (3)	C10—C11	1.387 (3)
O1—H1	0.8400	C11—C12	1.383 (3)
N1—C7	1.284 (2)	C12—C13	1.387 (3)
N1—C8	1.409 (2)	C3—H3	0.9500
N2—C12	1.473 (2)	C4—H4	0.9500
C1—C6	1.405 (2)	C6—H6	0.9500
C1—C7	1.453 (2)	C7—H7	0.9500
C1—C2	1.411 (2)	C10—H10	0.9500
C2—C3	1.399 (3)	C11—H11	0.9500
C3—C4	1.376 (3)	C13—H13	0.9500
C4—C5	1.395 (2)
C2—O1—H1	109.00	F1—C9—C10	118.47 (15)
C7—N1—C8	121.86 (16)	C8—C9—C10	123.70 (16)
O2—N2—C12	118.63 (16)	C9—C10—C11	118.36 (16)
O3—N2—C12	118.09 (18)	C10—C11—C12	118.40 (17)
O2—N2—O3	123.29 (18)	N2—C12—C11	118.69 (16)
C2—C1—C7	121.43 (15)	C11—C12—C13	123.40 (17)
C6—C1—C7	119.05 (15)	N2—C12—C13	117.91 (16)
C2—C1—C6	119.52 (16)	C8—C13—C12	118.76 (16)
O1—C2—C3	117.94 (15)	C2—C3—H3	120.00
C1—C2—C3	119.50 (16)	C4—C3—H3	120.00
O1—C2—C1	122.56 (16)	C3—C4—H4	120.00
C2—C3—C4	120.43 (16)	C5—C4—H4	120.00
C3—C4—C5	120.02 (17)	C1—C6—H6	120.00
Br1—C5—C4	119.11 (13)	C5—C6—H6	120.00
Br1—C5—C6	119.98 (13)	N1—C7—H7	120.00
C4—C5—C6	120.88 (16)	C1—C7—H7	120.00
C1—C6—C5	119.65 (15)	C9—C10—H10	121.00
N1—C7—C1	120.45 (16)	C11—C10—H10	121.00
N1—C8—C9	116.27 (16)	C10—C11—H11	121.00
N1—C8—C13	126.35 (16)	C12—C11—H11	121.00
C9—C8—C13	117.38 (16)	C8—C13—H13	121.00
F1—C9—C8	117.83 (16)	C12—C13—H13	121.00
C8—N1—C7—C1	−179.92 (16)	C3—C4—C5—C6	0.4 (3)
C7—N1—C8—C9	179.13 (17)	C3—C4—C5—Br1	−177.66 (14)
C7—N1—C8—C13	−1.3 (3)	Br1—C5—C6—C1	177.55 (13)
O3—N2—C12—C13	−4.7 (3)	C4—C5—C6—C1	−0.5 (3)
O2—N2—C12—C11	−3.3 (3)	N1—C8—C9—C10	179.72 (16)
O2—N2—C12—C13	175.80 (17)	C13—C8—C9—F1	−179.08 (16)
O3—N2—C12—C11	176.20 (19)	C13—C8—C9—C10	0.1 (3)
C7—C1—C2—C3	178.71 (17)	N1—C8—C9—F1	0.5 (2)
C7—C1—C6—C5	−178.80 (17)	N1—C8—C13—C12	−179.49 (17)
C2—C1—C7—N1	0.1 (3)	C9—C8—C13—C12	0.1 (3)
C2—C1—C6—C5	0.7 (3)	F1—C9—C10—C11	178.83 (16)
C6—C1—C2—C3	−0.8 (3)	C8—C9—C10—C11	−0.4 (3)
C7—C1—C2—O1	−1.2 (3)	C9—C10—C11—C12	0.4 (3)
C6—C1—C7—N1	179.58 (16)	C10—C11—C12—N2	178.83 (16)
C6—C1—C2—O1	179.35 (16)	C10—C11—C12—C13	−0.3 (3)
O1—C2—C3—C4	−179.43 (16)	N2—C12—C13—C8	−179.08 (16)
C1—C2—C3—C4	0.7 (3)	C11—C12—C13—C8	0.0 (3)
C2—C3—C4—C5	−0.5 (3)

D—H···A	D—H	H···A	D···A	D—H···A
O1—H1···N1	0.84	1.86	2.601 (2)	146
C7—H7···O3i	0.95	2.45	3.399 (3)	173
C13—H13···O3i	0.95	2.48	3.430 (3)	173

Table 1

Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
O1—H1⋯N1	0.84	1.86	2.601 (2)	146
C7—H7⋯O3i	0.95	2.45	3.399 (3)	173
C13—H13⋯O3i	0.95	2.48	3.430 (3)	173

Symmetry code: (i) .