3-(4-Bromo­phenyl­imino­meth­yl)benzene-1,2-diol

In the solid state, the title mol­ecule, C₁₃H₁₀BrNO₂, exhibits two intra­molecular hydrogen bonds, namely an O—H...O hydrogen bond between vicinal hydr­oxy groups and an N—H...O hydrogen bond involving hydr­oxy and imine groups. In the crystal structure, symmetry-related mol­ecules are linked by bifurcated O—H...O hydrogen bonds to form centrosymmetric hydrogen-bonded dimers.

Key indicators

• Single-crystal X-ray study
• T = 173 K
• Mean [sigma](C-C)= 0.003 Å
• R factor = 0.032
• wR factor = 0.076
• Data-to-parameter ratio = 20.0

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Computing details

Data collection: X-AREA (Stoe & Cie, 2006); cell refinement: X-AREA; data reduction: X-RED32 (Stoe & Cie, 2006); program(s) used to solve structure: SHELXS97 (Sheldrick, 1997); program(s) used to refine structure: SHELXL97 (Sheldrick, 1997); molecular graphics: PLATON (Spek, 2003); software used to prepare material for publication: SHELXL97.

3-(4-Bromophenyliminomethyl)benzene-1,2-diol

Crystal data

C13H10BrNO2	Z = 2
Mr = 292.13	F(000) = 292
Triclinic, P1	Dx = 1.665 Mg m^−3
Hall symbol: -P 1	Mo Kα radiation, λ = 0.71073 Å
a = 6.0312 (12) Å	Cell parameters from 7425 reflections
b = 8.7087 (15) Å	θ = 1.7–29.6°
c = 11.837 (2) Å	µ = 3.51 mm^−1
α = 87.234 (15)°	T = 173 K
β = 81.945 (15)°	Plate, orange-red
γ = 71.189 (14)°	0.41 × 0.35 × 0.21 mm
V = 582.71 (19) Å^3

Data collection

Stoe IPDS-2 diffractometer	3121 independent reflections
Radiation source: fine-focus sealed tube	2733 reflections with I > 2σ(I)
Graphite monochromator	Rint = 0.031
Detector resolution: 6.67 pixels mm^-1	θmax = 29.2°, θmin = 1.7°
φ and ω scans	h = −8→8
Absorption correction: integration (X-RED32; Stoe & Cie, 2006)	k = −11→11
Tmin = 0.269, Tmax = 0.500	l = −16→16
7421 measured reflections

Refinement

Refinement on F^2	Primary atom site location: structure-invariant direct methods
Least-squares matrix: full	Secondary atom site location: difference Fourier map
R[F^2 > 2σ(F^2)] = 0.032	Hydrogen site location: inferred from neighbouring sites
wR(F^2) = 0.076	H-atom parameters constrained
S = 1.05	w = 1/[σ^2(Fo^2) + (0.0257P)^2 + 0.6141P] where P = (Fo^2 + 2Fc^2)/3
3121 reflections	(Δ/σ)max = 0.001
156 parameters	Δρmax = 0.85 e Å^−3
0 restraints	Δρmin = −0.77 e Å^−3

Special details

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 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 (Ų)

	x	y	z	Uiso*/Ueq
Br1	0.18618 (5)	−0.37185 (3)	0.94410 (2)	0.0402 (1)
O1	0.3014 (2)	0.46724 (17)	0.60514 (13)	0.0246 (4)
O2	0.2511 (2)	0.74287 (18)	0.47649 (13)	0.0279 (4)
N1	0.1008 (3)	0.2933 (2)	0.73726 (14)	0.0236 (5)
C1	0.1524 (4)	−0.1606 (2)	0.88345 (17)	0.0266 (5)
C2	−0.0254 (4)	−0.0908 (2)	0.81691 (18)	0.0265 (6)
C3	−0.0466 (4)	0.0615 (2)	0.76946 (17)	0.0252 (5)
C4	0.1092 (3)	0.1422 (2)	0.78856 (16)	0.0223 (5)
C5	0.2901 (4)	0.0681 (3)	0.85422 (18)	0.0275 (6)
C6	0.3105 (4)	−0.0833 (3)	0.90279 (18)	0.0294 (6)
C7	−0.0998 (3)	0.4043 (2)	0.73342 (17)	0.0235 (5)
C8	−0.1171 (3)	0.5547 (2)	0.67180 (16)	0.0219 (5)
C9	0.0834 (3)	0.5785 (2)	0.60771 (16)	0.0203 (5)
C10	0.0607 (3)	0.7199 (2)	0.54292 (16)	0.0216 (5)
C11	−0.1575 (3)	0.8386 (2)	0.54499 (17)	0.0245 (5)
C12	−0.3562 (4)	0.8171 (3)	0.61025 (19)	0.0274 (5)
C13	−0.3369 (3)	0.6757 (2)	0.67184 (18)	0.0254 (5)
H1	0.29280	0.38760	0.64640	0.0370*
H2	0.37200	0.66320	0.48370	0.0420*
H2A	−0.13170	−0.14630	0.80380	0.0320*
H3A	−0.16830	0.11070	0.72370	0.0300*
H5A	0.39980	0.12160	0.86570	0.0330*
H6A	0.43170	−0.13300	0.94870	0.0350*
H7A	−0.23920	0.38720	0.77170	0.0280*
H11A	−0.17180	0.93520	0.50160	0.0290*
H12A	−0.50500	0.89980	0.61240	0.0330*
H13A	−0.47370	0.66030	0.71460	0.0300*

Atomic displacement parameters (Ų)

	U^11	U^22	U^33	U^12	U^13	U^23
Br1	0.0560 (2)	0.0233 (1)	0.0350 (1)	−0.0075 (1)	−0.0006 (1)	0.0091 (1)
O1	0.0191 (6)	0.0191 (6)	0.0320 (7)	−0.0037 (5)	0.0003 (5)	0.0064 (5)
O2	0.0220 (7)	0.0229 (7)	0.0369 (8)	−0.0067 (5)	−0.0025 (6)	0.0110 (6)
N1	0.0262 (8)	0.0220 (8)	0.0231 (8)	−0.0093 (6)	−0.0009 (6)	0.0008 (6)
C1	0.0336 (10)	0.0184 (8)	0.0227 (9)	−0.0044 (7)	0.0021 (7)	0.0042 (7)
C2	0.0312 (10)	0.0228 (9)	0.0270 (10)	−0.0117 (8)	−0.0025 (8)	0.0034 (7)
C3	0.0275 (9)	0.0233 (9)	0.0256 (9)	−0.0092 (8)	−0.0048 (7)	0.0043 (7)
C4	0.0247 (9)	0.0205 (8)	0.0198 (8)	−0.0063 (7)	0.0006 (7)	0.0002 (7)
C5	0.0270 (9)	0.0285 (10)	0.0282 (10)	−0.0100 (8)	−0.0054 (8)	0.0008 (8)
C6	0.0302 (10)	0.0274 (10)	0.0266 (10)	−0.0031 (8)	−0.0069 (8)	0.0037 (8)
C7	0.0247 (9)	0.0233 (9)	0.0228 (9)	−0.0097 (7)	0.0009 (7)	−0.0006 (7)
C8	0.0232 (9)	0.0198 (8)	0.0226 (9)	−0.0073 (7)	−0.0010 (7)	−0.0017 (7)
C9	0.0204 (8)	0.0175 (8)	0.0223 (8)	−0.0048 (7)	−0.0032 (7)	0.0000 (6)
C10	0.0225 (8)	0.0194 (8)	0.0240 (9)	−0.0078 (7)	−0.0042 (7)	0.0016 (7)
C11	0.0272 (9)	0.0189 (8)	0.0278 (10)	−0.0063 (7)	−0.0080 (7)	0.0025 (7)
C12	0.0225 (9)	0.0236 (9)	0.0328 (10)	−0.0020 (7)	−0.0053 (8)	−0.0024 (8)
C13	0.0211 (9)	0.0260 (9)	0.0270 (9)	−0.0057 (7)	0.0003 (7)	−0.0034 (8)

Geometric parameters (Å, º)

Br1—C1	1.9009 (18)	C8—C13	1.402 (3)
O1—C9	1.356 (2)	C8—C9	1.404 (3)
O2—C10	1.363 (2)	C9—C10	1.397 (2)
O1—H1	0.8400	C10—C11	1.385 (3)
O2—H2	0.8400	C11—C12	1.393 (3)
N1—C7	1.287 (3)	C12—C13	1.381 (3)
N1—C4	1.411 (2)	C2—H2A	0.9500
C1—C6	1.380 (3)	C3—H3A	0.9500
C1—C2	1.382 (3)	C5—H5A	0.9500
C2—C3	1.389 (2)	C6—H6A	0.9500
C3—C4	1.389 (3)	C7—H7A	0.9500
C4—C5	1.395 (3)	C11—H11A	0.9500
C5—C6	1.388 (3)	C12—H12A	0.9500
C7—C8	1.449 (2)	C13—H13A	0.9500
Br1···Br1^i	3.7271 (8)	C7···H3A	2.7300
Br1···C4^ii	3.731 (2)	C7···H1	2.4100
Br1···H13A^iii	3.2300	C8···H2A^ix	3.0700
O1···O2	2.735 (2)	C12···H2^x	3.0000
O1···N1	2.574 (2)	C12···H2A^ix	2.9000
O1···O2^iv	2.797 (2)	C13···H2^x	3.0500
O2···C7^v	3.217 (3)	C13···H2A^ix	2.9000
O2···O1	2.735 (2)	H1···N1	1.8300
O2···O1^iv	2.797 (2)	H1···C4	3.0500
O2···C12^vi	3.267 (3)	H1···C7	2.4100
O1···H13A^vi	2.9200	H1···O2^iv	2.8300
O1···H2^iv	2.0900	H1···H2^iv	2.3000
O1···H2	2.2800	H2···O1	2.2800
O2···H1^iv	2.8300	H2···C12^vi	3.0000
O2···H3A^v	2.6700	H2···C13^vi	3.0500
O2···H11A^vii	2.7100	H2···O1^iv	2.0900
N1···O1	2.574 (2)	H2···H1^iv	2.3000
N1···H1	1.8300	H2A···C8^viii	3.0700
C2···C11^viii	3.549 (3)	H2A···C12^viii	2.9000
C4···Br1^ii	3.731 (2)	H2A···C13^viii	2.9000
C6···C13^iii	3.528 (3)	H3A···C7	2.7300
C7···C10^v	3.448 (3)	H3A···H7A	2.3900
C7···O2^v	3.217 (3)	H3A···O2^v	2.6700
C8···C10^v	3.481 (3)	H5A···H6A^xii	2.5700
C8···C9^v	3.516 (3)	H6A···H5A^xii	2.5700
C9···C8^v	3.516 (3)	H7A···C3	2.7000
C9···C9^v	3.365 (3)	H7A···H3A	2.3900
C10···C7^v	3.448 (3)	H7A···H13A	2.4600
C10···C8^v	3.481 (3)	H11A···O2^vii	2.7100
C11···C2^ix	3.549 (3)	H11A···H12A^xiii	2.5400
C12···O2^x	3.267 (3)	H12A···H11A^xiii	2.5400
C13···C6^xi	3.528 (3)	H13A···Br1^xi	3.2300
C1···H13A^iii	2.8800	H13A···O1^x	2.9200
C3···H7A	2.7000	H13A···C1^xi	2.8800
C4···H1	3.0500	H13A···C6^xi	3.0700
C6···H13A^iii	3.0700	H13A···H7A	2.4600
C9—O1—H1	109.00	C9—C10—C11	120.10 (17)
C10—O2—H2	109.00	O2—C10—C9	120.86 (16)
C4—N1—C7	119.84 (18)	C10—C11—C12	120.35 (18)
Br1—C1—C2	118.80 (16)	C11—C12—C13	120.0 (2)
C2—C1—C6	121.55 (18)	C8—C13—C12	120.55 (19)
Br1—C1—C6	119.60 (17)	C1—C2—H2A	120.00
C1—C2—C3	119.1 (2)	C3—C2—H2A	120.00
C2—C3—C4	120.4 (2)	C2—C3—H3A	120.00
C3—C4—C5	119.55 (18)	C4—C3—H3A	120.00
N1—C4—C3	122.03 (17)	C4—C5—H5A	120.00
N1—C4—C5	118.29 (18)	C6—C5—H5A	120.00
C4—C5—C6	120.3 (2)	C1—C6—H6A	120.00
C1—C6—C5	119.1 (2)	C5—C6—H6A	120.00
N1—C7—C8	121.32 (18)	N1—C7—H7A	119.00
C7—C8—C13	120.17 (17)	C8—C7—H7A	119.00
C7—C8—C9	120.58 (16)	C10—C11—H11A	120.00
C9—C8—C13	119.20 (16)	C12—C11—H11A	120.00
O1—C9—C10	118.07 (17)	C11—C12—H12A	120.00
O1—C9—C8	122.14 (16)	C13—C12—H12A	120.00
C8—C9—C10	119.78 (16)	C8—C13—H13A	120.00
O2—C10—C11	119.04 (16)	C12—C13—H13A	120.00
C7—N1—C4—C3	43.4 (3)	C7—C8—C9—O1	−3.4 (3)
C7—N1—C4—C5	−140.9 (2)	C7—C8—C9—C10	175.87 (17)
C4—N1—C7—C8	−173.90 (17)	C13—C8—C9—O1	179.18 (17)
Br1—C1—C2—C3	−178.06 (16)	C13—C8—C9—C10	−1.5 (3)
C6—C1—C2—C3	−0.7 (3)	C7—C8—C13—C12	−177.83 (19)
Br1—C1—C6—C5	177.38 (17)	C9—C8—C13—C12	−0.4 (3)
C2—C1—C6—C5	0.0 (3)	O1—C9—C10—O2	1.9 (3)
C1—C2—C3—C4	0.1 (3)	O1—C9—C10—C11	−178.50 (17)
C2—C3—C4—N1	176.77 (18)	C8—C9—C10—O2	−177.39 (17)
C2—C3—C4—C5	1.1 (3)	C8—C9—C10—C11	2.2 (3)
N1—C4—C5—C6	−177.61 (19)	O2—C10—C11—C12	178.70 (18)
C3—C4—C5—C6	−1.8 (3)	C9—C10—C11—C12	−0.9 (3)
C4—C5—C6—C1	1.2 (3)	C10—C11—C12—C13	−1.1 (3)
N1—C7—C8—C9	4.6 (3)	C11—C12—C13—C8	1.7 (3)
N1—C7—C8—C13	−178.06 (19)

Symmetry codes: (i) −x, −y−1, −z+2; (ii) −x, −y, −z+2; (iii) x+1, y−1, z; (iv) −x+1, −y+1, −z+1; (v) −x, −y+1, −z+1; (vi) x+1, y, z; (vii) −x, −y+2, −z+1; (viii) x, y−1, z; (ix) x, y+1, z; (x) x−1, y, z; (xi) x−1, y+1, z; (xii) −x+1, −y, −z+2; (xiii) −x−1, −y+2, −z+1.

Hydrogen-bond geometry (Å, º)

D—H···A	D—H	H···A	D···A	D—H···A
O2—H2···O1	0.84	2.28	2.735 (2)	114
O1—H1···N1	0.84	1.83	2.574 (2)	147
O2—H2···O1^iv	0.84	2.09	2.797 (2)	141

Symmetry code: (iv) −x+1, −y+1, −z+1.