(E)-3-[(2-Bromo­phen­yl)imino­meth­yl]benzene-1,2-diol

The title compound, C₁₃H₁₀BrNO₂, crystallizes in an enol–imine form. The mol­ecule is roughly planar, with a dihedral angle of 5.13 (10)° between the aromatic rings. Intra­molecular O—H...N hydrogen bonding generates an S(6) ring motif, whereas inter­molecular O—H...O hydrogen bonding links the mol­ecules into centrosymmetric R₂²(10) dimers.

Key indicators

• Single-crystal X-ray study
• T = 296 K
• Mean [sigma](C-C)= 0.004 Å
• R factor = 0.031
• wR factor = 0.073
• Data-to-parameter ratio = 14.1

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Computing details

Data collection: X-AREA (Stoe & Cie, 2002); cell refinement: X-AREA; data reduction: X-RED32 (Stoe & Cie, 2002); program(s) used to solve structure: SHELXS97 (Sheldrick, 1997); program(s) used to refine structure: SHELXL97 (Sheldrick, 1997); molecular graphics: ORTEP-3 for Windows (Farrugia, 1997); software used to prepare material for publication: WinGX (Farrugia, 1999).

(E)-3-[(2-Bromophenyl)iminomethyl]benzene-1,2-diol

Crystal data

C13H10BrNO2	F(000) = 584
Mr = 292.13	Dx = 1.714 Mg m^−3
Monoclinic, P21/c	Melting point: 398 K
Hall symbol: -P 2ybc	Mo Kα radiation, λ = 0.71073 Å
a = 7.2118 (6) Å	Cell parameters from 9250 reflections
b = 7.8271 (8) Å	θ = 2.0–27.9°
c = 20.9993 (15) Å	µ = 3.62 mm^−1
β = 107.283 (6)°	T = 296 K
V = 1131.84 (17) Å^3	Prismatic stick, red
Z = 4	0.57 × 0.31 × 0.09 mm

Data collection

Stoe IPDS II diffractometer	2218 independent reflections
Radiation source: sealed X-ray tube, 12 x 0.4 mm long-fine focus	1661 reflections with I > 2σ(I)
Plane graphite monochromator	Rint = 0.038
Detector resolution: 6.67 pixels mm^-1	θmax = 26.0°, θmin = 2.0°
ω scans	h = −8→8
Absorption correction: integration (X-RED; Stoe & Cie, 2002)	k = −9→9
Tmin = 0.290, Tmax = 0.730	l = −25→25
9250 measured reflections

Refinement

Refinement on F^2	Secondary atom site location: difference Fourier map
Least-squares matrix: full	Hydrogen site location: inferred from neighbouring sites
R[F^2 > 2σ(F^2)] = 0.031	H-atom parameters constrained
wR(F^2) = 0.074	w = 1/[σ^2(Fo^2) + (0.0351P)^2 + 0.351P] where P = (Fo^2 + 2Fc^2)/3
S = 1.03	(Δ/σ)max < 0.001
2218 reflections	Δρmax = 0.26 e Å^−3
157 parameters	Δρmin = −0.38 e Å^−3
0 restraints	Extinction correction: SHELXL97 (Sheldrick, 1997), Fc^*=kFc[1+0.001xFc^2λ^3/sin(2θ)]^-1/4
Primary atom site location: structure-invariant direct methods	Extinction coefficient: 0.0069 (8)

Special details

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.

Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Ų)

	x	y	z	Uiso*/Ueq
C1	0.0835 (4)	0.8966 (3)	0.40361 (12)	0.0374 (6)
C2	0.0654 (4)	0.7303 (3)	0.42620 (12)	0.0371 (6)
C3	−0.0213 (4)	0.6033 (3)	0.37895 (13)	0.0413 (6)
C4	−0.0890 (4)	0.6446 (4)	0.31252 (13)	0.0464 (6)
H4	−0.1467	0.5605	0.2817	0.056*
C5	−0.0728 (4)	0.8095 (4)	0.29059 (14)	0.0501 (7)
H5	−0.1197	0.8348	0.2454	0.060*
C6	0.0115 (4)	0.9349 (4)	0.33492 (13)	0.0464 (7)
H6	0.0216	1.0454	0.3199	0.056*
C7	0.1799 (4)	1.0274 (3)	0.44869 (13)	0.0415 (6)
H7	0.1866	1.1368	0.4323	0.050*
C8	0.3588 (4)	1.1247 (3)	0.55723 (13)	0.0389 (6)
C9	0.3766 (4)	1.2938 (4)	0.54018 (15)	0.0489 (7)
H9	0.3227	1.3287	0.4962	0.059*
C10	0.4731 (4)	1.4110 (4)	0.58766 (17)	0.0565 (8)
H10	0.4836	1.5240	0.5755	0.068*
C11	0.5534 (4)	1.3614 (4)	0.65265 (17)	0.0576 (8)
H11	0.6179	1.4409	0.6844	0.069*
C12	0.5390 (4)	1.1950 (4)	0.67090 (15)	0.0532 (8)
H12	0.5932	1.1614	0.7150	0.064*
C13	0.4433 (4)	1.0774 (3)	0.62320 (13)	0.0424 (6)
Br1	0.43102 (6)	0.84786 (4)	0.649487 (15)	0.06559 (16)
N1	0.2582 (3)	0.9987 (3)	0.51163 (10)	0.0387 (5)
O1	0.1281 (3)	0.6871 (2)	0.48997 (9)	0.0493 (5)
H1	0.1739	0.7713	0.5124	0.074*
O2	−0.0338 (3)	0.4389 (3)	0.39812 (10)	0.0570 (5)
H2	−0.0506	0.4376	0.4351	0.086*

Atomic displacement parameters (Ų)

	U^11	U^22	U^33	U^12	U^13	U^23
C1	0.0412 (14)	0.0403 (14)	0.0315 (12)	0.0014 (11)	0.0121 (10)	0.0010 (10)
C2	0.0384 (13)	0.0410 (14)	0.0315 (12)	−0.0010 (11)	0.0099 (10)	0.0005 (10)
C3	0.0449 (15)	0.0381 (14)	0.0425 (14)	−0.0025 (11)	0.0155 (12)	−0.0032 (11)
C4	0.0441 (14)	0.0553 (17)	0.0373 (13)	−0.0031 (13)	0.0082 (11)	−0.0074 (13)
C5	0.0534 (16)	0.0602 (19)	0.0331 (13)	0.0015 (14)	0.0075 (12)	0.0024 (12)
C6	0.0554 (16)	0.0457 (16)	0.0378 (14)	0.0010 (13)	0.0133 (12)	0.0073 (12)
C7	0.0491 (15)	0.0365 (14)	0.0413 (14)	0.0009 (12)	0.0172 (12)	0.0038 (11)
C8	0.0373 (13)	0.0370 (14)	0.0445 (14)	−0.0013 (11)	0.0153 (11)	−0.0054 (11)
C9	0.0556 (17)	0.0428 (16)	0.0503 (16)	−0.0071 (13)	0.0189 (13)	−0.0013 (12)
C10	0.0588 (18)	0.0394 (15)	0.076 (2)	−0.0120 (14)	0.0273 (17)	−0.0092 (15)
C11	0.0513 (17)	0.0547 (19)	0.0647 (19)	−0.0093 (15)	0.0142 (14)	−0.0233 (16)
C12	0.0516 (17)	0.056 (2)	0.0468 (16)	0.0047 (14)	0.0062 (13)	−0.0120 (13)
C13	0.0452 (15)	0.0395 (14)	0.0415 (14)	0.0037 (12)	0.0111 (12)	−0.0045 (11)
Br1	0.0994 (3)	0.04270 (18)	0.04540 (19)	0.00748 (18)	0.00737 (15)	0.00468 (14)
N1	0.0436 (12)	0.0371 (12)	0.0351 (11)	−0.0034 (9)	0.0112 (9)	−0.0010 (9)
O1	0.0699 (13)	0.0396 (11)	0.0341 (9)	−0.0087 (9)	0.0089 (9)	0.0029 (8)
O2	0.0822 (14)	0.0410 (12)	0.0497 (12)	−0.0108 (10)	0.0223 (11)	−0.0040 (9)

Geometric parameters (Å, º)

C1—C2	1.404 (4)	C8—C9	1.387 (4)
C1—C6	1.412 (3)	C8—C13	1.388 (4)
C1—C7	1.427 (4)	C8—N1	1.415 (3)
C2—O1	1.324 (3)	C9—C10	1.381 (4)
C2—C3	1.413 (4)	C9—H9	0.9300
C3—O2	1.359 (3)	C10—C11	1.371 (5)
C3—C4	1.373 (4)	C10—H10	0.9300
C4—C5	1.387 (4)	C11—C12	1.370 (4)
C4—H4	0.9300	C11—H11	0.9300
C5—C6	1.365 (4)	C12—C13	1.384 (4)
C5—H5	0.9300	C12—H12	0.9300
C6—H6	0.9300	C13—Br1	1.890 (3)
C7—N1	1.293 (3)	O1—H1	0.8200
C7—H7	0.9300	O2—H2	0.8200
C2—C1—C6	119.9 (2)	C9—C8—C13	117.7 (2)
C2—C1—C7	121.1 (2)	C9—C8—N1	123.9 (2)
C6—C1—C7	118.9 (2)	C13—C8—N1	118.3 (2)
O1—C2—C1	122.7 (2)	C10—C9—C8	120.9 (3)
O1—C2—C3	118.5 (2)	C10—C9—H9	119.6
C1—C2—C3	118.8 (2)	C8—C9—H9	119.6
O2—C3—C4	119.3 (2)	C11—C10—C9	120.2 (3)
O2—C3—C2	120.9 (2)	C11—C10—H10	119.9
C4—C3—C2	119.8 (3)	C9—C10—H10	119.9
C3—C4—C5	121.1 (3)	C12—C11—C10	120.2 (3)
C3—C4—H4	119.4	C12—C11—H11	119.9
C5—C4—H4	119.4	C10—C11—H11	119.9
C6—C5—C4	120.5 (3)	C11—C12—C13	119.5 (3)
C6—C5—H5	119.8	C11—C12—H12	120.2
C4—C5—H5	119.8	C13—C12—H12	120.2
C5—C6—C1	119.8 (3)	C12—C13—C8	121.4 (3)
C5—C6—H6	120.1	C12—C13—Br1	118.5 (2)
C1—C6—H6	120.1	C8—C13—Br1	120.0 (2)
N1—C7—C1	122.2 (2)	C7—N1—C8	123.4 (2)
N1—C7—H7	118.9	C2—O1—H1	109.5
C1—C7—H7	118.9	C3—O2—H2	109.5
C6—C1—C2—O1	−179.3 (3)	C6—C1—C7—N1	−176.3 (3)
C7—C1—C2—O1	3.0 (4)	C13—C8—C9—C10	−0.8 (4)
C6—C1—C2—C3	1.4 (4)	N1—C8—C9—C10	178.5 (3)
C7—C1—C2—C3	−176.3 (2)	C8—C9—C10—C11	0.1 (5)
O1—C2—C3—O2	−2.4 (4)	C9—C10—C11—C12	0.2 (5)
C1—C2—C3—O2	176.9 (3)	C10—C11—C12—C13	0.2 (5)
O1—C2—C3—C4	179.5 (2)	C11—C12—C13—C8	−0.9 (4)
C1—C2—C3—C4	−1.2 (4)	C11—C12—C13—Br1	178.6 (2)
O2—C3—C4—C5	−177.7 (3)	C9—C8—C13—C12	1.2 (4)
C2—C3—C4—C5	0.4 (4)	N1—C8—C13—C12	−178.1 (2)
C3—C4—C5—C6	0.0 (4)	C9—C8—C13—Br1	−178.3 (2)
C4—C5—C6—C1	0.2 (4)	N1—C8—C13—Br1	2.4 (3)
C2—C1—C6—C5	−1.0 (4)	C1—C7—N1—C8	178.4 (2)
C7—C1—C6—C5	176.8 (3)	C9—C8—N1—C7	3.2 (4)
C2—C1—C7—N1	1.5 (4)	C13—C8—N1—C7	−177.6 (3)

Hydrogen-bond geometry (Å, º)

D—H···A	D—H	H···A	D···A	D—H···A
O2—H2···O1^i	0.82	2.07	2.812 (3)	151
O1—H1···N1	0.82	1.88	2.604 (3)	146

Symmetry code: (i) −x, −y+1, −z+1.