N-(4-Bromo­benzyl­idene)-2-hydroxy­aniline

N-(4-Bromo­benzyl­idene)-2-hydroxy­aniline, C₁₃H₁₀BrNO, exists as a planar mol­ecule in which the hydr­oxy group is intra­molecularly hydrogen bonded to the imino N atom.

Key indicators

• Single-crystal X-ray study
• T = 292 K
• Mean [sigma](C-C) = 0.004 Å
• R factor = 0.038
• wR factor = 0.110
• Data-to-parameter ratio = 17.5

checkCIF/PLATON results

No syntax errors found



Alert level C
PLAT061_ALERT_3_C Tmax/Tmin Range Test RR' too Large .............       0.89
PLAT417_ALERT_2_C Short Inter D-H..H-D       H1     ..  H1      ..       2.13 Ang.

   0 ALERT level A = In general: serious problem
   0 ALERT level B = Potentially serious problem
   2 ALERT level C = Check and explain
   0 ALERT level G = General alerts; check

   0 ALERT type 1 CIF construction/syntax error, inconsistent or missing data
   1 ALERT type 2 Indicator that the structure model may be wrong or deficient
   1 ALERT type 3 Indicator that the structure quality may be low
   0 ALERT type 4 Improvement, methodology, query or suggestion
   0 ALERT type 5 Informative message, check

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Computing details

Data collection: SMART (Bruker, 2003); cell refinement: SAINT (Bruker, 2003); data reduction: SAINT; program(s) used to solve structure: SHELXS97 (Sheldrick, 1997); program(s) used to refine structure: SHELXL97 (Sheldrick, 1997); molecular graphics: X-SEED (Barbour, 2001); software used to prepare material for publication: SHELXL97.

N-(4-Bromobenzylidene)-2-hydroxyaniline

Crystal data

C13H10BrNO	F(000) = 552
Mr = 276.13	Dx = 1.603 Mg m^−3
Monoclinic, P21/n	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: -P 2yn	Cell parameters from 2244 reflections
a = 13.389 (1) Å	θ = 3.0–24.4°
b = 5.8745 (5) Å	µ = 3.57 mm^−1
c = 14.902 (1) Å	T = 292 K
β = 102.457 (1)°	Block, yellow
V = 1144.50 (15) Å^3	0.20 × 0.10 × 0.08 mm
Z = 4

Data collection

Bruker APEX CCD area-detector diffractometer	2608 independent reflections
Radiation source: fine-focus sealed tube	1677 reflections with I > 2σ(I)
Graphite monochromator	Rint = 0.029
φ and ω scans	θmax = 27.5°, θmin = 1.9°
Absorption correction: multi-scan (SADABS; Sheldrick, 1996)	h = −17→17
Tmin = 0.442, Tmax = 0.752	k = −7→7
10362 measured reflections	l = −19→19

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)] = 0.038	Hydrogen site location: inferred from neighbouring sites
wR(F^2) = 0.110	H atoms treated by a mixture of independent and constrained refinement
S = 1.02	w = 1/[σ^2(Fo^2) + (0.0539P)^2 + 0.1771P] where P = (Fo^2 + 2Fc^2)/3
2608 reflections	(Δ/σ)max = 0.001
149 parameters	Δρmax = 0.34 e Å^−3
1 restraint	Δρmin = −0.38 e Å^−3

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

	x	y	z	Uiso*/Ueq
Br1	0.94568 (2)	1.25502 (6)	0.38929 (3)	0.0863 (2)
O1	0.3953 (2)	0.5077 (3)	0.4465 (1)	0.0669 (5)
N1	0.4529 (1)	0.8854 (4)	0.3784 (1)	0.0486 (5)
C1	0.3198 (2)	0.6571 (4)	0.4094 (2)	0.0489 (6)
C2	0.2192 (2)	0.6069 (5)	0.4088 (2)	0.0563 (6)
C3	0.1441 (2)	0.7597 (4)	0.3714 (2)	0.0567 (7)
C4	0.1691 (2)	0.9617 (5)	0.3337 (2)	0.0566 (6)
C5	0.2693 (2)	1.0125 (4)	0.3336 (2)	0.0494 (6)
C6	0.3470 (2)	0.8611 (4)	0.3725 (2)	0.0456 (5)
C7	0.4899 (2)	1.0675 (4)	0.3536 (2)	0.0511 (6)
C8	0.5995 (2)	1.1039 (4)	0.3611 (2)	0.0469 (6)
C9	0.6326 (2)	1.3041 (5)	0.3283 (2)	0.0572 (7)
C10	0.7347 (2)	1.3504 (5)	0.3355 (2)	0.0592 (7)
C11	0.8047 (2)	1.1925 (5)	0.3766 (2)	0.0519 (6)
C12	0.7749 (2)	0.9902 (5)	0.4102 (2)	0.0565 (6)
C13	0.6724 (2)	0.9475 (4)	0.4025 (2)	0.0527 (6)
H1	0.451 (1)	0.568 (5)	0.440 (2)	0.09 (1)*
H2	0.2022	0.4706	0.4335	0.068*
H3	0.0761	0.7273	0.3713	0.068*
H4	0.1177	1.0639	0.3083	0.068*
H5	0.2853	1.1479	0.3076	0.059*
H7	0.4451	1.1839	0.3295	0.061*
H9	0.5843	1.4108	0.3007	0.069*
H10	0.7556	1.4857	0.3128	0.071*
H12	0.8236	0.8841	0.4376	0.068*
H13	0.6518	0.8122	0.4254	0.063*

Atomic displacement parameters (Ų)

	U^11	U^22	U^33	U^12	U^13	U^23
Br1	0.0511 (2)	0.1027 (3)	0.1085 (3)	−0.0145 (2)	0.0248 (2)	0.0003 (2)
O1	0.059 (1)	0.055 (1)	0.085 (1)	0.007 (1)	0.012 (1)	0.016 (1)
N1	0.044 (1)	0.050 (1)	0.052 (1)	0.000 (1)	0.010 (1)	0.003 (1)
C1	0.054 (2)	0.045 (1)	0.046 (1)	0.001 (1)	0.009 (1)	−0.003 (1)
C2	0.061 (2)	0.052 (2)	0.058 (2)	−0.008 (1)	0.018 (1)	−0.001 (1)
C3	0.045 (1)	0.068 (2)	0.059 (2)	−0.005 (1)	0.015 (1)	−0.006 (1)
C4	0.047 (1)	0.063 (2)	0.059 (2)	0.007 (1)	0.010 (1)	0.000 (1)
C5	0.048 (1)	0.048 (2)	0.052 (1)	−0.001 (1)	0.011 (1)	0.004 (1)
C6	0.045 (1)	0.048 (1)	0.043 (1)	−0.002 (1)	0.007 (1)	−0.002 (1)
C7	0.048 (1)	0.048 (2)	0.055 (2)	0.005 (1)	0.008 (1)	0.002 (1)
C8	0.046 (1)	0.046 (1)	0.046 (1)	−0.002 (1)	0.006 (1)	−0.002 (1)
C9	0.050 (1)	0.054 (2)	0.065 (2)	0.001 (1)	0.007 (1)	0.010 (1)
C10	0.068 (2)	0.051 (2)	0.060 (2)	−0.008 (1)	0.017 (1)	0.003 (1)
C11	0.043 (1)	0.062 (2)	0.052 (1)	−0.008 (1)	0.013 (1)	−0.007 (1)
C12	0.050 (1)	0.055 (2)	0.064 (2)	0.004 (1)	0.010 (1)	0.001 (1)
C13	0.052 (1)	0.047 (1)	0.059 (2)	−0.002 (1)	0.011 (1)	0.003 (1)

Geometric parameters (Å, º)

Br1—C11	1.892 (2)	C10—C11	1.366 (4)
O1—C1	1.362 (3)	C11—C12	1.382 (4)
N1—C7	1.267 (3)	C12—C13	1.376 (3)
N1—C6	1.410 (3)	O1—H1	0.85 (1)
C1—C2	1.376 (3)	C2—H2	0.93
C1—C6	1.399 (4)	C3—H3	0.93
C2—C3	1.374 (4)	C4—H4	0.93
C3—C4	1.384 (4)	C5—H5	0.93
C4—C5	1.375 (3)	C7—H7	0.93
C5—C6	1.396 (3)	C9—H9	0.93
C7—C8	1.464 (3)	C10—H10	0.93
C8—C9	1.382 (4)	C12—H12	0.93
C8—C13	1.385 (3)	C13—H13	0.93
C9—C10	1.375 (4)
C7—N1—C6	121.2 (2)	C12—C13—C8	120.7 (2)
O1—C1—C2	120.3 (2)	C1—O1—H1	106 (2)
O1—C1—C6	118.5 (2)	C1—C2—H2	120.3
C2—C1—C6	121.2 (2)	C3—C2—H2	120.3
C1—C2—C3	119.5 (2)	C2—C3—H3	119.8
C2—C3—C4	120.3 (2)	C4—C3—H3	119.8
C5—C4—C3	120.5 (2)	C5—C4—H4	119.7
C4—C5—C6	120.1 (2)	C3—C4—H4	119.7
C5—C6—C1	118.4 (2)	C4—C5—H5	120.0
C5—C6—N1	127.7 (2)	C6—C5—H5	120.0
C1—C6—N1	114.0 (2)	N1—C7—H7	118.3
N1—C7—C8	123.4 (2)	C8—C7—H7	118.3
C9—C8—C13	118.2 (2)	C10—C9—H9	119.0
C9—C8—C7	119.4 (2)	C8—C9—H9	119.0
C13—C8—C7	122.4 (2)	C11—C10—H10	120.8
C10—C9—C8	122.0 (3)	C9—C10—H10	120.8
C11—C10—C9	118.4 (3)	C13—C12—H12	120.4
C10—C11—C12	121.5 (2)	C11—C12—H12	120.4
C10—C11—Br1	119.1 (2)	C12—C13—H13	119.6
C12—C11—Br1	119.4 (2)	C8—C13—H13	119.6
C13—C12—C11	119.2 (2)
O1—C1—C2—C3	179.8 (2)	C6—N1—C7—C8	178.0 (2)
C6—C1—C2—C3	−0.1 (4)	N1—C7—C8—C9	177.0 (2)
C1—C2—C3—C4	0.6 (4)	N1—C7—C8—C13	−5.0 (4)
C2—C3—C4—C5	−0.2 (4)	C13—C8—C9—C10	0.4 (4)
C3—C4—C5—C6	−0.7 (4)	C7—C8—C9—C10	178.4 (2)
C4—C5—C6—C1	1.2 (3)	C8—C9—C10—C11	−0.3 (4)
C4—C5—C6—N1	−180.0 (2)	C9—C10—C11—C12	0.3 (4)
O1—C1—C6—C5	179.3 (2)	C9—C10—C11—Br1	−178.8 (2)
C2—C1—C6—C5	−0.8 (4)	C10—C11—C12—C13	−0.5 (4)
O1—C1—C6—N1	0.3 (3)	Br1—C11—C12—C13	178.7 (2)
C2—C1—C6—N1	−179.8 (2)	C11—C12—C13—C8	0.6 (4)
C7—N1—C6—C5	5.9 (4)	C9—C8—C13—C12	−0.5 (4)
C7—N1—C6—C1	−175.2 (2)	C7—C8—C13—C12	−178.4 (2)

Hydrogen-bond geometry (Å, º)

D—H···A	D—H	H···A	D···A	D—H···A
O1—H1···N1	0.85 (1)	2.08 (3)	2.624 (3)	122 (3)
O1—H1···O1^i	0.85 (1)	2.41 (3)	2.913 (4)	119 (3)

Symmetry code: (i) −x+1, −y+1, −z+1.