4-Bromo-2-(2-pyridyl­methyl­imino­methyl)­phenol

Two mol­ecules of the title compound, C₁₃H₁₁BrN₂O, are linked by an intermolecular Br...N_pyridyl interaction of 3.263 (4) Å across a center of inversion. The imino N atom is engaged in intramolecular hydrogen bonding with the phenol group [O...N = 2.595 (5) Å].

Key indicators

• Single-crystal X-ray study
• T = 298 K
• Mean [sigma](C-C) = 0.007 Å
• R factor = 0.045
• wR factor = 0.108
• Data-to-parameter ratio = 13.3

checkCIF/PLATON results

No syntax errors found



Alert level A
PLAT029_ALERT_3_A _diffrn_measured_fraction_theta_full Low .......       0.97
PLAT052_ALERT_1_A (Proper) Absorption Correction Method Missing ..          ?
PLAT057_ALERT_3_A Correction for Absorption Required   RT(exp)   =       1.39

Alert level C
PLAT125_ALERT_4_C No _symmetry_space_group_name_Hall Given .......          ?
PLAT341_ALERT_3_C Low Bond Precision on C-C bonds (x 1000) Ang ...          7
PLAT431_ALERT_2_C Short Inter HL..A Contact  Br1    ..  N2       =       3.26 Ang.

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

   1 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
   3 ALERT type 3 Indicator that the structure quality may be low
   1 ALERT type 4 Improvement, methodology, query or suggestion

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Computing details

Data collection: XSCANS (Bruker, 1997); cell refinement: LEAST SQUARES in XSCANS; data reduction: REDUCE in XSCANS; program(s) used to solve structure: SHELXS97 (Sheldrick, 1997); program(s) used to refine structure: SHELXL97 (Sheldrick, 1997); molecular graphics: ORTEPII (Johnson, 1976); software used to prepare material for publication: SHELXL97.

2-(3-Pyridylmethyliminomethyl)-4-bromophenol

Crystal data

C13H11BrN2O	Z = 2
Mr = 291.15	F(000) = 292
Triclinic, P1	Dx = 1.601 Mg m^−3
a = 4.474 (1) Å	Mo Kα radiation, λ = 0.71073 Å
b = 9.529 (2) Å	Cell parameters from 25 reflections
c = 14.271 (2) Å	θ = 4.5–12.7°
α = 92.65 (1)°	µ = 3.39 mm^−1
β = 93.72 (1)°	T = 298 K
γ = 95.16 (2)°	Block, yellow
V = 603.8 (2) Å^3	0.20 × 0.20 × 0.10 mm

Data collection

Siemens P4 four-circle diffractometer	1416 reflections with I > 2σ(I)
Radiation source: fine-focus sealed tube	Rint = 0.030
Graphite monochromator	θmax = 25.0°, θmin = 2.2°
ω–2θ scan	h = −5→1
Absorption correction: ψ scan (North et al., 1996)	k = −11→11
Tmin = 0.531, Tmax = 0.713	l = −16→16
2912 measured reflections	3 standard reflections every 97 reflections
2069 independent reflections	intensity decay: none

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)] = 0.045	Hydrogen site location: inferred from neighbouring sites
wR(F^2) = 0.108	H-atom parameters constrained
S = 1.01	w = 1/[σ^2(Fo^2) + (0.0478P)^2 + 0.2428P] where P = (Fo^2 + 2Fc^2)/3
2069 reflections	(Δ/σ)max = 0.001
155 parameters	Δρmax = 0.32 e Å^−3
0 restraints	Δρmin = −0.28 e Å^−3

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

	x	y	z	Uiso*/Ueq
Br1	0.3034 (1)	0.24335 (6)	0.58068 (3)	0.0790 (3)
O1	0.6041 (8)	0.2028 (3)	0.1768 (2)	0.071 (1)
N1	0.9805 (8)	0.4255 (4)	0.2113 (3)	0.056 (1)
N2	0.9128 (9)	0.7314 (4)	0.2056 (3)	0.061 (1)
C1	0.6918 (9)	0.3203 (4)	0.3293 (3)	0.048 (1)
C2	0.548 (1)	0.2130 (4)	0.2681 (3)	0.052 (1)
C3	0.339 (1)	0.1133 (5)	0.3018 (3)	0.064 (1)
C4	0.270 (1)	0.1215 (5)	0.3945 (4)	0.065 (1)
C5	0.412 (1)	0.2293 (5)	0.4542 (3)	0.057 (1)
C6	0.620 (1)	0.3267 (4)	0.4223 (3)	0.053 (1)
C7	0.9191 (9)	0.4232 (4)	0.2968 (3)	0.052 (1)
C8	1.205 (1)	0.5345 (5)	0.1849 (3)	0.067 (1)
C9	1.0506 (9)	0.6552 (4)	0.1442 (3)	0.051 (1)
C10	1.050 (1)	0.6829 (5)	0.0507 (3)	0.066 (1)
C11	0.907 (1)	0.7953 (6)	0.0192 (4)	0.080 (2)
C12	0.768 (1)	0.8748 (5)	0.0819 (4)	0.077 (2)
C13	0.778 (1)	0.8385 (5)	0.1731 (4)	0.070 (1)
H1	0.7223	0.2694	0.1649	0.106*
H3	0.2461	0.0408	0.2613	0.077*
H4	0.1296	0.0553	0.4167	0.077*
H6	0.7149	0.3978	0.4636	0.063*
H7	1.0221	0.4891	0.3401	0.063*
H8a	1.3285	0.4952	0.1388	0.080*
H8b	1.3348	0.5689	0.2398	0.080*
H10	1.1459	0.6266	0.0093	0.079*
H11	0.9041	0.8166	−0.0438	0.095*
H12	0.6697	0.9518	0.0630	0.092*
H13	0.6820	0.8931	0.2155	0.084*

Atomic displacement parameters (Ų)

	U^11	U^22	U^33	U^12	U^13	U^23
Br1	0.0971 (5)	0.0796 (4)	0.0632 (3)	0.0097 (3)	0.0178 (3)	0.0149 (2)
O1	0.081 (3)	0.067 (2)	0.063 (2)	0.003 (2)	0.007 (2)	−0.010 (2)
N1	0.052 (2)	0.051 (2)	0.065 (2)	0.011 (2)	0.007 (2)	0.011 (2)
N2	0.068 (3)	0.059 (2)	0.059 (2)	0.010 (2)	0.007 (2)	0.006 (2)
C1	0.046 (3)	0.043 (2)	0.057 (2)	0.013 (2)	−0.005 (2)	0.003 (2)
C2	0.053 (3)	0.048 (2)	0.057 (3)	0.015 (2)	0.003 (2)	0.001 (2)
C3	0.062 (3)	0.049 (3)	0.079 (3)	0.003 (2)	0.006 (3)	−0.010 (2)
C4	0.065 (3)	0.047 (3)	0.083 (3)	0.005 (2)	0.016 (3)	0.009 (2)
C5	0.061 (3)	0.056 (3)	0.057 (2)	0.016 (2)	0.007 (2)	0.011 (2)
C6	0.057 (3)	0.049 (2)	0.053 (2)	0.006 (2)	−0.001 (2)	0.001 (2)
C7	0.048 (3)	0.045 (2)	0.063 (3)	0.010 (2)	−0.009 (2)	0.004 (2)
C8	0.054 (3)	0.065 (3)	0.083 (3)	0.007 (2)	0.013 (2)	0.015 (3)
C9	0.042 (2)	0.052 (2)	0.059 (3)	−0.006 (2)	0.005 (2)	0.009 (2)
C10	0.072 (3)	0.060 (3)	0.065 (3)	−0.008 (3)	0.014 (2)	0.002 (2)
C11	0.100 (4)	0.076 (4)	0.061 (3)	−0.004 (3)	−0.002 (3)	0.019 (3)
C12	0.077 (4)	0.056 (3)	0.098 (4)	0.003 (3)	−0.006 (3)	0.025 (3)
C13	0.070 (3)	0.056 (3)	0.084 (3)	0.007 (3)	0.010 (3)	0.002 (3)

Geometric parameters (Å, º)

Br1—C5	1.901 (4)	C10—C11	1.377 (7)
O1—C2	1.343 (5)	C11—C12	1.361 (8)
N1—C7	1.269 (5)	C12—C13	1.361 (7)
N1—C8	1.458 (6)	O1—H1	0.82
N2—C9	1.330 (5)	C3—H3	0.93
N2—C13	1.319 (6)	C4—H4	0.93
C1—C2	1.396 (6)	C6—H6	0.93
C1—C6	1.385 (6)	C7—H7	0.93
C1—C7	1.461 (6)	C8—H8a	0.97
C2—C3	1.395 (6)	C8—H8b	0.97
C3—C4	1.379 (6)	C10—H10	0.93
C4—C5	1.384 (6)	C11—H11	0.93
C5—C6	1.370 (6)	C12—H12	0.93
C8—C9	1.513 (6)	C13—H13	0.93
C9—C10	1.371 (6)
C7—N1—C8	118.3 (4)	C2—O1—H1	109.5
C9—N2—C13	116.9 (4)	C4—C3—H3	119.7
C6—C1—C2	119.1 (4)	C2—C3—H3	119.7
C6—C1—C7	120.1 (4)	C3—C4—H4	120.4
C2—C1—C7	120.8 (4)	C5—C4—H4	120.4
O1—C2—C1	121.8 (4)	C5—C6—H6	119.6
O1—C2—C3	118.5 (4)	C1—C6—H6	119.6
C1—C2—C3	119.6 (4)	N1—C7—H7	118.9
C2—C3—C4	120.5 (4)	C1—C7—H7	118.9
C3—C4—C5	119.2 (4)	N1—C8—H8a	109.7
C4—C5—C6	120.8 (4)	C9—C8—H8a	109.7
C4—C5—Br1	118.8 (3)	N1—C8—H8b	109.7
C6—C5—Br1	120.4 (3)	C9—C8—H8b	109.7
C5—C6—C1	120.7 (4)	H8a—C8—H8b	108.2
N1—C7—C1	122.2 (4)	C9—C10—H10	120.5
N1—C8—C9	109.9 (4)	C11—C10—H10	120.5
N2—C9—C8	115.0 (4)	C12—C11—H11	120.6
N2—C9—C10	122.5 (4)	C10—C11—H11	120.6
C10—C9—C8	122.5 (4)	C11—C12—H12	121.0
C9—C10—C11	119.0 (5)	C13—C12—H12	121.0
C12—C11—C10	118.7 (5)	N2—C13—H13	117.6
C11—C12—C13	118.1 (5)	C12—C13—H13	117.6
N2—C13—C12	124.7 (5)
C6—C1—C2—O1	178.8 (4)	C6—C1—C7—N1	−176.4 (4)
C7—C1—C2—O1	−2.4 (6)	C2—C1—C7—N1	4.8 (6)
C6—C1—C2—C3	−1.0 (6)	C7—N1—C8—C9	−98.3 (5)
C7—C1—C2—C3	177.9 (4)	C13—N2—C9—C10	−1.2 (6)
O1—C2—C3—C4	−178.6 (4)	C13—N2—C9—C8	179.4 (4)
C1—C2—C3—C4	1.2 (6)	N1—C8—C9—N2	69.4 (5)
C2—C3—C4—C5	−0.4 (7)	N1—C8—C9—C10	−110.0 (5)
C3—C4—C5—C6	−0.5 (7)	N2—C9—C10—C11	1.1 (7)
C3—C4—C5—Br1	177.8 (3)	C8—C9—C10—C11	−179.6 (4)
C4—C5—C6—C1	0.7 (6)	C9—C10—C11—C12	−0.3 (8)
Br1—C5—C6—C1	−177.5 (3)	C10—C11—C12—C13	−0.3 (8)
C2—C1—C6—C5	0.0 (6)	C9—N2—C13—C12	0.5 (7)
C7—C1—C6—C5	−178.8 (4)	C11—C12—C13—N2	0.2 (8)
C8—N1—C7—C1	178.4 (3)

Hydrogen-bond geometry (Å, º)

D—H···A	D—H	H···A	D···A	D—H···A
O1—H1···N1	0.82	1.87	2.595 (5)	147