Literature DB >> 21200969

(E)-4-Bromo-2-[(4-ethyl-phen-yl)imino-meth-yl]phenol.

Sehriman Atalay, Talip Kaya Erdem, Ferda Erşahin, Nihat Tınkılıç.

Abstract

In the title compound, C(15)H(14)BrNO, the dihedral angle between the two benzene rings is 43.99 (2)°. The mol-ecular conformation is influenced by an intra-molecular O-H⋯N hydrogen bond.

Entities: Chemical Disease Species

Year: 2007 PMID： 21200969 PMCID： PMC2915047 DOI： 10.1107/S1600536807058618

Source DB: PubMed Journal: Acta Crystallogr Sect E Struct Rep Online ISSN： 1600-5368

Related literature

For related literature, see: Akkaya et al. (2007 ▶); Atalay et al. (2005 ▶, 2006 ▶); Calligaris & Randaccio (1987 ▶).

Experimental

Crystal data

C15H14BrNO M = 304.18 Orthorhombic, a = 6.2280 (6) Å b = 7.0292 (7) Å c = 30.237 (4) Å V = 1323.7 (3) Å3 Z = 4 Mo Kα radiation μ = 3.09 mm−1 T = 293 (2) K 0.48 × 0.31 × 0.05 mm

Data collection

Stoe IPDS 2 diffractometer Absorption correction: integration (X-RED32; Stoe & Cie, 2002 ▶) T min = 0.521, T max = 0.809 7324 measured reflections 1318 independent reflections 819 reflections with I > 2σ(I) R int = 0.102

Refinement

R[F 2 > 2σ(F 2)] = 0.041 wR(F 2) = 0.109 S = 0.92 1318 reflections 165 parameters 1 restraint H-atom parameters constrained Δρmax = 0.41 e Å−3 Δρmin = −0.41 e Å−3 Absolute structure: Flack (1983 ▶), with 1231 Friedel pairs Flack parameter: 0.10 (3) 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: ORTEPIII (Burnett & Johnson, 1996 ▶); software used to prepare material for publication: WinGX (Farrugia, 1999 ▶) and PARST (Nardelli, 1995 ▶). Crystal structure: contains datablocks global, I. DOI: 10.1107/S1600536807058618/wn2219sup1.cif Structure factors: contains datablocks I. DOI: 10.1107/S1600536807058618/wn2219Isup2.hkl Additional supplementary materials: crystallographic information; 3D view; checkCIF report

C₁₅H₁₄BrNO	D_x = 1.526 Mg m⁻³
M_r = 304.18	Mo Kα radiation λ = 0.71073 Å
Orthorhombic, Pna2₁	Cell parameters from 9683 reflections
a = 6.2280 (6) Å	θ = 1.4–26.1º
b = 7.0292 (7) Å	µ = 3.09 mm⁻¹
c = 30.237 (4) Å	T = 293 (2) K
V = 1323.7 (3) Å³	Plate, yellow
Z = 4	0.48 × 0.31 × 0.05 mm
F₀₀₀ = 616

STOE IPDS 2 diffractometer	1318 independent reflections
Radiation source: fine-focus sealed tube	819 reflections with I > 2σ(I)
Monochromator: graphite	R_int = 0.102
Detector resolution: 6.67 pixels mm^-1	θ_max = 26.0º
T = 293(2) K	θ_min = 1.4º
w scans	h = −7→7
Absorption correction: integration(X-RED32; Stoe & Cie, 2002)	k = −8→8
T_min = 0.521, T_max = 0.809	l = −36→36
7324 measured reflections

Refinement on F²	Hydrogen site location: inferred from neighbouring sites
Least-squares matrix: full	H-atom parameters constrained
R[F² > 2σ(F²)] = 0.041	w = 1/[σ²(F_o²) + (0.0574P)²] where P = (F_o² + 2F_c²)/3
wR(F²) = 0.109	(Δ/σ)_max < 0.001
S = 0.92	Δρ_max = 0.41 e Å⁻³
1318 reflections	Δρ_min = −0.41 e Å⁻³
165 parameters	Extinction correction: SHELXL, Fc^*=kFc[1+0.001xFc²λ³/sin(2θ)]^-1/4
1 restraint	Extinction coefficient: 0.0011 (7)
Primary atom site location: structure-invariant direct methods	Absolute structure: Flack (1983), 1231 Friedel pairs
Secondary atom site location: difference Fourier map	Flack parameter: 0.10 (3)

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.

	x	y	z	U_iso*/U_eq
C7	0.6103 (14)	0.4481 (11)	0.6165 (3)	0.0602 (19)
H7	0.7542	0.4132	0.6152	0.072*
C5	0.6251 (12)	0.4361 (11)	0.6979 (3)	0.0562 (18)
H5	0.7652	0.3907	0.6964	0.067*
C3	0.3255 (13)	0.5382 (12)	0.7420 (3)	0.063 (2)
H3	0.2663	0.5628	0.7697	0.076*
C12	0.9101 (13)	0.5783 (11)	0.4937 (3)	0.063 (2)
H12	1.0455	0.6323	0.4904	0.075*
C1	0.2969 (13)	0.5335 (10)	0.6631 (3)	0.0576 (18)
C4	0.5322 (13)	0.4707 (12)	0.7385 (3)	0.0582 (19)
C11	0.8254 (11)	0.5622 (12)	0.5348 (3)	0.0578 (19)
H11	0.9024	0.6024	0.5594	0.069*
C6	0.5101 (12)	0.4686 (10)	0.6591 (2)	0.0512 (16)
C9	0.5119 (15)	0.4235 (12)	0.5023 (3)	0.061 (2)
H9	0.3741	0.3737	0.5048	0.073*
C8	0.6088 (16)	0.4367 (13)	0.4610 (3)	0.066 (2)
H8	0.5380	0.3889	0.4363	0.079*
C13	0.8010 (18)	0.5166 (17)	0.4562 (4)	0.067 (3)
C14	0.9191 (18)	0.5424 (16)	0.4110 (4)	0.092 (3)
H14A	0.9304	0.6775	0.4049	0.111*
H14B	1.0639	0.4932	0.4140	0.111*
C2	0.2089 (15)	0.5685 (12)	0.7048 (5)	0.057 (3)
H2	0.0688	0.6131	0.7070	0.069*
C10	0.6197 (12)	0.4841 (10)	0.5396 (2)	0.0523 (18)
C15	0.819 (3)	0.451 (3)	0.3735 (8)	0.141 (9)
H15A	0.8126	0.3164	0.3784	0.169*
H15B	0.9021	0.4763	0.3473	0.169*
H15C	0.6765	0.5002	0.3697	0.169*
N1	0.5106 (11)	0.4758 (10)	0.5806 (2)	0.0553 (18)
O1	0.1708 (9)	0.5649 (9)	0.6266 (3)	0.067 (2)
H1	0.2389	0.5395	0.6042	0.100*
Br1	0.70006 (13)	0.43768 (13)	0.78954 (7)	0.0838 (4)

	U¹¹	U²²	U³³	U¹²	U¹³	U²³
C7	0.063 (4)	0.051 (5)	0.067 (5)	−0.009 (4)	0.004 (4)	−0.001 (4)
C5	0.047 (4)	0.051 (5)	0.070 (5)	−0.007 (3)	−0.004 (4)	0.003 (4)
C3	0.054 (5)	0.063 (5)	0.073 (5)	0.001 (4)	0.013 (4)	0.002 (4)
C12	0.056 (4)	0.048 (5)	0.084 (6)	−0.005 (4)	0.003 (4)	0.004 (4)
C1	0.057 (4)	0.049 (4)	0.067 (4)	−0.002 (4)	−0.005 (4)	−0.002 (4)
C4	0.054 (4)	0.045 (5)	0.076 (5)	−0.007 (3)	−0.007 (4)	−0.001 (4)
C11	0.051 (5)	0.054 (5)	0.069 (5)	−0.005 (4)	−0.010 (4)	0.003 (4)
C6	0.044 (4)	0.052 (4)	0.058 (4)	0.001 (3)	0.001 (3)	0.001 (4)
C9	0.050 (5)	0.057 (6)	0.075 (5)	0.000 (4)	−0.004 (4)	−0.008 (4)
C8	0.071 (5)	0.061 (6)	0.066 (5)	−0.007 (5)	−0.008 (4)	−0.007 (4)
C13	0.073 (6)	0.061 (6)	0.066 (6)	0.009 (5)	0.005 (5)	−0.001 (5)
C14	0.090 (7)	0.102 (8)	0.086 (6)	−0.015 (6)	0.017 (6)	−0.001 (7)
C2	0.053 (5)	0.049 (5)	0.070 (7)	0.002 (4)	0.001 (5)	0.001 (5)
C10	0.050 (4)	0.044 (5)	0.063 (4)	0.008 (3)	−0.002 (4)	−0.004 (4)
C15	0.112 (13)	0.22 (2)	0.094 (15)	−0.025 (11)	0.020 (10)	−0.015 (12)
N1	0.056 (4)	0.054 (5)	0.056 (4)	0.004 (4)	−0.003 (3)	−0.003 (4)
O1	0.040 (3)	0.089 (5)	0.073 (4)	0.009 (3)	−0.005 (3)	−0.002 (4)
Br1	0.0808 (5)	0.1063 (7)	0.0642 (4)	0.0050 (5)	−0.0098 (8)	−0.0008 (10)

C7—N1	1.264 (10)	C11—H11	0.9300
C7—C6	1.440 (11)	C9—C10	1.378 (11)
C7—H7	0.9300	C9—C8	1.391 (12)
C5—C4	1.379 (12)	C9—H9	0.9300
C5—C6	1.394 (11)	C8—C13	1.330 (14)
C5—H5	0.9300	C8—H8	0.9300
C3—C2	1.357 (18)	C13—C14	1.562 (15)
C3—C4	1.376 (12)	C14—C15	1.45 (2)
C3—H3	0.9300	C14—H14A	0.9700
C12—C11	1.356 (11)	C14—H14B	0.9700
C12—C13	1.390 (14)	C2—H2	0.9300
C12—H12	0.9300	C10—N1	1.417 (10)
C1—O1	1.371 (12)	C15—H15A	0.9600
C1—C2	1.397 (17)	C15—H15B	0.9600
C1—C6	1.409 (10)	C15—H15C	0.9600
C4—Br1	1.878 (9)	O1—H1	0.8200
C11—C10	1.401 (10)

N1—C7—C6	122.6 (8)	C13—C8—C9	121.1 (8)
N1—C7—H7	118.7	C13—C8—H8	119.4
C6—C7—H7	118.7	C9—C8—H8	119.4
C4—C5—C6	120.4 (7)	C8—C13—C12	118.8 (9)
C4—C5—H5	119.8	C8—C13—C14	124.6 (10)
C6—C5—H5	119.8	C12—C13—C14	116.5 (9)
C2—C3—C4	119.4 (9)	C15—C14—C13	115.7 (11)
C2—C3—H3	120.3	C15—C14—H14A	108.4
C4—C3—H3	120.3	C13—C14—H14A	108.4
C11—C12—C13	122.1 (8)	C15—C14—H14B	108.4
C11—C12—H12	119.0	C13—C14—H14B	108.4
C13—C12—H12	119.0	H14A—C14—H14B	107.4
O1—C1—C2	118.2 (8)	C3—C2—C1	120.8 (8)
O1—C1—C6	121.6 (7)	C3—C2—H2	119.6
C2—C1—C6	120.2 (8)	C1—C2—H2	119.6
C3—C4—C5	121.5 (8)	C9—C10—C11	118.9 (7)
C3—C4—Br1	120.0 (7)	C9—C10—N1	118.0 (7)
C5—C4—Br1	118.4 (6)	C11—C10—N1	123.0 (7)
C12—C11—C10	118.8 (7)	C14—C15—H15A	109.5
C12—C11—H11	120.6	C14—C15—H15B	109.5
C10—C11—H11	120.6	H15A—C15—H15B	109.5
C5—C6—C1	117.8 (7)	C14—C15—H15C	109.5
C5—C6—C7	121.0 (7)	H15A—C15—H15C	109.5
C1—C6—C7	121.1 (7)	H15B—C15—H15C	109.5
C10—C9—C8	120.1 (8)	C7—N1—C10	121.5 (7)
C10—C9—H9	119.9	C1—O1—H1	109.5
C8—C9—H9	119.9

C2—C3—C4—C5	1.1 (12)	C9—C8—C13—C14	−178.3 (9)
C2—C3—C4—Br1	177.4 (6)	C11—C12—C13—C8	−1.0 (15)
C6—C5—C4—C3	−0.1 (12)	C11—C12—C13—C14	−179.5 (9)
C6—C5—C4—Br1	−176.5 (6)	C8—C13—C14—C15	−7.7 (18)
C13—C12—C11—C10	−1.2 (13)	C12—C13—C14—C15	170.7 (12)
C4—C5—C6—C1	−1.3 (10)	C4—C3—C2—C1	−0.5 (13)
C4—C5—C6—C7	174.8 (8)	O1—C1—C2—C3	179.3 (8)
O1—C1—C6—C5	−178.5 (7)	C6—C1—C2—C3	−0.9 (13)
C2—C1—C6—C5	1.8 (11)	C8—C9—C10—C11	1.3 (12)
O1—C1—C6—C7	5.4 (11)	C8—C9—C10—N1	177.2 (8)
C2—C1—C6—C7	−174.3 (8)	C12—C11—C10—C9	1.0 (11)
N1—C7—C6—C5	179.7 (8)	C12—C11—C10—N1	−174.7 (7)
N1—C7—C6—C1	−4.3 (12)	C6—C7—N1—C10	170.0 (7)
C10—C9—C8—C13	−3.6 (14)	C9—C10—N1—C7	149.2 (8)
C9—C8—C13—C12	3.4 (15)	C11—C10—N1—C7	−35.1 (12)

D—H···A	D—H	H···A	D···A	D—H···A
O1—H1···N1	0.82	1.89	2.609 (10)	146

Table 1

Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
O1—H1⋯N1	0.82	1.89	2.609 (10)	146

1 in total

1. 2,4-Di-bromo-6-{[(5-chloro-2-methyl-phen-yl)imino]-meth-yl}phenol.

Authors: Yunfa Zheng
Journal: Acta Crystallogr Sect E Struct Rep Online Date: 2013-06-29

1 in total