N'-[(E)-(5-Bromo-2-hydroxy-phen-yl)(phen-yl)methyl-ene]benzohydrazide.

In the title compound, C(20)H(15)BrN(2)O(2), the C=N double bond displays a trans configuration. The crystal structure features an intra-molecular O-H⋯N hydrogen bond.

Related literature

For literature on similar Schiff bases, see: Carcelli et al. (1995 ▶); Salem (1998 ▶); Singh et al. (1982 ▶).

Experimental

Crystal data

C20H15BrN2O2

M = 395.25

Monoclinic,

a = 17.505 (5) Å

b = 13.761 (4) Å

c = 7.219 (2) Å

β = 94.546 (6)°

V = 1733.4 (9) Å3

Z = 4

Mo Kα radiation

μ = 2.39 mm−1

T = 298 (2) K

0.12 × 0.10 × 0.06 mm

Data collection

Bruker SMART diffractometer

Absorption correction: multi-scan (SADABS; Sheldrick, 1996 ▶) T min = 0.763, T max = 0.870

9019 measured reflections

3078 independent reflections

1722 reflections with I > 2σ(I)

R int = 0.059

Refinement

R[F 2 > 2σ(F 2)] = 0.044

wR(F 2) = 0.101

S = 1.00

3078 reflections

197 parameters

H-atom parameters constrained

Δρmax = 0.31 e Å−3

Δρmin = −0.28 e Å−3

Data collection: SMART (Bruker, 1996 ▶); cell refinement: SAINT (Bruker, 1996 ▶); data reduction: SAINT; program(s) used to solve structure: SHELXS97 (Sheldrick, 2008 ▶); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008 ▶); molecular graphics: SHELXTL (Sheldrick, 2008 ▶); software used to prepare material for publication: SHELXTL.

Crystal structure: contains datablocks I, global. DOI: 10.1107/S1600536809002918/ng2531sup1.cif

Structure factors: contains datablocks I. DOI: 10.1107/S1600536809002918/ng2531Isup2.hkl

Additional supplementary materials: crystallographic information; 3D view; checkCIF report

C20H15BrN2O2	F(000) = 800
Mr = 395.25	Dx = 1.515 Mg m−3
Monoclinic, P21/c	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: -P 2ybc	Cell parameters from 1125 reflections
a = 17.505 (5) Å	θ = 2.3–17.9°
b = 13.761 (4) Å	µ = 2.39 mm−1
c = 7.219 (2) Å	T = 298 K
β = 94.546 (6)°	Block, yellow
V = 1733.4 (9) Å3	0.12 × 0.10 × 0.06 mm
Z = 4

Bruker SMART diffractometer	3078 independent reflections
Radiation source: fine-focus sealed tube	1722 reflections with I > 2σ(I)
graphite	Rint = 0.059
φ and ω scans	θmax = 25.1°, θmin = 1.9°
Absorption correction: multi-scan (SADABS; Sheldrick, 1996)	h = −19→20
Tmin = 0.763, Tmax = 0.870	k = −13→16
9019 measured reflections	l = −8→7

Refinement on F2	Primary atom site location: structure-invariant direct methods
Least-squares matrix: full	Secondary atom site location: difference Fourier map
R[F2 > 2σ(F2)] = 0.044	Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.101	H-atom parameters constrained
S = 1.00	w = 1/[σ2(Fo2) + (0.038P)2 + 0.0901P] where P = (Fo2 + 2Fc2)/3
3078 reflections	(Δ/σ)max < 0.001
197 parameters	Δρmax = 0.31 e Å−3
0 restraints	Δρmin = −0.28 e Å−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	Uiso*/Ueq
Br1	0.42053 (3)	0.11003 (4)	0.37885 (7)	0.0690 (2)
O1	0.69581 (16)	0.35312 (19)	0.2430 (4)	0.0600 (8)
H1	0.7343	0.3203	0.2327	0.090*
O2	0.89683 (17)	0.2957 (2)	0.1320 (5)	0.0729 (9)
N1	0.7724 (2)	0.1958 (2)	0.2165 (4)	0.0524 (9)
N2	0.84133 (19)	0.1530 (2)	0.1895 (5)	0.0573 (9)
H2	0.8456	0.0908	0.1935	0.069*
C1	0.6363 (2)	0.2941 (3)	0.2723 (5)	0.0469 (10)
C2	0.6425 (2)	0.1921 (3)	0.2769 (5)	0.0428 (10)
C3	0.5771 (2)	0.1384 (3)	0.3098 (5)	0.0463 (10)
H3	0.5799	0.0710	0.3158	0.056*
C4	0.5090 (2)	0.1842 (3)	0.3332 (5)	0.0495 (11)
C5	0.5032 (3)	0.2842 (3)	0.3297 (5)	0.0548 (11)
H5	0.4571	0.3148	0.3481	0.066*
C6	0.5670 (3)	0.3371 (3)	0.2983 (5)	0.0566 (12)
H6	0.5635	0.4045	0.2944	0.068*
C7	0.7149 (2)	0.1422 (3)	0.2494 (5)	0.0441 (10)
C8	0.7210 (2)	0.0332 (3)	0.2583 (6)	0.0419 (10)
C9	0.7594 (2)	−0.0103 (3)	0.4116 (6)	0.0553 (12)
H9	0.7792	0.0275	0.5109	0.066*
C10	0.7682 (3)	−0.1098 (3)	0.4170 (6)	0.0641 (12)
H10	0.7951	−0.1388	0.5187	0.077*
C11	0.7376 (3)	−0.1661 (3)	0.2735 (7)	0.0608 (12)
H11	0.7434	−0.2332	0.2783	0.073*
C12	0.6986 (2)	−0.1235 (3)	0.1229 (7)	0.0579 (12)
H12	0.6768	−0.1620	0.0268	0.069*
C13	0.6915 (2)	−0.0232 (3)	0.1130 (6)	0.0513 (11)
H13	0.6667	0.0057	0.0083	0.062*
C14	0.9034 (2)	0.2088 (3)	0.1563 (6)	0.0527 (11)
C15	0.9765 (2)	0.1545 (3)	0.1514 (5)	0.0471 (10)
C16	0.9902 (3)	0.0672 (3)	0.2383 (6)	0.0570 (12)
H16	0.9524	0.0391	0.3043	0.068*
C17	1.0594 (3)	0.0201 (3)	0.2294 (6)	0.0652 (13)
H17	1.0681	−0.0391	0.2895	0.078*
C18	1.1156 (3)	0.0609 (4)	0.1314 (7)	0.0701 (14)
H18	1.1622	0.0293	0.1232	0.084*
C19	1.1021 (3)	0.1485 (4)	0.0465 (7)	0.0726 (14)
H19	1.1401	0.1766	−0.0188	0.087*
C20	1.0337 (3)	0.1958 (3)	0.0553 (6)	0.0584 (12)
H20	1.0256	0.2556	−0.0031	0.070*

	U11	U22	U33	U12	U13	U23
Br1	0.0514 (3)	0.0762 (4)	0.0801 (4)	0.0014 (3)	0.0099 (2)	0.0023 (3)
O1	0.065 (2)	0.0412 (17)	0.074 (2)	−0.0003 (15)	0.0062 (18)	−0.0016 (16)
O2	0.063 (2)	0.0396 (18)	0.115 (3)	−0.0032 (16)	0.0033 (18)	0.0054 (19)
N1	0.049 (2)	0.047 (2)	0.062 (2)	−0.0002 (19)	0.0078 (18)	−0.0026 (18)
N2	0.047 (2)	0.042 (2)	0.084 (3)	−0.0039 (18)	0.0108 (19)	−0.0040 (19)
C1	0.057 (3)	0.043 (3)	0.041 (2)	0.001 (2)	0.003 (2)	0.000 (2)
C2	0.050 (3)	0.045 (3)	0.034 (2)	0.007 (2)	0.0050 (19)	0.001 (2)
C3	0.049 (3)	0.049 (3)	0.041 (2)	0.007 (2)	−0.0006 (19)	0.003 (2)
C4	0.047 (3)	0.061 (3)	0.041 (2)	0.005 (2)	0.0044 (19)	0.001 (2)
C5	0.054 (3)	0.056 (3)	0.054 (3)	0.013 (2)	0.002 (2)	−0.005 (2)
C6	0.073 (3)	0.041 (3)	0.055 (3)	0.011 (3)	0.000 (2)	−0.001 (2)
C7	0.044 (3)	0.044 (3)	0.044 (2)	−0.002 (2)	0.0040 (19)	−0.001 (2)
C8	0.037 (2)	0.039 (3)	0.050 (3)	−0.0013 (19)	0.0071 (19)	0.002 (2)
C9	0.062 (3)	0.052 (3)	0.051 (3)	0.003 (2)	0.003 (2)	−0.003 (2)
C10	0.075 (3)	0.056 (3)	0.062 (3)	0.012 (3)	0.008 (2)	0.013 (3)
C11	0.063 (3)	0.040 (3)	0.083 (4)	0.005 (2)	0.024 (3)	0.006 (3)
C12	0.054 (3)	0.051 (3)	0.070 (3)	−0.007 (2)	0.012 (2)	−0.012 (3)
C13	0.051 (3)	0.048 (3)	0.054 (3)	0.005 (2)	0.002 (2)	−0.001 (2)
C14	0.054 (3)	0.044 (3)	0.060 (3)	−0.012 (2)	0.000 (2)	−0.003 (2)
C15	0.046 (3)	0.043 (3)	0.052 (3)	−0.008 (2)	−0.001 (2)	−0.003 (2)
C16	0.058 (3)	0.051 (3)	0.062 (3)	−0.004 (2)	0.005 (2)	−0.001 (3)
C17	0.074 (4)	0.049 (3)	0.070 (3)	0.005 (3)	−0.012 (3)	−0.001 (3)
C18	0.050 (3)	0.084 (4)	0.075 (4)	0.009 (3)	−0.003 (3)	−0.022 (3)
C19	0.051 (3)	0.101 (4)	0.067 (3)	−0.012 (3)	0.011 (2)	0.000 (3)
C20	0.057 (3)	0.060 (3)	0.058 (3)	−0.011 (3)	0.003 (2)	0.010 (2)

Br1—C4	1.905 (4)	C9—C10	1.378 (5)
O1—C1	1.350 (4)	C9—H9	0.9300
O1—H1	0.8200	C10—C11	1.368 (5)
O2—C14	1.213 (4)	C10—H10	0.9300
N1—C7	1.284 (4)	C11—C12	1.369 (5)
N1—N2	1.370 (4)	C11—H11	0.9300
N2—C14	1.367 (5)	C12—C13	1.387 (5)
N2—H2	0.8600	C12—H12	0.9300
C1—C6	1.376 (5)	C13—H13	0.9300
C1—C2	1.409 (5)	C14—C15	1.484 (6)
C2—C3	1.397 (5)	C15—C16	1.369 (5)
C2—C7	1.469 (5)	C15—C20	1.384 (5)
C3—C4	1.370 (5)	C16—C17	1.380 (6)
C3—H3	0.9300	C16—H16	0.9300
C4—C5	1.380 (5)	C17—C18	1.377 (6)
C5—C6	1.368 (5)	C17—H17	0.9300
C5—H5	0.9300	C18—C19	1.364 (7)
C6—H6	0.9300	C18—H18	0.9300
C7—C8	1.506 (5)	C19—C20	1.370 (6)
C8—C13	1.373 (5)	C19—H19	0.9300
C8—C9	1.384 (5)	C20—H20	0.9300
C1—O1—H1	109.5	C11—C10—H10	119.8
C7—N1—N2	119.5 (3)	C9—C10—H10	119.8
C14—N2—N1	120.3 (4)	C10—C11—C12	120.0 (4)
C14—N2—H2	119.9	C10—C11—H11	120.0
N1—N2—H2	119.9	C12—C11—H11	120.0
O1—C1—C6	117.5 (4)	C11—C12—C13	120.2 (4)
O1—C1—C2	123.0 (4)	C11—C12—H12	119.9
C6—C1—C2	119.4 (4)	C13—C12—H12	119.9
C3—C2—C1	117.9 (4)	C8—C13—C12	119.8 (4)
C3—C2—C7	120.2 (4)	C8—C13—H13	120.1
C1—C2—C7	121.8 (4)	C12—C13—H13	120.1
C4—C3—C2	120.7 (4)	O2—C14—N2	120.8 (4)
C4—C3—H3	119.7	O2—C14—C15	124.4 (4)
C2—C3—H3	119.7	N2—C14—C15	114.8 (4)
C3—C4—C5	121.3 (4)	C16—C15—C20	118.8 (4)
C3—C4—Br1	120.2 (3)	C16—C15—C14	123.5 (4)
C5—C4—Br1	118.5 (3)	C20—C15—C14	117.7 (4)
C6—C5—C4	118.3 (4)	C15—C16—C17	121.0 (4)
C6—C5—H5	120.8	C15—C16—H16	119.5
C4—C5—H5	120.8	C17—C16—H16	119.5
C5—C6—C1	122.3 (4)	C18—C17—C16	119.9 (5)
C5—C6—H6	118.8	C18—C17—H17	120.1
C1—C6—H6	118.8	C16—C17—H17	120.1
N1—C7—C2	117.1 (4)	C19—C18—C17	119.1 (5)
N1—C7—C8	121.7 (4)	C19—C18—H18	120.4
C2—C7—C8	121.2 (3)	C17—C18—H18	120.4
C13—C8—C9	119.7 (4)	C18—C19—C20	121.4 (5)
C13—C8—C7	120.6 (4)	C18—C19—H19	119.3
C9—C8—C7	119.6 (4)	C20—C19—H19	119.3
C10—C9—C8	119.9 (4)	C19—C20—C15	119.9 (4)
C10—C9—H9	120.1	C19—C20—H20	120.1
C8—C9—H9	120.1	C15—C20—H20	120.1
C11—C10—C9	120.3 (4)
C7—N1—N2—C14	−179.3 (4)	C2—C7—C8—C9	−106.2 (4)
O1—C1—C2—C3	179.5 (3)	C13—C8—C9—C10	0.5 (6)
C6—C1—C2—C3	−0.6 (5)	C7—C8—C9—C10	−177.1 (4)
O1—C1—C2—C7	−0.1 (6)	C8—C9—C10—C11	−1.6 (6)
C6—C1—C2—C7	179.8 (3)	C9—C10—C11—C12	0.6 (6)
C1—C2—C3—C4	1.2 (5)	C10—C11—C12—C13	1.6 (6)
C7—C2—C3—C4	−179.2 (3)	C9—C8—C13—C12	1.6 (6)
C2—C3—C4—C5	−1.6 (6)	C7—C8—C13—C12	179.1 (4)
C2—C3—C4—Br1	−179.8 (3)	C11—C12—C13—C8	−2.6 (6)
C3—C4—C5—C6	1.3 (6)	N1—N2—C14—O2	−7.3 (6)
Br1—C4—C5—C6	179.5 (3)	N1—N2—C14—C15	173.2 (3)
C4—C5—C6—C1	−0.7 (6)	O2—C14—C15—C16	156.7 (4)
O1—C1—C6—C5	−179.8 (3)	N2—C14—C15—C16	−23.8 (5)
C2—C1—C6—C5	0.3 (6)	O2—C14—C15—C20	−22.5 (6)
N2—N1—C7—C2	−179.9 (3)	N2—C14—C15—C20	157.0 (4)
N2—N1—C7—C8	−0.3 (5)	C20—C15—C16—C17	−0.7 (6)
C3—C2—C7—N1	178.8 (3)	C14—C15—C16—C17	−179.8 (4)
C1—C2—C7—N1	−1.6 (5)	C15—C16—C17—C18	−0.2 (6)
C3—C2—C7—C8	−0.8 (5)	C16—C17—C18—C19	0.9 (7)
C1—C2—C7—C8	178.8 (3)	C17—C18—C19—C20	−0.6 (7)
N1—C7—C8—C13	−103.3 (4)	C18—C19—C20—C15	−0.3 (7)
C2—C7—C8—C13	76.3 (5)	C16—C15—C20—C19	0.9 (6)
N1—C7—C8—C9	74.2 (5)	C14—C15—C20—C19	−179.9 (4)

D—H···A	D—H	H···A	D···A	D—H···A
O1—H1···N1	0.82	1.85	2.562 (4)	145

Table 1

Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
O1—H1⋯N1	0.82	1.85	2.562 (4)	145