N'-[(E)-(5-Bromo-2-hydroxy-phen-yl)(phen-yl)methyl-idene]-4-chloro-benzo-hydrazide.

The Schiff base, C(20)H(14)BrClN(2)O(2), displays a trans conformation with respect to the C=N double bond. The aromatic rings at either end of the -C(=O)-NH-N=C- fragment are nearly parallel [dihedral angle = 3.4 (5)°]. The hydr-oxy group forms an intra-molecular hydrogen bond to the imino N atom.

Related literature

The chemistry of aroylhydrazones continues to attract much attention due to their ability to coordinate to n class="Chemical">metal ions (Singh et al., 1982 ▶; Salem, 1998 ▶) and their biological activity (Singh et al., 1982 ▶; Carcelli et al., 1995 ▶).

Experimental

Crystal data

C20H14BrClN2O2

M = 429.69

Triclinic,

a = 7.3664 (8) Å

b = 10.6894 (11) Å

c = 12.3029 (14) Å

α = 71.976 (2)°

β = 82.228 (2)°

γ = 85.466 (2)°

V = 912.05 (17) Å3

Z = 2

Mo Kα radiation

μ = 2.42 mm−1

T = 273 K

0.20 × 0.16 × 0.13 mm

Data collection

Bruker SMART area-detector diffractometer

Absorption correction: multi-scan (SADABS; Sheldrick, 1996 ▶) T min = 0.644, T max = 0.744

4841 measured reflections

3189 independent reflections

2467 reflections with I > 2σ(I)

R int = 0.015

Refinement

R[F 2 > 2σ(F 2)] = 0.034

wR(F 2) = 0.085

S = 1.04

3189 reflections

237 parameters

H-atom parameters constrained

Δρmax = 0.32 e Å−3

Δρmin = −0.44 e Å−3

Data collection: SMART (Bruker, 1996 ▶); cell refinement: SAINT (Bruker, 1996 ▶); data reduction: SAIn class="Chemical">NT; 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/S1600536809027949/ng2613sup1.cif

Structure factors: contains datablocks I. DOI: 10.1107/S1600536809027949/ng2613Isup2.hkl

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

C20H14BrClN2O2	Z = 2
Mr = 429.69	F(000) = 432
Triclinic, P1	Dx = 1.565 Mg m−3
Hall symbol: -P 1	Mo Kα radiation, λ = 0.71073 Å
a = 7.3664 (8) Å	Cell parameters from 1806 reflections
b = 10.6894 (11) Å	θ = 2.8–25.3°
c = 12.3029 (14) Å	µ = 2.42 mm−1
α = 71.976 (2)°	T = 273 K
β = 82.228 (2)°	Block, yellow
γ = 85.466 (2)°	0.20 × 0.16 × 0.13 mm
V = 912.05 (17) Å3

Bruker SMART area-detector diffractometer	3189 independent reflections
Radiation source: fine-focus sealed tube	2467 reflections with I > 2σ(I)
graphite	Rint = 0.015
φ and ω scans	θmax = 25.1°, θmin = 1.8°
Absorption correction: multi-scan (SADABS; Sheldrick, 1996)	h = −8→8
Tmin = 0.644, Tmax = 0.744	k = −8→12
4841 measured reflections	l = −14→14

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)] = 0.034	Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.085	H-atom parameters constrained
S = 1.04	w = 1/[σ2(Fo2) + (0.0366P)2 + 0.3768P] where P = (Fo2 + 2Fc2)/3
3189 reflections	(Δ/σ)max = 0.001
237 parameters	Δρmax = 0.32 e Å−3
0 restraints	Δρmin = −0.43 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	0.36717 (5)	1.17236 (4)	1.00467 (3)	0.06975 (17)
Cl1	0.08513 (13)	0.47987 (9)	0.23226 (8)	0.0729 (3)
O1	0.3069 (3)	1.25145 (19)	0.50596 (17)	0.0627 (6)
H1	0.2882	1.1830	0.4931	0.094*
O2	0.2209 (3)	1.0374 (2)	0.33927 (17)	0.0587 (6)
N1	0.2632 (3)	1.0045 (2)	0.55663 (18)	0.0454 (6)
N2	0.2388 (3)	0.9007 (2)	0.51767 (19)	0.0480 (6)
H2	0.2367	0.8215	0.5636	0.058*
C1	0.3457 (4)	1.1936 (3)	0.8483 (2)	0.0465 (7)
C2	0.3209 (4)	1.0858 (3)	0.8134 (2)	0.0432 (6)
H2A	0.3141	1.0027	0.8673	0.052*
C3	0.3060 (3)	1.0998 (2)	0.6988 (2)	0.0389 (6)
C4	0.3189 (4)	1.2264 (3)	0.6188 (2)	0.0455 (7)
C5	0.3465 (4)	1.3328 (3)	0.6566 (3)	0.0540 (8)
H5	0.3564	1.4163	0.6036	0.065*
C6	0.3595 (4)	1.3169 (3)	0.7695 (3)	0.0534 (8)
H6	0.3775	1.3891	0.7932	0.064*
C7	0.2801 (4)	0.9829 (3)	0.6636 (2)	0.0397 (6)
C8	0.2759 (4)	0.8493 (2)	0.7500 (2)	0.0380 (6)
C9	0.4302 (4)	0.7655 (3)	0.7577 (2)	0.0474 (7)
H9	0.5367	0.7920	0.7083	0.057*
C10	0.4261 (5)	0.6424 (3)	0.8389 (3)	0.0544 (8)
H10	0.5296	0.5861	0.8433	0.065*
C11	0.2707 (5)	0.6030 (3)	0.9127 (3)	0.0524 (8)
H11	0.2690	0.5206	0.9677	0.063*
C12	0.1173 (4)	0.6854 (3)	0.9054 (3)	0.0534 (8)
H12	0.0117	0.6586	0.9557	0.064*
C13	0.1186 (4)	0.8074 (3)	0.8242 (2)	0.0485 (7)
H13	0.0134	0.8620	0.8190	0.058*
C14	0.2180 (4)	0.9262 (3)	0.4043 (2)	0.0415 (6)
C15	0.1925 (4)	0.8100 (3)	0.3660 (2)	0.0394 (6)
C16	0.1873 (4)	0.6816 (3)	0.4374 (2)	0.0548 (8)
H16	0.2020	0.6634	0.5147	0.066*
C17	0.1604 (5)	0.5797 (3)	0.3946 (3)	0.0593 (8)
H17	0.1600	0.4931	0.4423	0.071*
C18	0.1345 (4)	0.6076 (3)	0.2821 (2)	0.0480 (7)
C19	0.1422 (4)	0.7332 (3)	0.2085 (3)	0.0555 (8)
H19	0.1275	0.7504	0.1312	0.067*
C20	0.1724 (4)	0.8337 (3)	0.2515 (2)	0.0491 (7)
H20	0.1792	0.9193	0.2021	0.059*

	U11	U22	U33	U12	U13	U23
Br1	0.0901 (3)	0.0740 (3)	0.0629 (2)	0.00901 (19)	−0.02581 (18)	−0.04231 (19)
Cl1	0.0828 (6)	0.0743 (6)	0.0825 (6)	−0.0160 (5)	−0.0070 (5)	−0.0520 (5)
O1	0.1015 (18)	0.0392 (12)	0.0457 (12)	−0.0063 (12)	−0.0087 (11)	−0.0094 (9)
O2	0.0902 (16)	0.0397 (12)	0.0469 (12)	−0.0099 (11)	−0.0193 (11)	−0.0075 (10)
N1	0.0639 (15)	0.0360 (13)	0.0407 (13)	−0.0063 (11)	−0.0108 (11)	−0.0149 (10)
N2	0.0763 (17)	0.0328 (13)	0.0384 (12)	−0.0087 (11)	−0.0132 (11)	−0.0115 (10)
C1	0.0478 (16)	0.0488 (18)	0.0520 (16)	0.0021 (13)	−0.0122 (13)	−0.0270 (14)
C2	0.0476 (16)	0.0391 (15)	0.0463 (16)	−0.0007 (12)	−0.0086 (13)	−0.0167 (13)
C3	0.0420 (15)	0.0330 (14)	0.0442 (15)	−0.0023 (11)	−0.0072 (12)	−0.0144 (12)
C4	0.0516 (17)	0.0392 (16)	0.0470 (17)	−0.0034 (13)	−0.0054 (13)	−0.0149 (13)
C5	0.068 (2)	0.0306 (15)	0.0629 (19)	−0.0036 (14)	−0.0084 (16)	−0.0122 (14)
C6	0.0555 (18)	0.0443 (18)	0.072 (2)	−0.0012 (14)	−0.0137 (15)	−0.0313 (16)
C7	0.0448 (15)	0.0379 (15)	0.0390 (15)	−0.0021 (12)	−0.0059 (12)	−0.0150 (12)
C8	0.0512 (16)	0.0305 (14)	0.0368 (14)	−0.0066 (12)	−0.0078 (12)	−0.0143 (11)
C9	0.0522 (18)	0.0433 (17)	0.0482 (16)	−0.0037 (14)	−0.0039 (13)	−0.0161 (13)
C10	0.064 (2)	0.0395 (17)	0.0618 (19)	0.0082 (15)	−0.0187 (17)	−0.0169 (15)
C11	0.077 (2)	0.0326 (16)	0.0472 (17)	−0.0099 (15)	−0.0152 (16)	−0.0066 (13)
C12	0.063 (2)	0.0460 (18)	0.0503 (17)	−0.0166 (16)	−0.0007 (15)	−0.0128 (14)
C13	0.0518 (18)	0.0431 (17)	0.0523 (17)	−0.0014 (13)	−0.0086 (14)	−0.0158 (14)
C14	0.0458 (16)	0.0412 (17)	0.0382 (15)	−0.0038 (12)	−0.0082 (12)	−0.0109 (13)
C15	0.0433 (15)	0.0388 (15)	0.0380 (14)	−0.0041 (12)	−0.0084 (12)	−0.0122 (12)
C16	0.083 (2)	0.0445 (17)	0.0403 (16)	−0.0140 (15)	−0.0156 (15)	−0.0112 (13)
C17	0.084 (2)	0.0423 (17)	0.0538 (19)	−0.0151 (16)	−0.0114 (17)	−0.0132 (14)
C18	0.0465 (16)	0.0549 (19)	0.0530 (17)	−0.0078 (14)	−0.0055 (13)	−0.0300 (15)
C19	0.069 (2)	0.064 (2)	0.0417 (16)	−0.0029 (16)	−0.0131 (14)	−0.0250 (15)
C20	0.0633 (19)	0.0458 (17)	0.0373 (15)	−0.0027 (14)	−0.0085 (13)	−0.0102 (13)

Br1—C1	1.893 (3)	C8—C13	1.386 (4)
Cl1—C18	1.740 (3)	C9—C10	1.384 (4)
O1—C4	1.344 (3)	C9—H9	0.9300
O1—H1	0.8200	C10—C11	1.368 (4)
O2—C14	1.210 (3)	C10—H10	0.9300
N1—C7	1.285 (3)	C11—C12	1.372 (4)
N1—N2	1.370 (3)	C11—H11	0.9300
N2—C14	1.364 (3)	C12—C13	1.376 (4)
N2—H2	0.8600	C12—H12	0.9300
C1—C6	1.375 (4)	C13—H13	0.9300
C1—C2	1.380 (4)	C14—C15	1.491 (4)
C2—C3	1.390 (4)	C15—C20	1.378 (4)
C2—H2A	0.9300	C15—C16	1.382 (4)
C3—C4	1.407 (4)	C16—C17	1.385 (4)
C3—C7	1.476 (3)	C16—H16	0.9300
C4—C5	1.392 (4)	C17—C18	1.359 (4)
C5—C6	1.363 (4)	C17—H17	0.9300
C5—H5	0.9300	C18—C19	1.368 (4)
C6—H6	0.9300	C19—C20	1.381 (4)
C7—C8	1.493 (4)	C19—H19	0.9300
C8—C9	1.385 (4)	C20—H20	0.9300
C4—O1—H1	109.5	C11—C10—H10	119.8
C7—N1—N2	119.3 (2)	C9—C10—H10	119.8
C14—N2—N1	118.3 (2)	C10—C11—C12	119.8 (3)
C14—N2—H2	120.8	C10—C11—H11	120.1
N1—N2—H2	120.8	C12—C11—H11	120.1
C6—C1—C2	120.4 (3)	C11—C12—C13	120.4 (3)
C6—C1—Br1	119.3 (2)	C11—C12—H12	119.8
C2—C1—Br1	120.2 (2)	C13—C12—H12	119.8
C1—C2—C3	120.9 (3)	C12—C13—C8	120.4 (3)
C1—C2—H2A	119.6	C12—C13—H13	119.8
C3—C2—H2A	119.6	C8—C13—H13	119.8
C2—C3—C4	118.4 (2)	O2—C14—N2	121.2 (2)
C2—C3—C7	119.9 (2)	O2—C14—C15	122.5 (2)
C4—C3—C7	121.8 (2)	N2—C14—C15	116.3 (2)
O1—C4—C5	117.2 (2)	C20—C15—C16	118.5 (3)
O1—C4—C3	123.5 (2)	C20—C15—C14	117.1 (2)
C5—C4—C3	119.3 (3)	C16—C15—C14	124.4 (2)
C6—C5—C4	121.3 (3)	C15—C16—C17	120.5 (3)
C6—C5—H5	119.3	C15—C16—H16	119.8
C4—C5—H5	119.3	C17—C16—H16	119.8
C5—C6—C1	119.7 (3)	C18—C17—C16	119.3 (3)
C5—C6—H6	120.2	C18—C17—H17	120.4
C1—C6—H6	120.2	C16—C17—H17	120.4
N1—C7—C3	116.0 (2)	C17—C18—C19	121.8 (3)
N1—C7—C8	123.7 (2)	C17—C18—Cl1	118.7 (2)
C3—C7—C8	120.2 (2)	C19—C18—Cl1	119.5 (2)
C9—C8—C13	118.9 (2)	C18—C19—C20	118.4 (3)
C9—C8—C7	120.4 (2)	C18—C19—H19	120.8
C13—C8—C7	120.7 (2)	C20—C19—H19	120.8
C10—C9—C8	120.1 (3)	C15—C20—C19	121.5 (3)
C10—C9—H9	120.0	C15—C20—H20	119.2
C8—C9—H9	120.0	C19—C20—H20	119.2
C11—C10—C9	120.4 (3)
C7—N1—N2—C14	178.9 (2)	C13—C8—C9—C10	−0.3 (4)
C6—C1—C2—C3	−1.2 (4)	C7—C8—C9—C10	179.2 (3)
Br1—C1—C2—C3	−179.6 (2)	C8—C9—C10—C11	−0.6 (4)
C1—C2—C3—C4	0.7 (4)	C9—C10—C11—C12	0.7 (4)
C1—C2—C3—C7	179.8 (2)	C10—C11—C12—C13	0.1 (4)
C2—C3—C4—O1	179.8 (3)	C11—C12—C13—C8	−1.0 (4)
C7—C3—C4—O1	0.8 (4)	C9—C8—C13—C12	1.1 (4)
C2—C3—C4—C5	0.2 (4)	C7—C8—C13—C12	−178.4 (3)
C7—C3—C4—C5	−178.9 (3)	N1—N2—C14—O2	0.0 (4)
O1—C4—C5—C6	179.7 (3)	N1—N2—C14—C15	179.8 (2)
C3—C4—C5—C6	−0.7 (4)	O2—C14—C15—C20	0.2 (4)
C4—C5—C6—C1	0.2 (5)	N2—C14—C15—C20	−179.6 (2)
C2—C1—C6—C5	0.7 (4)	O2—C14—C15—C16	−179.6 (3)
Br1—C1—C6—C5	179.2 (2)	N2—C14—C15—C16	0.5 (4)
N2—N1—C7—C3	180.0 (2)	C20—C15—C16—C17	−0.7 (5)
N2—N1—C7—C8	0.4 (4)	C14—C15—C16—C17	179.1 (3)
C2—C3—C7—N1	178.4 (2)	C15—C16—C17—C18	−1.6 (5)
C4—C3—C7—N1	−2.5 (4)	C16—C17—C18—C19	2.9 (5)
C2—C3—C7—C8	−2.0 (4)	C16—C17—C18—Cl1	−175.6 (2)
C4—C3—C7—C8	177.1 (2)	C17—C18—C19—C20	−1.7 (5)
N1—C7—C8—C9	79.9 (3)	Cl1—C18—C19—C20	176.7 (2)
C3—C7—C8—C9	−99.7 (3)	C16—C15—C20—C19	1.9 (4)
N1—C7—C8—C13	−100.6 (3)	C14—C15—C20—C19	−177.9 (3)
C3—C7—C8—C13	79.9 (3)	C18—C19—C20—C15	−0.7 (5)

D—H···A	D—H	H···A	D···A	D—H···A
O1—H1···N1	0.82	1.84	2.554 (3)	145

Table 1

Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
O1—H1⋯N1	0.82	1.84	2.554 (3)	145