N'-(3-Bromo-5-chloro-2-hydroxy-benzyl-idene)-2-chloro-benzohydrazide methanol solvate.

In the title compound, C(14)H(9)BrCl(2)N(2)O(2)·CH(4)O, the dihedral angle between the two benzene rings is 49.2 (2)° and an intra-molecular O-H⋯N hydrogen bond occurs. In the crystal struture, mol-ecules are linked by O-H⋯O and N-H⋯O hydrogen bonds.

Related literature

For related structures, see: Fun et al. (2008 ▶); Ali et al. (2007 ▶); Zhi & Yang (2007 ▶).

Experimental

Crystal data

C14H9BrCl2N2O2·CH4O

M = 420.08

Monoclinic,

a = 11.221 (4) Å

b = 9.642 (3) Å

c = 15.908 (5) Å

β = 97.537 (5)°

V = 1706.3 (10) Å3

Z = 4

Mo Kα radiation

μ = 2.74 mm−1

T = 298 K

0.17 × 0.15 × 0.12 mm

Data collection

Bruker SMART 1000 CCD diffractometer

Absorption correction: multi-scan (SADABS; Bruker, 2001 ▶) T min = 0.653, T max = 0.735

9257 measured reflections

3666 independent reflections

2345 reflections with I > 2σ(I)

R int = 0.035

Refinement

R[F 2 > 2σ(F 2)] = 0.039

wR(F 2) = 0.103

S = 1.02

3666 reflections

214 parameters

1 restraint

H atoms treated by a mixture of independent and constrained refinement

Δρmax = 0.49 e Å−3

Δρmin = −0.46 e Å−3

Data collection: SMART (Bruker, 2007 ▶); cell refinement: SAINT (Bruker, 2007 ▶); data reduction: SAINT; program(s) used to solve structure: SHELXTL (Sheldrick, 2008 ▶); program(s) used to refine structure: SHELXTL; molecular graphics: SHELXTL; software used to prepare material for publication: SHELXTL.

Crystal structure: contains datablocks global, I. DOI: 10.1107/S1600536809009647/hb2928sup1.cif

Structure factors: contains datablocks I. DOI: 10.1107/S1600536809009647/hb2928Isup2.hkl

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

C14H9BrCl2N2O2·CH4O	F(000) = 840
Mr = 420.08	Dx = 1.635 Mg m−3
Monoclinic, P21/n	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: -P 2yn	Cell parameters from 2864 reflections
a = 11.221 (4) Å	θ = 2.3–24.0°
b = 9.642 (3) Å	µ = 2.74 mm−1
c = 15.908 (5) Å	T = 298 K
β = 97.537 (5)°	Block, yellow
V = 1706.3 (10) Å3	0.17 × 0.15 × 0.12 mm
Z = 4

Bruker SMART 1000 CCD diffractometer	3666 independent reflections
Radiation source: fine-focus sealed tube	2345 reflections with I > 2σ(I)
graphite	Rint = 0.035
ω scans	θmax = 27.0°, θmin = 2.1°
Absorption correction: multi-scan (SADABS; Bruker, 2001)	h = −14→14
Tmin = 0.653, Tmax = 0.735	k = −12→7
9257 measured reflections	l = −20→19

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)] = 0.039	Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.103	H atoms treated by a mixture of independent and constrained refinement
S = 1.02	w = 1/[σ2(Fo2) + (0.0477P)2 + 0.4564P] where P = (Fo2 + 2Fc2)/3
3666 reflections	(Δ/σ)max < 0.001
214 parameters	Δρmax = 0.49 e Å−3
1 restraint	Δρmin = −0.45 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	−0.32199 (3)	0.42107 (4)	0.05220 (3)	0.06886 (17)
Cl1	−0.23673 (8)	0.95108 (9)	−0.05322 (6)	0.0633 (3)
Cl2	0.49315 (8)	0.21596 (9)	0.18697 (6)	0.0627 (3)
N1	0.1502 (2)	0.5525 (2)	0.14404 (16)	0.0412 (6)
N2	0.2713 (2)	0.5514 (3)	0.17335 (16)	0.0421 (6)
O1	−0.06054 (19)	0.4397 (2)	0.12117 (14)	0.0502 (6)
H1	0.0113	0.4451	0.1388	0.075*
O2	0.25707 (19)	0.3476 (2)	0.24068 (15)	0.0588 (6)
O3	0.1088 (2)	0.2995 (3)	0.36033 (16)	0.0635 (6)
H3	0.1265	0.3411	0.3188	0.095*
C1	−0.0179 (2)	0.6676 (3)	0.06979 (17)	0.0372 (7)
C2	−0.0965 (3)	0.5573 (3)	0.07949 (18)	0.0379 (7)
C3	−0.2162 (3)	0.5705 (3)	0.04383 (18)	0.0422 (7)
C4	−0.2581 (3)	0.6892 (3)	0.00215 (18)	0.0467 (8)
H4	−0.3384	0.6963	−0.0210	0.056*
C5	−0.1803 (3)	0.7973 (3)	−0.00500 (19)	0.0440 (7)
C6	−0.0613 (3)	0.7871 (3)	0.02778 (18)	0.0432 (7)
H6	−0.0094	0.8606	0.0218	0.052*
C7	0.1096 (3)	0.6595 (3)	0.10313 (18)	0.0416 (7)
H7	0.1609	0.7323	0.0945	0.050*
C8	0.3161 (3)	0.4461 (3)	0.22296 (19)	0.0397 (7)
C9	0.4474 (3)	0.4648 (3)	0.25564 (19)	0.0407 (7)
C10	0.5333 (3)	0.3652 (3)	0.24473 (18)	0.0428 (7)
C11	0.6517 (3)	0.3836 (4)	0.2764 (2)	0.0564 (9)
H11	0.7084	0.3163	0.2683	0.068*
C12	0.6858 (3)	0.5040 (4)	0.3207 (2)	0.0635 (10)
H12	0.7661	0.5173	0.3423	0.076*
C13	0.6033 (3)	0.6032 (4)	0.3332 (2)	0.0596 (10)
H13	0.6271	0.6831	0.3636	0.072*
C14	0.4840 (3)	0.5842 (3)	0.3004 (2)	0.0510 (8)
H14	0.4278	0.6521	0.3085	0.061*
C15	−0.0087 (4)	0.3311 (6)	0.3718 (4)	0.1076 (17)
H15A	−0.0086	0.4056	0.4118	0.161*
H15B	−0.0459	0.2509	0.3928	0.161*
H15C	−0.0527	0.3587	0.3186	0.161*
H2	0.313 (3)	0.628 (3)	0.162 (2)	0.080*

	U11	U22	U33	U12	U13	U23
Br1	0.0512 (2)	0.0795 (3)	0.0725 (3)	−0.0221 (2)	−0.00436 (17)	0.0152 (2)
Cl1	0.0609 (6)	0.0508 (5)	0.0712 (6)	0.0094 (4)	−0.0180 (4)	0.0155 (4)
Cl2	0.0639 (5)	0.0534 (5)	0.0687 (6)	0.0050 (4)	0.0001 (4)	−0.0110 (5)
N1	0.0336 (13)	0.0412 (14)	0.0463 (14)	0.0017 (11)	−0.0044 (11)	−0.0008 (12)
N2	0.0308 (13)	0.0403 (14)	0.0524 (15)	−0.0008 (11)	−0.0044 (11)	0.0080 (13)
O1	0.0432 (12)	0.0457 (13)	0.0583 (14)	−0.0038 (10)	−0.0059 (11)	0.0127 (11)
O2	0.0429 (12)	0.0537 (14)	0.0781 (17)	−0.0067 (12)	0.0015 (11)	0.0232 (13)
O3	0.0563 (14)	0.0545 (15)	0.0815 (18)	0.0038 (12)	0.0158 (12)	−0.0002 (13)
C1	0.0387 (16)	0.0364 (16)	0.0347 (15)	0.0018 (13)	−0.0019 (13)	−0.0008 (13)
C2	0.0409 (16)	0.0401 (16)	0.0315 (15)	0.0009 (14)	0.0002 (12)	0.0011 (13)
C3	0.0393 (16)	0.0503 (19)	0.0365 (16)	−0.0029 (15)	0.0025 (13)	−0.0018 (15)
C4	0.0357 (16)	0.065 (2)	0.0379 (17)	0.0051 (17)	−0.0002 (13)	0.0001 (16)
C5	0.0471 (17)	0.0391 (17)	0.0434 (18)	0.0091 (15)	−0.0032 (14)	0.0033 (15)
C6	0.0443 (17)	0.0383 (17)	0.0448 (17)	−0.0007 (14)	−0.0024 (14)	0.0006 (15)
C7	0.0361 (16)	0.0420 (17)	0.0438 (18)	−0.0011 (14)	−0.0056 (13)	0.0011 (15)
C8	0.0371 (16)	0.0413 (17)	0.0397 (16)	0.0020 (14)	0.0014 (13)	0.0037 (15)
C9	0.0381 (16)	0.0418 (17)	0.0404 (17)	0.0004 (14)	−0.0020 (13)	0.0077 (14)
C10	0.0435 (17)	0.0456 (17)	0.0376 (17)	0.0022 (15)	−0.0012 (14)	0.0030 (14)
C11	0.0411 (18)	0.064 (2)	0.062 (2)	0.0125 (17)	−0.0019 (16)	0.0058 (19)
C12	0.0423 (19)	0.076 (3)	0.067 (2)	−0.002 (2)	−0.0128 (17)	0.004 (2)
C13	0.055 (2)	0.053 (2)	0.065 (2)	0.0002 (18)	−0.0144 (18)	−0.0064 (18)
C14	0.0508 (19)	0.0451 (19)	0.054 (2)	0.0036 (16)	−0.0054 (16)	0.0038 (16)
C15	0.066 (3)	0.105 (4)	0.155 (5)	0.020 (3)	0.027 (3)	0.001 (4)

Br1—C3	1.883 (3)	C4—H4	0.9300
Cl1—C5	1.749 (3)	C5—C6	1.372 (4)
Cl2—C10	1.735 (3)	C6—H6	0.9300
N1—C7	1.272 (4)	C7—H7	0.9300
N1—N2	1.378 (3)	C8—C9	1.508 (4)
N2—C8	1.343 (4)	C9—C14	1.387 (4)
N2—H2	0.91 (3)	C9—C10	1.388 (4)
O1—C2	1.348 (3)	C10—C11	1.369 (4)
O1—H1	0.8200	C11—C12	1.386 (5)
O2—C8	1.212 (3)	C11—H11	0.9300
O3—C15	1.388 (5)	C12—C13	1.364 (5)
O3—H3	0.8200	C12—H12	0.9300
C1—C6	1.387 (4)	C13—C14	1.383 (5)
C1—C2	1.404 (4)	C13—H13	0.9300
C1—C7	1.461 (4)	C14—H14	0.9300
C2—C3	1.393 (4)	C15—H15A	0.9600
C3—C4	1.374 (4)	C15—H15B	0.9600
C4—C5	1.374 (4)	C15—H15C	0.9600
C7—N1—N2	116.8 (2)	O2—C8—N2	123.8 (3)
C8—N2—N1	118.7 (2)	O2—C8—C9	123.5 (3)
C8—N2—H2	125 (2)	N2—C8—C9	112.7 (3)
N1—N2—H2	116 (2)	C14—C9—C10	118.3 (3)
C2—O1—H1	109.5	C14—C9—C8	119.1 (3)
C15—O3—H3	109.5	C10—C9—C8	122.5 (3)
C6—C1—C2	119.7 (3)	C11—C10—C9	121.4 (3)
C6—C1—C7	119.0 (3)	C11—C10—Cl2	118.3 (3)
C2—C1—C7	121.3 (3)	C9—C10—Cl2	120.2 (2)
O1—C2—C3	119.2 (3)	C10—C11—C12	119.0 (3)
O1—C2—C1	122.6 (3)	C10—C11—H11	120.5
C3—C2—C1	118.2 (3)	C12—C11—H11	120.5
C4—C3—C2	121.6 (3)	C13—C12—C11	121.0 (3)
C4—C3—Br1	119.5 (2)	C13—C12—H12	119.5
C2—C3—Br1	118.9 (2)	C11—C12—H12	119.5
C3—C4—C5	119.4 (3)	C12—C13—C14	119.6 (3)
C3—C4—H4	120.3	C12—C13—H13	120.2
C5—C4—H4	120.3	C14—C13—H13	120.2
C6—C5—C4	120.7 (3)	C13—C14—C9	120.7 (3)
C6—C5—Cl1	120.4 (2)	C13—C14—H14	119.6
C4—C5—Cl1	118.8 (2)	C9—C14—H14	119.6
C5—C6—C1	120.4 (3)	O3—C15—H15A	109.5
C5—C6—H6	119.8	O3—C15—H15B	109.5
C1—C6—H6	119.8	H15A—C15—H15B	109.5
N1—C7—C1	119.8 (3)	O3—C15—H15C	109.5
N1—C7—H7	120.1	H15A—C15—H15C	109.5
C1—C7—H7	120.1	H15B—C15—H15C	109.5

D—H···A	D—H	H···A	D···A	D—H···A
O1—H1···N1	0.82	1.86	2.585 (3)	146
O3—H3···O2	0.82	2.04	2.727 (3)	141
N2—H2···O3i	0.91 (3)	1.93 (3)	2.830 (4)	176 (4)

Table 1

Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
O1—H1⋯N1	0.82	1.86	2.585 (3)	146
O3—H3⋯O2	0.82	2.04	2.727 (3)	141
N2—H2⋯O3i	0.91 (3)	1.93 (3)	2.830 (4)	176 (4)

Symmetry code: (i) .