2-Chloro-N′-(3,5-dibromo-2-hydroxy­benzyl­idene)benzohydrazide methanol solvate

Tang, C.-B.

doi:10.1107/S160053680801965X

organic compounds

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doi:10.1107/S160053680801965X

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2-Chloro-N′-(3,5-dibromo-2-hydroxybenzylidene)benzohydrazide methanol solvate

Chun-Bao Tang ^a ^*

^aDepartment of Chemistry, Jiaying University, Meizhou 514015, People's Republic of China
^*Correspondence e-mail: chunbao_tang@163.com

(Received 25 June 2008; accepted 27 June 2008; online 5 July 2008)

The title Schiff base compound, C₁₄H₉Br₂ClN₂O₂·CH₄O, was derived from the condensation reaction of 3,5-dibromosalicylaldehyde with 2-chlorobenzohydrazide. The dihedral angle between the two benzene rings is 48.2 (2)°. In the crystal structure, molecules are linked through O—H⋯O and N—H⋯O intermolecular hydrogen bonds, forming layers parallel to the bc plane. There is also an O—H⋯N intramolecular hydrogen bond.

Related literature

For related structures, see: Tang (2006 ); Tang, (2007a ,b ,c ,d ). For reference structural data, see: Allen et al. (1987 ).

Experimental

Crystal data

C₁₄H₉Br₂ClN₂O₂·CH₄O
M_r = 464.54
Monoclinic, P 2₁ /c
a = 11.156 (4) Å
b = 9.696 (3) Å
c = 18.536 (3) Å
β = 120.356 (8)°
V = 1730.1 (9) Å³
Z = 4
Mo Kα radiation
μ = 4.85 mm⁻¹
T = 298 (2) K
0.23 × 0.20 × 0.20 mm

Data collection

Bruker SMART CCD area-detector diffractometer
Absorption correction: multi-scan (SADABS; Sheldrick, 1996 ) T_min = 0.402, T_max = 0.444 (expected range = 0.343–0.379)
9035 measured reflections
3627 independent reflections
1895 reflections with I > 2σ(I)
R_int = 0.101

Refinement

R[F² > 2σ(F²)] = 0.069
wR(F²) = 0.160
S = 0.92
3627 reflections
215 parameters
1 restraint
H atoms treated by a mixture of independent and constrained refinement
Δρ_max = 0.81 e Å⁻³
Δρ_min = −0.71 e Å⁻³

Table 1
Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
O3—H3A⋯O2ⁱ	0.82	2.05	2.697 (9)	136
N2—H2⋯O3	0.89 (7)	1.946 (17)	2.840 (7)	173 (8)
O1—H1⋯N1	0.82	1.91	2.590 (6)	140
Symmetry code: (i) $[-x, y-{\script{1\over 2}}, -z+{\script{3\over 2}}]$ .

Data collection: SMART (Bruker, 2002 ); cell refinement: SAINT (Bruker, 2002); 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: SHELXL97.

Supporting information

Crystal structure: contains datablocks global, I. DOI: 10.1107/S160053680801965X/at2583sup1.cif

Structure factors: contains datablock I. DOI: 10.1107/S160053680801965X/at2583Isup2.hkl

checkCIF report

Comment top

Recently, the author has reported the structures of several Schiff base compounds (Tang, 2006;Tang, 2007a,b,c,d) and, in continuation of work in this area, reports herein the structure of the title compound, (I), a new Schiff base compound.

In the title compound (Fig. 1), the dihedral angle between the two benzene rings is 48.2 (2)°. The torsion angles C1—C7—N1—N2, C7—N1—N2—C8, and N1—N2—C8—C9 are 0.1 (2), 4.8 (2), and 4.3 (2)°, respectively. All the bond lengths are within normal values (Allen et al., 1987).

In the crystal structure of the compound, molecules are linked through O–H···O intermolecular hydrogen bonds (Table 1), forming layers parallel to the bc plane (Fig. 2).

Related literature top

For related structures, see: Tang (2006); Tang, (2007a,b,c,d). For reference structural data, see: Allen et al. (1987).

Experimental top

3,5-Dibromosalicylaldehyde (0.1 mmol, 28.0 mg) and 2-chlorobenzohydrazide (0.1 mmol, 17.0 mg) were dissolved in a methanol solution (20 ml). The mixture was stirred at reflux for 10 min to give a clear colorless solution. Colourless block-like crystals of the compound were formed by slow evaporation of the solvent over several days.

Computing details top

Data collection: SMART (Bruker, 2002); cell refinement: SAINT (Bruker, 2002); data reduction: SAINT (Bruker, 2002); 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: SHELXL97 (Sheldrick, 2008).

Figures top

	Fig. 1. The molecular structure of the compound, showing the atom-numbering scheme. Displacement ellipsoids are drawn at the 30% probability level.
	Fig. 2. Molecular packing of (I) with hydrogen bonds drawn as dashed lines.

2-Chloro-N'-(3,5-dibromo-2-hydroxybenzylidene)benzohydrazide methanol solvate top

Crystal data top

C₁₄H₉Br₂ClN₂O₂·CH₄O	F(000) = 912
M_r = 464.54	D_x = 1.783 Mg m⁻³
Monoclinic, P2₁/c	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: -P 2ybc	Cell parameters from 2286 reflections
a = 11.156 (4) Å	θ = 2.4–24.5°
b = 9.696 (3) Å	µ = 4.85 mm⁻¹
c = 18.536 (3) Å	T = 298 K
β = 120.356 (8)°	Block, colourless
V = 1730.1 (9) Å³	0.23 × 0.20 × 0.20 mm
Z = 4

Data collection top

Bruker SMART CCD area-detector diffractometer	3627 independent reflections
Radiation source: fine-focus sealed tube	1895 reflections with I > 2σ(I)
Graphite monochromator	R_int = 0.101
ω scans	θ_max = 27.0°, θ_min = 2.1°
Absorption correction: multi-scan (SADABS; Sheldrick, 1996)	h = −14→14
T_min = 0.402, T_max = 0.444	k = −12→10
9035 measured reflections	l = −23→22

Refinement top

Refinement on F²	Secondary atom site location: difference Fourier map
Least-squares matrix: full	Hydrogen site location: inferred from neighbouring sites
R[F² > 2σ(F²)] = 0.069	H atoms treated by a mixture of independent and constrained refinement
wR(F²) = 0.160	w = 1/[σ²(F_o²) + (0.0746P)²] where P = (F_o² + 2F_c²)/3
S = 0.92	(Δ/σ)_max < 0.001
3627 reflections	Δρ_max = 0.81 e Å⁻³
215 parameters	Δρ_min = −0.71 e Å⁻³
1 restraint	Extinction correction: SHELXL97 (Sheldrick, 2008), Fc^*=kFc[1+0.001xFc²λ³/sin(2θ)]^-1/4
Primary atom site location: structure-invariant direct methods	Extinction coefficient: 0.0119 (12)

Crystal data top

C₁₄H₉Br₂ClN₂O₂·CH₄O	V = 1730.1 (9) Å³
M_r = 464.54	Z = 4
Monoclinic, P2₁/c	Mo Kα radiation
a = 11.156 (4) Å	µ = 4.85 mm⁻¹
b = 9.696 (3) Å	T = 298 K
c = 18.536 (3) Å	0.23 × 0.20 × 0.20 mm
β = 120.356 (8)°

Data collection top

Bruker SMART CCD area-detector diffractometer	3627 independent reflections
Absorption correction: multi-scan (SADABS; Sheldrick, 1996)	1895 reflections with I > 2σ(I)
T_min = 0.402, T_max = 0.444	R_int = 0.101
9035 measured reflections

Refinement top

R[F² > 2σ(F²)] = 0.069	1 restraint
wR(F²) = 0.160	H atoms treated by a mixture of independent and constrained refinement
S = 0.92	Δρ_max = 0.81 e Å⁻³
3627 reflections	Δρ_min = −0.71 e Å⁻³
215 parameters

Special details top

Geometry. All esds (except the esd in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell esds are taken into account individually in the estimation of esds in distances, angles and torsion angles; correlations between esds in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell esds is used for estimating esds 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 > 2sigma(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.

Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Å²) top

	x	y	z	U_iso*/U_eq
Br1	−0.36755 (9)	1.09036 (8)	0.95218 (6)	0.0603 (4)
Br2	−0.19725 (9)	0.54059 (7)	1.04896 (6)	0.0557 (3)
Cl1	0.3094 (2)	1.28217 (17)	0.81645 (14)	0.0580 (6)
O1	−0.1788 (5)	1.0664 (4)	0.8816 (3)	0.0443 (14)
H1	−0.1429	1.0532	0.8531	0.067*
O2	0.0171 (5)	1.1554 (5)	0.7617 (4)	0.0543 (15)
O3	0.2494 (6)	0.7016 (5)	0.8572 (4)	0.0560 (16)
H3A	0.1924	0.6511	0.8203	0.084*
N1	0.0034 (6)	0.9492 (5)	0.8546 (4)	0.0373 (16)
N2	0.0939 (6)	0.9488 (5)	0.8251 (4)	0.0388 (16)
C1	−0.0946 (7)	0.8351 (6)	0.9261 (4)	0.0325 (16)
C2	−0.1773 (7)	0.9478 (5)	0.9204 (4)	0.0307 (16)
C3	−0.2590 (7)	0.9362 (6)	0.9571 (5)	0.0374 (18)
C4	−0.2624 (7)	0.8177 (6)	0.9961 (5)	0.0400 (19)
H4	−0.3182	0.8124	1.0200	0.048*
C5	−0.1835 (7)	0.7073 (6)	0.9999 (5)	0.0386 (18)
C6	−0.0988 (7)	0.7157 (6)	0.9662 (5)	0.0389 (19)
H6	−0.0438	0.6407	0.9702	0.047*
C7	0.0008 (7)	0.8415 (6)	0.8926 (5)	0.0415 (19)
H7	0.0583	0.7672	0.8993	0.050*
C8	0.0941 (7)	1.0545 (6)	0.7797 (5)	0.0353 (18)
C9	0.1906 (7)	1.0373 (6)	0.7455 (4)	0.0357 (17)
C10	0.2917 (8)	1.1341 (6)	0.7595 (5)	0.0415 (19)
C11	0.3785 (8)	1.1138 (7)	0.7278 (5)	0.049 (2)
H11	0.4449	1.1799	0.7366	0.058*
C12	0.3676 (9)	0.9973 (8)	0.6836 (6)	0.059 (3)
H12	0.4265	0.9842	0.6624	0.071*
C13	0.2705 (9)	0.9004 (7)	0.6706 (6)	0.056 (2)
H13	0.2645	0.8205	0.6412	0.068*
C14	0.1819 (8)	0.9187 (7)	0.7002 (5)	0.048 (2)
H14	0.1152	0.8521	0.6901	0.057*
C15	0.3807 (10)	0.6749 (9)	0.8694 (7)	0.092 (4)
H15A	0.4377	0.7555	0.8916	0.138*
H15B	0.3730	0.6508	0.8170	0.138*
H15C	0.4221	0.5998	0.9080	0.138*
H2	0.149 (7)	0.875 (5)	0.839 (5)	0.080*

Atomic displacement parameters (Å²) top

	U¹¹	U²²	U³³	U¹²	U¹³	U²³
Br1	0.0653 (7)	0.0618 (5)	0.0723 (7)	0.0269 (4)	0.0484 (6)	0.0132 (4)
Br2	0.0785 (8)	0.0421 (4)	0.0704 (7)	0.0006 (4)	0.0551 (6)	0.0114 (4)
Cl1	0.0664 (17)	0.0464 (10)	0.0727 (16)	−0.0114 (9)	0.0436 (15)	−0.0142 (10)
O1	0.055 (4)	0.040 (2)	0.055 (4)	0.009 (2)	0.040 (3)	0.008 (2)
O2	0.050 (4)	0.047 (3)	0.080 (4)	0.019 (3)	0.044 (4)	0.025 (3)
O3	0.044 (4)	0.045 (3)	0.080 (5)	0.002 (2)	0.033 (4)	0.002 (3)
N1	0.048 (4)	0.030 (3)	0.050 (4)	0.008 (2)	0.037 (4)	0.005 (3)
N2	0.047 (4)	0.030 (3)	0.057 (4)	0.007 (2)	0.039 (4)	0.011 (3)
C1	0.028 (5)	0.034 (3)	0.034 (4)	0.005 (3)	0.015 (4)	0.007 (3)
C2	0.030 (5)	0.027 (3)	0.030 (4)	−0.001 (3)	0.012 (4)	0.004 (3)
C3	0.036 (5)	0.037 (3)	0.042 (5)	0.006 (3)	0.021 (4)	−0.004 (3)
C4	0.038 (5)	0.051 (4)	0.044 (5)	0.000 (4)	0.030 (5)	−0.004 (4)
C5	0.049 (5)	0.035 (3)	0.041 (5)	−0.006 (3)	0.030 (5)	0.004 (3)
C6	0.038 (5)	0.031 (3)	0.059 (6)	0.005 (3)	0.032 (5)	−0.001 (3)
C7	0.049 (5)	0.029 (3)	0.059 (6)	0.002 (3)	0.036 (5)	−0.001 (3)
C8	0.039 (5)	0.033 (3)	0.042 (5)	−0.004 (3)	0.026 (4)	−0.007 (3)
C9	0.034 (5)	0.038 (3)	0.039 (5)	0.003 (3)	0.022 (4)	0.010 (3)
C10	0.051 (6)	0.041 (3)	0.043 (5)	−0.003 (3)	0.032 (5)	−0.003 (3)
C11	0.046 (6)	0.050 (4)	0.064 (6)	−0.009 (3)	0.039 (5)	−0.003 (4)
C12	0.065 (6)	0.071 (5)	0.074 (7)	0.004 (4)	0.059 (6)	0.004 (5)
C13	0.077 (7)	0.052 (4)	0.063 (6)	0.005 (4)	0.052 (6)	−0.004 (4)
C14	0.061 (6)	0.040 (4)	0.052 (6)	−0.003 (3)	0.036 (5)	0.003 (4)
C15	0.069 (8)	0.083 (6)	0.148 (11)	0.012 (6)	0.072 (9)	0.010 (7)

Geometric parameters (Å, º) top

Br1—C3	1.897 (6)	C4—H4	0.9300
Br2—C5	1.899 (6)	C5—C6	1.372 (8)
Cl1—C10	1.733 (6)	C6—H6	0.9300
O1—C2	1.352 (6)	C7—H7	0.9300
O1—H1	0.8200	C8—C9	1.509 (8)
O2—C8	1.232 (7)	C9—C10	1.387 (9)
O3—C15	1.389 (9)	C9—C14	1.399 (9)
O3—H3A	0.8200	C10—C11	1.377 (8)
N1—C7	1.269 (7)	C11—C12	1.365 (10)
N1—N2	1.369 (6)	C11—H11	0.9300
N2—C8	1.327 (7)	C12—C13	1.361 (10)
N2—H2	0.89 (7)	C12—H12	0.9300
C1—C6	1.390 (8)	C13—C14	1.362 (9)
C1—C2	1.400 (8)	C13—H13	0.9300
C1—C7	1.480 (8)	C14—H14	0.9300
C2—C3	1.389 (8)	C15—H15A	0.9600
C3—C4	1.368 (8)	C15—H15B	0.9600
C4—C5	1.366 (8)	C15—H15C	0.9600

C2—O1—H1	109.5	O2—C8—N2	124.1 (5)
C15—O3—H3A	109.5	O2—C8—C9	121.5 (6)
C7—N1—N2	116.6 (5)	N2—C8—C9	114.3 (5)
C8—N2—N1	119.3 (5)	C10—C9—C14	118.1 (5)
C8—N2—H2	125 (5)	C10—C9—C8	122.2 (6)
N1—N2—H2	115 (5)	C14—C9—C8	119.7 (5)
C6—C1—C2	119.4 (5)	C11—C10—C9	120.3 (6)
C6—C1—C7	119.0 (5)	C11—C10—Cl1	119.3 (5)
C2—C1—C7	121.5 (5)	C9—C10—Cl1	120.4 (4)
O1—C2—C3	119.6 (5)	C12—C11—C10	120.4 (6)
O1—C2—C1	122.3 (5)	C12—C11—H11	119.8
C3—C2—C1	118.1 (5)	C10—C11—H11	119.8
C4—C3—C2	121.8 (5)	C13—C12—C11	120.0 (6)
C4—C3—Br1	119.9 (4)	C13—C12—H12	120.0
C2—C3—Br1	118.3 (5)	C11—C12—H12	120.0
C5—C4—C3	119.7 (5)	C12—C13—C14	120.9 (7)
C5—C4—H4	120.1	C12—C13—H13	119.6
C3—C4—H4	120.1	C14—C13—H13	119.6
C4—C5—C6	120.3 (5)	C13—C14—C9	120.3 (7)
C4—C5—Br2	119.0 (4)	C13—C14—H14	119.8
C6—C5—Br2	120.6 (5)	C9—C14—H14	119.8
C5—C6—C1	120.7 (5)	O3—C15—H15A	109.5
C5—C6—H6	119.7	O3—C15—H15B	109.5
C1—C6—H6	119.7	H15A—C15—H15B	109.5
N1—C7—C1	119.4 (5)	O3—C15—H15C	109.5
N1—C7—H7	120.3	H15A—C15—H15C	109.5
C1—C7—H7	120.3	H15B—C15—H15C	109.5

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
O3—H3A···O2ⁱ	0.82	2.05	2.697 (9)	136
N2—H2···O3	0.89 (7)	1.95 (2)	2.840 (7)	173 (8)
O1—H1···N1	0.82	1.91	2.590 (6)	140

Symmetry code: (i) −x, y−1/2, −z+3/2.

Experimental details

Crystal data
Chemical formula	C₁₄H₉Br₂ClN₂O₂·CH₄O
M_r	464.54
Crystal system, space group	Monoclinic, P2₁/c
Temperature (K)	298
a, b, c (Å)	11.156 (4), 9.696 (3), 18.536 (3)
β (°)	120.356 (8)
V (Å³)	1730.1 (9)
Z	4
Radiation type	Mo Kα
µ (mm⁻¹)	4.85
Crystal size (mm)	0.23 × 0.20 × 0.20

Data collection
Diffractometer	Bruker SMART CCD area-detector diffractometer
Absorption correction	Multi-scan (SADABS; Sheldrick, 1996)
T_min, T_max	0.402, 0.444
No. of measured, independent and observed [I > 2σ(I)] reflections	9035, 3627, 1895
R_int	0.101
(sin θ/λ)_max (Å⁻¹)	0.639

Refinement
R[F² > 2σ(F²)], wR(F²), S	0.069, 0.160, 0.92
No. of reflections	3627
No. of parameters	215
No. of restraints	1
H-atom treatment	H atoms treated by a mixture of independent and constrained refinement
Δρ_max, Δρ_min (e Å⁻³)	0.81, −0.71

Computer programs: SMART (Bruker, 2002), SAINT (Bruker, 2002), SHELXS97 (Sheldrick, 2008), SHELXL97 (Sheldrick, 2008), SHELXTL (Sheldrick, 2008).

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
O3—H3A···O2ⁱ	0.82	2.05	2.697 (9)	136.1
N2—H2···O3	0.89 (7)	1.946 (17)	2.840 (7)	173 (8)
O1—H1···N1	0.82	1.91	2.590 (6)	140.1

Symmetry code: (i) −x, y−1/2, −z+3/2.

Acknowledgements

Financial support from the Jiaying University research fund is gratefully acknowledged.

References

Allen, F. H., Kennard, O., Watson, D. G., Brammer, L., Orpen, A. G. & Taylor, R. (1987). J. Chem. Soc. Perkin Trans. 2, pp. S1–19. CrossRef Web of Science Google Scholar
Bruker (2002). SAINT and SMART. Bruker AXS Inc., Madison, Wisconsin, USA. Google Scholar
Sheldrick, G. M. (1996). SADABS. University of Göttingen, Germany. Google Scholar
Sheldrick, G. M. (2008). Acta Cryst. A64, 112–122. Web of Science CrossRef CAS IUCr Journals Google Scholar
Tang, C.-B. (2006). Acta Cryst. E62, m2629–m2630. Web of Science CSD CrossRef IUCr Journals Google Scholar
Tang, C.-B. (2007a). Acta Cryst. E63, m2654. Web of Science CSD CrossRef IUCr Journals Google Scholar
Tang, C.-B. (2007b). Acta Cryst. E63, m2785–m2786. Web of Science CSD CrossRef IUCr Journals Google Scholar
Tang, C.-B. (2007c). Acta Cryst. E63, o4545. Web of Science CSD CrossRef IUCr Journals Google Scholar
Tang, C.-B. (2007d). Acta Cryst. E63, o4841. Web of Science CSD CrossRef IUCr Journals Google Scholar

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organic compounds\(\def\hfill{\hskip 5em}\def\hfil{\hskip 3em}\def\eqno#1{\hfil {#1}}\)

2-Chloro-N′-(3,5-di­bromo-2-hy­droxy­benzyl­­idene)benzohydrazide methanol solvate

Related literature

Experimental

Crystal data

Data collection

Refinement

Supporting information

Acknowledgements

References

organic compounds

2-Chloro-N′-(3,5-dibromo-2-hydroxybenzylidene)benzohydrazide methanol solvate