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ISSN: 2056-9890

N′-(3-Bromo-5-chloro-2-hy­droxy­benzyl­­idene)-3,4,5-tri­hydroxy­benzohydrazide methanol solvate

aDepartment of Chemistry, University of Malaya, 50603 Kuala Lumpur, Malaysia
*Correspondence e-mail: seikweng@um.edu.my

(Received 18 March 2009; accepted 23 March 2009; online 28 March 2009)

The benzohydrazide mol­ecule of the title compound, C14H10BrClN2O5·CH3OH, is non-planar, the two aromatic rings at either side of the –C(=O)–NH–N=CH– unit being twisted by 5.9 (1)°. The benzohydrazide mol­ecule is linked to the solvent mol­ecule by an O—H⋯O hydrogen bond. Mol­ecules are connected by further O—H⋯O hydrogen bonds and an N—H⋯O link into a two-dimensional array.

Related literature

For the the parent N′-(2-hydroxy­benzyl­idene)benzohydrazide, see: Lyubchova et al. (1995[Lyubchova, A., Cossé-Barbi, A., Doucet, J. P., Robert, F., Souron, J.-P. & Quarton, M. (1995). Acta Cryst. C51, 1893-1895.]). For other N′-(2-hydr­oxy-5-nitro­benzyl­idene)benzohydrazides, see: Ali et al. (2005[Ali, H. M., Puvaneswary, S. & Ng, S. W. (2005). Acta Cryst. E61, o3464-o3465.]); Lyubchova et al. (1995[Lyubchova, A., Cossé-Barbi, A., Doucet, J. P., Robert, F., Souron, J.-P. & Quarton, M. (1995). Acta Cryst. C51, 1893-1895.]); Xu & Liu (2006[Xu, H.-M. & Liu, S.-X. (2006). Acta Cryst. E62, o3026-o3027.]).

[Scheme 1]

Experimental

Crystal data
  • C14H10BrClN2O5·CH4O

  • Mr = 433.64

  • Monoclinic, C 2/c

  • a = 21.6157 (3) Å

  • b = 12.7408 (2) Å

  • c = 17.0803 (2) Å

  • β = 136.641 (1)°

  • V = 3229.57 (8) Å3

  • Z = 8

  • Mo Kα radiation

  • μ = 2.75 mm−1

  • T = 123 K

  • 0.20 × 0.15 × 0.10 mm

Data collection
  • Bruker SMART APEX diffractometer

  • Absorption correction: multi-scan (SADABS; Sheldrick, 1996[Sheldrick, G. M. (1996). SADABS. University of Göttingen, Germany.]) Tmin = 0.610, Tmax = 0.771

  • 15301 measured reflections

  • 3714 independent reflections

  • 3407 reflections with I > 2σ(I)

  • Rint = 0.016

Refinement
  • R[F2 > 2σ(F2)] = 0.023

  • wR(F2) = 0.068

  • S = 1.03

  • 3714 reflections

  • 251 parameters

  • 6 restraints

  • H atoms treated by a mixture of independent and constrained refinement

  • Δρmax = 0.43 e Å−3

  • Δρmin = −0.35 e Å−3

Table 1
Hydrogen-bond geometry (Å, °)

D—H⋯A D—H H⋯A DA D—H⋯A
O1—H1⋯O5i 0.83 (1) 2.03 (3) 2.607 (2) 126 (3)
O3—H3⋯O6ii 0.83 (1) 2.05 (1) 2.856 (2) 165 (3)
O4—H4⋯O1iii 0.83 (1) 2.20 (1) 3.027 (2) 173 (2)
O5—H5⋯O2iii 0.82 (1) 1.79 (1) 2.608 (2) 176 (2)
O6—H6⋯O2 0.83 (1) 2.04 (1) 2.843 (2) 164 (2)
N2—H2⋯O6iii 0.87 (1) 2.25 (1) 3.112 (2) 169 (2)
Symmetry codes: (i) [-x+{\script{1\over 2}}, y+{\script{1\over 2}}, -z+{\script{3\over 2}}]; (ii) [-x+{\script{1\over 2}}, -y+{\script{3\over 2}}, -z+2]; (iii) [-x+{\script{1\over 2}}, y-{\script{1\over 2}}, -z+{\script{3\over 2}}].

Data collection: APEX2 (Bruker, 2008[Bruker (2008). APEX2 and SAINT. Bruker AXS Inc., Madison, Wisconsin, USA.]); cell refinement: SAINT (Bruker, 2008[Bruker (2008). APEX2 and SAINT. Bruker AXS Inc., Madison, Wisconsin, USA.]); data reduction: SAINT; program(s) used to solve structure: SHELXS97 (Sheldrick, 2008[Sheldrick, G. M. (2008). Acta Cryst. A64, 112-122.]); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008[Sheldrick, G. M. (2008). Acta Cryst. A64, 112-122.]); molecular graphics: X-SEED (Barbour, 2001[Barbour, L. J. (2001). J. Supramol. Chem. 1, 189-191.]); software used to prepare material for publication: publCIF (Westrip, 2009[Westrip, S. P. (2009). publCIF. In preparation.]).

Supporting information


Related literature top

For the the parent N'-(2-hydroxybenzylidene)benzohydrazide, see: Lyubchova et al. (1995). For other N'-(2-hydroxy-5-nitrobenzylidene)benzohydrazides, see: Ali et al. (2005); Lyubchova et al. (1995); Xu & Liu (2006).

Experimental top

3-Bromo-5-chloro-2-hydroxybenzaldehyde (0.47 g, 2 mmol) and 3,4,5-trihydroxybenzoylhydrazide (0.36 g, 2 mmol) were heated in ethanol (50 ml) for several hours. The solvent was removed and the product recrystallized from methanol.

Refinement top

Carbon-bound H-atoms were placed in calculated positions [C—H 0.95 Å, U(H) = 1.2U(C)], and were included in the refinement in the riding model approximation.

The amino and hydroxy H-atoms were located in a difference Fourier map, and were refined with distance restraints of N–H 0.88±0.01 Å and O–H 0.84±0.01 Å, respectively; their temperature factors were refined isotropically.

Computing details top

Data collection: APEX2 (Bruker, 2008); cell refinement: SAINT (Bruker, 2008); data reduction: SAINT (Bruker, 2008); program(s) used to solve structure: SHELXS97 (Sheldrick, 2008); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008); molecular graphics: X-SEED (Barbour, 2001); software used to prepare material for publication: publCIF (Westrip, 2009).

Figures top
[Figure 1] Fig. 1. Thermal ellipsoid plot (Barbour, 2001) of C14H10BrClNO5.CH3OH at the 70% probability level; hydrogen atoms are drawn as spheres of arbitrary radius.
N'-(3-Bromo-5-chloro-2-hydroxybenzylidene)-3,4,5-trihydroxybenzohydrazide methanol solvate top
Crystal data top
C14H10BrClN2O5·CH4OF(000) = 1744
Mr = 433.64Dx = 1.784 Mg m3
Monoclinic, C2/cMo Kα radiation, λ = 0.71073 Å
Hall symbol: -C 2ycCell parameters from 8789 reflections
a = 21.6157 (3) Åθ = 2.7–28.3°
b = 12.7408 (2) ŵ = 2.75 mm1
c = 17.0803 (2) ÅT = 123 K
β = 136.641 (1)°Polyhedral, tan
V = 3229.57 (8) Å30.20 × 0.15 × 0.10 mm
Z = 8
Data collection top
Bruker SMART APEX
diffractometer
3714 independent reflections
Radiation source: fine-focus sealed tube3407 reflections with I > 2σ(I)
Graphite monochromatorRint = 0.016
ω scansθmax = 27.5°, θmin = 2.0°
Absorption correction: multi-scan
(SADABS; Sheldrick, 1996)
h = 2826
Tmin = 0.610, Tmax = 0.771k = 1616
15301 measured reflectionsl = 2221
Refinement top
Refinement on F2Primary atom site location: structure-invariant direct methods
Least-squares matrix: fullSecondary atom site location: difference Fourier map
R[F2 > 2σ(F2)] = 0.023Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.068H atoms treated by a mixture of independent and constrained refinement
S = 1.03 w = 1/[σ2(Fo2) + (0.0429P)2 + 3.4447P]
where P = (Fo2 + 2Fc2)/3
3714 reflections(Δ/σ)max = 0.001
251 parametersΔρmax = 0.43 e Å3
6 restraintsΔρmin = 0.35 e Å3
Crystal data top
C14H10BrClN2O5·CH4OV = 3229.57 (8) Å3
Mr = 433.64Z = 8
Monoclinic, C2/cMo Kα radiation
a = 21.6157 (3) ŵ = 2.75 mm1
b = 12.7408 (2) ÅT = 123 K
c = 17.0803 (2) Å0.20 × 0.15 × 0.10 mm
β = 136.641 (1)°
Data collection top
Bruker SMART APEX
diffractometer
3714 independent reflections
Absorption correction: multi-scan
(SADABS; Sheldrick, 1996)
3407 reflections with I > 2σ(I)
Tmin = 0.610, Tmax = 0.771Rint = 0.016
15301 measured reflections
Refinement top
R[F2 > 2σ(F2)] = 0.0236 restraints
wR(F2) = 0.068H atoms treated by a mixture of independent and constrained refinement
S = 1.03Δρmax = 0.43 e Å3
3714 reflectionsΔρmin = 0.35 e Å3
251 parameters
Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Å2) top
xyzUiso*/Ueq
Br10.044783 (12)0.783092 (13)0.137916 (14)0.02172 (7)
Cl10.01420 (3)0.35175 (3)0.10946 (4)0.02369 (10)
N10.18779 (9)0.61375 (11)0.54542 (11)0.0148 (3)
N20.23179 (9)0.58418 (11)0.65407 (11)0.0154 (3)
O10.13116 (9)0.74001 (9)0.37133 (11)0.0211 (3)
O20.20939 (8)0.74133 (9)0.69379 (10)0.0187 (2)
O30.36037 (9)0.69205 (10)1.09583 (10)0.0219 (3)
O40.37603 (8)0.47725 (9)1.12740 (10)0.0189 (2)
O50.31633 (9)0.34724 (9)0.95863 (10)0.0205 (3)
O60.15053 (8)0.88367 (9)0.75713 (10)0.0196 (2)
C10.10878 (11)0.64859 (12)0.31698 (13)0.0155 (3)
C20.06644 (11)0.65171 (12)0.20499 (14)0.0156 (3)
C30.03858 (11)0.56163 (13)0.14173 (13)0.0172 (3)
H3A0.00880.56550.06520.021*
C40.05469 (11)0.46540 (12)0.19171 (14)0.0168 (3)
C50.09940 (10)0.45814 (12)0.30364 (13)0.0158 (3)
H5A0.11170.39140.33730.019*
C60.12644 (10)0.54979 (12)0.36718 (13)0.0151 (3)
C70.17192 (10)0.53678 (12)0.48399 (13)0.0155 (3)
H70.19070.46840.51630.019*
C80.23645 (10)0.64897 (12)0.72065 (13)0.0147 (3)
C90.27436 (10)0.60244 (12)0.82779 (13)0.0143 (3)
C100.30257 (11)0.66835 (12)0.91445 (13)0.0161 (3)
H100.29970.74240.90560.019*
C110.33473 (11)0.62583 (12)1.01356 (13)0.0156 (3)
C120.34227 (10)0.51690 (12)1.02835 (13)0.0146 (3)
C130.31234 (10)0.45163 (12)0.94055 (13)0.0147 (3)
C140.27745 (10)0.49359 (12)0.84020 (13)0.0146 (3)
H140.25570.44860.78000.018*
C150.06333 (12)0.92150 (14)0.65359 (15)0.0237 (4)
H15A0.04450.97810.67150.036*
H15B0.01960.86400.61600.036*
H15C0.06640.94820.60270.036*
H10.154 (2)0.731 (3)0.4365 (15)0.087 (13)*
H30.3635 (18)0.6613 (19)1.1413 (18)0.044 (7)*
H40.3783 (17)0.4119 (8)1.129 (2)0.036 (7)*
H50.3065 (15)0.3125 (16)0.9101 (15)0.030 (6)*
H60.1634 (16)0.8331 (14)0.741 (2)0.037 (7)*
H20.2604 (14)0.5242 (11)0.6799 (18)0.029 (6)*
Atomic displacement parameters (Å2) top
U11U22U33U12U13U23
Br10.02904 (11)0.01747 (10)0.01845 (10)0.00031 (6)0.01720 (9)0.00285 (6)
Cl10.0373 (2)0.01580 (19)0.01895 (19)0.00382 (16)0.02079 (19)0.00522 (14)
N10.0169 (6)0.0172 (6)0.0109 (6)0.0006 (5)0.0103 (5)0.0013 (5)
N20.0205 (6)0.0142 (6)0.0119 (6)0.0032 (5)0.0120 (6)0.0031 (5)
O10.0321 (7)0.0152 (5)0.0161 (6)0.0006 (5)0.0175 (6)0.0016 (5)
O20.0293 (6)0.0135 (5)0.0186 (6)0.0039 (5)0.0191 (5)0.0034 (4)
O30.0374 (7)0.0154 (5)0.0171 (6)0.0039 (5)0.0212 (6)0.0038 (5)
O40.0294 (6)0.0154 (6)0.0142 (5)0.0022 (5)0.0166 (5)0.0019 (4)
O50.0378 (7)0.0109 (5)0.0182 (6)0.0028 (5)0.0221 (6)0.0017 (4)
O60.0251 (6)0.0178 (6)0.0186 (6)0.0016 (5)0.0168 (5)0.0013 (5)
C10.0184 (7)0.0151 (7)0.0154 (7)0.0006 (6)0.0131 (7)0.0020 (6)
C20.0186 (7)0.0153 (7)0.0153 (7)0.0015 (6)0.0130 (7)0.0026 (6)
C30.0185 (7)0.0226 (8)0.0135 (7)0.0012 (6)0.0126 (7)0.0011 (6)
C40.0202 (7)0.0170 (7)0.0169 (7)0.0017 (6)0.0147 (7)0.0037 (6)
C50.0184 (7)0.0153 (7)0.0164 (7)0.0005 (6)0.0136 (6)0.0007 (6)
C60.0164 (7)0.0182 (7)0.0129 (7)0.0004 (6)0.0113 (6)0.0003 (6)
C70.0173 (7)0.0156 (7)0.0135 (7)0.0006 (6)0.0112 (6)0.0017 (6)
C80.0165 (7)0.0151 (7)0.0138 (7)0.0016 (6)0.0114 (6)0.0007 (5)
C90.0158 (7)0.0158 (7)0.0126 (7)0.0010 (6)0.0107 (6)0.0009 (6)
C100.0212 (8)0.0123 (7)0.0166 (8)0.0005 (6)0.0144 (7)0.0003 (6)
C110.0198 (7)0.0148 (7)0.0140 (7)0.0021 (6)0.0129 (6)0.0030 (6)
C120.0168 (7)0.0167 (7)0.0123 (7)0.0009 (6)0.0112 (6)0.0013 (6)
C130.0180 (7)0.0121 (7)0.0168 (7)0.0016 (6)0.0136 (6)0.0006 (6)
C140.0189 (7)0.0136 (7)0.0144 (7)0.0005 (6)0.0131 (6)0.0005 (5)
C150.0247 (8)0.0219 (8)0.0214 (8)0.0000 (7)0.0158 (7)0.0015 (7)
Geometric parameters (Å, º) top
Br1—C21.8852 (15)C3—C41.386 (2)
Cl1—C41.7460 (16)C3—H3A0.9500
N1—C71.287 (2)C4—C51.382 (2)
N1—N21.3870 (18)C5—C61.400 (2)
N2—C81.348 (2)C5—H5A0.9500
N2—H20.874 (10)C6—C71.457 (2)
O1—C11.3415 (19)C7—H70.9500
O1—H10.832 (10)C8—C91.480 (2)
O2—C81.2438 (19)C9—C141.397 (2)
O3—C111.3642 (19)C9—C101.398 (2)
O3—H30.828 (10)C10—C111.390 (2)
O4—C121.3619 (18)C10—H100.9500
O4—H40.833 (10)C11—C121.399 (2)
O5—C131.3538 (18)C12—C131.396 (2)
O5—H50.820 (10)C13—C141.383 (2)
O6—C151.437 (2)C14—H140.9500
O6—H60.828 (10)C15—H15A0.9800
C1—C21.397 (2)C15—H15B0.9800
C1—C61.410 (2)C15—H15C0.9800
C2—C31.379 (2)
C7—N1—N2113.63 (13)C6—C7—H7118.5
C8—N2—N1121.35 (13)O2—C8—N2122.77 (14)
C8—N2—H2121.2 (15)O2—C8—C9121.61 (14)
N1—N2—H2117.2 (15)N2—C8—C9115.61 (13)
C1—O1—H1112 (3)C14—C9—C10119.97 (14)
C11—O3—H3111.6 (19)C14—C9—C8120.49 (14)
C12—O4—H4112.6 (18)C10—C9—C8119.44 (14)
C13—O5—H5111.9 (17)C11—C10—C9120.15 (14)
C15—O6—H6107.8 (17)C11—C10—H10119.9
O1—C1—C2118.05 (14)C9—C10—H10119.9
O1—C1—C6123.52 (14)O3—C11—C10118.85 (14)
C2—C1—C6118.42 (14)O3—C11—C12121.39 (14)
C3—C2—C1121.82 (14)C10—C11—C12119.75 (14)
C3—C2—Br1119.27 (12)O4—C12—C13121.65 (14)
C1—C2—Br1118.90 (12)O4—C12—C11118.63 (14)
C2—C3—C4118.86 (14)C13—C12—C11119.67 (14)
C2—C3—H3A120.6O5—C13—C14123.32 (14)
C4—C3—H3A120.6O5—C13—C12115.94 (14)
C5—C4—C3121.40 (14)C14—C13—C12120.69 (14)
C5—C4—Cl1119.65 (12)C13—C14—C9119.64 (14)
C3—C4—Cl1118.92 (12)C13—C14—H14120.2
C4—C5—C6119.62 (14)C9—C14—H14120.2
C4—C5—H5A120.2O6—C15—H15A109.5
C6—C5—H5A120.2O6—C15—H15B109.5
C5—C6—C1119.81 (14)H15A—C15—H15B109.5
C5—C6—C7116.89 (14)O6—C15—H15C109.5
C1—C6—C7123.30 (14)H15A—C15—H15C109.5
N1—C7—C6122.97 (14)H15B—C15—H15C109.5
N1—C7—H7118.5
C7—N1—N2—C8165.52 (15)N1—N2—C8—C9172.04 (14)
O1—C1—C2—C3177.88 (15)O2—C8—C9—C14159.38 (15)
C6—C1—C2—C32.7 (2)N2—C8—C9—C1419.4 (2)
O1—C1—C2—Br10.8 (2)O2—C8—C9—C1017.1 (2)
C6—C1—C2—Br1178.63 (11)N2—C8—C9—C10164.18 (15)
C1—C2—C3—C41.2 (2)C14—C9—C10—C110.8 (2)
Br1—C2—C3—C4179.92 (12)C8—C9—C10—C11177.25 (14)
C2—C3—C4—C51.3 (2)C9—C10—C11—O3178.92 (15)
C2—C3—C4—Cl1176.64 (12)C9—C10—C11—C122.6 (2)
C3—C4—C5—C62.2 (2)O3—C11—C12—O40.0 (2)
Cl1—C4—C5—C6175.66 (12)C10—C11—C12—O4178.42 (14)
C4—C5—C6—C10.7 (2)O3—C11—C12—C13177.72 (14)
C4—C5—C6—C7179.02 (14)C10—C11—C12—C133.9 (2)
O1—C1—C6—C5178.92 (15)O4—C12—C13—O52.0 (2)
C2—C1—C6—C51.7 (2)C11—C12—C13—O5175.63 (14)
O1—C1—C6—C70.8 (2)O4—C12—C13—C14179.35 (14)
C2—C1—C6—C7178.61 (14)C11—C12—C13—C141.7 (2)
N2—N1—C7—C6179.99 (14)O5—C13—C14—C9178.84 (15)
C5—C6—C7—N1169.07 (15)C12—C13—C14—C91.7 (2)
C1—C6—C7—N110.7 (2)C10—C9—C14—C133.0 (2)
N1—N2—C8—O26.7 (2)C8—C9—C14—C13179.38 (14)
Hydrogen-bond geometry (Å, º) top
D—H···AD—HH···AD···AD—H···A
O1—H1···O5i0.83 (1)2.03 (3)2.607 (2)126 (3)
O3—H3···O6ii0.83 (1)2.05 (1)2.856 (2)165 (3)
O4—H4···O1iii0.83 (1)2.20 (1)3.027 (2)173 (2)
O5—H5···O2iii0.82 (1)1.79 (1)2.608 (2)176 (2)
O6—H6···O20.83 (1)2.04 (1)2.843 (2)164 (2)
N2—H2···O6iii0.87 (1)2.25 (1)3.112 (2)169 (2)
Symmetry codes: (i) x+1/2, y+1/2, z+3/2; (ii) x+1/2, y+3/2, z+2; (iii) x+1/2, y1/2, z+3/2.

Experimental details

Crystal data
Chemical formulaC14H10BrClN2O5·CH4O
Mr433.64
Crystal system, space groupMonoclinic, C2/c
Temperature (K)123
a, b, c (Å)21.6157 (3), 12.7408 (2), 17.0803 (2)
β (°) 136.641 (1)
V3)3229.57 (8)
Z8
Radiation typeMo Kα
µ (mm1)2.75
Crystal size (mm)0.20 × 0.15 × 0.10
Data collection
DiffractometerBruker SMART APEX
diffractometer
Absorption correctionMulti-scan
(SADABS; Sheldrick, 1996)
Tmin, Tmax0.610, 0.771
No. of measured, independent and
observed [I > 2σ(I)] reflections
15301, 3714, 3407
Rint0.016
(sin θ/λ)max1)0.650
Refinement
R[F2 > 2σ(F2)], wR(F2), S 0.023, 0.068, 1.03
No. of reflections3714
No. of parameters251
No. of restraints6
H-atom treatmentH atoms treated by a mixture of independent and constrained refinement
Δρmax, Δρmin (e Å3)0.43, 0.35

Computer programs: APEX2 (Bruker, 2008), SAINT (Bruker, 2008), SHELXS97 (Sheldrick, 2008), SHELXL97 (Sheldrick, 2008), X-SEED (Barbour, 2001), publCIF (Westrip, 2009).

Hydrogen-bond geometry (Å, º) top
D—H···AD—HH···AD···AD—H···A
O1—H1···O5i0.83 (1)2.03 (3)2.607 (2)126 (3)
O3—H3···O6ii0.83 (1)2.05 (1)2.856 (2)165 (3)
O4—H4···O1iii0.83 (1)2.20 (1)3.027 (2)173 (2)
O5—H5···O2iii0.82 (1)1.79 (1)2.608 (2)176 (2)
O6—H6···O20.83 (1)2.04 (1)2.843 (2)164 (2)
N2—H2···O6iii0.87 (1)2.25 (1)3.112 (2)169 (2)
Symmetry codes: (i) x+1/2, y+1/2, z+3/2; (ii) x+1/2, y+3/2, z+2; (iii) x+1/2, y1/2, z+3/2.
 

Acknowledgements

We thank the University of Malaya for supporting this study.

References

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