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Acta Crystallogr Sect E Struct Rep Online. 2008 July 1; 64(Pt 7): o1298.
Published online 2008 June 19. doi:  10.1107/S1600536808018205
PMCID: PMC2961683

N′-(5-Bromo-2-methoxy­benzyl­idene)-3-hydroxy­benzohydrazide methanol hemisolvate

Abstract

The asymmetric unit of the title compound, C15H13BrN2O3·0.5CH3OH, contains two Schiff base mol­ecules and a methanol mol­ecule of crystallization. The dihedral angles between the benzene rings in the two mol­ecules are 23.8 (2) and 18.6 (2)°. In the crystal structure, mol­ecules are linked through inter­molecular N—H(...)O, O—H(...)O and O—H(...)N hydrogen bonds, forming a three-dimensional network.

Related literature

For related literature, see: Zhou & Tang (2007 [triangle]); Zhou & Xiao (2007 [triangle]). For related structures, see: Ali et al. (2007 [triangle]); Butcher et al. (2007 [triangle]); He (2008 [triangle]); Jing & Yu (2007 [triangle]); Nie (2008 [triangle]).

An external file that holds a picture, illustration, etc.
Object name is e-64-o1298-scheme1.jpg

Experimental

Crystal data

  • C15H13BrN2O3·0.5CH4O
  • M r = 365.21
  • Monoclinic, An external file that holds a picture, illustration, etc.
Object name is e-64-o1298-efi1.jpg
  • a = 12.906 (2) Å
  • b = 11.177 (2) Å
  • c = 22.607 (3) Å
  • β = 93.706 (3)°
  • V = 3254.3 (9) Å3
  • Z = 8
  • Mo Kα radiation
  • μ = 2.54 mm−1
  • T = 298 (2) K
  • 0.20 × 0.18 × 0.17 mm

Data collection

  • Bruker SMART CCD area-detector diffractometer
  • Absorption correction: multi-scan (SADABS; Bruker, 2001 [triangle]) T min = 0.630, T max = 0.672
  • 21623 measured reflections
  • 6725 independent reflections
  • 2610 reflections with I > 2σ(I)
  • R int = 0.104

Refinement

  • R[F 2 > 2σ(F 2)] = 0.061
  • wR(F 2) = 0.170
  • S = 0.98
  • 6725 reflections
  • 409 parameters
  • 2 restraints
  • H atoms treated by a mixture of independent and constrained refinement
  • Δρmax = 0.51 e Å−3
  • Δρmin = −0.47 e Å−3

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

Table 1
Hydrogen-bond geometry (Å, °)

Supplementary Material

Crystal structure: contains datablocks global, I. DOI: 10.1107/S1600536808018205/at2575sup1.cif

Structure factors: contains datablocks I. DOI: 10.1107/S1600536808018205/at2575Isup2.hkl

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

Acknowledgments

The author thanks Kaili College for financial support.

supplementary crystallographic information

Comment

Recently, we have reported two metal complexes with Schiff base ligands (Zhou & Tang, 2007; Zhou & Xiao, 2007). We report herein the crystal structure of the title Schiff base compound (I), Fig. 1.

The asymmetric unit of (I) consists of two Schiff base molecules and a methanol molecule of crystallization. The dihedral angles are 23.8 (2) ° and 18.6 (2) °, respectively, between the benzene rings (C1-C6) and (C10-C15) for molecule A, and (C16-C21), (C25-C3015) for molecule B. All the bond values are comparable to the similar compounds (Ali et al., 2007; Nie, 2008; He, 2008; Butcher et al., 2007; Jing & Yu, 2007).

In the crystal structure, molecules are linked through intermolecular N–H···O, O–H···O and O—H···N hydrogen bonds (Table 1) to form a three-dimensional network (Fig. 2).

Experimental

2-Methoxy-5-bromobenzaldehyde (1.0 mmol, 215.0 mg) and 3-hydroxybenzohydrazide (1.0 mmol, 152.1 mg) were dissolved in methanol (30 ml). The mixture was stirred at reflux for 30 min to give a colourless solution. After keeping the solution in air for a few days, colourless block-like crystals were formed.

Refinement

H2 and H4A were located in a difference Fourier map and refined isotropically, with Uiso fixed at 0.08 Å2. Other H atoms were positioned geometrically and refined using a riding model with d(O–H) = 0.82 Å, Uiso = 1.5Ueq(O), and d(C–H) = 0.93 - 0.96 Å, Uiso = 1.2 or 1.5Ueq(C).

Figures

Fig. 1.
The molecular structure of (I), with displacement ellipsoids drawn at the 30% probability level.
Fig. 2.
The molecular packing of (I), viewed along the c axis. Hydrogen bonds are shown as dashed lines.

Crystal data

C15H13BrN2O3·0.5CH4OF000 = 1480
Mr = 365.21Dx = 1.491 Mg m3
Monoclinic, P21/nMo Kα radiation λ = 0.71073 Å
Hall symbol: -P 2ynCell parameters from 1690 reflections
a = 12.906 (2) Åθ = 2.4–24.1º
b = 11.177 (2) ŵ = 2.54 mm1
c = 22.607 (3) ÅT = 298 (2) K
β = 93.706 (3)ºBlock, colourless
V = 3254.3 (9) Å30.20 × 0.18 × 0.17 mm
Z = 8

Data collection

Bruker SMART CCD area-detector diffractometer6725 independent reflections
Radiation source: fine-focus sealed tube2610 reflections with I > 2σ(I)
Monochromator: graphiteRint = 0.104
T = 298(2) Kθmax = 26.5º
ω scansθmin = 1.8º
Absorption correction: multi-scan(SADABS; Bruker, 2001)h = −16→16
Tmin = 0.630, Tmax = 0.672k = −13→14
21623 measured reflectionsl = −28→27

Refinement

Refinement on F2Secondary atom site location: difference Fourier map
Least-squares matrix: fullHydrogen site location: inferred from neighbouring sites
R[F2 > 2σ(F2)] = 0.061H atoms treated by a mixture of independent and constrained refinement
wR(F2) = 0.170  w = 1/[σ2(Fo2) + (0.0522P)2] where P = (Fo2 + 2Fc2)/3
S = 0.98(Δ/σ)max = 0.001
6725 reflectionsΔρmax = 0.51 e Å3
409 parametersΔρmin = −0.47 e Å3
2 restraintsExtinction correction: none
Primary atom site location: structure-invariant direct methods

Special details

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.

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

xyzUiso*/Ueq
Br10.89733 (6)−0.03746 (6)0.19990 (3)0.0896 (3)
Br2−0.27606 (8)0.47236 (11)0.74505 (4)0.1632 (5)
O10.4978 (3)−0.1249 (3)0.31384 (17)0.0705 (11)
O20.8013 (2)0.2809 (3)0.44744 (14)0.0499 (9)
O30.6978 (3)0.6557 (3)0.55948 (18)0.0680 (11)
H30.73890.67280.53460.102*
O40.1231 (4)0.3770 (4)0.6320 (2)0.0868 (14)
O5−0.1758 (3)0.7734 (3)0.48927 (15)0.0563 (10)
O6−0.0715 (3)1.1472 (3)0.37821 (15)0.0551 (10)
H6−0.12261.16030.39700.083*
O70.5718 (3)0.8519 (4)0.5649 (3)0.0984 (16)
H70.60180.79230.55370.148*
N10.6877 (3)0.1219 (3)0.38704 (17)0.0435 (10)
N20.6465 (3)0.1906 (4)0.43049 (18)0.0454 (11)
N3−0.0639 (3)0.6176 (4)0.55665 (18)0.0489 (11)
N4−0.0209 (3)0.6887 (4)0.51548 (18)0.0448 (11)
C10.6526 (4)−0.0203 (5)0.3091 (2)0.0476 (14)
C20.5840 (4)−0.1083 (5)0.2848 (2)0.0494 (14)
C30.6097 (5)−0.1693 (5)0.2347 (2)0.0599 (16)
H3A0.5641−0.22610.21790.072*
C40.7018 (5)−0.1475 (5)0.2094 (2)0.0623 (16)
H40.7181−0.18920.17560.075*
C50.7690 (4)−0.0647 (5)0.2338 (2)0.0532 (15)
C60.7453 (4)−0.0001 (4)0.2831 (2)0.0466 (14)
H6A0.79160.05710.29900.056*
C70.4258 (4)−0.2131 (5)0.2916 (3)0.0795 (19)
H7A0.4041−0.19490.25120.119*
H7B0.3664−0.21330.31510.119*
H7C0.4582−0.29040.29360.119*
C80.6233 (4)0.0517 (5)0.3595 (2)0.0485 (14)
H80.55600.04600.37170.058*
C90.7095 (4)0.2717 (4)0.4583 (2)0.0403 (12)
C100.6619 (4)0.3512 (4)0.5019 (2)0.0424 (13)
C110.7043 (4)0.4646 (4)0.5105 (2)0.0441 (13)
H110.76130.48770.49010.053*
C120.6614 (4)0.5429 (5)0.5494 (2)0.0475 (13)
C130.5772 (4)0.5085 (5)0.5794 (2)0.0562 (15)
H130.54870.56100.60580.067*
C140.5352 (4)0.3978 (5)0.5707 (2)0.0610 (16)
H140.47750.37580.59080.073*
C150.5772 (4)0.3173 (5)0.5321 (2)0.0533 (15)
H150.54860.24140.52670.064*
C160.0358 (7)0.3912 (5)0.6599 (3)0.075 (2)
C17−0.0323 (5)0.4802 (5)0.6358 (2)0.0563 (16)
C18−0.1248 (5)0.5010 (5)0.6608 (3)0.0716 (19)
H18−0.16930.55980.64480.086*
C19−0.1527 (7)0.4368 (8)0.7089 (3)0.105 (3)
C20−0.0841 (10)0.3495 (9)0.7327 (4)0.134 (5)
H20−0.10130.30620.76580.161*
C210.0056 (9)0.3278 (7)0.7085 (3)0.116 (4)
H210.04910.26840.72470.140*
C220.1976 (6)0.2885 (6)0.6549 (3)0.125 (3)
H22A0.22290.31050.69420.187*
H22B0.25460.28460.62970.187*
H22C0.16450.21160.65590.187*
C230.0025 (4)0.5525 (4)0.5873 (2)0.0501 (14)
H230.07190.55180.57840.060*
C24−0.0810 (4)0.7700 (4)0.4857 (2)0.0422 (13)
C25−0.0264 (4)0.8531 (4)0.4470 (2)0.0411 (13)
C26−0.0762 (4)0.9601 (4)0.43118 (19)0.0412 (12)
H26−0.14120.97710.44450.049*
C27−0.0283 (4)1.0406 (5)0.3956 (2)0.0429 (13)
C280.0680 (4)1.0164 (5)0.3763 (2)0.0561 (15)
H280.10071.07200.35320.067*
C290.1162 (4)0.9099 (5)0.3910 (2)0.0577 (15)
H290.18060.89270.37680.069*
C300.0696 (4)0.8282 (4)0.4267 (2)0.0455 (13)
H300.10300.75680.43700.055*
C310.6289 (6)0.9488 (7)0.5556 (5)0.173 (5)
H31A0.58891.01940.56220.260*
H31B0.64910.94840.51540.260*
H31C0.68980.94830.58230.260*
H20.5782 (11)0.183 (5)0.434 (2)0.080*
H4A0.0489 (9)0.695 (5)0.520 (2)0.080*

Atomic displacement parameters (Å2)

U11U22U33U12U13U23
Br10.1071 (6)0.0787 (5)0.0892 (5)0.0026 (4)0.0552 (4)0.0009 (4)
Br20.1725 (10)0.2271 (12)0.0980 (7)−0.1320 (9)0.0695 (6)−0.0473 (7)
O10.057 (3)0.071 (3)0.084 (3)−0.018 (2)0.008 (2)−0.022 (2)
O20.035 (2)0.056 (2)0.059 (2)0.0003 (18)0.0038 (17)−0.0118 (18)
O30.067 (3)0.046 (2)0.096 (3)−0.010 (2)0.042 (2)−0.018 (2)
O40.119 (4)0.055 (3)0.082 (3)0.019 (3)−0.028 (3)0.003 (2)
O50.040 (2)0.060 (2)0.070 (3)0.0084 (19)0.0117 (19)0.0173 (19)
O60.061 (3)0.046 (2)0.060 (2)0.0045 (19)0.0187 (19)0.0093 (19)
O70.047 (3)0.057 (3)0.193 (5)−0.005 (2)0.028 (3)−0.036 (3)
N10.047 (3)0.036 (3)0.048 (3)0.000 (2)0.004 (2)−0.008 (2)
N20.039 (3)0.044 (3)0.054 (3)−0.006 (2)0.012 (2)−0.017 (2)
N30.049 (3)0.046 (3)0.052 (3)−0.010 (2)0.005 (2)−0.001 (2)
N40.033 (3)0.048 (3)0.054 (3)−0.004 (2)0.004 (2)0.011 (2)
C10.060 (4)0.041 (3)0.042 (3)0.002 (3)0.000 (3)0.001 (3)
C20.055 (4)0.041 (3)0.051 (4)0.007 (3)−0.004 (3)−0.006 (3)
C30.081 (5)0.045 (4)0.051 (4)0.001 (3)−0.011 (3)−0.006 (3)
C40.094 (5)0.046 (4)0.047 (4)0.002 (4)0.012 (3)−0.009 (3)
C50.073 (4)0.043 (4)0.046 (3)0.000 (3)0.019 (3)0.005 (3)
C60.054 (4)0.036 (3)0.050 (3)−0.002 (3)0.002 (3)0.002 (3)
C70.056 (4)0.071 (4)0.110 (5)−0.014 (4)−0.009 (4)0.000 (4)
C80.045 (3)0.049 (4)0.053 (3)−0.001 (3)0.014 (3)−0.004 (3)
C90.041 (3)0.036 (3)0.044 (3)0.002 (3)0.004 (3)0.001 (3)
C100.038 (3)0.042 (3)0.047 (3)0.002 (3)0.004 (2)−0.005 (3)
C110.034 (3)0.045 (3)0.054 (3)0.000 (3)0.011 (2)−0.004 (3)
C120.042 (3)0.043 (3)0.059 (3)−0.002 (3)0.015 (3)−0.007 (3)
C130.064 (4)0.050 (4)0.058 (4)−0.003 (3)0.025 (3)−0.018 (3)
C140.064 (4)0.065 (4)0.057 (4)−0.011 (3)0.028 (3)−0.013 (3)
C150.059 (4)0.049 (4)0.053 (4)−0.020 (3)0.013 (3)−0.011 (3)
C160.134 (7)0.033 (4)0.055 (5)−0.025 (4)−0.021 (5)0.008 (3)
C170.075 (4)0.049 (4)0.044 (4)−0.025 (3)−0.002 (3)0.003 (3)
C180.096 (5)0.069 (5)0.048 (4)−0.043 (4)−0.002 (4)−0.001 (3)
C190.151 (8)0.114 (7)0.050 (5)−0.074 (6)0.016 (5)−0.008 (5)
C200.235 (15)0.115 (9)0.052 (6)−0.108 (10)0.002 (7)0.018 (5)
C210.219 (12)0.061 (5)0.063 (6)−0.039 (7)−0.034 (6)0.020 (5)
C220.175 (8)0.067 (5)0.120 (6)0.046 (5)−0.082 (6)−0.020 (4)
C230.054 (4)0.042 (3)0.054 (4)−0.001 (3)0.002 (3)0.001 (3)
C240.038 (3)0.041 (3)0.047 (3)−0.001 (3)0.001 (3)−0.004 (3)
C250.040 (3)0.042 (3)0.041 (3)−0.006 (3)0.002 (2)−0.001 (3)
C260.040 (3)0.048 (3)0.035 (3)0.000 (3)0.000 (2)−0.003 (3)
C270.050 (3)0.038 (3)0.042 (3)0.002 (3)0.005 (3)−0.002 (3)
C280.051 (4)0.057 (4)0.062 (4)−0.004 (3)0.018 (3)0.010 (3)
C290.043 (3)0.061 (4)0.071 (4)0.003 (3)0.022 (3)0.005 (3)
C300.038 (3)0.046 (3)0.052 (3)0.009 (3)0.005 (3)0.000 (3)
C310.093 (6)0.077 (6)0.357 (15)−0.022 (5)0.076 (8)−0.013 (8)

Geometric parameters (Å, °)

Br1—C51.893 (5)C10—C111.389 (6)
Br2—C191.879 (9)C11—C121.382 (6)
O1—C21.342 (6)C11—H110.9300
O1—C71.423 (6)C12—C131.372 (7)
O2—C91.230 (5)C13—C141.360 (7)
O3—C121.360 (5)C13—H130.9300
O3—H30.8200C14—C151.387 (7)
O4—C161.336 (8)C14—H140.9300
O4—C221.452 (6)C15—H150.9300
O5—C241.233 (5)C16—C211.384 (9)
O6—C271.363 (5)C16—C171.413 (8)
O6—H60.8200C17—C181.374 (8)
O7—C311.335 (7)C17—C231.456 (7)
O7—H70.8200C18—C191.370 (9)
N1—C81.276 (5)C18—H180.9300
N1—N21.379 (5)C19—C201.401 (12)
N2—C91.346 (6)C20—C211.335 (12)
N2—H20.894 (10)C20—H200.9300
N3—C231.290 (6)C21—H210.9300
N3—N41.369 (5)C22—H22A0.9600
N4—C241.347 (6)C22—H22B0.9600
N4—H4A0.902 (10)C22—H22C0.9600
C1—C61.384 (7)C23—H230.9300
C1—C21.411 (7)C24—C251.484 (6)
C1—C81.465 (7)C25—C301.377 (6)
C2—C31.380 (7)C25—C261.393 (6)
C3—C41.374 (7)C26—C271.380 (6)
C3—H3A0.9300C26—H260.9300
C4—C51.361 (7)C27—C281.371 (7)
C4—H40.9300C28—C291.374 (7)
C5—C61.380 (7)C28—H280.9300
C6—H6A0.9300C29—C301.382 (6)
C7—H7A0.9600C29—H290.9300
C7—H7B0.9600C30—H300.9300
C7—H7C0.9600C31—H31A0.9600
C8—H80.9300C31—H31B0.9600
C9—C101.489 (6)C31—H31C0.9600
C10—C151.379 (6)
C2—O1—C7117.8 (4)C10—C15—C14119.2 (5)
C12—O3—H3109.5C10—C15—H15120.4
C16—O4—C22118.1 (6)C14—C15—H15120.4
C27—O6—H6109.5O4—C16—C21127.1 (8)
C31—O7—H7109.5O4—C16—C17115.0 (6)
C8—N1—N2114.9 (4)C21—C16—C17117.8 (8)
C9—N2—N1117.3 (4)C18—C17—C16119.7 (6)
C9—N2—H2126 (3)C18—C17—C23122.3 (6)
N1—N2—H2116 (3)C16—C17—C23117.9 (6)
C23—N3—N4114.1 (4)C19—C18—C17121.2 (7)
C24—N4—N3119.1 (4)C19—C18—H18119.4
C24—N4—H4A123 (3)C17—C18—H18119.4
N3—N4—H4A115 (3)C18—C19—C20118.5 (9)
C6—C1—C2119.1 (5)C18—C19—Br2120.6 (8)
C6—C1—C8120.9 (5)C20—C19—Br2120.8 (7)
C2—C1—C8119.9 (5)C21—C20—C19120.8 (9)
O1—C2—C3125.8 (5)C21—C20—H20119.6
O1—C2—C1115.2 (5)C19—C20—H20119.6
C3—C2—C1119.1 (5)C20—C21—C16121.9 (10)
C4—C3—C2120.9 (5)C20—C21—H21119.0
C4—C3—H3A119.5C16—C21—H21119.0
C2—C3—H3A119.5O4—C22—H22A109.5
C5—C4—C3119.9 (5)O4—C22—H22B109.5
C5—C4—H4120.1H22A—C22—H22B109.5
C3—C4—H4120.1O4—C22—H22C109.5
C4—C5—C6121.0 (5)H22A—C22—H22C109.5
C4—C5—Br1119.8 (4)H22B—C22—H22C109.5
C6—C5—Br1119.2 (4)N3—C23—C17119.4 (5)
C5—C6—C1120.0 (5)N3—C23—H23120.3
C5—C6—H6A120.0C17—C23—H23120.3
C1—C6—H6A120.0O5—C24—N4122.0 (5)
O1—C7—H7A109.5O5—C24—C25122.1 (5)
O1—C7—H7B109.5N4—C24—C25116.0 (5)
H7A—C7—H7B109.5C30—C25—C26119.9 (5)
O1—C7—H7C109.5C30—C25—C24122.8 (5)
H7A—C7—H7C109.5C26—C25—C24117.4 (4)
H7B—C7—H7C109.5C27—C26—C25119.6 (5)
N1—C8—C1121.7 (5)C27—C26—H26120.2
N1—C8—H8119.2C25—C26—H26120.2
C1—C8—H8119.2O6—C27—C28116.3 (5)
O2—C9—N2121.6 (5)O6—C27—C26123.3 (5)
O2—C9—C10121.7 (5)C28—C27—C26120.4 (5)
N2—C9—C10116.7 (4)C27—C28—C29120.0 (5)
C15—C10—C11119.9 (4)C27—C28—H28120.0
C15—C10—C9122.5 (5)C29—C28—H28120.0
C11—C10—C9117.5 (4)C28—C29—C30120.4 (5)
C12—C11—C10119.8 (5)C28—C29—H29119.8
C12—C11—H11120.1C30—C29—H29119.8
C10—C11—H11120.1C25—C30—C29119.7 (5)
O3—C12—C13117.0 (5)C25—C30—H30120.1
O3—C12—C11123.1 (5)C29—C30—H30120.1
C13—C12—C11119.9 (5)O7—C31—H31A109.5
C14—C13—C12120.3 (5)O7—C31—H31B109.5
C14—C13—H13119.8H31A—C31—H31B109.5
C12—C13—H13119.8O7—C31—H31C109.5
C13—C14—C15120.8 (5)H31A—C31—H31C109.5
C13—C14—H14119.6H31B—C31—H31C109.5
C15—C14—H14119.6

Hydrogen-bond geometry (Å, °)

D—H···AD—HH···AD···AD—H···A
N4—H4A···O2i0.902 (10)2.045 (18)2.923 (5)164 (5)
N2—H2···O7i0.894 (10)1.977 (13)2.866 (5)173 (5)
O7—H7···O30.821.962.737 (5)157
O6—H6···N1ii0.822.483.140 (5)138
O6—H6···O2ii0.822.062.777 (5)146
O3—H3···N3iii0.822.643.110 (6)118
O3—H3···O5iii0.821.922.692 (5)157

Symmetry codes: (i) −x+1, −y+1, −z+1; (ii) x−1, y+1, z; (iii) x+1, y, z.

Footnotes

Supplementary data and figures for this paper are available from the IUCr electronic archives (Reference: AT2575).

References

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