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Acta Crystallogr Sect E Struct Rep Online. 2008 February 1; 64(Pt 2): o514.
Published online 2008 January 25. doi:  10.1107/S1600536808002250
PMCID: PMC2960470

N′-(5-Bromo-2-hydroxy­benzyl­idene)-3-hydroxy­benzohydrazide

Abstract

The asymmetric unit of the title compound, C14H11BrN2O3, contains two crystallographically independent mol­ecules with slightly different conformations with respect to the aromatic rings; the dihedral angles between the two benzene rings in the two mol­ecules are 55.0 (7) and 16.3 (7)°. In the crystal structure, mol­ecules are linked through inter­molecular N—H(...)O, O—H(...)O and O—H(...)N hydrogen bonds, forming chains running along the a axis.

Related literature

For related literature, see: Akitsu & Einaga (2006 [triangle]); Bahner et al. (1968 [triangle]); Butcher et al. (2005 [triangle]); Hodnett & Mooney (1970 [triangle]); Merchant & Chothia (1970 [triangle]); Pradeep (2005 [triangle]); Sigman & Jacobsen (1998 [triangle]).

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Object name is e-64-0o514-scheme1.jpg

Experimental

Crystal data

  • C14H11BrN2O3
  • M r = 335.16
  • Triclinic, An external file that holds a picture, illustration, etc.
Object name is e-64-0o514-efi1.jpg
  • a = 6.295 (3) Å
  • b = 14.988 (4) Å
  • c = 15.423 (3) Å
  • α = 70.97 (2)°
  • β = 80.64 (2)°
  • γ = 78.02 (2)°
  • V = 1338.6 (8) Å3
  • Z = 4
  • Mo Kα radiation
  • μ = 3.08 mm−1
  • T = 298 (2) K
  • 0.20 × 0.18 × 0.18 mm

Data collection

  • Bruker SMART APEX area-detector diffractometer
  • Absorption correction: multi-scan (SADABS; Sheldrick, 1996 [triangle]) T min = 0.549, T max = 0.577
  • 11037 measured reflections
  • 5652 independent reflections
  • 2286 reflections with I > 2σ(I)
  • R int = 0.078

Refinement

  • R[F 2 > 2σ(F 2)] = 0.072
  • wR(F 2) = 0.193
  • S = 0.93
  • 5652 reflections
  • 371 parameters
  • 2 restraints
  • H atoms treated by a mixture of independent and constrained refinement
  • Δρmax = 0.70 e Å−3
  • Δρmin = −0.50 e Å−3

Data collection: SMART (Siemens, 1996 [triangle]); cell refinement: SAINT (Siemens, 1996 [triangle]); data reduction: SAINT; program(s) used to solve structure: SHELXS97 (Sheldrick, 2008 [triangle]); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008 [triangle]); molecular graphics: SHELXTL (Sheldrick, 2008 [triangle]); software used to prepare material for publication: SHELXL97.

Table 1
Hydrogen-bond geometry (Å, °)

Supplementary Material

Crystal structure: contains datablocks global, I. DOI: 10.1107/S1600536808002250/rz2193sup1.cif

Structure factors: contains datablocks I. DOI: 10.1107/S1600536808002250/rz2193Isup2.hkl

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

supplementary crystallographic information

Comment

Schiff base compounds have been widely investigated due to their easy synthesis, versatile structures and widely applications (Sigman & Jacobsen, 1998; Akitsu & Einaga, 2006; Pradeep, 2005; Butcher et al., 2005). The excellent antibacterial and antitumor properties of such compounds have attracted much interest in recent years (Hodnett & Mooney, 1970; Bahner et al., 1968; Merchant & Chothia, 1970). In order to further investigate the structures of such compounds, a new Schiff base compound is reported in this paper.

The asymmetric unit of the title compound contains two crystallographically independent molecules (Fig. 1) with slightly different conformation with respect to the aromatic ring planes. The dihedral angles between the two benzene rings in the molecules are 55.0 (7) and 16.3 (7)°, respectively. The molecular conformation is stabilized by intramolecular N—H···O hydrogen bonding interactions (Table 1). In the crystal structure, molecules are linked through intermolecular N–H···O and O–H···O hydrogen bonds (Table 1), forming chains running along the a axis (Fig. 2).

Experimental

The title compound was obtained by stirring of 5-bromosalicylaldehyde (0.1 mmol, 20.1 mg) and 3-hydroxybenzoic acid hydrazide (0.1 mmol, 15.2 mg) in a methanol solution (10 ml) at room temperature. Yellow block-shaped single crystals suitable for X-ray diffraction were formed from the solution after three days.

Refinement

H2 and H4B were located from a difference Fourier map and refined isotropically, with N–H distances restrained to 0.90 (1) Å, and with Uiso(H) set to 0.08 Å2. Other H atoms were positioned geometrically (C–H = 0.93Å and O–H = 0.82 Å) and refined as riding, with Uiso(H) = 1.2Ueq(C) and 1.5Ueq(O).

Figures

Fig. 1.
The molecular structure of the title compound with 30% probability ellipsoids.
Fig. 2.
Molecular packing of the title compound. Hydrogen atoms not involved in intermolecular hydrogen bonds (dashed lines) are omitted for clarity.

Crystal data

C14H11BrN2O3Z = 4
Mr = 335.16F000 = 672
Triclinic, P1Dx = 1.663 Mg m3
Hall symbol: -P 1Mo Kα radiation λ = 0.71073 Å
a = 6.295 (3) ÅCell parameters from 819 reflections
b = 14.988 (4) Åθ = 2.3–24.3º
c = 15.423 (3) ŵ = 3.08 mm1
α = 70.97 (2)ºT = 298 (2) K
β = 80.64 (2)ºBlock, yellow
γ = 78.02 (2)º0.20 × 0.18 × 0.18 mm
V = 1338.6 (8) Å3

Data collection

Bruker SMART APEX area-detector diffractometer5652 independent reflections
Radiation source: fine-focus sealed tube2286 reflections with I > 2σ(I)
Monochromator: graphiteRint = 0.078
T = 298(2) Kθmax = 27.0º
ω scansθmin = 1.4º
Absorption correction: multi-scan(SADABS; Sheldrick, 1996)h = −7→7
Tmin = 0.549, Tmax = 0.577k = −19→19
11037 measured reflectionsl = −19→19

Refinement

Refinement on F2Secondary atom site location: difference Fourier map
Least-squares matrix: fullHydrogen site location: inferred from neighbouring sites
R[F2 > 2σ(F2)] = 0.072H atoms treated by a mixture of independent and constrained refinement
wR(F2) = 0.193  w = 1/[σ2(Fo2) + (0.0728P)2] where P = (Fo2 + 2Fc2)/3
S = 0.93(Δ/σ)max < 0.001
5652 reflectionsΔρmax = 0.70 e Å3
371 parametersΔρmin = −0.50 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
Br10.88585 (14)0.92277 (7)0.36574 (6)0.0631 (3)
Br21.22791 (15)0.68828 (8)0.26774 (6)0.0759 (4)
O10.1995 (9)0.8047 (5)0.6860 (4)0.0657 (17)
H10.22240.81730.73120.099*
O20.1318 (8)0.8815 (4)0.9236 (4)0.0558 (15)
O30.1855 (9)1.0107 (5)1.1872 (4)0.0620 (16)
H30.07781.03651.15930.093*
O40.5513 (9)0.5809 (5)0.5941 (4)0.0649 (17)
H40.58710.58660.64060.097*
O50.5448 (9)0.6020 (4)0.8512 (3)0.0600 (16)
O60.7038 (9)0.5109 (5)1.1850 (3)0.0656 (17)
H60.57970.50501.18050.098*
N10.4379 (10)0.8497 (4)0.7878 (4)0.0450 (16)
N20.4909 (11)0.8521 (5)0.8700 (4)0.0530 (18)
N30.8090 (10)0.6223 (5)0.6916 (4)0.0504 (18)
N40.8723 (10)0.6282 (5)0.7716 (4)0.0491 (17)
C10.5485 (13)0.8594 (5)0.6307 (5)0.047 (2)
C20.3583 (13)0.8316 (6)0.6156 (6)0.050 (2)
C30.3325 (14)0.8293 (6)0.5294 (6)0.058 (2)
H3A0.20830.81020.52070.069*
C40.4872 (14)0.8549 (6)0.4561 (6)0.059 (2)
H4A0.46820.85300.39820.070*
C50.6726 (13)0.8837 (5)0.4693 (5)0.049 (2)
C60.7046 (12)0.8877 (5)0.5549 (5)0.049 (2)
H6A0.82760.90880.56210.059*
C70.5847 (14)0.8639 (5)0.7195 (5)0.051 (2)
H70.71720.87740.72690.061*
C80.3276 (13)0.8706 (5)0.9354 (5)0.044 (2)
C90.3987 (13)0.8760 (5)1.0207 (5)0.044 (2)
C100.2543 (12)0.9334 (5)1.0679 (5)0.045 (2)
H100.11600.96071.04930.054*
C110.3203 (13)0.9490 (6)1.1430 (5)0.052 (2)
C120.5208 (13)0.9068 (6)1.1729 (5)0.053 (2)
H120.56490.91821.22250.064*
C130.6573 (14)0.8467 (6)1.1277 (6)0.061 (2)
H130.78980.81491.15030.073*
C140.6038 (13)0.8326 (6)1.0512 (6)0.056 (2)
H140.70170.79501.02010.067*
C150.9095 (12)0.6284 (5)0.5347 (5)0.044 (2)
C160.7120 (13)0.6035 (5)0.5224 (5)0.046 (2)
C170.6807 (13)0.5990 (6)0.4375 (6)0.057 (2)
H170.55590.57840.43140.069*
C180.8289 (13)0.6240 (6)0.3624 (6)0.056 (2)
H180.80240.62290.30510.067*
C191.0199 (13)0.6510 (6)0.3722 (5)0.052 (2)
C201.0584 (12)0.6519 (6)0.4565 (5)0.049 (2)
H201.18850.66870.46210.059*
C210.9532 (13)0.6323 (5)0.6225 (5)0.048 (2)
H211.09010.64250.62860.058*
C220.7317 (13)0.6159 (5)0.8508 (5)0.046 (2)
C230.8148 (11)0.6196 (5)0.9341 (5)0.0408 (19)
C240.7138 (12)0.5723 (5)1.0196 (5)0.048 (2)
H240.59210.54511.02200.057*
C250.7917 (13)0.5653 (6)1.1006 (5)0.047 (2)
C260.9760 (13)0.6038 (6)1.0988 (6)0.052 (2)
H261.03200.59641.15340.063*
C271.0751 (12)0.6534 (5)1.0148 (5)0.047 (2)
H271.19330.68241.01330.056*
C280.9992 (12)0.6601 (5)0.9322 (6)0.050 (2)
H281.07030.69120.87610.060*
H20.615 (7)0.860 (6)0.886 (5)0.080*
H4B1.004 (6)0.643 (6)0.771 (5)0.080*

Atomic displacement parameters (Å2)

U11U22U33U12U13U23
Br10.0515 (6)0.0820 (7)0.0483 (6)−0.0067 (5)0.0040 (4)−0.0167 (5)
Br20.0608 (6)0.1244 (10)0.0477 (6)−0.0376 (6)0.0053 (5)−0.0243 (6)
O10.055 (4)0.095 (5)0.056 (4)−0.035 (3)0.002 (3)−0.025 (4)
O20.038 (3)0.077 (4)0.058 (4)−0.011 (3)−0.001 (3)−0.029 (3)
O30.043 (3)0.100 (5)0.056 (4)−0.015 (3)0.002 (3)−0.042 (4)
O40.054 (4)0.095 (5)0.051 (4)−0.033 (3)−0.002 (3)−0.017 (4)
O50.045 (4)0.090 (5)0.048 (3)−0.031 (3)−0.005 (3)−0.013 (3)
O60.045 (4)0.112 (5)0.042 (3)−0.028 (4)−0.001 (3)−0.019 (3)
N10.046 (4)0.049 (4)0.042 (4)−0.005 (3)0.000 (3)−0.019 (3)
N20.043 (4)0.076 (5)0.041 (4)−0.007 (4)−0.001 (3)−0.023 (4)
N30.039 (4)0.067 (5)0.040 (4)−0.005 (3)−0.003 (3)−0.013 (4)
N40.035 (4)0.071 (5)0.045 (4)−0.018 (4)−0.002 (3)−0.017 (4)
C10.053 (5)0.034 (5)0.048 (5)−0.004 (4)0.003 (4)−0.011 (4)
C20.041 (5)0.057 (6)0.055 (6)−0.011 (4)−0.008 (4)−0.016 (4)
C30.052 (6)0.068 (6)0.057 (6)−0.017 (5)−0.009 (5)−0.019 (5)
C40.061 (6)0.075 (7)0.049 (5)−0.020 (5)−0.001 (5)−0.028 (5)
C50.051 (5)0.044 (5)0.039 (5)0.008 (4)0.000 (4)−0.006 (4)
C60.042 (5)0.052 (6)0.055 (5)−0.011 (4)−0.010 (4)−0.013 (4)
C70.054 (5)0.058 (6)0.043 (5)−0.014 (4)−0.001 (4)−0.017 (4)
C80.048 (5)0.040 (5)0.046 (5)−0.011 (4)−0.005 (4)−0.013 (4)
C90.049 (5)0.041 (5)0.039 (5)−0.007 (4)−0.002 (4)−0.012 (4)
C100.038 (5)0.053 (5)0.039 (5)−0.009 (4)0.003 (4)−0.010 (4)
C110.046 (5)0.066 (6)0.043 (5)−0.018 (5)0.001 (4)−0.013 (4)
C120.052 (6)0.069 (6)0.040 (5)−0.010 (5)−0.009 (4)−0.016 (4)
C130.057 (6)0.054 (6)0.058 (6)0.002 (5)−0.015 (5)−0.001 (5)
C140.049 (5)0.062 (6)0.057 (6)−0.007 (5)−0.007 (4)−0.019 (5)
C150.039 (5)0.057 (6)0.040 (5)−0.012 (4)−0.006 (4)−0.015 (4)
C160.049 (5)0.050 (5)0.041 (5)−0.014 (4)−0.008 (4)−0.011 (4)
C170.046 (5)0.076 (7)0.057 (6)−0.020 (5)−0.008 (5)−0.021 (5)
C180.049 (5)0.065 (6)0.059 (6)−0.008 (5)−0.016 (5)−0.023 (5)
C190.047 (5)0.067 (6)0.041 (5)−0.010 (4)−0.005 (4)−0.017 (4)
C200.037 (5)0.064 (6)0.052 (5)−0.022 (4)−0.001 (4)−0.018 (4)
C210.041 (5)0.053 (6)0.047 (5)−0.009 (4)−0.007 (4)−0.009 (4)
C220.036 (5)0.041 (5)0.056 (5)−0.012 (4)0.000 (4)−0.009 (4)
C230.031 (4)0.041 (5)0.056 (5)−0.005 (4)−0.012 (4)−0.019 (4)
C240.033 (4)0.057 (6)0.059 (5)−0.023 (4)0.011 (4)−0.024 (4)
C250.040 (5)0.058 (6)0.049 (5)−0.002 (4)−0.005 (4)−0.025 (4)
C260.045 (5)0.061 (6)0.056 (5)−0.007 (4)−0.006 (4)−0.027 (5)
C270.042 (5)0.040 (5)0.061 (5)−0.013 (4)−0.012 (4)−0.012 (4)
C280.044 (5)0.049 (5)0.059 (5)−0.015 (4)0.001 (4)−0.015 (4)

Geometric parameters (Å, °)

Br1—C51.928 (7)C9—C141.400 (10)
Br2—C191.912 (8)C9—C101.401 (9)
O1—C21.368 (9)C10—C111.395 (10)
O1—H10.8200C10—H100.9300
O2—C81.245 (9)C11—C121.369 (11)
O3—C111.392 (9)C12—C131.388 (10)
O3—H30.8200C12—H120.9300
O4—C161.377 (8)C13—C141.369 (11)
O4—H40.8200C13—H130.9300
O5—C221.235 (8)C14—H140.9300
O6—C251.388 (9)C15—C201.396 (9)
O6—H60.8200C15—C161.427 (10)
N1—C71.276 (8)C15—C211.447 (10)
N1—N21.375 (8)C16—C171.380 (10)
N2—C81.371 (9)C17—C181.365 (10)
N2—H20.90 (6)C17—H170.9300
N3—C211.273 (8)C18—C191.391 (11)
N3—N41.390 (8)C18—H180.9300
N4—C221.371 (9)C19—C201.365 (10)
N4—H4B0.90 (5)C20—H200.9300
C1—C61.410 (10)C21—H210.9300
C1—C21.422 (10)C22—C231.485 (10)
C1—C71.450 (10)C23—C241.397 (10)
C2—C31.377 (10)C23—C281.410 (10)
C3—C41.374 (10)C24—C251.380 (10)
C3—H3A0.9300C24—H240.9300
C4—C51.391 (11)C25—C261.392 (10)
C4—H4A0.9300C26—C271.386 (10)
C5—C61.388 (10)C26—H260.9300
C6—H6A0.9300C27—C281.398 (10)
C7—H70.9300C27—H270.9300
C8—C91.488 (10)C28—H280.9300
C2—O1—H1109.5C14—C13—C12122.3 (8)
C11—O3—H3109.5C14—C13—H13118.8
C16—O4—H4109.5C12—C13—H13118.8
C25—O6—H6109.5C13—C14—C9118.7 (8)
C7—N1—N2116.6 (7)C13—C14—H14120.7
C8—N2—N1119.5 (6)C9—C14—H14120.7
C8—N2—H2107 (5)C20—C15—C16116.6 (7)
N1—N2—H2132 (5)C20—C15—C21120.9 (7)
C21—N3—N4115.7 (7)C16—C15—C21122.5 (7)
C22—N4—N3120.6 (6)O4—C16—C17118.2 (7)
C22—N4—H4B119 (5)O4—C16—C15121.7 (7)
N3—N4—H4B120 (5)C17—C16—C15120.1 (7)
C6—C1—C2118.4 (7)C18—C17—C16121.5 (8)
C6—C1—C7118.5 (8)C18—C17—H17119.3
C2—C1—C7123.1 (7)C16—C17—H17119.3
O1—C2—C3118.5 (7)C17—C18—C19119.3 (8)
O1—C2—C1121.2 (7)C17—C18—H18120.3
C3—C2—C1120.4 (8)C19—C18—H18120.3
C4—C3—C2121.1 (8)C20—C19—C18120.0 (7)
C4—C3—H3A119.4C20—C19—Br2119.8 (6)
C2—C3—H3A119.4C18—C19—Br2120.2 (6)
C3—C4—C5119.3 (8)C19—C20—C15122.4 (7)
C3—C4—H4A120.4C19—C20—H20118.8
C5—C4—H4A120.4C15—C20—H20118.8
C6—C5—C4121.6 (7)N3—C21—C15121.7 (7)
C6—C5—Br1119.2 (7)N3—C21—H21119.2
C4—C5—Br1119.2 (6)C15—C21—H21119.2
C5—C6—C1119.3 (8)O5—C22—N4120.2 (7)
C5—C6—H6A120.4O5—C22—C23122.6 (7)
C1—C6—H6A120.4N4—C22—C23117.2 (7)
N1—C7—C1121.1 (8)C24—C23—C28118.4 (7)
N1—C7—H7119.5C24—C23—C22117.1 (7)
C1—C7—H7119.5C28—C23—C22124.2 (7)
O2—C8—N2121.4 (7)C25—C24—C23121.1 (7)
O2—C8—C9122.5 (7)C25—C24—H24119.5
N2—C8—C9116.1 (7)C23—C24—H24119.5
C14—C9—C10119.9 (7)C24—C25—O6120.9 (7)
C14—C9—C8123.5 (7)C24—C25—C26120.6 (8)
C10—C9—C8116.5 (7)O6—C25—C26118.2 (7)
C11—C10—C9119.3 (7)C27—C26—C25119.3 (8)
C11—C10—H10120.4C27—C26—H26120.4
C9—C10—H10120.4C25—C26—H26120.4
C12—C11—O3118.7 (7)C26—C27—C28120.6 (7)
C12—C11—C10120.9 (8)C26—C27—H27119.7
O3—C11—C10120.3 (7)C28—C27—H27119.7
C11—C12—C13118.8 (8)C27—C28—C23119.9 (7)
C11—C12—H12120.6C27—C28—H28120.0
C13—C12—H12120.6C23—C28—H28120.0

Hydrogen-bond geometry (Å, °)

D—H···AD—HH···AD···AD—H···A
N4—H4B···O6i0.90 (5)2.60 (8)3.045 (9)111 (6)
N2—H2···O3ii0.90 (6)2.39 (7)3.021 (9)127 (7)
O6—H6···O5iii0.822.142.760 (8)132
O4—H4···N30.821.952.665 (8)145
O3—H3···O2iv0.821.932.737 (8)167
O1—H1···N10.821.942.654 (8)145

Symmetry codes: (i) −x+2, −y+1, −z+2; (ii) −x+1, −y+2, −z+2; (iii) −x+1, −y+1, −z+2; (iv) −x, −y+2, −z+2.

Footnotes

Supplementary data and figures for this paper are available from the IUCr electronic archives (Reference: RZ2193).

References

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  • Butcher, R. J., Basu Baul, T. S., Singh, K. S. & Smith, F. E. (2005). Acta Cryst. E61, o1007–o1009.
  • Hodnett, E. M. & Mooney, P. D. (1970). J. Med. Chem.13, 786–786. [PubMed]
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