Supporting information
Crystallographic Information File (CIF) https://doi.org/10.1107/S1600536807040603/at2377sup1.cif | |
Structure factor file (CIF format) https://doi.org/10.1107/S1600536807040603/at2377Isup2.hkl |
CCDC reference: 660328
Key indicators
- Single-crystal X-ray study
- T = 173 K
- Mean (C-C) = 0.003 Å
- R factor = 0.032
- wR factor = 0.064
- Data-to-parameter ratio = 17.7
checkCIF/PLATON results
No syntax errors found
Alert level C PLAT062_ALERT_4_C Rescale T(min) & T(max) by ..................... 0.94 PLAT222_ALERT_3_C Large Non-Solvent H Ueq(max)/Ueq(min) ... 3.45 Ratio PLAT431_ALERT_2_C Short Inter HL..A Contact Br1 .. O17 .. 3.33 Ang.
Alert level G ABSTM02_ALERT_3_G When printed, the submitted absorption T values will be replaced by the scaled T values. Since the ratio of scaled T's is identical to the ratio of reported T values, the scaling does not imply a change to the absorption corrections used in the study. Ratio of Tmax expected/reported 0.935 Tmax scaled 0.541 Tmin scaled 0.497 REFLT03_ALERT_4_G Please check that the estimate of the number of Friedel pairs is correct. If it is not, please give the correct count in the _publ_section_exptl_refinement section of the submitted CIF. From the CIF: _diffrn_reflns_theta_max 27.56 From the CIF: _reflns_number_total 3536 Count of symmetry unique reflns 2039 Completeness (_total/calc) 173.42% TEST3: Check Friedels for noncentro structure Estimate of Friedel pairs measured 1497 Fraction of Friedel pairs measured 0.734 Are heavy atom types Z>Si present yes
0 ALERT level A = In general: serious problem 0 ALERT level B = Potentially serious problem 3 ALERT level C = Check and explain 2 ALERT level G = General alerts; check 0 ALERT type 1 CIF construction/syntax error, inconsistent or missing data 1 ALERT type 2 Indicator that the structure model may be wrong or deficient 2 ALERT type 3 Indicator that the structure quality may be low 2 ALERT type 4 Improvement, methodology, query or suggestion 0 ALERT type 5 Informative message, check
A mixture of 2-bromo-5-methoxybenzohydrazide (0.735 g, 0.003 mol) and 4-hydroxybenzaldehyde (0.366 g, 0.003 mol) in 15 ml of absolute ethanol containing 2 drops of sulfuric acid was refluxed for about 3 h. On cooling, the solid separated was filtered and recrystalized from DMF (m.p.: above 523 K). Analysis found: C 51.51, H 3.71, N 7.95%; C15H13BrN2O3, requires: C 51.60, H 3.75, N 8.02%.
H atoms were found in a difference map, but those bonded to C were refined using a riding model with C—H = 0.95 Å and Uiso(H) = 1.2Ueq(C) for Caromatic and C—H = 0.98 Å and Uiso(H) = 1.5Ueq(C) for Cmethyl. The methyl group was allowed to rotate but not to tip. The H atoms bonded to N and O were freely refined.
Schiff bases are known to have biological activities such as antimicrobial (El-Masry et al., 2000; Pandey et al., 1999), antifungal (Singh et al., 1988; Varma et al., 1986), antitumor (Hodnett et al., 1970; Misra et al. 1981; Desai et al., 2001), and as herbicides. Schiff bases have also been employed as ligands for complexation of metal ions (Aydoğan et al., 2001). On the industrial scale, they have wide range of applications such as dyes and pigments (Taggi et al., 2002). The crystal structures of 2-bromo-N-[(E)-4-chlorobenzylidene]-5-methoxybenzohydrazide (Butcher et al., 2007), 2-bromo-5-methoxy-N-[(E)-(2-nitrophenyl)methylene]benzohydrazide (Yathirajan et al., 2007), 2-bromo-N-[(E)-(4-fluorophenyl)methylene]-5-methoxybenzohydrazide monohydrate (Narayana et al., 2007), N'-[(1E)-(5-chloro-2-hydroxyphenyl)(phenyl)methylene]-2-hydroxybenzohydrazide (Chang et al., 2007), 2'-(3,4-dimethoxybenzylidene)-2-hydroxybenzohydrazide, (Yang & Pan, 2004) and 2'-(2-fluorobenzylidene)-2-hydroxybenzohydrazide (Yang & Pan, 2005) have been reported. A new Schiff base, C15H13BrN2O3, was synthesized and its crystal structure is here reported.
Geometric parameters of the title compound (Fig. 1) are in the usual ranges. The C═N double bond is trans configured. The C═N—N—CO– moiety itself is planar (r.m.s. deviation 0.044 Å). It makes a dihedral angle of 10.73 (19)°, with the hydroxyphenyl ring, but forms a dihedral angle of 67.90 (8)° with the other aromatic ring. The crystal packing is stabilized by N—H···O, O—H···O and O—H···N hydrogen bonds. The hydroxyl group forms a bifurcated H bond to the hydrazon N atom and the carbonyl group.
For related structures, see: Yang & Pan (2004; 2005); Butcher et al. (2007); Chang et al. (2007); Narayana et al. (2007); Yathirajan et al. (2007). For related literature, see: Hodnett & Dunn (1970); Misra et al. (1981); Varma et al. (1986); Singh & Dash (1988); Pandey et al. (1999); El-Masry et al. (2000); Aydoğan et al. (2001); Desai et al. (2001); Taggi et al. (2002).
Data collection: X-AREA (Stoe & Cie, 2001); cell refinement: X-AREA; data reduction: X-AREA [Or X-RED ?]; program(s) used to solve structure: SHELXS97 (Sheldrick, 1990); program(s) used to refine structure: SHELXL97 (Sheldrick, 1997); molecular graphics: PLATON (Spek, 2003); software used to prepare material for publication: SHELXL97.
Fig. 1. Perspective view of the title compound with the atom numbering; displacement ellipsoids are at the 50% probability level. | |
Fig. 2. The formation of the title compound. |
C15H13BrN2O3 | F(000) = 704 |
Mr = 349.18 | Dx = 1.503 Mg m−3 |
Orthorhombic, P212121 | Mo Kα radiation, λ = 0.71073 Å |
Hall symbol: P 2ac 2ab | Cell parameters from 13820 reflections |
a = 9.4902 (6) Å | θ = 3.9–27.7° |
b = 10.9347 (8) Å | µ = 2.68 mm−1 |
c = 14.8687 (10) Å | T = 173 K |
V = 1542.96 (18) Å3 | Block, colourless |
Z = 4 | 0.27 × 0.25 × 0.23 mm |
Stoe IPDSII two-circle diffractometer | 3536 independent reflections |
Radiation source: fine-focus sealed tube | 3204 reflections with I > 2σ(I) |
Graphite monochromator | Rint = 0.044 |
ω scans | θmax = 27.6°, θmin = 4.0° |
Absorption correction: multi-scan (MULABS; Spek, 2003; Blessing, 1995) | h = −12→10 |
Tmin = 0.532, Tmax = 0.578 | k = −14→11 |
13120 measured reflections | l = −19→19 |
Refinement on F2 | Hydrogen site location: inferred from neighbouring sites |
Least-squares matrix: full | H atoms treated by a mixture of independent and constrained refinement |
R[F2 > 2σ(F2)] = 0.032 | w = 1/[σ2(Fo2) + (0.0288P)2 + 0.3101P] where P = (Fo2 + 2Fc2)/3 |
wR(F2) = 0.064 | (Δ/σ)max = 0.001 |
S = 1.06 | Δρmax = 0.37 e Å−3 |
3536 reflections | Δρmin = −0.58 e Å−3 |
200 parameters | Extinction correction: SHELXL97 (Sheldrick, 1997), Fc*=kFc[1+0.001xFc2λ3/sin(2θ)]-1/4 |
0 restraints | Extinction coefficient: 0.0078 (8) |
Primary atom site location: structure-invariant direct methods | Absolute structure: Flack (1983), with 1510 Friedel pairs |
Secondary atom site location: difference Fourier map | Absolute structure parameter: −0.004 (8) |
C15H13BrN2O3 | V = 1542.96 (18) Å3 |
Mr = 349.18 | Z = 4 |
Orthorhombic, P212121 | Mo Kα radiation |
a = 9.4902 (6) Å | µ = 2.68 mm−1 |
b = 10.9347 (8) Å | T = 173 K |
c = 14.8687 (10) Å | 0.27 × 0.25 × 0.23 mm |
Stoe IPDSII two-circle diffractometer | 3536 independent reflections |
Absorption correction: multi-scan (MULABS; Spek, 2003; Blessing, 1995) | 3204 reflections with I > 2σ(I) |
Tmin = 0.532, Tmax = 0.578 | Rint = 0.044 |
13120 measured reflections |
R[F2 > 2σ(F2)] = 0.032 | H atoms treated by a mixture of independent and constrained refinement |
wR(F2) = 0.064 | Δρmax = 0.37 e Å−3 |
S = 1.06 | Δρmin = −0.58 e Å−3 |
3536 reflections | Absolute structure: Flack (1983), with 1510 Friedel pairs |
200 parameters | Absolute structure parameter: −0.004 (8) |
0 restraints |
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 | 0.82669 (3) | 0.43390 (3) | 0.193021 (18) | 0.03868 (10) | |
C1 | 0.6507 (2) | 0.6879 (2) | 0.18939 (15) | 0.0214 (5) | |
O1 | 0.6900 (3) | 0.78219 (16) | 0.22737 (11) | 0.0330 (5) | |
O2 | 0.0445 (2) | 0.60418 (16) | 0.63181 (11) | 0.0272 (4) | |
H2 | 0.068 (5) | 0.664 (4) | 0.665 (3) | 0.076 (14)* | |
N1 | 0.5450 (2) | 0.6169 (2) | 0.21810 (12) | 0.0241 (4) | |
H1 | 0.527 (3) | 0.552 (3) | 0.1878 (17) | 0.022 (6)* | |
N2 | 0.4773 (2) | 0.64534 (18) | 0.29896 (13) | 0.0232 (4) | |
C2 | 0.3686 (2) | 0.5793 (2) | 0.31537 (15) | 0.0237 (5) | |
H2A | 0.3412 | 0.5197 | 0.2723 | 0.028* | |
C11 | 0.7159 (3) | 0.6461 (2) | 0.10162 (15) | 0.0211 (5) | |
C12 | 0.7929 (3) | 0.5383 (2) | 0.09271 (16) | 0.0247 (5) | |
C13 | 0.8508 (3) | 0.5061 (3) | 0.00963 (17) | 0.0319 (6) | |
H13 | 0.9046 | 0.4332 | 0.0040 | 0.038* | |
C14 | 0.8296 (3) | 0.5809 (3) | −0.06481 (15) | 0.0324 (5) | |
H14 | 0.8690 | 0.5590 | −0.1213 | 0.039* | |
C15 | 0.7508 (3) | 0.6875 (3) | −0.05688 (16) | 0.0275 (6) | |
C16 | 0.6950 (3) | 0.7216 (2) | 0.02622 (15) | 0.0234 (5) | |
H16 | 0.6431 | 0.7955 | 0.0318 | 0.028* | |
O17 | 0.7327 (2) | 0.7531 (2) | −0.13480 (12) | 0.0392 (5) | |
C17 | 0.6250 (4) | 0.8451 (3) | −0.1348 (2) | 0.0440 (8) | |
H17A | 0.5357 | 0.8090 | −0.1149 | 0.066* | |
H17B | 0.6139 | 0.8779 | −0.1957 | 0.066* | |
H17C | 0.6517 | 0.9112 | −0.0937 | 0.066* | |
C21 | 0.2849 (3) | 0.5918 (2) | 0.39774 (14) | 0.0214 (5) | |
C22 | 0.1683 (3) | 0.5158 (2) | 0.40985 (14) | 0.0260 (5) | |
H22 | 0.1440 | 0.4586 | 0.3643 | 0.031* | |
C23 | 0.0871 (3) | 0.5224 (2) | 0.48754 (16) | 0.0258 (5) | |
H23 | 0.0065 | 0.4717 | 0.4945 | 0.031* | |
C24 | 0.1255 (3) | 0.6041 (2) | 0.55512 (14) | 0.0205 (5) | |
C25 | 0.2405 (3) | 0.6819 (2) | 0.54426 (17) | 0.0239 (5) | |
H25 | 0.2646 | 0.7383 | 0.5903 | 0.029* | |
C26 | 0.3199 (3) | 0.6764 (2) | 0.46560 (14) | 0.0252 (5) | |
H26 | 0.3979 | 0.7299 | 0.4577 | 0.030* |
U11 | U22 | U33 | U12 | U13 | U23 | |
Br1 | 0.04558 (16) | 0.03697 (14) | 0.03348 (13) | 0.01019 (15) | −0.00287 (13) | 0.00721 (12) |
C1 | 0.0258 (13) | 0.0210 (10) | 0.0173 (9) | −0.0010 (9) | 0.0012 (10) | −0.0001 (9) |
O1 | 0.0473 (13) | 0.0280 (9) | 0.0236 (7) | −0.0128 (10) | 0.0101 (9) | −0.0082 (7) |
O2 | 0.0409 (11) | 0.0212 (9) | 0.0195 (7) | −0.0053 (8) | 0.0122 (8) | −0.0018 (7) |
N1 | 0.0281 (11) | 0.0262 (11) | 0.0180 (9) | −0.0055 (9) | 0.0068 (8) | −0.0077 (8) |
N2 | 0.0271 (10) | 0.0270 (10) | 0.0154 (8) | 0.0011 (8) | 0.0064 (9) | −0.0035 (8) |
C2 | 0.0282 (12) | 0.0240 (12) | 0.0189 (9) | 0.0019 (10) | 0.0023 (9) | −0.0016 (9) |
C11 | 0.0220 (12) | 0.0224 (12) | 0.0188 (10) | −0.0060 (10) | 0.0024 (9) | −0.0031 (8) |
C12 | 0.0256 (14) | 0.0246 (13) | 0.0239 (11) | 0.0005 (10) | −0.0013 (9) | −0.0013 (9) |
C13 | 0.0303 (16) | 0.0316 (14) | 0.0338 (13) | 0.0099 (12) | 0.0025 (11) | −0.0088 (10) |
C14 | 0.0340 (13) | 0.0398 (15) | 0.0232 (10) | 0.0041 (15) | 0.0083 (11) | −0.0064 (10) |
C15 | 0.0294 (15) | 0.0355 (15) | 0.0177 (11) | −0.0026 (12) | 0.0026 (10) | −0.0002 (10) |
C16 | 0.0230 (15) | 0.0251 (12) | 0.0222 (10) | −0.0043 (11) | 0.0049 (10) | −0.0022 (9) |
O17 | 0.0472 (13) | 0.0501 (13) | 0.0204 (8) | 0.0101 (10) | 0.0085 (8) | 0.0074 (9) |
C17 | 0.052 (2) | 0.0474 (19) | 0.0329 (14) | 0.0081 (15) | 0.0011 (13) | 0.0137 (13) |
C21 | 0.0248 (12) | 0.0220 (12) | 0.0174 (9) | 0.0016 (9) | 0.0019 (8) | −0.0023 (8) |
C22 | 0.0321 (13) | 0.0262 (11) | 0.0197 (9) | −0.0033 (13) | 0.0023 (11) | −0.0065 (8) |
C23 | 0.0286 (14) | 0.0257 (12) | 0.0230 (11) | −0.0080 (10) | 0.0052 (10) | −0.0034 (9) |
C24 | 0.0286 (12) | 0.0163 (11) | 0.0165 (9) | 0.0026 (9) | 0.0055 (9) | 0.0003 (8) |
C25 | 0.0315 (14) | 0.0197 (12) | 0.0205 (11) | −0.0010 (11) | 0.0039 (10) | −0.0054 (9) |
C26 | 0.0265 (13) | 0.0241 (11) | 0.0248 (10) | −0.0046 (13) | 0.0029 (12) | −0.0023 (9) |
Br1—C12 | 1.905 (2) | C15—O17 | 1.373 (3) |
C1—O1 | 1.234 (3) | C15—C16 | 1.395 (3) |
C1—N1 | 1.338 (3) | C16—H16 | 0.9500 |
C1—C11 | 1.515 (3) | O17—C17 | 1.434 (4) |
O2—C24 | 1.375 (3) | C17—H17A | 0.9800 |
O2—H2 | 0.84 (5) | C17—H17B | 0.9800 |
N1—N2 | 1.398 (3) | C17—H17C | 0.9800 |
N1—H1 | 0.86 (3) | C21—C22 | 1.396 (4) |
N2—C2 | 1.282 (3) | C21—C26 | 1.409 (3) |
C2—C21 | 1.466 (3) | C22—C23 | 1.390 (3) |
C2—H2A | 0.9500 | C22—H22 | 0.9500 |
C11—C12 | 1.393 (3) | C23—C24 | 1.394 (3) |
C11—C16 | 1.406 (3) | C23—H23 | 0.9500 |
C12—C13 | 1.397 (3) | C24—C25 | 1.392 (4) |
C13—C14 | 1.391 (4) | C25—C26 | 1.393 (3) |
C13—H13 | 0.9500 | C25—H25 | 0.9500 |
C14—C15 | 1.390 (4) | C26—H26 | 0.9500 |
C14—H14 | 0.9500 | ||
O1—C1—N1 | 124.5 (2) | C15—C16—H16 | 120.1 |
O1—C1—C11 | 121.5 (2) | C11—C16—H16 | 120.1 |
N1—C1—C11 | 114.0 (2) | C15—O17—C17 | 117.1 (2) |
C24—O2—H2 | 110 (3) | O17—C17—H17A | 109.5 |
C1—N1—N2 | 119.3 (2) | O17—C17—H17B | 109.5 |
C1—N1—H1 | 117.8 (18) | H17A—C17—H17B | 109.5 |
N2—N1—H1 | 122.7 (18) | O17—C17—H17C | 109.5 |
C2—N2—N1 | 114.07 (19) | H17A—C17—H17C | 109.5 |
N2—C2—C21 | 122.8 (2) | H17B—C17—H17C | 109.5 |
N2—C2—H2A | 118.6 | C22—C21—C26 | 119.1 (2) |
C21—C2—H2A | 118.6 | C22—C21—C2 | 118.8 (2) |
C12—C11—C16 | 119.7 (2) | C26—C21—C2 | 122.1 (2) |
C12—C11—C1 | 123.5 (2) | C23—C22—C21 | 121.0 (2) |
C16—C11—C1 | 116.9 (2) | C23—C22—H22 | 119.5 |
C11—C12—C13 | 120.2 (2) | C21—C22—H22 | 119.5 |
C11—C12—Br1 | 121.37 (17) | C22—C23—C24 | 119.2 (2) |
C13—C12—Br1 | 118.36 (19) | C22—C23—H23 | 120.4 |
C14—C13—C12 | 119.9 (2) | C24—C23—H23 | 120.4 |
C14—C13—H13 | 120.0 | O2—C24—C25 | 122.3 (2) |
C12—C13—H13 | 120.0 | O2—C24—C23 | 116.9 (2) |
C15—C14—C13 | 120.2 (2) | C25—C24—C23 | 120.9 (2) |
C15—C14—H14 | 119.9 | C26—C25—C24 | 119.7 (2) |
C13—C14—H14 | 119.9 | C26—C25—H25 | 120.1 |
O17—C15—C14 | 115.7 (2) | C24—C25—H25 | 120.1 |
O17—C15—C16 | 124.1 (3) | C25—C26—C21 | 120.1 (2) |
C14—C15—C16 | 120.2 (2) | C25—C26—H26 | 120.0 |
C15—C16—C11 | 119.7 (2) | C21—C26—H26 | 120.0 |
O1—C1—N1—N2 | −3.6 (4) | C14—C15—C16—C11 | −1.5 (4) |
C11—C1—N1—N2 | 179.3 (2) | C12—C11—C16—C15 | 0.4 (4) |
C1—N1—N2—C2 | 173.1 (2) | C1—C11—C16—C15 | −179.2 (2) |
N1—N2—C2—C21 | 178.2 (2) | C14—C15—O17—C17 | 164.8 (3) |
O1—C1—C11—C12 | 115.3 (3) | C16—C15—O17—C17 | −14.7 (4) |
N1—C1—C11—C12 | −67.5 (3) | N2—C2—C21—C22 | −180.0 (2) |
O1—C1—C11—C16 | −65.2 (3) | N2—C2—C21—C26 | −1.1 (4) |
N1—C1—C11—C16 | 112.0 (3) | C26—C21—C22—C23 | −0.1 (4) |
C16—C11—C12—C13 | 0.9 (4) | C2—C21—C22—C23 | 178.7 (2) |
C1—C11—C12—C13 | −179.6 (2) | C21—C22—C23—C24 | −1.7 (4) |
C16—C11—C12—Br1 | 179.08 (19) | C22—C23—C24—O2 | −177.9 (2) |
C1—C11—C12—Br1 | −1.4 (3) | C22—C23—C24—C25 | 2.3 (4) |
C11—C12—C13—C14 | −1.1 (4) | O2—C24—C25—C26 | 179.0 (2) |
Br1—C12—C13—C14 | −179.3 (2) | C23—C24—C25—C26 | −1.2 (4) |
C12—C13—C14—C15 | −0.1 (4) | C24—C25—C26—C21 | −0.6 (4) |
C13—C14—C15—O17 | −178.2 (3) | C22—C21—C26—C25 | 1.3 (4) |
C13—C14—C15—C16 | 1.4 (4) | C2—C21—C26—C25 | −177.5 (2) |
O17—C15—C16—C11 | 178.0 (2) |
D—H···A | D—H | H···A | D···A | D—H···A |
O2—H2···O1i | 0.84 (5) | 2.07 (4) | 2.799 (3) | 145 (4) |
O2—H2···N2i | 0.84 (5) | 2.32 (5) | 2.995 (3) | 137 (4) |
N1—H1···O2ii | 0.86 (3) | 2.01 (3) | 2.866 (3) | 170 (3) |
Symmetry codes: (i) x−1/2, −y+3/2, −z+1; (ii) −x+1/2, −y+1, z−1/2. |
Experimental details
Crystal data | |
Chemical formula | C15H13BrN2O3 |
Mr | 349.18 |
Crystal system, space group | Orthorhombic, P212121 |
Temperature (K) | 173 |
a, b, c (Å) | 9.4902 (6), 10.9347 (8), 14.8687 (10) |
V (Å3) | 1542.96 (18) |
Z | 4 |
Radiation type | Mo Kα |
µ (mm−1) | 2.68 |
Crystal size (mm) | 0.27 × 0.25 × 0.23 |
Data collection | |
Diffractometer | Stoe IPDSII two-circle |
Absorption correction | Multi-scan (MULABS; Spek, 2003; Blessing, 1995) |
Tmin, Tmax | 0.532, 0.578 |
No. of measured, independent and observed [I > 2σ(I)] reflections | 13120, 3536, 3204 |
Rint | 0.044 |
(sin θ/λ)max (Å−1) | 0.651 |
Refinement | |
R[F2 > 2σ(F2)], wR(F2), S | 0.032, 0.064, 1.06 |
No. of reflections | 3536 |
No. of parameters | 200 |
H-atom treatment | H atoms treated by a mixture of independent and constrained refinement |
Δρmax, Δρmin (e Å−3) | 0.37, −0.58 |
Absolute structure | Flack (1983), with 1510 Friedel pairs |
Absolute structure parameter | −0.004 (8) |
Computer programs: X-AREA (Stoe & Cie, 2001), X-AREA [Or X-RED ?], SHELXS97 (Sheldrick, 1990), SHELXL97 (Sheldrick, 1997), PLATON (Spek, 2003), SHELXL97.
D—H···A | D—H | H···A | D···A | D—H···A |
O2—H2···O1i | 0.84 (5) | 2.07 (4) | 2.799 (3) | 145 (4) |
O2—H2···N2i | 0.84 (5) | 2.32 (5) | 2.995 (3) | 137 (4) |
N1—H1···O2ii | 0.86 (3) | 2.01 (3) | 2.866 (3) | 170 (3) |
Symmetry codes: (i) x−1/2, −y+3/2, −z+1; (ii) −x+1/2, −y+1, z−1/2. |
Schiff bases are known to have biological activities such as antimicrobial (El-Masry et al., 2000; Pandey et al., 1999), antifungal (Singh et al., 1988; Varma et al., 1986), antitumor (Hodnett et al., 1970; Misra et al. 1981; Desai et al., 2001), and as herbicides. Schiff bases have also been employed as ligands for complexation of metal ions (Aydoğan et al., 2001). On the industrial scale, they have wide range of applications such as dyes and pigments (Taggi et al., 2002). The crystal structures of 2-bromo-N-[(E)-4-chlorobenzylidene]-5-methoxybenzohydrazide (Butcher et al., 2007), 2-bromo-5-methoxy-N-[(E)-(2-nitrophenyl)methylene]benzohydrazide (Yathirajan et al., 2007), 2-bromo-N-[(E)-(4-fluorophenyl)methylene]-5-methoxybenzohydrazide monohydrate (Narayana et al., 2007), N'-[(1E)-(5-chloro-2-hydroxyphenyl)(phenyl)methylene]-2-hydroxybenzohydrazide (Chang et al., 2007), 2'-(3,4-dimethoxybenzylidene)-2-hydroxybenzohydrazide, (Yang & Pan, 2004) and 2'-(2-fluorobenzylidene)-2-hydroxybenzohydrazide (Yang & Pan, 2005) have been reported. A new Schiff base, C15H13BrN2O3, was synthesized and its crystal structure is here reported.
Geometric parameters of the title compound (Fig. 1) are in the usual ranges. The C═N double bond is trans configured. The C═N—N—CO– moiety itself is planar (r.m.s. deviation 0.044 Å). It makes a dihedral angle of 10.73 (19)°, with the hydroxyphenyl ring, but forms a dihedral angle of 67.90 (8)° with the other aromatic ring. The crystal packing is stabilized by N—H···O, O—H···O and O—H···N hydrogen bonds. The hydroxyl group forms a bifurcated H bond to the hydrazon N atom and the carbonyl group.