




Supporting information
![]() | Crystallographic Information File (CIF) https://doi.org/10.1107/S1600536808015912/sj2509sup1.cif |
![]() | Structure factor file (CIF format) https://doi.org/10.1107/S1600536808015912/sj2509Isup2.hkl |
CCDC reference: 696474
Key indicators
- Single-crystal X-ray study
- T = 298 K
- Mean
(C-C) = 0.003 Å
- R factor = 0.031
- wR factor = 0.060
- Data-to-parameter ratio = 15.7
checkCIF/PLATON results
No syntax errors found
Alert level C PLAT230_ALERT_2_C Hirshfeld Test Diff for C12 -- C13 .. 5.68 su PLAT062_ALERT_4_C Rescale T(min) & T(max) by ..................... 0.96 PLAT731_ALERT_1_C Bond Calc 0.90(3), Rep 0.904(10) ...... 3.00 su-Ra N2 -H2A 1.555 1.555 PLAT735_ALERT_1_C D-H Calc 0.90(3), Rep 0.904(10) ...... 3.00 su-Ra N2 -H2A 1.555 1.555 PLAT736_ALERT_1_C H...A Calc 2.14(3), Rep 2.136(14) ...... 2.14 su-Ra H2A -O1 1.555 2.555
Alert level G 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 26.58 From the CIF: _reflns_number_total 2757 Count of symmetry unique reflns 1614 Completeness (_total/calc) 170.82% TEST3: Check Friedels for noncentro structure Estimate of Friedel pairs measured 1143 Fraction of Friedel pairs measured 0.708 Are heavy atom types Z>Si present yes
0 ALERT level A = In general: serious problem 0 ALERT level B = Potentially serious problem 5 ALERT level C = Check and explain 1 ALERT level G = General alerts; check 3 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 0 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
The compound was prepared by refluxing equimolar quantities of 4-hydroxybenzaldehyde with 3-bromobenzohydrazide in methanol. Colourless block-like crystals were formed when the solution was evaporated in air for about a week.
H2A was located in a difference Fourier map and refined isotropically, with the N—H distance restrained to 0.90 (1) Å. The other H atoms were placed in idealized positions and constrained to ride on their parent atoms, with C—H distances of 0.93 Å, the O—H distance 0.82 Å, and with Uiso(H) set at 1.2Ueq(C) and 1.5Ueq(O).
Data collection: SMART (Bruker, 2007); cell refinement: SAINT (Bruker, 2007); data reduction: SAINT (Bruker, 2007); program(s) used to solve structure: SHELXTL (Sheldrick, 2008); program(s) used to refine structure: SHELXTL (Sheldrick, 2008); molecular graphics: SHELXTL (Sheldrick, 2008); software used to prepare material for publication: SHELXTL (Sheldrick, 2008).
![]() | Fig. 1. The molecular structure of (I) with ellipsoids drawn at the 30% probability level. |
![]() | Fig. 2. The molecular packing of (I), viewed along the a axis. Hydrogen bonds are drawn as dashed lines. |
C14H11BrN2O2 | F(000) = 640 |
Mr = 319.16 | Dx = 1.591 Mg m−3 |
Orthorhombic, P212121 | Mo Kα radiation, λ = 0.71073 Å |
Hall symbol: P 2ac 2ab | Cell parameters from 1827 reflections |
a = 7.5576 (11) Å | θ = 2.3–24.5° |
b = 11.7337 (18) Å | µ = 3.09 mm−1 |
c = 15.021 (2) Å | T = 298 K |
V = 1332.0 (3) Å3 | Block, colourless |
Z = 4 | 0.20 × 0.17 × 0.16 mm |
Bruker SMART CCD area-detector diffractometer | 2757 independent reflections |
Radiation source: fine-focus sealed tube | 2145 reflections with I > 2σ(I) |
Graphite monochromator | Rint = 0.038 |
ω scans | θmax = 26.6°, θmin = 2.2° |
Absorption correction: multi-scan (SADABS; Bruker, 2001) | h = −9→9 |
Tmin = 0.577, Tmax = 0.638 | k = −10→14 |
7740 measured reflections | l = −18→18 |
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)] = 0.031 | H atoms treated by a mixture of independent and constrained refinement |
wR(F2) = 0.059 | w = 1/[σ2(Fo2) + (0.0151P)2] where P = (Fo2 + 2Fc2)/3 |
S = 0.97 | (Δ/σ)max = 0.001 |
2757 reflections | Δρmax = 0.17 e Å−3 |
176 parameters | Δρmin = −0.29 e Å−3 |
1 restraint | Absolute structure: Flack (1983), with 1154 Friedel pairs |
Primary atom site location: structure-invariant direct methods | Absolute structure parameter: 0.006 (9) |
C14H11BrN2O2 | V = 1332.0 (3) Å3 |
Mr = 319.16 | Z = 4 |
Orthorhombic, P212121 | Mo Kα radiation |
a = 7.5576 (11) Å | µ = 3.09 mm−1 |
b = 11.7337 (18) Å | T = 298 K |
c = 15.021 (2) Å | 0.20 × 0.17 × 0.16 mm |
Bruker SMART CCD area-detector diffractometer | 2757 independent reflections |
Absorption correction: multi-scan (SADABS; Bruker, 2001) | 2145 reflections with I > 2σ(I) |
Tmin = 0.577, Tmax = 0.638 | Rint = 0.038 |
7740 measured reflections |
R[F2 > 2σ(F2)] = 0.031 | H atoms treated by a mixture of independent and constrained refinement |
wR(F2) = 0.059 | Δρmax = 0.17 e Å−3 |
S = 0.97 | Δρmin = −0.29 e Å−3 |
2757 reflections | Absolute structure: Flack (1983), with 1154 Friedel pairs |
176 parameters | Absolute structure parameter: 0.006 (9) |
1 restraint |
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 | 0.04594 (5) | 0.39161 (3) | 0.901456 (17) | 0.06805 (13) | |
O1 | 0.1347 (3) | −0.14174 (14) | 0.15827 (10) | 0.0414 (5) | |
H1 | 0.0663 | −0.1163 | 0.1208 | 0.062* | |
O2 | 0.0446 (3) | 0.45672 (13) | 0.48129 (10) | 0.0435 (4) | |
N1 | 0.1134 (3) | 0.23480 (18) | 0.46451 (12) | 0.0380 (6) | |
N2 | 0.1329 (3) | 0.29110 (18) | 0.54514 (12) | 0.0372 (5) | |
C1 | 0.1401 (3) | 0.0602 (2) | 0.38450 (14) | 0.0310 (6) | |
C2 | 0.0757 (3) | 0.1044 (2) | 0.30437 (14) | 0.0343 (6) | |
H2 | 0.0339 | 0.1789 | 0.3024 | 0.041* | |
C3 | 0.0735 (3) | 0.03889 (19) | 0.22853 (14) | 0.0331 (6) | |
H3 | 0.0315 | 0.0692 | 0.1754 | 0.040* | |
C4 | 0.1341 (3) | −0.0726 (2) | 0.23148 (14) | 0.0309 (6) | |
C5 | 0.1975 (3) | −0.1177 (2) | 0.31015 (15) | 0.0357 (6) | |
H5 | 0.2381 | −0.1925 | 0.3120 | 0.043* | |
C6 | 0.2003 (3) | −0.0514 (2) | 0.38585 (15) | 0.0352 (6) | |
H6 | 0.2432 | −0.0820 | 0.4387 | 0.042* | |
C7 | 0.1494 (3) | 0.1299 (2) | 0.46504 (15) | 0.0348 (6) | |
H7 | 0.1829 | 0.0958 | 0.5183 | 0.042* | |
C8 | 0.0976 (3) | 0.4039 (2) | 0.54681 (14) | 0.0339 (6) | |
C9 | 0.1227 (3) | 0.4615 (2) | 0.63473 (15) | 0.0333 (6) | |
C10 | 0.0837 (3) | 0.4069 (2) | 0.71421 (14) | 0.0373 (6) | |
H10 | 0.0457 | 0.3315 | 0.7143 | 0.045* | |
C11 | 0.1020 (4) | 0.4657 (2) | 0.79290 (15) | 0.0405 (7) | |
C12 | 0.1571 (4) | 0.5781 (2) | 0.79396 (18) | 0.0482 (8) | |
H12 | 0.1689 | 0.6169 | 0.8476 | 0.058* | |
C13 | 0.1942 (4) | 0.6314 (2) | 0.7149 (2) | 0.0516 (8) | |
H13 | 0.2320 | 0.7068 | 0.7151 | 0.062* | |
C14 | 0.1760 (4) | 0.5743 (2) | 0.63504 (17) | 0.0425 (7) | |
H14 | 0.1995 | 0.6116 | 0.5817 | 0.051* | |
H2A | 0.195 (4) | 0.257 (2) | 0.5890 (15) | 0.080* |
U11 | U22 | U33 | U12 | U13 | U23 | |
Br1 | 0.0960 (3) | 0.0793 (2) | 0.02888 (14) | 0.0102 (2) | 0.00631 (17) | −0.00726 (16) |
O1 | 0.0589 (13) | 0.0376 (10) | 0.0276 (8) | 0.0034 (9) | −0.0034 (9) | −0.0093 (8) |
O2 | 0.0655 (12) | 0.0350 (10) | 0.0301 (8) | 0.0023 (10) | −0.0072 (10) | 0.0018 (8) |
N1 | 0.0566 (16) | 0.0338 (13) | 0.0237 (10) | 0.0039 (11) | −0.0060 (10) | −0.0063 (9) |
N2 | 0.0581 (16) | 0.0306 (13) | 0.0230 (11) | 0.0104 (11) | −0.0077 (10) | −0.0070 (9) |
C1 | 0.0354 (14) | 0.0340 (13) | 0.0236 (13) | −0.0019 (11) | −0.0012 (10) | −0.0033 (10) |
C2 | 0.0435 (16) | 0.0295 (12) | 0.0298 (11) | −0.0011 (13) | 0.0013 (11) | −0.0003 (11) |
C3 | 0.0424 (16) | 0.0334 (14) | 0.0235 (11) | 0.0021 (12) | −0.0035 (11) | 0.0015 (10) |
C4 | 0.0343 (14) | 0.0348 (15) | 0.0238 (12) | −0.0046 (11) | 0.0011 (11) | −0.0070 (10) |
C5 | 0.0470 (17) | 0.0258 (14) | 0.0343 (12) | 0.0036 (13) | −0.0010 (11) | −0.0011 (12) |
C6 | 0.0452 (16) | 0.0362 (14) | 0.0243 (13) | 0.0032 (11) | −0.0068 (11) | 0.0013 (11) |
C7 | 0.0414 (15) | 0.0393 (17) | 0.0238 (11) | 0.0003 (13) | −0.0026 (11) | −0.0027 (11) |
C8 | 0.0370 (16) | 0.0361 (15) | 0.0287 (12) | −0.0032 (13) | 0.0000 (10) | −0.0013 (12) |
C9 | 0.0362 (15) | 0.0342 (15) | 0.0297 (12) | 0.0039 (12) | −0.0045 (11) | −0.0069 (11) |
C10 | 0.0434 (17) | 0.0381 (14) | 0.0304 (12) | 0.0049 (13) | −0.0038 (11) | −0.0097 (12) |
C11 | 0.0450 (18) | 0.0456 (17) | 0.0308 (13) | 0.0094 (13) | −0.0012 (11) | −0.0093 (12) |
C12 | 0.0512 (19) | 0.055 (2) | 0.0388 (15) | 0.0096 (15) | −0.0131 (14) | −0.0196 (14) |
C13 | 0.054 (2) | 0.0368 (17) | 0.0644 (19) | 0.0002 (14) | −0.0103 (15) | −0.0221 (15) |
C14 | 0.0483 (18) | 0.0370 (17) | 0.0421 (15) | −0.0020 (13) | −0.0031 (13) | −0.0037 (12) |
Br1—C11 | 1.896 (3) | C5—C6 | 1.378 (3) |
O1—C4 | 1.367 (3) | C5—H5 | 0.9300 |
O1—H1 | 0.8200 | C6—H6 | 0.9300 |
O2—C8 | 1.230 (3) | C7—H7 | 0.9300 |
N1—C7 | 1.260 (3) | C8—C9 | 1.495 (3) |
N1—N2 | 1.387 (2) | C9—C14 | 1.384 (4) |
N2—C8 | 1.351 (3) | C9—C10 | 1.387 (3) |
N2—H2A | 0.904 (10) | C10—C11 | 1.376 (3) |
C1—C6 | 1.386 (3) | C10—H10 | 0.9300 |
C1—C2 | 1.398 (3) | C11—C12 | 1.382 (4) |
C1—C7 | 1.462 (3) | C12—C13 | 1.371 (4) |
C2—C3 | 1.374 (3) | C12—H12 | 0.9300 |
C2—H2 | 0.9300 | C13—C14 | 1.381 (4) |
C3—C4 | 1.386 (3) | C13—H13 | 0.9300 |
C3—H3 | 0.9300 | C14—H14 | 0.9300 |
C4—C5 | 1.381 (3) | ||
C4—O1—H1 | 109.5 | N1—C7—H7 | 119.0 |
C7—N1—N2 | 115.88 (19) | C1—C7—H7 | 119.0 |
C8—N2—N1 | 117.51 (19) | O2—C8—N2 | 122.9 (2) |
C8—N2—H2A | 121.7 (19) | O2—C8—C9 | 121.4 (2) |
N1—N2—H2A | 119 (2) | N2—C8—C9 | 115.7 (2) |
C6—C1—C2 | 118.5 (2) | C14—C9—C10 | 120.1 (2) |
C6—C1—C7 | 120.0 (2) | C14—C9—C8 | 118.2 (2) |
C2—C1—C7 | 121.4 (2) | C10—C9—C8 | 121.7 (2) |
C3—C2—C1 | 120.7 (2) | C11—C10—C9 | 119.1 (2) |
C3—C2—H2 | 119.7 | C11—C10—H10 | 120.5 |
C1—C2—H2 | 119.7 | C9—C10—H10 | 120.5 |
C2—C3—C4 | 119.8 (2) | C10—C11—C12 | 121.3 (2) |
C2—C3—H3 | 120.1 | C10—C11—Br1 | 119.1 (2) |
C4—C3—H3 | 120.1 | C12—C11—Br1 | 119.65 (19) |
O1—C4—C5 | 117.4 (2) | C13—C12—C11 | 119.1 (2) |
O1—C4—C3 | 122.4 (2) | C13—C12—H12 | 120.4 |
C5—C4—C3 | 120.2 (2) | C11—C12—H12 | 120.4 |
C6—C5—C4 | 119.7 (2) | C12—C13—C14 | 120.7 (3) |
C6—C5—H5 | 120.2 | C12—C13—H13 | 119.6 |
C4—C5—H5 | 120.2 | C14—C13—H13 | 119.6 |
C5—C6—C1 | 121.1 (2) | C13—C14—C9 | 119.7 (3) |
C5—C6—H6 | 119.5 | C13—C14—H14 | 120.1 |
C1—C6—H6 | 119.5 | C9—C14—H14 | 120.1 |
N1—C7—C1 | 122.1 (2) |
D—H···A | D—H | H···A | D···A | D—H···A |
O1—H1···O2i | 0.82 | 1.95 | 2.750 (2) | 166 |
O1—H1···N1i | 0.82 | 2.56 | 3.003 (3) | 116 |
N2—H2A···O1ii | 0.90 (1) | 2.14 (1) | 3.007 (3) | 162 (3) |
Symmetry codes: (i) −x, y−1/2, −z+1/2; (ii) −x+1/2, −y, z+1/2. |
Experimental details
Crystal data | |
Chemical formula | C14H11BrN2O2 |
Mr | 319.16 |
Crystal system, space group | Orthorhombic, P212121 |
Temperature (K) | 298 |
a, b, c (Å) | 7.5576 (11), 11.7337 (18), 15.021 (2) |
V (Å3) | 1332.0 (3) |
Z | 4 |
Radiation type | Mo Kα |
µ (mm−1) | 3.09 |
Crystal size (mm) | 0.20 × 0.17 × 0.16 |
Data collection | |
Diffractometer | Bruker SMART CCD area-detector diffractometer |
Absorption correction | Multi-scan (SADABS; Bruker, 2001) |
Tmin, Tmax | 0.577, 0.638 |
No. of measured, independent and observed [I > 2σ(I)] reflections | 7740, 2757, 2145 |
Rint | 0.038 |
(sin θ/λ)max (Å−1) | 0.630 |
Refinement | |
R[F2 > 2σ(F2)], wR(F2), S | 0.031, 0.059, 0.97 |
No. of reflections | 2757 |
No. of parameters | 176 |
No. of restraints | 1 |
H-atom treatment | H atoms treated by a mixture of independent and constrained refinement |
Δρmax, Δρmin (e Å−3) | 0.17, −0.29 |
Absolute structure | Flack (1983), with 1154 Friedel pairs |
Absolute structure parameter | 0.006 (9) |
Computer programs: SMART (Bruker, 2007), SAINT (Bruker, 2007), SHELXTL (Sheldrick, 2008).
D—H···A | D—H | H···A | D···A | D—H···A |
O1—H1···O2i | 0.82 | 1.95 | 2.750 (2) | 166 |
O1—H1···N1i | 0.82 | 2.56 | 3.003 (3) | 116 |
N2—H2A···O1ii | 0.904 (10) | 2.136 (14) | 3.007 (3) | 162 (3) |
Symmetry codes: (i) −x, y−1/2, −z+1/2; (ii) −x+1/2, −y, z+1/2. |
We have recently reported some transition metal complexes with Schiff base ligands (Cao, 2007a,b). We report herein the crystal structure of the title compound, (I), derived from the reaction of 4-hydroxybenzaldehyde with an equimolar quantity of 3-bromobenzohydrazide in methanol.
In compound (I), Fig. 1, the dihedral angle between the two benzene rings is 40.1 (2)°. In the crystal structure, molecules are linked through intermolecular O—H···O, O—H···N, and N—H···O hydrogen bonds, Table 1, to form a three-dimensional network, Figure 2.