


Supporting information
![]() | Crystallographic Information File (CIF) https://doi.org/10.1107/S1600536809049952/cv2651sup1.cif |
![]() | Structure factor file (CIF format) https://doi.org/10.1107/S1600536809049952/cv2651Isup2.hkl |
CCDC reference: 766703
Key indicators
- Single-crystal X-ray study
- T = 298 K
- Mean
(C-C) = 0.012 Å
- R factor = 0.064
- wR factor = 0.189
- Data-to-parameter ratio = 13.9
checkCIF/PLATON results
No syntax errors found
Alert level C PLAT026_ALERT_3_C Ratio Observed / Unique Reflections too Low .... 41 Perc. PLAT242_ALERT_2_C Check Low Ueq as Compared to Neighbors for C13 PLAT341_ALERT_3_C Low Bond Precision on C-C Bonds (x 1000) Ang .. 12 PLAT911_ALERT_3_C Missing # FCF Refl Between THmin & STh/L= 0.595 18 PLAT125_ALERT_4_C No _symmetry_space_group_name_Hall Given ....... ? PLAT234_ALERT_4_C Large Hirshfeld Difference C5 -- C6 .. 0.17 Ang.
Alert level G PLAT083_ALERT_2_G SHELXL Second Parameter in WGHT Unusually Large. 6.19
0 ALERT level A = In general: serious problem 0 ALERT level B = Potentially serious problem 6 ALERT level C = Check and explain 1 ALERT level G = General alerts; check 0 ALERT type 1 CIF construction/syntax error, inconsistent or missing data 2 ALERT type 2 Indicator that the structure model may be wrong or deficient 3 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
Benzohydrazide (5.0 mmol), 20 ml e thanol and 4-bromoacetophenone (5.0 mmol) were mixed in 50 ml flash. After refluxing 3 h, the resulting mixture was cooled to room temperature, and recrystalized from ethanol, and afforded the title compound as a crystalline solid. Elemental analysis: calculated for C15H13BrN2O: C 56.80, H 4.13, N 8.83%; found: C 56.78, H 4.24, N 8.69%.
All H atoms were placed in geometrically idealized positions (N—H 0.86 Å, C—H=0.93–0.96 Å) and treated as riding on their parent atoms, with Uiso(H) = 1.2–1.5 Ueq(C, N).
Data collection: SMART (Siemens, 1996); cell refinement: SAINT (Siemens, 1996); data reduction: SAINT (Siemens, 1996); program(s) used to solve structure: SHELXS97 (Sheldrick, 2008); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008); molecular graphics: SHELXTL (Sheldrick, 2008); software used to prepare material for publication: SHELXTL (Sheldrick, 2008).
![]() | Fig. 1. A view of (I) showing the atomic numbering scheme and 30% probability displacement ellipsoids. |
C15H13BrN2O | F(000) = 1280 |
Mr = 317.18 | Dx = 1.540 Mg m−3 |
Monoclinic, P21/c | Mo Kα radiation, λ = 0.71073 Å |
a = 9.9770 (11) Å | Cell parameters from 1649 reflections |
b = 31.487 (3) Å | θ = 2.6–22.4° |
c = 8.7613 (9) Å | µ = 3.00 mm−1 |
β = 96.104 (1)° | T = 298 K |
V = 2736.8 (5) Å3 | Block, colourless |
Z = 8 | 0.49 × 0.18 × 0.12 mm |
Bruker SMART APEX CCD area-detector diffractometer | 4804 independent reflections |
Radiation source: fine-focus sealed tube | 1961 reflections with I > 2σ(I) |
Graphite monochromator | Rint = 0.079 |
phi and ω scans | θmax = 25.0°, θmin = 1.3° |
Absorption correction: multi-scan (SADABS; Sheldrick, 1996) | h = −11→10 |
Tmin = 0.321, Tmax = 0.715 | k = −37→37 |
13558 measured reflections | l = −9→10 |
Refinement on F2 | Primary atom site location: structure-invariant direct methods |
Least-squares matrix: full | Secondary atom site location: difference Fourier map |
R[F2 > 2σ(F2)] = 0.064 | Hydrogen site location: inferred from neighbouring sites |
wR(F2) = 0.189 | H-atom parameters constrained |
S = 1.02 | w = 1/[σ2(Fo2) + (0.0544P)2 + 6.194P] where P = (Fo2 + 2Fc2)/3 |
4804 reflections | (Δ/σ)max < 0.001 |
345 parameters | Δρmax = 0.47 e Å−3 |
0 restraints | Δρmin = −0.44 e Å−3 |
C15H13BrN2O | V = 2736.8 (5) Å3 |
Mr = 317.18 | Z = 8 |
Monoclinic, P21/c | Mo Kα radiation |
a = 9.9770 (11) Å | µ = 3.00 mm−1 |
b = 31.487 (3) Å | T = 298 K |
c = 8.7613 (9) Å | 0.49 × 0.18 × 0.12 mm |
β = 96.104 (1)° |
Bruker SMART APEX CCD area-detector diffractometer | 4804 independent reflections |
Absorption correction: multi-scan (SADABS; Sheldrick, 1996) | 1961 reflections with I > 2σ(I) |
Tmin = 0.321, Tmax = 0.715 | Rint = 0.079 |
13558 measured reflections |
R[F2 > 2σ(F2)] = 0.064 | 0 restraints |
wR(F2) = 0.189 | H-atom parameters constrained |
S = 1.02 | Δρmax = 0.47 e Å−3 |
4804 reflections | Δρmin = −0.44 e Å−3 |
345 parameters |
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 | 0.05576 (10) | 0.04761 (3) | 0.12825 (13) | 0.0742 (4) | |
Br2 | 0.53233 (12) | 0.04532 (3) | 0.13223 (14) | 0.0925 (5) | |
N1 | 0.1623 (6) | 0.30472 (16) | 0.1860 (7) | 0.0375 (17) | |
H1 | 0.2450 | 0.3123 | 0.2070 | 0.045* | |
N2 | 0.1275 (6) | 0.26193 (18) | 0.1697 (8) | 0.0414 (18) | |
N3 | 0.6642 (6) | 0.30098 (17) | 0.1957 (7) | 0.0415 (18) | |
H3 | 0.7454 | 0.3084 | 0.2272 | 0.050* | |
N4 | 0.6303 (6) | 0.25836 (18) | 0.1760 (7) | 0.0375 (17) | |
O1 | −0.0567 (5) | 0.32437 (15) | 0.1524 (7) | 0.0512 (16) | |
O2 | 0.4486 (5) | 0.32125 (15) | 0.1277 (6) | 0.0465 (15) | |
C1 | 0.0627 (8) | 0.3340 (2) | 0.1678 (9) | 0.037 (2) | |
C2 | 0.1063 (8) | 0.3795 (2) | 0.1712 (9) | 0.036 (2) | |
C3 | 0.2317 (9) | 0.3936 (3) | 0.2308 (11) | 0.056 (3) | |
H3A | 0.2965 | 0.3740 | 0.2693 | 0.067* | |
C4 | 0.2627 (9) | 0.4362 (3) | 0.2342 (13) | 0.077 (3) | |
H4 | 0.3476 | 0.4454 | 0.2750 | 0.092* | |
C5 | 0.1660 (12) | 0.4652 (3) | 0.1765 (13) | 0.084 (4) | |
H5 | 0.1857 | 0.4941 | 0.1776 | 0.100* | |
C6 | 0.0444 (10) | 0.4515 (3) | 0.1191 (11) | 0.066 (3) | |
H6 | −0.0198 | 0.4711 | 0.0792 | 0.079* | |
C7 | 0.0123 (8) | 0.4089 (2) | 0.1179 (10) | 0.052 (2) | |
H7 | −0.0741 | 0.4002 | 0.0806 | 0.063* | |
C8 | 0.3318 (7) | 0.2479 (2) | 0.3464 (9) | 0.039 (2) | |
H8A | 0.4062 | 0.2526 | 0.2873 | 0.058* | |
H8B | 0.3543 | 0.2257 | 0.4196 | 0.058* | |
H8C | 0.3132 | 0.2736 | 0.3996 | 0.058* | |
C9 | 0.2105 (7) | 0.2354 (2) | 0.2421 (9) | 0.032 (2) | |
C10 | 0.1756 (7) | 0.1897 (2) | 0.2133 (9) | 0.034 (2) | |
C11 | 0.2275 (8) | 0.1584 (2) | 0.3126 (9) | 0.041 (2) | |
H11 | 0.2867 | 0.1656 | 0.3979 | 0.049* | |
C12 | 0.1921 (8) | 0.1161 (2) | 0.2866 (10) | 0.045 (2) | |
H12 | 0.2287 | 0.0953 | 0.3537 | 0.053* | |
C13 | 0.1045 (8) | 0.1051 (2) | 0.1637 (10) | 0.036 (2) | |
C14 | 0.0528 (8) | 0.1356 (2) | 0.0611 (10) | 0.046 (2) | |
H14 | −0.0047 | 0.1281 | −0.0253 | 0.055* | |
C15 | 0.0875 (7) | 0.1777 (2) | 0.0884 (9) | 0.036 (2) | |
H15 | 0.0505 | 0.1984 | 0.0210 | 0.044* | |
C16 | 0.5674 (8) | 0.3303 (2) | 0.1644 (9) | 0.0331 (19) | |
C17 | 0.6123 (7) | 0.3751 (2) | 0.1748 (10) | 0.037 (2) | |
C18 | 0.5576 (8) | 0.4041 (2) | 0.0657 (10) | 0.051 (2) | |
H18 | 0.4952 | 0.3948 | −0.0137 | 0.061* | |
C19 | 0.5939 (10) | 0.4464 (3) | 0.0728 (13) | 0.074 (3) | |
H19 | 0.5593 | 0.4653 | −0.0029 | 0.089* | |
C20 | 0.6835 (10) | 0.4602 (3) | 0.1961 (14) | 0.073 (3) | |
H20 | 0.7081 | 0.4887 | 0.2034 | 0.088* | |
C21 | 0.7347 (10) | 0.4324 (3) | 0.3050 (13) | 0.071 (3) | |
H21 | 0.7933 | 0.4420 | 0.3874 | 0.085* | |
C22 | 0.7009 (8) | 0.3897 (3) | 0.2950 (11) | 0.056 (3) | |
H22 | 0.7380 | 0.3709 | 0.3695 | 0.068* | |
C23 | 0.8370 (8) | 0.2420 (2) | 0.3406 (11) | 0.052 (2) | |
H23A | 0.9101 | 0.2458 | 0.2791 | 0.077* | |
H23B | 0.8582 | 0.2194 | 0.4125 | 0.077* | |
H23C | 0.8231 | 0.2678 | 0.3953 | 0.077* | |
C24 | 0.7126 (7) | 0.2313 (2) | 0.2401 (9) | 0.034 (2) | |
C25 | 0.6731 (8) | 0.1857 (2) | 0.2140 (9) | 0.036 (2) | |
C26 | 0.7538 (8) | 0.1525 (2) | 0.2651 (11) | 0.057 (3) | |
H26 | 0.8374 | 0.1581 | 0.3188 | 0.068* | |
C27 | 0.7146 (10) | 0.1107 (3) | 0.2391 (12) | 0.065 (3) | |
H27 | 0.7719 | 0.0886 | 0.2734 | 0.078* | |
C28 | 0.5913 (10) | 0.1022 (3) | 0.1627 (11) | 0.058 (3) | |
C29 | 0.5083 (9) | 0.1343 (3) | 0.1057 (10) | 0.057 (3) | |
H29 | 0.4250 | 0.1285 | 0.0518 | 0.069* | |
C30 | 0.5519 (8) | 0.1757 (3) | 0.1305 (10) | 0.057 (3) | |
H30 | 0.4973 | 0.1977 | 0.0892 | 0.069* |
U11 | U22 | U33 | U12 | U13 | U23 | |
Br1 | 0.0932 (8) | 0.0335 (5) | 0.0912 (9) | −0.0095 (5) | −0.0117 (6) | −0.0017 (5) |
Br2 | 0.1330 (11) | 0.0416 (6) | 0.1011 (11) | −0.0177 (6) | 0.0043 (8) | −0.0026 (6) |
N1 | 0.032 (4) | 0.021 (3) | 0.058 (5) | −0.003 (3) | 0.001 (3) | −0.001 (3) |
N2 | 0.033 (4) | 0.028 (3) | 0.063 (6) | −0.002 (3) | 0.005 (4) | 0.004 (3) |
N3 | 0.032 (4) | 0.027 (3) | 0.064 (6) | 0.000 (3) | −0.002 (4) | 0.001 (3) |
N4 | 0.035 (4) | 0.037 (4) | 0.041 (5) | −0.003 (3) | 0.005 (4) | 0.001 (3) |
O1 | 0.034 (3) | 0.038 (3) | 0.083 (5) | −0.005 (3) | 0.008 (3) | −0.003 (3) |
O2 | 0.028 (3) | 0.038 (3) | 0.072 (5) | −0.004 (2) | 0.000 (3) | −0.004 (3) |
C1 | 0.031 (5) | 0.035 (4) | 0.045 (6) | −0.001 (4) | 0.006 (4) | 0.000 (4) |
C2 | 0.036 (5) | 0.034 (4) | 0.040 (6) | 0.000 (4) | 0.008 (4) | 0.000 (4) |
C3 | 0.045 (6) | 0.046 (5) | 0.075 (8) | 0.003 (4) | 0.000 (5) | −0.018 (5) |
C4 | 0.045 (6) | 0.048 (6) | 0.137 (11) | −0.015 (5) | 0.006 (6) | −0.030 (6) |
C5 | 0.096 (9) | 0.037 (6) | 0.123 (11) | −0.003 (6) | 0.036 (8) | 0.001 (6) |
C6 | 0.067 (7) | 0.033 (5) | 0.099 (9) | 0.001 (5) | 0.019 (6) | 0.008 (5) |
C7 | 0.050 (5) | 0.036 (5) | 0.072 (7) | 0.005 (4) | 0.006 (5) | 0.010 (4) |
C8 | 0.043 (5) | 0.033 (4) | 0.039 (6) | −0.006 (4) | −0.003 (4) | 0.003 (4) |
C9 | 0.034 (5) | 0.029 (4) | 0.035 (6) | 0.001 (3) | 0.005 (4) | 0.008 (4) |
C10 | 0.033 (5) | 0.032 (4) | 0.036 (6) | 0.002 (3) | 0.005 (4) | 0.005 (4) |
C11 | 0.045 (5) | 0.039 (4) | 0.037 (6) | −0.003 (4) | −0.004 (4) | −0.004 (4) |
C12 | 0.054 (6) | 0.034 (4) | 0.044 (6) | −0.005 (4) | −0.004 (5) | 0.014 (4) |
C13 | 0.045 (5) | 0.021 (4) | 0.044 (6) | −0.002 (3) | 0.008 (4) | 0.002 (4) |
C14 | 0.051 (6) | 0.039 (5) | 0.044 (6) | −0.011 (4) | −0.003 (4) | −0.003 (4) |
C15 | 0.041 (5) | 0.036 (4) | 0.032 (6) | 0.001 (4) | 0.003 (4) | 0.009 (4) |
C16 | 0.035 (5) | 0.032 (4) | 0.033 (6) | −0.002 (4) | 0.008 (4) | −0.009 (4) |
C17 | 0.033 (5) | 0.038 (4) | 0.042 (6) | 0.003 (4) | 0.015 (4) | −0.010 (4) |
C18 | 0.052 (6) | 0.040 (5) | 0.059 (7) | −0.003 (4) | −0.001 (5) | 0.005 (4) |
C19 | 0.085 (8) | 0.031 (5) | 0.108 (10) | −0.006 (5) | 0.018 (7) | 0.001 (5) |
C20 | 0.075 (8) | 0.035 (5) | 0.114 (11) | −0.010 (5) | 0.031 (7) | −0.024 (6) |
C21 | 0.064 (7) | 0.055 (6) | 0.094 (9) | −0.016 (5) | 0.012 (6) | −0.036 (6) |
C22 | 0.043 (6) | 0.058 (6) | 0.068 (7) | 0.002 (4) | 0.004 (5) | −0.015 (5) |
C23 | 0.035 (5) | 0.048 (5) | 0.070 (7) | 0.000 (4) | −0.002 (5) | 0.000 (5) |
C24 | 0.024 (5) | 0.043 (5) | 0.036 (6) | 0.005 (4) | 0.015 (4) | −0.002 (4) |
C25 | 0.035 (5) | 0.033 (4) | 0.042 (6) | 0.007 (4) | 0.010 (4) | 0.007 (4) |
C26 | 0.046 (6) | 0.042 (5) | 0.081 (8) | 0.005 (4) | 0.001 (5) | 0.009 (5) |
C27 | 0.070 (7) | 0.035 (5) | 0.090 (9) | 0.013 (5) | 0.007 (6) | 0.005 (5) |
C28 | 0.064 (7) | 0.042 (5) | 0.070 (8) | −0.001 (5) | 0.008 (6) | −0.005 (5) |
C29 | 0.054 (6) | 0.051 (5) | 0.065 (7) | −0.006 (5) | −0.003 (5) | −0.013 (5) |
C30 | 0.050 (6) | 0.049 (5) | 0.071 (8) | 0.003 (4) | −0.004 (5) | −0.004 (5) |
Br1—C13 | 1.891 (7) | C12—C13 | 1.358 (10) |
Br2—C28 | 1.895 (8) | C12—H12 | 0.9300 |
N1—C1 | 1.353 (9) | C13—C14 | 1.379 (10) |
N1—N2 | 1.395 (7) | C14—C15 | 1.382 (9) |
N1—H1 | 0.8600 | C14—H14 | 0.9300 |
N2—C9 | 1.293 (9) | C15—H15 | 0.9300 |
N3—C16 | 1.343 (8) | C16—C17 | 1.481 (9) |
N3—N4 | 1.390 (7) | C17—C22 | 1.380 (11) |
N3—H3 | 0.8600 | C17—C18 | 1.390 (10) |
N4—C24 | 1.272 (9) | C18—C19 | 1.380 (10) |
O1—C1 | 1.223 (8) | C18—H18 | 0.9300 |
O2—C16 | 1.228 (8) | C19—C20 | 1.396 (13) |
C1—C2 | 1.496 (9) | C19—H19 | 0.9300 |
C2—C7 | 1.366 (10) | C20—C21 | 1.356 (13) |
C2—C3 | 1.376 (10) | C20—H20 | 0.9300 |
C3—C4 | 1.378 (10) | C21—C22 | 1.385 (11) |
C3—H3A | 0.9300 | C21—H21 | 0.9300 |
C4—C5 | 1.384 (13) | C22—H22 | 0.9300 |
C4—H4 | 0.9300 | C23—C24 | 1.482 (10) |
C5—C6 | 1.334 (12) | C23—H23A | 0.9600 |
C5—H5 | 0.9300 | C23—H23B | 0.9600 |
C6—C7 | 1.380 (10) | C23—H23C | 0.9600 |
C6—H6 | 0.9300 | C24—C25 | 1.498 (10) |
C7—H7 | 0.9300 | C25—C26 | 1.367 (10) |
C8—C9 | 1.490 (10) | C25—C30 | 1.382 (10) |
C8—H8A | 0.9600 | C26—C27 | 1.385 (11) |
C8—H8B | 0.9600 | C26—H26 | 0.9300 |
C8—H8C | 0.9600 | C27—C28 | 1.363 (12) |
C9—C10 | 1.496 (9) | C27—H27 | 0.9300 |
C10—C11 | 1.380 (9) | C28—C29 | 1.368 (11) |
C10—C15 | 1.382 (10) | C29—C30 | 1.385 (10) |
C11—C12 | 1.388 (9) | C29—H29 | 0.9300 |
C11—H11 | 0.9300 | C30—H30 | 0.9300 |
C1—N1—N2 | 118.4 (6) | C15—C14—H14 | 120.5 |
C1—N1—H1 | 120.8 | C14—C15—C10 | 121.8 (7) |
N2—N1—H1 | 120.8 | C14—C15—H15 | 119.1 |
C9—N2—N1 | 115.7 (6) | C10—C15—H15 | 119.1 |
C16—N3—N4 | 118.5 (6) | O2—C16—N3 | 123.3 (6) |
C16—N3—H3 | 120.7 | O2—C16—C17 | 120.9 (7) |
N4—N3—H3 | 120.7 | N3—C16—C17 | 115.8 (7) |
C24—N4—N3 | 117.1 (6) | C22—C17—C18 | 118.6 (7) |
O1—C1—N1 | 122.6 (7) | C22—C17—C16 | 122.0 (8) |
O1—C1—C2 | 121.2 (7) | C18—C17—C16 | 119.3 (8) |
N1—C1—C2 | 116.2 (7) | C19—C18—C17 | 121.4 (9) |
C7—C2—C3 | 118.3 (7) | C19—C18—H18 | 119.3 |
C7—C2—C1 | 117.0 (7) | C17—C18—H18 | 119.3 |
C3—C2—C1 | 124.6 (7) | C18—C19—C20 | 118.6 (9) |
C4—C3—C2 | 121.0 (8) | C18—C19—H19 | 120.7 |
C4—C3—H3A | 119.5 | C20—C19—H19 | 120.7 |
C2—C3—H3A | 119.5 | C21—C20—C19 | 120.4 (9) |
C3—C4—C5 | 119.2 (9) | C21—C20—H20 | 119.8 |
C3—C4—H4 | 120.4 | C19—C20—H20 | 119.8 |
C5—C4—H4 | 120.4 | C20—C21—C22 | 120.7 (10) |
C6—C5—C4 | 119.7 (9) | C20—C21—H21 | 119.6 |
C6—C5—H5 | 120.1 | C22—C21—H21 | 119.6 |
C4—C5—H5 | 120.1 | C17—C22—C21 | 120.3 (9) |
C5—C6—C7 | 121.2 (9) | C17—C22—H22 | 119.9 |
C5—C6—H6 | 119.4 | C21—C22—H22 | 119.9 |
C7—C6—H6 | 119.4 | C24—C23—H23A | 109.5 |
C2—C7—C6 | 120.5 (8) | C24—C23—H23B | 109.5 |
C2—C7—H7 | 119.8 | H23A—C23—H23B | 109.5 |
C6—C7—H7 | 119.8 | C24—C23—H23C | 109.5 |
C9—C8—H8A | 109.5 | H23A—C23—H23C | 109.5 |
C9—C8—H8B | 109.5 | H23B—C23—H23C | 109.5 |
H8A—C8—H8B | 109.5 | N4—C24—C23 | 124.7 (7) |
C9—C8—H8C | 109.5 | N4—C24—C25 | 115.3 (7) |
H8A—C8—H8C | 109.5 | C23—C24—C25 | 119.9 (7) |
H8B—C8—H8C | 109.5 | C26—C25—C30 | 116.8 (7) |
N2—C9—C8 | 124.5 (6) | C26—C25—C24 | 123.2 (8) |
N2—C9—C10 | 114.4 (7) | C30—C25—C24 | 120.0 (7) |
C8—C9—C10 | 121.1 (6) | C25—C26—C27 | 121.9 (9) |
C11—C10—C15 | 117.8 (7) | C25—C26—H26 | 119.0 |
C11—C10—C9 | 121.2 (7) | C27—C26—H26 | 119.0 |
C15—C10—C9 | 121.0 (7) | C28—C27—C26 | 119.4 (8) |
C10—C11—C12 | 120.7 (8) | C28—C27—H27 | 120.3 |
C10—C11—H11 | 119.7 | C26—C27—H27 | 120.3 |
C12—C11—H11 | 119.7 | C27—C28—C29 | 121.0 (8) |
C13—C12—C11 | 120.5 (7) | C27—C28—Br2 | 120.3 (7) |
C13—C12—H12 | 119.8 | C29—C28—Br2 | 118.7 (7) |
C11—C12—H12 | 119.8 | C28—C29—C30 | 118.2 (8) |
C12—C13—C14 | 120.2 (7) | C28—C29—H29 | 120.9 |
C12—C13—Br1 | 120.5 (6) | C30—C29—H29 | 120.9 |
C14—C13—Br1 | 119.3 (6) | C25—C30—C29 | 122.7 (8) |
C13—C14—C15 | 119.1 (8) | C25—C30—H30 | 118.7 |
C13—C14—H14 | 120.5 | C29—C30—H30 | 118.7 |
D—H···A | D—H | H···A | D···A | D—H···A |
N3—H3···O1i | 0.86 | 2.20 | 2.943 (8) | 144 |
N1—H1···O2 | 0.86 | 2.23 | 3.000 (8) | 149 |
Symmetry code: (i) x+1, y, z. |
Experimental details
Crystal data | |
Chemical formula | C15H13BrN2O |
Mr | 317.18 |
Crystal system, space group | Monoclinic, P21/c |
Temperature (K) | 298 |
a, b, c (Å) | 9.9770 (11), 31.487 (3), 8.7613 (9) |
β (°) | 96.104 (1) |
V (Å3) | 2736.8 (5) |
Z | 8 |
Radiation type | Mo Kα |
µ (mm−1) | 3.00 |
Crystal size (mm) | 0.49 × 0.18 × 0.12 |
Data collection | |
Diffractometer | Bruker SMART APEX CCD area-detector diffractometer |
Absorption correction | Multi-scan (SADABS; Sheldrick, 1996) |
Tmin, Tmax | 0.321, 0.715 |
No. of measured, independent and observed [I > 2σ(I)] reflections | 13558, 4804, 1961 |
Rint | 0.079 |
(sin θ/λ)max (Å−1) | 0.595 |
Refinement | |
R[F2 > 2σ(F2)], wR(F2), S | 0.064, 0.189, 1.02 |
No. of reflections | 4804 |
No. of parameters | 345 |
H-atom treatment | H-atom parameters constrained |
Δρmax, Δρmin (e Å−3) | 0.47, −0.44 |
Computer programs: SMART (Siemens, 1996), SAINT (Siemens, 1996), SHELXS97 (Sheldrick, 2008), SHELXL97 (Sheldrick, 2008), SHELXTL (Sheldrick, 2008).
D—H···A | D—H | H···A | D···A | D—H···A |
N3—H3···O1i | 0.86 | 2.20 | 2.943 (8) | 144.1 |
N1—H1···O2 | 0.86 | 2.23 | 3.000 (8) | 148.5 |
Symmetry code: (i) x+1, y, z. |
Schiff base compounds are known as having strong anticancer activity (Chakraborty & Patel, 1996) and various biological properties (Jeewoth et al., 1999). Herewith we present the title compound (I) - a new Shiff base compound.
In (I) (Fig. 1), the bond lengths an angles are normal and are comparable to the values observed in similar compounds (Nie et al., 2008; Fun et al., 2008; Cui et al., 2009). The asymmetric unit of (I), contains two independent molecules A and B, respectively. In molecule A, two aromatic rings form a dihedral angle of 32.4 (4) °, while in molecule B this angle is 27.5 (4) °. The C=N bond lengths in the molecules are 1.293 (9)° and 1.272 (9)° (C9=N2,C24=N4), showing the double-bond character.
Weak intermolecular N—H···O hydrogen bonds (Table 1) link molecules into one-dimensional chain propagated in direction [100].