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The asymmetric unit of the title compound, C15H13BrN2O, contains two independent mol­ecules with different conformations; the two aromatic rings form dihedral angles of 32.4 (4) and 27.5 (4)° in the two mol­ecules. In the crystal structure, inter­molecular N—H...O hydrogen bonds link mol­ecules into chains propagating in [100].

Supporting information

cif

Crystallographic Information File (CIF) https://doi.org/10.1107/S1600536809049952/cv2651sup1.cif
Contains datablocks I, global

hkl

Structure factor file (CIF format) https://doi.org/10.1107/S1600536809049952/cv2651Isup2.hkl
Contains datablock I

CCDC reference: 766703

Key indicators

  • Single-crystal X-ray study
  • T = 298 K
  • Mean [sigma](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

Comment top

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].

Related literature top

For the biological properties of Schiff base ligands, see: Chakraborty & Patel (1996); Jeewoth et al.(1999). For related crystal structures, see: Fun et al. (2008); Cui et al. (2009); Nie (2008).

Experimental top

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%.

Refinement top

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).

Computing details top

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).

Figures top
[Figure 1] Fig. 1. A view of (I) showing the atomic numbering scheme and 30% probability displacement ellipsoids.
(E)-N'-[1-(4-Bromophenyl)ethylidene]benzohydrazide top
Crystal data top
C15H13BrN2OF(000) = 1280
Mr = 317.18Dx = 1.540 Mg m3
Monoclinic, P21/cMo Kα radiation, λ = 0.71073 Å
a = 9.9770 (11) ÅCell parameters from 1649 reflections
b = 31.487 (3) Åθ = 2.6–22.4°
c = 8.7613 (9) ŵ = 3.00 mm1
β = 96.104 (1)°T = 298 K
V = 2736.8 (5) Å3Block, colourless
Z = 80.49 × 0.18 × 0.12 mm
Data collection top
Bruker SMART APEX CCD area-detector
diffractometer
4804 independent reflections
Radiation source: fine-focus sealed tube1961 reflections with I > 2σ(I)
Graphite monochromatorRint = 0.079
phi and ω scansθmax = 25.0°, θmin = 1.3°
Absorption correction: multi-scan
(SADABS; Sheldrick, 1996)
h = 1110
Tmin = 0.321, Tmax = 0.715k = 3737
13558 measured reflectionsl = 910
Refinement top
Refinement on F2Primary atom site location: structure-invariant direct methods
Least-squares matrix: fullSecondary atom site location: difference Fourier map
R[F2 > 2σ(F2)] = 0.064Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.189H-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 parametersΔρmax = 0.47 e Å3
0 restraintsΔρmin = 0.44 e Å3
Crystal data top
C15H13BrN2OV = 2736.8 (5) Å3
Mr = 317.18Z = 8
Monoclinic, P21/cMo Kα radiation
a = 9.9770 (11) ŵ = 3.00 mm1
b = 31.487 (3) ÅT = 298 K
c = 8.7613 (9) Å0.49 × 0.18 × 0.12 mm
β = 96.104 (1)°
Data collection top
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 = 0.715Rint = 0.079
13558 measured reflections
Refinement top
R[F2 > 2σ(F2)] = 0.0640 restraints
wR(F2) = 0.189H-atom parameters constrained
S = 1.02Δρmax = 0.47 e Å3
4804 reflectionsΔρmin = 0.44 e Å3
345 parameters
Special details top

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) top
xyzUiso*/Ueq
Br10.05576 (10)0.04761 (3)0.12825 (13)0.0742 (4)
Br20.53233 (12)0.04532 (3)0.13223 (14)0.0925 (5)
N10.1623 (6)0.30472 (16)0.1860 (7)0.0375 (17)
H10.24500.31230.20700.045*
N20.1275 (6)0.26193 (18)0.1697 (8)0.0414 (18)
N30.6642 (6)0.30098 (17)0.1957 (7)0.0415 (18)
H30.74540.30840.22720.050*
N40.6303 (6)0.25836 (18)0.1760 (7)0.0375 (17)
O10.0567 (5)0.32437 (15)0.1524 (7)0.0512 (16)
O20.4486 (5)0.32125 (15)0.1277 (6)0.0465 (15)
C10.0627 (8)0.3340 (2)0.1678 (9)0.037 (2)
C20.1063 (8)0.3795 (2)0.1712 (9)0.036 (2)
C30.2317 (9)0.3936 (3)0.2308 (11)0.056 (3)
H3A0.29650.37400.26930.067*
C40.2627 (9)0.4362 (3)0.2342 (13)0.077 (3)
H40.34760.44540.27500.092*
C50.1660 (12)0.4652 (3)0.1765 (13)0.084 (4)
H50.18570.49410.17760.100*
C60.0444 (10)0.4515 (3)0.1191 (11)0.066 (3)
H60.01980.47110.07920.079*
C70.0123 (8)0.4089 (2)0.1179 (10)0.052 (2)
H70.07410.40020.08060.063*
C80.3318 (7)0.2479 (2)0.3464 (9)0.039 (2)
H8A0.40620.25260.28730.058*
H8B0.35430.22570.41960.058*
H8C0.31320.27360.39960.058*
C90.2105 (7)0.2354 (2)0.2421 (9)0.032 (2)
C100.1756 (7)0.1897 (2)0.2133 (9)0.034 (2)
C110.2275 (8)0.1584 (2)0.3126 (9)0.041 (2)
H110.28670.16560.39790.049*
C120.1921 (8)0.1161 (2)0.2866 (10)0.045 (2)
H120.22870.09530.35370.053*
C130.1045 (8)0.1051 (2)0.1637 (10)0.036 (2)
C140.0528 (8)0.1356 (2)0.0611 (10)0.046 (2)
H140.00470.12810.02530.055*
C150.0875 (7)0.1777 (2)0.0884 (9)0.036 (2)
H150.05050.19840.02100.044*
C160.5674 (8)0.3303 (2)0.1644 (9)0.0331 (19)
C170.6123 (7)0.3751 (2)0.1748 (10)0.037 (2)
C180.5576 (8)0.4041 (2)0.0657 (10)0.051 (2)
H180.49520.39480.01370.061*
C190.5939 (10)0.4464 (3)0.0728 (13)0.074 (3)
H190.55930.46530.00290.089*
C200.6835 (10)0.4602 (3)0.1961 (14)0.073 (3)
H200.70810.48870.20340.088*
C210.7347 (10)0.4324 (3)0.3050 (13)0.071 (3)
H210.79330.44200.38740.085*
C220.7009 (8)0.3897 (3)0.2950 (11)0.056 (3)
H220.73800.37090.36950.068*
C230.8370 (8)0.2420 (2)0.3406 (11)0.052 (2)
H23A0.91010.24580.27910.077*
H23B0.85820.21940.41250.077*
H23C0.82310.26780.39530.077*
C240.7126 (7)0.2313 (2)0.2401 (9)0.034 (2)
C250.6731 (8)0.1857 (2)0.2140 (9)0.036 (2)
C260.7538 (8)0.1525 (2)0.2651 (11)0.057 (3)
H260.83740.15810.31880.068*
C270.7146 (10)0.1107 (3)0.2391 (12)0.065 (3)
H270.77190.08860.27340.078*
C280.5913 (10)0.1022 (3)0.1627 (11)0.058 (3)
C290.5083 (9)0.1343 (3)0.1057 (10)0.057 (3)
H290.42500.12850.05180.069*
C300.5519 (8)0.1757 (3)0.1305 (10)0.057 (3)
H300.49730.19770.08920.069*
Atomic displacement parameters (Å2) top
U11U22U33U12U13U23
Br10.0932 (8)0.0335 (5)0.0912 (9)0.0095 (5)0.0117 (6)0.0017 (5)
Br20.1330 (11)0.0416 (6)0.1011 (11)0.0177 (6)0.0043 (8)0.0026 (6)
N10.032 (4)0.021 (3)0.058 (5)0.003 (3)0.001 (3)0.001 (3)
N20.033 (4)0.028 (3)0.063 (6)0.002 (3)0.005 (4)0.004 (3)
N30.032 (4)0.027 (3)0.064 (6)0.000 (3)0.002 (4)0.001 (3)
N40.035 (4)0.037 (4)0.041 (5)0.003 (3)0.005 (4)0.001 (3)
O10.034 (3)0.038 (3)0.083 (5)0.005 (3)0.008 (3)0.003 (3)
O20.028 (3)0.038 (3)0.072 (5)0.004 (2)0.000 (3)0.004 (3)
C10.031 (5)0.035 (4)0.045 (6)0.001 (4)0.006 (4)0.000 (4)
C20.036 (5)0.034 (4)0.040 (6)0.000 (4)0.008 (4)0.000 (4)
C30.045 (6)0.046 (5)0.075 (8)0.003 (4)0.000 (5)0.018 (5)
C40.045 (6)0.048 (6)0.137 (11)0.015 (5)0.006 (6)0.030 (6)
C50.096 (9)0.037 (6)0.123 (11)0.003 (6)0.036 (8)0.001 (6)
C60.067 (7)0.033 (5)0.099 (9)0.001 (5)0.019 (6)0.008 (5)
C70.050 (5)0.036 (5)0.072 (7)0.005 (4)0.006 (5)0.010 (4)
C80.043 (5)0.033 (4)0.039 (6)0.006 (4)0.003 (4)0.003 (4)
C90.034 (5)0.029 (4)0.035 (6)0.001 (3)0.005 (4)0.008 (4)
C100.033 (5)0.032 (4)0.036 (6)0.002 (3)0.005 (4)0.005 (4)
C110.045 (5)0.039 (4)0.037 (6)0.003 (4)0.004 (4)0.004 (4)
C120.054 (6)0.034 (4)0.044 (6)0.005 (4)0.004 (5)0.014 (4)
C130.045 (5)0.021 (4)0.044 (6)0.002 (3)0.008 (4)0.002 (4)
C140.051 (6)0.039 (5)0.044 (6)0.011 (4)0.003 (4)0.003 (4)
C150.041 (5)0.036 (4)0.032 (6)0.001 (4)0.003 (4)0.009 (4)
C160.035 (5)0.032 (4)0.033 (6)0.002 (4)0.008 (4)0.009 (4)
C170.033 (5)0.038 (4)0.042 (6)0.003 (4)0.015 (4)0.010 (4)
C180.052 (6)0.040 (5)0.059 (7)0.003 (4)0.001 (5)0.005 (4)
C190.085 (8)0.031 (5)0.108 (10)0.006 (5)0.018 (7)0.001 (5)
C200.075 (8)0.035 (5)0.114 (11)0.010 (5)0.031 (7)0.024 (6)
C210.064 (7)0.055 (6)0.094 (9)0.016 (5)0.012 (6)0.036 (6)
C220.043 (6)0.058 (6)0.068 (7)0.002 (4)0.004 (5)0.015 (5)
C230.035 (5)0.048 (5)0.070 (7)0.000 (4)0.002 (5)0.000 (5)
C240.024 (5)0.043 (5)0.036 (6)0.005 (4)0.015 (4)0.002 (4)
C250.035 (5)0.033 (4)0.042 (6)0.007 (4)0.010 (4)0.007 (4)
C260.046 (6)0.042 (5)0.081 (8)0.005 (4)0.001 (5)0.009 (5)
C270.070 (7)0.035 (5)0.090 (9)0.013 (5)0.007 (6)0.005 (5)
C280.064 (7)0.042 (5)0.070 (8)0.001 (5)0.008 (6)0.005 (5)
C290.054 (6)0.051 (5)0.065 (7)0.006 (5)0.003 (5)0.013 (5)
C300.050 (6)0.049 (5)0.071 (8)0.003 (4)0.004 (5)0.004 (5)
Geometric parameters (Å, º) top
Br1—C131.891 (7)C12—C131.358 (10)
Br2—C281.895 (8)C12—H120.9300
N1—C11.353 (9)C13—C141.379 (10)
N1—N21.395 (7)C14—C151.382 (9)
N1—H10.8600C14—H140.9300
N2—C91.293 (9)C15—H150.9300
N3—C161.343 (8)C16—C171.481 (9)
N3—N41.390 (7)C17—C221.380 (11)
N3—H30.8600C17—C181.390 (10)
N4—C241.272 (9)C18—C191.380 (10)
O1—C11.223 (8)C18—H180.9300
O2—C161.228 (8)C19—C201.396 (13)
C1—C21.496 (9)C19—H190.9300
C2—C71.366 (10)C20—C211.356 (13)
C2—C31.376 (10)C20—H200.9300
C3—C41.378 (10)C21—C221.385 (11)
C3—H3A0.9300C21—H210.9300
C4—C51.384 (13)C22—H220.9300
C4—H40.9300C23—C241.482 (10)
C5—C61.334 (12)C23—H23A0.9600
C5—H50.9300C23—H23B0.9600
C6—C71.380 (10)C23—H23C0.9600
C6—H60.9300C24—C251.498 (10)
C7—H70.9300C25—C261.367 (10)
C8—C91.490 (10)C25—C301.382 (10)
C8—H8A0.9600C26—C271.385 (11)
C8—H8B0.9600C26—H260.9300
C8—H8C0.9600C27—C281.363 (12)
C9—C101.496 (9)C27—H270.9300
C10—C111.380 (9)C28—C291.368 (11)
C10—C151.382 (10)C29—C301.385 (10)
C11—C121.388 (9)C29—H290.9300
C11—H110.9300C30—H300.9300
C1—N1—N2118.4 (6)C15—C14—H14120.5
C1—N1—H1120.8C14—C15—C10121.8 (7)
N2—N1—H1120.8C14—C15—H15119.1
C9—N2—N1115.7 (6)C10—C15—H15119.1
C16—N3—N4118.5 (6)O2—C16—N3123.3 (6)
C16—N3—H3120.7O2—C16—C17120.9 (7)
N4—N3—H3120.7N3—C16—C17115.8 (7)
C24—N4—N3117.1 (6)C22—C17—C18118.6 (7)
O1—C1—N1122.6 (7)C22—C17—C16122.0 (8)
O1—C1—C2121.2 (7)C18—C17—C16119.3 (8)
N1—C1—C2116.2 (7)C19—C18—C17121.4 (9)
C7—C2—C3118.3 (7)C19—C18—H18119.3
C7—C2—C1117.0 (7)C17—C18—H18119.3
C3—C2—C1124.6 (7)C18—C19—C20118.6 (9)
C4—C3—C2121.0 (8)C18—C19—H19120.7
C4—C3—H3A119.5C20—C19—H19120.7
C2—C3—H3A119.5C21—C20—C19120.4 (9)
C3—C4—C5119.2 (9)C21—C20—H20119.8
C3—C4—H4120.4C19—C20—H20119.8
C5—C4—H4120.4C20—C21—C22120.7 (10)
C6—C5—C4119.7 (9)C20—C21—H21119.6
C6—C5—H5120.1C22—C21—H21119.6
C4—C5—H5120.1C17—C22—C21120.3 (9)
C5—C6—C7121.2 (9)C17—C22—H22119.9
C5—C6—H6119.4C21—C22—H22119.9
C7—C6—H6119.4C24—C23—H23A109.5
C2—C7—C6120.5 (8)C24—C23—H23B109.5
C2—C7—H7119.8H23A—C23—H23B109.5
C6—C7—H7119.8C24—C23—H23C109.5
C9—C8—H8A109.5H23A—C23—H23C109.5
C9—C8—H8B109.5H23B—C23—H23C109.5
H8A—C8—H8B109.5N4—C24—C23124.7 (7)
C9—C8—H8C109.5N4—C24—C25115.3 (7)
H8A—C8—H8C109.5C23—C24—C25119.9 (7)
H8B—C8—H8C109.5C26—C25—C30116.8 (7)
N2—C9—C8124.5 (6)C26—C25—C24123.2 (8)
N2—C9—C10114.4 (7)C30—C25—C24120.0 (7)
C8—C9—C10121.1 (6)C25—C26—C27121.9 (9)
C11—C10—C15117.8 (7)C25—C26—H26119.0
C11—C10—C9121.2 (7)C27—C26—H26119.0
C15—C10—C9121.0 (7)C28—C27—C26119.4 (8)
C10—C11—C12120.7 (8)C28—C27—H27120.3
C10—C11—H11119.7C26—C27—H27120.3
C12—C11—H11119.7C27—C28—C29121.0 (8)
C13—C12—C11120.5 (7)C27—C28—Br2120.3 (7)
C13—C12—H12119.8C29—C28—Br2118.7 (7)
C11—C12—H12119.8C28—C29—C30118.2 (8)
C12—C13—C14120.2 (7)C28—C29—H29120.9
C12—C13—Br1120.5 (6)C30—C29—H29120.9
C14—C13—Br1119.3 (6)C25—C30—C29122.7 (8)
C13—C14—C15119.1 (8)C25—C30—H30118.7
C13—C14—H14120.5C29—C30—H30118.7
Hydrogen-bond geometry (Å, º) top
D—H···AD—HH···AD···AD—H···A
N3—H3···O1i0.862.202.943 (8)144
N1—H1···O20.862.233.000 (8)149
Symmetry code: (i) x+1, y, z.

Experimental details

Crystal data
Chemical formulaC15H13BrN2O
Mr317.18
Crystal system, space groupMonoclinic, P21/c
Temperature (K)298
a, b, c (Å)9.9770 (11), 31.487 (3), 8.7613 (9)
β (°) 96.104 (1)
V3)2736.8 (5)
Z8
Radiation typeMo Kα
µ (mm1)3.00
Crystal size (mm)0.49 × 0.18 × 0.12
Data collection
DiffractometerBruker SMART APEX CCD area-detector
diffractometer
Absorption correctionMulti-scan
(SADABS; Sheldrick, 1996)
Tmin, Tmax0.321, 0.715
No. of measured, independent and
observed [I > 2σ(I)] reflections
13558, 4804, 1961
Rint0.079
(sin θ/λ)max1)0.595
Refinement
R[F2 > 2σ(F2)], wR(F2), S 0.064, 0.189, 1.02
No. of reflections4804
No. of parameters345
H-atom treatmentH-atom parameters constrained
Δρmax, Δρmin (e Å3)0.47, 0.44

Computer programs: SMART (Siemens, 1996), SAINT (Siemens, 1996), SHELXS97 (Sheldrick, 2008), SHELXL97 (Sheldrick, 2008), SHELXTL (Sheldrick, 2008).

Hydrogen-bond geometry (Å, º) top
D—H···AD—HH···AD···AD—H···A
N3—H3···O1i0.862.202.943 (8)144.1
N1—H1···O20.862.233.000 (8)148.5
Symmetry code: (i) x+1, y, z.
 

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