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The title Schiff base compound, C13H10BrN3O2, was derived from the condensation reaction of salicylaldehyde with 5-bromo­nicotinohydrazide. The dihedral angle between the benzene ring and the pyridine ring is 13.2 (4)°. In the crystal structure, mol­ecules are linked through N—H...O and C—H...O inter­molecular hydrogen bonds, forming chains running along the c axis.

Supporting information

cif

Crystallographic Information File (CIF) https://doi.org/10.1107/S1600536807054712/sj2400sup1.cif
Contains datablocks global, I

hkl

Structure factor file (CIF format) https://doi.org/10.1107/S1600536807054712/sj2400Isup2.hkl
Contains datablock I

CCDC reference: 672820

Key indicators

  • Single-crystal X-ray study
  • T = 293 K
  • Mean [sigma](C-C) = 0.007 Å
  • R factor = 0.057
  • wR factor = 0.137
  • Data-to-parameter ratio = 15.2

checkCIF/PLATON results

No syntax errors found



Alert level C PLAT062_ALERT_4_C Rescale T(min) & T(max) by ..................... 0.93 PLAT152_ALERT_1_C Supplied and Calc Volume s.u. Inconsistent ..... ? PLAT242_ALERT_2_C Check Low Ueq as Compared to Neighbors for C11 PLAT341_ALERT_3_C Low Bond Precision on C-C Bonds (x 1000) Ang ... 7
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 0.931 Tmax scaled 0.531 Tmin scaled 0.493 PLAT199_ALERT_1_G Check the Reported _cell_measurement_temperature 293 K PLAT200_ALERT_1_G Check the Reported _diffrn_ambient_temperature . 293 K PLAT860_ALERT_3_G Note: Number of Least-Squares Restraints ....... 1
0 ALERT level A = In general: serious problem 0 ALERT level B = Potentially serious problem 4 ALERT level C = Check and explain 4 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 3 ALERT type 3 Indicator that the structure quality may be low 1 ALERT type 4 Improvement, methodology, query or suggestion 0 ALERT type 5 Informative message, check

Comment top

Recently, the author has reported the structures of several Schiff base complexes (Tang, 2006, 2007a,b) and, in continuation of work in this area, reports herein the structure of the title compound, (I), Fig. 1, a new Schiff base compound.

In the title compound (Fig. 1), the dihedral angle between the benzene ring and the pyridine ring is 13.2 (4)°. The torsion angles C1—C7—N1—N2, C7—N1—N2—C8, and N1—N2—C8—C9 are 1.7 (4), 10.8 (4), and 3.4 (4)°, respectively. All the bond lengths are within normal values (Allen et al., 1987).

In the crystal structure of the compound, molecules are linked through N–H···O and C–H···O intermolecular hydrogen bonds (Table 1), forming chains running along the c axis (Fig. 2).

Related literature top

For related structures, see: Tang, (2007a,b,c) and for reference structural data, see: Allen et al. (1987).

Experimental top

Salicylaldehyde (0.1 mmol, 12.2 mg) and 5-bromonicotinic acid hydrazide (0.1 mmol, 21.6 mg) were dissolved in an ethanol solution (20 ml). The mixture was stirred at reflux for 10 min to give a clear yellowish solution. Yellowish needle-like crystals of the compound were formed by slow evaporation of the solvent over several days.

Refinement top

H2 was located from a difference Fourier map and refined isotropically, with the N–H distance restrained to 0.90 (1) Å, and with the Uiso(H) fixed at 0.08 Å2. Other H atoms were constrained to ideal geometries, with C–H = 0.93 Å, Uiso(H) = 1.2Ueq(C) and 0.82 Å, Uiso = 1.5Ueq (O) for the OH group..

Computing details top

Data collection: SMART (Bruker, 2002); cell refinement: SAINT (Bruker, 2002); data reduction: SAINT (Bruker, 2002); program(s) used to solve structure: SHELXS97 (Sheldrick, 1997a); program(s) used to refine structure: SHELXL97 (Sheldrick, 1997a); molecular graphics: SHELXTL (Sheldrick, 1997b); software used to prepare material for publication: SHELXL97 (Sheldrick, 1997a).

Figures top
[Figure 1] Fig. 1. The molecular structure of the compound, showing the atom-numbering scheme. Displacement ellipsoids are drawn at the 30% probability level.
[Figure 2] Fig. 2. Molecular packing of (I) with hydrogen bonds drawn as dashed lines.
5-Bromo-N'-(2-hydroxybenzylidene)nicotinohydrazide top
Crystal data top
C13H10BrN3O2F(000) = 640
Mr = 320.15Dx = 1.638 Mg m3
Monoclinic, P21/cMo Kα radiation, λ = 0.71073 Å
Hall symbol: -P 2ybcCell parameters from 929 reflections
a = 10.940 (2) Åθ = 2.6–24.0°
b = 13.673 (3) ŵ = 3.17 mm1
c = 8.6900 (17) ÅT = 293 K
β = 92.88 (3)°Cut from needle, colorless
V = 1298.2 (4) Å30.23 × 0.20 × 0.20 mm
Z = 4
Data collection top
Bruker SMART CCD area detector
diffractometer
2679 independent reflections
Radiation source: fine-focus sealed tube1498 reflections with I > 2σ(I)
Graphite monochromatorRint = 0.079
ω scansθmax = 26.5°, θmin = 1.9°
Absorption correction: multi-scan
(SADABS; Sheldrick, 1996)
h = 1313
Tmin = 0.530, Tmax = 0.570k = 1717
10307 measured reflectionsl = 1010
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)] = 0.057Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.137H atoms treated by a mixture of independent and constrained refinement
S = 1.00 w = 1/[σ2(Fo2) + (0.0496P)2 + 0.272P]
where P = (Fo2 + 2Fc2)/3
2679 reflections(Δ/σ)max < 0.001
176 parametersΔρmax = 0.54 e Å3
1 restraintΔρmin = 0.59 e Å3
Crystal data top
C13H10BrN3O2V = 1298.2 (4) Å3
Mr = 320.15Z = 4
Monoclinic, P21/cMo Kα radiation
a = 10.940 (2) ŵ = 3.17 mm1
b = 13.673 (3) ÅT = 293 K
c = 8.6900 (17) Å0.23 × 0.20 × 0.20 mm
β = 92.88 (3)°
Data collection top
Bruker SMART CCD area detector
diffractometer
2679 independent reflections
Absorption correction: multi-scan
(SADABS; Sheldrick, 1996)
1498 reflections with I > 2σ(I)
Tmin = 0.530, Tmax = 0.570Rint = 0.079
10307 measured reflections
Refinement top
R[F2 > 2σ(F2)] = 0.0571 restraint
wR(F2) = 0.137H atoms treated by a mixture of independent and constrained refinement
S = 1.00Δρmax = 0.54 e Å3
2679 reflectionsΔρmin = 0.59 e Å3
176 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
Br10.85979 (6)0.19758 (4)1.10713 (8)0.0724 (3)
O10.5721 (4)0.3989 (3)0.7037 (4)0.0600 (10)
H10.61970.36070.74820.090*
O20.7822 (3)0.1592 (2)0.8338 (4)0.0491 (9)
N10.7140 (4)0.3355 (3)0.9392 (4)0.0407 (10)
N20.7708 (4)0.2650 (3)1.0324 (4)0.0427 (10)
N30.9790 (4)0.0604 (4)1.3039 (5)0.0622 (13)
C10.6465 (4)0.5014 (3)0.9151 (5)0.0390 (11)
C20.5799 (4)0.4870 (4)0.7732 (5)0.0428 (12)
C30.5214 (5)0.5671 (4)0.7012 (6)0.0560 (15)
H30.47720.55840.60800.067*
C40.5287 (5)0.6577 (4)0.7664 (7)0.0613 (16)
H40.49000.71010.71630.074*
C50.5919 (6)0.6727 (4)0.9040 (7)0.0612 (15)
H50.59570.73500.94670.073*
C60.6502 (5)0.5954 (4)0.9801 (6)0.0520 (13)
H60.69200.60591.07450.062*
C70.7063 (4)0.4212 (3)0.9972 (5)0.0430 (12)
H70.74030.43241.09590.052*
C80.7997 (4)0.1786 (3)0.9701 (5)0.0390 (12)
C90.8541 (4)0.1038 (3)1.0785 (5)0.0368 (11)
C100.8345 (4)0.0060 (3)1.0471 (5)0.0419 (12)
H100.78770.01310.95990.050*
C110.8848 (4)0.0628 (3)1.1463 (5)0.0417 (12)
C120.9565 (5)0.0326 (4)1.2724 (6)0.0585 (15)
H120.99070.07991.33840.070*
C130.9273 (5)0.1269 (4)1.2081 (5)0.0486 (13)
H130.94150.19261.22990.058*
H20.777 (5)0.278 (4)1.1340 (17)0.080*
Atomic displacement parameters (Å2) top
U11U22U33U12U13U23
Br10.0660 (4)0.0424 (4)0.1080 (6)0.0007 (3)0.0041 (4)0.0148 (3)
O10.075 (3)0.049 (2)0.054 (2)0.008 (2)0.014 (2)0.0102 (19)
O20.077 (3)0.0414 (19)0.0277 (19)0.0006 (17)0.0089 (17)0.0015 (15)
N10.051 (3)0.038 (2)0.033 (2)0.0049 (19)0.0038 (19)0.0082 (19)
N20.061 (3)0.040 (2)0.027 (2)0.002 (2)0.004 (2)0.0015 (19)
N30.070 (3)0.066 (3)0.049 (3)0.017 (3)0.019 (2)0.005 (2)
C10.041 (3)0.038 (3)0.038 (3)0.003 (2)0.001 (2)0.003 (2)
C20.045 (3)0.045 (3)0.039 (3)0.003 (2)0.006 (2)0.002 (2)
C30.066 (4)0.058 (4)0.044 (3)0.018 (3)0.003 (3)0.005 (3)
C40.069 (4)0.044 (3)0.071 (4)0.018 (3)0.010 (3)0.012 (3)
C50.074 (4)0.043 (3)0.067 (4)0.005 (3)0.005 (3)0.002 (3)
C60.057 (4)0.050 (3)0.048 (3)0.002 (3)0.002 (3)0.005 (3)
C70.048 (3)0.043 (3)0.039 (3)0.005 (2)0.002 (2)0.001 (2)
C80.042 (3)0.043 (3)0.032 (3)0.001 (2)0.002 (2)0.003 (2)
C90.038 (3)0.039 (3)0.033 (3)0.004 (2)0.000 (2)0.003 (2)
C100.041 (3)0.044 (3)0.041 (3)0.001 (2)0.001 (2)0.007 (2)
C110.037 (3)0.041 (3)0.047 (3)0.003 (2)0.006 (2)0.005 (2)
C120.060 (4)0.063 (4)0.052 (4)0.018 (3)0.003 (3)0.015 (3)
C130.054 (3)0.046 (3)0.044 (3)0.004 (3)0.011 (3)0.007 (3)
Geometric parameters (Å, º) top
Br1—C111.892 (5)C3—H30.9300
O1—C21.349 (5)C4—C51.367 (8)
O1—H10.8200C4—H40.9300
O2—C81.220 (5)C5—C61.385 (7)
N1—C71.280 (5)C5—H50.9300
N1—N21.386 (5)C6—H60.9300
N2—C81.344 (6)C7—H70.9300
N2—H20.899 (10)C8—C91.493 (6)
N3—C121.321 (6)C9—C101.380 (6)
N3—C131.339 (6)C9—C131.385 (6)
C1—C61.404 (6)C10—C111.372 (6)
C1—C21.414 (6)C10—H100.9300
C1—C71.447 (6)C11—C121.378 (7)
C2—C31.400 (6)C12—H120.9300
C3—C41.362 (7)C13—H130.9300
C2—O1—H1109.5C1—C6—H6119.9
C7—N1—N2116.3 (4)N1—C7—C1122.4 (4)
C8—N2—N1118.9 (4)N1—C7—H7118.8
C8—N2—H2124 (4)C1—C7—H7118.8
N1—N2—H2117 (4)O2—C8—N2123.6 (4)
C12—N3—C13117.1 (5)O2—C8—C9120.1 (4)
C6—C1—C2118.8 (4)N2—C8—C9116.2 (4)
C6—C1—C7119.5 (4)C10—C9—C13117.3 (4)
C2—C1—C7121.7 (4)C10—C9—C8119.1 (4)
O1—C2—C3118.8 (4)C13—C9—C8123.6 (4)
O1—C2—C1122.2 (4)C11—C10—C9119.1 (5)
C3—C2—C1119.0 (5)C11—C10—H10120.4
C4—C3—C2120.6 (5)C9—C10—H10120.4
C4—C3—H3119.7C10—C11—C12119.3 (5)
C2—C3—H3119.7C10—C11—Br1120.3 (4)
C3—C4—C5121.1 (5)C12—C11—Br1120.4 (4)
C3—C4—H4119.4N3—C12—C11123.1 (5)
C5—C4—H4119.4N3—C12—H12118.5
C4—C5—C6120.3 (5)C11—C12—H12118.5
C4—C5—H5119.9N3—C13—C9124.1 (5)
C6—C5—H5119.9N3—C13—H13117.9
C5—C6—C1120.2 (5)C9—C13—H13117.9
C5—C6—H6119.9
Hydrogen-bond geometry (Å, º) top
D—H···AD—HH···AD···AD—H···A
N2—H2···O2i0.90 (1)1.94 (2)2.814 (5)164 (5)
O1—H1···N10.821.942.651 (5)145
C7—H7···O2i0.932.443.195 (5)138
Symmetry code: (i) x, y+1/2, z+1/2.

Experimental details

Crystal data
Chemical formulaC13H10BrN3O2
Mr320.15
Crystal system, space groupMonoclinic, P21/c
Temperature (K)293
a, b, c (Å)10.940 (2), 13.673 (3), 8.6900 (17)
β (°) 92.88 (3)
V3)1298.2 (4)
Z4
Radiation typeMo Kα
µ (mm1)3.17
Crystal size (mm)0.23 × 0.20 × 0.20
Data collection
DiffractometerBruker SMART CCD area detector
diffractometer
Absorption correctionMulti-scan
(SADABS; Sheldrick, 1996)
Tmin, Tmax0.530, 0.570
No. of measured, independent and
observed [I > 2σ(I)] reflections
10307, 2679, 1498
Rint0.079
(sin θ/λ)max1)0.628
Refinement
R[F2 > 2σ(F2)], wR(F2), S 0.057, 0.137, 1.00
No. of reflections2679
No. of parameters176
No. of restraints1
H-atom treatmentH atoms treated by a mixture of independent and constrained refinement
Δρmax, Δρmin (e Å3)0.54, 0.59

Computer programs: SMART (Bruker, 2002), SAINT (Bruker, 2002), SHELXS97 (Sheldrick, 1997a), SHELXL97 (Sheldrick, 1997a), SHELXTL (Sheldrick, 1997b).

Hydrogen-bond geometry (Å, º) top
D—H···AD—HH···AD···AD—H···A
N2—H2···O2i0.899 (10)1.937 (18)2.814 (5)164 (5)
O1—H1···N10.821.942.651 (5)145
C7—H7···O2i0.932.443.195 (5)138
Symmetry code: (i) x, y+1/2, z+1/2.
 

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