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The geometric parameters of the title mol­ecule, C15H12BrN3O4, are in the usual ranges. The dihedral angle between the two benzene rings is 49.69 (10)°. In the crystal structure, mol­ecules are connected by inter­molecular N—H...O hydrogen bonds to form a one-dimensional chain in the c-axis direction.

Supporting information

cif

Crystallographic Information File (CIF) https://doi.org/10.1107/S1600536807034150/lh2458sup1.cif
Contains datablocks I, global

hkl

Structure factor file (CIF format) https://doi.org/10.1107/S1600536807034150/lh2458Isup2.hkl
Contains datablock I

CCDC reference: 657787

Key indicators

  • Single-crystal X-ray study
  • T = 173 K
  • Mean [sigma](C-C) = 0.005 Å
  • R factor = 0.042
  • wR factor = 0.103
  • Data-to-parameter ratio = 13.2

checkCIF/PLATON results

No syntax errors found



Alert level C PLAT222_ALERT_3_C Large Non-Solvent H Ueq(max)/Ueq(min) ... 3.77 Ratio PLAT431_ALERT_2_C Short Inter HL..A Contact Br1 .. O4 .. 3.18 Ang.
0 ALERT level A = In general: serious problem 0 ALERT level B = Potentially serious problem 2 ALERT level C = Check and explain 0 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 1 ALERT type 3 Indicator that the structure quality may be low 0 ALERT type 4 Improvement, methodology, query or suggestion 0 ALERT type 5 Informative message, check

Comment top

Schiff bases are used as substrates in the preparation of number of industrial and biologically active compounds via ring closure, cycloaddition and replacement reactions. Some Schiff base derivatives were reported to possess antimicrobial, anti-inflammatory and central nervous system activities and moreover, Schiff bases are also known to have biological activities such as antimicrobial, antifungal, antitumor, and as herbicides (Varma et al., 1986; Misra et al., 1981; Agarwal et al., 1983; Singh et al., 1988; Hodnett et al., 1970). The title compound has been synthesized and its crystal structure is reported herein.

The geometric parameters of the title molecule, C15H12BrN3O4, are in the usual ranges. The dihedral angle between the two benzene rings is 49.69 (10)°. In the crystal structure, molecules are connected by intermolecular N—H···O hydrogen bonds to form one-dimensional chain in the c axis direction.

Similar structures related to the title compound that have already been reported are 2-chloro-3,4-dimethoxybenzaldehyde (4-nitrophenyl)hydrazone (Shan et al., 2004), 1-(4-fluoro-2-hydroxyphenyl)ethanone 4-nitrobenzoylhydrazone (Ali et al., 2004) and 3-(2-bromo-5-methoxyphenyl)-5-methyl-1-(4-phenyl-1,3-thiazol-2-yl)- 1H-1,2,4-triazole (Yathirajan et al., 2006).

Related literature top

For related structures, see: Shan et al. (2004); Ali et al. (2004); Yathirajan et al. (2006). For related literature, see: Varma et al. (1986); Misra et al. (1981); Agarwal et al. (1983); Singh & Dash (1988); Hodnett & Dunn (1970).

Experimental top

A mixture of 2-bromo-5-methoxybenzohydrazide (0.735 g, 0.003 mol) and 4-nitrobenzaldehyde (0.453 g, 0.003 mol) in 15 ml of absolute alcohol containing 2 drops of dilute sulfuric acid was refluxed for about 3 h. On cooling, the solid separated was filtered and recrystallized from ethyl acetate (m.p.: 462–464 K). Analysis for C15H12BrN3O4: Found (Calculated): C: 47.55 (47.64); H: 3.16 (3.20); N:11.06% (11.11%).

Refinement top

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) [C—H = 0.98 Å and Uiso(H) = 1.5Ueq(C) for the methyl group, which was allowed to rotate but not to tip]. The H atom bonded to N was freely refined.

Structure description top

Schiff bases are used as substrates in the preparation of number of industrial and biologically active compounds via ring closure, cycloaddition and replacement reactions. Some Schiff base derivatives were reported to possess antimicrobial, anti-inflammatory and central nervous system activities and moreover, Schiff bases are also known to have biological activities such as antimicrobial, antifungal, antitumor, and as herbicides (Varma et al., 1986; Misra et al., 1981; Agarwal et al., 1983; Singh et al., 1988; Hodnett et al., 1970). The title compound has been synthesized and its crystal structure is reported herein.

The geometric parameters of the title molecule, C15H12BrN3O4, are in the usual ranges. The dihedral angle between the two benzene rings is 49.69 (10)°. In the crystal structure, molecules are connected by intermolecular N—H···O hydrogen bonds to form one-dimensional chain in the c axis direction.

Similar structures related to the title compound that have already been reported are 2-chloro-3,4-dimethoxybenzaldehyde (4-nitrophenyl)hydrazone (Shan et al., 2004), 1-(4-fluoro-2-hydroxyphenyl)ethanone 4-nitrobenzoylhydrazone (Ali et al., 2004) and 3-(2-bromo-5-methoxyphenyl)-5-methyl-1-(4-phenyl-1,3-thiazol-2-yl)- 1H-1,2,4-triazole (Yathirajan et al., 2006).

For related structures, see: Shan et al. (2004); Ali et al. (2004); Yathirajan et al. (2006). For related literature, see: Varma et al. (1986); Misra et al. (1981); Agarwal et al. (1983); Singh & Dash (1988); Hodnett & Dunn (1970).

Computing details top

Data collection: X-AREA (Stoe & Cie, 2001); cell refinement: X-AREA; data reduction: X-AREA; 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.

Figures top
[Figure 1] Fig. 1. The molecular structure with the atom numbering; displacement ellipsoids are at the 50% probability level.
[Figure 2] Fig. 2. The reaction scheme
2-Bromo-5-methoxy-N'-[(E)-(4-nitrophenyl)methylene]benzohydrazide top
Crystal data top
C15H12BrN3O4F(000) = 760
Mr = 378.19Dx = 1.665 Mg m3
Monoclinic, P21/cMo Kα radiation, λ = 0.71073 Å
Hall symbol: -P 2ybcCell parameters from 9399 reflections
a = 7.2604 (8) Åθ = 3.6–25.7°
b = 21.8931 (19) ŵ = 2.75 mm1
c = 9.5795 (12) ÅT = 173 K
β = 97.882 (9)°Block, light yellow
V = 1508.3 (3) Å30.33 × 0.32 × 0.30 mm
Z = 4
Data collection top
Stoe IPDS II two-circle
diffractometer
2818 independent reflections
Radiation source: fine-focus sealed tube2368 reflections with I > 2σ(I)
Graphite monochromatorRint = 0.060
ω scansθmax = 25.7°, θmin = 3.5°
Absorption correction: multi-scan
(MULABS; Spek, 2003; Blessing, 1995)
h = 88
Tmin = 0.414, Tmax = 0.436k = 2426
9259 measured reflectionsl = 119
Refinement top
Refinement on F2Secondary atom site location: difference Fourier map
Least-squares matrix: fullHydrogen site location: inferred from neighbouring sites
R[F2 > 2σ(F2)] = 0.042H atoms treated by a mixture of independent and constrained refinement
wR(F2) = 0.103 w = 1/[σ2(Fo2) + (0.0687P)2]
where P = (Fo2 + 2Fc2)/3
S = 1.02(Δ/σ)max = 0.001
2818 reflectionsΔρmax = 0.79 e Å3
214 parametersΔρmin = 1.01 e Å3
0 restraintsExtinction correction: SHELXL97 (Sheldrick, 1997), Fc*=kFc[1+0.001xFc2λ3/sin(2θ)]-1/4
Primary atom site location: structure-invariant direct methodsExtinction coefficient: 0.0053 (10)
Crystal data top
C15H12BrN3O4V = 1508.3 (3) Å3
Mr = 378.19Z = 4
Monoclinic, P21/cMo Kα radiation
a = 7.2604 (8) ŵ = 2.75 mm1
b = 21.8931 (19) ÅT = 173 K
c = 9.5795 (12) Å0.33 × 0.32 × 0.30 mm
β = 97.882 (9)°
Data collection top
Stoe IPDS II two-circle
diffractometer
2818 independent reflections
Absorption correction: multi-scan
(MULABS; Spek, 2003; Blessing, 1995)
2368 reflections with I > 2σ(I)
Tmin = 0.414, Tmax = 0.436Rint = 0.060
9259 measured reflections
Refinement top
R[F2 > 2σ(F2)] = 0.0420 restraints
wR(F2) = 0.103H atoms treated by a mixture of independent and constrained refinement
S = 1.02Δρmax = 0.79 e Å3
2818 reflectionsΔρmin = 1.01 e Å3
214 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
Br10.32579 (4)0.100500 (15)0.57802 (4)0.02733 (15)
O10.5025 (3)0.22410 (11)0.7115 (2)0.0269 (5)
O21.0036 (3)0.15890 (12)0.3018 (3)0.0331 (6)
O30.1301 (4)0.64942 (13)0.5891 (4)0.0529 (8)
O40.0367 (4)0.60609 (13)0.7701 (3)0.0408 (7)
N10.4881 (3)0.28121 (12)0.5111 (3)0.0196 (5)
H10.502 (4)0.2827 (16)0.425 (4)0.017 (8)*
N20.4182 (3)0.33185 (12)0.5697 (3)0.0204 (5)
N30.1128 (4)0.60476 (13)0.6635 (3)0.0293 (7)
C10.5290 (4)0.22977 (14)0.5886 (3)0.0184 (6)
C20.3788 (4)0.37684 (15)0.4844 (3)0.0219 (6)
H20.39590.37260.38830.026*
C110.6152 (4)0.18073 (14)0.5101 (3)0.0186 (6)
C120.5502 (4)0.12071 (15)0.5056 (3)0.0208 (6)
C130.6396 (4)0.07531 (16)0.4399 (4)0.0251 (7)
H130.59440.03460.43830.030*
C140.7945 (5)0.08914 (16)0.3766 (4)0.0261 (7)
H140.85870.05760.33500.031*
C150.8564 (4)0.14933 (16)0.3737 (3)0.0232 (7)
C160.7690 (4)0.19505 (15)0.4417 (3)0.0205 (6)
H160.81330.23590.44180.025*
C171.0707 (5)0.22025 (19)0.2950 (5)0.0428 (10)
H17A0.97180.24630.24710.064*
H17B1.17750.22080.24260.064*
H17C1.10890.23560.39070.064*
C210.3078 (4)0.43461 (14)0.5336 (3)0.0197 (6)
C220.2838 (4)0.48389 (15)0.4405 (3)0.0216 (6)
H220.31000.47890.34670.026*
C230.2223 (4)0.54005 (15)0.4830 (4)0.0230 (7)
H230.20670.57360.41970.028*
C240.1842 (4)0.54577 (14)0.6200 (4)0.0221 (7)
C250.2056 (4)0.49770 (15)0.7154 (3)0.0234 (7)
H250.17750.50280.80870.028*
C260.2688 (4)0.44214 (15)0.6716 (3)0.0221 (7)
H260.28580.40890.73580.026*
Atomic displacement parameters (Å2) top
U11U22U33U12U13U23
Br10.0317 (2)0.0242 (2)0.0281 (2)0.00598 (13)0.01127 (13)0.00084 (14)
O10.0430 (12)0.0234 (12)0.0163 (12)0.0023 (10)0.0114 (9)0.0011 (9)
O20.0347 (12)0.0298 (14)0.0395 (14)0.0040 (10)0.0224 (10)0.0036 (11)
O30.077 (2)0.0188 (14)0.068 (2)0.0059 (13)0.0277 (17)0.0039 (15)
O40.0419 (14)0.0404 (17)0.0426 (16)0.0102 (11)0.0143 (12)0.0153 (13)
N10.0288 (12)0.0176 (13)0.0143 (13)0.0045 (10)0.0094 (10)0.0007 (11)
N20.0234 (12)0.0165 (13)0.0224 (14)0.0013 (10)0.0075 (10)0.0029 (11)
N30.0263 (13)0.0224 (16)0.0389 (18)0.0001 (11)0.0031 (12)0.0104 (14)
C10.0185 (12)0.0187 (16)0.0184 (16)0.0015 (11)0.0041 (11)0.0015 (13)
C20.0221 (13)0.0228 (17)0.0215 (16)0.0008 (12)0.0058 (12)0.0021 (13)
C110.0231 (13)0.0178 (16)0.0150 (14)0.0038 (11)0.0033 (11)0.0017 (12)
C120.0243 (14)0.0195 (16)0.0187 (15)0.0003 (12)0.0032 (12)0.0017 (13)
C130.0329 (15)0.0158 (16)0.0265 (18)0.0025 (13)0.0039 (13)0.0013 (14)
C140.0320 (16)0.0218 (17)0.0253 (17)0.0088 (12)0.0065 (13)0.0055 (14)
C150.0233 (14)0.0283 (18)0.0186 (15)0.0050 (12)0.0048 (11)0.0002 (13)
C160.0217 (13)0.0180 (15)0.0221 (16)0.0016 (11)0.0036 (11)0.0004 (13)
C170.0408 (19)0.037 (2)0.058 (3)0.0026 (16)0.0311 (18)0.001 (2)
C210.0154 (12)0.0183 (15)0.0252 (16)0.0023 (11)0.0020 (11)0.0018 (13)
C220.0254 (14)0.0222 (17)0.0184 (15)0.0016 (12)0.0069 (11)0.0004 (13)
C230.0226 (13)0.0180 (16)0.0280 (17)0.0002 (11)0.0026 (12)0.0016 (14)
C240.0171 (12)0.0193 (16)0.0298 (17)0.0011 (11)0.0026 (12)0.0079 (14)
C250.0210 (13)0.0267 (17)0.0237 (17)0.0014 (12)0.0073 (12)0.0025 (14)
C260.0198 (13)0.0241 (17)0.0225 (16)0.0015 (11)0.0037 (11)0.0013 (13)
Geometric parameters (Å, º) top
Br1—C121.908 (3)C13—H130.9500
O1—C11.225 (4)C14—C151.394 (5)
O2—C151.364 (4)C14—H140.9500
O2—C171.434 (5)C15—C161.394 (4)
O3—N31.226 (4)C16—H160.9500
O4—N31.227 (4)C17—H17A0.9800
N1—C11.359 (4)C17—H17B0.9800
N1—N21.371 (4)C17—H17C0.9800
N1—H10.85 (4)C21—C221.395 (4)
N2—C21.287 (4)C21—C261.400 (5)
N3—C241.473 (4)C22—C231.388 (5)
C1—C111.497 (4)C22—H220.9500
C2—C211.468 (5)C23—C241.384 (5)
C2—H20.9500C23—H230.9500
C11—C121.395 (4)C24—C251.389 (5)
C11—C161.405 (4)C25—C261.385 (5)
C12—C131.385 (5)C25—H250.9500
C13—C141.382 (5)C26—H260.9500
C15—O2—C17117.5 (3)C14—C15—C16120.0 (3)
C1—N1—N2120.8 (3)C15—C16—C11120.0 (3)
C1—N1—H1121 (2)C15—C16—H16120.0
N2—N1—H1118 (2)C11—C16—H16120.0
C2—N2—N1114.9 (3)O2—C17—H17A109.5
O3—N3—O4124.0 (3)O2—C17—H17B109.5
O3—N3—C24117.8 (3)H17A—C17—H17B109.5
O4—N3—C24118.2 (3)O2—C17—H17C109.5
O1—C1—N1123.9 (3)H17A—C17—H17C109.5
O1—C1—C11122.8 (3)H17B—C17—H17C109.5
N1—C1—C11113.3 (3)C22—C21—C26119.3 (3)
N2—C2—C21120.9 (3)C22—C21—C2118.7 (3)
N2—C2—H2119.6C26—C21—C2122.0 (3)
C21—C2—H2119.6C23—C22—C21121.0 (3)
C12—C11—C16118.9 (3)C23—C22—H22119.5
C12—C11—C1121.9 (3)C21—C22—H22119.5
C16—C11—C1119.2 (3)C24—C23—C22118.2 (3)
C13—C12—C11120.8 (3)C24—C23—H23120.9
C13—C12—Br1118.4 (2)C22—C23—H23120.9
C11—C12—Br1120.6 (2)C23—C24—C25122.5 (3)
C14—C13—C12120.2 (3)C23—C24—N3118.1 (3)
C14—C13—H13119.9C25—C24—N3119.4 (3)
C12—C13—H13119.9C26—C25—C24118.5 (3)
C13—C14—C15120.0 (3)C26—C25—H25120.7
C13—C14—H14120.0C24—C25—H25120.7
C15—C14—H14120.0C25—C26—C21120.5 (3)
O2—C15—C14115.6 (3)C25—C26—H26119.7
O2—C15—C16124.3 (3)C21—C26—H26119.7
C1—N1—N2—C2177.6 (3)C14—C15—C16—C111.6 (4)
N2—N1—C1—O12.2 (4)C12—C11—C16—C151.5 (4)
N2—N1—C1—C11176.2 (2)C1—C11—C16—C15177.0 (3)
N1—N2—C2—C21178.3 (2)N2—C2—C21—C22174.0 (3)
O1—C1—C11—C1251.0 (4)N2—C2—C21—C264.1 (4)
N1—C1—C11—C12130.5 (3)C26—C21—C22—C230.1 (4)
O1—C1—C11—C16127.4 (3)C2—C21—C22—C23178.1 (3)
N1—C1—C11—C1651.0 (3)C21—C22—C23—C240.4 (4)
C16—C11—C12—C132.6 (4)C22—C23—C24—C250.1 (4)
C1—C11—C12—C13175.8 (3)C22—C23—C24—N3177.9 (3)
C16—C11—C12—Br1172.9 (2)O3—N3—C24—C2316.3 (4)
C1—C11—C12—Br18.6 (4)O4—N3—C24—C23162.5 (3)
C11—C12—C13—C140.6 (5)O3—N3—C24—C25165.6 (3)
Br1—C12—C13—C14175.1 (2)O4—N3—C24—C2515.7 (4)
C12—C13—C14—C152.6 (5)C23—C24—C25—C260.5 (4)
C17—O2—C15—C14179.4 (3)N3—C24—C25—C26178.5 (2)
C17—O2—C15—C160.6 (5)C24—C25—C26—C210.8 (4)
C13—C14—C15—O2176.3 (3)C22—C21—C26—C250.5 (4)
C13—C14—C15—C163.7 (5)C2—C21—C26—C25178.7 (3)
O2—C15—C16—C11178.4 (3)
Hydrogen-bond geometry (Å, º) top
D—H···AD—HH···AD···AD—H···A
N1—H1···O1i0.85 (4)2.05 (4)2.889 (4)171 (3)
Symmetry code: (i) x, y+1/2, z1/2.

Experimental details

Crystal data
Chemical formulaC15H12BrN3O4
Mr378.19
Crystal system, space groupMonoclinic, P21/c
Temperature (K)173
a, b, c (Å)7.2604 (8), 21.8931 (19), 9.5795 (12)
β (°) 97.882 (9)
V3)1508.3 (3)
Z4
Radiation typeMo Kα
µ (mm1)2.75
Crystal size (mm)0.33 × 0.32 × 0.30
Data collection
DiffractometerStoe IPDS II two-circle
Absorption correctionMulti-scan
(MULABS; Spek, 2003; Blessing, 1995)
Tmin, Tmax0.414, 0.436
No. of measured, independent and
observed [I > 2σ(I)] reflections
9259, 2818, 2368
Rint0.060
(sin θ/λ)max1)0.610
Refinement
R[F2 > 2σ(F2)], wR(F2), S 0.042, 0.103, 1.02
No. of reflections2818
No. of parameters214
H-atom treatmentH atoms treated by a mixture of independent and constrained refinement
Δρmax, Δρmin (e Å3)0.79, 1.01

Computer programs: X-AREA (Stoe & Cie, 2001), X-AREA, SHELXS97 (Sheldrick, 1990), SHELXL97 (Sheldrick, 1997), PLATON (Spek, 2003), SHELXL97.

Hydrogen-bond geometry (Å, º) top
D—H···AD—HH···AD···AD—H···A
N1—H1···O1i0.85 (4)2.05 (4)2.889 (4)171 (3)
Symmetry code: (i) x, y+1/2, z1/2.
 

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