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organic compounds\(\def\hfill{\hskip 5em}\def\hfil{\hskip 3em}\def\eqno#1{\hfil {#1}}\)

Journal logoCRYSTALLOGRAPHIC
COMMUNICATIONS
ISSN: 2056-9890
Volume 64| Part 12| December 2008| Page o2260
doi:10.1107/S1600536808035472

(E)-N′-(5-Bromo-2-meth­oxy­benzyl­­idene)-4-meth­oxy­benzohydrazide

Hong-Yan Bana* and Cong-Ming Lib

aSchool of Chemical Engineering, University of Science and Technology Liaoning, Anshan 114051, People's Republic of China, and bCollege of Sciences, Shenyang University, Shenyang 110044, People's Republic of China
*Correspondence e-mail: hongyan_ban@163.com

(Received 9 October 2008; accepted 29 October 2008; online 8 November 2008)

In the title compound, C16H15BrN2O3, the benzohydrazide group is not planar and the mol­ecule exists in a trans configuration with respect to the methyl­idene unit. The dihedral angle between the two substituted benzene rings is 75.6 (2)°. In the crystal structure, mol­ecules are linked by inter­molecular N—H⋯O hydrogen bonds involving carbonyl and amine functionalities, to form chains parallel to the c cell axis.

Related literature

For the biological activities of hydrazones, see: Zhong et al. (2007[Zhong, X., Wei, H.-L., Liu, W.-S., Wang, D.-Q. & Wang, X. (2007). Bioorg. Med. Chem. Lett. 17, 3774-3777.]); Raj et al. (2007[Raj, K. K. V., Narayana, B., Ashalatha, B. V., Kumari, N. S. & Sarojini, B. K. (2007). Eur. J. Med. Chem. 42, 425-429.]); Jimenez-Pulido et al. (2008[Jimenez-Pulido, S. B., Linares-Ordonez, F. M., Martinez-Martos, J. M., Moreno-Carretero, M. N., Quiros-Olozabal, M. & Ramirez-Exposito, M. J. (2008). J. Inorg. Biochem. 102, 1677-1683.]). For related structures, see: Yehye et al. (2008[Yehye, W. A., Rahman, N. A., Ariffin, A. & Ng, S. W. (2008). Acta Cryst. E64, o1824.]); Fun, Patil, Jebas et al. (2008[Fun, H.-K., Patil, P. S., Jebas, S. R., Sujith, K. V. & Kalluraya, B. (2008). Acta Cryst. E64, o1594-o1595.]); Fun, Patil, Rao et al. (2008[Fun, H.-K., Patil, P. S., Rao, J. N., Kalluraya, B. & Chantrapromma, S. (2008). Acta Cryst. E64, o1707.]); Yang et al. (2008[Yang, T., Cao, G.-B., Xiang, J.-M. & Zhang, L.-H. (2008). Acta Cryst. E64, o1186.]); Ejsmont et al. (2008[Ejsmont, K., Zareef, M., Arfan, M., Bashir, S. A. & Zaleski, J. (2008). Acta Cryst. E64, o1128.]).

[Scheme 1]

Experimental

Crystal data

  • C16H15BrN2O3

  • Mr = 363.21

  • Monoclinic, P 21 /c

  • a = 12.438 (4) Å

  • b = 16.684 (6) Å

  • c = 7.863 (3) Å

  • β = 108.218 (6)°

  • V = 1549.8 (9) Å3

  • Z = 4

  • Mo Kα radiation

  • μ = 2.67 mm−1

  • T = 298 (2) K

  • 0.20 × 0.20 × 0.18 mm
Data collection

  • Bruker SMART CCD area-detector diffractometer

  • Absorption correction: multi-scan (SADABS; Bruker, 1998[Bruker (1998). SMART, SAINT and SADABS. Bruker AXS Inc., Madison, Wisconsin, USA.]) Tmin = 0.593, Tmax = 0.620

  • 8697 measured reflections

  • 3245 independent reflections

  • 2068 reflections with I > 2σ(I)

  • Rint = 0.034
Refinement

  • R[F2 > 2σ(F2)] = 0.038

  • wR(F2) = 0.093

  • S = 1.01

  • 3245 reflections

  • 205 parameters

  • 1 restraint

  • H atoms treated by a mixture of independent and constrained refinement

  • Δρmax = 0.50 e Å−3

  • Δρmin = −0.47 e Å−3

Table 1
Hydrogen-bond geometry (Å, °)

D—H⋯A D—H H⋯A D⋯A D—H⋯A
N2—H2⋯O2i 0.890 (10) 1.966 (12) 2.835 (3) 165 (2)
Symmetry code: (i) [x, -y+{\script{1\over 2}}, z-{\script{1\over 2}}].

Data collection: SMART (Bruker, 1998[Bruker (1998). SMART, SAINT and SADABS. Bruker AXS Inc., Madison, Wisconsin, USA.]); cell refinement: SAINT (Bruker, 1998[Bruker (1998). SMART, SAINT and SADABS. Bruker AXS Inc., Madison, Wisconsin, USA.]); data reduction: SAINT; program(s) used to solve structure: SHELXS97 (Sheldrick, 2008[Sheldrick, G. M. (2008). Acta Cryst. A64, 112-122.]); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008[Sheldrick, G. M. (2008). Acta Cryst. A64, 112-122.]); molecular graphics: SHELXTL (Sheldrick, 2008[Sheldrick, G. M. (2008). Acta Cryst. A64, 112-122.]); software used to prepare material for publication: SHELXTL.

Supporting information

Crystal structure: contains datablocks global, I. DOI: 10.1107/S1600536808035472/bh2202sup1.cif

Structure factors: contains datablock I. DOI: 10.1107/S1600536808035472/bh2202Isup2.hkl

checkCIF report


Comment top

Hydrazones derived from the condensation of aldehydes with hydrazides have been demonstrated to possess excellent biological activities (Zhong et al., 2007; Raj et al., 2007; Jimenez-Pulido et al., 2008). Due to the easy synthesis of such compounds, a great deal of hydrazones have been synthesized and structurally characterized (Yehye et al., 2008; Fun, Patil, Jebas et al., 2008; Fun, Patil, Rao et al., 2008;Yang et al., 2008; Ejsmont et al., 2008). We report herein the crystal structure of the title new compound, (I).

In the structure of the title compound (Fig. 1) the molecule exists in a trans configuration with respect to the methylidene unit. The dihedral angle between the two substituted benzene rings is 75.6 (2)°. In both the 5-bromo-2-methoxyphenyl unit and the 4-methoxyphenyl unit, the methoxy groups are nearly coplanar with the corresponding mean planes of the C1···C6 and C9···C14 rings, respectively. Atoms C16 and C15 deviate from their corresponding benzene rings by 0.058 (2) and 0.059 (2) Å respectively. The torsion angle of C7—N1—N2—C8 is 19.4 (3)°. The bond lengths and angles are found in expected ranges.

In the crystal structure, molecules are linked by intermolecular N—H···O hydrogen bonds involving carbonyl and amine groups (Table 1), to form chains parallel to the c axis (Fig. 2).

Related literature top

For the biological activities of hydrazones, see: Zhong et al. (2007); Raj et al. (2007); Jimenez-Pulido et al. (2008). For related literature, see: Yehye et al. (2008); Fun, Patil, Jebas et al. (2008); Fun, Patil, Rao et al. (2008); Yang et al. (2008); Ejsmont et al. (2008).

Experimental top

The compound was prepared by refluxing 5-bromo-2-methoxybenzaldehyde (1.0 mmol) with 4-methoxybenzohydrazide (1.0 mmol) in methanol (100 ml). Excess methanol was removed from the mixture by distillation. The colorless solid product was filtered, and washed three times with methanol. Colorless block crystals of the title compound were obtained from a methanol solution by slow evaporation in air.

Refinement top

H2 was located in a difference map and refined isotropically, with N2—H2 distance restrained to 0.90 (1) Å. Other H atoms were placed in calculated positions (C—H = 0.93–0.96 Å) and refined as riding atoms with Uiso(H) = 1.2Ueq(C) and 1.5Ueq(methyl C). A rotating group model was used for the methyl groups.

Computing details top

Data collection: SMART (Bruker, 1998); cell refinement: SAINT (Bruker, 1998); data reduction: SAINT (Bruker, 1998); 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. The molecular structure of (I), showing 30% probability displacement ellipsoids for the non-hydrogen atoms.
[Figure 2] Fig. 2. The packing diagram of (I), viewed along the b axis. Hydrogen bonds are shown as dashed lines.
(E)-N'-(5-Bromo-2-methoxybenzylidene)-4-methoxybenzohydrazide top
Crystal data top
C16H15BrN2O3F(000) = 736
Mr = 363.21Dx = 1.557 Mg m−3
Monoclinic, P21/cMo Kα radiation, λ = 0.71073 Å
Hall symbol: -P 2ybcCell parameters from 2110 reflections
a = 12.438 (4) Åθ = 2.4–24.5°
b = 16.684 (6) ŵ = 2.67 mm−1
c = 7.863 (3) ÅT = 298 K
β = 108.218 (6)°Block, colorless
V = 1549.8 (9) Å30.20 × 0.20 × 0.18 mm
Z = 4
Data collection top
Bruker SMART CCD area-detector
diffractometer		3245 independent reflections
Radiation source: fine-focus sealed tube2068 reflections with I > 2σ(I)
Graphite monochromatorRint = 0.034
ω scansθmax = 26.7°, θmin = 1.7°
Absorption correction: multi-scan
(SADABS; Bruker, 1998)		h = −14→15
Tmin = 0.593, Tmax = 0.620k = −20→21
8697 measured reflectionsl = −9→9
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)] = 0.038Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.093H atoms treated by a mixture of independent and constrained refinement
S = 1.01 w = 1/[σ2(Fo2) + (0.0407P)2 + 0.1883P]
where P = (Fo2 + 2Fc2)/3
3245 reflections(Δ/σ)max = 0.001
205 parametersΔρmax = 0.50 e Å−3
1 restraintΔρmin = −0.47 e Å−3
Crystal data top
C16H15BrN2O3V = 1549.8 (9) Å3
Mr = 363.21Z = 4
Monoclinic, P21/cMo Kα radiation
a = 12.438 (4) ŵ = 2.67 mm−1
b = 16.684 (6) ÅT = 298 K
c = 7.863 (3) Å0.20 × 0.20 × 0.18 mm
β = 108.218 (6)°
Data collection top
Bruker SMART CCD area-detector
diffractometer		3245 independent reflections
Absorption correction: multi-scan
(SADABS; Bruker, 1998)		2068 reflections with I > 2σ(I)
Tmin = 0.593, Tmax = 0.620Rint = 0.034
8697 measured reflections
Refinement top
R[F2 > 2σ(F2)] = 0.0381 restraint
wR(F2) = 0.093H atoms treated by a mixture of independent and constrained refinement
S = 1.01Δρmax = 0.50 e Å−3
3245 reflectionsΔρmin = −0.47 e Å−3
205 parameters
Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Å2) top
xyzUiso*/Ueq
Br1−0.31436 (3)0.22534 (2)0.94364 (5)0.07161 (17)
N10.10628 (17)0.23762 (13)0.8539 (3)0.0380 (5)
N20.19688 (18)0.26531 (13)0.8053 (3)0.0384 (5)
O10.01300 (15)0.01461 (11)0.7292 (3)0.0509 (5)
O20.26258 (15)0.33509 (11)1.0641 (2)0.0455 (5)
O30.61120 (16)0.44804 (12)0.6741 (3)0.0603 (6)
C1−0.0401 (2)0.14085 (16)0.8049 (3)0.0383 (6)
C2−0.0634 (2)0.05851 (16)0.7802 (3)0.0414 (7)
C3−0.1589 (2)0.02734 (18)0.8110 (4)0.0490 (7)
H3−0.1738−0.02730.79670.059*
C4−0.2318 (2)0.07627 (19)0.8625 (4)0.0498 (8)
H4−0.29570.05480.88280.060*
C5−0.2101 (2)0.15743 (18)0.8841 (4)0.0460 (7)
C6−0.1148 (2)0.18901 (17)0.8578 (3)0.0429 (7)
H6−0.10000.24350.87570.051*
C70.0603 (2)0.17374 (16)0.7739 (3)0.0389 (6)
H70.09150.14810.69530.047*
C80.2703 (2)0.31655 (15)0.9165 (4)0.0369 (6)
C90.3602 (2)0.34885 (15)0.8498 (3)0.0354 (6)
C100.3494 (2)0.35720 (16)0.6705 (4)0.0425 (7)
H100.28330.34000.58520.051*
C110.4338 (2)0.39027 (18)0.6149 (4)0.0493 (7)
H110.42460.39540.49340.059*
C120.5326 (2)0.41596 (16)0.7408 (4)0.0432 (7)
C130.5452 (2)0.40845 (18)0.9203 (4)0.0482 (7)
H130.61150.42561.00540.058*
C140.4593 (2)0.37549 (17)0.9738 (4)0.0462 (7)
H140.46810.37111.09530.055*
C150.7161 (3)0.4720 (2)0.7978 (5)0.0739 (11)
H15A0.70310.51290.87490.111*
H15B0.76440.49260.73380.111*
H15C0.75170.42670.86840.111*
C16−0.0095 (3)−0.06880 (17)0.6972 (4)0.0563 (8)
H16A−0.0110−0.09430.80590.084*
H16B0.0488−0.09250.65750.084*
H16C−0.0814−0.07570.60680.084*
H20.212 (2)0.2407 (14)0.715 (3)0.044 (8)*
Atomic displacement parameters (Å2) top
U11U22U33U12U13U23
Br10.0574 (2)0.0821 (3)0.0863 (3)0.00286 (18)0.0383 (2)−0.0118 (2)
N10.0331 (12)0.0430 (14)0.0405 (13)−0.0059 (10)0.0154 (10)−0.0001 (10)
N20.0398 (13)0.0409 (13)0.0403 (14)−0.0086 (11)0.0208 (11)−0.0065 (11)
O10.0498 (12)0.0413 (11)0.0670 (14)−0.0080 (9)0.0260 (11)−0.0072 (10)
O20.0488 (11)0.0473 (11)0.0470 (12)−0.0117 (9)0.0244 (10)−0.0083 (9)
O30.0472 (13)0.0689 (14)0.0728 (15)−0.0201 (11)0.0300 (11)−0.0025 (12)
C10.0363 (15)0.0414 (16)0.0361 (15)−0.0074 (12)0.0098 (13)−0.0008 (12)
C20.0401 (16)0.0453 (17)0.0371 (16)−0.0058 (13)0.0098 (13)−0.0017 (13)
C30.0483 (17)0.0462 (17)0.0525 (19)−0.0146 (14)0.0158 (15)−0.0021 (14)
C40.0411 (17)0.060 (2)0.0503 (18)−0.0150 (15)0.0176 (15)0.0009 (15)
C50.0404 (16)0.058 (2)0.0410 (17)−0.0019 (14)0.0145 (14)0.0009 (14)
C60.0437 (16)0.0433 (16)0.0412 (17)−0.0049 (13)0.0125 (14)−0.0019 (13)
C70.0372 (15)0.0417 (16)0.0404 (16)−0.0035 (13)0.0158 (13)−0.0020 (13)
C80.0368 (15)0.0318 (14)0.0436 (17)0.0025 (12)0.0147 (13)0.0013 (12)
C90.0328 (14)0.0328 (14)0.0422 (17)−0.0033 (11)0.0142 (13)−0.0010 (12)
C100.0350 (15)0.0479 (17)0.0422 (17)−0.0075 (13)0.0086 (13)−0.0016 (13)
C110.0504 (18)0.0560 (19)0.0450 (17)−0.0098 (14)0.0201 (15)0.0023 (14)
C120.0365 (16)0.0385 (15)0.057 (2)−0.0043 (12)0.0184 (15)−0.0021 (13)
C130.0340 (16)0.0556 (19)0.054 (2)−0.0106 (13)0.0128 (14)−0.0093 (15)
C140.0453 (17)0.0554 (18)0.0400 (17)−0.0063 (14)0.0165 (14)−0.0055 (14)
C150.048 (2)0.087 (3)0.096 (3)−0.0268 (18)0.036 (2)−0.017 (2)
C160.062 (2)0.0428 (18)0.067 (2)−0.0070 (15)0.0239 (17)−0.0084 (15)
Geometric parameters (Å, º) top
Br1—C51.888 (3)C6—H60.9300
N1—C71.278 (3)C7—H70.9300
N1—N21.378 (3)C8—C91.477 (3)
N2—C81.352 (3)C9—C101.381 (4)
N2—H20.890 (10)C9—C141.385 (4)
O1—C21.355 (3)C10—C111.372 (4)
O1—C161.426 (3)C10—H100.9300
O2—C81.233 (3)C11—C121.383 (4)
O3—C121.355 (3)C11—H110.9300
O3—C151.419 (4)C12—C131.377 (4)
C1—C61.386 (4)C13—C141.379 (4)
C1—C21.405 (4)C13—H130.9300
C1—C71.453 (3)C14—H140.9300
C2—C31.386 (4)C15—H15A0.9600
C3—C41.371 (4)C15—H15B0.9600
C3—H30.9300C15—H15C0.9600
C4—C51.381 (4)C16—H16A0.9600
C4—H40.9300C16—H16B0.9600
C5—C61.371 (4)C16—H16C0.9600
C7—N1—N2115.0 (2)C10—C9—C14117.8 (2)
C8—N2—N1118.5 (2)C10—C9—C8123.9 (2)
C8—N2—H2122.6 (17)C14—C9—C8118.2 (2)
N1—N2—H2117.5 (17)C11—C10—C9121.8 (3)
C2—O1—C16117.6 (2)C11—C10—H10119.1
C12—O3—C15117.8 (2)C9—C10—H10119.1
C6—C1—C2118.7 (2)C10—C11—C12119.6 (3)
C6—C1—C7121.5 (2)C10—C11—H11120.2
C2—C1—C7119.8 (2)C12—C11—H11120.2
O1—C2—C3124.6 (3)O3—C12—C13124.6 (2)
O1—C2—C1115.9 (2)O3—C12—C11115.6 (3)
C3—C2—C1119.5 (3)C13—C12—C11119.7 (3)
C4—C3—C2120.7 (3)C12—C13—C14119.9 (3)
C4—C3—H3119.7C12—C13—H13120.0
C2—C3—H3119.7C14—C13—H13120.0
C3—C4—C5119.9 (3)C13—C14—C9121.2 (3)
C3—C4—H4120.0C13—C14—H14119.4
C5—C4—H4120.0C9—C14—H14119.4
C6—C5—C4120.2 (3)O3—C15—H15A109.5
C6—C5—Br1120.0 (2)O3—C15—H15B109.5
C4—C5—Br1119.8 (2)H15A—C15—H15B109.5
C5—C6—C1121.0 (3)O3—C15—H15C109.5
C5—C6—H6119.5H15A—C15—H15C109.5
C1—C6—H6119.5H15B—C15—H15C109.5
N1—C7—C1120.5 (2)O1—C16—H16A109.5
N1—C7—H7119.7O1—C16—H16B109.5
C1—C7—H7119.7H16A—C16—H16B109.5
O2—C8—N2122.1 (2)O1—C16—H16C109.5
O2—C8—C9122.2 (2)H16A—C16—H16C109.5
N2—C8—C9115.7 (2)H16B—C16—H16C109.5
Hydrogen-bond geometry (Å, º) top
D—H···AD—HH···AD···AD—H···A
N2—H2···O2i0.89 (1)1.97 (1)2.835 (3)165 (2)
Symmetry code: (i) x, −y+1/2, z−1/2.

Experimental details

Crystal data
Chemical formulaC16H15BrN2O3
Mr363.21
Crystal system, space groupMonoclinic, P21/c
Temperature (K)298
a, b, c (Å)12.438 (4), 16.684 (6), 7.863 (3)
β (°) 108.218 (6)
V (Å3)1549.8 (9)
Z4
Radiation typeMo Kα
µ (mm−1)2.67
Crystal size (mm)0.20 × 0.20 × 0.18
Data collection
DiffractometerBruker SMART CCD area-detector
diffractometer
Absorption correctionMulti-scan
(SADABS; Bruker, 1998)
Tmin, Tmax0.593, 0.620
No. of measured, independent and
observed [I > 2σ(I)] reflections		8697, 3245, 2068
Rint0.034
(sin θ/λ)max (Å−1)0.633
Refinement
R[F2 > 2σ(F2)], wR(F2), S 0.038, 0.093, 1.01
No. of reflections3245
No. of parameters205
No. of restraints1
H-atom treatmentH atoms treated by a mixture of independent and constrained refinement
Δρmax, Δρmin (e Å−3)0.50, −0.47

Computer programs: SMART (Bruker, 1998), SAINT (Bruker, 1998), SHELXS97 (Sheldrick, 2008), SHELXL97 (Sheldrick, 2008), SHELXTL (Sheldrick, 2008).

Hydrogen-bond geometry (Å, º) top
D—H···AD—HH···AD···AD—H···A
N2—H2···O2i0.890 (10)1.966 (12)2.835 (3)165 (2)
Symmetry code: (i) x, −y+1/2, z−1/2.
 

Acknowledgements

Financial support of this work was provided by the Research Foundation of Liaoning Province (project No. 2008470).

References

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Journal logoCRYSTALLOGRAPHIC
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ISSN: 2056-9890
Volume 64| Part 12| December 2008| Page o2260
doi:10.1107/S1600536808035472
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