(1E,2E)-1,2-Bis(3-bromo-4-meth­oxy­benzyl­idene)hydrazine

Jasinski, J.P.; Golen, J.A.; Chidan Kumar, C.S.; Narayana, B.; Yathirajan, H.S.

doi:10.1107/S1600536811016904

organic compounds

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ISSN: 2056-9890

Volume 67| Part 6| June 2011| Page o1379

doi:10.1107/S1600536811016904

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(1E,2E)-1,2-Bis(3-bromo-4-methoxybenzylidene)hydrazine

Jerry P. Jasinski,^a ^* James A. Golen,^a C. S. Chidan Kumar,^b B. Narayana ^c and H. S. Yathirajan ^b

^aDepartment of Chemistry, Keene State College, 229 Main Street, Keene, NH 03435-2001, USA, ^bDepartment of Studies in Chemistry, University of Mysore, Manasagangotri, Mysore 570 006, India, and ^cDepartment of Studies in Chemistry, Mangalore University, Mangalagangotri 574 199, India
^*Correspondence e-mail: jjasinski@keene.edu

(Received 3 May 2011; accepted 4 May 2011; online 11 May 2011)

In the title compound, C₁₆H₁₄Br₂N₂O₂, the dihedral angle between the mean planes of the two benzene rings is 33.4 (2)°. The hydrazine group is twisted slightly, with C—N—N—C and C—C—N—N torsion angles of 167.5 (4) and 177.2 (4)/174.2 (4)°, respectively.

Related literature

For antitubercular behaviour in isonicotinoyl hydrazones, see: Kucukguzel et al. (1999 ); Rollas et al. (2002 ). For the coordination chemistry of azine compounds containing both a diamine linkage and an N—N bond, see: Armstrong et al. (1998 ); Kesslen & Euler (1999 ); Kundu et al. (2005 ); Xu et al. (1997 ). For related structures, see: Zheng et al. (2005 , 2006 ); Zheng & Zhao (2006 ); Odabaşoğlu et al. (2007 ).

Experimental

Crystal data

C₁₆H₁₄Br₂N₂O₂
M_r = 426.11
Monoclinic, P 2₁ /c
a = 10.1354 (8) Å
b = 10.550 (1) Å
c = 15.6055 (12) Å
β = 96.680 (7)°
V = 1657.3 (2) Å³
Z = 4
Mo Kα radiation
μ = 4.90 mm⁻¹
T = 173 K
0.20 × 0.15 × 0.10 mm

Data collection

Oxford Xcalibur Eos Gemini diffractometer
Absorption correction: multi-scan (CrysAlis RED; Oxford Diffraction, 2010 $[Oxford Diffraction (2010). CrysAlis PRO and CrysAlis RED. Oxford Diffraction Ltd, Yarnton, Oxfordshire, England.]$ ) T_min = 0.441, T_max = 0.640
14411 measured reflections
3941 independent reflections
2537 reflections with I > 2σ(I)
R_int = 0.061

Refinement

R[F² > 2σ(F²)] = 0.053
wR(F²) = 0.120
S = 1.09
3941 reflections
201 parameters
H-atom parameters constrained
Δρ_max = 0.53 e Å⁻³
Δρ_min = −0.64 e Å⁻³

Data collection: CrysAlis PRO (Oxford Diffraction, 2010 $[Oxford Diffraction (2010). CrysAlis PRO and CrysAlis RED. Oxford Diffraction Ltd, Yarnton, Oxfordshire, England.]$ ); cell refinement: CrysAlis PRO; data reduction: CrysAlis RED (Oxford Diffraction, 2010 $[Oxford Diffraction (2010). CrysAlis PRO and CrysAlis RED. Oxford Diffraction Ltd, Yarnton, Oxfordshire, England.]$ ); 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.

Supporting information

Crystal structure: contains datablocks global, I. DOI: 10.1107/S1600536811016904/tk2741sup1.cif

Structure factors: contains datablock I. DOI: 10.1107/S1600536811016904/tk2741Isup2.hkl

Supporting information file. DOI: 10.1107/S1600536811016904/tk2741Isup3.cml

checkCIF report

Comment top

Hydrazones are known to possess antimicrobial, anticonvulsant, analgesic, anti-inflammatory, antiplatelet, antitubercular and antitumoral activities. For example, isonicotinoyl hydrazones are antitubercular; 4-fluorobenzoic acid [(5-nitro-2-furyl)methylene]-hydrazide (Rollas et al., 2002) and 2,3,4-pentanetrione-3-[4-[[(5-nitro-2-furyl)methylene]hydrazine] carbonyl]phenyl]hydrazone (Kucukguzel et al., 1999) have antibacterial activity. A number of azine compounds containing both a diamine linkage and an N—N bond have been investigated in terms of their crystallography and coordination chemistry (Kundu et al., 2005; Kesslen & Euler, 1999; Armstrong et al., 1998; Xu et al., 1997). The crystal structures of N,N'-Bis(3-nitrobenzylidene)hydrazine (Zheng et al., 2005), N,N'-Bis(2,6-dichlorobenzylidene)hydrazine (Zheng et al., 2006), N,N'-Bis(9-anthracenylidene)hydrazine (Zheng & Zhao, 2006), 4-Fluorobenzaldehyde [(E)-4-fluorobenzylidene] hydrazone (Odabaşoğlu et al., 2007) have been reported. In view of the importance of hydrazones, the title compound, C₁₆H₁₄Br₂N₂O₂, (I), is synthesized, Fig. 1, and its crystal structure is reported here.

In (I) the dihedral angle between the mean planes of the two benzene rings is 33.4 (2)° (Fig. 2). The hydrazine group is twisted slightly with C9—N1—N2—C10, N2—N1—C9—C5 and N1—N2—C10—C11 torsion angles of 167.5 (4) and 177.2 (4) and 174.2 (4)°, respectively. The crystal packing is stabilized by weak van der Waals interactions.

Related literature top

For antitubercular behaviour in isonicotinoyl hydrazones, see: Kucukguzel et al. (1999); Rollas et al. (2002). For coordination chemistry of azine compounds containing both a diamine linkage and an N—N bond, see: Armstrong et al. (1998); Kesslen & Euler (1999); Kundu et al. (2005); Xu et al. (1997). For related structures, see: Zheng et al. (2005, 2006); Zheng & Zhao (2006); Odabaşoğlu et al. (2007).

Experimental top

A mixture of 3-bromo-4-methoxy benzaldehyde (4.3 g, 0.02 mol) and hydrazine hydrate (0.5 ml, 0.01 mol) in 15 ml of ethanol containing 2 drops of 4 M sulfuric acid was refluxed for about 3 h (Fig. 1). On cooling, the solid separated, was filtered and recrystallized from N,N-dimethylformamide (m.p. 453–455 K).

Computing details top

Data collection: CrysAlis PRO (Oxford Diffraction, 2010); cell refinement: CrysAlis PRO (Oxford Diffraction, 2010); data reduction: CrysAlis RED (Oxford Diffraction, 2010); 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

	Fig. 1. Reaction scheme for the title compound.
	Fig. 2. Molecular structure of the title compound showing the atom labeling scheme and 50% probability displacement ellipsoids.

(1E,2E)-1,2-Bis(3-bromo-4-methoxybenzylidene)hydrazine top

Crystal data top

C₁₆H₁₄Br₂N₂O₂	F(000) = 840
M_r = 426.11	D_x = 1.708 Mg m⁻³
Monoclinic, P2₁/c	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: -P 2ybc	Cell parameters from 3889 reflections
a = 10.1354 (8) Å	θ = 3.0–32.2°
b = 10.550 (1) Å	µ = 4.90 mm⁻¹
c = 15.6055 (12) Å	T = 173 K
β = 96.680 (7)°	Block, yellow
V = 1657.3 (2) Å³	0.20 × 0.15 × 0.10 mm
Z = 4

Data collection top

Oxford Xcalibur Eos Gemini diffractometer	3941 independent reflections
Radiation source: Enhance (Mo) X-ray Source	2537 reflections with I > 2σ(I)
Graphite monochromator	R_int = 0.061
Detector resolution: 16.1500 pixels mm^-1	θ_max = 27.9°, θ_min = 3.0°
ω scans	h = −13→13
Absorption correction: multi-scan (CrysAlis RED; Oxford Diffraction, 2010)	k = −13→13
T_min = 0.441, T_max = 0.640	l = −20→20
14411 measured reflections

Refinement top

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)] = 0.053	Hydrogen site location: inferred from neighbouring sites
wR(F²) = 0.120	H-atom parameters constrained
S = 1.09	w = 1/[σ²(F_o²) + (0.0419P)² + 0.0769P] where P = (F_o² + 2F_c²)/3
3941 reflections	(Δ/σ)_max = 0.002
201 parameters	Δρ_max = 0.53 e Å⁻³
0 restraints	Δρ_min = −0.64 e Å⁻³

Crystal data top

C₁₆H₁₄Br₂N₂O₂	V = 1657.3 (2) Å³
M_r = 426.11	Z = 4
Monoclinic, P2₁/c	Mo Kα radiation
a = 10.1354 (8) Å	µ = 4.90 mm⁻¹
b = 10.550 (1) Å	T = 173 K
c = 15.6055 (12) Å	0.20 × 0.15 × 0.10 mm
β = 96.680 (7)°

Data collection top

Oxford Xcalibur Eos Gemini diffractometer	3941 independent reflections
Absorption correction: multi-scan (CrysAlis RED; Oxford Diffraction, 2010)	2537 reflections with I > 2σ(I)
T_min = 0.441, T_max = 0.640	R_int = 0.061
14411 measured reflections

Refinement top

R[F² > 2σ(F²)] = 0.053	0 restraints
wR(F²) = 0.120	H-atom parameters constrained
S = 1.09	Δρ_max = 0.53 e Å⁻³
3941 reflections	Δρ_min = −0.64 e Å⁻³
201 parameters

Special details top

Geometry. All esds (except the esd in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell esds are taken into account individually in the estimation of esds in distances, angles and torsion angles; correlations between esds in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell esds is used for estimating esds 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

	x	y	z	U_iso*/U_eq
Br1	0.58094 (5)	0.79236 (5)	1.06171 (3)	0.06434 (19)
Br2	0.19292 (5)	0.55086 (6)	0.31176 (3)	0.0745 (2)
O1	0.7706 (3)	0.5773 (3)	1.09367 (19)	0.0569 (8)
O2	−0.0712 (3)	0.6690 (3)	0.3128 (2)	0.0651 (9)
N1	0.3700 (4)	0.6100 (4)	0.7479 (2)	0.0593 (10)
N2	0.3124 (4)	0.5901 (4)	0.6626 (2)	0.0564 (10)
C1	0.8682 (5)	0.4829 (5)	1.1222 (3)	0.0741 (15)
H1B	0.9152	0.5082	1.1781	0.111*
H1C	0.9319	0.4750	1.0799	0.111*
H1D	0.8241	0.4013	1.1283	0.111*
C2	0.6994 (4)	0.5613 (4)	1.0151 (3)	0.0464 (10)
C3	0.6047 (4)	0.6531 (4)	0.9888 (3)	0.0472 (10)
C4	0.5291 (4)	0.6453 (4)	0.9104 (3)	0.0490 (10)
H4A	0.4646	0.7088	0.8938	0.059*
C5	0.5461 (4)	0.5448 (4)	0.8545 (3)	0.0498 (11)
C6	0.6410 (4)	0.4535 (4)	0.8803 (3)	0.0531 (11)
H6A	0.6539	0.3847	0.8429	0.064*
C7	0.7170 (4)	0.4611 (5)	0.9595 (3)	0.0543 (12)
H7A	0.7815	0.3977	0.9761	0.065*
C9	0.4677 (5)	0.5372 (5)	0.7703 (3)	0.0547 (12)
H9A	0.4905	0.4751	0.7305	0.066*
C10	0.2020 (5)	0.6449 (5)	0.6464 (3)	0.0553 (11)
H10A	0.1649	0.6860	0.6922	0.066*
C11	0.1288 (4)	0.6482 (4)	0.5605 (3)	0.0482 (10)
C12	0.1842 (4)	0.6029 (4)	0.4883 (3)	0.0502 (11)
H12A	0.2701	0.5657	0.4953	0.060*
C13	0.1157 (4)	0.6119 (4)	0.4083 (3)	0.0467 (10)
C14	−0.0115 (4)	0.6638 (4)	0.3947 (3)	0.0487 (10)
C15	−0.0675 (4)	0.7078 (5)	0.4665 (3)	0.0584 (12)
H15A	−0.1545	0.7427	0.4596	0.070*
C16	0.0030 (5)	0.7007 (4)	0.5478 (3)	0.0575 (12)
H16A	−0.0358	0.7327	0.5959	0.069*
C17	−0.2036 (5)	0.7208 (5)	0.2988 (3)	0.0742 (15)
H17A	−0.2363	0.7163	0.2372	0.111*
H17B	−0.2020	0.8094	0.3177	0.111*
H17C	−0.2624	0.6718	0.3319	0.111*

Atomic displacement parameters (Å²) top

	U¹¹	U²²	U³³	U¹²	U¹³	U²³
Br1	0.0684 (3)	0.0498 (3)	0.0762 (4)	0.0041 (2)	0.0140 (2)	−0.0208 (2)
Br2	0.0810 (4)	0.0889 (5)	0.0578 (3)	0.0361 (3)	0.0266 (2)	0.0049 (3)
O1	0.0587 (18)	0.052 (2)	0.0613 (19)	0.0032 (15)	0.0121 (15)	−0.0035 (15)
O2	0.0606 (19)	0.068 (2)	0.067 (2)	0.0150 (17)	0.0113 (15)	−0.0011 (17)
N1	0.069 (2)	0.058 (3)	0.053 (2)	0.000 (2)	0.0149 (18)	−0.0042 (19)
N2	0.068 (3)	0.052 (3)	0.052 (2)	−0.009 (2)	0.0194 (18)	−0.0028 (18)
C1	0.071 (3)	0.072 (4)	0.080 (4)	0.023 (3)	0.010 (3)	0.007 (3)
C2	0.049 (2)	0.038 (3)	0.056 (3)	−0.007 (2)	0.024 (2)	−0.0015 (19)
C3	0.045 (2)	0.037 (3)	0.064 (3)	−0.0049 (19)	0.027 (2)	−0.010 (2)
C4	0.044 (2)	0.042 (3)	0.065 (3)	−0.0026 (19)	0.021 (2)	−0.004 (2)
C5	0.049 (2)	0.046 (3)	0.059 (3)	−0.011 (2)	0.027 (2)	−0.008 (2)
C6	0.061 (3)	0.042 (3)	0.062 (3)	0.000 (2)	0.029 (2)	−0.007 (2)
C7	0.057 (3)	0.047 (3)	0.064 (3)	0.008 (2)	0.026 (2)	0.003 (2)
C9	0.062 (3)	0.051 (3)	0.056 (3)	−0.013 (2)	0.029 (2)	−0.007 (2)
C10	0.069 (3)	0.043 (3)	0.059 (3)	−0.008 (2)	0.025 (2)	−0.007 (2)
C11	0.059 (3)	0.034 (3)	0.055 (3)	−0.002 (2)	0.022 (2)	0.0010 (19)
C12	0.053 (3)	0.036 (3)	0.065 (3)	0.002 (2)	0.022 (2)	0.002 (2)
C13	0.052 (2)	0.037 (3)	0.055 (3)	0.006 (2)	0.019 (2)	0.0032 (19)
C14	0.052 (2)	0.037 (3)	0.060 (3)	−0.002 (2)	0.018 (2)	−0.002 (2)
C15	0.051 (3)	0.046 (3)	0.081 (3)	0.006 (2)	0.024 (2)	−0.001 (2)
C16	0.063 (3)	0.044 (3)	0.070 (3)	0.000 (2)	0.028 (2)	−0.012 (2)
C17	0.065 (3)	0.074 (4)	0.082 (4)	0.019 (3)	0.006 (3)	−0.001 (3)

Geometric parameters (Å, º) top

Br1—C3	1.891 (4)	C6—C7	1.380 (6)
Br2—C13	1.889 (4)	C6—H6A	0.9500
O1—C2	1.359 (5)	C7—H7A	0.9500
O1—C1	1.437 (5)	C9—H9A	0.9500
O2—C14	1.351 (5)	C10—C11	1.456 (6)
O2—C17	1.442 (5)	C10—H10A	0.9500
N1—C9	1.269 (6)	C11—C16	1.383 (6)
N1—N2	1.405 (5)	C11—C12	1.399 (5)
N2—C10	1.259 (6)	C12—C13	1.361 (6)
C1—H1B	0.9800	C12—H12A	0.9500
C1—H1C	0.9800	C13—C14	1.394 (6)
C1—H1D	0.9800	C14—C15	1.392 (6)
C2—C3	1.391 (6)	C15—C16	1.383 (6)
C2—C7	1.393 (6)	C15—H15A	0.9500
C3—C4	1.369 (6)	C16—H16A	0.9500
C4—C5	1.396 (6)	C17—H17A	0.9800
C4—H4A	0.9500	C17—H17B	0.9800
C5—C6	1.387 (6)	C17—H17C	0.9800
C5—C9	1.456 (6)

C2—O1—C1	117.9 (4)	N1—C9—H9A	118.6
C14—O2—C17	117.7 (4)	C5—C9—H9A	118.6
C9—N1—N2	113.3 (4)	N2—C10—C11	122.8 (4)
C10—N2—N1	112.5 (4)	N2—C10—H10A	118.6
O1—C1—H1B	109.5	C11—C10—H10A	118.6
O1—C1—H1C	109.5	C16—C11—C12	118.1 (4)
H1B—C1—H1C	109.5	C16—C11—C10	120.3 (4)
O1—C1—H1D	109.5	C12—C11—C10	121.5 (4)
H1B—C1—H1D	109.5	C13—C12—C11	120.3 (4)
H1C—C1—H1D	109.5	C13—C12—H12A	119.8
O1—C2—C3	117.1 (4)	C11—C12—H12A	119.8
O1—C2—C7	124.3 (4)	C12—C13—C14	122.1 (4)
C3—C2—C7	118.6 (4)	C12—C13—Br2	119.6 (3)
C4—C3—C2	121.1 (4)	C14—C13—Br2	118.4 (3)
C4—C3—Br1	119.2 (3)	O2—C14—C15	124.7 (4)
C2—C3—Br1	119.7 (3)	O2—C14—C13	117.6 (4)
C3—C4—C5	120.5 (4)	C15—C14—C13	117.7 (4)
C3—C4—H4A	119.8	C16—C15—C14	120.3 (4)
C5—C4—H4A	119.8	C16—C15—H15A	119.9
C6—C5—C4	118.5 (4)	C14—C15—H15A	119.9
C6—C5—C9	120.7 (4)	C11—C16—C15	121.5 (4)
C4—C5—C9	120.7 (4)	C11—C16—H16A	119.3
C7—C6—C5	121.0 (4)	C15—C16—H16A	119.3
C7—C6—H6A	119.5	O2—C17—H17A	109.5
C5—C6—H6A	119.5	O2—C17—H17B	109.5
C6—C7—C2	120.2 (4)	H17A—C17—H17B	109.5
C6—C7—H7A	119.9	O2—C17—H17C	109.5
C2—C7—H7A	119.9	H17A—C17—H17C	109.5
N1—C9—C5	122.8 (4)	H17B—C17—H17C	109.5

C9—N1—N2—C10	167.5 (4)	N1—N2—C10—C11	174.2 (4)
C1—O1—C2—C3	179.5 (4)	N2—C10—C11—C16	174.6 (4)
C1—O1—C2—C7	−1.6 (6)	N2—C10—C11—C12	−7.6 (7)
O1—C2—C3—C4	179.5 (3)	C16—C11—C12—C13	0.6 (7)
C7—C2—C3—C4	0.5 (6)	C10—C11—C12—C13	−177.3 (4)
O1—C2—C3—Br1	0.3 (5)	C11—C12—C13—C14	−1.1 (7)
C7—C2—C3—Br1	−178.7 (3)	C11—C12—C13—Br2	179.7 (3)
C2—C3—C4—C5	−0.4 (6)	C17—O2—C14—C15	−1.6 (7)
Br1—C3—C4—C5	178.8 (3)	C17—O2—C14—C13	179.0 (4)
C3—C4—C5—C6	0.0 (6)	C12—C13—C14—O2	179.8 (4)
C3—C4—C5—C9	−178.9 (4)	Br2—C13—C14—O2	−1.0 (5)
C4—C5—C6—C7	0.2 (6)	C12—C13—C14—C15	0.4 (7)
C9—C5—C6—C7	179.1 (4)	Br2—C13—C14—C15	179.6 (3)
C5—C6—C7—C2	0.0 (6)	O2—C14—C15—C16	−178.6 (4)
O1—C2—C7—C6	−179.2 (4)	C13—C14—C15—C16	0.8 (7)
C3—C2—C7—C6	−0.4 (6)	C12—C11—C16—C15	0.6 (7)
N2—N1—C9—C5	177.2 (4)	C10—C11—C16—C15	178.4 (4)
C6—C5—C9—N1	171.8 (4)	C14—C15—C16—C11	−1.3 (7)
C4—C5—C9—N1	−9.3 (6)

Experimental details

Crystal data
Chemical formula	C₁₆H₁₄Br₂N₂O₂
M_r	426.11
Crystal system, space group	Monoclinic, P2₁/c
Temperature (K)	173
a, b, c (Å)	10.1354 (8), 10.550 (1), 15.6055 (12)
β (°)	96.680 (7)
V (Å³)	1657.3 (2)
Z	4
Radiation type	Mo Kα
µ (mm⁻¹)	4.90
Crystal size (mm)	0.20 × 0.15 × 0.10

Data collection
Diffractometer	Oxford Xcalibur Eos Gemini diffractometer
Absorption correction	Multi-scan (CrysAlis RED; Oxford Diffraction, 2010)
T_min, T_max	0.441, 0.640
No. of measured, independent and observed [I > 2σ(I)] reflections	14411, 3941, 2537
R_int	0.061
(sin θ/λ)_max (Å⁻¹)	0.658

Refinement
R[F² > 2σ(F²)], wR(F²), S	0.053, 0.120, 1.09
No. of reflections	3941
No. of parameters	201
H-atom treatment	H-atom parameters constrained
Δρ_max, Δρ_min (e Å⁻³)	0.53, −0.64

Computer programs: CrysAlis PRO (Oxford Diffraction, 2010), CrysAlis RED (Oxford Diffraction, 2010), SHELXS97 (Sheldrick, 2008), SHELXL97 (Sheldrick, 2008), SHELXTL (Sheldrick, 2008).

Acknowledgements

CSC and HSY thank the University of Mysore for research facilities. JPJ acknowledges the NSF–MRI programme (grant No. CHE1039027) for funds to purchase the X-ray diffractometer.

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