N′-(3-Bromo-5-chloro-2-hy­droxy­benzyl­idene)-2H-1,3-benzodioxole-5-carbo­hydrazide

Wei, J.; Ban, H.-Y.; Sun, X.-Z.

doi:10.1107/S160053681201433X

organic compounds

CRYSTALLOGRAPHIC
COMMUNICATIONS

ISSN: 2056-9890

Volume 68| Part 5| May 2012| Pages o1336-o1337

doi:10.1107/S160053681201433X

Open

access

N′-(3-Bromo-5-chloro-2-hydroxybenzylidene)-2H-1,3-benzodioxole-5-carbohydrazide

Jiao Wei,^a Hong-Yan Ban ^a ^* and Xiao-Zhi Sun ^a

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

(Received 31 March 2012; accepted 3 April 2012; online 6 April 2012)

The asymmetric unit of the title hydrazone compound, C₁₅H₁₀BrClN₂O₄, contains two independent molecules. The dihedral angles between the benzene rings are 38.7 (3)° in one molecule and 24.3 (3)° in the other. Both molecules exist in trans conformations with respect to the C=N double bonds of the central methylidene units. Intramolecular O—H⋯N contacts are observed in both molecules, forming S(6) rings. In the crystal, molecules are linked through N—H⋯O hydrogen bonds into chains along the a axis.

Related literature

For the biological activity of hydrazones, see: Zhong et al. (2007 ); Raj et al. (2007 ); Jimenez-Pulido et al. (2008 ). For related structures, see: Ban (2010 ); Ban & Li (2008a ,b ); Li & Ban (2009a ,b ); Yehye et al. (2008 ); Fun et al. (2008a ,b ); Yang et al. (2008 ); Ejsmont et al. (2008 ); Yang (2006 ). For hydrogen-bond motifs, see: Bernstein et al. (1995 ).

Experimental

Crystal data

C₁₅H₁₀BrClN₂O₄
M_r = 397.61
Triclinic, $[P \overline 1]$
a = 9.769 (2) Å
b = 13.041 (3) Å
c = 13.251 (3) Å
α = 75.558 (2)°
β = 78.745 (2)°
γ = 76.527 (2)°
V = 1572.9 (6) Å³
Z = 4
Mo Kα radiation
μ = 2.80 mm⁻¹
T = 298 K
0.12 × 0.10 × 0.10 mm

Data collection

Bruker SMART CCD area-detector diffractometer
Absorption correction: multi-scan (SADABS; Sheldrick, 1996 ) T_min = 0.730, T_max = 0.767
8062 measured reflections
5662 independent reflections
3817 reflections with I > 2σ(I)
R_int = 0.019

Refinement

R[F² > 2σ(F²)] = 0.048
wR(F²) = 0.137
S = 1.01
5662 reflections
423 parameters
2 restraints
H atoms treated by a mixture of independent and constrained refinement
Δρ_max = 1.23 e Å⁻³
Δρ_min = −0.40 e Å⁻³

Table 1
Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
N2—H2⋯O4ⁱ	0.90 (1)	2.00 (2)	2.872 (4)	162 (5)
O3—H3⋯N3	0.82	1.92	2.637 (4)	145
O1—H1⋯N1	0.82	1.85	2.561 (4)	145
Symmetry code: (i) -x+1, -y+1, -z+1.

Data collection: SMART (Bruker, 1998 ); cell refinement: SAINT (Bruker, 1998); data reduction: SAINT; 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/S160053681201433X/sj5231sup1.cif

Structure factors: contains datablock I. DOI: 10.1107/S160053681201433X/sj5231Isup2.hkl

Supporting information file. DOI: 10.1107/S160053681201433X/sj5231Isup3.cml

checkCIF report

Comment top

Hydrazone compounds 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 number of hydrazone compounds have been synthesized and structurally characterized (Yehye et al., 2008; Fun et al., 2008a,b; Yang et al., 2008; Ejsmont et al., 2008; Yang, 2006). Recently, we have reported several such compounds (Ban, 2010; Ban & Li, 2008a,b; Li & Ban, 2009a,b). We report here the crystal structure of the new title benzohydrazide derivative.

The asymmetric unit of the title hydrazone compound, Fig. 1, contains two independent molecules. The dihedral angles between the two benzene rings are 38.7 (3) and 24.3 (3)°, respectively. The molecules exist in trans configuration with respect to the central methylidene units. Intramolecular O1—H1···N1 and O3—H3···N3 contacts are observed forming S(6) rings (Bernstein et al., 1995). In the crystal structure, molecules are linked through intermolecular N—H···O hydrogen bonds (Table 1), forming chains along the a axis, Fig. 2.

Related literature top

For the biological activity of hydrazones, see: Zhong et al. (2007); Raj et al. (2007); Jimenez-Pulido et al. (2008). For related structures, see: Ban (2010); Ban & Li (2008a,b); Li & Ban (2009a,b); Yehye et al. (2008); Fun et al. (2008a,b); Yang et al. (2008); Ejsmont et al. (2008); Yang (2006). For hydrogen-bond motifs, see: Bernstein et al. (1995).

Experimental top

The title compound was prepared by refluxing 3-bromo-5-chlorosalicylaldehyde (1.0 mol, 0.23 g) with [3,4]dioxolebenzohydrazide (1.0 mol, 0.18 g) in methanol (50 ml). Excess methanol was removed from the mixture by distillation. A colourless solid product was filtered, and washed three times with methanol. Colourless block-shaped crystals of the title compound were obtained from a methanol solution of the compound by slow evaporation in air.

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

	Fig. 1. The molecular structure of the title compound, showing 30% probability displacement ellipsoids for the non-hydrogen atoms. Intramolecular hydrogen bonds are shown as dashed lines.
	Fig. 2. The packing diagram of the title compound, viewed along the c axis. Hydrogen bonds are shown as dashed lines.

N'-(3-Bromo-5-chloro-2-hydroxybenzylidene)-2H-1,3-benzodioxole- 5-carbohydrazide top

Crystal data top

C₁₅H₁₀BrClN₂O₄	Z = 4
M_r = 397.61	F(000) = 792
Triclinic, P1	D_x = 1.679 Mg m⁻³
Hall symbol: -P 1	Mo Kα radiation, λ = 0.71073 Å
a = 9.769 (2) Å	Cell parameters from 2572 reflections
b = 13.041 (3) Å	θ = 2.5–25.0°
c = 13.251 (3) Å	µ = 2.80 mm⁻¹
α = 75.558 (2)°	T = 298 K
β = 78.745 (2)°	Block, colourless
γ = 76.527 (2)°	0.12 × 0.10 × 0.10 mm
V = 1572.9 (6) Å³

Data collection top

Bruker SMART CCD area-detector diffractometer	5662 independent reflections
Radiation source: fine-focus sealed tube	3817 reflections with I > 2σ(I)
Graphite monochromator	R_int = 0.019
ω scans	θ_max = 25.5°, θ_min = 3.6°
Absorption correction: multi-scan (SADABS; Sheldrick, 1996)	h = −11→11
T_min = 0.730, T_max = 0.767	k = −15→14
8062 measured reflections	l = −16→15

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)] = 0.048	Hydrogen site location: inferred from neighbouring sites
wR(F²) = 0.137	H atoms treated by a mixture of independent and constrained refinement
S = 1.01	w = 1/[σ²(F_o²) + (0.0804P)²] where P = (F_o² + 2F_c²)/3
5662 reflections	(Δ/σ)_max = 0.001
423 parameters	Δρ_max = 1.23 e Å⁻³
2 restraints	Δρ_min = −0.40 e Å⁻³

Crystal data top

C₁₅H₁₀BrClN₂O₄	γ = 76.527 (2)°
M_r = 397.61	V = 1572.9 (6) Å³
Triclinic, P1	Z = 4
a = 9.769 (2) Å	Mo Kα radiation
b = 13.041 (3) Å	µ = 2.80 mm⁻¹
c = 13.251 (3) Å	T = 298 K
α = 75.558 (2)°	0.12 × 0.10 × 0.10 mm
β = 78.745 (2)°

Data collection top

Bruker SMART CCD area-detector diffractometer	5662 independent reflections
Absorption correction: multi-scan (SADABS; Sheldrick, 1996)	3817 reflections with I > 2σ(I)
T_min = 0.730, T_max = 0.767	R_int = 0.019
8062 measured reflections

Refinement top

R[F² > 2σ(F²)] = 0.048	2 restraints
wR(F²) = 0.137	H atoms treated by a mixture of independent and constrained refinement
S = 1.01	Δρ_max = 1.23 e Å⁻³
5662 reflections	Δρ_min = −0.40 e Å⁻³
423 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

	x	y	z	U_iso*/U_eq
Br1	−0.32727 (5)	0.72347 (4)	1.11304 (4)	0.0705 (2)
Br2	0.88064 (7)	−0.00317 (5)	0.23324 (6)	0.0941 (3)
Cl1	0.21177 (17)	0.81156 (13)	1.05109 (10)	0.0840 (4)
Cl2	0.35756 (17)	0.02462 (10)	0.11594 (10)	0.0753 (4)
N1	0.0059 (3)	0.5383 (2)	0.8013 (2)	0.0388 (7)
N2	0.0549 (3)	0.4803 (2)	0.7245 (2)	0.0388 (7)
N3	0.5226 (3)	0.3717 (2)	0.3015 (2)	0.0395 (7)
N4	0.4588 (3)	0.4720 (2)	0.3202 (3)	0.0404 (7)
O1	−0.1949 (3)	0.6081 (2)	0.9379 (2)	0.0517 (7)
H1	−0.1559	0.5706	0.8951	0.078*
O2	−0.1698 (3)	0.4846 (2)	0.7053 (2)	0.0543 (7)
O3	0.7314 (3)	0.2028 (2)	0.2949 (2)	0.0504 (7)
H3	0.6932	0.2628	0.3057	0.076*
O4	0.6578 (3)	0.4993 (2)	0.3652 (2)	0.0463 (6)
O5	−0.0839 (3)	0.2765 (2)	0.4030 (2)	0.0548 (7)
O6	0.1385 (3)	0.1716 (2)	0.4079 (3)	0.0657 (9)
O7	0.4445 (3)	0.8606 (2)	0.4909 (2)	0.0552 (8)
O8	0.2603 (3)	0.9451 (2)	0.3952 (3)	0.0622 (8)
C1	0.0423 (4)	0.6396 (3)	0.9147 (3)	0.0409 (9)
C2	−0.0981 (4)	0.6516 (3)	0.9635 (3)	0.0407 (9)
C3	−0.1388 (5)	0.7108 (3)	1.0418 (3)	0.0486 (10)
C4	−0.0453 (5)	0.7608 (3)	1.0691 (3)	0.0576 (11)
H4	−0.0752	0.8024	1.1199	0.069*
C5	0.0917 (6)	0.7474 (4)	1.0197 (3)	0.0557 (11)
C6	0.1375 (5)	0.6876 (3)	0.9435 (3)	0.0492 (10)
H6	0.2318	0.6793	0.9113	0.059*
C7	0.0940 (4)	0.5775 (3)	0.8325 (3)	0.0389 (8)
H7	0.1896	0.5668	0.8035	0.047*
C8	−0.0431 (4)	0.4514 (3)	0.6826 (3)	0.0374 (8)
C9	0.0141 (4)	0.3772 (3)	0.6091 (3)	0.0375 (8)
C10	−0.0726 (4)	0.3719 (3)	0.5385 (3)	0.0378 (8)
H10	−0.1616	0.4166	0.5342	0.045*
C11	−0.0211 (4)	0.2988 (3)	0.4768 (3)	0.0383 (8)
C12	0.1124 (4)	0.2353 (3)	0.4811 (3)	0.0481 (10)
C13	0.1984 (5)	0.2380 (4)	0.5486 (4)	0.0615 (13)
H13	0.2874	0.1931	0.5513	0.074*
C14	0.1469 (4)	0.3115 (3)	0.6138 (3)	0.0511 (10)
H14	0.2027	0.3164	0.6612	0.061*
C15	0.0072 (5)	0.1843 (4)	0.3712 (4)	0.0587 (12)
H15A	−0.0344	0.1207	0.4013	0.070*
H15B	0.0218	0.1947	0.2950	0.070*
C16	0.5024 (4)	0.2181 (3)	0.2431 (3)	0.0416 (9)
C17	0.6426 (4)	0.1645 (3)	0.2551 (3)	0.0420 (9)
C18	0.6890 (5)	0.0671 (3)	0.2240 (3)	0.0537 (11)
C19	0.6042 (6)	0.0232 (3)	0.1819 (4)	0.0625 (12)
H19	0.6384	−0.0424	0.1613	0.075*
C20	0.4687 (5)	0.0778 (3)	0.1709 (3)	0.0518 (10)
C21	0.4175 (5)	0.1738 (3)	0.2008 (3)	0.0486 (10)
H21	0.3248	0.2097	0.1928	0.058*
C22	0.4453 (4)	0.3235 (3)	0.2702 (3)	0.0432 (9)
H22	0.3508	0.3557	0.2645	0.052*
C23	0.5344 (4)	0.5333 (3)	0.3475 (3)	0.0359 (8)
C24	0.4563 (4)	0.6435 (3)	0.3554 (3)	0.0339 (8)
C25	0.4952 (4)	0.6931 (3)	0.4253 (3)	0.0376 (8)
H25	0.5668	0.6581	0.4661	0.045*
C26	0.4240 (4)	0.7935 (3)	0.4306 (3)	0.0395 (9)
C27	0.3156 (4)	0.8472 (3)	0.3720 (3)	0.0416 (9)
C28	0.2767 (4)	0.8009 (3)	0.3039 (3)	0.0453 (9)
H28	0.2038	0.8368	0.2646	0.054*
C29	0.3496 (4)	0.6983 (3)	0.2953 (3)	0.0411 (9)
H29	0.3265	0.6652	0.2480	0.049*
C30	0.3443 (5)	0.9591 (3)	0.4641 (4)	0.0557 (11)
H30A	0.2843	0.9769	0.5273	0.067*
H30B	0.3942	1.0177	0.4303	0.067*
H2	0.146 (2)	0.472 (4)	0.693 (4)	0.080*
H4A	0.3647 (15)	0.492 (4)	0.319 (4)	0.080*

Atomic displacement parameters (Å²) top

	U¹¹	U²²	U³³	U¹²	U¹³	U²³
Br1	0.0662 (3)	0.0716 (3)	0.0670 (3)	−0.0066 (2)	0.0176 (2)	−0.0304 (2)
Br2	0.0815 (4)	0.0707 (4)	0.1334 (5)	0.0298 (3)	−0.0303 (4)	−0.0577 (4)
Cl1	0.1060 (11)	0.1103 (11)	0.0655 (7)	−0.0541 (9)	−0.0172 (7)	−0.0390 (7)
Cl2	0.1106 (11)	0.0657 (8)	0.0708 (7)	−0.0447 (7)	−0.0206 (7)	−0.0219 (6)
N1	0.0374 (17)	0.0426 (17)	0.0378 (16)	−0.0042 (14)	−0.0025 (13)	−0.0166 (14)
N2	0.0320 (16)	0.0453 (18)	0.0431 (17)	−0.0064 (14)	0.0003 (13)	−0.0223 (14)
N3	0.0398 (17)	0.0308 (16)	0.0480 (17)	0.0007 (13)	−0.0049 (14)	−0.0172 (14)
N4	0.0302 (16)	0.0333 (16)	0.0592 (19)	−0.0001 (13)	−0.0061 (14)	−0.0186 (14)
O1	0.0400 (15)	0.0580 (18)	0.0614 (18)	−0.0081 (13)	−0.0004 (13)	−0.0270 (14)
O2	0.0298 (14)	0.0656 (18)	0.0775 (19)	−0.0028 (13)	−0.0023 (13)	−0.0440 (16)
O3	0.0434 (16)	0.0454 (16)	0.0669 (17)	0.0004 (12)	−0.0123 (13)	−0.0256 (14)
O4	0.0269 (14)	0.0460 (15)	0.0688 (17)	−0.0012 (11)	−0.0088 (12)	−0.0211 (13)
O5	0.0484 (16)	0.0596 (18)	0.0627 (17)	0.0092 (14)	−0.0202 (14)	−0.0336 (15)
O6	0.0516 (18)	0.0624 (19)	0.098 (2)	0.0120 (15)	−0.0205 (16)	−0.0581 (18)
O7	0.0619 (18)	0.0482 (16)	0.0630 (17)	0.0101 (14)	−0.0245 (15)	−0.0329 (14)
O8	0.066 (2)	0.0450 (16)	0.082 (2)	0.0141 (14)	−0.0274 (16)	−0.0353 (15)
C1	0.046 (2)	0.042 (2)	0.0371 (19)	−0.0084 (17)	−0.0055 (16)	−0.0121 (16)
C2	0.048 (2)	0.036 (2)	0.041 (2)	−0.0087 (17)	−0.0067 (17)	−0.0116 (16)
C3	0.058 (3)	0.042 (2)	0.041 (2)	−0.0035 (19)	−0.0014 (18)	−0.0106 (18)
C4	0.085 (3)	0.052 (3)	0.040 (2)	−0.021 (2)	0.000 (2)	−0.0193 (19)
C5	0.081 (3)	0.060 (3)	0.037 (2)	−0.025 (2)	−0.015 (2)	−0.0151 (19)
C6	0.056 (3)	0.055 (2)	0.042 (2)	−0.017 (2)	−0.0079 (18)	−0.0140 (19)
C7	0.0341 (19)	0.045 (2)	0.0378 (19)	−0.0039 (17)	−0.0038 (15)	−0.0134 (17)
C8	0.0309 (19)	0.040 (2)	0.043 (2)	−0.0047 (16)	−0.0042 (15)	−0.0152 (16)
C9	0.0297 (18)	0.0350 (19)	0.050 (2)	−0.0051 (15)	−0.0019 (16)	−0.0168 (16)
C10	0.0310 (18)	0.040 (2)	0.0422 (19)	−0.0004 (16)	−0.0045 (15)	−0.0155 (16)
C11	0.0341 (19)	0.041 (2)	0.0406 (19)	−0.0023 (16)	−0.0057 (15)	−0.0144 (16)
C12	0.040 (2)	0.042 (2)	0.068 (3)	0.0003 (18)	−0.0067 (19)	−0.031 (2)
C13	0.042 (2)	0.053 (3)	0.102 (4)	0.014 (2)	−0.026 (2)	−0.047 (3)
C14	0.039 (2)	0.051 (2)	0.072 (3)	0.0023 (18)	−0.022 (2)	−0.030 (2)
C15	0.058 (3)	0.053 (3)	0.072 (3)	0.007 (2)	−0.019 (2)	−0.037 (2)
C16	0.046 (2)	0.036 (2)	0.045 (2)	−0.0074 (17)	−0.0051 (17)	−0.0129 (16)
C17	0.049 (2)	0.036 (2)	0.042 (2)	−0.0043 (17)	−0.0066 (17)	−0.0146 (17)
C18	0.063 (3)	0.042 (2)	0.054 (2)	0.004 (2)	−0.011 (2)	−0.0182 (19)
C19	0.086 (4)	0.040 (2)	0.064 (3)	−0.005 (2)	−0.008 (2)	−0.023 (2)
C20	0.073 (3)	0.041 (2)	0.049 (2)	−0.021 (2)	−0.008 (2)	−0.0163 (19)
C21	0.049 (2)	0.045 (2)	0.056 (2)	−0.0101 (19)	−0.0122 (19)	−0.0141 (19)
C22	0.037 (2)	0.039 (2)	0.057 (2)	−0.0028 (17)	−0.0084 (17)	−0.0186 (18)
C23	0.033 (2)	0.0370 (19)	0.0387 (19)	−0.0071 (16)	0.0000 (15)	−0.0133 (16)
C24	0.0285 (18)	0.0319 (18)	0.0411 (19)	−0.0044 (14)	−0.0017 (15)	−0.0112 (15)
C25	0.0328 (19)	0.039 (2)	0.0391 (19)	0.0005 (16)	−0.0055 (15)	−0.0121 (16)
C26	0.039 (2)	0.043 (2)	0.0391 (19)	−0.0039 (17)	−0.0061 (16)	−0.0171 (17)
C27	0.041 (2)	0.033 (2)	0.050 (2)	0.0025 (16)	−0.0072 (17)	−0.0157 (17)
C28	0.046 (2)	0.040 (2)	0.053 (2)	−0.0036 (18)	−0.0173 (18)	−0.0127 (18)
C29	0.042 (2)	0.036 (2)	0.051 (2)	−0.0074 (16)	−0.0118 (18)	−0.0136 (17)
C30	0.064 (3)	0.046 (2)	0.062 (3)	0.008 (2)	−0.019 (2)	−0.031 (2)

Geometric parameters (Å, º) top

Br1—C3	1.888 (4)	C7—H7	0.9300
Br2—C18	1.896 (4)	C8—C9	1.484 (5)
Cl1—C5	1.752 (5)	C9—C14	1.381 (5)
Cl2—C20	1.761 (4)	C9—C10	1.403 (5)
N1—C7	1.274 (5)	C10—C11	1.354 (5)
N1—N2	1.365 (4)	C10—H10	0.9300
N2—C8	1.359 (5)	C11—C12	1.376 (5)
N2—H2	0.899 (10)	C12—C13	1.352 (6)
N3—C22	1.268 (5)	C13—C14	1.392 (6)
N3—N4	1.372 (4)	C13—H13	0.9300
N4—C23	1.355 (5)	C14—H14	0.9300
N4—H4A	0.898 (10)	C15—H15A	0.9700
O1—C2	1.343 (5)	C15—H15B	0.9700
O1—H1	0.8200	C16—C21	1.379 (5)
O2—C8	1.216 (4)	C16—C17	1.405 (6)
O3—C17	1.338 (5)	C16—C22	1.464 (5)
O3—H3	0.8200	C17—C18	1.381 (5)
O4—C23	1.231 (4)	C18—C19	1.373 (6)
O5—C11	1.370 (4)	C19—C20	1.365 (7)
O5—C15	1.422 (5)	C19—H19	0.9300
O6—C12	1.379 (4)	C20—C21	1.362 (6)
O6—C15	1.419 (5)	C21—H21	0.9300
O7—C26	1.392 (4)	C22—H22	0.9300
O7—C30	1.434 (5)	C23—C24	1.481 (5)
O8—C27	1.351 (4)	C24—C29	1.388 (5)
O8—C30	1.410 (5)	C24—C25	1.405 (5)
C1—C2	1.388 (5)	C25—C26	1.343 (5)
C1—C6	1.390 (6)	C25—H25	0.9300
C1—C7	1.459 (5)	C26—C27	1.385 (5)
C2—C3	1.389 (5)	C27—C28	1.355 (5)
C3—C4	1.383 (6)	C28—C29	1.383 (5)
C4—C5	1.363 (7)	C28—H28	0.9300
C4—H4	0.9300	C29—H29	0.9300
C5—C6	1.372 (6)	C30—H30A	0.9700
C6—H6	0.9300	C30—H30B	0.9700

C7—N1—N2	118.6 (3)	C13—C14—H14	119.6
C8—N2—N1	117.5 (3)	O6—C15—O5	107.1 (3)
C8—N2—H2	120 (3)	O6—C15—H15A	110.3
N1—N2—H2	121 (3)	O5—C15—H15A	110.3
C22—N3—N4	115.6 (3)	O6—C15—H15B	110.3
C23—N4—N3	120.5 (3)	O5—C15—H15B	110.3
C23—N4—H4A	122 (3)	H15A—C15—H15B	108.6
N3—N4—H4A	117 (3)	C21—C16—C17	120.1 (3)
C2—O1—H1	109.5	C21—C16—C22	118.5 (3)
C17—O3—H3	109.5	C17—C16—C22	121.3 (3)
C11—O5—C15	105.9 (3)	O3—C17—C18	119.3 (4)
C12—O6—C15	106.2 (3)	O3—C17—C16	123.4 (3)
C26—O7—C30	105.0 (3)	C18—C17—C16	117.3 (4)
C27—O8—C30	106.7 (3)	C19—C18—C17	122.5 (4)
C2—C1—C6	120.0 (3)	C19—C18—Br2	119.5 (3)
C2—C1—C7	121.7 (3)	C17—C18—Br2	117.9 (3)
C6—C1—C7	118.3 (4)	C20—C19—C18	118.7 (4)
O1—C2—C1	122.5 (3)	C20—C19—H19	120.7
O1—C2—C3	119.2 (4)	C18—C19—H19	120.7
C1—C2—C3	118.3 (4)	C21—C20—C19	121.2 (4)
C4—C3—C2	121.9 (4)	C21—C20—Cl2	118.9 (4)
C4—C3—Br1	119.1 (3)	C19—C20—Cl2	119.9 (3)
C2—C3—Br1	119.0 (3)	C20—C21—C16	120.2 (4)
C5—C4—C3	118.3 (4)	C20—C21—H21	119.9
C5—C4—H4	120.8	C16—C21—H21	119.9
C3—C4—H4	120.8	N3—C22—C16	121.1 (3)
C4—C5—C6	121.8 (4)	N3—C22—H22	119.5
C4—C5—Cl1	119.3 (3)	C16—C22—H22	119.5
C6—C5—Cl1	118.8 (4)	O4—C23—N4	122.4 (3)
C5—C6—C1	119.6 (4)	O4—C23—C24	122.8 (3)
C5—C6—H6	120.2	N4—C23—C24	114.7 (3)
C1—C6—H6	120.2	C29—C24—C25	120.1 (3)
N1—C7—C1	118.8 (3)	C29—C24—C23	122.1 (3)
N1—C7—H7	120.6	C25—C24—C23	117.8 (3)
C1—C7—H7	120.6	C26—C25—C24	116.8 (3)
O2—C8—N2	121.2 (3)	C26—C25—H25	121.6
O2—C8—C9	122.8 (3)	C24—C25—H25	121.6
N2—C8—C9	115.9 (3)	C25—C26—C27	123.0 (3)
C14—C9—C10	121.0 (3)	C25—C26—O7	128.1 (3)
C14—C9—C8	120.6 (3)	C27—C26—O7	108.9 (3)
C10—C9—C8	118.3 (3)	O8—C27—C28	128.5 (3)
C11—C10—C9	117.0 (3)	O8—C27—C26	110.4 (3)
C11—C10—H10	121.5	C28—C27—C26	121.1 (3)
C9—C10—H10	121.5	C27—C28—C29	117.4 (3)
C10—C11—O5	128.8 (3)	C27—C28—H28	121.3
C10—C11—C12	121.2 (3)	C29—C28—H28	121.3
O5—C11—C12	109.9 (3)	C28—C29—C24	121.6 (3)
C13—C12—C11	123.2 (3)	C28—C29—H29	119.2
C13—C12—O6	128.1 (3)	C24—C29—H29	119.2
C11—C12—O6	108.7 (3)	O8—C30—O7	108.6 (3)
C12—C13—C14	116.6 (4)	O8—C30—H30A	110.0
C12—C13—H13	121.7	O7—C30—H30A	110.0
C14—C13—H13	121.7	O8—C30—H30B	110.0
C9—C14—C13	120.9 (4)	O7—C30—H30B	110.0
C9—C14—H14	119.6	H30A—C30—H30B	108.4

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
N2—H2···O4ⁱ	0.90 (1)	2.00 (2)	2.872 (4)	162 (5)
O3—H3···N3	0.82	1.92	2.637 (4)	145
O1—H1···N1	0.82	1.85	2.561 (4)	145

Symmetry code: (i) −x+1, −y+1, −z+1.

Experimental details

Crystal data
Chemical formula	C₁₅H₁₀BrClN₂O₄
M_r	397.61
Crystal system, space group	Triclinic, P1
Temperature (K)	298
a, b, c (Å)	9.769 (2), 13.041 (3), 13.251 (3)
α, β, γ (°)	75.558 (2), 78.745 (2), 76.527 (2)
V (Å³)	1572.9 (6)
Z	4
Radiation type	Mo Kα
µ (mm⁻¹)	2.80
Crystal size (mm)	0.12 × 0.10 × 0.10

Data collection
Diffractometer	Bruker SMART CCD area-detector diffractometer
Absorption correction	Multi-scan (SADABS; Sheldrick, 1996)
T_min, T_max	0.730, 0.767
No. of measured, independent and observed [I > 2σ(I)] reflections	8062, 5662, 3817
R_int	0.019
(sin θ/λ)_max (Å⁻¹)	0.606

Refinement
R[F² > 2σ(F²)], wR(F²), S	0.048, 0.137, 1.01
No. of reflections	5662
No. of parameters	423
No. of restraints	2
H-atom treatment	H atoms treated by a mixture of independent and constrained refinement
Δρ_max, Δρ_min (e Å⁻³)	1.23, −0.40

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···A	D—H	H···A	D···A	D—H···A
N2—H2···O4ⁱ	0.899 (10)	2.00 (2)	2.872 (4)	162 (5)
O3—H3···N3	0.82	1.92	2.637 (4)	145.3
O1—H1···N1	0.82	1.85	2.561 (4)	145.0

Symmetry code: (i) −x+1, −y+1, −z+1.

Acknowledgements

The authors acknowledge the 7th issue of the Undergraduate's Research and Training Project of the University of Science and Technology Liaoning, and the Youth Foundation of the University of Science and Technology Liaoning (2010Y06).

References

Ban, H.-Y. (2010). Acta Cryst. E66, o3240. Web of Science CSD CrossRef IUCr Journals Google Scholar
Ban, H.-Y. & Li, C.-M. (2008a). Acta Cryst. E64, o2177. Web of Science CrossRef IUCr Journals Google Scholar
Ban, H.-Y. & Li, C.-M. (2008b). Acta Cryst. E64, o2260. Web of Science CrossRef IUCr Journals Google Scholar
Bernstein, J., Davis, R. E., Shimoni, L. & Chang, N.-L. (1995). Angew. Chem. Int. Ed. Engl. 34, 1555–1573. CrossRef CAS Web of Science Google Scholar
Bruker (1998). SMART and SAINT. Bruker AXS Inc., Madison, Wisconsin, USA. Google Scholar
Ejsmont, K., Zareef, M., Arfan, M., Bashir, S. A. & Zaleski, J. (2008). Acta Cryst. E64, o1128. Web of Science CSD CrossRef IUCr Journals Google Scholar
Fun, H.-K., Patil, P. S., Jebas, S. R., Sujith, K. V. & Kalluraya, B. (2008a). Acta Cryst. E64, o1594–o1595. Web of Science CSD CrossRef IUCr Journals Google Scholar
Fun, H.-K., Patil, P. S., Rao, J. N., Kalluraya, B. & Chantrapromma, S. (2008b). Acta Cryst. E64, o1707. Web of Science CSD CrossRef IUCr Journals Google Scholar
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. Web of Science CSD CrossRef PubMed CAS Google Scholar
Li, C.-M. & Ban, H.-Y. (2009a). Acta Cryst. E65, o876. Web of Science CSD CrossRef IUCr Journals Google Scholar
Li, C.-M. & Ban, H.-Y. (2009b). Acta Cryst. E65, o883. Web of Science CSD CrossRef IUCr Journals Google Scholar
Raj, K. K. V., Narayana, B., Ashalatha, B. V., Kumari, N. S. & Sarojini, B. K. (2007). Eur. J. Med. Chem. 42, 425–429. PubMed CAS Google Scholar
Sheldrick, G. M. (1996). SADABS. University of Göttingen, Gemany. Google Scholar
Sheldrick, G. M. (2008). Acta Cryst. A64, 112–122. Web of Science CrossRef CAS IUCr Journals Google Scholar
Yang, D.-S. (2006). Acta Cryst. E62, o3792–o3793. Web of Science CSD CrossRef IUCr Journals Google Scholar
Yang, T., Cao, G.-B., Xiang, J.-M. & Zhang, L.-H. (2008). Acta Cryst. E64, o1186. Web of Science CSD CrossRef IUCr Journals Google Scholar
Yehye, W. A., Rahman, N. A., Ariffin, A. & Ng, S. W. (2008). Acta Cryst. E64, o1824. Web of Science CSD CrossRef IUCr Journals Google Scholar
Zhong, X., Wei, H.-L., Liu, W.-S., Wang, D.-Q. & Wang, X. (2007). Bioorg. Med. Chem. Lett. 17, 3774–3777. Web of Science CSD CrossRef PubMed CAS Google Scholar

This is an open-access article distributed under the terms of the Creative Commons Attribution (CC-BY) Licence, which permits unrestricted use, distribution, and reproduction in any medium, provided the original authors and source are cited.

CRYSTALLOGRAPHIC
COMMUNICATIONS

ISSN: 2056-9890

Volume 68| Part 5| May 2012| Pages o1336-o1337

doi:10.1107/S160053681201433X

Open

access

Format		BIBTeX
		EndNote
		RefMan
		Refer
		Medline
		CIF
		SGML
		Plain Text

Format		BIBTeX
		EndNote
		RefMan
		Refer
		Medline
		CIF
		SGML
		Plain Text

Search IUCr Journals		doi		Advanced search
Author		volume	page

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

N′-(3-Bromo-5-chloro-2-hy­dr­oxy­benzyl­­idene)-2H-1,3-benzodioxole-5-carbo­hydrazide

Related literature

Experimental

Crystal data

Data collection

Refinement

Supporting information

Acknowledgements

References

organic compounds

N′-(3-Bromo-5-chloro-2-hydroxybenzylidene)-2H-1,3-benzodioxole-5-carbohydrazide