(E)-4-Amino-N′-(5-chloro-2-hy­droxy­benzyl­idene)benzohydrazide

Shi, Z.-F.; Li, J.-M.

doi:10.1107/S160053681201803X

organic compounds

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ISSN: 2056-9890

Volume 68| Part 5| May 2012| Pages o1546-o1547

doi:10.1107/S160053681201803X

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(E)-4-Amino-N′-(5-chloro-2-hydroxybenzylidene)benzohydrazide

Zhong-Feng Shi ^a,^b and Jia-Ming Li ^a ^*

^aCollege of Chemistry and Chemical Engineering, Qinzhou University, Qinzhou, Guangxi 535000, People's Republic of China, and ^bGuangxi Key Laboratory of Petrochemical Resource Processing and Process Intensification Technology, Guangxi University, Nanning, Guangxi 530004, People's Republic of China
^*Correspondence e-mail: ljmmarise@163.com

(Received 21 April 2012; accepted 23 April 2012; online 28 April 2012)

The title compound, C₁₄H₁₂ClN₃O₂, displays an E conformation with respect to the C=N double bond. The dihedral angle between the benzene rings is 41.3 (5)°. The molecular structure is stabilized by an intramolecular O—H⋯N hydrogen bond. In the crystal, N—H⋯O and weak N—H⋯Cl hydrogen bonds link the molecules into a three-dimensional architecture. In addition, there are weak C—H⋯π stacking interactions.

Related literature

For the biological properties of Schiff base and hydrazone compounds, see: Kucukguzel et al. (2006 ); Khattab (2005 ); Karthikeyan et al. (2006 ). For closely related structures and background references, see: Bernhardt et al. (2003 , 2005 ); Armstrong et al. (2003 ); Cao (2009 ); Yang (2009 ); Zhou & Yang (2010 ); Zhang et al., (2009 ).

Experimental

Crystal data

C₁₄H₁₂ClN₃O₂
M_r = 289.72
Orthorhombic, P n a 2₁
a = 9.3375 (16) Å
b = 9.7194 (16) Å
c = 14.214 (3) Å
V = 1290.0 (4) Å³
Z = 4
Mo Kα radiation
μ = 0.30 mm⁻¹
T = 296 K
0.20 × 0.15 × 0.10 mm

Data collection

Bruker SMART CCD area-detector diffractometer
Absorption correction: multi-scan (SADABS; Sheldrick, 1996 ) T_min = 0.947, T_max = 0.970
8516 measured reflections
2944 independent reflections
2866 reflections with I > 2σ(I)
R_int = 0.038

Refinement

R[F² > 2σ(F²)] = 0.033
wR(F²) = 0.084
S = 1.10
2944 reflections
182 parameters
H-atom parameters constrained
Δρ_max = 0.36 e Å⁻³
Δρ_min = −0.16 e Å⁻³
Absolute structure: Flack (1983 ), 1407 Friedel pairs
Flack parameter: 0.09 (9)

Table 1
Hydrogen-bond geometry (Å, °)

Cg1 and Cg2 are the centroids of the C1–C6 and C9–C14 rings, respectively.

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
N2—H2A⋯O1ⁱ	0.86	2.12	2.921 (2)	156
N1—H1A⋯Cl1ⁱⁱ	0.86	2.94	3.680 (2)	145
N1—H1B⋯O1ⁱⁱⁱ	0.86	2.19	2.978 (3)	151
O2—H2⋯N3	0.82	1.88	2.588 (3)	145
C5—H5⋯Cg2^iv	0.93	2.92	3.473 (3)	120
C14—H14⋯Cg1^v	0.93	2.83	3.641 (3)	147
Symmetry codes: (i) $[x-{\script{1\over 2}}, -y+{\script{3\over 2}}, z]$ ; (ii) x, y, z-1; (iii) $[-x+2, -y+1, z-{\script{1\over 2}}]$ ; (iv) $[-x+2, -y+2, z-{\script{1\over 2}}]$ ; (v) $[x+{\script{3\over 2}}, -y+{\script{1\over 2}}, z]$ .

Data collection: SMART (Bruker, 2007 ); cell refinement: SAINT (Bruker, 2007); 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/S160053681201803X/tk5088sup1.cif

Structure factors: contains datablock I. DOI: 10.1107/S160053681201803X/tk5088Isup2.hkl

Supporting information file. DOI: 10.1107/S160053681201803X/tk5088Isup3.cml

checkCIF report

Comment top

Schiff bases are an important class of compounds in the medicinal and pharmaceutical fields and have been found to play a role in the development of coordination chemistry as they readily form stable complexes with most transition metals. These complexes show interesting properties, e.g. their ability to reversibly bind oxygen, catalytic activity in hydrogenation of olefins and transfer of an amino group, photochromic properties, and complexing ability towards toxic metals (Karthikeyan et al., 2006; Khattab, 2005; Kucukguzel et al., 2006). Recently, hydrazone Schiff base compounds (Cao, 2009; Yang, 2009; Zhou & Yang, 2010; Zhang et al., 2009) derived from the reaction of aldehydes with hydrazines have been demonstrated to possess excellent biological activities, such as anti-bacterial, anti-convulsant, and anti-tubercular (Bernhardt & Caldwell et al., 2003; Bernhardt & Chin et al., 2005; Armstrong et al., 2003). In order to explore new anti-bacterial materials, a new hydrazone derivatives was prepared and characterized. It can be seen that in addition to the presence of the typical functional group —CO—NH—N═ CH—, the compound has chloro, hydroxy and amino substituents, which may enhance its biological properties.

As shown in Fig. 1, the molecule displays an E configuration with respect to the C═N double bond. The dihedral angle between the two benzene rings is 41.3 (5)°. The bond lengths and angles are as expected for a compound of this type and agree with the other ligands belonging to the hydrazone series, mentioned above. The C8═N3 and C7═O1 bond lengths of 1.287 (3) and 1.238 (3) Å, respectively, conform to the values for double bonds. Whereas the C1—N1, C7—N2, C10—O2 and N2—N3 [1.367 (3), 1.370 (3), 1.355 (3) and 1.368 (3) Å, respectively] bond lengths correspond to a single bond. In the crystal packing, it is noted that amino H (H1A, H1B) and amide H2A are involved in forming intermolecular N—H···O and N—H···Cl hydrogen bonds (Fig. 2 and Table 1), linking the molecules into a three-dimensional supramolecular structure. In addition, neighbouring molecules are also interact through weak C—H···π stacking interactions, Table 1.

Related literature top

For the biological properties of Schiff base and hydrazone compounds, see: Kucukguzel et al. (2006); Khattab (2005); Karthikeyan et al. (2006). For closely related structures and background references, see: Bernhardt et al. (2003, 2005); Armstrong et al. (2003); Cao (2009); Yang (2009); Zhou & Yang (2010); Zhang et al., (2009).

Experimental top

To a methanol solution (20 ml) of 5-chloro-2-hydroxybenzaldehyde (1 mmol, 0.157 g) and 4-aminobenzohydrazide (1 mmol, 0.151 g), a few drops of acetic acid were added. The mixture was refluxed for 2 h and then cooled to room temperature to give a yellow solution. Crystals of the title compound were formed by gradual evaporation of the solvent over a period of six days at room temperature.

Computing details top

Data collection: SMART (Bruker, 2007); cell refinement: SAINT (Bruker, 2007); data reduction: SAINT (Bruker, 2007); 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, with displacement ellipsoids at the 30% probability level.
	Fig. 2. Crystal packing in the title compound where molecules are linked via N—H···O and N—H···Cl hydrogen bonds (dashed lines). Except for those involved in hydrogen-bonding interactions, H atoms have been omitted for clarity.

(E)-4-Amino-N'-(5-chloro-2-hydroxybenzylidene)benzohydrazide top

Crystal data top

C₁₄H₁₂ClN₃O₂	F(000) = 600
M_r = 289.72	D_x = 1.487 Mg m⁻³
Orthorhombic, Pna2₁	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: P 2c -2n	Cell parameters from 6341 reflections
a = 9.3375 (16) Å	θ = 1.4–27.5°
b = 9.7194 (16) Å	µ = 0.30 mm⁻¹
c = 14.214 (3) Å	T = 296 K
V = 1290.0 (4) Å³	Block, yellow
Z = 4	0.20 × 0.15 × 0.10 mm

Data collection top

Bruker SMART CCD area-detector diffractometer	2944 independent reflections
Radiation source: fine-focus sealed tube	2866 reflections with I > 2σ(I)
Graphite monochromator	R_int = 0.038
ϕ and ω scans	θ_max = 27.5°, θ_min = 2.5°
Absorption correction: multi-scan (SADABS; Sheldrick, 1996)	h = −11→12
T_min = 0.947, T_max = 0.970	k = −12→9
8516 measured reflections	l = −18→18

Refinement top

Refinement on F²	Secondary atom site location: difference Fourier map
Least-squares matrix: full	Hydrogen site location: inferred from neighbouring sites
R[F² > 2σ(F²)] = 0.033	H-atom parameters constrained
wR(F²) = 0.084	w = 1/[σ²(F_o²) + (0.0553P)² + 0.2086P] where P = (F_o² + 2F_c²)/3
S = 1.10	(Δ/σ)_max < 0.001
2944 reflections	Δρ_max = 0.36 e Å⁻³
182 parameters	Δρ_min = −0.16 e Å⁻³
0 restraints	Absolute structure: Flack (1983), 1407 Friedel pairs
Primary atom site location: structure-invariant direct methods	Absolute structure parameter: 0.09 (9)

Crystal data top

C₁₄H₁₂ClN₃O₂	V = 1290.0 (4) Å³
M_r = 289.72	Z = 4
Orthorhombic, Pna2₁	Mo Kα radiation
a = 9.3375 (16) Å	µ = 0.30 mm⁻¹
b = 9.7194 (16) Å	T = 296 K
c = 14.214 (3) Å	0.20 × 0.15 × 0.10 mm

Data collection top

Bruker SMART CCD area-detector diffractometer	2944 independent reflections
Absorption correction: multi-scan (SADABS; Sheldrick, 1996)	2866 reflections with I > 2σ(I)
T_min = 0.947, T_max = 0.970	R_int = 0.038
8516 measured reflections

Refinement top

R[F² > 2σ(F²)] = 0.033	H-atom parameters constrained
wR(F²) = 0.084	Δρ_max = 0.36 e Å⁻³
S = 1.10	Δρ_min = −0.16 e Å⁻³
2944 reflections	Absolute structure: Flack (1983), 1407 Friedel pairs
182 parameters	Absolute structure parameter: 0.09 (9)
0 restraints

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 > 2sigma(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
Cl1	0.75084 (6)	0.97018 (6)	0.79216 (7)	0.03468 (17)
O1	1.14409 (16)	0.65129 (17)	0.27805 (12)	0.0267 (4)
O2	1.19222 (18)	0.8254 (2)	0.51735 (12)	0.0343 (4)
H2	1.1593	0.8184	0.4641	0.051*
N1	0.8561 (3)	0.6238 (2)	−0.12949 (16)	0.0377 (5)
H1A	0.7980	0.6813	−0.1551	0.045*
H1B	0.8867	0.5542	−0.1610	0.045*
N2	0.94718 (19)	0.78349 (19)	0.30263 (14)	0.0224 (4)
H2A	0.8682	0.8164	0.2816	0.027*
N3	0.9907 (2)	0.8088 (2)	0.39290 (13)	0.0224 (4)
C1	0.8999 (2)	0.6432 (2)	−0.03874 (17)	0.0262 (5)
C2	0.9933 (3)	0.5508 (2)	0.00555 (18)	0.0270 (5)
H2B	1.0272	0.4748	−0.0273	0.032*
C3	1.0352 (2)	0.5718 (2)	0.09760 (17)	0.0255 (5)
H3	1.0982	0.5103	0.1257	0.031*
C4	0.9840 (2)	0.6846 (2)	0.14908 (16)	0.0220 (4)
C5	0.8906 (3)	0.7754 (3)	0.10492 (17)	0.0286 (5)
H5	0.8548	0.8503	0.1382	0.034*
C6	0.8504 (3)	0.7562 (3)	0.01244 (17)	0.0308 (5)
H6	0.7895	0.8193	−0.0161	0.037*
C7	1.0335 (2)	0.7040 (2)	0.24690 (16)	0.0220 (4)
C8	0.9037 (2)	0.8682 (2)	0.45000 (17)	0.0239 (5)
H8	0.8149	0.8985	0.4294	0.029*
C9	0.9471 (2)	0.8871 (2)	0.54757 (16)	0.0230 (4)
C10	1.0863 (2)	0.8585 (2)	0.57817 (17)	0.0247 (5)
C11	1.1199 (2)	0.8632 (2)	0.67355 (18)	0.0274 (5)
H11	1.2124	0.8434	0.6930	0.033*
C12	1.0177 (3)	0.8968 (2)	0.73943 (16)	0.0268 (5)
H12	1.0402	0.8979	0.8031	0.032*
C13	0.8807 (3)	0.9291 (2)	0.70915 (17)	0.0256 (5)
C14	0.8452 (3)	0.9260 (2)	0.61485 (16)	0.0253 (5)
H14	0.7534	0.9497	0.5959	0.030*

Atomic displacement parameters (Å²) top

	U¹¹	U²²	U³³	U¹²	U¹³	U²³
Cl1	0.0388 (3)	0.0439 (3)	0.0213 (3)	0.0096 (2)	0.0028 (2)	−0.0028 (3)
O1	0.0207 (7)	0.0360 (8)	0.0235 (9)	0.0020 (6)	−0.0044 (6)	0.0024 (7)
O2	0.0268 (9)	0.0562 (11)	0.0198 (8)	0.0067 (8)	−0.0026 (7)	0.0004 (8)
N1	0.0550 (14)	0.0359 (11)	0.0221 (11)	0.0034 (10)	−0.0080 (10)	−0.0054 (9)
N2	0.0218 (8)	0.0301 (9)	0.0155 (8)	0.0004 (7)	−0.0036 (7)	0.0002 (7)
N3	0.0232 (9)	0.0287 (9)	0.0152 (8)	−0.0022 (7)	−0.0037 (7)	0.0020 (7)
C1	0.0289 (11)	0.0308 (12)	0.0188 (10)	−0.0055 (9)	−0.0003 (8)	0.0001 (9)
C2	0.0284 (11)	0.0270 (10)	0.0254 (11)	0.0000 (9)	0.0027 (9)	−0.0042 (10)
C3	0.0228 (10)	0.0289 (11)	0.0247 (12)	0.0021 (9)	−0.0020 (9)	−0.0010 (9)
C4	0.0227 (10)	0.0267 (10)	0.0166 (10)	−0.0023 (8)	−0.0013 (8)	−0.0002 (8)
C5	0.0374 (12)	0.0291 (11)	0.0195 (11)	0.0054 (9)	−0.0026 (9)	−0.0010 (9)
C6	0.0403 (14)	0.0317 (11)	0.0206 (11)	0.0065 (10)	−0.0077 (10)	0.0004 (9)
C7	0.0236 (10)	0.0239 (10)	0.0185 (11)	−0.0033 (8)	−0.0003 (9)	0.0029 (8)
C8	0.0235 (10)	0.0288 (11)	0.0195 (11)	−0.0007 (8)	−0.0047 (8)	0.0018 (9)
C9	0.0271 (11)	0.0239 (10)	0.0180 (10)	−0.0009 (8)	−0.0033 (8)	0.0010 (9)
C10	0.0263 (11)	0.0274 (10)	0.0205 (11)	0.0000 (8)	−0.0032 (9)	−0.0010 (9)
C11	0.0258 (11)	0.0325 (11)	0.0239 (12)	0.0019 (9)	−0.0093 (9)	−0.0012 (9)
C12	0.0360 (12)	0.0299 (11)	0.0146 (10)	0.0002 (9)	−0.0062 (9)	−0.0001 (9)
C13	0.0322 (12)	0.0248 (10)	0.0197 (11)	0.0011 (8)	0.0015 (9)	−0.0022 (9)
C14	0.0252 (11)	0.0293 (10)	0.0215 (11)	0.0019 (9)	−0.0033 (8)	0.0009 (9)

Geometric parameters (Å, º) top

Cl1—C13	1.741 (2)	C4—C5	1.392 (3)
O1—C7	1.235 (2)	C4—C7	1.479 (3)
O2—C10	1.355 (3)	C5—C6	1.381 (3)
O2—H2	0.8200	C5—H5	0.9300
N1—C1	1.367 (3)	C6—H6	0.9300
N1—H1A	0.8600	C8—C9	1.458 (3)
N1—H1B	0.8600	C8—H8	0.9300
N2—N3	1.369 (3)	C9—C10	1.399 (3)
N2—C7	1.370 (3)	C9—C14	1.403 (3)
N2—H2A	0.8600	C10—C11	1.393 (3)
N3—C8	1.287 (3)	C11—C12	1.378 (3)
C1—C6	1.396 (3)	C11—H11	0.9300
C1—C2	1.402 (3)	C12—C13	1.390 (3)
C2—C3	1.382 (3)	C12—H12	0.9300
C2—H2B	0.9300	C13—C14	1.382 (3)
C3—C4	1.402 (3)	C14—H14	0.9300
C3—H3	0.9300

C10—O2—H2	109.5	C1—C6—H6	119.6
C1—N1—H1A	120.0	O1—C7—N2	121.3 (2)
C1—N1—H1B	120.0	O1—C7—C4	123.1 (2)
H1A—N1—H1B	120.0	N2—C7—C4	115.54 (19)
N3—N2—C7	117.90 (19)	N3—C8—C9	118.7 (2)
N3—N2—H2A	121.1	N3—C8—H8	120.6
C7—N2—H2A	121.1	C9—C8—H8	120.6
C8—N3—N2	118.93 (19)	C10—C9—C14	118.3 (2)
N1—C1—C6	120.1 (2)	C10—C9—C8	122.0 (2)
N1—C1—C2	121.5 (2)	C14—C9—C8	119.6 (2)
C6—C1—C2	118.4 (2)	O2—C10—C11	117.7 (2)
C3—C2—C1	120.6 (2)	O2—C10—C9	122.0 (2)
C3—C2—H2B	119.7	C11—C10—C9	120.4 (2)
C1—C2—H2B	119.7	C12—C11—C10	120.9 (2)
C2—C3—C4	120.8 (2)	C12—C11—H11	119.6
C2—C3—H3	119.6	C10—C11—H11	119.6
C4—C3—H3	119.6	C11—C12—C13	119.0 (2)
C5—C4—C3	118.3 (2)	C11—C12—H12	120.5
C5—C4—C7	122.7 (2)	C13—C12—H12	120.5
C3—C4—C7	118.9 (2)	C14—C13—C12	121.2 (2)
C6—C5—C4	121.0 (2)	C14—C13—Cl1	119.69 (19)
C6—C5—H5	119.5	C12—C13—Cl1	119.13 (18)
C4—C5—H5	119.5	C13—C14—C9	120.3 (2)
C5—C6—C1	120.8 (2)	C13—C14—H14	119.9
C5—C6—H6	119.6	C9—C14—H14	119.9

C7—N2—N3—C8	−171.4 (2)	N2—N3—C8—C9	176.14 (19)
N1—C1—C2—C3	−179.5 (2)	N3—C8—C9—C10	8.1 (3)
C6—C1—C2—C3	−0.2 (4)	N3—C8—C9—C14	−167.4 (2)
C1—C2—C3—C4	0.9 (4)	C14—C9—C10—O2	−177.5 (2)
C2—C3—C4—C5	−0.5 (3)	C8—C9—C10—O2	6.9 (3)
C2—C3—C4—C7	−179.1 (2)	C14—C9—C10—C11	2.7 (3)
C3—C4—C5—C6	−0.7 (4)	C8—C9—C10—C11	−172.9 (2)
C7—C4—C5—C6	177.9 (2)	O2—C10—C11—C12	179.7 (2)
C4—C5—C6—C1	1.4 (4)	C9—C10—C11—C12	−0.4 (4)
N1—C1—C6—C5	178.3 (2)	C10—C11—C12—C13	−1.4 (4)
C2—C1—C6—C5	−1.0 (4)	C11—C12—C13—C14	1.0 (4)
N3—N2—C7—O1	3.3 (3)	C11—C12—C13—Cl1	179.46 (18)
N3—N2—C7—C4	−177.71 (18)	C12—C13—C14—C9	1.3 (4)
C5—C4—C7—O1	−158.2 (2)	Cl1—C13—C14—C9	−177.17 (17)
C3—C4—C7—O1	20.4 (3)	C10—C9—C14—C13	−3.1 (3)
C5—C4—C7—N2	22.8 (3)	C8—C9—C14—C13	172.6 (2)
C3—C4—C7—N2	−158.6 (2)

Hydrogen-bond geometry (Å, º) top

Cg1 and Cg2 are the centroids of the C1–C6 and C9–C14 rings, respectively.

D—H···A	D—H	H···A	D···A	D—H···A
N2—H2A···O1ⁱ	0.86	2.12	2.921 (2)	156
N1—H1A···Cl1ⁱⁱ	0.86	2.94	3.680 (2)	145
N1—H1B···O1ⁱⁱⁱ	0.86	2.19	2.978 (3)	151
O2—H2···N3	0.82	1.88	2.588 (3)	145
C5—H5···Cg2^iv	0.93	2.92	3.473 (3)	120
C14—H14···Cg1^v	0.93	2.83	3.641 (3)	147

Symmetry codes: (i) x−1/2, −y+3/2, z; (ii) x, y, z−1; (iii) −x+2, −y+1, z−1/2; (iv) −x+2, −y+2, z−1/2; (v) x+3/2, −y+1/2, z.

Experimental details

Crystal data
Chemical formula	C₁₄H₁₂ClN₃O₂
M_r	289.72
Crystal system, space group	Orthorhombic, Pna2₁
Temperature (K)	296
a, b, c (Å)	9.3375 (16), 9.7194 (16), 14.214 (3)
V (Å³)	1290.0 (4)
Z	4
Radiation type	Mo Kα
µ (mm⁻¹)	0.30
Crystal size (mm)	0.20 × 0.15 × 0.10

Data collection
Diffractometer	Bruker SMART CCD area-detector diffractometer
Absorption correction	Multi-scan (SADABS; Sheldrick, 1996)
T_min, T_max	0.947, 0.970
No. of measured, independent and observed [I > 2σ(I)] reflections	8516, 2944, 2866
R_int	0.038
(sin θ/λ)_max (Å⁻¹)	0.649

Refinement
R[F² > 2σ(F²)], wR(F²), S	0.033, 0.084, 1.10
No. of reflections	2944
No. of parameters	182
H-atom treatment	H-atom parameters constrained
Δρ_max, Δρ_min (e Å⁻³)	0.36, −0.16
Absolute structure	Flack (1983), 1407 Friedel pairs
Absolute structure parameter	0.09 (9)

Computer programs: SMART (Bruker, 2007), SAINT (Bruker, 2007), SHELXS97 (Sheldrick, 2008), SHELXL97 (Sheldrick, 2008), SHELXTL (Sheldrick, 2008).

Hydrogen-bond geometry (Å, º) top

Cg1 and Cg2 are the centroids of the C1–C6 and C9–C14 rings, respectively.

D—H···A	D—H	H···A	D···A	D—H···A
N2—H2A···O1ⁱ	0.86	2.12	2.921 (2)	156.1
N1—H1A···Cl1ⁱⁱ	0.86	2.94	3.680 (2)	145.4
N1—H1B···O1ⁱⁱⁱ	0.86	2.19	2.978 (3)	151.3
O2—H2···N3	0.82	1.88	2.588 (3)	145
C5—H5···Cg2^iv	0.93	2.92	3.473 (3)	120
C14—H14···Cg1^v	0.93	2.83	3.641 (3)	147

Symmetry codes: (i) x−1/2, −y+3/2, z; (ii) x, y, z−1; (iii) −x+2, −y+1, z−1/2; (iv) −x+2, −y+2, z−1/2; (v) x+3/2, −y+1/2, z.

Acknowledgements

This work was supported by the Natural Science Foundation of Guangxi Province (grant No. 2011GXNSFB018023) and the Natural Science Foundation of Education Bureau of Guangxi Province (grant No. 201106LX535). This work was also supported by the Program for Excellent Talents in Guangxi Higher Education Institutions and the Dean Project of Guangxi Key Laboratory of Petrochemical Resource Processing and Process Intensification Technology (grant No. K011).

References

Armstrong, C. M., Bernhardt, P. V., Chin, P. & Richardson, D. R. (2003). Eur. J. Inorg. Chem. pp. 1145–1156. CSD CrossRef Google Scholar
Bernhardt, P. V., Caldwell, L. M., Chaston, T. B., Chin, P. & Richardson, D. R. (2003). J. Biol. Inorg. Chem. 8, 866–880. Web of Science CSD CrossRef PubMed CAS Google Scholar
Bernhardt, P. V., Chin, P., Sharpe, P. C., Wang, J. Y. C. & Richardson, D. R. (2005). J. Biol. Inorg. Chem. 10, 761–777. Web of Science CSD CrossRef PubMed CAS Google Scholar
Bruker (2007). SMART and SAINT. Bruker AXS Inc., Madison, Wisconsin, USA. Google Scholar
Cao, G.-B. (2009). Acta Cryst. E65, o2415. Web of Science CSD CrossRef IUCr Journals Google Scholar
Flack, H. D. (1983). Acta Cryst. A39, 876–881. CrossRef CAS Web of Science IUCr Journals Google Scholar
Karthikeyan, M. S., Prasad, D. J., Poojary, B., Bhat, K. S., Holla, B. S. & Kumari, N. S. (2006). Bioorg. Med. Chem. 14, 7482–7489. Web of Science CrossRef PubMed CAS Google Scholar
Khattab, S. N. (2005). Molecules, 10, 1218–1228. Web of Science CrossRef PubMed CAS Google Scholar
Kucukguzel, G., Kocatepe, A., De Clercq, E., Sahi, F. & Gulluce, M. (2006). Eur. J. Med. Chem. 41, 353–359. Web of Science CrossRef PubMed Google Scholar
Sheldrick, G. M. (1996). SADABS. University of Göttingen, Germany. Google Scholar
Sheldrick, G. M. (2008). Acta Cryst. A64, 112–122. Web of Science CrossRef CAS IUCr Journals Google Scholar
Yang, D.-S. (2009). Acta Cryst. E65, o2864. Web of Science CrossRef IUCr Journals Google Scholar
Zhang, M.-J., Yin, L.-Z., Wang, D.-C., Deng, X.-M. & Liu, J.-B. (2009). Acta Cryst. E65, o508. Web of Science CSD CrossRef IUCr Journals Google Scholar
Zhou, C.-S. & Yang, T. (2010). Acta Cryst. E66, o365. Web of Science CSD CrossRef IUCr Journals Google Scholar

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Volume 68| Part 5| May 2012| Pages o1546-o1547

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