(E)-N′-(3,4-Dihydroxy­benzyl­idene)-4-nitro­benzohydrazide

Qiu, F.; He, X.-J.; Sun, Y.-X.; Zhu, X.

doi:10.1107/S1600536809029705

organic compounds

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ISSN: 2056-9890

Volume 65| Part 8| August 2009| Page o2050

doi:10.1107/S1600536809029705

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(E)-N′-(3,4-Dihydroxybenzylidene)-4-nitrobenzohydrazide

Feng Qiu,^a ^* Xiao-Jing He,^a Ya-Xin Sun ^a and Xu Zhu ^a

^aShengjing Hospital of China Medical University, Shenyang 110004, People's Republic of China
^*Correspondence e-mail: ydqiufeng@126.com

(Received 22 July 2009; accepted 26 July 2009; online 31 July 2009)

In the title Schiff base compound, C₁₄H₁₁N₃O₅, the dihedral angle between the two benzene rings is 1.6 (1)°. The molecule displays an E configuration about the C=N bond. An intramolecular O—H⋯O hydrogen bond is observed. In the crystal, molecules are linked into layers parallel to (101) by O—H⋯O, N—H⋯O and C—H⋯O hydrogen bonds. One of the hydroxyl groups is disordered over two positions, with occupancies of 0.643 (5) and 0.357 (5).

Related literature

For the biological properties of Schiff base compounds, see: Kucukguzel et al. (2006 ); Khattab (2005 ); Karthikeyan et al. (2006 ); Okabe et al. (1993 ). For bond-length data, see: Allen et al. (1987 ). For related structures, see: Shan et al. (2008 ); Fun et al. (2008 ); Yang (2008 ); Ma et al. (2008 ); Diao et al. (2008a ,b ); Ejsmont et al. (2008 ); Qiu & Zhao (2008 ).

Experimental

Crystal data

C₁₄H₁₁N₃O₅
M_r = 301.26
Monoclinic, P 2₁ /c
a = 7.666 (1) Å
b = 13.196 (2) Å
c = 13.176 (2) Å
β = 95.361 (3)°
V = 1327.1 (3) Å³
Z = 4
Mo Kα radiation
μ = 0.12 mm⁻¹
T = 298 K
0.20 × 0.20 × 0.18 mm

Data collection

Bruker SMART CCD area-detector diffractometer
Absorption correction: multi-scan (SADABS; Bruker, 2001 ) T_min = 0.977, T_max = 0.979
8322 measured reflections
3204 independent reflections
1364 reflections with I > 2σ(I)
R_int = 0.056

Refinement

R[F² > 2σ(F²)] = 0.069
wR(F²) = 0.161
S = 1.02
3204 reflections
210 parameters
2 restraints
H-atom parameters constrained
Δρ_max = 0.17 e Å⁻³
Δρ_min = −0.23 e Å⁻³

Table 1
Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
O3—H3A⋯O2	0.82	2.17	2.636 (4)	116
O2—H2A⋯O1ⁱ	0.82	1.91	2.722 (3)	171
O3′—H3′⋯O1ⁱ	0.82	1.84	2.548 (7)	144
N2—H2B⋯O4ⁱⁱ	0.90	2.26	3.121 (3)	158
C5—H5⋯O5ⁱⁱ	0.93	2.48	3.210 (4)	135
C10—H10⋯O2ⁱⁱⁱ	0.93	2.58	3.467 (3)	159
C11—H11⋯O1ⁱ	0.93	2.56	3.192 (4)	126
Symmetry codes: (i) $[-x+1, y-{\script{1\over 2}}, -z+{\script{1\over 2}}]$ ; (ii) $[-x+2, y-{\script{1\over 2}}, -z-{\script{1\over 2}}]$ ; (iii) $[-x+1, y+{\script{1\over 2}}, -z+{\script{1\over 2}}]$ .

Data collection: SMART (Bruker, 2007 ); cell refinement: SAINT (Bruker, 2007); data reduction: SAINT; program(s) used to solve structure: SHELXTL (Sheldrick, 2008 ); program(s) used to refine structure: SHELXTL; molecular graphics: SHELXTL; software used to prepare material for publication: SHELXTL.

Supporting information

Crystal structure: contains datablocks global, I. DOI: 10.1107/S1600536809029705/ci2865sup1.cif

Structure factors: contains datablock I. DOI: 10.1107/S1600536809029705/ci2865Isup2.hkl

checkCIF report

Comment top

Hydrazones and Schiff bases have been attracted much attention for their excellent biological properties, especially for their potential pharmacological and antitumor properties (Kucukguzel et al., 2006; Khattab et al., 2005; Karthikeyan et al., 2006; Okabe et al., 1993). Recently, a large number of hydrazone derivatives have been prepared and structurally characterized (Shan et al., 2008; Fun et al., 2008; Yang, 2008; Ma et al., 2008; Diao et al., 2008a,b; Ejsmont et al., 2008). As part of the ongoing study (Qiu & Zhao, 2008), we report herein the crystal structure of the title compound.

The molecular structure of the title compound is shown in Fig. 1. The bond distances (Allen et al., 1987) and angles are normal. The dihedral angle between the two benzene rings is 1.6 (1)°. The displays an E configuration about the C═N bond. The nitro group is almost coplanar with the attached benzene ring [O4—N1—C1—C6 = -3.5 (5)° and O5—N1—C1—C2 = -3.1 (5)°].

The molecules are linked into layers parallel to the (101) by O—H···O, N—H···O and C—H···O hydrogen bonds (Fig. 2 and Table 1).

Related literature top

For the biological properties of Schiff base compounds, see: Kucukguzel et al. (2006); Khattab et al. (2005); Karthikeyan et al. (2006); Okabe et al. (1993). For bond-length data, see: Allen et al. (1987). For related structures, see: Shan et al. (2008); Fun et al. (2008); Yang (2008); Ma et al. (2008); Diao et al. (2008a,b); Ejsmont et al. (2008); Qiu & Zhao (2008).

Experimental top

3,4-Dihydroxybenzaldehyde (1.0 mmol, 138.1 mg) was dissolved in methanol (50 ml), then 4-nitrobenzohydrazide (1.0 mmol, 181.2 mg) was added slowly into the solution, and the mixture was kept at reflux with continuous stirring for 3 h. After the solution had cooled to room temperature colourless tiny crystals appeared. The tiny crystals were filtered and washed with methanol for three times. Recrystallization from an absolute methanol yielded block-shaped single crystals of the title compound.

Computing details top

Data collection: SMART (Bruker, 2007); cell refinement: SAINT (Bruker, 2007); data reduction: SAINT (Bruker, 2007); program(s) used to solve structure: SHELXTL (Sheldrick, 2008); program(s) used to refine structure: SHELXTL (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 30% probability displacement ellipsoids for non-H atoms. Only the major disorder component of a hydroxyl group is shown.
	Fig. 2. Molecular packing as viewed along the a axis. O—H···O and N—H···O hydrogen bonds are shown as dashed lines.

(E)-N'-(3,4-Dihydroxybenzylidene)-4-nitrobenzohydrazide top

Crystal data top

C₁₄H₁₁N₃O₅	F(000) = 624
M_r = 301.26	D_x = 1.508 Mg m⁻³
Monoclinic, P2₁/c	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: -P 2ybc	Cell parameters from 1038 reflections
a = 7.666 (1) Å	θ = 2.5–24.5°
b = 13.196 (2) Å	µ = 0.12 mm⁻¹
c = 13.176 (2) Å	T = 298 K
β = 95.361 (3)°	Block, colourless
V = 1327.1 (3) Å³	0.20 × 0.20 × 0.18 mm
Z = 4

Data collection top

Bruker SMART CCD area-detector diffractometer	3204 independent reflections
Radiation source: fine-focus sealed tube	1364 reflections with I > 2σ(I)
Graphite monochromator	R_int = 0.056
ω scans	θ_max = 28.3°, θ_min = 2.2°
Absorption correction: multi-scan (SADABS; Bruker, 2001)	h = −10→10
T_min = 0.977, T_max = 0.979	k = −16→17
8322 measured reflections	l = −17→10

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)] = 0.069	Hydrogen site location: inferred from neighbouring sites
wR(F²) = 0.161	H-atom parameters constrained
S = 1.02	w = 1/[σ²(F_o²) + (0.0491P)² + 0.4176P] where P = (F_o² + 2F_c²)/3
3204 reflections	(Δ/σ)_max = 0.001
210 parameters	Δρ_max = 0.17 e Å⁻³
2 restraints	Δρ_min = −0.23 e Å⁻³

Crystal data top

C₁₄H₁₁N₃O₅	V = 1327.1 (3) Å³
M_r = 301.26	Z = 4
Monoclinic, P2₁/c	Mo Kα radiation
a = 7.666 (1) Å	µ = 0.12 mm⁻¹
b = 13.196 (2) Å	T = 298 K
c = 13.176 (2) Å	0.20 × 0.20 × 0.18 mm
β = 95.361 (3)°

Data collection top

Bruker SMART CCD area-detector diffractometer	3204 independent reflections
Absorption correction: multi-scan (SADABS; Bruker, 2001)	1364 reflections with I > 2σ(I)
T_min = 0.977, T_max = 0.979	R_int = 0.056
8322 measured reflections

Refinement top

R[F² > 2σ(F²)] = 0.069	2 restraints
wR(F²) = 0.161	H-atom parameters constrained
S = 1.02	Δρ_max = 0.17 e Å⁻³
3204 reflections	Δρ_min = −0.23 e Å⁻³
210 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 > 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	Occ. (<1)
O1	0.6818 (3)	1.15446 (15)	0.09056 (17)	0.0606 (6)
O2	0.5123 (3)	0.56081 (15)	0.27427 (16)	0.0661 (7)
H2A	0.4520	0.5825	0.3177	0.099*
O3	0.6235 (5)	0.5128 (2)	0.0971 (3)	0.0814 (15)	0.643 (5)
H3A	0.6013	0.4782	0.1460	0.122*	0.643 (5)
O4	1.0449 (3)	1.43595 (18)	−0.3087 (2)	0.0749 (7)
O5	0.9668 (4)	1.5401 (2)	−0.1968 (2)	0.1037 (10)
N1	0.9797 (4)	1.4543 (2)	−0.2301 (2)	0.0648 (8)
N2	0.7625 (3)	1.03529 (18)	−0.01803 (18)	0.0508 (7)
H2B	0.7895	1.0090	−0.0778	0.061*
N3	0.7082 (3)	0.9614 (2)	0.04686 (19)	0.0524 (7)
C1	0.9174 (4)	1.3697 (2)	−0.1705 (2)	0.0513 (8)
C2	0.8561 (4)	1.3914 (2)	−0.0783 (3)	0.0601 (9)
H2	0.8517	1.4579	−0.0552	0.072*
C3	0.8013 (4)	1.3123 (2)	−0.0209 (2)	0.0572 (9)
H3	0.7599	1.3255	0.0419	0.069*
C4	0.8072 (4)	1.2134 (2)	−0.0558 (2)	0.0438 (7)
C5	0.8690 (4)	1.1948 (2)	−0.1500 (2)	0.0521 (8)
H5	0.8723	1.1288	−0.1745	0.063*
C6	0.9252 (4)	1.2736 (2)	−0.2070 (2)	0.0558 (9)
H6	0.9679	1.2613	−0.2696	0.067*
C7	0.7446 (4)	1.1325 (2)	0.0104 (2)	0.0475 (8)
C8	0.7224 (4)	0.8695 (2)	0.0199 (2)	0.0501 (8)
H8	0.7655	0.8536	−0.0418	0.060*
C9	0.6702 (4)	0.7893 (2)	0.0869 (2)	0.0468 (8)
C10	0.6126 (4)	0.8135 (2)	0.1810 (2)	0.0522 (9)
H10	0.6094	0.8811	0.2008	0.063*
C11	0.5601 (4)	0.7403 (2)	0.2447 (2)	0.0544 (9)
H11	0.5232	0.7582	0.3076	0.065*	0.643 (5)
C12	0.5617 (4)	0.6395 (2)	0.2157 (2)	0.0480 (8)
C13	0.6193 (4)	0.6140 (2)	0.1230 (2)	0.0532 (8)
H13	0.6224	0.5464	0.1034	0.064*	0.357 (5)
C14	0.6724 (4)	0.6884 (2)	0.0591 (2)	0.0522 (9)
H14	0.7103	0.6705	−0.0034	0.063*
O3'	0.5167 (10)	0.7811 (5)	0.3302 (5)	0.076 (3)	0.357 (5)
H3'	0.4225	0.7579	0.3439	0.115*	0.357 (5)

Atomic displacement parameters (Å²) top

	U¹¹	U²²	U³³	U¹²	U¹³	U²³
O1	0.0805 (16)	0.0506 (14)	0.0549 (14)	0.0031 (12)	0.0283 (12)	−0.0007 (11)
O2	0.0902 (17)	0.0484 (14)	0.0645 (15)	0.0031 (12)	0.0320 (13)	0.0033 (11)
O3	0.140 (4)	0.037 (2)	0.073 (3)	0.005 (2)	0.046 (2)	−0.0088 (18)
O4	0.0773 (17)	0.0780 (18)	0.0740 (18)	−0.0035 (14)	0.0315 (14)	0.0168 (14)
O5	0.155 (3)	0.0525 (17)	0.111 (2)	−0.0188 (18)	0.056 (2)	0.0086 (16)
N1	0.072 (2)	0.052 (2)	0.072 (2)	−0.0078 (16)	0.0208 (17)	0.0113 (17)
N2	0.0662 (18)	0.0403 (16)	0.0484 (16)	−0.0003 (13)	0.0187 (14)	−0.0016 (13)
N3	0.0616 (17)	0.0433 (16)	0.0541 (16)	−0.0017 (13)	0.0149 (14)	0.0068 (13)
C1	0.052 (2)	0.051 (2)	0.053 (2)	0.0002 (16)	0.0145 (17)	0.0112 (16)
C2	0.072 (2)	0.043 (2)	0.068 (2)	0.0001 (17)	0.022 (2)	−0.0005 (18)
C3	0.067 (2)	0.051 (2)	0.056 (2)	0.0041 (18)	0.0228 (18)	−0.0038 (17)
C4	0.0455 (18)	0.0404 (19)	0.0466 (19)	0.0010 (14)	0.0104 (15)	0.0028 (15)
C5	0.066 (2)	0.0407 (19)	0.053 (2)	0.0041 (16)	0.0205 (17)	0.0017 (15)
C6	0.062 (2)	0.056 (2)	0.052 (2)	0.0038 (17)	0.0179 (17)	0.0021 (17)
C7	0.0461 (19)	0.049 (2)	0.048 (2)	0.0023 (15)	0.0087 (16)	−0.0006 (16)
C8	0.054 (2)	0.047 (2)	0.051 (2)	0.0012 (16)	0.0123 (16)	0.0010 (16)
C9	0.0479 (19)	0.0414 (19)	0.052 (2)	−0.0001 (15)	0.0093 (16)	0.0005 (16)
C10	0.064 (2)	0.0330 (18)	0.062 (2)	−0.0018 (15)	0.0148 (18)	−0.0035 (15)
C11	0.066 (2)	0.047 (2)	0.052 (2)	0.0009 (17)	0.0120 (18)	−0.0043 (17)
C12	0.056 (2)	0.0382 (19)	0.052 (2)	−0.0007 (15)	0.0152 (17)	0.0068 (15)
C13	0.062 (2)	0.0387 (19)	0.060 (2)	0.0011 (16)	0.0156 (18)	−0.0049 (17)
C14	0.057 (2)	0.050 (2)	0.052 (2)	0.0006 (16)	0.0160 (17)	−0.0035 (16)
O3'	0.116 (7)	0.066 (5)	0.053 (4)	−0.018 (4)	0.040 (4)	−0.011 (3)

Geometric parameters (Å, º) top

O1—C7	1.236 (3)	C4—C7	1.487 (4)
O2—C12	1.367 (3)	C5—C6	1.375 (4)
O2—H2A	0.82	C5—H5	0.93
O3—C13	1.379 (4)	C6—H6	0.93
O3—H3A	0.82	C8—C9	1.458 (4)
O4—N1	1.216 (3)	C8—H8	0.93
O5—N1	1.221 (3)	C9—C14	1.382 (4)
N1—C1	1.469 (4)	C9—C10	1.390 (4)
N2—C7	1.346 (4)	C10—C11	1.365 (4)
N2—N3	1.386 (3)	C10—H10	0.93
N2—H2B	0.90	C11—O3'	1.319 (5)
N3—C8	1.271 (3)	C11—C12	1.385 (4)
C1—C6	1.360 (4)	C11—H11	0.93
C1—C2	1.373 (4)	C12—C13	1.380 (4)
C2—C3	1.377 (4)	C13—C14	1.379 (4)
C2—H2	0.93	C13—H13	0.93
C3—C4	1.387 (4)	C14—H14	0.93
C3—H3	0.93	O3'—H3'	0.82
C4—C5	1.390 (4)

C12—O2—H2A	109.5	O1—C7—C4	120.4 (3)
C13—O3—H3A	109.5	N2—C7—C4	118.3 (3)
O4—N1—O5	123.0 (3)	N3—C8—C9	119.2 (3)
O4—N1—C1	118.9 (3)	N3—C8—H8	120.4
O5—N1—C1	118.1 (3)	C9—C8—H8	120.4
C7—N2—N3	117.0 (2)	C14—C9—C10	118.1 (3)
C7—N2—H2B	130.3	C14—C9—C8	121.8 (3)
N3—N2—H2B	112.0	C10—C9—C8	120.1 (3)
C8—N3—N2	117.4 (3)	C11—C10—C9	121.5 (3)
C6—C1—C2	122.4 (3)	C11—C10—H10	119.2
C6—C1—N1	119.5 (3)	C9—C10—H10	119.2
C2—C1—N1	118.0 (3)	O3'—C11—C10	110.5 (4)
C1—C2—C3	118.4 (3)	O3'—C11—C12	129.6 (4)
C1—C2—H2	120.8	C10—C11—C12	119.9 (3)
C3—C2—H2	120.8	C10—C11—H11	120.0
C2—C3—C4	120.7 (3)	C12—C11—H11	120.0
C2—C3—H3	119.7	O2—C12—C13	116.3 (3)
C4—C3—H3	119.7	O2—C12—C11	124.3 (3)
C3—C4—C5	119.1 (3)	C13—C12—C11	119.4 (3)
C3—C4—C7	117.4 (3)	C14—C13—O3	121.6 (3)
C5—C4—C7	123.5 (3)	C14—C13—C12	120.3 (3)
C6—C5—C4	120.3 (3)	O3—C13—C12	118.1 (3)
C6—C5—H5	119.9	C14—C13—H13	119.8
C4—C5—H5	119.9	C12—C13—H13	119.8
C1—C6—C5	119.1 (3)	C13—C14—C9	120.8 (3)
C1—C6—H6	120.4	C13—C14—H14	119.6
C5—C6—H6	120.4	C9—C14—H14	119.5
O1—C7—N2	121.3 (3)	C11—O3'—H3'	109.5

C7—N2—N3—C8	179.0 (3)	C5—C4—C7—N2	5.9 (4)
O4—N1—C1—C6	−3.5 (5)	N2—N3—C8—C9	178.7 (3)
O5—N1—C1—C6	178.1 (3)	N3—C8—C9—C14	176.0 (3)
O4—N1—C1—C2	175.3 (3)	N3—C8—C9—C10	−2.7 (5)
O5—N1—C1—C2	−3.1 (5)	C14—C9—C10—C11	0.2 (5)
C6—C1—C2—C3	0.2 (5)	C8—C9—C10—C11	178.9 (3)
N1—C1—C2—C3	−178.5 (3)	C9—C10—C11—O3'	178.0 (4)
C1—C2—C3—C4	−0.3 (5)	C9—C10—C11—C12	−0.7 (5)
C2—C3—C4—C5	−0.2 (5)	O3'—C11—C12—O2	1.3 (7)
C2—C3—C4—C7	−179.6 (3)	C10—C11—C12—O2	179.7 (3)
C3—C4—C5—C6	0.7 (5)	O3'—C11—C12—C13	−177.4 (5)
C7—C4—C5—C6	−179.8 (3)	C10—C11—C12—C13	1.1 (5)
C2—C1—C6—C5	0.3 (5)	O2—C12—C13—C14	−179.8 (3)
N1—C1—C6—C5	179.1 (3)	C11—C12—C13—C14	−1.0 (5)
C4—C5—C6—C1	−0.8 (5)	O2—C12—C13—O3	−0.3 (5)
N3—N2—C7—O1	−0.3 (4)	C11—C12—C13—O3	178.5 (3)
N3—N2—C7—C4	178.0 (2)	O3—C13—C14—C9	−178.9 (3)
C3—C4—C7—O1	3.6 (4)	C12—C13—C14—C9	0.5 (5)
C5—C4—C7—O1	−175.8 (3)	C10—C9—C14—C13	−0.1 (5)
C3—C4—C7—N2	−174.6 (3)	C8—C9—C14—C13	−178.8 (3)

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
O3—H3A···O2	0.82	2.17	2.636 (4)	116
O2—H2A···O1ⁱ	0.82	1.91	2.722 (3)	171
O3′—H3′···O1ⁱ	0.82	1.84	2.548 (7)	144
N2—H2B···O4ⁱⁱ	0.90	2.26	3.121 (3)	158
C5—H5···O5ⁱⁱ	0.93	2.48	3.210 (4)	135
C10—H10···O2ⁱⁱⁱ	0.93	2.58	3.467 (3)	159
C11—H11···O1ⁱ	0.93	2.56	3.192 (4)	126

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

Experimental details

Crystal data
Chemical formula	C₁₄H₁₁N₃O₅
M_r	301.26
Crystal system, space group	Monoclinic, P2₁/c
Temperature (K)	298
a, b, c (Å)	7.666 (1), 13.196 (2), 13.176 (2)
β (°)	95.361 (3)
V (Å³)	1327.1 (3)
Z	4
Radiation type	Mo Kα
µ (mm⁻¹)	0.12
Crystal size (mm)	0.20 × 0.20 × 0.18

Data collection
Diffractometer	Bruker SMART CCD area-detector diffractometer
Absorption correction	Multi-scan (SADABS; Bruker, 2001)
T_min, T_max	0.977, 0.979
No. of measured, independent and observed [I > 2σ(I)] reflections	8322, 3204, 1364
R_int	0.056
(sin θ/λ)_max (Å⁻¹)	0.667

Refinement
R[F² > 2σ(F²)], wR(F²), S	0.069, 0.161, 1.02
No. of reflections	3204
No. of parameters	210
No. of restraints	2
H-atom treatment	H-atom parameters constrained
Δρ_max, Δρ_min (e Å⁻³)	0.17, −0.23

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

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
O3—H3A···O2	0.82	2.17	2.636 (4)	116
O2—H2A···O1ⁱ	0.82	1.91	2.722 (3)	171
O3'—H3'···O1ⁱ	0.82	1.84	2.548 (7)	144
N2—H2B···O4ⁱⁱ	0.90	2.26	3.121 (3)	158
C5—H5···O5ⁱⁱ	0.93	2.48	3.210 (4)	135
C10—H10···O2ⁱⁱⁱ	0.93	2.58	3.467 (3)	159
C11—H11···O1ⁱ	0.93	2.56	3.192 (4)	126

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

References

Allen, F. H., Kennard, O., Watson, D. G., Brammer, L., Orpen, A. G. & Taylor, R. (1987). J. Chem. Soc. Perkin Trans. 2, pp. S1–19. CrossRef Web of Science Google Scholar
Bruker (2001). SADABS. Bruker AXS Inc., Madison, Wisconsin, USA. Google Scholar
Bruker (2007). SMART and SAINT. Bruker AXS Inc., Madison, Wisconsin, USA. Google Scholar
Diao, Y.-P., Huang, S.-S., Zhang, J.-K. & Kang, T.-G. (2008a). Acta Cryst. E64, o470. Web of Science CSD CrossRef IUCr Journals Google Scholar
Diao, Y.-P., Zhen, Y.-H., Han, X. & Deng, S. (2008b). Acta Cryst. E64, o101. Web of Science CSD CrossRef IUCr Journals 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., Sujith, K. V., Patil, P. S., Kalluraya, B. & Chantrapromma, S. (2008). Acta Cryst. E64, o1961–o1962. Web of Science CSD CrossRef 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
Ma, H.-B., Huang, S.-S. & Diao, Y.-P. (2008). Acta Cryst. E64, o210. Web of Science CSD CrossRef IUCr Journals Google Scholar
Okabe, N., Nakamura, T. & Fukuda, H. (1993). Acta Cryst. C49, 1678–1680. CSD CrossRef CAS Web of Science IUCr Journals Google Scholar
Qiu, F. & Zhao, L.-M. (2008). Acta Cryst. E64, o2067. Web of Science CrossRef IUCr Journals Google Scholar
Shan, S., Tian, Y.-L., Wang, S.-H., Wang, W.-L. & Xu, Y.-L. (2008). Acta Cryst. E64, o1363. Web of Science CSD CrossRef IUCr Journals Google Scholar
Sheldrick, G. M. (2008). Acta Cryst. A64, 112–122. Web of Science CrossRef CAS IUCr Journals Google Scholar
Yang, D.-S. (2008). Acta Cryst. E64, o1759. Web of Science CSD CrossRef IUCr Journals Google Scholar

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Volume 65| Part 8| August 2009| Page o2050

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