4-Dimethyl­amino-N′-(2-meth­oxy­benzyl­idene)benzohydrazide

Su, F.; Gu, Z.-G.; Lin, J.

doi:10.1107/S1600536811025220

organic compounds

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ISSN: 2056-9890

Volume 67| Part 8| August 2011| Page o1896

doi:10.1107/S1600536811025220

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4-Dimethylamino-N′-(2-methoxybenzylidene)benzohydrazide

Fu Su,^a Zheng-Gui Gu ^a and Jun Lin ^a ^*

^aJiangsu Centre of Extraction Seperation Engineering Technology, College of Chemistry and Materials Science, Nanjing Normal University, Nanjing 210046, People's Republic of China
^*Correspondence e-mail: douduo2011@163.com

(Received 17 June 2011; accepted 27 June 2011; online 2 July 2011)

In the title molecule, C₁₇H₁₉N₃O₂, the dihedral angle between the two benzene rings is 14.05 (15)°. In the crystal, molecules are linked through intermolecular N—H⋯O hydrogen bonds, forming chains along b.

Related literature

For the biological properties of hydrazones, see: Ajani et al. (2010 ); Zhang et al. (2010 ); Angelusiu et al. (2010 ). For similar structures, see: Huang & Wu (2010 ); Khaledi et al. (2010 ); Zhou & Yang (2010 ); Ji & Lu (2010 ); Singh & Singh (2010 ); Ahmad et al. (2010 ); Su et al. (2011 ).

Experimental

Crystal data

C₁₇H₁₉N₃O₂
M_r = 297.35
Orthorhombic, P b c a
a = 16.065 (3) Å
b = 7.946 (2) Å
c = 24.534 (3) Å
V = 3131.8 (11) Å³
Z = 8
Mo Kα radiation
μ = 0.09 mm⁻¹
T = 298 K
0.13 × 0.10 × 0.08 mm

Data collection

Bruker SMART CCD area-detector diffractometer
Absorption correction: multi-scan (SADABS; Bruker, 2001 ) T_min = 0.989, T_max = 0.993
13733 measured reflections
2800 independent reflections
1570 reflections with I > 2σ(I)
R_int = 0.094

Refinement

R[F² > 2σ(F²)] = 0.064
wR(F²) = 0.140
S = 0.99
2800 reflections
203 parameters
H-atom parameters constrained
Δρ_max = 0.20 e Å⁻³
Δρ_min = −0.18 e Å⁻³

Table 1
Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
N2—H2⋯O2ⁱ	0.91	2.07	2.966 (3)	169
Symmetry code: (i) $[-x+{\script{1\over 2}}, y+{\script{1\over 2}}, z]$ .

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/S1600536811025220/su2286sup1.cif

Structure factors: contains datablock I. DOI: 10.1107/S1600536811025220/su2286Isup2.hkl

Supporting information file. DOI: 10.1107/S1600536811025220/su2286Isup3.cml

checkCIF report

Comment top

In 2010, much attention has been focused on the biological properties of hydrazone compounds (Ajani et al., 2010; Zhang et al., 2010; Angelusiu et al., 2010). The crystal structures of a number of hydrazone compounds have also been determined (Huang & Wu, 2010; Khaledi et al., 2010; Zhou & Yang, 2010; Ji & Lu, 2010; Singh & Singh, 2010; Ahmad et al., 2010). Herein, we report on the synthesis and crystal structure of a new hydrazone compound, prepared by the reaction of 2-methoxybenzaldehyde with 4-dimethylaminobenzohydrazide.

In the molecule of the title compound, Fig. 1, the dihedral angle between the two benzene rings is 14.05 (15) °. All the bond values are comparable with those in the similar compound, N'-(4-Diethylamino-2-hydroxybenzylidene)-4-(dimethylamino)benzohydrazide methanol monosolvate, we reported recently (Su et al., 2011).

In the crystal structure, the hydrazone molecules are linked through intermolecular N–H···O hydrogen bonds (Table 1), to form 1D chains along b (Fig. 2).

Related literature top

For the biological properties of hydrazones, see: Ajani et al. (2010); Zhang et al. (2010); Angelusiu et al. (2010). For similar structures, see: Huang & Wu (2010); Khaledi et al. (2010); Zhou & Yang (2010); Ji & Lu (2010); Singh & Singh (2010); Ahmad et al. (2010); Su et al. (2011).

Experimental top

The reaction of 2-methoxybenzaldehyde (0.136 g, 1 mmol) with 4-dimethylaminobenzohydrazide (0.179 g, 1 mmol) in 30 ml methanol at room temperature afforded the title compound. Colourless single crystals were formed by gradual evaporation of the solution in air.

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 molecule showing 30% probability displacement ellipsoids and the atomic numbering. Hydrogen bonds are drawn as dashed lines.
	Fig. 2. Crystal packing of the title compound, viewed down the a axis. Intermolecular interactions are drawn as dashed lines.

4-Dimethylamino-N'-(2-methoxybenzylidene)benzohydrazide top

Crystal data top

C₁₇H₁₉N₃O₂	F(000) = 1264
M_r = 297.35	D_x = 1.261 Mg m⁻³
Orthorhombic, Pbca	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: -P 2ac 2ab	Cell parameters from 1584 reflections
a = 16.065 (3) Å	θ = 2.5–24.5°
b = 7.946 (2) Å	µ = 0.09 mm⁻¹
c = 24.534 (3) Å	T = 298 K
V = 3131.8 (11) Å³	Block, colourless
Z = 8	0.13 × 0.10 × 0.08 mm

Data collection top

Bruker SMART CCD area-detector diffractometer	2800 independent reflections
Radiation source: fine-focus sealed tube	1570 reflections with I > 2σ(I)
Graphite monochromator	R_int = 0.094
ω scans	θ_max = 25.1°, θ_min = 2.1°
Absorption correction: multi-scan (SADABS; Bruker, 2001)	h = −19→14
T_min = 0.989, T_max = 0.993	k = −9→9
13733 measured reflections	l = −29→28

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)] = 0.064	H-atom parameters constrained
wR(F²) = 0.140	w = 1/[σ²(F_o²) + (0.0579P)²] where P = (F_o² + 2F_c²)/3
S = 0.99	(Δ/σ)_max < 0.001
2800 reflections	Δρ_max = 0.20 e Å⁻³
203 parameters	Δρ_min = −0.18 e Å⁻³
0 restraints	Extinction correction: SHELXL97 (Sheldrick, 2008), Fc^*=kFc[1+0.001xFc²λ³/sin(2θ)]^-1/4
Primary atom site location: structure-invariant direct methods	Extinction coefficient: 0.0028 (7)

Crystal data top

C₁₇H₁₉N₃O₂	V = 3131.8 (11) Å³
M_r = 297.35	Z = 8
Orthorhombic, Pbca	Mo Kα radiation
a = 16.065 (3) Å	µ = 0.09 mm⁻¹
b = 7.946 (2) Å	T = 298 K
c = 24.534 (3) Å	0.13 × 0.10 × 0.08 mm

Data collection top

Bruker SMART CCD area-detector diffractometer	2800 independent reflections
Absorption correction: multi-scan (SADABS; Bruker, 2001)	1570 reflections with I > 2σ(I)
T_min = 0.989, T_max = 0.993	R_int = 0.094
13733 measured reflections

Refinement top

R[F² > 2σ(F²)] = 0.064	0 restraints
wR(F²) = 0.140	H-atom parameters constrained
S = 0.99	Δρ_max = 0.20 e Å⁻³
2800 reflections	Δρ_min = −0.18 e Å⁻³
203 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
O1	0.48383 (13)	0.6587 (3)	0.24567 (9)	0.0662 (7)
O2	0.14952 (11)	0.4522 (2)	0.11421 (8)	0.0472 (6)
N1	0.26607 (14)	0.5707 (3)	0.17978 (9)	0.0416 (6)
N2	0.24365 (13)	0.6531 (3)	0.13259 (8)	0.0416 (6)
H2	0.2698	0.7527	0.1273	0.050*
N3	0.05256 (15)	0.9526 (3)	−0.07705 (10)	0.0528 (7)
C1	0.34787 (17)	0.5653 (4)	0.25970 (11)	0.0411 (7)
C2	0.42874 (18)	0.5812 (4)	0.27952 (11)	0.0436 (7)
C3	0.4498 (2)	0.5152 (4)	0.32985 (13)	0.0559 (9)
H3	0.5038	0.5257	0.3431	0.067*
C4	0.3908 (2)	0.4350 (5)	0.35968 (13)	0.0665 (10)
H4	0.4047	0.3937	0.3940	0.080*
C5	0.3123 (2)	0.4135 (5)	0.34093 (14)	0.0695 (11)
H5	0.2736	0.3542	0.3615	0.083*
C6	0.29024 (19)	0.4800 (4)	0.29113 (13)	0.0588 (9)
H6	0.2360	0.4674	0.2785	0.071*
C7	0.5688 (2)	0.6547 (5)	0.26050 (16)	0.0847 (12)
H7A	0.5767	0.7171	0.2936	0.127*
H7B	0.6016	0.7041	0.2320	0.127*
H7C	0.5858	0.5401	0.2660	0.127*
C8	0.32433 (17)	0.6371 (3)	0.20687 (11)	0.0411 (7)
H8	0.3521	0.7310	0.1934	0.049*
C9	0.18162 (16)	0.5881 (4)	0.10239 (11)	0.0364 (7)
C10	0.15273 (16)	0.6857 (3)	0.05514 (10)	0.0353 (7)
C11	0.20007 (16)	0.8036 (4)	0.02693 (10)	0.0410 (8)
H11	0.2546	0.8242	0.0378	0.049*
C12	0.16804 (18)	0.8897 (4)	−0.01651 (11)	0.0460 (8)
H12	0.2016	0.9663	−0.0349	0.055*
C13	0.08536 (17)	0.8651 (4)	−0.03401 (11)	0.0387 (7)
C14	0.03883 (17)	0.7460 (4)	−0.00569 (11)	0.0428 (8)
H14	−0.0160	0.7254	−0.0160	0.051*
C15	0.07247 (17)	0.6587 (3)	0.03703 (11)	0.0405 (7)
H15	0.0401	0.5781	0.0545	0.049*
C16	−0.03085 (19)	0.9181 (4)	−0.09651 (12)	0.0630 (10)
H16A	−0.0354	0.8013	−0.1060	0.095*
H16B	−0.0421	0.9861	−0.1280	0.095*
H16C	−0.0703	0.9442	−0.0684	0.095*
C17	0.1000 (2)	1.0754 (5)	−0.10564 (15)	0.0850 (12)
H17A	0.1213	1.1568	−0.0803	0.128*
H17B	0.0653	1.1308	−0.1319	0.128*
H17C	0.1456	1.0215	−0.1240	0.128*

Atomic displacement parameters (Å²) top

	U¹¹	U²²	U³³	U¹²	U¹³	U²³
O1	0.0498 (14)	0.0811 (17)	0.0678 (14)	−0.0141 (13)	−0.0137 (12)	0.0283 (13)
O2	0.0488 (12)	0.0363 (12)	0.0566 (13)	−0.0065 (10)	−0.0030 (10)	0.0106 (10)
N1	0.0426 (14)	0.0413 (15)	0.0410 (14)	0.0018 (13)	−0.0046 (12)	0.0138 (12)
N2	0.0451 (14)	0.0384 (15)	0.0413 (13)	−0.0043 (12)	−0.0076 (12)	0.0132 (11)
N3	0.0532 (16)	0.0579 (18)	0.0473 (15)	0.0045 (14)	−0.0077 (13)	0.0092 (14)
C1	0.0442 (18)	0.0409 (18)	0.0383 (16)	0.0080 (15)	0.0006 (14)	0.0076 (14)
C2	0.0500 (19)	0.0403 (18)	0.0404 (17)	0.0013 (15)	−0.0037 (15)	0.0065 (15)
C3	0.064 (2)	0.053 (2)	0.050 (2)	0.0052 (18)	−0.0167 (17)	0.0033 (17)
C4	0.082 (3)	0.077 (3)	0.0406 (19)	0.023 (2)	−0.0012 (19)	0.0167 (19)
C5	0.059 (2)	0.089 (3)	0.061 (2)	0.017 (2)	0.0184 (19)	0.033 (2)
C6	0.0423 (19)	0.075 (2)	0.059 (2)	0.0147 (17)	0.0046 (16)	0.0217 (19)
C7	0.052 (2)	0.089 (3)	0.113 (3)	−0.012 (2)	−0.017 (2)	0.027 (2)
C8	0.0428 (17)	0.0364 (17)	0.0442 (17)	0.0034 (15)	0.0008 (14)	0.0058 (15)
C9	0.0333 (16)	0.0327 (17)	0.0432 (17)	0.0046 (14)	0.0030 (13)	0.0020 (14)
C10	0.0389 (17)	0.0317 (16)	0.0352 (15)	0.0019 (13)	−0.0008 (13)	−0.0013 (13)
C11	0.0367 (16)	0.0471 (19)	0.0391 (17)	−0.0054 (14)	−0.0056 (14)	0.0044 (14)
C12	0.0526 (19)	0.0443 (19)	0.0412 (17)	−0.0085 (15)	0.0032 (15)	0.0094 (15)
C13	0.0444 (17)	0.0364 (18)	0.0353 (15)	0.0056 (15)	−0.0035 (14)	−0.0031 (14)
C14	0.0404 (16)	0.0459 (19)	0.0423 (17)	−0.0048 (15)	−0.0070 (14)	−0.0044 (15)
C15	0.0424 (18)	0.0375 (18)	0.0414 (17)	−0.0033 (14)	−0.0007 (14)	0.0001 (14)
C16	0.069 (2)	0.068 (2)	0.0512 (19)	0.0169 (19)	−0.0200 (17)	−0.0021 (18)
C17	0.077 (3)	0.099 (3)	0.079 (3)	−0.002 (2)	−0.007 (2)	0.050 (2)

Geometric parameters (Å, º) top

O1—C2	1.361 (3)	C7—H7A	0.9600
O1—C7	1.413 (3)	C7—H7B	0.9600
O2—C9	1.231 (3)	C7—H7C	0.9600
N1—C8	1.263 (3)	C8—H8	0.9300
N1—N2	1.378 (3)	C9—C10	1.470 (4)
N2—C9	1.345 (3)	C10—C15	1.381 (3)
N2—H2	0.9056	C10—C11	1.391 (3)
N3—C13	1.369 (3)	C11—C12	1.367 (4)
N3—C17	1.424 (4)	C11—H11	0.9300
N3—C16	1.449 (4)	C12—C13	1.410 (4)
C1—C6	1.383 (4)	C12—H12	0.9300
C1—C2	1.393 (4)	C13—C14	1.392 (4)
C1—C8	1.466 (4)	C14—C15	1.368 (4)
C2—C3	1.383 (4)	C14—H14	0.9300
C3—C4	1.357 (4)	C15—H15	0.9300
C3—H3	0.9300	C16—H16A	0.9600
C4—C5	1.353 (4)	C16—H16B	0.9600
C4—H4	0.9300	C16—H16C	0.9600
C5—C6	1.378 (4)	C17—H17A	0.9600
C5—H5	0.9300	C17—H17B	0.9600
C6—H6	0.9300	C17—H17C	0.9600

C2—O1—C7	117.4 (2)	C1—C8—H8	120.2
C8—N1—N2	115.9 (2)	O2—C9—N2	121.1 (2)
C9—N2—N1	118.3 (2)	O2—C9—C10	121.1 (3)
C9—N2—H2	127.0	N2—C9—C10	117.8 (2)
N1—N2—H2	114.4	C15—C10—C11	117.1 (2)
C13—N3—C17	121.4 (3)	C15—C10—C9	117.8 (2)
C13—N3—C16	121.0 (3)	C11—C10—C9	125.1 (2)
C17—N3—C16	117.6 (3)	C12—C11—C10	121.3 (3)
C6—C1—C2	118.3 (3)	C12—C11—H11	119.4
C6—C1—C8	120.7 (3)	C10—C11—H11	119.4
C2—C1—C8	120.9 (3)	C11—C12—C13	121.5 (3)
O1—C2—C3	123.8 (3)	C11—C12—H12	119.2
O1—C2—C1	115.7 (2)	C13—C12—H12	119.2
C3—C2—C1	120.4 (3)	N3—C13—C14	121.6 (3)
C4—C3—C2	119.2 (3)	N3—C13—C12	121.8 (3)
C4—C3—H3	120.4	C14—C13—C12	116.6 (2)
C2—C3—H3	120.4	C15—C14—C13	121.0 (3)
C5—C4—C3	121.8 (3)	C15—C14—H14	119.5
C5—C4—H4	119.1	C13—C14—H14	119.5
C3—C4—H4	119.1	C14—C15—C10	122.5 (3)
C4—C5—C6	119.5 (3)	C14—C15—H15	118.8
C4—C5—H5	120.2	C10—C15—H15	118.8
C6—C5—H5	120.2	N3—C16—H16A	109.5
C5—C6—C1	120.7 (3)	N3—C16—H16B	109.5
C5—C6—H6	119.7	H16A—C16—H16B	109.5
C1—C6—H6	119.7	N3—C16—H16C	109.5
O1—C7—H7A	109.5	H16A—C16—H16C	109.5
O1—C7—H7B	109.5	H16B—C16—H16C	109.5
H7A—C7—H7B	109.5	N3—C17—H17A	109.5
O1—C7—H7C	109.5	N3—C17—H17B	109.5
H7A—C7—H7C	109.5	H17A—C17—H17B	109.5
H7B—C7—H7C	109.5	N3—C17—H17C	109.5
N1—C8—C1	119.6 (3)	H17A—C17—H17C	109.5
N1—C8—H8	120.2	H17B—C17—H17C	109.5

C8—N1—N2—C9	−179.6 (2)	O2—C9—C10—C15	23.9 (4)
C7—O1—C2—C3	7.1 (4)	N2—C9—C10—C15	−155.4 (2)
C7—O1—C2—C1	−170.6 (3)	O2—C9—C10—C11	−156.0 (3)
C6—C1—C2—O1	176.7 (3)	N2—C9—C10—C11	24.7 (4)
C8—C1—C2—O1	−3.2 (4)	C15—C10—C11—C12	0.6 (4)
C6—C1—C2—C3	−1.1 (4)	C9—C10—C11—C12	−179.6 (3)
C8—C1—C2—C3	179.0 (3)	C10—C11—C12—C13	1.1 (4)
O1—C2—C3—C4	−177.7 (3)	C17—N3—C13—C14	179.4 (3)
C1—C2—C3—C4	0.0 (5)	C16—N3—C13—C14	−3.1 (4)
C2—C3—C4—C5	1.9 (5)	C17—N3—C13—C12	−1.2 (4)
C3—C4—C5—C6	−2.6 (6)	C16—N3—C13—C12	176.2 (3)
C4—C5—C6—C1	1.4 (5)	C11—C12—C13—N3	179.1 (3)
C2—C1—C6—C5	0.4 (5)	C11—C12—C13—C14	−1.5 (4)
C8—C1—C6—C5	−179.6 (3)	N3—C13—C14—C15	179.6 (3)
N2—N1—C8—C1	175.3 (2)	C12—C13—C14—C15	0.2 (4)
C6—C1—C8—N1	−28.0 (4)	C13—C14—C15—C10	1.5 (4)
C2—C1—C8—N1	152.0 (3)	C11—C10—C15—C14	−1.8 (4)
N1—N2—C9—O2	−5.2 (4)	C9—C10—C15—C14	178.3 (2)
N1—N2—C9—C10	174.1 (2)

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
N2—H2···O2ⁱ	0.91	2.07	2.966 (3)	169

Symmetry code: (i) −x+1/2, y+1/2, z.

Experimental details

Crystal data
Chemical formula	C₁₇H₁₉N₃O₂
M_r	297.35
Crystal system, space group	Orthorhombic, Pbca
Temperature (K)	298
a, b, c (Å)	16.065 (3), 7.946 (2), 24.534 (3)
V (Å³)	3131.8 (11)
Z	8
Radiation type	Mo Kα
µ (mm⁻¹)	0.09
Crystal size (mm)	0.13 × 0.10 × 0.08

Data collection
Diffractometer	Bruker SMART CCD area-detector diffractometer
Absorption correction	Multi-scan (SADABS; Bruker, 2001)
T_min, T_max	0.989, 0.993
No. of measured, independent and observed [I > 2σ(I)] reflections	13733, 2800, 1570
R_int	0.094
(sin θ/λ)_max (Å⁻¹)	0.598

Refinement
R[F² > 2σ(F²)], wR(F²), S	0.064, 0.140, 0.99
No. of reflections	2800
No. of parameters	203
H-atom treatment	H-atom parameters constrained
Δρ_max, Δρ_min (e Å⁻³)	0.20, −0.18

Computer programs: SMART (Bruker, 2007), SAINT (Bruker, 2007), 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···O2ⁱ	0.91	2.07	2.966 (3)	169

Symmetry code: (i) −x+1/2, y+1/2, z.

Acknowledgements

This project was funded by the Priority Academic Program Development of Jiangsu Higher Education Institutions.

References

Ahmad, T., Zia-ur-Rehman, M., Siddiqui, H. L., Mahmud, S. & Parvez, M. (2010). Acta Cryst. E66, o1022. Web of Science CSD CrossRef IUCr Journals Google Scholar
Ajani, O. O., Obafemi, C. A., Nwinyi, O. C. & Akinpelu, D. A. (2010). Bioorg. Med. Chem. 18, 214–221. Web of Science CrossRef PubMed CAS Google Scholar
Angelusiu, M. V., Barbuceanu, S. F., Draghici, C. & Almajan, G. L. (2010). Eur. J. Med. Chem. 45, 2055–2062. Web of Science CrossRef CAS PubMed 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
Huang, H.-T. & Wu, H.-Y. (2010). Acta Cryst. E66, o2729–o2730. Web of Science CSD CrossRef IUCr Journals Google Scholar
Ji, X.-H. & Lu, J.-F. (2010). Acta Cryst. E66, o1514. Web of Science CSD CrossRef IUCr Journals Google Scholar
Khaledi, H., Alhadi, A. A., Mohd Ali, H., Robinson, W. T. & Abdulla, M. A. (2010). Acta Cryst. E66, o105–o106. 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
Singh, V. P. & Singh, S. (2010). Acta Cryst. E66, o1172. Web of Science CSD CrossRef IUCr Journals Google Scholar
Su, F., Gu, Z.-G. & Lin, J. (2011). Acta Cryst. E67, o1634. Web of Science CSD CrossRef IUCr Journals Google Scholar
Zhang, Y.-H., Zhang, L., Liu, L., Guo, J.-X., Wu, D.-L., Xu, G.-C., Wang, X.-H. & Jia, D.-Z. (2010). Inorg. Chim. Acta, 363, 289–293. Web of Science CSD CrossRef CAS Google Scholar
Zhou, C.-S. & Yang, T. (2010). Acta Cryst. E66, o290. Web of Science CSD CrossRef IUCr Journals Google Scholar