3,3′-(m-Phenyl­enedi­oxy)diphthalonitrile

Lv, W.; Wang, K.; Zhang, D.; Jiang, J.; Zhang, X.

doi:10.1107/S1600536810011578

organic compounds

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ISSN: 2056-9890

Volume 66| Part 5| May 2010| Page o1011

https://doi.org/10.1107/S1600536810011578

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3,3′-(m-Phenylenedioxy)diphthalonitrile

Wei Lv,^a Kang Wang,^b Daopeng Zhang,^a Jianzhuang Jiang ^a ^* and Xiaomei Zhang ^a ^*

^aDepartment of Chemistry, Shandong University, Jinan 250100, People's Republic of China, and ^bDepartment of Chemistry, University of Science and Technology Beijing, Beijing 100083, People's Republic of China
^*Correspondence e-mail: jianzhuang@ustb.edu.cn, zhangxiaomei@sdu.edu.cn

(Received 13 March 2010; accepted 26 March 2010; online 2 April 2010)

In the title compound, C₂₂H₁₀N₄O₂, the dihedral angles between the mean planes of the central benzene ring and the pendant rings are 79.20 (6) and 80.29 (6)°. The dihedral angle between the pendant rings is 10.27 (7)°.

Related literature

For background to `semi-rigid' molecules as ligands, see: Wang et al. (2005 , 2009 ). For related structures, see: Huang et al. (2005 ); Zhang & Lu (2007 ).

Experimental

Crystal data

C₂₂H₁₀N₄O₂
M_r = 362.34
Monoclinic, C 2/c
a = 15.668 (3) Å
b = 12.722 (3) Å
c = 19.004 (5) Å
β = 109.911 (6)°
V = 3561.7 (14) Å³
Z = 8
Mo Kα radiation
μ = 0.09 mm⁻¹
T = 298 K
0.20 × 0.15 × 0.10 mm

Data collection

Bruker SMART 1000 CCD diffractometer
Absorption correction: multi-scan (SADABS; Siemens, 1996 ) T_min = 0.982, T_max = 0.991
10307 measured reflections
3992 independent reflections
3145 reflections with I > 2σ(I)
R_int = 0.034

Refinement

R[F² > 2σ(F²)] = 0.039
wR(F²) = 0.111
S = 1.03
3992 reflections
254 parameters
H-atom parameters constrained
Δρ_max = 0.20 e Å⁻³
Δρ_min = −0.16 e Å⁻³

Data collection: SMART (Siemens, 1996); cell refinement: SAINT (Siemens, 1996); 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 I, global. DOI: https://doi.org/10.1107/S1600536810011578/hb5363sup1.cif

Structure factors: contains datablock I. DOI: https://doi.org/10.1107/S1600536810011578/hb5363Isup2.hkl

checkCIF report

Comment top

In the past few years, the semirigidity of molecules have been extensively employed for search of novel functional compounds. For example,a new family of multidentate O-donor ligands with a semirigid V-shaped molecular framework have been used to construct metal-organic coordination frameworks (Wang et al., 2009; Wang et al., 2005), in which some showed interesting properties. Here, we present the structure of a new semirigid organic ligand.

The crystal structure of the title compound is given in Fig. 1. As can be found, all the bond lengths and angles are normal and correspond to those observed in related compound (Huang et al., 2005; Zhang et al., 2007). The aromatic rings (C3—C8 and C15—C20) in sides of the molecule are in the same direction of the aromatic rings(C9—C14) with a cis configuration. The three dihedral angles in the title compound are 79.81Å for C3—C8 and C9—C14, 80.83Å for C15—C20 and C9—C14,and 10.54 Å for C3—C8 and C15—C20, respectively.

Related literature top

For background to `semi-rigid' molecules as ligands, see: Wang et al. (2005, 2009). For related structures, see: Huang et al. (2005); Zhang & Lu (2007).

Experimental top

Resorcinol (0.53 g, 5 mmol) and anhydrous K₂CO₃ was added to the solution of 2,3-dicyanophenyl nitrate (1.73 g, 10 mmol) in DMSO (25 ml). A kind of brown solution was generated after the solution was stirred for 48 hours at room temperature. The brown solution was added to 200 ml water, and was stirred for 30 min at room temperature. The precipitate formed was filtered, and washed by water. Yellow rods of (I) were obtained by solvent evaporation of the solution of the title compound in acetonitrile. Yield: 1.65 g, 91.2% Anal. for: C₂₂H₁₀N₄O₂ Calc. C, 72.92; H, 2.76; N, 15.47; Found: C, 72.85; H, 2.88; N, 15.44.

Structure description top

For background to `semi-rigid' molecules as ligands, see: Wang et al. (2005, 2009). For related structures, see: Huang et al. (2005); Zhang & Lu (2007).

Computing details top

Data collection: SMART (Siemens, 1996); cell refinement: SAINT (Siemens, 1996); data reduction: SAINT (Siemens, 1996); 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 (I). Displacement ellipsoids are drawn at 30% probability level.

3,3'-(m-Phenylenedioxy)diphthalonitrile top

Crystal data top

C₂₂H₁₀N₄O₂	F(000) = 1488
M_r = 362.34	D_x = 1.351 Mg m⁻³
Monoclinic, C2/c	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: -C 2yc	Cell parameters from 4716 reflections
a = 15.668 (3) Å	θ = 2.6–27.4°
b = 12.722 (3) Å	µ = 0.09 mm⁻¹
c = 19.004 (5) Å	T = 298 K
β = 109.911 (6)°	Rod, yellow
V = 3561.7 (14) Å³	0.20 × 0.15 × 0.10 mm
Z = 8

Data collection top

Bruker SMART 1000 CCD diffractometer	3992 independent reflections
Radiation source: fine-focus sealed tube	3145 reflections with I > 2σ(I)
Graphite monochromator	R_int = 0.034
ω scans	θ_max = 27.6°, θ_min = 2.1°
Absorption correction: multi-scan (SADABS; Siemens, 1996)	h = −14→20
T_min = 0.982, T_max = 0.991	k = −15→15
10307 measured reflections	l = −24→23

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)] = 0.039	H-atom parameters constrained
wR(F²) = 0.111	w = 1/[σ²(F_o²) + (0.0506P)² + 1.0114P] where P = (F_o² + 2F_c²)/3
S = 1.03	(Δ/σ)_max < 0.001
3992 reflections	Δρ_max = 0.20 e Å⁻³
254 parameters	Δρ_min = −0.16 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: 0.0032 (4)

Crystal data top

C₂₂H₁₀N₄O₂	V = 3561.7 (14) Å³
M_r = 362.34	Z = 8
Monoclinic, C2/c	Mo Kα radiation
a = 15.668 (3) Å	µ = 0.09 mm⁻¹
b = 12.722 (3) Å	T = 298 K
c = 19.004 (5) Å	0.20 × 0.15 × 0.10 mm
β = 109.911 (6)°

Data collection top

Bruker SMART 1000 CCD diffractometer	3992 independent reflections
Absorption correction: multi-scan (SADABS; Siemens, 1996)	3145 reflections with I > 2σ(I)
T_min = 0.982, T_max = 0.991	R_int = 0.034
10307 measured reflections

Refinement top

R[F² > 2σ(F²)] = 0.039	0 restraints
wR(F²) = 0.111	H-atom parameters constrained
S = 1.03	Δρ_max = 0.20 e Å⁻³
3992 reflections	Δρ_min = −0.16 e Å⁻³
254 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
C2	0.24878 (8)	0.23670 (11)	0.58469 (7)	0.0496 (3)
O1	0.41988 (6)	0.16069 (8)	0.64684 (5)	0.0597 (3)
O2	0.73624 (5)	0.20407 (7)	0.70914 (6)	0.0582 (3)
C9	0.49526 (7)	0.15184 (9)	0.62398 (7)	0.0425 (3)
C10	0.57791 (7)	0.17608 (9)	0.67719 (7)	0.0437 (3)
H10	0.5826	0.1926	0.7260	0.052*
C20	0.88271 (8)	0.16165 (10)	0.78616 (7)	0.0438 (3)
C11	0.65301 (7)	0.17492 (9)	0.65542 (7)	0.0459 (3)
C14	0.48704 (8)	0.12738 (10)	0.55183 (7)	0.0474 (3)
H14	0.4308	0.1110	0.5168	0.057*
C3	0.26451 (7)	0.12567 (10)	0.58820 (6)	0.0420 (3)
C4	0.19286 (7)	0.05388 (10)	0.56020 (6)	0.0443 (3)
C15	0.79734 (7)	0.12689 (9)	0.74065 (7)	0.0448 (3)
C12	0.64815 (9)	0.15132 (11)	0.58405 (8)	0.0554 (3)
H12	0.7000	0.1512	0.5707	0.067*
N3	0.23572 (10)	0.32515 (11)	0.58276 (8)	0.0727 (4)
C21	0.90124 (8)	0.27171 (11)	0.79679 (8)	0.0535 (3)
C8	0.35196 (8)	0.08751 (11)	0.61986 (7)	0.0466 (3)
C16	0.77924 (9)	0.02090 (10)	0.73059 (8)	0.0558 (3)
H16	0.7222	−0.0022	0.7005	0.067*
C5	0.20892 (9)	−0.05263 (11)	0.56674 (8)	0.0528 (3)
H5	0.1612	−0.1000	0.5485	0.063*
C19	0.95031 (8)	0.08725 (11)	0.82021 (7)	0.0499 (3)
C13	0.56427 (9)	0.12762 (11)	0.53235 (8)	0.0543 (3)
H13	0.5597	0.1115	0.4835	0.065*
N2	1.11044 (8)	0.15377 (13)	0.89675 (8)	0.0774 (4)
C1	0.10262 (8)	0.09249 (11)	0.52163 (8)	0.0524 (3)
C6	0.29672 (9)	−0.08846 (11)	0.60074 (8)	0.0585 (3)
H6	0.3077	−0.1604	0.6061	0.070*
C18	0.93170 (10)	−0.01859 (12)	0.80996 (8)	0.0630 (4)
H18	0.9762	−0.0681	0.8328	0.076*
C17	0.84594 (11)	−0.05017 (12)	0.76525 (9)	0.0661 (4)
H17	0.8332	−0.1216	0.7585	0.079*
C22	1.03960 (9)	0.12385 (12)	0.86413 (8)	0.0577 (4)
N4	0.03136 (8)	0.12171 (11)	0.48961 (8)	0.0725 (4)
C7	0.36803 (9)	−0.01905 (12)	0.62679 (8)	0.0564 (3)
H7	0.4269	−0.0441	0.6490	0.068*
N1	0.91780 (9)	0.35902 (11)	0.80612 (9)	0.0809 (4)

Atomic displacement parameters (Å²) top

	U¹¹	U²²	U³³	U¹²	U¹³	U²³
C2	0.0399 (6)	0.0575 (8)	0.0501 (7)	−0.0042 (6)	0.0137 (5)	−0.0057 (6)
O1	0.0322 (4)	0.0797 (7)	0.0681 (6)	−0.0119 (4)	0.0181 (4)	−0.0269 (5)
O2	0.0293 (4)	0.0448 (5)	0.0869 (7)	−0.0052 (3)	0.0020 (4)	−0.0088 (4)
C9	0.0287 (5)	0.0456 (6)	0.0512 (7)	−0.0002 (4)	0.0111 (5)	−0.0022 (5)
C10	0.0347 (6)	0.0455 (6)	0.0463 (6)	−0.0043 (5)	0.0080 (5)	−0.0018 (5)
C20	0.0333 (6)	0.0515 (7)	0.0468 (6)	−0.0069 (5)	0.0137 (5)	−0.0004 (5)
C11	0.0286 (5)	0.0389 (6)	0.0635 (8)	−0.0048 (4)	0.0071 (5)	−0.0023 (5)
C14	0.0357 (6)	0.0514 (7)	0.0482 (7)	−0.0012 (5)	0.0056 (5)	−0.0031 (5)
C3	0.0334 (5)	0.0526 (7)	0.0406 (6)	−0.0027 (5)	0.0134 (5)	−0.0007 (5)
C4	0.0323 (6)	0.0554 (7)	0.0442 (6)	−0.0035 (5)	0.0117 (5)	0.0026 (5)
C15	0.0326 (5)	0.0463 (7)	0.0540 (7)	−0.0043 (5)	0.0129 (5)	−0.0004 (5)
C12	0.0422 (7)	0.0545 (7)	0.0764 (9)	−0.0084 (6)	0.0290 (6)	−0.0085 (7)
N3	0.0745 (9)	0.0599 (8)	0.0802 (9)	0.0003 (7)	0.0219 (7)	−0.0093 (6)
C21	0.0306 (6)	0.0589 (8)	0.0642 (8)	−0.0086 (5)	0.0076 (5)	−0.0030 (6)
C8	0.0313 (5)	0.0621 (8)	0.0462 (6)	−0.0049 (5)	0.0128 (5)	−0.0072 (5)
C16	0.0443 (7)	0.0484 (7)	0.0661 (8)	−0.0098 (6)	0.0077 (6)	0.0010 (6)
C5	0.0432 (7)	0.0544 (8)	0.0602 (8)	−0.0089 (6)	0.0168 (6)	0.0020 (6)
C19	0.0383 (6)	0.0640 (8)	0.0453 (6)	−0.0011 (6)	0.0116 (5)	0.0054 (6)
C13	0.0537 (7)	0.0589 (8)	0.0534 (7)	−0.0065 (6)	0.0223 (6)	−0.0070 (6)
N2	0.0416 (7)	0.1071 (11)	0.0731 (8)	−0.0068 (7)	0.0059 (6)	0.0123 (8)
C1	0.0369 (6)	0.0569 (8)	0.0581 (7)	−0.0078 (6)	0.0094 (6)	0.0031 (6)
C6	0.0523 (8)	0.0527 (8)	0.0718 (9)	0.0046 (6)	0.0229 (7)	0.0087 (7)
C18	0.0578 (8)	0.0600 (9)	0.0630 (8)	0.0099 (7)	0.0098 (7)	0.0136 (7)
C17	0.0674 (9)	0.0459 (7)	0.0737 (9)	−0.0043 (6)	0.0093 (8)	0.0075 (7)
C22	0.0395 (7)	0.0768 (10)	0.0532 (7)	0.0029 (6)	0.0111 (6)	0.0111 (7)
N4	0.0399 (6)	0.0705 (8)	0.0914 (10)	−0.0021 (6)	0.0018 (6)	0.0083 (7)
C7	0.0360 (6)	0.0694 (9)	0.0617 (8)	0.0092 (6)	0.0140 (6)	0.0056 (7)
N1	0.0538 (7)	0.0594 (8)	0.1145 (12)	−0.0151 (6)	0.0094 (8)	−0.0088 (8)

Geometric parameters (Å, º) top

C2—N3	1.1421 (19)	C15—C16	1.3777 (18)
C2—C3	1.4315 (19)	C12—C13	1.3798 (19)
O1—C8	1.3750 (15)	C12—H12	0.9300
O1—C9	1.3949 (14)	C21—N1	1.1406 (19)
O2—C15	1.3596 (15)	C8—C7	1.377 (2)
O2—C11	1.4048 (14)	C16—C17	1.369 (2)
C9—C14	1.3686 (17)	C16—H16	0.9300
C9—C10	1.3795 (16)	C5—C6	1.3828 (19)
C10—C11	1.3740 (16)	C5—H5	0.9300
C10—H10	0.9300	C19—C18	1.377 (2)
C20—C15	1.3946 (16)	C19—C22	1.4406 (18)
C20—C19	1.4035 (18)	C13—H13	0.9300
C20—C21	1.4303 (19)	N2—C22	1.1369 (18)
C11—C12	1.3657 (19)	C1—N4	1.1368 (16)
C14—C13	1.3808 (18)	C6—C7	1.377 (2)
C14—H14	0.9300	C6—H6	0.9300
C3—C8	1.3834 (16)	C18—C17	1.382 (2)
C3—C4	1.4038 (16)	C18—H18	0.9300
C4—C5	1.3761 (19)	C17—H17	0.9300
C4—C1	1.4393 (17)	C7—H7	0.9300

N3—C2—C3	178.96 (15)	N1—C21—C20	178.61 (16)
C8—O1—C9	117.33 (9)	O1—C8—C7	122.54 (11)
C15—O2—C11	118.00 (9)	O1—C8—C3	116.79 (12)
C14—C9—C10	121.99 (11)	C7—C8—C3	120.59 (11)
C14—C9—O1	121.98 (10)	C17—C16—C15	119.49 (12)
C10—C9—O1	115.89 (11)	C17—C16—H16	120.3
C11—C10—C9	117.60 (11)	C15—C16—H16	120.3
C11—C10—H10	121.2	C4—C5—C6	119.28 (12)
C9—C10—H10	121.2	C4—C5—H5	120.4
C15—C20—C19	119.07 (12)	C6—C5—H5	120.4
C15—C20—C21	120.25 (11)	C18—C19—C20	120.26 (12)
C19—C20—C21	120.67 (11)	C18—C19—C22	121.00 (13)
C12—C11—C10	122.52 (11)	C20—C19—C22	118.73 (13)
C12—C11—O2	120.25 (11)	C12—C13—C14	121.25 (12)
C10—C11—O2	117.16 (11)	C12—C13—H13	119.4
C9—C14—C13	118.43 (11)	C14—C13—H13	119.4
C9—C14—H14	120.8	N4—C1—C4	178.29 (16)
C13—C14—H14	120.8	C7—C6—C5	120.85 (13)
C8—C3—C4	118.83 (12)	C7—C6—H6	119.6
C8—C3—C2	119.73 (11)	C5—C6—H6	119.6
C4—C3—C2	121.43 (10)	C19—C18—C17	119.06 (13)
C5—C4—C3	120.56 (11)	C19—C18—H18	120.5
C5—C4—C1	119.98 (11)	C17—C18—H18	120.5
C3—C4—C1	119.41 (12)	C16—C17—C18	121.77 (14)
O2—C15—C16	124.39 (11)	C16—C17—H17	119.1
O2—C15—C20	115.27 (10)	C18—C17—H17	119.1
C16—C15—C20	120.34 (11)	N2—C22—C19	177.82 (15)
C11—C12—C13	118.21 (12)	C8—C7—C6	119.83 (12)
C11—C12—H12	120.9	C8—C7—H7	120.1
C13—C12—H12	120.9	C6—C7—H7	120.1

C8—O1—C9—C14	41.14 (17)	C9—O1—C8—C3	−129.48 (12)
C8—O1—C9—C10	−143.02 (12)	C4—C3—C8—O1	−179.70 (10)
C14—C9—C10—C11	−0.04 (18)	C2—C3—C8—O1	0.21 (16)
O1—C9—C10—C11	−175.87 (11)	C4—C3—C8—C7	−2.83 (18)
C9—C10—C11—C12	0.24 (18)	C2—C3—C8—C7	177.08 (12)
C9—C10—C11—O2	177.36 (10)	O2—C15—C16—C17	−179.83 (13)
C15—O2—C11—C12	−77.49 (16)	C20—C15—C16—C17	−0.4 (2)
C15—O2—C11—C10	105.33 (13)	C3—C4—C5—C6	−0.51 (19)
C10—C9—C14—C13	−0.24 (19)	C1—C4—C5—C6	176.87 (12)
O1—C9—C14—C13	175.35 (12)	C15—C20—C19—C18	−1.39 (19)
C8—C3—C4—C5	2.48 (17)	C21—C20—C19—C18	179.66 (13)
C2—C3—C4—C5	−177.43 (11)	C15—C20—C19—C22	176.97 (12)
C8—C3—C4—C1	−174.92 (11)	C21—C20—C19—C22	−1.98 (18)
C2—C3—C4—C1	5.17 (17)	C11—C12—C13—C14	−0.1 (2)
C11—O2—C15—C16	−8.46 (19)	C9—C14—C13—C12	0.3 (2)
C11—O2—C15—C20	172.12 (11)	C4—C5—C6—C7	−1.1 (2)
C19—C20—C15—O2	−179.22 (11)	C20—C19—C18—C17	0.6 (2)
C21—C20—C15—O2	−0.27 (17)	C22—C19—C18—C17	−177.77 (14)
C19—C20—C15—C16	1.32 (19)	C15—C16—C17—C18	−0.4 (2)
C21—C20—C15—C16	−179.72 (13)	C19—C18—C17—C16	0.4 (2)
C10—C11—C12—C13	−0.2 (2)	O1—C8—C7—C6	177.91 (12)
O2—C11—C12—C13	−177.18 (11)	C3—C8—C7—C6	1.2 (2)
C9—O1—C8—C7	53.72 (17)	C5—C6—C7—C8	0.8 (2)

Experimental details

Crystal data
Chemical formula	C₂₂H₁₀N₄O₂
M_r	362.34
Crystal system, space group	Monoclinic, C2/c
Temperature (K)	298
a, b, c (Å)	15.668 (3), 12.722 (3), 19.004 (5)
β (°)	109.911 (6)
V (Å³)	3561.7 (14)
Z	8
Radiation type	Mo Kα
µ (mm⁻¹)	0.09
Crystal size (mm)	0.20 × 0.15 × 0.10

Data collection
Diffractometer	Bruker SMART 1000 CCD
Absorption correction	Multi-scan (SADABS; Siemens, 1996)
T_min, T_max	0.982, 0.991
No. of measured, independent and observed [I > 2σ(I)] reflections	10307, 3992, 3145
R_int	0.034
(sin θ/λ)_max (Å⁻¹)	0.651

Refinement
R[F² > 2σ(F²)], wR(F²), S	0.039, 0.111, 1.03
No. of reflections	3992
No. of parameters	254
H-atom treatment	H-atom parameters constrained
Δρ_max, Δρ_min (e Å⁻³)	0.20, −0.16

Computer programs: SMART (Siemens, 1996), SAINT (Siemens, 1996), SHELXS97 (Sheldrick, 2008), SHELXL97 (Sheldrick, 2008), SHELXTL (Sheldrick, 2008).

Acknowledgements

This work was supported by Professor Yongzhong Bian, the Doctoral Foundation of Shandong (grant No. 2007BS04027) and Postdoctoral Scientific Foundation of China and Shandong (grant Nos. 200603070 and 20070411093).

References

Huang, X., Zhao, F., Wang, R.-J., Zhang, F. & Tung, C.-H. (2005). Acta Cryst. E61, o4384–o4386. 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
Siemens (1996). SMART, SAINT and SADABS. Siemens Analytical X-ray Instruments Inc., Madison, Wisconsin, USA. Google Scholar
Wang, X., Qin, C., Wang, E., Li, Y., Su, Z., Xu, L. & Carlucci, L. (2005). Angew. Chem. Int. Ed. 44, 5824–5827 Web of Science CSD CrossRef CAS Google Scholar
Wang, H., Zhang, D., Sun, D., Chen, Y., Zhang, L., Tian, L., Jiang, J. & Ni, Z.-H. (2009). Cryst. Growth Des. pp. 5273–5282 CrossRef Google Scholar
Zhang, X.-M. & Lu, J.-T. (2007). Acta Cryst. E63, o3861. Web of Science CSD CrossRef IUCr Journals Google Scholar