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

Journal logoCRYSTALLOGRAPHIC
COMMUNICATIONS
ISSN: 2056-9890
Volume 67| Part 10| October 2011| Page o2787
https://doi.org/10.1107/S1600536811039043

Monoclinic polymorph of 4-[(1H-benz­imidazol-1-yl)meth­yl]benzoic acid

Hai-Wei Kuaia* and Xiao-Chun Chenga

aFaculty of Life Science and Chemical Engineering, Huaiyin Institute of Technology, Huaian 223003, People's Republic of China
*Correspondence e-mail: hyitshy@126.com

(Received 13 August 2011; accepted 22 September 2011; online 30 September 2011)

Three polymorphs of the title compound, C15H12N2O2, were obtained accidentally as single crystals in the hydro­thermal reaction of the title compound with manganese bromide in the presence of N,N′-dimethyl­formamide at 373 K. Here we report the structure of the first polymorph. The benzimidazole ring is almost planar, the maximum deviation from the mean plane being 0.016 (1) Å. The benzimidazole and benzene rings are approximately perpendicular, making a dihedral angle 85.56 (7)°, which is a reflection of the axial rotation of the flexible benzimidazolyl arm. In the crystal, adjacent mol­ecules are connected through O—H⋯N hydrogen bonds into a chain along [100], and neighboring chains are further linked by via weak C—H⋯O hydrogen-bonding inter­actions, forming a two-dimensional network.

Related literature

For two other polymorphs of the title compound, see Kuai & Cheng (2011a[Kuai, H.-W. & Cheng, X.-C. (2011a). Acta Cryst. E67, submitted (AA2024).],b[Kuai, H.-W. & Cheng, X.-C. (2011b). Acta Cryst. E67, submitted (AA2025).]). For the synthesis of 4-[(1H-benzo[d]imidazol-1-yl)meth­yl]benzoic acid, see: Hua et al. (2010[Hua, Q., Zhao, Y., Xu, G.-C., Chen, M.-S., Su, Z., Cai, K. & Sun, W.-Y. (2010). Cryst. Growth Des. 10, 2553-2562.]). For background to metal-organic hybrid materials, see: Das & Bharadwaj (2009[Das, M. C. & Bharadwaj, P. K. (2009). J. Am. Chem. Soc. 131, 10942-10943.]); Kuai et al. (2011[Kuai, H.-W., Cheng, X.-C. & Zhu, X.-H. (2011). J. Coord. Chem. 64, 1636-1644.]).

[Scheme 1]

Experimental

Crystal data

  • C15H12N2O2

  • Mr = 252.27

  • Monoclinic, P 21 /c

  • a = 10.435 (2) Å

  • b = 14.360 (3) Å

  • c = 8.2922 (17) Å

  • β = 96.925 (3)°

  • V = 1233.5 (4) Å3

  • Z = 4

  • Mo Kα radiation

  • μ = 0.09 mm−1

  • T = 293 K

  • 0.20 × 0.20 × 0.16 mm
Data collection

  • Bruker SMART APEX CCD diffractometer

  • Absorption correction: multi-scan (SADABS; Sheldrick, 1996[Sheldrick, G. M. (1996). SADABS. University of Göttingen, Germany.]) Tmin = 0.982, Tmax = 0.985

  • 6155 measured reflections

  • 2157 independent reflections

  • 1294 reflections with I > 2σ(I)

  • Rint = 0.065
Refinement

  • R[F2 > 2σ(F2)] = 0.041

  • wR(F2) = 0.082

  • S = 0.82

  • 2157 reflections

  • 160 parameters

  • H-atom parameters constrained

  • Δρmax = 0.13 e Å−3

  • Δρmin = −0.19 e Å−3

Table 1
Hydrogen-bond geometry (Å, °)

D—H⋯A D—H H⋯A D⋯A D—H⋯A
O1—H12⋯N12i 0.82 1.83 2.652 (2) 178
C12—H7⋯O2ii 0.93 2.49 3.213 (3) 135
Symmetry codes: (i) [x+1, -y+{\script{1\over 2}}, z+{\script{1\over 2}}]; (ii) x-1, y, z.

Data collection: SMART (Bruker, 1998[Bruker (1998). SMART and SAINT. Bruker AXS Inc., Madison, Wisconsin, USA.]); cell refinement: SAINT (Bruker, 1998[Bruker (1998). SMART and SAINT. Bruker AXS Inc., Madison, Wisconsin, USA.]); data reduction: SAINT; program(s) used to solve structure: SHELXS97 (Sheldrick, 2008[Sheldrick, G. M. (2008). Acta Cryst. A64, 112-122.]); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008[Sheldrick, G. M. (2008). Acta Cryst. A64, 112-122.]); molecular graphics: SHELXTL (Sheldrick, 2008[Sheldrick, G. M. (2008). Acta Cryst. A64, 112-122.]); software used to prepare material for publication: SHELXTL.

Supporting information

Crystal structure: contains datablocks I, global. DOI: https://doi.org/10.1107/S1600536811039043/aa2023sup1.cif

Supporting information file. DOI: https://doi.org/10.1107/S1600536811039043/aa2023Isup2.cdx

Structure factors: contains datablock I. DOI: https://doi.org/10.1107/S1600536811039043/aa2023Isup3.hkl

Supporting information file. DOI: https://doi.org/10.1107/S1600536811039043/aa2023Isup4.cml

checkCIF report


Comment top

The title compound, 4-((1H-benzo[d]imidazol-1-yl)methyl)benzoic acid (HL), are usually regarded as an excellent candidate for building block in molecular self-assembly engineerings due to its variable conformations and coordination modes (Das et al., 2009). During assemblies of coordination polymers, we accidentally obtained three different kind of single crystals of the title compound, which can be proved by different unit cell parameters (or space group). Here, we will introduce one of them. The single crystals of the title compound, C15H12N2O2, were accidentally obtained by the hydrothermal reaction at 373 K of the HL with manganese bromide in the presence of N,N'-dimethylformamide as alkaline medium for the deprotonation. As shown in Fig. 1, the asymmetric unit consists of only one HL molecule. Interestingly, though crystallizing from alkaline solution, the HL remains the intact carboxylic group in the crystal structure. The flexible benzimidazolyl arm is apt to axially rotate. as a result, the benzimidazolyl ring and central benzene rings are approximately vertical, inclined at a dihedral angle of 85.56 (6) °; The torsion angles of N11-C11-C1-C2 and N11-C11-C1-C6 are -56.9 (3) ° and 125.4 (2) °, respectively. Adjacent molecules are connected through O-H···N hydrogen bonds into a one-dimensional chain along [100] deirction, and neighboring chains are further linked via C-H···O weak hydrogen bonding interaction to form a two-dimensional network (Fig. 2).

Related literature top

For two other polymorphs of the title compound, see Kuai & Cheng (2011a,b). For the synthesis of 4-[(1H-benzo[d]imidazol-1-yl)methyl]benzoic acid, see: Hua et al. (2010). For background to metal-organic hybrid materials, see: Das & Bharadwaj (2009); Kuai et al. (2011).

Experimental top

Reaction mixture of MnBr2 (21.5 mg, 0.1 mmol), 4-((1H-benzo[d]imidazol-1-yl)methyl)benzoic acid (25.2 mg, 0.1 mmol) and 2 ml N,N'-dimethylformamide (DMF) in 8 ml H2O were sealed in a 16 ml Teflon-lined stainless steel container and keeped at 373 K for 3 days. After cooling to the room temperature, colourless block crystals of the title compound were obtained.

Refinement top

All hydrogen atoms were located in geometrically idealized positions and constrained to ride on their parent atoms, with C—H = 0.93 and 0.97 Å, O—H = 0.82 Å and Uiso(H) = 1.2Ueq(C, O).

Structure description top

The title compound, 4-((1H-benzo[d]imidazol-1-yl)methyl)benzoic acid (HL), are usually regarded as an excellent candidate for building block in molecular self-assembly engineerings due to its variable conformations and coordination modes (Das et al., 2009). During assemblies of coordination polymers, we accidentally obtained three different kind of single crystals of the title compound, which can be proved by different unit cell parameters (or space group). Here, we will introduce one of them. The single crystals of the title compound, C15H12N2O2, were accidentally obtained by the hydrothermal reaction at 373 K of the HL with manganese bromide in the presence of N,N'-dimethylformamide as alkaline medium for the deprotonation. As shown in Fig. 1, the asymmetric unit consists of only one HL molecule. Interestingly, though crystallizing from alkaline solution, the HL remains the intact carboxylic group in the crystal structure. The flexible benzimidazolyl arm is apt to axially rotate. as a result, the benzimidazolyl ring and central benzene rings are approximately vertical, inclined at a dihedral angle of 85.56 (6) °; The torsion angles of N11-C11-C1-C2 and N11-C11-C1-C6 are -56.9 (3) ° and 125.4 (2) °, respectively. Adjacent molecules are connected through O-H···N hydrogen bonds into a one-dimensional chain along [100] deirction, and neighboring chains are further linked via C-H···O weak hydrogen bonding interaction to form a two-dimensional network (Fig. 2).

For two other polymorphs of the title compound, see Kuai & Cheng (2011a,b). For the synthesis of 4-[(1H-benzo[d]imidazol-1-yl)methyl]benzoic acid, see: Hua et al. (2010). For background to metal-organic hybrid materials, see: Das & Bharadwaj (2009); Kuai et al. (2011).

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
[Figure 1] Fig. 1. : The crystal structure of the title compound showing 30% probability displacement ellipsoids.
[Figure 2] Fig. 2. : The packing diagram of the title compound. Hydrogen bonds are shown as dashed lines.
4-[(1H-Benzimidazol-1-yl)methyl]benzoic acid top
Crystal data top
C15H12N2O2F(000) = 528
Mr = 252.27Dx = 1.358 Mg m−3
Monoclinic, P21/cMo Kα radiation, λ = 0.71073 Å
Hall symbol: -P 2ybcCell parameters from 961 reflections
a = 10.435 (2) Åθ = 2.8–20.1°
b = 14.360 (3) ŵ = 0.09 mm−1
c = 8.2922 (17) ÅT = 293 K
β = 96.925 (3)°Block, colourless
V = 1233.5 (4) Å30.20 × 0.20 × 0.16 mm
Z = 4
Data collection top
Bruker SMART APEX CCD
diffractometer		2157 independent reflections
Radiation source: fine-focus sealed tube1294 reflections with I > 2σ(I)
Graphite monochromatorRint = 0.065
phi and ω scansθmax = 25.0°, θmin = 2.0°
Absorption correction: multi-scan
(SADABS; Sheldrick, 1996)		h = −12→12
Tmin = 0.982, Tmax = 0.985k = −17→14
6155 measured reflectionsl = −9→9
Refinement top
Refinement on F2Primary atom site location: structure-invariant direct methods
Least-squares matrix: fullSecondary atom site location: difference Fourier map
R[F2 > 2σ(F2)] = 0.041Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.082H-atom parameters constrained
S = 0.82 w = 1/[σ2(Fo2) + (0.0242P)2]
where P = (Fo2 + 2Fc2)/3
2157 reflections(Δ/σ)max < 0.001
160 parametersΔρmax = 0.13 e Å−3
0 restraintsΔρmin = −0.19 e Å−3
Crystal data top
C15H12N2O2V = 1233.5 (4) Å3
Mr = 252.27Z = 4
Monoclinic, P21/cMo Kα radiation
a = 10.435 (2) ŵ = 0.09 mm−1
b = 14.360 (3) ÅT = 293 K
c = 8.2922 (17) Å0.20 × 0.20 × 0.16 mm
β = 96.925 (3)°
Data collection top
Bruker SMART APEX CCD
diffractometer		2157 independent reflections
Absorption correction: multi-scan
(SADABS; Sheldrick, 1996)		1294 reflections with I > 2σ(I)
Tmin = 0.982, Tmax = 0.985Rint = 0.065
6155 measured reflections
Refinement top
R[F2 > 2σ(F2)] = 0.0410 restraints
wR(F2) = 0.082H-atom parameters constrained
S = 0.82Δρmax = 0.13 e Å−3
2157 reflectionsΔρmin = −0.19 e Å−3
160 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
xyzUiso*/Ueq
N110.62238 (13)0.42913 (9)0.16767 (19)0.0384 (4)
N120.43462 (14)0.36669 (10)0.06416 (19)0.043
O21.30575 (12)0.33153 (9)0.43647 (18)0.062
O11.19958 (12)0.20370 (10)0.49287 (19)0.0694 (5)
H121.27290.18340.51650.083*
C140.63655 (16)0.40473 (11)0.0100 (2)0.0362 (5)
C41.07691 (16)0.33415 (13)0.3955 (2)0.0406 (5)
C150.73758 (18)0.41493 (12)−0.0828 (3)0.0479 (5)
H80.81560.4417−0.04060.057*
C130.51859 (17)0.36548 (12)−0.0533 (2)0.0383 (5)
C20.84621 (17)0.33703 (13)0.3785 (2)0.0473 (5)
H10.76930.30750.39390.057*
C110.71733 (16)0.47882 (13)0.2797 (2)0.0469 (5)
H60.68150.49000.38060.056*
H50.73470.53880.23330.056*
C10.84294 (16)0.42581 (13)0.3160 (2)0.0402 (5)
C411.20563 (18)0.28995 (15)0.4421 (2)0.0468 (5)
C120.50053 (17)0.40470 (12)0.1920 (2)0.0445 (5)
H70.46710.41400.28980.053*
C51.07310 (18)0.42162 (14)0.3297 (3)0.0515 (6)
H31.14970.45030.31060.062*
C180.49941 (19)0.33416 (13)−0.2123 (3)0.0488 (5)
H110.42140.3075−0.25500.059*
C60.95772 (18)0.46810 (14)0.2912 (3)0.0523 (6)
H40.95730.52800.24840.063*
C170.5994 (2)0.34376 (13)−0.3053 (3)0.0563 (6)
H100.58880.3235−0.41260.068*
C30.96226 (17)0.29079 (13)0.4188 (2)0.0506 (6)
H20.96300.23090.46140.061*
C160.7167 (2)0.38356 (13)−0.2405 (3)0.0557 (6)
H90.78270.3890−0.30600.067*
Atomic displacement parameters (Å2) top
U11U22U33U12U13U23
N110.0279 (9)0.0422 (10)0.0433 (11)0.0015 (7)−0.0023 (8)−0.0023 (8)
N120.0320.0440.053−0.002−0.001−0.001
O20.0290.0700.085−0.0060.0010.011
O10.0326 (8)0.0644 (11)0.1098 (14)0.0077 (7)0.0023 (8)0.0228 (9)
C140.0324 (11)0.0324 (11)0.0427 (13)0.0008 (8)−0.0007 (9)0.0012 (9)
C40.0299 (11)0.0493 (13)0.0418 (13)0.0004 (9)0.0014 (9)0.0007 (10)
C150.0392 (12)0.0494 (13)0.0543 (15)−0.0065 (10)0.0027 (11)−0.0049 (11)
C130.0350 (11)0.0304 (11)0.0474 (13)0.0020 (8)−0.0033 (10)0.0027 (10)
C20.0282 (11)0.0524 (14)0.0612 (15)−0.0028 (9)0.0046 (10)−0.0005 (11)
C110.0361 (12)0.0481 (13)0.0539 (14)0.0039 (9)−0.0054 (10)−0.0101 (10)
C10.0323 (11)0.0425 (13)0.0435 (13)0.0008 (9)−0.0046 (9)−0.0076 (10)
C410.0355 (12)0.0548 (14)0.0494 (14)0.0029 (10)0.0021 (10)0.0018 (11)
C120.0339 (11)0.0472 (12)0.0523 (14)0.0060 (9)0.0048 (10)0.0027 (10)
C50.0338 (12)0.0566 (14)0.0634 (15)−0.0062 (10)0.0022 (11)0.0068 (12)
C180.0425 (12)0.0451 (13)0.0553 (15)−0.0032 (10)−0.0078 (11)−0.0021 (11)
C60.0415 (13)0.0460 (13)0.0668 (16)−0.0013 (10)−0.0032 (11)0.0092 (11)
C170.0699 (16)0.0486 (14)0.0492 (15)−0.0045 (11)0.0024 (13)−0.0046 (11)
C30.0354 (12)0.0473 (13)0.0683 (16)0.0006 (10)0.0035 (11)0.0103 (11)
C160.0605 (15)0.0514 (14)0.0574 (16)−0.0101 (11)0.0164 (13)−0.0028 (12)
Geometric parameters (Å, º) top
N11—C121.357 (2)C2—C31.386 (2)
N11—C141.379 (2)C2—H10.9300
N11—C111.460 (2)C11—C11.514 (2)
N12—C121.311 (2)C11—H60.9700
N12—C131.387 (2)C11—H50.9700
O2—C411.209 (2)C1—C61.380 (2)
O1—C411.312 (2)C12—H70.9300
O1—H120.8200C5—C61.380 (2)
C14—C151.386 (2)C5—H30.9300
C14—C131.397 (2)C18—C171.377 (2)
C4—C51.368 (2)C18—H110.9300
C4—C31.383 (2)C6—H40.9300
C4—C411.494 (2)C17—C161.398 (3)
C15—C161.375 (3)C17—H100.9300
C15—H80.9300C3—H20.9300
C13—C181.384 (3)C16—H90.9300
C2—C11.375 (2)
C12—N11—C14106.55 (15)C2—C1—C11121.50 (16)
C12—N11—C11127.41 (16)C6—C1—C11119.67 (18)
C14—N11—C11125.84 (15)O2—C41—O1123.63 (18)
C12—N12—C13105.01 (15)O2—C41—C4122.30 (19)
C41—O1—H12109.5O1—C41—C4114.05 (16)
N11—C14—C15132.49 (17)N12—C12—N11113.38 (17)
N11—C14—C13105.55 (15)N12—C12—H7123.3
C15—C14—C13121.93 (18)N11—C12—H7123.3
C5—C4—C3119.02 (17)C4—C5—C6121.26 (17)
C5—C4—C41118.38 (17)C4—C5—H3119.4
C3—C4—C41122.59 (18)C6—C5—H3119.4
C16—C15—C14116.72 (19)C17—C18—C13117.92 (19)
C16—C15—H8121.6C17—C18—H11121.0
C14—C15—H8121.6C13—C18—H11121.0
C18—C13—N12129.94 (18)C5—C6—C1120.08 (19)
C18—C13—C14120.54 (18)C5—C6—H4120.0
N12—C13—C14109.51 (17)C1—C6—H4120.0
C1—C2—C3121.09 (17)C18—C17—C16120.9 (2)
C1—C2—H1119.5C18—C17—H10119.6
C3—C2—H1119.5C16—C17—H10119.6
N11—C11—C1112.67 (15)C4—C3—C2119.73 (18)
N11—C11—H6109.1C4—C3—H2120.1
C1—C11—H6109.1C2—C3—H2120.1
N11—C11—H5109.1C15—C16—C17121.99 (19)
C1—C11—H5109.1C15—C16—H9119.0
H6—C11—H5107.8C17—C16—H9119.0
C2—C1—C6118.79 (17)
C12—N11—C14—C15178.01 (19)C3—C4—C41—O2−172.53 (19)
C11—N11—C14—C152.8 (3)C5—C4—C41—O1−175.23 (18)
C12—N11—C14—C13−0.18 (18)C3—C4—C41—O15.9 (3)
C11—N11—C14—C13−175.40 (16)C13—N12—C12—N110.2 (2)
N11—C14—C15—C16−178.63 (19)C14—N11—C12—N120.0 (2)
C13—C14—C15—C16−0.7 (3)C11—N11—C12—N12175.12 (17)
C12—N12—C13—C18−179.09 (19)C3—C4—C5—C62.0 (3)
C12—N12—C13—C14−0.3 (2)C41—C4—C5—C6−176.89 (19)
N11—C14—C13—C18179.22 (16)N12—C13—C18—C17178.11 (18)
C15—C14—C13—C180.8 (3)C14—C13—C18—C17−0.6 (3)
N11—C14—C13—N120.3 (2)C4—C5—C6—C1−1.2 (3)
C15—C14—C13—N12−178.13 (16)C2—C1—C6—C5−0.4 (3)
C12—N11—C11—C1124.04 (18)C11—C1—C6—C5177.53 (19)
C14—N11—C11—C1−61.7 (2)C13—C18—C17—C160.3 (3)
C3—C2—C1—C61.1 (3)C5—C4—C3—C2−1.3 (3)
C3—C2—C1—C11−176.76 (18)C41—C4—C3—C2177.59 (18)
N11—C11—C1—C2−56.8 (2)C1—C2—C3—C4−0.3 (3)
N11—C11—C1—C6125.34 (19)C14—C15—C16—C170.4 (3)
C5—C4—C41—O26.3 (3)C18—C17—C16—C15−0.2 (3)
Hydrogen-bond geometry (Å, º) top
D—H···AD—HH···AD···AD—H···A
O1—H12···N12i0.821.832.652 (2)178
C12—H7···O2ii0.932.493.213 (3)135
Symmetry codes: (i) x+1, −y+1/2, z+1/2; (ii) x−1, y, z.

Experimental details

Crystal data
Chemical formulaC15H12N2O2
Mr252.27
Crystal system, space groupMonoclinic, P21/c
Temperature (K)293
a, b, c (Å)10.435 (2), 14.360 (3), 8.2922 (17)
β (°) 96.925 (3)
V (Å3)1233.5 (4)
Z4
Radiation typeMo Kα
µ (mm−1)0.09
Crystal size (mm)0.20 × 0.20 × 0.16
Data collection
DiffractometerBruker SMART APEX CCD
Absorption correctionMulti-scan
(SADABS; Sheldrick, 1996)
Tmin, Tmax0.982, 0.985
No. of measured, independent and
observed [I > 2σ(I)] reflections		6155, 2157, 1294
Rint0.065
(sin θ/λ)max (Å−1)0.595
Refinement
R[F2 > 2σ(F2)], wR(F2), S 0.041, 0.082, 0.82
No. of reflections2157
No. of parameters160
H-atom treatmentH-atom parameters constrained
Δρmax, Δρmin (e Å−3)0.13, −0.19

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···AD—HH···AD···AD—H···A
O1—H12···N12i0.821.832.652 (2)177.5
C12—H7···O2ii0.932.493.213 (3)135.0
Symmetry codes: (i) x+1, −y+1/2, z+1/2; (ii) x−1, y, z.
 

Acknowledgements

The authors gratefully acknowledge the Natural Science Foundation of Jiangsu Province of China (BK2008195) for financial support of this work.

References

First citationBruker (1998). SMART and SAINT. Bruker AXS Inc., Madison, Wisconsin, USA.  Google Scholar
 First citationDas, M. C. & Bharadwaj, P. K. (2009). J. Am. Chem. Soc. 131, 10942–10943.  Web of Science CSD CrossRef PubMed CAS Google Scholar
 First citationHua, Q., Zhao, Y., Xu, G.-C., Chen, M.-S., Su, Z., Cai, K. & Sun, W.-Y. (2010). Cryst. Growth Des. 10, 2553–2562.  Web of Science CSD CrossRef CAS Google Scholar
 First citationKuai, H.-W. & Cheng, X.-C. (2011a). Acta Cryst. E67, submitted (AA2024).  CrossRef IUCr Journals Google Scholar
 First citationKuai, H.-W. & Cheng, X.-C. (2011b). Acta Cryst. E67, submitted (AA2025).  CrossRef IUCr Journals Google Scholar
 First citationKuai, H.-W., Cheng, X.-C. & Zhu, X.-H. (2011). J. Coord. Chem. 64, 1636–1644.  Web of Science CSD CrossRef Google Scholar
 First citationSheldrick, G. M. (1996). SADABS. University of Göttingen, Germany.  Google Scholar
 First citationSheldrick, G. M. (2008). Acta Cryst. A64, 112–122.  Web of Science CrossRef CAS IUCr Journals 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.

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ISSN: 2056-9890
Volume 67| Part 10| October 2011| Page o2787
https://doi.org/10.1107/S1600536811039043
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