Poly[[bis­(μ-3-amino-5-carb­oxy­benzoato-κ2N:O1)diaqua­zinc] dihydrate]

Zhang, K.-L.; Qiu, T.-T.; Ng, S.W.

doi:10.1107/S1600536812031789

metal-organic compounds

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ISSN: 2056-9890

Volume 68| Part 8| August 2012| Page m1088

https://doi.org/10.1107/S1600536812031789

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Poly[[bis(μ-3-amino-5-carboxybenzoato-κ²N:O¹)diaquazinc] dihydrate]

Kou-Lin Zhang,^a Ting-Ting Qiu ^a and Seik Weng Ng ^b,^c ^*

^aCollege of Chemistry and Chemical Engineering, Yangzhou University, Yangzhou 225002, People's Republic of China, ^bDepartment of Chemistry, University of Malaya, 50603 Kuala Lumpur, Malaysia, and ^cChemistry Department, King Abdulaziz University, PO Box 80203 Jeddah, Saudi Arabia
^*Correspondence e-mail: seikweng@um.edu.my

(Received 2 July 2012; accepted 12 July 2012; online 18 July 2012)

The Zn^II atom in the title polymeric compound, {[Zn(C₈H₆NO₄)₂(H₂O)₂]·2H₂O}_n, lies on a center of inversion and is coordinated by two amine N atoms and two carboxylate O atoms from two 3-amino-5-carboxybenzoate anions along with two water molecules in a distorted octahedral geometry. The bridging nature of the anion generates a layer motif parallel to (100). Hydrogen bonds of the N—H⋯O and O—H⋯O types exist in the structure. One H atom of the coordinated water molecule and one H atom of the solvent water molecule are each disordered over two positions in a 1:1 ratio.

Related literature

For catena-poly[(5-aminoisophthalato)aquazinc], see: Wu et al. (2002 ).

Experimental

Crystal data

[Zn(C₈H₆NO₄)₂(H₂O)₂]·2H₂O
M_r = 497.71
Monoclinic, C 2/c
a = 14.2209 (10) Å
b = 11.2252 (8) Å
c = 12.7139 (9) Å
β = 113.286 (1)°
V = 1864.2 (2) Å³
Z = 4
Mo Kα radiation
μ = 1.39 mm⁻¹
T = 293 K
0.30 × 0.26 × 0.18 mm

Data collection

Bruker SMART APEX diffractometer
Absorption correction: multi-scan (SADABS; Sheldrick, 1996 ) T_min = 0.680, T_max = 0.788
8005 measured reflections
2130 independent reflections
1843 reflections with I > 2σ(I)
R_int = 0.018

Refinement

R[F² > 2σ(F²)] = 0.034
wR(F²) = 0.098
S = 1.07
2130 reflections
144 parameters
H-atom parameters constrained
Δρ_max = 0.37 e Å⁻³
Δρ_min = −0.37 e Å⁻³

Table 1
Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
O3—H1⋯O2Wⁱ	0.84	1.84	2.675 (3)	172
O1W—H2⋯O2ⁱⁱ	0.84	1.97	2.695 (3)	143
O2W—H4⋯O2	0.84	1.79	2.619 (3)	170
O2W—H5⋯O2Wⁱⁱⁱ	0.84	2.03	2.869 (5)	171
O2W—H5′⋯O1^iv	0.84	2.31	3.106 (3)	158
O2W—H5′⋯O1W^iv	0.84	2.35	2.910 (3)	125
N1—H6⋯O4^v	0.88	2.14	3.013 (3)	172
N1—H7⋯O4^vi	0.88	2.21	3.059 (2)	161
Symmetry codes: (i) $[x, -y, z+{\script{1\over 2}}]$ ; (ii) $[-x+{\script{1\over 2}}, -y+{\script{1\over 2}}, -z]$ ; (iii) $[-x, y, -z+{\script{1\over 2}}]$ ; (iv) $[-x+{\script{1\over 2}}, y-{\script{1\over 2}}, -z+{\script{1\over 2}}]$ ; (v) -x, -y+1, -z+1; (vi) $[x, -y+1, z-{\script{1\over 2}}]$ .

Data collection: APEX2 (Bruker, 2005 ); cell refinement: SAINT (Bruker, 2005); data reduction: SAINT; program(s) used to solve structure: SHELXS97 (Sheldrick, 2008 ); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008); molecular graphics: OLEX (Dolomanov et al., 2003 ) and X-SEED (Barbour, 2001 ); software used to prepare material for publication: publCIF (Westrip, 2010 ).

Supporting information

Crystal structure: contains datablocks global, I. DOI: https://doi.org/10.1107/S1600536812031789/xu5588sup1.cif

Structure factors: contains datablock I. DOI: https://doi.org/10.1107/S1600536812031789/xu5588Isup2.hkl

checkCIF report

Comment top

5-Aminoisophthalic acid furnishes a zinc derivative in which the ligand is dibasic; the dianion functions in a u3-bridging mode in monoaqua compound, which adopts a chain structure (Wu et al., 2002). The title compound (Scheme I) was the unexpected when nicotinamide was added to the reaction.

The Zn^II atom in of polymeric [Zn(H₂O)₂(C₈H₆NO₄)2^.2H₂O]_n lies in a octahedron that is composed of two amino N atoms and two carboxyl O atoms (from two 5-aminoisophthalate anions) along with two water molecules (Fig. 1). The bridging nature of the anion generates a layer motif parallel to [1 0 0] (Fig. 2). Hydrogen bonds of the N–H···O and O–H···O type exist within the layer (Table 1).

Related literature top

For catena-poly[(5-aminoisophthalato)aquazinc], see: Wu et al. (2002).

Experimental top

5-Aminoisophthalic acid (0.030 g, 0.165 mmol) and sodium hydroxide (0.013 g, 0.330 mmol) were dissolved in a water/methanol (1:1 v/v; 10 ml) mixture. Zinc acetate hexahydrate (0.049 g, 0.165 mmol) dissolved in a water/methanol (1:1 v/v; 3 ml) mixture and nicotinamide (0.050 g, 0.33 mmol) dissolved in water (3 ml) were added. The solution was filtered. Light brown crystals were isolated after several days.

Structure description top

For catena-poly[(5-aminoisophthalato)aquazinc], see: Wu et al. (2002).

Computing details top

Data collection: APEX2 (Bruker, 2005); cell refinement: SAINT (Bruker, 2005); data reduction: SAINT (Bruker, 2005); program(s) used to solve structure: SHELXS97 (Sheldrick, 2008); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008); molecular graphics: OLEX (Dolomanov et al., 2003) and X-SEED (Barbour, 2001); software used to prepare material for publication: publCIF (Westrip, 2010).

Figures top

	Fig. 1. Thermal ellipsoid plot (Barbour, 2001) of a portion of polymeric Zn(H₂O)₂(C₈H₆NO₄)2^.2H₂O at the 50% probability level; hydrogen atoms are drawn as spheres of arbitrary radius. The disorder in the hydrogen atoms of the coordinated and lattice water molecules is not shown.
	Fig. 2. Layer motif represented as an OLEX-type (Dolomanov et al., 2003) of network.

Poly[[bis(µ-3-amino-5-carboxybenzoato- κ²N:O¹)diaquazinc] dihydrate] top

Crystal data top

[Zn(C₈H₆NO₄)₂(H₂O)₂]·2H₂O	F(000) = 1024
M_r = 497.71	D_x = 1.773 Mg m⁻³
Monoclinic, C2/c	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: -C 2yc	Cell parameters from 4815 reflections
a = 14.2209 (10) Å	θ = 2.4–28.2°
b = 11.2252 (8) Å	µ = 1.39 mm⁻¹
c = 12.7139 (9) Å	T = 293 K
β = 113.286 (1)°	Prism, light brown
V = 1864.2 (2) Å³	0.30 × 0.26 × 0.18 mm
Z = 4

Data collection top

Bruker SMART APEX diffractometer	2130 independent reflections
Radiation source: fine-focus sealed tube	1843 reflections with I > 2σ(I)
Graphite monochromator	R_int = 0.018
ω scans	θ_max = 27.5°, θ_min = 2.4°
Absorption correction: multi-scan (SADABS; Sheldrick, 1996)	h = −18→15
T_min = 0.680, T_max = 0.788	k = −14→14
8005 measured reflections	l = −16→16

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)] = 0.034	Hydrogen site location: inferred from neighbouring sites
wR(F²) = 0.098	H-atom parameters constrained
S = 1.07	w = 1/[σ²(F_o²) + (0.0506P)² + 3.2779P] where P = (F_o² + 2F_c²)/3
2130 reflections	(Δ/σ)_max = 0.001
144 parameters	Δρ_max = 0.37 e Å⁻³
0 restraints	Δρ_min = −0.37 e Å⁻³

Crystal data top

[Zn(C₈H₆NO₄)₂(H₂O)₂]·2H₂O	V = 1864.2 (2) Å³
M_r = 497.71	Z = 4
Monoclinic, C2/c	Mo Kα radiation
a = 14.2209 (10) Å	µ = 1.39 mm⁻¹
b = 11.2252 (8) Å	T = 293 K
c = 12.7139 (9) Å	0.30 × 0.26 × 0.18 mm
β = 113.286 (1)°

Data collection top

Bruker SMART APEX diffractometer	2130 independent reflections
Absorption correction: multi-scan (SADABS; Sheldrick, 1996)	1843 reflections with I > 2σ(I)
T_min = 0.680, T_max = 0.788	R_int = 0.018
8005 measured reflections

Refinement top

R[F² > 2σ(F²)] = 0.034	0 restraints
wR(F²) = 0.098	H-atom parameters constrained
S = 1.07	Δρ_max = 0.37 e Å⁻³
2130 reflections	Δρ_min = −0.37 e Å⁻³
144 parameters

Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Å²) top

	x	y	z	U_iso*/U_eq	Occ. (<1)
Zn1	0.2500	0.2500	0.0000	0.02950 (14)
O1	0.20751 (15)	0.32463 (16)	0.12770 (14)	0.0412 (4)
O2	0.1529 (2)	0.1571 (2)	0.1754 (2)	0.0655 (7)
O3	0.09628 (17)	0.14472 (16)	0.53610 (16)	0.0436 (4)
H1	0.0885	0.1154	0.5929	0.065*
O4	0.07472 (15)	0.31377 (16)	0.61500 (15)	0.0408 (4)
O1W	0.35790 (16)	0.38916 (19)	0.03707 (18)	0.0531 (5)
H2	0.3743	0.3994	−0.0189	0.080*
H3	0.4102	0.3714	0.0953	0.080*	0.50
H3'	0.3322	0.4522	0.0496	0.080*	0.50
O2W	0.0898 (2)	−0.04635 (18)	0.22475 (18)	0.0594 (6)
H4	0.1052	0.0229	0.2118	0.089*
H5	0.0334	−0.0439	0.2320	0.089*	0.50
H5'	0.1397	−0.0755	0.2797	0.089*	0.50
N1	0.12864 (15)	0.64309 (17)	0.36983 (16)	0.0312 (4)
H6	0.0705	0.6633	0.3742	0.037*
H7	0.1250	0.6675	0.3025	0.037*
C1	0.1718 (2)	0.2655 (2)	0.1878 (2)	0.0349 (5)
C2	0.15207 (17)	0.3304 (2)	0.28176 (18)	0.0291 (4)
C3	0.15228 (17)	0.4538 (2)	0.28397 (18)	0.0294 (5)
H3A	0.1667	0.4963	0.2293	0.035*
C4	0.13087 (16)	0.5152 (2)	0.36787 (17)	0.0274 (4)
C5	0.11166 (17)	0.4506 (2)	0.45058 (18)	0.0295 (5)
H5A	0.0982	0.4904	0.5073	0.035*
C6	0.11247 (17)	0.3261 (2)	0.44894 (17)	0.0277 (4)
C7	0.13167 (19)	0.2662 (2)	0.3638 (2)	0.0302 (5)
H7A	0.1309	0.1834	0.3618	0.036*
C8	0.09264 (19)	0.2626 (2)	0.54063 (19)	0.0309 (5)

Atomic displacement parameters (Å²) top

	U¹¹	U²²	U³³	U¹²	U¹³	U²³
Zn1	0.0412 (2)	0.0297 (2)	0.0248 (2)	−0.00028 (15)	0.02079 (16)	−0.00161 (13)
O1	0.0631 (12)	0.0436 (10)	0.0312 (9)	0.0127 (9)	0.0339 (8)	0.0038 (7)
O2	0.121 (2)	0.0466 (12)	0.0583 (13)	−0.0156 (13)	0.0664 (14)	−0.0190 (10)
O3	0.0725 (13)	0.0354 (9)	0.0375 (9)	0.0045 (9)	0.0374 (9)	0.0025 (7)
O4	0.0639 (12)	0.0404 (10)	0.0321 (9)	−0.0022 (9)	0.0340 (8)	−0.0024 (7)
O1W	0.0501 (11)	0.0531 (12)	0.0538 (12)	−0.0046 (9)	0.0181 (9)	−0.0207 (10)
O2W	0.1023 (18)	0.0426 (11)	0.0469 (11)	0.0111 (11)	0.0441 (12)	0.0074 (9)
N1	0.0419 (11)	0.0334 (10)	0.0242 (9)	0.0046 (8)	0.0194 (8)	0.0030 (7)
C1	0.0436 (13)	0.0414 (14)	0.0258 (11)	0.0043 (10)	0.0203 (10)	−0.0048 (9)
C2	0.0323 (11)	0.0388 (12)	0.0199 (9)	0.0037 (9)	0.0142 (8)	−0.0027 (8)
C3	0.0324 (11)	0.0394 (12)	0.0203 (9)	0.0035 (9)	0.0148 (8)	0.0011 (8)
C4	0.0290 (10)	0.0343 (11)	0.0208 (9)	0.0016 (9)	0.0118 (8)	−0.0011 (8)
C5	0.0340 (11)	0.0367 (12)	0.0227 (10)	0.0037 (9)	0.0165 (9)	−0.0024 (8)
C6	0.0295 (11)	0.0366 (11)	0.0200 (9)	0.0015 (9)	0.0129 (8)	0.0000 (8)
C7	0.0376 (12)	0.0323 (11)	0.0256 (10)	0.0033 (9)	0.0178 (9)	−0.0022 (8)
C8	0.0356 (11)	0.0380 (12)	0.0233 (10)	0.0028 (9)	0.0160 (9)	0.0013 (8)

Geometric parameters (Å, º) top

Zn1—O1W	2.108 (2)	O2W—H5'	0.8407
Zn1—O1Wⁱ	2.108 (2)	N1—C4	1.436 (3)
Zn1—O1	2.1163 (16)	N1—Zn1^iv	2.214 (2)
Zn1—O1ⁱ	2.1163 (16)	N1—H6	0.8800
Zn1—N1ⁱⁱ	2.214 (2)	N1—H7	0.8800
Zn1—N1ⁱⁱⁱ	2.214 (2)	C1—C2	1.517 (3)
O1—C1	1.261 (3)	C2—C7	1.390 (3)
O2—C1	1.243 (3)	C2—C3	1.386 (3)
O3—C8	1.326 (3)	C3—C4	1.401 (3)
O3—H1	0.8400	C3—H3A	0.9300
O4—C8	1.217 (3)	C4—C5	1.390 (3)
O1W—H2	0.8400	C5—C6	1.398 (3)
O1W—H3	0.8400	C5—H5A	0.9300
O1W—H3'	0.8400	C6—C7	1.390 (3)
O2W—H4	0.8408	C6—C8	1.486 (3)
O2W—H5	0.8425	C7—H7A	0.9300

O1W—Zn1—O1Wⁱ	180.00 (9)	Zn1^iv—N1—H6	106.7
O1W—Zn1—O1	86.47 (8)	C4—N1—H7	106.7
O1Wⁱ—Zn1—O1	93.53 (8)	Zn1^iv—N1—H7	106.7
O1W—Zn1—O1ⁱ	93.53 (8)	H6—N1—H7	106.6
O1Wⁱ—Zn1—O1ⁱ	86.47 (8)	O2—C1—O1	123.9 (2)
O1—Zn1—O1ⁱ	180.00 (8)	O2—C1—C2	118.2 (2)
O1W—Zn1—N1ⁱⁱ	92.80 (8)	O1—C1—C2	117.9 (2)
O1Wⁱ—Zn1—N1ⁱⁱ	87.20 (8)	C7—C2—C3	120.2 (2)
O1—Zn1—N1ⁱⁱ	89.10 (7)	C7—C2—C1	120.1 (2)
O1ⁱ—Zn1—N1ⁱⁱ	90.90 (7)	C3—C2—C1	119.8 (2)
O1W—Zn1—N1ⁱⁱⁱ	87.20 (8)	C2—C3—C4	120.5 (2)
O1Wⁱ—Zn1—N1ⁱⁱⁱ	92.80 (8)	C2—C3—H3A	119.7
O1—Zn1—N1ⁱⁱⁱ	90.90 (7)	C4—C3—H3A	119.7
O1ⁱ—Zn1—N1ⁱⁱⁱ	89.10 (7)	C5—C4—C3	119.1 (2)
N1ⁱⁱ—Zn1—N1ⁱⁱⁱ	180.00 (18)	C5—C4—N1	119.72 (19)
C1—O1—Zn1	124.19 (16)	C3—C4—N1	121.18 (19)
C8—O3—H1	109.5	C4—C5—C6	120.31 (19)
Zn1—O1W—H2	109.5	C4—C5—H5A	119.8
Zn1—O1W—H3	109.5	C6—C5—H5A	119.8
H2—O1W—H3	109.5	C7—C6—C5	120.1 (2)
Zn1—O1W—H3'	109.5	C7—C6—C8	122.4 (2)
H2—O1W—H3'	109.5	C5—C6—C8	117.58 (19)
H3—O1W—H3'	109.5	C2—C7—C6	119.8 (2)
H4—O2W—H5	108.9	C2—C7—H7A	120.1
H4—O2W—H5'	108.8	C6—C7—H7A	120.1
H5—O2W—H5'	116.7	O4—C8—O3	121.9 (2)
C4—N1—Zn1^iv	122.60 (14)	O4—C8—C6	123.1 (2)
C4—N1—H6	106.7	O3—C8—C6	114.96 (19)

O1W—Zn1—O1—C1	−150.9 (2)	Zn1^iv—N1—C4—C5	72.4 (2)
O1Wⁱ—Zn1—O1—C1	29.1 (2)	Zn1^iv—N1—C4—C3	−107.5 (2)
N1ⁱⁱ—Zn1—O1—C1	116.2 (2)	C3—C4—C5—C6	−0.8 (3)
N1ⁱⁱⁱ—Zn1—O1—C1	−63.8 (2)	N1—C4—C5—C6	179.3 (2)
Zn1—O1—C1—O2	−3.4 (4)	C4—C5—C6—C7	−0.6 (3)
Zn1—O1—C1—C2	175.68 (15)	C4—C5—C6—C8	179.3 (2)
O2—C1—C2—C7	11.5 (4)	C3—C2—C7—C6	−0.7 (3)
O1—C1—C2—C7	−167.7 (2)	C1—C2—C7—C6	−179.2 (2)
O2—C1—C2—C3	−167.1 (3)	C5—C6—C7—C2	1.3 (3)
O1—C1—C2—C3	13.8 (3)	C8—C6—C7—C2	−178.5 (2)
C7—C2—C3—C4	−0.7 (3)	C7—C6—C8—O4	−179.2 (2)
C1—C2—C3—C4	177.9 (2)	C5—C6—C8—O4	1.0 (3)
C2—C3—C4—C5	1.4 (3)	C7—C6—C8—O3	1.0 (3)
C2—C3—C4—N1	−178.7 (2)	C5—C6—C8—O3	−178.8 (2)

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

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
O3—H1···O2W^v	0.84	1.84	2.675 (3)	172
O1W—H2···O2ⁱ	0.84	1.97	2.695 (3)	143
O2W—H4···O2	0.84	1.79	2.619 (3)	170
O2W—H5···O2W^vi	0.84	2.03	2.869 (5)	171
O2W—H5′···O1ⁱⁱⁱ	0.84	2.31	3.106 (3)	158
O2W—H5′···O1Wⁱⁱⁱ	0.84	2.35	2.910 (3)	125
N1—H6···O4^vii	0.88	2.14	3.013 (3)	172
N1—H7···O4ⁱⁱ	0.88	2.21	3.059 (2)	161

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

Experimental details

Crystal data
Chemical formula	[Zn(C₈H₆NO₄)₂(H₂O)₂]·2H₂O
M_r	497.71
Crystal system, space group	Monoclinic, C2/c
Temperature (K)	293
a, b, c (Å)	14.2209 (10), 11.2252 (8), 12.7139 (9)
β (°)	113.286 (1)
V (Å³)	1864.2 (2)
Z	4
Radiation type	Mo Kα
µ (mm⁻¹)	1.39
Crystal size (mm)	0.30 × 0.26 × 0.18

Data collection
Diffractometer	Bruker SMART APEX
Absorption correction	Multi-scan (SADABS; Sheldrick, 1996)
T_min, T_max	0.680, 0.788
No. of measured, independent and observed [I > 2σ(I)] reflections	8005, 2130, 1843
R_int	0.018
(sin θ/λ)_max (Å⁻¹)	0.650

Refinement
R[F² > 2σ(F²)], wR(F²), S	0.034, 0.098, 1.07
No. of reflections	2130
No. of parameters	144
H-atom treatment	H-atom parameters constrained
Δρ_max, Δρ_min (e Å⁻³)	0.37, −0.37

Computer programs: APEX2 (Bruker, 2005), SAINT (Bruker, 2005), SHELXS97 (Sheldrick, 2008), SHELXL97 (Sheldrick, 2008), OLEX (Dolomanov et al., 2003) and X-SEED (Barbour, 2001), publCIF (Westrip, 2010).

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
O3—H1···O2Wⁱ	0.84	1.84	2.675 (3)	172.3
O1W—H2···O2ⁱⁱ	0.84	1.97	2.695 (3)	143.1
O2W—H4···O2	0.84	1.79	2.619 (3)	169.9
O2W—H5···O2Wⁱⁱⁱ	0.84	2.03	2.869 (5)	170.9
O2W—H5'···O1^iv	0.84	2.31	3.106 (3)	157.9
O2W—H5'···O1W^iv	0.84	2.35	2.910 (3)	124.5
N1—H6···O4^v	0.88	2.14	3.013 (3)	171.9
N1—H7···O4^vi	0.88	2.21	3.059 (2)	161.3

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

Acknowledgements

This study is a project funded by the Priority Academic Development Program of Jiangsu Higher Education Institution. We thank Yangzhou University and the Ministry of Higher Education of Malaysia (grant No. UM.C/HIR/MOHE/SC/12) for supporting this study.

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