2,2′-(4,6-Dinitro-1,3-phenyl­enedi­oxy)diacetic acid dihydrate

Ma, D.-S.; Zhang, X.-M.; Mu, D.; Hou, G.-F.

doi:10.1107/S1600536809041397

organic compounds

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ISSN: 2056-9890

Volume 65| Part 11| November 2009| Page o2756

https://doi.org/10.1107/S1600536809041397

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2,2′-(4,6-Dinitro-1,3-phenylenedioxy)diacetic acid dihydrate

Dong-Sheng Ma,^a ^* Xiu-Mei Zhang,^a Dan Mu ^a and Guang-Feng Hou ^a

^aCollege of Chemistry and Materials Science, Heilongjiang University, Harbin 150080, People's Republic of China
^*Correspondence e-mail: hgf1000@163.com

(Received 9 October 2009; accepted 10 October 2009; online 17 October 2009)

In the title compound, C₁₀H₈N₂O₁₀·2H₂O, the skeleton of the dicarboxylic acid molecule is approximately planar, the largest deviation being 0.477 (1) Å for an O atom of a nitro group; this nitro group is twisted out of the plane of the ring by 24.6 (1)°. Adjacent molecules are linked by O—H⋯O hydrogen bonds, which connect the dicarboxylic acid and water molecules into a three-dimensional supramolecular network.

Related literature

For general background to flexible aromatic carboxylic acids, see: Coronado et al. (2000 ). For the synthesis and related structures, see: Gao et al. (2006 ) Ma et al. (2009 )

Experimental

Crystal data

C₁₀H₈N₂O₁₀·2H₂O
M_r = 352.22
Monoclinic, P 2₁ /n
a = 8.4438 (17) Å
b = 16.049 (3) Å
c = 10.539 (2) Å
β = 93.13 (3)°
V = 1426.0 (5) Å³
Z = 4
Mo Kα radiation
μ = 0.16 mm⁻¹
T = 291 K
0.19 × 0.18 × 0.17 mm

Data collection

Rigaku R-AXIS RAPID diffractometer
Absorption correction: multi-scan (ABSCOR; Higashi, 1995 ) T_min = 0.972, T_max = 0.974
10898 measured reflections
2461 independent reflections
2059 reflections with I > 2σ(I)
R_int = 0.021

Refinement

R[F² > 2σ(F²)] = 0.045
wR(F²) = 0.130
S = 1.06
2461 reflections
217 parameters
H-atom parameters constrained
Δρ_max = 0.60 e Å⁻³
Δρ_min = −0.25 e Å⁻³

Table 1
Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
O2—H10⋯O12	0.85	1.79	2.569 (2)	152
O6—H6⋯O11	0.85	1.75	2.592 (2)	169
O12—H11⋯O3ⁱ	0.85	1.86	2.707 (2)	171
O12—H12⋯O5ⁱⁱ	0.85	2.00	2.775 (2)	152
O11—H15⋯O10ⁱⁱⁱ	0.85	2.04	2.852 (2)	160
O11—H14⋯O7^iv	0.85	2.25	3.017 (3)	151
O11—H14⋯O9ⁱⁱ	0.85	2.38	2.925 (2)	123
Symmetry codes: (i) -x+2, -y+1, -z+1; (ii) $[-x+{\script{1\over 2}}, y-{\script{1\over 2}}, -z+{\script{3\over 2}}]$ ; (iii) $[x-{\script{3\over 2}}, -y+{\script{3\over 2}}, z+{\script{1\over 2}}]$ ; (iv) $[-x-{\script{1\over 2}}, y-{\script{1\over 2}}, -z+{\script{3\over 2}}]$ .

Data collection: RAPID-AUTO (Rigaku, 1998 ); cell refinement: RAPID-AUTO; data reduction: CrystalClear (Rigaku/MSC, 2002 ); 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: SHELXL97.

Supporting information

Crystal structure: contains datablocks I, global. DOI: https://doi.org/10.1107/S1600536809041397/ng2661sup1.cif

Structure factors: contains datablock I. DOI: https://doi.org/10.1107/S1600536809041397/ng2661Isup2.hkl

checkCIF report

Comment top

Flexible aromatic carboxylic acid with oxygen is a kind of biological activity of the organic carboxylic acid, not only in agriculture, such as plant growth regulators and herbicides it is applied, but also it is important to the synthesis of some organic medicine centre body. Compared with other rigid carboxylic acid ligands, such flexible aromatic carboxylic acid have highly plasticity and spatial configuration of, so it provides a rich and colorful way to identify and assemble for constructing a novel topological network structure with the special physical and chemical properties (Coronado et al., 2000; Gao et al., 2006). In this paper, we report the synthesis and crystal structures of a new flexible aromatic carboxylic acid compound.

In the crystal structure, the skeletons of the dicarboxylic acid molecule is approximately co-planar with the largest deviation being 0.477 (1) Å from O7 of one twisty nitro group [dihedral angles = 24.6 (1)°] (Figure 1).

There are six symmetry-independent 'active' H atoms in the crystal structure, all of them participate in hydrogen bonds, which link the dicarboxylic acid and water molecules into a three-dimensional supramolecular network (Figure 2, Table 1).

Related literature top

For general background, see: Coronado et al. (2000). For the synthesis and related structures, see: Gao et al. (2006) Ma et al. (2009)

Experimental top

The synthesis of target product is as follows: chlorine acetic acid (51.6 g, 0.54 mol), sodalye (36.3 g, 0.90 mol) and resorcinol (20 g, 0.18 mol) were dissolved into 200 ml distilled water with stirring. The mixture was heated to refluxed for 6 h, then the pH value was adjusted to about 2.0 by using 3 M hydrochloric acid. After cooling to the room temperature, 10.8 g (27%) yellow precipitate was obtained. The 10.8 g above yellow product was dissolved into 100 ml concentrated sulfuric acid with stirring, and then the mixture of nitric acid (9.45 g, 0.15 mol) and sulfuric acid (20.58 g, 0.21 mol) was dropped into the above solution with keeping the reaction temperature under 0° C for 1 h. Then the rection solution is stirred about 5h at room temperature. The mixture was poured into 500 ml water solution, the crude product were obtained (37%). The product was suitable for X-ray test obtained by recrystallization from water solution.

Structure description top

For general background, see: Coronado et al. (2000). For the synthesis and related structures, see: Gao et al. (2006) Ma et al. (2009)

Computing details top

Data collection: RAPID-AUTO (Rigaku, 1998); cell refinement: RAPID-AUTO (Rigaku, 1998); data reduction: CrystalClear (Rigaku/MSC, 2002); 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: SHELXL97 (Sheldrick, 2008).

Figures top

	Fig. 1. The molecular structure of the title compound, showing displacement ellipsoids at the 50% probability level for non-H atoms.
	Fig. 2. A partial packing view, showing the three-dimensional supramolecular network. Dashed lines indicate the hydrogen-bonding interactions and no involving H atoms have been omitted.

2,2'-(4,6-Dinitro-1,3-phenylenedioxy)diacetic acid dihydrate top

Crystal data top

C₁₀H₈N₂O₁₀·2H₂O	F(000) = 728
M_r = 352.22	D_x = 1.641 Mg m⁻³
Monoclinic, P2₁/n	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: -P 2yn	Cell parameters from 10730 reflections
a = 8.4438 (17) Å	θ = 3.0–27.6°
b = 16.049 (3) Å	µ = 0.16 mm⁻¹
c = 10.539 (2) Å	T = 291 K
β = 93.13 (3)°	Block, colorless
V = 1426.0 (5) Å³	0.19 × 0.18 × 0.17 mm
Z = 4

Data collection top

Rigaku R-AXIS RAPID diffractometer	2461 independent reflections
Radiation source: fine-focus sealed tube	2059 reflections with I > 2σ(I)
Graphite monochromator	R_int = 0.021
ω scans	θ_max = 25.0°, θ_min = 3.0°
Absorption correction: multi-scan (ABSCOR; Higashi, 1995)	h = −10→10
T_min = 0.972, T_max = 0.974	k = −18→19
10898 measured reflections	l = −12→12

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)] = 0.045	Hydrogen site location: inferred from neighbouring sites
wR(F²) = 0.130	H-atom parameters constrained
S = 1.06	w = 1/[σ²(F_o²) + (0.0711P)² + 0.5856P] where P = (F_o² + 2F_c²)/3
2461 reflections	(Δ/σ)_max < 0.001
217 parameters	Δρ_max = 0.60 e Å⁻³
0 restraints	Δρ_min = −0.25 e Å⁻³

Crystal data top

C₁₀H₈N₂O₁₀·2H₂O	V = 1426.0 (5) Å³
M_r = 352.22	Z = 4
Monoclinic, P2₁/n	Mo Kα radiation
a = 8.4438 (17) Å	µ = 0.16 mm⁻¹
b = 16.049 (3) Å	T = 291 K
c = 10.539 (2) Å	0.19 × 0.18 × 0.17 mm
β = 93.13 (3)°

Data collection top

Rigaku R-AXIS RAPID diffractometer	2461 independent reflections
Absorption correction: multi-scan (ABSCOR; Higashi, 1995)	2059 reflections with I > 2σ(I)
T_min = 0.972, T_max = 0.974	R_int = 0.021
10898 measured reflections

Refinement top

R[F² > 2σ(F²)] = 0.045	0 restraints
wR(F²) = 0.130	H-atom parameters constrained
S = 1.06	Δρ_max = 0.60 e Å⁻³
2461 reflections	Δρ_min = −0.25 e Å⁻³
217 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

	x	y	z	U_iso*/U_eq
C1	0.5107 (2)	0.77890 (11)	0.61383 (18)	0.0337 (4)
C2	0.3605 (2)	0.76229 (11)	0.65578 (19)	0.0361 (4)
H2	0.3261	0.7073	0.6589	0.043*
C3	0.2606 (2)	0.82504 (11)	0.69305 (17)	0.0329 (4)
C4	0.3158 (2)	0.90822 (12)	0.68891 (18)	0.0350 (4)
C5	0.4650 (2)	0.92555 (11)	0.65097 (18)	0.0362 (4)
H5	0.5007	0.9804	0.6511	0.043*
C6	0.5625 (2)	0.86256 (12)	0.61261 (17)	0.0347 (4)
C7	0.5601 (2)	0.63511 (12)	0.5756 (2)	0.0411 (5)
H7A	0.4729	0.6256	0.5135	0.049*
H7B	0.5256	0.6202	0.6589	0.049*
C8	0.7010 (2)	0.58376 (13)	0.54410 (19)	0.0403 (5)
C9	0.0654 (2)	0.72769 (11)	0.7455 (2)	0.0394 (5)
H9A	0.1410	0.6975	0.8007	0.047*
H9B	0.0592	0.7006	0.6631	0.047*
C10	−0.0949 (2)	0.72744 (12)	0.80110 (18)	0.0356 (4)
N1	0.2172 (2)	0.97868 (10)	0.72076 (18)	0.0455 (4)
N2	0.7145 (2)	0.88676 (11)	0.56748 (17)	0.0419 (4)
O1	0.60775 (16)	0.72016 (8)	0.57395 (15)	0.0444 (4)
O2	0.6797 (2)	0.50642 (10)	0.5751 (2)	0.0691 (6)
H10	0.7650	0.4796	0.5655	0.104*
O3	0.8147 (2)	0.61073 (11)	0.4960 (2)	0.0658 (5)
O4	0.11529 (16)	0.81155 (8)	0.73285 (14)	0.0411 (4)
O5	−0.17145 (17)	0.78783 (9)	0.82313 (16)	0.0507 (4)
O6	−0.13690 (18)	0.65015 (9)	0.82352 (16)	0.0517 (4)
H6	−0.2275	0.6472	0.8546	0.077*
O7	0.0758 (2)	0.97067 (11)	0.7144 (3)	0.0895 (8)
O8	0.2816 (2)	1.04435 (10)	0.7480 (2)	0.0735 (6)
O9	0.7504 (2)	0.96008 (10)	0.5705 (2)	0.0785 (6)
O10	0.8007 (2)	0.83474 (11)	0.5236 (2)	0.0708 (6)
O12	0.8696 (2)	0.38512 (11)	0.53639 (19)	0.0681 (5)
H11	0.9690	0.3912	0.5312	0.102*
H12	0.8403	0.3486	0.5886	0.102*
O11	−0.41411 (19)	0.62047 (11)	0.90755 (19)	0.0658 (5)
H15	−0.4880	0.6455	0.9437	0.099*
H14	−0.4372	0.5696	0.8938	0.099*

Atomic displacement parameters (Å²) top

	U¹¹	U²²	U³³	U¹²	U¹³	U²³
C1	0.0292 (10)	0.0329 (10)	0.0396 (10)	−0.0014 (7)	0.0066 (7)	−0.0016 (8)
C2	0.0316 (10)	0.0276 (9)	0.0500 (11)	−0.0041 (7)	0.0097 (8)	−0.0008 (8)
C3	0.0278 (9)	0.0306 (9)	0.0406 (9)	−0.0009 (7)	0.0058 (7)	0.0007 (8)
C4	0.0348 (10)	0.0284 (9)	0.0421 (10)	0.0001 (7)	0.0048 (8)	0.0011 (8)
C5	0.0387 (11)	0.0282 (9)	0.0419 (10)	−0.0061 (8)	0.0029 (8)	0.0038 (8)
C6	0.0292 (10)	0.0357 (10)	0.0394 (10)	−0.0059 (8)	0.0037 (7)	0.0029 (8)
C7	0.0317 (10)	0.0316 (10)	0.0609 (12)	−0.0027 (8)	0.0118 (9)	−0.0036 (9)
C8	0.0323 (10)	0.0401 (11)	0.0492 (11)	−0.0007 (8)	0.0087 (8)	−0.0063 (9)
C9	0.0355 (11)	0.0279 (9)	0.0563 (12)	−0.0013 (8)	0.0160 (9)	−0.0007 (8)
C10	0.0315 (10)	0.0360 (10)	0.0398 (10)	−0.0018 (8)	0.0067 (8)	−0.0027 (8)
N1	0.0459 (11)	0.0298 (9)	0.0621 (11)	0.0026 (7)	0.0157 (8)	0.0040 (8)
N2	0.0323 (9)	0.0402 (10)	0.0539 (10)	−0.0082 (7)	0.0071 (7)	0.0044 (8)
O1	0.0322 (7)	0.0332 (7)	0.0699 (10)	−0.0040 (6)	0.0209 (7)	−0.0073 (7)
O2	0.0519 (10)	0.0419 (9)	0.1163 (15)	0.0113 (7)	0.0309 (10)	0.0068 (9)
O3	0.0457 (10)	0.0585 (10)	0.0968 (13)	0.0050 (8)	0.0355 (9)	0.0015 (9)
O4	0.0300 (7)	0.0279 (7)	0.0669 (9)	−0.0009 (5)	0.0168 (6)	0.0000 (6)
O5	0.0364 (8)	0.0441 (8)	0.0733 (10)	0.0032 (6)	0.0183 (7)	−0.0047 (7)
O6	0.0414 (8)	0.0395 (8)	0.0765 (10)	−0.0070 (6)	0.0258 (7)	0.0029 (7)
O7	0.0444 (11)	0.0385 (9)	0.189 (2)	0.0076 (8)	0.0335 (13)	0.0009 (11)
O8	0.0688 (12)	0.0327 (9)	0.1204 (16)	−0.0043 (8)	0.0192 (11)	−0.0199 (9)
O9	0.0521 (11)	0.0445 (10)	0.1419 (19)	−0.0196 (8)	0.0315 (11)	−0.0013 (10)
O10	0.0527 (10)	0.0550 (10)	0.1092 (15)	−0.0120 (8)	0.0448 (10)	−0.0093 (10)
O12	0.0514 (10)	0.0634 (11)	0.0912 (13)	0.0040 (8)	0.0191 (9)	0.0121 (9)
O11	0.0462 (10)	0.0549 (10)	0.0995 (14)	−0.0074 (8)	0.0323 (9)	−0.0081 (9)

Geometric parameters (Å, º) top

C1—O1	1.332 (2)	C8—O2	1.298 (3)
C1—C2	1.392 (3)	C9—O4	1.419 (2)
C1—C6	1.412 (3)	C9—C10	1.504 (3)
C2—C3	1.384 (3)	C9—H9A	0.9700
C2—H2	0.9300	C9—H9B	0.9700
C3—O4	1.336 (2)	C10—O5	1.195 (2)
C3—C4	1.415 (3)	C10—O6	1.315 (2)
C4—C5	1.371 (3)	N1—O7	1.200 (2)
C4—N1	1.454 (3)	N1—O8	1.213 (2)
C5—C6	1.379 (3)	N2—O9	1.215 (2)
C5—H5	0.9300	N2—O10	1.216 (2)
C6—N2	1.446 (2)	O2—H10	0.8500
C7—O1	1.423 (2)	O6—H6	0.8500
C7—C8	1.499 (3)	O12—H11	0.8500
C7—H7A	0.9700	O12—H12	0.8500
C7—H7B	0.9700	O11—H15	0.8500
C8—O3	1.191 (3)	O11—H14	0.8500

O1—C1—C2	123.49 (17)	O3—C8—O2	125.5 (2)
O1—C1—C6	118.27 (16)	O3—C8—C7	124.2 (2)
C2—C1—C6	118.24 (17)	O2—C8—C7	110.32 (17)
C3—C2—C1	122.07 (17)	O4—C9—C10	108.50 (15)
C3—C2—H2	119.0	O4—C9—H9A	110.0
C1—C2—H2	119.0	C10—C9—H9A	110.0
O4—C3—C2	123.74 (16)	O4—C9—H9B	110.0
O4—C3—C4	118.18 (16)	C10—C9—H9B	110.0
C2—C3—C4	118.08 (17)	H9A—C9—H9B	108.4
C5—C4—C3	120.65 (17)	O5—C10—O6	125.20 (18)
C5—C4—N1	117.14 (17)	O5—C10—C9	125.55 (18)
C3—C4—N1	122.19 (17)	O6—C10—C9	109.24 (16)
C4—C5—C6	120.67 (17)	O7—N1—O8	122.56 (19)
C4—C5—H5	119.7	O7—N1—C4	118.99 (18)
C6—C5—H5	119.7	O8—N1—C4	118.39 (18)
C5—C6—C1	120.27 (17)	O9—N2—O10	121.43 (18)
C5—C6—N2	117.05 (17)	O9—N2—C6	118.43 (18)
C1—C6—N2	122.64 (17)	O10—N2—C6	120.08 (17)
O1—C7—C8	107.23 (15)	C1—O1—C7	119.71 (15)
O1—C7—H7A	110.3	C8—O2—H10	109.0
C8—C7—H7A	110.3	C3—O4—C9	117.76 (14)
O1—C7—H7B	110.3	C10—O6—H6	112.3
C8—C7—H7B	110.3	H11—O12—H12	116.4
H7A—C7—H7B	108.5	H15—O11—H14	111.3

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
O2—H10···O12	0.85	1.79	2.569 (2)	152
O6—H6···O11	0.85	1.75	2.592 (2)	169
O12—H11···O3ⁱ	0.85	1.86	2.707 (2)	171
O12—H12···O5ⁱⁱ	0.85	2.00	2.775 (2)	152
O11—H15···O10ⁱⁱⁱ	0.85	2.04	2.852 (2)	160
O11—H14···O7^iv	0.85	2.25	3.017 (3)	151
O11—H14···O9ⁱⁱ	0.85	2.38	2.925 (2)	123

Symmetry codes: (i) −x+2, −y+1, −z+1; (ii) −x+1/2, y−1/2, −z+3/2; (iii) x−3/2, −y+3/2, z+1/2; (iv) −x−1/2, y−1/2, −z+3/2.

Experimental details

Crystal data
Chemical formula	C₁₀H₈N₂O₁₀·2H₂O
M_r	352.22
Crystal system, space group	Monoclinic, P2₁/n
Temperature (K)	291
a, b, c (Å)	8.4438 (17), 16.049 (3), 10.539 (2)
β (°)	93.13 (3)
V (Å³)	1426.0 (5)
Z	4
Radiation type	Mo Kα
µ (mm⁻¹)	0.16
Crystal size (mm)	0.19 × 0.18 × 0.17

Data collection
Diffractometer	Rigaku R-AXIS RAPID
Absorption correction	Multi-scan (ABSCOR; Higashi, 1995)
T_min, T_max	0.972, 0.974
No. of measured, independent and observed [I > 2σ(I)] reflections	10898, 2461, 2059
R_int	0.021
(sin θ/λ)_max (Å⁻¹)	0.594

Refinement
R[F² > 2σ(F²)], wR(F²), S	0.045, 0.130, 1.06
No. of reflections	2461
No. of parameters	217
H-atom treatment	H-atom parameters constrained
Δρ_max, Δρ_min (e Å⁻³)	0.60, −0.25

Computer programs: RAPID-AUTO (Rigaku, 1998), CrystalClear (Rigaku/MSC, 2002), 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
O2—H10···O12	0.85	1.79	2.569 (2)	151.6
O6—H6···O11	0.85	1.75	2.592 (2)	168.5
O12—H11···O3ⁱ	0.85	1.86	2.707 (2)	170.9
O12—H12···O5ⁱⁱ	0.85	2.00	2.775 (2)	151.5
O11—H15···O10ⁱⁱⁱ	0.85	2.04	2.852 (2)	159.9
O11—H14···O7^iv	0.85	2.25	3.017 (3)	150.9
O11—H14···O9ⁱⁱ	0.85	2.38	2.925 (2)	122.6

Symmetry codes: (i) −x+2, −y+1, −z+1; (ii) −x+1/2, y−1/2, −z+3/2; (iii) x−3/2, −y+3/2, z+1/2; (iv) −x−1/2, y−1/2, −z+3/2.

Acknowledgements

The authors thank Heilongjiang University for supporting this study.

References

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