Dibenzo-18-crown-6–picric acid–water (1/2/3)

Saleh, M.I.; Kusrini, E.; Rosli, M.M.; Fun, H.-K.

doi:10.1107/S1600536808018485

organic compounds

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ISSN: 2056-9890

Volume 64| Part 7| July 2008| Pages o1318-o1319

doi:10.1107/S1600536808018485

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Dibenzo-18-crown-6–picric acid–water (1/2/3)

Muhammad Idiris Saleh,^a Eny Kusrini,^a Mohd Mustaqim Rosli ^b and Hoong-Kun Fun ^b ^*

^aSchool of Chemical Sciences, Universiti Sains Malaysia, 11800 USM, Penang, Malaysia, and ^bX-ray Crystallography Unit, School of Physics, Universiti Sains Malaysia, 11800 USM, Penang, Malaysia
^*Correspondence e-mail: hkfun@usm.my

(Received 16 June 2008; accepted 18 June 2008; online 21 June 2008)

In the crown ether ring of the title compound, C₂₀H₂₄O₆·2C₆H₃N₃O₇·3H₂O, the O—C(H₂)—C(H₂)—O torsion angles indicate a gauche conformation of the ethyleneoxy units, while the C—O—C—C torsion angles indicate planarity of these segments; the dihedral angle between the two benzene rings is 44.53 (13)°. In both picric acid molecules, one of the nitro groups is twisted away from the attached ring. The molecules are linked into chains along the b axis via intermolecular O—H⋯O hydrogen bonds. In addition, the crystal structure is stabilized by C—H⋯O hydrogen bonds and π–π interactions [centroid–centroid distance between benzene rings = 3.5697 (16) Å].

Related literature

For bond-length data, see: Allen et al. (1987 ). For related literature, see: Bush & Truter (1971 ); Colquhoun et al. (1986 ); Kanters et al. (1986 ); Lu et al. (1993a ,b ); Robinson et al. (1987 ); Saleh et al. (1996 , 1997 ); You et al. (2002 ); Zhou et al. (1996 ).

Experimental

Crystal data

C₂₀H₂₄O₆·2C₆H₃N₃O₇·3H₂O
M_r = 872.67
Orthorhombic, P n a 2₁
a = 16.4192 (2) Å
b = 7.0845 (1) Å
c = 31.4135 (4) Å
V = 3654.08 (8) Å³
Z = 4
Mo Kα radiation
μ = 0.14 mm⁻¹
T = 100.0 (1) K
0.36 × 0.32 × 0.16 mm

Data collection

Bruker SMART APEXII CCD area-detector diffractometer
Absorption correction: multi-scan (SADABS; Bruker, 2005 ) T_min = 0.952, T_max = 0.979
37248 measured reflections
5431 independent reflections
4559 reflections with I > 2σ(I)
R_int = 0.045

Refinement

R[F² > 2σ(F²)] = 0.044
wR(F²) = 0.110
S = 1.06
5431 reflections
550 parameters
1 restraint
H-atom parameters constrained
Δρ_max = 0.40 e Å⁻³
Δρ_min = −0.33 e Å⁻³

Table 1
Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
O7—H1O7⋯O3W	1.00	1.92	2.618 (3)	124
O7—H1O7⋯O13	1.00	1.84	2.664 (3)	138
O7—H1O7⋯N3	1.00	2.49	2.985 (3)	110
O1W—H1W1⋯O6	0.87	2.14	2.978 (3)	162
O1W—H2W1⋯O2W	0.94	2.03	2.900 (4)	152
O2W—H1W2⋯O1ⁱ	0.85	2.56	3.215 (3)	135
O2W—H1W2⋯O2ⁱ	0.85	2.45	3.265 (3)	162
O2W—H2W2⋯O4ⁱ	0.85	2.42	3.198 (3)	152
O2W—H2W2⋯O5ⁱ	0.85	2.43	3.155 (3)	144
O3W—H1W3⋯O3	0.85	2.02	2.861 (3)	173
O3W—H2W3⋯O1W	0.95	1.96	2.881 (3)	163
O14—H14B⋯O1W	0.78	2.06	2.732 (3)	144
O14—H14B⋯O20	0.78	2.05	2.632 (3)	131
C3—H3A⋯O11ⁱⁱ	0.93	2.60	3.323 (4)	136
C7—H7A⋯O6ⁱⁱⁱ	0.97	2.58	3.393 (3)	142
C7—H7B⋯O19^iv	0.97	2.59	3.135 (4)	116
C9—H9A⋯O12ⁱⁱⁱ	0.97	2.39	3.341 (4)	165
C19—H19A⋯O19^v	0.97	2.53	3.301 (3)	137
Symmetry codes: (i) x, y+1, z; (ii) $[-x+{\script{1\over 2}}, y-{\script{1\over 2}}, z+{\script{1\over 2}}]$ ; (iii) $[x-{\script{1\over 2}}, -y+{\script{1\over 2}}, z]$ ; (iv) x, y-1, z; (v) $[x+{\script{1\over 2}}, -y+{\script{1\over 2}}, z]$ .

Data collection: APEX2 (Bruker, 2005); cell refinement: APEX2; data reduction: SAINT (Bruker, 2005); program(s) used to solve structure: SHELXTL (Sheldrick, 2008 ); program(s) used to refine structure: SHELXTL; molecular graphics: SHELXTL; software used to prepare material for publication: SHELXTL and PLATON (Spek, 2003 ).

Supporting information

Crystal structure: contains datablocks global, I. DOI: 10.1107/S1600536808018485/ci2617sup1.cif

Structure factors: contains datablock I. DOI: 10.1107/S1600536808018485/ci2617Isup2.hkl

checkCIF report

Comment top

The lanthanide complexes with crown ethers have been previously reported e.g. [Ln(NO₃)₂(H₂O)₂(DB30C10)₂].[Ln(NO₃)₅]. CH₃CN {Ln = Sm - Lu} (Lu et al., 1993a), [Gd(NO₃)₃(H₂O)₃].(DB24C8) (Lu et al., 1993b) and Ln(Pic)₃.(B15C5)₂nH₂O {Ln = Nd, Sm, Er} (Zhou et al., 1996) where DB30C10 is dibenzo-30-crown-10, DB24C8 is dibenzo-24-crown-8, B15C5 is benzo-15-crown-5 and Pic is picrate anion. The complexation of dibenzo-18-crown-6 (DB18C6) with alkali and transition metal ions have also been reported e.g. NaBr(DB18C6).2H₂O (Bush & Truter, 1971), [Ga(CH₃)₃]₂(DB18C6) (Robinson et al., 1987) and [(H₃O(DB18C6)]₂[HPMo₁₂O₄₀].DB18C6.3CH₃CN.H₂O (You et al., 2002) where HPMo₁₂O₄₀ is 12-molybdophosphate acid. Additionally, different products without lanthanide coordination with crown ether in the presence of picric acid have also been observed namely [NH₄(Pic)(DB18C6)] (Kanters et al., 1986), DB18C6.2HPic and DB24C8.2HPic (Colquhoun et al., 1986), D15C5.2HPic (Saleh et al., 1996) where DD18C6 is N,N'-dibenzyl-1,14, 10,13,-tetraoxa-7,16-diazacyclooctadecane.

In our study, no complexation product was obtained from a solution mixture containing dibenzo-18-crown-6, terbium nitrate and picric acid and instead the formation of DB18C6 with three water molecules in the presence of two picric acid have taken place. The product has a red colour consistent with a charge transfer interaction between the π-electron-rich benzene rings of the DB18C6 and the lack of π-electron in the HPic molecules.

The molecular structure of the title compound is shown in Fig.1. Bond lengths and angles have normal values (Allen et al., 1987). The dihedral angle between the two benzene rings (C1-C6 and C11-C16) in dibenzo-18-crown-6 unit is 44.53 (13)°. In the crown ether, the O-C(H₂)-C(H₂)-O torsion angles indicate a gauche conformation of the ethyleneoxy units, while the C-O-C-C torsion angles indicate planarity of these segments. In both picric acid units, one of the nitro groups is twisted away from the attached ring [O8—N1—C22—C21 = 52.9 (4)°, O9—N1—C22—C23 49.9 (4)°, O15—N4—C28—C29 = 146.4 (3)° and O16—N4—C28—C27 = 148.9 (3)°].

In the crystal structure, O—H···O, O—H···N and C—H···O hydrogen bonds are observed (Table 1). The molecules are linked into chains along the b axis via intermolecular O—H···O hydrogen bonds (Fig. 2). In addition, π-π interactions involving the C1-C6 (centroid Cg1) and C27-C32 (centroid Cg2) benzene rings are observed, with a Cg1···Cg2(x, -1+y, z) distance of 3.5697 (16) Å.

Related literature top

For bond-length data, see: Allen et al. (1987). For related literature, see: Bush & Truter (1971); Colquhoun et al. (1986); Kanters et al. (1986); Lu et al. (1993a,b); Robinson et al. (1987); Saleh et al. (1996, 1997); You et al. (2002); Zhou et al. (1996).

Experimental top

The title compound was prepared by the reaction of dibenzo-18-crown-6 (0.17 g, 0.46 mmol) and terbium nitrate (0.43 g, 1 mmol) in the presence of picric acid (0.93 g, 4.06 mmol) in a CH₃CN-CH₃OH-CHCl₃-H₂O (2:1:1:1 v/v) solution (20 ml). The solution was heated in a water bath with continous stirring for 5 min at 313-323 K. The solution was left to evaporate at room temperature. Red crystals were obtained after one week (yield 90%, decomposition point 381.6-412.0 K). Elemental analysis data: Calcuclated (found): C 44.00 (45.87), H 4.13 (4.32), N 9.63 (8.38)%.

Computing details top

Data collection: APEX2 (Bruker, 2005); cell refinement: APEX2 (Bruker, 2005); data reduction: SAINT (Bruker, 2005); program(s) used to solve structure: SHELXTL (Sheldrick, 2008); program(s) used to refine structure: SHELXTL (Sheldrick, 2008); molecular graphics: SHELXTL (Sheldrick, 2008); software used to prepare material for publication: SHELXTL (Sheldrick, 2008) and PLATON (Spek, 2003).

Figures top

	Fig. 1. The asymmetric unit of the title compound, showing 50% probability displacement ellipsoids and the atomic numbering.
	Fig. 2. The crystal packing of the title compound, viewed down the b axis. Hydrogen bonds are shown as dashed lines.

Dibenzo-18-crown-6–picric acid–water (1/2/3) top

Crystal data top

C₂₀H₂₄O₆·2C₆H₃N₃O₇·3H₂O	F(000) = 1816
M_r = 872.67	D_x = 1.586 Mg m⁻³
Orthorhombic, Pna2₁	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: P 2c -2n	Cell parameters from 8814 reflections
a = 16.4192 (2) Å	θ = 2.6–30.1°
b = 7.0845 (1) Å	µ = 0.14 mm⁻¹
c = 31.4135 (4) Å	T = 100 K
V = 3654.08 (8) Å³	Block, red
Z = 4	0.36 × 0.32 × 0.16 mm

Data collection top

Bruker SMART APEXII CCD area-detector diffractometer	5431 independent reflections
Radiation source: fine-focus sealed tube	4559 reflections with I > 2σ(I)
Graphite monochromator	R_int = 0.045
Detector resolution: 8.33 pixels mm^-1	θ_max = 30.1°, θ_min = 2.5°
ω scans	h = −17→23
Absorption correction: multi-scan (SADABS; Bruker, 2005)	k = −9→9
T_min = 0.952, T_max = 0.979	l = −43→44
37248 measured reflections

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)] = 0.044	Hydrogen site location: inferred from neighbouring sites
wR(F²) = 0.110	H-atom parameters constrained
S = 1.06	w = 1/[σ²(F_o²) + (0.0586P)² + 0.3893P] where P = (F_o² + 2F_c²)/3
5431 reflections	(Δ/σ)_max = 0.001
550 parameters	Δρ_max = 0.40 e Å⁻³
1 restraint	Δρ_min = −0.33 e Å⁻³

Crystal data top

C₂₀H₂₄O₆·2C₆H₃N₃O₇·3H₂O	V = 3654.08 (8) Å³
M_r = 872.67	Z = 4
Orthorhombic, Pna2₁	Mo Kα radiation
a = 16.4192 (2) Å	µ = 0.14 mm⁻¹
b = 7.0845 (1) Å	T = 100 K
c = 31.4135 (4) Å	0.36 × 0.32 × 0.16 mm

Data collection top

Bruker SMART APEXII CCD area-detector diffractometer	5431 independent reflections
Absorption correction: multi-scan (SADABS; Bruker, 2005)	4559 reflections with I > 2σ(I)
T_min = 0.952, T_max = 0.979	R_int = 0.045
37248 measured reflections

Refinement top

R[F² > 2σ(F²)] = 0.044	1 restraint
wR(F²) = 0.110	H-atom parameters constrained
S = 1.06	Δρ_max = 0.40 e Å⁻³
5431 reflections	Δρ_min = −0.33 e Å⁻³
550 parameters

Special details top

Experimental. The low-temperature data was collected with the Oxford Cyrosystem Cobra low-temperature attachment.

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	0.17228 (11)	0.0965 (3)	0.33490 (6)	0.0194 (4)
O2	0.02175 (11)	0.0646 (3)	0.31441 (6)	0.0205 (4)
O3	−0.03139 (11)	0.0282 (3)	0.22594 (6)	0.0225 (4)
O4	0.09157 (11)	0.0249 (3)	0.16058 (6)	0.0239 (4)
O5	0.23885 (11)	0.0985 (3)	0.18147 (6)	0.0226 (4)
O6	0.29382 (11)	0.1294 (3)	0.26846 (6)	0.0193 (4)
C1	0.11872 (16)	0.1717 (4)	0.36375 (8)	0.0179 (5)
C2	0.13993 (16)	0.2525 (4)	0.40216 (8)	0.0197 (5)
H2A	0.1944	0.2613	0.4099	0.024*
C3	0.07934 (18)	0.3210 (4)	0.42944 (8)	0.0220 (5)
H3A	0.0936	0.3756	0.4553	0.026*
C4	−0.00162 (18)	0.3077 (4)	0.41795 (9)	0.0233 (6)
H4A	−0.0418	0.3546	0.4360	0.028*
C5	−0.02333 (17)	0.2239 (4)	0.37928 (8)	0.0208 (5)
H5A	−0.0780	0.2141	0.3718	0.025*
C6	0.03588 (16)	0.1556 (4)	0.35220 (8)	0.0194 (5)
C7	−0.06112 (16)	0.0602 (4)	0.30033 (9)	0.0219 (5)
H7A	−0.0794	0.1867	0.2934	0.026*
H7B	−0.0958	0.0107	0.3227	0.026*
C8	−0.06605 (16)	−0.0636 (4)	0.26173 (8)	0.0230 (6)
H8A	−0.0373	−0.1808	0.2671	0.028*
H8B	−0.1226	−0.0938	0.2559	0.028*
C9	−0.02913 (17)	−0.0983 (5)	0.19033 (9)	0.0260 (6)
H9A	−0.0838	−0.1413	0.1838	0.031*
H9B	0.0038	−0.2077	0.1973	0.031*
C10	0.00626 (17)	0.0008 (5)	0.15248 (9)	0.0264 (6)
H10A	−0.0019	−0.0738	0.1269	0.032*
H10B	−0.0197	0.1225	0.1485	0.032*
C11	0.13815 (17)	0.1008 (4)	0.12882 (8)	0.0208 (5)
C12	0.11157 (18)	0.1340 (4)	0.08740 (9)	0.0247 (6)
H12A	0.0577	0.1105	0.0799	0.030*
C13	0.16674 (19)	0.2032 (4)	0.05716 (9)	0.0278 (6)
H13A	0.1496	0.2247	0.0294	0.033*
C14	0.24573 (19)	0.2392 (4)	0.06832 (9)	0.0277 (6)
H14A	0.2819	0.2846	0.0480	0.033*
C15	0.27260 (18)	0.2088 (4)	0.10966 (9)	0.0243 (6)
H15A	0.3263	0.2346	0.1170	0.029*
C16	0.21896 (18)	0.1396 (4)	0.14004 (8)	0.0217 (5)
C17	0.32251 (16)	0.1243 (4)	0.19333 (9)	0.0234 (6)
H17A	0.3351	0.2577	0.1955	0.028*
H17B	0.3580	0.0686	0.1721	0.028*
C18	0.33476 (16)	0.0296 (4)	0.23549 (9)	0.0230 (6)
H18A	0.3142	−0.0986	0.2341	0.028*
H18B	0.3925	0.0238	0.2419	0.028*
C19	0.30305 (16)	0.0303 (4)	0.30759 (8)	0.0201 (5)
H19A	0.3603	0.0237	0.3150	0.024*
H19B	0.2829	−0.0977	0.3044	0.024*
C20	0.25708 (15)	0.1275 (4)	0.34246 (8)	0.0200 (5)
H20A	0.2726	0.0762	0.3699	0.024*
H20B	0.2690	0.2616	0.3423	0.024*
O7	0.04207 (12)	0.5129 (3)	0.14168 (6)	0.0255 (4)
H1O7	0.0768	0.5063	0.1676	0.038*
O8	−0.08444 (13)	0.6214 (3)	0.09050 (7)	0.0345 (5)
O9	−0.05274 (14)	0.4429 (4)	0.03674 (7)	0.0388 (6)
O10	0.18091 (15)	0.7752 (5)	−0.03288 (7)	0.0483 (7)
O11	0.28256 (15)	0.8540 (4)	0.00640 (8)	0.0461 (7)
O12	0.28468 (13)	0.6902 (4)	0.15276 (8)	0.0399 (6)
O13	0.18305 (14)	0.5543 (4)	0.18259 (7)	0.0398 (6)
N1	−0.03549 (14)	0.5511 (4)	0.06579 (8)	0.0251 (5)
N2	0.21475 (14)	0.7882 (4)	0.00136 (8)	0.0273 (5)
N3	0.21571 (15)	0.6291 (3)	0.15208 (8)	0.0264 (5)
C21	0.08740 (17)	0.5840 (4)	0.11077 (8)	0.0219 (5)
C22	0.05087 (16)	0.6039 (4)	0.07059 (9)	0.0212 (5)
C23	0.09073 (16)	0.6653 (4)	0.03478 (9)	0.0215 (5)
H23A	0.0646	0.6701	0.0085	0.026*
C24	0.17102 (16)	0.7197 (4)	0.03915 (9)	0.0229 (5)
C25	0.21134 (16)	0.7102 (4)	0.07728 (9)	0.0228 (6)
H25A	0.2653	0.7486	0.0795	0.027*
C26	0.16965 (17)	0.6419 (4)	0.11252 (9)	0.0223 (5)
O14	0.20351 (12)	0.6284 (3)	0.35095 (6)	0.0259 (4)
H14B	0.1775	0.5883	0.3321	0.039*
O15	0.32541 (13)	0.5815 (4)	0.40398 (8)	0.0403 (6)
O16	0.33764 (14)	0.8326 (4)	0.44252 (8)	0.0440 (6)
O17	0.09655 (17)	1.0026 (4)	0.52185 (7)	0.0429 (6)
O18	−0.02186 (15)	0.9577 (3)	0.49381 (8)	0.0367 (5)
O19	−0.04855 (12)	0.6963 (3)	0.35674 (7)	0.0290 (5)
O20	0.05487 (13)	0.5990 (3)	0.32031 (6)	0.0302 (5)
N4	0.29744 (15)	0.7191 (4)	0.42194 (8)	0.0304 (6)
N5	0.05197 (17)	0.9451 (4)	0.49329 (8)	0.0299 (6)
N6	0.02454 (15)	0.6709 (3)	0.35237 (8)	0.0241 (5)
C27	0.16382 (16)	0.6979 (4)	0.38383 (8)	0.0195 (5)
C28	0.20853 (16)	0.7523 (4)	0.42021 (9)	0.0222 (5)
C29	0.17357 (18)	0.8335 (4)	0.45523 (9)	0.0245 (6)
H29A	0.2055	0.8720	0.4781	0.029*
C30	0.09002 (17)	0.8576 (4)	0.45611 (8)	0.0216 (5)
C31	0.04172 (17)	0.8047 (4)	0.42235 (9)	0.0206 (5)
H31A	−0.0145	0.8201	0.4233	0.025*
C32	0.07929 (16)	0.7278 (4)	0.38689 (8)	0.0199 (5)
O1W	0.18431 (15)	0.4638 (4)	0.27295 (7)	0.0412 (6)
H1W1	0.2163	0.3723	0.2656	0.062*
H2W1	0.1914	0.5915	0.2655	0.062*
O2W	0.14735 (14)	0.8507 (3)	0.24985 (8)	0.0364 (5)
H1W2	0.1246	0.9207	0.2683	0.055*
H2W2	0.1497	0.9124	0.2267	0.055*
O3W	0.04390 (14)	0.3916 (3)	0.22039 (7)	0.0332 (5)
H1W3	0.0251	0.2805	0.2233	0.050*
H2W3	0.0825	0.4299	0.2411	0.050*

Atomic displacement parameters (Å²) top

	U¹¹	U²²	U³³	U¹²	U¹³	U²³
O1	0.0148 (8)	0.0239 (9)	0.0195 (9)	0.0007 (7)	0.0003 (7)	−0.0020 (7)
O2	0.0156 (9)	0.0249 (10)	0.0211 (9)	0.0016 (7)	−0.0020 (7)	−0.0030 (7)
O3	0.0206 (10)	0.0275 (11)	0.0195 (9)	−0.0027 (8)	0.0004 (7)	−0.0026 (8)
O4	0.0170 (9)	0.0357 (11)	0.0189 (9)	−0.0007 (8)	−0.0011 (7)	0.0010 (8)
O5	0.0174 (9)	0.0322 (11)	0.0183 (9)	−0.0007 (8)	−0.0005 (7)	0.0020 (8)
O6	0.0176 (9)	0.0231 (10)	0.0173 (8)	0.0037 (7)	0.0004 (7)	0.0023 (7)
C1	0.0201 (12)	0.0146 (12)	0.0190 (12)	−0.0006 (9)	0.0024 (10)	0.0041 (9)
C2	0.0212 (12)	0.0183 (13)	0.0197 (12)	−0.0032 (10)	−0.0002 (10)	0.0035 (10)
C3	0.0307 (14)	0.0204 (13)	0.0150 (12)	−0.0013 (11)	0.0008 (10)	0.0015 (10)
C4	0.0299 (14)	0.0211 (14)	0.0190 (12)	0.0018 (11)	0.0064 (10)	0.0028 (10)
C5	0.0196 (12)	0.0214 (13)	0.0214 (12)	0.0009 (10)	0.0032 (10)	0.0027 (10)
C6	0.0218 (12)	0.0187 (13)	0.0177 (11)	0.0009 (10)	0.0007 (10)	0.0019 (10)
C7	0.0137 (12)	0.0288 (15)	0.0231 (13)	−0.0004 (10)	−0.0016 (10)	0.0009 (11)
C8	0.0142 (12)	0.0315 (15)	0.0233 (13)	−0.0036 (10)	−0.0013 (10)	0.0013 (11)
C9	0.0188 (13)	0.0347 (16)	0.0245 (14)	−0.0062 (11)	0.0012 (11)	−0.0065 (12)
C10	0.0214 (13)	0.0370 (16)	0.0206 (13)	−0.0007 (11)	−0.0046 (11)	−0.0049 (12)
C11	0.0239 (13)	0.0201 (13)	0.0183 (12)	0.0025 (10)	0.0023 (10)	−0.0008 (10)
C12	0.0278 (14)	0.0245 (14)	0.0220 (13)	0.0057 (11)	−0.0033 (11)	−0.0010 (11)
C13	0.0384 (17)	0.0267 (15)	0.0183 (13)	0.0075 (12)	0.0002 (11)	−0.0005 (11)
C14	0.0355 (16)	0.0268 (15)	0.0208 (13)	0.0038 (12)	0.0078 (12)	0.0041 (11)
C15	0.0240 (14)	0.0261 (14)	0.0229 (13)	0.0007 (11)	0.0044 (11)	0.0042 (11)
C16	0.0257 (14)	0.0215 (13)	0.0180 (12)	0.0028 (11)	0.0010 (10)	0.0015 (10)
C17	0.0156 (12)	0.0315 (15)	0.0230 (13)	−0.0007 (11)	0.0031 (10)	0.0014 (11)
C18	0.0186 (13)	0.0280 (14)	0.0223 (13)	0.0046 (11)	0.0013 (10)	−0.0012 (11)
C19	0.0160 (11)	0.0225 (13)	0.0218 (12)	0.0021 (10)	−0.0007 (10)	0.0056 (10)
C20	0.0162 (12)	0.0243 (14)	0.0195 (12)	−0.0027 (10)	−0.0010 (10)	0.0030 (10)
O7	0.0242 (10)	0.0329 (11)	0.0195 (9)	0.0007 (8)	0.0015 (7)	0.0023 (8)
O8	0.0232 (11)	0.0472 (14)	0.0329 (11)	−0.0034 (9)	0.0035 (9)	−0.0018 (10)
O9	0.0335 (12)	0.0450 (14)	0.0378 (12)	−0.0024 (10)	−0.0104 (10)	−0.0134 (11)
O10	0.0374 (13)	0.083 (2)	0.0246 (11)	−0.0052 (13)	0.0017 (10)	0.0164 (12)
O11	0.0358 (13)	0.0645 (18)	0.0381 (13)	−0.0178 (12)	0.0138 (10)	−0.0073 (12)
O12	0.0249 (11)	0.0551 (15)	0.0399 (13)	−0.0047 (10)	−0.0115 (10)	0.0029 (11)
O13	0.0362 (13)	0.0625 (17)	0.0207 (10)	−0.0072 (11)	−0.0047 (9)	0.0043 (10)
N1	0.0214 (11)	0.0278 (13)	0.0261 (12)	−0.0022 (9)	−0.0042 (10)	0.0019 (10)
N2	0.0242 (12)	0.0275 (13)	0.0302 (13)	0.0034 (10)	0.0071 (10)	0.0011 (10)
N3	0.0261 (12)	0.0295 (13)	0.0236 (12)	0.0017 (10)	−0.0040 (10)	−0.0014 (10)
C21	0.0237 (14)	0.0226 (13)	0.0195 (12)	0.0026 (10)	0.0016 (10)	−0.0018 (10)
C22	0.0193 (12)	0.0205 (13)	0.0239 (13)	0.0010 (10)	−0.0008 (10)	−0.0009 (11)
C23	0.0248 (13)	0.0216 (13)	0.0182 (12)	0.0050 (11)	−0.0023 (10)	−0.0003 (10)
C24	0.0229 (13)	0.0217 (14)	0.0240 (13)	0.0029 (11)	0.0041 (11)	−0.0001 (11)
C25	0.0188 (12)	0.0240 (14)	0.0256 (13)	0.0037 (10)	−0.0004 (10)	−0.0036 (11)
C26	0.0213 (13)	0.0247 (14)	0.0209 (12)	0.0037 (11)	−0.0030 (10)	−0.0031 (10)
O14	0.0263 (10)	0.0257 (10)	0.0257 (10)	0.0009 (8)	0.0046 (8)	0.0024 (8)
O15	0.0242 (11)	0.0390 (14)	0.0577 (16)	0.0068 (10)	0.0023 (11)	0.0085 (12)
O16	0.0276 (12)	0.0609 (17)	0.0435 (14)	−0.0110 (11)	−0.0089 (10)	−0.0007 (12)
O17	0.0616 (17)	0.0411 (14)	0.0258 (11)	0.0082 (12)	−0.0068 (11)	−0.0077 (10)
O18	0.0403 (13)	0.0372 (13)	0.0326 (11)	0.0081 (10)	0.0125 (10)	0.0039 (10)
O19	0.0199 (10)	0.0311 (11)	0.0360 (11)	−0.0020 (8)	−0.0055 (9)	0.0018 (9)
O20	0.0365 (12)	0.0303 (11)	0.0238 (10)	0.0038 (9)	−0.0043 (9)	−0.0057 (9)
N4	0.0196 (12)	0.0391 (16)	0.0323 (13)	−0.0040 (11)	−0.0009 (10)	0.0122 (12)
N5	0.0426 (16)	0.0243 (13)	0.0228 (12)	0.0038 (11)	0.0046 (11)	0.0027 (10)
N6	0.0280 (12)	0.0209 (12)	0.0233 (11)	−0.0010 (9)	−0.0019 (10)	0.0004 (9)
C27	0.0222 (13)	0.0157 (12)	0.0206 (12)	−0.0003 (10)	0.0023 (10)	0.0034 (9)
C28	0.0196 (12)	0.0232 (14)	0.0239 (13)	−0.0001 (10)	−0.0014 (10)	0.0075 (11)
C29	0.0287 (14)	0.0239 (14)	0.0210 (13)	−0.0031 (11)	−0.0045 (11)	0.0050 (11)
C30	0.0272 (14)	0.0183 (13)	0.0195 (12)	0.0023 (10)	0.0012 (10)	0.0028 (10)
C31	0.0222 (13)	0.0139 (12)	0.0259 (13)	0.0000 (10)	0.0001 (10)	0.0052 (10)
C32	0.0200 (12)	0.0182 (13)	0.0214 (12)	−0.0008 (10)	−0.0040 (10)	0.0035 (10)
O1W	0.0504 (15)	0.0448 (14)	0.0284 (11)	0.0117 (11)	0.0058 (10)	0.0067 (10)
O2W	0.0409 (13)	0.0325 (12)	0.0357 (12)	−0.0035 (10)	0.0007 (10)	0.0013 (9)
O3W	0.0317 (12)	0.0357 (12)	0.0321 (11)	−0.0066 (9)	−0.0024 (9)	0.0036 (10)

Geometric parameters (Å, º) top

O1—C1	1.370 (3)	C19—H19A	0.97
O1—C20	1.429 (3)	C19—H19B	0.97
O2—C6	1.371 (3)	C20—H20A	0.97
O2—C7	1.431 (3)	C20—H20B	0.97
O3—C8	1.418 (3)	O7—C21	1.323 (3)
O3—C9	1.434 (3)	O7—H1O7	0.99
O4—C11	1.367 (3)	O8—N1	1.223 (3)
O4—C10	1.434 (3)	O9—N1	1.225 (3)
O5—C16	1.373 (3)	O10—N2	1.214 (3)
O5—C17	1.435 (3)	O11—N2	1.217 (3)
O6—C18	1.423 (3)	O12—N3	1.213 (3)
O6—C19	1.424 (3)	O13—N3	1.219 (3)
C1—C2	1.380 (4)	N1—C22	1.474 (4)
C1—C6	1.412 (4)	N2—C24	1.470 (4)
C2—C3	1.400 (4)	N3—C26	1.457 (4)
C2—H2A	0.93	C21—C22	1.405 (4)
C3—C4	1.381 (4)	C21—C26	1.413 (4)
C3—H3A	0.93	C22—C23	1.372 (4)
C4—C5	1.398 (4)	C23—C24	1.380 (4)
C4—H4A	0.93	C23—H23A	0.93
C5—C6	1.379 (4)	C24—C25	1.370 (4)
C5—H5A	0.93	C25—C26	1.389 (4)
C7—C8	1.499 (4)	C25—H25A	0.93
C7—H7A	0.97	O14—C27	1.317 (3)
C7—H7B	0.97	O14—H14B	0.78
C8—H8A	0.97	O15—N4	1.216 (4)
C8—H8B	0.97	O16—N4	1.225 (4)
C9—C10	1.499 (4)	O17—N5	1.228 (4)
C9—H9A	0.97	O18—N5	1.216 (3)
C9—H9B	0.97	O19—N6	1.221 (3)
C10—H10A	0.97	O20—N6	1.234 (3)
C10—H10B	0.97	N4—C28	1.480 (4)
C11—C12	1.392 (4)	N5—C30	1.462 (4)
C11—C16	1.400 (4)	N6—C32	1.465 (4)
C12—C13	1.401 (4)	C27—C32	1.407 (4)
C12—H12A	0.93	C27—C28	1.412 (4)
C13—C14	1.368 (4)	C28—C29	1.368 (4)
C13—H13A	0.93	C29—C30	1.383 (4)
C14—C15	1.388 (4)	C29—H29A	0.93
C14—H14A	0.93	C30—C31	1.376 (4)
C15—C16	1.388 (4)	C31—C32	1.385 (4)
C15—H15A	0.93	C31—H31A	0.93
C17—C18	1.498 (4)	O1W—H1W1	0.86
C17—H17A	0.97	O1W—H2W1	0.94
C17—H17B	0.97	O2W—H1W2	0.85
C18—H18A	0.97	O2W—H2W2	0.85
C18—H18B	0.97	O3W—H1W3	0.85
C19—C20	1.498 (4)	O3W—H2W3	0.95

C1—O1—C20	117.1 (2)	O6—C18—H18B	109.4
C6—O2—C7	116.1 (2)	C17—C18—H18B	109.4
C8—O3—C9	110.0 (2)	H18A—C18—H18B	108.0
C11—O4—C10	117.6 (2)	O6—C19—C20	110.5 (2)
C16—O5—C17	116.5 (2)	O6—C19—H19A	109.5
C18—O6—C19	109.43 (19)	C20—C19—H19A	109.5
O1—C1—C2	125.3 (2)	O6—C19—H19B	109.5
O1—C1—C6	114.6 (2)	C20—C19—H19B	109.5
C2—C1—C6	120.1 (2)	H19A—C19—H19B	108.1
C1—C2—C3	120.0 (2)	O1—C20—C19	107.4 (2)
C1—C2—H2A	120.0	O1—C20—H20A	110.2
C3—C2—H2A	120.0	C19—C20—H20A	110.2
C4—C3—C2	120.0 (3)	O1—C20—H20B	110.2
C4—C3—H3A	120.0	C19—C20—H20B	110.2
C2—C3—H3A	120.0	H20A—C20—H20B	108.5
C3—C4—C5	120.1 (3)	C21—O7—H1O7	107.2
C3—C4—H4A	120.0	O8—N1—O9	125.1 (2)
C5—C4—H4A	120.0	O8—N1—C22	117.6 (2)
C6—C5—C4	120.3 (3)	O9—N1—C22	117.2 (2)
C6—C5—H5A	119.8	O10—N2—O11	124.3 (3)
C4—C5—H5A	119.8	O10—N2—C24	117.8 (2)
O2—C6—C5	125.4 (2)	O11—N2—C24	117.9 (2)
O2—C6—C1	115.1 (2)	O12—N3—O13	123.5 (2)
C5—C6—C1	119.5 (2)	O12—N3—C26	118.5 (2)
O2—C7—C8	108.3 (2)	O13—N3—C26	118.0 (2)
O2—C7—H7A	110.0	O7—C21—C22	117.2 (2)
C8—C7—H7A	110.0	O7—C21—C26	128.3 (2)
O2—C7—H7B	110.0	C22—C21—C26	114.5 (2)
C8—C7—H7B	110.0	C23—C22—C21	124.4 (2)
H7A—C7—H7B	108.4	C23—C22—N1	117.1 (2)
O3—C8—C7	110.6 (2)	C21—C22—N1	118.5 (2)
O3—C8—H8A	109.5	C22—C23—C24	117.6 (3)
C7—C8—H8A	109.5	C22—C23—H23A	121.2
O3—C8—H8B	109.5	C24—C23—H23A	121.2
C7—C8—H8B	109.5	C25—C24—C23	122.3 (3)
H8A—C8—H8B	108.1	C25—C24—N2	119.1 (2)
O3—C9—C10	109.6 (2)	C23—C24—N2	118.6 (2)
O3—C9—H9A	109.7	C24—C25—C26	118.4 (3)
C10—C9—H9A	109.7	C24—C25—H25A	120.8
O3—C9—H9B	109.7	C26—C25—H25A	120.8
C10—C9—H9B	109.7	C25—C26—C21	122.8 (2)
H9A—C9—H9B	108.2	C25—C26—N3	116.5 (2)
O4—C10—C9	107.1 (2)	C21—C26—N3	120.8 (2)
O4—C10—H10A	110.3	C27—O14—H14B	117.3
C9—C10—H10A	110.3	O15—N4—O16	124.6 (3)
O4—C10—H10B	110.3	O15—N4—C28	118.9 (3)
C9—C10—H10B	110.3	O16—N4—C28	116.5 (3)
H10A—C10—H10B	108.6	O18—N5—O17	124.1 (3)
O4—C11—C12	125.0 (3)	O18—N5—C30	117.9 (3)
O4—C11—C16	115.1 (2)	O17—N5—C30	118.0 (3)
C12—C11—C16	119.9 (2)	O19—N6—O20	123.3 (2)
C11—C12—C13	119.3 (3)	O19—N6—C32	118.6 (2)
C11—C12—H12A	120.3	O20—N6—C32	118.0 (2)
C13—C12—H12A	120.3	O14—C27—C32	126.7 (2)
C14—C13—C12	120.3 (3)	O14—C27—C28	118.7 (2)
C14—C13—H13A	119.8	C32—C27—C28	114.6 (2)
C12—C13—H13A	119.8	C29—C28—C27	123.2 (3)
C13—C14—C15	120.8 (3)	C29—C28—N4	116.8 (2)
C13—C14—H14A	119.6	C27—C28—N4	120.0 (2)
C15—C14—H14A	119.6	C28—C29—C30	119.0 (3)
C16—C15—C14	119.8 (3)	C28—C29—H29A	120.5
C16—C15—H15A	120.1	C30—C29—H29A	120.5
C14—C15—H15A	120.1	C31—C30—C29	121.5 (3)
O5—C16—C15	125.1 (3)	C31—C30—N5	119.0 (3)
O5—C16—C11	115.0 (2)	C29—C30—N5	119.5 (2)
C15—C16—C11	119.8 (2)	C30—C31—C32	118.0 (3)
O5—C17—C18	107.5 (2)	C30—C31—H31A	121.0
O5—C17—H17A	110.2	C32—C31—H31A	121.0
C18—C17—H17A	110.2	C31—C32—C27	123.6 (2)
O5—C17—H17B	110.2	C31—C32—N6	115.5 (2)
C18—C17—H17B	110.2	C27—C32—N6	120.9 (2)
H17A—C17—H17B	108.5	H1W1—O1W—H2W1	125.3
O6—C18—C17	111.0 (2)	H1W2—O2W—H2W2	107.7
O6—C18—H18A	109.4	H1W3—O3W—H2W3	115.7
C17—C18—H18A	109.4

C20—O1—C1—C2	−9.1 (4)	O9—N1—C22—C21	−128.6 (3)
C20—O1—C1—C6	173.1 (2)	C21—C22—C23—C24	−3.3 (4)
O1—C1—C2—C3	−178.6 (2)	N1—C22—C23—C24	178.4 (2)
C6—C1—C2—C3	−1.0 (4)	C22—C23—C24—C25	1.4 (4)
C1—C2—C3—C4	0.1 (4)	C22—C23—C24—N2	−179.3 (2)
C2—C3—C4—C5	0.7 (4)	O10—N2—C24—C25	171.8 (3)
C3—C4—C5—C6	−0.6 (4)	O11—N2—C24—C25	−8.1 (4)
C7—O2—C6—C5	7.2 (4)	O10—N2—C24—C23	−7.6 (4)
C7—O2—C6—C1	−175.0 (2)	O11—N2—C24—C23	172.5 (3)
C4—C5—C6—O2	177.4 (3)	C23—C24—C25—C26	0.5 (4)
C4—C5—C6—C1	−0.3 (4)	N2—C24—C25—C26	−178.8 (2)
O1—C1—C6—O2	1.1 (3)	C24—C25—C26—C21	−0.7 (4)
C2—C1—C6—O2	−176.8 (2)	C24—C25—C26—N3	178.2 (3)
O1—C1—C6—C5	179.0 (2)	O7—C21—C26—C25	178.3 (3)
C2—C1—C6—C5	1.1 (4)	C22—C21—C26—C25	−0.9 (4)
C6—O2—C7—C8	−173.3 (2)	O7—C21—C26—N3	−0.6 (4)
C9—O3—C8—C7	174.3 (2)	C22—C21—C26—N3	−179.8 (2)
O2—C7—C8—O3	−73.2 (3)	O12—N3—C26—C25	5.1 (4)
C8—O3—C9—C10	179.1 (2)	O13—N3—C26—C25	−173.7 (3)
C11—O4—C10—C9	175.4 (2)	O12—N3—C26—C21	−175.9 (3)
O3—C9—C10—O4	71.5 (3)	O13—N3—C26—C21	5.3 (4)
C10—O4—C11—C12	−8.7 (4)	O14—C27—C28—C29	177.0 (3)
C10—O4—C11—C16	173.5 (2)	C32—C27—C28—C29	−2.1 (4)
O4—C11—C12—C13	−176.6 (3)	O14—C27—C28—N4	−4.0 (4)
C16—C11—C12—C13	1.1 (4)	C32—C27—C28—N4	176.8 (2)
C11—C12—C13—C14	−0.5 (4)	O15—N4—C28—C29	146.4 (3)
C12—C13—C14—C15	−0.3 (5)	O16—N4—C28—C29	−32.1 (4)
C13—C14—C15—C16	0.5 (5)	O15—N4—C28—C27	−32.6 (4)
C17—O5—C16—C15	−2.1 (4)	O16—N4—C28—C27	148.9 (3)
C17—O5—C16—C11	175.8 (2)	C27—C28—C29—C30	2.6 (4)
C14—C15—C16—O5	177.9 (3)	N4—C28—C29—C30	−176.4 (2)
C14—C15—C16—C11	0.1 (4)	C28—C29—C30—C31	−1.1 (4)
O4—C11—C16—O5	−1.0 (3)	C28—C29—C30—N5	−179.7 (2)
C12—C11—C16—O5	−178.9 (2)	O18—N5—C30—C31	4.1 (4)
O4—C11—C16—C15	177.0 (2)	O17—N5—C30—C31	−175.3 (3)
C12—C11—C16—C15	−0.9 (4)	O18—N5—C30—C29	−177.2 (3)
C16—O5—C17—C18	−166.7 (2)	O17—N5—C30—C29	3.4 (4)
C19—O6—C18—C17	176.9 (2)	C29—C30—C31—C32	−0.7 (4)
O5—C17—C18—O6	−69.8 (3)	N5—C30—C31—C32	177.9 (2)
C18—O6—C19—C20	−177.3 (2)	C30—C31—C32—C27	1.2 (4)
C1—O1—C20—C19	179.0 (2)	C30—C31—C32—N6	178.9 (2)
O6—C19—C20—O1	72.0 (3)	O14—C27—C32—C31	−178.9 (3)
O7—C21—C22—C23	−176.3 (3)	C28—C27—C32—C31	0.2 (4)
C26—C21—C22—C23	3.0 (4)	O14—C27—C32—N6	3.6 (4)
O7—C21—C22—N1	2.0 (4)	C28—C27—C32—N6	−177.4 (2)
C26—C21—C22—N1	−178.7 (2)	O19—N6—C32—C31	0.9 (4)
O8—N1—C22—C23	−128.7 (3)	O20—N6—C32—C31	−178.9 (2)
O9—N1—C22—C23	49.9 (4)	O19—N6—C32—C27	178.6 (2)
O8—N1—C22—C21	52.9 (4)	O20—N6—C32—C27	−1.2 (4)

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
O7—H1O7···O3W	1.00	1.92	2.618 (3)	124
O7—H1O7···O13	1.00	1.84	2.664 (3)	138
O7—H1O7···N3	1.00	2.49	2.985 (3)	110
O1W—H1W1···O6	0.87	2.14	2.978 (3)	162
O1W—H2W1···O2W	0.94	2.03	2.900 (4)	152
O2W—H1W2···O1ⁱ	0.85	2.56	3.215 (3)	135
O2W—H1W2···O2ⁱ	0.85	2.45	3.265 (3)	162
O2W—H2W2···O4ⁱ	0.85	2.42	3.198 (3)	152
O2W—H2W2···O5ⁱ	0.85	2.43	3.155 (3)	144
O3W—H1W3···O3	0.85	2.02	2.861 (3)	173
O3W—H2W3···O1W	0.95	1.96	2.881 (3)	163
O14—H14B···O1W	0.78	2.06	2.732 (3)	144
O14—H14B···O20	0.78	2.05	2.632 (3)	131
C3—H3A···O11ⁱⁱ	0.93	2.60	3.323 (4)	136
C7—H7A···O6ⁱⁱⁱ	0.97	2.58	3.393 (3)	142
C7—H7B···O19^iv	0.97	2.59	3.135 (4)	116
C9—H9A···O12ⁱⁱⁱ	0.97	2.39	3.341 (4)	165
C19—H19A···O19^v	0.97	2.53	3.301 (3)	137

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

Experimental details

Crystal data
Chemical formula	C₂₀H₂₄O₆·2C₆H₃N₃O₇·3H₂O
M_r	872.67
Crystal system, space group	Orthorhombic, Pna2₁
Temperature (K)	100
a, b, c (Å)	16.4192 (2), 7.0845 (1), 31.4135 (4)
V (Å³)	3654.08 (8)
Z	4
Radiation type	Mo Kα
µ (mm⁻¹)	0.14
Crystal size (mm)	0.36 × 0.32 × 0.16

Data collection
Diffractometer	Bruker SMART APEXII CCD area-detector diffractometer
Absorption correction	Multi-scan (SADABS; Bruker, 2005)
T_min, T_max	0.952, 0.979
No. of measured, independent and observed [I > 2σ(I)] reflections	37248, 5431, 4559
R_int	0.045
(sin θ/λ)_max (Å⁻¹)	0.705

Refinement
R[F² > 2σ(F²)], wR(F²), S	0.044, 0.110, 1.06
No. of reflections	5431
No. of parameters	550
No. of restraints	1
H-atom treatment	H-atom parameters constrained
Δρ_max, Δρ_min (e Å⁻³)	0.40, −0.33

Computer programs: APEX2 (Bruker, 2005), SAINT (Bruker, 2005), SHELXTL (Sheldrick, 2008) and PLATON (Spek, 2003).

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
O7—H1O7···O3W	1.00	1.92	2.618 (3)	124
O7—H1O7···O13	1.00	1.84	2.664 (3)	138
O7—H1O7···N3	1.00	2.49	2.985 (3)	110
O1W—H1W1···O6	0.87	2.14	2.978 (3)	162
O1W—H2W1···O2W	0.94	2.03	2.900 (4)	152
O2W—H1W2···O1ⁱ	0.85	2.56	3.215 (3)	135
O2W—H1W2···O2ⁱ	0.85	2.45	3.265 (3)	162
O2W—H2W2···O4ⁱ	0.85	2.42	3.198 (3)	152
O2W—H2W2···O5ⁱ	0.85	2.43	3.155 (3)	144
O3W—H1W3···O3	0.85	2.02	2.861 (3)	173
O3W—H2W3···O1W	0.95	1.96	2.881 (3)	163
O14—H14B···O1W	0.78	2.06	2.732 (3)	144
O14—H14B···O20	0.78	2.05	2.632 (3)	131
C3—H3A···O11ⁱⁱ	0.93	2.60	3.323 (4)	136
C7—H7A···O6ⁱⁱⁱ	0.97	2.58	3.393 (3)	142
C7—H7B···O19^iv	0.97	2.59	3.135 (4)	116
C9—H9A···O12ⁱⁱⁱ	0.97	2.39	3.341 (4)	165
C19—H19A···O19^v	0.97	2.53	3.301 (3)	137

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

Acknowledgements

The authors thank the Malaysian Government and Universiti Sains Malaysia for providing SAGA (No. 304/PKIMIA/653010/A118) and FRGS (No.203/PKIMIA/671020) research grants.

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