Crystal structure of poly[di­aqua­bis­(μ5-benzene-1,3-di­carboxyl­ato)(N,N-di­methyl­formamide)­cadmium(II)disodium(I)]

Sangsawang, M.; Chainok, K.; Wannarit, N.

doi:10.1107/S2056989017013871

research communications

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ISSN: 2056-9890

Volume 73| Part 11| November 2017| Pages 1599-1602

https://doi.org/10.1107/S2056989017013871

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Crystal structure of poly[diaquabis(μ₅-benzene-1,3-dicarboxylato)(N,N-dimethylformamide)cadmium(II)disodium(I)]

Matimon Sangsawang,^a Kittipong Chainok ^b and Nanthawat Wannarit ^a ^*

^aDepartment of Chemistry, Faculty of Science and Technology, Thammasat University, Khlong Laung, Pathumthani 12121, Thailand, and ^bMaterials and Textile Technology, Faculty of Science and Technology, Thammasat University, Khlong Laung, Pathumthani 12121, Thailand
^*Correspondence e-mail: nwan0110@tu.ac.th

Edited by T. J. Prior, University of Hull, England (Received 2 September 2017; accepted 26 September 2017; online 3 October 2017)

The title compound, [CdNa₂(C₈H₄O₄)₂(C₃H₇NO)(H₂O)₂]_n or [CdNa₂(1,3-bdc)₂(DMF)(H₂O)₂]_n, is a new Cd^II–Na^I heterobimetallic coordination polymer. The asymmetric unit consists of one Cd^II atom, two Na^I atoms, two 1,3-bdc ligands, two coordinated water molecules and one coordinated DMF molecule. The Cd^II atom exhibits a seven-coordinate geometry, while the Na^I atoms can be considered to be pentacoordinate. The metal ions and their symmetry-related equivalents are connected via chelating–bridging carboxylate groups of the 1,3-bdc ligands to generate a three-dimensional framework. In the crystal, there are classical O—H⋯O hydrogen bonds involving the coordinated water molecules and the 1,3-bdc carboxylate groups and π–π stacking between the benzene rings of the 1,3-bdc ligands present within the frameworks.

Keywords: crystal structure; Cd^II–Na^I bimetallic; three-dimensional framework.

CCDC reference: 1576543

1. Chemical context

Porous coordination polymers or metal–organic frameworks (MOFs) constructed from d¹⁰ transition metals and benzene polycarboxylate bridging ligands have been widely studied (Yaghi et al., 1999 ; Lin et al., 2008 ; Seco et al., 2017 ) due to the varieties of coordination framework topologies and also potential applications in gas adsorption (Suh et al., 2012 ), photoluminescence (Wang et al., 2012 ) and photocatalysis (Wu et al., 2017 ). Among the most common ligands in this class, the rigid and planar backbone of benzene dicarboxylates such as benzene-1,3-dicarboxylic acid (1,3-H₂bdc) and benzene-1,4-dicarboxylic acid (1,4-H₂bdc) are widely employed in the construction of these solids owing to their rich coordination modes. Studies incorporating alkaline metal ions into d¹⁰-MOFs with one type of bridging ligand to construct novel heterobimetallic d¹⁰-alkaline metal ion MOFs have been undertaken (Lin et al., 2010a ,b ). The alkali metal ions could provide an unpredictable coordination number and pH-dependent self-assembly in the construction of coordination frameworks with various types of topology and dimensionality (Borah et al., 2011 ; Chen et al., 2011 ). However, the members of three-dimensional coordination framework heterobimetallic Zn^II or Cd^II /Na^I MOFs with benzenepolycarboxylate ligands are still limited; previous reports include [ZnNa(1,2,4-btc)] where 1,2,4-btc = benzene-1,2,4-tricarboxylate (Wang et al., 2004 ), [Zn₂Na₂(1,4-bdc)₃·(DMF)₂·(m-H₂O)₂] where 1,4-bdcH₂ = benzene-1,4-dicarboxylic acid (Xu et al., 2004 ), {[CdNa(1,3-bdc)₂]·[NH₂(CH₃)₂]} where 1,3-bdcH₂ = benzene-1,3-dicarboxylic acid (Che et al., 2007 ), [CdNa(OH-1,3-bdc)₂(H₂O)₂]·2H₂O where OH-1,3-bdcH₂ = 5-hydroxybenzene-1,3-dicarboxylic acid (Du et al., 2013 ) and [Cd₈Na(ntc)₆(H₂O)₈] where ntcH₃ = 5-nitrobenzene-1,2,3-tricarboxylic acid (Yang et al., 2014 ). With the aim of searching for new members of this heterobimetallic MOFs system containing benzene-1,3-dicarboxylic acid (1,3-bdcH₂), we explored mixed sources of Zn^II/Cd^II–Na^I with this ligand. The expected products are prepared by using a direct synthetic method, mixing metal nitrate salts, 1,3-bdcH₂ and NaOH (mole ratio 1:1:2) in water, methanol and DMF solvents. However, only the Cd^II–Na^I MOF product has been successfully synthesized. As part of our ongoing studies on this complex, we describe here the synthesis and crystal structure of a novel three-dimensional heterobimetallic Cd^II–Na^I MOF, [CdNa₂(1,3-bdc)₂(DMF)(H₂O)₂]_n (I).

2. Structural commentary

The title compound (I) crystallizes in the tetragonal crystal system with polar P4₃ space group. The asymmetric unit of (I) consists of one Cd^II ion, two crystallographically independent Na(I) ions, two 1,3-bdc ligands, two coordinated water molecules and one DMF molecules, as shown in Fig. 1. Each Cd^II ion is coordinated by seven carboxylate oxygen atoms from four different 1,3-bdc ligands with the Cd—O bond distances range between 2.301 (3) and 2.555 (3) Å (Table 1). The Na1 ion is surrounded by three carboxylate oxygen atoms of three different 1,3-bdc ligands, one oxygen atom from a water molecule, and one DMF molecule with the Na—O bond distances ranging between 2.304 (7) and 2.498 (11) Å, while the Na2 ion adopts a five-coordinate [4 + 1] coordination with four oxygen atoms from three different 1,3-bdc ligands and one oxygen atom from a water molecule. The Na—O bond distances are in the range 2.275 (5) to 2.354 (8) Å. Fig. 2 shows the coordination modes of the 1,3-bdc ligand in compound (I). The 1,3-bdc molecule is fully deprotonated and coordinated to the Cd^II and Na^I ions in a μ₅-coordination mode, creating a one-dimensional heterobimetallic chain running parallel to the c axis, Fig. 3. Adjacent chains are further connected through the 1,3-bdc ligands in the a- and b-axis directions, generating a three-dimensional framework structure as shown in Fig. 4. The coordinated water and DMF molecules adopt a monodentate coordination mode and serve as a terminal pendant ligand pointing inside the channels.

Table 1
Selected geometric parameters (Å, °)

Cd1—O1	2.301 (3)	Na1—O4ⁱ	2.441 (5)
Cd1—O2	2.555 (3)	Na1—O9	2.304 (7)
Cd1—O3ⁱ	2.496 (3)	Na1—O11B	2.498 (11)
Cd1—O4ⁱ	2.385 (3)	Na1—O11A	2.475 (18)
Cd1—O5	2.284 (4)	Na2—O4^iv	2.655 (5)
Cd1—O7ⁱⁱ	2.396 (3)	Na2—O5	2.277 (5)
Cd1—O8ⁱⁱ	2.472 (3)	Na2—O7ⁱⁱ	2.282 (4)
Na1—O1	2.368 (5)	Na2—O8^v	2.275 (5)
Na1—O3ⁱⁱⁱ	2.339 (5)	Na2—O10	2.354 (8)

O1—Cd1—O2	53.12 (15)	O1—Na1—O4ⁱ	77.84 (17)
O1—Cd1—O3ⁱ	131.59 (15)	O1—Na1—O11B	104.1 (3)
O1—Cd1—O4ⁱ	80.31 (12)	O3ⁱⁱⁱ—Na1—O1	151.1 (2)
O1—Cd1—O7ⁱⁱ	125.91 (12)	O3ⁱⁱⁱ—Na1—O4ⁱ	94.59 (15)
O1—Cd1—O8ⁱⁱ	92.04 (13)	O3ⁱⁱⁱ—Na1—O11B	82.9 (3)
O3ⁱ—Cd1—O2	173.00 (16)	O4ⁱ—Na1—O11B	177.4 (3)
O4ⁱ—Cd1—O2	132.60 (15)	O9—Na1—O1	95.8 (2)
O4ⁱ—Cd1—O3ⁱ	53.37 (13)	O9—Na1—O3ⁱⁱⁱ	112.0 (2)
O4ⁱ—Cd1—O7ⁱⁱ	122.40 (12)	O9—Na1—O4ⁱ	88.3 (2)
O4ⁱ—Cd1—O8ⁱⁱ	78.81 (13)	O9—Na1—O11B	93.2 (4)
O5—Cd1—O1	125.67 (14)	O5—Na2—O4^iv	95.45 (19)
O5—Cd1—O2	90.36 (16)	O5—Na2—O7ⁱⁱ	83.03 (18)
O5—Cd1—O3ⁱ	82.65 (15)	O5—Na2—O10	104.5 (2)
O5—Cd1—O4ⁱ	128.83 (14)	O7ⁱⁱ—Na2—O4^iv	94.98 (14)
O5—Cd1—O7ⁱⁱ	80.41 (12)	O7ⁱⁱ—Na2—O10	80.5 (2)
O5—Cd1—O8ⁱⁱ	133.24 (16)	O8^v—Na2—O4^iv	77.02 (13)
O7ⁱⁱ—Cd1—O2	85.03 (15)	O8^v—Na2—O5	110.18 (16)
O7ⁱⁱ—Cd1—O3ⁱ	94.01 (14)	O8^v—Na2—O7ⁱⁱ	164.93 (18)
O7ⁱⁱ—Cd1—O8ⁱⁱ	53.55 (14)	O8^v—Na2—O10	102.3 (2)
O8ⁱⁱ—Cd1—O2	93.07 (11)	O10—Na2—O4^iv	158.8 (2)
O8ⁱⁱ—Cd1—O3ⁱ	91.92 (10)
Symmetry codes: (i) x, y-1, z; (ii) x-1, y, z; (iii) $[-y+1, x, z-{\script{1\over 4}}]$ ; (iv) $[y-1, -x, z+{\script{1\over 4}}]$ ; (v) $[y, -x+1, z+{\script{1\over 4}}]$ .

Figure 1
Asymmetric unit of (I) with the atomic-numbering scheme. Displacement ellipsoids are drawn at the 50% probability level.

Figure 2
Coordination mode of the μ₅-1,3-bdc bridging ligands found in (I). All hydrogen atoms are omitted for clarity.

Figure 3
Perspective view along the crystallographic c axis of (a) the three-dimensional framework of (I) (the coordination polyhedra for Cd^II and Na^I are pink and green, respectively) and (b) helical chain-like structure of the Cd—Na clusters (dark blue = Cd, blue = Na and red = O).

Figure 4
Perspective view of the three-dimensional framework of (I) (the coordination polyhedra for Cd^II and Na^I are pink and green, respectively). All hydrogen atoms are omitted for clarity.

3. Supramolecular features

In the crystal of (I), classical O—H⋯O hydrogen bonds and aromatic π–π stacking interactions are observed and these interactions presumably help to stabilize the frameworks. All water molecules are shown to act as O—H⋯O hydrogen-bond donors towards the carboxylate groups of the 1,3-bdc ligands (Table 2). The π–π stacking interactions are between symmetry-related aromatic rings of the 1,3-bdc ligands with a Cg1⋯Cg2ⁱ distance of 3.588 (3) Å and a dihedral angle of 3.8 (4)° [Cg1 and Cg2 are the centroids of the C1–C6 and C9–C14 rings, respectively; symmetry code: (i) –y, x, z – 1/4].

Table 2
Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
O9—H9B⋯O6	0.90	2.22	3.074 (8)	159
O10—H10B⋯O6^v	0.86	2.29	3.073 (8)	152
Symmetry code: (v) $[y, -x+1, z+{\script{1\over 4}}]$ .

4. Database survey

To the best of our knowledge of structures closely related to (I), only the three-dimensional coordination framework {[CdNa(1,3-bdc)₂]·[NH₂(CH₃)₂]} has been reported (Che et al., 2007). This compound crystallized in the centrosymmetric space group C2/c. The Cd^II and Na^I centers are linked by a 1,3-bdc ligand in a μ₄-coordination mode. The DMF solvent decomposes under solvothermal synthesis, with the construction of a 3D coordination framework with open channels containing NH₂(CH₃)₂ molecules. In comparison, compound (I) contains coordinated H₂O and DMF molecules projecting into the framework channels. Other related three-dimensional heterobimetallic d¹⁰–Na^I coordination frameworks containing benzenepolycarboxylate ligands have been published, such as [CdNa(OH-1,3-bdc)₂(H₂O)₂]·2H₂O where OH-1,3-bdcH₂ = 5-hydroxy-benzene-1,3-dicarboxylic acid (Du et al., 2013), [Zn₂Na₂(1,4-bdc)₃·(DMF)₂·(m-H₂O)₂] where 1,4-bdcH₂ = benzene-1,4-dicarboxylic acid (Xu et al., 2004), [ZnNa(1,2,4-btc)] where 1,2,4-btc = 1,2,4-benzenetricarboxylate (Wang et al., 2004), and [Cd₈Na(ntc)₆(H₂O)₈] where ntcH₃ = 5-nitrobenzene-1,2,3-tricarboxylic acid (Yang et al., 2014). The three-dimensional coordination framework topologies of these compounds are the result of the construction of different types of metal centers, geometries and carboxylate ligand derivatives. It is found that the carboxylate ligand derivatives in the structure of these related compounds exhibit a μ₄-coordination mode.

5. Synthesis and crystallization

A mixture solution of 1,3-bdcH₂ (1.0 mmol) and NaOH (2.0 mmol) in 10 mL of distilled water was slowly dropped to a methanolic solution (10 ml) of Cd(NO₃)₂·4H₂O (1.0 mmol). The reaction mixture was stirred at 333 K for 30 min and allowed to cool to room temperature and then filtered. The filtrate was allowed to stand to slowly evaporate at ambient temperature. Colorless block-shaped crystals suitable for single crystal X-ray diffraction were obtained after three days (76% yield based on Cd).

6. Refinement

Crystal data, data collection and structure refinement details are summarized in Table 3. All hydrogen atoms except those of water molecules were generated geometrically and refined isotropically using a riding model, with C—H = 0.93 Å and U_iso(H) = 1.2U_eq(C). The coordinated DMF molecule was found to be disordered with two sets of sites with a refined occupancy ratio of 0.382 (10) and 0.618 (10).

Table 3
Experimental details

Crystal data
Chemical formula	[CdNa₂(C₈H₄O₄)₂(C₃H₇NO)(H₂O)₂]
M_r	595.73
Crystal system, space group	Tetragonal, P4₃
Temperature (K)	296
a, c (Å)	10.1437 (8), 21.4664 (15)
V (Å³)	2208.8 (4)
Z	4
Radiation type	Mo Kα
μ (mm⁻¹)	1.09
Crystal size (mm)	0.35 × 0.21 × 0.16

Data collection
Diffractometer	Bruker APEXII D8 QUEST CMOS
Absorption correction	Multi-scan (SADABS, Bruker, 2013 )
T_min, T_max	0.647, 0.704
No. of measured, independent and observed [I > 2σ(I)] reflections	56814, 5708, 5301
R_int	0.074
(sin θ/λ)_max (Å⁻¹)	0.676

Refinement
R[F² > 2σ(F²)], wR(F²), S	0.028, 0.068, 1.03
No. of reflections	5708
No. of parameters	351
No. of restraints	160
H-atom treatment	H-atom parameters constrained
Δρ_max, Δρ_min (e Å⁻³)	0.52, −0.45
Absolute structure	Flack x determined using 2427 quotients [(I⁺)−(I⁻)]/[(I⁺)+(I⁻)] (Parsons et al., 2013 )
Absolute structure parameter	0.081 (13)
Computer programs: APEX2 and SAINT (Bruker, 2013), SHELXT (Sheldrick, 2015a ), SHELXL (Sheldrick, 2015b ) and OLEX2 (Dolomanov et al., 2009 ).

Supporting information

CCDC reference: 1576543

Crystal structure: contains datablock I. DOI: https://doi.org/10.1107/S2056989017013871/pj2046sup1.cif

Structure factors: contains datablock I. DOI: https://doi.org/10.1107/S2056989017013871/pj2046Isup2.hkl

checkCIF report

Computing details top

Data collection: APEX2 (Bruker, 2013); cell refinement: SAINT (Bruker, 2013); data reduction: SAINT (Bruker, 2013); program(s) used to solve structure: SHELXT (Sheldrick, 2015a); program(s) used to refine structure: SHELXL (Sheldrick, 2015b); molecular graphics: OLEX2 (Dolomanov et al., 2009); software used to prepare material for publication: OLEX2 (Dolomanov et al., 2009).

Poly[diaquabis(µ₅-benzene-1,3-dicarboxylato)(N,N-dimethylformamide)cadmium(II)disodium(I)] top

Crystal data top

[CdNa₂(C₈H₄O₄)₂(C₃H₇NO)(H₂O)₂]	D_x = 1.791 Mg m⁻³
M_r = 595.73	Mo Kα radiation, λ = 0.71073 Å
Tetragonal, P4₃	Cell parameters from 9769 reflections
a = 10.1437 (8) Å	θ = 2.7–28.3°
c = 21.4664 (15) Å	µ = 1.09 mm⁻¹
V = 2208.8 (4) Å³	T = 296 K
Z = 4	Block, colourless
F(000) = 1192	0.35 × 0.21 × 0.16 mm

Data collection top

Bruker APEXII D8 QUEST CMOS diffractometer	5301 reflections with I > 2σ(I)
Detector resolution: 10.5 pixels mm^-1	R_int = 0.074
ω and φ scans	θ_max = 28.7°, θ_min = 2.8°
Absorption correction: multi-scan (SADABS, Bruker, 2013)	h = −13→13
T_min = 0.647, T_max = 0.704	k = −12→13
56814 measured reflections	l = −28→29
5708 independent reflections

Refinement top

Refinement on F²	H-atom parameters constrained
Least-squares matrix: full	w = 1/[σ²(F_o²) + (0.0375P)² + 0.6193P] where P = (F_o² + 2F_c²)/3
R[F² > 2σ(F²)] = 0.028	(Δ/σ)_max < 0.001
wR(F²) = 0.068	Δρ_max = 0.52 e Å⁻³
S = 1.03	Δρ_min = −0.45 e Å⁻³
5708 reflections	Extinction correction: SHELXL, Fc^*=kFc[1+0.001xFc²λ³/sin(2θ)]^-1/4
351 parameters	Extinction coefficient: 0.0050 (7)
160 restraints	Absolute structure: Flack x determined using 2427 quotients [(I⁺)-(I^-)]/[(I⁺)+(I^-)] (Parsons et al., 2013)
Hydrogen site location: mixed	Absolute structure parameter: 0.081 (13)

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.

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

	x	y	z	U_iso*/U_eq	Occ. (<1)
Cd1	0.08591 (2)	0.23028 (2)	0.49814 (3)	0.02155 (9)
Na1	0.1091 (4)	0.2329 (2)	0.33008 (17)	0.0575 (9)
Na2	0.1037 (2)	0.2125 (3)	0.66027 (15)	0.0510 (8)
O1	0.0894 (3)	0.3769 (3)	0.41640 (17)	0.0357 (8)
O2	0.0886 (4)	0.4817 (3)	0.5052 (3)	0.0458 (10)
O3	0.1045 (3)	0.9851 (3)	0.5013 (2)	0.0349 (6)
O4	0.0482 (4)	1.0819 (3)	0.41384 (15)	0.0354 (8)
O5	0.2394 (3)	0.2174 (5)	0.57576 (19)	0.0502 (10)
O6	0.3488 (3)	0.2217 (4)	0.4890 (2)	0.0490 (10)
O7	0.9433 (3)	0.2411 (4)	0.58696 (16)	0.0337 (7)
O8	0.8424 (3)	0.2200 (3)	0.4971 (2)	0.0319 (6)
O9	0.3263 (6)	0.1781 (9)	0.3477 (3)	0.111 (2)
H9A	0.3381	0.0906	0.3450	0.166*
H9B	0.3540	0.2025	0.3857	0.166*
O10	0.0517 (7)	0.4353 (7)	0.6789 (3)	0.118 (2)
H10A	0.0182	0.4694	0.6461	0.178*
H10B	0.1218	0.4773	0.6885	0.178*
C1	0.0879 (4)	0.6114 (4)	0.4125 (2)	0.0251 (8)
C2	0.0830 (4)	0.7316 (4)	0.4438 (2)	0.0236 (8)
H2	0.0798	0.7328	0.4871	0.028*
C3	0.0829 (4)	0.8496 (4)	0.4111 (2)	0.0225 (8)
C4	0.0860 (5)	0.8478 (4)	0.3463 (2)	0.0312 (10)
H4	0.0847	0.9267	0.3242	0.037*
C5	0.0909 (5)	0.7295 (4)	0.3148 (2)	0.0364 (12)
H5	0.0935	0.7284	0.2715	0.044*
C6	0.0918 (5)	0.6114 (4)	0.3481 (2)	0.0335 (10)
H6	0.0951	0.5317	0.3268	0.040*
C7	0.0881 (4)	0.4829 (4)	0.4476 (3)	0.0314 (10)
C8	0.0788 (4)	0.9796 (4)	0.4444 (2)	0.0249 (8)
C9	0.4717 (4)	0.2316 (4)	0.5837 (2)	0.0257 (8)
C10	0.5928 (4)	0.2363 (4)	0.5534 (2)	0.0245 (9)
H10	0.5962	0.2377	0.5101	0.029*
C11	0.7089 (4)	0.2390 (4)	0.58795 (19)	0.0220 (8)
C12	0.7034 (4)	0.2399 (5)	0.6526 (2)	0.0286 (9)
H12	0.7809	0.2424	0.6758	0.034*
C13	0.5834 (4)	0.2370 (4)	0.6825 (2)	0.0327 (10)
H13	0.5802	0.2389	0.7258	0.039*
C14	0.4674 (4)	0.2313 (4)	0.6486 (2)	0.0285 (9)
H14	0.3867	0.2273	0.6691	0.034*
C15	0.3461 (4)	0.2229 (4)	0.5460 (2)	0.0300 (9)
C16	0.8396 (4)	0.2330 (4)	0.5549 (2)	0.0227 (8)
O11B	0.1647 (14)	0.3817 (14)	0.2412 (5)	0.082 (3)	0.618 (10)
N1	0.3469 (8)	0.4165 (5)	0.1823 (3)	0.0859 (17)
C17B	0.2980 (15)	0.3983 (11)	0.2335 (6)	0.088 (3)	0.618 (10)
H17B	0.3526	0.3957	0.2683	0.106*	0.618 (10)
C18B	0.2609 (14)	0.4209 (11)	0.1244 (7)	0.093 (3)	0.618 (10)
H18A	0.2369	0.3328	0.1127	0.140*	0.618 (10)
H18B	0.3088	0.4617	0.0910	0.140*	0.618 (10)
H18C	0.1828	0.4711	0.1330	0.140*	0.618 (10)
C19B	0.4849 (13)	0.4221 (13)	0.1669 (8)	0.099 (3)	0.618 (10)
H19A	0.5354	0.4346	0.2043	0.149*	0.618 (10)
H19B	0.5005	0.4943	0.1390	0.149*	0.618 (10)
H19C	0.5109	0.3411	0.1473	0.149*	0.618 (10)
C18A	0.439 (2)	0.424 (2)	0.2384 (9)	0.105 (5)	0.382 (10)
H18D	0.3884	0.4164	0.2760	0.157*	0.382 (10)
H18E	0.4851	0.5063	0.2380	0.157*	0.382 (10)
H18F	0.5015	0.3527	0.2364	0.157*	0.382 (10)
C19A	0.433 (3)	0.417 (3)	0.1269 (10)	0.110 (6)	0.382 (10)
H19D	0.4565	0.5063	0.1169	0.165*	0.382 (10)
H19E	0.3865	0.3786	0.0923	0.165*	0.382 (10)
H19F	0.5109	0.3670	0.1353	0.165*	0.382 (10)
C17A	0.2249 (19)	0.401 (2)	0.1936 (11)	0.098 (4)	0.382 (10)
H17A	0.1610	0.3926	0.1628	0.117*	0.382 (10)
O11A	0.198 (3)	0.396 (2)	0.2554 (10)	0.102 (5)	0.382 (10)

Atomic displacement parameters (Å²) top

	U¹¹	U²²	U³³	U¹²	U¹³	U²³
Cd1	0.02087 (14)	0.02266 (15)	0.02112 (12)	0.00064 (10)	−0.00023 (11)	−0.00002 (11)
Na1	0.096 (2)	0.0428 (14)	0.0337 (16)	−0.0075 (12)	0.0048 (15)	−0.0055 (8)
Na2	0.0289 (10)	0.0944 (19)	0.0298 (14)	−0.0066 (10)	−0.0059 (9)	0.0114 (12)
O1	0.0375 (18)	0.0144 (13)	0.055 (2)	−0.0009 (11)	−0.0018 (15)	0.0020 (13)
O2	0.062 (2)	0.0262 (15)	0.049 (3)	−0.0022 (14)	−0.001 (2)	0.0105 (18)
O3	0.0471 (16)	0.0271 (13)	0.0305 (15)	0.0009 (12)	−0.0002 (19)	−0.0023 (17)
O4	0.055 (2)	0.0144 (13)	0.0365 (18)	0.0024 (13)	0.0009 (15)	0.0005 (12)
O5	0.0156 (15)	0.083 (3)	0.052 (2)	−0.0012 (16)	−0.0008 (14)	0.005 (2)
O6	0.0319 (17)	0.079 (3)	0.036 (3)	−0.0123 (16)	−0.0103 (17)	0.007 (2)
O7	0.0159 (13)	0.048 (2)	0.0369 (17)	−0.0016 (13)	−0.0045 (12)	0.0016 (15)
O8	0.0263 (13)	0.0429 (15)	0.0265 (13)	0.0009 (11)	0.0044 (17)	0.0006 (18)
O9	0.087 (4)	0.193 (8)	0.052 (3)	0.004 (5)	−0.013 (3)	0.003 (4)
O10	0.113 (5)	0.122 (5)	0.120 (6)	−0.002 (4)	−0.047 (4)	0.049 (4)
C1	0.025 (2)	0.0149 (17)	0.035 (2)	−0.0004 (15)	0.0015 (16)	0.0031 (16)
C2	0.025 (2)	0.0183 (19)	0.027 (2)	−0.0009 (15)	−0.0013 (15)	0.0021 (14)
C3	0.026 (2)	0.0151 (18)	0.026 (2)	−0.0021 (14)	−0.0009 (16)	0.0006 (15)
C4	0.041 (3)	0.022 (2)	0.030 (2)	0.0029 (18)	0.0003 (19)	0.0024 (17)
C5	0.055 (3)	0.028 (2)	0.027 (2)	0.002 (2)	0.0015 (19)	−0.0009 (16)
C6	0.038 (3)	0.020 (2)	0.042 (3)	0.0019 (18)	0.001 (2)	−0.0050 (18)
C7	0.022 (2)	0.0180 (19)	0.054 (3)	−0.0016 (15)	−0.0008 (19)	0.0063 (19)
C8	0.0244 (19)	0.0190 (19)	0.031 (2)	−0.0021 (15)	0.0077 (16)	−0.0011 (16)
C9	0.0167 (18)	0.027 (2)	0.033 (2)	−0.0001 (15)	−0.0045 (16)	0.0025 (17)
C10	0.0184 (19)	0.030 (2)	0.026 (2)	−0.0022 (16)	−0.0008 (14)	0.0035 (15)
C11	0.0165 (17)	0.0230 (19)	0.0265 (19)	−0.0025 (14)	−0.0009 (15)	0.0003 (15)
C12	0.023 (2)	0.039 (2)	0.024 (2)	−0.0001 (17)	−0.0057 (16)	−0.0027 (18)
C13	0.032 (2)	0.041 (3)	0.024 (2)	−0.002 (2)	0.0034 (16)	−0.0011 (17)
C14	0.019 (2)	0.034 (2)	0.032 (2)	0.0019 (17)	0.0061 (16)	−0.0008 (18)
C15	0.0143 (18)	0.029 (2)	0.046 (3)	−0.0017 (15)	−0.0069 (18)	0.0079 (19)
C16	0.0159 (17)	0.0210 (18)	0.031 (2)	−0.0006 (14)	0.0001 (15)	0.0015 (15)
O11B	0.125 (6)	0.051 (6)	0.068 (6)	−0.015 (4)	0.025 (4)	−0.027 (5)
N1	0.135 (5)	0.030 (2)	0.093 (3)	0.000 (3)	0.035 (3)	−0.001 (2)
C17B	0.127 (6)	0.047 (5)	0.091 (4)	−0.012 (4)	0.028 (3)	−0.004 (3)
C18B	0.143 (6)	0.041 (6)	0.095 (5)	0.012 (5)	0.029 (4)	−0.008 (4)
C19B	0.135 (5)	0.048 (6)	0.115 (7)	0.001 (4)	0.036 (4)	0.017 (6)
C18A	0.144 (7)	0.073 (12)	0.098 (5)	−0.018 (7)	0.030 (5)	0.008 (6)
C19A	0.136 (8)	0.099 (18)	0.095 (5)	0.006 (9)	0.035 (5)	0.005 (7)
C17A	0.137 (5)	0.057 (10)	0.100 (6)	−0.008 (4)	0.040 (4)	−0.029 (6)
O11A	0.155 (10)	0.052 (9)	0.100 (6)	−0.039 (9)	0.046 (6)	−0.037 (7)

Geometric parameters (Å, º) top

Cd1—O1	2.301 (3)	C1—C7	1.505 (6)
Cd1—O2	2.555 (3)	C2—H2	0.9300
Cd1—O3ⁱ	2.496 (3)	C2—C3	1.388 (5)
Cd1—O4ⁱ	2.385 (3)	C3—C4	1.391 (6)
Cd1—O5	2.284 (4)	C3—C8	1.501 (5)
Cd1—O7ⁱⁱ	2.396 (3)	C4—H4	0.9300
Cd1—O8ⁱⁱ	2.472 (3)	C4—C5	1.379 (6)
Na1—Na2ⁱⁱⁱ	3.914 (6)	C5—H5	0.9300
Na1—O1	2.368 (5)	C5—C6	1.395 (7)
Na1—O3^iv	2.339 (5)	C6—H6	0.9300
Na1—O4ⁱ	2.441 (5)	C9—C10	1.390 (6)
Na1—O9	2.304 (7)	C9—C14	1.395 (6)
Na1—O11B	2.498 (11)	C9—C15	1.511 (6)
Na1—O11A	2.475 (18)	C10—H10	0.9300
Na2—Cd1^v	3.791 (3)	C10—C11	1.392 (5)
Na2—Na1^v	3.914 (6)	C11—C12	1.390 (6)
Na2—O4^vi	2.655 (5)	C11—C16	1.505 (5)
Na2—O5	2.277 (5)	C12—H12	0.9300
Na2—O7ⁱⁱ	2.282 (4)	C12—C13	1.376 (6)
Na2—O8^vii	2.275 (5)	C13—H13	0.9300
Na2—O10	2.354 (8)	C13—C14	1.385 (6)
O1—C7	1.266 (6)	C14—H14	0.9300
O2—C7	1.237 (8)	O11B—C17B	1.373 (18)
O3—Cd1^viii	2.495 (3)	N1—C17B	1.221 (13)
O3—Na1^vii	2.339 (5)	N1—C18B	1.517 (15)
O3—C8	1.250 (6)	N1—C19B	1.439 (14)
O4—Cd1^viii	2.385 (3)	N1—C18A	1.526 (18)
O4—Na1^viii	2.442 (5)	N1—C19A	1.473 (17)
O4—Na2^ix	2.655 (5)	N1—C17A	1.271 (19)
O4—C8	1.266 (5)	C17B—H17B	0.9300
O5—C15	1.259 (6)	C18B—H18A	0.9600
O6—C15	1.224 (7)	C18B—H18B	0.9600
O7—Cd1^x	2.396 (3)	C18B—H18C	0.9600
O7—Na2^x	2.282 (4)	C19B—H19A	0.9600
O7—C16	1.259 (5)	C19B—H19B	0.9600
O8—Cd1^x	2.472 (3)	C19B—H19C	0.9600
O8—Na2^iv	2.275 (5)	C18A—H18D	0.9600
O8—C16	1.248 (6)	C18A—H18E	0.9600
O9—H9A	0.8971	C18A—H18F	0.9600
O9—H9B	0.8991	C19A—H19D	0.9600
O10—H10A	0.8544	C19A—H19E	0.9600
O10—H10B	0.8548	C19A—H19F	0.9600
C1—C2	1.393 (6)	C17A—H17A	0.9300
C1—C6	1.383 (7)	C17A—O11A	1.36 (2)

O1—Cd1—O2	53.12 (15)	Na2—O10—H10B	109.5
O1—Cd1—O3ⁱ	131.59 (15)	H10A—O10—H10B	109.2
O1—Cd1—O4ⁱ	80.31 (12)	C2—C1—C7	121.2 (4)
O1—Cd1—O7ⁱⁱ	125.91 (12)	C6—C1—C2	118.9 (4)
O1—Cd1—O8ⁱⁱ	92.04 (13)	C6—C1—C7	120.0 (4)
O3ⁱ—Cd1—O2	173.00 (16)	C1—C2—H2	119.6
O4ⁱ—Cd1—O2	132.60 (15)	C3—C2—C1	120.7 (4)
O4ⁱ—Cd1—O3ⁱ	53.37 (13)	C3—C2—H2	119.6
O4ⁱ—Cd1—O7ⁱⁱ	122.40 (12)	C2—C3—C4	119.7 (4)
O4ⁱ—Cd1—O8ⁱⁱ	78.81 (13)	C2—C3—C8	121.1 (4)
O5—Cd1—O1	125.67 (14)	C4—C3—C8	119.2 (3)
O5—Cd1—O2	90.36 (16)	C3—C4—H4	119.9
O5—Cd1—O3ⁱ	82.65 (15)	C5—C4—C3	120.2 (4)
O5—Cd1—O4ⁱ	128.83 (14)	C5—C4—H4	119.9
O5—Cd1—O7ⁱⁱ	80.41 (12)	C4—C5—H5	120.1
O5—Cd1—O8ⁱⁱ	133.24 (16)	C4—C5—C6	119.8 (5)
O7ⁱⁱ—Cd1—O2	85.03 (15)	C6—C5—H5	120.1
O7ⁱⁱ—Cd1—O3ⁱ	94.01 (14)	C1—C6—C5	120.8 (4)
O7ⁱⁱ—Cd1—O8ⁱⁱ	53.55 (14)	C1—C6—H6	119.6
O8ⁱⁱ—Cd1—O2	93.07 (11)	C5—C6—H6	119.6
O8ⁱⁱ—Cd1—O3ⁱ	91.92 (10)	O1—C7—C1	118.1 (5)
O1—Na1—Na2ⁱⁱⁱ	77.99 (11)	O2—C7—O1	121.4 (4)
O1—Na1—O4ⁱ	77.84 (17)	O2—C7—C1	120.5 (4)
O1—Na1—O11B	104.1 (3)	O3—C8—O4	121.4 (4)
O1—Na1—O11A	97.1 (6)	O3—C8—C3	119.9 (4)
O3^iv—Na1—Na2ⁱⁱⁱ	77.96 (14)	O4—C8—C3	118.7 (4)
O3^iv—Na1—O1	151.1 (2)	C10—C9—C14	119.7 (4)
O3^iv—Na1—O4ⁱ	94.59 (15)	C10—C9—C15	119.8 (4)
O3^iv—Na1—O11B	82.9 (3)	C14—C9—C15	120.5 (4)
O3^iv—Na1—O11A	93.0 (6)	C9—C10—H10	120.0
O4ⁱ—Na1—Na2ⁱⁱⁱ	41.86 (11)	C9—C10—C11	120.0 (4)
O4ⁱ—Na1—O11B	177.4 (3)	C11—C10—H10	120.0
O4ⁱ—Na1—O11A	171.5 (7)	C10—C11—C16	119.6 (4)
O9—Na1—Na2ⁱⁱⁱ	130.1 (2)	C12—C11—C10	119.9 (4)
O9—Na1—O1	95.8 (2)	C12—C11—C16	120.4 (4)
O9—Na1—O3^iv	112.0 (2)	C11—C12—H12	120.0
O9—Na1—O4ⁱ	88.3 (2)	C13—C12—C11	120.1 (4)
O9—Na1—O11B	93.2 (4)	C13—C12—H12	120.0
O9—Na1—O11A	85.4 (8)	C12—C13—H13	119.7
O11B—Na1—Na2ⁱⁱⁱ	136.6 (4)	C12—C13—C14	120.5 (4)
O11A—Na1—Na2ⁱⁱⁱ	144.3 (8)	C14—C13—H13	119.7
Cd1^v—Na2—Na1^v	55.94 (8)	C9—C14—H14	120.1
O4^vi—Na2—Cd1^v	38.59 (8)	C13—C14—C9	119.9 (4)
O4^vi—Na2—Na1^v	37.86 (11)	C13—C14—H14	120.1
O5—Na2—Cd1^v	102.07 (15)	O5—C15—C9	117.2 (4)
O5—Na2—Na1^v	57.70 (14)	O6—C15—O5	121.7 (4)
O5—Na2—O4^vi	95.45 (19)	O6—C15—C9	121.1 (4)
O5—Na2—O7ⁱⁱ	83.03 (18)	O7—C16—C11	118.4 (4)
O5—Na2—O10	104.5 (2)	O8—C16—O7	122.1 (4)
O7ⁱⁱ—Na2—Cd1^v	133.31 (13)	O8—C16—C11	119.5 (3)
O7ⁱⁱ—Na2—Na1^v	92.36 (13)	C17B—O11B—Na1	112.8 (9)
O7ⁱⁱ—Na2—O4^vi	94.98 (14)	C17B—N1—C18B	120.6 (10)
O7ⁱⁱ—Na2—O10	80.5 (2)	C17B—N1—C19B	127.4 (12)
O8^vii—Na2—Cd1^v	38.84 (9)	C19B—N1—C18B	111.8 (9)
O8^vii—Na2—Na1^v	89.00 (13)	C19A—N1—C18A	106.0 (13)
O8^vii—Na2—O4^vi	77.02 (13)	C17A—N1—C18A	116.8 (12)
O8^vii—Na2—O5	110.18 (16)	C17A—N1—C19A	136.9 (17)
O8^vii—Na2—O7ⁱⁱ	164.93 (18)	O11B—C17B—H17B	119.1
O8^vii—Na2—O10	102.3 (2)	N1—C17B—O11B	121.8 (13)
O10—Na2—Cd1^v	139.3 (2)	N1—C17B—H17B	119.1
O10—Na2—Na1^v	161.7 (2)	N1—C18B—H18A	109.5
O10—Na2—O4^vi	158.8 (2)	N1—C18B—H18B	109.5
Cd1—O1—Na1	101.49 (13)	N1—C18B—H18C	109.5
C7—O1—Cd1	98.4 (3)	H18A—C18B—H18B	109.5
C7—O1—Na1	159.7 (3)	H18A—C18B—H18C	109.5
C7—O2—Cd1	87.1 (3)	H18B—C18B—H18C	109.5
Na1^vii—O3—Cd1^viii	117.93 (19)	N1—C19B—H19A	109.5
C8—O3—Cd1^viii	90.1 (3)	N1—C19B—H19B	109.5
C8—O3—Na1^vii	143.6 (3)	N1—C19B—H19C	109.5
Cd1^viii—O4—Na1^viii	97.02 (13)	H19A—C19B—H19B	109.5
Cd1^viii—O4—Na2^ix	97.42 (13)	H19A—C19B—H19C	109.5
Na1^viii—O4—Na2^ix	100.28 (18)	H19B—C19B—H19C	109.5
C8—O4—Cd1^viii	94.9 (3)	N1—C18A—H18D	109.5
C8—O4—Na1^viii	146.5 (3)	N1—C18A—H18E	109.5
C8—O4—Na2^ix	109.1 (3)	N1—C18A—H18F	109.5
Na2—O5—Cd1	99.83 (14)	H18D—C18A—H18E	109.5
C15—O5—Cd1	102.4 (3)	H18D—C18A—H18F	109.5
C15—O5—Na2	157.7 (3)	H18E—C18A—H18F	109.5
Na2^x—O7—Cd1^x	96.46 (14)	N1—C19A—H19D	109.5
C16—O7—Cd1^x	93.8 (3)	N1—C19A—H19E	109.5
C16—O7—Na2^x	164.5 (3)	N1—C19A—H19F	109.5
Na2^iv—O8—Cd1^x	105.91 (16)	H19D—C19A—H19E	109.5
C16—O8—Cd1^x	90.5 (2)	H19D—C19A—H19F	109.5
C16—O8—Na2^iv	149.8 (3)	H19E—C19A—H19F	109.5
Na1—O9—H9A	110.8	N1—C17A—H17A	123.6
Na1—O9—H9B	112.4	N1—C17A—O11A	113 (2)
H9A—O9—H9B	106.7	O11A—C17A—H17A	123.6
Na2—O10—H10A	109.8	C17A—O11A—Na1	136.8 (17)

Cd1—O1—C7—O2	1.6 (5)	C4—C3—C8—O3	−164.6 (4)
Cd1—O1—C7—C1	−179.3 (3)	C4—C3—C8—O4	15.9 (6)
Cd1—O2—C7—O1	−1.5 (4)	C4—C5—C6—C1	0.0 (7)
Cd1—O2—C7—C1	179.5 (4)	C6—C1—C2—C3	−0.5 (6)
Cd1^viii—O3—C8—O4	−5.0 (4)	C6—C1—C7—O1	−1.3 (6)
Cd1^viii—O3—C8—C3	175.5 (3)	C6—C1—C7—O2	177.8 (5)
Cd1^viii—O4—C8—O3	5.2 (4)	C7—C1—C2—C3	180.0 (4)
Cd1^viii—O4—C8—C3	−175.2 (3)	C7—C1—C6—C5	179.6 (4)
Cd1—O5—C15—O6	−6.1 (6)	C8—C3—C4—C5	179.5 (4)
Cd1—O5—C15—C9	173.6 (3)	C9—C10—C11—C12	−1.4 (6)
Cd1^x—O7—C16—O8	1.9 (4)	C9—C10—C11—C16	175.0 (4)
Cd1^x—O7—C16—C11	−178.2 (3)	C10—C9—C14—C13	0.6 (7)
Cd1^x—O8—C16—O7	−1.9 (4)	C10—C9—C15—O5	179.3 (4)
Cd1^x—O8—C16—C11	178.3 (3)	C10—C9—C15—O6	−1.0 (7)
Na1—O1—C7—O2	−166.8 (7)	C10—C11—C12—C13	0.5 (7)
Na1—O1—C7—C1	12.2 (11)	C10—C11—C16—O7	177.1 (4)
Na1^vii—O3—C8—O4	−147.3 (4)	C10—C11—C16—O8	−3.1 (6)
Na1^vii—O3—C8—C3	33.1 (7)	C11—C12—C13—C14	1.0 (7)
Na1^viii—O4—C8—O3	115.7 (5)	C12—C11—C16—O7	−6.5 (6)
Na1^viii—O4—C8—C3	−64.7 (7)	C12—C11—C16—O8	173.4 (4)
Na1—O11B—C17B—N1	148.4 (9)	C12—C13—C14—C9	−1.5 (7)
Na2^ix—O4—C8—O3	−94.4 (4)	C14—C9—C10—C11	0.8 (6)
Na2^ix—O4—C8—C3	85.2 (4)	C14—C9—C15—O5	1.0 (6)
Na2—O5—C15—O6	−179.4 (8)	C14—C9—C15—O6	−179.2 (5)
Na2—O5—C15—C9	0.4 (13)	C15—C9—C10—C11	−177.4 (4)
Na2^x—O7—C16—O8	−129.6 (10)	C15—C9—C14—C13	178.9 (4)
Na2^x—O7—C16—C11	50.2 (13)	C16—C11—C12—C13	−175.9 (4)
Na2^iv—O8—C16—O7	122.2 (5)	N1—C17A—O11A—Na1	−116 (3)
Na2^iv—O8—C16—C11	−57.7 (7)	C17B—N1—C17A—O11A	6.5 (16)
C1—C2—C3—C4	0.9 (6)	C18B—N1—C17B—O11B	−0.2 (17)
C1—C2—C3—C8	−179.5 (4)	C18B—N1—C17A—O11A	−174 (2)
C2—C1—C6—C5	0.0 (7)	C19B—N1—C17B—O11B	−173.3 (11)
C2—C1—C7—O1	178.3 (4)	C18A—N1—C17B—O11B	175.3 (18)
C2—C1—C7—O2	−2.6 (6)	C18A—N1—C17A—O11A	2 (3)
C2—C3—C4—C5	−0.9 (7)	C19A—N1—C17B—O11B	−142 (6)
C2—C3—C8—O3	15.8 (6)	C19A—N1—C17A—O11A	174 (2)
C2—C3—C8—O4	−163.7 (4)	C17A—N1—C17B—O11B	0.1 (14)
C3—C4—C5—C6	0.5 (7)

Symmetry codes: (i) x, y−1, z; (ii) x−1, y, z; (iii) −y, x, z−1/4; (iv) −y+1, x, z−1/4; (v) y, −x, z+1/4; (vi) y−1, −x, z+1/4; (vii) y, −x+1, z+1/4; (viii) x, y+1, z; (ix) −y, x+1, z−1/4; (x) x+1, y, z.

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
O9—H9B···O6	0.90	2.22	3.074 (8)	159
O10—H10B···O6^vii	0.86	2.29	3.073 (8)	152
C4—H4···O3^xi	0.93	2.49	3.385 (6)	161
C6—H6···O1	0.93	2.48	2.791 (5)	100
C6—H6···O11B	0.93	2.48	3.347 (14)	155
C10—H10···O10^iv	0.93	2.59	3.277 (8)	131
C14—H14···O8^vii	0.93	2.48	3.366 (5)	159
C18B—H18A···Cg3^iv	-	2.54	3.387 (11)	148
C19B—H19B···Cg4^xii	-	2.93	3.696 (15)	138
C19A—H19D···Cg4^xii	-	2.67	3.53 (4)	151

Symmetry codes: (iv) −y+1, x, z−1/4; (vii) y, −x+1, z+1/4; (xi) −y+1, x+1, z−1/4; (xii) −x+1, −y+1, z−1/2.

Acknowledgements

The authors acknowledge the Department of Chemistry, Faculty of Science and Technology, Thammasat University, Thailand, for financial support and the Central Scientific Instrument Center (CSIC) for funds to purchase the X-ray diffractometer at the Faculty of Science and Technology, Thammasat University, Thailand.

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