Crystal structure of catena-poly[[di­aqua(4,5-di­aza­fluoren-9-one-κ2N,N′)cadmium]-μ-2-hydroxy-5-sulfonato­benzoato-κ3O1,O1′:O5]

Wang, C.-X.; Li, Z.-F.

doi:10.1107/S1600536814023472

metal-organic compounds

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ISSN: 2056-9890

Volume 70| Part 11| November 2014| Pages m387-m388

doi:10.1107/S1600536814023472

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Crystal structure of catena-poly[[diaqua(4,5-diazafluoren-9-one-κ²N,N′)cadmium]-μ-2-hydroxy-5-sulfonatobenzoato-κ³O¹,O^1′:O⁵]

Chun-Xiang Wang ^a and Zhi-Feng Li ^a ^*

^aSchool of Materials Science and Engineering, Jiangxi University of Science and Technology, Ganzhou 341000, People's Republic of China
^*Correspondence e-mail: jxlzfeng@163.com

Edited by W. Imhof, University Koblenz-Landau, Germany (Received 10 October 2014; accepted 25 October 2014; online 31 October 2014)

In the polymeric title compound, [Cd(C₇H₄O₆S)(C₁₁H₆N₂O)(H₂O)₂]_n, the Cd²⁺ atom is seven-coordinated by two water O atoms, by three O atoms from two 2-hydroxy-5-sulfonatobenzoate (Hssal²⁻) ligands and by two N atoms from a 4,5-diazafluoren-9-one (Dafo) ligand in a distorted pentagonal–bipyramidal geometry. The Cd²⁺ atoms are monodentately coordinated by the sulfonate group of one Hssal²⁻ ligand and bidentately coordinated by the carboxylate group of another Hssal²⁻ ligand, generating zigzag chains running parallel to [010]. The chains are linked by O—H⋯O hydrogen bonds into a three-dimensional architecture.

Keywords: crystal structure; one-dimensional coordination polymer; 4,5-diazafluoren-9-one; 2-hydroxy-5-sulfonatobenzoate; cadmium complex; hydrogen bonding.

CCDC reference: 1030993

1. Related literature

For information on compounds with metal–organic framework structures, see: Song et al. (2007 ); Yan et al. (2009 ). For related Cd²⁺ compounds, see: Sun et al. (2010 ).

2. Experimental

2.1. Crystal data

[Cd(C₇H₄O₆S)(C₁₁H₆N₂O)(H₂O)₂]
M_r = 546.77
Monoclinic, P 2₁
a = 7.6233 (6) Å
b = 12.8461 (10) Å
c = 9.4625 (7) Å
β = 98.155 (1)°
V = 917.29 (12) Å³
Z = 2
Mo Kα radiation
μ = 1.37 mm⁻¹
T = 296 K
0.35 × 0.32 × 0.20 mm

2.2. Data collection

Bruker SMART APEXII CCD area-detector diffractometer
Absorption correction: multi-scan (SADABS; Sheldrick, 2003 ) T_min = 0.677, T_max = 0.823
5158 measured reflections
3545 independent reflections
3469 reflections with I > 2σ(I)
R_int = 0.010

2.3. Refinement

R[F² > 2σ(F²)] = 0.015
wR(F²) = 0.037
S = 1.02
3545 reflections
281 parameters
1 restraint
H-atom parameters constrained
Δρ_max = 0.32 e Å⁻³
Δρ_min = −0.23 e Å⁻³
Absolute structure: Flack (1983 ), 1559 Friedel pairs
Absolute structure parameter: 0.040 (13)

Table 1
Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
O8—H8A⋯O6ⁱ	0.85	1.96	2.801 (3)	171
O8—H8B⋯O4ⁱⁱ	0.85	1.93	2.758 (3)	164
O9—H9A⋯O5ⁱⁱⁱ	0.85	1.98	2.771 (3)	154
O9—H9B⋯O1^iv	0.85	2.00	2.820 (3)	161
Symmetry codes: (i) $[-x+1, y+{\script{1\over 2}}, -z+1]$ ; (ii) x, y, z-1; (iii) x+1, y, z; (iv) x, y, z+1.

Data collection: APEX2 (Bruker, 2004 ); cell refinement: SAINT (Bruker, 2004); data reduction: SAINT; 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.

Supporting information

CCDC reference: 1030993

Crystal structure: contains datablocks I, New_Global_Publ_Block. DOI: 10.1107/S1600536814023472/im2455sup1.cif

Structure factors: contains datablock I. DOI: 10.1107/S1600536814023472/im2455Isup2.hkl

checkCIF report

Comment top

In order to understand the coordination chemistry of H₃ssal and to prepare new supramolecular materials with intriguing structures and potential physical properties, 5-sulfosalicylic acid and chelating bipyridyl-like ligands were widely used to construct coordination complexes (Yan et al., 2009). Nevertheless, the Dafo ligand was seldom referred as one of these bipyridyl-like ligands. We chose 2-hydroxy-5-sulfobenzoic acid as an organic carboxylate anion and 4,5-diazafluoren-9-one as a neutral ligand with a N₂-donor set to generate the coordination compound, [Cd(C₁₁H₆N₂O)(C₇H₄O₆S)(H₂O)₂]_n, which is reported here, under hydrothermal conditions.

As shown in Fig. 1, the asymmetric unit of the title compound consists of one Cd²⁺ cation, one Hssal^2- anion, one Dafo ligand and two aqua ligands. Each Cd(II) center adopts a distorted pentagonal bipyramidal geometry and is seven-coordinated by one sulfonato oxygen atom and two carboxylate oxygen atoms from two different Hssal^2- ligands, two N atoms from one Dafo molecule and two water O atoms. The oxygen atoms from the Hssal^2- ligands and the nitrogen atoms form the basal plane while the axial positions are occupied by two water oxygen atoms. The Cd—O distances are in the range of 2.285 (2) - 2.629 (2) Å, with an average bond length of 2.3736 (2) Å, which are all within the normal range generally found in the literature (Sun et al., 2010). Hssal^2- functions as a tridentate ligand, in which two carboxylate oxygen atoms chelate one Cd atom and one sulfonato oxygen atom binds to another Cd atom. Thus the Cd(II) centers are bridged by the Hssal^2- ligands to generate one-dimensional zigzag chains along [010]. Moreover, an extensive hydrogen bond network is observed in the crystal structure of the title compound in which the aqua ligands (O8 and O9) act as the hydrogen donors towards sulfonato oxygen atoms O5 and O6, the hydroxyl oxygen atom O4 and the ketone oxygen atom O1, respectively.

Related literature top

For information on compounds with metal–organic framework structures, see: Song et al. (2007); Yan et al. (2009). For related Cd²⁺ compounds, see: Sun et al. (2010).

Experimental top

A mixture of Cd(NO₃)₂ × 4 H₂O (1.00 mmol, 0.3085 g), 5-sulfosalicylic acid (H₃ssal) dihydrate (1 mmol, 0.2542 g), 4,5-diazafluoren-9-one (Dafo) (1 mmol, 0.1822 g), NaOH (1.00 mmol, 0.04 g) and H₂O (10.0 ml) was heated in a 23 ml Teflon-lined stainless steel reactor at 443 K for 72 h. The yellow plate-like crystals were filtered and washed with water and acetone. Yield: 8% based on Cd.

Computing details top

Data collection: APEX2 (Bruker, 2004); cell refinement: SAINT (Bruker, 2004); data reduction: SAINT (Bruker, 2004); 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

Fig. 1. The asymmetric unit of the title compounds showing displacement ellipsoids at the 30% probability level and H atoms as small spheres of arbitrary radii. Symmetry code: (i) 1 - x, 0.5 + y, 2 - z.

Fig. 2. The one-dimensional zigzag-like chain structure of the title compound. H atoms are omitted for clarity.

catena-Poly[[diaqua(4,5-diazafluoren-9-one-κ²N,N')cadmium]-µ-2-hydroxy-5-sulfonatobenzoato-κ³O¹,O^1':O⁵] top

Crystal data top

[Cd(C₇H₄O₆S)(C₁₁H₆N₂O)(H₂O)₂]	F(000) = 544
M_r = 546.77	D_x = 1.980 Mg m⁻³
Monoclinic, P2₁	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: P 2yb	Cell parameters from 387 reflections
a = 7.6233 (6) Å	θ = 2.1–27.5°
b = 12.8461 (10) Å	µ = 1.37 mm⁻¹
c = 9.4625 (7) Å	T = 296 K
β = 98.155 (1)°	Plate, yellow
V = 917.29 (12) Å³	0.35 × 0.32 × 0.20 mm
Z = 2

Data collection top

Bruker SMART APEXII CCD area-detector diffractometer	3545 independent reflections
Radiation source: fine-focus sealed tube	3469 reflections with I > 2σ(I)
Graphite monochromator	R_int = 0.010
ϕ and ω scans	θ_max = 26.7°, θ_min = 2.2°
Absorption correction: multi-scan (SADABS; Sheldrick, 2003)	h = −9→8
T_min = 0.677, T_max = 0.823	k = −16→16
5158 measured reflections	l = −9→11

Refinement top

Refinement on F²	Hydrogen site location: inferred from neighbouring sites
Least-squares matrix: full	H-atom parameters constrained
R[F² > 2σ(F²)] = 0.015	w = 1/[σ²(F_o²) + (0.0198P)²] where P = (F_o² + 2F_c²)/3
wR(F²) = 0.037	(Δ/σ)_max = 0.010
S = 1.02	Δρ_max = 0.32 e Å⁻³
3545 reflections	Δρ_min = −0.23 e Å⁻³
281 parameters	Extinction correction: SHELXL97 (Sheldrick, 2008), Fc^*=kFc[1+0.001xFc²λ³/sin(2θ)]^-1/4
1 restraint	Extinction coefficient: 0.0055 (5)
Primary atom site location: structure-invariant direct methods	Absolute structure: Flack (1983), 1559 Friedel pairs
Secondary atom site location: difference Fourier map	Absolute structure parameter: 0.040 (13)

Crystal data top

[Cd(C₇H₄O₆S)(C₁₁H₆N₂O)(H₂O)₂]	V = 917.29 (12) Å³
M_r = 546.77	Z = 2
Monoclinic, P2₁	Mo Kα radiation
a = 7.6233 (6) Å	µ = 1.37 mm⁻¹
b = 12.8461 (10) Å	T = 296 K
c = 9.4625 (7) Å	0.35 × 0.32 × 0.20 mm
β = 98.155 (1)°

Data collection top

Bruker SMART APEXII CCD area-detector diffractometer	3545 independent reflections
Absorption correction: multi-scan (SADABS; Sheldrick, 2003)	3469 reflections with I > 2σ(I)
T_min = 0.677, T_max = 0.823	R_int = 0.010
5158 measured reflections

Refinement top

R[F² > 2σ(F²)] = 0.015	H-atom parameters constrained
wR(F²) = 0.037	Δρ_max = 0.32 e Å⁻³
S = 1.02	Δρ_min = −0.23 e Å⁻³
3545 reflections	Absolute structure: Flack (1983), 1559 Friedel pairs
281 parameters	Absolute structure parameter: 0.040 (13)
1 restraint

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	0.7119 (3)	0.11149 (18)	0.4387 (2)	0.0325 (5)
H1	0.6659	0.0842	0.5167	0.039*
C2	0.7228 (3)	0.04706 (19)	0.3233 (3)	0.0369 (5)
H2	0.6851	−0.0217	0.3254	0.044*
C3	0.7902 (3)	0.08485 (19)	0.2036 (3)	0.0377 (5)
H3	0.7993	0.0427	0.1251	0.045*
C4	0.8423 (3)	0.18736 (18)	0.2071 (2)	0.0305 (5)
C5	0.9171 (3)	0.2583 (2)	0.1039 (3)	0.0349 (5)
C6	0.9390 (2)	0.3622 (3)	0.17581 (19)	0.0327 (4)
C7	1.0001 (3)	0.4579 (2)	0.1391 (3)	0.0412 (6)
H7	1.0365	0.4693	0.0506	0.049*
C8	1.0049 (3)	0.5374 (2)	0.2407 (3)	0.0434 (6)
H8	1.0489	0.6026	0.2215	0.052*
C9	0.9445 (3)	0.51923 (17)	0.3698 (3)	0.0355 (5)
H9	0.9428	0.5746	0.4329	0.043*
C10	0.8864 (2)	0.3516 (2)	0.3100 (2)	0.0280 (4)
C11	0.8275 (3)	0.24562 (16)	0.3282 (2)	0.0282 (4)
C12	0.4313 (3)	0.19306 (15)	0.9233 (2)	0.0248 (4)
C13	0.3771 (3)	0.11221 (16)	1.0031 (2)	0.0261 (4)
H13	0.3678	0.0454	0.9650	0.031*
C14	0.3361 (3)	0.12964 (15)	1.1403 (2)	0.0241 (4)
C15	0.3489 (3)	0.23148 (16)	1.1954 (2)	0.0262 (4)
C16	0.4067 (3)	0.31269 (17)	1.1150 (2)	0.0308 (5)
H16	0.4169	0.3797	1.1525	0.037*
C17	0.4488 (3)	0.29364 (16)	0.9797 (2)	0.0291 (5)
H17	0.4885	0.3475	0.9267	0.035*
C18	0.2836 (3)	0.04158 (16)	1.2294 (2)	0.0277 (4)
Cd1	0.760273 (16)	0.360333 (13)	0.613628 (12)	0.02682 (5)
N1	0.7645 (2)	0.21201 (14)	0.44437 (19)	0.0281 (4)
N2	0.8881 (2)	0.42577 (14)	0.4086 (2)	0.0301 (4)
O1	0.9547 (2)	0.23396 (15)	−0.01156 (18)	0.0460 (4)
O2	0.2854 (2)	−0.04920 (12)	1.18426 (18)	0.0392 (4)
O3	0.2427 (2)	0.06334 (13)	1.35128 (17)	0.0377 (4)
O4	0.3065 (2)	0.25331 (12)	1.32612 (16)	0.0344 (4)
H4	0.2813	0.1972	1.3664	0.052*
O5	0.3267 (2)	0.22249 (15)	0.65477 (18)	0.0418 (4)
O6	0.4806 (2)	0.06102 (12)	0.72661 (17)	0.0394 (4)
O7	0.6409 (2)	0.22356 (13)	0.73467 (17)	0.0359 (4)
O8	0.4984 (2)	0.40770 (12)	0.48081 (17)	0.0338 (3)
O9	1.0370 (2)	0.32540 (13)	0.73495 (18)	0.0411 (4)
S1	0.47242 (7)	0.17302 (4)	0.74579 (5)	0.02593 (11)
H8B	0.4229	0.3687	0.4315	0.039*
H8A	0.5159	0.4564	0.4233	0.039*
H9B	1.0268	0.3091	0.8205	0.039*
H9A	1.1283	0.3117	0.6959	0.039*

Atomic displacement parameters (Å²) top

	U¹¹	U²²	U³³	U¹²	U¹³	U²³
C1	0.0372 (12)	0.0294 (11)	0.0329 (12)	0.0010 (9)	0.0118 (9)	0.0016 (9)
C2	0.0391 (13)	0.0270 (11)	0.0451 (15)	−0.0021 (9)	0.0082 (10)	−0.0056 (11)
C3	0.0377 (12)	0.0425 (13)	0.0347 (13)	0.0024 (10)	0.0114 (10)	−0.0125 (10)
C4	0.0337 (11)	0.0356 (12)	0.0240 (11)	0.0049 (9)	0.0107 (9)	−0.0025 (9)
C5	0.0299 (13)	0.0481 (14)	0.0279 (13)	0.0057 (10)	0.0082 (10)	0.0006 (10)
C6	0.0330 (9)	0.0392 (10)	0.0272 (9)	0.0066 (15)	0.0087 (7)	0.0022 (14)
C7	0.0398 (14)	0.0481 (15)	0.0389 (15)	0.0024 (12)	0.0163 (11)	0.0146 (11)
C8	0.0424 (13)	0.0349 (13)	0.0545 (16)	−0.0024 (10)	0.0125 (11)	0.0125 (11)
C9	0.0366 (12)	0.0270 (11)	0.0434 (14)	0.0001 (9)	0.0071 (10)	0.0021 (10)
C10	0.0302 (9)	0.0285 (11)	0.0262 (9)	0.0045 (11)	0.0072 (7)	0.0026 (11)
C11	0.0319 (11)	0.0293 (11)	0.0241 (11)	0.0025 (8)	0.0067 (9)	−0.0001 (9)
C12	0.0305 (10)	0.0242 (10)	0.0207 (10)	−0.0005 (8)	0.0074 (8)	−0.0005 (8)
C13	0.0307 (10)	0.0236 (9)	0.0240 (10)	−0.0010 (8)	0.0036 (8)	0.0008 (8)
C14	0.0245 (10)	0.0249 (10)	0.0228 (10)	−0.0005 (7)	0.0031 (8)	0.0026 (8)
C15	0.0296 (10)	0.0283 (10)	0.0207 (10)	0.0004 (8)	0.0029 (8)	−0.0002 (8)
C16	0.0447 (12)	0.0220 (9)	0.0269 (11)	−0.0046 (9)	0.0090 (9)	−0.0044 (9)
C17	0.0397 (12)	0.0227 (10)	0.0256 (11)	−0.0037 (8)	0.0071 (9)	0.0032 (8)
C18	0.0285 (11)	0.0284 (11)	0.0266 (11)	0.0005 (9)	0.0053 (8)	0.0068 (9)
Cd1	0.03529 (8)	0.02431 (7)	0.02215 (7)	0.00261 (8)	0.00855 (5)	−0.00201 (7)
N1	0.0358 (10)	0.0268 (9)	0.0236 (9)	−0.0001 (7)	0.0108 (7)	0.0002 (7)
N2	0.0338 (10)	0.0278 (9)	0.0300 (10)	0.0024 (7)	0.0088 (8)	0.0016 (7)
O1	0.0552 (11)	0.0605 (11)	0.0258 (9)	0.0062 (9)	0.0179 (8)	−0.0043 (8)
O2	0.0571 (11)	0.0267 (8)	0.0356 (10)	−0.0041 (7)	0.0131 (8)	0.0045 (7)
O3	0.0517 (10)	0.0372 (9)	0.0275 (8)	−0.0024 (7)	0.0170 (7)	0.0068 (7)
O4	0.0516 (10)	0.0311 (8)	0.0230 (8)	−0.0039 (7)	0.0136 (7)	−0.0024 (6)
O5	0.0477 (10)	0.0529 (11)	0.0247 (9)	0.0116 (9)	0.0054 (7)	0.0019 (8)
O6	0.0644 (11)	0.0250 (8)	0.0316 (9)	−0.0041 (7)	0.0169 (8)	−0.0068 (6)
O7	0.0396 (9)	0.0381 (9)	0.0330 (9)	−0.0065 (7)	0.0155 (7)	−0.0005 (7)
O8	0.0406 (8)	0.0270 (7)	0.0325 (9)	−0.0018 (7)	0.0012 (7)	0.0018 (7)
O9	0.0377 (9)	0.0494 (11)	0.0376 (9)	0.0065 (7)	0.0103 (7)	0.0094 (7)
S1	0.0351 (3)	0.0234 (2)	0.0208 (2)	−0.0010 (2)	0.0093 (2)	−0.00040 (19)

Geometric parameters (Å, º) top

C1—N1	1.351 (3)	C14—C15	1.407 (3)
C1—C2	1.382 (3)	C14—C18	1.499 (3)
C1—H1	0.9300	C15—O4	1.351 (3)
C2—C3	1.395 (4)	C15—C16	1.399 (3)
C2—H2	0.9300	C16—C17	1.385 (3)
C3—C4	1.375 (3)	C16—H16	0.9300
C3—H3	0.9300	C17—H17	0.9300
C4—C11	1.386 (3)	C18—O2	1.243 (3)
C4—C5	1.506 (3)	C18—O3	1.268 (3)
C5—O1	1.209 (3)	Cd1—O8	2.2857 (16)
C5—C6	1.497 (4)	Cd1—O9	2.2984 (16)
C6—C7	1.376 (4)	Cd1—O2ⁱ	2.3061 (16)
C6—C10	1.391 (3)	Cd1—O7	2.3501 (16)
C7—C8	1.399 (4)	Cd1—N2	2.4404 (19)
C7—H7	0.9300	Cd1—N1	2.4922 (18)
C8—C9	1.385 (4)	Cd1—O3ⁱ	2.6294 (17)
C8—H8	0.9300	O2—Cd1ⁱⁱ	2.3061 (16)
C9—N2	1.344 (3)	O3—Cd1ⁱⁱ	2.6294 (17)
C9—H9	0.9300	O4—H4	0.8504
C10—N2	1.333 (3)	O5—S1	1.4518 (18)
C10—C11	1.452 (3)	O6—S1	1.4527 (16)
C11—N1	1.333 (3)	O7—S1	1.4561 (17)
C12—C13	1.381 (3)	O8—H8B	0.8500
C12—C17	1.397 (3)	O8—H8A	0.8519
C12—S1	1.771 (2)	O9—H9B	0.8507
C13—C14	1.395 (3)	O9—H9A	0.8510
C13—H13	0.9300

N1—C1—C2	123.6 (2)	C16—C17—H17	120.2
N1—C1—H1	118.2	C12—C17—H17	120.2
C2—C1—H1	118.2	O2—C18—O3	122.4 (2)
C1—C2—C3	120.2 (2)	O2—C18—C14	119.85 (19)
C1—C2—H2	119.9	O3—C18—C14	117.73 (19)
C3—C2—H2	119.9	O8—Cd1—O9	174.22 (6)
C4—C3—C2	116.9 (2)	O8—Cd1—O2ⁱ	95.69 (6)
C4—C3—H3	121.6	O9—Cd1—O2ⁱ	85.41 (6)
C2—C3—H3	121.6	O8—Cd1—O7	95.66 (6)
C3—C4—C11	118.7 (2)	O9—Cd1—O7	90.12 (6)
C3—C4—C5	134.4 (2)	O2ⁱ—Cd1—O7	81.84 (6)
C11—C4—C5	107.0 (2)	O8—Cd1—N2	83.53 (6)
O1—C5—C6	128.0 (2)	O9—Cd1—N2	91.30 (6)
O1—C5—C4	126.1 (2)	O2ⁱ—Cd1—N2	127.58 (6)
C6—C5—C4	105.86 (19)	O7—Cd1—N2	150.56 (6)
C7—C6—C10	118.0 (3)	O8—Cd1—N1	86.57 (6)
C7—C6—C5	134.6 (2)	O9—Cd1—N1	94.42 (6)
C10—C6—C5	107.4 (2)	O2ⁱ—Cd1—N1	159.30 (6)
C6—C7—C8	117.1 (2)	O7—Cd1—N1	77.46 (6)
C6—C7—H7	121.5	N2—Cd1—N1	73.11 (6)
C8—C7—H7	121.5	O8—Cd1—O3ⁱ	77.46 (5)
C9—C8—C7	120.2 (2)	O9—Cd1—O3ⁱ	98.87 (6)
C9—C8—H8	119.9	O2ⁱ—Cd1—O3ⁱ	52.44 (5)
C7—C8—H8	119.9	O7—Cd1—O3ⁱ	132.00 (5)
N2—C9—C8	123.4 (2)	N2—Cd1—O3ⁱ	76.72 (5)
N2—C9—H9	118.3	N1—Cd1—O3ⁱ	147.20 (5)
C8—C9—H9	118.3	C11—N1—C1	114.62 (19)
N2—C10—C6	126.4 (3)	C11—N1—Cd1	108.76 (13)
N2—C10—C11	124.04 (19)	C1—N1—Cd1	136.50 (16)
C6—C10—C11	109.5 (2)	C10—N2—C9	114.8 (2)
N1—C11—C4	126.0 (2)	C10—N2—Cd1	110.21 (14)
N1—C11—C10	123.74 (19)	C9—N2—Cd1	134.77 (16)
C4—C11—C10	110.22 (19)	C18—O2—Cd1ⁱⁱ	100.22 (14)
C13—C12—C17	120.43 (19)	C18—O3—Cd1ⁱⁱ	84.48 (13)
C13—C12—S1	121.07 (15)	C15—O4—H4	109.5
C17—C12—S1	118.46 (16)	S1—O7—Cd1	140.81 (11)
C12—C13—C14	120.76 (19)	Cd1—O8—H8B	128.0
C12—C13—H13	119.6	Cd1—O8—H8A	110.0
C14—C13—H13	119.6	H8B—O8—H8A	103.7
C13—C14—C15	118.78 (18)	Cd1—O9—H9B	108.8
C13—C14—C18	121.01 (18)	Cd1—O9—H9A	124.9
C15—C14—C18	120.19 (18)	H9B—O9—H9A	123.6
O4—C15—C16	118.54 (19)	O5—S1—O6	113.71 (11)
O4—C15—C14	121.31 (19)	O5—S1—O7	111.74 (11)
C16—C15—C14	120.15 (19)	O6—S1—O7	112.26 (10)
C17—C16—C15	120.2 (2)	O5—S1—C12	106.01 (10)
C17—C16—H16	119.9	O6—S1—C12	106.20 (9)
C15—C16—H16	119.9	O7—S1—C12	106.27 (10)
C16—C17—C12	119.62 (19)

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

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
O8—H8A···O6ⁱⁱⁱ	0.85	1.96	2.801 (3)	171
O8—H8B···O4^iv	0.85	1.93	2.758 (3)	164
O9—H9A···O5^v	0.85	1.98	2.771 (3)	154
O9—H9B···O1^vi	0.85	2.00	2.820 (3)	161

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

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
O8—H8A···O6ⁱ	0.85	1.96	2.801 (3)	171
O8—H8B···O4ⁱⁱ	0.85	1.93	2.758 (3)	164
O9—H9A···O5ⁱⁱⁱ	0.85	1.98	2.771 (3)	154
O9—H9B···O1^iv	0.85	2.00	2.820 (3)	161

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

Acknowledgements

This work was supported by the Natural Science Foundation of Jiangxi Province (grant No. 2010GQC0064), the Science and Technology Support Fundation of Jiangxi Province (grant Nos. 2012BBE500038 and 20141BBE50019) and Jiangxi University of Science and Technology Foundation (grant No. 3304000027).

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