catena-Poly[[[bis­[μ-3-(4-carb­oxy­phen­oxy)propionato]-κ3O1,O1′:O1;κ3O1:O1,O1′-bis­[aqua­(N,N-dimethyl­formamide-κO)cadmium]]-μ-4,4′-bipyridine-κ2N:N′] dinitrate]

Gao, S.; Ng, S.W.

doi:10.1107/S1600536812002991

metal-organic compounds

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ISSN: 2056-9890

Volume 68| Part 2| February 2012| Page m214

doi:10.1107/S1600536812002991

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catena-Poly[[[bis[μ-3-(4-carboxyphenoxy)propionato]-κ³O¹,O^1′:O¹;κ³O¹:O¹,O^1′-bis[aqua(N,N-dimethylformamide-κO)cadmium]]-μ-4,4′-bipyridine-κ²N:N′] dinitrate]

Shan Gao ^a and Seik Weng Ng ^b,^c ^*

^aKey Laboratory of Functional Inorganic Materials Chemistry, Ministry of Education, Heilongjiang University, Harbin 150080, People's Republic of China, ^bDepartment of Chemistry, University of Malaya, 50603 Kuala Lumpur, Malaysia, and ^cChemistry Department, Faculty of Science, King Abdulaziz University, PO Box 80203 Jeddah, Saudi Arabia
^*Correspondence e-mail: seikweng@um.edu.my

(Received 24 January 2012; accepted 24 January 2012; online 31 January 2012)

In the title coordination polymer, {[Cd₂(C₁₀H₉O₅)₂(C₁₀H₈N₂)₂(C₃H₇NO)₂(H₂O)₂](NO₃)₂}_n, the 3-(4-carboxyphenoxy)propionate monoanion O,O′-chelates to a Cd^II cation through the aliphatic carboxylate end. One of these O atoms is also connected to the metal cation from an inversion-related metal atom. The five O atoms bonded to the metal centre form a pentagon, above and below which are located the N atoms of the 4,4′-bipyridine molecules. The polycationic ribbon propagates along the b axis of the unit cell. The (aromatic) carboxyl end of the monoanion connects adjacent ribbons into a layer motif in the (102) plane. The nitrate ions are hydrogen bonded to the layer. The geometry of the Cd^II atom is a trans-N₂O₅Cd pentagonal bipyramid.

Related literature

For 3-(4-carboxyphenoxy)propionic acid, see: Gao & Ng (2006 ).

Experimental

Crystal data

[Cd₂(C₁₀H₉O₅)₂(C₁₀H₈N₂)₂(C₃H₇NO)₂(H₂O)₂](NO₃)₂
M_r = 1261.76
Triclinic, $[P \overline 1]$
a = 9.1020 (5) Å
b = 11.6866 (5) Å
c = 13.3534 (5) Å
α = 69.1646 (11)°
β = 84.2052 (16)°
γ = 76.9358 (16)°
V = 1292.84 (10) Å³
Z = 1
Mo Kα radiation
μ = 0.91 mm⁻¹
T = 293 K
0.19 × 0.12 × 0.11 mm

Data collection

Rigaku R-AXIS RAPID IP diffractometer
Absorption correction: multi-scan (ABSCOR; Higashi, 1995 ) T_min = 0.847, T_max = 0.907
12594 measured reflections
5822 independent reflections
4760 reflections with I > 2σ(I)
R_int = 0.031

Refinement

R[F² > 2σ(F²)] = 0.030
wR(F²) = 0.077
S = 1.08
5822 reflections
345 parameters
H-atom parameters constrained
Δρ_max = 0.95 e Å⁻³
Δρ_min = −0.59 e Å⁻³

Table 1
Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
O5—H5⋯O4ⁱ	0.84	1.80	2.629 (3)	171
O1W—H11⋯O7	0.84	1.94	2.754 (4)	164
O1W—H12⋯O2ⁱⁱ	0.84	2.03	2.763 (3)	145
Symmetry codes: (i) -x+2, -y+1, -z; (ii) -x+1, -y+2, -z+1.

Data collection: RAPID-AUTO (Rigaku, 1998 ); cell refinement: RAPID-AUTO; data reduction: CrystalClear (Rigaku, 2002 ); program(s) used to solve structure: SHELXS97 (Sheldrick, 2008 ); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008); molecular graphics: X-SEED (Barbour, 2001 ); software used to prepare material for publication: publCIF (Westrip, 2010 ).

Supporting information

Crystal structure: contains datablocks global, I. DOI: 10.1107/S1600536812002991/bt5796sup1.cif

Structure factors: contains datablock I. DOI: 10.1107/S1600536812002991/bt5796Isup2.hkl

checkCIF report

Comment top

We reported the crystal structure of 3-(4-carboxyphenoxy)propropionic acid (Gao & Ng, 2006). We also reported the crystal structures of some metal derivatives. In the coordination polymer, [Cd₂(H₂O)₂(C₁₀H₈N₂)₂(DMF)₂(C₁₀H₈O₅)₂]_n 2n(NO₃) (Scheme I), the 3-(4-carboxyphenoxy)propionate monoanion O,O'-chelates to a Cd^II atom atom through the aliphatic (negatively-charged) carboxyl –CO₂ end; one of the O atoms is also connected to an inversion-related metal atom. The carboxyl O atoms, the carboxyl O atom of an inversion-related dianion, and the O atoms of the water and DMF molecules comprise a pentagon, above and below which are located the N atoms of the 4,4'-bipyridine heterocycle (Fig. 1). The polycationic ribbon propogates along the b-axis of the unit cell; the (aromatic) carboxylic acid end of the monoanion connects adjacent ribbons (Fig. 2) into a layer motif; the nitrate ions are hydrogen bonded to the layer (Table 1).

Related literature top

For 3-(4-carboxyphenoxy)propropionic acid, see: Gao & Ng (2006).

Experimental top

Cadmium nitrate and 3-(4-carboxyphenoxy)propionic acid (1 mmol) were mixed in a water-DMF (3/1) mixture (10 ml). 4,4'-Bipyridine dissolved in methanol (5 ml) was added. The mixture was stirred until the reactants dissolved. Yellow crystals were isolated after a few days.

Computing details top

Data collection: RAPID-AUTO (Rigaku, 1998); cell refinement: RAPID-AUTO (Rigaku, 1998); data reduction: CrystalClear (Rigaku, 2002); program(s) used to solve structure: SHELXS97 (Sheldrick, 2008); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008); molecular graphics: X-SEED (Barbour, 2001); software used to prepare material for publication: publCIF (Westrip, 2010).

Figures top

	Fig. 1. Anitoropic displacement ellipsoid plot (Barbour, 2001) of a portion of polymeric [Cd₂(H₂O)₂(C₁₀H₈N₂)₂(C₃H₇NO)₂(C₁₀H₈O₅)₂]_n 2n(NO₃) at the 50% probability level; hydrogen atoms are drawn as spheres of arbitrary radius.
	Fig. 2. Polycationic ribbon motif.

catena-Poly[[[bis[µ-3-(4-carboxyphenoxy)propionato]- κ³O¹,O^1':O¹; κ³O¹:O¹,O^1'- bis[aqua(N,N-dimethylformamide-κO)cadmium]]-µ- 4,4'-bipyridine-κ²N:N'] dinitrate] top

Crystal data top

[Cd₂(C₁₀H₉O₅)₂(C₁₀H₈N₂)₂(C₃H₇NO)₂(H₂O)₂](NO₃)₂	Z = 1
M_r = 1261.76	F(000) = 640
Triclinic, P1	D_x = 1.621 Mg m⁻³
Hall symbol: -P 1	Mo Kα radiation, λ = 0.71073 Å
a = 9.1020 (5) Å	Cell parameters from 10397 reflections
b = 11.6866 (5) Å	θ = 3.2–27.5°
c = 13.3534 (5) Å	µ = 0.91 mm⁻¹
α = 69.1646 (11)°	T = 293 K
β = 84.2052 (16)°	Prism, yellow
γ = 76.9358 (16)°	0.19 × 0.12 × 0.11 mm
V = 1292.84 (10) Å³

Data collection top

Rigaku R-AXIS RAPID IP diffractometer	5822 independent reflections
Radiation source: fine-focus sealed tube	4760 reflections with I > 2σ(I)
Graphite monochromator	R_int = 0.031
ω scan	θ_max = 27.5°, θ_min = 3.2°
Absorption correction: multi-scan (ABSCOR; Higashi, 1995)	h = −11→11
T_min = 0.847, T_max = 0.907	k = −15→14
12594 measured reflections	l = −17→16

Refinement top

Refinement on F²	Primary atom site location: structure-invariant direct methods
Least-squares matrix: full	Secondary atom site location: difference Fourier map
R[F² > 2σ(F²)] = 0.030	Hydrogen site location: inferred from neighbouring sites
wR(F²) = 0.077	H-atom parameters constrained
S = 1.08	w = 1/[σ²(F_o²) + (0.0367P)² + 0.2058P] where P = (F_o² + 2F_c²)/3
5822 reflections	(Δ/σ)_max = 0.001
345 parameters	Δρ_max = 0.95 e Å⁻³
0 restraints	Δρ_min = −0.59 e Å⁻³

Crystal data top

[Cd₂(C₁₀H₉O₅)₂(C₁₀H₈N₂)₂(C₃H₇NO)₂(H₂O)₂](NO₃)₂	γ = 76.9358 (16)°
M_r = 1261.76	V = 1292.84 (10) Å³
Triclinic, P1	Z = 1
a = 9.1020 (5) Å	Mo Kα radiation
b = 11.6866 (5) Å	µ = 0.91 mm⁻¹
c = 13.3534 (5) Å	T = 293 K
α = 69.1646 (11)°	0.19 × 0.12 × 0.11 mm
β = 84.2052 (16)°

Data collection top

Rigaku R-AXIS RAPID IP diffractometer	5822 independent reflections
Absorption correction: multi-scan (ABSCOR; Higashi, 1995)	4760 reflections with I > 2σ(I)
T_min = 0.847, T_max = 0.907	R_int = 0.031
12594 measured reflections

Refinement top

R[F² > 2σ(F²)] = 0.030	0 restraints
wR(F²) = 0.077	H-atom parameters constrained
S = 1.08	Δρ_max = 0.95 e Å⁻³
5822 reflections	Δρ_min = −0.59 e Å⁻³
345 parameters

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

	x	y	z	U_iso*/U_eq
Cd1	0.18002 (2)	0.944005 (16)	0.589093 (15)	0.02562 (7)
O1	0.0904 (2)	1.01688 (18)	0.40717 (15)	0.0361 (4)
O2	0.3311 (2)	1.00556 (19)	0.41763 (15)	0.0390 (5)
O3	0.3901 (3)	0.8936 (2)	0.23010 (18)	0.0493 (6)
O4	0.8546 (3)	0.4867 (2)	0.0878 (2)	0.0620 (7)
O5	0.9522 (3)	0.6549 (2)	0.0014 (2)	0.0741 (8)
H5	1.0193	0.6153	−0.0288	0.111*
O6	0.1426 (3)	0.8763 (2)	0.77857 (16)	0.0479 (5)
O7	0.5403 (4)	0.6153 (3)	0.6982 (3)	0.0893 (10)
O8	0.7250 (5)	0.6396 (4)	0.7677 (4)	0.1299 (16)
O9	0.7435 (3)	0.4764 (3)	0.7307 (3)	0.0829 (9)
O1W	0.4333 (2)	0.8691 (2)	0.64542 (17)	0.0486 (5)
H11	0.4611	0.7941	0.6493	0.073*
H12	0.4890	0.9124	0.6010	0.073*
N1	0.1779 (3)	0.74731 (19)	0.58879 (18)	0.0307 (5)
N2	0.1773 (3)	0.1380 (2)	0.59570 (18)	0.0315 (5)
N3	0.2606 (4)	0.7602 (3)	0.9348 (2)	0.0646 (9)
N4	0.6706 (4)	0.5765 (3)	0.7332 (3)	0.0596 (8)
C1	0.2171 (3)	1.0305 (2)	0.3627 (2)	0.0282 (5)
C2	0.2299 (4)	1.0791 (3)	0.2418 (2)	0.0423 (7)
H2A	0.2158	1.1695	0.2170	0.051*
H2B	0.1497	1.0586	0.2130	0.051*
C3	0.3801 (4)	1.0261 (3)	0.1987 (2)	0.0440 (7)
H3A	0.3853	1.0634	0.1213	0.053*
H3B	0.4624	1.0431	0.2284	0.053*
C4	0.5115 (4)	0.8267 (3)	0.1927 (2)	0.0413 (7)
C5	0.5131 (4)	0.7005 (3)	0.2196 (2)	0.0426 (7)
H5A	0.4373	0.6657	0.2639	0.051*
C6	0.6268 (4)	0.6263 (3)	0.1807 (2)	0.0412 (7)
H6	0.6275	0.5416	0.1990	0.049*
C7	0.7403 (4)	0.6773 (3)	0.1143 (2)	0.0415 (7)
C8	0.7405 (4)	0.8018 (3)	0.0913 (3)	0.0515 (8)
H8	0.8178	0.8360	0.0485	0.062*
C9	0.6276 (4)	0.8772 (3)	0.1307 (3)	0.0514 (8)
H9	0.6299	0.9608	0.1156	0.062*
C10	0.8552 (4)	0.5984 (3)	0.0665 (3)	0.0481 (8)
C11	0.0810 (3)	0.6805 (2)	0.6513 (2)	0.0339 (6)
H11A	0.0148	0.7150	0.6957	0.041*
C12	0.0742 (3)	0.5627 (2)	0.6532 (2)	0.0330 (6)
H12A	0.0044	0.5198	0.6978	0.040*
C13	0.1722 (3)	0.5090 (2)	0.5881 (2)	0.0279 (5)
C14	0.2714 (3)	0.5799 (2)	0.5215 (2)	0.0366 (6)
H14	0.3376	0.5486	0.4752	0.044*
C15	0.2709 (3)	0.6963 (3)	0.5248 (2)	0.0362 (6)
H15	0.3385	0.7419	0.4802	0.043*
C16	0.0616 (3)	0.2007 (3)	0.6371 (2)	0.0376 (7)
H16	−0.0188	0.1622	0.6681	0.045*
C17	0.0552 (3)	0.3203 (3)	0.6364 (2)	0.0381 (7)
H17	−0.0282	0.3605	0.6661	0.046*
C18	0.1735 (3)	0.3800 (2)	0.5914 (2)	0.0278 (5)
C19	0.2945 (4)	0.3138 (3)	0.5491 (3)	0.0428 (7)
H19	0.3768	0.3498	0.5180	0.051*
C20	0.2921 (4)	0.1946 (3)	0.5536 (3)	0.0448 (8)
H20	0.3748	0.1515	0.5258	0.054*
C21	0.2327 (4)	0.7857 (3)	0.8328 (3)	0.0483 (8)
H21	0.2858	0.7304	0.7998	0.058*
C22	0.1831 (6)	0.8376 (5)	0.9937 (4)	0.0898 (16)
H22A	0.1137	0.9066	0.9477	0.135*
H22B	0.2548	0.8687	1.0197	0.135*
H22C	0.1286	0.7895	1.0532	0.135*
C23	0.3709 (7)	0.6488 (6)	0.9891 (4)	0.118 (2)
H23A	0.4105	0.6049	0.9405	0.177*
H23B	0.3234	0.5955	1.0496	0.177*
H23C	0.4516	0.6725	1.0131	0.177*

Atomic displacement parameters (Å²) top

	U¹¹	U²²	U³³	U¹²	U¹³	U²³
Cd1	0.02636 (11)	0.01654 (10)	0.03726 (12)	−0.00540 (7)	−0.00062 (7)	−0.01261 (7)
O1	0.0260 (11)	0.0386 (11)	0.0424 (11)	−0.0067 (9)	0.0057 (8)	−0.0140 (9)
O2	0.0319 (12)	0.0424 (12)	0.0433 (11)	−0.0115 (9)	0.0017 (9)	−0.0139 (9)
O3	0.0467 (14)	0.0443 (13)	0.0622 (14)	−0.0143 (11)	0.0238 (11)	−0.0283 (11)
O4	0.0743 (19)	0.0414 (14)	0.0691 (16)	−0.0119 (13)	0.0278 (13)	−0.0256 (12)
O5	0.071 (2)	0.0525 (16)	0.101 (2)	−0.0199 (14)	0.0489 (16)	−0.0380 (14)
O6	0.0440 (14)	0.0504 (14)	0.0415 (12)	−0.0020 (11)	−0.0028 (10)	−0.0107 (10)
O7	0.053 (2)	0.0577 (19)	0.136 (3)	−0.0091 (15)	−0.0075 (18)	−0.0079 (17)
O8	0.117 (3)	0.103 (3)	0.207 (5)	−0.016 (3)	−0.031 (3)	−0.094 (3)
O9	0.0556 (19)	0.0490 (17)	0.140 (3)	−0.0094 (14)	0.0235 (17)	−0.0346 (17)
O1W	0.0314 (12)	0.0417 (13)	0.0651 (14)	−0.0108 (10)	−0.0036 (10)	−0.0068 (10)
N1	0.0271 (13)	0.0192 (11)	0.0485 (13)	−0.0045 (9)	0.0000 (10)	−0.0154 (9)
N2	0.0354 (14)	0.0206 (11)	0.0442 (13)	−0.0074 (10)	0.0013 (10)	−0.0176 (9)
N3	0.067 (2)	0.085 (2)	0.0376 (16)	−0.0242 (19)	−0.0111 (14)	−0.0075 (15)
N4	0.048 (2)	0.0435 (18)	0.082 (2)	−0.0156 (15)	0.0143 (16)	−0.0162 (16)
C1	0.0261 (15)	0.0209 (13)	0.0382 (14)	−0.0021 (10)	0.0038 (11)	−0.0136 (10)
C2	0.0413 (19)	0.0419 (18)	0.0391 (16)	−0.0022 (14)	0.0030 (13)	−0.0133 (13)
C3	0.045 (2)	0.0462 (19)	0.0393 (16)	−0.0087 (15)	0.0126 (13)	−0.0168 (13)
C4	0.0386 (18)	0.0471 (19)	0.0437 (16)	−0.0108 (14)	0.0100 (13)	−0.0241 (14)
C5	0.046 (2)	0.0458 (19)	0.0416 (16)	−0.0171 (15)	0.0112 (13)	−0.0201 (14)
C6	0.0432 (19)	0.0402 (17)	0.0424 (16)	−0.0103 (14)	0.0013 (13)	−0.0165 (13)
C7	0.0402 (19)	0.0414 (18)	0.0432 (16)	−0.0053 (14)	0.0039 (13)	−0.0178 (13)
C8	0.043 (2)	0.048 (2)	0.064 (2)	−0.0125 (16)	0.0207 (16)	−0.0238 (16)
C9	0.053 (2)	0.0385 (18)	0.064 (2)	−0.0141 (16)	0.0206 (16)	−0.0226 (15)
C10	0.052 (2)	0.044 (2)	0.0466 (18)	−0.0062 (16)	0.0070 (15)	−0.0173 (14)
C11	0.0347 (16)	0.0250 (14)	0.0473 (16)	−0.0079 (12)	0.0073 (12)	−0.0198 (12)
C12	0.0342 (16)	0.0243 (14)	0.0431 (15)	−0.0092 (12)	0.0067 (12)	−0.0146 (11)
C13	0.0296 (15)	0.0186 (13)	0.0395 (14)	−0.0058 (10)	−0.0031 (11)	−0.0135 (10)
C14	0.0381 (17)	0.0232 (14)	0.0516 (17)	−0.0076 (12)	0.0113 (13)	−0.0192 (12)
C15	0.0321 (16)	0.0223 (14)	0.0550 (17)	−0.0101 (12)	0.0089 (13)	−0.0142 (12)
C16	0.0368 (17)	0.0273 (15)	0.0560 (18)	−0.0141 (13)	0.0092 (13)	−0.0212 (13)
C17	0.0345 (17)	0.0276 (15)	0.0587 (18)	−0.0085 (12)	0.0114 (13)	−0.0247 (13)
C18	0.0285 (15)	0.0208 (13)	0.0392 (14)	−0.0050 (10)	−0.0014 (11)	−0.0161 (11)
C19	0.0383 (18)	0.0313 (16)	0.069 (2)	−0.0170 (13)	0.0179 (15)	−0.0288 (14)
C20	0.0414 (19)	0.0325 (16)	0.072 (2)	−0.0119 (14)	0.0160 (15)	−0.0332 (15)
C21	0.045 (2)	0.052 (2)	0.0461 (18)	−0.0156 (16)	0.0003 (15)	−0.0119 (15)
C22	0.113 (4)	0.113 (4)	0.062 (3)	−0.055 (3)	0.011 (3)	−0.037 (3)
C23	0.119 (5)	0.124 (5)	0.078 (3)	−0.006 (4)	−0.051 (3)	0.007 (3)

Geometric parameters (Å, º) top

Cd1—O1	2.4304 (19)	C4—C9	1.380 (4)
Cd1—O1ⁱ	2.398 (2)	C4—C5	1.386 (4)
Cd1—O2	2.5080 (19)	C5—C6	1.378 (4)
Cd1—O6	2.381 (2)	C5—H5A	0.9300
Cd1—O1W	2.370 (2)	C6—C7	1.388 (4)
Cd1—N1	2.305 (2)	C6—H6	0.9300
Cd1—N2ⁱⁱ	2.294 (2)	C7—C8	1.376 (4)
O1—C1	1.259 (3)	C7—C10	1.482 (4)
O1—Cd1ⁱ	2.3985 (19)	C8—C9	1.387 (4)
O2—C1	1.251 (3)	C8—H8	0.9300
O3—C4	1.363 (4)	C9—H9	0.9300
O3—C3	1.436 (4)	C11—C12	1.384 (3)
O4—C10	1.235 (4)	C11—H11A	0.9300
O5—C10	1.293 (4)	C12—C13	1.387 (4)
O5—H5	0.8400	C12—H12A	0.9300
O6—C21	1.225 (4)	C13—C14	1.394 (4)
O7—N4	1.245 (4)	C13—C18	1.490 (3)
O8—N4	1.206 (4)	C14—C15	1.376 (4)
O9—N4	1.218 (4)	C14—H14	0.9300
O1W—H11	0.8400	C15—H15	0.9300
O1W—H12	0.8400	C16—C17	1.382 (4)
N1—C11	1.335 (4)	C16—H16	0.9300
N1—C15	1.338 (3)	C17—C18	1.385 (4)
N2—C20	1.332 (4)	C17—H17	0.9300
N2—C16	1.333 (4)	C18—C19	1.389 (4)
N2—Cd1ⁱⁱⁱ	2.294 (2)	C19—C20	1.379 (4)
N3—C21	1.324 (4)	C19—H19	0.9300
N3—C22	1.428 (5)	C20—H20	0.9300
N3—C23	1.453 (6)	C21—H21	0.9300
C1—C2	1.510 (4)	C22—H22A	0.9600
C2—C3	1.515 (4)	C22—H22B	0.9600
C2—H2A	0.9700	C22—H22C	0.9600
C2—H2B	0.9700	C23—H23A	0.9600
C3—H3A	0.9700	C23—H23B	0.9600
C3—H3B	0.9700	C23—H23C	0.9600

N2ⁱⁱ—Cd1—N1	177.79 (8)	C6—C5—H5A	120.0
N2ⁱⁱ—Cd1—O1W	92.00 (8)	C4—C5—H5A	120.0
N1—Cd1—O1W	88.38 (8)	C5—C6—C7	120.4 (3)
N2ⁱⁱ—Cd1—O6	87.14 (8)	C5—C6—H6	119.8
N1—Cd1—O6	90.79 (8)	C7—C6—H6	119.8
O1W—Cd1—O6	79.50 (8)	C8—C7—C6	119.0 (3)
N2ⁱⁱ—Cd1—O1ⁱ	91.36 (8)	C8—C7—C10	121.4 (3)
N1—Cd1—O1ⁱ	87.59 (7)	C6—C7—C10	119.7 (3)
O1W—Cd1—O1ⁱ	161.18 (7)	C7—C8—C9	121.2 (3)
O6—Cd1—O1ⁱ	82.19 (7)	C7—C8—H8	119.4
N2ⁱⁱ—Cd1—O1	96.38 (7)	C9—C8—H8	119.4
N1—Cd1—O1	85.10 (7)	C4—C9—C8	119.2 (3)
O1W—Cd1—O1	127.31 (7)	C4—C9—H9	120.4
O6—Cd1—O1	152.60 (8)	C8—C9—H9	120.4
O1ⁱ—Cd1—O1	70.59 (7)	O4—C10—O5	123.4 (3)
N2ⁱⁱ—Cd1—O2	87.11 (7)	O4—C10—C7	121.0 (3)
N1—Cd1—O2	95.10 (7)	O5—C10—C7	115.6 (3)
O1W—Cd1—O2	76.40 (7)	N1—C11—C12	123.3 (3)
O6—Cd1—O2	154.98 (8)	N1—C11—H11A	118.4
O1ⁱ—Cd1—O2	122.27 (6)	C12—C11—H11A	118.4
O1—Cd1—O2	52.37 (6)	C11—C12—C13	119.5 (3)
C1—O1—Cd1ⁱ	153.61 (18)	C11—C12—H12A	120.3
C1—O1—Cd1	95.24 (16)	C13—C12—H12A	120.3
Cd1ⁱ—O1—Cd1	109.41 (7)	C12—C13—C14	117.1 (2)
C1—O2—Cd1	91.80 (16)	C12—C13—C18	121.2 (2)
C4—O3—C3	117.4 (2)	C14—C13—C18	121.7 (2)
C10—O5—H5	120.0	C15—C14—C13	119.6 (3)
C21—O6—Cd1	117.7 (2)	C15—C14—H14	120.2
Cd1—O1W—H11	109.5	C13—C14—H14	120.2
Cd1—O1W—H12	109.5	N1—C15—C14	123.3 (3)
H11—O1W—H12	109.5	N1—C15—H15	118.4
C11—N1—C15	117.2 (2)	C14—C15—H15	118.4
C11—N1—Cd1	121.05 (17)	N2—C16—C17	123.2 (3)
C15—N1—Cd1	121.72 (18)	N2—C16—H16	118.4
C20—N2—C16	117.1 (2)	C17—C16—H16	118.4
C20—N2—Cd1ⁱⁱⁱ	120.16 (18)	C16—C17—C18	119.8 (3)
C16—N2—Cd1ⁱⁱⁱ	122.71 (18)	C16—C17—H17	120.1
C21—N3—C22	121.9 (4)	C18—C17—H17	120.1
C21—N3—C23	119.2 (4)	C17—C18—C19	116.8 (2)
C22—N3—C23	119.0 (4)	C17—C18—C13	122.0 (2)
O8—N4—O9	120.3 (4)	C19—C18—C13	121.2 (2)
O8—N4—O7	119.6 (4)	C20—C19—C18	119.7 (3)
O9—N4—O7	120.1 (4)	C20—C19—H19	120.2
O2—C1—O1	120.6 (2)	C18—C19—H19	120.2
O2—C1—C2	120.1 (2)	N2—C20—C19	123.4 (3)
O1—C1—C2	119.3 (2)	N2—C20—H20	118.3
C1—C2—C3	113.3 (3)	C19—C20—H20	118.3
C1—C2—H2A	108.9	O6—C21—N3	125.3 (4)
C3—C2—H2A	108.9	O6—C21—H21	117.4
C1—C2—H2B	108.9	N3—C21—H21	117.4
C3—C2—H2B	108.9	N3—C22—H22A	109.5
H2A—C2—H2B	107.7	N3—C22—H22B	109.5
O3—C3—C2	106.8 (2)	H22A—C22—H22B	109.5
O3—C3—H3A	110.4	N3—C22—H22C	109.5
C2—C3—H3A	110.4	H22A—C22—H22C	109.5
O3—C3—H3B	110.4	H22B—C22—H22C	109.5
C2—C3—H3B	110.4	N3—C23—H23A	109.5
H3A—C3—H3B	108.6	N3—C23—H23B	109.5
O3—C4—C9	124.3 (3)	H23A—C23—H23B	109.5
O3—C4—C5	115.8 (3)	N3—C23—H23C	109.5
C9—C4—C5	120.0 (3)	H23A—C23—H23C	109.5
C6—C5—C4	120.1 (3)	H23B—C23—H23C	109.5

N2ⁱⁱ—Cd1—O1—C1	81.21 (16)	C3—O3—C4—C9	2.8 (5)
N1—Cd1—O1—C1	−100.43 (16)	C3—O3—C4—C5	−176.5 (3)
O1W—Cd1—O1—C1	−16.23 (19)	O3—C4—C5—C6	176.5 (3)
O6—Cd1—O1—C1	177.34 (16)	C9—C4—C5—C6	−2.8 (5)
O1ⁱ—Cd1—O1—C1	170.41 (19)	C4—C5—C6—C7	−0.1 (5)
O2—Cd1—O1—C1	−0.14 (14)	C5—C6—C7—C8	2.3 (5)
N2ⁱⁱ—Cd1—O1—Cd1ⁱ	−89.19 (9)	C5—C6—C7—C10	−175.3 (3)
N1—Cd1—O1—Cd1ⁱ	89.16 (9)	C6—C7—C8—C9	−1.7 (5)
O1W—Cd1—O1—Cd1ⁱ	173.37 (7)	C10—C7—C8—C9	175.9 (3)
O6—Cd1—O1—Cd1ⁱ	6.93 (19)	O3—C4—C9—C8	−175.8 (3)
O1ⁱ—Cd1—O1—Cd1ⁱ	0.0	C5—C4—C9—C8	3.4 (5)
O2—Cd1—O1—Cd1ⁱ	−170.55 (12)	C7—C8—C9—C4	−1.2 (6)
N2ⁱⁱ—Cd1—O2—C1	−100.20 (16)	C8—C7—C10—O4	179.8 (3)
N1—Cd1—O2—C1	79.95 (16)	C6—C7—C10—O4	−2.6 (5)
O1W—Cd1—O2—C1	167.04 (16)	C8—C7—C10—O5	−1.0 (5)
O6—Cd1—O2—C1	−177.12 (17)	C6—C7—C10—O5	176.6 (3)
O1ⁱ—Cd1—O2—C1	−10.41 (17)	C15—N1—C11—C12	0.7 (4)
O1—Cd1—O2—C1	0.14 (14)	Cd1—N1—C11—C12	179.3 (2)
N2ⁱⁱ—Cd1—O6—C21	−125.3 (2)	N1—C11—C12—C13	0.3 (4)
N1—Cd1—O6—C21	55.5 (2)	C11—C12—C13—C14	−1.4 (4)
O1W—Cd1—O6—C21	−32.7 (2)	C11—C12—C13—C18	177.1 (3)
O1ⁱ—Cd1—O6—C21	142.9 (2)	C12—C13—C14—C15	1.5 (4)
O1—Cd1—O6—C21	136.3 (2)	C18—C13—C14—C15	−177.0 (3)
O2—Cd1—O6—C21	−48.4 (3)	C11—N1—C15—C14	−0.6 (4)
O1W—Cd1—N1—C11	119.7 (2)	Cd1—N1—C15—C14	−179.2 (2)
O6—Cd1—N1—C11	40.2 (2)	C13—C14—C15—N1	−0.5 (5)
O1ⁱ—Cd1—N1—C11	−41.9 (2)	C20—N2—C16—C17	1.1 (5)
O1—Cd1—N1—C11	−112.6 (2)	Cd1ⁱⁱⁱ—N2—C16—C17	−176.5 (2)
O2—Cd1—N1—C11	−164.1 (2)	N2—C16—C17—C18	−0.3 (5)
O1W—Cd1—N1—C15	−61.8 (2)	C16—C17—C18—C19	−0.3 (4)
O6—Cd1—N1—C15	−141.2 (2)	C16—C17—C18—C13	179.7 (3)
O1ⁱ—Cd1—N1—C15	136.6 (2)	C12—C13—C18—C17	17.2 (4)
O1—Cd1—N1—C15	65.9 (2)	C14—C13—C18—C17	−164.4 (3)
O2—Cd1—N1—C15	14.4 (2)	C12—C13—C18—C19	−162.9 (3)
Cd1—O2—C1—O1	−0.3 (2)	C14—C13—C18—C19	15.6 (4)
Cd1—O2—C1—C2	178.9 (2)	C17—C18—C19—C20	0.0 (5)
Cd1ⁱ—O1—C1—O2	159.6 (3)	C13—C18—C19—C20	180.0 (3)
Cd1—O1—C1—O2	0.3 (3)	C16—N2—C20—C19	−1.4 (5)
Cd1ⁱ—O1—C1—C2	−19.6 (5)	Cd1ⁱⁱⁱ—N2—C20—C19	176.2 (3)
Cd1—O1—C1—C2	−178.9 (2)	C18—C19—C20—N2	0.9 (5)
O2—C1—C2—C3	33.5 (4)	Cd1—O6—C21—N3	156.6 (3)
O1—C1—C2—C3	−147.4 (3)	C22—N3—C21—O6	1.3 (6)
C4—O3—C3—C2	174.9 (3)	C23—N3—C21—O6	179.9 (4)
C1—C2—C3—O3	63.2 (3)

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

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
O5—H5···O4^iv	0.84	1.80	2.629 (3)	171
O1W—H11···O7	0.84	1.94	2.754 (4)	164
O1W—H12···O2^v	0.84	2.03	2.763 (3)	145

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

Experimental details

Crystal data
Chemical formula	[Cd₂(C₁₀H₉O₅)₂(C₁₀H₈N₂)₂(C₃H₇NO)₂(H₂O)₂](NO₃)₂
M_r	1261.76
Crystal system, space group	Triclinic, P1
Temperature (K)	293
a, b, c (Å)	9.1020 (5), 11.6866 (5), 13.3534 (5)
α, β, γ (°)	69.1646 (11), 84.2052 (16), 76.9358 (16)
V (Å³)	1292.84 (10)
Z	1
Radiation type	Mo Kα
µ (mm⁻¹)	0.91
Crystal size (mm)	0.19 × 0.12 × 0.11

Data collection
Diffractometer	Rigaku R-AXIS RAPID IP diffractometer
Absorption correction	Multi-scan (ABSCOR; Higashi, 1995)
T_min, T_max	0.847, 0.907
No. of measured, independent and observed [I > 2σ(I)] reflections	12594, 5822, 4760
R_int	0.031
(sin θ/λ)_max (Å⁻¹)	0.649

Refinement
R[F² > 2σ(F²)], wR(F²), S	0.030, 0.077, 1.08
No. of reflections	5822
No. of parameters	345
H-atom treatment	H-atom parameters constrained
Δρ_max, Δρ_min (e Å⁻³)	0.95, −0.59

Computer programs: RAPID-AUTO (Rigaku, 1998), CrystalClear (Rigaku, 2002), SHELXS97 (Sheldrick, 2008), SHELXL97 (Sheldrick, 2008), X-SEED (Barbour, 2001), publCIF (Westrip, 2010).

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
O5—H5···O4ⁱ	0.84	1.80	2.629 (3)	171
O1W—H11···O7	0.84	1.94	2.754 (4)	164
O1W—H12···O2ⁱⁱ	0.84	2.03	2.763 (3)	145

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

Acknowledgements

This work is supported by the Key Project of the Natural Science Foundation of Heilongjiang Province (grant No. ZD200903), the Key Project of the Education Bureau of Heilongjiang Province (grants No. 12511z023, No. 2011CJHB006), the Innovation Team of the Education Bureau of Heilongjiang Province (grant No. 2010 t d03), Heilongjiang University (Hdtd2010–04) and the Ministry of Higher Education of Malaysia (grant No. UM.C/HIR/MOHE/SC/12).

References

Barbour, L. J. (2001). J. Supramol. Chem. 1, 189–191. CrossRef CAS Google Scholar
Gao, S. & Ng, S. W. (2006). Acta Cryst. E62, o3420–o3421. Web of Science CSD CrossRef IUCr Journals Google Scholar
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Sheldrick, G. M. (2008). Acta Cryst. A64, 112–122. Web of Science CrossRef CAS IUCr Journals Google Scholar
Westrip, S. P. (2010). J. Appl. Cryst. 43, 920–925. Web of Science CrossRef CAS IUCr Journals Google Scholar

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