Diaqua­[N,N′-bis­(3-carboxy­prop-2-enoyl)pyridine-2,6-dicarbo­hydrazidato(2–)]cadmium(II) N,N-dimethyl­formamide disolvate

Cao, Q.; Li, D.

doi:10.1107/S1600536809011003

metal-organic compounds

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ISSN: 2056-9890

Volume 65| Part 4| April 2009| Pages m464-m465

doi:10.1107/S1600536809011003

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Diaqua[N,N′-bis(3-carboxyprop-2-enoyl)pyridine-2,6-dicarbohydrazidato(2–)]cadmium(II) N,N-dimethylformamide disolvate

Quanfu Cao ^a and Dacheng Li ^a ^*

^aCollege of Chemistry and Chemical Engineering, Liaocheng University, Liaocheng 252059, People's Republic of China
^*Correspondence e-mail: lidacheng62@lcu.edu.cn

(Received 18 February 2009; accepted 25 March 2009; online 31 March 2009)

In the title complex, [Cd(C₁₅H₁₁N₅O₈)(H₂O)₂]·2C₃H₇NO, the Cd^II ion is located on a twofold rotation axis and is seven-coordinated in a distorted pentagonal-bipyramidal manner. The asymmetric unit comprises one metal ion, one doubly deprotonated N,N′-bis(3-carboxyprop-2-enoyl)pyridine-2,6-dicarbohydrazide ligand, two coordinating water molecules and two dimethylformamide solvent molecules. In the crystal, a two-dimensional network is formed through N—H⋯O and O—H⋯O hydrogen bonds.

Related literature

For polydimensional supermolecular architectures formed by aromatic hydrazides through hydrogen bonds and π–π interactions, see: Bacchi et al. (1993 ); Bermejo et al. (1999 ). The condensation products of 2,6-picolylhydrazide with anhydrides have been found to adopt a pentagonal-bipyramidal coordination in various metal complexes, see: Pelizzi et al. (1987 ); Wang et al. (2005 ). For the chelating behaviour of N,N′-acetyl-2,6-picolylhydrazide with Fe³⁺, see: Cao et al. (2008 ). For our continuing study of aroylhydrazides, see: Dou et al. (2006 ). For Cd—O(carbonyl) bond lengths in other seven-coordinated pentagonal-bipyramidal cadmium complexes, see: Charles et al. (1983 ).

Experimental

Crystal data

[Cd(C₁₅H₁₁N₅O₈)(H₂O)₂]·2C₃H₇NO
M_r = 683.91
Monoclinic, C 2/c
a = 18.6176 (2) Å
b = 12.6065 (8) Å
c = 12.0038 (6) Å
β = 99.51°
V = 2778.6 (2) Å³
Z = 4
Mo Kα radiation
μ = 0.86 mm⁻¹
T = 298 K
0.20 × 0.18 × 0.17 mm

Data collection

Siemens SMART CCD area-detector diffractometer
Absorption correction: multi-scan (SADABS; Sheldrick, 1996 ) T_min = 0.847, T_max = 0.868
6846 measured reflections
2448 independent reflections
2071 reflections with I > 2σ(I)
R_int = 0.028

Refinement

R[F² > 2σ(F²)] = 0.027
wR(F²) = 0.075
S = 1.00
2448 reflections
189 parameters
H-atom parameters constrained
Δρ_max = 0.73 e Å⁻³
Δρ_min = −0.48 e Å⁻³

Table 1
Selected bond lengths (Å)

Cd1—N2ⁱ	2.287 (2)
Cd1—O5ⁱ	2.3412 (19)
Cd1—N1	2.387 (3)
Cd1—O2ⁱ	2.4441 (19)
N2—N3	1.369 (3)
Symmetry code: (i) $[-x+1, y, -z+{\script{3\over 2}}]$ .

Table 2
Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
O5—H5A⋯O4ⁱⁱ	0.85	1.97	2.802 (3)	165
O5—H5B⋯O1ⁱⁱⁱ	0.85	1.84	2.685 (3)	174
N3—H3A⋯O6	0.86	1.97	2.808 (3)	163
O3—H3⋯O2	0.82	1.68	2.498 (3)	175
Symmetry codes: (ii) -x+1, -y, -z+1; (iii) -x+1, -y+1, -z+1.

Data collection: SMART (Siemens, 1996 ); cell refinement: SAINT (Siemens, 1996); 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

Crystal structure: contains datablocks global, I. DOI: 10.1107/S1600536809011003/kp2207sup1.cif

Structure factors: contains datablock I. DOI: 10.1107/S1600536809011003/kp2207Isup2.hkl

checkCIF report

Comment top

Containing N, O and other coordinating sites, aromatic hydrazides can form poly-dimensional supermolecular architectures through hydrogen bonds and π-π interactions (Bacchi et al., 1993, Bermejo et al., 1999). The condensation products of 2,6-picolylhydrazide with anhydrides have been found to adopt a pentagonal-bipyramidal stereochemistry in various metal complexes, in which they may participate as neutral and/or dianionic ligands (Pelizzi, et al., 1987, Wang et al., 2005). Previously we have examined the chelating behaviour of N,N'-acetyl-2,6-picolylhydrazide with Fe³⁺ (Cao, et al., 2008). As a part of continuing study of our research on aroylhydrazide in our laboratory (Dou, et al., 2006), we synthesized N,N'-bis(3-carboxy-cis-propenoyl)- 2,6-picolyldihydrazide and obtained its Cd(II) complex (I).

The molecular structure of the complex (Fig. 1) and its characteristic geometry parameteres (Table 1) reveal one cadmium ion which is located on the 2-fold rotation axis, one deprotonated ligand, two coordinated H₂O molecules and two solvent DMF molecules. The divalent anionic H₂L^2- acts as a pentadentate chelating ligand to two cadmium atoms.The remainder coordinating sites of Cd²⁺ are occupied by two O atoms from water molecules in trans-positions which complete the seven-coordinated pentagonal- bipyramid. Two deprotonated amide nitrogen atoms, two carbonyl O atoms, one pyridine N atom complete the equatorial plane and the mean deviation is 0.0064 Å indicating that the five atoms are ideally coplanar. Such planarity was observed in [Cd(H₂daps)Cl₂](CHCl₃)(CH₃OH) (less than 0.007 Å) (H₂daps = 2,6-diacetylpridine bis(salicyloylhydrazone) (Pelizzi, et al., 1987). The Cd—N distances are in the range of 2.287 (2) Å to 2.387 (3) Å; its average value of 2.320 (2) Å is shorter than those observed in [Cd(L^')(1.5H₂O)]n (L' = N,N'-bis(4-pyridylcarboxyl)- 2,6-pyridine dicarbohydrazide) (Wang et al., 2005) and [Cd(H₂daps)Cl₂](CHCl₃)(CH₃OH) (Pelizzi, et al., 1987). Both, two Cd—O(carbonyl) bond lengths (2.4441 (19) Å) are comparable to those in other seven-coordinated pentagonal-bipyramidal cadmium complexes (Charles et al., 1983). The Cd—O (water) distance is 2.341 (2) Å, being shorter than the mean lengths of Cd—O in the the equatorial plane of 2.444 (19) Å.

The crystal structure of the title complex is predominantly determined by N—H···O and O—H···O hydrogen bonds (Table 2 and Fig. 2) generating 2-D network.

Related literature top

For polydimensional supermolecular architectures formed by aromatic hydrazides through hydrogen bonds and π–π interactions, see: Bacchi et al. (1993); Bermejo et al. (1999). The condensation products of 2,6-picolylhydrazide with anhydrides have been found to adopt a pentagonal-bipyramidal stereochemistry in various metal complexes, see: Pelizzi et al. (1987); Wang et al. (2005). For the chelating behaviour of N,N'-acetyl-2,6-picolylhydrazide with Fe³⁺, see: Cao et al. (2008). For our continuing study of aroylhydrazides, see: Dou et al. (2006). For Cd—O(carbonyl) bond lengths in other seven-coordinated pentagonal-bipyramidal cadmium complexes, see: Charles et al. (1983).

Experimental top

All chemicals were of reagent grade and were used without further purification. A solution of cadmium nitrate tetrahydrate (2 mmol, 0.457 g) dissolved in methanol (10 ml) was added dropwise to a DMF solution containing the ligand (2 mmol, 0.783 g). The mixture was stirred at room temperature for 6 h and then filtered.The filtrate was left to evaporate slowly at room temperature and yellow block-shaped crystals suitable for X-ray diffraction analysis were obtained after three weeks (m.p. >573 K). Elemental analysis calculated for (I): C: 36.88, H: 4.27, N: 14.34%; found: C: 36.11, H: 4.66, N: 14.02%. IR (KBr pellet, cm^-1): 3467 (O—H), 3134 (N—H), 1709 (C=O) (acid carboxyl segment), 1647 (C=C).

Computing details top

Data collection: SMART (Siemens, 1996); cell refinement: SAINT (Siemens, 1996); data reduction: SAINT (Siemens, 1996); 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 molecular stucture of the complex (I) showing the atomic numbering scheme. Displacement ellipsoids are drawn at the 30% probability level. [Symmetry codes: -x + 1,y,-z + 3/2]
	Fig. 2. Part of the crystal structure of the complex, showing hydrogen bonds as dashed lines. [Symmetry codes: (i) -x + 1, -y, -z + 1; (ii) -x + 1, -y + 1, -z + 1].

Diaqua[N,N'-bis(3-carboxyprop-2-enoyl)pyridine-2,6- dicarbohydrazidato(2-)]cadmium(II) N,N-dimethylformamide disolvate top

Crystal data top

[Cd(C₁₅H₁₁N₅O₈)(H₂O)₂]·2C₃H₇NO	F(000) = 1392
M_r = 683.91	D_x = 1.635 Mg m⁻³
Monoclinic, C2/c	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: -C 2yc	Cell parameters from 3321 reflections
a = 18.6176 (2) Å	θ = 2.5–27.6°
b = 12.6065 (8) Å	µ = 0.86 mm⁻¹
c = 12.0038 (6) Å	T = 298 K
β = 99.51°	Block, yellow
V = 2778.6 (2) Å³	0.20 × 0.18 × 0.17 mm
Z = 4

Data collection top

Siemens SMART CCD area-detector diffractometer	2448 independent reflections
Radiation source: fine-focus sealed tube	2071 reflections with I > 2σ(I)
Graphite monochromator	R_int = 0.028
ϕ and ω scans	θ_max = 25.0°, θ_min = 2.0°
Absorption correction: multi-scan (SADABS; Sheldrick, 1996)	h = −22→21
T_min = 0.847, T_max = 0.868	k = −14→8
6846 measured reflections	l = −14→14

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)] = 0.027	Hydrogen site location: inferred from neighbouring sites
wR(F²) = 0.075	H-atom parameters constrained
S = 1.00	w = 1/[σ²(F_o²) + (0.0426P)² + 1.9365P] where P = (F_o² + 2F_c²)/3
2448 reflections	(Δ/σ)_max = 0.001
189 parameters	Δρ_max = 0.73 e Å⁻³
0 restraints	Δρ_min = −0.48 e Å⁻³

Crystal data top

[Cd(C₁₅H₁₁N₅O₈)(H₂O)₂]·2C₃H₇NO	V = 2778.6 (2) Å³
M_r = 683.91	Z = 4
Monoclinic, C2/c	Mo Kα radiation
a = 18.6176 (2) Å	µ = 0.86 mm⁻¹
b = 12.6065 (8) Å	T = 298 K
c = 12.0038 (6) Å	0.20 × 0.18 × 0.17 mm
β = 99.51°

Data collection top

Siemens SMART CCD area-detector diffractometer	2448 independent reflections
Absorption correction: multi-scan (SADABS; Sheldrick, 1996)	2071 reflections with I > 2σ(I)
T_min = 0.847, T_max = 0.868	R_int = 0.028
6846 measured reflections

Refinement top

R[F² > 2σ(F²)] = 0.027	0 restraints
wR(F²) = 0.075	H-atom parameters constrained
S = 1.00	Δρ_max = 0.73 e Å⁻³
2448 reflections	Δρ_min = −0.48 e Å⁻³
189 parameters

Special details top

Geometry. All e.s.d.'s (except the e.s.d. in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell e.s.d.'s are taken into account individually in the estimation of e.s.d.'s in distances, angles and torsion angles; correlations between e.s.d.'s in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell e.s.d.'s is used for estimating e.s.d.'s involving l.s. planes.

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

	x	y	z	U_iso*/U_eq
Cd1	0.5000	0.32546 (2)	0.7500	0.03647 (12)
N1	0.5000	0.5148 (2)	0.7500	0.0315 (7)
N2	0.56574 (12)	0.39595 (18)	0.62292 (19)	0.0356 (5)
N3	0.59654 (12)	0.32818 (17)	0.55520 (19)	0.0346 (5)
H3A	0.6204	0.3519	0.5049	0.042*
N4	0.73608 (14)	0.4660 (2)	0.2710 (2)	0.0474 (6)
O1	0.60699 (11)	0.53782 (16)	0.53204 (17)	0.0457 (5)
O2	0.55458 (11)	0.18980 (15)	0.64485 (17)	0.0413 (5)
O3	0.55912 (13)	−0.00807 (17)	0.6368 (2)	0.0596 (6)
H3	0.5574	0.0566	0.6435	0.089*
O4	0.60364 (16)	−0.12393 (19)	0.5313 (2)	0.0733 (8)
O5	0.39670 (11)	0.29907 (15)	0.61261 (16)	0.0420 (5)
H5A	0.3988	0.2396	0.5800	0.050*
H5B	0.3967	0.3475	0.5634	0.050*
O6	0.68682 (14)	0.3634 (2)	0.3932 (2)	0.0656 (7)
C1	0.57294 (15)	0.4982 (2)	0.6033 (2)	0.0345 (6)
C2	0.53537 (14)	0.5671 (2)	0.6791 (2)	0.0340 (6)
C3	0.53679 (16)	0.6767 (2)	0.6772 (3)	0.0403 (7)
H3B	0.5619	0.7127	0.6280	0.048*
C4	0.5000	0.7315 (3)	0.7500	0.0414 (10)
H4	0.5000	0.8053	0.7500	0.050*
C5	0.58854 (14)	0.2254 (2)	0.5694 (2)	0.0336 (6)
C6	0.62026 (18)	0.1570 (2)	0.4921 (3)	0.0460 (8)
H6	0.6438	0.1921	0.4403	0.055*
C7	0.62029 (19)	0.0514 (2)	0.4854 (3)	0.0523 (8)
H7	0.6419	0.0254	0.4264	0.063*
C8	0.59292 (18)	−0.0317 (2)	0.5527 (3)	0.0483 (8)
C9	0.70087 (17)	0.4503 (3)	0.3561 (3)	0.0519 (8)
H9	0.6854	0.5100	0.3910	0.062*
C10	0.75008 (19)	0.5723 (3)	0.2334 (3)	0.0612 (10)
H10A	0.7260	0.6230	0.2741	0.092*
H10B	0.7320	0.5786	0.1540	0.092*
H10C	0.8016	0.5856	0.2472	0.092*
C11	0.7598 (2)	0.3769 (3)	0.2101 (3)	0.0672 (10)
H11A	0.7465	0.3119	0.2431	0.101*
H11B	0.8117	0.3796	0.2143	0.101*
H11C	0.7368	0.3801	0.1325	0.101*

Atomic displacement parameters (Å²) top

	U¹¹	U²²	U³³	U¹²	U¹³	U²³
Cd1	0.0481 (2)	0.02519 (17)	0.03978 (19)	0.000	0.01812 (13)	0.000
N1	0.0379 (17)	0.0217 (16)	0.0355 (18)	0.000	0.0083 (14)	0.000
N2	0.0455 (13)	0.0251 (12)	0.0391 (14)	0.0013 (10)	0.0155 (11)	−0.0008 (10)
N3	0.0424 (13)	0.0293 (13)	0.0351 (13)	−0.0007 (10)	0.0150 (10)	0.0013 (10)
N4	0.0528 (15)	0.0427 (15)	0.0515 (16)	0.0070 (12)	0.0226 (13)	0.0104 (12)
O1	0.0627 (13)	0.0346 (12)	0.0450 (12)	0.0011 (10)	0.0240 (10)	0.0079 (9)
O2	0.0546 (12)	0.0284 (11)	0.0466 (12)	0.0010 (9)	0.0247 (10)	−0.0009 (9)
O3	0.0866 (17)	0.0307 (12)	0.0707 (16)	−0.0033 (11)	0.0394 (14)	−0.0011 (11)
O4	0.116 (2)	0.0311 (14)	0.0787 (19)	−0.0008 (13)	0.0324 (16)	−0.0118 (12)
O5	0.0580 (12)	0.0299 (10)	0.0391 (11)	−0.0008 (9)	0.0109 (9)	0.0010 (9)
O6	0.0778 (17)	0.0552 (15)	0.0728 (17)	−0.0020 (13)	0.0393 (14)	0.0140 (13)
C1	0.0398 (15)	0.0314 (16)	0.0321 (15)	−0.0003 (12)	0.0055 (12)	0.0047 (12)
C2	0.0387 (15)	0.0285 (15)	0.0346 (15)	0.0005 (12)	0.0053 (12)	0.0035 (12)
C3	0.0521 (17)	0.0254 (15)	0.0437 (17)	−0.0033 (13)	0.0093 (14)	0.0056 (12)
C4	0.058 (3)	0.020 (2)	0.047 (3)	0.000	0.008 (2)	0.000
C5	0.0384 (15)	0.0285 (16)	0.0358 (16)	0.0001 (12)	0.0119 (12)	0.0030 (12)
C6	0.0576 (19)	0.0354 (18)	0.0506 (19)	0.0015 (14)	0.0253 (15)	0.0005 (14)
C7	0.069 (2)	0.0397 (19)	0.054 (2)	0.0049 (16)	0.0299 (17)	−0.0071 (15)
C8	0.064 (2)	0.0311 (18)	0.0510 (19)	−0.0008 (14)	0.0121 (16)	−0.0051 (14)
C9	0.0539 (19)	0.050 (2)	0.056 (2)	0.0015 (16)	0.0210 (16)	0.0046 (16)
C10	0.062 (2)	0.054 (2)	0.072 (3)	0.0002 (17)	0.0235 (19)	0.0211 (19)
C11	0.079 (3)	0.060 (2)	0.069 (3)	0.012 (2)	0.032 (2)	0.004 (2)

Geometric parameters (Å, º) top

Cd1—N2ⁱ	2.287 (2)	O5—H5A	0.8500
Cd1—N2	2.287 (2)	O5—H5B	0.8500
Cd1—O5ⁱ	2.3412 (19)	O6—C9	1.227 (4)
Cd1—O5	2.3412 (19)	C1—C2	1.511 (4)
Cd1—N1	2.387 (3)	C2—C3	1.382 (4)
Cd1—O2ⁱ	2.4441 (19)	C3—C4	1.382 (4)
Cd1—O2	2.4441 (19)	C3—H3B	0.9300
N1—C2ⁱ	1.334 (3)	C4—C3ⁱ	1.382 (4)
N1—C2	1.334 (3)	C4—H4	0.9300
N2—C1	1.321 (4)	C5—C6	1.460 (4)
N2—N3	1.369 (3)	C6—C7	1.335 (4)
N3—C5	1.319 (3)	C6—H6	0.9300
N3—H3A	0.8600	C7—C8	1.465 (4)
N4—C9	1.316 (4)	C7—H7	0.9300
N4—C11	1.448 (4)	C9—H9	0.9300
N4—C10	1.452 (4)	C10—H10A	0.9600
O1—C1	1.250 (3)	C10—H10B	0.9600
O2—C5	1.269 (3)	C10—H10C	0.9600
O3—C8	1.309 (4)	C11—H11A	0.9600
O3—H3	0.8200	C11—H11B	0.9600
O4—C8	1.214 (4)	C11—H11C	0.9600

N2ⁱ—Cd1—N2	134.27 (11)	O1—C1—C2	121.3 (2)
N2ⁱ—Cd1—O5ⁱ	93.05 (8)	N2—C1—C2	112.5 (2)
N2—Cd1—O5ⁱ	93.28 (8)	N1—C2—C3	121.2 (3)
N2ⁱ—Cd1—O5	93.28 (8)	N1—C2—C1	115.2 (2)
N2—Cd1—O5	93.05 (8)	C3—C2—C1	123.6 (3)
O5ⁱ—Cd1—O5	163.66 (9)	C4—C3—C2	118.5 (3)
N2ⁱ—Cd1—N1	67.13 (6)	C4—C3—H3B	120.8
N2—Cd1—N1	67.13 (6)	C2—C3—H3B	120.8
O5ⁱ—Cd1—N1	98.17 (5)	C3ⁱ—C4—C3	120.0 (4)
O5—Cd1—N1	98.17 (5)	C3ⁱ—C4—H4	120.0
N2ⁱ—Cd1—O2ⁱ	67.27 (7)	C3—C4—H4	120.0
N2—Cd1—O2ⁱ	158.46 (8)	O2—C5—N3	121.3 (2)
O5ⁱ—Cd1—O2ⁱ	84.26 (7)	O2—C5—C6	123.1 (2)
O5—Cd1—O2ⁱ	84.33 (7)	N3—C5—C6	115.6 (2)
N1—Cd1—O2ⁱ	134.40 (4)	C7—C6—C5	129.2 (3)
N2ⁱ—Cd1—O2	158.46 (8)	C7—C6—H6	115.4
N2—Cd1—O2	67.27 (7)	C5—C6—H6	115.4
O5ⁱ—Cd1—O2	84.33 (7)	C6—C7—C8	132.6 (3)
O5—Cd1—O2	84.26 (7)	C6—C7—H7	113.7
N1—Cd1—O2	134.40 (4)	C8—C7—H7	113.7
O2ⁱ—Cd1—O2	91.20 (9)	O4—C8—O3	119.9 (3)
C2ⁱ—N1—C2	120.7 (3)	O4—C8—C7	118.9 (3)
C2ⁱ—N1—Cd1	119.64 (16)	O3—C8—C7	121.2 (3)
C2—N1—Cd1	119.64 (16)	O6—C9—N4	125.4 (3)
C1—N2—N3	116.0 (2)	O6—C9—H9	117.3
C1—N2—Cd1	125.41 (19)	N4—C9—H9	117.3
N3—N2—Cd1	118.45 (16)	N4—C10—H10A	109.5
C5—N3—N2	118.0 (2)	N4—C10—H10B	109.5
C5—N3—H3A	121.0	H10A—C10—H10B	109.5
N2—N3—H3A	121.0	N4—C10—H10C	109.5
C9—N4—C11	120.5 (3)	H10A—C10—H10C	109.5
C9—N4—C10	121.2 (3)	H10B—C10—H10C	109.5
C11—N4—C10	118.3 (3)	N4—C11—H11A	109.5
C5—O2—Cd1	114.84 (16)	N4—C11—H11B	109.5
C8—O3—H3	109.5	H11A—C11—H11B	109.5
Cd1—O5—H5A	110.8	N4—C11—H11C	109.5
Cd1—O5—H5B	107.1	H11A—C11—H11C	109.5
H5A—O5—H5B	108.0	H11B—C11—H11C	109.5
O1—C1—N2	126.2 (3)

N2ⁱ—Cd1—N1—C2ⁱ	0.87 (14)	O5—Cd1—O2—C5	92.38 (19)
N2—Cd1—N1—C2ⁱ	−179.13 (14)	N1—Cd1—O2—C5	−3.4 (2)
O5ⁱ—Cd1—N1—C2ⁱ	−89.00 (14)	O2ⁱ—Cd1—O2—C5	176.6 (2)
O5—Cd1—N1—C2ⁱ	91.00 (14)	N3—N2—C1—O1	−2.6 (4)
O2ⁱ—Cd1—N1—C2ⁱ	0.95 (15)	Cd1—N2—C1—O1	−177.9 (2)
O2—Cd1—N1—C2ⁱ	−179.05 (15)	N3—N2—C1—C2	178.2 (2)
N2ⁱ—Cd1—N1—C2	−179.13 (14)	Cd1—N2—C1—C2	2.8 (3)
N2—Cd1—N1—C2	0.87 (14)	C2ⁱ—N1—C2—C3	0.3 (2)
O5ⁱ—Cd1—N1—C2	91.00 (14)	Cd1—N1—C2—C3	−179.7 (2)
O5—Cd1—N1—C2	−89.00 (14)	C2ⁱ—N1—C2—C1	−179.9 (2)
O2ⁱ—Cd1—N1—C2	−179.05 (15)	Cd1—N1—C2—C1	0.1 (2)
O2—Cd1—N1—C2	0.95 (15)	O1—C1—C2—N1	179.0 (2)
N2ⁱ—Cd1—N2—C1	−2.1 (2)	N2—C1—C2—N1	−1.7 (3)
O5ⁱ—Cd1—N2—C1	−99.6 (2)	O1—C1—C2—C3	−1.2 (4)
O5—Cd1—N2—C1	95.5 (2)	N2—C1—C2—C3	178.1 (3)
N1—Cd1—N2—C1	−2.1 (2)	N1—C2—C3—C4	−0.6 (4)
O2ⁱ—Cd1—N2—C1	177.7 (2)	C1—C2—C3—C4	179.6 (2)
O2—Cd1—N2—C1	178.0 (3)	C2—C3—C4—C3ⁱ	0.29 (19)
N2ⁱ—Cd1—N2—N3	−177.3 (2)	Cd1—O2—C5—N3	3.8 (3)
O5ⁱ—Cd1—N2—N3	85.19 (19)	Cd1—O2—C5—C6	−175.4 (2)
O5—Cd1—N2—N3	−79.74 (19)	N2—N3—C5—O2	−1.3 (4)
N1—Cd1—N2—N3	−177.3 (2)	N2—N3—C5—C6	177.9 (2)
O2ⁱ—Cd1—N2—N3	2.5 (3)	O2—C5—C6—C7	−0.1 (5)
O2—Cd1—N2—N3	2.74 (17)	N3—C5—C6—C7	−179.3 (4)
C1—N2—N3—C5	−177.8 (2)	C5—C6—C7—C8	−3.2 (7)
Cd1—N2—N3—C5	−2.1 (3)	C6—C7—C8—O4	−176.1 (4)
N2ⁱ—Cd1—O2—C5	176.8 (2)	C6—C7—C8—O3	2.0 (6)
N2—Cd1—O2—C5	−3.36 (18)	C11—N4—C9—O6	2.1 (5)
O5ⁱ—Cd1—O2—C5	−99.33 (19)	C10—N4—C9—O6	−180.0 (3)

Symmetry code: (i) −x+1, y, −z+3/2.

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
O5—H5A···O4ⁱⁱ	0.85	1.97	2.802 (3)	165
O5—H5B···O1ⁱⁱⁱ	0.85	1.84	2.685 (3)	174
N3—H3A···O6	0.86	1.97	2.808 (3)	163
O3—H3···O2	0.82	1.68	2.498 (3)	175

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

Experimental details

Crystal data
Chemical formula	[Cd(C₁₅H₁₁N₅O₈)(H₂O)₂]·2C₃H₇NO
M_r	683.91
Crystal system, space group	Monoclinic, C2/c
Temperature (K)	298
a, b, c (Å)	18.6176 (2), 12.6065 (8), 12.0038 (6)
β (°)	99.51
V (Å³)	2778.6 (2)
Z	4
Radiation type	Mo Kα
µ (mm⁻¹)	0.86
Crystal size (mm)	0.20 × 0.18 × 0.17

Data collection
Diffractometer	Siemens SMART CCD area-detector diffractometer
Absorption correction	Multi-scan (SADABS; Sheldrick, 1996)
T_min, T_max	0.847, 0.868
No. of measured, independent and observed [I > 2σ(I)] reflections	6846, 2448, 2071
R_int	0.028
(sin θ/λ)_max (Å⁻¹)	0.595

Refinement
R[F² > 2σ(F²)], wR(F²), S	0.027, 0.075, 1.00
No. of reflections	2448
No. of parameters	189
H-atom treatment	H-atom parameters constrained
Δρ_max, Δρ_min (e Å⁻³)	0.73, −0.48

Computer programs: SMART (Siemens, 1996), SAINT (Siemens, 1996), SHELXS97 (Sheldrick, 2008), SHELXL97 (Sheldrick, 2008), SHELXTL (Sheldrick, 2008).

Selected bond lengths (Å) top

Cd1—N2ⁱ	2.287 (2)	N2—C1	1.321 (4)
Cd1—O5ⁱ	2.3412 (19)	N2—N3	1.369 (3)
Cd1—N1	2.387 (3)	N3—C5	1.319 (3)
Cd1—O2ⁱ	2.4441 (19)	O2—C5	1.269 (3)
N1—C2ⁱ	1.334 (3)

Symmetry code: (i) −x+1, y, −z+3/2.

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
O5—H5A···O4ⁱⁱ	0.85	1.97	2.802 (3)	165.2
O5—H5B···O1ⁱⁱⁱ	0.85	1.84	2.685 (3)	173.8
N3—H3A···O6	0.86	1.97	2.808 (3)	163.0
O3—H3···O2	0.82	1.68	2.498 (3)	174.8

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

Acknowledgements

We gratefully acknowledge financial support by the Natural Science Foundation of China (grant No. 20671048).

References

Bacchi, A., Battaglia, L. P., Carcelli, M., Pelizzi, C., Pelizzi, G., Solinas, C. & Zoroddu, M. A. (1993). J. Chem. Soc. Dalton Trans. pp. 775–779. CSD CrossRef Web of Science Google Scholar
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Volume 65| Part 4| April 2009| Pages m464-m465

doi:10.1107/S1600536809011003

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metal-organic compounds\(\def\hfill{\hskip 5em}\def\hfil{\hskip 3em}\def\eqno#1{\hfil {#1}}\)

Di­aqua­[N,N′-bis­­(3-carb­oxy­prop-2-enoyl)pyridine-2,6-dicarbo­hydrazidato(2–)]cadmium(II) N,N-di­methyl­formamide disolvate

Related literature

Experimental

Crystal data

Data collection

Refinement

Supporting information

Acknowledgements

References

metal-organic compounds

Diaqua[N,N′-bis(3-carboxyprop-2-enoyl)pyridine-2,6-dicarbohydrazidato(2–)]cadmium(II) N,N-dimethylformamide disolvate