catena-Poly[[bis­[2-(2,3-dimethyl­anilino)benzoato-κO]cadmium(II)]-di-μ-3-pyridylmethanol-κ2N:O;κ2O:N]

Moncol, J.; Mikloš, D.; Segľa, P.; Koman, M.; Lis, T.

doi:10.1107/S1600536808003000

metal-organic compounds

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ISSN: 2056-9890

Volume 64| Part 3| March 2008| Pages m440-m441

doi:10.1107/S1600536808003000

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catena-Poly[[bis[2-(2,3-dimethylanilino)benzoato-κO]cadmium(II)]-di-μ-3-pyridylmethanol-κ²N:O;κ²O:N]

Jan Moncol,^a ^* Dušan Mikloš,^a Peter Segľa,^a Marian Koman ^a and Tadeusz Lis ^b

^aDepartment of Inorganic Chemistry, Slovak, Technical University, Radlinského 9, SK-812 37 Bratislava, Slovakia, and ^bFaculty of Chemistry, University of Wrocław, 14 Joliot-Curie St, 50-383 Wrocław, Poland
^*Correspondence e-mail: jan.moncol@stuba.sk

(Received 22 January 2008; accepted 28 January 2008; online 6 February 2008)

In the crystal structure of the title compound, [Cd(C₁₅H₁₄NO₂)₂(C₆H₇NO)₂]_n, the Cd atom displays a distorted octahedral geometry, including two pyridine N atoms and two hydroxyl O from four symmetry-related 3-pyridylmethanol (3-pyme) ligands and two carboxylate O atoms from mefenamate [2-(2,3-dimethylanilino)benzoate] anions. The Cd atoms are connected via the bridging 3-pyme ligands into chains, that extend in the a-axis direction. The Cd atom is located on a center of inversion, whereas the 3-pyme ligands and the mefenamate anions occupy general positions.

Related literature

For related literature, see: Cini (2000 ); Lörinc et al. (2004 ); Moncol et al. (2006 ); Valach et al. (1997 ); Weder et al. (2002 ).

Experimental

Crystal data

[Cd(C₁₅H₁₄NO₂)₂(C₆H₇NO)₂]
M_r = 811.20
Triclinic, $[P \overline 1]$
a = 6.829 (2) Å
b = 7.765 (2) Å
c = 16.930 (4) Å
α = 79.25 (3)°
β = 85.31 (3)°
γ = 86.71 (3)°
V = 878.2 (4) Å³
Z = 1
Mo Kα radiation
μ = 0.68 mm⁻¹
T = 100 (2) K
0.15 × 0.08 × 0.02 mm

Data collection

Kuma KM-4 CCD diffractometer
Absorption correction: analytical (Clark & Reid, 1995 ) T_min = 0.915, T_max = 0.985
16779 measured reflections
6275 independent reflections
5024 reflections with I > 2σ(I)
R_int = 0.063

Refinement

R[F² > 2σ(F²)] = 0.062
wR(F²) = 0.087
S = 1.01
6275 reflections
243 parameters
H-atom parameters constrained
Δρ_max = 1.29 e Å⁻³
Δρ_min = −0.99 e Å⁻³

Table 1
Selected geometric parameters (Å, °)

Cd—O2	2.2475 (17)
Cd—O3ⁱ	2.3400 (17)
Cd—N2	2.348 (2)

O2—Cd—O3ⁱ	91.10 (6)
O2—Cd—N2	89.76 (7)
O3ⁱ—Cd—N2	94.51 (7)
Symmetry code: (i) x+1, y, z.

Table 2
Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
N1—H1N⋯O1	0.91	1.97	2.696 (3)	135
O3—H3O⋯O1ⁱⁱ	0.84	1.78	2.600 (2)	164
Symmetry code: (ii) -x, -y+1, -z+1.

Data collection: CrysAlis CCD (Oxford Diffraction, 2006 $[Oxford Diffraction (2006). KM-4 CCD/Xcalibur Software (including CrysAlis CCD and CrysAlis RED). Versions 1.171. Oxford Diffraction Poland, Wrocław, Poland.]$ ); cell refinement: CrysAlis RED (Oxford Diffraction, 2006 $[Oxford Diffraction (2006). KM-4 CCD/Xcalibur Software (including CrysAlis CCD and CrysAlis RED). Versions 1.171. Oxford Diffraction Poland, Wrocław, Poland.]$ ); data reduction: CrysAlis RED; program(s) used to solve structure: SHELXS97 (Sheldrick, 2008 ); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008); molecular graphics: XP in SHELXTL (Sheldrick, 2008); software used to prepare material for publication: enCIFer (Allen et al., 2004 ).

Supporting information

Crystal structure: contains datablocks global, I. DOI: 10.1107/S1600536808003000/nc2089sup1.cif

Structure factors: contains datablock I. DOI: 10.1107/S1600536808003000/nc2089Isup2.hkl

checkCIF report

Comment top

The importance of metal complexes with non-steroidal anti-inflammatory drugs (NSAIDs) as ligands has been stressed in several review papers (Cini, 2000; Weder et al., 2002). One of these NSAIDs are fenamates, which are derivatives of N-phenylantranilic acid and 2-phenylaminonicotinic acid (mefenamic acid, niflumic acid, tolfenamic acid, flufenamic acid). As part of our efforts to investigate metal(II) complexes based on fenamates, we describe the X-ray characterization of the title compound.

The Cd^II atom are in a distorted octahedral coordination formed by two carboxyl O atoms of mefenamate anions [Cd–O2 = 2.2475 (17) Å], two pyridine N atoms of 3-pyridylmethanol ligands (3-pyme) [Cd–N2 = 2.348 (2) Å] and two hydroxyl O atoms of adjacent 3-pyridylmethanol ligands [Cd–O3 = 2.3400 (17) Å] /Fig. 1). Each of the Cd atoms is connected via two symmetry related 3-pyridylmethanol into chains, that elongated in the direction of the crystallographic a axis.

The uncoordinated O atom of the carboxylate group of the mefenamate anion forms an intramolecular N–H···O hydrogen bonds to the amine H atoms as well as as intermolecular O–H···O hydrogen bonds to the hydroxyl H atoms of the 3-pyridylmethanol ligand, creating six-membered rings (Table 2).

The crystal structure of (I) can be compared with those of polymeric copper(II) carboxylate complexes [Cu(RCO₂)₂(3-pyme)₂]_n, which forms either coordination polymers with two bridging 3-pyme ligands between two Cu^II atoms or two-dimensional coordination polymer with only one bridging 3-pyme ligand between two Cu^II atoms (Moncol et al., 2006). [Cu(niflumate)₂(3-pyme)₂]_n for example is one-dimensional coordination polymer, (Valach et al., 1997), while [Cu(flufenamate)₂(3-pyme)₂]_n is two-dimensional coordination polymer (Lörinc et al., 2004).

Related literature top

For related literature, see: Cini (2000); Lörinc et al. (2004); Moncol et al. (2006); Valach et al. (1997); Weder et al. (2002).

Experimental top

The title complex was prepared by adding 3-pyridylmethanol (5 cm³) to a solution of Cd(mefenamato)₂.H₂O (1.25 mmol) in methanol (20 cm³). The fine white microcrystals which are formed by slow evaporation of the solvent on standing for a few days at room temperature were separated, washed with ethanol and dried in vacuo, yield 85%. The Anal. Calc.: C, 62.18; H, 5.22; N, 6.91; Cd, 13.86; Found: C, 61.82; H, 5.31; N, 7.00; Cd, 13.45. IR (KBr) cm^-1: 3279 ν(N–H); 1610 ν_as(COO^-); 1385 ν_s(COO^-); 1056 ν(C–O)_3-pyme; 643 δ(py)_3-pyme.

Computing details top

Data collection: CrysAlis CCD (Oxford Diffraction, 2006); cell refinement: CrysAlis RED (Oxford Diffraction, 2006); data reduction: CrysAlis RED (Oxford Diffraction, 2006); program(s) used to solve structure: SHELXS97 (Sheldrick, 2008); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008); molecular graphics: XP in SHELXTL (Sheldrick, 2008); software used to prepare material for publication: enCIFer (Allen et al., 2004).

Figures top

	Fig. 1. Perspective view of (I), with the atom numbering scheme and thermal ellipsoids drawn at the 30% probability level. Symmetry codes: i = x + 1, y, z, ii = x - 1, y, z.
	Fig. 2. The crystal packing of the title compound viewed along the b axis. Symmetry codes: ii = x - 1, y, z.

catena-Poly[[bis[2-(2,3-dimethylanilino)benzoato-κO]cadmium(II)]-di-µ- 3-pyridylmethanol-κ²N:O;κ²O:N] top

Crystal data top

[Cd(C₁₅H₁₄NO₂)₂(C₆H₇NO)₂]	Z = 1
M_r = 811.20	F(000) = 418
Triclinic, P1	D_x = 1.534 Mg m⁻³
Hall symbol: -P 1	Mo Kα radiation, λ = 0.71073 Å
a = 6.829 (2) Å	Cell parameters from 9193 reflections
b = 7.765 (2) Å	θ = 4–32°
c = 16.930 (4) Å	µ = 0.68 mm⁻¹
α = 79.25 (3)°	T = 100 K
β = 85.31 (3)°	Plate, colourless
γ = 86.71 (3)°	0.15 × 0.08 × 0.02 mm
V = 878.2 (4) Å³

Data collection top

Kuma KM-4 CCD diffractometer	6275 independent reflections
Radiation source: fine-focus sealed tube	5024 reflections with I > 2σ(I)
Graphite monochromator	R_int = 0.063
ω scans	θ_max = 32.5°, θ_min = 4.6°
Absorption correction: analytical (Clark & Reid, 1995)	h = −10→9
T_min = 0.915, T_max = 0.985	k = −11→11
16779 measured reflections	l = −23→25

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)] = 0.062	Hydrogen site location: inferred from neighbouring sites
wR(F²) = 0.087	H-atom parameters constrained
S = 1.01	w = 1/[σ²(F_o²) + (0.0274P)²] where P = (F_o² + 2F_c²)/3
6275 reflections	(Δ/σ)_max < 0.001
243 parameters	Δρ_max = 1.29 e Å⁻³
0 restraints	Δρ_min = −0.99 e Å⁻³

Crystal data top

[Cd(C₁₅H₁₄NO₂)₂(C₆H₇NO)₂]	γ = 86.71 (3)°
M_r = 811.20	V = 878.2 (4) Å³
Triclinic, P1	Z = 1
a = 6.829 (2) Å	Mo Kα radiation
b = 7.765 (2) Å	µ = 0.68 mm⁻¹
c = 16.930 (4) Å	T = 100 K
α = 79.25 (3)°	0.15 × 0.08 × 0.02 mm
β = 85.31 (3)°

Data collection top

Kuma KM-4 CCD diffractometer	6275 independent reflections
Absorption correction: analytical (Clark & Reid, 1995)	5024 reflections with I > 2σ(I)
T_min = 0.915, T_max = 0.985	R_int = 0.063
16779 measured reflections

Refinement top

R[F² > 2σ(F²)] = 0.062	0 restraints
wR(F²) = 0.087	H-atom parameters constrained
S = 1.01	Δρ_max = 1.29 e Å⁻³
6275 reflections	Δρ_min = −0.99 e Å⁻³
243 parameters

Special details top

Experimental. face-indexed (CrysAlis RED; Oxford Diffraction, 2006)

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
Cd	0.5000	0.5000	0.5000	0.01174 (8)
N1	0.7197 (3)	0.2022 (3)	0.20406 (12)	0.0165 (5)
N2	0.2681 (3)	0.7076 (2)	0.43955 (11)	0.0116 (4)
O1	0.5810 (2)	0.2645 (2)	0.35027 (10)	0.0179 (4)
O2	0.6740 (2)	0.5163 (2)	0.38047 (9)	0.0142 (4)
O3	−0.3074 (2)	0.7089 (2)	0.53597 (9)	0.0139 (4)
C1	0.6931 (3)	0.3927 (3)	0.34046 (14)	0.0130 (5)
C2	0.8654 (3)	0.3967 (3)	0.27859 (14)	0.0116 (5)
C3	1.0243 (3)	0.4955 (3)	0.28732 (15)	0.0158 (5)
H3	1.0159	0.5627	0.3290	0.019*
C4	1.1945 (4)	0.4974 (3)	0.23628 (15)	0.0176 (5)
H4	1.3022	0.5640	0.2433	0.021*
C5	1.2045 (4)	0.4011 (3)	0.17537 (15)	0.0178 (6)
H5	1.3208	0.4008	0.1405	0.021*
C6	1.0488 (3)	0.3050 (3)	0.16404 (14)	0.0148 (5)
H6	1.0583	0.2418	0.1209	0.018*
C7	0.8761 (3)	0.2994 (3)	0.21548 (14)	0.0127 (5)
C8	0.7302 (3)	0.0801 (3)	0.14937 (15)	0.0151 (5)
C9	0.7325 (3)	0.1415 (3)	0.06625 (15)	0.0154 (5)
C10	0.7413 (3)	0.0186 (3)	0.01387 (15)	0.0144 (5)
C11	0.7457 (3)	−0.1599 (3)	0.04723 (15)	0.0175 (5)
H11	0.7522	−0.2432	0.0124	0.021*
C12	0.7409 (4)	−0.2189 (3)	0.12952 (16)	0.0193 (6)
H12	0.7423	−0.3411	0.1507	0.023*
C13	0.7341 (3)	−0.0990 (3)	0.18106 (15)	0.0175 (5)
H13	0.7321	−0.1388	0.2377	0.021*
C14	0.7222 (4)	0.3341 (3)	0.03169 (15)	0.0175 (5)
H14A	0.6992	0.4009	0.0756	0.026*
H14B	0.6142	0.3600	−0.0040	0.026*
H14C	0.8465	0.3673	0.0010	0.026*
C15	0.7481 (4)	0.0776 (4)	−0.07602 (15)	0.0188 (6)
H15A	0.8841	0.0999	−0.0970	0.028*
H15B	0.6663	0.1855	−0.0890	0.028*
H15C	0.6983	−0.0141	−0.1007	0.028*
C21	−0.2568 (3)	0.8672 (3)	0.48322 (15)	0.0130 (5)
H21A	−0.2578	0.9633	0.5144	0.016*
H21B	−0.3555	0.8987	0.4426	0.016*
C22	−0.0558 (3)	0.8469 (3)	0.44113 (14)	0.0119 (5)
C23	−0.0057 (4)	0.9524 (3)	0.36745 (15)	0.0164 (5)
H23	−0.0984	1.0372	0.3428	0.020*
C24	0.1808 (3)	0.9330 (3)	0.33008 (15)	0.0176 (5)
H24	0.2169	1.0035	0.2794	0.021*
C25	0.3126 (3)	0.8097 (3)	0.36774 (14)	0.0145 (5)
H25	0.4399	0.7964	0.3419	0.017*
C26	0.0861 (3)	0.7263 (3)	0.47475 (14)	0.0116 (5)
H26	0.0531	0.6532	0.5251	0.014*
H1N	0.6340	0.1764	0.2482	0.014*
H3O	−0.3791	0.7267	0.5766	0.014*

Atomic displacement parameters (Å²) top

	U¹¹	U²²	U³³	U¹²	U¹³	U²³
Cd	0.01022 (13)	0.01148 (13)	0.01335 (14)	0.00098 (10)	0.00044 (9)	−0.00282 (10)
N1	0.0151 (10)	0.0236 (12)	0.0118 (11)	−0.0023 (9)	0.0033 (8)	−0.0071 (9)
N2	0.0111 (9)	0.0112 (10)	0.0129 (10)	−0.0010 (8)	0.0005 (8)	−0.0036 (8)
O1	0.0177 (9)	0.0199 (9)	0.0169 (9)	−0.0040 (8)	0.0039 (7)	−0.0068 (8)
O2	0.0170 (8)	0.0127 (8)	0.0124 (9)	0.0014 (7)	0.0046 (7)	−0.0041 (7)
O3	0.0138 (8)	0.0140 (9)	0.0142 (9)	−0.0035 (7)	0.0045 (7)	−0.0045 (7)
C1	0.0142 (11)	0.0138 (12)	0.0097 (12)	0.0040 (10)	−0.0026 (9)	0.0003 (10)
C2	0.0127 (11)	0.0110 (11)	0.0095 (11)	0.0022 (9)	0.0006 (9)	0.0008 (9)
C3	0.0185 (12)	0.0152 (12)	0.0136 (13)	0.0013 (10)	−0.0017 (10)	−0.0025 (10)
C4	0.0165 (12)	0.0196 (13)	0.0164 (13)	−0.0033 (10)	0.0010 (10)	−0.0027 (11)
C5	0.0140 (12)	0.0219 (14)	0.0143 (13)	0.0017 (10)	0.0061 (10)	0.0007 (11)
C6	0.0171 (12)	0.0165 (12)	0.0101 (12)	0.0041 (10)	0.0000 (9)	−0.0031 (10)
C7	0.0134 (11)	0.0116 (12)	0.0126 (12)	0.0008 (9)	−0.0007 (9)	−0.0017 (10)
C8	0.0089 (11)	0.0211 (13)	0.0154 (13)	0.0000 (10)	0.0009 (9)	−0.0048 (11)
C9	0.0095 (11)	0.0168 (13)	0.0192 (13)	0.0011 (9)	0.0003 (9)	−0.0025 (11)
C10	0.0071 (11)	0.0196 (13)	0.0167 (13)	0.0022 (9)	−0.0010 (9)	−0.0044 (11)
C11	0.0141 (12)	0.0232 (14)	0.0171 (13)	−0.0024 (10)	−0.0001 (10)	−0.0084 (11)
C12	0.0179 (13)	0.0156 (13)	0.0236 (14)	−0.0018 (10)	−0.0015 (11)	−0.0009 (11)
C13	0.0159 (12)	0.0208 (14)	0.0155 (13)	−0.0022 (10)	−0.0012 (10)	−0.0023 (11)
C14	0.0191 (13)	0.0173 (13)	0.0162 (13)	0.0013 (10)	−0.0006 (10)	−0.0042 (11)
C15	0.0166 (12)	0.0224 (14)	0.0176 (13)	0.0029 (11)	0.0003 (10)	−0.0055 (11)
C21	0.0113 (11)	0.0102 (11)	0.0172 (13)	0.0003 (9)	−0.0009 (9)	−0.0023 (10)
C22	0.0116 (11)	0.0108 (11)	0.0143 (12)	−0.0020 (9)	−0.0006 (9)	−0.0045 (10)
C23	0.0168 (12)	0.0144 (12)	0.0174 (13)	0.0011 (10)	−0.0033 (10)	−0.0009 (11)
C24	0.0177 (12)	0.0189 (13)	0.0135 (13)	−0.0018 (10)	0.0006 (10)	0.0032 (11)
C25	0.0147 (12)	0.0163 (13)	0.0124 (12)	−0.0036 (10)	0.0032 (9)	−0.0030 (10)
C26	0.0133 (11)	0.0116 (12)	0.0094 (11)	−0.0019 (9)	0.0024 (9)	−0.0018 (9)

Geometric parameters (Å, º) top

Cd—O2ⁱ	2.2475 (17)	C8—C9	1.398 (3)
Cd—O2	2.2475 (17)	C9—C10	1.415 (3)
Cd—O3ⁱⁱ	2.3400 (17)	C9—C14	1.501 (3)
Cd—O3ⁱⁱⁱ	2.3400 (17)	C10—C11	1.396 (3)
Cd—N2	2.348 (2)	C10—C15	1.503 (3)
Cd—N2ⁱ	2.348 (2)	C11—C12	1.381 (3)
N1—C7	1.389 (3)	C11—H11	0.9500
N1—C8	1.439 (3)	C12—C13	1.386 (4)
N1—H1N	0.91	C12—H12	0.9500
N2—C25	1.344 (3)	C13—H13	0.9500
N2—C26	1.346 (3)	C14—H14A	0.9800
O1—C1	1.269 (3)	C14—H14B	0.9800
O2—C1	1.269 (3)	C14—H14C	0.9800
O3—C21	1.420 (3)	C15—H15A	0.9800
O3—Cd^iv	2.3400 (17)	C15—H15B	0.9800
O3—H3O	0.84	C15—H15C	0.9800
C1—C2	1.507 (3)	C21—C22	1.508 (3)
C2—C3	1.397 (3)	C21—H21A	0.9900
C2—C7	1.414 (3)	C21—H21B	0.9900
C3—C4	1.389 (3)	C22—C23	1.387 (3)
C3—H3	0.9500	C22—C26	1.388 (3)
C4—C5	1.378 (4)	C23—C24	1.388 (3)
C4—H4	0.9500	C23—H23	0.9500
C5—C6	1.379 (3)	C24—C25	1.379 (3)
C5—H5	0.9500	C24—H24	0.9500
C6—C7	1.405 (3)	C25—H25	0.9500
C6—H6	0.9500	C26—H26	0.9500
C8—C13	1.394 (3)

O2ⁱ—Cd—O2	180.000 (1)	C8—C9—C10	119.0 (2)
O2ⁱ—Cd—O3ⁱⁱ	91.10 (6)	C8—C9—C14	121.6 (2)
O2—Cd—O3ⁱⁱ	88.90 (6)	C10—C9—C14	119.5 (2)
O2ⁱ—Cd—O3ⁱⁱⁱ	88.90 (6)	C11—C10—C9	118.7 (2)
O2—Cd—O3ⁱⁱⁱ	91.10 (6)	C11—C10—C15	120.2 (2)
O3ⁱⁱ—Cd—O3ⁱⁱⁱ	180.00 (5)	C9—C10—C15	121.1 (2)
O2ⁱ—Cd—N2	90.24 (7)	C12—C11—C10	121.8 (2)
O2—Cd—N2	89.76 (7)	C12—C11—H11	119.1
O3ⁱⁱ—Cd—N2	85.49 (7)	C10—C11—H11	119.1
O3ⁱⁱⁱ—Cd—N2	94.51 (7)	C11—C12—C13	119.8 (2)
O2ⁱ—Cd—N2ⁱ	89.76 (7)	C11—C12—H12	120.1
O2—Cd—N2ⁱ	90.24 (7)	C13—C12—H12	120.1
O3ⁱⁱ—Cd—N2ⁱ	94.51 (7)	C12—C13—C8	119.6 (2)
O3ⁱⁱⁱ—Cd—N2ⁱ	85.49 (7)	C12—C13—H13	120.2
N2—Cd—N2ⁱ	180.00 (9)	C8—C13—H13	120.2
C7—N1—C8	124.02 (19)	C9—C14—H14A	109.5
C7—N1—H1N	114.1	C9—C14—H14B	109.5
C8—N1—H1N	115.4	H14A—C14—H14B	109.5
C25—N2—C26	118.0 (2)	C9—C14—H14C	109.5
C25—N2—Cd	120.73 (15)	H14A—C14—H14C	109.5
C26—N2—Cd	121.31 (15)	H14B—C14—H14C	109.5
C1—O2—Cd	124.12 (15)	C10—C15—H15A	109.5
C21—O3—Cd^iv	123.21 (14)	C10—C15—H15B	109.5
C21—O3—H3O	112.5	H15A—C15—H15B	109.5
Cd^iv—O3—H3O	96.9	C10—C15—H15C	109.5
O2—C1—O1	124.7 (2)	H15A—C15—H15C	109.5
O2—C1—C2	117.3 (2)	H15B—C15—H15C	109.5
O1—C1—C2	117.9 (2)	O3—C21—C22	110.59 (18)
C3—C2—C7	119.4 (2)	O3—C21—H21A	109.5
C3—C2—C1	117.5 (2)	C22—C21—H21A	109.5
C7—C2—C1	123.1 (2)	O3—C21—H21B	109.5
C4—C3—C2	121.4 (2)	C22—C21—H21B	109.5
C4—C3—H3	119.3	H21A—C21—H21B	108.1
C2—C3—H3	119.3	C23—C22—C26	117.8 (2)
C5—C4—C3	118.9 (2)	C23—C22—C21	120.4 (2)
C5—C4—H4	120.6	C26—C22—C21	121.9 (2)
C3—C4—H4	120.6	C22—C23—C24	119.5 (2)
C4—C5—C6	121.2 (2)	C22—C23—H23	120.2
C4—C5—H5	119.4	C24—C23—H23	120.2
C6—C5—H5	119.4	C25—C24—C23	118.9 (2)
C5—C6—C7	120.9 (2)	C25—C24—H24	120.6
C5—C6—H6	119.5	C23—C24—H24	120.6
C7—C6—H6	119.5	N2—C25—C24	122.6 (2)
N1—C7—C6	120.8 (2)	N2—C25—H25	118.7
N1—C7—C2	121.0 (2)	C24—C25—H25	118.7
C6—C7—C2	118.2 (2)	N2—C26—C22	123.3 (2)
C13—C8—C9	121.2 (2)	N2—C26—H26	118.4
C13—C8—N1	118.7 (2)	C22—C26—H26	118.4
C9—C8—N1	120.1 (2)

O2ⁱ—Cd—N2—C25	162.39 (18)	C1—C2—C7—C6	−176.3 (2)
O2—Cd—N2—C25	−17.61 (18)	C7—N1—C8—C13	106.9 (3)
O3ⁱⁱ—Cd—N2—C25	−106.52 (18)	C7—N1—C8—C9	−74.3 (3)
O3ⁱⁱⁱ—Cd—N2—C25	73.48 (18)	C13—C8—C9—C10	−0.7 (3)
O2ⁱ—Cd—N2—C26	−18.75 (17)	N1—C8—C9—C10	−179.5 (2)
O2—Cd—N2—C26	161.25 (17)	C13—C8—C9—C14	178.1 (2)
O3ⁱⁱ—Cd—N2—C26	72.33 (17)	N1—C8—C9—C14	−0.7 (3)
O3ⁱⁱⁱ—Cd—N2—C26	−107.67 (17)	C8—C9—C10—C11	0.5 (3)
O3ⁱⁱ—Cd—O2—C1	−26.22 (17)	C14—C9—C10—C11	−178.4 (2)
O3ⁱⁱⁱ—Cd—O2—C1	153.78 (17)	C8—C9—C10—C15	−178.8 (2)
N2—Cd—O2—C1	−111.71 (18)	C14—C9—C10—C15	2.3 (3)
N2ⁱ—Cd—O2—C1	68.29 (18)	C9—C10—C11—C12	0.3 (4)
Cd—O2—C1—O1	19.1 (3)	C15—C10—C11—C12	179.6 (2)
Cd—O2—C1—C2	−159.04 (14)	C10—C11—C12—C13	−0.9 (4)
O2—C1—C2—C3	21.1 (3)	C11—C12—C13—C8	0.6 (4)
O1—C1—C2—C3	−157.2 (2)	C9—C8—C13—C12	0.1 (4)
O2—C1—C2—C7	−162.0 (2)	N1—C8—C13—C12	178.9 (2)
O1—C1—C2—C7	19.8 (3)	Cd^iv—O3—C21—C22	−96.45 (19)
C7—C2—C3—C4	−1.3 (4)	O3—C21—C22—C23	155.3 (2)
C1—C2—C3—C4	175.7 (2)	O3—C21—C22—C26	−26.0 (3)
C2—C3—C4—C5	0.8 (4)	C26—C22—C23—C24	0.6 (4)
C3—C4—C5—C6	0.6 (4)	C21—C22—C23—C24	179.3 (2)
C4—C5—C6—C7	−1.4 (4)	C22—C23—C24—C25	−0.6 (4)
C8—N1—C7—C6	10.3 (3)	C26—N2—C25—C24	1.0 (4)
C8—N1—C7—C2	−170.3 (2)	Cd—N2—C25—C24	179.88 (18)
C5—C6—C7—N1	−179.8 (2)	C23—C24—C25—N2	−0.2 (4)
C5—C6—C7—C2	0.8 (3)	C25—N2—C26—C22	−1.0 (3)
C3—C2—C7—N1	−178.9 (2)	Cd—N2—C26—C22	−179.84 (17)
C1—C2—C7—N1	4.2 (3)	C23—C22—C26—N2	0.2 (4)
C3—C2—C7—C6	0.6 (3)	C21—C22—C26—N2	−178.5 (2)

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

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
N1—H1N···O1	0.91	1.97	2.696 (3)	135
O3—H3O···O1ⁱⁱ	0.84	1.78	2.600 (2)	164

Symmetry code: (ii) −x, −y+1, −z+1.

Experimental details

Crystal data
Chemical formula	[Cd(C₁₅H₁₄NO₂)₂(C₆H₇NO)₂]
M_r	811.20
Crystal system, space group	Triclinic, P1
Temperature (K)	100
a, b, c (Å)	6.829 (2), 7.765 (2), 16.930 (4)
α, β, γ (°)	79.25 (3), 85.31 (3), 86.71 (3)
V (Å³)	878.2 (4)
Z	1
Radiation type	Mo Kα
µ (mm⁻¹)	0.68
Crystal size (mm)	0.15 × 0.08 × 0.02

Data collection
Diffractometer	Kuma KM-4 CCD diffractometer
Absorption correction	Analytical (Clark & Reid, 1995)
T_min, T_max	0.915, 0.985
No. of measured, independent and observed [I > 2σ(I)] reflections	16779, 6275, 5024
R_int	0.063
(sin θ/λ)_max (Å⁻¹)	0.756

Refinement
R[F² > 2σ(F²)], wR(F²), S	0.062, 0.087, 1.01
No. of reflections	6275
No. of parameters	243
H-atom treatment	H-atom parameters constrained
Δρ_max, Δρ_min (e Å⁻³)	1.29, −0.99

Computer programs: CrysAlis CCD (Oxford Diffraction, 2006), CrysAlis RED (Oxford Diffraction, 2006), SHELXS97 (Sheldrick, 2008), SHELXL97 (Sheldrick, 2008), XP in SHELXTL (Sheldrick, 2008), enCIFer (Allen et al., 2004).

Selected geometric parameters (Å, º) top

Cd—O2	2.2475 (17)	Cd—N2	2.348 (2)
Cd—O3ⁱ	2.3400 (17)

O2—Cd—O3ⁱ	91.10 (6)	O3ⁱ—Cd—N2	94.51 (7)
O2—Cd—N2	89.76 (7)

Symmetry code: (i) x+1, y, z.

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
N1—H1N···O1	0.91	1.97	2.696 (3)	135.2
O3—H3O···O1ⁱⁱ	0.84	1.78	2.600 (2)	163.8

Symmetry code: (ii) −x, −y+1, −z+1.

Acknowledgements

We thank the Scientific Grant Agency of the Ministry of Education of the Slovak Republic and the Slovak Academy of Sciences (1/4454/07 and 1/0353/08).

References

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