Bis{6-meth­oxy-2-[(4-methyl­phen­yl)­iminio­meth­yl]phenolato-κ2O,O′}bis­(nitrato-κ2O,O′)cadmium(II)

Li, H.-Q.; Xian, H.-D.; Liu, J.-F.; Zhao, G.-L.

doi:10.1107/S1600536808033539

metal-organic compounds

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ISSN: 2056-9890

Volume 64| Part 11| November 2008| Pages m1482-m1483

doi:10.1107/S1600536808033539

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Bis{6-methoxy-2-[(4-methylphenyl)iminiomethyl]phenolato-κ²O,O′}bis(nitrato-κ²O,O′)cadmium(II)

Hua-Qiong Li,^a Hui-Duo Xian,^a Jian-Feng Liu ^a and Guo-Liang Zhao ^a ^*

^aZhejiang Key Laboratory for Reactive Chemistry on Solid Surfaces, Institute of Physical Chemistry, Zhejiang Normal University, Jinhua, Zhejiang 321004, People's Republic of China, and, College of Chemistry and Life Science, Zhejiang Normal University, Jinhua 321004, Zhejiang, People's Republic of China
^*Correspondence e-mail: sky53@zjnu.cn

(Received 27 September 2008; accepted 15 October 2008; online 31 October 2008)

The Schiff base 6-methoxy-2-[(4-methylphenyl)iminomethyl]phenol (HL) forms a neutral complex with cadmium(II) nitrate, [Cd(NO₃)₂(C₁₅H₁₅NO₂)₂], in which the four O atoms of the two independent ligands are coordinated to the metal center and the protonated imine N atoms are involved in a hydrogen bond with the phenoxide group. Intramolecular N—H⋯O hydrogen-bonding interactions stabilize the structure. Each organic ligand assumes a zwitterionic form, chelating to the metal atom through the two O atoms, while the two nitrate groups also exhibit chelating behavior, leading to a distorted octahedral coordination of the Cd atom.

Related literature

For related literature, see: Dominiak et al. (2003 ); Elmali et al. (2003 ); Filarowski et al. (1998 ); Müller et al. (2001 ); Novitchi et al. (2008 ); Schiff (1864 ); West (1960 ); Woźniak et al. (1995 ); Yu et al. (2007 ); Zhao et al. (2007 ); Zhou et al. (2007 ); Zhou & Zhao (2007 ).

Experimental

Crystal data

[Cd(NO₃)₂(C₁₅H₁₅NO₂)₂]
M_r = 718.99
Monoclinic, P 2₁ /c
a = 10.8009 (4) Å
b = 27.3377 (10) Å
c = 10.5878 (4) Å
β = 90.208 (2)°
V = 3126.3 (2) Å³
Z = 4
Mo Kα radiation
μ = 0.76 mm⁻¹
T = 296 (2) K
0.35 × 0.30 × 0.11 mm

Data collection

Bruker APEXII area-detector diffractometer
Absorption correction: multi-scan (SADABS; Sheldrick, 1996 ) T_min = 0.765, T_max = 0.923
31192 measured reflections
5498 independent reflections
3112 reflections with I > 2σ(I)
R_int = 0.090

Refinement

R[F² > 2σ(F²)] = 0.059
wR(F²) = 0.178
S = 0.98
5498 reflections
389 parameters
3 restraints
H-atom parameters constrained
Δρ_max = 0.92 e Å⁻³
Δρ_min = −0.75 e Å⁻³

Table 1
Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
N1—H1D⋯O2	0.86	1.94	2.616 (6)	135
N2—H2A⋯O4	0.86	1.90	2.577 (7)	135

Data collection: APEX2 (Bruker, 2006 ); cell refinement: SAINT (Bruker, 2006); data reduction: SAINT; program(s) used to solve structure: SHELXTL (Sheldrick, 2008 ); program(s) used to refine structure: SHELXTL; molecular graphics: SHELXTL; software used to prepare material for publication: SHELXTL.

Supporting information

Crystal structure: contains datablocks I, global. DOI: 10.1107/S1600536808033539/at2640sup1.cif

Structure factors: contains datablock I. DOI: 10.1107/S1600536808033539/at2640Isup2.hkl

checkCIF report

Comment top

Since the Schiff bases, the products of condensation of carbonyl compounds with primary amines, were discovered in 1864 by Hugo Schiff (Schiff, 1864), the studies on this kind of compounds containing imine group were carried out widely in different application fields. And recently, the metal complexes with the Schiff base ligands derived from substituted salicylaldehyde and aniline, have received attention due to their applications in catalysis, nuclear medicine (Zhou et al., 2007), magnetism (Elmali et al., 2003) and novel structural features (Müller et al., 2001; Novitchi et al., 2008). They include complexes with a methoxy group in the ortho position (West, 1960) which can bind to the metal too. Zhao and co-workers had reported complexes of this series with several transitional and rare earth metals (Zhou & Zhao, 2007; Yu et al., 2007; Zhao et al., 2007). Here we decribe the synthesis and crystal structure of a new cadmium(II) complex (Fig. 1), Cd(HL)₂(NO₃)₂, involving the Schiff base HL.

The most interesting feature of the complex is the two N—H···O intramolecular hydrogen bonds. In fact, there is a proton-transfer equilibrium between the OH and NH tautomers (Dominiak et al., 2003). And it is reported that the products of condensation of salicylaldehydes with anilines show intermolecular proton-transfer equilibrium and double fluorescence (Filarowski et al., 1998; Woźniak et al., 1995). In addition, the title complex has the Cd atom in a geometry that can be better described as a bicapped trigonal antiprism (Fig. 2).

Related literature top

For related literature, see: Dominiak et al. (2003); Elmali et al. (2003); Filarowski et al. (1998); Müller et al. (2001); Novitchi et al. (2008); Schiff (1864); West (1960); Woźniak et al. (1995); Yu et al. (2007); Zhao et al. (2007); Zhou et al. (2007); Zhou & Zhao (2007).

Experimental top

First, the ligand was prepared by the direct solid-phase reaction of o-vanillin (10 mmol, 1.5251 g) and p-toluidine (10 mmol, 1.0700 g). The reactants were ground in an agate mortar. The colour of the mixture changed from light yellow to orange. Then, for the preparation of the complex, the solution of Cd(NO₃)₂.4H₂O (1 mmol, 0.3091 g) in methanol (10 ml) was added to a methanol (30 ml) solution of the Schiff base ligand (2 mmol, 0.4812 g). Red crystals were obtained after two weeks.

Computing details top

Data collection: APEX2 (Bruker, 2006); cell refinement: SAINT (Bruker, 2006); data reduction: SAINT (Bruker, 2006); program(s) used to solve structure: SHELXTL (Sheldrick, 2008); program(s) used to refine structure: SHELXTL (Sheldrick, 2008); molecular graphics: SHELXTL (Sheldrick, 2008); software used to prepare material for publication: SHELXTL (Sheldrick, 2008).

Figures top

	Fig. 1. The molecular structure of complex, showing the atom-labelling scheme. Displacement ellipsoids are drawn at the 30% probability level.
	Fig. 2. Eight-coordinate geometry of Cd.

Bis{6-methoxy-2-[(4-methylphenyl)iminiomethyl]phenolato- κ²O,O'}bis(nitrato-κ²O,O')cadmium(II) top

Crystal data top

[Cd(NO₃)₂(C₁₅H₁₅NO₂)₂]	F(000) = 1464
M_r = 718.99	D_x = 1.528 Mg m⁻³
Monoclinic, P2₁/c	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: -P 2ybc	Cell parameters from 8740 reflections
a = 10.8009 (4) Å	θ = 1.9–25.0°
b = 27.3377 (10) Å	µ = 0.76 mm⁻¹
c = 10.5878 (4) Å	T = 296 K
β = 90.208 (2)°	Block, red
V = 3126.3 (2) Å³	0.35 × 0.30 × 0.11 mm
Z = 4

Data collection top

Bruker APEXII area-detector diffractometer	5498 independent reflections
Radiation source: fine-focus sealed tube	3112 reflections with I > 2σ(I)
Graphite monochromator	R_int = 0.090
ω scans	θ_max = 25.0°, θ_min = 1.9°
Absorption correction: multi-scan (SADABS; Sheldrick, 1996)	h = −12→12
T_min = 0.765, T_max = 0.923	k = −32→32
31192 measured reflections	l = −12→12

Refinement top

Refinement on F²	Secondary atom site location: difference Fourier map
Least-squares matrix: full	Hydrogen site location: inferred from neighbouring sites
R[F² > 2σ(F²)] = 0.059	H-atom parameters constrained
wR(F²) = 0.178	w = 1/[σ²(F_o²) + (0.1P)²] where P = (F_o² + 2F_c²)/3
S = 0.98	(Δ/σ)_max = 0.003
5498 reflections	Δρ_max = 0.92 e Å⁻³
389 parameters	Δρ_min = −0.75 e Å⁻³
3 restraints	Extinction correction: SHELXTL (Sheldrick, 2008), Fc^*=kFc[1+0.001xFc²λ³/sin(2θ)]^-1/4
Primary atom site location: structure-invariant direct methods	Extinction coefficient: 0.0013 (4)

Crystal data top

[Cd(NO₃)₂(C₁₅H₁₅NO₂)₂]	V = 3126.3 (2) Å³
M_r = 718.99	Z = 4
Monoclinic, P2₁/c	Mo Kα radiation
a = 10.8009 (4) Å	µ = 0.76 mm⁻¹
b = 27.3377 (10) Å	T = 296 K
c = 10.5878 (4) Å	0.35 × 0.30 × 0.11 mm
β = 90.208 (2)°

Data collection top

Bruker APEXII area-detector diffractometer	5498 independent reflections
Absorption correction: multi-scan (SADABS; Sheldrick, 1996)	3112 reflections with I > 2σ(I)
T_min = 0.765, T_max = 0.923	R_int = 0.090
31192 measured reflections

Refinement top

R[F² > 2σ(F²)] = 0.059	3 restraints
wR(F²) = 0.178	H-atom parameters constrained
S = 0.98	Δρ_max = 0.92 e Å⁻³
5498 reflections	Δρ_min = −0.75 e Å⁻³
389 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.

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
Cd1	0.52395 (5)	0.120056 (16)	0.72358 (4)	0.0622 (2)
N1	0.6050 (5)	0.0522 (2)	0.3386 (4)	0.0599 (14)
H1D	0.6111	0.0635	0.4141	0.072*
O1	0.2880 (4)	0.08774 (19)	0.6790 (4)	0.0758 (14)
C1	1.0356 (10)	0.0759 (4)	0.0381 (11)	0.177 (6)
H1A	1.1044	0.0861	0.0893	0.265*
H1B	1.0161	0.1011	−0.0220	0.265*
H1C	1.0567	0.0464	−0.0060	0.265*
O2	0.4950 (4)	0.07844 (15)	0.5476 (3)	0.0573 (11)
N2	0.2895 (5)	0.2425 (2)	0.5429 (5)	0.0717 (16)
H2A	0.3209	0.2145	0.5612	0.086*
C2	0.9263 (10)	0.0668 (4)	0.1200 (10)	0.110 (3)
O3	0.6180 (5)	0.18717 (18)	0.8523 (4)	0.0833 (16)
N3	0.4284 (6)	0.0859 (3)	0.9582 (6)	0.0827 (19)
C3	0.9270 (9)	0.0774 (3)	0.2471 (10)	0.110 (3)
H3A	0.9996	0.0881	0.2857	0.132*
O4	0.4455 (4)	0.19201 (16)	0.6736 (4)	0.0681 (12)
N4	0.7851 (7)	0.1171 (3)	0.6646 (8)	0.088 (2)
C4	0.8199 (8)	0.0723 (3)	0.3176 (7)	0.090 (2)
H4A	0.8209	0.0800	0.4032	0.108*
O5	0.4001 (6)	0.1286 (2)	0.9256 (5)	0.0974 (18)
C5	0.7126 (7)	0.0561 (2)	0.2624 (6)	0.0632 (17)
O6	0.4965 (5)	0.06211 (19)	0.8850 (5)	0.0908 (16)
C6	0.7084 (7)	0.0448 (3)	0.1345 (6)	0.085 (2)
H6A	0.6371	0.0326	0.0963	0.102*
O7	0.3892 (6)	0.0678 (2)	1.0554 (5)	0.118 (2)
C7	0.8180 (10)	0.0526 (4)	0.0660 (8)	0.107 (3)
H7A	0.8161	0.0478	−0.0209	0.129*
C8	0.4994 (7)	0.0337 (2)	0.3078 (6)	0.0651 (19)
H8A	0.4935	0.0178	0.2303	0.078*
O8	0.8962 (7)	0.1137 (3)	0.6465 (8)	0.148 (3)
O9	0.7315 (5)	0.0961 (2)	0.7569 (5)	0.0932 (15)
C9	0.3925 (7)	0.0357 (2)	0.3828 (6)	0.0635 (18)
O10	0.7174 (5)	0.1395 (2)	0.5923 (5)	0.0983 (17)
C10	0.2830 (8)	0.0150 (3)	0.3372 (7)	0.082 (2)
H10A	0.2832	−0.0015	0.2604	0.098*
C11	0.1761 (9)	0.0187 (3)	0.4042 (8)	0.103 (3)
H11A	0.1039	0.0046	0.3730	0.124*
C12	0.1741 (8)	0.0431 (3)	0.5180 (7)	0.089 (2)
H12A	0.0999	0.0459	0.5617	0.107*
C13	0.2790 (6)	0.0631 (2)	0.5672 (6)	0.0599 (17)
C14	0.3929 (6)	0.0600 (2)	0.5020 (5)	0.0560 (16)
C15	0.1807 (7)	0.0849 (3)	0.7610 (7)	0.098 (3)
H15B	0.1649	0.0514	0.7821	0.147*
H15C	0.1100	0.0984	0.7183	0.147*
H30A	0.1965	0.1032	0.8369	0.147*
C16	−0.1017 (8)	0.2383 (4)	0.1810 (8)	0.135 (4)
H16A	−0.1112	0.2701	0.1441	0.203*
H16B	−0.1776	0.2288	0.2210	0.203*
H16C	−0.0817	0.2151	0.1161	0.203*
C17	0.0001 (9)	0.2395 (3)	0.2769 (9)	0.1052 (15)
C18	0.0332 (8)	0.2003 (3)	0.3448 (8)	0.1052 (15)
H18A	−0.0100	0.1714	0.3320	0.126*
C19	0.1278 (9)	0.2004 (3)	0.4330 (8)	0.1052 (15)
H19A	0.1452	0.1725	0.4799	0.126*
C20	0.1959 (9)	0.2424 (3)	0.4501 (9)	0.1052 (15)
C21	0.1634 (8)	0.2822 (3)	0.3850 (8)	0.105 (3)
H21A	0.2063	0.3114	0.3967	0.126*
C22	0.0648 (8)	0.2800 (3)	0.2990 (8)	0.105 (3)
H22A	0.0434	0.3083	0.2553	0.126*
C23	0.3343 (7)	0.2797 (3)	0.6043 (6)	0.0704 (19)
H23A	0.3031	0.3105	0.5846	0.084*
C24	0.4257 (7)	0.2769 (2)	0.6977 (6)	0.0648 (18)
C25	0.4601 (8)	0.3203 (3)	0.7604 (7)	0.091 (3)
H25A	0.4252	0.3500	0.7369	0.109*
C26	0.5450 (8)	0.3182 (3)	0.8558 (7)	0.092 (3)
H26A	0.5659	0.3467	0.8988	0.111*
C27	0.6008 (8)	0.2744 (3)	0.8898 (6)	0.081 (2)
H27A	0.6598	0.2737	0.9540	0.097*
C28	0.5685 (7)	0.2320 (3)	0.8280 (6)	0.0646 (18)
C29	0.4791 (6)	0.2322 (2)	0.7297 (6)	0.0576 (16)
C30	0.6976 (8)	0.1818 (3)	0.9596 (7)	0.105 (3)
H30B	0.7201	0.2136	0.9910	0.158*
H30C	0.7709	0.1644	0.9355	0.158*
H30D	0.6551	0.1640	1.0244	0.158*

Atomic displacement parameters (Å²) top

	U¹¹	U²²	U³³	U¹²	U¹³	U²³
Cd1	0.0739 (4)	0.0603 (4)	0.0524 (3)	0.0070 (3)	−0.0105 (2)	−0.0061 (2)
N1	0.074 (4)	0.060 (3)	0.047 (3)	0.005 (3)	0.000 (3)	−0.003 (2)
O1	0.057 (3)	0.108 (4)	0.062 (3)	−0.009 (3)	0.013 (2)	−0.016 (3)
C1	0.154 (11)	0.172 (12)	0.206 (12)	−0.010 (9)	0.122 (10)	0.007 (10)
O2	0.057 (3)	0.067 (3)	0.048 (2)	−0.005 (2)	−0.003 (2)	−0.012 (2)
N2	0.087 (4)	0.056 (4)	0.072 (4)	0.002 (3)	−0.016 (3)	0.000 (3)
C2	0.114 (8)	0.111 (8)	0.106 (8)	0.015 (6)	0.059 (7)	0.008 (6)
O3	0.099 (4)	0.074 (4)	0.076 (3)	0.013 (3)	−0.043 (3)	−0.019 (3)
N3	0.093 (5)	0.099 (6)	0.055 (4)	0.011 (4)	−0.013 (3)	0.002 (4)
C3	0.101 (7)	0.096 (7)	0.134 (8)	−0.018 (5)	0.038 (6)	−0.008 (6)
O4	0.080 (3)	0.056 (3)	0.069 (3)	0.002 (2)	−0.022 (2)	−0.009 (2)
N4	0.075 (5)	0.099 (6)	0.090 (5)	−0.002 (4)	0.001 (4)	−0.023 (4)
C4	0.099 (7)	0.096 (6)	0.075 (5)	−0.008 (5)	0.026 (5)	−0.006 (4)
O5	0.128 (5)	0.097 (5)	0.068 (3)	0.024 (4)	0.014 (2)	−0.012 (3)
C5	0.073 (5)	0.060 (4)	0.056 (4)	0.014 (4)	0.019 (3)	0.004 (3)
O6	0.126 (5)	0.078 (3)	0.069 (3)	0.021 (3)	0.010 (3)	0.0088 (19)
C6	0.091 (6)	0.108 (6)	0.054 (4)	0.028 (5)	0.008 (4)	0.001 (4)
O7	0.120 (5)	0.160 (6)	0.074 (4)	−0.002 (4)	0.021 (3)	0.033 (4)
C7	0.138 (9)	0.119 (8)	0.065 (5)	0.046 (7)	0.041 (6)	0.012 (5)
C8	0.102 (6)	0.053 (4)	0.041 (3)	0.000 (4)	−0.003 (4)	−0.004 (3)
O8	0.069 (5)	0.185 (8)	0.190 (8)	0.017 (4)	−0.015 (5)	−0.039 (5)
O9	0.086 (2)	0.099 (4)	0.095 (4)	0.027 (3)	−0.017 (3)	−0.006 (3)
C9	0.088 (5)	0.053 (4)	0.049 (4)	−0.006 (4)	−0.002 (3)	−0.004 (3)
O10	0.074 (4)	0.129 (5)	0.092 (4)	0.000 (4)	−0.020 (3)	0.018 (4)
C10	0.097 (7)	0.078 (5)	0.070 (5)	−0.020 (5)	−0.010 (4)	−0.020 (4)
C11	0.092 (7)	0.118 (8)	0.100 (7)	−0.039 (6)	−0.005 (5)	−0.007 (6)
C12	0.079 (6)	0.103 (7)	0.084 (5)	−0.025 (5)	−0.003 (4)	−0.001 (5)
C13	0.055 (4)	0.067 (5)	0.058 (4)	−0.004 (3)	0.005 (3)	−0.002 (3)
C14	0.076 (5)	0.047 (4)	0.045 (3)	−0.003 (3)	−0.004 (3)	0.001 (3)
C15	0.076 (6)	0.126 (8)	0.091 (6)	0.003 (5)	0.028 (4)	−0.021 (5)
C16	0.098 (8)	0.212 (13)	0.097 (7)	0.001 (7)	−0.038 (6)	−0.023 (7)
C17	0.121 (4)	0.090 (4)	0.104 (3)	−0.013 (3)	−0.045 (3)	−0.003 (3)
C18	0.121 (4)	0.090 (4)	0.104 (3)	−0.013 (3)	−0.045 (3)	−0.003 (3)
C19	0.121 (4)	0.090 (4)	0.104 (3)	−0.013 (3)	−0.045 (3)	−0.003 (3)
C20	0.121 (4)	0.090 (4)	0.104 (3)	−0.013 (3)	−0.045 (3)	−0.003 (3)
C21	0.113 (7)	0.086 (6)	0.116 (7)	−0.010 (5)	−0.053 (6)	0.017 (5)
C22	0.098 (7)	0.109 (8)	0.108 (7)	0.006 (5)	−0.041 (5)	0.019 (5)
C23	0.078 (5)	0.057 (5)	0.076 (5)	0.012 (4)	−0.006 (4)	0.001 (4)
C24	0.082 (5)	0.060 (4)	0.053 (4)	−0.001 (4)	−0.015 (4)	0.000 (3)
C25	0.131 (8)	0.058 (5)	0.083 (5)	−0.003 (4)	−0.031 (5)	−0.005 (4)
C26	0.122 (8)	0.066 (5)	0.089 (6)	−0.011 (5)	−0.020 (5)	−0.018 (4)
C27	0.107 (7)	0.079 (6)	0.056 (4)	−0.015 (5)	−0.021 (4)	−0.012 (4)
C28	0.069 (5)	0.074 (5)	0.051 (4)	−0.001 (4)	−0.004 (3)	−0.008 (3)
C29	0.060 (4)	0.057 (4)	0.056 (4)	−0.001 (3)	−0.003 (3)	−0.006 (3)
C30	0.125 (8)	0.107 (7)	0.083 (5)	0.019 (6)	−0.048 (5)	−0.013 (5)

Geometric parameters (Å, º) top

Cd1—O2	2.204 (4)	C9—C10	1.397 (9)
Cd1—O4	2.205 (4)	C9—C14	1.426 (8)
Cd1—O6	2.350 (5)	C10—C11	1.361 (11)
Cd1—O9	2.361 (5)	C10—H10A	0.9300
Cd1—O3	2.500 (5)	C11—C12	1.377 (11)
Cd1—O5	2.538 (5)	C11—H11A	0.9300
Cd1—O10	2.569 (6)	C12—C13	1.360 (9)
N1—C8	1.288 (8)	C12—H12A	0.9300
N1—C5	1.421 (8)	C13—C14	1.416 (9)
N1—H1D	0.8600	C15—H15B	0.9600
O1—C13	1.366 (7)	C15—H15C	0.9600
O1—C15	1.452 (7)	C15—H30A	0.9600
C1—C2	1.488 (11)	C16—C17	1.495 (11)
C1—H1A	0.9600	C16—H16A	0.9600
C1—H1B	0.9600	C16—H16B	0.9600
C1—H1C	0.9600	C16—H16C	0.9600
O2—C14	1.304 (7)	C17—C22	1.330 (11)
N2—C23	1.299 (8)	C17—C18	1.337 (12)
N2—C20	1.407 (9)	C18—C19	1.381 (11)
N2—H2A	0.8600	C18—H18A	0.9300
C2—C7	1.356 (12)	C19—C20	1.376 (12)
C2—C3	1.376 (12)	C19—H19A	0.9300
O3—C28	1.361 (8)	C20—C21	1.334 (11)
O3—C30	1.429 (8)	C21—C22	1.400 (10)
N3—O7	1.220 (7)	C21—H21A	0.9300
N3—O6	1.253 (7)	C22—H22A	0.9300
N3—O5	1.254 (8)	C23—C24	1.397 (9)
C3—C4	1.386 (10)	C23—H23A	0.9300
C3—H3A	0.9300	C24—C29	1.394 (9)
O4—C29	1.299 (7)	C24—C25	1.407 (9)
N4—O8	1.219 (9)	C25—C26	1.362 (10)
N4—O10	1.222 (9)	C25—H25A	0.9300
N4—O9	1.274 (8)	C26—C27	1.390 (10)
C4—C5	1.371 (10)	C26—H26A	0.9300
C4—H4A	0.9300	C27—C28	1.374 (9)
C5—C6	1.389 (9)	C27—H27A	0.9300
C6—C7	1.407 (11)	C28—C29	1.418 (9)
C6—H6A	0.9300	C30—H30B	0.9600
C7—H7A	0.9300	C30—H30C	0.9600
C8—C9	1.404 (9)	C30—H30D	0.9600
C8—H8A	0.9300

O2—Cd1—O4	101.81 (15)	C11—C10—C9	120.6 (7)
O2—Cd1—O6	104.42 (17)	C11—C10—H10A	119.7
O4—Cd1—O6	136.58 (18)	C9—C10—H10A	119.7
O2—Cd1—O9	96.59 (17)	C10—C11—C12	120.6 (8)
O4—Cd1—O9	130.3 (2)	C10—C11—H11A	119.7
O6—Cd1—O9	80.0 (2)	C12—C11—H11A	119.7
O2—Cd1—O3	153.63 (17)	C13—C12—C11	120.9 (8)
O4—Cd1—O3	68.35 (15)	C13—C12—H12A	119.5
O6—Cd1—O3	98.63 (18)	C11—C12—H12A	119.5
O9—Cd1—O3	74.81 (18)	C12—C13—O1	126.0 (6)
O2—Cd1—O5	133.35 (18)	C12—C13—C14	120.9 (6)
O4—Cd1—O5	85.23 (18)	O1—C13—C14	113.1 (5)
O6—Cd1—O5	51.73 (17)	O2—C14—C13	122.1 (5)
O9—Cd1—O5	113.7 (2)	O2—C14—C9	120.5 (6)
O3—Cd1—O5	71.77 (19)	C13—C14—C9	117.3 (6)
O2—Cd1—O10	76.28 (18)	O1—C15—H15B	109.5
O4—Cd1—O10	89.88 (18)	O1—C15—H15C	109.5
O6—Cd1—O10	129.65 (19)	H15B—C15—H15C	109.5
O9—Cd1—O10	50.56 (19)	O1—C15—H30A	109.5
O3—Cd1—O10	79.22 (19)	H15B—C15—H30A	109.5
O5—Cd1—O10	150.3 (2)	H15C—C15—H30A	109.5
C8—N1—C5	127.6 (6)	C17—C16—H16A	109.5
C8—N1—H1D	116.2	C17—C16—H16B	109.5
C5—N1—H1D	116.2	H16A—C16—H16B	109.5
C13—O1—C15	116.0 (5)	C17—C16—H16C	109.5
C2—C1—H1A	109.5	H16A—C16—H16C	109.5
C2—C1—H1B	109.5	H16B—C16—H16C	109.5
H1A—C1—H1B	109.5	C22—C17—C18	115.6 (8)
C2—C1—H1C	109.5	C22—C17—C16	121.5 (9)
H1A—C1—H1C	109.5	C18—C17—C16	122.9 (9)
H1B—C1—H1C	109.5	C17—C18—C19	123.9 (9)
C14—O2—Cd1	129.0 (4)	C17—C18—H18A	118.0
C23—N2—C20	128.0 (7)	C19—C18—H18A	118.0
C23—N2—H2A	116.0	C20—C19—C18	118.9 (9)
C20—N2—H2A	116.0	C20—C19—H19A	120.5
C7—C2—C3	118.3 (8)	C18—C19—H19A	120.5
C7—C2—C1	119.1 (10)	C21—C20—C19	118.2 (9)
C3—C2—C1	122.2 (11)	C21—C20—N2	123.2 (8)
C28—O3—C30	118.5 (6)	C19—C20—N2	118.4 (8)
C28—O3—Cd1	113.5 (4)	C20—C21—C22	120.0 (9)
C30—O3—Cd1	126.9 (5)	C20—C21—H21A	120.0
O7—N3—O6	121.2 (8)	C22—C21—H21A	120.0
O7—N3—O5	121.6 (7)	C17—C22—C21	123.2 (9)
O6—N3—O5	117.2 (6)	C17—C22—H22A	118.4
C2—C3—C4	120.3 (9)	C21—C22—H22A	118.4
C2—C3—H3A	119.9	N2—C23—C24	125.0 (7)
C4—C3—H3A	119.9	N2—C23—H23A	117.5
C29—O4—Cd1	122.5 (4)	C24—C23—H23A	117.5
O8—N4—O10	121.9 (8)	C29—C24—C23	120.6 (6)
O8—N4—O9	122.4 (9)	C29—C24—C25	121.1 (6)
O10—N4—O9	115.7 (7)	C23—C24—C25	118.3 (7)
C5—C4—C3	120.6 (8)	C26—C25—C24	119.4 (7)
C5—C4—H4A	119.7	C26—C25—H25A	120.3
C3—C4—H4A	119.7	C24—C25—H25A	120.3
N3—O5—Cd1	91.0 (4)	C25—C26—C27	121.2 (7)
C4—C5—C6	120.8 (7)	C25—C26—H26A	119.4
C4—C5—N1	118.3 (6)	C27—C26—H26A	119.4
C6—C5—N1	120.9 (7)	C28—C27—C26	119.7 (7)
N3—O6—Cd1	100.1 (4)	C28—C27—H27A	120.2
C5—C6—C7	116.4 (8)	C26—C27—H27A	120.2
C5—C6—H6A	121.8	O3—C28—C27	124.7 (7)
C7—C6—H6A	121.8	O3—C28—C29	114.1 (6)
C2—C7—C6	123.5 (8)	C27—C28—C29	121.2 (7)
C2—C7—H7A	118.3	O4—C29—C24	121.1 (6)
C6—C7—H7A	118.3	O4—C29—C28	121.4 (6)
N1—C8—C9	124.7 (6)	C24—C29—C28	117.5 (6)
N1—C8—H8A	117.6	O3—C30—H30B	109.5
C9—C8—H8A	117.6	O3—C30—H30C	109.5
N4—O9—Cd1	101.2 (5)	H30B—C30—H30C	109.5
C10—C9—C8	119.0 (6)	O3—C30—H30D	109.5
C10—C9—C14	119.7 (7)	H30B—C30—H30D	109.5
C8—C9—C14	121.3 (6)	H30C—C30—H30D	109.5
N4—O10—Cd1	92.5 (5)

O4—Cd1—O2—C14	−75.0 (5)	N1—C8—C9—C14	0.9 (11)
O6—Cd1—O2—C14	70.1 (5)	O8—N4—O10—Cd1	179.5 (7)
O9—Cd1—O2—C14	151.4 (5)	O9—N4—O10—Cd1	2.0 (7)
O3—Cd1—O2—C14	−139.7 (5)	O2—Cd1—O10—N4	−112.0 (5)
O5—Cd1—O2—C14	19.6 (6)	O4—Cd1—O10—N4	145.9 (5)
O10—Cd1—O2—C14	−161.9 (5)	O6—Cd1—O10—N4	−14.4 (6)
O2—Cd1—O3—C28	74.8 (6)	O9—Cd1—O10—N4	−1.2 (4)
O4—Cd1—O3—C28	2.5 (4)	O3—Cd1—O10—N4	77.9 (5)
O6—Cd1—O3—C28	−134.4 (5)	O5—Cd1—O10—N4	65.7 (7)
O9—Cd1—O3—C28	148.5 (5)	C8—C9—C10—C11	−176.4 (7)
O5—Cd1—O3—C28	−89.6 (5)	C14—C9—C10—C11	1.5 (11)
O10—Cd1—O3—C28	96.7 (5)	C9—C10—C11—C12	0.2 (14)
O2—Cd1—O3—C30	−117.5 (6)	C10—C11—C12—C13	−1.5 (14)
O4—Cd1—O3—C30	170.3 (7)	C11—C12—C13—O1	−179.6 (7)
O6—Cd1—O3—C30	33.4 (6)	C11—C12—C13—C14	1.0 (12)
O9—Cd1—O3—C30	−43.7 (6)	C15—O1—C13—C12	11.0 (10)
O5—Cd1—O3—C30	78.2 (6)	C15—O1—C13—C14	−169.6 (6)
O10—Cd1—O3—C30	−95.5 (6)	Cd1—O2—C14—C13	−2.6 (8)
C7—C2—C3—C4	1.7 (15)	Cd1—O2—C14—C9	177.4 (4)
C1—C2—C3—C4	174.4 (9)	C12—C13—C14—O2	−179.3 (6)
O2—Cd1—O4—C29	−155.5 (5)	O1—C13—C14—O2	1.2 (9)
O6—Cd1—O4—C29	78.3 (5)	C12—C13—C14—C9	0.7 (10)
O9—Cd1—O4—C29	−46.1 (6)	O1—C13—C14—C9	−178.7 (5)
O3—Cd1—O4—C29	−1.1 (5)	C10—C9—C14—O2	178.1 (6)
O5—Cd1—O4—C29	71.2 (5)	C8—C9—C14—O2	−4.1 (9)
O10—Cd1—O4—C29	−79.5 (5)	C10—C9—C14—C13	−1.9 (9)
C2—C3—C4—C5	0.9 (14)	C8—C9—C14—C13	175.9 (6)
O7—N3—O5—Cd1	−178.1 (7)	C22—C17—C18—C19	−0.1 (17)
O6—N3—O5—Cd1	0.2 (7)	C16—C17—C18—C19	179.2 (9)
O2—Cd1—O5—N3	71.9 (5)	C17—C18—C19—C20	−2.3 (17)
O4—Cd1—O5—N3	173.6 (5)	C18—C19—C20—C21	3.3 (16)
O6—Cd1—O5—N3	−0.2 (4)	C18—C19—C20—N2	178.1 (9)
O9—Cd1—O5—N3	−54.1 (5)	C23—N2—C20—C21	20.2 (15)
O3—Cd1—O5—N3	−117.6 (5)	C23—N2—C20—C19	−154.3 (9)
O10—Cd1—O5—N3	−105.0 (5)	C19—C20—C21—C22	−1.9 (16)
C3—C4—C5—C6	−0.5 (12)	N2—C20—C21—C22	−176.5 (9)
C3—C4—C5—N1	−179.1 (7)	C18—C17—C22—C21	1.5 (17)
C8—N1—C5—C4	−173.1 (7)	C16—C17—C22—C21	−177.8 (9)
C8—N1—C5—C6	8.2 (10)	C20—C21—C22—C17	−0.5 (17)
O7—N3—O6—Cd1	178.0 (6)	C20—N2—C23—C24	178.5 (8)
O5—N3—O6—Cd1	−0.3 (8)	N2—C23—C24—C29	1.8 (12)
O2—Cd1—O6—N3	−134.3 (4)	N2—C23—C24—C25	−176.7 (7)
O4—Cd1—O6—N3	−8.9 (6)	C29—C24—C25—C26	−1.5 (12)
O9—Cd1—O6—N3	131.4 (5)	C23—C24—C25—C26	177.1 (8)
O3—Cd1—O6—N3	58.6 (5)	C24—C25—C26—C27	1.9 (14)
O5—Cd1—O6—N3	0.2 (4)	C25—C26—C27—C28	−1.2 (13)
O10—Cd1—O6—N3	141.8 (4)	C30—O3—C28—C27	8.4 (11)
C4—C5—C6—C7	−2.2 (11)	Cd1—O3—C28—C27	177.3 (6)
N1—C5—C6—C7	176.4 (6)	C30—O3—C28—C29	−172.4 (6)
C3—C2—C7—C6	−4.7 (16)	Cd1—O3—C28—C29	−3.6 (7)
C1—C2—C7—C6	−177.7 (8)	C26—C27—C28—O3	179.2 (7)
C5—C6—C7—C2	5.0 (13)	C26—C27—C28—C29	0.1 (11)
C5—N1—C8—C9	−172.6 (6)	Cd1—O4—C29—C24	−178.6 (5)
O8—N4—O9—Cd1	−179.7 (7)	Cd1—O4—C29—C28	−0.5 (8)
O10—N4—O9—Cd1	−2.2 (8)	C23—C24—C29—O4	0.1 (10)
O2—Cd1—O9—N4	67.4 (4)	C25—C24—C29—O4	178.6 (7)
O4—Cd1—O9—N4	−44.2 (5)	C23—C24—C29—C28	−178.1 (6)
O6—Cd1—O9—N4	170.9 (5)	C25—C24—C29—C28	0.4 (10)
O3—Cd1—O9—N4	−87.2 (4)	O3—C28—C29—O4	2.9 (9)
O5—Cd1—O9—N4	−148.9 (4)	C27—C28—C29—O4	−177.9 (6)
O10—Cd1—O9—N4	1.2 (4)	O3—C28—C29—C24	−178.9 (6)
N1—C8—C9—C10	178.8 (6)	C27—C28—C29—C24	0.3 (10)

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
N1—H1D···O2	0.86	1.94	2.616 (6)	135
N2—H2A···O4	0.86	1.90	2.577 (7)	135

Experimental details

Crystal data
Chemical formula	[Cd(NO₃)₂(C₁₅H₁₅NO₂)₂]
M_r	718.99
Crystal system, space group	Monoclinic, P2₁/c
Temperature (K)	296
a, b, c (Å)	10.8009 (4), 27.3377 (10), 10.5878 (4)
β (°)	90.208 (2)
V (Å³)	3126.3 (2)
Z	4
Radiation type	Mo Kα
µ (mm⁻¹)	0.76
Crystal size (mm)	0.35 × 0.30 × 0.11

Data collection
Diffractometer	Bruker APEXII area-detector diffractometer
Absorption correction	Multi-scan (SADABS; Sheldrick, 1996)
T_min, T_max	0.765, 0.923
No. of measured, independent and observed [I > 2σ(I)] reflections	31192, 5498, 3112
R_int	0.090
(sin θ/λ)_max (Å⁻¹)	0.595

Refinement
R[F² > 2σ(F²)], wR(F²), S	0.059, 0.178, 0.98
No. of reflections	5498
No. of parameters	389
No. of restraints	3
H-atom treatment	H-atom parameters constrained
Δρ_max, Δρ_min (e Å⁻³)	0.92, −0.75

Computer programs: APEX2 (Bruker, 2006), SAINT (Bruker, 2006), SHELXTL (Sheldrick, 2008).

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
N1—H1D···O2	0.86	1.94	2.616 (6)	135
N2—H2A···O4	0.86	1.90	2.577 (7)	135

References

Bruker (2006). APEX2 and SAINT. Bruker AXS Inc., Madison, Wisconsin, USA. Google Scholar
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Volume 64| Part 11| November 2008| Pages m1482-m1483

doi:10.1107/S1600536808033539

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