Dichlorido[2,2′-(1,10-phenanthrolin-2-ylimino)diethanol]cadmium(II)

Zhang, S.G.; Xie, L.M.

doi:10.1107/S1600536809037465

metal-organic compounds

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ISSN: 2056-9890

Volume 65| Part 10| October 2009| Page m1235

doi:10.1107/S1600536809037465

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Dichlorido[2,2′-(1,10-phenanthrolin-2-ylimino)diethanol]cadmium(II)

Shi Guo Zhang ^a ^* and Long Miao Xie ^b

^aDepartment of Chemistry and Chemical Engineering, Institute of Materials Chemistry, Binzhou University, Binzhou 256603, People's Republic of China, and ^bDepartment of Chemistry, Shandong Normal University, Jinan 250014, People's Republic of China
^*Correspondence e-mail: zhangshiguo1970@yahoo.com.cn

(Received 8 July 2009; accepted 16 September 2009; online 19 September 2009)

In the title complex, [CdCl₂(C₁₆H₁₇N₃O₂)], the metal atom exhibits a distorted trigonal-bipyramidal coordination geometry. O—H⋯O and O—H⋯Cl hydrogen bonds involving hydroxy groups and one of coordinated Cl atoms link complexes in the crystal packing. There is a π–π stacking interaction between adjacent 1,10-phenanthroline rings, with a distance of 3.675 (2) Å between the centroids of the pyridine and benzene rings.

Related literature

For related structures, see: Jin & Li (2009 ); Zhang et al. (2008 ).

Experimental

Crystal data

[CdCl₂(C₁₆H₁₇N₃O₂)]
M_r = 466.63
Monoclinic, P 2₁ /n
a = 7.9435 (15) Å
b = 22.548 (4) Å
c = 9.5216 (18) Å
β = 98.808 (3)°
V = 1685.3 (5) Å³
Z = 4
Mo Kα radiation
μ = 1.63 mm⁻¹
T = 298 K
0.24 × 0.11 × 0.05 mm

Data collection

Bruker SMART APEX CCD diffractometer
Absorption correction: multi-scan (SADABS; Sheldrick, 1996 ) T_min = 0.696, T_max = 0.923
9776 measured reflections
3641 independent reflections
2933 reflections with I > 2σ(I)
R_int = 0.040

Refinement

R[F² > 2σ(F²)] = 0.039
wR(F²) = 0.087
S = 1.03
3641 reflections
217 parameters
2 restraints
H-atom parameters constrained
Δρ_max = 0.54 e Å⁻³
Δρ_min = −0.40 e Å⁻³

Table 1
Selected geometric parameters (Å, °)

Cd1—N3	2.235 (3)
Cd1—O2	2.279 (2)
Cd1—N2	2.470 (3)
Cd1—Cl1	2.4752 (11)
Cd1—Cl2	2.4800 (10)

N3—Cd1—O2	136.77 (9)
N3—Cd1—N2	72.40 (9)
O2—Cd1—N2	78.60 (9)
N3—Cd1—Cl1	106.83 (7)
O2—Cd1—Cl1	112.94 (7)
N2—Cd1—Cl1	110.02 (7)
N3—Cd1—Cl2	98.90 (8)
O2—Cd1—Cl2	90.69 (7)
N2—Cd1—Cl2	150.32 (7)
Cl1—Cd1—Cl2	99.66 (4)

Table 2
Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
O2—H7⋯O1ⁱ	0.85	1.84	2.670 (4)	165
O1—H6⋯Cl1ⁱⁱ	0.85	2.34	3.157 (3)	162
Symmetry codes: (i) $[x+{\script{1\over 2}}, -y+{\script{1\over 2}}, z-{\script{1\over 2}}]$ ; (ii) x, y, z+1.

Data collection: SMART (Bruker, 1997 ); cell refinement: SAINT (Bruker, 1997); 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 and local programs.

Supporting information

Crystal structure: contains datablocks I, global. DOI: 10.1107/S1600536809037465/kp2226sup1.cif

Structure factors: contains datablock I. DOI: 10.1107/S1600536809037465/kp2226Isup2.hkl

checkCIF report

Comment top

Derivatives of 1,10-phenanthroline play an important role in modern coordination chemistry and a lot of complexes have been published with this type of ligands (see Zhang et al., 2008). Although compound 2,2'-(1,10-phenanthrolin-2-ylimino)diethanol has been published (see Jin et al., 2009) but its complex has not been available. Herein we report the crystal structure of Cd^II complex with 2,2'-(1,10-phenanthrolin-2-ylimino)diethanol as the ligand. The Cd1 atom reveals a distorted trigonal bipyramidal coordination (Fig. 1 and Table 1). O—H···O hydrogen bond between hydroxyl groups and O—H···Cl hydrogen bond connect the complexes (Fig. 2 and Table 2). There is a π–π stacking interaction involving symmetry-related 1,10-phenanthroline rings, with the relevant distances being Cg1···Cg2ⁱ = 3.675 (2) Å and Cg1···Cg2ⁱ_perp = 3.509 Å; α is 0.71° [symmetry code: (i) -x, -y, 1 - z; Cg1 and Cg2 are the centroids of C3—C7/N2 ring and C6C7C10C13 ring, respectively; Cg1···Cg2_perp is the perpendicular distance from ring Cg1 to ring Cg2ⁱ; α is the dihedral angle between the Cg1 ring plane and the Cg2 ring plane].

Related literature top

For related structures, see: Jin et al. (2009); Zhang et al. (2008).

Experimental top

10 ml methanol solution of 2,2'-(1,10-phenanthrolin-2-ylimino)diethanol (0.0439 g, 0.155 mmol) was added into 10 ml H₂O solution containing CdCl₂.2.5 H₂O (0.0354 g, 0.155 mmol) and the mixture was stirred for a few m. The colourless single crystals were obtained after the filtrate had been allowed to stand at room temperature for two weeks.

Computing details top

Data collection: SMART (Bruker, 1997); cell refinement: SAINT (Bruker, 1997); data reduction: SAINT (Bruker, 1997); 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) and local programs.

Figures top

	Fig. 1. Structure of title complex with the atom-numbering scheme. Displacement ellipsoids are drawn at the 30% probability level.
	Fig. 2. The crystal structure with hydrogen bonds shown as dashed lines.

Dichlorido[2,2'-(1,10-phenanthrolin-2-ylimino)diethanol]cadmium(II) top

Crystal data top

[CdCl₂(C₁₆H₁₇N₃O₂)]	F(000) = 928
M_r = 466.63	D_x = 1.839 Mg m⁻³
Monoclinic, P2₁/n	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: -P 2yn	Cell parameters from 2277 reflections
a = 7.9435 (15) Å	θ = 2.4–24.0°
b = 22.548 (4) Å	µ = 1.63 mm⁻¹
c = 9.5216 (18) Å	T = 298 K
β = 98.808 (3)°	Prism, colourless
V = 1685.3 (5) Å³	0.24 × 0.11 × 0.05 mm
Z = 4

Data collection top

Bruker SMART APEX CCD diffractometer	3641 independent reflections
Radiation source: fine-focus sealed tube	2933 reflections with I > 2σ(I)
Graphite monochromator	R_int = 0.040
ϕ and ω scans	θ_max = 27.0°, θ_min = 1.8°
Absorption correction: multi-scan (SADABS; Sheldrick, 1996)	h = −10→9
T_min = 0.696, T_max = 0.923	k = −28→24
9776 measured reflections	l = −11→12

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)] = 0.039	Hydrogen site location: inferred from neighbouring sites
wR(F²) = 0.087	H-atom parameters constrained
S = 1.03	w = 1/[σ²(F_o²) + (0.0368P)²] where P = (F_o² + 2F_c²)/3
3641 reflections	(Δ/σ)_max = 0.003
217 parameters	Δρ_max = 0.54 e Å⁻³
2 restraints	Δρ_min = −0.40 e Å⁻³

Crystal data top

[CdCl₂(C₁₆H₁₇N₃O₂)]	V = 1685.3 (5) Å³
M_r = 466.63	Z = 4
Monoclinic, P2₁/n	Mo Kα radiation
a = 7.9435 (15) Å	µ = 1.63 mm⁻¹
b = 22.548 (4) Å	T = 298 K
c = 9.5216 (18) Å	0.24 × 0.11 × 0.05 mm
β = 98.808 (3)°

Data collection top

Bruker SMART APEX CCD diffractometer	3641 independent reflections
Absorption correction: multi-scan (SADABS; Sheldrick, 1996)	2933 reflections with I > 2σ(I)
T_min = 0.696, T_max = 0.923	R_int = 0.040
9776 measured reflections

Refinement top

R[F² > 2σ(F²)] = 0.039	2 restraints
wR(F²) = 0.087	H-atom parameters constrained
S = 1.03	Δρ_max = 0.54 e Å⁻³
3641 reflections	Δρ_min = −0.40 e Å⁻³
217 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
C1	0.1374 (5)	0.21631 (17)	0.8042 (4)	0.0422 (9)
H1A	0.2248	0.1869	0.8330	0.051*
H1B	0.1863	0.2473	0.7526	0.051*
C2	−0.0096 (5)	0.18806 (15)	0.7096 (3)	0.0349 (8)
H2A	−0.0637	0.1594	0.7641	0.042*
H2B	−0.0931	0.2183	0.6761	0.042*
C3	0.1122 (4)	0.10255 (14)	0.5974 (3)	0.0289 (7)
C4	0.1161 (5)	0.07105 (15)	0.7281 (4)	0.0368 (9)
H4	0.0798	0.0894	0.8057	0.044*
C5	0.1724 (5)	0.01476 (16)	0.7386 (4)	0.0386 (9)
H5	0.1720	−0.0059	0.8231	0.046*
C6	0.2315 (4)	−0.01327 (14)	0.6243 (4)	0.0316 (8)
C7	0.2289 (4)	0.02028 (14)	0.4999 (3)	0.0272 (7)
C8	0.0074 (5)	0.19041 (15)	0.4534 (4)	0.0386 (9)
H8A	−0.0969	0.2128	0.4539	0.046*
H8B	−0.0132	0.1620	0.3761	0.046*
C9	0.1446 (5)	0.23235 (16)	0.4243 (4)	0.0483 (10)
H9A	0.1064	0.2550	0.3388	0.058*
H9B	0.1724	0.2598	0.5030	0.058*
C10	0.2929 (5)	−0.07252 (15)	0.6327 (4)	0.0418 (9)
H10	0.2950	−0.0934	0.7172	0.050*
C11	0.3475 (5)	−0.09907 (16)	0.5234 (4)	0.0426 (10)
H11	0.3859	−0.1381	0.5319	0.051*
C12	0.2908 (4)	−0.00865 (14)	0.3824 (4)	0.0298 (8)
C13	0.3472 (4)	−0.06791 (14)	0.3938 (4)	0.0351 (8)
C14	0.4001 (5)	−0.09367 (17)	0.2731 (5)	0.0476 (10)
H14	0.4379	−0.1327	0.2769	0.057*
C15	0.3964 (5)	−0.06231 (18)	0.1520 (5)	0.0523 (11)
H15	0.4297	−0.0796	0.0719	0.063*
C16	0.3424 (5)	−0.00404 (17)	0.1491 (4)	0.0452 (10)
H16	0.3409	0.0176	0.0658	0.054*
Cd1	0.22860 (3)	0.118861 (11)	0.25829 (3)	0.03483 (11)
Cl1	−0.04098 (14)	0.13138 (5)	0.09231 (11)	0.0546 (3)
Cl2	0.43311 (13)	0.15483 (4)	0.10510 (10)	0.0440 (2)
N1	0.0451 (4)	0.15814 (11)	0.5862 (3)	0.0301 (6)
N2	0.1698 (3)	0.07740 (11)	0.4860 (3)	0.0267 (6)
N3	0.2925 (4)	0.02232 (13)	0.2602 (3)	0.0335 (7)
O1	0.0806 (3)	0.24096 (10)	0.9274 (2)	0.0452 (7)
H6	0.0645	0.2146	0.9874	0.068*
O2	0.2902 (3)	0.19779 (11)	0.4069 (3)	0.0488 (7)
H7	0.3766	0.2187	0.3977	0.073*

Atomic displacement parameters (Å²) top

	U¹¹	U²²	U³³	U¹²	U¹³	U²³
C1	0.045 (2)	0.042 (2)	0.038 (2)	0.0009 (18)	0.0019 (18)	−0.0076 (17)
C2	0.037 (2)	0.037 (2)	0.0319 (19)	0.0038 (16)	0.0070 (16)	−0.0047 (15)
C3	0.0278 (18)	0.0306 (18)	0.0274 (18)	−0.0018 (14)	0.0010 (14)	−0.0002 (14)
C4	0.047 (2)	0.038 (2)	0.0260 (18)	−0.0003 (17)	0.0101 (16)	−0.0003 (15)
C5	0.043 (2)	0.041 (2)	0.031 (2)	−0.0045 (18)	0.0050 (16)	0.0087 (16)
C6	0.0280 (19)	0.0268 (18)	0.037 (2)	−0.0029 (14)	−0.0034 (15)	0.0027 (14)
C7	0.0239 (18)	0.0242 (17)	0.0321 (18)	−0.0029 (14)	0.0001 (14)	0.0000 (13)
C8	0.045 (2)	0.037 (2)	0.034 (2)	0.0105 (17)	0.0083 (17)	0.0059 (16)
C9	0.068 (3)	0.034 (2)	0.047 (2)	0.010 (2)	0.022 (2)	0.0033 (17)
C10	0.037 (2)	0.034 (2)	0.052 (2)	0.0017 (17)	0.0003 (19)	0.0122 (17)
C11	0.037 (2)	0.0249 (19)	0.064 (3)	0.0020 (16)	0.003 (2)	0.0088 (18)
C12	0.0255 (18)	0.0251 (17)	0.037 (2)	−0.0037 (14)	−0.0007 (15)	−0.0024 (14)
C13	0.0260 (19)	0.0278 (19)	0.051 (2)	−0.0035 (15)	0.0043 (16)	−0.0070 (16)
C14	0.042 (2)	0.031 (2)	0.071 (3)	−0.0002 (18)	0.013 (2)	−0.016 (2)
C15	0.058 (3)	0.048 (3)	0.055 (3)	−0.006 (2)	0.025 (2)	−0.023 (2)
C16	0.056 (3)	0.045 (2)	0.037 (2)	−0.005 (2)	0.0134 (19)	−0.0097 (17)
Cd1	0.04436 (19)	0.03078 (16)	0.03027 (16)	0.00004 (12)	0.00864 (12)	0.00178 (11)
Cl1	0.0468 (6)	0.0775 (8)	0.0375 (6)	−0.0090 (5)	0.0002 (5)	0.0155 (5)
Cl2	0.0523 (6)	0.0405 (5)	0.0431 (5)	0.0007 (4)	0.0191 (5)	0.0054 (4)
N1	0.0351 (17)	0.0281 (15)	0.0280 (15)	0.0048 (12)	0.0076 (12)	−0.0010 (12)
N2	0.0291 (16)	0.0244 (14)	0.0262 (15)	−0.0020 (12)	0.0026 (12)	0.0003 (11)
N3	0.0387 (17)	0.0314 (16)	0.0307 (16)	−0.0009 (13)	0.0061 (13)	−0.0043 (12)
O1	0.0655 (19)	0.0362 (14)	0.0326 (15)	0.0092 (13)	0.0034 (13)	−0.0036 (11)
O2	0.0503 (17)	0.0341 (14)	0.0693 (19)	−0.0079 (13)	0.0323 (14)	−0.0100 (13)

Geometric parameters (Å, º) top

C1—O1	1.431 (4)	C9—H9A	0.9700
C1—C2	1.503 (5)	C9—H9B	0.9700
C1—H1A	0.9700	C10—C11	1.329 (5)
C1—H1B	0.9700	C10—H10	0.9300
C2—N1	1.476 (4)	C11—C13	1.420 (5)
C2—H2A	0.9700	C11—H11	0.9300
C2—H2B	0.9700	C12—N3	1.359 (4)
C3—N2	1.344 (4)	C12—C13	1.408 (4)
C3—N1	1.360 (4)	C13—C14	1.408 (5)
C3—C4	1.429 (4)	C14—C15	1.349 (6)
C4—C5	1.344 (5)	C14—H14	0.9300
C4—H4	0.9300	C15—C16	1.381 (5)
C5—C6	1.400 (5)	C15—H15	0.9300
C5—H5	0.9300	C16—N3	1.325 (4)
C6—C7	1.403 (4)	C16—H16	0.9300
C6—C10	1.420 (4)	Cd1—N3	2.235 (3)
C7—N2	1.370 (4)	Cd1—O2	2.279 (2)
C7—C12	1.445 (5)	Cd1—N2	2.470 (3)
C8—N1	1.450 (4)	Cd1—Cl1	2.4752 (11)
C8—C9	1.500 (5)	Cd1—Cl2	2.4800 (10)
C8—H8A	0.9700	O1—H6	0.8482
C8—H8B	0.9700	O2—H7	0.8481
C9—O2	1.425 (4)

O1—C1—C2	110.0 (3)	C10—C11—C13	120.0 (3)
O1—C1—H1A	109.7	C10—C11—H11	120.0
C2—C1—H1A	109.7	C13—C11—H11	120.0
O1—C1—H1B	109.7	N3—C12—C13	120.6 (3)
C2—C1—H1B	109.7	N3—C12—C7	118.7 (3)
H1A—C1—H1B	108.2	C13—C12—C7	120.7 (3)
N1—C2—C1	112.0 (3)	C14—C13—C12	117.4 (3)
N1—C2—H2A	109.2	C14—C13—C11	123.0 (3)
C1—C2—H2A	109.2	C12—C13—C11	119.6 (3)
N1—C2—H2B	109.2	C15—C14—C13	120.7 (4)
C1—C2—H2B	109.2	C15—C14—H14	119.6
H2A—C2—H2B	107.9	C13—C14—H14	119.6
N2—C3—N1	120.2 (3)	C14—C15—C16	118.8 (4)
N2—C3—C4	120.9 (3)	C14—C15—H15	120.6
N1—C3—C4	118.8 (3)	C16—C15—H15	120.6
C5—C4—C3	119.7 (3)	N3—C16—C15	122.8 (4)
C5—C4—H4	120.1	N3—C16—H16	118.6
C3—C4—H4	120.1	C15—C16—H16	118.6
C4—C5—C6	121.1 (3)	N3—Cd1—O2	136.77 (9)
C4—C5—H5	119.5	N3—Cd1—N2	72.40 (9)
C6—C5—H5	119.5	O2—Cd1—N2	78.60 (9)
C5—C6—C7	116.7 (3)	N3—Cd1—Cl1	106.83 (7)
C5—C6—C10	122.3 (3)	O2—Cd1—Cl1	112.94 (7)
C7—C6—C10	121.0 (3)	N2—Cd1—Cl1	110.02 (7)
N2—C7—C6	123.3 (3)	N3—Cd1—Cl2	98.90 (8)
N2—C7—C12	120.1 (3)	O2—Cd1—Cl2	90.69 (7)
C6—C7—C12	116.6 (3)	N2—Cd1—Cl2	150.32 (7)
N1—C8—C9	114.7 (3)	Cl1—Cd1—Cl2	99.66 (4)
N1—C8—H8A	108.6	C3—N1—C8	123.9 (3)
C9—C8—H8A	108.6	C3—N1—C2	121.2 (3)
N1—C8—H8B	108.6	C8—N1—C2	114.7 (3)
C9—C8—H8B	108.6	C3—N2—C7	118.2 (3)
H8A—C8—H8B	107.6	C3—N2—Cd1	131.8 (2)
O2—C9—C8	107.6 (3)	C7—N2—Cd1	109.5 (2)
O2—C9—H9A	110.2	C16—N3—C12	119.7 (3)
C8—C9—H9A	110.2	C16—N3—Cd1	121.7 (3)
O2—C9—H9B	110.2	C12—N3—Cd1	118.4 (2)
C8—C9—H9B	110.2	C1—O1—H6	112.3
H9A—C9—H9B	108.5	C9—O2—Cd1	113.5 (2)
C11—C10—C6	122.0 (4)	C9—O2—H7	113.0
C11—C10—H10	119.0	Cd1—O2—H7	118.1
C6—C10—H10	119.0

O1—C1—C2—N1	−175.8 (3)	N1—C3—N2—C7	−176.9 (3)
N2—C3—C4—C5	−2.4 (5)	C4—C3—N2—C7	1.4 (5)
N1—C3—C4—C5	176.0 (3)	N1—C3—N2—Cd1	12.5 (5)
C3—C4—C5—C6	1.6 (5)	C4—C3—N2—Cd1	−169.2 (2)
C4—C5—C6—C7	0.1 (5)	C6—C7—N2—C3	0.3 (5)
C4—C5—C6—C10	179.5 (3)	C12—C7—N2—C3	179.5 (3)
C5—C6—C7—N2	−1.0 (5)	C6—C7—N2—Cd1	172.9 (2)
C10—C6—C7—N2	179.5 (3)	C12—C7—N2—Cd1	−7.9 (3)
C5—C6—C7—C12	179.7 (3)	N3—Cd1—N2—C3	179.4 (3)
C10—C6—C7—C12	0.2 (5)	O2—Cd1—N2—C3	31.8 (3)
N1—C8—C9—O2	65.3 (4)	Cl1—Cd1—N2—C3	−78.6 (3)
C5—C6—C10—C11	179.4 (4)	Cl2—Cd1—N2—C3	102.6 (3)
C7—C6—C10—C11	−1.2 (5)	N3—Cd1—N2—C7	8.15 (19)
C6—C10—C11—C13	0.6 (6)	O2—Cd1—N2—C7	−139.4 (2)
N2—C7—C12—N3	1.4 (5)	Cl1—Cd1—N2—C7	110.14 (19)
C6—C7—C12—N3	−179.3 (3)	Cl2—Cd1—N2—C7	−68.6 (2)
N2—C7—C12—C13	−178.1 (3)	C15—C16—N3—C12	−1.1 (6)
C6—C7—C12—C13	1.2 (5)	C15—C16—N3—Cd1	174.3 (3)
N3—C12—C13—C14	−1.7 (5)	C13—C12—N3—C16	2.2 (5)
C7—C12—C13—C14	177.8 (3)	C7—C12—N3—C16	−177.3 (3)
N3—C12—C13—C11	178.7 (3)	C13—C12—N3—Cd1	−173.3 (2)
C7—C12—C13—C11	−1.7 (5)	C7—C12—N3—Cd1	7.1 (4)
C10—C11—C13—C14	−178.7 (4)	O2—Cd1—N3—C16	−133.4 (3)
C10—C11—C13—C12	0.8 (5)	N2—Cd1—N3—C16	176.4 (3)
C12—C13—C14—C15	0.1 (5)	Cl1—Cd1—N3—C16	70.2 (3)
C11—C13—C14—C15	179.6 (4)	Cl2—Cd1—N3—C16	−32.8 (3)
C13—C14—C15—C16	1.0 (6)	O2—Cd1—N3—C12	42.1 (3)
C14—C15—C16—N3	−0.6 (6)	N2—Cd1—N3—C12	−8.1 (2)
N2—C3—N1—C8	9.4 (5)	Cl1—Cd1—N3—C12	−114.3 (2)
C4—C3—N1—C8	−169.0 (3)	Cl2—Cd1—N3—C12	142.7 (2)
N2—C3—N1—C2	−176.3 (3)	C8—C9—O2—Cd1	47.5 (3)
C4—C3—N1—C2	5.3 (5)	N3—Cd1—O2—C9	−133.1 (2)
C9—C8—N1—C3	−95.7 (4)	N2—Cd1—O2—C9	−84.7 (2)
C9—C8—N1—C2	89.6 (4)	Cl1—Cd1—O2—C9	22.3 (2)
C1—C2—N1—C3	82.0 (4)	Cl2—Cd1—O2—C9	123.1 (2)
C1—C2—N1—C8	−103.1 (3)

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
O2—H7···O1ⁱ	0.85	1.84	2.670 (4)	165
O1—H6···Cl1ⁱⁱ	0.85	2.34	3.157 (3)	162

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

Experimental details

Crystal data
Chemical formula	[CdCl₂(C₁₆H₁₇N₃O₂)]
M_r	466.63
Crystal system, space group	Monoclinic, P2₁/n
Temperature (K)	298
a, b, c (Å)	7.9435 (15), 22.548 (4), 9.5216 (18)
β (°)	98.808 (3)
V (Å³)	1685.3 (5)
Z	4
Radiation type	Mo Kα
µ (mm⁻¹)	1.63
Crystal size (mm)	0.24 × 0.11 × 0.05

Data collection
Diffractometer	Bruker SMART APEX CCD diffractometer
Absorption correction	Multi-scan (SADABS; Sheldrick, 1996)
T_min, T_max	0.696, 0.923
No. of measured, independent and observed [I > 2σ(I)] reflections	9776, 3641, 2933
R_int	0.040
(sin θ/λ)_max (Å⁻¹)	0.639

Refinement
R[F² > 2σ(F²)], wR(F²), S	0.039, 0.087, 1.03
No. of reflections	3641
No. of parameters	217
No. of restraints	2
H-atom treatment	H-atom parameters constrained
Δρ_max, Δρ_min (e Å⁻³)	0.54, −0.40

Computer programs: SMART (Bruker, 1997), SAINT (Bruker, 1997), SHELXTL (Sheldrick, 2008) and local programs.

Selected geometric parameters (Å, º) top

Cd1—N3	2.235 (3)	Cd1—Cl1	2.4752 (11)
Cd1—O2	2.279 (2)	Cd1—Cl2	2.4800 (10)
Cd1—N2	2.470 (3)

N3—Cd1—O2	136.77 (9)	N2—Cd1—Cl1	110.02 (7)
N3—Cd1—N2	72.40 (9)	N3—Cd1—Cl2	98.90 (8)
O2—Cd1—N2	78.60 (9)	O2—Cd1—Cl2	90.69 (7)
N3—Cd1—Cl1	106.83 (7)	N2—Cd1—Cl2	150.32 (7)
O2—Cd1—Cl1	112.94 (7)	Cl1—Cd1—Cl2	99.66 (4)

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
O2—H7···O1ⁱ	0.85	1.84	2.670 (4)	164.9
O1—H6···Cl1ⁱⁱ	0.85	2.34	3.157 (3)	162.0

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

Acknowledgements

The authors thank the Project of Scientific Studies Development of Shandong Provincial Education Department (No. J08LC51) and the Natural Science Foundation of Shandong Province of China (grant No. Y2007B26).

References

Bruker (1997). SMART and SAINT. Bruker AXS Inc., Madison, Wisconsin, USA. Google Scholar
Jin, X. & Li, J. M. (2009). Acta Cryst. E65, o541. Web of Science CSD CrossRef IUCr Journals Google Scholar
Sheldrick, G. M. (1996). SADABS. University of Göttingen, Germany. Google Scholar
Sheldrick, G. M. (2008). Acta Cryst. A64, 112–122. Web of Science CrossRef CAS IUCr Journals Google Scholar
Zhang, S. G., Hu, T. Q. & Li, H. (2008). Acta Cryst. E64, m769. Web of Science CSD CrossRef IUCr Journals Google Scholar