catena-Poly[[{2-meth­oxy-6-[(4-methyl­phen­yl)imino­meth­yl]phenolato}­cad­mium(II)]-di-μ2-chlorido-[dimethanol­cadmium(II)]-di-μ2-chlorido-[{2-meth­oxy-6-[(4-methyl­phen­yl)imino­meth­yl]­phenolato}cadmium(II)]-di-μ2-chlorido]

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

doi:10.1107/S1600536808033527

metal-organic compounds

CRYSTALLOGRAPHIC
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ISSN: 2056-9890

Volume 64| Part 11| November 2008| Page m1445

doi:10.1107/S1600536808033527

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catena-Poly[[{2-methoxy-6-[(4-methylphenyl)iminomethyl]phenolato}cadmium(II)]-di-μ₂-chlorido-[dimethanolcadmium(II)]-di-μ₂-chlorido-[{2-methoxy-6-[(4-methylphenyl)iminomethyl]phenolato}cadmium(II)]-di-μ₂-chlorido]

Hui-Duo Xian,^a Hua-Qiong Li,^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 6 October 2008; accepted 15 October 2008; online 18 October 2008)

The structure of the title compound, [Cd₃Cl₆(C₁₅H₁₅NO₂)₂(CH₄O)₂]_n, is based on a layered zigzag polymeric chain along the c axis. The Cd^II ions are linked by double chlorine bridges alternating between one CdCl₄(CH₃OH)₂ and two CdCl₄(C₁₅H₁₅NO₂) octahedral coordination units. Additional intrachain N—H⋯O and O—H⋯Cl hydrogen-bond interactions stabilize this arrangement.

Related literature

For related literature, see: Henkel & Krebs (2004 ); Suen & Wang (2007 ); Wang et al. (2005 ); Zhang & Bu (2008 ); De Girolamo et al. (2007 ).

Experimental

Crystal data

[Cd₃Cl₆(C₁₅H₁₅NO₂)₂(CH₄O)₂]
M_r = 1096.57
Monoclinic, C 2/c
a = 19.7697 (5) Å
b = 13.9554 (3) Å
c = 15.1449 (4) Å
β = 110.4230 (10)°
V = 3915.74 (17) Å³
Z = 4
Mo Kα radiation
μ = 2.07 mm⁻¹
T = 296 (2) K
0.15 × 0.13 × 0.05 mm

Data collection

Bruker APEXII area-detector diffractometer
Absorption correction: multi-scan (SADABS; Sheldrick, 1996 ) T_min = 0.736, T_max = 0.898
13592 measured reflections
3350 independent reflections
2773 reflections with I > 2σ(I)
R_int = 0.033

Refinement

R[F² > 2σ(F²)] = 0.026
wR(F²) = 0.060
S = 1.05
3350 reflections
226 parameters
1 restraint
H atoms treated by a mixture of independent and constrained refinement
Δρ_max = 0.36 e Å⁻³
Δρ_min = −0.34 e Å⁻³

Table 1
Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
N1—H1D⋯O1	0.86	1.88	2.574 (3)	137
O3—H3C⋯Cl3	0.838 (19)	2.38 (2)	3.213 (3)	170 (5)

Data collection: APEX2 (Bruker, 2006 ); cell refinement: SAINT (Bruker, 2006); 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: SHELXL97 (Sheldrick, 2008).

Supporting information

Crystal structure: contains datablocks I, global. DOI: 10.1107/S1600536808033527/at2645sup1.cif

Structure factors: contains datablock I. DOI: 10.1107/S1600536808033527/at2645Isup2.hkl

checkCIF report

Comment top

There has been an increasing interest in the coordination chemistry of cadmium in recent years due to the increased recognition of its role in biological organisms (Henkel & Krebs, 2004), as well as in molecular-based materials (De Girolamo et al., 2007). In the quest for molecular-based materials with interesting properties, much attention has been given to one-, two- and three-dimensional extended solids which involve cadmium (Suen & Wang, 2007; Wang et al., 2005; Zhang & Bu, 2008). Complexes of the type CdX₂ (X = CI or Br) with organic bases typically form one- or two-dimensional halogen-bridged chain compounds with six-coordination octahedral cadmium(II). Here, we describe the synthesis and crystal structure of the cadmium(II) chloride complex with 2-[(4-methylphenylimino)methyl]-6-methoxyphenol.

The crystal structure of the title compound (I) has features of the monoclinic space group C2/c. As illustrated in Fig. 1, the structure comprises an alternating polymeric chain layer along the c axis. The Cd^II ions are linked into an infinite chain by double chlorine bridges, The Cd(1)···Cd(2) and Cd(1)···Cd(1A) distances in the molecule are 3.7087 (3) and 3.8756 (4) Å, respectively.

Related literature top

For related literature, see: Henkel & Krebs (2004); Suen & Wang (2007); Wang et al. (2005); Zhang & Bu (2008); De Girolamo et al. (2007). It would be much more useful to readers if the "Related literature" section had some kind of simple sub-division, so that, instead of just "For related literature, see···" it said, for example, "For general background, see··· For related structures, see···; etc. Please revise this section as indicated.

Experimental top

A solution of CdCl₂ (2 mmol) in methanol (20 ml) was added to a methanol solution (20 ml) of the Schiff base ligand (2 mmol, 0.48 g). Red crystals of (I) were isolated after two weeks.

Computing details top

Data collection: SMART (Bruker, 2004); cell refinement: SAINT (Bruker, 2004); data reduction: SAINT (Bruker, 2004); 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: SHELXL97 (Sheldrick, 2008).

Figures top

Fig. 1. The structure of title compound, with displacement ellipsoids for non-H atoms drawn at the 50% probability level.

catena-Poly[[{2-methoxy-6-[(4-methylphenyl)iminomethyl]phenolato}cadmium(II)]- di-µ₂-chlorido-[dimethanolcadmium(II)]-di-µ₂-chlorido-[{2-methoxy-6- [(4-methylphenyl)iminomethyl]phenolato}cadmium(II)]-di-µ₂-chlorido] top

Crystal data top

[Cd₃Cl₆(C₁₅H₁₅NO₂)₂(CH₄O)₂]	F(000) = 2152
M_r = 1096.57	D_x = 1.860 Mg m⁻³
Monoclinic, C2/c	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: -C 2yc	Cell parameters from 3942 reflections
a = 19.7697 (5) Å	θ = 1.8–25.0°
b = 13.9554 (3) Å	µ = 2.07 mm⁻¹
c = 15.1449 (4) Å	T = 296 K
β = 110.423 (1)°	Block, red
V = 3915.74 (17) Å³	0.15 × 0.13 × 0.05 mm
Z = 4

Data collection top

Bruker APEXII diffractometer	3350 independent reflections
Radiation source: fine-focus sealed tube	2773 reflections with I > 2σ(I)
Graphite monochromator	R_int = 0.033
ω scans	θ_max = 25.0°, θ_min = 1.8°
Absorption correction: multi-scan (SADABS; Sheldrick, 1996)	h = −23→23
T_min = 0.736, T_max = 0.898	k = −16→16
13592 measured reflections	l = −15→18

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)] = 0.026	Hydrogen site location: inferred from neighbouring sites
wR(F²) = 0.060	H atoms treated by a mixture of independent and constrained refinement
S = 1.05	w = 1/[σ²(F_o²) + (0.0247P)² + 2.9063P] where P = (F_o² + 2F_c²)/3
3350 reflections	(Δ/σ)_max = 0.002
226 parameters	Δρ_max = 0.36 e Å⁻³
1 restraint	Δρ_min = −0.34 e Å⁻³

Crystal data top

[Cd₃Cl₆(C₁₅H₁₅NO₂)₂(CH₄O)₂]	V = 3915.74 (17) Å³
M_r = 1096.57	Z = 4
Monoclinic, C2/c	Mo Kα radiation
a = 19.7697 (5) Å	µ = 2.07 mm⁻¹
b = 13.9554 (3) Å	T = 296 K
c = 15.1449 (4) Å	0.15 × 0.13 × 0.05 mm
β = 110.423 (1)°

Data collection top

Bruker APEXII diffractometer	3350 independent reflections
Absorption correction: multi-scan (SADABS; Sheldrick, 1996)	2773 reflections with I > 2σ(I)
T_min = 0.736, T_max = 0.898	R_int = 0.033
13592 measured reflections

Refinement top

R[F² > 2σ(F²)] = 0.026	1 restraint
wR(F²) = 0.060	H atoms treated by a mixture of independent and constrained refinement
S = 1.05	Δρ_max = 0.36 e Å⁻³
3350 reflections	Δρ_min = −0.34 e Å⁻³
226 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	0.542829 (14)	1.284415 (15)	−0.113758 (18)	0.04061 (9)
Cd2	0.5000	1.5000	0.0000	0.04260 (11)
N1	0.46501 (15)	0.97593 (18)	−0.16754 (19)	0.0373 (6)
H1D	0.4710	1.0367	−0.1704	0.045*
O1	0.53998 (12)	1.12806 (14)	−0.10453 (16)	0.0440 (6)
O2	0.65586 (13)	1.21264 (15)	0.01463 (18)	0.0502 (6)
O3	0.41084 (17)	1.48567 (18)	−0.1495 (2)	0.0734 (9)
H3C	0.406 (3)	1.431 (2)	−0.174 (3)	0.110*
Cl1	0.59671 (6)	1.44929 (6)	−0.07253 (8)	0.0632 (3)
Cl2	0.48990 (5)	1.31686 (6)	0.02126 (6)	0.0447 (2)
Cl3	0.41178 (5)	1.27831 (6)	−0.24124 (6)	0.0449 (2)
C1	0.2053 (2)	0.8336 (3)	−0.4388 (3)	0.0702 (12)
H1A	0.2054	0.7648	−0.4396	0.105*
H1B	0.1995	0.8574	−0.5005	0.105*
H1C	0.1661	0.8558	−0.4206	0.105*
C2	0.27528 (19)	0.8692 (2)	−0.3696 (3)	0.0470 (9)
C3	0.3294 (2)	0.8076 (2)	−0.3173 (3)	0.0534 (10)
H3A	0.3228	0.7420	−0.3272	0.064*
C4	0.3923 (2)	0.8400 (2)	−0.2515 (3)	0.0487 (9)
H4A	0.4278	0.7968	−0.2177	0.058*
C5	0.40256 (18)	0.9373 (2)	−0.2360 (2)	0.0361 (8)
C6	0.3509 (2)	1.0007 (2)	−0.2894 (3)	0.0433 (8)
H6A	0.3586	1.0664	−0.2814	0.052*
C7	0.28796 (19)	0.9666 (2)	−0.3544 (3)	0.0469 (9)
H7A	0.2530	1.0098	−0.3891	0.056*
C8	0.51477 (18)	0.9305 (2)	−0.1005 (2)	0.0373 (8)
H8A	0.5095	0.8648	−0.0947	0.045*
C9	0.57599 (18)	0.9754 (2)	−0.0364 (2)	0.0356 (8)
C10	0.6274 (2)	0.9190 (2)	0.0325 (3)	0.0498 (9)
H10A	0.6196	0.8537	0.0365	0.060*
C11	0.6876 (2)	0.9600 (3)	0.0925 (3)	0.0557 (10)
H11A	0.7218	0.9222	0.1367	0.067*
C12	0.6997 (2)	1.0591 (3)	0.0893 (3)	0.0510 (9)
H12A	0.7414	1.0863	0.1315	0.061*
C13	0.65035 (18)	1.1156 (2)	0.0245 (2)	0.0398 (8)
C14	0.58669 (17)	1.0755 (2)	−0.0415 (2)	0.0344 (7)
C15	0.7108 (2)	1.2622 (3)	0.0885 (3)	0.0693 (12)
H15A	0.7460	1.2170	0.1252	0.104*
H15B	0.6893	1.2942	0.1282	0.104*
H15C	0.7338	1.3084	0.0614	0.104*
C16	0.3865 (3)	1.5562 (4)	−0.2154 (3)	0.110 (2)
H16A	0.3495	1.5309	−0.2701	0.165*
H16B	0.4257	1.5796	−0.2329	0.165*
H16C	0.3670	1.6078	−0.1897	0.165*

Atomic displacement parameters (Å²) top

	U¹¹	U²²	U³³	U¹²	U¹³	U²³
Cd1	0.04572 (18)	0.02655 (13)	0.04443 (16)	−0.00188 (10)	0.00927 (13)	−0.00170 (10)
Cd2	0.0499 (3)	0.02725 (18)	0.0422 (2)	0.00221 (15)	0.00547 (19)	−0.00150 (14)
N1	0.0407 (18)	0.0263 (13)	0.0430 (17)	−0.0029 (12)	0.0120 (15)	−0.0001 (12)
O1	0.0432 (15)	0.0273 (11)	0.0472 (14)	0.0025 (10)	−0.0022 (12)	0.0032 (10)
O2	0.0454 (16)	0.0383 (13)	0.0571 (16)	−0.0100 (11)	0.0055 (13)	−0.0043 (11)
O3	0.086 (2)	0.0433 (16)	0.0607 (19)	0.0093 (15)	−0.0132 (17)	−0.0099 (14)
Cl1	0.0737 (7)	0.0389 (5)	0.0889 (8)	−0.0198 (5)	0.0433 (6)	−0.0183 (5)
Cl2	0.0541 (6)	0.0300 (4)	0.0472 (5)	−0.0023 (4)	0.0141 (5)	0.0016 (4)
Cl3	0.0422 (5)	0.0437 (5)	0.0436 (5)	−0.0017 (4)	0.0085 (4)	−0.0031 (4)
C1	0.044 (3)	0.060 (3)	0.087 (3)	−0.001 (2)	−0.002 (2)	−0.008 (2)
C2	0.039 (2)	0.045 (2)	0.053 (2)	−0.0029 (17)	0.0115 (19)	−0.0053 (17)
C3	0.054 (3)	0.0310 (18)	0.065 (3)	−0.0059 (17)	0.009 (2)	−0.0031 (17)
C4	0.047 (2)	0.0344 (19)	0.052 (2)	0.0025 (16)	0.002 (2)	0.0024 (16)
C5	0.036 (2)	0.0332 (17)	0.0384 (19)	−0.0032 (14)	0.0118 (17)	−0.0014 (14)
C6	0.048 (2)	0.0312 (17)	0.048 (2)	−0.0007 (16)	0.0138 (19)	0.0014 (15)
C7	0.038 (2)	0.0418 (19)	0.052 (2)	0.0071 (16)	0.005 (2)	0.0014 (17)
C8	0.043 (2)	0.0285 (16)	0.039 (2)	0.0009 (15)	0.0134 (18)	0.0027 (14)
C9	0.038 (2)	0.0323 (16)	0.0347 (19)	0.0039 (14)	0.0108 (17)	0.0013 (14)
C10	0.059 (3)	0.0365 (19)	0.047 (2)	0.0086 (18)	0.009 (2)	0.0056 (16)
C11	0.055 (3)	0.048 (2)	0.048 (2)	0.0139 (19)	−0.002 (2)	0.0068 (18)
C12	0.040 (2)	0.058 (2)	0.044 (2)	0.0038 (18)	0.0008 (19)	−0.0074 (18)
C13	0.040 (2)	0.0357 (18)	0.040 (2)	−0.0002 (15)	0.0102 (18)	−0.0027 (15)
C14	0.037 (2)	0.0319 (17)	0.0341 (18)	0.0030 (14)	0.0121 (17)	−0.0015 (14)
C15	0.069 (3)	0.059 (2)	0.066 (3)	−0.026 (2)	0.005 (2)	−0.016 (2)
C16	0.148 (6)	0.076 (3)	0.062 (3)	0.018 (3)	−0.018 (3)	−0.001 (3)

Geometric parameters (Å, º) top

Cd1—O1	2.188 (2)	C2—C7	1.387 (5)
Cd1—Cl1	2.5208 (9)	C3—C4	1.371 (5)
Cd1—O2	2.597 (2)	C3—H3A	0.9300
Cd1—Cl3	2.6374 (9)	C4—C5	1.382 (4)
Cd1—Cl2	2.6410 (9)	C4—H4A	0.9300
Cd1—Cl3ⁱ	2.6476 (9)	C5—C6	1.380 (4)
Cd2—O3ⁱⁱ	2.343 (3)	C6—C7	1.375 (5)
Cd2—O3	2.343 (3)	C6—H6A	0.9300
Cd2—Cl2	2.5924 (8)	C7—H7A	0.9300
Cd2—Cl2ⁱⁱ	2.5924 (8)	C8—C9	1.407 (4)
Cd2—Cl1	2.6133 (10)	C8—H8A	0.9300
Cd2—Cl1ⁱⁱ	2.6133 (10)	C9—C10	1.414 (4)
N1—C8	1.306 (4)	C9—C14	1.418 (4)
N1—C5	1.413 (4)	C10—C11	1.348 (5)
N1—H1D	0.8600	C10—H10A	0.9300
O1—C14	1.299 (4)	C11—C12	1.408 (5)
O2—C13	1.372 (4)	C11—H11A	0.9300
O2—C15	1.435 (4)	C12—C13	1.366 (5)
O3—C16	1.365 (5)	C12—H12A	0.9300
O3—H3C	0.838 (19)	C13—C14	1.421 (4)
Cl3—Cd1ⁱ	2.6476 (9)	C15—H15A	0.9600
C1—C2	1.499 (5)	C15—H15B	0.9600
C1—H1A	0.9600	C15—H15C	0.9600
C1—H1B	0.9600	C16—H16A	0.9600
C1—H1C	0.9600	C16—H16B	0.9600
C2—C3	1.385 (5)	C16—H16C	0.9600

O1—Cd1—Cl1	155.83 (6)	C3—C2—C1	122.3 (3)
O1—Cd1—O2	66.56 (7)	C7—C2—C1	120.7 (3)
Cl1—Cd1—O2	89.30 (5)	C4—C3—C2	122.4 (3)
O1—Cd1—Cl3	88.51 (6)	C4—C3—H3A	118.8
Cl1—Cd1—Cl3	115.66 (3)	C2—C3—H3A	118.8
O2—Cd1—Cl3	154.74 (5)	C3—C4—C5	119.3 (3)
O1—Cd1—Cl2	95.48 (6)	C3—C4—H4A	120.3
Cl1—Cd1—Cl2	84.21 (3)	C5—C4—H4A	120.3
O2—Cd1—Cl2	87.50 (6)	C6—C5—C4	119.7 (3)
Cl3—Cd1—Cl2	91.09 (3)	C6—C5—N1	117.7 (3)
O1—Cd1—Cl3ⁱ	92.56 (6)	C4—C5—N1	122.6 (3)
Cl1—Cd1—Cl3ⁱ	89.92 (3)	C7—C6—C5	119.8 (3)
O2—Cd1—Cl3ⁱ	99.00 (6)	C7—C6—H6A	120.1
Cl3—Cd1—Cl3ⁱ	85.55 (3)	C5—C6—H6A	120.1
Cl2—Cd1—Cl3ⁱ	171.21 (3)	C6—C7—C2	121.7 (3)
O3ⁱⁱ—Cd2—O3	180.00 (12)	C6—C7—H7A	119.2
O3ⁱⁱ—Cd2—Cl2	91.64 (7)	C2—C7—H7A	119.2
O3—Cd2—Cl2	88.36 (7)	N1—C8—C9	123.6 (3)
O3ⁱⁱ—Cd2—Cl2ⁱⁱ	88.36 (7)	N1—C8—H8A	118.2
O3—Cd2—Cl2ⁱⁱ	91.64 (7)	C9—C8—H8A	118.2
Cl2—Cd2—Cl2ⁱⁱ	180.000 (1)	C8—C9—C10	119.0 (3)
O3ⁱⁱ—Cd2—Cl1	90.88 (9)	C8—C9—C14	120.7 (3)
O3—Cd2—Cl1	89.12 (9)	C10—C9—C14	120.4 (3)
Cl2—Cd2—Cl1	83.37 (3)	C11—C10—C9	120.0 (3)
Cl2ⁱⁱ—Cd2—Cl1	96.63 (3)	C11—C10—H10A	120.0
O3ⁱⁱ—Cd2—Cl1ⁱⁱ	89.12 (9)	C9—C10—H10A	120.0
O3—Cd2—Cl1ⁱⁱ	90.88 (9)	C10—C11—C12	120.9 (3)
Cl2—Cd2—Cl1ⁱⁱ	96.63 (3)	C10—C11—H11A	119.5
Cl2ⁱⁱ—Cd2—Cl1ⁱⁱ	83.37 (3)	C12—C11—H11A	119.5
Cl1—Cd2—Cl1ⁱⁱ	180.000 (1)	C13—C12—C11	120.3 (3)
C8—N1—C5	127.9 (3)	C13—C12—H12A	119.9
C8—N1—H1D	116.1	C11—C12—H12A	119.9
C5—N1—H1D	116.1	C12—C13—O2	125.7 (3)
C14—O1—Cd1	125.63 (19)	C12—C13—C14	120.9 (3)
C13—O2—C15	117.3 (3)	O2—C13—C14	113.4 (3)
C13—O2—Cd1	112.48 (19)	O1—C14—C9	121.0 (3)
C15—O2—Cd1	128.1 (2)	O1—C14—C13	121.5 (3)
C16—O3—Cd2	126.9 (3)	C9—C14—C13	117.5 (3)
C16—O3—H3C	112 (4)	O2—C15—H15A	109.5
Cd2—O3—H3C	116 (4)	O2—C15—H15B	109.5
Cd1—Cl1—Cd2	92.48 (3)	H15A—C15—H15B	109.5
Cd2—Cl2—Cd1	90.25 (3)	O2—C15—H15C	109.5
Cd1—Cl3—Cd1ⁱ	94.33 (3)	H15A—C15—H15C	109.5
C2—C1—H1A	109.5	H15B—C15—H15C	109.5
C2—C1—H1B	109.5	O3—C16—H16A	109.5
H1A—C1—H1B	109.5	O3—C16—H16B	109.5
C2—C1—H1C	109.5	H16A—C16—H16B	109.5
H1A—C1—H1C	109.5	O3—C16—H16C	109.5
H1B—C1—H1C	109.5	H16A—C16—H16C	109.5
C3—C2—C7	117.0 (3)	H16B—C16—H16C	109.5

Cl1—Cd1—O1—C14	9.2 (3)	Cl2—Cd1—Cl3—Cd1ⁱ	168.17 (2)
O2—Cd1—O1—C14	6.0 (2)	Cl3ⁱ—Cd1—Cl3—Cd1ⁱ	−3.70 (4)
Cl3—Cd1—O1—C14	−169.9 (2)	C7—C2—C3—C4	1.6 (6)
Cl2—Cd1—O1—C14	−78.9 (2)	C1—C2—C3—C4	−177.5 (4)
Cl3ⁱ—Cd1—O1—C14	104.7 (2)	C2—C3—C4—C5	0.3 (6)
O1—Cd1—O2—C13	−5.0 (2)	C3—C4—C5—C6	−2.7 (5)
Cl1—Cd1—O2—C13	176.3 (2)	C3—C4—C5—N1	178.1 (3)
Cl3—Cd1—O2—C13	4.8 (3)	C8—N1—C5—C6	168.6 (3)
Cl2—Cd1—O2—C13	92.1 (2)	C8—N1—C5—C4	−12.3 (5)
Cl3ⁱ—Cd1—O2—C13	−93.9 (2)	C4—C5—C6—C7	3.3 (5)
O1—Cd1—O2—C15	−167.6 (3)	N1—C5—C6—C7	−177.6 (3)
Cl1—Cd1—O2—C15	13.8 (3)	C5—C6—C7—C2	−1.4 (5)
Cl3—Cd1—O2—C15	−157.7 (3)	C3—C2—C7—C6	−1.0 (5)
Cl2—Cd1—O2—C15	−70.5 (3)	C1—C2—C7—C6	178.1 (4)
Cl3ⁱ—Cd1—O2—C15	103.6 (3)	C5—N1—C8—C9	178.9 (3)
Cl2—Cd2—O3—C16	−174.9 (4)	N1—C8—C9—C10	−178.8 (3)
Cl2ⁱⁱ—Cd2—O3—C16	5.1 (4)	N1—C8—C9—C14	0.3 (5)
Cl1—Cd2—O3—C16	−91.5 (4)	C8—C9—C10—C11	177.7 (3)
Cl1ⁱⁱ—Cd2—O3—C16	88.5 (4)	C14—C9—C10—C11	−1.4 (5)
O1—Cd1—Cl1—Cd2	−113.74 (16)	C9—C10—C11—C12	1.6 (6)
O2—Cd1—Cl1—Cd2	−110.81 (6)	C10—C11—C12—C13	−0.4 (6)
Cl3—Cd1—Cl1—Cd2	65.17 (4)	C11—C12—C13—O2	179.8 (3)
Cl2—Cd1—Cl1—Cd2	−23.25 (3)	C11—C12—C13—C14	−0.9 (5)
Cl3ⁱ—Cd1—Cl1—Cd2	150.19 (3)	C15—O2—C13—C12	−12.1 (5)
O3ⁱⁱ—Cd2—Cl1—Cd1	115.31 (7)	Cd1—O2—C13—C12	−176.7 (3)
O3—Cd2—Cl1—Cd1	−64.69 (7)	C15—O2—C13—C14	168.6 (3)
Cl2—Cd2—Cl1—Cd1	23.75 (3)	Cd1—O2—C13—C14	4.0 (3)
Cl2ⁱⁱ—Cd2—Cl1—Cd1	−156.25 (3)	Cd1—O1—C14—C9	173.8 (2)
O3ⁱⁱ—Cd2—Cl2—Cd1	−113.28 (9)	Cd1—O1—C14—C13	−6.4 (4)
O3—Cd2—Cl2—Cd1	66.72 (9)	C8—C9—C14—O1	0.8 (5)
Cl1—Cd2—Cl2—Cd1	−22.59 (3)	C10—C9—C14—O1	179.9 (3)
Cl1ⁱⁱ—Cd2—Cl2—Cd1	157.41 (3)	C8—C9—C14—C13	−178.9 (3)
O1—Cd1—Cl2—Cd2	179.14 (6)	C10—C9—C14—C13	0.1 (5)
Cl1—Cd1—Cl2—Cd2	23.43 (3)	C12—C13—C14—O1	−178.8 (3)
O2—Cd1—Cl2—Cd2	112.98 (5)	O2—C13—C14—O1	0.6 (4)
O1—Cd1—Cl3—Cd1ⁱ	−96.38 (6)	C12—C13—C14—C9	1.0 (5)
Cl1—Cd1—Cl3—Cd1ⁱ	84.07 (3)	O2—C13—C14—C9	−179.6 (3)
O2—Cd1—Cl3—Cd1ⁱ	−105.40 (14)

Symmetry codes: (i) −x+1, y, −z−1/2; (ii) −x+1, −y+3, −z.

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
N1—H1D···O1	0.86	1.88	2.574 (3)	137
O3—H3C···Cl3	0.84 (2)	2.38 (2)	3.213 (3)	170 (5)

Experimental details

Crystal data
Chemical formula	[Cd₃Cl₆(C₁₅H₁₅NO₂)₂(CH₄O)₂]
M_r	1096.57
Crystal system, space group	Monoclinic, C2/c
Temperature (K)	296
a, b, c (Å)	19.7697 (5), 13.9554 (3), 15.1449 (4)
β (°)	110.423 (1)
V (Å³)	3915.74 (17)
Z	4
Radiation type	Mo Kα
µ (mm⁻¹)	2.07
Crystal size (mm)	0.15 × 0.13 × 0.05

Data collection
Diffractometer	Bruker APEXII diffractometer
Absorption correction	Multi-scan (SADABS; Sheldrick, 1996)
T_min, T_max	0.736, 0.898
No. of measured, independent and observed [I > 2σ(I)] reflections	13592, 3350, 2773
R_int	0.033
(sin θ/λ)_max (Å⁻¹)	0.595

Refinement
R[F² > 2σ(F²)], wR(F²), S	0.026, 0.060, 1.05
No. of reflections	3350
No. of parameters	226
No. of restraints	1
H-atom treatment	H atoms treated by a mixture of independent and constrained refinement
Δρ_max, Δρ_min (e Å⁻³)	0.36, −0.34

Computer programs: SMART (Bruker, 2004), SAINT (Bruker, 2004), SHELXS97 (Sheldrick, 2008), SHELXL97 (Sheldrick, 2008), SHELXTL (Sheldrick, 2008).

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
N1—H1D···O1	0.86	1.88	2.574 (3)	136.8
O3—H3C···Cl3	0.838 (19)	2.38 (2)	3.213 (3)	170 (5)

References

Bruker (2006). SAINT and APEX2. Bruker AXS Inc., Madison, Wisconsin, USA. Google Scholar
De Girolamo, J., Reiss, P. & Pron, A. (2007). J. Phys. Chem. C, 111, 14681–14688. Web of Science CrossRef CAS Google Scholar
Henkel, G. & Krebs, B. (2004). Chem. Rev. 104, 801–824. Web of Science CrossRef PubMed CAS 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
Suen, M. C. & Wang, J. C. (2007). J. Coord. Chem. 60, 2197–2205. Web of Science CSD CrossRef CAS Google Scholar
Wang, X. L., Qin, C., Wang, E. B. & Xu, L. (2005). J. Mol. Struct. 749, 45–50. Web of Science CSD CrossRef CAS Google Scholar
Zhang, J. & Bu, X. H. (2008). Chem. Commun. pp. 444–446. Web of Science CSD CrossRef Google Scholar

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Volume 64| Part 11| November 2008| Page m1445

doi:10.1107/S1600536808033527

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