Abstract
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 CdII 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,
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[F 2 > 2σ(F 2)] = 0.026
wR(F 2) = 0.060
S = 1.05
3350 reflections
226 parameters
1 restraint
H atoms treated by a mixture of independent and constrained refinement
Δρmax = 0.36 e Å−3
Δρmin = −0.34 e Å−3
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 ▶).
Supplementary Material
Crystal structure: contains datablocks I, global. DOI: 10.1107/S1600536808033527/at2645sup1.cif
Structure factors: contains datablocks I. DOI: 10.1107/S1600536808033527/at2645Isup2.hkl
Additional supplementary materials: crystallographic information; 3D view; checkCIF report
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) |
supplementary crystallographic information
Comment
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 CdII 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.
Experimental
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.
Refinement
The H atoms bonded to C and N atoms were positioned geometrically and refined using a riding model [aromatic C—H 0.93 Å, methylic C—H = 0.96 Å and N—H = 0.86 Å, Uiso(H) = 1.2 or 1.5Ueq(C, N)]. The H atoms bonded to O atoms were located in a difference Fourier maps and refined with O—H distance restraints of 0.85 (2) and Uiso(H) = 1.5Ueq(O).
Figures
Fig. 1.
The structure of title compound, with displacement ellipsoids for non-H atoms drawn at the 50% probability level.
Crystal data
| [Cd3Cl6(C15H15NO2)2(CH4O)2] | F(000) = 2152 |
| Mr = 1096.57 | Dx = 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
| Bruker APEXII diffractometer | 3350 independent reflections |
| Radiation source: fine-focus sealed tube | 2773 reflections with I > 2σ(I) |
| graphite | Rint = 0.033 |
| ω scans | θmax = 25.0°, θmin = 1.8° |
| Absorption correction: multi-scan (SADABS; Sheldrick, 1996) | h = −23→23 |
| Tmin = 0.736, Tmax = 0.898 | k = −16→16 |
| 13592 measured reflections | l = −15→18 |
Refinement
| 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(Fo2) + (0.0247P)2 + 2.9063P] where P = (Fo2 + 2Fc2)/3 |
| 3350 reflections | (Δ/σ)max = 0.002 |
| 226 parameters | Δρmax = 0.36 e Å−3 |
| 1 restraint | Δρmin = −0.34 e Å−3 |
Special details
| 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)
| x | y | z | Uiso*/Ueq | ||
| 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)
| 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, °)
| 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, °)
| 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) |
Footnotes
Supplementary data and figures for this paper are available from the IUCr electronic archives (Reference: AT2645).
References
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Associated Data
This section collects any data citations, data availability statements, or supplementary materials included in this article.
Supplementary Materials
Crystal structure: contains datablocks I, global. DOI: 10.1107/S1600536808033527/at2645sup1.cif
Structure factors: contains datablocks I. DOI: 10.1107/S1600536808033527/at2645Isup2.hkl
Additional supplementary materials: crystallographic information; 3D view; checkCIF report