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Acta Crystallogr Sect E Struct Rep Online. 2010 June 1; 66(Pt 6): m663.
Published online 2010 May 15. doi:  10.1107/S1600536810016910
PMCID: PMC2979538

Dichlorido[2-(3,5-dimethyl-1H-pyrazol-1-yl-κN 2)-1,10-phenanthroline-κ2 N,N′]cadmium(II)

Abstract

The asymmetric unit of the title compound, [CdCl2(C17H14N4)], contains two independent mol­ecules in which the CdII ions are in distorted trigonal-bipyramidal CdN3Cl2 coordination environments. In the crystal structure, there is a π–π stacking inter­action involving a pyridine ring and a symmetry-related benzene ring, with a centroid–centroid distance of 3.5088 (19) Å.

Related literature

For a related structure, see: Wang et al. (2009 [triangle]).

An external file that holds a picture, illustration, etc.
Object name is e-66-0m663-scheme1.jpg

Experimental

Crystal data

  • [CdCl2(C17H14N4)]
  • M r = 457.63
  • Triclinic, An external file that holds a picture, illustration, etc.
Object name is e-66-0m663-efi1.jpg
  • a = 10.6268 (12) Å
  • b = 10.7903 (12) Å
  • c = 15.6828 (17) Å
  • α = 84.220 (2)°
  • β = 80.051 (2)°
  • γ = 74.864 (1)°
  • V = 1706.9 (3) Å3
  • Z = 4
  • Mo Kα radiation
  • μ = 1.60 mm−1
  • T = 298 K
  • 0.36 × 0.25 × 0.19 mm

Data collection

  • Bruker SMART APEX CCD diffractometer
  • Absorption correction: multi-scan (SADABS; Sheldrick, 1996 [triangle]) T min = 0.597, T max = 0.751
  • 9365 measured reflections
  • 6562 independent reflections
  • 5658 reflections with I > 2σ(I)
  • R int = 0.017

Refinement

  • R[F 2 > 2σ(F 2)] = 0.029
  • wR(F 2) = 0.078
  • S = 1.05
  • 6562 reflections
  • 437 parameters
  • H-atom parameters constrained
  • Δρmax = 0.44 e Å−3
  • Δρmin = −0.57 e Å−3

Data collection: SMART (Bruker, 1997 [triangle]); cell refinement: SAINT (Bruker, 1997 [triangle]); data reduction: SAINT; program(s) used to solve structure: SHELXTL (Sheldrick, 2008 [triangle]); program(s) used to refine structure: SHELXTL; molecular graphics: SHELXTL; software used to prepare material for publication: SHELXTL.

Supplementary Material

Crystal structure: contains datablocks I, global. DOI: 10.1107/S1600536810016910/lh5038sup1.cif

Structure factors: contains datablocks I. DOI: 10.1107/S1600536810016910/lh5038Isup2.hkl

Additional supplementary materials: crystallographic information; 3D view; checkCIF report

Acknowledgments

This work was supported by the the Shandong Province Natural Science Foundation (Nos ZR2009BM024 and Y2007B42), a Project of Shandong Province Higher Educational Science and Technology Program (No. J09LB08) and the Universities Outstanding Young Teachers Domestic Visiting Scholar Project of Shandong Province.

supplementary crystallographic information

Comment

Derivatives of 1,10-phenanthroline play an important role in modern coordination chemistry and many complexes have been reported with these types of compounds as ligands, but to date only one other structure has been reported which contains the ligand 2-(3,5-Dimethyl-1H-pyrazol-1-yl)-1,10-phenanthroline (Wang et al., 2009). Herein we report the crystal structure of the title complex (I).

The asymmetric unit of the title complex in shown in Fig. 1. There are two independent molecules in the asymmetric unit. The CdII ions are coordinated by three N atoms and two chloride ligands in distorted trigonal bipyramidal geometries. This coordination geometry is essentially the same as in the previously reported CdII complex (Wang et al., 2009). Generally, the CdII ion assumes a six atom coordination mode but the coordination in the title complex may be attributed to the chelation mode of the 2-(3,5-Dimethyl-1H-pyrazol-1-yl)-1,10-phenanthroline ligand. In the crystal structure, there is a π–π stacking interaction involving the pyridine ring and a symmetry related benzene ring with the relevant distances being Cg1···Cg2i = 3.5088 (19) Å and Cg1···Cg2iperp = 3.461 Å (symmetry code: (i) 1-x, 2-y, -z; Cg1 and Cg2 are the centroids of C29-C33/N8 pyridine ring and C25-C30 benzene ring, respectively; Cg1···Cg2iperp is the perpendicular distance from Cg1 ring to Cg2i ring).

Experimental

A 10 ml methanol solution of 2-(3,5-Dimethyl-1H-pyrazol-1-yl)-1,10-phenanthroline (0.0539 g, 0.196 mmol) was added into 10 ml H2O solution containing CdCl22.56H2O (0.0459 g, 0.201 mmol), and the mixed soluton was stirred for a few minutes. The colorless single crystals were obtained after the filtrate had been allowed to stand at room temperature for about a week.

Refinement

All H atoms were placed in calculated positions and refined as riding with C—H = 0.96 Å, Uiso = 1.5Ueq(C) for methyl H and C—H = 0.93 Å, Uiso = 1.2Ueq(C) for other H atoms.

Figures

Fig. 1.
The asymmetric unit of the title compound with the atom-numbering scheme. Displacement ellipsoids are drawn at the 30% probability level.

Crystal data

[CdCl2(C17H14N4)]Z = 4
Mr = 457.63F(000) = 904
Triclinic, P1Dx = 1.781 Mg m3
Hall symbol: -P 1Mo Kα radiation, λ = 0.71073 Å
a = 10.6268 (12) ÅCell parameters from 5552 reflections
b = 10.7903 (12) Åθ = 2.4–28.1°
c = 15.6828 (17) ŵ = 1.60 mm1
α = 84.220 (2)°T = 298 K
β = 80.051 (2)°Block, colorless
γ = 74.864 (1)°0.36 × 0.25 × 0.19 mm
V = 1706.9 (3) Å3

Data collection

Bruker SMART APEX CCD diffractometer6562 independent reflections
Radiation source: fine-focus sealed tube5658 reflections with I > 2σ(I)
graphiteRint = 0.017
[var phi] and ω scansθmax = 26.0°, θmin = 2.0°
Absorption correction: multi-scan (SADABS; Sheldrick, 1996)h = −13→12
Tmin = 0.597, Tmax = 0.751k = −13→12
9365 measured reflectionsl = −14→19

Refinement

Refinement on F2Primary atom site location: structure-invariant direct methods
Least-squares matrix: fullSecondary atom site location: difference Fourier map
R[F2 > 2σ(F2)] = 0.029Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.078H-atom parameters constrained
S = 1.05w = 1/[σ2(Fo2) + (0.0404P)2 + 0.2293P] where P = (Fo2 + 2Fc2)/3
6562 reflections(Δ/σ)max = 0.099
437 parametersΔρmax = 0.44 e Å3
0 restraintsΔρmin = −0.57 e Å3

Special details

Geometry. All esds (except the esd in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell esds are taken into account individually in the estimation of esds in distances, angles and torsion angles; correlations between esds in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell esds is used for estimating esds 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)

xyzUiso*/Ueq
C10.0105 (3)0.8006 (3)0.1063 (2)0.0478 (7)
C2−0.0464 (3)0.9331 (3)0.1130 (2)0.0538 (8)
H2−0.07220.99190.06780.065*
C30.0501 (4)0.7214 (4)0.0295 (2)0.0601 (9)
H3A0.14410.70220.01340.090*
H3B0.00870.7681−0.01800.090*
H3C0.02280.64270.04330.090*
C4−0.1026 (4)1.0890 (3)0.2347 (3)0.0689 (11)
H4A−0.11481.15490.18880.103*
H4B−0.03761.10070.26670.103*
H4C−0.18461.09420.27280.103*
C50.0030 (3)0.8096 (3)0.3282 (2)0.0390 (6)
C6−0.0555 (3)0.8921 (3)0.3966 (2)0.0487 (8)
H6−0.10490.97520.38560.058*
C7−0.0377 (3)0.8472 (3)0.4782 (2)0.0475 (8)
H7−0.07610.90030.52380.057*
C80.0372 (3)0.7223 (3)0.49604 (19)0.0393 (7)
C90.0894 (3)0.6466 (3)0.42457 (18)0.0359 (6)
C100.0607 (3)0.6677 (3)0.58028 (19)0.0466 (8)
H100.02490.71710.62800.056*
C110.1327 (3)0.5477 (3)0.5924 (2)0.0465 (7)
H110.14740.51590.64810.056*
C120.1647 (3)0.5155 (3)0.43745 (18)0.0358 (6)
C130.1877 (3)0.4668 (3)0.52115 (18)0.0399 (7)
C140.2625 (3)0.3394 (3)0.5303 (2)0.0466 (7)
H140.28070.30370.58460.056*
C150.2792 (3)0.3240 (3)0.3788 (2)0.0452 (7)
H150.31060.27440.33080.054*
C160.3081 (3)0.2685 (3)0.4597 (2)0.0500 (8)
H160.35800.18410.46510.060*
C170.3677 (3)0.7559 (3)0.4634 (2)0.0537 (8)
H17A0.42270.79340.49000.081*
H17B0.32780.70120.50570.081*
H17C0.30000.82280.44150.081*
C180.4929 (3)0.5453 (3)0.3842 (2)0.0495 (8)
H180.47450.48310.42660.059*
C190.4497 (3)0.6781 (3)0.3903 (2)0.0428 (7)
C200.5672 (3)0.5232 (3)0.3044 (2)0.0446 (7)
C210.6377 (4)0.3967 (3)0.2680 (3)0.0615 (10)
H21A0.60420.38800.21640.092*
H21B0.62400.32860.31000.092*
H21C0.73040.39210.25410.092*
C220.6184 (3)0.6828 (3)0.1799 (2)0.0416 (7)
C230.6857 (4)0.5978 (3)0.1149 (2)0.0562 (9)
H230.69980.50930.12580.067*
C240.7292 (3)0.6480 (3)0.0362 (2)0.0563 (9)
H240.77250.5928−0.00750.068*
C250.7108 (3)0.7799 (3)0.0189 (2)0.0442 (7)
C260.6429 (3)0.8578 (3)0.08726 (18)0.0378 (6)
C270.7545 (3)0.8400 (4)−0.0627 (2)0.0538 (9)
H270.79750.7893−0.10880.065*
C280.7342 (3)0.9674 (4)−0.0735 (2)0.0508 (8)
H280.76571.0035−0.12670.061*
C290.6659 (3)1.0500 (3)−0.00618 (19)0.0431 (7)
C300.6183 (3)0.9951 (3)0.07433 (18)0.0372 (6)
C310.6410 (3)1.1837 (3)−0.0158 (2)0.0512 (8)
H310.67081.2233−0.06810.061*
C320.5733 (3)1.2558 (3)0.0512 (2)0.0543 (8)
H320.55751.34490.04580.065*
C330.5276 (3)1.1942 (3)0.1286 (2)0.0493 (8)
H330.47911.24450.17360.059*
C34−0.0569 (3)0.9600 (3)0.1969 (2)0.0481 (8)
Cd10.48003 (2)0.95308 (2)0.270728 (13)0.03849 (8)
Cd20.14567 (2)0.54306 (2)0.234337 (13)0.03963 (8)
Cl10.60242 (9)1.01735 (10)0.36848 (6)0.0642 (2)
Cl20.24121 (8)1.03443 (9)0.30304 (5)0.0550 (2)
Cl30.35931 (8)0.52714 (9)0.14531 (6)0.0584 (2)
Cl40.01029 (9)0.42021 (9)0.18715 (5)0.0559 (2)
N1−0.0097 (2)0.8449 (2)0.24047 (17)0.0433 (6)
N20.0327 (3)0.7477 (2)0.18384 (17)0.0463 (6)
N30.0710 (2)0.6911 (2)0.34320 (15)0.0369 (5)
N40.2094 (2)0.4436 (2)0.36694 (15)0.0376 (5)
N50.4937 (2)0.7375 (2)0.31787 (16)0.0433 (6)
N60.5672 (2)0.6416 (2)0.26423 (16)0.0419 (6)
N70.5973 (2)0.8080 (2)0.16565 (15)0.0370 (5)
N80.5498 (2)1.0681 (2)0.14081 (16)0.0409 (6)

Atomic displacement parameters (Å2)

U11U22U33U12U13U23
C10.0436 (17)0.0536 (19)0.0458 (18)−0.0113 (14)−0.0139 (14)0.0090 (15)
C20.0459 (18)0.056 (2)0.055 (2)−0.0098 (15)−0.0118 (15)0.0182 (16)
C30.062 (2)0.068 (2)0.049 (2)−0.0108 (18)−0.0173 (17)0.0014 (17)
C40.076 (3)0.0362 (18)0.079 (3)−0.0009 (17)0.008 (2)0.0052 (18)
C50.0349 (14)0.0368 (15)0.0448 (17)−0.0063 (12)−0.0079 (13)−0.0035 (13)
C60.0477 (18)0.0375 (17)0.058 (2)−0.0049 (14)−0.0033 (15)−0.0133 (15)
C70.0443 (17)0.0455 (18)0.053 (2)−0.0130 (14)0.0031 (15)−0.0191 (15)
C80.0359 (15)0.0468 (17)0.0385 (16)−0.0162 (13)−0.0001 (12)−0.0112 (13)
C90.0327 (14)0.0409 (16)0.0369 (15)−0.0125 (12)−0.0043 (12)−0.0087 (12)
C100.0434 (17)0.064 (2)0.0369 (16)−0.0223 (16)0.0043 (13)−0.0168 (15)
C110.0452 (17)0.067 (2)0.0331 (16)−0.0233 (16)−0.0056 (13)−0.0040 (15)
C120.0320 (14)0.0416 (16)0.0366 (15)−0.0134 (12)−0.0062 (12)−0.0016 (12)
C130.0341 (15)0.0522 (18)0.0371 (16)−0.0176 (13)−0.0062 (12)−0.0004 (13)
C140.0400 (16)0.059 (2)0.0425 (18)−0.0159 (14)−0.0125 (14)0.0110 (15)
C150.0429 (17)0.0401 (17)0.0505 (19)−0.0078 (13)−0.0032 (14)−0.0062 (14)
C160.0419 (17)0.0450 (18)0.062 (2)−0.0092 (14)−0.0122 (16)0.0068 (16)
C170.0515 (19)0.061 (2)0.0455 (19)−0.0177 (16)0.0027 (15)0.0041 (16)
C180.0538 (19)0.0452 (18)0.056 (2)−0.0240 (15)−0.0173 (16)0.0109 (15)
C190.0390 (16)0.0489 (18)0.0430 (17)−0.0175 (13)−0.0064 (13)0.0037 (14)
C200.0441 (17)0.0384 (16)0.056 (2)−0.0122 (13)−0.0169 (15)−0.0023 (14)
C210.079 (3)0.0358 (17)0.072 (2)−0.0122 (17)−0.020 (2)−0.0031 (17)
C220.0387 (16)0.0397 (17)0.0466 (18)−0.0106 (13)−0.0026 (13)−0.0076 (14)
C230.064 (2)0.0377 (17)0.064 (2)−0.0087 (15)0.0013 (18)−0.0145 (16)
C240.060 (2)0.055 (2)0.051 (2)−0.0104 (17)0.0038 (17)−0.0224 (17)
C250.0387 (16)0.0526 (19)0.0415 (17)−0.0109 (14)−0.0017 (13)−0.0128 (14)
C260.0333 (14)0.0460 (17)0.0343 (15)−0.0102 (12)−0.0038 (12)−0.0054 (13)
C270.0504 (19)0.074 (3)0.0352 (17)−0.0124 (17)0.0019 (14)−0.0157 (16)
C280.0451 (18)0.074 (2)0.0319 (16)−0.0166 (16)−0.0009 (13)−0.0011 (15)
C290.0357 (15)0.059 (2)0.0357 (16)−0.0151 (14)−0.0066 (12)0.0013 (14)
C300.0325 (14)0.0450 (16)0.0358 (15)−0.0119 (12)−0.0056 (12)−0.0029 (13)
C310.0485 (18)0.060 (2)0.0466 (19)−0.0204 (16)−0.0090 (15)0.0117 (16)
C320.057 (2)0.0468 (19)0.058 (2)−0.0166 (16)−0.0083 (17)0.0063 (16)
C330.057 (2)0.0434 (18)0.0464 (18)−0.0148 (15)−0.0002 (15)−0.0054 (14)
C340.0359 (16)0.0398 (17)0.063 (2)−0.0065 (13)−0.0025 (15)0.0074 (15)
Cd10.04044 (13)0.03712 (13)0.03636 (13)−0.01020 (9)0.00171 (9)−0.00644 (9)
Cd20.04436 (13)0.03821 (13)0.03451 (13)−0.00638 (9)−0.00465 (9)−0.00639 (9)
Cl10.0600 (5)0.0840 (7)0.0571 (5)−0.0265 (5)−0.0122 (4)−0.0152 (5)
Cl20.0421 (4)0.0694 (6)0.0472 (5)−0.0050 (4)0.0000 (3)−0.0101 (4)
Cl30.0481 (4)0.0586 (5)0.0576 (5)−0.0058 (4)0.0042 (4)0.0072 (4)
Cl40.0632 (5)0.0629 (5)0.0477 (5)−0.0248 (4)−0.0041 (4)−0.0153 (4)
N10.0424 (14)0.0364 (13)0.0478 (15)−0.0027 (11)−0.0101 (12)0.0000 (11)
N20.0522 (15)0.0404 (14)0.0442 (15)−0.0040 (12)−0.0117 (12)−0.0044 (12)
N30.0367 (12)0.0344 (13)0.0393 (13)−0.0067 (10)−0.0065 (10)−0.0048 (10)
N40.0377 (12)0.0359 (13)0.0384 (13)−0.0078 (10)−0.0036 (10)−0.0060 (10)
N50.0473 (14)0.0365 (13)0.0438 (15)−0.0109 (11)0.0015 (12)−0.0039 (11)
N60.0465 (14)0.0344 (13)0.0459 (15)−0.0130 (11)−0.0040 (12)−0.0045 (11)
N70.0377 (12)0.0355 (13)0.0372 (13)−0.0099 (10)0.0001 (10)−0.0071 (10)
N80.0408 (13)0.0401 (14)0.0417 (14)−0.0112 (11)−0.0012 (11)−0.0068 (11)

Geometric parameters (Å, °)

C1—N21.322 (4)C19—N51.321 (4)
C1—C21.407 (5)C20—N61.366 (4)
C1—C31.485 (5)C20—C211.492 (4)
C2—C341.356 (5)C21—H21A0.9600
C2—H20.9300C21—H21B0.9600
C3—H3A0.9600C21—H21C0.9600
C3—H3B0.9600C22—N71.313 (4)
C3—H3C0.9600C22—C231.410 (4)
C4—C341.496 (5)C22—N61.414 (4)
C4—H4A0.9600C23—C241.353 (5)
C4—H4B0.9600C23—H230.9300
C4—H4C0.9600C24—C251.390 (5)
C5—N31.314 (4)C24—H240.9300
C5—C61.415 (4)C25—C261.406 (4)
C5—N11.410 (4)C25—C271.435 (5)
C6—C71.349 (5)C26—N71.354 (4)
C6—H60.9300C26—C301.435 (4)
C7—C81.403 (4)C27—C281.333 (5)
C7—H70.9300C27—H270.9300
C8—C91.401 (4)C28—C291.422 (4)
C8—C101.427 (4)C28—H280.9300
C9—N31.346 (4)C29—C311.395 (5)
C9—C121.445 (4)C29—C301.409 (4)
C10—C111.335 (5)C30—N81.357 (3)
C10—H100.9300C31—C321.357 (5)
C11—C131.434 (4)C31—H310.9300
C11—H110.9300C32—C331.397 (4)
C12—N41.360 (3)C32—H320.9300
C12—C131.401 (4)C33—N81.318 (4)
C13—C141.404 (4)C33—H330.9300
C14—C161.355 (5)C34—N11.372 (4)
C14—H140.9300Cd1—N52.344 (2)
C15—N41.322 (4)Cd1—N72.347 (2)
C15—C161.396 (5)Cd1—N82.386 (3)
C15—H150.9300Cd1—Cl12.4283 (9)
C16—H160.9300Cd1—Cl22.4393 (8)
C17—C191.499 (4)Cd2—N32.348 (2)
C17—H17A0.9600Cd2—N22.353 (3)
C17—H17B0.9600Cd2—N42.365 (2)
C17—H17C0.9600Cd2—Cl32.4254 (9)
C18—C201.366 (5)Cd2—Cl42.4365 (8)
C18—C191.394 (4)N1—N21.376 (3)
C18—H180.9300N5—N61.384 (3)
N2—C1—C2109.0 (3)C24—C23—H23120.8
N2—C1—C3120.3 (3)C22—C23—H23120.8
C2—C1—C3130.6 (3)C23—C24—C25121.7 (3)
C34—C2—C1107.9 (3)C23—C24—H24119.2
C34—C2—H2126.1C25—C24—H24119.2
C1—C2—H2126.1C24—C25—C26116.3 (3)
C1—C3—H3A109.5C24—C25—C27124.8 (3)
C1—C3—H3B109.5C26—C25—C27118.9 (3)
H3A—C3—H3B109.5N7—C26—C25122.2 (3)
C1—C3—H3C109.5N7—C26—C30118.1 (2)
H3A—C3—H3C109.5C25—C26—C30119.7 (3)
H3B—C3—H3C109.5C28—C27—C25121.0 (3)
C34—C4—H4A109.5C28—C27—H27119.5
C34—C4—H4B109.5C25—C27—H27119.5
H4A—C4—H4B109.5C27—C28—C29122.0 (3)
C34—C4—H4C109.5C27—C28—H28119.0
H4A—C4—H4C109.5C29—C28—H28119.0
H4B—C4—H4C109.5C31—C29—C30117.7 (3)
N3—C5—C6121.4 (3)C31—C29—C28123.4 (3)
N3—C5—N1114.9 (2)C30—C29—C28118.9 (3)
C6—C5—N1123.7 (3)N8—C30—C29122.1 (3)
C7—C6—C5118.4 (3)N8—C30—C26118.5 (2)
C7—C6—H6120.8C29—C30—C26119.5 (3)
C5—C6—H6120.8C32—C31—C29119.8 (3)
C6—C7—C8121.6 (3)C32—C31—H31120.1
C6—C7—H7119.2C29—C31—H31120.1
C8—C7—H7119.2C31—C32—C33119.0 (3)
C9—C8—C7116.1 (3)C31—C32—H32120.5
C9—C8—C10118.8 (3)C33—C32—H32120.5
C7—C8—C10125.0 (3)N8—C33—C32123.2 (3)
N3—C9—C8122.3 (3)N8—C33—H33118.4
N3—C9—C12118.0 (2)C32—C33—H33118.4
C8—C9—C12119.7 (3)C2—C34—N1106.0 (3)
C11—C10—C8121.7 (3)C2—C34—C4127.7 (3)
C11—C10—H10119.1N1—C34—C4126.2 (3)
C8—C10—H10119.1N5—Cd1—N766.71 (8)
C10—C11—C13121.3 (3)N5—Cd1—N8136.81 (8)
C10—C11—H11119.4N7—Cd1—N870.12 (8)
C13—C11—H11119.4N5—Cd1—Cl1101.73 (7)
N4—C12—C13122.5 (3)N7—Cd1—Cl1118.21 (6)
N4—C12—C9118.0 (2)N8—Cd1—Cl199.48 (6)
C13—C12—C9119.5 (3)N5—Cd1—Cl298.31 (7)
C12—C13—C14117.4 (3)N7—Cd1—Cl2126.95 (6)
C12—C13—C11118.9 (3)N8—Cd1—Cl2106.32 (6)
C14—C13—C11123.7 (3)Cl1—Cd1—Cl2114.58 (3)
C16—C14—C13119.9 (3)N3—Cd2—N266.81 (8)
C16—C14—H14120.1N3—Cd2—N470.35 (8)
C13—C14—H14120.1N2—Cd2—N4137.15 (8)
N4—C15—C16123.3 (3)N3—Cd2—Cl3120.27 (6)
N4—C15—H15118.4N2—Cd2—Cl399.63 (7)
C16—C15—H15118.4N4—Cd2—Cl3100.85 (6)
C14—C16—C15119.0 (3)N3—Cd2—Cl4124.42 (6)
C14—C16—H16120.5N2—Cd2—Cl497.38 (7)
C15—C16—H16120.5N4—Cd2—Cl4107.40 (6)
C19—C17—H17A109.5Cl3—Cd2—Cl4114.71 (3)
C19—C17—H17B109.5C34—N1—N2110.2 (3)
H17A—C17—H17B109.5C34—N1—C5133.2 (3)
C19—C17—H17C109.5N2—N1—C5116.6 (2)
H17A—C17—H17C109.5C1—N2—N1106.8 (3)
H17B—C17—H17C109.5C1—N2—Cd2133.9 (2)
C20—C18—C19107.4 (3)N1—N2—Cd2118.69 (18)
C20—C18—H18126.3C5—N3—C9120.2 (2)
C19—C18—H18126.3C5—N3—Cd2122.30 (19)
N5—C19—C18110.1 (3)C9—N3—Cd2117.18 (18)
N5—C19—C17119.5 (3)C15—N4—C12117.9 (3)
C18—C19—C17130.4 (3)C15—N4—Cd2125.92 (19)
C18—C20—N6106.0 (3)C12—N4—Cd2116.11 (18)
C18—C20—C21127.8 (3)C19—N5—N6106.0 (2)
N6—C20—C21126.2 (3)C19—N5—Cd1134.7 (2)
C20—C21—H21A109.5N6—N5—Cd1119.24 (17)
C20—C21—H21B109.5C20—N6—N5110.4 (2)
H21A—C21—H21B109.5C20—N6—C22133.3 (3)
C20—C21—H21C109.5N5—N6—C22116.2 (2)
H21A—C21—H21C109.5C22—N7—C26119.7 (2)
H21B—C21—H21C109.5C22—N7—Cd1122.74 (19)
N7—C22—C23121.7 (3)C26—N7—Cd1117.51 (18)
N7—C22—N6114.9 (2)C33—N8—C30118.2 (3)
C23—C22—N6123.5 (3)C33—N8—Cd1126.0 (2)
C24—C23—C22118.4 (3)C30—N8—Cd1115.84 (18)
N2—C1—C2—C340.7 (4)C6—C5—N3—C9−1.8 (4)
C3—C1—C2—C34−176.7 (3)N1—C5—N3—C9−179.9 (2)
N3—C5—C6—C71.4 (5)C6—C5—N3—Cd2171.8 (2)
N1—C5—C6—C7179.2 (3)N1—C5—N3—Cd2−6.3 (3)
C5—C6—C7—C80.4 (5)C8—C9—N3—C50.5 (4)
C6—C7—C8—C9−1.5 (4)C12—C9—N3—C5179.9 (2)
C6—C7—C8—C10179.9 (3)C8—C9—N3—Cd2−173.3 (2)
C7—C8—C9—N31.1 (4)C12—C9—N3—Cd26.1 (3)
C10—C8—C9—N3179.7 (3)N2—Cd2—N3—C51.7 (2)
C7—C8—C9—C12−178.3 (3)N4—Cd2—N3—C5−179.3 (2)
C10—C8—C9—C120.3 (4)Cl3—Cd2—N3—C589.4 (2)
C9—C8—C10—C111.2 (4)Cl4—Cd2—N3—C5−81.2 (2)
C7—C8—C10—C11179.7 (3)N2—Cd2—N3—C9175.4 (2)
C8—C10—C11—C13−1.3 (5)N4—Cd2—N3—C9−5.52 (18)
N3—C9—C12—N4−1.9 (4)Cl3—Cd2—N3—C9−96.85 (19)
C8—C9—C12—N4177.5 (2)Cl4—Cd2—N3—C992.54 (19)
N3—C9—C12—C13178.9 (2)C16—C15—N4—C120.4 (4)
C8—C9—C12—C13−1.7 (4)C16—C15—N4—Cd2−176.6 (2)
N4—C12—C13—C141.4 (4)C13—C12—N4—C15−1.3 (4)
C9—C12—C13—C14−179.4 (2)C9—C12—N4—C15179.5 (3)
N4—C12—C13—C11−177.6 (2)C13—C12—N4—Cd2176.0 (2)
C9—C12—C13—C111.6 (4)C9—C12—N4—Cd2−3.2 (3)
C10—C11—C13—C12−0.1 (4)N3—Cd2—N4—C15−178.5 (3)
C10—C11—C13—C14−179.1 (3)N2—Cd2—N4—C15−177.2 (2)
C12—C13—C14—C16−0.6 (4)Cl3—Cd2—N4—C15−60.0 (2)
C11—C13—C14—C16178.3 (3)Cl4—Cd2—N4—C1560.4 (2)
C13—C14—C16—C15−0.2 (4)N3—Cd2—N4—C124.46 (18)
N4—C15—C16—C140.3 (5)N2—Cd2—N4—C125.7 (2)
C20—C18—C19—N50.3 (4)Cl3—Cd2—N4—C12122.91 (18)
C20—C18—C19—C17−178.7 (3)Cl4—Cd2—N4—C12−116.68 (18)
C19—C18—C20—N6−0.1 (3)C18—C19—N5—N6−0.3 (3)
C19—C18—C20—C21178.4 (3)C17—C19—N5—N6178.8 (3)
N7—C22—C23—C240.1 (5)C18—C19—N5—Cd1−177.2 (2)
N6—C22—C23—C24179.3 (3)C17—C19—N5—Cd11.9 (5)
C22—C23—C24—C251.0 (5)N7—Cd1—N5—C19−179.4 (3)
C23—C24—C25—C26−0.9 (5)N8—Cd1—N5—C19−177.5 (3)
C23—C24—C25—C27179.8 (3)Cl1—Cd1—N5—C1964.7 (3)
C24—C25—C26—N7−0.2 (4)Cl2—Cd1—N5—C19−52.7 (3)
C27—C25—C26—N7179.1 (3)N7—Cd1—N5—N64.00 (19)
C24—C25—C26—C30−179.2 (3)N8—Cd1—N5—N66.0 (3)
C27—C25—C26—C300.1 (4)Cl1—Cd1—N5—N6−111.87 (19)
C24—C25—C27—C28−179.1 (3)Cl2—Cd1—N5—N6130.76 (19)
C26—C25—C27—C281.6 (5)C18—C20—N6—N5−0.1 (3)
C25—C27—C28—C29−1.7 (5)C21—C20—N6—N5−178.6 (3)
C27—C28—C29—C31−178.8 (3)C18—C20—N6—C22−175.3 (3)
C27—C28—C29—C300.0 (5)C21—C20—N6—C226.2 (5)
C31—C29—C30—N80.4 (4)C19—N5—N6—C200.2 (3)
C28—C29—C30—N8−178.5 (3)Cd1—N5—N6—C20177.69 (18)
C31—C29—C30—C26−179.4 (3)C19—N5—N6—C22176.3 (3)
C28—C29—C30—C261.7 (4)Cd1—N5—N6—C22−6.2 (3)
N7—C26—C30—N8−0.6 (4)N7—C22—N6—C20179.7 (3)
C25—C26—C30—N8178.4 (3)C23—C22—N6—C200.5 (5)
N7—C26—C30—C29179.3 (3)N7—C22—N6—N54.7 (4)
C25—C26—C30—C29−1.7 (4)C23—C22—N6—N5−174.5 (3)
C30—C29—C31—C320.1 (4)C23—C22—N7—C26−1.3 (4)
C28—C29—C31—C32179.0 (3)N6—C22—N7—C26179.6 (2)
C29—C31—C32—C33−1.1 (5)C23—C22—N7—Cd1178.0 (2)
C31—C32—C33—N81.8 (5)N6—C22—N7—Cd1−1.1 (4)
C1—C2—C34—N1−1.3 (4)C25—C26—N7—C221.3 (4)
C1—C2—C34—C4175.3 (3)C30—C26—N7—C22−179.7 (3)
C2—C34—N1—N21.4 (3)C25—C26—N7—Cd1−178.0 (2)
C4—C34—N1—N2−175.3 (3)C30—C26—N7—Cd10.9 (3)
C2—C34—N1—C5−178.7 (3)N5—Cd1—N7—C22−1.5 (2)
C4—C34—N1—C54.6 (5)N8—Cd1—N7—C22180.0 (2)
N3—C5—N1—C34−170.7 (3)Cl1—Cd1—N7—C2289.7 (2)
C6—C5—N1—C3411.3 (5)Cl2—Cd1—N7—C22−84.2 (2)
N3—C5—N1—N29.2 (4)N5—Cd1—N7—C26177.9 (2)
C6—C5—N1—N2−168.8 (3)N8—Cd1—N7—C26−0.70 (19)
C2—C1—N2—N10.1 (3)Cl1—Cd1—N7—C26−91.0 (2)
C3—C1—N2—N1177.8 (3)Cl2—Cd1—N7—C2695.15 (19)
C2—C1—N2—Cd2−171.1 (2)C32—C33—N8—C30−1.3 (5)
C3—C1—N2—Cd26.7 (5)C32—C33—N8—Cd1178.8 (2)
C34—N1—N2—C1−0.9 (3)C29—C30—N8—C330.2 (4)
C5—N1—N2—C1179.2 (3)C26—C30—N8—C33180.0 (3)
C34—N1—N2—Cd2171.84 (19)C29—C30—N8—Cd1−179.9 (2)
C5—N1—N2—Cd2−8.1 (3)C26—C30—N8—Cd1−0.1 (3)
N3—Cd2—N2—C1173.9 (3)N5—Cd1—N8—C33178.4 (2)
N4—Cd2—N2—C1172.6 (3)N7—Cd1—N8—C33−179.7 (3)
Cl3—Cd2—N2—C155.0 (3)Cl1—Cd1—N8—C33−63.0 (3)
Cl4—Cd2—N2—C1−61.8 (3)Cl2—Cd1—N8—C3356.2 (3)
N3—Cd2—N2—N13.51 (19)N5—Cd1—N8—C30−1.5 (3)
N4—Cd2—N2—N12.2 (3)N7—Cd1—N8—C300.39 (18)
Cl3—Cd2—N2—N1−115.4 (2)Cl1—Cd1—N8—C30117.09 (19)
Cl4—Cd2—N2—N1127.9 (2)Cl2—Cd1—N8—C30−123.68 (18)

Footnotes

Supplementary data and figures for this paper are available from the IUCr electronic archives (Reference: LH5038).

References

  • Bruker (1997). SMART and SAINT Bruker AXS Inc., Madison, Wisconsin, USA.
  • Sheldrick, G. M. (1996). SADABS University of Göttingen, Germany.
  • Sheldrick, G. M. (2008). Acta Cryst. A64, 112–122. [PubMed]
  • Wang, Y. Q., Meng, L. & Shi, J. M. (2009). Acta Cryst. E65, m1317. [PMC free article] [PubMed]

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