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Acta Cryst. (2007). E63, m2453    [ doi:10.1107/S1600536807041980 ]

Di-[mu]-chlorido-bis(chlorido{2-[(2S)-pyrrolidin-2-yl]-1H-benzimidazole}cadmium(II))

D.-W. Fu and H.-Y. Ye

Abstract top

The title binuclear compound, [Cd2Cl4(C11H12N3)2], was synthesized by the hydrothermal reaction of CdCl2 and the homochiral ligand 2-[(2S)-pyrrolidin-2-yl]-1H-benzimidazole. Each of the two crystallographically independent Cd atoms has a slightly distorted trigonal-bipyramidal geometry and is coordinated by two N atoms from the organic ligand, and by one terminal and two bridging Cl- anions. The crystal structure involves intermolecular N-H...Cl hydrogen bonds. One C atom of a pyrrolidine ring is disordered over two positions; the site occupany factors are ca 0.8 and 0.2.

Comment top

Phenomena such as triboluminescence, second harmonic generation (SHG), piezoelectricity, pyroelectricity and ferroelectricity are only found in noncentrosymmetric bulk materials (Zyss, 1993; Agullo-Lopez et al., 1994; Newnham et al., 1975). There has been very strong interest in employing crystal-engineering strategies to generate materials with desirable properties. Such approaches have succeeded in producing chiral or noncentrosymmetric coordination polymers and organic compounds (Qu et al., 2004). We have focused on the synthesis of noncentrosymmetric coordination compounds by the hydrothermal reaction of the chiral ligand and inoganic salt. Here we report the crystal structure of the title compound prepared from CdCl2 and benzimidazole-derived chiral ligand.

As shown in Fig. 1, the Cd ions are chelated by the chiral organic ligand and thus the compound has to form chiral crystals. Each of the two crystallographically independent pentacoordinated Cd atoms has a slightly distorted trigonal-bipyramidal geometry and is coordinated by two N atoms from the organic ligand, and by one terminal and two bridging Cl− anions. The two Cd centers are bridged by two chlorine atoms to give a dicadmium framework with a Cd—Cd separation of 3.8485 (16) Å and a Cl—Cl distance of 3.472 (2) Å.

Related literature top

For the physical properties of noncentrosymmetric solid materials, see: Zyss (1993); Agullo-Lopez et al. (1994); Newnham et al. (1975); Qu et al. (2004). For synthesis of the organic ligand, see: Aminabhavi et al. (1986).

Experimental top

The homochiral ligand, (S)-2-[pyrrolidin-2-yl]-1H-benzimidazole, was synthesized by the reaction of (S)-pyrrolidine-2-carboxylic acid and benzene-1,2-diamine according to the procedure described in the literature (Aminabhavi et al., 1986). A mixture of S-2-(pyrrolidin-2-yl)-1H-benzimidazole (18.7 mg, 0.1 mmol) and CdCl2 (18.3 mg, 0.1 mmol) and water (1 ml) sealed in a glass tube were kept at 70 °C. Crystals suitable for X-ray analysis were obtained after 3 days.

Refinement top

All H atoms were included in calculated positions with C—H = 0.93–0.97 Å and N—H=0.86 Å and with Uiso(H) = 1.2Ueq(C,N). One of the pyrrolidine rings is disordered with the C10 atom occupying two positions, C10 nad C10', with the occupancy factors of 0.81 (2) and 0.19 (2), respectively.

Computing details top

Data collection: CrystalClear (Rigaku, 2005); cell refinement: CrystalClear (Rigaku, 2005); data reduction: CrystalClear (Rigaku, 2005); program(s) used to solve structure: SHELXS97 (Sheldrick, 1997); program(s) used to refine structure: SHELXL97 (Sheldrick, 1997); molecular graphics: SHELXTL/PC (Sheldrick, 1999); software used to prepare material for publication: SHELXTL/PC (Sheldrick, 1999).

Figures top
[Figure 1] Fig. 1. A view of the title compound with the atomic numbering scheme. Displacement ellipsoids were drawn at the 30% probability level and all hydrogen atoms, except H8a and H19a, were omitted for clarity.
Di-µ-chlorido-bis(chlorido{2-[(2S)-pyrrolidin-2-yl]-1H- benzimidazole}cadmium(II)) top
Crystal data top
[Cd2Cl4(C11H12N3)2]F000 = 728
Mr = 741.09Dx = 1.860 Mg m−3
Monoclinic, P21Mo Kα radiation
λ = 0.71073 Å
Hall symbol: P 2ybCell parameters from 11574 reflections
a = 9.365 (6) Åθ = 3.3–27.4º
b = 8.103 (5) ŵ = 2.03 mm−1
c = 17.691 (12) ÅT = 293 (2) K
β = 99.673 (12)ºPrism, colourless
V = 1323.4 (15) Å30.4 × 0.3 × 0.3 mm
Z = 2
Data collection top
Rigaku Mercury2 CCD
diffractometer		6010 independent reflections
Radiation source: fine-focus sealed tube5622 reflections with I > 2σ(I)
Monochromator: graphiteRint = 0.036
Detector resolution: 13.66 pixels mm-1θmax = 27.5º
T = 293(2) Kθmin = 3.4º
ω scansh = −12→12
Absorption correction: multi-scan
(CrystalClear; Rigaku, 2005)		k = −10→10
Tmin = 0.701, Tmax = 1.000l = −22→22
13823 measured reflections
Refinement top
Refinement on F2Hydrogen site location: inferred from neighbouring sites
Least-squares matrix: fullH-atom parameters constrained
R[F2 > 2σ(F2)] = 0.027  w = 1/[σ2(Fo2) + (0.0194P)2 + 0.0229P]
where P = (Fo2 + 2Fc2)/3
wR(F2) = 0.061(Δ/σ)max = 0.001
S = 1.04Δρmax = 0.57 e Å−3
6010 reflectionsΔρmin = −0.30 e Å−3
317 parametersExtinction correction: none
1 restraintAbsolute structure: Flack (1983)
Primary atom site location: structure-invariant direct methodsFlack parameter: −0.03 (2)
Secondary atom site location: difference Fourier map
Crystal data top
[Cd2Cl4(C11H12N3)2]V = 1323.4 (15) Å3
Mr = 741.09Z = 2
Monoclinic, P21Mo Kα
a = 9.365 (6) ŵ = 2.03 mm−1
b = 8.103 (5) ÅT = 293 (2) K
c = 17.691 (12) Å0.4 × 0.3 × 0.3 mm
β = 99.673 (12)º
Data collection top
Rigaku Mercury2 CCD
diffractometer		6010 independent reflections
Absorption correction: multi-scan
(CrystalClear; Rigaku, 2005)		5622 reflections with I > 2σ(I)
Tmin = 0.701, Tmax = 1.000Rint = 0.036
13823 measured reflections
Refinement top
R[F2 > 2σ(F2)] = 0.027H-atom parameters constrained
wR(F2) = 0.061Δρmax = 0.57 e Å−3
S = 1.04Δρmin = −0.30 e Å−3
6010 reflectionsAbsolute structure: Flack (1983)
317 parametersFlack parameter: −0.03 (2)
1 restraint
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
xyzUiso*/UeqOcc. (<1)
Cd10.89212 (3)0.09969 (3)0.681550 (14)0.03784 (7)
Cd20.70149 (3)−0.19423 (3)0.803532 (14)0.03883 (7)
Cl10.94116 (11)−0.02794 (13)0.81846 (6)0.0536 (3)
Cl20.64668 (9)−0.04558 (12)0.67049 (5)0.0442 (2)
Cl31.03862 (11)−0.05990 (11)0.60033 (5)0.0499 (2)
Cl40.55426 (12)−0.04372 (12)0.88338 (6)0.0538 (2)
N10.8156 (3)0.2880 (3)0.57844 (15)0.0387 (6)
H1A0.85860.23800.54280.046*
N20.9917 (3)0.3464 (3)0.72100 (14)0.0341 (6)
N31.0317 (3)0.6107 (4)0.69852 (15)0.0389 (6)
H3A1.02330.70520.67610.047*
N40.8371 (3)−0.4053 (4)0.88192 (15)0.0398 (6)
H4C0.9229−0.40630.86550.048*
N50.5980 (3)−0.4390 (3)0.76447 (15)0.0359 (7)
N60.5622 (3)−0.7033 (4)0.78519 (16)0.0403 (7)
H6A0.5742−0.79960.80570.048*
C10.4788 (4)−0.4917 (4)0.71093 (19)0.0372 (8)
C20.3925 (4)−0.4088 (6)0.6516 (2)0.0499 (9)
H2A0.4059−0.29690.64340.060*
C30.2868 (4)−0.4999 (6)0.6066 (2)0.0522 (10)
H3B0.2275−0.44760.56620.063*
C40.2664 (4)−0.6681 (6)0.6188 (2)0.0504 (10)
H4A0.1945−0.72500.58640.061*
C50.3504 (4)−0.7521 (5)0.6781 (2)0.0478 (9)
H5A0.3363−0.86340.68740.057*
C60.4568 (4)−0.6603 (4)0.7237 (2)0.0389 (8)
C70.6417 (4)−0.5683 (4)0.80687 (18)0.0344 (8)
C80.7681 (4)−0.5709 (4)0.87137 (19)0.0400 (8)
H8A0.8393−0.65130.85940.048*
C90.7265 (5)−0.6156 (6)0.9492 (2)0.0632 (12)0.83 (2)
H9A0.6288−0.65920.94270.076*0.83 (2)
H9B0.7927−0.69710.97570.076*0.83 (2)
C9'0.7265 (5)−0.6156 (6)0.9492 (2)0.0632 (12)0.17 (2)
H9'A0.6271−0.58490.95120.076*0.17 (2)
H9'B0.7386−0.73280.95960.076*0.17 (2)
C100.7372 (11)−0.4563 (12)0.9930 (3)0.067 (3)0.83 (2)
H10A0.6478−0.39390.98140.080*0.83 (2)
H10B0.7588−0.47611.04790.080*0.83 (2)
C10'0.827 (6)−0.520 (3)1.0028 (14)0.060 (11)0.17 (2)
H10C0.9152−0.58191.01880.072*0.17 (2)
H10D0.7845−0.49501.04790.072*0.17 (2)
C110.8590 (5)−0.3676 (6)0.9658 (2)0.0608 (12)0.83 (2)
H11A0.8537−0.24980.97470.073*0.83 (2)
H11B0.9520−0.40840.99150.073*0.83 (2)
C11'0.8590 (5)−0.3676 (6)0.9658 (2)0.0608 (12)0.17 (2)
H11C0.9581−0.33360.98400.073*0.17 (2)
H11D0.7944−0.28010.97620.073*0.17 (2)
C121.0924 (3)0.4106 (4)0.78235 (18)0.0330 (7)
C131.1658 (4)0.3332 (5)0.8477 (2)0.0488 (10)
H13A1.14990.22290.85820.059*
C141.2641 (5)0.4293 (6)0.8966 (2)0.0565 (11)
H14A1.31550.38090.94050.068*
C151.2880 (4)0.5930 (6)0.8813 (2)0.0527 (10)
H15A1.35530.65200.91560.063*
C161.2163 (4)0.6723 (5)0.8167 (2)0.0479 (10)
H16A1.23200.78270.80640.057*
C171.1176 (4)0.5762 (4)0.76791 (18)0.0360 (7)
C180.9634 (4)0.4698 (4)0.67212 (18)0.0321 (7)
C190.8754 (4)0.4578 (4)0.59312 (18)0.0341 (7)
H19A0.94020.48040.55630.041*
C200.7473 (4)0.5766 (5)0.5758 (2)0.0531 (10)
H20A0.77570.67930.55430.064*
H20B0.70660.60060.62160.064*
C210.6403 (4)0.4832 (5)0.5179 (2)0.0514 (10)
H21A0.54220.52390.51560.062*
H21B0.66640.48890.46720.062*
C220.6568 (4)0.3081 (6)0.5497 (2)0.0472 (8)
H22A0.60210.29450.59130.057*
H22B0.62310.22780.51010.057*
Atomic displacement parameters (Å2) top
U11U22U33U12U13U23
Cd10.04699 (14)0.02405 (12)0.04211 (14)−0.00259 (11)0.00645 (10)0.00146 (10)
Cd20.05097 (15)0.02408 (12)0.04213 (14)−0.00421 (11)0.00980 (11)−0.00005 (10)
Cl10.0559 (6)0.0497 (6)0.0501 (5)−0.0185 (5)−0.0057 (4)0.0168 (5)
Cl20.0464 (5)0.0394 (5)0.0442 (5)−0.0079 (4)−0.0002 (4)0.0072 (4)
Cl30.0707 (6)0.0331 (4)0.0523 (5)0.0026 (4)0.0285 (5)0.0066 (4)
Cl40.0748 (6)0.0339 (5)0.0594 (6)0.0037 (5)0.0305 (5)0.0009 (4)
N10.0454 (16)0.0296 (14)0.0396 (15)0.0028 (13)0.0031 (12)−0.0069 (13)
N20.0406 (15)0.0281 (15)0.0321 (14)−0.0051 (12)0.0015 (12)0.0026 (11)
N30.0501 (16)0.0257 (14)0.0388 (15)−0.0055 (15)0.0017 (12)0.0033 (14)
N40.0415 (15)0.0361 (14)0.0431 (15)−0.0023 (15)0.0108 (12)0.0015 (14)
N50.0498 (17)0.0247 (15)0.0336 (15)−0.0022 (12)0.0082 (12)−0.0002 (11)
N60.0535 (17)0.0223 (13)0.0452 (16)−0.0026 (15)0.0084 (13)0.0002 (14)
C10.0413 (19)0.0369 (18)0.0348 (18)−0.0063 (16)0.0101 (14)−0.0011 (15)
C20.052 (2)0.047 (2)0.050 (2)−0.007 (2)0.0064 (17)0.012 (2)
C30.045 (2)0.068 (3)0.042 (2)−0.002 (2)0.0037 (17)0.007 (2)
C40.040 (2)0.068 (3)0.045 (2)−0.016 (2)0.0108 (16)−0.014 (2)
C50.052 (2)0.037 (2)0.058 (2)−0.0125 (18)0.0189 (18)−0.0133 (18)
C60.0426 (19)0.034 (2)0.0428 (19)−0.0035 (15)0.0161 (15)−0.0043 (15)
C70.045 (2)0.0286 (17)0.0333 (17)−0.0022 (15)0.0158 (15)0.0020 (14)
C80.051 (2)0.0294 (17)0.0381 (18)−0.0009 (16)0.0027 (15)−0.0003 (14)
C90.086 (3)0.058 (3)0.043 (2)−0.027 (2)0.003 (2)0.012 (2)
C9'0.086 (3)0.058 (3)0.043 (2)−0.027 (2)0.003 (2)0.012 (2)
C100.089 (5)0.076 (6)0.038 (3)−0.021 (4)0.019 (3)−0.006 (3)
C10'0.11 (3)0.041 (15)0.029 (12)0.020 (16)−0.002 (14)0.000 (10)
C110.079 (3)0.054 (3)0.045 (2)−0.019 (2)−0.002 (2)−0.0026 (19)
C11'0.079 (3)0.054 (3)0.045 (2)−0.019 (2)−0.002 (2)−0.0026 (19)
C120.0392 (17)0.0326 (18)0.0283 (16)−0.0026 (14)0.0085 (13)0.0002 (13)
C130.055 (2)0.048 (2)0.0392 (19)−0.0135 (18)−0.0050 (16)0.0118 (17)
C140.063 (3)0.065 (3)0.037 (2)−0.015 (2)−0.0062 (18)0.0075 (19)
C150.052 (2)0.068 (3)0.0374 (19)−0.017 (2)0.0045 (16)−0.012 (2)
C160.051 (2)0.039 (2)0.053 (2)−0.0126 (17)0.0070 (18)−0.0086 (18)
C170.0454 (18)0.0308 (18)0.0328 (17)−0.0022 (16)0.0097 (14)−0.0050 (14)
C180.0384 (18)0.0268 (16)0.0319 (16)−0.0034 (14)0.0088 (14)0.0010 (14)
C190.0390 (17)0.0338 (17)0.0305 (17)−0.0015 (14)0.0086 (13)0.0017 (14)
C200.063 (2)0.034 (2)0.059 (2)0.0101 (19)0.0006 (19)0.0048 (18)
C210.044 (2)0.056 (3)0.051 (2)0.0107 (19)−0.0026 (16)0.0069 (19)
C220.0424 (19)0.048 (2)0.048 (2)−0.003 (2)−0.0006 (15)0.000 (2)
Geometric parameters (Å, °) top
Cd1—N22.266 (3)C5—C61.388 (5)
Cd1—N12.394 (3)C5—H5A0.9300
Cd1—Cl32.5063 (14)C7—C81.500 (5)
Cd1—Cl22.5605 (16)C8—C91.536 (5)
Cd1—Cl12.6026 (18)C8—H8A0.9800
Cd1—Cd23.8485 (16)C9—C101.500 (9)
Cd2—N52.264 (3)C9—H9A0.9700
Cd2—N42.422 (3)C9—H9B0.9700
Cd2—Cl42.4574 (14)C10—C111.495 (7)
Cd2—Cl12.5931 (16)C10—H10A0.9700
Cd2—Cl22.6169 (17)C10—H10B0.9700
Cl1—Cl23.472 (2)C10'—H10C0.9700
N1—C191.492 (4)C10'—H10D0.9700
N1—C221.497 (4)C11—H11A0.9700
N1—H1A0.9002C11—H11B0.9700
N2—C181.319 (4)C12—C131.391 (5)
N2—C121.412 (4)C12—C171.393 (5)
N3—C181.353 (4)C13—C141.391 (6)
N3—C171.379 (4)C13—H13A0.9300
N3—H3A0.8600C14—C151.379 (7)
N4—C81.488 (5)C14—H14A0.9299
N4—C111.495 (5)C15—C161.382 (6)
N4—H4C0.9001C15—H15A0.9300
N5—C71.313 (4)C16—C171.392 (5)
N5—C11.404 (4)C16—H16A0.9300
N6—C71.343 (4)C18—C191.502 (4)
N6—C61.384 (4)C19—C201.529 (5)
N6—H6A0.8600C19—H19A0.9800
C1—C21.386 (5)C20—C211.511 (5)
C1—C61.406 (5)C20—H20A0.9700
C2—C31.376 (6)C20—H20B0.9701
C2—H2A0.9300C21—C221.525 (6)
C3—C41.398 (6)C21—H21A0.9700
C3—H3B0.9300C21—H21B0.9699
C4—C51.380 (6)C22—H22A0.9700
C4—H4A0.9300C22—H22B0.9701
N2—Cd1—N174.18 (10)N6—C6—C1105.5 (3)
N2—Cd1—Cl3113.28 (8)C5—C6—C1122.5 (4)
N1—Cd1—Cl390.84 (8)N5—C7—N6112.5 (3)
N2—Cd1—Cl2138.31 (7)N5—C7—C8125.2 (3)
N1—Cd1—Cl294.86 (8)N6—C7—C8122.3 (3)
Cl3—Cd1—Cl2106.85 (5)N4—C8—C7110.7 (3)
N2—Cd1—Cl193.71 (8)N4—C8—C9105.7 (3)
N1—Cd1—Cl1161.07 (7)C7—C8—C9113.5 (3)
Cl3—Cd1—Cl1107.49 (5)N4—C8—H8A109.3
Cl2—Cd1—Cl184.50 (3)C7—C8—H8A108.9
N2—Cd1—Cd2125.37 (7)C9—C8—H8A108.7
N1—Cd1—Cd2135.57 (7)C10—C9—C8104.8 (4)
Cl3—Cd1—Cd2110.63 (5)C10—C9—H9A110.8
Cl2—Cd1—Cd242.55 (3)C8—C9—H9A110.8
Cl1—Cd1—Cd242.11 (3)C10—C9—H9B110.8
N5—Cd2—N473.29 (11)C8—C9—H9B110.8
N5—Cd2—Cl4110.95 (8)H9A—C9—H9B108.9
N4—Cd2—Cl4108.18 (8)C11—C10—C9103.6 (5)
N5—Cd2—Cl1143.62 (8)C11—C10—H10A111.0
N4—Cd2—Cl186.97 (8)C9—C10—H10A111.0
Cl4—Cd2—Cl1104.08 (5)C11—C10—H10B111.0
N5—Cd2—Cl296.87 (8)C9—C10—H10B111.0
N4—Cd2—Cl2147.63 (7)H10A—C10—H10B109.0
Cl4—Cd2—Cl2104.14 (5)H10C—C10'—H10D108.3
Cl1—Cd2—Cl283.57 (4)N4—C11—C10103.7 (4)
N5—Cd2—Cd1125.88 (7)N4—C11—H11A111.0
N4—Cd2—Cd1120.66 (8)C10—C11—H11A111.0
Cl4—Cd2—Cd1111.91 (5)N4—C11—H11B111.0
Cl1—Cd2—Cd142.30 (3)C10—C11—H11B111.0
Cl2—Cd2—Cd141.42 (3)H11A—C11—H11B109.0
Cd2—Cl1—Cd195.59 (4)C13—C12—C17120.7 (3)
Cd2—Cl1—Cl248.51 (3)C13—C12—N2130.2 (3)
Cd1—Cl1—Cl247.23 (3)C17—C12—N2109.0 (3)
Cd1—Cl2—Cd296.03 (3)C12—C13—C14116.6 (4)
Cd1—Cl2—Cl148.26 (4)C12—C13—H13A121.8
Cd2—Cl2—Cl147.92 (3)C14—C13—H13A121.6
C19—N1—C22106.4 (3)C15—C14—C13121.9 (4)
C19—N1—Cd1113.56 (19)C15—C14—H14A119.4
C22—N1—Cd1118.7 (2)C13—C14—H14A118.7
C19—N1—H1A109.8C14—C15—C16122.5 (4)
C22—N1—H1A110.3C14—C15—H15A118.8
Cd1—N1—H1A97.7C16—C15—H15A118.8
C18—N2—C12105.0 (3)C15—C16—C17115.6 (4)
C18—N2—Cd1116.1 (2)C15—C16—H16A122.6
C12—N2—Cd1138.5 (2)C17—C16—H16A121.8
C18—N3—C17107.9 (3)N3—C17—C16131.8 (4)
C18—N3—H3A126.2N3—C17—C12105.5 (3)
C17—N3—H3A125.9C16—C17—C12122.7 (3)
C8—N4—C11107.0 (3)N2—C18—N3112.5 (3)
C8—N4—Cd2112.98 (19)N2—C18—C19125.4 (3)
C11—N4—Cd2113.3 (3)N3—C18—C19122.0 (3)
C8—N4—H4C110.1N1—C19—C18110.7 (3)
C11—N4—H4C110.0N1—C19—C20106.7 (3)
Cd2—N4—H4C103.5C18—C19—C20115.8 (3)
C7—N5—C1106.2 (3)N1—C19—H19A108.2
C7—N5—Cd2116.6 (2)C18—C19—H19A107.6
C1—N5—Cd2136.3 (2)C20—C19—H19A107.6
C7—N6—C6107.9 (3)C21—C20—C19103.2 (3)
C7—N6—H6A126.2C21—C20—H20A111.0
C6—N6—H6A125.9C19—C20—H20A111.1
C2—C1—N5131.3 (3)C21—C20—H20B110.9
C2—C1—C6120.7 (4)C19—C20—H20B111.4
N5—C1—C6107.9 (3)H20A—C20—H20B109.1
C3—C2—C1116.7 (4)C20—C21—C22101.6 (3)
C3—C2—H2A122.3C20—C21—H21A111.9
C1—C2—H2A121.0C22—C21—H21A111.6
C2—C3—C4122.5 (4)C20—C21—H21B111.2
C2—C3—H3B118.6C22—C21—H21B111.1
C4—C3—H3B118.9H21A—C21—H21B109.2
C5—C4—C3121.5 (4)N1—C22—C21105.0 (3)
C5—C4—H4A119.1N1—C22—H22A110.6
C3—C4—H4A119.4C21—C22—H22A110.6
C4—C5—C6116.1 (4)N1—C22—H22B110.9
C4—C5—H5A122.2C21—C22—H22B110.9
C6—C5—H5A121.8H22A—C22—H22B108.9
N6—C6—C5132.0 (4)
Hydrogen-bond geometry (Å, °) top
D—H···AD—HH···AD···AD—H···A
N3—H3A···Cl3i0.862.353.191 (3)168
N6—H6A···Cl4ii0.862.433.267 (4)164
Symmetry codes: (i) x, y+1, z; (ii) x, y−1, z.
Table 1
Selected geometric parameters (Å) top
Cd1—N22.266 (3)Cd1—Cl12.6026 (18)
Cd1—N12.394 (3)Cd1—Cd23.8485 (16)
Cd1—Cl32.5063 (14)Cl1—Cl23.472 (2)
Cd1—Cl22.5605 (16)
Table 2
Hydrogen-bond geometry (Å, °) top
D—H···AD—HH···AD···AD—H···A
N3—H3A···Cl3i0.862.353.191 (3)168
N6—H6A···Cl4ii0.862.433.267 (4)164
Symmetry codes: (i) x, y+1, z; (ii) x, y−1, z.
Acknowledgements top

This work was supported by a start-up grant from SEU XRG.

references
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