catena-Poly[[(benzoato-κ2O,O′)chloridocadmium(II)]-μ-2,2′-diphenyl-1,1′-(butane-1,4-di­yl)diimidazole-κ2N3:N3′]

Liu, Y.-Y.; Ma, J.-F.; Zhang, L.-P.

doi:10.1107/S1600536807036628

Buy article online - an online subscription or single-article purchase is required to access this article.

catena-Poly[[(benzoato-κ²O,O′)chloridocadmium(II)]-μ-2,2′-diphenyl-1,1′-(butane-1,4-diyl)diimidazole-κ²N³:N^3′]

Y.-Y. Liu, J.-F. Ma and L.-P. Zhang

The title Cd^II coordination polymer, [Cd(C₇H₅O₂)Cl(C₂₂H₂₂N₄)]_n, was obtained by reaction of CdCl₂·2.5H₂O, benzoic acid (HL) and 2,2′-diphenyl-1,1′-(butane-1,4-diyl)diimidazole (bbip). Each Cd^II cation is five-coordinated by a ClO₂N₂ donor set in a distorted trigonal–bipyramidal geometry. In the bbip ligand, three C atoms and one N atom are disordered equally over two positions; another two C atoms are disordered over two positions, the site-occupancy ratio being 0.6:0.4. The bbip ligand acts as a bridging bidentate ligand, linking Cd^II centres into a one-dimensional zigzag chain; adjacent chains are further connected through face-to-face π–π interactions between the imidazole rings [with an average face-to-face distance of 3.560 (8) Å], resulting in the formation of a two-dimensional supramolecular layer.

Read article Similar articles

Supporting information

	Crystallographic Information File (CIF) https://doi.org/10.1107/S1600536807036628/pr2014sup1.cif Contains datablocks global, I
	Structure factor file (CIF format) https://doi.org/10.1107/S1600536807036628/pr2014Isup2.hkl Contains datablock I

CCDC reference: 660087

checkCIF report

Key indicators

Single-crystal X-ray study
T = 293 K
Mean (C-C) = 0.009 Å
H-atom completeness 63%
Disorder in main residue
R factor = 0.052
wR factor = 0.161
Data-to-parameter ratio = 20.0

checkCIF/PLATON results

No syntax errors found



Alert level B
PLAT201_ALERT_2_B Isotropic non-H Atoms in Main Residue(s) .......          2

Alert level C
CHEMW03_ALERT_2_C The ratio of given/expected molecular weight as
            calculated from the _atom_site* data lies outside
            the range 0.99 <> 1.01
           From the CIF: _cell_formula_units_Z                    4
           From the CIF: _chemical_formula_weight           611.40
           TEST: Calculate formula weight from _atom_site_*
           atom     mass    num     sum
           C        12.01   29.00  348.32
           H         1.01   17.00   17.14
           N        14.01    4.00   56.03
           O        16.00    2.00   32.00
           Cd      112.41    1.00  112.41
           Cl       35.45    1.00   35.45
           Calculated formula weight              601.34
PLAT041_ALERT_1_C Calc. and Rep. SumFormula Strings    Differ ....          ?
PLAT042_ALERT_1_C Calc. and Rep. MoietyFormula Strings Differ ....          ?
PLAT043_ALERT_1_C Check Reported Molecular Weight ................     611.40
PLAT044_ALERT_1_C Calculated and Reported Dx Differ ..............          ?
PLAT062_ALERT_4_C Rescale T(min) & T(max) by .....................       1.04
PLAT068_ALERT_1_C Reported F000 Differs from Calcd (or Missing)...          ?
PLAT220_ALERT_2_C Large Non-Solvent    C     Ueq(max)/Ueq(min) ...       3.26 Ratio
PLAT241_ALERT_2_C Check High      Ueq as Compared to Neighbors for         O1
PLAT241_ALERT_2_C Check High      Ueq as Compared to Neighbors for         O2
PLAT241_ALERT_2_C Check High      Ueq as Compared to Neighbors for        C28
PLAT242_ALERT_2_C Check Low       Ueq as Compared to Neighbors for        Cd1
PLAT242_ALERT_2_C Check Low       Ueq as Compared to Neighbors for         N2
PLAT242_ALERT_2_C Check Low       Ueq as Compared to Neighbors for        C24
PLAT301_ALERT_3_C Main Residue  Disorder .........................      14.00 Perc.
PLAT342_ALERT_3_C Low Bond Precision on C-C Bonds (x 1000) Ang ...          9
PLAT369_ALERT_2_C Long   C(sp2)-C(sp2) Bond  C23    -   C24    ...       1.54 Ang.
PLAT601_ALERT_2_C Structure Contains Solvent Accessible VOIDS of .      36.00 A   3 
PLAT764_ALERT_4_C Overcomplete CIF Bond List Detected (Rep/Expd) .       1.31 Ratio

Alert level G
FORMU01_ALERT_2_G  There is a discrepancy between the atom counts in the
            _chemical_formula_sum and the formula from the _atom_site* data.
            Atom count from _chemical_formula_sum:C29 H27 Cd1 Cl1 N4 O2
            Atom count from the _atom_site data:  C29 H17 Cd1 Cl1 N4 O2
CELLZ01_ALERT_1_G Difference between formula and atom_site contents detected.
CELLZ01_ALERT_1_G WARNING: H atoms missing from atom site list. Is this intentional?
           From the CIF: _cell_formula_units_Z    4
           From the CIF: _chemical_formula_sum  C29 H27 Cd Cl N4 O2
           TEST: Compare cell contents of formula and atom_site data

           atom    Z*formula  cif sites diff
           C        116.00    116.00    0.00
           H        108.00     68.00   40.00
           Cd         4.00      4.00    0.00
           Cl         4.00      4.00    0.00
           N         16.00     16.00    0.00
           O          8.00      8.00    0.00
PLAT199_ALERT_1_G Check the Reported _cell_measurement_temperature        293 K
PLAT200_ALERT_1_G Check the Reported _diffrn_ambient_temperature .        293 K

   0 ALERT level A = In general: serious problem
   1 ALERT level B = Potentially serious problem
  19 ALERT level C = Check and explain
   5 ALERT level G = General alerts; check

   9 ALERT type 1 CIF construction/syntax error, inconsistent or missing data
  12 ALERT type 2 Indicator that the structure model may be wrong or deficient
   2 ALERT type 3 Indicator that the structure quality may be low
   2 ALERT type 4 Improvement, methodology, query or suggestion
   0 ALERT type 5 Informative message, check

Comment top

As part of an investigation of the transition metal application there is a need to prepare further examples of these compounds. In this paper, the structure of the title compound, (I), is described.

As shown in Fig. 1, the Cd^II ions is coordinated by one Cl^- anion, two oxygen atoms from the chelating carboxylate of L anion and two nitrogen atoms of two bbip ligands. Each Cd^II cation has a distorted trigonal bipyramidal coordination sphere. As illustrated in Fig. 2, each bbip molecule in (I) coordinates to two Cd^II cations through its two aromatic N atoms, thus acing as a bridging bidentate ligand. The Cd^II cations are bridged by bbip ligand to form a zigzag chain along the c axis, with the separation between the Cd^II atoms bridged by bbip ligand of 14.509 (1) Å. A fascinating structural feature of (I) is that there exist face-to-face π-π interactions between the imidazolyl ring and phenyl ring of adjacent bbip ligands (with the centroid-to-centriod and average face-to-face distances of 3.644 (7)–3.752 (2) Å and 3.647 (8)–3.760 (2) Å, respectively. Fig. 2). Along the b axis, parallel 1-D chains further stack to form 2-D supermolecular structure (Fig. 3) via face-to-face π-π interactions between imidazolyl rings, with the centroid-to-centriod distance of 3.607 (2) Å and average face-to-face distance of 3.560 (8) Å.

Related literature top

The bond distances and angles are normal (Ma et al., 2000).

Experimental top

The ligand bbip was synthesized according to the literature (Ma et al., 2000) but an imidazole was replaced by 2-phenylimidazole. A mixture of CdCl₂.2.5H₂O (0.091 g, 0.4 mmol), HL (0.049 g, 0.4 mmol), bbip (0.137 g, 0.40 mmol), and water (8 ml) was sealed in a Teflon reactor (15 ml) and heated at 160 °C for 3 days. After the mixture had been cooled to room temperature at 10 °C.h^-1, colorless crystals of (I) were obtained. Yield: 73%.

Structure description top

As part of an investigation of the transition metal application there is a need to prepare further examples of these compounds. In this paper, the structure of the title compound, (I), is described.

The bond distances and angles are normal (Ma et al., 2000).

Computing details top

Data collection: SMART (Bruker, 1997); cell refinement: SAINT (Bruker, 1999); data reduction: SAINT; program(s) used to solve structure: SHELXS97 (Sheldrick, 1997); program(s) used to refine structure: SHELXL97 (Sheldrick, 1997); molecular graphics: SHELXTL-Plus (Sheldrick, 1990); software used to prepare material for publication: SHELXL97.

Figures top

	Fig. 1. A view of the local coordination of the Cd^II cation in (I). Displacement ellipsoids are drawn at the 30% probability level and H atoms have been omitted for clarity.
	Fig. 2. View of the face-to-face π-π interactions in bbip ligands. L^- and Cl^- anions have been omitted for clarity.
	Fig. 3. The packing diagram of part of the crystal structure of (I), showing the face-to-face π-π interactions. L^- and Cl^- anions have been omitted for clarity.

catena-Poly[[(benzoato-κ²O,O')chloridocadmium(II)]-µ-2,2'-diphenyl-1,1'-˘butane-1,4-diyl)diimidazole-κ²N³:N^3'] top

Crystal data top

[Cd(C₇H₅O₂)Cl(C₂₂H₂₂N₄)]	F(000) = 1240
M_r = 611.40	D_x = 1.450 Mg m⁻³
Monoclinic, P2₁/c	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: -P 2ybc	Cell parameters from 4217 reflections
a = 20.0290 (16) Å	θ = 2.1–28.3°
b = 9.0893 (7) Å	µ = 0.91 mm⁻¹
c = 15.5393 (13) Å	T = 293 K
β = 98.197 (2)°	Block, colorless
V = 2800.0 (4) Å³	0.32 × 0.25 × 0.22 mm
Z = 4

Data collection top

Bruker APEX CCD area-detector diffractometer	6748 independent reflections
Radiation source: fine-focus sealed tube	4217 reflections with I > 2σ(I)
Graphite monochromator	R_int = 0.035
ω scans	θ_max = 28.3°, θ_min = 2.1°
Absorption correction: multi-scan (SADABS; Sheldrick, 1996)	h = −22→26
T_min = 0.74, T_max = 0.79	k = −11→12
16824 measured reflections	l = −19→20

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)] = 0.052	Hydrogen site location: inferred from neighbouring sites
wR(F²) = 0.161	H-atom parameters constrained
S = 1.00	w = 1/[σ²(F_o²) + (0.0894P)²] where P = (F_o² + 2F_c²)/3
6748 reflections	(Δ/σ)_max = 0.001
338 parameters	Δρ_max = 0.85 e Å⁻³
0 restraints	Δρ_min = −0.54 e Å⁻³

Crystal data top

[Cd(C₇H₅O₂)Cl(C₂₂H₂₂N₄)]	V = 2800.0 (4) Å³
M_r = 611.40	Z = 4
Monoclinic, P2₁/c	Mo Kα radiation
a = 20.0290 (16) Å	µ = 0.91 mm⁻¹
b = 9.0893 (7) Å	T = 293 K
c = 15.5393 (13) Å	0.32 × 0.25 × 0.22 mm
β = 98.197 (2)°

Data collection top

Bruker APEX CCD area-detector diffractometer	6748 independent reflections
Absorption correction: multi-scan (SADABS; Sheldrick, 1996)	4217 reflections with I > 2σ(I)
T_min = 0.74, T_max = 0.79	R_int = 0.035
16824 measured reflections

Refinement top

R[F² > 2σ(F²)] = 0.052	0 restraints
wR(F²) = 0.161	H-atom parameters constrained
S = 1.00	Δρ_max = 0.85 e Å⁻³
6748 reflections	Δρ_min = −0.54 e Å⁻³
338 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	Occ. (<1)
Cd1	0.222863 (16)	1.42407 (3)	0.871874 (19)	0.05373 (15)
C1	0.2233 (3)	1.1196 (6)	0.7681 (3)	0.0660 (13)
C2	0.1379 (6)	1.1311 (14)	0.6578 (7)	0.061 (3)	0.50
C2'	0.1237 (6)	1.0990 (12)	0.6842 (8)	0.053 (3)*	0.50
C3	0.1337 (2)	1.2422 (6)	0.7139 (3)	0.0653 (12)
C4	0.1836 (2)	0.3373 (5)	0.4985 (3)	0.0509 (10)
C5	0.2792 (2)	0.2428 (5)	0.5504 (3)	0.0597 (11)
H5	0.3165	0.1806	0.5583	0.072*
C6	0.2715 (2)	0.3616 (6)	0.5988 (3)	0.0619 (12)
H6	0.3015	0.3952	0.6459	0.074*
C7	0.2856 (3)	1.0733 (6)	0.8239 (4)	0.0708 (14)
C8	0.3412 (3)	1.1618 (7)	0.8307 (4)	0.0845 (16)
H8	0.3412	1.2462	0.7969	0.101*
C9	0.3981 (3)	1.1239 (9)	0.8890 (5)	0.104 (2)
H9	0.4361	1.1839	0.8947	0.125*
C10	0.3982 (3)	1.0008 (9)	0.9369 (5)	0.101 (2)
H10	0.4368	0.9760	0.9748	0.121*
C11	0.3434 (3)	0.9120 (7)	0.9313 (5)	0.094 (2)
H11	0.3443	0.8278	0.9655	0.113*
C12	0.2868 (3)	0.9470 (6)	0.8750 (4)	0.0795 (16)
H12	0.2490	0.8866	0.8708	0.095*
C13	0.1176 (2)	0.3626 (5)	0.4443 (3)	0.0573 (11)
C14	0.0745 (2)	0.2432 (6)	0.4254 (3)	0.0688 (13)
H14	0.0858	0.1515	0.4498	0.083*
C15	0.0152 (3)	0.2619 (8)	0.3703 (4)	0.0871 (17)
H15	−0.0130	0.1815	0.3562	0.104*
C16	−0.0034 (3)	0.3980 (9)	0.3355 (5)	0.098 (2)
H16	−0.0443	0.4102	0.2995	0.117*
C17	0.0394 (3)	0.5151 (8)	0.3547 (4)	0.0872 (17)
H17	0.0274	0.6070	0.3311	0.105*
C18	0.0988 (2)	0.4988 (6)	0.4072 (3)	0.0654 (12)
H18	0.1274	0.5792	0.4188	0.078*
C19'	0.2226 (6)	0.9355 (13)	0.6431 (8)	0.064 (3)*	0.40
C19	0.1970 (4)	0.8646 (10)	0.6951 (5)	0.0617 (19)*	0.60
C20	0.1926 (4)	0.8506 (11)	0.5946 (6)	0.058 (2)*	0.50
C20'	0.1816 (6)	0.8000 (14)	0.6443 (8)	0.081 (3)*	0.50
C21	0.2224 (4)	0.7045 (11)	0.5700 (6)	0.064 (2)*	0.60
C21'	0.2161 (6)	0.6732 (14)	0.6005 (8)	0.053 (3)*	0.40
C22	0.1782 (6)	0.5320 (15)	0.6152 (8)	0.067 (3)*	0.50
C22'	0.1852 (5)	0.5691 (12)	0.5948 (7)	0.050 (2)*	0.50
C23	0.3401 (3)	1.5518 (5)	0.8487 (4)	0.0688 (13)
C24	0.4080 (3)	1.6253 (7)	0.8387 (4)	0.0763 (14)
C25	0.4608 (3)	1.6183 (9)	0.9056 (5)	0.105 (2)
H25	0.4565	1.5642	0.9553	0.126*
C26	0.5195 (4)	1.6906 (12)	0.8992 (6)	0.137 (3)
H26	0.5549	1.6859	0.9448	0.164*
C27	0.5269 (4)	1.7698 (14)	0.8265 (8)	0.155 (4)
H27	0.5670	1.8192	0.8226	0.186*
C28	0.4739 (4)	1.7760 (14)	0.7586 (6)	0.162 (4)
H28	0.4784	1.8288	0.7085	0.195*
C29	0.4158 (4)	1.7046 (9)	0.7657 (4)	0.114 (2)
H29	0.3803	1.7094	0.7202	0.137*
N1	0.19153 (17)	1.2451 (4)	0.7736 (2)	0.0558 (9)
N2	0.1798 (4)	1.0148 (7)	0.7192 (4)	0.0441 (16)	0.50
N2'	0.1943 (5)	1.0566 (10)	0.6890 (6)	0.059 (2)*	0.50
N3	0.21146 (18)	0.4242 (4)	0.5661 (2)	0.0585 (10)
N4	0.22479 (16)	0.2261 (4)	0.4880 (2)	0.0517 (8)
O1	0.29828 (19)	1.5411 (5)	0.7832 (3)	0.0891 (12)
O2	0.33107 (18)	1.5115 (4)	0.9222 (3)	0.0798 (10)
Cl	0.13732 (7)	1.61591 (14)	0.86482 (10)	0.0804 (4)

Atomic displacement parameters (Å²) top

	U¹¹	U²²	U³³	U¹²	U¹³	U²³
Cd1	0.0710 (3)	0.0409 (2)	0.0458 (2)	−0.00401 (14)	−0.00363 (15)	−0.00112 (12)
C1	0.072 (3)	0.062 (3)	0.059 (3)	0.005 (2)	−0.005 (2)	−0.025 (2)
C2	0.063 (7)	0.073 (7)	0.050 (6)	−0.005 (5)	0.016 (5)	−0.013 (5)
C3	0.066 (3)	0.064 (3)	0.062 (3)	0.001 (2)	−0.004 (2)	−0.009 (2)
C4	0.055 (2)	0.050 (2)	0.046 (2)	0.0013 (19)	−0.0006 (18)	−0.0086 (18)
C5	0.058 (3)	0.067 (3)	0.050 (2)	0.012 (2)	−0.0049 (19)	−0.003 (2)
C6	0.057 (3)	0.071 (3)	0.054 (2)	0.001 (2)	−0.006 (2)	−0.008 (2)
C7	0.060 (3)	0.067 (3)	0.083 (4)	0.007 (2)	0.000 (3)	−0.029 (3)
C8	0.068 (3)	0.081 (4)	0.101 (4)	0.004 (3)	−0.002 (3)	−0.008 (3)
C9	0.065 (4)	0.105 (5)	0.134 (6)	−0.004 (3)	−0.020 (4)	−0.017 (5)
C10	0.075 (4)	0.110 (6)	0.108 (5)	0.021 (4)	−0.020 (3)	−0.015 (4)
C11	0.087 (4)	0.083 (4)	0.108 (5)	0.026 (3)	−0.005 (4)	−0.011 (3)
C12	0.070 (3)	0.070 (4)	0.094 (4)	0.013 (3)	−0.001 (3)	−0.020 (3)
C13	0.049 (2)	0.057 (3)	0.063 (3)	0.001 (2)	0.002 (2)	−0.014 (2)
C14	0.054 (3)	0.070 (3)	0.081 (3)	−0.005 (2)	0.004 (2)	−0.008 (3)
C15	0.058 (3)	0.100 (5)	0.099 (4)	−0.012 (3)	−0.004 (3)	−0.022 (4)
C16	0.061 (3)	0.120 (6)	0.103 (5)	0.014 (4)	−0.018 (3)	−0.020 (4)
C17	0.066 (3)	0.087 (4)	0.101 (4)	0.018 (3)	−0.013 (3)	−0.005 (4)
C18	0.056 (3)	0.059 (3)	0.078 (3)	0.006 (2)	−0.003 (2)	−0.006 (3)
C23	0.076 (3)	0.054 (3)	0.072 (3)	−0.001 (2)	−0.005 (3)	−0.008 (2)
C24	0.059 (3)	0.086 (4)	0.085 (4)	−0.006 (3)	0.010 (3)	−0.015 (3)
C25	0.064 (4)	0.128 (6)	0.117 (6)	−0.001 (4)	−0.007 (3)	−0.013 (4)
C26	0.065 (4)	0.196 (10)	0.146 (8)	−0.028 (5)	0.008 (4)	−0.032 (7)
C27	0.089 (6)	0.205 (11)	0.180 (10)	−0.037 (6)	0.050 (6)	−0.038 (9)
C28	0.116 (7)	0.241 (13)	0.142 (8)	−0.049 (8)	0.057 (6)	0.001 (8)
C29	0.102 (5)	0.155 (7)	0.087 (5)	−0.038 (5)	0.024 (4)	0.003 (4)
N1	0.065 (2)	0.046 (2)	0.054 (2)	0.0006 (17)	0.0000 (17)	−0.0097 (16)
N2	0.063 (4)	0.033 (3)	0.033 (3)	−0.009 (3)	−0.002 (3)	−0.003 (3)
N3	0.055 (2)	0.063 (2)	0.055 (2)	0.0071 (17)	−0.0039 (17)	−0.0193 (17)
N4	0.0530 (19)	0.051 (2)	0.0474 (19)	0.0031 (16)	−0.0040 (15)	−0.0065 (15)
O1	0.083 (3)	0.107 (3)	0.073 (2)	−0.023 (2)	−0.004 (2)	−0.018 (2)
O2	0.079 (2)	0.078 (3)	0.078 (3)	−0.019 (2)	−0.0043 (19)	0.012 (2)
Cl	0.0931 (9)	0.0445 (6)	0.0991 (10)	0.0147 (6)	−0.0011 (8)	0.0033 (6)

Geometric parameters (Å, º) top

Cd1—N1	2.258 (3)	C15—H15	0.9300
Cd1—N4ⁱ	2.259 (3)	C16—C17	1.372 (9)
Cd1—O2	2.336 (3)	C16—H16	0.9300
Cd1—O1	2.430 (4)	C17—C18	1.351 (7)
Cd1—Cl	2.4361 (13)	C17—H17	0.9300
C1—N1	1.315 (6)	C18—H18	0.9300
C1—N2'	1.403 (10)	C19'—C20	1.182 (14)
C1—N2	1.434 (8)	C19'—C19	1.205 (14)
C1—C7	1.475 (7)	C19'—N2'	1.470 (15)
C2—C2'	0.608 (12)	C19'—C20'	1.482 (18)
C2—C3	1.344 (11)	C19'—N2	1.716 (15)
C2—N2'	1.347 (14)	C19—C20'	0.997 (12)
C2—N2	1.583 (14)	C19—N2	1.469 (11)
C2'—N2	1.404 (13)	C19—C20	1.557 (12)
C2'—C3	1.386 (12)	C19—N2'	1.748 (13)
C2'—N2'	1.459 (15)	C20—C20'	0.951 (13)
C3—N1	1.378 (5)	C20—C21	1.526 (13)
C4—N4	1.330 (5)	C20—C21'	1.679 (16)
C4—N3	1.368 (5)	C20'—C21'	1.551 (17)
C4—C13	1.482 (6)	C21—C21'	0.581 (13)
C5—C6	1.337 (7)	C21—C22'	1.517 (15)
C5—N4	1.361 (5)	C21'—C22'	1.128 (15)
C5—H5	0.9300	C21'—C22	1.526 (18)
C6—N3	1.360 (5)	C22—N3	1.460 (13)
C6—H6	0.9300	C22'—N3	1.509 (11)
C7—C8	1.366 (8)	C23—O1	1.227 (6)
C7—C12	1.394 (8)	C23—O2	1.236 (6)
C8—C9	1.394 (8)	C24—C29	1.371 (9)
C8—H8	0.9300	C24—C25	1.376 (8)
C9—C10	1.343 (10)	C25—C26	1.362 (10)
C9—H9	0.9300	C25—H25	0.9300
C10—C11	1.356 (10)	C26—C27	1.366 (13)
C10—H10	0.9300	C26—H26	0.9300
C11—C12	1.368 (8)	C27—C28	1.386 (11)
C11—H11	0.9300	C27—H27	0.9300
C12—H12	0.9300	C28—C29	1.351 (10)
C13—C14	1.391 (6)	C28—H28	0.9300
C13—C18	1.394 (7)	C29—H29	0.9300
C14—C15	1.372 (7)	N2—N2'	0.699 (9)
C14—H14	0.9300	N4—Cd1ⁱⁱ	2.259 (3)
C15—C16	1.380 (9)

N1—Cd1—N4ⁱ	94.39 (13)	C19'—C20—C21'	118.6 (10)
N1—Cd1—O2	128.78 (14)	C19—C20—C21'	92.8 (7)
N4ⁱ—Cd1—O2	91.65 (12)	C20—C20'—C19	106.1 (15)
N1—Cd1—O1	93.84 (13)	C20—C20'—C19'	52.8 (10)
N4ⁱ—Cd1—O1	140.93 (13)	C19—C20'—C19'	53.9 (9)
O2—Cd1—O1	54.47 (13)	C20—C20'—C21'	80.4 (11)
N1—Cd1—Cl	111.06 (10)	C19—C20'—C21'	132.7 (12)
N4ⁱ—Cd1—Cl	113.59 (10)	C19'—C20'—C21'	109.2 (10)
O2—Cd1—Cl	112.63 (11)	C20—C20'—C21	61.1 (10)
O1—Cd1—Cl	98.70 (11)	C19—C20'—C21	134.3 (11)
N1—C1—N2'	105.5 (5)	C19'—C20'—C21	95.3 (9)
N1—C1—N2	110.3 (5)	C21'—C21—C20	94.9 (19)
N1—C1—C7	125.9 (4)	C22'—C21—C20	114.8 (8)
N2'—C1—C7	127.4 (5)	C21'—C21—C20'	61.9 (18)
N2—C1—C7	121.4 (5)	C22'—C21—C20'	86.7 (7)
C2'—C2—C3	81.0 (17)	C20—C21—C22	113.0 (7)
C2'—C2—N2'	88 (2)	C20'—C21—C22	83.4 (7)
C3—C2—N2'	105.7 (8)	C21—C21'—C22'	122 (2)
C2'—C2—N2	62.0 (18)	C21—C21'—C22	135 (2)
C3—C2—N2	100.8 (7)	C21—C21'—C20'	99 (2)
C2—C2'—N2	96 (2)	C22'—C21'—C20'	112.5 (11)
C2—C2'—C3	73.3 (17)	C22—C21'—C20'	107.3 (10)
N2—C2'—C3	108.3 (8)	C21—C21'—C20	64.9 (17)
C2—C2'—N2'	67.4 (18)	C22'—C21'—C20	130.8 (11)
C3—C2'—N2'	97.9 (8)	C22—C21'—C20	132.4 (10)
C2—C3—N1	109.0 (6)	N3—C22—C21'	102.3 (9)
N1—C3—C2'	108.1 (6)	N3—C22—C21	95.0 (7)
N4—C4—N3	109.9 (3)	C21'—C22'—N3	123.0 (10)
N4—C4—C13	124.6 (4)	N3—C22'—C21	115.4 (8)
N3—C4—C13	125.5 (4)	O1—C23—O2	124.8 (5)
C6—C5—N4	110.2 (4)	O1—C23—C24	117.2 (5)
C6—C5—H5	124.9	O2—C23—C24	118.0 (5)
N4—C5—H5	124.9	O1—C23—Cd1	64.6 (3)
C5—C6—N3	107.2 (4)	O2—C23—Cd1	60.2 (3)
C5—C6—H6	126.4	C24—C23—Cd1	178.2 (4)
N3—C6—H6	126.4	C29—C24—C25	118.9 (6)
C8—C7—C12	119.6 (5)	C29—C24—C23	121.2 (5)
C8—C7—C1	119.3 (5)	C25—C24—C23	119.8 (6)
C12—C7—C1	120.9 (5)	C26—C25—C24	120.1 (8)
C7—C8—C9	119.1 (6)	C26—C25—H25	120.0
C7—C8—H8	120.4	C24—C25—H25	120.0
C9—C8—H8	120.4	C25—C26—C27	120.8 (8)
C10—C9—C8	120.2 (6)	C25—C26—H26	119.6
C10—C9—H9	119.9	C27—C26—H26	119.6
C8—C9—H9	119.9	C26—C27—C28	119.3 (8)
C9—C10—C11	121.5 (6)	C26—C27—H27	120.3
C9—C10—H10	119.2	C28—C27—H27	120.3
C11—C10—H10	119.2	C29—C28—C27	119.5 (9)
C10—C11—C12	119.5 (7)	C29—C28—H28	120.2
C10—C11—H11	120.2	C27—C28—H28	120.2
C12—C11—H11	120.2	C28—C29—C24	121.4 (7)
C11—C12—C7	120.1 (6)	C28—C29—H29	119.3
C11—C12—H12	120.0	C24—C29—H29	119.3
C7—C12—H12	120.0	C1—N1—C3	107.9 (4)
C14—C13—C18	118.9 (4)	C1—N1—Cd1	125.3 (3)
C14—C13—C4	118.4 (4)	C3—N1—Cd1	126.5 (3)
C18—C13—C4	122.6 (4)	N2'—N2—C2'	80.3 (12)
C15—C14—C13	119.3 (5)	N2'—N2—C1	73.3 (10)
C15—C14—H14	120.3	C2'—N2—C1	103.6 (7)
C13—C14—H14	120.3	N2'—N2—C19	101.5 (12)
C14—C15—C16	121.1 (5)	C2'—N2—C19	127.7 (7)
C14—C15—H15	119.4	C1—N2—C19	127.2 (6)
C16—C15—H15	119.4	N2'—N2—C2	57.8 (11)
C17—C16—C15	119.0 (5)	C1—N2—C2	96.0 (6)
C17—C16—H16	120.5	C19—N2—C2	126.2 (6)
C15—C16—H16	120.5	N2'—N2—C19'	57.9 (11)
C18—C17—C16	121.0 (6)	C2'—N2—C19'	114.4 (8)
C18—C17—H17	119.5	C1—N2—C19'	108.5 (7)
C16—C17—H17	119.5	C2—N2—C19'	98.0 (7)
C17—C18—C13	120.6 (5)	N2—N2'—C2	96.2 (13)
C17—C18—H18	119.7	N2—N2'—C1	78.2 (11)
C13—C18—H18	119.7	C2—N2'—C1	109.3 (8)
C20—C19'—C19	81.5 (10)	N2—N2'—C19'	98.3 (13)
C20—C19'—N2'	127.0 (11)	C2—N2'—C19'	124.3 (10)
C19—C19'—N2'	81.0 (9)	C1—N2'—C19'	126.2 (9)
N2'—C19'—C20'	111.3 (10)	N2—N2'—C2'	71.6 (11)
C20—C19'—N2	117.0 (10)	C1—N2'—C2'	102.4 (7)
C19—C19'—N2	57.2 (7)	C19'—N2'—C2'	127.7 (9)
C20'—C19'—N2	90.4 (8)	N2—N2'—C19	55.4 (10)
C20'—C19—C19'	84.1 (12)	C2—N2'—C19	122.6 (8)
C20'—C19—N2	133.7 (11)	C1—N2'—C19	110.7 (7)
C19'—C19—N2	79.2 (8)	C2'—N2'—C19	106.8 (7)
C19'—C19—C20	48.6 (7)	C6—N3—C4	106.7 (4)
N2—C19—C20	110.5 (7)	C6—N3—C22	122.1 (6)
C20'—C19—N2'	122.8 (11)	C4—N3—C22	128.4 (6)
C19'—C19—N2'	56.1 (7)	C6—N3—C22'	125.6 (5)
C20—C19—N2'	91.8 (6)	C4—N3—C22'	127.5 (5)
C20'—C20—C19'	87.4 (13)	C4—N4—C5	106.0 (3)
C20'—C20—C21	85.8 (11)	C4—N4—Cd1ⁱⁱ	128.1 (3)
C19'—C20—C21	123.1 (10)	C5—N4—Cd1ⁱⁱ	123.9 (3)
C19'—C20—C19	49.9 (8)	C23—O1—Cd1	88.3 (4)
C21—C20—C19	110.7 (7)	C23—O2—Cd1	92.4 (3)
C20'—C20—C21'	65.6 (11)

C3—C2—C2'—N2	−107.4 (8)	C26—C27—C28—C29	0.6 (17)
N2'—C2—C2'—N2	−1.2 (10)	C27—C28—C29—C24	−0.4 (16)
N2'—C2—C2'—C3	106.3 (7)	C25—C24—C29—C28	−0.2 (12)
N2—C2—C2'—C3	107.4 (8)	C23—C24—C29—C28	176.3 (8)
C3—C2—C2'—N2'	−106.3 (7)	N2'—C1—N1—C3	15.6 (7)
N2—C2—C2'—N2'	1.2 (10)	N2—C1—N1—C3	−13.9 (6)
C2'—C2—C3—N1	92.2 (18)	C7—C1—N1—C3	−176.3 (5)
N2'—C2—C3—N1	6.9 (11)	N2'—C1—N1—Cd1	−169.0 (5)
N2—C2—C3—N1	33.2 (9)	N2—C1—N1—Cd1	161.5 (4)
N2'—C2—C3—C2'	−85 (2)	C7—C1—N1—Cd1	−0.9 (8)
N2—C2—C3—C2'	−59.1 (17)	C2—C3—N1—C1	−14.6 (8)
N2—C2'—C3—C2	90 (2)	C2'—C3—N1—C1	12.5 (7)
N2'—C2'—C3—C2	63.5 (17)	C2—C3—N1—Cd1	170.1 (7)
C2—C2'—C3—N1	−96.6 (18)	C2'—C3—N1—Cd1	−162.9 (6)
N2—C2'—C3—N1	−6.1 (10)	N4ⁱ—Cd1—N1—C1	−54.7 (4)
N2'—C2'—C3—N1	−33.1 (9)	O2—Cd1—N1—C1	40.9 (5)
N4—C5—C6—N3	−1.0 (6)	O1—Cd1—N1—C1	87.0 (4)
N1—C1—C7—C8	−55.0 (8)	Cl—Cd1—N1—C1	−172.1 (4)
N2'—C1—C7—C8	110.4 (8)	C23—Cd1—N1—C1	66.8 (4)
N2—C1—C7—C8	144.4 (6)	N4ⁱ—Cd1—N1—C3	119.8 (4)
N1—C1—C7—C12	119.7 (6)	O2—Cd1—N1—C3	−144.5 (4)
N2'—C1—C7—C12	−74.8 (9)	O1—Cd1—N1—C3	−98.4 (4)
N2—C1—C7—C12	−40.9 (8)	Cl—Cd1—N1—C3	2.4 (4)
C12—C7—C8—C9	−0.1 (9)	C23—Cd1—N1—C3	−118.7 (4)
C1—C7—C8—C9	174.7 (5)	C2—C2'—N2—N2'	2 (2)
C7—C8—C9—C10	0.8 (10)	C3—C2'—N2—N2'	−72.0 (13)
C8—C9—C10—C11	−1.1 (12)	C2—C2'—N2—C1	72.3 (19)
C9—C10—C11—C12	0.7 (11)	C3—C2'—N2—C1	−1.9 (10)
C10—C11—C12—C7	0.0 (9)	N2'—C2'—N2—C1	70.1 (10)
C8—C7—C12—C11	−0.2 (9)	C2—C2'—N2—C19	−95 (2)
C1—C7—C12—C11	−174.9 (5)	C3—C2'—N2—C19	−169.0 (8)
N4—C4—C13—C14	45.0 (7)	N2'—C2'—N2—C19	−97.0 (14)
N3—C4—C13—C14	−135.3 (5)	C3—C2'—N2—C2	−74.2 (18)
N4—C4—C13—C18	−131.0 (5)	N2'—C2'—N2—C2	−2 (2)
N3—C4—C13—C18	48.8 (7)	C2—C2'—N2—C19'	−46 (2)
C18—C13—C14—C15	0.6 (7)	C3—C2'—N2—C19'	−119.9 (9)
C4—C13—C14—C15	−175.5 (4)	N2'—C2'—N2—C19'	−47.9 (11)
C13—C14—C15—C16	−1.9 (9)	N1—C1—N2—N2'	85.1 (12)
C14—C15—C16—C17	1.8 (10)	C7—C1—N2—N2'	−111.6 (12)
C15—C16—C17—C18	−0.4 (10)	N1—C1—N2—C2'	9.8 (8)
C16—C17—C18—C13	−0.9 (9)	N2'—C1—N2—C2'	−75.3 (11)
C14—C13—C18—C17	0.8 (7)	C7—C1—N2—C2'	173.2 (7)
C4—C13—C18—C17	176.7 (5)	N1—C1—N2—C19	177.0 (7)
C20—C19'—C19—C20'	6.7 (11)	N2'—C1—N2—C19	91.9 (14)
N2'—C19'—C19—C20'	136.5 (10)	C7—C1—N2—C19	−19.7 (11)
N2—C19'—C19—C20'	136.7 (10)	N1—C1—N2—C2	31.3 (7)
C20—C19'—C19—N2	−130.0 (8)	N2'—C1—N2—C2	−53.8 (10)
N2'—C19'—C19—N2	−0.2 (6)	C7—C1—N2—C2	−165.3 (6)
C20'—C19'—C19—N2	−136.7 (10)	N1—C1—N2—C19'	131.8 (6)
N2'—C19'—C19—C20	129.8 (10)	N2'—C1—N2—C19'	46.7 (11)
C20'—C19'—C19—C20	−6.7 (11)	C7—C1—N2—C19'	−64.8 (8)
N2—C19'—C19—C20	130.0 (8)	C20'—C19—N2—N2'	−70.5 (19)
C20—C19'—C19—N2'	−129.8 (10)	C19'—C19—N2—N2'	0.3 (14)
C20'—C19'—C19—N2'	−136.5 (10)	C20—C19—N2—N2'	−37.5 (13)
N2—C19'—C19—N2'	0.2 (6)	C20'—C19—N2—C2'	16 (2)
C19—C19'—C20—C20'	−7.0 (11)	C19'—C19—N2—C2'	86.8 (12)
N2'—C19'—C20—C20'	−78.8 (16)	C20—C19—N2—C2'	49.0 (12)
N2—C19'—C20—C20'	−53.3 (13)	N2'—C19—N2—C2'	86.5 (14)
C19—C19'—C20—C21	−90.2 (12)	C20'—C19—N2—C1	−148.2 (14)
N2'—C19'—C20—C21	−162.0 (11)	C19'—C19—N2—C1	−77.3 (10)
C20'—C19'—C20—C21	−83.2 (13)	C20—C19—N2—C1	−115.2 (8)
N2—C19'—C20—C21	−136.5 (10)	N2'—C19—N2—C1	−77.7 (13)
N2'—C19'—C20—C19	−71.8 (13)	C20'—C19—N2—C2	−12.2 (19)
C20'—C19'—C20—C19	7.0 (11)	C19'—C19—N2—C2	58.7 (11)
N2—C19'—C20—C19	−46.3 (8)	C20—C19—N2—C2	20.8 (12)
C19—C19'—C20—C21'	−67.3 (12)	N2'—C19—N2—C2	58.3 (12)
N2'—C19'—C20—C21'	−139.1 (12)	C20'—C19—N2—C19'	−70.8 (16)
C20'—C19'—C20—C21'	−60.3 (11)	C20—C19—N2—C19'	−37.9 (8)
N2—C19'—C20—C21'	−113.6 (11)	N2'—C19—N2—C19'	−0.3 (14)
C19'—C19—C20—C20'	168.6 (18)	C2'—C2—N2—N2'	−177 (2)
N2—C19—C20—C20'	−137.9 (15)	C3—C2—N2—N2'	−103.7 (14)
N2'—C19—C20—C20'	−151.7 (15)	C3—C2—N2—C2'	73.6 (18)
C20'—C19—C20—C19'	−168.6 (18)	N2'—C2—N2—C2'	177 (2)
N2—C19—C20—C19'	53.5 (10)	C2'—C2—N2—C1	−111.4 (19)
N2'—C19—C20—C19'	39.6 (9)	C3—C2—N2—C1	−37.8 (9)
C20'—C19—C20—C21	−52.3 (14)	N2'—C2—N2—C1	66.0 (11)
C19'—C19—C20—C21	116.4 (12)	C2'—C2—N2—C19	102.4 (19)
N2—C19—C20—C21	169.8 (7)	C3—C2—N2—C19	176.0 (7)
N2'—C19—C20—C21	156.0 (7)	N2'—C2—N2—C19	−80.2 (14)
C20'—C19—C20—C21'	−42.8 (14)	C2'—C2—N2—C19'	138.9 (19)
C19'—C19—C20—C21'	125.8 (11)	C3—C2—N2—C19'	−147.5 (8)
N2—C19—C20—C21'	179.3 (7)	N2'—C2—N2—C19'	−43.8 (12)
N2'—C19—C20—C21'	165.5 (7)	C20—C19'—N2—N2'	−121.4 (17)
C19'—C20—C20'—C19	8.7 (14)	C19—C19'—N2—N2'	−179.6 (16)
C21—C20—C20'—C19	132.1 (11)	C20'—C19'—N2—N2'	−152.3 (15)
C21'—C20—C20'—C19	131.9 (13)	C20—C19'—N2—C2'	−61.6 (14)
C21—C20—C20'—C19'	123.4 (10)	C19—C19'—N2—C2'	−119.9 (10)
C19—C20—C20'—C19'	−8.7 (14)	N2'—C19'—N2—C2'	59.7 (13)
C21'—C20—C20'—C19'	123.2 (9)	C20'—C19'—N2—C2'	−92.5 (10)
C19'—C20—C20'—C21'	−123.2 (9)	C20—C19'—N2—C1	−176.8 (10)
C21—C20—C20'—C21'	0.3 (8)	C19—C19'—N2—C1	125.0 (8)
C19—C20—C20'—C21'	−131.9 (13)	N2'—C19'—N2—C1	−55.4 (12)
C19'—C20—C20'—C21	−123.4 (10)	C20'—C19'—N2—C1	152.3 (8)
C19—C20—C20'—C21	−132.1 (11)	C20—C19'—N2—C19	58.2 (10)
C21'—C20—C20'—C21	−0.3 (8)	N2'—C19'—N2—C19	179.6 (16)
C19'—C19—C20'—C20	−8.6 (14)	C20'—C19'—N2—C19	27.3 (7)
N2—C19—C20'—C20	60.3 (19)	C20—C19'—N2—C2	−77.7 (12)
N2'—C19—C20'—C20	34.3 (18)	C19—C19'—N2—C2	−135.9 (9)
N2—C19—C20'—C19'	68.9 (14)	N2'—C19'—N2—C2	43.7 (12)
C20—C19—C20'—C19'	8.6 (14)	C20'—C19'—N2—C2	−108.6 (9)
N2'—C19—C20'—C19'	42.8 (10)	C2'—N2—N2'—C2	−1.0 (9)
C19'—C19—C20'—C21'	83.2 (18)	C1—N2—N2'—C2	−108.5 (8)
N2—C19—C20'—C21'	152.1 (13)	C19—N2—N2'—C2	125.8 (8)
C20—C19—C20'—C21'	92 (2)	C19'—N2—N2'—C2	126.1 (11)
N2'—C19—C20'—C21'	126.0 (15)	C2'—N2—N2'—C1	107.5 (6)
C19'—C19—C20'—C21	56.6 (17)	C19—N2—N2'—C1	−125.7 (6)
N2—C19—C20'—C21	125.5 (14)	C2—N2—N2'—C1	108.5 (8)
C20—C19—C20'—C21	65.2 (16)	C19'—N2—N2'—C1	−125.4 (9)
N2'—C19—C20'—C21	99.4 (16)	C2'—N2—N2'—C19'	−127.1 (9)
C19—C19'—C20'—C20	169.7 (17)	C1—N2—N2'—C19'	125.4 (9)
N2'—C19'—C20'—C20	122.8 (14)	C19—N2—N2'—C19'	−0.3 (11)
N2—C19'—C20'—C20	134.4 (12)	C2—N2—N2'—C19'	−126.1 (11)
C20—C19'—C20'—C19	−169.7 (17)	C1—N2—N2'—C2'	−107.5 (6)
N2'—C19'—C20'—C19	−46.8 (11)	C19—N2—N2'—C2'	126.8 (8)
N2—C19'—C20'—C19	−35.2 (8)	C2—N2—N2'—C2'	1.0 (9)
C20—C19'—C20'—C21'	60.9 (12)	C19'—N2—N2'—C2'	127.1 (9)
C19—C19'—C20'—C21'	−129.4 (14)	C2'—N2—N2'—C19	−126.8 (8)
N2'—C19'—C20'—C21'	−176.3 (10)	C1—N2—N2'—C19	125.7 (6)
N2—C19'—C20'—C21'	−164.6 (9)	C2—N2—N2'—C19	−125.8 (8)
C20—C19'—C20'—C21	47.2 (10)	C19'—N2—N2'—C19	0.3 (11)
C19—C19'—C20'—C21	−143.1 (12)	C2'—C2—N2'—N2	2 (2)
N2'—C19'—C20'—C21	170.0 (9)	C3—C2—N2'—N2	82.4 (14)
N2—C19'—C20'—C21	−178.4 (7)	C2'—C2—N2'—C1	−77.3 (19)
C20'—C20—C21—C21'	−1 (2)	C3—C2—N2'—C1	2.8 (12)
C19'—C20—C21—C21'	83 (2)	N2—C2—N2'—C1	−79.6 (12)
C19—C20—C21—C21'	28 (2)	C2'—C2—N2'—C19'	106.8 (19)
C20'—C20—C21—C22'	34.6 (12)	C3—C2—N2'—C19'	−173.1 (10)
C19'—C20—C21—C22'	118.6 (12)	N2—C2—N2'—C19'	104.5 (16)
C19—C20—C21—C22'	63.8 (10)	C3—C2—N2'—C2'	80.1 (18)
C21'—C20—C21—C22'	35.3 (15)	N2—C2—N2'—C2'	−2 (2)
C19'—C20—C21—C20'	84.1 (14)	C2'—C2—N2'—C19	55 (2)
C19—C20—C21—C20'	29.2 (8)	C3—C2—N2'—C19	135.0 (9)
C21'—C20—C21—C20'	1 (2)	N2—C2—N2'—C19	52.5 (10)
C20'—C20—C21—C22	28.2 (12)	N1—C1—N2'—N2	−104.2 (11)
C19'—C20—C21—C22	112.3 (12)	C7—C1—N2'—N2	88.0 (13)
C19—C20—C21—C22	57.4 (9)	N1—C1—N2'—C2	−11.7 (10)
C21'—C20—C21—C22	28.9 (16)	N2—C1—N2'—C2	92.4 (13)
C20—C20'—C21—C21'	179 (2)	C7—C1—N2'—C2	−179.5 (8)
C19—C20'—C21—C21'	95 (3)	N1—C1—N2'—C19'	164.1 (9)
C19'—C20'—C21—C21'	137 (2)	N2—C1—N2'—C19'	−91.7 (15)
C20—C20'—C21—C22'	−148.9 (11)	C7—C1—N2'—C19'	−3.7 (14)
C19—C20'—C21—C22'	126.5 (18)	N1—C1—N2'—C2'	−36.3 (9)
C19'—C20'—C21—C22'	169.2 (9)	N2—C1—N2'—C2'	67.9 (11)
C21'—C20'—C21—C22'	31.9 (17)	C7—C1—N2'—C2'	155.9 (7)
C19—C20'—C21—C20	−84.5 (19)	N1—C1—N2'—C19	−149.8 (5)
C19'—C20'—C21—C20	−41.9 (9)	N2—C1—N2'—C19	−45.7 (10)
C21'—C20'—C21—C20	−179 (2)	C7—C1—N2'—C19	42.4 (10)
C20—C20'—C21—C22	−154.0 (11)	C20—C19'—N2'—N2	72.4 (18)
C19—C20'—C21—C22	121.4 (18)	C19—C19'—N2'—N2	0.3 (13)
C19'—C20'—C21—C22	164.1 (9)	C20'—C19'—N2'—N2	30.0 (16)
C21'—C20'—C21—C22	26.8 (18)	C20—C19'—N2'—C2	−31 (2)
C20—C21—C21'—C22'	124.0 (17)	C19—C19'—N2'—C2	−103.0 (13)
C20'—C21—C21'—C22'	124 (2)	C20'—C19'—N2'—C2	−73.4 (15)
C22—C21—C21'—C22'	−1.7 (12)	N2—C19'—N2'—C2	−103.4 (16)
C22'—C21—C21'—C22	1.7 (12)	C20—C19'—N2'—C1	153.8 (12)
C20—C21—C21'—C22	126 (2)	C19—C19'—N2'—C1	81.8 (11)
C20'—C21—C21'—C22	125 (3)	C20'—C19'—N2'—C1	111.4 (12)
C22'—C21—C21'—C20'	−124 (2)	N2—C19'—N2'—C1	81.4 (14)
C20—C21—C21'—C20'	0.4 (13)	C20—C19'—N2'—C2'	−1 (2)
C22—C21—C21'—C20'	−125 (3)	C19—C19'—N2'—C2'	−72.8 (13)
C22'—C21—C21'—C20	−124.0 (17)	C20'—C19'—N2'—C2'	−43.1 (16)
C20'—C21—C21'—C20	−0.4 (13)	N2—C19'—N2'—C2'	−73.1 (13)
C22—C21—C21'—C20	−126 (2)	C20—C19'—N2'—C19	72.0 (13)
C20—C20'—C21'—C21	−1 (2)	C20'—C19'—N2'—C19	29.6 (7)
C19—C20'—C21'—C21	−104 (3)	N2—C19'—N2'—C19	−0.3 (13)
C19'—C20'—C21'—C21	−46 (2)	C2—C2'—N2'—N2	−178 (2)
C20—C20'—C21'—C22'	−130.6 (14)	C3—C2'—N2'—N2	114.3 (12)
C19—C20'—C21'—C22'	126.2 (18)	N2—C2'—N2'—C2	178 (2)
C19'—C20'—C21'—C22'	−175.6 (12)	C3—C2'—N2'—C2	−68.2 (17)
C21—C20'—C21'—C22'	−130 (3)	C2—C2'—N2'—C1	109.6 (18)
C20—C20'—C21'—C22	−143.3 (12)	N2—C2'—N2'—C1	−72.9 (10)
C19—C20'—C21'—C22	113.6 (18)	C3—C2'—N2'—C1	41.4 (9)
C19'—C20'—C21'—C22	171.8 (10)	C2—C2'—N2'—C19'	−91 (2)
C21—C20'—C21'—C22	−143 (2)	N2—C2'—N2'—C19'	86.3 (14)
C19—C20'—C21'—C20	−103 (2)	C3—C2'—N2'—C19'	−159.4 (10)
C19'—C20'—C21'—C20	−44.9 (9)	C2—C2'—N2'—C19	−134.0 (18)
C21—C20'—C21'—C20	1 (2)	N2—C2'—N2'—C19	43.5 (9)
C20'—C20—C21'—C21	179 (2)	C3—C2'—N2'—C19	157.8 (7)
C19'—C20—C21'—C21	−109 (2)	C20'—C19—N2'—N2	125.9 (16)
C19—C20—C21'—C21	−153.5 (19)	C19'—C19—N2'—N2	−179.6 (16)
C20'—C20—C21'—C22'	67.9 (17)	C20—C19—N2'—N2	145.2 (13)
C19'—C20—C21'—C22'	140.1 (15)	C20'—C19—N2'—C2	52.6 (16)
C21—C20—C21'—C22'	−111 (3)	C19'—C19—N2'—C2	107.1 (13)
C19—C20—C21'—C22'	95.2 (15)	N2—C19—N2'—C2	−73.4 (13)
C20'—C20—C21'—C22	50.6 (15)	C20—C19—N2'—C2	71.8 (10)
C19'—C20—C21'—C22	122.8 (14)	C20'—C19—N2'—C1	−175.9 (11)
C21—C20—C21'—C22	−129 (3)	C19'—C19—N2'—C1	−121.4 (11)
C19—C20—C21'—C22	77.9 (13)	N2—C19—N2'—C1	58.2 (11)
C19'—C20—C21'—C20'	72.3 (14)	C20—C19—N2'—C1	−156.6 (7)
C21—C20—C21'—C20'	−179 (2)	C20'—C19—N2'—C19'	−54.5 (13)
C19—C20—C21'—C20'	27.3 (9)	N2—C19—N2'—C19'	179.6 (16)
C21—C21'—C22—N3	54 (3)	C20—C19—N2'—C19'	−35.2 (8)
C22'—C21'—C22—N3	60 (4)	C20'—C19—N2'—C2'	73.4 (14)
C20'—C21'—C22—N3	175.9 (9)	C19'—C19—N2'—C2'	127.9 (11)
C20—C21'—C22—N3	149.0 (11)	N2—C19—N2'—C2'	−52.5 (11)
C22'—C21'—C22—C21	6 (5)	C20—C19—N2'—C2'	92.7 (8)
C20'—C21'—C22—C21	122 (3)	C5—C6—N3—C4	1.2 (5)
C20—C21'—C22—C21	95 (3)	C5—C6—N3—C22	163.7 (7)
C21'—C21—C22—N3	−128 (3)	C5—C6—N3—C22'	−173.6 (7)
C22'—C21—C22—N3	62 (6)	N4—C4—N3—C6	−1.0 (5)
C20—C21—C22—N3	170.6 (7)	C13—C4—N3—C6	179.2 (4)
C20'—C21—C22—N3	−174.4 (7)	N4—C4—N3—C22	−162.0 (8)
C22'—C21—C22—C21'	−170 (7)	C13—C4—N3—C22	18.2 (10)
C20—C21—C22—C21'	−62 (3)	N4—C4—N3—C22'	173.7 (7)
C20'—C21—C22—C21'	−46 (3)	C13—C4—N3—C22'	−6.1 (9)
C21—C21'—C22'—N3	72 (3)	C21'—C22—N3—C6	80.4 (10)
C22—C21'—C22'—N3	−103 (4)	C21—C22—N3—C6	90.1 (7)
C20'—C21'—C22'—N3	−171.3 (9)	C21'—C22—N3—C4	−121.2 (8)
C20—C21'—C22'—N3	154.7 (10)	C21—C22—N3—C4	−111.5 (7)
C22—C21'—C22'—C21	−175 (4)	C21'—C22—N3—C22'	−26.4 (18)
C20'—C21'—C22'—C21	117 (3)	C21—C22—N3—C22'	−16.7 (19)
C20—C21'—C22'—C21	83 (3)	C21'—C22'—N3—C6	49.6 (15)
C20—C21—C22'—C21'	−65 (2)	C21—C22'—N3—C6	69.6 (10)
C20'—C21—C22'—C21'	−47 (2)	C21'—C22'—N3—C4	−124.0 (12)
C22—C21—C22'—C21'	9 (6)	C21—C22'—N3—C4	−104.0 (8)
C21'—C21—C22'—N3	−118 (3)	C21'—C22'—N3—C22	136 (3)
C20—C21—C22'—N3	176.5 (7)	C21—C22'—N3—C22	156 (3)
C20'—C21—C22'—N3	−165.5 (8)	N3—C4—N4—C5	0.4 (5)
C22—C21—C22'—N3	−109 (6)	C13—C4—N4—C5	−179.9 (4)
N1—Cd1—C23—O1	49.2 (3)	N3—C4—N4—Cd1ⁱⁱ	−163.9 (3)
N4ⁱ—Cd1—C23—O1	156.9 (3)	C13—C4—N4—Cd1ⁱⁱ	15.9 (6)
O2—Cd1—C23—O1	−178.5 (5)	C6—C5—N4—C4	0.4 (5)
Cl—Cd1—C23—O1	−73.7 (3)	C6—C5—N4—Cd1ⁱⁱ	165.5 (3)
N1—Cd1—C23—O2	−132.3 (3)	O2—C23—O1—Cd1	−1.6 (6)
N4ⁱ—Cd1—C23—O2	−24.6 (4)	C24—C23—O1—Cd1	−179.6 (4)
O1—Cd1—C23—O2	178.5 (5)	N1—Cd1—O1—C23	−135.5 (3)
Cl—Cd1—C23—O2	104.8 (3)	N4ⁱ—Cd1—O1—C23	−33.7 (4)
O1—C23—C24—C29	14.5 (9)	O2—Cd1—O1—C23	0.8 (3)
O2—C23—C24—C29	−163.7 (6)	Cl—Cd1—O1—C23	112.5 (3)
O1—C23—C24—C25	−169.0 (6)	O1—C23—O2—Cd1	1.6 (6)
O2—C23—C24—C25	12.8 (8)	C24—C23—O2—Cd1	179.7 (4)
C29—C24—C25—C26	0.6 (11)	N1—Cd1—O2—C23	61.2 (4)
C23—C24—C25—C26	−176.0 (7)	N4ⁱ—Cd1—O2—C23	158.2 (3)
C24—C25—C26—C27	−0.4 (14)	O1—Cd1—O2—C23	−0.8 (3)
C25—C26—C27—C28	−0.2 (17)	Cl—Cd1—O2—C23	−85.3 (3)

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

Experimental details

Crystal data
Chemical formula	[Cd(C₇H₅O₂)Cl(C₂₂H₂₂N₄)]
M_r	611.40
Crystal system, space group	Monoclinic, P2₁/c
Temperature (K)	293
a, b, c (Å)	20.0290 (16), 9.0893 (7), 15.5393 (13)
β (°)	98.197 (2)
V (Å³)	2800.0 (4)
Z	4
Radiation type	Mo Kα
µ (mm⁻¹)	0.91
Crystal size (mm)	0.32 × 0.25 × 0.22

Data collection
Diffractometer	Bruker APEX CCD area-detector
Absorption correction	Multi-scan (SADABS; Sheldrick, 1996)
T_min, T_max	0.74, 0.79
No. of measured, independent and observed [I > 2σ(I)] reflections	16824, 6748, 4217
R_int	0.035
(sin θ/λ)_max (Å⁻¹)	0.667

Refinement
R[F² > 2σ(F²)], wR(F²), S	0.052, 0.161, 1.00
No. of reflections	6748
No. of parameters	338
H-atom treatment	H-atom parameters constrained
Δρ_max, Δρ_min (e Å⁻³)	0.85, −0.54

Computer programs: SMART (Bruker, 1997), SAINT (Bruker, 1999), SAINT, SHELXS97 (Sheldrick, 1997), SHELXL97 (Sheldrick, 1997), SHELXTL-Plus (Sheldrick, 1990), SHELXL97.

Selected geometric parameters (Å, º) top

Cd1—N1	2.258 (3)	Cd1—O1	2.430 (4)
Cd1—N4ⁱ	2.259 (3)	Cd1—Cl	2.4361 (13)
Cd1—O2	2.336 (3)

N1—Cd1—N4ⁱ	94.39 (13)	O2—Cd1—O1	54.47 (13)
N1—Cd1—O2	128.78 (14)	N1—Cd1—Cl	111.06 (10)
N4ⁱ—Cd1—O2	91.65 (12)	N4ⁱ—Cd1—Cl	113.59 (10)
N1—Cd1—O1	93.84 (13)	O2—Cd1—Cl	112.63 (11)
N4ⁱ—Cd1—O1	140.93 (13)	O1—Cd1—Cl	98.70 (11)

Symmetry code: (i) x, −y+3/2, z+1/2.

Subscribe to Acta Crystallographica Section E: Crystallographic Communications

Buy online

You may purchase this article in PDF and/or HTML formats. For purchasers in the European Community who do not have a VAT number, VAT will be added at the local rate. Payments to the IUCr are handled by WorldPay, who will accept payment by credit card in several currencies. To purchase the article, please complete the form below (fields marked * are required), and then click on `Continue'.

E-mail address*
Repeat e-mail address* (for error checking)

Format*	PDF (US $40)
	HTML (US $40)
	PDF+HTML (US $50)
In order for VAT to be shown for your country javascript needs to be enabled.

VAT number (non-UK EC countries only)
Country*

Terms and conditions of use
Contact us

Format		BIBTeX
		EndNote
		RefMan
		Refer
		Medline
		CIF
		SGML
		Text
		Plain Text

Format		BIBTeX
		EndNote
		RefMan
		Refer
		Medline
		CIF
		SGML
		Text
		Plain Text

Search IUCr Journals		doi		Advanced search
Author		volume	page