catena-Poly[[[diiodidocadmium(II)]-μ-1-(4-pyridylmeth­yl)-1H-benzimidazole] methanol hemisolvate]

Wang, J.-J.; Yan, L.-F.; Hu, T.-L.

doi:10.1107/S1600536807061302

catena-Poly[[[diiodidocadmium(II)]-μ-1-(4-pyridylmethyl)-1H-benzimidazole] methanol hemisolvate]

In the title coordination polymer, {[CdI₂(C₁₃H₁₁N₃)]·0.5CH₄O}_n, each Cd^II center is four-coordinated by two N-atom donors from two 1-(4-pyridylmethyl)-1H-benzimidazole (L) ligands and two iodide anions, forming a tetrahedral coordination geometry. L ligands bridge adjacent Cd^II ions, generating two crystallographically independent approximately orthogonal one-dimensional chains. The methanol solvent molecule associates with one of the chains via O—H

I interactions.

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Supporting information

	Crystallographic Information File (CIF) https://doi.org/10.1107/S1600536807061302/sq2002sup1.cif Contains datablocks global, I
	Structure factor file (CIF format) https://doi.org/10.1107/S1600536807061302/sq2002Isup2.hkl Contains datablock I

CCDC reference: 674231

checkCIF report

Key indicators

Single-crystal X-ray study
T = 293 K
Mean (C-C) = 0.007 Å
R factor = 0.024
wR factor = 0.054
Data-to-parameter ratio = 16.3

checkCIF/PLATON results

No syntax errors found



Alert level C
PLAT041_ALERT_1_C Calc. and Rep. SumFormula Strings    Differ ....          ?
PLAT042_ALERT_1_C Calc. and Rep. MoietyFormula Strings Differ ....          ?
PLAT045_ALERT_1_C Calculated and Reported Z Differ by ............       0.50 Ratio
PLAT716_ALERT_1_C H...A   Unknown or Inconsistent Label ..........          I
                    H1     I
PLAT717_ALERT_1_C D...A   Unknown or Inconsistent Label ..........          I
                    O1     I
PLAT718_ALERT_1_C D-H..A  Unknown or Inconsistent Label ..........          I
                    O1     H1     I
PLAT755_ALERT_4_C D-H     Calc     0.82000, Rep     0.82(2) ......  Senseless su
              O1   -H1      1.555   1.555

Alert level G
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
   0 ALERT level B = Potentially serious problem
   7 ALERT level C = Check and explain
   2 ALERT level G = General alerts; check

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

Comment top

N-containing heterocyclic aromatic compounds are extensively used as bridging ligands in coordination and metallosupramolecular chemistry (Steel, 2005). In recent years, benzimidazole groups have been used to link different alkyl or aromatic groups to form a series of bi- and multi-dentate flexible ligands, which can adopt different conformations according to the different geometric requirements of the metal centers when forming complexes (Li et al., 2007). Many complexes with these ligands show unique structural topologies and interesting properties (Meng et al., 2004). Recently, Liu and co-workers synthesized a flexible bridging ligand 1-(pyridin-4-ylmethyl)-1H-benzo[d]imidazole (L) as well as its chiral one-dimensional double helix polymer, [Ag(L)(NO₃)]_n (Huang et al., 2006). We herein report the crystal structure of a cadmium complex of this ligand (I).

In the molecule of (I), (Fig. 1 and 2), the bond lengths and angles (Table 1) are generally within normal ranges (Allen et al., 1987). The Cd^II center is tetrahedrally coordinated by two N atoms from two L ligands (L = 1-(pyridin-4-ylmethyl)-1H-benzo[d]imidazole) and two iodide ions. In the extended structure of (I), the Cd^II centers are interconnected by L ligands to form two one-dimensional chains along two different directions (Fig. 3). The chain containing Cd1 is along the c direction and the other one containing Cd2 is along the b direction, making them essentially orthogonal. The methanol solvate molecules are associated with the Cd1 chains via O—H···I interactions.

Related literature top

For a review of N-containing heterocyclic aromatic compounds as bridging ligands, see: Steel (2005). For a discussion of benzimidazole ligands in complexes, see: Li et al. (2007); Meng et al. (2004). For an example of a silver coordination polymer of the present ligand, see: Huang et al. (2006). For bond-length data, see: Allen et al. (1987).

Experimental top

The ligand 1-(pyridin-4-ylmethyl)-1H-benzo[d]imidazole (L) was synthesized according to a reported method (Li et al., 2007). The reaction of L (58 mg, 0.2 mmol), NaI (30 mg, 0.2 mmol) and Cd(ClO₄)₂ (31 mg, 0.1 mmol) in a solution of methanol and water (v/v = 1:1,10 ml) for a few minutes afforded a white solid, which was separated by filtration. The resulting solution was kept at room temperature. Colorless single crystals suitable for X-ray analysis were obtained by slow evaporation of the solvent after several days (yield: 40%).

Structure description top

Computing details top

Data collection: CrystalClear (Rigaku/MSC, 2005); cell refinement: CrystalClear (Rigaku/MSC, 2005); data reduction: CrystalClear (Rigaku/MSC, 2005); program(s) used to solve structure: SHELXS97 (Sheldrick, 1997); program(s) used to refine structure: SHELXL97 (Sheldrick, 1997); molecular graphics: SHELXTL (Bruker, 1998); software used to prepare material for publication: SHELXTL (Bruker, 1998).

Figures top

	Fig. 1. The coordination environment of Cd1, showing the atom-labelling scheme. Displacement ellipsoids are drawn at the 30% probability level. [symmetry code: (A) x, 3/2 - y, 1/2 + z].
	Fig. 2. The coordination environment of Cd2, showing the atom-labelling scheme. Displacement ellipsoids are drawn at the 30% probability level. [symmetry code: (B) 1 - x, -1/2 + y, 3/2 - z].
	Fig. 3. View of the two crystallographically independent one-dimensional chains that run along the b and c axes.

catena-Poly[[[diiodidocadmium(II)]-µ-1-(4-pyridylmethyl)- 1H-benzimidazole] methanol hemisolvate] top

Crystal data top

[CdI₂(C₁₃H₁₁N₃)]·0.5CH₄O	F(000) = 2184
M_r = 591.47	D_x = 2.337 Mg m⁻³
Monoclinic, P2₁/c	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: -P 2ybc	Cell parameters from 9593 reflections
a = 17.469 (4) Å	θ = 2.7–25.0°
b = 12.913 (3) Å	µ = 4.97 mm⁻¹
c = 16.814 (3) Å	T = 293 K
β = 117.56 (3)°	Block, colorless
V = 3362.6 (16) Å³	0.10 × 0.06 × 0.04 mm
Z = 8

Data collection top

Rigaku R-AXIS RAPID-S diffractometer	5901 independent reflections
Radiation source: fine-focus sealed tube	5155 reflections with I > 2σ(I)
Graphite monochromator	R_int = 0.066
ω scans	θ_max = 25.0°, θ_min = 2.1°
Absorption correction: multi-scan (SADABS; Bruker, 1998)	h = −20→20
T_min = 0.637, T_max = 0.826	k = −15→15
33513 measured reflections	l = −19→19

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)] = 0.024	Hydrogen site location: inferred from neighbouring sites
wR(F²) = 0.054	H-atom parameters constrained
S = 1.02	w = 1/[σ²(F_o²) + (0.0176P)²] where P = (F_o² + 2F_c²)/3
5901 reflections	(Δ/σ)_max = 0.001
363 parameters	Δρ_max = 1.49 e Å⁻³
0 restraints	Δρ_min = −0.81 e Å⁻³

Crystal data top

[CdI₂(C₁₃H₁₁N₃)]·0.5CH₄O	V = 3362.6 (16) Å³
M_r = 591.47	Z = 8
Monoclinic, P2₁/c	Mo Kα radiation
a = 17.469 (4) Å	µ = 4.97 mm⁻¹
b = 12.913 (3) Å	T = 293 K
c = 16.814 (3) Å	0.10 × 0.06 × 0.04 mm
β = 117.56 (3)°

Data collection top

Rigaku R-AXIS RAPID-S diffractometer	5901 independent reflections
Absorption correction: multi-scan (SADABS; Bruker, 1998)	5155 reflections with I > 2σ(I)
T_min = 0.637, T_max = 0.826	R_int = 0.066
33513 measured reflections

Refinement top

R[F² > 2σ(F²)] = 0.024	0 restraints
wR(F²) = 0.054	H-atom parameters constrained
S = 1.02	Δρ_max = 1.49 e Å⁻³
5901 reflections	Δρ_min = −0.81 e Å⁻³
363 parameters

Special details top

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

Refinement. Refinement of F² against ALL reflections. The weighted R-factor wR and goodness of fit S are based on F², conventional R-factors R are based on F, with F set to zero for negative F². The threshold expression of F² > σ(F²) is used only for calculating R-factors(gt) etc. and is not relevant to the choice of reflections for refinement. R-factors based on F² are statistically about twice as large as those based on F, and R- factors based on ALL data will be even larger.

Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Å²) top

	x	y	z	U_iso*/U_eq
Cd1	0.185504 (19)	0.46826 (2)	0.868473 (19)	0.01644 (8)
Cd2	0.272027 (19)	0.52226 (2)	0.547057 (19)	0.01630 (8)
I1	0.356936 (18)	0.51615 (2)	0.948024 (19)	0.02392 (8)
I2	0.109810 (19)	0.27969 (2)	0.825044 (19)	0.02452 (8)
I3	0.2197 (2)	0.3922 (2)	0.6382 (2)	0.0220 (8)
I4	0.178051 (18)	0.61285 (2)	0.385404 (17)	0.02101 (8)
N1	0.1207 (2)	0.5680 (2)	0.7429 (2)	0.0166 (8)
N2	0.0638 (2)	0.8382 (2)	0.4991 (2)	0.0158 (8)
N3	0.1338 (2)	0.9484 (3)	0.4526 (2)	0.0169 (8)
N4	0.32450 (19)	0.6665 (2)	0.6382 (2)	0.0142 (8)
N5	0.4629 (2)	0.9308 (2)	0.8829 (2)	0.0159 (8)
N6	0.6033 (2)	0.9608 (3)	0.9407 (2)	0.0178 (8)
C1	0.1638 (2)	0.6488 (3)	0.7339 (3)	0.0159 (9)
H1A	0.2159	0.6671	0.7826	0.019*
C2	0.1355 (2)	0.7062 (3)	0.6570 (3)	0.0160 (9)
H2A	0.1694	0.7594	0.6531	0.019*
C3	0.0561 (3)	0.6843 (3)	0.5853 (3)	0.0155 (9)
C4	0.0106 (3)	0.5992 (3)	0.5937 (3)	0.0190 (10)
H4A	−0.0423	0.5802	0.5464	0.023*
C5	0.0448 (3)	0.5442 (3)	0.6721 (3)	0.0171 (9)
H5A	0.0141	0.4877	0.6767	0.020*
C6	0.0143 (3)	0.7484 (3)	0.5008 (3)	0.0236 (10)
H6A	0.0044	0.7044	0.4501	0.028*
H6B	−0.0415	0.7718	0.4928	0.028*
C7	0.0926 (2)	0.8603 (3)	0.4385 (3)	0.0167 (9)
H7A	0.0837	0.8165	0.3911	0.020*
C8	0.1326 (2)	0.9898 (3)	0.5286 (3)	0.0152 (9)
C13	0.0877 (2)	0.9230 (3)	0.5583 (3)	0.0135 (9)
C12	0.0736 (3)	0.9453 (3)	0.6317 (3)	0.0175 (10)
H12A	0.0428	0.9009	0.6499	0.021*
C11	0.1082 (3)	1.0372 (3)	0.6757 (3)	0.0220 (10)
H11A	0.0999	1.0559	0.7246	0.026*
C10	0.1551 (3)	1.1025 (3)	0.6488 (3)	0.0220 (10)
H10A	0.1790	1.1624	0.6816	0.026*
C9	0.1674 (3)	1.0815 (3)	0.5751 (3)	0.0186 (10)
H9A	0.1978	1.1269	0.5571	0.022*
C14	0.3534 (2)	0.6536 (3)	0.7270 (3)	0.0176 (9)
H14A	0.3621	0.5867	0.7500	0.021*
C15	0.3706 (2)	0.7354 (3)	0.7848 (3)	0.0191 (10)
H15A	0.3915	0.7236	0.8459	0.023*
C16	0.3568 (2)	0.8352 (3)	0.7520 (3)	0.0152 (9)
C17	0.3283 (2)	0.8485 (3)	0.6601 (3)	0.0161 (9)
H17A	0.3200	0.9147	0.6356	0.019*
C18	0.3127 (2)	0.7629 (3)	0.6064 (3)	0.0175 (10)
H18A	0.2931	0.7726	0.5452	0.021*
C19	0.3725 (2)	0.9284 (3)	0.8137 (3)	0.0174 (9)
H19A	0.3589	0.9917	0.7788	0.021*
H19B	0.3351	0.9241	0.8419	0.021*
C20	0.5281 (3)	0.9789 (3)	0.8737 (3)	0.0162 (9)
H20A	0.5194	1.0200	0.8248	0.019*
C21	0.5015 (3)	0.8769 (3)	0.9641 (3)	0.0165 (9)
C22	0.4677 (3)	0.8140 (3)	1.0078 (3)	0.0217 (10)
H22A	0.4086	0.8028	0.9843	0.026*
C23	0.5263 (3)	0.7690 (3)	1.0875 (3)	0.0273 (11)
H23A	0.5064	0.7264	1.1186	0.033*
C24	0.6145 (3)	0.7866 (3)	1.1220 (3)	0.0257 (11)
H24A	0.6522	0.7539	1.1751	0.031*
C25	0.6478 (3)	0.8505 (3)	1.0806 (3)	0.0224 (10)
H25A	0.7068	0.8631	1.1054	0.027*
C26	0.5893 (3)	0.8961 (3)	0.9996 (3)	0.0166 (9)
C27	0.4068 (3)	0.1849 (4)	0.6542 (3)	0.0435 (14)
H27A	0.4159	0.2210	0.7078	0.065*
H27B	0.3462	0.1835	0.6132	0.065*
H27C	0.4370	0.2200	0.6268	0.065*
O1	0.4380 (2)	0.0826 (2)	0.6760 (2)	0.0395 (9)
H1	0.4366	0.0545	0.6316	0.059*

Atomic displacement parameters (Å²) top

	U¹¹	U²²	U³³	U¹²	U¹³	U²³
Cd1	0.01903 (18)	0.01604 (18)	0.01442 (17)	−0.00084 (13)	0.00788 (14)	0.00038 (13)
Cd2	0.01569 (17)	0.01688 (18)	0.01279 (17)	0.00087 (13)	0.00356 (14)	−0.00074 (13)
I1	0.01795 (16)	0.03018 (19)	0.01836 (16)	−0.00153 (13)	0.00393 (13)	0.00307 (13)
I2	0.02970 (18)	0.01589 (16)	0.03350 (18)	−0.00305 (13)	0.01931 (15)	−0.00410 (13)
I3	0.0239 (2)	0.0196 (2)	0.0212 (2)	−0.0028 (1)	0.0092 (1)	0.0016 (1)
I4	0.02138 (17)	0.02211 (17)	0.01193 (15)	0.00291 (12)	0.00126 (13)	0.00017 (12)
N1	0.016 (2)	0.0158 (19)	0.020 (2)	−0.0012 (15)	0.0105 (17)	0.0010 (16)
N2	0.0174 (19)	0.0115 (19)	0.0131 (18)	−0.0013 (15)	0.0024 (16)	0.0025 (15)
N3	0.018 (2)	0.017 (2)	0.0158 (19)	0.0003 (16)	0.0082 (16)	0.0001 (16)
N4	0.0109 (18)	0.017 (2)	0.0118 (18)	−0.0015 (14)	0.0023 (15)	−0.0026 (15)
N5	0.0129 (19)	0.019 (2)	0.0110 (18)	−0.0038 (15)	0.0017 (16)	−0.0074 (15)
N6	0.0146 (19)	0.021 (2)	0.0166 (19)	−0.0021 (16)	0.0060 (17)	−0.0012 (16)
C1	0.015 (2)	0.012 (2)	0.019 (2)	−0.0009 (18)	0.0061 (19)	−0.0015 (18)
C2	0.015 (2)	0.011 (2)	0.023 (2)	−0.0002 (18)	0.010 (2)	0.0030 (18)
C3	0.019 (2)	0.012 (2)	0.016 (2)	0.0034 (18)	0.0081 (19)	0.0012 (18)
C4	0.014 (2)	0.022 (3)	0.015 (2)	−0.0021 (18)	0.0015 (19)	0.0004 (19)
C5	0.016 (2)	0.016 (2)	0.018 (2)	−0.0031 (18)	0.006 (2)	−0.0014 (19)
C6	0.020 (2)	0.019 (2)	0.022 (2)	−0.009 (2)	0.002 (2)	0.002 (2)
C7	0.020 (2)	0.017 (2)	0.010 (2)	0.0059 (19)	0.0049 (19)	0.0017 (18)
C8	0.009 (2)	0.017 (2)	0.016 (2)	0.0036 (17)	0.0027 (19)	0.0048 (18)
C13	0.013 (2)	0.009 (2)	0.014 (2)	0.0031 (17)	0.0028 (18)	0.0014 (18)
C12	0.020 (2)	0.018 (2)	0.017 (2)	−0.0009 (19)	0.010 (2)	0.0047 (19)
C11	0.033 (3)	0.022 (3)	0.013 (2)	0.008 (2)	0.012 (2)	0.006 (2)
C10	0.029 (3)	0.015 (2)	0.016 (2)	0.002 (2)	0.006 (2)	0.0008 (19)
C9	0.023 (2)	0.014 (2)	0.021 (2)	0.0011 (19)	0.011 (2)	0.0048 (19)
C14	0.014 (2)	0.018 (2)	0.017 (2)	0.0009 (18)	0.0036 (19)	0.0007 (19)
C15	0.015 (2)	0.026 (3)	0.011 (2)	−0.0033 (19)	0.0015 (19)	−0.0015 (19)
C16	0.007 (2)	0.017 (2)	0.019 (2)	−0.0032 (18)	0.0026 (18)	−0.0049 (19)
C17	0.014 (2)	0.012 (2)	0.020 (2)	0.0001 (17)	0.0055 (19)	0.0048 (18)
C18	0.017 (2)	0.022 (3)	0.011 (2)	−0.0009 (19)	0.0038 (19)	0.0006 (19)
C19	0.011 (2)	0.021 (2)	0.016 (2)	−0.0028 (18)	0.0024 (19)	−0.0068 (19)
C20	0.020 (2)	0.017 (2)	0.009 (2)	0.0006 (19)	0.005 (2)	−0.0014 (18)
C21	0.023 (2)	0.015 (2)	0.011 (2)	0.0011 (19)	0.007 (2)	−0.0030 (18)
C22	0.023 (3)	0.025 (3)	0.017 (2)	−0.007 (2)	0.009 (2)	−0.006 (2)
C23	0.040 (3)	0.025 (3)	0.021 (3)	−0.003 (2)	0.017 (2)	0.000 (2)
C24	0.034 (3)	0.022 (3)	0.014 (2)	0.001 (2)	0.005 (2)	0.004 (2)
C25	0.019 (2)	0.021 (2)	0.020 (2)	0.001 (2)	0.003 (2)	−0.003 (2)
C26	0.017 (2)	0.016 (2)	0.015 (2)	0.0023 (18)	0.006 (2)	−0.0025 (18)
C27	0.041 (3)	0.042 (3)	0.041 (3)	0.006 (3)	0.014 (3)	0.005 (3)
O1	0.054 (2)	0.029 (2)	0.0241 (19)	−0.0026 (18)	0.0081 (19)	0.0014 (16)

Geometric parameters (Å, º) top

Cd1—N3ⁱ	2.271 (3)	C8—C13	1.405 (5)
Cd1—N1	2.278 (3)	C13—C12	1.395 (5)
Cd1—I2	2.7051 (6)	C12—C11	1.382 (5)
Cd1—I1	2.7264 (10)	C12—H12A	0.9300
Cd2—N6ⁱⁱ	2.236 (3)	C11—C10	1.388 (5)
Cd2—N4	2.315 (3)	C11—H11A	0.9300
Cd2—I3	2.702 (6)	C10—C9	1.380 (5)
Cd2—I4	2.706 (1)	C10—H10A	0.9300
N1—C1	1.334 (5)	C9—H9A	0.9300
N1—C5	1.346 (5)	C14—C15	1.372 (5)
N2—C7	1.359 (5)	C14—H14A	0.9300
N2—C13	1.407 (5)	C15—C16	1.379 (5)
N2—C6	1.453 (5)	C15—H15A	0.9300
N3—C7	1.308 (5)	C16—C17	1.398 (5)
N3—C8	1.394 (5)	C16—C19	1.529 (5)
N3—Cd1ⁱⁱⁱ	2.271 (3)	C17—C18	1.373 (5)
N4—C18	1.333 (5)	C17—H17A	0.9300
N4—C14	1.347 (5)	C18—H18A	0.9300
N5—C20	1.366 (5)	C19—H19A	0.9700
N5—C21	1.397 (5)	C19—H19B	0.9700
N5—C19	1.465 (5)	C20—H20A	0.9300
N6—C20	1.297 (5)	C21—C26	1.386 (5)
N6—C26	1.401 (5)	C21—C22	1.396 (5)
N6—Cd2^iv	2.236 (3)	C22—C23	1.383 (6)
C1—C2	1.369 (5)	C22—H22A	0.9300
C1—H1A	0.9300	C23—C24	1.391 (6)
C2—C3	1.382 (5)	C23—H23A	0.9300
C2—H2A	0.9300	C24—C25	1.370 (5)
C3—C4	1.402 (5)	C24—H24A	0.9300
C3—C6	1.509 (5)	C25—C26	1.400 (5)
C4—C5	1.367 (5)	C25—H25A	0.9300
C4—H4A	0.9300	C27—O1	1.412 (5)
C5—H5A	0.9300	C27—H27A	0.9600
C6—H6A	0.9700	C27—H27B	0.9600
C6—H6B	0.9700	C27—H27C	0.9600
C7—H7A	0.9300	O1—H1	0.8200
C8—C9	1.394 (5)

N3ⁱ—Cd1—N1	97.99 (11)	C11—C12—H12A	122.0
N3ⁱ—Cd1—I2	108.01 (8)	C13—C12—H12A	122.0
N1—Cd1—I2	106.72 (8)	C12—C11—C10	121.7 (4)
N3ⁱ—Cd1—I1	104.48 (8)	C12—C11—H11A	119.2
N1—Cd1—I1	106.76 (8)	C10—C11—H11A	119.2
I2—Cd1—I1	128.711 (15)	C9—C10—C11	122.3 (4)
N6ⁱⁱ—Cd2—N4	98.86 (12)	C9—C10—H10A	118.9
N6ⁱⁱ—Cd2—I3	107.34 (9)	C11—C10—H10A	118.9
N4—Cd2—I3	105.01 (8)	C10—C9—C8	117.5 (4)
N6ⁱⁱ—Cd2—I4	110.99 (9)	C10—C9—H9A	121.3
N4—Cd2—I4	100.80 (8)	C8—C9—H9A	121.3
I3—Cd2—I4	129.14 (8)	N4—C14—C15	122.5 (4)
C1—N1—C5	117.1 (3)	N4—C14—H14A	118.7
C1—N1—Cd1	118.8 (3)	C15—C14—H14A	118.7
C5—N1—Cd1	123.7 (3)	C14—C15—C16	119.7 (4)
C7—N2—C13	106.0 (3)	C14—C15—H15A	120.1
C7—N2—C6	127.6 (3)	C16—C15—H15A	120.1
C13—N2—C6	126.3 (3)	C15—C16—C17	117.7 (4)
C7—N3—C8	105.0 (3)	C15—C16—C19	121.4 (4)
C7—N3—Cd1ⁱⁱⁱ	130.1 (3)	C17—C16—C19	120.9 (3)
C8—N3—Cd1ⁱⁱⁱ	124.6 (3)	C18—C17—C16	119.3 (4)
C18—N4—C14	118.0 (3)	C18—C17—H17A	120.4
C18—N4—Cd2	123.1 (3)	C16—C17—H17A	120.4
C14—N4—Cd2	117.7 (3)	N4—C18—C17	122.8 (4)
C20—N5—C21	106.6 (3)	N4—C18—H18A	118.6
C20—N5—C19	124.6 (3)	C17—C18—H18A	118.6
C21—N5—C19	128.3 (3)	N5—C19—C16	110.2 (3)
C20—N6—C26	106.4 (3)	N5—C19—H19A	109.6
C20—N6—Cd2^iv	124.7 (3)	C16—C19—H19A	109.6
C26—N6—Cd2^iv	128.9 (3)	N5—C19—H19B	109.6
N1—C1—C2	123.6 (4)	C16—C19—H19B	109.6
N1—C1—H1A	118.2	H19A—C19—H19B	108.1
C2—C1—H1A	118.2	N6—C20—N5	112.5 (4)
C1—C2—C3	119.5 (4)	N6—C20—H20A	123.7
C1—C2—H2A	120.3	N5—C20—H20A	123.7
C3—C2—H2A	120.3	C26—C21—C22	122.0 (4)
C2—C3—C4	117.3 (4)	C26—C21—N5	105.6 (3)
C2—C3—C6	124.3 (4)	C22—C21—N5	132.4 (4)
C4—C3—C6	118.4 (4)	C23—C22—C21	116.8 (4)
C5—C4—C3	119.3 (4)	C23—C22—H22A	121.6
C5—C4—H4A	120.4	C21—C22—H22A	121.6
C3—C4—H4A	120.4	C22—C23—C24	121.0 (4)
N1—C5—C4	123.1 (4)	C22—C23—H23A	119.5
N1—C5—H5A	118.4	C24—C23—H23A	119.5
C4—C5—H5A	118.4	C25—C24—C23	122.3 (4)
N2—C6—C3	115.0 (3)	C25—C24—H24A	118.8
N2—C6—H6A	108.5	C23—C24—H24A	118.8
C3—C6—H6A	108.5	C24—C25—C26	117.2 (4)
N2—C6—H6B	108.5	C24—C25—H25A	121.4
C3—C6—H6B	108.5	C26—C25—H25A	121.4
H6A—C6—H6B	107.5	C21—C26—C25	120.5 (4)
N3—C7—N2	114.2 (3)	C21—C26—N6	108.9 (3)
N3—C7—H7A	122.9	C25—C26—N6	130.6 (4)
N2—C7—H7A	122.9	O1—C27—H27A	109.5
N3—C8—C9	130.7 (4)	O1—C27—H27B	109.5
N3—C8—C13	109.8 (4)	H27A—C27—H27B	109.5
C9—C8—C13	119.5 (4)	O1—C27—H27C	109.5
C12—C13—C8	123.0 (4)	H27A—C27—H27C	109.5
C12—C13—N2	132.1 (4)	H27B—C27—H27C	109.5
C8—C13—N2	105.0 (3)	C27—O1—H1	109.5
C11—C12—C13	116.0 (4)

N3ⁱ—Cd1—N1—C1	92.6 (3)	N2—C13—C12—C11	179.2 (4)
I2—Cd1—N1—C1	−155.8 (3)	C13—C12—C11—C10	−0.8 (6)
I1—Cd1—N1—C1	−15.2 (3)	C12—C11—C10—C9	2.3 (6)
N3ⁱ—Cd1—N1—C5	−94.8 (3)	C11—C10—C9—C8	−1.6 (6)
I2—Cd1—N1—C5	16.8 (3)	N3—C8—C9—C10	179.5 (4)
I1—Cd1—N1—C5	157.4 (3)	C13—C8—C9—C10	−0.4 (6)
N6ⁱⁱ—Cd2—N4—C18	107.4 (3)	C18—N4—C14—C15	0.2 (6)
I3—Cd2—N4—C18	−141.9 (3)	Cd2—N4—C14—C15	−167.5 (3)
I4—Cd2—N4—C18	−6.1 (3)	N4—C14—C15—C16	1.1 (6)
N6ⁱⁱ—Cd2—N4—C14	−85.6 (3)	C14—C15—C16—C17	−2.3 (6)
I3—Cd2—N4—C14	25.1 (3)	C14—C15—C16—C19	178.2 (4)
I4—Cd2—N4—C14	160.9 (3)	C15—C16—C17—C18	2.1 (6)
C5—N1—C1—C2	−1.2 (6)	C19—C16—C17—C18	−178.4 (3)
Cd1—N1—C1—C2	171.9 (3)	C14—N4—C18—C17	−0.4 (6)
N1—C1—C2—C3	3.5 (6)	Cd2—N4—C18—C17	166.6 (3)
C1—C2—C3—C4	−3.7 (6)	C16—C17—C18—N4	−0.8 (6)
C1—C2—C3—C6	173.8 (4)	C20—N5—C19—C16	88.7 (5)
C2—C3—C4—C5	1.9 (6)	C21—N5—C19—C16	−83.1 (4)
C6—C3—C4—C5	−175.7 (4)	C15—C16—C19—N5	59.9 (5)
C1—N1—C5—C4	−0.8 (6)	C17—C16—C19—N5	−119.7 (4)
Cd1—N1—C5—C4	−173.4 (3)	C26—N6—C20—N5	0.2 (4)
C3—C4—C5—N1	0.3 (6)	Cd2^iv—N6—C20—N5	179.3 (2)
C7—N2—C6—C3	121.7 (4)	C21—N5—C20—N6	−0.1 (5)
C13—N2—C6—C3	−61.8 (5)	C19—N5—C20—N6	−173.4 (3)
C2—C3—C6—N2	−0.4 (6)	C20—N5—C21—C26	0.0 (4)
C4—C3—C6—N2	177.1 (3)	C19—N5—C21—C26	172.9 (3)
C8—N3—C7—N2	−0.3 (4)	C20—N5—C21—C22	−179.4 (4)
Cd1ⁱⁱⁱ—N3—C7—N2	−174.1 (2)	C19—N5—C21—C22	−6.5 (7)
C13—N2—C7—N3	1.3 (4)	C26—C21—C22—C23	−1.6 (6)
C6—N2—C7—N3	178.3 (3)	N5—C21—C22—C23	177.7 (4)
C7—N3—C8—C9	179.2 (4)	C21—C22—C23—C24	0.2 (6)
Cd1ⁱⁱⁱ—N3—C8—C9	−6.6 (6)	C22—C23—C24—C25	1.5 (7)
C7—N3—C8—C13	−0.9 (4)	C23—C24—C25—C26	−1.8 (6)
Cd1ⁱⁱⁱ—N3—C8—C13	173.3 (2)	C22—C21—C26—C25	1.3 (6)
N3—C8—C13—C12	−178.0 (3)	N5—C21—C26—C25	−178.1 (3)
C9—C8—C13—C12	1.9 (6)	C22—C21—C26—N6	179.6 (4)
N3—C8—C13—N2	1.6 (4)	N5—C21—C26—N6	0.2 (4)
C9—C8—C13—N2	−178.4 (3)	C24—C25—C26—C21	0.4 (6)
C7—N2—C13—C12	177.9 (4)	C24—C25—C26—N6	−177.5 (4)
C6—N2—C13—C12	0.8 (6)	C20—N6—C26—C21	−0.2 (4)
C7—N2—C13—C8	−1.7 (4)	Cd2^iv—N6—C26—C21	−179.2 (3)
C6—N2—C13—C8	−178.8 (3)	C20—N6—C26—C25	177.8 (4)
C8—C13—C12—C11	−1.2 (6)	Cd2^iv—N6—C26—C25	−1.2 (6)

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

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
O1—H1···I2^v	0.82	2.88	3.647 (5)	155

Symmetry code: (v) x, −y+1/2, z−1/2.

Experimental details

Crystal data
Chemical formula	[CdI₂(C₁₃H₁₁N₃)]·0.5CH₄O
M_r	591.47
Crystal system, space group	Monoclinic, P2₁/c
Temperature (K)	293
a, b, c (Å)	17.469 (4), 12.913 (3), 16.814 (3)
β (°)	117.56 (3)
V (Å³)	3362.6 (16)
Z	8
Radiation type	Mo Kα
µ (mm⁻¹)	4.97
Crystal size (mm)	0.10 × 0.06 × 0.04

Data collection
Diffractometer	Rigaku R-AXIS RAPID-S
Absorption correction	Multi-scan (SADABS; Bruker, 1998)
T_min, T_max	0.637, 0.826
No. of measured, independent and observed [I > 2σ(I)] reflections	33513, 5901, 5155
R_int	0.066
(sin θ/λ)_max (Å⁻¹)	0.595

Refinement
R[F² > 2σ(F²)], wR(F²), S	0.024, 0.054, 1.02
No. of reflections	5901
No. of parameters	363
H-atom treatment	H-atom parameters constrained
Δρ_max, Δρ_min (e Å⁻³)	1.49, −0.81

Computer programs: CrystalClear (Rigaku/MSC, 2005), SHELXS97 (Sheldrick, 1997), SHELXL97 (Sheldrick, 1997), SHELXTL (Bruker, 1998).

Selected geometric parameters (Å, º) top

Cd1—N3ⁱ	2.271 (3)	Cd2—N6ⁱⁱ	2.236 (3)
Cd1—N1	2.278 (3)	Cd2—N4	2.315 (3)
Cd1—I2	2.7051 (6)	Cd2—I3	2.702 (6)
Cd1—I1	2.7264 (10)	Cd2—I4	2.706 (1)

N3ⁱ—Cd1—N1	97.99 (11)	N6ⁱⁱ—Cd2—N4	98.86 (12)
N3ⁱ—Cd1—I2	108.01 (8)	N6ⁱⁱ—Cd2—I3	107.34 (9)
N1—Cd1—I2	106.72 (8)	N4—Cd2—I3	105.01 (8)
N3ⁱ—Cd1—I1	104.48 (8)	N6ⁱⁱ—Cd2—I4	110.99 (9)
N1—Cd1—I1	106.76 (8)	N4—Cd2—I4	100.80 (8)
I2—Cd1—I1	128.711 (15)	I3—Cd2—I4	129.14 (8)

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