catena-Poly[[aqua­bis­(3-chloro­benzoato-κ2O,O′)cadmium]-μ-N,N-di­ethyl­nico­tin­amide-κ2N1:O]

Bozkurt, N.; Tunç, T.; Çaylak Delibaş, N.; Necefoğlu, H.; Hökelek, T.

doi:10.1107/S160053681301965X

metal-organic compounds

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ISSN: 2056-9890

Volume 69| Part 8| August 2013| Pages m466-m467

doi:10.1107/S160053681301965X

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catena-Poly[[aquabis(3-chlorobenzoato-κ²O,O′)cadmium]-μ-N,N-diethylnicotinamide-κ²N¹:O]

Nihat Bozkurt,^a Tuncay Tunç,^b Nagihan Çaylak Delibaş,^c Hacali Necefoğlu ^a and Tuncer Hökelek ^d ^*

^aDepartment of Chemistry, Kafkas University, 36100 Kars, Turkey, ^bAksaray University, Science Education Department, 68100, Aksaray, Turkey, ^cDepartment of Physics, Sakarya University, 54187 Esentepe, Sakarya, Turkey, and ^dDepartment of Physics, Hacettepe University, 06800 Beytepe, Ankara, Turkey
^*Correspondence e-mail: merzifon@hacettepe.edu.tr

(Received 11 July 2013; accepted 16 July 2013; online 20 July 2013)

In the crystal of the title Cd^II polymeric complex, [Cd(C₇H₄ClO₂)₂(C₁₀H₁₄N₂O)(H₂O)]_n, the Cd^II cation is chelated by two chlorobenzoate anions and coordinated by two N,N-diethylnicotinamide (DENA) ligands and one water molecule in a distorted NO₆ pentagonal–bipyramidal geometry. The Cd^II cations are bridged by the pyridine N atom and carbonyl O atom of the DENA ligand to form a polymeric chain running along the b axis. Intermolecular O—H⋯O hydrogen bonds between coordinating water molecules and carboxylate groups link adjacent chains into layers parallel to the bc plane. π–π contacts between benzene rings [shortest centroid–centroid distance = 3.912 (2) Å] further stabilizes the crystal structure. In the molecule, weak C—H⋯O hydrogen bonds occur between the pyridine ring and carboxylate groups; the dihedral angles between the carboxylate groups and adjacent benzene rings are 4.6 (3) and 12.8 (3)°, while the benzene rings are oriented at a dihedral angle of 1.89 (13)°.

Related literature

For niacin, see: Krishnamachari (1974 ). For N,N-diethylnicotinamide, see: Bigoli et al. (1972 ). For related structures, see: Çaylak Delibaş et al. (2013 ); Greenaway et al. (1984 ); Hökelek et al. (1995 ); Hökelek & Necefoğlu (1996 ); Hökelek et al. (2009a ,b ,c ,d ,e ,f ,g ); Hökelek et al. (2011 ); Necefoğlu et al. (2010a ,b ); Sertçelik et al. (2013 ).

Experimental

Crystal data

[Cd(C₇H₄ClO₂)₂(C₁₀H₁₄N₂O)(H₂O)]
M_r = 619.76
Monoclinic, C 2/c
a = 25.1809 (5) Å
b = 7.0161 (3) Å
c = 30.6755 (6) Å
β = 106.203 (3)°
V = 5204.2 (3) Å³
Z = 8
Mo Kα radiation
μ = 1.09 mm⁻¹
T = 296 K
0.35 × 0.15 × 0.10 mm

Data collection

Bruker SMART BREEZE CCD diffractometer
Absorption correction: multi-scan (SADABS; Bruker, 2012 ) T_min = 0.823, T_max = 0.897
100329 measured reflections
6531 independent reflections
6170 reflections with I > 2σ(I)
R_int = 0.026

Refinement

R[F² > 2σ(F²)] = 0.046
wR(F²) = 0.093
S = 1.35
6531 reflections
326 parameters
4 restraints
H atoms treated by a mixture of independent and constrained refinement
Δρ_max = 0.77 e Å⁻³
Δρ_min = −1.02 e Å⁻³

Table 1
Selected bond lengths (Å)

Cd1—O1	2.504 (3)
Cd1—O2	2.323 (3)
Cd1—O3	2.421 (3)
Cd1—O4	2.360 (3)
Cd1—O5	2.410 (3)
Cd1—O6	2.314 (3)
Cd1—N1	2.305 (3)

Table 2
Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
O6—H61⋯O2ⁱ	0.85 (4)	1.94 (4)	2.753 (5)	160 (4)
O6—H62⋯O4ⁱ	0.86 (4)	2.11 (4)	2.838 (4)	142 (5)
C15—H15⋯O1	0.93	2.52	3.181 (5)	128
C19—H19⋯O3	0.93	2.47	3.130 (5)	128
Symmetry code: (i) -x+1, -y+2, -z.

Data collection: APEX2 (Bruker, 2012); cell refinement: SAINT (Bruker, 2012); data reduction: SAINT; program(s) used to solve structure: SHELXS97 (Sheldrick, 2008 ); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008); molecular graphics: ORTEP-3 for Windows (Farrugia, 2012 ); software used to prepare material for publication: WinGX (Farrugia, 2012) and PLATON (Spek, 2009 ).

Supporting information

Crystal structure: contains datablocks I, global. DOI: 10.1107/S160053681301965X/xu5721sup1.cif

Structure factors: contains datablock I. DOI: 10.1107/S160053681301965X/xu5721Isup2.hkl

checkCIF report

Comment top

As a part of our ongoing investigation on transition metal complexes of nicotinamide (NA), one form of niacin (Krishnamachari, 1974), and/or the nicotinic acid derivative N,N-diethylnicotinamide (DENA), an important respiratory stimulant (Bigoli et al., 1972), the title compound was synthesized and its crystal structure is reported herein.

The structures of some DENA and/or NA complexes of the Cu²⁺, Zn²⁺ and Co²⁺ ions, [Cu₂(C₆H₅COO)₄(C₁₀H₁₄N₂O)₂] (Hökelek et al., 1995); [Cu₂(C₈H₇O₂)₄(C₆H₆N₂O)₂] (Necefoğlu et al., 2010a); [Zn₂(C₁₁H₁₄NO₂)₄(C₁₀H₁₄N₂O)₂] (Hökelek et al., 2009a); [Zn₂(C₈H₈NO₂)₄(C₁₀H₁₄N₂O)₂].2H₂O (Hökelek et al., 2009b); [Zn₂(C₉H₁₀NO₂)₄(C₁₀H₁₄N₂O)₂] (Hökelek et al., 2009c); [Zn₂(C₈H₇O₂)₄(C₁₀H₁₄N₂O)₂] (Necefoğlu et al., 2010b) and [Co₂(C₁₁H₁₄NO₂)₄(C₁₀H₁₄N₂O)₂] (Hökelek et al., 2011) have also been determined. In these structures, the benzoate ion acts as a bidentate ligand.

The asymmetric unit of the title Cd^II complex, [Cd(CB)₂(DENA)(H₂O)]_n, contains two 3-chlorobenzoate (CB), one N,N-diethylnicotinamide (DENA) ligands and one coordinated water molecule; the CB ions act as bidentate ligands (Fig. 1). The coordination number of the Cd^II ion is six. Intramolecular C—H···O hydrogen bonds (Fig. 1 and Table 2) link the DENA ligand to the carboxyl groups. The O1—Cd1—O2 and O3—Cd1—O4 angles are 53.75 (10)° and 54.23 (9) °, respectively. The corresponding O—M—O (where M is a , metal) angles are 53.50 (14)° in [Cu₂(C₈H₅O₃)₄(C₆H₆N₂O)₄] (Sertçelik et al., 2013), 53.45 (4)° and 51.97 (4)° in [Cd(C₇H₅O₃)₂(C₆H₆NO)(H₂O)₂].2(H₂O) (Çaylak Delibaş et al., 2013), 52.91 (4)° and 53.96 (4)° in [Cd(C₈H₅O₃)₂(C₆H₆N₂O)₂(H₂O)].H₂O (Hökelek et al., 2009d), 60.70 (4)° in [Co(C₉H₁₀NO₂)₂(C₆H₆N₂O)(H₂O)₂] (Hökelek et al., 2009e), 58.45 (9)° in [Mn(C₉H₁₀NO₂)₂- (C₆H₆N₂O)(H₂O)₂] (Hökelek et al., 2009f), 60.03 (6)° in [Zn(C₈H₈NO₂)₂(C₆H₆N₂O)₂].H₂O (Hökelek et al., 2009g), 58.3 (3)° in [Zn₂(C₁₀H₁₄N₂O)₂(C₇H₅O₃)₄].2H₂O (Hökelek & Necefoğlu, 1996) and 55.2 (1)° in [Cu(Asp)₂(py)₂] (where Asp is acetylsalicylate and py is pyridine) (Greenaway et al., 1984). The dihedral angles between the planar carboxylate groups [(O1/O2/C1) and (O3/O4/C8)] and the adjacent benzene rings A (C2—C7) and B (C9—C14) are 4.56 (28)° and 12.84 (26)°, respectively, while that between rings A, B and C (N1/C15–C19) are A/B = 1.89 (13), A/C = 34.83 (13) and B/C = 35.13 (11) °.

In the crystal, the Cd^II ions [Cd1···Cd1a = 7.0161 (5) Å; symmetry code: (a) x, y - 1, z] are bridged by the N and O atoms of the DENA ligands forming polymeric chains running along the b-axis direction, where the coordination number of each Cd^II atom is seven within a CdO₆N donor set (Fig. 2). The average Cd—O distance is 2.389 (3) Å (Table 1). The Cd atom lies 0.0972 (3) Å below and 0.0127 (3) Å above of the carboxylate groups [(O1/O2/C1) and (O3/O4/C8)], respectively. Strong intermolecular O—H···O hydrogen bonds (Table 2) between water molecules and carboxylate groups link the adjacent chains into layers parallel to the bc plane. π···π contacts between the benzene rings Cg1—Cg2ⁱ, [symmetry code: (i) 1 - x, 2 - y, - z, where Cg1 and Cg2 are the centroids of the rings A (C2—C7) and B (C9—C14), respectively] may further stabilize the structure, with centroid-centroid distance of 3.912 (2) Å.

Related literature top

For niacin, see: Krishnamachari (1974). For N,N-diethylnicotinamide, see: Bigoli et al. (1972). For related structures, see: Çaylak Delibaş et al. (2013); Greenaway et al. (1984); Hökelek et al. (1995); Hökelek & Necefoğlu (1996); Hökelek et al. (2009a,b,c,d,e,f,g); Hökelek et al. (2011); Necefoğlu et al. (2010a,b); Sertçelik et al. (2013).

Experimental top

The title compound was prepared by the reaction of CdSO₄.8H₂O (1.283 g, 5 mmol) in H₂O (100 ml) and diethylnicotinamide (1.780 g, 10 mmol) in H₂O (10 ml) with sodium 3-chlorobenzoate (1.790 g, 10 mmol) in H₂O (100 ml). The mixture was filtered and set aside to crystallize at ambient temperature for ten days, giving colorless single crystals.

Computing details top

Data collection: APEX2 (Bruker, 2012); cell refinement: SAINT (Bruker, 2012); data reduction: SAINT (Bruker, 2012); program(s) used to solve structure: SHELXS97 (Sheldrick, 2008); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008); molecular graphics: ORTEP-3 for Windows (Farrugia, 2012); software used to prepare material for publication: WinGX (Farrugia, 2012) and PLATON (Spek, 2009).

Figures top

	Fig. 1. The asymmetric unit of the title molecule with the atom-numbering scheme. Displacement ellipsoids are drawn at the 50% probability level. Hydrogen bonds are shown as dashed lines.
	Fig. 2. Part of the polymeric chain of the title compound [symmetry codes: (a) x, y - 1, z; (b) x, 1 + y, z]. Hydrogen atoms have been omitted for clarity.

catena-Poly[[aquabis(3-chlorobenzoato-κ²O,O')cadmium]-µ-N,N-diethylnicotinamide-κ²N¹:O] top

Crystal data top

[Cd(C₇H₄ClO₂)₂(C₁₀H₁₄N₂O)(H₂O)]	F(000) = 2496
M_r = 619.76	D_x = 1.582 Mg m⁻³
Monoclinic, C2/c	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: -C2yc	Cell parameters from 9713 reflections
a = 25.1809 (5) Å	θ = 2.5–28.4°
b = 7.0161 (3) Å	µ = 1.09 mm⁻¹
c = 30.6755 (6) Å	T = 296 K
β = 106.203 (3)°	Rod-shaped, colourless
V = 5204.2 (3) Å³	0.35 × 0.15 × 0.10 mm
Z = 8

Data collection top

Bruker SMART BREEZE CCD diffractometer	6531 independent reflections
Radiation source: fine-focus sealed tube	6170 reflections with I > 2σ(I)
Graphite monochromator	R_int = 0.026
ϕ and ω scans	θ_max = 28.4°, θ_min = 1.4°
Absorption correction: multi-scan (SADABS; Bruker, 2012)	h = −33→33
T_min = 0.823, T_max = 0.897	k = −9→9
100329 measured reflections	l = −41→40

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)] = 0.046	Hydrogen site location: inferred from neighbouring sites
wR(F²) = 0.093	H atoms treated by a mixture of independent and constrained refinement
S = 1.35	w = 1/[σ²(F_o²) + (0.0097P)² + 22.0143P] where P = (F_o² + 2F_c²)/3
6531 reflections	(Δ/σ)_max = 0.001
326 parameters	Δρ_max = 0.77 e Å⁻³
4 restraints	Δρ_min = −1.02 e Å⁻³

Crystal data top

[Cd(C₇H₄ClO₂)₂(C₁₀H₁₄N₂O)(H₂O)]	V = 5204.2 (3) Å³
M_r = 619.76	Z = 8
Monoclinic, C2/c	Mo Kα radiation
a = 25.1809 (5) Å	µ = 1.09 mm⁻¹
b = 7.0161 (3) Å	T = 296 K
c = 30.6755 (6) Å	0.35 × 0.15 × 0.10 mm
β = 106.203 (3)°

Data collection top

Bruker SMART BREEZE CCD diffractometer	6531 independent reflections
Absorption correction: multi-scan (SADABS; Bruker, 2012)	6170 reflections with I > 2σ(I)
T_min = 0.823, T_max = 0.897	R_int = 0.026
100329 measured reflections

Refinement top

R[F² > 2σ(F²)] = 0.046	4 restraints
wR(F²) = 0.093	H atoms treated by a mixture of independent and constrained refinement
S = 1.35	w = 1/[σ²(F_o²) + (0.0097P)² + 22.0143P] where P = (F_o² + 2F_c²)/3
6531 reflections	Δρ_max = 0.77 e Å⁻³
326 parameters	Δρ_min = −1.02 e Å⁻³

Special details top

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 > 2sigma(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	0.430006 (10)	0.86384 (4)	0.032753 (9)	0.03649 (8)
Cl1	0.67865 (6)	0.6435 (2)	0.24132 (4)	0.0797 (4)
Cl2	0.20678 (5)	1.2006 (2)	−0.17853 (4)	0.0741 (4)
O1	0.50773 (11)	0.7328 (5)	0.09538 (10)	0.0534 (7)
O2	0.50591 (11)	1.0331 (5)	0.07578 (9)	0.0533 (7)
O3	0.35198 (12)	0.9354 (4)	−0.03179 (10)	0.0547 (8)
O4	0.41552 (11)	1.1524 (4)	−0.00840 (9)	0.0500 (7)
O5	0.39003 (12)	0.9782 (4)	0.09065 (10)	0.0498 (7)
O6	0.47410 (12)	0.7107 (5)	−0.01422 (11)	0.0485 (7)
H61	0.472 (2)	0.785 (7)	−0.0367 (12)	0.083 (19)*
H62	0.5081 (12)	0.709 (10)	0.0016 (18)	0.13 (3)*
N1	0.38036 (12)	0.6005 (4)	0.04343 (10)	0.0349 (6)
N2	0.42885 (14)	1.1630 (5)	0.15138 (11)	0.0453 (8)
C1	0.52769 (14)	0.8941 (6)	0.10063 (12)	0.0420 (9)
C2	0.57856 (13)	0.9332 (6)	0.13935 (12)	0.0368 (8)
C3	0.60309 (14)	0.7865 (6)	0.16792 (12)	0.0410 (8)
H3	0.5892	0.6631	0.1627	0.049*
C4	0.64831 (15)	0.8243 (6)	0.20430 (13)	0.0451 (9)
C5	0.66979 (17)	1.0049 (8)	0.21233 (15)	0.0575 (12)
H5	0.7004	1.0287	0.2369	0.069*
C6	0.6455 (2)	1.1492 (8)	0.18368 (16)	0.0648 (13)
H6	0.6597	1.2721	0.1888	0.078*
C7	0.59975 (17)	1.1136 (6)	0.14707 (15)	0.0516 (10)
H7	0.5835	1.2125	0.1278	0.062*
C8	0.37094 (14)	1.0967 (5)	−0.03489 (11)	0.0367 (8)
C9	0.33859 (14)	1.2296 (5)	−0.07074 (11)	0.0328 (7)
C10	0.29377 (14)	1.1625 (5)	−0.10465 (11)	0.0364 (7)
H10	0.2847	1.0337	−0.1060	0.044*
C11	0.26293 (16)	1.2868 (6)	−0.13623 (13)	0.0458 (9)
C12	0.2747 (2)	1.4770 (7)	−0.13478 (15)	0.0583 (12)
H12	0.2530	1.5599	−0.1561	0.070*
C13	0.3196 (2)	1.5445 (6)	−0.10090 (16)	0.0606 (12)
H13	0.3280	1.6737	−0.0994	0.073*
C14	0.35155 (18)	1.4214 (6)	−0.06956 (13)	0.0465 (9)
H14	0.3821	1.4673	−0.0474	0.056*
C15	0.40358 (14)	0.4560 (5)	0.07000 (12)	0.0363 (7)
H15	0.4418	0.4552	0.0822	0.044*
C16	0.37313 (15)	0.3070 (5)	0.08017 (12)	0.0346 (7)
C17	0.31657 (15)	0.3072 (6)	0.06121 (13)	0.0442 (9)
H17	0.2951	0.2065	0.0665	0.053*
C18	0.29234 (16)	0.4580 (7)	0.03445 (15)	0.0523 (10)
H18	0.2542	0.4629	0.0220	0.063*
C19	0.32558 (15)	0.6014 (6)	0.02650 (13)	0.0442 (9)
H19	0.3091	0.7037	0.0085	0.053*
C20	0.39878 (15)	1.1380 (5)	0.10824 (13)	0.0408 (8)
C21	0.43608 (18)	1.3440 (7)	0.17587 (14)	0.0530 (10)
H21A	0.4277	1.3260	0.2046	0.064*
H21B	0.4101	1.4362	0.1583	0.064*
C22	0.4944 (2)	1.4228 (8)	0.18486 (17)	0.0724 (14)
H22A	0.4972	1.5408	0.2012	0.109*
H22B	0.5026	1.4446	0.1565	0.109*
H22C	0.5203	1.3328	0.2026	0.109*
C23	0.4519 (2)	0.9923 (7)	0.17814 (16)	0.0606 (12)
H23A	0.4863	1.0261	0.2004	0.073*
H23B	0.4601	0.8969	0.1581	0.073*
C24	0.4129 (3)	0.9093 (9)	0.2021 (2)	0.097 (2)
H24A	0.4306	0.8052	0.2210	0.146*
H24B	0.3802	0.8641	0.1802	0.146*
H24C	0.4029	1.0056	0.2207	0.146*

Atomic displacement parameters (Å²) top

	U¹¹	U²²	U³³	U¹²	U¹³	U²³
Cd1	0.03456 (13)	0.03444 (13)	0.03743 (13)	−0.00848 (11)	0.00502 (9)	0.00642 (11)
Cl1	0.0728 (8)	0.0926 (10)	0.0612 (7)	0.0290 (8)	−0.0022 (6)	0.0143 (7)
Cl2	0.0523 (6)	0.1018 (11)	0.0533 (6)	−0.0002 (7)	−0.0100 (5)	0.0020 (7)
O1	0.0415 (15)	0.0632 (19)	0.0483 (16)	−0.0173 (14)	0.0008 (12)	−0.0009 (14)
O2	0.0414 (15)	0.070 (2)	0.0435 (15)	−0.0062 (14)	0.0043 (12)	0.0154 (15)
O3	0.0528 (16)	0.0446 (16)	0.0570 (17)	−0.0091 (13)	−0.0005 (13)	0.0198 (14)
O4	0.0392 (14)	0.0561 (17)	0.0474 (15)	−0.0072 (13)	−0.0002 (11)	0.0094 (14)
O5	0.0609 (17)	0.0322 (14)	0.0653 (18)	−0.0061 (13)	0.0322 (15)	−0.0015 (13)
O6	0.0440 (16)	0.0526 (17)	0.0512 (17)	−0.0086 (13)	0.0173 (13)	0.0004 (14)
N1	0.0369 (14)	0.0292 (15)	0.0384 (15)	−0.0081 (12)	0.0103 (12)	0.0011 (12)
N2	0.0537 (19)	0.0402 (18)	0.0457 (18)	0.0070 (15)	0.0200 (15)	0.0106 (14)
C1	0.0291 (16)	0.063 (3)	0.0349 (18)	−0.0060 (17)	0.0107 (14)	0.0010 (18)
C2	0.0260 (15)	0.049 (2)	0.0356 (17)	−0.0057 (14)	0.0095 (13)	−0.0025 (15)
C3	0.0344 (17)	0.048 (2)	0.0401 (19)	−0.0016 (16)	0.0102 (15)	−0.0038 (17)
C4	0.0351 (18)	0.060 (3)	0.0383 (19)	0.0069 (17)	0.0074 (15)	−0.0016 (18)
C5	0.041 (2)	0.080 (3)	0.045 (2)	−0.013 (2)	0.0015 (18)	−0.014 (2)
C6	0.062 (3)	0.059 (3)	0.068 (3)	−0.023 (2)	0.008 (2)	−0.014 (2)
C7	0.049 (2)	0.046 (2)	0.058 (2)	−0.0066 (19)	0.0110 (19)	0.002 (2)
C8	0.0339 (17)	0.045 (2)	0.0324 (17)	−0.0001 (15)	0.0108 (13)	0.0058 (15)
C9	0.0377 (17)	0.0326 (17)	0.0300 (16)	−0.0011 (14)	0.0128 (13)	0.0032 (13)
C10	0.0373 (17)	0.0345 (18)	0.0376 (18)	−0.0006 (14)	0.0109 (14)	0.0006 (14)
C11	0.041 (2)	0.060 (3)	0.0341 (19)	0.0080 (18)	0.0072 (15)	0.0051 (18)
C12	0.070 (3)	0.053 (3)	0.048 (2)	0.018 (2)	0.011 (2)	0.018 (2)
C13	0.085 (3)	0.033 (2)	0.061 (3)	0.003 (2)	0.016 (2)	0.007 (2)
C14	0.059 (2)	0.037 (2)	0.040 (2)	−0.0086 (18)	0.0097 (17)	−0.0011 (16)
C15	0.0350 (17)	0.0350 (18)	0.0388 (18)	−0.0089 (14)	0.0102 (14)	0.0001 (15)
C16	0.0413 (18)	0.0294 (16)	0.0366 (17)	−0.0043 (14)	0.0168 (14)	−0.0004 (14)
C17	0.0406 (19)	0.041 (2)	0.054 (2)	−0.0147 (16)	0.0187 (17)	0.0038 (17)
C18	0.0332 (18)	0.060 (3)	0.061 (3)	−0.0097 (18)	0.0097 (17)	0.012 (2)
C19	0.0403 (19)	0.039 (2)	0.052 (2)	−0.0046 (16)	0.0100 (16)	0.0093 (17)
C20	0.0464 (19)	0.0345 (18)	0.049 (2)	−0.0065 (16)	0.0265 (17)	0.0047 (16)
C21	0.061 (3)	0.055 (3)	0.043 (2)	0.009 (2)	0.0142 (19)	0.0029 (19)
C22	0.070 (3)	0.079 (4)	0.062 (3)	−0.010 (3)	0.010 (2)	0.000 (3)
C23	0.069 (3)	0.056 (3)	0.065 (3)	0.022 (2)	0.032 (2)	0.024 (2)
C24	0.116 (5)	0.085 (4)	0.117 (5)	0.037 (4)	0.076 (4)	0.059 (4)

Geometric parameters (Å, º) top

Cd1—O1	2.504 (3)	C9—C10	1.386 (5)
Cd1—O2	2.323 (3)	C9—C14	1.383 (5)
Cd1—O3	2.421 (3)	C10—C11	1.372 (5)
Cd1—O4	2.360 (3)	C10—H10	0.9300
Cd1—O5	2.410 (3)	C11—C12	1.365 (6)
Cd1—O6	2.314 (3)	C12—C13	1.388 (7)
Cd1—N1	2.305 (3)	C12—H12	0.9300
Cd1—C1	2.752 (4)	C13—H13	0.9300
Cd1—C8	2.732 (3)	C14—C13	1.373 (6)
Cl1—C4	1.732 (4)	C14—H14	0.9300
Cl2—C11	1.739 (4)	C15—C16	1.383 (5)
O1—C1	1.230 (5)	C15—H15	0.9300
O3—C8	1.242 (4)	C16—C17	1.380 (5)
O4—C8	1.251 (4)	C16—C20ⁱ	1.502 (5)
O6—H61	0.856 (17)	C17—C18	1.373 (6)
O6—H62	0.86 (2)	C17—H17	0.9300
O5—C20	1.237 (5)	C18—H18	0.9300
N1—C15	1.330 (4)	C19—C18	1.374 (5)
N1—C19	1.331 (5)	C19—H19	0.9300
N2—C21	1.461 (5)	C20—N2	1.340 (5)
N2—C23	1.476 (5)	C20—C16ⁱⁱ	1.502 (5)
C1—O2	1.265 (5)	C21—C22	1.521 (6)
C2—C1	1.509 (5)	C21—H21A	0.9700
C2—C3	1.381 (5)	C21—H21B	0.9700
C2—C7	1.368 (6)	C22—H22A	0.9600
C3—C4	1.380 (5)	C22—H22B	0.9600
C3—H3	0.9300	C22—H22C	0.9600
C4—C5	1.372 (6)	C23—C24	1.500 (6)
C5—C6	1.368 (7)	C23—H23A	0.9700
C5—H5	0.9300	C23—H23B	0.9700
C6—H6	0.9300	C24—H24A	0.9600
C7—C6	1.389 (6)	C24—H24B	0.9600
C7—H7	0.9300	C24—H24C	0.9600
C9—C8	1.497 (5)

O1—Cd1—C1	26.54 (11)	C7—C6—H6	119.8
O1—Cd1—C8	161.03 (10)	C2—C7—C6	120.1 (4)
O2—Cd1—O1	53.75 (10)	C2—C7—H7	119.9
O2—Cd1—O3	135.22 (10)	C6—C7—H7	119.9
O2—Cd1—O4	81.10 (10)	O3—C8—Cd1	62.38 (19)
O2—Cd1—O5	81.83 (10)	O3—C8—O4	122.0 (3)
O2—Cd1—C1	27.21 (11)	O3—C8—C9	118.8 (3)
O2—Cd1—C8	108.24 (11)	O4—C8—Cd1	59.57 (19)
O3—Cd1—O1	170.39 (10)	O4—C8—C9	119.2 (3)
O3—Cd1—C1	162.33 (11)	C9—C8—Cd1	178.0 (3)
O3—Cd1—C8	27.04 (10)	C10—C9—C8	120.1 (3)
O4—Cd1—O1	134.15 (9)	C14—C9—C8	120.7 (3)
O4—Cd1—O3	54.23 (9)	C14—C9—C10	119.1 (3)
O4—Cd1—O5	94.28 (10)	C9—C10—H10	120.1
O4—Cd1—C1	108.10 (11)	C11—C10—C9	119.7 (4)
O4—Cd1—C8	27.19 (10)	C11—C10—H10	120.1
O5—Cd1—O1	87.40 (10)	C10—C11—Cl2	119.2 (3)
O5—Cd1—O3	97.07 (11)	C12—C11—C10	121.6 (4)
O5—Cd1—C1	83.43 (10)	C12—C11—Cl2	119.2 (3)
O5—Cd1—C8	96.30 (10)	C11—C12—C13	118.8 (4)
O6—Cd1—O1	84.21 (11)	C11—C12—H12	120.6
O6—Cd1—O2	97.43 (11)	C13—C12—H12	120.6
O6—Cd1—O3	90.46 (11)	C12—C13—H13	119.8
O6—Cd1—O4	95.42 (11)	C14—C13—C12	120.4 (4)
O6—Cd1—O5	170.03 (11)	C14—C13—H13	119.8
O6—Cd1—C1	91.39 (11)	C9—C14—H14	119.8
O6—Cd1—C8	93.37 (11)	C13—C14—C9	120.4 (4)
N1—Cd1—O1	86.30 (10)	C13—C14—H14	119.8
N1—Cd1—O2	136.21 (10)	N1—C15—C16	122.6 (3)
N1—Cd1—O3	86.21 (10)	N1—C15—H15	118.7
N1—Cd1—O4	139.00 (10)	C16—C15—H15	118.7
N1—Cd1—O5	78.90 (10)	C15—C16—C20ⁱ	123.4 (3)
N1—Cd1—O6	95.16 (10)	C17—C16—C15	118.4 (3)
N1—Cd1—C1	111.11 (11)	C17—C16—C20ⁱ	118.1 (3)
N1—Cd1—C8	112.67 (10)	C16—C17—H17	120.4
C8—Cd1—C1	135.29 (12)	C18—C17—C16	119.1 (3)
C1—O1—Cd1	88.1 (2)	C18—C17—H17	120.4
C1—O2—Cd1	95.6 (2)	C17—C18—C19	118.7 (4)
C8—O3—Cd1	90.6 (2)	C17—C18—H18	120.7
C8—O4—Cd1	93.2 (2)	C19—C18—H18	120.7
C20—O5—Cd1	124.3 (2)	N1—C19—C18	122.9 (4)
Cd1—O6—H61	107 (4)	N1—C19—H19	118.5
Cd1—O6—H62	103 (5)	C18—C19—H19	118.5
H61—O6—H62	107 (4)	O5—C20—N2	122.2 (4)
C15—N1—Cd1	122.3 (2)	O5—C20—C16ⁱⁱ	118.0 (3)
C15—N1—C19	118.2 (3)	N2—C20—C16ⁱⁱ	119.8 (3)
C19—N1—Cd1	119.0 (2)	N2—C21—C22	112.6 (4)
C20—N2—C21	125.2 (3)	N2—C21—H21A	109.1
C20—N2—C23	118.0 (4)	N2—C21—H21B	109.1
C21—N2—C23	116.5 (3)	C22—C21—H21A	109.1
O1—C1—Cd1	65.4 (2)	C22—C21—H21B	109.1
O1—C1—O2	122.5 (3)	H21A—C21—H21B	107.8
O1—C1—C2	119.7 (4)	C21—C22—H22A	109.5
O2—C1—Cd1	57.16 (19)	C21—C22—H22B	109.5
O2—C1—C2	117.7 (4)	C21—C22—H22C	109.5
C2—C1—Cd1	173.1 (3)	H22A—C22—H22B	109.5
C3—C2—C1	119.7 (3)	H22A—C22—H22C	109.5
C7—C2—C1	120.6 (4)	H22B—C22—H22C	109.5
C7—C2—C3	119.7 (3)	N2—C23—C24	112.3 (4)
C2—C3—H3	120.3	N2—C23—H23A	109.2
C4—C3—C2	119.5 (4)	N2—C23—H23B	109.2
C4—C3—H3	120.3	C24—C23—H23A	109.2
C3—C4—Cl1	120.2 (3)	C24—C23—H23B	109.2
C5—C4—Cl1	118.6 (3)	H23A—C23—H23B	107.9
C5—C4—C3	121.2 (4)	C23—C24—H24A	109.5
C4—C5—H5	120.5	C23—C24—H24B	109.5
C6—C5—C4	119.0 (4)	C23—C24—H24C	109.5
C6—C5—H5	120.5	H24A—C24—H24B	109.5
C5—C6—C7	120.5 (4)	H24A—C24—H24C	109.5
C5—C6—H6	119.8	H24B—C24—H24C	109.5

O2—Cd1—O1—C1	1.3 (2)	Cd1—O5—C20—N2	−109.6 (3)
O4—Cd1—O1—C1	13.0 (3)	Cd1—O5—C20—C16ⁱⁱ	72.2 (4)
O5—Cd1—O1—C1	−80.5 (2)	C15—N1—Cd1—O1	−9.4 (3)
O6—Cd1—O1—C1	104.9 (2)	C15—N1—Cd1—O2	−31.9 (3)
N1—Cd1—O1—C1	−159.5 (2)	C15—N1—Cd1—O3	164.6 (3)
C8—Cd1—O1—C1	21.4 (5)	C15—N1—Cd1—O4	178.8 (2)
O1—Cd1—O2—C1	−1.3 (2)	C15—N1—Cd1—O5	−97.5 (3)
O3—Cd1—O2—C1	−176.7 (2)	C15—N1—Cd1—O6	74.4 (3)
O4—Cd1—O2—C1	−172.8 (2)	C15—N1—Cd1—C1	−19.0 (3)
O5—Cd1—O2—C1	91.5 (2)	C15—N1—Cd1—C8	170.3 (3)
O6—Cd1—O2—C1	−78.4 (2)	C19—N1—Cd1—O1	163.1 (3)
N1—Cd1—O2—C1	27.0 (3)	C19—N1—Cd1—O2	140.6 (3)
C8—Cd1—O2—C1	−174.5 (2)	C19—N1—Cd1—O3	−22.9 (3)
O2—Cd1—O3—C8	4.5 (3)	C19—N1—Cd1—O4	−8.6 (4)
O4—Cd1—O3—C8	−0.2 (2)	C19—N1—Cd1—O5	75.1 (3)
O5—Cd1—O3—C8	90.0 (2)	C19—N1—Cd1—O6	−113.0 (3)
O6—Cd1—O3—C8	−96.5 (2)	C19—N1—Cd1—C1	153.5 (3)
N1—Cd1—O3—C8	168.3 (2)	C19—N1—Cd1—C8	−17.2 (3)
C1—Cd1—O3—C8	−0.5 (5)	Cd1—N1—C15—C16	173.3 (3)
O1—Cd1—O4—C8	174.0 (2)	C19—N1—C15—C16	0.7 (5)
O2—Cd1—O4—C8	−176.5 (2)	Cd1—N1—C19—C18	−174.4 (3)
O3—Cd1—O4—C8	0.2 (2)	C15—N1—C19—C18	−1.5 (6)
O5—Cd1—O4—C8	−95.5 (2)	C20—N2—C21—C22	−109.8 (5)
O6—Cd1—O4—C8	86.8 (2)	C23—N2—C21—C22	76.9 (5)
N1—Cd1—O4—C8	−17.5 (3)	C20—N2—C23—C24	−89.3 (5)
C1—Cd1—O4—C8	−179.9 (2)	C21—N2—C23—C24	84.5 (6)
O1—Cd1—C1—O2	177.7 (4)	O1—C1—O2—Cd1	2.4 (4)
O2—Cd1—C1—O1	−177.7 (4)	C2—C1—O2—Cd1	−174.6 (3)
O3—Cd1—C1—O1	−170.0 (3)	C3—C2—C1—O1	1.6 (5)
O3—Cd1—C1—O2	7.8 (5)	C3—C2—C1—O2	178.7 (3)
O4—Cd1—C1—O1	−170.3 (2)	C7—C2—C1—O1	−176.8 (4)
O4—Cd1—C1—O2	7.5 (2)	C7—C2—C1—O2	0.4 (5)
O5—Cd1—C1—O1	97.4 (2)	C1—C2—C3—C4	−177.5 (3)
O5—Cd1—C1—O2	−84.9 (2)	C7—C2—C3—C4	0.9 (6)
O6—Cd1—C1—O1	−74.1 (2)	C1—C2—C7—C6	177.9 (4)
O6—Cd1—C1—O2	103.6 (2)	C3—C2—C7—C6	−0.5 (6)
N1—Cd1—C1—O1	22.0 (3)	C2—C3—C4—Cl1	178.4 (3)
N1—Cd1—C1—O2	−160.3 (2)	C2—C3—C4—C5	−0.8 (6)
C8—Cd1—C1—O1	−170.3 (2)	Cl1—C4—C5—C6	−178.9 (4)
C8—Cd1—C1—O2	7.4 (3)	C3—C4—C5—C6	0.3 (7)
O1—Cd1—C8—O3	166.4 (3)	C4—C5—C6—C7	0.1 (7)
O1—Cd1—C8—O4	−13.3 (5)	C2—C7—C6—C5	0.0 (7)
O2—Cd1—C8—O3	−176.6 (2)	C10—C9—C8—O3	−11.4 (5)
O2—Cd1—C8—O4	3.7 (2)	C10—C9—C8—O4	170.1 (3)
O3—Cd1—C8—O4	−179.7 (4)	C14—C9—C8—O3	166.1 (4)
O4—Cd1—C8—O3	179.7 (4)	C14—C9—C8—O4	−12.4 (5)
O5—Cd1—C8—O3	−93.2 (2)	C8—C9—C10—C11	177.2 (3)
O5—Cd1—C8—O4	87.1 (2)	C14—C9—C10—C11	−0.3 (5)
O6—Cd1—C8—O3	84.4 (2)	C8—C9—C14—C13	−175.9 (4)
O6—Cd1—C8—O4	−95.3 (2)	C10—C9—C14—C13	1.6 (6)
N1—Cd1—C8—O3	−12.6 (3)	C9—C10—C11—Cl2	−179.9 (3)
N1—Cd1—C8—O4	167.7 (2)	C9—C10—C11—C12	−1.1 (6)
C1—Cd1—C8—O3	179.8 (2)	C10—C11—C12—C13	1.1 (7)
C1—Cd1—C8—O4	0.1 (3)	Cl2—C11—C12—C13	−180.0 (4)
Cd1—O1—C1—O2	−2.3 (4)	C11—C12—C13—C14	0.2 (7)
Cd1—O1—C1—C2	174.8 (3)	C9—C14—C13—C12	−1.6 (7)
Cd1—O3—C8—O4	0.3 (4)	N1—C15—C16—C17	1.3 (5)
Cd1—O3—C8—C9	−178.2 (3)	N1—C15—C16—C20ⁱ	176.9 (3)
Cd1—O4—C8—O3	−0.3 (4)	C15—C16—C17—C18	−2.4 (6)
Cd1—O4—C8—C9	178.1 (3)	C20ⁱ—C16—C17—C18	−178.4 (4)
C20—O5—Cd1—O1	91.2 (3)	C16—C17—C18—C19	1.7 (6)
C20—O5—Cd1—O2	37.5 (3)	N1—C19—C18—C17	0.3 (7)
C20—O5—Cd1—O3	−97.3 (3)	O5—C20—N2—C21	−173.2 (4)
C20—O5—Cd1—O4	−42.9 (3)	O5—C20—N2—C23	0.0 (5)
C20—O5—Cd1—N1	178.0 (3)	C16ⁱⁱ—C20—N2—C21	5.0 (5)
C20—O5—Cd1—C1	64.9 (3)	C16ⁱⁱ—C20—N2—C23	178.2 (3)
C20—O5—Cd1—C8	−70.1 (3)

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

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
O6—H61···O2ⁱⁱⁱ	0.85 (4)	1.94 (4)	2.753 (5)	160 (4)
O6—H62···O4ⁱⁱⁱ	0.86 (4)	2.11 (4)	2.838 (4)	142 (5)
C15—H15···O1	0.93	2.52	3.181 (5)	128
C19—H19···O3	0.93	2.47	3.130 (5)	128

Symmetry code: (iii) −x+1, −y+2, −z.

Selected bond lengths (Å) top

Cd1—O1	2.504 (3)	Cd1—O5	2.410 (3)
Cd1—O2	2.323 (3)	Cd1—O6	2.314 (3)
Cd1—O3	2.421 (3)	Cd1—N1	2.305 (3)
Cd1—O4	2.360 (3)

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
O6—H61···O2ⁱ	0.85 (4)	1.94 (4)	2.753 (5)	160 (4)
O6—H62···O4ⁱ	0.86 (4)	2.11 (4)	2.838 (4)	142 (5)
C15—H15···O1	0.93	2.52	3.181 (5)	128
C19—H19···O3	0.93	2.47	3.130 (5)	128

Symmetry code: (i) −x+1, −y+2, −z.

Acknowledgements

The authors acknowledge the Aksaray University, Science and Technology Application and Research Center, Aksaray, Turkey, for the use of the Bruker SMART BREEZE CCD diffractometer (purchased under grant No. 2010K120480 of the State of Planning Organization).

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