Reaction of 2-[(2-amino­eth­yl)amino]­ethanol with pyridine-2-carbaldehyde and complexation of the products with Cu^II and Cd^II along with docking studies

The reaction between 2-[2-(amino­eth­yl)amino]­ethanol and pyridine-2-carbaldehyde in a 1:2 molar ratio affords a mixture containing 2-({2-[(pyridin-2-yl­methyl­idene)amino]­eth­yl}amino)­ethanol (PMAE) and 2-[2-(pyridin-2-yl)oxazolidin-3-yl]-N-(pyridin-2-yl­methyl­idene)ethanamine (POPME). Treatment of this mixture with copper(II) chloride or cadmium(II) chloride gave tri­chlorido­[(2-hy­droxy­eth­yl)({2-[(pyridin-2-yl­methyl­idene)amino]­eth­yl})aza­nium]copper(II) monohydrate, [Cu(C₁₀H₁₆N₃O)Cl₃]·H₂O or [Cu(HPMAE)Cl₃]·H₂O, 1, and di­chlorido­{2-[2-(pyridin-2-yl)oxazolidin-3-yl]-N-(pyridin-2-yl­methyl­idene)ethanamine}­cadmium(II), [CdCl₂(C₁₆H₁₈N₄O)] or [CdCl₂(POPME)], 2, which were characterized by elemental analysis, FT–IR, Raman and ¹H NMR spec­troscopy and single-crystal X-ray diffraction. PMAE is potentially a tetra­dentate N₃O-donor ligand but coordinates to copper here as an N₂ donor. In the structure of 1, the geometry around the Cu atom is distorted square pyramidal. In 2, the Cd atom has a distorted octa­hedral geometry. In addition to the hydrogen bonds, there are π–π stacking inter­actions between the pyridine rings in the crystal packing of 1 and 2. The ability of PMAE, POPME and 1 to inter­act with ten selected biomolecules (BRAF kinase, CatB, DNA gyrase, HDAC7, rHA, RNR, TrxR, TS, Top II and B-DNA) was investigated by docking studies and compared with doxorubicin.

Computing details

Data collection: CrysAlis PRO (Agilent, 2012) for km42; CrysAlis PRO (Agilent, 2013) for zk1. Cell refinement: CrysAlis PRO (Agilent, 2012) for km42; CrysAlis PRO (Agilent, 2013) for zk1. Data reduction: CrysAlis PRO (Agilent, 2012) for km42; CrysAlis PRO (Agilent, 2013) for zk1. For both structures, program(s) used to solve structure: SHELXS97 (Sheldrick, 2008); program(s) used to refine structure: SHELXL2018 (Sheldrick, 2015). Molecular graphics: OLEX2 (Dolomanov et al., 2009), ORTEP-3 (Farrugia, 2012), DIAMOND (Bergerhoff et al.., 1996) and Mercury (Macrae et al., 2008) for km42; OLEX2 (Dolomanov et al., 2009), ORTEP-3 (Farrugia, 2012) and DIAMOND (Bergerhoff et al.., 1996) for zk1. For both structures, software used to prepare material for publication: OLEX2 (Dolomanov et al., 2009).

Trichlorido[(2-hydroxyethyl)({2-[(pyridin-2-ylmethylidene)amino]ethyl})azanium]copper(II) monohydrate (km42)

Crystal data

[Cu(C10H16N3O)Cl3]·H2O	F(000) = 780
Mr = 382.16	Dx = 1.715 Mg m^−3
Monoclinic, P21/n	Mo Kα radiation, λ = 0.71073 Å
a = 7.1296 (2) Å	Cell parameters from 3732 reflections
b = 6.9197 (3) Å	θ = 2.9–29.2°
c = 30.0061 (11) Å	µ = 2.02 mm^−1
β = 91.066 (3)°	T = 150 K
V = 1480.10 (9) Å^3	Block, green
Z = 4	0.08 × 0.07 × 0.06 mm

Data collection

Agilent Xcalibur Eos Gemini ultra diffractometer	3419 independent reflections
Radiation source: Enhance (Mo) X-ray Source	3199 reflections with I > 2σ(I)
Graphite monochromator	Rint = 0.028
Detector resolution: 16.2705 pixels mm^-1	θmax = 29.2°, θmin = 2.9°
ω scans	h = −8→9
Absorption correction: multi-scan (CrysAlis PRO; Agilent, 2012)	k = −5→8
Tmin = 0.908, Tmax = 1.000	l = −39→33
6897 measured reflections

Refinement

Refinement on F^2	Primary atom site location: structure-invariant direct methods
Least-squares matrix: full	Hydrogen site location: mixed
R[F^2 > 2σ(F^2)] = 0.068	H atoms treated by a mixture of independent and constrained refinement
wR(F^2) = 0.146	w = 1/[σ^2(Fo^2) + (0.0128P)^2 + 11.3982P] where P = (Fo^2 + 2Fc^2)/3
S = 1.38	(Δ/σ)max < 0.001
3419 reflections	Δρmax = 0.91 e Å^−3
181 parameters	Δρmin = −0.79 e Å^−3
2 restraints

Special details

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

Refinement. Suitable crystals of 1 and 2 were mounted in oil and diffraction data was collected at 150 K using a Rigaku Oxford Diffraction Xcalibur Gemini Ultra diffractometer fitted with a Mo source emitting graphite-monochromated Mo Kα radiation (λ = 0.71073 Å). Data integration, scaling and empirical absorption correction was carried out using the CrysAlis PRO program package. The structure was solved using direct methods SHELXS (Sheldrick, 1990) and refined by full-matrix least-squares against F² using SHELXL (Sheldrick, 1990). The non-H atoms were refined anisotropically and H atoms were placed at idealized positions and refined using a riding model. All calculations were carried out using the program OLEX2 (Dolomanov et al.., 2009). Diagrams of the molecular structures and unit cells were created using ORTEP-3 (Farrugia, 1997) and DIAMOND (Bergerhoff et al.., 1996) software.

Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Ų)

	x	y	z	Uiso*/Ueq
Cu1	0.20878 (9)	−0.23132 (10)	0.38743 (2)	0.01491 (18)
Cl1	0.35986 (19)	−0.3746 (2)	0.32813 (5)	0.0193 (3)
Cl2	−0.09932 (18)	−0.0913 (2)	0.36009 (4)	0.0191 (3)
Cl3	0.0783 (2)	−0.5160 (2)	0.40924 (5)	0.0203 (3)
N1	0.2317 (6)	−0.1284 (7)	0.45117 (15)	0.0164 (9)
N2	0.3408 (6)	0.0219 (7)	0.37536 (15)	0.0152 (9)
O1	−0.0961 (6)	0.6030 (7)	0.28176 (14)	0.0250 (9)
H1	−0.097297	0.677287	0.303899	0.037*
C10	−0.1836 (8)	0.4253 (9)	0.2928 (2)	0.0211 (12)
H10A	−0.305409	0.414037	0.276686	0.025*
H10B	−0.207415	0.421208	0.325224	0.025*
N3	0.1053 (6)	0.2490 (7)	0.31210 (15)	0.0174 (10)
H3A	0.157593	0.368345	0.315040	0.021*
H3B	0.063540	0.212671	0.339320	0.021*
C2	0.1917 (8)	−0.1099 (10)	0.52984 (19)	0.0208 (12)
H2	0.154751	−0.171083	0.556628	0.025*
C5	0.3035 (7)	0.0538 (8)	0.45260 (18)	0.0149 (11)
O2	0.3733 (7)	0.4831 (8)	0.5851 (2)	0.0389 (13)
C8	0.2534 (8)	0.1097 (9)	0.29789 (18)	0.0185 (11)
H8A	0.305307	0.152730	0.269173	0.022*
H8B	0.196436	−0.019426	0.293270	0.022*
C6	0.3678 (7)	0.1252 (9)	0.40979 (19)	0.0174 (11)
H6	0.428706	0.246908	0.407729	0.021*
C7	0.4111 (7)	0.0949 (9)	0.33252 (18)	0.0167 (11)
H7A	0.509339	0.006780	0.321521	0.020*
H7B	0.468339	0.223902	0.337119	0.020*
C3	0.2595 (8)	0.0769 (10)	0.53068 (19)	0.0226 (13)
H3	0.266624	0.146866	0.557899	0.027*
C9	−0.0588 (8)	0.2616 (9)	0.28035 (18)	0.0191 (11)
H9A	−0.013635	0.281233	0.249679	0.023*
H9B	−0.130448	0.139135	0.280951	0.023*
C1	0.1780 (8)	−0.2083 (9)	0.48930 (19)	0.0187 (11)
H1A	0.128866	−0.335900	0.488864	0.022*
C4	0.3172 (8)	0.1611 (9)	0.49131 (19)	0.0181 (11)
H4	0.364761	0.289349	0.490983	0.022*
H2A	0.251 (5)	0.452 (17)	0.585 (4)	0.09 (4)*
H2B	0.42 (2)	0.45 (3)	0.612 (3)	0.21 (9)*

Atomic displacement parameters (Ų)

	U^11	U^22	U^33	U^12	U^13	U^23
Cu1	0.0162 (3)	0.0122 (3)	0.0164 (3)	−0.0026 (3)	0.0016 (2)	−0.0002 (3)
Cl1	0.0210 (6)	0.0148 (7)	0.0222 (7)	−0.0010 (5)	0.0056 (5)	−0.0019 (5)
Cl2	0.0146 (6)	0.0210 (7)	0.0216 (7)	−0.0003 (5)	0.0013 (5)	0.0033 (5)
Cl3	0.0229 (7)	0.0143 (7)	0.0237 (7)	−0.0041 (5)	0.0041 (5)	0.0013 (5)
N1	0.013 (2)	0.018 (2)	0.019 (2)	0.0004 (19)	−0.0016 (17)	0.0017 (19)
N2	0.011 (2)	0.015 (2)	0.019 (2)	0.0015 (18)	0.0009 (17)	0.0006 (18)
O1	0.028 (2)	0.020 (2)	0.027 (2)	0.0023 (19)	−0.0019 (18)	0.0003 (18)
C10	0.014 (3)	0.027 (3)	0.022 (3)	0.002 (2)	−0.002 (2)	−0.001 (2)
N3	0.019 (2)	0.016 (2)	0.017 (2)	0.000 (2)	0.0006 (17)	−0.0005 (19)
C2	0.017 (3)	0.027 (3)	0.018 (3)	0.006 (2)	0.001 (2)	0.003 (2)
C5	0.009 (2)	0.016 (3)	0.019 (3)	0.003 (2)	−0.0024 (19)	−0.001 (2)
O2	0.026 (3)	0.033 (3)	0.058 (4)	−0.009 (2)	−0.004 (2)	0.006 (3)
C8	0.024 (3)	0.017 (3)	0.015 (3)	0.002 (2)	0.003 (2)	0.000 (2)
C6	0.008 (2)	0.017 (3)	0.026 (3)	0.003 (2)	0.000 (2)	0.000 (2)
C7	0.012 (2)	0.017 (3)	0.021 (3)	0.001 (2)	0.002 (2)	0.003 (2)
C3	0.018 (3)	0.032 (4)	0.018 (3)	0.003 (3)	0.000 (2)	−0.005 (2)
C9	0.024 (3)	0.017 (3)	0.016 (3)	0.000 (2)	−0.003 (2)	−0.001 (2)
C1	0.016 (3)	0.017 (3)	0.023 (3)	−0.002 (2)	0.000 (2)	0.001 (2)
C4	0.014 (2)	0.017 (3)	0.023 (3)	−0.001 (2)	−0.001 (2)	−0.002 (2)

Geometric parameters (Å, º)

Cu1—Cl1	2.3196 (15)	C2—C3	1.380 (9)
Cu1—Cl2	2.5239 (15)	C2—C1	1.396 (8)
Cu1—Cl3	2.2796 (15)	C5—C6	1.458 (8)
Cu1—N1	2.045 (5)	C5—C4	1.381 (8)
Cu1—N2	2.025 (5)	O2—H2A	0.90 (2)
N1—C5	1.361 (8)	O2—H2B	0.90 (2)
N1—C1	1.334 (7)	C8—H8A	0.9900
N2—C6	1.268 (7)	C8—H8B	0.9900
N2—C7	1.477 (7)	C8—C7	1.520 (7)
O1—H1	0.8400	C6—H6	0.9500
O1—C10	1.421 (8)	C7—H7A	0.9900
C10—H10A	0.9900	C7—H7B	0.9900
C10—H10B	0.9900	C3—H3	0.9500
C10—C9	1.492 (8)	C3—C4	1.386 (8)
N3—H3A	0.9100	C9—H9A	0.9900
N3—H3B	0.9100	C9—H9B	0.9900
N3—C8	1.497 (7)	C1—H1A	0.9500
N3—C9	1.498 (7)	C4—H4	0.9500
C2—H2	0.9500
Cl1—Cu1—Cl2	109.18 (5)	N1—C5—C4	123.1 (5)
Cl3—Cu1—Cl1	92.80 (6)	C4—C5—C6	122.7 (5)
Cl3—Cu1—Cl2	93.88 (5)	H2A—O2—H2B	106 (10)
N1—Cu1—Cl1	146.75 (13)	N3—C8—H8A	109.3
N1—Cu1—Cl2	102.96 (13)	N3—C8—H8B	109.3
N1—Cu1—Cl3	93.35 (15)	N3—C8—C7	111.4 (4)
N2—Cu1—Cl1	90.49 (14)	H8A—C8—H8B	108.0
N2—Cu1—Cl2	90.83 (13)	C7—C8—H8A	109.3
N2—Cu1—Cl3	173.04 (14)	C7—C8—H8B	109.3
N2—Cu1—N1	80.58 (19)	N2—C6—C5	118.8 (5)
C5—N1—Cu1	112.1 (4)	N2—C6—H6	120.6
C1—N1—Cu1	129.7 (4)	C5—C6—H6	120.6
C1—N1—C5	118.1 (5)	N2—C7—C8	111.1 (4)
C6—N2—Cu1	114.0 (4)	N2—C7—H7A	109.4
C6—N2—C7	117.9 (5)	N2—C7—H7B	109.4
C7—N2—Cu1	128.2 (4)	C8—C7—H7A	109.4
C10—O1—H1	109.5	C8—C7—H7B	109.4
O1—C10—H10A	109.8	H7A—C7—H7B	108.0
O1—C10—H10B	109.8	C2—C3—H3	120.4
O1—C10—C9	109.4 (5)	C2—C3—C4	119.2 (6)
H10A—C10—H10B	108.2	C4—C3—H3	120.4
C9—C10—H10A	109.8	C10—C9—N3	110.3 (5)
C9—C10—H10B	109.8	C10—C9—H9A	109.6
H3A—N3—H3B	107.7	C10—C9—H9B	109.6
C8—N3—H3A	108.8	N3—C9—H9A	109.6
C8—N3—H3B	108.8	N3—C9—H9B	109.6
C8—N3—C9	113.8 (4)	H9A—C9—H9B	108.1
C9—N3—H3A	108.8	N1—C1—C2	121.9 (6)
C9—N3—H3B	108.8	N1—C1—H1A	119.0
C3—C2—H2	120.3	C2—C1—H1A	119.0
C3—C2—C1	119.4 (6)	C5—C4—C3	118.2 (6)
C1—C2—H2	120.3	C5—C4—H4	120.9
N1—C5—C6	114.2 (5)	C3—C4—H4	120.9

Dichlorido{2-[2-(pyridin-2-yl)oxazolidin-3-yl]-N-(pyridin-2-ylmethylidene)ethanamine}cadmium(II) (zk1)

Crystal data

[CdCl2(C16H18N4O)]	F(000) = 928
Mr = 465.64	Dx = 1.827 Mg m^−3
Monoclinic, P21/c	Mo Kα radiation, λ = 0.71073 Å
a = 14.0924 (3) Å	Cell parameters from 3581 reflections
b = 7.7111 (2) Å	θ = 2.6–28.8°
c = 15.5819 (4) Å	µ = 1.62 mm^−1
β = 90.317 (3)°	T = 150 K
V = 1693.21 (8) Å^3	Plate, colourless
Z = 4	0.12 × 0.07 × 0.02 mm

Data collection

Agilent Xcalibur Eos Gemini ultra diffractometer	3937 independent reflections
Radiation source: Enhance (Mo) X-ray Source	3468 reflections with I > 2σ(I)
Graphite monochromator	Rint = 0.025
Detector resolution: 16.2705 pixels mm^-1	θmax = 29.2°, θmin = 2.6°
ω scans	h = −19→17
Absorption correction: multi-scan (CrysAlis PRO; Agilent, 2013)	k = −10→10
Tmin = 0.843, Tmax = 1.000	l = −20→20
7994 measured reflections

Refinement

Refinement on F^2	Primary atom site location: structure-invariant direct methods
Least-squares matrix: full	Hydrogen site location: inferred from neighbouring sites
R[F^2 > 2σ(F^2)] = 0.026	H-atom parameters constrained
wR(F^2) = 0.054	w = 1/[σ^2(Fo^2) + (0.0182P)^2 + 0.5445P] where P = (Fo^2 + 2Fc^2)/3
S = 1.04	(Δ/σ)max = 0.002
3937 reflections	Δρmax = 0.40 e Å^−3
217 parameters	Δρmin = −0.40 e Å^−3
0 restraints

Special details

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

Refinement. Suitable crystals of 1 and 2 were mounted in oil and diffraction data was collected at 150 K using a Rigaku Oxford Diffraction Xcalibur Gemini Ultra diffractometer fitted with a Mo source emitting graphite-monochromated Mo Kα radiation (λ = 0.71073 Å). Data integration, scaling and empirical absorption correction was carried out using the CrysAlis PRO program package. The structure was solved using direct methods SHELXS (Sheldrick, 1990) and refined by full-matrix least-squares against F² using SHELXL (Sheldrick, 1990). The non-H atoms were refined anisotropically and H atoms were placed at idealized positions and refined using a riding model. All calculations were carried out using the program OLEX2 (Dolomanov et al.., 2009). Diagrams of the molecular structures and unit cells were created using ORTEP-3 (Farrugia, 1997) and DIAMOND (Bergerhoff et al.., 1996) software.

Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Ų)

	x	y	z	Uiso*/Ueq
Cd1	0.72322 (2)	0.77644 (2)	0.39286 (2)	0.01457 (6)
Cl1	0.69652 (4)	0.54339 (7)	0.27381 (4)	0.02331 (13)
Cl2	0.80606 (4)	0.58248 (8)	0.49548 (4)	0.02552 (14)
O1	0.92207 (12)	1.1591 (2)	0.26533 (10)	0.0219 (4)
N1	0.57343 (14)	0.7700 (2)	0.46709 (12)	0.0167 (4)
N3	0.80051 (13)	0.9556 (2)	0.28314 (11)	0.0149 (4)
C13	0.93979 (17)	1.2066 (3)	0.44397 (15)	0.0192 (5)
H13	0.978734	1.270889	0.407964	0.023*
N4	0.81023 (13)	1.0105 (2)	0.45978 (12)	0.0165 (4)
N2	0.60811 (13)	0.9484 (2)	0.32241 (12)	0.0176 (4)
C2	0.46469 (17)	0.6640 (3)	0.57199 (16)	0.0237 (5)
H2	0.455209	0.608317	0.624197	0.028*
C5	0.49914 (16)	0.8322 (3)	0.42215 (15)	0.0176 (5)
C1	0.55591 (17)	0.6888 (3)	0.54096 (15)	0.0207 (5)
H1	0.606892	0.647073	0.573001	0.025*
C16	0.82574 (17)	1.0119 (3)	0.54507 (15)	0.0198 (5)
H16	0.787628	0.943211	0.579774	0.024*
C3	0.38868 (18)	0.7225 (3)	0.52470 (17)	0.0261 (6)
H3	0.326940	0.704118	0.543395	0.031*
C11	0.84039 (16)	1.1186 (3)	0.31545 (14)	0.0160 (5)
H11	0.793262	1.210708	0.307416	0.019*
C15	0.89576 (17)	1.1110 (3)	0.58327 (15)	0.0235 (5)
H15	0.903037	1.112324	0.642619	0.028*
C6	0.52171 (16)	0.9310 (3)	0.34342 (15)	0.0189 (5)
H6	0.473605	0.979249	0.310037	0.023*
C12	0.86610 (16)	1.1084 (3)	0.41011 (14)	0.0150 (5)
C7	0.63678 (16)	1.0547 (3)	0.25001 (15)	0.0198 (5)
H7A	0.645255	1.173848	0.268419	0.024*
H7B	0.587896	1.052234	0.205957	0.024*
C4	0.40591 (17)	0.8099 (3)	0.44832 (17)	0.0227 (5)
H4	0.355897	0.852522	0.415349	0.027*
C14	0.95479 (17)	1.2081 (3)	0.53170 (16)	0.0231 (5)
H14	1.003759	1.273393	0.555563	0.028*
C9	0.88601 (16)	0.8642 (3)	0.25202 (15)	0.0185 (5)
H9A	0.869661	0.779612	0.208315	0.022*
H9B	0.918823	0.806116	0.298736	0.022*
C8	0.72977 (16)	0.9848 (3)	0.21379 (14)	0.0189 (5)
H8A	0.717758	0.876428	0.184015	0.023*
H8B	0.755034	1.066845	0.172643	0.023*
C10	0.94624 (17)	1.0093 (3)	0.21502 (15)	0.0216 (5)
H10A	1.013267	0.982586	0.220492	0.026*
H10B	0.931198	1.027972	0.154904	0.026*

Atomic displacement parameters (Ų)

	U^11	U^22	U^33	U^12	U^13	U^23
Cd1	0.01251 (9)	0.01589 (9)	0.01528 (9)	−0.00011 (6)	−0.00260 (6)	0.00226 (6)
Cl1	0.0278 (3)	0.0191 (3)	0.0230 (3)	−0.0044 (2)	−0.0026 (3)	−0.0031 (2)
Cl2	0.0244 (3)	0.0246 (3)	0.0275 (3)	0.0028 (2)	−0.0079 (3)	0.0081 (3)
O1	0.0256 (9)	0.0207 (8)	0.0194 (8)	−0.0070 (7)	0.0072 (7)	−0.0016 (7)
N1	0.0167 (10)	0.0165 (10)	0.0170 (10)	0.0003 (8)	−0.0016 (8)	−0.0016 (8)
N3	0.0161 (10)	0.0149 (9)	0.0137 (9)	0.0001 (8)	−0.0033 (8)	−0.0017 (8)
C13	0.0198 (12)	0.0162 (11)	0.0217 (12)	0.0007 (10)	−0.0001 (10)	−0.0034 (10)
N4	0.0157 (10)	0.0177 (10)	0.0161 (9)	0.0013 (8)	−0.0019 (8)	0.0002 (8)
N2	0.0175 (10)	0.0171 (10)	0.0180 (10)	0.0014 (8)	−0.0036 (8)	−0.0008 (8)
C2	0.0265 (14)	0.0197 (12)	0.0249 (13)	−0.0025 (11)	0.0083 (11)	−0.0028 (10)
C5	0.0156 (11)	0.0144 (11)	0.0227 (12)	0.0011 (9)	−0.0010 (10)	−0.0059 (10)
C1	0.0206 (12)	0.0211 (12)	0.0204 (12)	−0.0004 (10)	−0.0014 (10)	−0.0014 (10)
C16	0.0204 (12)	0.0227 (12)	0.0165 (11)	0.0047 (10)	0.0004 (10)	0.0010 (10)
C3	0.0191 (13)	0.0224 (13)	0.0369 (15)	−0.0020 (10)	0.0107 (12)	−0.0082 (11)
C11	0.0153 (11)	0.0138 (11)	0.0190 (11)	0.0011 (9)	−0.0016 (9)	0.0015 (9)
C15	0.0287 (14)	0.0258 (13)	0.0158 (12)	0.0080 (11)	−0.0058 (11)	−0.0063 (10)
C6	0.0176 (12)	0.0185 (12)	0.0207 (12)	0.0033 (9)	−0.0072 (10)	−0.0037 (10)
C12	0.0150 (11)	0.0148 (11)	0.0152 (11)	0.0045 (9)	−0.0009 (9)	−0.0013 (9)
C7	0.0204 (12)	0.0211 (12)	0.0177 (11)	0.0024 (10)	−0.0090 (10)	0.0033 (10)
C4	0.0135 (12)	0.0212 (13)	0.0335 (14)	0.0014 (10)	−0.0022 (11)	−0.0095 (11)
C14	0.0194 (12)	0.0241 (13)	0.0256 (13)	0.0024 (10)	−0.0051 (11)	−0.0100 (11)
C9	0.0177 (12)	0.0178 (12)	0.0200 (12)	0.0015 (10)	0.0007 (10)	0.0011 (10)
C8	0.0216 (12)	0.0226 (12)	0.0125 (11)	−0.0017 (10)	−0.0037 (9)	0.0000 (10)
C10	0.0206 (12)	0.0214 (12)	0.0228 (12)	0.0009 (10)	0.0037 (10)	0.0009 (10)

Geometric parameters (Å, º)

Cd1—Cl1	2.6085 (6)	C5—C4	1.389 (3)
Cd1—Cl2	2.4772 (6)	C1—H1	0.9300
Cd1—N1	2.4132 (19)	C16—H16	0.9300
Cd1—N3	2.4573 (18)	C16—C15	1.380 (3)
Cd1—N4	2.4153 (19)	C3—H3	0.9300
Cd1—N2	2.3610 (19)	C3—C4	1.390 (4)
O1—C11	1.429 (3)	C11—H11	0.9800
O1—C10	1.438 (3)	C11—C12	1.519 (3)
N1—C5	1.345 (3)	C15—H15	0.9300
N1—C1	1.335 (3)	C15—C14	1.380 (3)
N3—C11	1.465 (3)	C6—H6	0.9300
N3—C9	1.480 (3)	C7—H7A	0.9700
N3—C8	1.483 (3)	C7—H7B	0.9700
C13—H13	0.9300	C7—C8	1.528 (3)
C13—C12	1.387 (3)	C4—H4	0.9300
C13—C14	1.382 (3)	C14—H14	0.9300
N4—C16	1.346 (3)	C9—H9A	0.9700
N4—C12	1.340 (3)	C9—H9B	0.9700
N2—C6	1.270 (3)	C9—C10	1.520 (3)
N2—C7	1.453 (3)	C8—H8A	0.9700
C2—H2	0.9300	C8—H8B	0.9700
C2—C1	1.389 (3)	C10—H10A	0.9700
C2—C3	1.373 (4)	C10—H10B	0.9700
C5—C6	1.480 (3)
Cl2—Cd1—Cl1	96.24 (2)	C2—C3—C4	118.6 (2)
N1—Cd1—Cl1	101.74 (5)	C4—C3—H3	120.7
N1—Cd1—Cl2	95.08 (5)	O1—C11—N3	107.95 (17)
N1—Cd1—N3	137.50 (6)	O1—C11—H11	108.6
N1—Cd1—N4	104.58 (6)	O1—C11—C12	110.70 (18)
N3—Cd1—Cl1	87.44 (4)	N3—C11—H11	108.6
N3—Cd1—Cl2	125.41 (5)	N3—C11—C12	112.23 (18)
N4—Cd1—Cl1	153.21 (5)	C12—C11—H11	108.6
N4—Cd1—Cl2	86.34 (5)	C16—C15—H15	120.6
N4—Cd1—N3	69.78 (6)	C16—C15—C14	118.7 (2)
N2—Cd1—Cl1	87.72 (5)	C14—C15—H15	120.6
N2—Cd1—Cl2	163.60 (5)	N2—C6—C5	118.6 (2)
N2—Cd1—N1	68.52 (6)	N2—C6—H6	120.7
N2—Cd1—N3	70.54 (6)	C5—C6—H6	120.7
N2—Cd1—N4	97.30 (6)	C13—C12—C11	121.0 (2)
C11—O1—C10	108.46 (17)	N4—C12—C13	121.9 (2)
C5—N1—Cd1	115.06 (15)	N4—C12—C11	116.89 (19)
C1—N1—Cd1	126.13 (16)	N2—C7—H7A	109.8
C1—N1—C5	118.0 (2)	N2—C7—H7B	109.8
C11—N3—Cd1	114.46 (13)	N2—C7—C8	109.30 (18)
C11—N3—C9	102.10 (17)	H7A—C7—H7B	108.3
C11—N3—C8	112.05 (17)	C8—C7—H7A	109.8
C9—N3—Cd1	108.97 (13)	C8—C7—H7B	109.8
C9—N3—C8	112.24 (17)	C5—C4—C3	118.8 (2)
C8—N3—Cd1	107.06 (13)	C5—C4—H4	120.6
C12—C13—H13	120.3	C3—C4—H4	120.6
C14—C13—H13	120.3	C13—C14—H14	120.6
C14—C13—C12	119.4 (2)	C15—C14—C13	118.8 (2)
C16—N4—Cd1	120.79 (15)	C15—C14—H14	120.6
C12—N4—Cd1	118.04 (14)	N3—C9—H9A	111.1
C12—N4—C16	118.2 (2)	N3—C9—H9B	111.1
C6—N2—Cd1	118.56 (16)	N3—C9—C10	103.38 (18)
C6—N2—C7	122.1 (2)	H9A—C9—H9B	109.1
C7—N2—Cd1	118.96 (14)	C10—C9—H9A	111.1
C1—C2—H2	120.4	C10—C9—H9B	111.1
C3—C2—H2	120.4	N3—C8—C7	111.02 (17)
C3—C2—C1	119.2 (2)	N3—C8—H8A	109.4
N1—C5—C6	116.4 (2)	N3—C8—H8B	109.4
N1—C5—C4	122.5 (2)	C7—C8—H8A	109.4
C4—C5—C6	121.0 (2)	C7—C8—H8B	109.4
N1—C1—C2	122.7 (2)	H8A—C8—H8B	108.0
N1—C1—H1	118.6	O1—C10—C9	104.47 (17)
C2—C1—H1	118.6	O1—C10—H10A	110.9
N4—C16—H16	118.6	O1—C10—H10B	110.9
N4—C16—C15	122.8 (2)	C9—C10—H10A	110.9
C15—C16—H16	118.6	C9—C10—H10B	110.9
C2—C3—H3	120.7	H10A—C10—H10B	108.9