metal-organic compounds
Di-μ-chlorido-bis(chlorido{8-[2-(dimethylamino)ethylamino]quinoline}cadmium) ethanol monosolvate
aDepartment of Chemistry, College of Science for Women, University of Baghdad, Iraq, and bSchool of Chemistry, Cardiff University, Main Building, Park Place, Cardiff CF10, 3AT, UK
*Correspondence e-mail: kariukib@cf.ac.uk
The title solvated bimetallic complex, [Cd2Cl4(C13H17N3)2]·C2H5OH, comprises two Cd2+ metal ions linked by a pair of μ2 Cl− ions. The coordination sphere around each Cd2+ ion is completed by three N atoms of a tridentate 8-[2-(dimethylamino)ethylamino]quinoline ligand and another chloride ion to form a distorted fac-CdN3Cl3 octahedron. The ethanol molecule is both an acceptor of an N—H⋯O and a donor of an O—H⋯Cl hydrogen bonds to its adjacent complex unit. In the crystal, weak aromatic π–π stacking is observed.
Keywords: crystal structure; cadmium; complex; quinoline.
CCDC reference: 2062006
Structure description
Part of our research in metal coordination chemistry includes the investigation of N-containing ligands with the quinoline moiety (Amoroso et al. 2009; Al-Sudani, 2014; Kariuki & Al-Sudani, 2014). The title structure, I, is an ethanol solvate of the complex previously obtained in hydrate form (Al-Sudani & Kariuki, 2013; Cambridge Structural Database refcode NIKROQ).
The I (Fig. 1) comprises one bimetallic complex unit and an ethanol solvent molecule, implying the dinuclear molecules lacks Unlike the hydrate form of the complex (Al-Sudani & Kariuki, 2013), the Cd2Cl2 core in I is not strictly planar. One Cd2+ ion deviates by 0.565 (1) Å from the plane of the other Cd2+ and two Cl− ions of the core (Fig. 2). The Cd1⋯Cd2 separation is 3.8061 (4) Å. The two pendant Cl− ions are oriented roughly perpendicular to, but on opposite sides, of the plane of the (Cd2Cl2) core in both the hydrate and ethanol solvate forms. Similar perpendicular arrangement of the pendant Cl− ions is observed in the Cl–(Cd2Cl2)–Cl fragments of other complexes with different ligands (Neis et al., 2010; Marsh 1999; Pauly et al., 2000). An alternative co-planar arrangement is also possible (Cannas et al., 1980).
ofBoth Cd2+ ions in I are coordinated by six atoms in a distorted octahedral geometry: three of the contacts are nitrogen atoms from a tridentate ligand and the rest are chloride ions. Distortions in the coordination from ideal 90° angles range from 71.48 (9)° (N3—Cd1—N2) to 105.73 (3)° (Cl1—Cd1–Cl2) for one Cd2+ ion and 71.04 (9) ° (N6—Cd2—N5) to 102.09 (7)° (N5—Cd2—Cl2) for the other. The corresponding angles for the hydrate structure are in the range 69.48 (5) to 101.08 (4)°. The N—C—C—N torsion angles in the ethane diamine are almost the same for both independent ligands [N1—C3—C4—N2 = 63.0 (4)° and N4—C16—C17—N5 = 63.3 (5)°] in I.
An intramolecular N—H⋯Cl hydrogen bond (Table 1, Fig. 3) is observed in the dinuclear molecule. The complex also donates an N—H⋯O hydrogen bond to the ethanol solvent molecule and accepts an O—H⋯Cl contact from the same molecule to generate an R(6)22 loop. In the extended structure, the quinoline ring systems of neighbouring complex units are involved in weak aromatic π–π stacking interactions. The groups involved are related by inversion symmetry with a c(i)⋯c(i)′ separation of 3.93 (1) Å [c(i) = the midpoint of the C9—C10 bond of the C5–C13/N3 ring system]. If a second longer inversion-related contact c(ii)⋯c(ii)′ of 4.56 (1) Å [c(ii) = midpoint of the C22—C23 bond of the C18–C26/N6 ring system] is considered to be a significant interaction, infinite chains running parallel to [101] result (Fig. 4).
|
Synthesis and crystallization
The 8-[2-(dimethylamino)ethylamino]quinoline ligand and cadmium dichloride were mixed in dry ethanol solvent at room temperature under a positive nitrogen pressure and the mixture was stirred at room temperature for several hours. The solution was then warmed to dissolve the material and the product was recrystallized on cooling to produce colourless crystals of I.
Refinement
Crystal data, data collection and structure .
details are summarized in Table 2Structural data
CCDC reference: 2062006
https://doi.org/10.1107/S2414314621001504/hb4375sup1.cif
contains datablock I. DOI:Structure factors: contains datablock I. DOI: https://doi.org/10.1107/S2414314621001504/hb4375Isup2.hkl
Data collection: CrysAlis PRO (Rigaku OD, 2019); cell
CrysAlis PRO (Rigaku OD, 2019); data reduction: CrysAlis PRO (Rigaku OD, 2019); program(s) used to solve structure: SHELXS (Sheldrick, 2008); program(s) used to refine structure: SHELXL (Sheldrick, 2015); molecular graphics: Mercury (Macrae et al., 2020); software used to prepare material for publication: WinGX (Farrugia, 2012).[Cd2Cl4(C13H17N3)2]·C2H6O | F(000) = 1688 |
Mr = 843.26 | Dx = 1.679 Mg m−3 |
Monoclinic, P21/c | Mo Kα radiation, λ = 0.71073 Å |
a = 11.9747 (6) Å | Cell parameters from 7578 reflections |
b = 15.6483 (7) Å | θ = 3.7–29.2° |
c = 17.8804 (8) Å | µ = 1.63 mm−1 |
β = 95.292 (4)° | T = 296 K |
V = 3336.2 (3) Å3 | Block, colourless |
Z = 4 | 0.16 × 0.13 × 0.10 mm |
Rigaku Oxford Diffraction SuperNova, Dual, Cu at home/near, Atlas diffractometer | 5798 reflections with I > 2σ(I) |
ω scans | Rint = 0.033 |
Absorption correction: gaussian (CrysAlisPro (Rigaku OD, 2019) | θmax = 29.9°, θmin = 1.7° |
Tmin = 0.897, Tmax = 1.000 | h = −16→15 |
29581 measured reflections | k = −21→20 |
8400 independent reflections | l = −23→24 |
Refinement on F2 | 0 restraints |
Least-squares matrix: full | Hydrogen site location: inferred from neighbouring sites |
R[F2 > 2σ(F2)] = 0.036 | H-atom parameters constrained |
wR(F2) = 0.086 | w = 1/[σ2(Fo2) + (0.0253P)2 + 3.3741P] where P = (Fo2 + 2Fc2)/3 |
S = 1.05 | (Δ/σ)max = 0.002 |
8400 reflections | Δρmax = 0.58 e Å−3 |
376 parameters | Δρmin = −0.86 e Å−3 |
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. The H atoms were positioned geometrically and refined using a riding model with Uiso(H) = 1.2Ueq(carrier) or 1.5Ueq(methyl C). The methyl groups were allowd to rotate, but not to tip, to best fit the electron density. |
x | y | z | Uiso*/Ueq | ||
C1 | 0.5109 (3) | 0.4794 (3) | 0.09136 (19) | 0.0610 (11) | |
H1A | 0.468166 | 0.531360 | 0.091253 | 0.092* | |
H1B | 0.466152 | 0.435355 | 0.066115 | 0.092* | |
H1C | 0.576927 | 0.488698 | 0.065837 | 0.092* | |
C2 | 0.6062 (4) | 0.3720 (3) | 0.1695 (3) | 0.0719 (13) | |
H2A | 0.673719 | 0.380147 | 0.145320 | 0.108* | |
H2B | 0.560683 | 0.329261 | 0.142997 | 0.108* | |
H2C | 0.624854 | 0.353891 | 0.220385 | 0.108* | |
C3 | 0.6125 (3) | 0.5191 (3) | 0.2093 (2) | 0.0579 (11) | |
H3A | 0.661288 | 0.544847 | 0.175199 | 0.069* | |
H3B | 0.659558 | 0.492550 | 0.249900 | 0.069* | |
C4 | 0.5426 (3) | 0.5879 (2) | 0.2411 (2) | 0.0531 (10) | |
H4A | 0.591226 | 0.631940 | 0.264266 | 0.064* | |
H4B | 0.494231 | 0.613984 | 0.200942 | 0.064* | |
C5 | 0.5393 (3) | 0.5251 (2) | 0.36625 (17) | 0.0358 (7) | |
C6 | 0.6046 (3) | 0.5815 (3) | 0.40930 (19) | 0.0453 (9) | |
H6 | 0.609177 | 0.638054 | 0.393875 | 0.054* | |
C7 | 0.6649 (3) | 0.5551 (3) | 0.4766 (2) | 0.0516 (10) | |
H7 | 0.709823 | 0.594159 | 0.504751 | 0.062* | |
C8 | 0.6582 (3) | 0.4734 (3) | 0.50079 (19) | 0.0486 (9) | |
H8 | 0.697695 | 0.456832 | 0.545688 | 0.058* | |
C9 | 0.5915 (3) | 0.4130 (2) | 0.45811 (18) | 0.0432 (9) | |
C10 | 0.5328 (3) | 0.4391 (2) | 0.38922 (17) | 0.0360 (7) | |
C11 | 0.5772 (4) | 0.3284 (3) | 0.4815 (2) | 0.0594 (11) | |
H11 | 0.613726 | 0.309528 | 0.526641 | 0.071* | |
C12 | 0.5104 (4) | 0.2742 (3) | 0.4385 (2) | 0.0670 (12) | |
H12 | 0.498995 | 0.218474 | 0.454222 | 0.080* | |
C13 | 0.4587 (3) | 0.3039 (3) | 0.3697 (2) | 0.0562 (10) | |
H13 | 0.415285 | 0.265768 | 0.339554 | 0.067* | |
C14 | −0.0799 (4) | 0.4866 (3) | 0.3591 (3) | 0.0781 (14) | |
H14A | −0.023902 | 0.450126 | 0.384180 | 0.117* | |
H14B | −0.103480 | 0.463456 | 0.310456 | 0.117* | |
H14C | −0.143177 | 0.490197 | 0.388244 | 0.117* | |
C15 | 0.0095 (4) | 0.6041 (4) | 0.4240 (2) | 0.0832 (15) | |
H15A | 0.039218 | 0.660568 | 0.419081 | 0.125* | |
H15B | 0.067710 | 0.566875 | 0.445384 | 0.125* | |
H15C | −0.050415 | 0.605741 | 0.456112 | 0.125* | |
C16 | −0.1216 (3) | 0.6266 (3) | 0.3123 (3) | 0.0659 (12) | |
H16A | −0.166148 | 0.592189 | 0.275586 | 0.079* | |
H16B | −0.170664 | 0.645949 | 0.349116 | 0.079* | |
C17 | −0.0792 (3) | 0.7015 (3) | 0.2743 (2) | 0.0576 (10) | |
H17A | −0.033743 | 0.735832 | 0.310602 | 0.069* | |
H17B | −0.141975 | 0.736112 | 0.254028 | 0.069* | |
C18 | −0.0760 (3) | 0.6499 (2) | 0.14515 (19) | 0.0409 (8) | |
C19 | −0.1360 (3) | 0.7065 (3) | 0.0994 (2) | 0.0609 (11) | |
H19 | −0.137400 | 0.763865 | 0.112889 | 0.073* | |
C20 | −0.1960 (4) | 0.6794 (3) | 0.0321 (2) | 0.0741 (14) | |
H20 | −0.236205 | 0.719086 | 0.001762 | 0.089* | |
C21 | −0.1958 (4) | 0.5963 (3) | 0.0110 (2) | 0.0626 (12) | |
H21 | −0.235248 | 0.579364 | −0.033762 | 0.075* | |
C22 | −0.1355 (3) | 0.5352 (2) | 0.05715 (19) | 0.0434 (8) | |
C23 | −0.0746 (3) | 0.5624 (2) | 0.12458 (18) | 0.0370 (7) | |
C24 | −0.1319 (4) | 0.4480 (3) | 0.0387 (2) | 0.0594 (11) | |
H24 | −0.171148 | 0.427885 | −0.005102 | 0.071* | |
C25 | −0.0715 (4) | 0.3937 (3) | 0.0846 (3) | 0.0722 (13) | |
H25 | −0.069524 | 0.335704 | 0.073334 | 0.087* | |
C26 | −0.0121 (4) | 0.4254 (3) | 0.1492 (2) | 0.0655 (12) | |
H26 | 0.030561 | 0.387245 | 0.179747 | 0.079* | |
C27 | 0.1593 (5) | 0.7698 (4) | 0.0786 (3) | 0.112 (2) | |
H27A | 0.127708 | 0.713794 | 0.082293 | 0.168* | |
H27B | 0.207118 | 0.770868 | 0.038332 | 0.168* | |
H27C | 0.100097 | 0.810805 | 0.068762 | 0.168* | |
C28 | 0.2249 (4) | 0.7913 (3) | 0.1491 (3) | 0.0789 (14) | |
H28A | 0.277926 | 0.745579 | 0.162022 | 0.095* | |
H28B | 0.267414 | 0.842890 | 0.141981 | 0.095* | |
N1 | 0.5435 (2) | 0.4533 (2) | 0.16910 (16) | 0.0465 (7) | |
N2 | 0.4735 (2) | 0.55133 (17) | 0.29757 (14) | 0.0367 (6) | |
H2 | 0.419375 | 0.594663 | 0.310394 | 0.044* | |
N3 | 0.4685 (2) | 0.38266 (18) | 0.34557 (15) | 0.0415 (7) | |
N4 | −0.0328 (3) | 0.5724 (2) | 0.35048 (17) | 0.0490 (8) | |
N5 | −0.0111 (2) | 0.67654 (17) | 0.21276 (15) | 0.0393 (6) | |
H5 | 0.033935 | 0.726058 | 0.200603 | 0.047* | |
N6 | −0.0127 (2) | 0.50655 (18) | 0.16967 (16) | 0.0434 (7) | |
Cd1 | 0.37193 (2) | 0.43475 (2) | 0.23492 (2) | 0.03457 (7) | |
Cd2 | 0.11394 (2) | 0.56817 (2) | 0.26458 (2) | 0.03612 (8) | |
Cl1 | 0.32762 (8) | 0.30005 (6) | 0.16560 (5) | 0.0542 (2) | |
Cl2 | 0.25905 (7) | 0.55385 (6) | 0.15909 (5) | 0.0450 (2) | |
Cl3 | 0.19490 (7) | 0.42895 (6) | 0.32090 (5) | 0.0450 (2) | |
Cl4 | 0.24434 (8) | 0.67656 (6) | 0.33611 (5) | 0.0487 (2) | |
O1 | 0.1615 (3) | 0.8033 (2) | 0.20690 (19) | 0.0813 (9) | |
H1 | 0.189522 | 0.777756 | 0.244020 | 0.122* |
U11 | U22 | U33 | U12 | U13 | U23 | |
C1 | 0.056 (2) | 0.094 (3) | 0.032 (2) | −0.003 (2) | −0.0001 (17) | 0.005 (2) |
C2 | 0.052 (3) | 0.088 (4) | 0.076 (3) | 0.021 (2) | 0.012 (2) | 0.004 (3) |
C3 | 0.040 (2) | 0.096 (3) | 0.037 (2) | −0.020 (2) | 0.0032 (16) | 0.006 (2) |
C4 | 0.064 (3) | 0.053 (2) | 0.039 (2) | −0.024 (2) | −0.0120 (17) | 0.0115 (18) |
C5 | 0.0321 (17) | 0.046 (2) | 0.0283 (16) | 0.0012 (15) | 0.0003 (13) | 0.0006 (15) |
C6 | 0.044 (2) | 0.053 (2) | 0.0384 (19) | −0.0063 (17) | 0.0016 (15) | −0.0013 (17) |
C7 | 0.043 (2) | 0.074 (3) | 0.037 (2) | −0.0076 (19) | −0.0017 (15) | −0.0125 (19) |
C8 | 0.039 (2) | 0.074 (3) | 0.0306 (18) | 0.0038 (19) | −0.0061 (14) | −0.0032 (19) |
C9 | 0.0387 (19) | 0.058 (2) | 0.0330 (18) | 0.0123 (17) | 0.0006 (14) | 0.0030 (17) |
C10 | 0.0304 (16) | 0.045 (2) | 0.0320 (17) | 0.0055 (15) | −0.0006 (12) | 0.0019 (15) |
C11 | 0.069 (3) | 0.064 (3) | 0.043 (2) | 0.014 (2) | −0.0100 (18) | 0.014 (2) |
C12 | 0.091 (3) | 0.050 (3) | 0.058 (3) | 0.005 (2) | −0.006 (2) | 0.018 (2) |
C13 | 0.066 (3) | 0.044 (2) | 0.056 (2) | 0.000 (2) | −0.0108 (19) | 0.0013 (19) |
C14 | 0.074 (3) | 0.073 (3) | 0.091 (4) | −0.016 (3) | 0.030 (3) | 0.008 (3) |
C15 | 0.083 (3) | 0.113 (4) | 0.054 (3) | −0.012 (3) | 0.012 (2) | −0.012 (3) |
C16 | 0.051 (2) | 0.075 (3) | 0.073 (3) | 0.013 (2) | 0.014 (2) | 0.003 (2) |
C17 | 0.063 (3) | 0.049 (2) | 0.061 (2) | 0.016 (2) | 0.008 (2) | −0.008 (2) |
C18 | 0.0350 (18) | 0.039 (2) | 0.047 (2) | 0.0029 (15) | −0.0057 (15) | −0.0014 (16) |
C19 | 0.069 (3) | 0.041 (2) | 0.067 (3) | 0.012 (2) | −0.020 (2) | −0.004 (2) |
C20 | 0.085 (3) | 0.066 (3) | 0.064 (3) | 0.024 (3) | −0.032 (2) | 0.005 (2) |
C21 | 0.067 (3) | 0.066 (3) | 0.050 (2) | 0.009 (2) | −0.0244 (19) | −0.002 (2) |
C22 | 0.0394 (19) | 0.048 (2) | 0.0405 (19) | −0.0004 (16) | −0.0075 (15) | −0.0035 (17) |
C23 | 0.0293 (16) | 0.042 (2) | 0.0380 (18) | 0.0012 (14) | −0.0040 (13) | −0.0002 (15) |
C24 | 0.070 (3) | 0.055 (3) | 0.049 (2) | −0.006 (2) | −0.0152 (19) | −0.014 (2) |
C25 | 0.098 (4) | 0.041 (2) | 0.072 (3) | 0.003 (2) | −0.029 (3) | −0.015 (2) |
C26 | 0.085 (3) | 0.040 (2) | 0.066 (3) | 0.008 (2) | −0.025 (2) | −0.005 (2) |
C27 | 0.116 (5) | 0.124 (6) | 0.096 (4) | −0.015 (4) | 0.008 (4) | −0.006 (4) |
C28 | 0.080 (3) | 0.079 (4) | 0.077 (3) | −0.006 (3) | 0.005 (3) | 0.008 (3) |
N1 | 0.0359 (16) | 0.064 (2) | 0.0386 (16) | 0.0012 (14) | −0.0001 (12) | 0.0056 (15) |
N2 | 0.0389 (15) | 0.0333 (15) | 0.0370 (15) | −0.0010 (12) | −0.0011 (11) | 0.0032 (12) |
N3 | 0.0457 (17) | 0.0372 (17) | 0.0401 (16) | 0.0039 (13) | −0.0053 (12) | 0.0035 (13) |
N4 | 0.0506 (18) | 0.051 (2) | 0.0455 (18) | 0.0058 (15) | 0.0060 (14) | 0.0003 (15) |
N5 | 0.0423 (16) | 0.0299 (15) | 0.0442 (16) | 0.0006 (12) | −0.0046 (12) | −0.0035 (13) |
N6 | 0.0494 (18) | 0.0318 (16) | 0.0458 (17) | 0.0027 (13) | −0.0123 (13) | −0.0022 (13) |
Cd1 | 0.03461 (13) | 0.03321 (14) | 0.03431 (13) | −0.00004 (10) | −0.00531 (9) | 0.00115 (10) |
Cd2 | 0.03520 (14) | 0.03407 (14) | 0.03719 (14) | 0.00278 (10) | −0.00686 (10) | −0.00189 (11) |
Cl1 | 0.0645 (6) | 0.0397 (5) | 0.0574 (6) | −0.0067 (4) | 0.0004 (4) | −0.0091 (4) |
Cl2 | 0.0485 (5) | 0.0479 (5) | 0.0370 (4) | 0.0107 (4) | −0.0046 (4) | 0.0047 (4) |
Cl3 | 0.0452 (5) | 0.0395 (5) | 0.0501 (5) | 0.0074 (4) | 0.0039 (4) | 0.0100 (4) |
Cl4 | 0.0523 (5) | 0.0419 (5) | 0.0483 (5) | −0.0069 (4) | −0.0145 (4) | −0.0010 (4) |
O1 | 0.080 (2) | 0.079 (2) | 0.082 (2) | −0.0113 (19) | −0.0056 (18) | 0.0220 (19) |
C1—N1 | 1.467 (4) | C16—H16B | 0.9700 |
C1—H1A | 0.9600 | C17—N5 | 1.481 (4) |
C1—H1B | 0.9600 | C17—H17A | 0.9700 |
C1—H1C | 0.9600 | C17—H17B | 0.9700 |
C2—N1 | 1.476 (5) | C18—C19 | 1.364 (5) |
C2—H2A | 0.9600 | C18—C23 | 1.418 (5) |
C2—H2B | 0.9600 | C18—N5 | 1.437 (4) |
C2—H2C | 0.9600 | C19—C20 | 1.409 (5) |
C3—N1 | 1.467 (5) | C19—H19 | 0.9300 |
C3—C4 | 1.508 (6) | C20—C21 | 1.354 (6) |
C3—H3A | 0.9700 | C20—H20 | 0.9300 |
C3—H3B | 0.9700 | C21—C22 | 1.417 (5) |
C4—N2 | 1.478 (4) | C21—H21 | 0.9300 |
C4—H4A | 0.9700 | C22—C24 | 1.405 (5) |
C4—H4B | 0.9700 | C22—C23 | 1.416 (4) |
C5—C6 | 1.368 (5) | C23—N6 | 1.361 (4) |
C5—C10 | 1.412 (5) | C24—C25 | 1.345 (6) |
C5—N2 | 1.455 (4) | C24—H24 | 0.9300 |
C6—C7 | 1.407 (5) | C25—C26 | 1.390 (5) |
C6—H6 | 0.9300 | C25—H25 | 0.9300 |
C7—C8 | 1.356 (6) | C26—N6 | 1.322 (5) |
C7—H7 | 0.9300 | C26—H26 | 0.9300 |
C8—C9 | 1.414 (5) | C27—C28 | 1.462 (7) |
C8—H8 | 0.9300 | C27—H27A | 0.9600 |
C9—C11 | 1.404 (5) | C27—H27B | 0.9600 |
C9—C10 | 1.421 (4) | C27—H27C | 0.9600 |
C10—N3 | 1.368 (4) | C28—O1 | 1.350 (5) |
C11—C12 | 1.356 (6) | C28—H28A | 0.9700 |
C11—H11 | 0.9300 | C28—H28B | 0.9700 |
C12—C13 | 1.404 (5) | N1—Cd1 | 2.477 (3) |
C12—H12 | 0.9300 | N2—Cd1 | 2.411 (3) |
C13—N3 | 1.315 (5) | N2—H2 | 0.9800 |
C13—H13 | 0.9300 | N3—Cd1 | 2.344 (3) |
C14—N4 | 1.469 (5) | N4—Cd2 | 2.439 (3) |
C14—H14A | 0.9600 | N5—Cd2 | 2.392 (3) |
C14—H14B | 0.9600 | N5—H5 | 0.9800 |
C14—H14C | 0.9600 | N6—Cd2 | 2.374 (3) |
C15—N4 | 1.452 (5) | Cd1—Cl1 | 2.4777 (9) |
C15—H15A | 0.9600 | Cd1—Cl2 | 2.6079 (9) |
C15—H15B | 0.9600 | Cd1—Cl3 | 2.7326 (9) |
C15—H15C | 0.9600 | Cd2—Cl3 | 2.5535 (9) |
C16—C17 | 1.468 (6) | Cd2—Cl4 | 2.5656 (9) |
C16—N4 | 1.478 (5) | Cd2—Cl2 | 2.6893 (9) |
C16—H16A | 0.9700 | O1—H1 | 0.8200 |
N1—C1—H1A | 109.5 | C23—C22—C21 | 119.1 (3) |
N1—C1—H1B | 109.5 | N6—C23—C22 | 121.3 (3) |
H1A—C1—H1B | 109.5 | N6—C23—C18 | 119.0 (3) |
N1—C1—H1C | 109.5 | C22—C23—C18 | 119.6 (3) |
H1A—C1—H1C | 109.5 | C25—C24—C22 | 119.8 (4) |
H1B—C1—H1C | 109.5 | C25—C24—H24 | 120.1 |
N1—C2—H2A | 109.5 | C22—C24—H24 | 120.1 |
N1—C2—H2B | 109.5 | C24—C25—C26 | 119.1 (4) |
H2A—C2—H2B | 109.5 | C24—C25—H25 | 120.5 |
N1—C2—H2C | 109.5 | C26—C25—H25 | 120.5 |
H2A—C2—H2C | 109.5 | N6—C26—C25 | 123.9 (4) |
H2B—C2—H2C | 109.5 | N6—C26—H26 | 118.1 |
N1—C3—C4 | 112.3 (3) | C25—C26—H26 | 118.1 |
N1—C3—H3A | 109.2 | C28—C27—H27A | 109.5 |
C4—C3—H3A | 109.2 | C28—C27—H27B | 109.5 |
N1—C3—H3B | 109.2 | H27A—C27—H27B | 109.5 |
C4—C3—H3B | 109.2 | C28—C27—H27C | 109.5 |
H3A—C3—H3B | 107.9 | H27A—C27—H27C | 109.5 |
N2—C4—C3 | 110.3 (3) | H27B—C27—H27C | 109.5 |
N2—C4—H4A | 109.6 | O1—C28—C27 | 113.4 (5) |
C3—C4—H4A | 109.6 | O1—C28—H28A | 108.9 |
N2—C4—H4B | 109.6 | C27—C28—H28A | 108.9 |
C3—C4—H4B | 109.6 | O1—C28—H28B | 108.9 |
H4A—C4—H4B | 108.1 | C27—C28—H28B | 108.9 |
C6—C5—C10 | 119.7 (3) | H28A—C28—H28B | 107.7 |
C6—C5—N2 | 122.0 (3) | C3—N1—C1 | 110.9 (3) |
C10—C5—N2 | 118.3 (3) | C3—N1—C2 | 109.8 (3) |
C5—C6—C7 | 120.9 (4) | C1—N1—C2 | 109.6 (3) |
C5—C6—H6 | 119.5 | C3—N1—Cd1 | 107.7 (2) |
C7—C6—H6 | 119.5 | C1—N1—Cd1 | 108.8 (2) |
C8—C7—C6 | 120.6 (4) | C2—N1—Cd1 | 109.9 (2) |
C8—C7—H7 | 119.7 | C5—N2—C4 | 113.1 (3) |
C6—C7—H7 | 119.7 | C5—N2—Cd1 | 112.9 (2) |
C7—C8—C9 | 120.4 (3) | C4—N2—Cd1 | 105.4 (2) |
C7—C8—H8 | 119.8 | C5—N2—H2 | 108.4 |
C9—C8—H8 | 119.8 | C4—N2—H2 | 108.4 |
C11—C9—C8 | 123.2 (3) | Cd1—N2—H2 | 108.4 |
C11—C9—C10 | 117.7 (3) | C13—N3—C10 | 118.7 (3) |
C8—C9—C10 | 119.1 (4) | C13—N3—Cd1 | 123.4 (2) |
N3—C10—C5 | 119.5 (3) | C10—N3—Cd1 | 117.7 (2) |
N3—C10—C9 | 121.1 (3) | C15—N4—C14 | 108.8 (4) |
C5—C10—C9 | 119.3 (3) | C15—N4—C16 | 113.4 (4) |
C12—C11—C9 | 120.2 (4) | C14—N4—C16 | 107.8 (3) |
C12—C11—H11 | 119.9 | C15—N4—Cd2 | 111.6 (3) |
C9—C11—H11 | 119.9 | C14—N4—Cd2 | 110.3 (2) |
C11—C12—C13 | 118.6 (4) | C16—N4—Cd2 | 104.7 (2) |
C11—C12—H12 | 120.7 | C18—N5—C17 | 114.2 (3) |
C13—C12—H12 | 120.7 | C18—N5—Cd2 | 113.0 (2) |
N3—C13—C12 | 123.5 (4) | C17—N5—Cd2 | 105.5 (2) |
N3—C13—H13 | 118.2 | C18—N5—H5 | 108.0 |
C12—C13—H13 | 118.2 | C17—N5—H5 | 108.0 |
N4—C14—H14A | 109.5 | Cd2—N5—H5 | 108.0 |
N4—C14—H14B | 109.5 | C26—N6—C23 | 118.0 (3) |
H14A—C14—H14B | 109.5 | C26—N6—Cd2 | 124.7 (2) |
N4—C14—H14C | 109.5 | C23—N6—Cd2 | 116.1 (2) |
H14A—C14—H14C | 109.5 | N3—Cd1—N2 | 71.48 (9) |
H14B—C14—H14C | 109.5 | N3—Cd1—N1 | 94.32 (10) |
N4—C15—H15A | 109.5 | N2—Cd1—N1 | 74.16 (10) |
N4—C15—H15B | 109.5 | N3—Cd1—Cl1 | 101.11 (7) |
H15A—C15—H15B | 109.5 | N2—Cd1—Cl1 | 162.14 (7) |
N4—C15—H15C | 109.5 | N1—Cd1—Cl1 | 90.61 (8) |
H15A—C15—H15C | 109.5 | N3—Cd1—Cl2 | 151.53 (7) |
H15B—C15—H15C | 109.5 | N2—Cd1—Cl2 | 85.18 (7) |
C17—C16—N4 | 114.0 (3) | N1—Cd1—Cl2 | 94.71 (7) |
C17—C16—H16A | 108.8 | Cl1—Cd1—Cl2 | 105.73 (3) |
N4—C16—H16A | 108.8 | N3—Cd1—Cl3 | 82.05 (7) |
C17—C16—H16B | 108.8 | N2—Cd1—Cl3 | 98.52 (7) |
N4—C16—H16B | 108.8 | N1—Cd1—Cl3 | 172.59 (7) |
H16A—C16—H16B | 107.6 | Cl1—Cd1—Cl3 | 96.41 (3) |
C16—C17—N5 | 111.8 (3) | Cl2—Cd1—Cl3 | 85.67 (3) |
C16—C17—H17A | 109.3 | N6—Cd2—N5 | 71.04 (9) |
N5—C17—H17A | 109.3 | N6—Cd2—N4 | 90.64 (10) |
C16—C17—H17B | 109.3 | N5—Cd2—N4 | 76.30 (10) |
N5—C17—H17B | 109.3 | N6—Cd2—Cl3 | 97.45 (7) |
H17A—C17—H17B | 107.9 | N5—Cd2—Cl3 | 163.54 (7) |
C19—C18—C23 | 119.3 (3) | N4—Cd2—Cl3 | 92.51 (8) |
C19—C18—N5 | 122.0 (3) | N6—Cd2—Cl4 | 160.78 (7) |
C23—C18—N5 | 118.7 (3) | N5—Cd2—Cl4 | 93.15 (7) |
C18—C19—C20 | 121.0 (4) | N4—Cd2—Cl4 | 96.26 (8) |
C18—C19—H19 | 119.5 | Cl3—Cd2—Cl4 | 100.13 (3) |
C20—C19—H19 | 119.5 | N6—Cd2—Cl2 | 82.90 (8) |
C21—C20—C19 | 120.9 (4) | N5—Cd2—Cl2 | 102.09 (7) |
C21—C20—H20 | 119.5 | N4—Cd2—Cl2 | 173.50 (8) |
C19—C20—H20 | 119.5 | Cl3—Cd2—Cl2 | 87.66 (3) |
C20—C21—C22 | 120.0 (4) | Cl4—Cd2—Cl2 | 90.11 (3) |
C20—C21—H21 | 120.0 | Cd1—Cl2—Cd2 | 91.85 (3) |
C22—C21—H21 | 120.0 | Cd2—Cl3—Cd1 | 92.05 (3) |
C24—C22—C23 | 117.9 (3) | C28—O1—H1 | 109.5 |
C24—C22—C21 | 123.0 (3) |
D—H···A | D—H | H···A | D···A | D—H···A |
N2—H2···Cl4 | 0.98 | 2.53 | 3.492 (3) | 166 |
N5—H5···O1 | 0.98 | 1.94 | 2.874 (4) | 158 |
O1—H1···Cl4 | 0.82 | 2.33 | 3.136 (3) | 166 |
Acknowledgements
We thank Cardiff University and the University of Baghdad for continued support.
References
Al-Sudani, A.-R. H. (2014). Acta Cryst. E70, m1. CSD CrossRef IUCr Journals Google Scholar
Al-Sudani, A.-R. H. & Kariuki, B. M. (2013). Acta Cryst. E69, m491–m492. CSD CrossRef CAS IUCr Journals Google Scholar
Amoroso, A. J., Edwards, P. G., Howard, S. T., Kariuki, B. M., Knight, J. C., Ooi, L., Malik, K. M. A., Stratford, L. & Al-Sudani, A.-R. H. (2009). Dalton Trans. pp. 8356–8362. CSD CrossRef Google Scholar
Cannas, M., Marongiu, G. & Saba, G. (1980). J. Chem. Soc. Dalton Trans. pp. 2090–2094. CSD CrossRef Web of Science Google Scholar
Farrugia, L. J. (2012). J. Appl. Cryst. 45, 849–854. Web of Science CrossRef CAS IUCr Journals Google Scholar
Kariuki, B. M. & Al-Sudani, A.-R. H. (2014). Acta Cryst. E70, m339–m340. CSD CrossRef IUCr Journals Google Scholar
Macrae, C. F., Sovago, I., Cottrell, S. J., Galek, P. T. A., McCabe, P., Pidcock, E., Platings, M., Shields, G. P., Stevens, J. S., Towler, M. & Wood, P. A. (2020). J. Appl. Cryst. 53, 226–235. Web of Science CrossRef CAS IUCr Journals Google Scholar
Marsh, R. E. (1999). Acta Cryst. B55, 931–936. Web of Science CSD CrossRef CAS IUCr Journals Google Scholar
Neis, C., Petry, D., Demangeon, A., Morgenstern, B., Kuppert, D., Huppert, J., Stucky, S. & Hegetschweiler, K. (2010). Inorg. Chem. 49, 10092–10107. Web of Science CSD CrossRef CAS PubMed Google Scholar
Pauly, J. W., Sander, J., Kuppert, D., Winter, M., Reiss, G. J., Zürcher, F., Hoffmann, R., Fässler, T. F. & Hegetschweiler, K. (2000). Chem. Eur. J. 6, 2830–2846. CrossRef PubMed CAS Google Scholar
Rigaku OD (2019). CrysAlis PRO. Rigaku Oxford Diffraction, Yarnton, England. Google Scholar
Sheldrick, G. M. (2008). Acta Cryst. A64, 112–122. Web of Science CrossRef CAS IUCr Journals Google Scholar
Sheldrick, G. M. (2015). Acta Cryst. C71, 3–8. Web of Science CrossRef IUCr Journals Google Scholar
This is an open-access article distributed under the terms of the Creative Commons Attribution (CC-BY) Licence, which permits unrestricted use, distribution, and reproduction in any medium, provided the original authors and source are cited.