metal-organic compounds
μ-1,2-bis(diphenylphosphanyl)ethane-κ2P:P′]bis[(N,N′-diethylthiourea-κS)iodidocopper(I)]
of bis[aDepartment of Chemistry, Faculty of Science, Prince of Songkla University, Hat Yai, Songkhla 90112, Thailand, and bDepartment of Chemistry, Youngstown State University, 1 University Plaza, 44555 Youngstown, OH, USA
*Correspondence e-mail: sumpun.w@psu.ac.th
The binuclear title complex, [Cu2I2(C26H24P2)2(C5H12N2S)2], lies about an inversion centre. The CuI atom displays a distorted tetrahedral coordination geometry defined by one S atom of an N,N′-diethylthiourea ligand, two P atoms derived from two bridging 1,2-bis(diphenylphosphanyl)ethane (dppe) ligands and one iodide ion. The dppe ligand bridges two symmetry-related CuI ions, forming a 10-membered Cu2P4C4 ring. An intramolecular N—H⋯I hydrogen bond is noted. In the crystal, N—H⋯I hydrogen bonds link complex molecules into layers parallel to (-101).
CCDC reference: 1415379
1. Related literature
For background to the coordination chemistry of copper(I) halides and pseudohalides, see: Dennehy et al. (2011); Oshio et al. (1996); Seward et al. (2003). For their potential applications, see: Corey et al. (1987); Dias et al. (2006). For relevant examples of discrete complexes, see: Dennehy et al. (2009).
2. Experimental
2.1. Crystal data
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2.3. Refinement
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Data collection: APEX2 (Bruker, 2013); cell SAINT (Bruker, 2013); data reduction: SAINT; program(s) used to solve structure: SHELXS97 (Sheldrick, 2008); program(s) used to refine structure: SHELXL2015 (Sheldrick, 2015) and SHELXLE (Hübschle et al., 2011); molecular graphics: Mercury (Macrae et al., 2008); software used to prepare material for publication: publCIF (Westrip, 2010).
Supporting information
CCDC reference: 1415379
https://doi.org/10.1107/S2056989015014176/tk5371sup1.cif
contains datablock I. DOI:Structure factors: contains datablock I. DOI: https://doi.org/10.1107/S2056989015014176/tk5371Isup2.hkl
N,N'-Diethylthiourea (0.07 g, 0.5 mmol) was dissolved in 30 cm3 of acetonitrile in a round flask equipped with reflux condenser and magnetic stirrer at 333 K and then CuI (0.1 g, 0.5 mmol) was added. The mixture was stirred for 2 h. 1,2-bis(diphenylphosphanyl)ethane (0.2 g, 0.5 mmol) was added and the reaction mixture was heated under reflux for 5 h where upon the precipitate gradually disappeared. The resulting clear solution was filtered and left to evaporate at room temperature. The colorless crystals, which deposited after standing for several days were filtered off and washed with acetone and dried in vacuo (M. pt = 557 K). Elemental analysis, calculated for [Cu2I2(C26H24P2)2(C5H12N2S)2]: C, 51.59; H, 4.97; N, 3.88; S, 4.44%, found: C, 55.69; H, 5.22; N, 3.62; S, 4.61%.
The (-1 8 3) reflection was affected by the beam-stop and was omitted from the final cycles of
H atoms bonded to C and N atoms were included in their calculated positions and were refined using a riding model using bond lengths of 0.95–0.99 Å and Uiso(H) = 1.2–1.5Ueq(C), and N—H = 0.88 Å (NH) and Uiso(H) = 1.2Ueq(N). The (-1 8 3) reflection was omitted owing to poor agreement.Coordination complexes of copper(I) halides or pseudo-halides with mixed P and S donor ligands have been of interest in coordination chemistry (Dennehy et al., 2011; Oshio et al., 1996; Sewead et al., 2003) due to their applications such as magnetism (Oshio et al., 1996) and biological or medicinal activities (Corey et al., 1987; Dias et al., 2006). In this work, a mixed ligand complex of copper(I) iodide with 1,2-bis(diphenylphosphanyl)ethane (dppe) and N,N'-diethylthiourea (detu) is reported. The binuclear copper(I) complex lies across an inversion center. The µ2-dppe bridges between CuI centers leads to a 10-membered Cu2P4C4 rhomboid, see Fig. 1. The Cu1—P1 and Cu1—P2 bond lengths are 2.2681 (6) and 2.2813 (6)Å, respectively. These values are slightly shorter than the equivalent distances found in [Cu(tsac)(PPh3)2], [Cu4(tsac)4(PPh3)3], [Cu2(tsac)2(dppm)2] and [Cu4(tsac)4(dppm)2], which are in the range 2.2799 (5) and 2.3119 (5) Å (Dennehy et al., 2009). There is an intramolecular N2—H2···I1 hydrogen bond. In the crystal, intermolecular N1—H1···I1 hydrogen bonds link complex molecules into a two-dimensional supramolecular network parallel to (-101) (Fig. 2. and Table 1)
Coordination complexes of copper(I) halides or pseudo-halides with mixed P and S donor ligands have been of interest in coordination chemistry (Dennehy et al., 2011; Oshio et al., 1996; Sewead et al., 2003) due to their applications such as magnetism (Oshio et al., 1996) and biological or medicinal activities (Corey et al., 1987; Dias et al., 2006). In this work, a mixed ligand complex of copper(I) iodide with 1,2-bis(diphenylphosphanyl)ethane (dppe) and N,N'-diethylthiourea (detu) is reported. The binuclear copper(I) complex lies across an inversion center. The µ2-dppe bridges between CuI centers leads to a 10-membered Cu2P4C4 rhomboid, see Fig. 1. The Cu1—P1 and Cu1—P2 bond lengths are 2.2681 (6) and 2.2813 (6)Å, respectively. These values are slightly shorter than the equivalent distances found in [Cu(tsac)(PPh3)2], [Cu4(tsac)4(PPh3)3], [Cu2(tsac)2(dppm)2] and [Cu4(tsac)4(dppm)2], which are in the range 2.2799 (5) and 2.3119 (5) Å (Dennehy et al., 2009). There is an intramolecular N2—H2···I1 hydrogen bond. In the crystal, intermolecular N1—H1···I1 hydrogen bonds link complex molecules into a two-dimensional supramolecular network parallel to (-101) (Fig. 2. and Table 1)
For background to the coordination chemistry of copper(I) halides and pseudohalides, see: Dennehy et al. (2011); Oshio et al. (1996); Sewead et al. (2003). For their potential applications, see: Corey et al. (1987); Dias et al. (2006). For relevant examples of discrete complexes, see: Dennehy et al. (2009).
N,N'-Diethylthiourea (0.07 g, 0.5 mmol) was dissolved in 30 cm3 of acetonitrile in a round flask equipped with reflux condenser and magnetic stirrer at 333 K and then CuI (0.1 g, 0.5 mmol) was added. The mixture was stirred for 2 h. 1,2-bis(diphenylphosphanyl)ethane (0.2 g, 0.5 mmol) was added and the reaction mixture was heated under reflux for 5 h where upon the precipitate gradually disappeared. The resulting clear solution was filtered and left to evaporate at room temperature. The colorless crystals, which deposited after standing for several days were filtered off and washed with acetone and dried in vacuo (M. pt = 557 K). Elemental analysis, calculated for [Cu2I2(C26H24P2)2(C5H12N2S)2]: C, 51.59; H, 4.97; N, 3.88; S, 4.44%, found: C, 55.69; H, 5.22; N, 3.62; S, 4.61%.
detailsThe (-1 8 3) reflection was affected by the beam-stop and was omitted from the final cycles of
H atoms bonded to C and N atoms were included in their calculated positions and were refined using a riding model using bond lengths of 0.95–0.99 Å and Uiso(H) = 1.2–1.5Ueq(C), and N—H = 0.88 Å (NH) and Uiso(H) = 1.2Ueq(N). The (-1 8 3) reflection was omitted owing to poor agreement.Data collection: APEX2 (Bruker, 2013); cell
SAINT (Bruker, 2013); data reduction: SAINT (Bruker, 2013); program(s) used to solve structure: SHELXS97 (Sheldrick, 2008); program(s) used to refine structure: SHELXL2015 (Sheldrick, 2015) and SHELXLE (Hübschle et al., 2011); molecular graphics: Mercury (Macrae et al., 2008); software used to prepare material for publication: publCIF (Westrip, 2010).[Cu2I2(C26H24P2)2(C5H12N2S)2] | F(000) = 1456 |
Mr = 1442.11 | Dx = 1.513 Mg m−3 |
Monoclinic, P21/n | Cu Kα radiation, λ = 1.54178 Å |
a = 12.2150 (8) Å | Cell parameters from 9846 reflections |
b = 15.1836 (9) Å | θ = 3.9–66.7° |
c = 17.1801 (10) Å | µ = 10.37 mm−1 |
β = 96.414 (2)° | T = 100 K |
V = 3166.4 (3) Å3 | Block, colourless |
Z = 2 | 0.16 × 0.15 × 0.08 mm |
Bruker Prospector CCD diffractometer | 5564 independent reflections |
Radiation source: I-mu-S microsource X-ray tube | 5556 reflections with I > 2σ(I) |
Laterally graded multilayer (Goebel) mirror monochromator | Rint = 0.028 |
ω and phi scans | θmax = 67.0°, θmin = 3.9° |
Absorption correction: multi-scan (SADABS; Bruker, 2013) | h = −14→12 |
Tmin = 0.433, Tmax = 0.753 | k = −18→17 |
23236 measured reflections | l = −20→20 |
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)] = 0.025 | Hydrogen site location: inferred from neighbouring sites |
wR(F2) = 0.063 | H-atom parameters constrained |
S = 1.13 | w = 1/[σ2(Fo2) + (0.0315P)2 + 3.4263P] where P = (Fo2 + 2Fc2)/3 |
5564 reflections | (Δ/σ)max = 0.003 |
345 parameters | Δρmax = 0.98 e Å−3 |
0 restraints | Δρmin = −0.92 e Å−3 |
[Cu2I2(C26H24P2)2(C5H12N2S)2] | V = 3166.4 (3) Å3 |
Mr = 1442.11 | Z = 2 |
Monoclinic, P21/n | Cu Kα radiation |
a = 12.2150 (8) Å | µ = 10.37 mm−1 |
b = 15.1836 (9) Å | T = 100 K |
c = 17.1801 (10) Å | 0.16 × 0.15 × 0.08 mm |
β = 96.414 (2)° |
Bruker Prospector CCD diffractometer | 5564 independent reflections |
Absorption correction: multi-scan (SADABS; Bruker, 2013) | 5556 reflections with I > 2σ(I) |
Tmin = 0.433, Tmax = 0.753 | Rint = 0.028 |
23236 measured reflections |
R[F2 > 2σ(F2)] = 0.025 | 0 restraints |
wR(F2) = 0.063 | H-atom parameters constrained |
S = 1.13 | Δρmax = 0.98 e Å−3 |
5564 reflections | Δρmin = −0.92 e Å−3 |
345 parameters |
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. |
x | y | z | Uiso*/Ueq | ||
I1 | 0.71658 (2) | 0.56133 (2) | 0.16309 (2) | 0.01039 (6) | |
Cu1 | 0.51704 (2) | 0.64264 (2) | 0.12681 (2) | 0.00798 (8) | |
S1 | 0.48147 (4) | 0.74104 (3) | 0.22620 (3) | 0.01238 (12) | |
P1 | 0.39142 (4) | 0.53264 (3) | 0.12684 (3) | 0.00711 (11) | |
P2 | 0.52134 (4) | 0.70642 (3) | 0.00696 (3) | 0.00768 (11) | |
N1 | 0.58767 (16) | 0.88958 (13) | 0.27366 (12) | 0.0163 (4) | |
H1 | 0.6493 | 0.9171 | 0.2902 | 0.020* | |
N2 | 0.69626 (15) | 0.77334 (13) | 0.24764 (11) | 0.0122 (4) | |
H2 | 0.7019 | 0.7167 | 0.2380 | 0.015* | |
C1 | 0.59546 (18) | 0.80593 (15) | 0.25058 (12) | 0.0109 (4) | |
C2 | 0.4851 (2) | 0.93892 (15) | 0.27369 (17) | 0.0198 (5) | |
H2A | 0.4929 | 0.9817 | 0.3174 | 0.024* | |
H2B | 0.4250 | 0.8977 | 0.2827 | 0.024* | |
C3 | 0.4547 (3) | 0.9875 (2) | 0.19789 (19) | 0.0348 (7) | |
H3A | 0.5135 | 1.0289 | 0.1891 | 0.052* | |
H3B | 0.3859 | 1.0199 | 0.2007 | 0.052* | |
H3C | 0.4448 | 0.9452 | 0.1546 | 0.052* | |
C4 | 0.79787 (18) | 0.82441 (16) | 0.25912 (14) | 0.0149 (5) | |
H4A | 0.8076 | 0.8487 | 0.3129 | 0.018* | |
H4B | 0.7936 | 0.8743 | 0.2218 | 0.018* | |
C5 | 0.89514 (18) | 0.76646 (16) | 0.24646 (14) | 0.0162 (5) | |
H5A | 0.8813 | 0.7370 | 0.1956 | 0.024* | |
H5B | 0.9055 | 0.7222 | 0.2881 | 0.024* | |
H5C | 0.9617 | 0.8027 | 0.2475 | 0.024* | |
C11 | 0.38548 (18) | 0.47611 (14) | 0.22045 (13) | 0.0103 (4) | |
C12 | 0.45710 (18) | 0.50116 (14) | 0.28549 (13) | 0.0124 (4) | |
H12 | 0.5106 | 0.5456 | 0.2807 | 0.015* | |
C13 | 0.4500 (2) | 0.46061 (16) | 0.35789 (13) | 0.0161 (5) | |
H13 | 0.4989 | 0.4777 | 0.4022 | 0.019* | |
C14 | 0.3723 (2) | 0.39590 (16) | 0.36541 (14) | 0.0196 (5) | |
H14 | 0.3673 | 0.3692 | 0.4149 | 0.024* | |
C15 | 0.3015 (2) | 0.36998 (17) | 0.30053 (15) | 0.0201 (5) | |
H15 | 0.2486 | 0.3250 | 0.3055 | 0.024* | |
C16 | 0.30793 (19) | 0.40978 (16) | 0.22830 (14) | 0.0149 (5) | |
H16 | 0.2594 | 0.3918 | 0.1840 | 0.018* | |
C21 | 0.24971 (18) | 0.57205 (14) | 0.10553 (14) | 0.0109 (4) | |
C22 | 0.1845 (2) | 0.55542 (16) | 0.03495 (15) | 0.0188 (5) | |
H22 | 0.2117 | 0.5190 | −0.0035 | 0.023* | |
C23 | 0.0792 (2) | 0.59235 (18) | 0.02086 (16) | 0.0240 (5) | |
H23 | 0.0359 | 0.5819 | −0.0277 | 0.029* | |
C24 | 0.0375 (2) | 0.64380 (17) | 0.07685 (17) | 0.0246 (6) | |
H24 | −0.0346 | 0.6678 | 0.0674 | 0.029* | |
C25 | 0.1021 (2) | 0.66008 (18) | 0.14715 (17) | 0.0245 (6) | |
H25 | 0.0739 | 0.6953 | 0.1860 | 0.029* | |
C26 | 0.2072 (2) | 0.62539 (17) | 0.16094 (14) | 0.0177 (5) | |
H26 | 0.2510 | 0.6381 | 0.2088 | 0.021* | |
C27 | 0.39162 (19) | 0.44094 (13) | 0.05650 (13) | 0.0098 (4) | |
H27A | 0.3228 | 0.4068 | 0.0578 | 0.012* | |
H27B | 0.3910 | 0.4658 | 0.0032 | 0.012* | |
C28 | 0.51050 (17) | 0.62207 (14) | −0.07137 (12) | 0.0090 (4) | |
H28A | 0.4406 | 0.5891 | −0.0713 | 0.011* | |
H28B | 0.5110 | 0.6507 | −0.1231 | 0.011* | |
C31 | 0.40910 (19) | 0.78228 (15) | −0.02656 (12) | 0.0126 (4) | |
C32 | 0.4258 (2) | 0.87216 (18) | −0.03567 (19) | 0.0302 (6) | |
H32 | 0.4977 | 0.8963 | −0.0252 | 0.036* | |
C33 | 0.3369 (3) | 0.9266 (2) | −0.0601 (2) | 0.0432 (8) | |
H33 | 0.3488 | 0.9880 | −0.0658 | 0.052* | |
C34 | 0.2325 (3) | 0.8932 (2) | −0.07599 (18) | 0.0343 (7) | |
H34 | 0.1728 | 0.9310 | −0.0933 | 0.041* | |
C35 | 0.2148 (2) | 0.8042 (2) | −0.06672 (16) | 0.0279 (6) | |
H35 | 0.1427 | 0.7805 | −0.0779 | 0.033* | |
C36 | 0.3023 (2) | 0.74917 (18) | −0.04106 (15) | 0.0205 (5) | |
H36 | 0.2893 | 0.6883 | −0.0333 | 0.025* | |
C41 | 0.64463 (18) | 0.76671 (14) | −0.01297 (13) | 0.0114 (4) | |
C42 | 0.7191 (2) | 0.79247 (18) | 0.04993 (15) | 0.0239 (6) | |
H42 | 0.7029 | 0.7809 | 0.1018 | 0.029* | |
C43 | 0.8164 (3) | 0.8347 (2) | 0.03845 (17) | 0.0333 (7) | |
H43 | 0.8658 | 0.8524 | 0.0823 | 0.040* | |
C44 | 0.8419 (2) | 0.8513 (2) | −0.03605 (18) | 0.0315 (7) | |
H44 | 0.9092 | 0.8794 | −0.0440 | 0.038* | |
C45 | 0.7686 (3) | 0.8267 (3) | −0.09912 (18) | 0.0423 (9) | |
H45 | 0.7856 | 0.8383 | −0.1508 | 0.051* | |
C46 | 0.6708 (3) | 0.7853 (2) | −0.08813 (15) | 0.0316 (7) | |
H46 | 0.6209 | 0.7694 | −0.1323 | 0.038* |
U11 | U22 | U33 | U12 | U13 | U23 | |
I1 | 0.01029 (9) | 0.00674 (9) | 0.01363 (9) | 0.00312 (4) | −0.00089 (6) | −0.00191 (4) |
Cu1 | 0.00902 (16) | 0.00693 (16) | 0.00820 (15) | −0.00076 (11) | 0.00197 (12) | −0.00022 (11) |
S1 | 0.0096 (2) | 0.0109 (3) | 0.0175 (3) | −0.00149 (19) | 0.0049 (2) | −0.0069 (2) |
P1 | 0.0074 (2) | 0.0068 (3) | 0.0076 (2) | −0.00001 (19) | 0.00262 (19) | −0.00070 (19) |
P2 | 0.0097 (3) | 0.0057 (2) | 0.0078 (2) | 0.00084 (19) | 0.00168 (19) | 0.00046 (19) |
N1 | 0.0105 (9) | 0.0122 (10) | 0.0262 (11) | −0.0006 (8) | 0.0025 (8) | −0.0094 (8) |
N2 | 0.0100 (9) | 0.0092 (9) | 0.0174 (9) | 0.0010 (7) | 0.0012 (7) | −0.0073 (7) |
C1 | 0.0121 (10) | 0.0117 (11) | 0.0096 (10) | 0.0003 (8) | 0.0036 (8) | −0.0022 (8) |
C2 | 0.0172 (12) | 0.0122 (12) | 0.0315 (14) | 0.0030 (9) | 0.0091 (11) | −0.0075 (9) |
C3 | 0.0314 (15) | 0.0299 (16) | 0.0441 (17) | 0.0096 (13) | 0.0083 (13) | 0.0068 (13) |
C4 | 0.0112 (11) | 0.0149 (11) | 0.0185 (11) | −0.0007 (9) | 0.0012 (9) | −0.0063 (9) |
C5 | 0.0105 (10) | 0.0172 (12) | 0.0208 (12) | −0.0002 (9) | 0.0011 (9) | −0.0089 (9) |
C11 | 0.0117 (10) | 0.0088 (10) | 0.0112 (10) | 0.0041 (8) | 0.0052 (8) | 0.0014 (8) |
C12 | 0.0144 (10) | 0.0090 (10) | 0.0146 (11) | 0.0020 (8) | 0.0051 (9) | −0.0004 (8) |
C13 | 0.0214 (12) | 0.0149 (11) | 0.0124 (11) | 0.0049 (10) | 0.0030 (9) | −0.0003 (9) |
C14 | 0.0248 (12) | 0.0197 (13) | 0.0164 (11) | 0.0054 (10) | 0.0115 (10) | 0.0085 (9) |
C15 | 0.0170 (11) | 0.0186 (12) | 0.0260 (13) | −0.0024 (10) | 0.0088 (10) | 0.0076 (10) |
C16 | 0.0106 (10) | 0.0166 (12) | 0.0181 (11) | −0.0015 (9) | 0.0036 (9) | 0.0029 (9) |
C21 | 0.0088 (10) | 0.0093 (10) | 0.0151 (11) | −0.0017 (8) | 0.0033 (9) | 0.0016 (8) |
C22 | 0.0156 (12) | 0.0219 (13) | 0.0185 (12) | 0.0035 (9) | 0.0002 (10) | −0.0044 (9) |
C23 | 0.0166 (12) | 0.0239 (14) | 0.0297 (14) | 0.0046 (11) | −0.0059 (10) | 0.0002 (11) |
C24 | 0.0120 (11) | 0.0191 (13) | 0.0425 (16) | 0.0048 (10) | 0.0023 (11) | 0.0007 (11) |
C25 | 0.0191 (12) | 0.0202 (13) | 0.0358 (15) | 0.0057 (10) | 0.0105 (11) | −0.0064 (11) |
C26 | 0.0175 (12) | 0.0161 (12) | 0.0200 (12) | 0.0017 (9) | 0.0042 (10) | −0.0048 (9) |
C27 | 0.0112 (11) | 0.0082 (11) | 0.0101 (10) | 0.0002 (8) | 0.0017 (8) | −0.0020 (7) |
C28 | 0.0111 (10) | 0.0075 (10) | 0.0085 (10) | 0.0002 (8) | 0.0016 (8) | −0.0017 (8) |
C31 | 0.0175 (11) | 0.0123 (11) | 0.0088 (10) | 0.0062 (9) | 0.0039 (8) | 0.0011 (8) |
C32 | 0.0274 (14) | 0.0171 (13) | 0.0456 (17) | 0.0059 (11) | 0.0025 (12) | 0.0054 (12) |
C33 | 0.045 (2) | 0.0210 (15) | 0.064 (2) | 0.0149 (14) | 0.0092 (17) | 0.0142 (15) |
C34 | 0.0319 (15) | 0.0399 (18) | 0.0315 (15) | 0.0273 (14) | 0.0049 (12) | 0.0107 (13) |
C35 | 0.0188 (13) | 0.0409 (17) | 0.0238 (13) | 0.0122 (12) | 0.0018 (10) | −0.0045 (12) |
C36 | 0.0179 (12) | 0.0221 (13) | 0.0218 (12) | 0.0057 (10) | 0.0042 (10) | −0.0024 (10) |
C41 | 0.0149 (11) | 0.0054 (10) | 0.0140 (11) | −0.0001 (8) | 0.0027 (9) | 0.0020 (8) |
C42 | 0.0278 (14) | 0.0278 (14) | 0.0154 (12) | −0.0125 (11) | 0.0003 (10) | 0.0057 (10) |
C43 | 0.0305 (15) | 0.0388 (17) | 0.0285 (15) | −0.0211 (13) | −0.0067 (12) | 0.0108 (13) |
C44 | 0.0245 (14) | 0.0330 (16) | 0.0371 (16) | −0.0154 (12) | 0.0042 (12) | 0.0131 (13) |
C45 | 0.0434 (18) | 0.063 (2) | 0.0220 (14) | −0.0303 (17) | 0.0116 (13) | 0.0075 (14) |
C46 | 0.0358 (16) | 0.0455 (18) | 0.0128 (12) | −0.0229 (14) | 0.0002 (11) | 0.0039 (12) |
I1—Cu1 | 2.7412 (4) | C21—C26 | 1.394 (3) |
Cu1—P1 | 2.2681 (6) | C21—C22 | 1.398 (4) |
Cu1—P2 | 2.2813 (6) | C22—C23 | 1.399 (4) |
Cu1—S1 | 2.3457 (6) | C22—H22 | 0.9500 |
S1—C1 | 1.719 (2) | C23—C24 | 1.380 (4) |
P1—C21 | 1.829 (2) | C23—H23 | 0.9500 |
P1—C11 | 1.832 (2) | C24—C25 | 1.389 (4) |
P1—C27 | 1.844 (2) | C24—H24 | 0.9500 |
P2—C41 | 1.827 (2) | C25—C26 | 1.384 (4) |
P2—C31 | 1.834 (2) | C25—H25 | 0.9500 |
P2—C28 | 1.852 (2) | C26—H26 | 0.9500 |
N1—C1 | 1.337 (3) | C27—C28i | 1.530 (3) |
N1—C2 | 1.459 (3) | C27—H27A | 0.9900 |
N1—H1 | 0.8800 | C27—H27B | 0.9900 |
N2—C1 | 1.333 (3) | C28—C27i | 1.530 (3) |
N2—C4 | 1.458 (3) | C28—H28A | 0.9900 |
N2—H2 | 0.8800 | C28—H28B | 0.9900 |
C2—C3 | 1.507 (4) | C31—C32 | 1.391 (4) |
C2—H2A | 0.9900 | C31—C36 | 1.394 (4) |
C2—H2B | 0.9900 | C32—C33 | 1.391 (4) |
C3—H3A | 0.9800 | C32—H32 | 0.9500 |
C3—H3B | 0.9800 | C33—C34 | 1.371 (5) |
C3—H3C | 0.9800 | C33—H33 | 0.9500 |
C4—C5 | 1.514 (3) | C34—C35 | 1.381 (5) |
C4—H4A | 0.9900 | C34—H34 | 0.9500 |
C4—H4B | 0.9900 | C35—C36 | 1.389 (4) |
C5—H5A | 0.9800 | C35—H35 | 0.9500 |
C5—H5B | 0.9800 | C36—H36 | 0.9500 |
C5—H5C | 0.9800 | C41—C42 | 1.389 (3) |
C11—C12 | 1.393 (3) | C41—C46 | 1.393 (3) |
C11—C16 | 1.399 (3) | C42—C43 | 1.384 (4) |
C12—C13 | 1.399 (3) | C42—H42 | 0.9500 |
C12—H12 | 0.9500 | C43—C44 | 1.374 (4) |
C13—C14 | 1.382 (4) | C43—H43 | 0.9500 |
C13—H13 | 0.9500 | C44—C45 | 1.378 (5) |
C14—C15 | 1.389 (4) | C44—H44 | 0.9500 |
C14—H14 | 0.9500 | C45—C46 | 1.381 (4) |
C15—C16 | 1.390 (3) | C45—H45 | 0.9500 |
C15—H15 | 0.9500 | C46—H46 | 0.9500 |
C16—H16 | 0.9500 | ||
P1—Cu1—P2 | 113.37 (2) | C15—C16—H16 | 119.8 |
P1—Cu1—S1 | 106.77 (2) | C11—C16—H16 | 119.8 |
P2—Cu1—S1 | 114.30 (2) | C26—C21—C22 | 118.6 (2) |
P1—Cu1—I1 | 104.637 (18) | C26—C21—P1 | 118.01 (18) |
P2—Cu1—I1 | 106.669 (17) | C22—C21—P1 | 123.33 (18) |
S1—Cu1—I1 | 110.709 (17) | C21—C22—C23 | 120.1 (2) |
C1—S1—Cu1 | 109.37 (7) | C21—C22—H22 | 119.9 |
C21—P1—C11 | 101.52 (10) | C23—C22—H22 | 119.9 |
C21—P1—C27 | 100.74 (10) | C24—C23—C22 | 120.6 (2) |
C11—P1—C27 | 102.98 (10) | C24—C23—H23 | 119.7 |
C21—P1—Cu1 | 112.59 (7) | C22—C23—H23 | 119.7 |
C11—P1—Cu1 | 116.01 (8) | C23—C24—C25 | 119.3 (2) |
C27—P1—Cu1 | 120.36 (7) | C23—C24—H24 | 120.4 |
C41—P2—C31 | 103.26 (10) | C25—C24—H24 | 120.4 |
C41—P2—C28 | 101.76 (10) | C26—C25—C24 | 120.5 (2) |
C31—P2—C28 | 102.47 (10) | C26—C25—H25 | 119.8 |
C41—P2—Cu1 | 118.97 (7) | C24—C25—H25 | 119.8 |
C31—P2—Cu1 | 117.28 (7) | C25—C26—C21 | 120.9 (2) |
C28—P2—Cu1 | 110.82 (7) | C25—C26—H26 | 119.5 |
C1—N1—C2 | 125.3 (2) | C21—C26—H26 | 119.5 |
C1—N1—H1 | 117.4 | C28i—C27—P1 | 114.89 (15) |
C2—N1—H1 | 117.4 | C28i—C27—H27A | 108.5 |
C1—N2—C4 | 124.98 (19) | P1—C27—H27A | 108.5 |
C1—N2—H2 | 117.5 | C28i—C27—H27B | 108.5 |
C4—N2—H2 | 117.5 | P1—C27—H27B | 108.5 |
N2—C1—N1 | 117.4 (2) | H27A—C27—H27B | 107.5 |
N2—C1—S1 | 120.29 (17) | C27i—C28—P2 | 108.66 (14) |
N1—C1—S1 | 122.29 (17) | C27i—C28—H28A | 110.0 |
N1—C2—C3 | 112.4 (2) | P2—C28—H28A | 110.0 |
N1—C2—H2A | 109.1 | C27i—C28—H28B | 110.0 |
C3—C2—H2A | 109.1 | P2—C28—H28B | 110.0 |
N1—C2—H2B | 109.1 | H28A—C28—H28B | 108.3 |
C3—C2—H2B | 109.1 | C32—C31—C36 | 118.7 (2) |
H2A—C2—H2B | 107.9 | C32—C31—P2 | 122.5 (2) |
C2—C3—H3A | 109.5 | C36—C31—P2 | 118.77 (18) |
C2—C3—H3B | 109.5 | C33—C32—C31 | 119.8 (3) |
H3A—C3—H3B | 109.5 | C33—C32—H32 | 120.1 |
C2—C3—H3C | 109.5 | C31—C32—H32 | 120.1 |
H3A—C3—H3C | 109.5 | C34—C33—C32 | 121.2 (3) |
H3B—C3—H3C | 109.5 | C34—C33—H33 | 119.4 |
N2—C4—C5 | 109.97 (19) | C32—C33—H33 | 119.4 |
N2—C4—H4A | 109.7 | C33—C34—C35 | 119.6 (3) |
C5—C4—H4A | 109.7 | C33—C34—H34 | 120.2 |
N2—C4—H4B | 109.7 | C35—C34—H34 | 120.2 |
C5—C4—H4B | 109.7 | C34—C35—C36 | 120.0 (3) |
H4A—C4—H4B | 108.2 | C34—C35—H35 | 120.0 |
C4—C5—H5A | 109.5 | C36—C35—H35 | 120.0 |
C4—C5—H5B | 109.5 | C35—C36—C31 | 120.8 (3) |
H5A—C5—H5B | 109.5 | C35—C36—H36 | 119.6 |
C4—C5—H5C | 109.5 | C31—C36—H36 | 119.6 |
H5A—C5—H5C | 109.5 | C42—C41—C46 | 117.8 (2) |
H5B—C5—H5C | 109.5 | C42—C41—P2 | 118.50 (18) |
C12—C11—C16 | 119.4 (2) | C46—C41—P2 | 123.68 (18) |
C12—C11—P1 | 119.57 (17) | C43—C42—C41 | 121.2 (2) |
C16—C11—P1 | 121.03 (17) | C43—C42—H42 | 119.4 |
C11—C12—C13 | 119.8 (2) | C41—C42—H42 | 119.4 |
C11—C12—H12 | 120.1 | C44—C43—C42 | 120.3 (3) |
C13—C12—H12 | 120.1 | C44—C43—H43 | 119.8 |
C14—C13—C12 | 120.5 (2) | C42—C43—H43 | 119.8 |
C14—C13—H13 | 119.7 | C43—C44—C45 | 119.2 (3) |
C12—C13—H13 | 119.7 | C43—C44—H44 | 120.4 |
C13—C14—C15 | 119.9 (2) | C45—C44—H44 | 120.4 |
C13—C14—H14 | 120.0 | C44—C45—C46 | 120.8 (3) |
C15—C14—H14 | 120.0 | C44—C45—H45 | 119.6 |
C14—C15—C16 | 120.0 (2) | C46—C45—H45 | 119.6 |
C14—C15—H15 | 120.0 | C45—C46—C41 | 120.7 (3) |
C16—C15—H15 | 120.0 | C45—C46—H46 | 119.6 |
C15—C16—C11 | 120.3 (2) | C41—C46—H46 | 119.6 |
C4—N2—C1—N1 | −7.2 (3) | P1—C21—C26—C25 | 177.6 (2) |
C4—N2—C1—S1 | 173.37 (18) | C21—P1—C27—C28i | −165.70 (16) |
C2—N1—C1—N2 | 174.1 (2) | C11—P1—C27—C28i | −61.09 (18) |
C2—N1—C1—S1 | −6.5 (3) | Cu1—P1—C27—C28i | 69.95 (17) |
Cu1—S1—C1—N2 | −33.6 (2) | C41—P2—C28—C27i | 66.78 (16) |
Cu1—S1—C1—N1 | 146.99 (17) | C31—P2—C28—C27i | 173.40 (15) |
C1—N1—C2—C3 | −90.6 (3) | Cu1—P2—C28—C27i | −60.70 (15) |
C1—N2—C4—C5 | −176.4 (2) | C41—P2—C31—C32 | −20.2 (2) |
C21—P1—C11—C12 | −123.32 (18) | C28—P2—C31—C32 | −125.7 (2) |
C27—P1—C11—C12 | 132.67 (18) | Cu1—P2—C31—C32 | 112.8 (2) |
Cu1—P1—C11—C12 | −0.9 (2) | C41—P2—C31—C36 | 161.93 (18) |
C21—P1—C11—C16 | 54.8 (2) | C28—P2—C31—C36 | 56.5 (2) |
C27—P1—C11—C16 | −49.2 (2) | Cu1—P2—C31—C36 | −65.11 (19) |
Cu1—P1—C11—C16 | 177.20 (16) | C36—C31—C32—C33 | −1.1 (4) |
C16—C11—C12—C13 | −0.7 (3) | P2—C31—C32—C33 | −178.9 (3) |
P1—C11—C12—C13 | 177.45 (17) | C31—C32—C33—C34 | −0.4 (5) |
C11—C12—C13—C14 | −0.1 (3) | C32—C33—C34—C35 | 0.8 (5) |
C12—C13—C14—C15 | 0.8 (4) | C33—C34—C35—C36 | 0.3 (4) |
C13—C14—C15—C16 | −0.7 (4) | C34—C35—C36—C31 | −1.9 (4) |
C14—C15—C16—C11 | −0.1 (4) | C32—C31—C36—C35 | 2.2 (4) |
C12—C11—C16—C15 | 0.8 (3) | P2—C31—C36—C35 | −179.84 (19) |
P1—C11—C16—C15 | −177.35 (18) | C31—P2—C41—C42 | 114.9 (2) |
C11—P1—C21—C26 | 56.7 (2) | C28—P2—C41—C42 | −139.1 (2) |
C27—P1—C21—C26 | 162.44 (19) | Cu1—P2—C41—C42 | −17.1 (2) |
Cu1—P1—C21—C26 | −68.06 (19) | C31—P2—C41—C46 | −67.9 (2) |
C11—P1—C21—C22 | −127.0 (2) | C28—P2—C41—C46 | 38.1 (3) |
C27—P1—C21—C22 | −21.2 (2) | Cu1—P2—C41—C46 | 160.1 (2) |
Cu1—P1—C21—C22 | 108.27 (19) | C46—C41—C42—C43 | −0.4 (4) |
C26—C21—C22—C23 | 0.3 (4) | P2—C41—C42—C43 | 177.0 (2) |
P1—C21—C22—C23 | −176.0 (2) | C41—C42—C43—C44 | −0.7 (5) |
C21—C22—C23—C24 | −1.5 (4) | C42—C43—C44—C45 | 1.1 (5) |
C22—C23—C24—C25 | 1.2 (4) | C43—C44—C45—C46 | −0.4 (6) |
C23—C24—C25—C26 | 0.2 (4) | C44—C45—C46—C41 | −0.7 (6) |
C24—C25—C26—C21 | −1.3 (4) | C42—C41—C46—C45 | 1.1 (5) |
C22—C21—C26—C25 | 1.1 (4) | P2—C41—C46—C45 | −176.2 (3) |
Symmetry code: (i) −x+1, −y+1, −z. |
D—H···A | D—H | H···A | D···A | D—H···A |
N1—H1···I1ii | 0.88 | 2.80 | 3.622 (2) | 156 |
N2—H2···I1 | 0.88 | 2.70 | 3.5517 (19) | 162 |
Symmetry code: (ii) −x+3/2, y+1/2, −z+1/2. |
D—H···A | D—H | H···A | D···A | D—H···A |
N1—H1···I1i | 0.88 | 2.80 | 3.622 (2) | 156 |
N2—H2···I1 | 0.88 | 2.70 | 3.5517 (19) | 162 |
Symmetry code: (i) −x+3/2, y+1/2, −z+1/2. |
Acknowledgements
We gratefully acknowledge financial support from the Strategic Scholarships Fellowships Frontier Research Networks (Specific for Southern Region), the Commission on Higher Education, Ministry of Education, and the Department of Chemistry and Graduate School, Prince of Songkla University. LK would like to thank Dr Matthias Zeller of Youngstown State University, Ohio, USA, for suggestions and assistance with the X-ray structure refinement.
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