metal-organic compounds
Chlorido[5-methoxy-1H-benzimidazole-2(3H)-thione-κS]bis(triphenylphosphane-κP)copper(I) methanol disolvate
aDaxing High School Attached to CNU, Beijing 102600, People's Republic of China
*Correspondence e-mail: mengqx90@163.com
In the title complex, [CuCl(C8H8N2OS)(C18H15P)2]·2CH3OH, the CuI ion is coordinated by one chloride anion, one S atom from the 5-methoxy-1H-benzimidazole-2(3H)-thione ligand and two P atoms from two triphenylphosphine ligands in a distorted tetrahedral geometry. One of the N-bound H atoms is involved in an intramolecular N—H⋯Cl hydrogen bond, while another one interacts with the solvent methanol molecule via an N—H⋯O hydrogen bond. Intermolecular O—H⋯Cl and O—H⋯O hydrogen bonds link two further complex molecules and four solvent molecules into a centrosymmetric structural unit. The short distance of 3.624 (4) Å between the centroids of the five- and the six-membered rings of two benzimidazole fragments indicates the presence of π–π interactions.
CCDC reference: 982066
Related literature
For the structures and properties of CuI complexes with triphenlyphosphine ligands, see: Gennari et al. (2006); Kitagawa et al. (1995); Raper (1994). For complexes with a 5-methoxy-1H-benzimidazole-2(3H)-thione ligand, see: Schneider et al. (2008). For related structures, see: Lobana & Castineiras (2002).
Experimental
Crystal data
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Data collection: SMART (Bruker, 2007); cell SAINT-Plus (Bruker, 2007); data reduction: SAINT-Plus; program(s) used to solve structure: SHELXS97 (Sheldrick, 2008); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008); molecular graphics: SHELXTL (Sheldrick, 2008); software used to prepare material for publication: SHELXTL.
Supporting information
CCDC reference: 982066
10.1107/S1600536814001251/cv5442sup1.cif
contains datablocks global, I. DOI:Structure factors: contains datablock I. DOI: 10.1107/S1600536814001251/cv5442Isup2.hkl
Supporting information file. DOI: 10.1107/S1600536814001251/cv5442Isup3.cdx
A mixture of CuCl (0.2 mmol) and 5-methoxy-1H-benzimidazole- 2(3H)-thione(0.2 mmol) in MeOH and CH2Cl2 (10 mL, v/v = 1:1) was stirred for 2 h and triphenylphosphine (0.2 mmol) was added to the mixture which was stirred for another 4 h. The insoluble residues were removed by filtration, and filtrate was evaporated slowly at room temperature for two weeks to yield colorless crystalline products.
H atoms were positioned geometrically [C—H = 0.93 – 0.96 Å, N—H = 0.86 Å, O—H = 0.82 Å] and refined as riding, with Uiso(H) = 1.2 – 1.5 Ueq of the parent atom.
Cu(I) complexes containing triphenlyphosphine and mercaptan ligands have received much attention in the past, mainly because of their interesting coordination chemistry and potential applications in photography, biochemistry and enzymatic reactions (Gennari et al., 2006; Kitagawa et al., 1995; Raper et al., 1994). However, only one structure was reported for metal-MOBMT complex (MOBMT = 5-methoxy-1H- benzimidazole-2(3H)-thione) (Schneider et al., 2008). Herewith we present the
of new Cu(I) complex with triphenlyphosphine and MOBMT ligands.In the title complex, MOMBT act as neutral, monodentate ligand with the S atom as a coordination atom. Other sites of the coordination tetrahedron are occupied by two P atoms from two triphenlyphosphine ligands and one halide anion. The Cu—S and Cu—P bond distances are similar to those reported in other copper(I) complexes (Lobana et al., 2002). The environment around copper(I) is distorted tetrahedral, angles around the Cu atom ranging from 102.1 (1)–122.0 (1)°. A dimer is formed by hydrogen bonds N—H···O, O—H···Cl, O—H···O between the unit [CuX(thione)(PPh3)2] and the solvent methanol molecules. An intramolecular N—H···Cl hydrogen bond is also observed (Table 1). Furthermore, the centroid to centroid distance between the parallel five- and six-membered rings of two benzimidazole fragments is 3.624 (4) Å, which suggests an existence of π···π interactions between them.
For the structures and properties of CuI complexes with triphenlyphosphine ligands, see: Gennari et al. (2006); Kitagawa et al. (1995); Raper (1994). For complexes with the 5-methoxy-1H-benzimidazole -2(3H)-thione ligand, see: Schneider et al. (2008). For related structures, see: Lobana & Castineiras (2002).
Data collection: SMART (Bruker, 2007); cell
SAINT-Plus (Bruker, 2007); data reduction: SAINT-Plus (Bruker, 2007); program(s) used to solve structure: SHELXS97 (Sheldrick, 2008); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008); molecular graphics: SHELXTL (Sheldrick, 2008); software used to prepare material for publication: SHELXTL (Sheldrick, 2008).Fig. 1. The molecular structure of the title compound showing the atomic numbering and 30% probability displacement ellipsoids. Solvent molecules and H atoms have been omitted for clarity. |
[CuCl(C8H8N2OS)(C18H15P)2]·2CH4O | F(000) = 1808 |
Mr = 867.84 | Dx = 1.293 Mg m−3 |
Monoclinic, P21/c | Mo Kα radiation, λ = 0.71073 Å |
Hall symbol: -P 2ybc | Cell parameters from 1965 reflections |
a = 12.8354 (9) Å | θ = 2.6–18.0° |
b = 18.4979 (17) Å | µ = 0.71 mm−1 |
c = 18.7933 (18) Å | T = 298 K |
β = 92.839 (12)° | Block, colorless |
V = 4456.6 (7) Å3 | 0.34 × 0.27 × 0.15 mm |
Z = 4 |
Bruker SMART APEX CCD area-detector diffractometer | 7835 independent reflections |
Radiation source: fine-focus sealed tube | 3113 reflections with I > 2σ(I) |
Graphite monochromator | Rint = 0.143 |
phi and ω scans | θmax = 25.0°, θmin = 2.6° |
Absorption correction: multi-scan (SADABS; Bruker, 2007) | h = −15→15 |
Tmin = 0.794, Tmax = 0.901 | k = −15→21 |
22332 measured reflections | l = −22→22 |
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)] = 0.086 | Hydrogen site location: inferred from neighbouring sites |
wR(F2) = 0.217 | H-atom parameters constrained |
S = 1.07 | w = 1/[σ2(Fo2) + (0.0574P)2] where P = (Fo2 + 2Fc2)/3 |
7835 reflections | (Δ/σ)max = 0.001 |
510 parameters | Δρmax = 1.53 e Å−3 |
0 restraints | Δρmin = −0.57 e Å−3 |
[CuCl(C8H8N2OS)(C18H15P)2]·2CH4O | V = 4456.6 (7) Å3 |
Mr = 867.84 | Z = 4 |
Monoclinic, P21/c | Mo Kα radiation |
a = 12.8354 (9) Å | µ = 0.71 mm−1 |
b = 18.4979 (17) Å | T = 298 K |
c = 18.7933 (18) Å | 0.34 × 0.27 × 0.15 mm |
β = 92.839 (12)° |
Bruker SMART APEX CCD area-detector diffractometer | 7835 independent reflections |
Absorption correction: multi-scan (SADABS; Bruker, 2007) | 3113 reflections with I > 2σ(I) |
Tmin = 0.794, Tmax = 0.901 | Rint = 0.143 |
22332 measured reflections |
R[F2 > 2σ(F2)] = 0.086 | 0 restraints |
wR(F2) = 0.217 | H-atom parameters constrained |
S = 1.07 | Δρmax = 1.53 e Å−3 |
7835 reflections | Δρmin = −0.57 e Å−3 |
510 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. |
Refinement. Refinement of F2 against ALL reflections. The weighted R-factor wR and goodness of fit S are based on F2, conventional R-factors R are based on F, with F set to zero for negative F2. The threshold expression of F2 > σ(F2) is used only for calculating R-factors(gt) etc. and is not relevant to the choice of reflections for refinement. R-factors based on F2 are statistically about twice as large as those based on F, and R- factors based on ALL data will be even larger. |
x | y | z | Uiso*/Ueq | ||
Cu1 | 0.30121 (7) | 0.43378 (5) | 0.23518 (5) | 0.0537 (3) | |
P1 | 0.47643 (15) | 0.42103 (10) | 0.21637 (10) | 0.0509 (5) | |
P2 | 0.24071 (15) | 0.44918 (10) | 0.34688 (10) | 0.0531 (6) | |
Cl1 | 0.22504 (15) | 0.32234 (10) | 0.18410 (10) | 0.0599 (5) | |
S1 | 0.22509 (17) | 0.53539 (11) | 0.17178 (11) | 0.0692 (7) | |
N1 | 0.1747 (4) | 0.4387 (3) | 0.0660 (3) | 0.0563 (16) | |
H1 | 0.1900 | 0.4013 | 0.0915 | 0.068* | |
N2 | 0.1489 (5) | 0.5499 (3) | 0.0335 (3) | 0.0628 (18) | |
H2 | 0.1446 | 0.5963 | 0.0348 | 0.075* | |
O1 | 0.0716 (5) | 0.3451 (4) | −0.1723 (3) | 0.0926 (19) | |
O2 | 0.1114 (6) | 0.6996 (4) | −0.0042 (5) | 0.130 (3) | |
H2A | 0.0639 | 0.6951 | −0.0347 | 0.195* | |
O3 | 0.9931 (7) | 0.2825 (5) | 0.1330 (5) | 0.158 (4) | |
H3 | 1.0532 | 0.2907 | 0.1475 | 0.236* | |
C1 | 0.1816 (6) | 0.5083 (4) | 0.0894 (4) | 0.059 (2) | |
C2 | 0.1233 (6) | 0.5082 (4) | −0.0262 (4) | 0.058 (2) | |
C3 | 0.1393 (6) | 0.4368 (4) | −0.0056 (4) | 0.0524 (19) | |
C4 | 0.1246 (6) | 0.3797 (4) | −0.0514 (4) | 0.065 (2) | |
H4 | 0.1378 | 0.3324 | −0.0368 | 0.078* | |
C5 | 0.0892 (6) | 0.3957 (5) | −0.1203 (5) | 0.066 (2) | |
C6 | 0.0695 (6) | 0.4672 (5) | −0.1402 (4) | 0.070 (2) | |
H6 | 0.0441 | 0.4766 | −0.1865 | 0.084* | |
C7 | 0.0856 (6) | 0.5234 (5) | −0.0950 (4) | 0.065 (2) | |
H7 | 0.0719 | 0.5707 | −0.1096 | 0.079* | |
C8 | 0.1079 (9) | 0.2732 (6) | −0.1583 (5) | 0.122 (4) | |
H8A | 0.1639 | 0.2744 | −0.1225 | 0.182* | |
H8B | 0.1324 | 0.2526 | −0.2013 | 0.182* | |
H8C | 0.0518 | 0.2444 | −0.1418 | 0.182* | |
C9 | 0.5097 (7) | 0.4059 (4) | 0.1244 (4) | 0.059 (2) | |
C10 | 0.6037 (7) | 0.3743 (5) | 0.1044 (5) | 0.082 (3) | |
H10 | 0.6544 | 0.3605 | 0.1388 | 0.099* | |
C11 | 0.6198 (9) | 0.3640 (5) | 0.0318 (7) | 0.094 (3) | |
H11 | 0.6812 | 0.3426 | 0.0180 | 0.113* | |
C12 | 0.5476 (11) | 0.3847 (6) | −0.0176 (6) | 0.095 (3) | |
H12 | 0.5605 | 0.3775 | −0.0653 | 0.115* | |
C13 | 0.4570 (9) | 0.4156 (6) | −0.0013 (6) | 0.096 (3) | |
H13 | 0.4079 | 0.4295 | −0.0367 | 0.116* | |
C14 | 0.4393 (7) | 0.4258 (4) | 0.0702 (5) | 0.072 (2) | |
H14 | 0.3770 | 0.4472 | 0.0822 | 0.087* | |
C15 | 0.5550 (6) | 0.4989 (4) | 0.2451 (5) | 0.059 (2) | |
C16 | 0.6271 (6) | 0.5323 (5) | 0.2041 (5) | 0.073 (2) | |
H16 | 0.6379 | 0.5151 | 0.1586 | 0.088* | |
C17 | 0.6840 (7) | 0.5918 (5) | 0.2304 (6) | 0.085 (3) | |
H17 | 0.7320 | 0.6139 | 0.2019 | 0.102* | |
C18 | 0.6702 (7) | 0.6179 (5) | 0.2974 (6) | 0.084 (3) | |
H18 | 0.7088 | 0.6572 | 0.3147 | 0.101* | |
C19 | 0.5988 (7) | 0.5855 (5) | 0.3385 (5) | 0.082 (3) | |
H19 | 0.5885 | 0.6028 | 0.3841 | 0.098* | |
C20 | 0.5415 (6) | 0.5266 (5) | 0.3126 (5) | 0.073 (2) | |
H20 | 0.4929 | 0.5053 | 0.3411 | 0.088* | |
C21 | 0.5458 (6) | 0.3451 (4) | 0.2602 (4) | 0.058 (2) | |
C22 | 0.6389 (7) | 0.3535 (5) | 0.2985 (5) | 0.088 (3) | |
H22 | 0.6673 | 0.3994 | 0.3055 | 0.106* | |
C23 | 0.6913 (8) | 0.2926 (6) | 0.3271 (6) | 0.109 (4) | |
H23 | 0.7547 | 0.2983 | 0.3526 | 0.131* | |
C24 | 0.6496 (8) | 0.2252 (5) | 0.3176 (5) | 0.089 (3) | |
H24 | 0.6857 | 0.1849 | 0.3354 | 0.106* | |
C25 | 0.5562 (8) | 0.2171 (5) | 0.2826 (5) | 0.084 (3) | |
H25 | 0.5263 | 0.1714 | 0.2779 | 0.101* | |
C26 | 0.5054 (7) | 0.2761 (5) | 0.2539 (4) | 0.072 (2) | |
H26 | 0.4414 | 0.2694 | 0.2293 | 0.086* | |
C27 | 0.2655 (6) | 0.3748 (4) | 0.4116 (4) | 0.057 (2) | |
C28 | 0.3502 (7) | 0.3323 (4) | 0.4029 (4) | 0.070 (2) | |
H28 | 0.3908 | 0.3396 | 0.3639 | 0.084* | |
C29 | 0.3773 (7) | 0.2775 (5) | 0.4521 (5) | 0.084 (3) | |
H29 | 0.4360 | 0.2489 | 0.4466 | 0.100* | |
C30 | 0.3162 (8) | 0.2672 (5) | 0.5073 (5) | 0.079 (3) | |
H30 | 0.3334 | 0.2310 | 0.5402 | 0.095* | |
C31 | 0.2305 (8) | 0.3080 (5) | 0.5166 (5) | 0.081 (3) | |
H31 | 0.1894 | 0.2996 | 0.5551 | 0.098* | |
C32 | 0.2046 (7) | 0.3622 (4) | 0.4682 (5) | 0.072 (2) | |
H32 | 0.1455 | 0.3902 | 0.4742 | 0.087* | |
C33 | 0.2920 (6) | 0.5294 (4) | 0.3946 (4) | 0.061 (2) | |
C34 | 0.3381 (7) | 0.5259 (5) | 0.4634 (5) | 0.081 (3) | |
H34 | 0.3414 | 0.4823 | 0.4881 | 0.097* | |
C35 | 0.3790 (8) | 0.5885 (6) | 0.4946 (5) | 0.103 (3) | |
H35 | 0.4107 | 0.5863 | 0.5402 | 0.123* | |
C36 | 0.3736 (8) | 0.6538 (6) | 0.4593 (6) | 0.101 (3) | |
H36 | 0.3992 | 0.6955 | 0.4815 | 0.121* | |
C37 | 0.3302 (7) | 0.6571 (5) | 0.3913 (6) | 0.089 (3) | |
H37 | 0.3290 | 0.7006 | 0.3665 | 0.106* | |
C38 | 0.2885 (7) | 0.5960 (5) | 0.3598 (5) | 0.080 (3) | |
H38 | 0.2571 | 0.5991 | 0.3142 | 0.095* | |
C39 | 0.0997 (6) | 0.4619 (4) | 0.3492 (4) | 0.063 (2) | |
C40 | 0.0361 (7) | 0.4197 (4) | 0.3041 (4) | 0.074 (2) | |
H40 | 0.0664 | 0.3882 | 0.2726 | 0.089* | |
C41 | −0.0717 (7) | 0.4236 (5) | 0.3052 (5) | 0.081 (3) | |
H41 | −0.1129 | 0.3936 | 0.2757 | 0.097* | |
C42 | −0.1163 (8) | 0.4702 (7) | 0.3483 (6) | 0.103 (3) | |
H42 | −0.1886 | 0.4728 | 0.3486 | 0.123* | |
C43 | −0.0571 (9) | 0.5136 (6) | 0.3914 (6) | 0.115 (4) | |
H43 | −0.0890 | 0.5469 | 0.4203 | 0.138* | |
C44 | 0.0514 (8) | 0.5090 (5) | 0.3931 (5) | 0.091 (3) | |
H44 | 0.0913 | 0.5381 | 0.4243 | 0.109* | |
C45 | 0.1070 (11) | 0.7687 (8) | 0.0263 (7) | 0.184 (6) | |
H45A | 0.0960 | 0.7643 | 0.0763 | 0.277* | |
H45B | 0.0505 | 0.7954 | 0.0036 | 0.277* | |
H45C | 0.1714 | 0.7936 | 0.0199 | 0.277* | |
C46 | 0.9510 (12) | 0.2268 (10) | 0.1738 (8) | 0.231 (10) | |
H46A | 0.9228 | 0.2470 | 0.2158 | 0.346* | |
H46B | 1.0049 | 0.1928 | 0.1874 | 0.346* | |
H46C | 0.8967 | 0.2026 | 0.1461 | 0.346* |
U11 | U22 | U33 | U12 | U13 | U23 | |
Cu1 | 0.0613 (6) | 0.0469 (6) | 0.0522 (6) | −0.0002 (5) | −0.0049 (4) | −0.0005 (5) |
P1 | 0.0540 (12) | 0.0396 (12) | 0.0584 (13) | −0.0011 (10) | −0.0033 (10) | 0.0018 (10) |
P2 | 0.0631 (13) | 0.0440 (13) | 0.0516 (13) | 0.0016 (10) | −0.0029 (10) | −0.0023 (10) |
Cl1 | 0.0783 (13) | 0.0395 (11) | 0.0605 (13) | −0.0042 (10) | −0.0093 (10) | −0.0004 (9) |
S1 | 0.0936 (16) | 0.0418 (12) | 0.0695 (15) | 0.0030 (11) | −0.0228 (12) | 0.0021 (11) |
N1 | 0.074 (4) | 0.038 (4) | 0.056 (4) | 0.002 (3) | −0.011 (3) | 0.005 (3) |
N2 | 0.074 (4) | 0.055 (5) | 0.057 (4) | 0.001 (4) | −0.009 (3) | 0.012 (4) |
O1 | 0.122 (5) | 0.075 (5) | 0.078 (4) | 0.021 (4) | −0.020 (4) | −0.010 (4) |
O2 | 0.162 (8) | 0.073 (5) | 0.150 (7) | −0.005 (5) | −0.045 (5) | 0.023 (5) |
O3 | 0.140 (7) | 0.146 (8) | 0.178 (8) | −0.042 (6) | −0.081 (6) | 0.048 (6) |
C1 | 0.065 (5) | 0.053 (6) | 0.059 (6) | 0.003 (4) | −0.006 (4) | 0.005 (5) |
C2 | 0.063 (5) | 0.054 (6) | 0.055 (6) | 0.002 (4) | −0.008 (4) | 0.010 (5) |
C3 | 0.068 (5) | 0.039 (5) | 0.049 (5) | 0.003 (4) | −0.006 (4) | 0.006 (4) |
C4 | 0.082 (6) | 0.051 (5) | 0.062 (6) | 0.012 (5) | −0.011 (5) | 0.004 (5) |
C5 | 0.082 (6) | 0.060 (6) | 0.055 (6) | 0.009 (5) | −0.007 (5) | −0.002 (5) |
C6 | 0.088 (6) | 0.068 (6) | 0.053 (6) | 0.012 (5) | −0.009 (4) | 0.005 (5) |
C7 | 0.082 (6) | 0.057 (6) | 0.057 (6) | 0.007 (5) | −0.005 (5) | 0.014 (5) |
C8 | 0.190 (11) | 0.079 (8) | 0.094 (8) | 0.007 (8) | −0.014 (8) | −0.016 (6) |
C9 | 0.069 (6) | 0.036 (5) | 0.073 (6) | −0.009 (4) | −0.001 (5) | 0.001 (4) |
C10 | 0.094 (7) | 0.066 (6) | 0.088 (8) | 0.007 (5) | 0.007 (6) | 0.000 (5) |
C11 | 0.122 (10) | 0.060 (7) | 0.103 (9) | 0.001 (6) | 0.045 (8) | −0.009 (6) |
C12 | 0.127 (10) | 0.078 (8) | 0.084 (9) | −0.028 (8) | 0.025 (8) | −0.018 (7) |
C13 | 0.116 (9) | 0.096 (8) | 0.077 (8) | −0.017 (7) | −0.002 (6) | −0.010 (6) |
C14 | 0.085 (6) | 0.071 (6) | 0.062 (6) | −0.011 (5) | 0.010 (5) | −0.013 (5) |
C15 | 0.055 (5) | 0.048 (5) | 0.072 (6) | −0.002 (4) | −0.004 (4) | 0.003 (4) |
C16 | 0.078 (6) | 0.056 (6) | 0.086 (7) | −0.006 (5) | 0.004 (5) | −0.002 (5) |
C17 | 0.078 (7) | 0.064 (7) | 0.113 (9) | −0.015 (5) | 0.010 (6) | −0.002 (6) |
C18 | 0.080 (7) | 0.065 (7) | 0.107 (9) | −0.006 (5) | −0.013 (6) | −0.010 (6) |
C19 | 0.085 (7) | 0.068 (7) | 0.093 (7) | −0.003 (5) | −0.005 (6) | −0.024 (5) |
C20 | 0.072 (6) | 0.062 (6) | 0.085 (7) | −0.005 (5) | −0.009 (5) | −0.007 (5) |
C21 | 0.056 (5) | 0.046 (5) | 0.073 (6) | 0.001 (4) | −0.001 (4) | −0.006 (4) |
C22 | 0.086 (7) | 0.054 (6) | 0.121 (8) | −0.003 (5) | −0.020 (6) | 0.009 (6) |
C23 | 0.105 (8) | 0.080 (8) | 0.139 (10) | 0.006 (7) | −0.042 (7) | 0.023 (7) |
C24 | 0.104 (8) | 0.047 (6) | 0.113 (8) | 0.013 (6) | −0.010 (6) | 0.015 (6) |
C25 | 0.098 (8) | 0.048 (6) | 0.106 (8) | 0.001 (6) | 0.001 (6) | 0.005 (5) |
C26 | 0.083 (6) | 0.043 (5) | 0.086 (6) | 0.005 (5) | −0.016 (5) | 0.000 (5) |
C27 | 0.073 (6) | 0.042 (5) | 0.056 (6) | 0.001 (4) | −0.005 (4) | −0.003 (4) |
C28 | 0.085 (6) | 0.059 (6) | 0.067 (6) | 0.002 (5) | 0.006 (5) | 0.014 (5) |
C29 | 0.091 (7) | 0.068 (7) | 0.091 (8) | 0.011 (5) | −0.008 (6) | 0.025 (6) |
C30 | 0.103 (8) | 0.062 (6) | 0.069 (7) | −0.010 (6) | −0.027 (6) | 0.012 (5) |
C31 | 0.114 (8) | 0.066 (7) | 0.064 (6) | −0.005 (6) | 0.004 (6) | 0.008 (5) |
C32 | 0.092 (7) | 0.058 (6) | 0.067 (6) | 0.005 (5) | 0.006 (5) | −0.003 (5) |
C33 | 0.077 (6) | 0.047 (5) | 0.060 (6) | 0.002 (4) | 0.003 (4) | −0.005 (4) |
C34 | 0.109 (7) | 0.056 (6) | 0.076 (7) | −0.008 (5) | −0.015 (6) | −0.010 (5) |
C35 | 0.139 (9) | 0.075 (8) | 0.089 (8) | −0.010 (7) | −0.037 (6) | −0.011 (6) |
C36 | 0.126 (9) | 0.064 (8) | 0.109 (9) | −0.010 (6) | −0.019 (7) | −0.025 (7) |
C37 | 0.128 (8) | 0.045 (6) | 0.092 (8) | −0.006 (6) | −0.011 (6) | −0.004 (5) |
C38 | 0.106 (7) | 0.052 (6) | 0.079 (6) | −0.006 (5) | −0.013 (5) | −0.009 (5) |
C39 | 0.075 (6) | 0.053 (5) | 0.061 (6) | 0.004 (5) | −0.001 (5) | −0.005 (4) |
C40 | 0.076 (7) | 0.064 (6) | 0.080 (6) | 0.006 (5) | −0.005 (5) | −0.009 (5) |
C41 | 0.064 (6) | 0.086 (7) | 0.092 (7) | −0.011 (6) | −0.003 (5) | −0.008 (6) |
C42 | 0.079 (7) | 0.113 (9) | 0.116 (9) | 0.001 (7) | −0.001 (7) | −0.015 (7) |
C43 | 0.093 (9) | 0.119 (10) | 0.133 (10) | 0.018 (8) | 0.014 (7) | −0.045 (8) |
C44 | 0.082 (8) | 0.091 (8) | 0.099 (8) | −0.001 (6) | 0.001 (6) | −0.025 (6) |
C45 | 0.219 (16) | 0.153 (15) | 0.176 (14) | −0.013 (12) | −0.046 (11) | −0.046 (12) |
C46 | 0.225 (17) | 0.24 (2) | 0.215 (17) | −0.121 (16) | −0.117 (14) | 0.093 (15) |
Cu1—P2 | 2.292 (2) | C19—C20 | 1.389 (11) |
Cu1—P1 | 2.306 (2) | C19—H19 | 0.9300 |
Cu1—S1 | 2.407 (2) | C20—H20 | 0.9300 |
Cu1—Cl1 | 2.456 (2) | C21—C22 | 1.373 (10) |
P1—C9 | 1.822 (8) | C21—C26 | 1.382 (10) |
P1—C15 | 1.825 (8) | C22—C23 | 1.405 (12) |
P1—C21 | 1.835 (8) | C22—H22 | 0.9300 |
P2—C39 | 1.828 (8) | C23—C24 | 1.365 (12) |
P2—C33 | 1.838 (8) | C23—H23 | 0.9300 |
P2—C27 | 1.853 (8) | C24—C25 | 1.348 (11) |
S1—C1 | 1.695 (8) | C24—H24 | 0.9300 |
N1—C1 | 1.362 (8) | C25—C26 | 1.368 (11) |
N1—C3 | 1.398 (8) | C25—H25 | 0.9300 |
N1—H1 | 0.8600 | C26—H26 | 0.9300 |
N2—C1 | 1.352 (8) | C27—C28 | 1.359 (10) |
N2—C2 | 1.387 (9) | C27—C32 | 1.371 (10) |
N2—H2 | 0.8600 | C28—C29 | 1.404 (10) |
O1—C5 | 1.363 (9) | C28—H28 | 0.9300 |
O1—C8 | 1.429 (10) | C29—C30 | 1.345 (11) |
O2—C45 | 1.403 (13) | C29—H29 | 0.9300 |
O2—H2A | 0.8200 | C30—C31 | 1.351 (11) |
O3—C46 | 1.410 (14) | C30—H30 | 0.9300 |
O3—H3 | 0.8200 | C31—C32 | 1.383 (11) |
C2—C7 | 1.387 (10) | C31—H31 | 0.9300 |
C2—C3 | 1.388 (9) | C32—H32 | 0.9300 |
C3—C4 | 1.370 (10) | C33—C38 | 1.394 (11) |
C4—C5 | 1.382 (10) | C33—C34 | 1.398 (10) |
C4—H4 | 0.9300 | C34—C35 | 1.388 (12) |
C5—C6 | 1.395 (10) | C34—H34 | 0.9300 |
C6—C7 | 1.352 (10) | C35—C36 | 1.380 (13) |
C6—H6 | 0.9300 | C35—H35 | 0.9300 |
C7—H7 | 0.9300 | C36—C37 | 1.370 (12) |
C8—H8A | 0.9600 | C36—H36 | 0.9300 |
C8—H8B | 0.9600 | C37—C38 | 1.371 (11) |
C8—H8C | 0.9600 | C37—H37 | 0.9300 |
C9—C14 | 1.378 (10) | C38—H38 | 0.9300 |
C9—C10 | 1.409 (11) | C39—C44 | 1.370 (11) |
C10—C11 | 1.403 (12) | C39—C40 | 1.387 (10) |
C10—H10 | 0.9300 | C40—C41 | 1.387 (10) |
C11—C12 | 1.336 (13) | C40—H40 | 0.9300 |
C11—H11 | 0.9300 | C41—C42 | 1.332 (12) |
C12—C13 | 1.344 (13) | C41—H41 | 0.9300 |
C12—H12 | 0.9300 | C42—C43 | 1.348 (13) |
C13—C14 | 1.387 (11) | C42—H42 | 0.9300 |
C13—H13 | 0.9300 | C43—C44 | 1.395 (11) |
C14—H14 | 0.9300 | C43—H43 | 0.9300 |
C15—C16 | 1.378 (10) | C44—H44 | 0.9300 |
C15—C20 | 1.387 (10) | C45—H45A | 0.9600 |
C16—C17 | 1.397 (11) | C45—H45B | 0.9600 |
C16—H16 | 0.9300 | C45—H45C | 0.9600 |
C17—C18 | 1.370 (12) | C46—H46A | 0.9600 |
C17—H17 | 0.9300 | C46—H46B | 0.9600 |
C18—C19 | 1.366 (12) | C46—H46C | 0.9600 |
C18—H18 | 0.9300 | ||
P2—Cu1—P1 | 122.03 (8) | C15—C20—C19 | 121.5 (8) |
P2—Cu1—S1 | 102.05 (8) | C15—C20—H20 | 119.2 |
P1—Cu1—S1 | 112.28 (8) | C19—C20—H20 | 119.2 |
P2—Cu1—Cl1 | 108.42 (7) | C22—C21—C26 | 117.5 (8) |
P1—Cu1—Cl1 | 103.10 (7) | C22—C21—P1 | 122.7 (7) |
S1—Cu1—Cl1 | 108.54 (7) | C26—C21—P1 | 119.8 (6) |
C9—P1—C15 | 104.5 (4) | C21—C22—C23 | 119.9 (9) |
C9—P1—C21 | 100.1 (4) | C21—C22—H22 | 120.1 |
C15—P1—C21 | 102.9 (3) | C23—C22—H22 | 120.1 |
C9—P1—Cu1 | 115.9 (3) | C24—C23—C22 | 120.4 (9) |
C15—P1—Cu1 | 113.8 (3) | C24—C23—H23 | 119.8 |
C21—P1—Cu1 | 117.7 (3) | C22—C23—H23 | 119.8 |
C39—P2—C33 | 102.5 (4) | C25—C24—C23 | 119.9 (9) |
C39—P2—C27 | 102.6 (4) | C25—C24—H24 | 120.1 |
C33—P2—C27 | 103.5 (4) | C23—C24—H24 | 120.1 |
C39—P2—Cu1 | 114.8 (3) | C24—C25—C26 | 120.0 (9) |
C33—P2—Cu1 | 114.7 (3) | C24—C25—H25 | 120.0 |
C27—P2—Cu1 | 117.0 (3) | C26—C25—H25 | 120.0 |
C1—S1—Cu1 | 109.2 (3) | C25—C26—C21 | 122.3 (8) |
C1—N1—C3 | 110.3 (6) | C25—C26—H26 | 118.9 |
C1—N1—H1 | 124.8 | C21—C26—H26 | 118.9 |
C3—N1—H1 | 124.8 | C28—C27—C32 | 119.0 (8) |
C1—N2—C2 | 111.3 (6) | C28—C27—P2 | 117.6 (7) |
C1—N2—H2 | 124.3 | C32—C27—P2 | 123.4 (7) |
C2—N2—H2 | 124.3 | C27—C28—C29 | 120.9 (8) |
C5—O1—C8 | 117.7 (7) | C27—C28—H28 | 119.6 |
C45—O2—H2A | 109.5 | C29—C28—H28 | 119.6 |
C46—O3—H3 | 109.5 | C30—C29—C28 | 118.3 (9) |
N2—C1—N1 | 105.9 (7) | C30—C29—H29 | 120.8 |
N2—C1—S1 | 128.1 (6) | C28—C29—H29 | 120.8 |
N1—C1—S1 | 126.0 (6) | C29—C30—C31 | 122.0 (9) |
N2—C2—C7 | 134.3 (8) | C29—C30—H30 | 119.0 |
N2—C2—C3 | 106.1 (7) | C31—C30—H30 | 119.0 |
C7—C2—C3 | 119.5 (8) | C30—C31—C32 | 119.4 (9) |
C4—C3—C2 | 123.0 (7) | C30—C31—H31 | 120.3 |
C4—C3—N1 | 130.7 (7) | C32—C31—H31 | 120.3 |
C2—C3—N1 | 106.3 (7) | C27—C32—C31 | 120.4 (9) |
C3—C4—C5 | 117.0 (8) | C27—C32—H32 | 119.8 |
C3—C4—H4 | 121.5 | C31—C32—H32 | 119.8 |
C5—C4—H4 | 121.5 | C38—C33—C34 | 118.4 (8) |
O1—C5—C4 | 124.1 (8) | C38—C33—P2 | 118.9 (6) |
O1—C5—C6 | 115.9 (7) | C34—C33—P2 | 122.7 (7) |
C4—C5—C6 | 120.0 (8) | C35—C34—C33 | 119.2 (9) |
C7—C6—C5 | 122.8 (8) | C35—C34—H34 | 120.4 |
C7—C6—H6 | 118.6 | C33—C34—H34 | 120.4 |
C5—C6—H6 | 118.6 | C36—C35—C34 | 121.1 (9) |
C6—C7—C2 | 117.7 (8) | C36—C35—H35 | 119.4 |
C6—C7—H7 | 121.2 | C34—C35—H35 | 119.4 |
C2—C7—H7 | 121.2 | C37—C36—C35 | 119.8 (9) |
O1—C8—H8A | 109.5 | C37—C36—H36 | 120.1 |
O1—C8—H8B | 109.5 | C35—C36—H36 | 120.1 |
H8A—C8—H8B | 109.5 | C36—C37—C38 | 119.8 (9) |
O1—C8—H8C | 109.5 | C36—C37—H37 | 120.1 |
H8A—C8—H8C | 109.5 | C38—C37—H37 | 120.1 |
H8B—C8—H8C | 109.5 | C37—C38—C33 | 121.6 (8) |
C14—C9—C10 | 116.9 (8) | C37—C38—H38 | 119.2 |
C14—C9—P1 | 119.0 (7) | C33—C38—H38 | 119.2 |
C10—C9—P1 | 124.1 (7) | C44—C39—C40 | 117.1 (8) |
C11—C10—C9 | 119.0 (9) | C44—C39—P2 | 125.1 (7) |
C11—C10—H10 | 120.5 | C40—C39—P2 | 117.8 (6) |
C9—C10—H10 | 120.5 | C39—C40—C41 | 121.4 (8) |
C12—C11—C10 | 120.4 (10) | C39—C40—H40 | 119.3 |
C12—C11—H11 | 119.8 | C41—C40—H40 | 119.3 |
C10—C11—H11 | 119.8 | C42—C41—C40 | 120.1 (9) |
C11—C12—C13 | 122.8 (11) | C42—C41—H41 | 120.0 |
C11—C12—H12 | 118.6 | C40—C41—H41 | 120.0 |
C13—C12—H12 | 118.6 | C41—C42—C43 | 120.3 (10) |
C12—C13—C14 | 117.6 (10) | C41—C42—H42 | 119.8 |
C12—C13—H13 | 121.2 | C43—C42—H42 | 119.8 |
C14—C13—H13 | 121.2 | C42—C43—C44 | 120.7 (10) |
C9—C14—C13 | 123.2 (9) | C42—C43—H43 | 119.7 |
C9—C14—H14 | 118.4 | C44—C43—H43 | 119.7 |
C13—C14—H14 | 118.4 | C39—C44—C43 | 120.4 (9) |
C16—C15—C20 | 117.6 (8) | C39—C44—H44 | 119.8 |
C16—C15—P1 | 124.4 (7) | C43—C44—H44 | 119.8 |
C20—C15—P1 | 118.0 (7) | O2—C45—H45A | 109.5 |
C15—C16—C17 | 120.6 (8) | O2—C45—H45B | 109.5 |
C15—C16—H16 | 119.7 | H45A—C45—H45B | 109.5 |
C17—C16—H16 | 119.7 | O2—C45—H45C | 109.5 |
C18—C17—C16 | 120.9 (9) | H45A—C45—H45C | 109.5 |
C18—C17—H17 | 119.5 | H45B—C45—H45C | 109.5 |
C16—C17—H17 | 119.5 | O3—C46—H46A | 109.5 |
C19—C18—C17 | 119.1 (9) | O3—C46—H46B | 109.5 |
C19—C18—H18 | 120.4 | H46A—C46—H46B | 109.5 |
C17—C18—H18 | 120.4 | O3—C46—H46C | 109.5 |
C18—C19—C20 | 120.3 (9) | H46A—C46—H46C | 109.5 |
C18—C19—H19 | 119.9 | H46B—C46—H46C | 109.5 |
C20—C19—H19 | 119.9 | ||
P2—Cu1—P1—C9 | 177.7 (3) | Cu1—P1—C15—C20 | 48.6 (7) |
S1—Cu1—P1—C9 | −60.8 (3) | C20—C15—C16—C17 | 0.1 (12) |
Cl1—Cu1—P1—C9 | 55.9 (3) | P1—C15—C16—C17 | −180.0 (6) |
P2—Cu1—P1—C15 | −61.1 (3) | C15—C16—C17—C18 | 0.5 (13) |
S1—Cu1—P1—C15 | 60.4 (3) | C16—C17—C18—C19 | −0.6 (14) |
Cl1—Cu1—P1—C15 | 177.0 (3) | C17—C18—C19—C20 | 0.2 (14) |
P2—Cu1—P1—C21 | 59.3 (3) | C16—C15—C20—C19 | −0.5 (12) |
S1—Cu1—P1—C21 | −179.2 (3) | P1—C15—C20—C19 | 179.5 (6) |
Cl1—Cu1—P1—C21 | −62.6 (3) | C18—C19—C20—C15 | 0.4 (13) |
P1—Cu1—P2—C39 | 177.6 (3) | C9—P1—C21—C22 | 102.6 (8) |
S1—Cu1—P2—C39 | 51.4 (3) | C15—P1—C21—C22 | −4.9 (8) |
Cl1—Cu1—P2—C39 | −63.0 (3) | Cu1—P1—C21—C22 | −130.8 (7) |
P1—Cu1—P2—C33 | 59.4 (3) | C9—P1—C21—C26 | −76.0 (7) |
S1—Cu1—P2—C33 | −66.9 (3) | C15—P1—C21—C26 | 176.5 (7) |
Cl1—Cu1—P2—C33 | 178.7 (3) | Cu1—P1—C21—C26 | 50.5 (7) |
P1—Cu1—P2—C27 | −62.1 (3) | C26—C21—C22—C23 | 2.5 (13) |
S1—Cu1—P2—C27 | 171.7 (3) | P1—C21—C22—C23 | −176.2 (7) |
Cl1—Cu1—P2—C27 | 57.2 (3) | C21—C22—C23—C24 | −0.7 (15) |
P2—Cu1—S1—C1 | −138.7 (3) | C22—C23—C24—C25 | −2.1 (16) |
P1—Cu1—S1—C1 | 89.0 (3) | C23—C24—C25—C26 | 2.8 (15) |
Cl1—Cu1—S1—C1 | −24.3 (3) | C24—C25—C26—C21 | −0.9 (14) |
C2—N2—C1—N1 | −1.4 (8) | C22—C21—C26—C25 | −1.8 (13) |
C2—N2—C1—S1 | 177.4 (6) | P1—C21—C26—C25 | 176.9 (7) |
C3—N1—C1—N2 | 1.1 (8) | C39—P2—C27—C28 | 153.8 (6) |
C3—N1—C1—S1 | −177.7 (6) | C33—P2—C27—C28 | −99.9 (7) |
Cu1—S1—C1—N2 | −168.8 (6) | Cu1—P2—C27—C28 | 27.3 (7) |
Cu1—S1—C1—N1 | 9.8 (7) | C39—P2—C27—C32 | −28.0 (7) |
C1—N2—C2—C7 | 179.0 (8) | C33—P2—C27—C32 | 78.3 (7) |
C1—N2—C2—C3 | 1.1 (8) | Cu1—P2—C27—C32 | −154.5 (6) |
N2—C2—C3—C4 | −178.2 (7) | C32—C27—C28—C29 | −1.8 (12) |
C7—C2—C3—C4 | 3.5 (12) | P2—C27—C28—C29 | 176.5 (6) |
N2—C2—C3—N1 | −0.4 (8) | C27—C28—C29—C30 | 1.2 (13) |
C7—C2—C3—N1 | −178.7 (7) | C28—C29—C30—C31 | −0.1 (13) |
C1—N1—C3—C4 | 177.2 (8) | C29—C30—C31—C32 | −0.3 (14) |
C1—N1—C3—C2 | −0.4 (8) | C28—C27—C32—C31 | 1.4 (12) |
C2—C3—C4—C5 | −2.0 (12) | P2—C27—C32—C31 | −176.8 (6) |
N1—C3—C4—C5 | −179.2 (7) | C30—C31—C32—C27 | −0.4 (13) |
C8—O1—C5—C4 | −10.8 (12) | C39—P2—C33—C38 | −75.4 (7) |
C8—O1—C5—C6 | 169.2 (8) | C27—P2—C33—C38 | 178.2 (7) |
C3—C4—C5—O1 | 179.4 (7) | Cu1—P2—C33—C38 | 49.6 (7) |
C3—C4—C5—C6 | −0.5 (12) | C39—P2—C33—C34 | 107.1 (7) |
O1—C5—C6—C7 | −178.4 (8) | C27—P2—C33—C34 | 0.7 (8) |
C4—C5—C6—C7 | 1.5 (13) | Cu1—P2—C33—C34 | −127.9 (6) |
C5—C6—C7—C2 | −0.1 (13) | C38—C33—C34—C35 | −0.3 (13) |
N2—C2—C7—C6 | 180.0 (8) | P2—C33—C34—C35 | 177.2 (7) |
C3—C2—C7—C6 | −2.3 (11) | C33—C34—C35—C36 | 0.9 (15) |
C15—P1—C9—C14 | −104.9 (6) | C34—C35—C36—C37 | −2.2 (16) |
C21—P1—C9—C14 | 148.8 (6) | C35—C36—C37—C38 | 2.7 (15) |
Cu1—P1—C9—C14 | 21.1 (7) | C36—C37—C38—C33 | −2.1 (14) |
C15—P1—C9—C10 | 75.4 (7) | C34—C33—C38—C37 | 0.9 (13) |
C21—P1—C9—C10 | −30.9 (7) | P2—C33—C38—C37 | −176.7 (7) |
Cu1—P1—C9—C10 | −158.6 (6) | C33—P2—C39—C44 | −15.7 (9) |
C14—C9—C10—C11 | −1.0 (11) | C27—P2—C39—C44 | 91.4 (8) |
P1—C9—C10—C11 | 178.7 (6) | Cu1—P2—C39—C44 | −140.6 (7) |
C9—C10—C11—C12 | 0.9 (14) | C33—P2—C39—C40 | 165.6 (6) |
C10—C11—C12—C13 | −0.4 (16) | C27—P2—C39—C40 | −87.3 (7) |
C11—C12—C13—C14 | 0.0 (16) | Cu1—P2—C39—C40 | 40.7 (7) |
C10—C9—C14—C13 | 0.6 (12) | C44—C39—C40—C41 | −2.0 (13) |
P1—C9—C14—C13 | −179.1 (7) | P2—C39—C40—C41 | 176.8 (7) |
C12—C13—C14—C9 | −0.1 (14) | C39—C40—C41—C42 | 2.3 (14) |
C9—P1—C15—C16 | −4.0 (8) | C40—C41—C42—C43 | −0.4 (17) |
C21—P1—C15—C16 | 100.2 (7) | C41—C42—C43—C44 | −1.8 (18) |
Cu1—P1—C15—C16 | −131.3 (6) | C40—C39—C44—C43 | −0.3 (14) |
C9—P1—C15—C20 | 176.0 (6) | P2—C39—C44—C43 | −178.9 (8) |
C21—P1—C15—C20 | −79.8 (6) | C42—C43—C44—C39 | 2.2 (17) |
D—H···A | D—H | H···A | D···A | D—H···A |
N1—H1···Cl1 | 0.86 | 2.30 | 3.136 (6) | 165 |
N2—H2···O2 | 0.86 | 2.08 | 2.893 (9) | 157 |
O2—H2A···O3i | 0.82 | 2.00 | 2.728 (10) | 148 |
O3—H3···Cl1ii | 0.82 | 2.35 | 3.170 (8) | 176 |
Symmetry codes: (i) −x+1, −y+1, −z; (ii) x+1, y, z. |
D—H···A | D—H | H···A | D···A | D—H···A |
N1—H1···Cl1 | 0.86 | 2.30 | 3.136 (6) | 165 |
N2—H2···O2 | 0.86 | 2.08 | 2.893 (9) | 157 |
O2—H2A···O3i | 0.82 | 2.00 | 2.728 (10) | 148 |
O3—H3···Cl1ii | 0.82 | 2.35 | 3.170 (8) | 176 |
Symmetry codes: (i) −x+1, −y+1, −z; (ii) x+1, y, z. |
Acknowledgements
The author thanks Liaocheng University for the X-ray
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Cu(I) complexes containing triphenlyphosphine and mercaptan ligands have received much attention in the past, mainly because of their interesting coordination chemistry and potential applications in photography, biochemistry and enzymatic reactions (Gennari et al., 2006; Kitagawa et al., 1995; Raper et al., 1994). However, only one structure was reported for metal-MOBMT complex (MOBMT = 5-methoxy-1H- benzimidazole-2(3H)-thione) (Schneider et al., 2008). Herewith we present the crystal structure of new Cu(I) complex with triphenlyphosphine and MOBMT ligands.
In the title complex, MOMBT act as neutral, monodentate ligand with the S atom as a coordination atom. Other sites of the coordination tetrahedron are occupied by two P atoms from two triphenlyphosphine ligands and one halide anion. The Cu—S and Cu—P bond distances are similar to those reported in other copper(I) complexes (Lobana et al., 2002). The environment around copper(I) is distorted tetrahedral, angles around the Cu atom ranging from 102.1 (1)–122.0 (1)°. A dimer is formed by hydrogen bonds N—H···O, O—H···Cl, O—H···O between the unit [CuX(thione)(PPh3)2] and the solvent methanol molecules. An intramolecular N—H···Cl hydrogen bond is also observed (Table 1). Furthermore, the centroid to centroid distance between the parallel five- and six-membered rings of two benzimidazole fragments is 3.624 (4) Å, which suggests an existence of π···π interactions between them.