metal-organic compounds
Tetrakis[μ2-5-nitro-2-(phenylsulfanyl)benzoato-κ2O:O′]bis[(acetonitrile-κN)copper(II)]
aSchool of Chemical Engineering and Pharmacy, Wuhan Institute of Technology, Wuhan, Hubei 430205, People's Republic of China
*Correspondence e-mail: longsihui@yahoo.com
The title compound, [Cu2(μ2-O2CC12H8NO2S)4(CH3CN)2], consists of a dinuclear and centrosymmetric complex based on two CuII atoms coordinated by four 5-nitro-2-phenylsulfanyl-benzoate anions and two acetonitrile ligands. Each benzoate anion acts as a bis-monodentate ligand while each acetonitrile acts as a monodentate ligand, leading to a square-pyramidal NO4 coordination environment for each CuII atom with the acetonitrile N atom at the apex. The intramolecular Cu⋯Cu distance in the dimer is 2.6478 (3) Å. The cohesion of the is ensured by (phenyl)C—H⋯O(nitro) hydrogen bonds and (phenyl)C—H⋯π interactions.
Keywords: crystal structure; copper; bis-monodentate coordination; dimeric complex; C—H⋯O hydogen bonding.
CCDC reference: 2009944
Structure description
The title compound was obtained serendipitously during efforts to make 5-nitro-2-phenylsulfanyl-benzoic acid by reacting 2-bromo-5-nitro-benzoic acid with benzenethiol through a modified Ullmann reaction with Cu/Cu2O as catalyst, K2CO3 as base, and ethoxyethanol as solvent (Liu et al., 2007). The complex likely formed between CuII generated in situ and 5-nitro-2-phenylsulfanyl-benzoate.
The title compound is a centrosymmetric dinuclear CuII complex with two pairs of bis-monodentate 5-nitro-2-phenylsulfanyl-benzoate anions and a pair of acetonitrile molecules as ligands (Fig. 1). The coordination of each copper(II) atom is square-pyramidal, with the acetonitrile N atom at the apex of the NO4 coordination set. The intramolecular Cu⋯Cu distance in the dimer is 2.6478 (3) Å (Fig. 1). The aromatic rings of the two independent benzoate moieties (denoted by suffix A and B for the two anions in the asymmetric unit) are nearly perpendicular with a dihedral angle of 86.55 (5)°. The negative charge of the carboxylate group is delocalized over the two O atoms in each of the anions, as indicated by the nearly identical length of the two C—O bonds [1.2574 (17) and 1.2624 (17) Å for molecule A and 1.2574 (17) and 1.2655 (16) Å for molecule B]. A weak intermolecular hydrogen bond is formed between the C9B—H9B group of a phenyl ring and the O19B atom of an inversion-related (−x + 1, −y + 2, −z + 1) NO2 group (Table 1), leading to the formation of supramolecular pillars along [100] and [010] (Fig. 2). An additional C—H⋯π interaction between C10A—H10A and the centroid of a neighbouring phenyl ring (Table 1) consolidates the three-dimensional network structure.
The molecular structure of the title complex is similar to that of tetrakis(μ2-benzoato-O,O')-bis(dimethylsulfoxide)dicopper(II) (Reyes-Ortega et al., 2005) and other related copper complexes (Vives et al., 2003).
Synthesis and crystallization
A mixture of benzenethiol (1.25 g, 11.4 mmol), 2-bromo-5-nitro-benzoic acid (2.16 g, 8.8 mmol), K2CO3 (1.21 g, 8.8 mmol), Cu powder (51 mg, 0.8 mmol), Cu2O (38 mg, 0.4 mmol) and 2-ethoxyethanol (3 ml) was heated to 403 K for 24 h. The reaction was cooled down to room temperature, and the solvent was removed under reduced pressure. The residue was poured into water (30 ml), treated with and the resulting suspension was filtered through Celite. Acidification of the filtrate with dilute HCl (pH 5) gave a bluish precipitate (crude product). The crude product was dissolved in aqueous Na2CO3 solution (5%wt, 100 ml) and the solution was filtered through Celite and subjected to acidification and subsequent precipitation to give a pure product. Blue rod-shaped crystals were grown from CH3CN solution by slow evaporation (Fig. 3).
Refinement
Crystal data, data collection and structure .
details are summarized in Table 2
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Structural data
CCDC reference: 2009944
https://doi.org/10.1107/S2414314620008019/wm4131sup1.cif
contains datablocks global, I. DOI:Structure factors: contains datablock I. DOI: https://doi.org/10.1107/S2414314620008019/wm4131Isup2.hkl
Data collection: COLLECT (Nonius, 2002); cell
DENZO-SMN (Otwinowski & Minor, 1997); data reduction: DENZO-SMN (Otwinowski & Minor, 1997); program(s) used to solve structure: SHELXS97 (Sheldrick, 2008); program(s) used to refine structure: SHELXL2018/3 (Sheldrick, 2015); molecular graphics: XP in SHELXTL (Sheldrick, 2008) and Mercury (Macrae et al., 2020); software used to prepare material for publication: publCIF (Westrip, 2010).[Cu2(C13H8NO4S)4(C2H3N)2] | Z = 1 |
Mr = 1306.24 | F(000) = 666 |
Triclinic, P1 | Dx = 1.565 Mg m−3 |
a = 10.7377 (1) Å | Mo Kα radiation, λ = 0.71073 Å |
b = 11.0957 (1) Å | Cell parameters from 6289 reflections |
c = 12.4857 (2) Å | θ = 1.0–27.5° |
α = 77.9948 (5)° | µ = 1.00 mm−1 |
β = 88.1362 (5)° | T = 90 K |
γ = 72.3710 (5)° | Rod, blue |
V = 1385.97 (3) Å3 | 0.50 × 0.40 × 0.20 mm |
Nonius KappaCCD diffractometer | 6335 independent reflections |
Radiation source: fine-focus sealed tube | 5914 reflections with I > 2σ(I) |
Detector resolution: 18 pixels mm-1 | Rint = 0.016 |
ω scans at fixed χ=55° | θmax = 27.5°, θmin = 1.7° |
Absorption correction: multi-scan (Scalepack; Otwinowski & Minor, 1997) | h = −13→13 |
Tmin = 0.636, Tmax = 0.826 | k = −14→14 |
12571 measured reflections | l = −16→16 |
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)] = 0.023 | Hydrogen site location: inferred from neighbouring sites |
wR(F2) = 0.061 | H-atom parameters constrained |
S = 1.05 | w = 1/[σ2(Fo2) + (0.0208P)2 + 0.9758P] where P = (Fo2 + 2Fc2)/3 |
6335 reflections | (Δ/σ)max = 0.002 |
380 parameters | Δρmax = 0.36 e Å−3 |
0 restraints | Δρmin = −0.39 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. |
x | y | z | Uiso*/Ueq | ||
Cu1 | 0.37846 (2) | 0.99509 (2) | 0.01065 (2) | 0.00993 (5) | |
C20 | 0.00546 (18) | 1.0018 (2) | 0.19864 (15) | 0.0383 (4) | |
H20A | 0.021784 | 0.918044 | 0.249462 | 0.057* | |
H20B | −0.082418 | 1.027638 | 0.165040 | 0.057* | |
H20C | 0.012133 | 1.066883 | 0.238691 | 0.057* | |
C21 | 0.10207 (15) | 0.99118 (16) | 0.11335 (13) | 0.0219 (3) | |
N22 | 0.17853 (12) | 0.98250 (13) | 0.04760 (11) | 0.0210 (3) | |
C1A | 0.73172 (13) | 0.54587 (13) | −0.03417 (11) | 0.0129 (3) | |
C2A | 0.63214 (13) | 0.61581 (13) | 0.02586 (10) | 0.0121 (3) | |
C3A | 0.57027 (13) | 0.55063 (13) | 0.10719 (11) | 0.0131 (3) | |
H3A | 0.502908 | 0.597453 | 0.147404 | 0.016* | |
C4A | 0.60775 (13) | 0.41742 (13) | 0.12878 (11) | 0.0135 (3) | |
C5A | 0.70116 (14) | 0.34601 (13) | 0.06829 (11) | 0.0154 (3) | |
H5A | 0.723021 | 0.254424 | 0.082499 | 0.018* | |
C6A | 0.76180 (14) | 0.41077 (14) | −0.01307 (12) | 0.0161 (3) | |
H6A | 0.825160 | 0.362840 | −0.055605 | 0.019* | |
S7A | 0.81150 (3) | 0.63183 (3) | −0.13466 (3) | 0.01537 (8) | |
C8A | 0.90777 (13) | 0.50792 (13) | −0.20027 (11) | 0.0141 (3) | |
C9A | 0.87216 (14) | 0.50745 (14) | −0.30608 (12) | 0.0164 (3) | |
H9A | 0.796224 | 0.570717 | −0.341701 | 0.020* | |
C10A | 0.94849 (14) | 0.41366 (15) | −0.35961 (12) | 0.0199 (3) | |
H10A | 0.925925 | 0.414027 | −0.432642 | 0.024* | |
C11A | 1.05753 (15) | 0.31967 (15) | −0.30620 (13) | 0.0220 (3) | |
H11A | 1.108205 | 0.254619 | −0.342354 | 0.026* | |
C12A | 1.09315 (14) | 0.31990 (15) | −0.20054 (13) | 0.0211 (3) | |
H12A | 1.167443 | 0.254741 | −0.164227 | 0.025* | |
C13A | 1.01995 (14) | 0.41563 (15) | −0.14789 (12) | 0.0176 (3) | |
H13A | 1.046003 | 0.418341 | −0.076659 | 0.021* | |
C14A | 0.58662 (13) | 0.76073 (13) | 0.00758 (10) | 0.0119 (2) | |
O15A | 0.32797 (9) | 1.18158 (9) | 0.00850 (8) | 0.0148 (2) | |
O16A | 0.46503 (10) | 0.81172 (9) | 0.01343 (8) | 0.0167 (2) | |
N17A | 0.54354 (12) | 0.34971 (12) | 0.21587 (9) | 0.0167 (2) | |
O18A | 0.57926 (13) | 0.23095 (10) | 0.23492 (9) | 0.0291 (3) | |
O19A | 0.45741 (11) | 0.41481 (10) | 0.26574 (9) | 0.0218 (2) | |
C1B | 0.47177 (13) | 0.84097 (13) | 0.39310 (11) | 0.0132 (3) | |
C2B | 0.55474 (13) | 0.90071 (13) | 0.32621 (11) | 0.0123 (3) | |
C3B | 0.66210 (13) | 0.91810 (13) | 0.37284 (11) | 0.0132 (3) | |
H3B | 0.718486 | 0.957058 | 0.328018 | 0.016* | |
C4B | 0.68656 (13) | 0.87855 (13) | 0.48456 (11) | 0.0135 (3) | |
C5B | 0.60457 (14) | 0.82457 (13) | 0.55299 (11) | 0.0146 (3) | |
H5B | 0.620979 | 0.800878 | 0.630000 | 0.018* | |
C6B | 0.49851 (13) | 0.80600 (13) | 0.50678 (11) | 0.0146 (3) | |
H6B | 0.442099 | 0.768585 | 0.553019 | 0.017* | |
S7B | 0.34082 (3) | 0.80704 (4) | 0.33483 (3) | 0.01856 (8) | |
C8B | 0.28760 (13) | 0.71437 (14) | 0.45143 (11) | 0.0161 (3) | |
C9B | 0.18868 (14) | 0.77613 (15) | 0.51410 (13) | 0.0203 (3) | |
H9B | 0.148411 | 0.866897 | 0.493867 | 0.024* | |
C10B | 0.14911 (15) | 0.70463 (16) | 0.60623 (13) | 0.0228 (3) | |
H10B | 0.082094 | 0.746774 | 0.649382 | 0.027* | |
C11B | 0.20682 (15) | 0.57216 (16) | 0.63558 (12) | 0.0221 (3) | |
H11B | 0.181478 | 0.523963 | 0.700033 | 0.026* | |
C12B | 0.30193 (15) | 0.50986 (15) | 0.57050 (13) | 0.0210 (3) | |
H12B | 0.339840 | 0.418677 | 0.589475 | 0.025* | |
C13B | 0.34171 (14) | 0.58063 (14) | 0.47772 (12) | 0.0177 (3) | |
H13B | 0.405530 | 0.537858 | 0.432525 | 0.021* | |
C14B | 0.53438 (13) | 0.94456 (13) | 0.20461 (11) | 0.0127 (3) | |
O15B | 0.36927 (9) | 1.03736 (9) | −0.14980 (8) | 0.01443 (19) | |
O16B | 0.42258 (10) | 0.95862 (10) | 0.16679 (8) | 0.0179 (2) | |
N17B | 0.80353 (12) | 0.89184 (12) | 0.53147 (10) | 0.0176 (2) | |
O18B | 0.81739 (12) | 0.86967 (12) | 0.63151 (9) | 0.0276 (3) | |
O19B | 0.88348 (10) | 0.92404 (11) | 0.46750 (9) | 0.0218 (2) |
U11 | U22 | U33 | U12 | U13 | U23 | |
Cu1 | 0.01075 (8) | 0.00931 (8) | 0.00903 (8) | −0.00330 (6) | 0.00151 (6) | −0.00015 (6) |
C20 | 0.0299 (9) | 0.0581 (13) | 0.0299 (9) | −0.0159 (9) | 0.0122 (8) | −0.0135 (9) |
C21 | 0.0170 (7) | 0.0264 (8) | 0.0228 (8) | −0.0082 (6) | −0.0015 (6) | −0.0034 (6) |
N22 | 0.0148 (6) | 0.0245 (7) | 0.0233 (6) | −0.0080 (5) | 0.0009 (5) | −0.0010 (5) |
C1A | 0.0140 (6) | 0.0137 (6) | 0.0112 (6) | −0.0047 (5) | 0.0003 (5) | −0.0022 (5) |
C2A | 0.0143 (6) | 0.0115 (6) | 0.0104 (6) | −0.0037 (5) | −0.0011 (5) | −0.0018 (5) |
C3A | 0.0150 (6) | 0.0133 (6) | 0.0105 (6) | −0.0037 (5) | 0.0001 (5) | −0.0025 (5) |
C4A | 0.0173 (6) | 0.0136 (6) | 0.0099 (6) | −0.0068 (5) | 0.0002 (5) | 0.0000 (5) |
C5A | 0.0183 (7) | 0.0106 (6) | 0.0163 (6) | −0.0035 (5) | −0.0010 (5) | −0.0019 (5) |
C6A | 0.0169 (7) | 0.0140 (7) | 0.0177 (7) | −0.0037 (5) | 0.0028 (5) | −0.0055 (5) |
S7A | 0.01914 (17) | 0.01343 (16) | 0.01462 (16) | −0.00625 (13) | 0.00703 (13) | −0.00429 (12) |
C8A | 0.0141 (6) | 0.0146 (6) | 0.0146 (6) | −0.0054 (5) | 0.0047 (5) | −0.0040 (5) |
C9A | 0.0135 (6) | 0.0179 (7) | 0.0165 (7) | −0.0030 (5) | 0.0004 (5) | −0.0036 (5) |
C10A | 0.0186 (7) | 0.0262 (8) | 0.0175 (7) | −0.0068 (6) | 0.0016 (5) | −0.0103 (6) |
C11A | 0.0177 (7) | 0.0212 (8) | 0.0286 (8) | −0.0039 (6) | 0.0068 (6) | −0.0122 (6) |
C12A | 0.0136 (7) | 0.0202 (7) | 0.0256 (8) | −0.0014 (6) | 0.0008 (6) | −0.0015 (6) |
C13A | 0.0154 (7) | 0.0230 (7) | 0.0142 (6) | −0.0067 (6) | 0.0008 (5) | −0.0022 (5) |
C14A | 0.0165 (6) | 0.0115 (6) | 0.0070 (6) | −0.0035 (5) | 0.0009 (5) | −0.0012 (5) |
O15A | 0.0164 (5) | 0.0110 (5) | 0.0177 (5) | −0.0050 (4) | 0.0039 (4) | −0.0039 (4) |
O16A | 0.0149 (5) | 0.0102 (5) | 0.0231 (5) | −0.0029 (4) | 0.0014 (4) | −0.0009 (4) |
N17A | 0.0243 (6) | 0.0150 (6) | 0.0116 (5) | −0.0087 (5) | 0.0004 (5) | −0.0004 (4) |
O18A | 0.0527 (8) | 0.0130 (5) | 0.0222 (6) | −0.0134 (5) | 0.0126 (5) | −0.0016 (4) |
O19A | 0.0243 (5) | 0.0208 (5) | 0.0188 (5) | −0.0072 (4) | 0.0082 (4) | −0.0015 (4) |
C1B | 0.0130 (6) | 0.0118 (6) | 0.0127 (6) | −0.0017 (5) | 0.0005 (5) | −0.0013 (5) |
C2B | 0.0140 (6) | 0.0098 (6) | 0.0109 (6) | −0.0008 (5) | 0.0020 (5) | −0.0017 (5) |
C3B | 0.0149 (6) | 0.0108 (6) | 0.0133 (6) | −0.0028 (5) | 0.0034 (5) | −0.0031 (5) |
C4B | 0.0135 (6) | 0.0125 (6) | 0.0147 (6) | −0.0032 (5) | 0.0003 (5) | −0.0043 (5) |
C5B | 0.0182 (7) | 0.0133 (6) | 0.0104 (6) | −0.0025 (5) | 0.0010 (5) | −0.0016 (5) |
C6B | 0.0154 (6) | 0.0151 (7) | 0.0118 (6) | −0.0042 (5) | 0.0032 (5) | −0.0007 (5) |
S7B | 0.01666 (17) | 0.02532 (19) | 0.01348 (16) | −0.01036 (14) | −0.00195 (13) | 0.00278 (13) |
C8B | 0.0139 (6) | 0.0204 (7) | 0.0144 (6) | −0.0077 (5) | 0.0000 (5) | −0.0006 (5) |
C9B | 0.0181 (7) | 0.0177 (7) | 0.0269 (8) | −0.0069 (6) | 0.0033 (6) | −0.0066 (6) |
C10B | 0.0210 (7) | 0.0297 (8) | 0.0239 (8) | −0.0124 (6) | 0.0093 (6) | −0.0134 (6) |
C11B | 0.0228 (7) | 0.0304 (8) | 0.0163 (7) | −0.0158 (7) | 0.0014 (6) | −0.0007 (6) |
C12B | 0.0194 (7) | 0.0187 (7) | 0.0226 (7) | −0.0060 (6) | −0.0029 (6) | 0.0015 (6) |
C13B | 0.0133 (6) | 0.0209 (7) | 0.0178 (7) | −0.0036 (5) | 0.0000 (5) | −0.0041 (6) |
C14B | 0.0167 (6) | 0.0088 (6) | 0.0111 (6) | −0.0020 (5) | 0.0016 (5) | −0.0018 (5) |
O15B | 0.0153 (5) | 0.0167 (5) | 0.0099 (4) | −0.0040 (4) | 0.0027 (4) | −0.0015 (4) |
O16B | 0.0172 (5) | 0.0245 (5) | 0.0104 (4) | −0.0073 (4) | 0.0004 (4) | 0.0017 (4) |
N17B | 0.0187 (6) | 0.0177 (6) | 0.0180 (6) | −0.0065 (5) | −0.0004 (5) | −0.0059 (5) |
O18B | 0.0295 (6) | 0.0413 (7) | 0.0168 (5) | −0.0159 (5) | −0.0035 (4) | −0.0080 (5) |
O19B | 0.0196 (5) | 0.0248 (6) | 0.0243 (5) | −0.0116 (4) | 0.0030 (4) | −0.0053 (4) |
Cu1—O16B | 1.9505 (10) | C13A—H13A | 0.9500 |
Cu1—O16A | 1.9576 (10) | C14A—O15Ai | 1.2574 (17) |
Cu1—O15B | 1.9588 (9) | C14A—O16A | 1.2624 (17) |
Cu1—O15A | 1.9685 (10) | N17A—O18A | 1.2287 (16) |
Cu1—N22 | 2.2206 (12) | N17A—O19A | 1.2287 (16) |
Cu1—Cu1i | 2.6478 (3) | C1B—C6B | 1.4062 (18) |
C20—C21 | 1.460 (2) | C1B—C2B | 1.4176 (18) |
C20—H20A | 0.9800 | C1B—S7B | 1.7746 (14) |
C20—H20B | 0.9800 | C2B—C3B | 1.3893 (19) |
C20—H20C | 0.9800 | C2B—C14B | 1.4966 (18) |
C21—N22 | 1.139 (2) | C3B—C4B | 1.3808 (19) |
C1A—C6A | 1.4032 (19) | C3B—H3B | 0.9500 |
C1A—C2A | 1.4123 (18) | C4B—C5B | 1.3862 (19) |
C1A—S7A | 1.7734 (14) | C4B—N17B | 1.4623 (18) |
C2A—C3A | 1.3919 (18) | C5B—C6B | 1.381 (2) |
C2A—C14A | 1.5017 (18) | C5B—H5B | 0.9500 |
C3A—C4A | 1.3785 (19) | C6B—H6B | 0.9500 |
C3A—H3A | 0.9500 | S7B—C8B | 1.7839 (14) |
C4A—C5A | 1.3865 (19) | C8B—C13B | 1.391 (2) |
C4A—N17A | 1.4654 (17) | C8B—C9B | 1.392 (2) |
C5A—C6A | 1.3816 (19) | C9B—C10B | 1.388 (2) |
C5A—H5A | 0.9500 | C9B—H9B | 0.9500 |
C6A—H6A | 0.9500 | C10B—C11B | 1.385 (2) |
S7A—C8A | 1.7840 (14) | C10B—H10B | 0.9500 |
C8A—C9A | 1.3887 (19) | C11B—C12B | 1.390 (2) |
C8A—C13A | 1.397 (2) | C11B—H11B | 0.9500 |
C9A—C10A | 1.392 (2) | C12B—C13B | 1.391 (2) |
C9A—H9A | 0.9500 | C12B—H12B | 0.9500 |
C10A—C11A | 1.387 (2) | C13B—H13B | 0.9500 |
C10A—H10A | 0.9500 | C14B—O16B | 1.2574 (17) |
C11A—C12A | 1.386 (2) | C14B—O15Bi | 1.2655 (16) |
C11A—H11A | 0.9500 | N17B—O18B | 1.2267 (16) |
C12A—C13A | 1.389 (2) | N17B—O19B | 1.2349 (16) |
C12A—H12A | 0.9500 | ||
O16B—Cu1—O16A | 87.64 (4) | C12A—C13A—C8A | 119.63 (13) |
O16B—Cu1—O15B | 168.27 (4) | C12A—C13A—H13A | 120.2 |
O16A—Cu1—O15B | 91.98 (4) | C8A—C13A—H13A | 120.2 |
O16B—Cu1—O15A | 89.65 (4) | O15Ai—C14A—O16A | 126.72 (13) |
O16A—Cu1—O15A | 168.31 (4) | O15Ai—C14A—C2A | 117.69 (12) |
O15B—Cu1—O15A | 88.37 (4) | O16A—C14A—C2A | 115.55 (12) |
O16B—Cu1—N22 | 90.57 (4) | C14Ai—O15A—Cu1 | 119.40 (9) |
O16A—Cu1—N22 | 97.89 (5) | C14A—O16A—Cu1 | 125.20 (9) |
O15B—Cu1—N22 | 101.10 (4) | O18A—N17A—O19A | 123.80 (12) |
O15A—Cu1—N22 | 93.50 (4) | O18A—N17A—C4A | 118.00 (12) |
O16B—Cu1—Cu1i | 83.35 (3) | O19A—N17A—C4A | 118.21 (11) |
O16A—Cu1—Cu1i | 81.95 (3) | C6B—C1B—C2B | 118.05 (12) |
O15B—Cu1—Cu1i | 84.98 (3) | C6B—C1B—S7B | 120.91 (10) |
O15A—Cu1—Cu1i | 86.45 (3) | C2B—C1B—S7B | 121.02 (10) |
N22—Cu1—Cu1i | 173.92 (4) | C3B—C2B—C1B | 119.99 (12) |
C21—C20—H20A | 109.5 | C3B—C2B—C14B | 117.13 (12) |
C21—C20—H20B | 109.5 | C1B—C2B—C14B | 122.86 (12) |
H20A—C20—H20B | 109.5 | C4B—C3B—C2B | 119.77 (12) |
C21—C20—H20C | 109.5 | C4B—C3B—H3B | 120.1 |
H20A—C20—H20C | 109.5 | C2B—C3B—H3B | 120.1 |
H20B—C20—H20C | 109.5 | C3B—C4B—C5B | 121.79 (13) |
N22—C21—C20 | 179.27 (17) | C3B—C4B—N17B | 118.98 (12) |
C21—N22—Cu1 | 142.80 (12) | C5B—C4B—N17B | 119.22 (12) |
C6A—C1A—C2A | 118.39 (12) | C6B—C5B—C4B | 118.55 (12) |
C6A—C1A—S7A | 122.63 (10) | C6B—C5B—H5B | 120.7 |
C2A—C1A—S7A | 118.97 (10) | C4B—C5B—H5B | 120.7 |
C3A—C2A—C1A | 120.17 (12) | C5B—C6B—C1B | 121.77 (13) |
C3A—C2A—C14A | 116.23 (12) | C5B—C6B—H6B | 119.1 |
C1A—C2A—C14A | 123.60 (12) | C1B—C6B—H6B | 119.1 |
C4A—C3A—C2A | 119.31 (13) | C1B—S7B—C8B | 101.35 (6) |
C4A—C3A—H3A | 120.3 | C13B—C8B—C9B | 120.08 (13) |
C2A—C3A—H3A | 120.3 | C13B—C8B—S7B | 120.24 (11) |
C3A—C4A—C5A | 121.98 (12) | C9B—C8B—S7B | 119.66 (11) |
C3A—C4A—N17A | 118.85 (12) | C10B—C9B—C8B | 119.76 (14) |
C5A—C4A—N17A | 119.13 (12) | C10B—C9B—H9B | 120.1 |
C6A—C5A—C4A | 118.65 (13) | C8B—C9B—H9B | 120.1 |
C6A—C5A—H5A | 120.7 | C11B—C10B—C9B | 120.33 (14) |
C4A—C5A—H5A | 120.7 | C11B—C10B—H10B | 119.8 |
C5A—C6A—C1A | 121.35 (13) | C9B—C10B—H10B | 119.8 |
C5A—C6A—H6A | 119.3 | C10B—C11B—C12B | 119.85 (14) |
C1A—C6A—H6A | 119.3 | C10B—C11B—H11B | 120.1 |
C1A—S7A—C8A | 102.32 (6) | C12B—C11B—H11B | 120.1 |
C9A—C8A—C13A | 120.39 (13) | C11B—C12B—C13B | 120.19 (14) |
C9A—C8A—S7A | 118.87 (11) | C11B—C12B—H12B | 119.9 |
C13A—C8A—S7A | 120.69 (11) | C13B—C12B—H12B | 119.9 |
C8A—C9A—C10A | 119.57 (13) | C12B—C13B—C8B | 119.66 (14) |
C8A—C9A—H9A | 120.2 | C12B—C13B—H13B | 120.2 |
C10A—C9A—H9A | 120.2 | C8B—C13B—H13B | 120.2 |
C11A—C10A—C9A | 119.95 (14) | O16B—C14B—O15Bi | 126.33 (12) |
C11A—C10A—H10A | 120.0 | O16B—C14B—C2B | 116.29 (12) |
C9A—C10A—H10A | 120.0 | O15Bi—C14B—C2B | 117.37 (12) |
C12A—C11A—C10A | 120.55 (14) | C14Bi—O15B—Cu1 | 121.32 (9) |
C12A—C11A—H11A | 119.7 | C14B—O16B—Cu1 | 123.77 (9) |
C10A—C11A—H11A | 119.7 | O18B—N17B—O19B | 123.72 (12) |
C11A—C12A—C13A | 119.84 (14) | O18B—N17B—C4B | 118.56 (12) |
C11A—C12A—H12A | 120.1 | O19B—N17B—C4B | 117.72 (12) |
C13A—C12A—H12A | 120.1 | ||
C6A—C1A—C2A—C3A | 2.85 (19) | C6B—C1B—C2B—C3B | 2.74 (19) |
S7A—C1A—C2A—C3A | −178.32 (10) | S7B—C1B—C2B—C3B | −175.48 (10) |
C6A—C1A—C2A—C14A | −177.17 (12) | C6B—C1B—C2B—C14B | −178.72 (12) |
S7A—C1A—C2A—C14A | 1.66 (18) | S7B—C1B—C2B—C14B | 3.05 (18) |
C1A—C2A—C3A—C4A | 0.4 (2) | C1B—C2B—C3B—C4B | −0.8 (2) |
C14A—C2A—C3A—C4A | −179.61 (12) | C14B—C2B—C3B—C4B | −179.46 (12) |
C2A—C3A—C4A—C5A | −3.2 (2) | C2B—C3B—C4B—C5B | −1.8 (2) |
C2A—C3A—C4A—N17A | 178.95 (12) | C2B—C3B—C4B—N17B | 177.03 (12) |
C3A—C4A—C5A—C6A | 2.6 (2) | C3B—C4B—C5B—C6B | 2.4 (2) |
N17A—C4A—C5A—C6A | −179.52 (12) | N17B—C4B—C5B—C6B | −176.42 (12) |
C4A—C5A—C6A—C1A | 0.8 (2) | C4B—C5B—C6B—C1B | −0.4 (2) |
C2A—C1A—C6A—C5A | −3.4 (2) | C2B—C1B—C6B—C5B | −2.1 (2) |
S7A—C1A—C6A—C5A | 177.77 (11) | S7B—C1B—C6B—C5B | 176.08 (11) |
C6A—C1A—S7A—C8A | 7.14 (13) | C6B—C1B—S7B—C8B | −5.99 (13) |
C2A—C1A—S7A—C8A | −171.63 (11) | C2B—C1B—S7B—C8B | 172.19 (11) |
C1A—S7A—C8A—C9A | 108.76 (12) | C1B—S7B—C8B—C13B | −89.83 (12) |
C1A—S7A—C8A—C13A | −73.62 (12) | C1B—S7B—C8B—C9B | 92.16 (12) |
C13A—C8A—C9A—C10A | 0.5 (2) | C13B—C8B—C9B—C10B | 3.4 (2) |
S7A—C8A—C9A—C10A | 178.11 (11) | S7B—C8B—C9B—C10B | −178.58 (12) |
C8A—C9A—C10A—C11A | 1.5 (2) | C8B—C9B—C10B—C11B | −0.5 (2) |
C9A—C10A—C11A—C12A | −1.5 (2) | C9B—C10B—C11B—C12B | −2.1 (2) |
C10A—C11A—C12A—C13A | −0.6 (2) | C10B—C11B—C12B—C13B | 1.7 (2) |
C11A—C12A—C13A—C8A | 2.6 (2) | C11B—C12B—C13B—C8B | 1.2 (2) |
C9A—C8A—C13A—C12A | −2.6 (2) | C9B—C8B—C13B—C12B | −3.7 (2) |
S7A—C8A—C13A—C12A | 179.85 (11) | S7B—C8B—C13B—C12B | 178.26 (11) |
C3A—C2A—C14A—O15Ai | 138.82 (13) | C3B—C2B—C14B—O16B | −162.85 (12) |
C1A—C2A—C14A—O15Ai | −41.16 (18) | C1B—C2B—C14B—O16B | 18.58 (19) |
C3A—C2A—C14A—O16A | −39.11 (17) | C3B—C2B—C14B—O15Bi | 17.83 (18) |
C1A—C2A—C14A—O16A | 140.91 (13) | C1B—C2B—C14B—O15Bi | −160.74 (13) |
O15Ai—C14A—O16A—Cu1 | −5.3 (2) | O15Bi—C14B—O16B—Cu1 | 6.7 (2) |
C2A—C14A—O16A—Cu1 | 172.44 (8) | C2B—C14B—O16B—Cu1 | −172.57 (9) |
C3A—C4A—N17A—O18A | −179.13 (13) | C3B—C4B—N17B—O18B | 172.27 (13) |
C5A—C4A—N17A—O18A | 2.94 (19) | C5B—C4B—N17B—O18B | −8.87 (19) |
C3A—C4A—N17A—O19A | 0.73 (19) | C3B—C4B—N17B—O19B | −8.25 (19) |
C5A—C4A—N17A—O19A | −177.20 (13) | C5B—C4B—N17B—O19B | 170.61 (13) |
Symmetry code: (i) −x+1, −y+2, −z. |
Cg4 is the centroid of the C8B–C13B ring. |
D—H···A | D—H | H···A | D···A | D—H···A |
C6B—H6B···O18Aii | 0.95 | 2.65 | 3.2785 (17) | 124 |
C9B—H9B···O19Biii | 0.95 | 2.39 | 3.2351 (19) | 148 |
C10—H10A···Cg4iv | 0.95 | 2.63 | 3.4171 (17) | 140 |
Symmetry codes: (ii) −x+1, −y+1, −z+1; (iii) −x+1, −y+2, −z+1; (iv) −x+1, −y+1, −z. |
Acknowledgements
The authors thank Dr Sean Parkin for assistance in preparing the manuscript.
Funding information
The authors acknowledge the Natural Science Foundation of Hubei Province for financial support (2014CFB787).
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