The title compound, [Cu
2(μ
2-O
2CC
12H
8NO
2S)
4(CH
3CN)
2], consists of a dinuclear and centrosymmetric complex based on two Cu
II 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 NO
4 coordination environment for each Cu
II 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 crystal structure is ensured by
(phenyl)C—H
O
(nitro) hydrogen bonds and
(phenyl)C—H
π interactions.
Supporting information
CCDC reference: 2009944
Key indicators
- Single-crystal X-ray study
- T = 90 K
- Mean (C-C) = 0.002 Å
- R factor = 0.023
- wR factor = 0.061
- Data-to-parameter ratio = 16.7
checkCIF/PLATON results
No syntax errors found
Alert level C
PLAT220_ALERT_2_C NonSolvent Resd 1 C Ueq(max) / Ueq(min) Range 3.2 Ratio
PLAT480_ALERT_4_C Long H...A H-Bond Reported H6B ..O18A . 2.65 Ang.
PLAT911_ALERT_3_C Missing FCF Refl Between Thmin & STh/L= 0.600 10 Report
PLAT913_ALERT_3_C Missing # of Very Strong Reflections in FCF .... 7 Note
Alert level G
PLAT154_ALERT_1_G The s.u.'s on the Cell Angles are Equal ..(Note) 0.0005 Degree
PLAT232_ALERT_2_G Hirshfeld Test Diff (M-X) Cu1 --N22 . 5.7 s.u.
PLAT794_ALERT_5_G Tentative Bond Valency for Cu1 (II) . 2.16 Info
PLAT912_ALERT_4_G Missing # of FCF Reflections Above STh/L= 0.600 6 Note
PLAT978_ALERT_2_G Number C-C Bonds with Positive Residual Density. 19 Info
0 ALERT level A = Most likely a serious problem - resolve or explain
0 ALERT level B = A potentially serious problem, consider carefully
4 ALERT level C = Check. Ensure it is not caused by an omission or oversight
5 ALERT level G = General information/check it is not something unexpected
1 ALERT type 1 CIF construction/syntax error, inconsistent or missing data
3 ALERT type 2 Indicator that the structure model may be wrong or deficient
2 ALERT type 3 Indicator that the structure quality may be low
2 ALERT type 4 Improvement, methodology, query or suggestion
1 ALERT type 5 Informative message, check
Data collection: COLLECT (Nonius, 2002); cell refinement: 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).
Tetrakis[µ
2-5-nitro-2-(phenylsulfanyl)benzoato-
κ2O:
O']bis[(acetonitrile-
κN)copper(II)]
top
Crystal data top
[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 |
Data collection top
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 top
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 |
Special details top
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. |
Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Å2) top | 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) | |
Atomic displacement parameters (Å2) top | 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) |
Geometric parameters (Å, º) top
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. |
Hydrogen-bond geometry (Å, º) topCg4 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. |