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The crystal structures of two compounds, CuL2 and LiNCS·HL [HL = 4'-[2-(tosylamino)benzylideneamino]-2,3-benzo-15-crown-5], have been determined from synchrotron powder diffraction data. Both compounds crystallize in the monoclinic space group P21/c and with one molecule in the asymmetric unit. In CuL2 the four N atoms of two bidentate L ligands coordinate the CuII ion in a distorted tetrahedral geometry with Cu-N distances of 1.98 (5)-2.05 (5) Å, while two O atoms from two sulfoxide groups complete the distorted octahedral Cu coordination [Cu-O 2.64 (4), 2.74 (4) Å]. In LiNCS·HL, lithium is coordinated by all five ether O atoms with Li-O distances of 2.03 (3)-2.50 (3) Å and an N atom from the thiocyanate moiety [Li-N 1.98 (3) Å] in a distorted pentagonal pyramidal geometry. Preliminary potentiometric selectivity measurements for ion-selective electrodes (ISEs) based on CuL2 and ZnL2 demonstrated significant differences in their selectivity. In order to find a possible reason for this, theoretical calculations at the DFT (B3LYP) level were performed. These calculations used the crystal structures of CuL2, LiNCS·HL, ZnL2 and HL as input geometries for the minimum energy optimization in vacuo. The results indicate that in ML2 complexes (M = Cu, Zn) the electronic structure of the metal ion determines the spatial orientation of benzo-15-crown-5 macrocycles, and their different orientation in CuL2 and ZnL2 results in different potentiometric selectivities of ISEs based on these compounds.

Supporting information

cif

Crystallographic Information File (CIF) https://doi.org/10.1107/S0108768107003898/kd5008sup1.cif
Contains datablocks CuL2, LiNCS, global

rtv

Rietveld powder data file (CIF format) https://doi.org/10.1107/S0108768107003898/kd5008LiNCSsup2.rtv
Contains datablock LiNCS

rtv

Rietveld powder data file (CIF format) https://doi.org/10.1107/S0108768107003898/kd5008CuL2sup3.rtv
Contains datablock CuL2

pdf

Portable Document Format (PDF) file https://doi.org/10.1107/S0108768107003898/kd5008sup4.pdf
Supplementary material

CCDC references: 650625; 650626

Computing details top

For both compounds, cell refinement: LSPAID (Visser et al., 1986); data reduction: MRIA (Zlokazov et al., 1992); program(s) used to solve structure: MRIA; program(s) used to refine structure: MRIA; molecular graphics: PLATON (Spek, 2003); software used to prepare material for publication: MRIA.

Figures top
[Figure 1]
[Figure 2]
[Figure 3]
[Figure 4]
[Figure 5]
[Figure 6]
(CuL2) top
Crystal data top
C56H62CuN4O14S2F(000) = 2396
Mr = 1142.79Dx = 1.436 Mg m3
Monoclinic, P21/cSynchrotron radiation, λ = 0.51966(1) Å
a = 19.0356 (6) ŵ = 0.30 mm1
b = 17.4332 (6) ÅT = 295 K
c = 17.4180 (6) ÅParticle morphology: no specific habit
β = 113.824 (3)°black
V = 5287.7 (3) Å3cylinder, 15 × 0.3 mm
Z = 4Specimen preparation: Prepared at 295 K and 101.3(2) kPa
Data collection top
ESRF powder
diffractometer
Data collection mode: transmission
Radiation source: BM1B bending magnet at ESRF, synchrotron radiationScan method: continuous
Si 111 double crystal monochromator2θmin = 1.017°, 2θmax = 22.014°, 2θstep = 0.003°
Specimen mounting: Specimen was sealed in a 0.3 mm diameter borosilicate glass capillary
Refinement top
Refinement on Inet277 parameters
Least-squares matrix: full with fixed elements per cycle233 restraints
Rp = 0.04672 constraints
Rwp = 0.063H-atom parameters not refined
Rexp = 0.048Weighting scheme based on measured s.u.'s
χ2 = 1.700(Δ/σ)max = 0.027
7000 data pointsBackground function: Chebyshev polynomial up to the 5th order
Profile function: split-type pseudo-Voigt (Toraya, 1986)Preferred orientation correction: March-Dollase texture correction (Dollase, 1986). Direction of preferred orientation - 100, texture parameter r = 0.94(2).
Crystal data top
C56H62CuN4O14S2V = 5287.7 (3) Å3
Mr = 1142.79Z = 4
Monoclinic, P21/cSynchrotron radiation, λ = 0.51966(1) Å
a = 19.0356 (6) ŵ = 0.30 mm1
b = 17.4332 (6) ÅT = 295 K
c = 17.4180 (6) Åcylinder, 15 × 0.3 mm
β = 113.824 (3)°
Data collection top
ESRF powder
diffractometer
Scan method: continuous
Specimen mounting: Specimen was sealed in a 0.3 mm diameter borosilicate glass capillary2θmin = 1.017°, 2θmax = 22.014°, 2θstep = 0.003°
Data collection mode: transmission
Refinement top
Rp = 0.0467000 data points
Rwp = 0.063277 parameters
Rexp = 0.048233 restraints
χ2 = 1.700H-atom parameters not refined
Special details top

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.

Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Å2) top
xyzUiso*/Ueq
C1A0.401 (3)0.094 (3)0.380 (4)0.05 (1)*
H1A0.42420.13930.37400.05*
C2A0.327 (3)0.096 (4)0.378 (3)0.05 (1) (1)*
C3A0.293 (3)0.028 (3)0.389 (4)0.05 (1)*
H3A0.24350.03000.38810.05*
C4A0.333 (3)0.042 (4)0.402 (3)0.05 (1)*
H4A0.30970.08650.40940.05*
C5A0.407 (3)0.044 (3)0.403 (3)0.05 (1)*
C6A0.441 (3)0.024 (3)0.393 (4)0.05 (1)*
H6A0.49070.02230.39470.05*
C7A0.448 (3)0.120 (4)0.417 (4)0.05 (1)*
H7A10.41520.15980.42270.05*
H7A20.49410.11780.46750.05*
H7A30.46060.13140.37030.05*
S8A0.2769 (10)0.1830 (10)0.3609 (11)0.034 (18)*
N9A0.236 (3)0.182 (3)0.426 (3)0.05 (1)*
C10A0.280 (3)0.196 (3)0.512 (4)0.05 (1)*
C11A0.362 (3)0.201 (4)0.544 (4)0.05 (1)*
H11A0.38600.19520.50750.05*
C12A0.406 (3)0.215 (4)0.629 (4)0.05 (1)*
H12A0.45890.22020.64880.05*
C13A0.369 (3)0.221 (4)0.685 (4)0.05 (1)*
H13A0.39820.22770.74150.05*
C14A0.290 (3)0.216 (3)0.655 (3)0.05 (1)*
H14A0.26700.22130.69240.05*
C15A0.243 (3)0.202 (3)0.568 (3)0.05 (1)*
C16A0.161 (3)0.202 (4)0.546 (4)0.05 (1)*
H16A0.14660.21050.59060.05*
N17A0.105 (3)0.191 (3)0.474 (3)0.05 (1)*
C18A0.027 (3)0.166 (4)0.458 (4)0.05 (1)*
C19A0.036 (3)0.201 (4)0.397 (4)0.05 (1)*
H19A0.02760.24170.36640.05*
C20A0.112 (3)0.178 (3)0.380 (4)0.05 (1)*
C21A0.124 (3)0.115 (3)0.425 (3)0.05 (1)*
C22A0.060 (3)0.080 (4)0.487 (4)0.05 (1)*
H22A0.06690.03830.51660.05*
C23A0.015 (3)0.105 (3)0.504 (4)0.05 (1)*
H23A0.05610.08160.54700.05*
O24A0.2144 (19)0.176 (2)0.279 (2)0.05 (1)*
O25A0.327 (2)0.247 (2)0.373 (2)0.05 (1)*
O26A0.172 (2)0.214 (2)0.321 (3)0.05 (1)*
O27A0.197 (2)0.093 (2)0.409 (2)0.05 (1)*
C28A0.223 (3)0.028 (4)0.441 (4)0.05 (1)*
H28A0.20590.03320.50110.05*
H28B0.20070.01860.42950.05*
C29A0.312 (3)0.025 (3)0.398 (4)0.05 (1)*
H29A0.32980.00030.34320.05*
H29B0.33370.00080.43240.05*
O30A0.328 (2)0.104 (2)0.390 (2)0.05 (1)*
C31A0.396 (3)0.147 (3)0.360 (4)0.05 (1)*
H31A0.43900.11620.35840.05*
H31B0.40700.16560.30380.05*
C32A0.382 (3)0.215 (4)0.422 (4)0.05 (1)*
H32A0.42920.23210.42560.05*
H32B0.34410.20320.47750.05*
O33A0.3550 (19)0.269 (2)0.382 (3)0.05 (1)*
C34A0.323 (3)0.342 (4)0.404 (4)0.05 (1)*
H34A0.29510.34790.46380.05*
H34B0.36080.38240.38220.05*
C35A0.267 (3)0.341 (3)0.358 (3)0.05 (1)*
H35A0.25750.39260.34450.05*
H35B0.21870.31770.39390.05*
O36A0.303 (2)0.297 (2)0.282 (2)0.05 (1)*
C37A0.259 (3)0.310 (4)0.234 (4)0.05 (1)*
H37A0.26000.36440.22130.05*
H37B0.28190.28270.18100.05*
C38A0.175 (3)0.284 (3)0.280 (4)0.05 (1)*
H38A0.15130.27870.24080.05*
H38B0.14660.32260.32140.05*
C1B0.014 (3)0.048 (4)0.165 (4)0.06 (1)*
H1B0.05370.05800.18110.05*
C2B0.044 (3)0.004 (4)0.210 (3)0.06 (1)*
C3B0.103 (3)0.020 (3)0.185 (4)0.06 (1)*
H3B0.14060.05540.21400.05*
C4B0.106 (3)0.018 (4)0.115 (4)0.06 (1)*
H4B0.14600.00870.09920.05*
C5B0.048 (3)0.070 (4)0.069 (4)0.06 (1)*
C6B0.012 (3)0.085 (4)0.094 (4)0.06 (1)*
H6B0.05060.11880.06320.05*
C7B0.052 (3)0.109 (3)0.007 (3)0.06 (1)*
H7B10.00840.14320.03120.05*
H7B20.09830.13840.00990.05*
H7B30.05020.07140.04730.05*
S8B0.0417 (11)0.0499 (12)0.2986 (13)0.054 (19)*
N9B0.030 (3)0.142 (3)0.284 (3)0.06 (1)*
C10B0.036 (3)0.171 (4)0.218 (4)0.06 (1)*
C11B0.103 (3)0.127 (3)0.176 (4)0.06 (1)*
H11B0.10420.07660.19400.05*
C12B0.166 (3)0.155 (3)0.109 (3)0.06 (1)*
H12B0.20930.12430.08330.05*
C13B0.165 (3)0.230 (3)0.079 (4)0.06 (1)*
H13B0.20660.24900.03340.05*
C14B0.101 (3)0.276 (4)0.120 (4)0.06 (1)*
H14B0.10150.32590.10140.05*
C15B0.035 (3)0.248 (4)0.189 (4)0.06 (1)*
C16B0.028 (3)0.301 (4)0.221 (4)0.06 (1)*
H16B0.02240.35000.19780.05*
N17B0.096 (3)0.283 (3)0.285 (3)0.06 (1)*
C18B0.153 (3)0.346 (3)0.320 (4)0.06 (1)*
C19B0.188 (3)0.359 (3)0.405 (3)0.06 (1)*
H19B0.17770.32770.44240.05*
C20B0.239 (3)0.422 (4)0.435 (4)0.06 (1)*
C21B0.251 (3)0.472 (4)0.377 (4)0.06 (1)*
C22B0.216 (3)0.457 (4)0.291 (3)0.06 (1)*
H22B0.22570.48740.25320.05*
C23B0.165 (3)0.395 (3)0.262 (4)0.06 (1)*
H23B0.13990.38650.20430.05*
O24B0.116 (2)0.042 (2)0.367 (2)0.06 (1)*
O25B0.0226 (19)0.025 (2)0.317 (3)0.06 (1)*
O26B0.2726 (18)0.445 (2)0.518 (2)0.06 (1)*
O27B0.301 (2)0.533 (2)0.407 (2)0.06 (1)*
C28B0.315 (3)0.587 (4)0.354 (4)0.06 (1)*
H28C0.26780.61360.32030.05*
H28D0.33230.56040.31570.05*
C29B0.376 (3)0.647 (4)0.403 (4)0.06 (1)*
H29C0.38390.68200.36430.05*
H29D0.35790.67600.43900.05*
O30B0.446 (2)0.610 (2)0.453 (3)0.06 (1)*
C31B0.507 (4)0.650 (4)0.517 (4)0.06 (1)*
H31C0.48520.68840.54140.05*
H31D0.53870.67490.49370.05*
C32B0.556 (3)0.594 (4)0.587 (4)0.06 (1)*
H32C0.56080.54450.56300.05*
H32D0.60680.61440.61800.05*
O33B0.5148 (19)0.585 (2)0.640 (2)0.06 (1)*
C34B0.509 (3)0.508 (4)0.664 (4)0.06 (1)*
H34C0.55990.48900.69670.05*
H34D0.48720.47700.61320.05*
C35B0.459 (3)0.497 (4)0.714 (3)0.06 (1)*
H35C0.49180.48430.77190.05*
H35D0.43120.54320.71320.05*
O36B0.408 (2)0.436 (2)0.677 (2)0.06 (1)*
C37B0.330 (3)0.441 (4)0.669 (4)0.06 (1)*
H37C0.31600.49490.66800.05*
H37D0.32560.41710.71690.05*
C38B0.278 (3)0.402 (3)0.588 (4)0.06 (1)*
H38C0.29820.35100.58490.05*
H38D0.22710.39500.58730.05*
Cu0.1231 (5)0.1930 (5)0.3659 (6)0.015 (4)*
Geometric parameters (Å, º) top
Cu—N9A1.98 (5)C20B—C21B1.42 (9)
Cu—N9B1.98 (5)C21A—C22A1.40 (8)
Cu—N17A2.05 (5)C21B—C22B1.40 (8)
Cu—N17B2.03 (5)C22A—C23A1.41 (9)
Cu—O24A2.74 (4)C22B—C23B1.38 (9)
Cu—O24B2.64 (4)C28A—C29A1.57 (9)
S8A—O24A1.45 (4)C28B—C29B1.54 (9)
S8A—O25A1.43 (4)C31A—C32A1.57 (9)
S8A—N9A1.61 (5)C31B—C32B1.55 (9)
S8A—C2A1.75 (7)C34A—C35A1.55 (9)
S8B—O24B1.44 (4)C34B—C35B1.54 (9)
S8B—O25B1.45 (4)C37A—C38A1.54 (9)
S8B—N9B1.63 (6)C37B—C38B1.53 (9)
S8B—C2B1.75 (6)C1A—H1A0.93
O26A—C20A1.34 (7)C1B—H1B0.93
O26A—C38A1.40 (6)C3A—H3A0.93
O26B—C20B1.38 (7)C3B—H3B0.93
O26B—C38B1.41 (7)C4A—H4A0.93
O27A—C21A1.35 (7)C4B—H4B0.93
O27A—C28A1.44 (8)C6A—H6A0.93
O27B—C21B1.38 (8)C6B—H6B0.93
O27B—C28B1.42 (8)C7A—H7A10.96
O30A—C29A1.41 (6)C7A—H7A20.96
O30A—C31A1.40 (7)C7A—H7A30.96
O30B—C29B1.42 (7)C7B—H7B10.96
O30B—C31B1.43 (8)C7B—H7B20.96
O33A—C32A1.38 (8)C7B—H7B30.96
O33A—C34A1.42 (8)C11A—H11A0.93
O33B—C32B1.44 (7)C11B—H11B0.92
O33B—C34B1.42 (8)C12A—H12A0.93
O36A—C35A1.42 (6)C12B—H12B0.93
O36A—C37A1.42 (7)C13A—H13A0.93
O36B—C35B1.42 (7)C13B—H13B0.93
O36B—C37B1.44 (8)C14A—H14A0.93
N9A—C10A1.41 (8)C14B—H14B0.93
N9B—C10B1.41 (8)C16A—H16A0.93
N17A—C16A1.29 (8)C16B—H16B0.93
N17A—C18A1.46 (9)C19A—H19A0.93
N17B—C16B1.36 (8)C19B—H19B0.93
N17B—C18B1.49 (8)C22A—H22A0.93
C1A—C2A1.40 (9)C22B—H22B0.93
C1A—C6A1.41 (8)C23A—H23A0.93
C1B—C2B1.39 (9)C23B—H23B0.93
C1B—C6B1.41 (9)C28A—H28A0.97
C2A—C3A1.40 (9)C28A—H28B0.97
C2B—C3B1.40 (9)C28B—H28C0.97
C3A—C4A1.41 (9)C28B—H28D0.97
C3B—C4B1.41 (9)C29A—H29A0.97
C4A—C5A1.40 (9)C29A—H29B0.97
C4B—C5B1.40 (9)C29B—H29C0.97
C5A—C6A1.39 (8)C29B—H29D0.97
C5A—C7A1.51 (9)C31A—H31A0.97
C5B—C6B1.40 (9)C31A—H31B0.97
C5B—C7B1.52 (8)C31B—H31C0.97
C10A—C11A1.43 (9)C31B—H31D0.96
C10A—C15A1.42 (8)C32A—H32A0.97
C10B—C11B1.42 (9)C32A—H32B0.97
C10B—C15B1.44 (10)C32B—H32C0.97
C11A—C12A1.40 (9)C32B—H32D0.97
C11B—C12B1.39 (8)C34A—H34A0.97
C12A—C13A1.40 (9)C34A—H34B0.97
C12B—C13B1.41 (7)C34B—H34C0.97
C13A—C14A1.38 (9)C34B—H34D0.97
C13B—C14B1.39 (9)C35A—H35A0.97
C14A—C15A1.44 (7)C35A—H35B0.97
C14B—C15B1.43 (9)C35B—H35C0.97
C15A—C16A1.45 (9)C35B—H35D0.97
C15B—C16B1.44 (9)C37A—H37A0.97
C18A—C19A1.38 (9)C37A—H37B0.97
C18A—C23A1.40 (9)C37B—H37C0.97
C18B—C19B1.37 (8)C37B—H37D0.97
C18B—C23B1.41 (8)C38A—H38A0.97
C19A—C20A1.41 (9)C38A—H38B0.97
C19B—C20B1.42 (9)C38B—H38C0.97
C20A—C21A1.42 (8)C38B—H38D0.97
O24A—Cu—O24B86.7 (11)C2A—C3A—H3A119
O24A—Cu—N9A59.2 (15)C4A—C3A—H3A121
O24A—Cu—N9B97.8 (18)C2B—C3B—H3B121
O24A—Cu—N17A152.3 (18)C4B—C3B—H3B120
O24A—Cu—N17B75.0 (18)C3A—C4A—H4A119
O24B—Cu—N9A87.0 (18)C5A—C4A—H4A121
O24B—Cu—N9B61.5 (17)C3B—C4B—H4B120
O24B—Cu—N17A87.0 (17)C5B—C4B—H4B120
O24B—Cu—N17B141.0 (16)C1A—C6A—H6A120
N9A—Cu—N9B143 (2)C5A—C6A—H6A119
N9A—Cu—N17A94 (2)C1B—C6B—H6B120
N9A—Cu—N17B111 (2)C5B—C6B—H6B120
N9B—Cu—N17A103 (2)C5A—C7A—H7A1109
N9B—Cu—N17B87 (2)C5A—C7A—H7A2109
N17A—Cu—N17B124 (2)C5A—C7A—H7A3109
O24A—S8A—O25A116 (2)H7A1—C7A—H7A2109
O24A—S8A—N9A105 (3)H7A1—C7A—H7A3109
O24A—S8A—C2A106 (2)H7A2—C7A—H7A3109
O25A—S8A—N9A113 (3)C5B—C7B—H7B1109
O25A—S8A—C2A111 (3)C5B—C7B—H7B2109
N9A—S8A—C2A105 (3)C5B—C7B—H7B3109
O24B—S8B—O25B115 (2)H7B1—C7B—H7B2109
O24B—S8B—N9B104 (3)H7B1—C7B—H7B3109
O24B—S8B—C2B109 (3)H7B2—C7B—H7B3110
O25B—S8B—N9B105 (3)C10A—C11A—H11A119
O25B—S8B—C2B112 (3)C12A—C11A—H11A120
N9B—S8B—C2B111 (3)C10B—C11B—H11B119
Cu—O24A—S8A84.2 (17)C12B—C11B—H11B120
Cu—O24B—S8B86.3 (18)C11A—C12A—H12A120
Cu—N17A—C18A111 (4)C13A—C12A—H12A120
C16A—N17A—C18A127 (6)C11B—C12B—H12B120
Cu—N17B—C16B130 (5)C13B—C12B—H12B120
Cu—N17B—C18B110 (4)C12A—C13A—H13A120
C16B—N17B—C18B117 (5)C14A—C13A—H13A119
C2A—C1A—C6A120 (5)C12B—C13B—H13B121
C2B—C1B—C6B120 (6)C14B—C13B—H13B120
S8A—C2A—C1A120 (5)C13A—C14A—H14A119
S8A—C2A—C3A120 (5)C15A—C14A—H14A119
C1A—C2A—C3A120 (6)C13B—C14B—H14B119
S8B—C2B—C1B121 (5)C15B—C14B—H14B120
S8B—C2B—C3B119 (5)N17A—C16A—H16A115
C1B—C2B—C3B120 (5)C15A—C16A—H16A115
C2A—C3A—C4A120 (6)N17B—C16B—H16B118
C2B—C3B—C4B120 (6)C15B—C16B—H16B119
C3A—C4A—C5A120 (6)C18A—C19A—H19A118
C3B—C4B—C5B120 (6)C20A—C19A—H19A119
C4A—C5A—C6A119 (5)C18B—C19B—H19B120
C4A—C5A—C7A118 (5)C20B—C19B—H19B120
C6A—C5A—C7A122 (6)C21A—C22A—H22A120
C4B—C5B—C6B120 (6)C23A—C22A—H22A119
C4B—C5B—C7B119 (6)C21B—C22B—H22B119
C6B—C5B—C7B121 (6)C23B—C22B—H22B120
C1A—C6A—C5A121 (6)C18A—C23A—H23A120
C1B—C6B—C5B120 (6)C22A—C23A—H23A119
N9A—C10A—C11A121 (5)C18B—C23B—H23B121
N9A—C10A—C15A120 (5)C22B—C23B—H23B120
C11A—C10A—C15A120 (6)O27A—C28A—H28A110
C20A—O26A—C38A130 (5)O27A—C28A—H28B110
C20B—O26B—C38B126 (4)C29A—C28A—H28A109
C21A—O27A—C28A128 (4)C29A—C28A—H28B110
C21B—O27B—C28B123 (4)H28A—C28A—H28B109
C29A—O30A—C31A134 (4)O27B—C28B—H28C110
C29B—O30B—C31B122 (5)O27B—C28B—H28D109
C32A—O33A—C34A130 (4)C29B—C28B—H28C109
C32B—O33B—C34B115 (4)C29B—C28B—H28D108
C35A—O36A—C37A110 (4)H28C—C28B—H28D107
C35B—O36B—C37B119 (4)O30A—C29A—H29A111
Cu—N9A—S8A111 (3)O30A—C29A—H29B112
Cu—N9A—C10A127 (4)C28A—C29A—H29A111
S8A—N9A—C10A120 (4)C28A—C29A—H29B112
Cu—N9B—S8B108 (3)H29A—C29A—H29B109
Cu—N9B—C10B132 (4)O30B—C29B—H29C110
S8B—N9B—C10B120 (5)O30B—C29B—H29D109
Cu—N17A—C16A121 (5)C28B—C29B—H29C110
N9B—C10B—C11B123 (6)C28B—C29B—H29D109
N9B—C10B—C15B119 (6)H29C—C29B—H29D109
C11B—C10B—C15B118 (6)O30A—C31A—H31A111
C10A—C11A—C12A121 (6)O30A—C31A—H31B111
C10B—C11B—C12B121 (5)C32A—C31A—H31A111
C11A—C12A—C13A119 (6)C32A—C31A—H31B111
C11B—C12B—C13B121 (5)H31A—C31A—H31B109
C12A—C13A—C14A121 (6)O30B—C31B—H31C109
C12B—C13B—C14B119 (6)O30B—C31B—H31D110
C13A—C14A—C15A121 (5)C32B—C31B—H31C109
C13B—C14B—C15B122 (6)C32B—C31B—H31D110
C10A—C15A—C14A118 (5)H31C—C31B—H31D109
C10A—C15A—C16A127 (5)O33A—C32A—H32A111
C14A—C15A—C16A115 (5)O33A—C32A—H32B111
C10B—C15B—C14B119 (6)C31A—C32A—H32A112
C10B—C15B—C16B126 (6)C31A—C32A—H32B112
C14B—C15B—C16B115 (6)H32A—C32A—H32B109
N17A—C16A—C15A129 (6)O33B—C32B—H32C110
N17B—C16B—C15B123 (6)O33B—C32B—H32D111
N17A—C18A—C19A121 (6)C31B—C32B—H32C110
N17A—C18A—C23A120 (6)C31B—C32B—H32D111
C19A—C18A—C23A119 (6)H32C—C32B—H32D109
N17B—C18B—C19B121 (5)O33A—C34A—H34A112
N17B—C18B—C23B117 (5)O33A—C34A—H34B112
C19B—C18B—C23B122 (5)C35A—C34A—H34A111
C18A—C19A—C20A122 (6)C35A—C34A—H34B110
C18B—C19B—C20B119 (5)H34A—C34A—H34B110
O26A—C20A—C19A121 (5)O33B—C34B—H34C109
O26A—C20A—C21A120 (5)O33B—C34B—H34D108
C19A—C20A—C21A119 (6)C35B—C34B—H34C109
O26B—C20B—C19B125 (5)C35B—C34B—H34D108
O26B—C20B—C21B115 (6)H34C—C34B—H34D108
C19B—C20B—C21B120 (6)O36A—C35A—H35A110
O27A—C21A—C20A119 (5)O36A—C35A—H35B110
O27A—C21A—C22A123 (5)C34A—C35A—H35A110
C20A—C21A—C22A119 (6)C34A—C35A—H35B109
O27B—C21B—C20B119 (5)H35A—C35A—H35B109
O27B—C21B—C22B122 (6)O36B—C35B—H35C109
C20B—C21B—C22B119 (6)O36B—C35B—H35D111
C21A—C22A—C23A121 (6)C34B—C35B—H35C109
C21B—C22B—C23B121 (6)C34B—C35B—H35D110
C18A—C23A—C22A120 (6)H35C—C35B—H35D109
C18B—C23B—C22B119 (6)O36A—C37A—H37A110
O27A—C28A—C29A108 (5)O36A—C37A—H37B109
O27B—C28B—C29B113 (5)C38A—C37A—H37A109
O30A—C29A—C28A100 (4)C38A—C37A—H37B109
O30B—C29B—C28B110 (5)H37A—C37A—H37B108
O30A—C31A—C32A106 (5)O36B—C37B—H37C110
O30B—C31B—C32B110 (5)O36B—C37B—H37D109
O33A—C32A—C31A99 (5)C38B—C37B—H37C110
O33B—C32B—C31B105 (5)C38B—C37B—H37D110
O33A—C34A—C35A99 (5)H37C—C37B—H37D108
O33B—C34B—C35B115 (5)O26A—C38A—H38A110
O36A—C35A—C34A112 (5)O26A—C38A—H38B109
O36B—C35B—C34B108 (5)C37A—C38A—H38A110
O36A—C37A—C38A112 (5)C37A—C38A—H38B109
O36B—C37B—C38B108 (5)H38A—C38A—H38B108
O26A—C38A—C37A110 (5)O26B—C38B—H38C110
O26B—C38B—C37B110 (5)O26B—C38B—H38D109
C2A—C1A—H1A120C37B—C38B—H38C110
C6A—C1A—H1A120C37B—C38B—H38D109
C2B—C1B—H1B120H38C—C38B—H38D109
C6B—C1B—H1B120
N17B—Cu—N9A—C10A111 (5)C31B—O30B—C29B—C28B167 (5)
O24A—Cu—N9B—S8B82 (3)C29B—O30B—C31B—C32B152 (5)
O24B—Cu—N9B—S8B0 (2)C34A—O33A—C32A—C31A172 (5)
N9A—Cu—N9B—S8B34 (5)C32A—O33A—C34A—C35A148 (6)
N17A—Cu—N9B—S8B80 (3)C34B—O33B—C32B—C31B135 (5)
N17B—Cu—N9B—S8B156 (3)C32B—O33B—C34B—C35B175 (5)
O24A—Cu—N9B—C10B94 (6)C37A—O36A—C35A—C34A168 (5)
O24B—Cu—N9B—C10B176 (7)C35A—O36A—C37A—C38A57 (6)
O24A—Cu—N17B—C18B82 (4)C37B—O36B—C35B—C34B140 (5)
O24B—Cu—N17B—C18B147 (3)C35B—O36B—C37B—C38B145 (4)
N9A—Cu—N17B—C18B34 (5)Cu—N9A—C10A—C15A15 (7)
N9B—Cu—N17B—C18B179 (4)S8A—N9A—C10A—C11A8 (7)
N17A—Cu—N17B—C18B76 (5)Cu—N9A—C10A—C11A167 (5)
N17B—Cu—O24B—S8B39 (4)S8A—N9A—C10A—C15A174 (4)
S8B—Cu—N9A—S8A84 (3)S8B—N9B—C10B—C11B17 (9)
O24A—Cu—N9A—S8A7 (2)S8B—N9B—C10B—C15B160 (5)
O24B—Cu—N9A—S8A95 (3)Cu—N9B—C10B—C15B15 (9)
N9B—Cu—N9A—S8A65 (5)Cu—N9B—C10B—C11B168 (5)
S8B—Cu—O24A—S8A124.5 (15)Cu—N17A—C18A—C23A127 (5)
O24B—Cu—O24A—S8A95.5 (17)Cu—N17A—C18A—C19A53 (7)
N9A—Cu—O24A—S8A7 (2)C18A—N17A—C16A—C15A158 (6)
N9B—Cu—O24A—S8A156 (2)C16A—N17A—C18A—C19A136 (7)
N17A—Cu—O24A—S8A18 (4)Cu—N17B—C18B—C23B152 (4)
N17B—Cu—O24A—S8A119 (2)Cu—N17B—C16B—C15B13 (9)
O24A—Cu—O24B—S8B100.4 (18)C18B—N17B—C16B—C15B172 (6)
N9A—Cu—O24B—S8B160 (2)C16B—N17B—C18B—C19B130 (6)
N9B—Cu—O24B—S8B0 (2)Cu—N17B—C18B—C19B33 (7)
N17A—Cu—O24B—S8B107 (2)C16B—N17B—C18B—C23B45 (8)
O24A—Cu—N17A—C18A146 (4)C6A—C1A—C2A—S8A179 (5)
O24B—Cu—N17A—C18A69 (4)C6A—C1A—C2A—C3A0 (9)
N9A—Cu—N17A—C18A156 (4)C2A—C1A—C6A—C5A1 (9)
N9B—Cu—N17A—C18A9 (5)C6B—C1B—C2B—S8B180 (5)
N17A—Cu—N9A—S8A179 (3)S8A—C2A—C3A—C4A179 (4)
N17B—Cu—N9A—S8A50 (3)C1A—C2A—C3A—C4A0 (8)
O24A—Cu—N9A—C10A167 (5)C1B—C2B—C3B—C4B1 (9)
O24B—Cu—N9A—C10A105 (5)S8B—C2B—C3B—C4B178 (5)
N9B—Cu—N9A—C10A135 (5)C2A—C3A—C4A—C5A1 (8)
N17A—Cu—N9A—C10A18 (5)C2B—C3B—C4B—C5B2 (9)
N9A—Cu—N17A—C16A16 (5)C3A—C4A—C5A—C6A1 (8)
N9B—Cu—N17A—C16A163 (5)C3A—C4A—C5A—C7A180 (5)
N17B—Cu—N17A—C16A102 (5)C3B—C4B—C5B—C7B179 (6)
N17A—Cu—N9B—C10B105 (6)C7A—C5A—C6A—C1A180 (6)
N17B—Cu—N9B—C10B20 (6)C4A—C5A—C6A—C1A1 (8)
O24A—Cu—N17A—C16A26 (7)C7B—C5B—C6B—C1B180 (6)
O24B—Cu—N17A—C16A103 (5)C11A—C10A—C15A—C14A2 (8)
N17B—Cu—N17A—C18A85 (5)C11A—C10A—C15A—C16A177 (6)
N9A—Cu—N9B—C10B141 (5)N9A—C10A—C11A—C12A180 (6)
O24A—Cu—N17B—C16B117 (6)N9A—C10A—C15A—C16A6 (9)
O24B—Cu—N17B—C16B53 (7)C15A—C10A—C11A—C12A3 (9)
N9A—Cu—N17B—C16B165 (5)N9A—C10A—C15A—C14A180 (5)
N9B—Cu—N17B—C16B18 (6)N9B—C10B—C11B—C12B177 (6)
N17A—Cu—N17B—C16B85 (6)N9B—C10B—C15B—C14B178 (6)
O24A—S8A—N9A—C10A173 (4)C11B—C10B—C15B—C16B178 (6)
O25A—S8A—N9A—Cu116 (3)C11B—C10B—C15B—C14B0 (9)
N9A—S8A—O24A—Cu8 (2)C15B—C10B—C11B—C12B0 (9)
C2A—S8A—N9A—Cu122 (3)C10B—C11B—C12B—C13B1 (9)
C2A—S8A—N9A—C10A76 (5)C11B—C12B—C13B—C14B3 (9)
O25A—S8A—N9A—C10A46 (5)C12A—C13A—C14A—C15A2 (9)
O25A—S8A—O24A—Cu118 (2)C12B—C13B—C14B—C15B3 (9)
C2A—S8A—O24A—Cu118 (2)C13A—C14A—C15A—C10A2 (8)
O24A—S8A—N9A—Cu11 (3)C13A—C14A—C15A—C16A177 (6)
O25A—S8A—C2A—C1A16 (5)C13B—C14B—C15B—C10B2 (9)
N9A—S8A—C2A—C1A138 (5)C13B—C14B—C15B—C16B176 (6)
O24A—S8A—C2A—C1A112 (5)C14A—C15A—C16A—N17A180 (6)
N9A—S8A—C2A—C3A42 (5)C14B—C15B—C16B—N17B178 (6)
O25A—S8A—C2A—C3A165 (4)N17A—C18A—C23A—C22A178 (6)
O24A—S8A—C2A—C3A68 (5)N17A—C18A—C19A—C20A180 (6)
O25B—S8B—N9B—Cu122 (3)C19A—C18A—C23A—C22A1 (9)
C2B—S8B—O24B—Cu119 (3)N17B—C18B—C23B—C22B178 (6)
Cu—S8B—N9B—C10B176 (7)C23B—C18B—C19B—C20B2 (9)
O24B—S8B—N9B—C10B177 (5)C19B—C18B—C23B—C22B2 (9)
C2B—S8B—N9B—Cu117 (3)N17B—C18B—C19B—C20B177 (5)
C2B—S8B—N9B—C10B59 (6)C18A—C19A—C20A—O26A179 (6)
O25B—S8B—N9B—C10B62 (5)C18A—C19A—C20A—C21A2 (9)
Cu—S8B—C2B—C3B21 (6)C18B—C19B—C20B—C21B2 (9)
O24B—S8B—C2B—C3B50 (6)C18B—C19B—C20B—O26B174 (6)
O25B—S8B—C2B—C3B178 (5)O26A—C20A—C21A—C22A179 (5)
O24B—S8B—N9B—Cu1 (4)C19A—C20A—C21A—O27A180 (5)
O24B—S8B—C2B—C1B130 (5)O26A—C20A—C21A—O27A1 (8)
O25B—S8B—C2B—C1B1 (6)C19A—C20A—C21A—C22A3 (8)
N9B—S8B—C2B—C1B115 (6)O26B—C20B—C21B—C22B176 (5)
O25B—S8B—O24B—Cu115 (2)C19B—C20B—C21B—O27B180 (5)
N9B—S8B—O24B—Cu0 (2)C19B—C20B—C21B—C22B3 (9)
N9B—S8B—C2B—C3B65 (6)O26B—C20B—C21B—O27B7 (9)
Cu—S8B—C2B—C1B159 (4)C20A—C21A—C22A—C23A1 (9)
C38A—O26A—C20A—C19A14 (9)O27A—C21A—C22A—C23A179 (5)
C20A—O26A—C38A—C37A166 (5)C20B—C21B—C22B—C23B4 (9)
C38A—O26A—C20A—C21A168 (5)O27B—C21B—C22B—C23B180 (6)
C38B—O26B—C20B—C21B171 (5)C21A—C22A—C23A—C18A0 (9)
C20B—O26B—C38B—C37B171 (5)C21B—C22B—C23B—C18B3 (9)
C38B—O26B—C20B—C19B17 (9)O27A—C28A—C29A—O30A35 (6)
C28A—O27A—C21A—C20A175 (5)O27B—C28B—C29B—O30B58 (7)
C28A—O27A—C21A—C22A7 (8)O30A—C31A—C32A—O33A92 (5)
C21A—O27A—C28A—C29A177 (5)O30B—C31B—C32B—O33B82 (6)
C28B—O27B—C21B—C22B5 (9)O33A—C34A—C35A—O36A35 (6)
C21B—O27B—C28B—C29B177 (5)O33B—C34B—C35B—O36B132 (5)
C28B—O27B—C21B—C20B178 (6)O36A—C37A—C38A—O26A40 (7)
C29A—O30A—C31A—C32A141 (5)O36B—C37B—C38B—O26B72 (6)
C31A—O30A—C29A—C28A177 (5)
(LiNCS) top
Crystal data top
C29H32LiN3O7S2F(000) = 1272
Mr = 605.66Dx = 1.295 Mg m3
Monoclinic, P21/cSynchrotron radiation, λ = 0.52000(1) Å
a = 9.2918 (3) ŵ = 0.12 mm1
b = 23.0117 (7) ÅT = 295 K
c = 15.2798 (5) ÅParticle morphology: no specific habit
β = 108.063 (2)°yellow
V = 3106.11 (17) Å3cylinder, 15 × 0.3 mm
Z = 4Specimen preparation: Prepared at 295 K and 101.3(2) kPa
Data collection top
ESRF powder
diffractometer
Data collection mode: transmission
Radiation source: BM1B bending magnet at ESRF, synchrotron radiationScan method: continuous
Si 111 double crystal monochromator2θmin = 3.024°, 2θmax = 23.024°, 2θstep = 0.004°
Specimen mounting: Specimen was sealed in a 0.3 mm diameter borosilicate glass capillary
Refinement top
Refinement on Inet213 parameters
Least-squares matrix: full with fixed elements per cycle124 restraints
Rp = 0.04439 constraints
Rwp = 0.055H-atom parameters not refined
Rexp = 0.027Weighting scheme based on measured s.u.'s
χ2 = 3.920(Δ/σ)max = 0.035
5001 data pointsBackground function: Chebyshev polynomial up to the 5th order
Profile function: split-type pseudo-Voigt (Toraya, 1986)Preferred orientation correction: March-Dollase texture correction (Dollase, 1986). Direction of preferred orientation - 001, texture parameter r = 0.910(9).
Crystal data top
C29H32LiN3O7S2V = 3106.11 (17) Å3
Mr = 605.66Z = 4
Monoclinic, P21/cSynchrotron radiation, λ = 0.52000(1) Å
a = 9.2918 (3) ŵ = 0.12 mm1
b = 23.0117 (7) ÅT = 295 K
c = 15.2798 (5) Åcylinder, 15 × 0.3 mm
β = 108.063 (2)°
Data collection top
ESRF powder
diffractometer
Scan method: continuous
Specimen mounting: Specimen was sealed in a 0.3 mm diameter borosilicate glass capillary2θmin = 3.024°, 2θmax = 23.024°, 2θstep = 0.004°
Data collection mode: transmission
Refinement top
Rp = 0.0445001 data points
Rwp = 0.055213 parameters
Rexp = 0.027124 restraints
χ2 = 3.920H-atom parameters not refined
Special details top

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.

Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Å2) top
xyzUiso*/Ueq
C10.7423 (14)0.2958 (5)0.0474 (9)0.034 (5)*
H10.68200.31190.07960.050*
C20.6752 (17)0.2707 (6)0.0392 (9)0.034 (5)*
C30.7670 (18)0.2493 (6)0.0888 (9)0.034 (1)*
H30.72330.23670.14900.050*
C40.9248 (17)0.2466 (6)0.0486 (9)0.034 (5)*
H40.98390.22660.07780.050*
C50.9926 (18)0.2743 (6)0.0363 (10)0.034 (5)*
C60.9004 (18)0.2965 (5)0.0855 (8)0.034 (5)*
H60.94440.31180.14400.050*
C71.1629 (17)0.2778 (6)0.0743 (8)0.034 (5)*
H7A1.20690.26050.03140.050*
H7B1.19680.25730.13180.050*
H7C1.19320.31770.08380.050*
S80.4794 (8)0.2611 (3)0.0808 (4)0.082 (8)*
N90.4078 (16)0.3236 (6)0.1250 (9)0.034 (5)*
H9B0.41870.34690.07940.050*
C100.4563 (19)0.3539 (10)0.1906 (13)0.034 (5)*
C110.5057 (17)0.3253 (6)0.2584 (10)0.034 (5)*
H110.51100.28490.25780.050*
C120.5464 (16)0.3558 (7)0.3258 (8)0.034 (5)*
H120.57730.33580.36970.050*
C130.5407 (14)0.4169 (6)0.3274 (8)0.034 (5)*
H130.57290.43750.37020.050*
C140.4865 (17)0.4461 (6)0.2645 (10)0.034 (5)*
H140.47220.48610.26980.050*
C150.4524 (16)0.4160 (7)0.1922 (9)0.034 (5)*
C160.4053 (16)0.4516 (6)0.1269 (9)0.034 (5)*
H160.40690.49180.13250.050*
N170.3599 (12)0.4289 (4)0.0593 (7)0.034 (5)*
C180.2904 (15)0.4635 (6)0.0021 (10)0.034 (5)*
C190.2885 (15)0.4413 (6)0.0825 (10)0.034 (5)*
H190.33210.40520.10190.050*
C200.221 (2)0.4727 (9)0.1389 (12)0.034 (5)*
C210.1504 (19)0.5264 (8)0.1077 (12)0.034 (5)*
C220.1619 (14)0.5501 (5)0.0252 (8)0.034 (5)*
H220.13020.58800.00900.050*
C230.2201 (15)0.5173 (6)0.0324 (7)0.034 (5)*
H230.21260.53080.09090.050*
O240.4429 (12)0.2225 (4)0.1593 (6)0.034 (5)*
O250.4152 (13)0.2436 (5)0.0105 (8)0.034 (5)*
O260.2132 (11)0.4505 (4)0.2206 (6)0.034 (5)*
O270.0917 (12)0.5572 (5)0.1652 (7)0.034 (5)*
C280.0445 (15)0.6164 (7)0.1523 (8)0.034 (5)*
H28A0.03050.62130.09240.050*
H28B0.13020.64120.15540.050*
C290.0243 (15)0.6328 (6)0.2297 (9)0.034 (5)*
H29A0.04080.67440.23000.050*
H29B0.12050.61320.21980.050*
O300.0807 (11)0.6149 (4)0.3146 (6)0.034 (5)*
C310.0385 (15)0.6308 (6)0.3933 (9)0.034 (5)*
H31A0.06290.61710.38700.050*
H31B0.04070.67270.40040.050*
C320.1550 (16)0.6018 (7)0.4778 (8)0.034 (5)*
H32A0.25380.61960.48960.050*
H32B0.12310.60610.53220.050*
O330.1609 (10)0.5421 (4)0.4556 (6)0.034 (5)*
C340.2534 (15)0.5072 (7)0.5275 (8)0.034 (5)*
H34A0.21800.50880.58080.050*
H34B0.35730.52060.54530.050*
C350.2422 (15)0.4441 (6)0.4895 (9)0.034 (5)*
H35A0.32110.42000.52940.050*
H35B0.14470.42720.48570.050*
O360.2598 (11)0.4479 (4)0.3997 (6)0.034 (5)*
C370.2527 (15)0.3924 (6)0.3568 (9)0.034 (5)*
H37A0.15170.37620.34320.050*
H37B0.32380.36580.39730.050*
C380.2931 (16)0.4013 (6)0.2667 (10)0.034 (5)*
H38A0.40120.40730.28070.050*
H38B0.26490.36710.22780.050*
S390.2921 (5)0.3885 (2)0.2488 (3)0.073 (8)*
C400.1545 (16)0.4374 (6)0.2745 (9)0.053 (11)*
N410.0681 (14)0.4732 (5)0.2815 (7)0.053 (11)*
Li420.115 (3)0.5193 (11)0.2887 (16)0.053 (11)*
Geometric parameters (Å, º) top
S8—O241.442 (11)C18—C191.40 (2)
S8—O251.442 (14)C19—C201.41 (2)
S8—N91.643 (15)C20—C211.42 (3)
S8—C21.742 (18)C21—C221.40 (2)
S39—C401.656 (15)C22—C231.395 (18)
O26—C201.37 (2)C28—C291.552 (19)
O26—C381.417 (17)C31—C321.555 (19)
O26—Li422.24 (3)C34—C351.55 (2)
O27—C211.36 (2)C37—C381.55 (2)
O27—C281.42 (2)C1—H10.93
O27—Li422.03 (3)C3—H30.93
O30—C291.424 (16)C4—H40.93
O30—C311.423 (17)C6—H60.93
O30—Li422.27 (3)C7—H7A0.96
O33—C321.421 (18)C7—H7B0.96
O33—C341.419 (16)C7—H7C0.96
O33—Li422.50 (3)C11—H110.93
O36—C351.433 (16)C12—H120.93
O36—C371.425 (16)C13—H130.93
O36—Li422.44 (3)C14—H140.93
N9—C101.40 (2)C16—H160.93
N17—C161.338 (18)C19—H190.93
N17—C181.471 (18)C22—H220.93
N41—C401.136 (19)C23—H230.93
N41—Li421.98 (3)C28—H28A0.97
N9—H9B0.86C28—H28B0.97
C1—C21.399 (18)C29—H29A0.97
C1—C61.41 (2)C29—H29B0.97
C2—C31.40 (2)C31—H31A0.97
C3—C41.40 (2)C31—H31B0.97
C4—C51.40 (2)C32—H32A0.97
C5—C61.40 (2)C32—H32B0.97
C5—C71.51 (2)C34—H34A0.97
C10—C111.42 (2)C34—H34B0.97
C10—C151.43 (3)C35—H35A0.97
C11—C121.39 (2)C35—H35B0.97
C12—C131.41 (2)C37—H37A0.97
C13—C141.39 (2)C37—H37B0.97
C14—C151.42 (2)C38—H38A0.97
C15—C161.46 (2)C38—H38B0.97
C18—C231.41 (2)
O24—S8—O25113.5 (8)H7A—C7—H7B109
O24—S8—N9103.7 (7)C5—C7—H7A109
O24—S8—C2109.6 (8)C5—C7—H7B109
O25—S8—N9110.1 (8)C5—C7—H7C109
O25—S8—C2112.8 (8)H7B—C7—H7C109
N9—S8—C2106.5 (8)C10—C11—H11119
C20—O26—C38125.5 (13)C12—C11—H11119
C20—O26—Li42108.2 (12)C13—C12—H12120
C38—O26—Li42123.9 (10)C11—C12—H12120
C21—O27—C28125.2 (12)O33—C32—H32B110
C21—O27—Li42115.1 (13)H32A—C32—H32B109
C28—O27—Li42118.5 (11)C31—C32—H32B110
C29—O30—C31113.8 (11)C31—C32—H32A110
C29—O30—Li42102.5 (9)C35—C34—H34B110
C31—O30—Li42119.1 (10)C35—C34—H34A110
C32—O33—C34115.0 (10)O33—C34—H34B110
C35—O36—C37112.7 (10)O33—C34—H34A110
C35—O36—Li42120.1 (10)H34A—C34—H34B109
C37—O36—Li42110.3 (9)O36—C35—H35A110
S8—N9—C10123.2 (13)O36—C35—H35B110
C16—N17—C18122.9 (11)C34—C35—H35A110
C40—N41—Li42165.3 (14)C34—C35—H35B110
C10—N9—H9B106.45H35A—C35—H35B109
S8—N9—H9B106.60O36—C37—H37A110
C2—C1—C6119.8 (13)O36—C37—H37B110
S8—C2—C3119.9 (11)C38—C37—H37A110
S8—C2—C1120.4 (12)C12—C13—H13120
C1—C2—C3119.4 (14)C14—C13—H13120
C18—C23—C22120.0 (11)C15—C14—H14119
O27—C28—C29108.2 (11)C13—C14—H14119
O30—C29—C28107.1 (11)N17—C16—H16119
O30—C31—C32106.8 (11)C15—C16—H16119
O33—C32—C31106.3 (10)C18—C19—H19119
C34—O33—Li42122.7 (12)C20—C19—H19119
C32—O33—Li42116.2 (11)C23—C22—H22120
O33—C34—C35106.7 (10)C21—C22—H22120
O36—C35—C34107.0 (10)C18—C23—H23120
O36—C37—C38107.4 (11)C22—C23—H23120
O26—C38—C37108.5 (11)O27—C28—H28A110
S39—C40—N41171.5 (13)O27—C28—H28B110
C2—C3—C4120.5 (12)H28A—C28—H28B108
C3—C4—C5119.7 (14)C29—C28—H28B110
C6—C5—C7121.1 (12)C29—C28—H28A110
C4—C5—C7119.7 (14)O30—C29—H29B110
C4—C5—C6119.1 (15)O30—C29—H29A110
C1—C6—C5120.7 (12)C28—C29—H29B110
N9—C10—C11122.5 (18)H29A—C29—H29B108
N9—C10—C15119.5 (16)C28—C29—H29A110
C11—C10—C15118.0 (16)C32—C31—H31A110
C10—C11—C12121.8 (15)C32—C31—H31B110
C11—C12—C13119.9 (13)O30—C31—H31A110
C12—C13—C14119.6 (12)O30—C31—H31B110
C13—C14—C15121.3 (13)H31A—C31—H31B109
C10—C15—C14119.1 (14)O33—C32—H32A110
C10—C15—C16124.4 (14)C38—C37—H37B110
C14—C15—C16116.4 (13)H37A—C37—H37B108
N17—C16—C15122.4 (12)C37—C38—H38A110
C19—C18—C23119.1 (13)C37—C38—H38B110
N17—C18—C23121.6 (12)O26—C38—H38B110
N17—C18—C19119.2 (12)O26—C38—H38A110
C18—C19—C20121.2 (14)H38A—C38—H38B108
O26—C20—C21118.6 (16)O30—Li42—N41111.3 (13)
O26—C20—C19122.0 (16)O36—Li42—N4187.7 (10)
C19—C20—C21119.2 (16)O27—Li42—O3076.3 (9)
O27—C21—C22122.0 (15)O27—Li42—O36144.2 (14)
O27—C21—C20118.4 (15)O27—Li42—N41109.5 (13)
C20—C21—C22119.0 (16)O30—Li42—O36127.4 (11)
C21—C22—C23120.6 (12)O26—Li42—O2779.1 (9)
C2—C1—H1120O26—Li42—O30149.5 (13)
C6—C1—H1120O26—Li42—O3668.4 (8)
C2—C3—H3120O26—Li42—N4193.7 (11)
C4—C3—H3120N41—Li42—O3392.7 (10)
C5—C4—H4120O27—Li42—O33142.1 (14)
C3—C4—H4120O26—Li42—O33131.1 (12)
C5—C6—H6120O30—Li42—O3367.0 (9)
C1—C6—H6120O36—Li42—O3363.5 (8)
H7A—C7—H7C110
O24—S8—N9—C1063.0 (16)Li42—O36—C37—C3849.8 (14)
O25—S8—N9—C10175.3 (14)C35—O36—Li42—O26164.2 (10)
C2—S8—N9—C1052.6 (16)Li42—O36—C35—C3447.8 (15)
O24—S8—C2—C38.8 (14)C35—O36—C37—C38173.0 (11)
O25—S8—C2—C3136.3 (12)C37—O36—C35—C34179.6 (11)
N9—S8—C2—C3102.8 (12)C35—O36—Li42—O27170 (2)
N9—S8—C2—C182.2 (12)C37—O36—Li42—O2630.6 (11)
O24—S8—C2—C1166.2 (10)C35—O36—Li42—N4169.3 (13)
O25—S8—C2—C138.7 (14)C37—O36—Li42—N4164.3 (12)
C20—O26—Li42—N41115.6 (12)S8—N9—C10—C1134 (2)
C20—O26—Li42—O276.4 (14)S8—N9—C10—C15148.2 (14)
C20—O26—Li42—O3030 (3)C16—N17—C18—C19160.7 (14)
C20—O26—Li42—O36158.4 (11)C18—N17—C16—C15170.6 (13)
Li42—O26—C20—C19175.2 (16)C16—N17—C18—C2322 (2)
C38—O26—Li42—O30133 (2)C6—C1—C2—S8171.7 (10)
C38—O26—Li42—O364.9 (13)C6—C1—C2—C33.4 (19)
C38—O26—Li42—N4181.1 (14)C2—C1—C6—C52.7 (18)
C38—O26—Li42—O27169.7 (11)C1—C2—C3—C47 (2)
C38—O26—C20—C1912 (2)S8—C2—C3—C4167.9 (11)
Li42—O26—C38—C3719.1 (17)C2—C3—C4—C510 (2)
Li42—O26—C20—C219 (2)C3—C4—C5—C69 (2)
C20—O26—C38—C37179.5 (14)C3—C4—C5—C7172.9 (13)
C38—O26—C20—C21171.7 (15)C7—C5—C6—C1176.6 (12)
C28—O27—C21—C20167.2 (15)C4—C5—C6—C15.7 (19)
C28—O27—Li42—O26171.7 (11)N9—C10—C15—C14173.4 (15)
C28—O27—Li42—N4198.1 (15)N9—C10—C15—C162 (3)
C28—O27—C21—C224 (2)C11—C10—C15—C145 (2)
C21—O27—C28—C29176.4 (14)C11—C10—C15—C16179.7 (15)
Li42—O27—C21—C200 (2)N9—C10—C11—C12176.6 (15)
C28—O27—Li42—O3010.0 (14)C15—C10—C11—C121 (2)
C21—O27—Li42—N4193.4 (16)C10—C11—C12—C131 (2)
C21—O27—Li42—O30158.5 (12)C11—C12—C13—C144 (2)
C21—O27—Li42—O263.3 (14)C12—C13—C14—C157 (2)
Li42—O27—C28—C2916.4 (17)C13—C14—C15—C108 (2)
C28—O27—Li42—O36147.0 (19)C13—C14—C15—C16176.3 (14)
C21—O27—Li42—O3621 (3)C10—C15—C16—N170 (2)
Li42—O27—C21—C22171.3 (15)C14—C15—C16—N17175.3 (14)
C31—O30—Li42—N4156.7 (15)N17—C18—C23—C22177.2 (12)
C29—O30—Li42—O2736.0 (11)N17—C18—C19—C20178.7 (14)
Li42—O30—C31—C3252.6 (15)C23—C18—C19—C202 (2)
C31—O30—Li42—O27162.6 (10)C19—C18—C23—C226 (2)
C29—O30—Li42—O2673 (3)C18—C19—C20—O26177.8 (15)
C31—O30—Li42—O26160 (2)C18—C19—C20—C212 (3)
C29—O30—C31—C32173.7 (11)O26—C20—C21—C22178.0 (15)
C29—O30—Li42—O36174.1 (14)C19—C20—C21—C226 (3)
C31—O30—Li42—O3647 (2)O26—C20—C21—O277 (3)
C29—O30—Li42—N4169.9 (13)C19—C20—C21—O27177.0 (15)
Li42—O30—C29—C2854.3 (13)O27—C21—C22—C23179.0 (14)
C31—O30—C29—C28175.7 (11)C20—C21—C22—C2310 (2)
C32—O33—C34—C35179.4 (11)C21—C22—C23—C1810 (2)
C34—O33—C32—C31175.4 (11)O27—C28—C29—O3049.4 (14)
C35—O36—Li42—O3046 (2)O30—C31—C32—O3351.2 (14)
C37—O36—Li42—O2757 (3)O33—C34—C35—O3645.8 (14)
C37—O36—Li42—O30179.6 (14)O36—C37—C38—O2644.9 (14)

Experimental details

(CuL2)(LiNCS)
Crystal data
Chemical formulaC56H62CuN4O14S2C29H32LiN3O7S2
Mr1142.79605.66
Crystal system, space groupMonoclinic, P21/cMonoclinic, P21/c
Temperature (K)295295
a, b, c (Å)19.0356 (6), 17.4332 (6), 17.4180 (6)9.2918 (3), 23.0117 (7), 15.2798 (5)
β (°) 113.824 (3) 108.063 (2)
V3)5287.7 (3)3106.11 (17)
Z44
Radiation typeSynchrotron, λ = 0.51966(1) ÅSynchrotron, λ = 0.52000(1) Å
µ (mm1)0.300.12
Specimen shape, size (mm)Cylinder, 15 × 0.3Cylinder, 15 × 0.3
Data collection
DiffractometerESRF powder
diffractometer
ESRF powder
diffractometer
Specimen mountingSpecimen was sealed in a 0.3 mm diameter borosilicate glass capillarySpecimen was sealed in a 0.3 mm diameter borosilicate glass capillary
Data collection modeTransmissionTransmission
Scan methodContinuousContinuous
2θ values (°)2θmin = 1.017 2θmax = 22.014 2θstep = 0.0032θmin = 3.024 2θmax = 23.024 2θstep = 0.004
Refinement
R factors and goodness of fitRp = 0.046, Rwp = 0.063, Rexp = 0.048, χ2 = 1.700Rp = 0.044, Rwp = 0.055, Rexp = 0.027, χ2 = 3.920
No. of data points70005001
No. of parameters277213
No. of restraints233124
H-atom treatmentH-atom parameters not refinedH-atom parameters not refined

Computer programs: LSPAID (Visser et al., 1986), MRIA (Zlokazov et al., 1992), MRIA, PLATON (Spek, 2003).

 

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