Copper cluster complex-catalyzed C–S bond formation
Chang Liao, Nien-Chi; Basha, R. Sidick; Shih, Bo-Hao; Liu, Chia-Chun; Wang, Miao-Han; Lin, Po-Heng; Lee, Chin-Fa; Catalysis Science & Technology 14 (2024) 6609–6620; doi:10.1039/D4CY00968A

data_1572695
_publ_section_title
;
 Copper cluster complex-catalyzed C--S bond formation
;
_journal_issue                   22
_journal_name_full               'Catalysis Science &amp; Technology'
_journal_page_first              6609
_journal_page_last               6620
_journal_paper_doi               10.1039/D4CY00968A
_journal_volume                  14
_journal_year                    2024
_chemical_formula_moiety         'C80 H88 Cu8 N22 O30, 2(N O3)'
_chemical_formula_sum            'C80 H88 Cu8 N24 O36'
_chemical_formula_weight         2470.06
_space_group_crystal_system      monoclinic
_space_group_IT_number           15
_space_group_name_Hall           '-C 2yc'
_space_group_name_H-M_alt        'C 1 2/c 1'
_atom_sites_solution_hydrogens   mixed
_audit_creation_date             2022-12-18
_audit_creation_method
;
Olex2 1.2-ac3
(compiled 2017.02.24 svn.r3390 for Rigaku Oxford Diffraction, GUI svn.r5318)
;
_audit_update_record
;
2022-12-20 deposited with the CCDC.	2024-09-26 downloaded from the CCDC.
;
_cell_angle_alpha                90
_cell_angle_beta                 114.638(3)
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   23.249(4)
_cell_length_b                   24.663(4)
_cell_length_c                   19.015(3)
_cell_measurement_reflns_used    26315
_cell_measurement_temperature    200(2)
_cell_measurement_theta_max      25.04
_cell_measurement_theta_min      2.03
_cell_volume                     9910(3)
_computing_molecular_graphics    'Olex2 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 (Dolomanov et al., 2009)'
_computing_structure_refinement  'XL (Sheldrick, 2008)'
_diffrn_ambient_temperature      200(2)
_diffrn_measured_fraction_theta_full 0.995
_diffrn_measured_fraction_theta_max 0.995
_diffrn_measurement_device_type  'Bruker APEX-II CCD'
_diffrn_measurement_method       '\f and \w scans'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0927
_diffrn_reflns_av_unetI/netI     0.1222
_diffrn_reflns_Laue_measured_fraction_full 0.995
_diffrn_reflns_Laue_measured_fraction_max 0.995
_diffrn_reflns_limit_h_max       14
_diffrn_reflns_limit_h_min       -27
_diffrn_reflns_limit_k_max       29
_diffrn_reflns_limit_k_min       -26
_diffrn_reflns_limit_l_max       22
_diffrn_reflns_limit_l_min       -22
_diffrn_reflns_number            26334
_diffrn_reflns_point_group_measured_fraction_full 0.995
_diffrn_reflns_point_group_measured_fraction_max 0.995
_diffrn_reflns_theta_full        25.041
_diffrn_reflns_theta_max         25.041
_diffrn_reflns_theta_min         1.269
_exptl_absorpt_coefficient_mu    1.778
_exptl_absorpt_correction_T_max  0.9653
_exptl_absorpt_correction_T_min  0.5670
_exptl_absorpt_correction_type   multi-scan
_exptl_crystal_colour            green(dark)
_exptl_crystal_density_diffrn    1.655
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       prism
_exptl_crystal_F_000             5024
_exptl_crystal_size_max          0.36
_exptl_crystal_size_mid          0.04
_exptl_crystal_size_min          0.02
_platon_squeeze_details
;
TITL CH17587A OLEX2: imported from CIF
CELL   23.2490   24.6630   19.0150     90.00    114.64     90.00
SPGR C2/c
C101 0.225 0.129 0.475 !       4.03 eA-3
C102 0.251 0.328 0.486 !       2.67 eA-3
C103 0.759 0.198 0.061 !       2.64 eA-3
C104 0.256 0.233 0.420 !       2.31 eA-3
C105 0.734 0.210 0.933 !       2.28 eA-3
C106 0.779 0.202-0.004 !       2.03 eA-3
C107 0.287 0.198 0.550 !       1.67 eA-3
C108 0.188 0.222 0.449 !       1.63 eA-3
C109 0.287 0.220 0.456 !       1.61 eA-3
Q110 0.157 0.009 0.830 !       1.52 eA-3
C111 0.203 0.259 0.467 !       1.48 eA-3
C112 0.221 0.316 0.519 !       1.47 eA-3
Q113 0.484 0.502 0.747 !       1.42 eA-3
C114 0.182 0.767 1.003 !       1.40 eA-3
C115 0.682 0.267 0.003 !       1.40 eA-3
Q116 0.205 0.198 0.422 !       1.37 eA-3
C117 0.841 0.146 0.050 !       1.29 eA-3
C118 0.250 0.230 0.504 !       1.29 eA-3
Q119 0.758 0.139 0.090 !       1.28 eA-3
C120 0.733 0.371 0.032 !       1.28 eA-3
C121 0.780 0.258 0.076 !       1.27 eA-3
Q122 0.286 0.155 0.562 !       1.25 eA-3
C123 0.210 0.216 0.439 !       1.22 eA-3
Q124 0.165 0.102 0.390 !       1.22 eA-3
Q125 0.264 0.010 0.483 !       1.19 eA-3
Q126 0.764 0.510 0.483 !       1.19 eA-3
Q127 0.163 0.255 0.484 !       1.19 eA-3
Q128 0.784 0.095 0.108 !       1.16 eA-3
Q129 0.697 0.243 0.905 !       1.14 eA-3
Q130 0.839 0.358 0.183 !       1.14 eA-3
Q131 0.767 0.387 0.018 !       1.13 eA-3
C132 0.213 0.353 0.486 !       1.13 eA-3
Q133 0.166 0.322 0.419 !       1.12 eA-3
C134 0.243 0.260 0.531 !       1.12 eA-3
Q135 0.783 0.176 0.943 !       1.11 eA-3
Q136 0.310 0.414 0.531 !       1.10 eA-3
Q137 0.609 0.315 0.328 !       1.10 eA-3
Q138 0.865 0.227 0.058 !       1.10 eA-3
Q139 0.340 0.323 0.590 !       1.10 eA-3
Q140 0.765 0.223 0.158 !       1.10 eA-3
Q141 0.187 0.246 0.342 !       1.09 eA-3
Q142 0.203 0.196 0.362 !       1.09 eA-3
Q143 0.229 0.385 0.404 !       1.09 eA-3
Q144 0.196 0.335 0.390 !       1.09 eA-3
Q145 0.805 0.310 0.347 !       1.09 eA-3
Q146 0.115 0.293 0.105 !       1.09 eA-3
Q147 0.828 0.311-0.003 !       1.07 eA-3
Q148 0.250 0.099 0.422 !       1.06 eA-3
C149 0.181 0.263 0.438 !       1.06 eA-3
Q150 0.538 0.361 0.876 !       1.06 eA-3
Q151 0.148 0.252 0.279 !       1.05 eA-3
Q152 0.361 0.282 0.747 !       1.03 eA-3
Q153 0.704 0.235 0.095 !       1.02 eA-3
Q154 1.000 0.273 0.252 !       1.02 eA-3
Q155 0.768 0.051 0.020 !       1.01 eA-3
Q156 0.168 0.363 0.440 !       1.00 eA-3
Q157 0.166 0.249 0.420 !       1.00 eA-3
Q158 0.772 0.366 0.940 !       0.99 eA-3
Q159 0.474 0.305 0.174 !       0.98 eA-3
Q160 0.696 0.109 0.654 !       0.98 eA-3
Q161 0.211 0.424 0.356 !       0.98 eA-3
Q162 0.905 0.234 0.185 !       0.98 eA-3
Q163 0.689 0.210 0.884 !       0.98 eA-3
Q164 0.257 0.327 0.641 !       0.97 eA-3
Q165 0.380 0.320 0.579 !       0.96 eA-3
Q166 0.312 0.181 0.519 !       0.96 eA-3
Q167 0.794 0.350 0.296 !       0.96 eA-3
Q168 0.203 0.352 0.153 !       0.96 eA-3
Q169 0.688 0.128 0.845 !       0.96 eA-3
Q170 0.460 0.181 0.797 !       0.93 eA-3
Q171 0.376 0.499 0.985 !       0.92 eA-3
Q172 0.335 0.283 0.621 !       0.92 eA-3
Q173 0.798 0.436 0.973 !       0.92 eA-3
Q174 0.797 0.281 0.139 !       0.91 eA-3
Q175 0.632 0.299 0.982 !       0.91 eA-3
Q176 0.220 0.482 0.075 !       0.90 eA-3
Q177 0.484 0.266 0.749 !       0.90 eA-3
Q178 0.898 0.196 0.277 !       0.89 eA-3
Q179 0.148 0.071-0.003 !       0.88 eA-3
Q180 1.002 0.280 0.703 !       0.88 eA-3
Q181 0.062 0.268 0.247 !       0.88 eA-3
Q182 0.687 0.013-0.001 !       0.88 eA-3
Q183 0.818 0.460 0.404 !       0.88 eA-3
Q184 0.039 0.243 0.267 !       0.87 eA-3
Q185 0.225 0.469 0.472 !       0.87 eA-3
Q186 1.000 0.180 0.253 !       0.87 eA-3
Q187 0.143 0.233 0.503 !       0.87 eA-3
Q188 0.826 0.142 0.126 !       0.87 eA-3
Q189 0.359 0.212 0.715 !       0.86 eA-3
Q190 0.859 0.712 0.715 !       0.86 eA-3
Q191 0.124 0.236 0.217 !       0.86 eA-3
Q192 0.915 0.315 0.255 !       0.86 eA-3
Q193 0.182 0.278 0.579 !       0.86 eA-3
Q194 0.782 0.476 0.940 !       0.85 eA-3
Q195 0.290 0.348 0.637 !       0.85 eA-3
Q196 0.790 0.848 0.637 !       0.85 eA-3
Q197 0.647 0.275 0.563 !       0.85 eA-3
Q198 0.844 0.166 0.985 !       0.85 eA-3
Q199 0.297 0.180 0.745 !       0.85 eA-3
;
_refine_diff_density_max         1.112
_refine_diff_density_min         -0.965
_refine_diff_density_rms         0.238
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   0.990
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     654
_refine_ls_number_reflns         8743
_refine_ls_number_restraints     72
_refine_ls_restrained_S_all      0.993
_refine_ls_R_factor_all          0.1590
_refine_ls_R_factor_gt           0.0713
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'w=1/[\s^2^(Fo^2^)+(0.1451P)^2^] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1880
_refine_ls_wR_factor_ref         0.2546
_reflns_Friedel_coverage         0.000
_reflns_number_gt                4422
_reflns_number_total             8743
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            d4cy00968a2.cif
_cod_data_source_block           ch17587a_sq
_cod_depositor_comments
'Adding full bibliography for 1572694--1572696.cif.'
_cod_database_code               1572695
_shelx_shelxl_version_number     2018/3
_shelx_estimated_absorpt_t_max   0.965
_shelx_estimated_absorpt_t_min   0.567
_olex2_refinement_description
;
1. Fixed Uiso
 At 1.2 times of:
  All N(H) groups
 At 1.5 times of:
  All C(H,H,H) groups
2. Uiso/Uaniso restraints and constraints
N10 \\sim C39: within 2A with sigma of 0.01 and sigma for terminal atoms of 0.02
C40 \\sim N10: within 2A with sigma of 0.01 and sigma for terminal atoms of 0.02
C38 \\sim N10: within 2A with sigma of 0.01 and sigma for terminal atoms of 0.02
O12 \\sim C38: within 2A with sigma of 0.01 and sigma for terminal atoms of 0.02
O18' \\sim N11': within 2A with sigma of 0.01 and sigma for terminal atoms of
0.02
O17' \\sim N11': within 2A with sigma of 0.01 and sigma for terminal atoms of
0.02
O16' \\sim N11': within 2A with sigma of 0.01 and sigma for terminal atoms of
0.02
O16 \\sim N11: within 2A with sigma of 0.01 and sigma for terminal atoms of 0.02
O17 \\sim N11: within 2A with sigma of 0.01 and sigma for terminal atoms of 0.02
O18 \\sim N11: within 2A with sigma of 0.01 and sigma for terminal atoms of 0.02
Uanis(N11) \\sim Ueq: with sigma of 0.01 and sigma for terminal atoms of 0.02
Uanis(O16') \\sim Ueq: with sigma of 0.01 and sigma for terminal atoms of 0.02
3. Others
 Fixed Sof: N11(0.55) N11'(0.45) O16(0.55) O17(0.55) O18(0.55) O16'(0.45)
 O17'(0.45) O18'(0.45)
 Fixed Uiso: H3A(0.127) H3B(0.127) H3C(0.127) H4(0.073) H5(0.078) H6(0.072)
 H8(0.066) H10(0.047) H12(0.057) H13(0.067) H14(0.061) H16A(0.124) H16B(0.124)
 H16C(0.124) H20A(0.097) H20B(0.097) H20C(0.097) H21(0.076) H22(0.078)
 H23(0.072) H25(0.06) H27(0.055) H29(0.073) H30(0.077) H31(0.073) H35(0.082)
 H36A(0.156) H36B(0.156) H36C(0.156) H37A(0.156) H37B(0.156) H37C(0.156)
 H38(0.232) H39A(0.148) H39B(0.148) H39C(0.148) H40A(0.185) H40B(0.185)
 H40C(0.185)
 Fixed X: H3A(0.511901) H3B(0.528801) H3C(0.5842) H4(0.6316) H5(0.690201)
 H6(0.6749) H8(0.619901) H10(0.397901) H12(0.320801) H13(0.2649) H14(0.2885)
 H16A(0.365701) H16B(0.303901) H16C(0.368501) H20A(0.685801) H20B(0.695701)
 H20C(0.7071) H21(0.679) H22(0.653901) H23(0.565901) H25(0.4819) H27(0.2753)
 H29(0.255) H30(0.2647) H31(0.3204) H35(0.454) H36A(0.353601) H36B(0.3738)
 H36C(0.4267) H37A(0.322701) H37B(0.372399) H37C(0.320001) H38(0.4526)
 H39A(0.563201) H39B(0.5143) H39C(0.572) H40A(0.5241) H40B(0.5107) H40C(0.4532)
 N11(0.3254) N11'(0.3255)
 Fixed Y: H3A(-0.224001) H3B(-0.215601) H3C(-0.2193) H4(-0.176099) H5(-
 0.116199) H6(-0.025401) H8(0.0516) H10(0.073) H12(0.0716) H13(0.108701)
 H14(0.197301) H16A(0.322901) H16B(0.285399) H16C(0.2627) H20A(0.193901)
 H20B(0.253901) H20C(0.242) H21(0.311901) H22(0.402399) H23(0.4409) H25(0.4407)
 H27(0.4713) H29(0.5498) H30(0.641901) H31(0.6975) H35(-0.0791) H36A(-0.146199)
 H36B(-0.153601) H36C(-0.1525) H37A(-0.0734) H37B(-0.024501) H37C(-0.027401)
 H38(0.6043) H39A(0.5784) H39B(0.5301) H39C(0.5398) H40A(0.661302)
 H40B(0.668001) H40C(0.658001)
 Fixed Z: H3A(0.392) H3B(0.481999) H3C(0.4531) H4(0.563301) H5(0.662301)
 H6(0.6485) H8(0.5782) H10(0.2244) H12(0.098101) H13(-0.0214) H14(-0.0466)
 H16A(-0.019601) H16B(-0.0497) H16C(-0.0493) H20A(0.2284) H20B(0.2637)
 H20C(0.1878) H21(0.119101) H22(0.0827) H23(0.0899) H25(0.127301) H27(0.2701)
 H29(0.325601) H30(0.3525) H31(0.3024) H35(0.312) H36A(0.1446) H36B(0.235499)
 H36C(0.2023) H37A(0.0991) H37B(0.123001) H37C(0.1569) H38(0.166201)
 H39A(0.061301) H39B(0.050301) H39C(0.1327) H40A(0.068201) H40B(0.143801)
 H40C(0.061301)
4.a Aromatic/amide H refined with riding coordinates:
 N2(H2), N7(H7)
4.b Fitted hexagon refined as free rotating group:
 C1(C2,C4,C5,C6,C7), C17(C11,C12,C13,C14,C15), C18(C24,C23,C22,C21,C19),
 C29(C28,C34,C32,C31,C30)
4.c Idealised Me refined as rotating group:
 C33(H33A,H33B,H33C)
;
_platon_squeeze_void_probe_radius 1.20
_olex2_submission_special_instructions 'No special instructions were received'