Accelerating the Insertion Reactions of (NHC)Cu-H via Remote Ligand Functionalization
Speelman, Amy L.; Tran, Ba; Erickson, Jeremy D.; Vasiliu, Monica; Dixon, David A.; Bullock, R. Morris; Chemical Science  (2021) –; doi:10.1039/D1SC01911B

data_1564269
_publ_section_title
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 Accelerating the Insertion Reactions of (NHC)Cu-H via Remote Ligand
 Functionalization
;
_journal_name_full               'Chemical Science'
_journal_paper_doi               10.1039/D1SC01911B
_journal_year                    2021
_chemical_formula_moiety         'C71 H60 Cl Cu N2, C H2 Cl2'
_chemical_formula_sum            'C72 H62 Cl3 Cu N2'
_chemical_formula_weight         1125.12
_chemical_properties_physical    Air-sensitive,Moisture-sensitive
_space_group_crystal_system      monoclinic
_space_group_IT_number           14
_space_group_name_Hall           '-P 2ybc'
_space_group_name_H-M_alt        'P 1 21/c 1'
_atom_sites_solution_hydrogens   geom
_audit_creation_date             2020-11-03
_audit_creation_method
;
Olex2 1.3-alpha
(compiled 2020.10.28 svn.r5b043f8a for OlexSys, GUI svn.r6176)
;
_audit_update_record
;
2020-12-11 deposited with the CCDC.	2021-07-23 downloaded from the CCDC.
;
_cell_angle_alpha                90
_cell_angle_beta                 91.726(4)
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   12.9250(11)
_cell_length_b                   18.7591(16)
_cell_length_c                   24.0140(19)
_cell_measurement_reflns_used    9134
_cell_measurement_temperature    100.0
_cell_measurement_theta_max      27.65
_cell_measurement_theta_min      2.527
_cell_volume                     5819.8(8)
_computing_cell_refinement       'SAINT v8.37A (Bruker, 2015)'
_computing_data_reduction        'SAINT v8.37A (Bruker, 2015)'
_computing_molecular_graphics    'Olex2 1.3-alpha (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 1.3-alpha (Dolomanov et al., 2009)'
_computing_structure_refinement  'SHELXL 2018/3 (Sheldrick, 2015)'
_diffrn_ambient_temperature      100.0
_diffrn_measured_fraction_theta_full 1.000
_diffrn_measured_fraction_theta_max 0.989
_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  0.1010
_diffrn_reflns_av_unetI/netI     0.0528
_diffrn_reflns_Laue_measured_fraction_full 1.000
_diffrn_reflns_Laue_measured_fraction_max 0.989
_diffrn_reflns_limit_h_max       16
_diffrn_reflns_limit_h_min       -16
_diffrn_reflns_limit_k_max       24
_diffrn_reflns_limit_k_min       -24
_diffrn_reflns_limit_l_max       31
_diffrn_reflns_limit_l_min       -30
_diffrn_reflns_number            159770
_diffrn_reflns_point_group_measured_fraction_full 1.000
_diffrn_reflns_point_group_measured_fraction_max 0.989
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         27.698
_diffrn_reflns_theta_min         1.914
_exptl_absorpt_coefficient_mu    0.558
_exptl_absorpt_correction_T_max  0.7077
_exptl_absorpt_correction_T_min  0.6148
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
SADABS-2014/5 (Bruker,2014/5) was used for absorption correction.
wR2(int) was 0.1601 before and 0.0985 after correction.
The Ratio of minimum to maximum transmission is 0.8687.
The \l/2 correction factor is 0.00150.
;
_exptl_crystal_colour            'clear colourless'
_exptl_crystal_colour_lustre     clear
_exptl_crystal_colour_primary    colourless
_exptl_crystal_density_diffrn    1.284
_exptl_crystal_description       needle
_exptl_crystal_F_000             2352
_exptl_crystal_size_max          0.16
_exptl_crystal_size_mid          0.08
_exptl_crystal_size_min          0.07
_refine_diff_density_max         1.456
_refine_diff_density_min         -1.402
_refine_diff_density_rms         0.118
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.097
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     705
_refine_ls_number_reflns         13472
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.097
_refine_ls_R_factor_all          0.0958
_refine_ls_R_factor_gt           0.0781
_refine_ls_shift/su_max          0.001
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'w=1/[\s^2^(Fo^2^)+(0.0928P)^2^+27.2452P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.2180
_refine_ls_wR_factor_ref         0.2297
_reflns_Friedel_coverage         0.000
_reflns_number_gt                10973
_reflns_number_total             13472
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            d1sc01911b3.cif
_cod_data_source_block           ba7_a
_cod_database_code               1564269
_shelx_shelxl_version_number     2018/3
_shelx_estimated_absorpt_t_max   0.962
_shelx_estimated_absorpt_t_min   0.916
_olex2_refinement_description
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups, All C(H,H) groups
 At 1.5 times of:
  All C(H,H,H) groups
2.a Ternary CH refined with riding coordinates:
 C10(H10), C25(H25), C59(H59), C44(H44)
2.b Secondary CH2 refined with riding coordinates:
 C23(H23A,H23B), C57(H57A,H57B), C72(H72A,H72B)
2.c Aromatic/amide H refined with riding coordinates:
 C2(H2), C3(H3), C18(H18), C6(H6), C40(H40), C8(H8), C27(H27), C50(H50),
 C67(H67), C46(H46), C42(H42), C16(H16), C65(H65), C47(H47), C68(H68), C22(H22),
  C12(H12), C37(H37), C31(H31), C71(H71), C33(H33), C56(H56), C55(H55),
 C69(H69), C19(H19), C52(H52), C61(H61), C35(H35), C34(H34), C20(H20), C48(H48),
  C21(H21), C29(H29), C54(H54), C28(H28), C70(H70), C36(H36), C15(H15),
 C14(H14), C63(H63), C13(H13), C64(H64), C30(H30), C49(H49), C62(H62), C53(H53)
2.d Idealised Me refined as rotating group:
 C58(H58A,H58B,H58C), C24(H24A,H24B,H24C)
;
_olex2_submission_special_instructions 'No special instructions were received'