CO<sub>2</sub> hydrosilylation catalyzed by an N-heterocyclic carbene (NHC)-stabilized stannyliumylidene.
Niu, Dechuang; Kostenko, Arseni; Kelly, John A.; Sarkar, Debotra; Xu, Huihui; Inoue, Shigeyoshi; Chemical science 16 (2025) 4014–4022; doi:10.1039/d4sc07116f

data_1573732
_publ_section_title
;
 CO<sub>2</sub> hydrosilylation catalyzed by an N-heterocyclic carbene
 (NHC)-stabilized stannyliumylidene.
;
_journal_issue                   9
_journal_name_full               'Chemical science'
_journal_page_first              4014
_journal_page_last               4022
_journal_paper_doi               10.1039/d4sc07116f
_journal_volume                  16
_journal_year                    2025
_chemical_formula_moiety         'C39 H49 N4 O2 Sn, C32 H12 B F24, C7 H8'
_chemical_formula_sum            'C79 H80 B5 F24 N5 O2 Sn'
_chemical_formula_weight         1760.22
_space_group_crystal_system      triclinic
_space_group_IT_number           2
_space_group_name_Hall           '-P 1'
_space_group_name_H-M_alt        'P -1'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     dual
_audit_creation_date             2023-04-11
_audit_creation_method
;
Olex2 1.5
(compiled 2023.03.06 svn.rbb2c1857 for OlexSys, GUI svn.r6748)
;
_audit_update_record
;
2023-04-11 deposited with the CCDC.	2025-01-16 downloaded from the CCDC.
;
_cell_angle_alpha                92.495(3)
_cell_angle_beta                 102.397(3)
_cell_angle_gamma                112.807(2)
_cell_formula_units_Z            2
_cell_length_a                   15.2450(13)
_cell_length_b                   17.2704(13)
_cell_length_c                   17.6243(14)
_cell_measurement_reflns_used    9316
_cell_measurement_temperature    100(2)
_cell_measurement_theta_max      25.39
_cell_measurement_theta_min      2.55
_cell_volume                     4136.1(6)
_computing_cell_refinement       'SAINT V8.40B (?, 2016)'
_computing_data_reduction        'SAINT V8.40B (?, 2016)'
_computing_molecular_graphics    'Olex2 1.5 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 1.5 (Dolomanov et al., 2009)'
_computing_structure_refinement  'SHELXL 2016/6 (Sheldrick, 2015)'
_computing_structure_solution    'SHELXT 2018/2 (Sheldrick, 2018)'
_diffrn_ambient_temperature      100.00
_diffrn_measured_fraction_theta_full 0.998
_diffrn_measured_fraction_theta_max 0.998
_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  0.0264
_diffrn_reflns_av_unetI/netI     0.0179
_diffrn_reflns_Laue_measured_fraction_full 0.998
_diffrn_reflns_Laue_measured_fraction_max 0.998
_diffrn_reflns_limit_h_max       18
_diffrn_reflns_limit_h_min       -18
_diffrn_reflns_limit_k_max       20
_diffrn_reflns_limit_k_min       -20
_diffrn_reflns_limit_l_max       21
_diffrn_reflns_limit_l_min       -21
_diffrn_reflns_number            93421
_diffrn_reflns_point_group_measured_fraction_full 0.998
_diffrn_reflns_point_group_measured_fraction_max 0.998
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         25.350
_diffrn_reflns_theta_min         2.342
_diffrn_source_current           50.0
_diffrn_source_power             2.5
_diffrn_source_voltage           50.0
_diffrn_standards_number         0
_exptl_absorpt_coefficient_mu    0.411
_exptl_absorpt_correction_T_max  0.7452
_exptl_absorpt_correction_T_min  0.6951
_exptl_absorpt_correction_type   none
_exptl_absorpt_process_details
;
SADABS-2016/2 (Bruker,2016/2) was used for absorption correction.
wR2(int) was 0.1251 before and 0.0428 after correction.
The Ratio of minimum to maximum transmission is 0.9328.
The \l/2 correction factor is Not present.
;
_exptl_crystal_colour            colourless
_exptl_crystal_colour_primary    colourless
_exptl_crystal_density_diffrn    1.413
_exptl_crystal_description       fragment
_exptl_crystal_F_000             1792
_exptl_crystal_size_max          0.382
_exptl_crystal_size_mid          0.287
_exptl_crystal_size_min          0.198
_refine_diff_density_max         1.237
_refine_diff_density_min         -0.808
_refine_diff_density_rms         0.074
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.067
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     1069
_refine_ls_number_reflns         15133
_refine_ls_number_restraints     272
_refine_ls_restrained_S_all      1.077
_refine_ls_R_factor_all          0.0457
_refine_ls_R_factor_gt           0.0418
_refine_ls_shift/su_max          0.004
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'w=1/[\s^2^(Fo^2^)+(0.0401P)^2^+8.8659P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1026
_refine_ls_wR_factor_ref         0.1061
_reflns_Friedel_coverage         0.000
_reflns_number_gt                14018
_reflns_number_total             15133
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            d4sc07116f2.cif
_cod_data_source_block           niude7_0m
_cod_depositor_comments
'Adding full bibliography for 1573732--1573734.cif.'
_cod_database_code               1573732
_shelx_shelxl_version_number     2016/6
_shelx_estimated_absorpt_t_max   0.923
_shelx_estimated_absorpt_t_min   0.859
_olex2_refinement_description
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups
 At 1.5 times of:
  All C(H,H,H) groups
2. Restrained distances
 C85-C82
 1.51 with sigma of 0.02
 C82-C81 = C82-C83 = C80-C79
 1.39 with sigma of 0.02
 C81-C80 = C79-C84 = C84-C83
 1.38 with sigma of 0.02
 C72-C73
 1.51 with sigma of 0.02
 C73-C78 = C73-C74 = C77-C76
 1.39 with sigma of 0.02
 C78-C77 = C76-C75 = C75-C74
 1.38 with sigma of 0.02
 C85-C81 = C85-C83
 2.52 with sigma of 0.04
 C82-C80
 2.42 with sigma of 0.04
 C82-C84
 2.41 with sigma of 0.04
 C81-C79
 2.39 with sigma of 0.04
 C80-C84 = C79-C83
 2.4 with sigma of 0.04
 C72-C78 = C72-C74
 2.52 with sigma of 0.04
 C73-C77
 2.42 with sigma of 0.04
 C73-C75
 2.41 with sigma of 0.04
 C78-C76
 2.39 with sigma of 0.04
 C77-C75 = C76-C74
 2.4 with sigma of 0.04
 C82-C81 \\sim C81-C80 \\sim C80-C79 \\sim C79-C84 \\sim C84-C83 \\sim C83-C82
 with sigma of 0.02
 C82-C84 \\sim C82-C80 \\sim C83-C79 \\sim C81-C83 \\sim C80-C84 \\sim C81-C79
 with sigma of 0.04
 C85-C83 \\sim C85-C81
 with sigma of 0.04
 C73-C78 \\sim C78-C77 \\sim C77-C76 \\sim C76-C75 \\sim C75-C74 \\sim C74-C73
 with sigma of 0.02
 C73-C75 \\sim C73-C77 \\sim C74-C76 \\sim C78-C74 \\sim C77-C75 \\sim C78-C76
 with sigma of 0.04
 C72-C74 \\sim C72-C78
 with sigma of 0.04
3. Restrained planarity
 C85, C82, C81, C80, C79, C84, C83
 with sigma of 0.1
 C72, C73, C78, C77, C76, C75, C74
 with sigma of 0.1
4. Uiso/Uaniso restraints and constraints
C85 \\sim C82 \\sim C81 \\sim C80 \\sim C79 \\sim C84 \\sim C83: within 2A with
sigma of 0.04 and sigma for terminal atoms of 0.08 within 2A
C72 \\sim C73 \\sim C78 \\sim C77 \\sim C76 \\sim C75 \\sim C74: within 2A with
sigma of 0.04 and sigma for terminal atoms of 0.08 within 2A
F22: within 2A with sigma of 0.04 and sigma for terminal atoms of 0.08 within 2A
5. Rigid body (RIGU) restrains
 C85, C82, C81, C80, C79, C84, C83
 with sigma for 1-2 distances of 0.004 and sigma for 1-3 distances of 0.004
 C72, C73, C78, C77, C76, C75, C74
 with sigma for 1-2 distances of 0.004 and sigma for 1-3 distances of 0.004
6. Others
 Fixed Sof: C85(0.5) H85A(0.5) H85B(0.5) H85C(0.5) C82(0.5) C81(0.5) H81(0.5)
 C80(0.5) H80(0.5) C79(0.5) H79(0.5) C84(0.5) H84(0.5) C83(0.5) H83(0.5)
 C72(0.5) H72A(0.5) H72B(0.5) H72C(0.5) C73(0.5) C78(0.5) H78(0.5) C77(0.5)
 H77(0.5) C76(0.5) H76(0.5) C75(0.5) H75(0.5) C74(0.5) H74(0.5)
7.a Me refined with riding coordinates:
 C72(H72A,H72B,H72C)
7.b Aromatic/amide H refined with riding coordinates:
 C3(H3), C4(H4), C5(H5), C9(H9), C11(H11), C18(H18), C20(H20), C41(H41),
 C43(H43), C45(H45), C49(H49), C51(H51), C53(H53), C57(H57), C59(H59), C61(H61),
  C65(H65), C67(H67), C69(H69), C81(H81), C80(H80), C79(H79), C84(H84),
 C83(H83), C78(H78), C77(H77), C76(H76), C75(H75), C74(H74)
7.c Idealised Me refined as rotating group:
 C13(H13A,H13B,H13C), C14(H14A,H14B,H14C), C15(H15A,H15B,H15C), C22(H22A,H22B,
 H22C), C23(H23A,H23B,H23C), C24(H24A,H24B,H24C), C28(H28A,H28B,H28C), C29(H29A,
 H29B,H29C), C30(H30A,H30B,H30C), C31(H31A,H31B,H31C), C36(H36A,H36B,H36C),
 C37(H37A,H37B,H37C), C38(H38A,H38B,H38C), C39(H39A,H39B,H39C), C85(H85A,H85B,
 H85C)
;
_smtbx_masks_void_probe_radius   1.2
_smtbx_masks_void_truncation_radius 1.2
_shelx_res_checksum              11601
_shelx_fab_checksum              1681
_olex2_submission_special_instructions 'No special instructions were received'