Iron-Catalyzed Regiodivergent Hydrostannation of Alkynes: Intermediacy of Fe(IV)‒H versus Fe(II)‒Vinylidene
Liu, Jianguo; Song, Heng; Wang, Tianlin; Jia, Jiong; Tong, Qing-Xiao; Tung, Chen-Ho; Wang, Wenguang; Journal of the American Chemical Society  (2020) –; doi:10.1021/jacs.0c11448

data_4135492
_publ_section_title
;
 Iron-Catalyzed Regiodivergent Hydrostannation of Alkynes: Intermediacy of
 Fe(IV)--H versus Fe(II)--Vinylidene
;
_journal_name_full               'Journal of the American Chemical Society'
_journal_paper_doi               10.1021/jacs.0c11448
_journal_year                    2020
_chemical_formula_moiety         'C36 H46 Fe N3 P Sn'
_chemical_formula_sum            'C36 H46 Fe N3 P Sn'
_chemical_formula_weight         726.27
_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
_audit_creation_date             2019-10-28
_audit_creation_method
;
Olex2 1.2
(compiled 2018.05.29 svn.r3508 for OlexSys, GUI svn.r5506)
;
_cell_angle_alpha                68.935(3)
_cell_angle_beta                 74.780(3)
_cell_angle_gamma                72.989(3)
_cell_formula_units_Z            2
_cell_length_a                   11.1228(4)
_cell_length_b                   12.5847(5)
_cell_length_c                   14.3033(5)
_cell_measurement_reflns_used    8592
_cell_measurement_temperature    173
_cell_measurement_theta_max      76.5357
_cell_measurement_theta_min      4.2228
_cell_volume                     1758.59(12)
_computing_molecular_graphics    'Olex2 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 (Dolomanov et al., 2009)'
_computing_structure_refinement  'ShelXL (Sheldrick, 2015)'
_diffrn_ambient_temperature      173
_diffrn_measured_fraction_theta_full 0.970
_diffrn_measured_fraction_theta_max 0.985
_diffrn_measurement_device_type  'four-circle diffractometer'
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54184
_diffrn_reflns_av_R_equivalents  0.0528
_diffrn_reflns_av_unetI/netI     0.0580
_diffrn_reflns_Laue_measured_fraction_full 0.970
_diffrn_reflns_Laue_measured_fraction_max 0.985
_diffrn_reflns_limit_h_max       12
_diffrn_reflns_limit_h_min       -13
_diffrn_reflns_limit_k_max       14
_diffrn_reflns_limit_k_min       -15
_diffrn_reflns_limit_l_max       17
_diffrn_reflns_limit_l_min       -17
_diffrn_reflns_number            16525
_diffrn_reflns_point_group_measured_fraction_full 0.970
_diffrn_reflns_point_group_measured_fraction_max 0.985
_diffrn_reflns_theta_full        67.684
_diffrn_reflns_theta_max         67.073
_diffrn_reflns_theta_min         4.223
_exptl_absorpt_coefficient_mu    9.583
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.27117
_exptl_absorpt_correction_type   multi-scan
_exptl_crystal_colour            'metallic orangish orange'
_exptl_crystal_colour_lustre     metallic
_exptl_crystal_colour_modifier   orangish
_exptl_crystal_colour_primary    orange
_exptl_crystal_density_diffrn    1.372
_exptl_crystal_description       block
_exptl_crystal_F_000             748
_exptl_crystal_size_max          0.088
_exptl_crystal_size_mid          0.056
_exptl_crystal_size_min          0.019
_refine_diff_density_max         1.577
_refine_diff_density_min         -0.830
_refine_diff_density_rms         0.103
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.065
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     406
_refine_ls_number_reflns         6178
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.065
_refine_ls_R_factor_all          0.0510
_refine_ls_R_factor_gt           0.0407
_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^)+(0.0573P)^2^+1.5563P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1036
_refine_ls_wR_factor_ref         0.1130
_reflns_Friedel_coverage         0.000
_reflns_number_gt                5358
_reflns_number_total             6178
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            ja0c11448_si_002.cif
_cod_data_source_block           3
_cod_database_code               4135492
_shelxl_version_number           2013-4
_shelx_estimated_absorpt_t_max   0.839
_shelx_estimated_absorpt_t_min   0.486
_olex2_refinement_description
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups, All C(H,H) groups, All N(H) groups
 At 1.5 times of:
  All C(H,H,H) groups
2. Others
 Fixed Sof: H31(0.6) H31A(0.4) C32A(0.6) H32A(0.6) H32B(0.6) H32C(0.6)
 C32B(0.4) H32D(0.4) H32E(0.4) H32F(0.4) H35A(0.6) H35(0.4) C36A(0.6) H36A(0.6)
 H36B(0.6) H36C(0.6) C36B(0.4) H36D(0.4) H36E(0.4) H36F(0.4)
3.a Secondary CH2 refined with riding coordinates:
 C29(H29A,H29B), C30(H30A,H30B), C33(H33A,H33B), C34(H34A,H34B)
3.b Aromatic/amide H refined with riding coordinates:
 C13(H13), C14(H14), C15(H15), C16(H16), C18(H18), C19(H19), C20(H20),
 C21(H21), C22(H22), C24(H24), C25(H25), C26(H26), C27(H27), C28(H28), C31(H31),
  C31(H31A), C35(H35A), C35(H35), N1(H1)
3.c Idealised Me refined as rotating group:
 C6(H6A,H6B,H6C), C7(H7A,H7B,H7C), C8(H8A,H8B,H8C), C9(H9A,H9B,H9C), C10(H10A,
 H10B,H10C), C32A(H32A,H32B,H32C), C32B(H32D,H32E,H32F), C36A(H36A,H36B,H36C),
 C36B(H36D,H36E,H36F)
;
_shelx_res_checksum              51930
_shelx_hkl_checksum              3704
_olex2_submission_special_instructions 'No special instructions were received'