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_4135490
_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         'C28 H30 Fe N P'
_chemical_formula_sum            'C28 H30 Fe N P'
_chemical_formula_weight         467.38
_space_group_crystal_system      monoclinic
_space_group_IT_number           14
_space_group_name_Hall           '-P 2yn'
_space_group_name_H-M_alt        'P 1 21/n 1'
_symmetry_Int_Tables_number      14
_atom_sites_solution_primary     iterative
_audit_creation_date             2020-01-08
_audit_creation_method
;
Olex2 1.2
(compiled 2018.05.29 svn.r3508 for OlexSys, GUI svn.r5506)
;
_cell_angle_alpha                90
_cell_angle_beta                 97.915(6)
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   9.068(4)
_cell_length_b                   18.588(9)
_cell_length_c                   14.778(7)
_cell_measurement_reflns_used    3018
_cell_measurement_temperature    173
_cell_measurement_theta_max      25.22
_cell_measurement_theta_min      2.49
_cell_volume                     2467(2)
_computing_cell_refinement       'SAINT V8.30C (?, 2016)'
_computing_data_reduction        'SAINT V8.30C (?, 2016)'
_computing_molecular_graphics    'Olex2 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 (Dolomanov et al., 2009)'
_computing_structure_refinement  'olex2.refine (Bourhis et al., 2015)'
_computing_structure_solution
;
Superflip (Palatinus & Chapuis, 2007;Palatinus & van der Lee, 2008;
Palatinus et al., 2012)
;
_diffrn_ambient_temperature      173
_diffrn_measured_fraction_theta_full 0.9989
_diffrn_measured_fraction_theta_max 0.9989
_diffrn_measurement_device_type  'Bruker APEX-II CCD'
_diffrn_measurement_method       '\f and \w scans'
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_type           synchrotron
_diffrn_radiation_wavelength     0.71
_diffrn_reflns_av_R_equivalents  0.0750
_diffrn_reflns_av_unetI/netI     0.0947
_diffrn_reflns_limit_h_max       11
_diffrn_reflns_limit_h_min       -11
_diffrn_reflns_limit_k_max       24
_diffrn_reflns_limit_k_min       -23
_diffrn_reflns_limit_l_max       19
_diffrn_reflns_limit_l_min       -19
_diffrn_reflns_number            16976
_diffrn_reflns_theta_full        24.9989
_diffrn_reflns_theta_max         25.00
_diffrn_reflns_theta_min         1.77
_diffrn_standards_number         0
_exptl_absorpt_coefficient_mu    0.689
_exptl_absorpt_correction_T_max  0.7456
_exptl_absorpt_correction_T_min  0.5436
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
SADABS-2012/1 (Bruker,2012) was used for absorption correction.
wR2(int) was 0.0733 before and 0.0620 after correction.
The Ratio of minimum to maximum transmission is 0.7291.
The \l/2 correction factor is 0.0015.
;
_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    1.2582
_exptl_crystal_description       cube
_exptl_crystal_F_000             986.1120
_exptl_crystal_size_max          0.09
_exptl_crystal_size_mid          0.05
_exptl_crystal_size_min          0.02
_refine_diff_density_max         1.6381
_refine_diff_density_min         -0.7373
_refine_diff_density_rms         0.1294
_refine_ls_d_res_high            0.8400
_refine_ls_d_res_low             11.4998
_refine_ls_goodness_of_fit_ref   1.0883
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_constraints    48
_refine_ls_number_parameters     289
_refine_ls_number_reflns         4356
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.0883
_refine_ls_R_factor_all          0.0898
_refine_ls_R_factor_gt           0.0515
_refine_ls_shift/su_max          0.0000
_refine_ls_shift/su_mean         0.0000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'w=1/[\s^2^(Fo^2^)+(0.0720P)^2^] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1207
_refine_ls_wR_factor_ref         0.1449
_reflns_Friedel_coverage         0.0
_reflns_limit_h_max              8
_reflns_limit_h_min              -10
_reflns_limit_k_max              22
_reflns_limit_k_min              0
_reflns_limit_l_max              17
_reflns_limit_l_min              -7
_reflns_number_gt                3025
_reflns_number_total             4356
_reflns_threshold_expression     I>=2u(I)
_cod_data_source_file            ja0c11448_si_002.cif
_cod_data_source_block           1
_cod_original_sg_symbol_Hall     '-P 2ybc (x-z,y,z)'
_cod_database_code               4135490
_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.a Aromatic/amide H refined with riding coordinates:
 C5(H5), C14(H14), C12(H12), C18(H18), C4(H4), C8(H8), C3(H3), C2(H2),
 C10(H10), C11(H11), C16(H16), C15(H15), C17(H17), C9(H9)
2.b Idealised Me refined as rotating group:
 C24(H24a,H24b,H24c), C28(H28a,H28b,H28c), C25(H25a,H25b,H25c), C26(H26a,H26b,
 H26c), C27(H27a,H27b,H27c)
;
_olex2_submission_special_instructions 'No special instructions were received'