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_4135493
_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         'C48 H76 Fe N P Sn2'
_chemical_formula_sum            'C48 H76 Fe N P Sn2'
_chemical_formula_weight         991.29
_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   mixed
_atom_sites_solution_primary     dual
_audit_creation_date             2020-08-07
_audit_creation_method
;
Olex2 1.2
(compiled 2018.05.29 svn.r3508 for OlexSys, GUI svn.r5506)
;
_cell_angle_alpha                80.482(3)
_cell_angle_beta                 81.219(4)
_cell_angle_gamma                66.868(5)
_cell_formula_units_Z            2
_cell_length_a                   10.3649(5)
_cell_length_b                   12.6600(6)
_cell_length_c                   20.0264(7)
_cell_measurement_reflns_used    7750
_cell_measurement_temperature    172.99(10)
_cell_measurement_theta_max      75.8770
_cell_measurement_theta_min      3.7810
_cell_volume                     2372.1(2)
_computing_cell_refinement       'CrysAlisPro 1.171.40.25a (Rigaku OD, 2018)'
_computing_data_collection       'CrysAlisPro 1.171.40.25a (Rigaku OD, 2018)'
_computing_data_reduction        'CrysAlisPro 1.171.40.25a (Rigaku OD, 2018)'
_computing_molecular_graphics    'Olex2 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 (Dolomanov et al., 2009)'
_computing_structure_refinement  'XL (Sheldrick, 2008)'
_computing_structure_solution    'ShelXT (Sheldrick, 2015)'
_diffrn_ambient_environment      N~2~
_diffrn_ambient_temperature      172.99(10)
_diffrn_detector                 'CCD plate'
_diffrn_detector_area_resol_mean 10.0000
_diffrn_detector_type            HyPix
_diffrn_measured_fraction_theta_full 0.979
_diffrn_measured_fraction_theta_max 0.924
_diffrn_measurement_details
;
List of Runs (angles in degrees, time in seconds):

  # Type    Start    End  Width  t~exp~   \w     \q     \k     \f   Frames
--------------------------------------------------------------------------
  1  \w     21.00  72.00   1.00    0.13    --   48.20-104.00  81.00   51
  2  \w   -118.00 -89.00   1.00    0.90    --  -86.25-104.00  81.00   29
  3  \w   -153.00-125.00   1.00    0.90    --  -86.25-104.00  81.00   28
  4  \w    -83.00 -58.00   1.00    0.90    --  -86.25 104.00-177.00   25
  5  \w    112.00 153.00   1.00    0.90    --  106.49 104.00-177.00   41
  6  \w     48.00 108.00   1.00    0.90    --  106.49-104.00  81.00   60
  7  \w    -60.00  19.00   1.00    0.13    --  -48.20  38.00-180.00   79
  8  \w    -69.00   7.00   1.00    0.13    --  -48.20 104.00-177.00   76
  9  \w   -114.00 -70.00   1.00    0.13    --  -48.20-125.00-120.00   44
 10  \w    -61.00  27.00   1.00    0.13    --  -48.20  19.00 120.00   88
 11  \w   -158.00 -73.00   1.00    0.90    --  -86.25 -38.00  90.00   85
 12  \w   -159.00 -72.00   1.00    0.90    --  -86.25 -57.00 150.00   87
 13  \w     34.00 109.00   1.00    0.90    --  106.49 -99.00 -30.00   75
 14  \w     45.00 117.00   1.00    0.90    --  106.49-125.00 -90.00   72
 15  \w     35.00 109.00   1.00    0.90    --  106.49 -99.00 -90.00   74
 16  \w     92.00 178.00   1.00    0.90    --  106.49  57.00 150.00   86
 17  \w    135.00 177.00   1.00    0.90    --  106.49  77.00 -30.00   42
 18  \w     85.00 178.00   1.00    0.90    --  106.49  77.00-150.00   93
 19  \w     35.00 109.00   1.00    0.90    --  106.49 -99.00 120.00   74
 20  \w     84.00 178.00   1.00    0.90    --  106.49  77.00  90.00   94
 21  \w     87.00 132.00   1.00    0.90    --  106.49  77.00 -30.00   45
;
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'XtaLAB Synergy, Dualflex, HyPix'
_diffrn_measurement_method       '\w scans'
_diffrn_orient_matrix_type
'CrysAlisPro convention (1999,Acta A55,543-557)'
_diffrn_orient_matrix_UB_11      0.1105054000
_diffrn_orient_matrix_UB_12      -0.0262143000
_diffrn_orient_matrix_UB_13      0.0501572000
_diffrn_orient_matrix_UB_21      0.0924152000
_diffrn_orient_matrix_UB_22      0.0430674000
_diffrn_orient_matrix_UB_23      -0.0565789000
_diffrn_orient_matrix_UB_31      -0.0749514000
_diffrn_orient_matrix_UB_32      0.1233159000
_diffrn_orient_matrix_UB_33      0.0206049000
_diffrn_radiation_monochromator  mirror
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54184
_diffrn_reflns_av_R_equivalents  0.0659
_diffrn_reflns_av_unetI/netI     0.0694
_diffrn_reflns_Laue_measured_fraction_full 0.979
_diffrn_reflns_Laue_measured_fraction_max 0.924
_diffrn_reflns_limit_h_max       13
_diffrn_reflns_limit_h_min       -12
_diffrn_reflns_limit_k_max       15
_diffrn_reflns_limit_k_min       -14
_diffrn_reflns_limit_l_max       25
_diffrn_reflns_limit_l_min       -24
_diffrn_reflns_number            22394
_diffrn_reflns_point_group_measured_fraction_full 0.979
_diffrn_reflns_point_group_measured_fraction_max 0.924
_diffrn_reflns_theta_full        67.684
_diffrn_reflns_theta_max         76.399
_diffrn_reflns_theta_min         3.823
_diffrn_source                   'micro-focus sealed X-ray tube'
_diffrn_source_type              'PhotonJet (Cu) X-ray Source'
_exptl_absorpt_coefficient_mu    11.266
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.33883
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
CrysAlisPro 1.171.40.25a (Rigaku Oxford Diffraction, 2018)
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_crystal_colour            'metallic yellowish yellow'
_exptl_crystal_colour_lustre     metallic
_exptl_crystal_colour_modifier   yellowish
_exptl_crystal_colour_primary    yellow
_exptl_crystal_density_diffrn    1.388
_exptl_crystal_description       needle
_exptl_crystal_F_000             1024
_exptl_crystal_size_max          0.06
_exptl_crystal_size_mid          0.04
_exptl_crystal_size_min          0.02
_refine_diff_density_max         1.664
_refine_diff_density_min         -0.986
_refine_diff_density_rms         0.145
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.054
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     495
_refine_ls_number_reflns         9197
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.054
_refine_ls_R_factor_all          0.0710
_refine_ls_R_factor_gt           0.0552
_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^)+(0.0647P)^2^+9.7679P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1355
_refine_ls_wR_factor_ref         0.1529
_reflns_Friedel_coverage         0.000
_reflns_number_gt                7532
_reflns_number_total             9197
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            ja0c11448_si_002.cif
_cod_data_source_block           4
_cod_database_code               4135493
_shelx_shelxl_version_number     2014/7
_chemical_oxdiff_formula         FeSnPNC
_shelx_estimated_absorpt_t_max   0.806
_shelx_estimated_absorpt_t_min   0.551
_reflns_odcompleteness_completeness 98.29
_reflns_odcompleteness_iscentric 1
_reflns_odcompleteness_theta     66.97
_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.a Secondary CH2 refined with riding coordinates:
 C29(H29A,H29B), C30(H30A,H30B), C31(H31A,H31B), C33(H33A,H33B), C34(H34A,
 H34B), C35(H35A,H35B), C37(H37A,H37B), C38(H38A,H38B), C39(H39A,H39B),
 C41(H41A,H41B), C42(H42A,H42B), C43(H43A,H43B), C45(H45A,H45B), C46(H46A,H46B),
  C47(H47A,H47B)
2.b Aromatic/amide H refined with riding coordinates:
 C12(H12), C13(H13), C14(H14), C15(H15), C18(H18), C19(H19), C20(H20),
 C21(H21), C22(H22), C24(H24), C25(H25), C26(H26), C27(H27), C28(H28)
2.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), C32(H32A,H32B,H32C), C36(H36A,H36B,H36C), C40(H40A,H40B,H40C),
 C44(H44A,H44B,H44C), C48(H48A,H48B,H48C)
;
_shelx_res_checksum              3470
_shelx_hkl_checksum              79823
_olex2_submission_special_instructions 'No special instructions were received'
_oxdiff_exptl_absorpt_empirical_details
;
Empirical correction (ABSPACK) includes:
- Absorption correction using spherical harmonics
- Frame scaling
;
_oxdiff_exptl_absorpt_empirical_full_max 1.856
_oxdiff_exptl_absorpt_empirical_full_min 0.497