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_4135497
_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         'C40 H51 Fe2 O P'
_chemical_formula_sum            'C40 H51 Fe2 O P'
_chemical_formula_weight         690.47
_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             2020-09-28
_audit_creation_method
;
Olex2 1.2
(compiled 2018.05.29 svn.r3508 for OlexSys, GUI svn.r5506)
;
_cell_angle_alpha                99.047(3)
_cell_angle_beta                 101.930(3)
_cell_angle_gamma                92.236(3)
_cell_formula_units_Z            2
_cell_length_a                   10.3227(4)
_cell_length_b                   12.8127(5)
_cell_length_c                   13.4047(5)
_cell_measurement_reflns_used    7360
_cell_measurement_temperature    172.99(10)
_cell_measurement_theta_max      76.1080
_cell_measurement_theta_min      3.4110
_cell_volume                     1708.36(12)
_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  'ShelXL (Sheldrick, 2015)'
_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 0.971
_diffrn_measured_fraction_theta_max 0.985
_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     24.00  60.00   1.00    0.10    --   48.45-113.00 -21.00   36
  2  \w    -76.00 -34.00   1.00    0.25    --  -86.25 113.00  70.00   42
  3  \w   -116.00 -83.00   1.00    0.25    --  -86.25-113.00 -21.00   33
  4  \w     86.00 112.00   1.00    0.25    --  106.49-113.00 -21.00   26
  5  \w     53.00  79.00   1.00    0.25    --  106.49-113.00 -21.00   26
  6  \w    100.00 125.00   1.00    0.25    --  106.49 113.00  70.00   25
  7  \w   -118.00 -70.00   1.00    0.10    --  -48.45-125.00  30.00   48
  8  \w    -83.00  -3.00   1.00    0.10    --  -48.45 113.00  70.00   80
  9  \w     37.00  63.00   1.00    0.10    --   48.45 -57.00 -60.00   26
 10  \w    -10.00  33.00   1.00    0.10    --   48.45 -57.00 -60.00   43
 11  \w    -24.00  61.00   1.00    0.10    --   48.45 -37.00  60.00   85
 12  \w    -19.00  58.00   1.00    0.10    --   48.45 -57.00-150.00   77
 13  \w   -100.00 -13.00   1.00    0.25    --  -86.25  15.00 -60.00   87
 14  \w     35.00 106.00   1.00    0.25    --  106.49 -94.00-150.00   71
 15  \w     34.00 107.00   1.00    0.25    --  106.49 -94.00 -60.00   73
 16  \w     35.00 107.00   1.00    0.25    --  106.49 -94.00 150.00   72
 17  \w     35.00 108.00   1.00    0.25    --  106.49 -94.00  90.00   73
 18  \w     98.00 177.00   1.00    0.25    --  106.49  30.00-180.00   79
 19  \w     34.00 129.00   1.00    0.25    --  106.49 -77.00 -30.00   95
 20  \w     93.00 178.00   1.00    0.25    --  106.49  15.00 120.00   85
 21  \w     85.00 176.00   1.00    0.25    --  106.49  77.00  30.00   91
;
_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      0.0447649000
_diffrn_orient_matrix_UB_12      -0.0326558000
_diffrn_orient_matrix_UB_13      0.1069386000
_diffrn_orient_matrix_UB_21      -0.0758465000
_diffrn_orient_matrix_UB_22      0.0891155000
_diffrn_orient_matrix_UB_23      0.0477376000
_diffrn_orient_matrix_UB_31      -0.1250535000
_diffrn_orient_matrix_UB_32      -0.0767926000
_diffrn_orient_matrix_UB_33      -0.0221155000
_diffrn_radiation_monochromator  mirror
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54184
_diffrn_reflns_av_R_equivalents  0.0443
_diffrn_reflns_av_unetI/netI     0.0514
_diffrn_reflns_Laue_measured_fraction_full 0.971
_diffrn_reflns_Laue_measured_fraction_max 0.985
_diffrn_reflns_limit_h_max       11
_diffrn_reflns_limit_h_min       -12
_diffrn_reflns_limit_k_max       15
_diffrn_reflns_limit_k_min       -15
_diffrn_reflns_limit_l_max       15
_diffrn_reflns_limit_l_min       -15
_diffrn_reflns_number            14961
_diffrn_reflns_point_group_measured_fraction_full 0.971
_diffrn_reflns_point_group_measured_fraction_max 0.985
_diffrn_reflns_theta_full        67.684
_diffrn_reflns_theta_max         67.072
_diffrn_reflns_theta_min         3.419
_diffrn_source                   'micro-focus sealed X-ray tube'
_diffrn_source_type              'PhotonJet (Cu) X-ray Source'
_exptl_absorpt_coefficient_mu    7.471
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.50793
_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 dark brown'
_exptl_crystal_density_diffrn    1.342
_exptl_crystal_description       block
_exptl_crystal_F_000             732
_exptl_crystal_size_max          0.09
_exptl_crystal_size_mid          0.05
_exptl_crystal_size_min          0.02
_refine_diff_density_max         0.277
_refine_diff_density_min         -0.519
_refine_diff_density_rms         0.069
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.046
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     402
_refine_ls_number_reflns         6001
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.046
_refine_ls_R_factor_all          0.0522
_refine_ls_R_factor_gt           0.0384
_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^)+(0.0333P)^2^+1.4833P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0866
_refine_ls_wR_factor_ref         0.0967
_reflns_Friedel_coverage         0.000
_reflns_number_gt                5129
_reflns_number_total             6001
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            ja0c11448_si_002.cif
_cod_data_source_block           10
_cod_original_cell_volume        1708.35(12)
_cod_database_code               4135497
_shelxl_version_number           2013-4
_chemical_oxdiff_formula         FePOC
_reflns_odcompleteness_completeness 98.72
_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
 At 1.5 times of:
  All C(H,H,H) groups
2.a Ternary CH refined with riding coordinates:
 C17(H17), C23(H23)
2.b Secondary CH2 refined with riding coordinates:
 C18(H18A,H18B), C19(H19A,H19B), C20(H20A,H20B), C21(H21A,H21B), C22(H22A,
 H22B), C24(H24A,H24B), C25(H25A,H25B), C26(H26A,H26B), C27(H27A,H27B),
 C28(H28A,H28B)
2.c Aromatic/amide H refined with riding coordinates:
 C12(H12), C13(H13), C14(H14), C15(H15), C30(H30), C32(H32), C33(H33),
 C34(H34), C35(H35), C36(H36), C37(H37), C38(H38), C39(H39), C40(H40)
2.d 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)
;
_shelx_res_checksum              58760
_shelx_hkl_checksum              51017
_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 1.379
_oxdiff_exptl_absorpt_empirical_full_min 0.738