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_4135495
_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 H36 Fe N P'
_chemical_formula_sum            'C36 H36 Fe N P'
_chemical_formula_weight         569.48
_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
_audit_creation_date             2020-08-12
_audit_creation_method
;
Olex2 1.2
(compiled 2018.05.29 svn.r3508 for OlexSys, GUI svn.r5506)
;
_cell_angle_alpha                100.883(2)
_cell_angle_beta                 90.650(2)
_cell_angle_gamma                113.739(4)
_cell_formula_units_Z            2
_cell_length_a                   10.2056(4)
_cell_length_b                   11.5487(4)
_cell_length_c                   13.9039(3)
_cell_measurement_reflns_used    8311
_cell_measurement_temperature    173.00(10)
_cell_measurement_theta_max      76.1360
_cell_measurement_theta_min      4.2490
_cell_volume                     1466.13(10)
_computing_cell_refinement       'CrysAlisPro 1.171.40.68a (Rigaku OD, 2019)'
_computing_data_collection       'CrysAlisPro 1.171.40.68a (Rigaku OD, 2019)'
_computing_data_reduction        'CrysAlisPro 1.171.40.68a (Rigaku OD, 2019)'
_computing_molecular_graphics    'Olex2 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 (Dolomanov et al., 2009)'
_computing_structure_refinement  'ShelXL (Sheldrick, 2015)'
_diffrn_ambient_environment      N~2~
_diffrn_ambient_temperature      173.00(10)
_diffrn_detector                 'Hybrid Pixel Array Detector'
_diffrn_detector_area_resol_mean 10.0000
_diffrn_detector_type            HyPix
_diffrn_measured_fraction_theta_full 0.985
_diffrn_measured_fraction_theta_max 0.934
_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     52.00 115.00   1.00    0.10    --   48.45  40.00-172.00   63
  2  \w    110.00 176.00   1.00    0.57    --  106.49  40.00-172.00   66
  3  \w    140.00 176.00   1.00    0.57    --  106.49  19.00 -60.00   36
  4  \w     95.00 135.00   1.00    0.57    --  106.49  19.00 -60.00   40
  5  \w     96.00 173.00   1.00    0.57    --  106.49  19.00  90.00   77
  6  \w     65.00 106.00   1.00    0.57    --  106.49 -99.00 -90.00   41
  7  \w     37.00 108.00   1.00    0.57    --  106.49-113.00-102.62   71
  8  \w     42.00 107.00   1.00    0.57    --  106.49-125.00  60.00   65
  9  \w     48.00 106.00   1.00    0.57    --  106.49-125.00  90.00   58
 10  \w     71.00 108.00   1.00    0.57    --  106.49-113.00 120.47   37
 11  \w     42.00  68.00   1.00    0.57    --  106.49-113.00 120.47   26
 12  \w     34.00  68.00   1.00    0.57    --  106.49 -99.00 120.00   34
 13  \w     74.00 106.00   1.00    0.57    --  106.49 -99.00 120.00   32
 14  \w     34.00 103.00   1.00    0.57    --  106.49 -99.00 -30.00   69
 15  \w     34.00 103.00   1.00    0.57    --  106.49 -99.00-180.00   69
 16  \w     34.00  62.00   1.00    0.57    --  106.49 -99.00 -90.00   28
 17  \w     39.00  66.00   1.00    0.57    --  106.49 -57.00 -30.00   27
 18  \w      7.00  42.00   1.00    0.10    --   48.45 -40.00  33.00   35
 19  \w    -24.00   2.00   1.00    0.10    --   48.45 -40.00  33.00   26
 20  \w     34.00  62.00   1.00    0.57    --  106.49 -57.00-180.00   28
 21  \w    -18.00  27.00   1.00    0.10    --  -48.45  19.00 -30.00   45
 22  \w    -44.00  24.00   1.00    0.10    --  -48.45  40.00-172.00   68
 23  \w    -41.00 -13.00   1.00    0.57    --  -86.25  40.00-172.00   28
 24  \w    -39.00 -13.00   1.00    0.57    --  -86.25  38.00 -90.00   26
 25  \w    -66.00 -17.00   1.00    0.57    --  -86.25  57.00 150.00   49
 26  \w   -110.00 -81.00   1.00    0.57    --  -86.25 -40.00  33.00   29
 27  \w   -159.00-116.00   1.00    0.57    --  -86.25 -40.00  33.00   43
 28  \w   -115.00 -73.00   1.00    0.10    --  -48.45-125.00 -30.00   42
 29  \w   -147.00 -74.00   1.00    0.57    --  -86.25-125.00-150.00   73
 30  \w   -119.00 -36.00   1.00    0.10    --  -48.45 -40.00  33.00   83
 31  \w    -81.00 -15.00   1.00    0.57    --  -86.25 125.00-120.00   66
;
_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      0.1527388000
_diffrn_orient_matrix_UB_12      0.0124856000
_diffrn_orient_matrix_UB_13      -0.0201534000
_diffrn_orient_matrix_UB_21      -0.0199909000
_diffrn_orient_matrix_UB_22      -0.1104018000
_diffrn_orient_matrix_UB_23      0.0535228000
_diffrn_orient_matrix_UB_31      -0.0610277000
_diffrn_orient_matrix_UB_32      -0.0994186000
_diffrn_orient_matrix_UB_33      -0.0978831000
_diffrn_radiation_monochromator  mirror
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54184
_diffrn_reflns_av_R_equivalents  0.0336
_diffrn_reflns_av_unetI/netI     0.0389
_diffrn_reflns_Laue_measured_fraction_full 0.985
_diffrn_reflns_Laue_measured_fraction_max 0.934
_diffrn_reflns_limit_h_max       12
_diffrn_reflns_limit_h_min       -12
_diffrn_reflns_limit_k_max       14
_diffrn_reflns_limit_k_min       -14
_diffrn_reflns_limit_l_max       15
_diffrn_reflns_limit_l_min       -17
_diffrn_reflns_number            15207
_diffrn_reflns_point_group_measured_fraction_full 0.985
_diffrn_reflns_point_group_measured_fraction_max 0.934
_diffrn_reflns_theta_full        67.684
_diffrn_reflns_theta_max         76.236
_diffrn_reflns_theta_min         4.279
_diffrn_source                   'micro-focus sealed X-ray tube'
_diffrn_source_type              'PhotonJet (Cu) X-ray Source'
_exptl_absorpt_coefficient_mu    4.817
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.75724
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
CrysAlisPro 1.171.40.68a (Rigaku Oxford Diffraction, 2019)
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_crystal_colour            'metallic intense red'
_exptl_crystal_density_diffrn    1.290
_exptl_crystal_description       block
_exptl_crystal_F_000             600
_exptl_crystal_size_max          0.1
_exptl_crystal_size_mid          0.05
_exptl_crystal_size_min          0.01
_refine_diff_density_max         0.492
_refine_diff_density_min         -0.341
_refine_diff_density_rms         0.137
_refine_ls_extinction_coef       0.0044(4)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc^2^\l^3^/sin(2\q)]^-1/4^
_refine_ls_extinction_method     SHELXL
_refine_ls_goodness_of_fit_ref   1.089
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     362
_refine_ls_number_reflns         5738
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.089
_refine_ls_R_factor_all          0.0409
_refine_ls_R_factor_gt           0.0378
_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^)+(0.0565P)^2^+0.3290P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0997
_refine_ls_wR_factor_ref         0.1014
_reflns_Friedel_coverage         0.000
_reflns_number_gt                5336
_reflns_number_total             5738
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            ja0c11448_si_002.cif
_cod_data_source_block           7
_cod_original_cell_volume        1466.13(9)
_cod_database_code               4135495
_shelxl_version_number           2013-4
_chemical_oxdiff_formula         FePNC
_shelx_estimated_absorpt_t_max   0.953
_shelx_estimated_absorpt_t_min   0.644
_diffrn_oxdiff_digest_frames
;
01a761f66437f4e9efb18be0ec73cecb5b0148090e5
;
_diffrn_oxdiff_digest_hkl
;
01577f1512d5272c4d25e11a45472835bcbd8b
;
_reflns_odcompleteness_completeness 98.74
_reflns_odcompleteness_iscentric 1
_reflns_odcompleteness_theta     66.97
_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:
 C16(H16), C15(H15), C28(H28), C30(H30), C14(H14), C32(H32), C22(H22),
 C13(H13), C20(H20), C21(H21), C27(H27), C18(H18), C34(H34), C24(H24), C36(H36),
  C26(H26), C33(H33), C19(H19), C25(H25), C35(H35)
2.b Idealised Me refined as rotating group:
 C7(H7A,H7B,H7C), C6(H6A,H6B,H6C), C8(H8A,H8B,H8C), C10(H10A,H10B,H10C),
 C9(H9A,H9B,H9C)
;
_shelx_res_checksum              98574
_shelx_hkl_checksum              64620
_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 1.307
_oxdiff_exptl_absorpt_empirical_full_min 0.744