Markovnikov-Selective, Activator-Free Iron-Catalyzed Vinylarene Hydroboration
MacNair, Alistair J.; Millet, Clément R. P.; Nichol, Gary S.; Ironmonger, Alan; Thomas, Stephen P.; ACS Catalysis 6 (2016) 7217–; doi:10.1021/acscatal.6b02281

data_4516714
_publ_section_title
;
 Markovnikov-Selective, Activator-Free Iron-Catalyzed Vinylarene
 Hydroboration
;
_journal_issue                   10
_journal_name_full               'ACS Catalysis'
_journal_page_first              7217
_journal_paper_doi               10.1021/acscatal.6b02281
_journal_volume                  6
_journal_year                    2016
_chemical_absolute_configuration ad
_chemical_formula_moiety         'C38 H42 Fe N4 O4, C4 H8 O'
_chemical_formula_sum            'C42 H50 Fe N4 O5'
_chemical_formula_weight         746.71
_space_group_crystal_system      monoclinic
_space_group_IT_number           4
_space_group_name_Hall           'P 2yb'
_space_group_name_H-M_alt        'P 1 21 1'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_audit_creation_date             2014-09-26
_audit_creation_method
;
Olex2 1.2-beta
(compiled 2014.09.19 svn.r3010 for OlexSys, GUI svn.r4874)
;
_cell_angle_alpha                90
_cell_angle_beta                 107.2868(10)
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   15.49431(14)
_cell_length_b                   16.23501(13)
_cell_length_c                   15.84297(16)
_cell_measurement_reflns_used    28503
_cell_measurement_temperature    120.0
_cell_measurement_theta_max      76.1180
_cell_measurement_theta_min      3.9730
_cell_volume                     3805.28(6)
_computing_cell_refinement
;
CrysAlisPro, Agilent Technologies,
Version 1.171.37.34k (release 13-08-2014 CrysAlis171 .NET)
(compiled Aug 13 2014,16:31:05)
;
_computing_data_collection
;
CrysAlisPro, Agilent Technologies,
Version 1.171.37.34k (release 13-08-2014 CrysAlis171 .NET)
(compiled Aug 13 2014,16:31:05)
;
_computing_data_reduction
;
CrysAlisPro, Agilent Technologies,
Version 1.171.37.34k (release 13-08-2014 CrysAlis171 .NET)
(compiled Aug 13 2014,16:31:05)
;
_computing_molecular_graphics    'Olex2 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 (Dolomanov et al., 2009)'
_computing_structure_refinement  'ShelXL (Sheldrick, 2008)'
_computing_structure_solution    'SIR2008 (Burla et al., 2007)'
_diffrn_ambient_environment      N~2~
_diffrn_ambient_temperature      120.0
_diffrn_detector                 'CCD plate'
_diffrn_detector_area_resol_mean 5.1574
_diffrn_detector_type            Atlas
_diffrn_measured_fraction_theta_full 1.000
_diffrn_measured_fraction_theta_max 0.994
_diffrn_measurement_details
;
  1 omega  -50.00   29.00   1.0000   10.0000
omega____ theta____ kappa____ phi______ frames
    -      -43.4186   38.0000  -90.0000 79

  2 omega -117.00  -12.00   1.0000   10.0000
omega____ theta____ kappa____ phi______ frames
    -      -43.4186  -77.0000  -30.0000 105

  3 omega -122.00   -7.00   1.0000   10.0000
omega____ theta____ kappa____ phi______ frames
    -      -43.4186  -19.0000   90.0000 115

  4 omega  -95.00   -2.00   1.0000   10.0000
omega____ theta____ kappa____ phi______ frames
    -      -43.4186  125.0000    0.0000 93

  5 omega   23.00   98.00   1.0000   10.0000
omega____ theta____ kappa____ phi______ frames
    -       43.4186 -125.0000  -30.0000 75

  6 omega   23.00   98.00   1.0000   10.0000
omega____ theta____ kappa____ phi______ frames
    -       43.4186 -125.0000 -180.0000 75

  7 omega   30.00  109.00   1.0000   30.0000
omega____ theta____ kappa____ phi______ frames
    -      111.0000  -94.0000   60.0000 79

  8 omega   36.00   91.00   1.0000   30.0000
omega____ theta____ kappa____ phi______ frames
    -      111.0000  -30.0000    0.0000 55

  9 omega   36.00   91.00   1.0000   30.0000
omega____ theta____ kappa____ phi______ frames
    -      111.0000  -30.0000  150.0000 55

 10 omega   30.00  109.00   1.0000   30.0000
omega____ theta____ kappa____ phi______ frames
    -      111.0000  -94.0000    0.0000 79

 11 omega   39.00  121.00   1.0000   30.0000
omega____ theta____ kappa____ phi______ frames
    -      111.0000 -125.0000  -60.0000 82

 12 omega   36.00   91.00   1.0000   30.0000
omega____ theta____ kappa____ phi______ frames
    -      111.0000  -30.0000  -60.0000 55

 13 omega   94.00  178.00   1.0000   30.0000
omega____ theta____ kappa____ phi______ frames
    -      111.0000  125.0000 -180.0000 84

 14 omega   40.00   98.00   1.0000   30.0000
omega____ theta____ kappa____ phi______ frames
    -      111.0000  -45.0000  150.0000 58

 15 omega   36.00   91.00   1.0000   30.0000
omega____ theta____ kappa____ phi______ frames
    -      111.0000  -30.0000   60.0000 55

 16 omega   87.00  178.00   1.0000   30.0000
omega____ theta____ kappa____ phi______ frames
    -      111.0000   30.0000  -30.0000 91

 17 omega   24.00  178.00   1.0000   30.0000
omega____ theta____ kappa____ phi______ frames
    -      111.0000    0.0000 -150.0000 154

 18 omega   30.00  109.00   1.0000   30.0000
omega____ theta____ kappa____ phi______ frames
    -      111.0000  -94.0000 -180.0000 79

 19 omega   39.00  121.00   1.0000   30.0000
omega____ theta____ kappa____ phi______ frames
    -      111.0000 -125.0000 -180.0000 82

 20 omega   39.00  121.00   1.0000   30.0000
omega____ theta____ kappa____ phi______ frames
    -      111.0000 -125.0000  -90.0000 82

 21 omega   39.00  121.00   1.0000   30.0000
omega____ theta____ kappa____ phi______ frames
    -      111.0000 -125.0000    0.0000 82

 22 omega   36.00   91.00   1.0000   30.0000
omega____ theta____ kappa____ phi______ frames
    -      111.0000  -30.0000 -120.0000 55

 23 omega   37.00  142.00   1.0000   30.0000
omega____ theta____ kappa____ phi______ frames
    -      111.0000  -77.0000   30.0000 105

 24 omega   39.00  121.00   1.0000   30.0000
omega____ theta____ kappa____ phi______ frames
    -      111.0000 -125.0000   60.0000 82

 25 omega   36.00   91.00   1.0000   30.0000
omega____ theta____ kappa____ phi______ frames
    -      111.0000  -30.0000  120.0000 55

 26 omega   41.00  139.00   1.0000   30.0000
omega____ theta____ kappa____ phi______ frames
    -      111.0000  -61.0000 -120.0000 98

 27 omega   75.00  101.00   1.0000   30.0000
omega____ theta____ kappa____ phi______ frames
    -      111.0000 -125.0000 -120.0000 26

 28 omega   61.00   91.00   1.0000   30.0000
omega____ theta____ kappa____ phi______ frames
    -      111.0000  -61.0000 -150.0000 30

 29 omega   66.00  109.00   1.0000   30.0000
omega____ theta____ kappa____ phi______ frames
    -      111.0000  -94.0000  150.0000 43

 30 omega   40.00   68.00   1.0000   30.0000
omega____ theta____ kappa____ phi______ frames
    -      111.0000  -45.0000 -120.0000 28

 31 omega  101.00  177.00   1.0000   30.0000
omega____ theta____ kappa____ phi______ frames
    -      111.0000   30.0000   60.0000 76

 32 omega   30.00   89.00   1.0000   30.0000
omega____ theta____ kappa____ phi______ frames
    -      111.0000  -94.0000  120.0000 59

 33 omega   59.00   85.00   1.0000   30.0000
omega____ theta____ kappa____ phi______ frames
    -      111.0000  -94.0000   30.0000 26

 34 omega   93.00  119.00   1.0000   30.0000
omega____ theta____ kappa____ phi______ frames
    -      111.0000 -125.0000  120.0000 26

 35 omega   74.00  137.00   1.0000   30.0000
omega____ theta____ kappa____ phi______ frames
    -      111.0000  -77.0000  -90.0000 63
;
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'Agilent Technologies SuperNova'
_diffrn_measurement_method       '\w scans'
_diffrn_orient_matrix_UB_11      0.0380092000
_diffrn_orient_matrix_UB_12      -0.0867875000
_diffrn_orient_matrix_UB_13      -0.0061526000
_diffrn_orient_matrix_UB_21      -0.0651805000
_diffrn_orient_matrix_UB_22      -0.0095420000
_diffrn_orient_matrix_UB_23      -0.0941566000
_diffrn_orient_matrix_UB_31      0.0717308000
_diffrn_orient_matrix_UB_32      0.0372173000
_diffrn_orient_matrix_UB_33      -0.0383374000
_diffrn_radiation_monochromator  mirror
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54184
_diffrn_reflns_av_R_equivalents  0.0438
_diffrn_reflns_av_unetI/netI     0.0409
_diffrn_reflns_Laue_measured_fraction_full 1.000
_diffrn_reflns_Laue_measured_fraction_max 0.994
_diffrn_reflns_limit_h_max       19
_diffrn_reflns_limit_h_min       -16
_diffrn_reflns_limit_k_max       20
_diffrn_reflns_limit_k_min       -19
_diffrn_reflns_limit_l_max       18
_diffrn_reflns_limit_l_min       -19
_diffrn_reflns_number            62592
_diffrn_reflns_point_group_measured_fraction_full 0.997
_diffrn_reflns_point_group_measured_fraction_max 0.982
_diffrn_reflns_theta_full        67.684
_diffrn_reflns_theta_max         76.311
_diffrn_reflns_theta_min         2.987
_diffrn_source                   'sealed X-ray tube'
_diffrn_source_type              'SuperNova (Cu) X-ray Source'
_exptl_absorpt_coefficient_mu    3.576
_exptl_absorpt_correction_T_max  0.966
_exptl_absorpt_correction_T_min  0.912
_exptl_absorpt_correction_type   gaussian
_exptl_absorpt_process_details
;
CrysAlisPro, Agilent Technologies,
Version 1.171.37.34k (release 13-08-2014 CrysAlis171 .NET)
(compiled Aug 13 2014,16:31:05)
Numerical absorption correction based on gaussian integration over
			a multifaceted crystal model
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_crystal_colour            yellow
_exptl_crystal_colour_primary    yellow
_exptl_crystal_density_diffrn    1.303
_exptl_crystal_description       block
_exptl_crystal_F_000             1584
_exptl_crystal_recrystallization_method
'The material was recrystallised from THF by slow evaporation'
_exptl_crystal_size_max          0.1516
_exptl_crystal_size_mid          0.1178
_exptl_crystal_size_min          0.0455
_refine_diff_density_max         0.465
_refine_diff_density_min         -0.280
_refine_diff_density_rms         0.041
_refine_ls_abs_structure_details
;
 Flack x determined using 6145 quotients [(I+)-(I-)]/[(I+)+(I-)]
 (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259).
;
_refine_ls_abs_structure_Flack   -0.0058(13)
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.026
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     953
_refine_ls_number_reflns         15668
_refine_ls_number_restraints     1
_refine_ls_restrained_S_all      1.026
_refine_ls_R_factor_all          0.0367
_refine_ls_R_factor_gt           0.0323
_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^)+(0.0474P)^2^+0.1294P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0783
_refine_ls_wR_factor_ref         0.0803
_reflns_Friedel_coverage         0.905
_reflns_Friedel_fraction_full    0.993
_reflns_Friedel_fraction_max     0.969
_reflns_number_gt                14557
_reflns_number_total             15668
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            cs6b02281_si_004.cif
_cod_data_source_block           se4003
_cod_database_code               4516714
_chemical_oxdiff_formula         'C38 H44 Fe N4 O2'
_chemical_oxdiff_usercomment     '@ 120 K '
_reflns_odcompleteness_completeness 99.97
_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 Secondary CH2 refined with riding coordinates:
 C4(H4A,H4B), C5(H5A,H5B), C28(H28A,H28B), C29(H29A,H29B), C53(H53A,H53B),
 C54(H54A,H54B), C78(H78A,H78B), C79(H79A,H79B), C112(H11A,H11B), C113(H11C,
 H11D), C114(H11E,H11F), C115(H11G,H11H), C102(H10A,H10B), C103(H10C,H10D),
 C104(H10E,H10F), C105(H10G,H10H)
2.b Aromatic/amide H refined with riding coordinates:
 C8(H8), C9(H9), C11(H11), C17(H17), C19(H19), C32(H32), C33(H33), C35(H35),
 C41(H41), C43(H43), C58(H58), C59(H59), C61(H61), C67(H67), C69(H69), C82(H82),
  C83(H83), C85(H85), C91(H91), C93(H93)
2.c Idealised Me refined as rotating group:
 C14(H14A,H14B,H14C), C21(H21A,H21B,H21C), C22(H22A,H22B,H22C), C23(H23A,H23B,
 H23C), C38(H38A,H38B,H38C), C45(H45A,H45B,H45C), C46(H46A,H46B,H46C), C47(H47A,
 H47B,H47C), C64(H64A,H64B,H64C), C71(H71A,H71B,H71C), C72(H72A,H72B,H72C),
 C73(H73A,H73B,H73C), C88(H88A,H88B,H88C), C95(H95A,H95B,H95C), C96(H96A,H96B,
 H96C), C97(H97A,H97B,H97C)
;
_shelx_res_checksum              98962
_shelx_hkl_checksum              73401
_shelx_shelxl_version_number     2014/7
_olex2_diffrn_ambient_temperature_device 'Oxford Cryosystems Cryostream 700+'
_olex2_exptl_crystal_mounting_method
'The crystal was mounted on a MITIGEN holder in Paratone oil.'
_olex2_submission_original_sample_id ajm302_cr
_olex2_submission_special_instructions 'No special instructions were received'