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_4516711
_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_formula_moiety         'C36 H38 Fe N4 O2, C4 H8 O'
_chemical_formula_sum            'C40 H46 Fe N4 O3'
_chemical_formula_weight         686.66
_space_group_crystal_system      orthorhombic
_space_group_IT_number           60
_space_group_name_Hall           '-P 2n 2ab'
_space_group_name_H-M_alt        'P b c n'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_audit_creation_date             2014-07-18
_audit_creation_method
;
Olex2 1.2
(compiled 2014.06.27 svn.r2953 for OlexSys, GUI svn.r4855)
;
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_formula_units_Z            8
_cell_length_a                   24.0256(5)
_cell_length_b                   13.1262(3)
_cell_length_c                   22.3213(6)
_cell_measurement_reflns_used    30173
_cell_measurement_temperature    120.0
_cell_measurement_theta_max      30.8090
_cell_measurement_theta_min      3.2480
_cell_volume                     7039.4(3)
_computing_cell_refinement
;
CrysAlisPro, Agilent Technologies,
Version 1.171.37.33 (release 27-03-2014 CrysAlis171 .NET)
(compiled Mar 27 2014,17:12:48)
;
_computing_data_collection
;
CrysAlisPro, Agilent Technologies,
Version 1.171.37.33 (release 27-03-2014 CrysAlis171 .NET)
(compiled Mar 27 2014,17:12:48)
;
_computing_data_reduction
;
CrysAlisPro, Agilent Technologies,
Version 1.171.37.33 (release 27-03-2014 CrysAlis171 .NET)
(compiled Mar 27 2014,17:12:48)
;
_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    'ShelXS (Sheldrick, 2008)'
_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 0.997
_diffrn_measured_fraction_theta_max 0.963
_diffrn_measurement_details
;
  1 omega  -86.00    9.00   1.0000   15.0000
omega____ theta____ kappa____ phi______ frames
    -      -13.2412  -38.0000 -150.0000 95

  2 omega  -80.00  -34.00   1.0000   15.0000
omega____ theta____ kappa____ phi______ frames
    -      -13.2412  144.0000   65.6532 46

  3 omega  -83.00   13.00   1.0000   15.0000
omega____ theta____ kappa____ phi______ frames
    -      -13.2412  -57.0000  -90.0000 96

  4 omega  -83.00   13.00   1.0000   15.0000
omega____ theta____ kappa____ phi______ frames
    -      -13.2412  -57.0000  120.0000 96

  5 omega  -83.00  -15.00   1.0000   15.0000
omega____ theta____ kappa____ phi______ frames
    -      -13.2412  -57.0000   90.0000 68

  6 omega   -2.00   23.00   1.0000   15.0000
omega____ theta____ kappa____ phi______ frames
    -      -13.2412  -99.0000  -90.0000 25

  7 omega  -92.00  -16.00   1.0000   15.0000
omega____ theta____ kappa____ phi______ frames
    -      -13.2412  -19.0000  150.0000 76

  8 omega  -16.00   40.00   1.0000   15.0000
omega____ theta____ kappa____ phi______ frames
    -       14.3350  -57.0000   60.0000 56

  9 omega  -37.00    6.00   1.0000   15.0000
omega____ theta____ kappa____ phi______ frames
    -       14.3350  -38.0000  -60.0000 43

 10 omega   36.00   61.00   1.0000   15.0000
omega____ theta____ kappa____ phi______ frames
    -       14.3350 -178.0000  -90.0000 25

 11 omega   35.00   89.00   1.0000   15.0000
omega____ theta____ kappa____ phi______ frames
    -       14.3350  178.0000 -120.0000 54

 12 omega   54.00   93.00   1.0000   15.0000
omega____ theta____ kappa____ phi______ frames
    -       14.3350 -178.0000   90.0000 39
;
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'Agilent Technologies SuperNova'
_diffrn_measurement_method       '\w scans'
_diffrn_orient_matrix_UB_11      0.0205120000
_diffrn_orient_matrix_UB_12      -0.0064904000
_diffrn_orient_matrix_UB_13      -0.0225249000
_diffrn_orient_matrix_UB_21      -0.0211217000
_diffrn_orient_matrix_UB_22      -0.0009166000
_diffrn_orient_matrix_UB_23      -0.0222033000
_diffrn_orient_matrix_UB_31      0.0021241000
_diffrn_orient_matrix_UB_32      0.0536322000
_diffrn_orient_matrix_UB_33      -0.0030982000
_diffrn_radiation_monochromator  mirror
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0553
_diffrn_reflns_av_unetI/netI     0.0310
_diffrn_reflns_Laue_measured_fraction_full 0.997
_diffrn_reflns_Laue_measured_fraction_max 0.963
_diffrn_reflns_limit_h_max       34
_diffrn_reflns_limit_h_min       -34
_diffrn_reflns_limit_k_max       17
_diffrn_reflns_limit_k_min       -18
_diffrn_reflns_limit_l_max       31
_diffrn_reflns_limit_l_min       -31
_diffrn_reflns_number            145241
_diffrn_reflns_point_group_measured_fraction_full 0.997
_diffrn_reflns_point_group_measured_fraction_max 0.963
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         31.177
_diffrn_reflns_theta_min         2.935
_diffrn_source                   'SuperNova (Mo) X-ray Source'
_exptl_absorpt_coefficient_mu    0.472
_exptl_absorpt_correction_T_max  0.984
_exptl_absorpt_correction_T_min  0.909
_exptl_absorpt_correction_type   gaussian
_exptl_absorpt_process_details
;
CrysAlisPro, Agilent Technologies,
Version 1.171.37.33 (release 27-03-2014 CrysAlis171 .NET)
(compiled Mar 27 2014,17:12:48)
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            'dark green'
_exptl_crystal_colour_modifier   dark
_exptl_crystal_colour_primary    green
_exptl_crystal_density_diffrn    1.296
_exptl_crystal_description       block
_exptl_crystal_F_000             2912
_exptl_crystal_recrystallization_method THF
_exptl_crystal_size_max          0.5841
_exptl_crystal_size_mid          0.2354
_exptl_crystal_size_min          0.0624
_refine_diff_density_max         0.408
_refine_diff_density_min         -0.430
_refine_diff_density_rms         0.060
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.080
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     439
_refine_ls_number_reflns         10975
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.080
_refine_ls_R_factor_all          0.0631
_refine_ls_R_factor_gt           0.0460
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'w=1/[\s^2^(Fo^2^)+(0.0368P)^2^+5.6501P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1030
_refine_ls_wR_factor_ref         0.1099
_reflns_Friedel_coverage         0.000
_reflns_number_gt                8858
_reflns_number_total             10975
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            cs6b02281_si_003.cif
_cod_data_source_block           se4002
_cod_database_code               4516711
_shelxl_version_number           2014-1
_chemical_oxdiff_formula         'C36 H40 Fe N4 O2'
_chemical_oxdiff_usercomment     '@ 120 K ajm278_rc1'
_reflns_odcompleteness_completeness 99.73
_reflns_odcompleteness_iscentric 1
_reflns_odcompleteness_theta     26.32
_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, All C(H,H,H,H,H,H) groups
2. Others
 Fixed Sof: H42A(0.5) H42B(0.5) H42C(0.5) H42D(0.5) H42E(0.5) H42F(0.5)
3.a Secondary CH2 refined with riding coordinates:
 C4(H4A,H4B), C5(H5A,H5B), C26(H26A,H26B), C27(H27A,H27B), C45(H45A,H45B),
 C46(H46A,H46B), C47(H47A,H47B), C48(H48A,H48B)
3.b Aromatic/amide H refined with riding coordinates:
 C8(H8), C9(H9), C10(H10), C11(H11), C15(H15), C17(H17), C30(H30), C31(H31),
 C32(H32), C33(H33), C37(H37), C39(H39)
3.c Disordered Me refined as rotating group:
 C42(H42A,H42B,H42C,H42D,H42E,H42F)
3.d Idealised Me refined as rotating group:
 C19(H19A,H19B,H19C), C20(H20A,H20B,H20C), C21(H21A,H21B,H21C), C41(H41A,H41B,
 H41C), C43(H43A,H43B,H43C)
;
_shelx_res_checksum              754
_shelx_hkl_checksum              96001
_olex2_exptl_crystal_mounting_method 'Mitegen tip, Paratone oil.'
_olex2_submission_original_sample_id ajm278_rc1
_olex2_submission_special_instructions 'No special instructions were received'