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_4516713
_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 H36 Fe N6 O6'
_chemical_formula_sum            'C36 H36 Fe N6 O6'
_chemical_formula_weight         704.56
_space_group_crystal_system      monoclinic
_space_group_IT_number           14
_space_group_name_Hall           '-P 2yn'
_space_group_name_H-M_alt        'P 1 21/n 1'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     heavy
_audit_creation_date             2014-10-08
_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                 97.427(3)
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   8.0949(2)
_cell_length_b                   23.7481(5)
_cell_length_c                   17.1961(5)
_cell_measurement_reflns_used    9263
_cell_measurement_temperature    120.0
_cell_measurement_theta_max      75.3560
_cell_measurement_theta_min      4.5150
_cell_volume                     3278.02(14)
_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    '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 1.000
_diffrn_measured_fraction_theta_max 0.993
_diffrn_measurement_details
;
  1 omega  -50.00   29.00   1.0000   15.0000
omega____ theta____ kappa____ phi______ frames
    -      -43.1686   38.0000  -60.0000 79

  2 omega  -50.00   29.00   1.0000   15.0000
omega____ theta____ kappa____ phi______ frames
    -      -43.1686   38.0000  150.0000 79

  3 omega  -96.00   -2.00   1.0000   15.0000
omega____ theta____ kappa____ phi______ frames
    -      -43.1686  125.0000  150.0000 94

  4 omega -122.00   -6.00   1.0000   15.0000
omega____ theta____ kappa____ phi______ frames
    -      -43.1686  -19.0000  -30.0000 116

  5 omega   23.00   98.00   1.0000   15.0000
omega____ theta____ kappa____ phi______ frames
    -       43.1686 -125.0000   30.0000 75

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

  7 omega   36.00   91.00   1.0000   30.0000
omega____ theta____ kappa____ phi______ frames
    -      111.0000  -30.0000   90.0000 55

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

  9 omega   94.00  178.00   1.0000   30.0000
omega____ theta____ kappa____ phi______ frames
    -      111.0000  125.0000   60.0000 84

 10 omega   94.00  178.00   1.0000   30.0000
omega____ theta____ kappa____ phi______ frames
    -      111.0000  125.0000 -150.0000 84

 11 omega   83.00  178.00   1.0000   30.0000
omega____ theta____ kappa____ phi______ frames
    -      111.0000   61.0000  120.0000 95

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

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

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

 15 omega   36.00   91.00   1.0000   30.0000
omega____ theta____ kappa____ phi______ frames
    -      111.0000  -30.0000 -180.0000 55

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

 17 omega   30.00  109.00   1.0000   30.0000
omega____ theta____ kappa____ phi______ frames
    -      111.0000  -94.0000  120.0000 79

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

 19 omega   87.00  178.00   1.0000   30.0000
omega____ theta____ kappa____ phi______ frames
    -      111.0000   30.0000 -150.0000 91

 20 omega   37.00  142.00   1.0000   30.0000
omega____ theta____ kappa____ phi______ frames
    -      111.0000  -77.0000  150.0000 105

 21 omega -117.00  -12.00   1.0000   15.0000
omega____ theta____ kappa____ phi______ frames
    -      -43.1686  -77.0000  -90.0000 105

 22 omega -117.00  -12.00   1.0000   15.0000
omega____ theta____ kappa____ phi______ frames
    -      -43.1686  -77.0000    0.0000 105

 23 omega -117.00  -12.00   1.0000   15.0000
omega____ theta____ kappa____ phi______ frames
    -      -43.1686  -77.0000 -180.0000 105

 24 omega  -70.00   27.00   1.0000   15.0000
omega____ theta____ kappa____ phi______ frames
    -      -43.1686   57.0000   30.0000 97

 25 omega -116.00  -21.00   1.0000   15.0000
omega____ theta____ kappa____ phi______ frames
    -      -43.1686  -38.0000  -60.0000 95

 26 omega -117.00  -12.00   1.0000   15.0000
omega____ theta____ kappa____ phi______ frames
    -      -43.1686  -77.0000   90.0000 105

 27 omega   66.00  178.00   1.0000   30.0000
omega____ theta____ kappa____ phi______ frames
    -      111.0000   15.0000    0.0000 112

 28 omega   87.00  178.00   1.0000   30.0000
omega____ theta____ kappa____ phi______ frames
    -      111.0000   30.0000  -90.0000 91

 29 omega   87.00  178.00   1.0000   30.0000
omega____ theta____ kappa____ phi______ frames
    -      111.0000   45.0000   60.0000 91
;
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'SuperNova, Dual, Cu at zero, Atlas'
_diffrn_measurement_method       '\w scans'
_diffrn_orient_matrix_UB_11      0.0493883000
_diffrn_orient_matrix_UB_12      0.0092846000
_diffrn_orient_matrix_UB_13      0.0886423000
_diffrn_orient_matrix_UB_21      0.1773714000
_diffrn_orient_matrix_UB_22      0.0163632000
_diffrn_orient_matrix_UB_23      -0.0149015000
_diffrn_orient_matrix_UB_31      -0.0542023000
_diffrn_orient_matrix_UB_32      0.0620638000
_diffrn_orient_matrix_UB_33      -0.0092943000
_diffrn_radiation_monochromator  mirror
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54184
_diffrn_reflns_av_R_equivalents  0.0772
_diffrn_reflns_av_unetI/netI     0.0498
_diffrn_reflns_Laue_measured_fraction_full 1.000
_diffrn_reflns_Laue_measured_fraction_max 0.993
_diffrn_reflns_limit_h_max       10
_diffrn_reflns_limit_h_min       -10
_diffrn_reflns_limit_k_max       29
_diffrn_reflns_limit_k_min       -25
_diffrn_reflns_limit_l_max       21
_diffrn_reflns_limit_l_min       -21
_diffrn_reflns_number            50139
_diffrn_reflns_point_group_measured_fraction_full 1.000
_diffrn_reflns_point_group_measured_fraction_max 0.993
_diffrn_reflns_theta_full        67.684
_diffrn_reflns_theta_max         76.258
_diffrn_reflns_theta_min         3.191
_diffrn_source                   'sealed X-ray tube'
_diffrn_source_type              'SuperNova (Cu) X-ray Source'
_exptl_absorpt_coefficient_mu    4.164
_exptl_absorpt_correction_T_max  0.999
_exptl_absorpt_correction_T_min  0.998
_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            red
_exptl_crystal_colour_primary    red
_exptl_crystal_density_diffrn    1.428
_exptl_crystal_description       cylinder
_exptl_crystal_F_000             1472
_exptl_crystal_recrystallization_method
'The material was recrystallised from THF by slow evaporation'
_exptl_crystal_size_length       0.000
_exptl_crystal_size_max          0.1412
_exptl_crystal_size_mid          0.0445
_exptl_crystal_size_min          0.0306
_exptl_crystal_size_rad          0.000
_refine_diff_density_max         0.252
_refine_diff_density_min         -0.377
_refine_diff_density_rms         0.054
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.034
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     449
_refine_ls_number_reflns         6812
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.034
_refine_ls_R_factor_all          0.0635
_refine_ls_R_factor_gt           0.0462
_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^)+(0.0387P)^2^+1.4399P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0933
_refine_ls_wR_factor_ref         0.1000
_reflns_Friedel_coverage         0.000
_reflns_number_gt                5437
_reflns_number_total             6812
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            cs6b02281_si_005.cif
_cod_data_source_block           se4004
_cod_original_cell_volume        3278.00(15)
_cod_database_code               4516713
_chemical_oxdiff_formula         'C36 H36 Fe N6 O6'
_chemical_oxdiff_usercomment     '@ 120 K ajm296_cr'
_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, All C(H,H,H,H,H,H) groups
2. Others
 Sof(H48D)=Sof(H48E)=Sof(H48F)=1-FVAR(1)
 Sof(H48A)=Sof(H48B)=Sof(H48C)=FVAR(1)
3.a Secondary CH2 refined with riding coordinates:
 C4(H4A,H4B), C5(H5A,H5B), C29(H29A,H29B), C30(H30A,H30B)
3.b Aromatic/amide H refined with riding coordinates:
 C8(H8), C9(H9), C11(H11), C18(H18), C20(H20), C33(H33), C34(H34), C36(H36),
 C43(H43), C45(H45)
3.c Disordered Me refined as rotating group:
 C48(H48A,H48B,H48C,H48D,H48E,H48F)
3.d Idealised Me refined as rotating group:
 C22(H22A,H22B,H22C), C23(H23A,H23B,H23C), C24(H24A,H24B,H24C), C47(H47A,H47B,
 H47C), C49(H49A,H49B,H49C)
;
_shelx_res_checksum              49268
_shelx_hkl_checksum              44784
_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 ajm296_cr
_olex2_submission_special_instructions 'No special instructions were received'