Catalytic Asymmetric C‒H Arylation of (η6-Arene)Chromium Complexes: Facile Access to Planar-Chiral Phosphines
Batuecas, María; Luo, Junfei; Gergelitsová, Ivana; Krämer, Katrina; Whitaker, Daniel; Vitorica-Yrezabal, Iñigo J.; Larrosa, Igor; ACS Catalysis 9 (2019) 5268–; doi:10.1021/acscatal.9b00918

data_4514780
_publ_section_title
;
 Catalytic Asymmetric C--H Arylation of (\h6-Arene)Chromium Complexes:
 Facile Access to Planar-Chiral Phosphines
;
_journal_issue                   6
_journal_name_full               'ACS Catalysis'
_journal_page_first              5268
_journal_paper_doi               10.1021/acscatal.9b00918
_journal_volume                  9
_journal_year                    2019
_chemical_absolute_configuration ad
_chemical_formula_moiety         'C44 H40 O P2'
_chemical_formula_sum            'C44 H40 O P2'
_chemical_formula_weight         646.70
_space_group_crystal_system      orthorhombic
_space_group_IT_number           19
_space_group_name_Hall           'P 2ac 2ab'
_space_group_name_H-M_alt        'P 21 21 21'
_symmetry_space_group_name_Hall  'P 2ac 2ab'
_symmetry_space_group_name_H-M   'P 21 21 21'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     dual
_audit_creation_date             2018-06-08
_audit_creation_method
;
Olex2 1.2
(compiled 2018.04.26 svn.r3504 for OlexSys, GUI svn.r5492)
;
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   9.9449(2)
_cell_length_b                   17.1268(4)
_cell_length_c                   19.9556(4)
_cell_measurement_reflns_used    12996
_cell_measurement_temperature    150.00(10)
_cell_measurement_theta_max      27.2480
_cell_measurement_theta_min      2.0390
_cell_volume                     3398.92(12)
_computing_cell_refinement       'CrysAlisPro 1.171.40.7b (Rigaku OD, 2018)'
_computing_data_collection       'CrysAlisPro 1.171.40.7b (Rigaku OD, 2018)'
_computing_data_reduction        'CrysAlisPro 1.171.40.7b (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      150.00(10)
_diffrn_detector                 'CCD plate'
_diffrn_measured_fraction_theta_full 0.999
_diffrn_measured_fraction_theta_max 0.922
_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     66.00 109.00   1.00    1.00    --   19.70  50.00 -90.00   43
  2  \w    -52.00 -26.00   1.00    1.00    --   19.70  50.00  30.00   26
  3  \w      4.00 108.00   1.00    1.00    --   19.70  50.00  30.00  104
  4  \w    -47.00  33.00   1.00    1.00    --   19.70  40.00 -30.00   80
  5  \w     -5.00 107.00   1.00    1.00    --   19.70  20.00 -90.00  112
  6  \w     42.00 103.00   1.00    1.00    --   19.70  60.00   0.00   61
  7  \w    -70.00  22.00   1.00    1.00    --   19.70  20.00-120.00   92
  8  \w    -70.00  15.00   1.00    1.00    --   19.70  50.00 -90.00   85
;
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'XtaLAB AFC11 (RINC): quarter-chi single'
_diffrn_measurement_method       '\w scans'
_diffrn_orient_matrix_type
'CrysAlisPro convention (1999,Acta A55,543-557)'
_diffrn_orient_matrix_UB_11      -0.0429319000
_diffrn_orient_matrix_UB_12      0.0060625000
_diffrn_orient_matrix_UB_13      -0.0279254000
_diffrn_orient_matrix_UB_21      0.0567125000
_diffrn_orient_matrix_UB_22      0.0084262000
_diffrn_orient_matrix_UB_23      -0.0203211000
_diffrn_orient_matrix_UB_31      0.0054488000
_diffrn_orient_matrix_UB_32      -0.0400751000
_diffrn_orient_matrix_UB_33      -0.0084305000
_diffrn_radiation_monochromator  mirror
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0458
_diffrn_reflns_av_unetI/netI     0.0430
_diffrn_reflns_Laue_measured_fraction_full 0.999
_diffrn_reflns_Laue_measured_fraction_max 0.922
_diffrn_reflns_limit_h_max       13
_diffrn_reflns_limit_h_min       -12
_diffrn_reflns_limit_k_max       22
_diffrn_reflns_limit_k_min       -23
_diffrn_reflns_limit_l_max       25
_diffrn_reflns_limit_l_min       -26
_diffrn_reflns_number            36911
_diffrn_reflns_point_group_measured_fraction_full 0.999
_diffrn_reflns_point_group_measured_fraction_max 0.892
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         29.152
_diffrn_reflns_theta_min         1.567
_diffrn_source                   'Rotating-anode X-ray tube (dual wavelength)'
_diffrn_source_type              'Rigaku (Mo) X-ray DW Source'
_exptl_absorpt_coefficient_mu    0.163
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.86186
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
CrysAlisPro 1.171.40.7b (Rigaku Oxford Diffraction, 2018)
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_crystal_colour            'clear light colourless'
_exptl_crystal_colour_lustre     clear
_exptl_crystal_colour_modifier   light
_exptl_crystal_colour_primary    colourless
_exptl_crystal_density_diffrn    1.264
_exptl_crystal_description       block
_exptl_crystal_F_000             1368
_exptl_crystal_size_max          0.2
_exptl_crystal_size_mid          0.2
_exptl_crystal_size_min          0.2
_refine_diff_density_max         0.237
_refine_diff_density_min         -0.220
_refine_diff_density_rms         0.041
_refine_ls_abs_structure_details
;
 Flack x determined using 2769 quotients [(I+)-(I-)]/[(I+)+(I-)]
 (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259).
;
_refine_ls_abs_structure_Flack   -0.05(4)
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.040
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     433
_refine_ls_number_reflns         8187
_refine_ls_number_restraints     72
_refine_ls_restrained_S_all      1.038
_refine_ls_R_factor_all          0.0500
_refine_ls_R_factor_gt           0.0381
_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^)+(0.0405P)^2^+0.5552P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0850
_refine_ls_wR_factor_ref         0.0895
_reflns_Friedel_coverage         0.743
_reflns_Friedel_fraction_full    1.000
_reflns_Friedel_fraction_max     0.855
_reflns_number_gt                7033
_reflns_number_total             8187
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            cs9b00918_si_002.cif
_cod_data_source_block           s5257l
_cod_original_cell_volume        3398.94(13)
_cod_database_code               4514780
_shelxl_version_number           2014/6
_shelx_estimated_absorpt_t_max   0.968
_shelx_estimated_absorpt_t_min   0.968
_reflns_odcompleteness_completeness 99.95
_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
2. Uiso/Uaniso restraints and constraints
O24 \\sim P23 \\sim P11 \\sim O12: within 2A with sigma of 0.002 and sigma for
terminal atoms of 0.004
3. Rigid body (RIGU) restrains
 O24, P23, C13, C25, C31, O12, P11, C43, C37, C1
 with sigma for 1-2 distances of 0.002 and sigma for 1-3 distances of 0.002
4. Others
 Fixed Sof: O24(0.5) O12(0.5)
5.a Secondary CH2 refined with riding coordinates:
 C16(H16A,H16B), C4(H4A,H4B), C19(H19A,H19B), C17(H17A,H17B), C7(H7A,H7B),
 C18(H18A,H18B), C5(H5A,H5B), C6(H6A,H6B)
5.b Aromatic/amide H refined with riding coordinates:
 C22(H22), C10(H10), C21(H21), C32(H32), C36(H36), C9(H9), C44(H44), C42(H42),
 C41(H41), C48(H48), C34(H34), C39(H39), C26(H26), C40(H40), C30(H30), C38(H38),
  C45(H45), C35(H35), C33(H33), C29(H29), C47(H47), C28(H28), C46(H46), C27(H27)
;
_shelx_res_checksum              99138
_shelx_hkl_checksum              41709
_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 1.143
_oxdiff_exptl_absorpt_empirical_full_min 0.834