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_4514408
_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         'C58 H63 Ag O3 P2, C4 H10 O, 0.78(H2 O)'
_chemical_formula_sum            'C62 H74.56 Ag O4.78 P2'
_chemical_formula_weight         1066.06
_space_group_crystal_system      monoclinic
_space_group_IT_number           5
_space_group_name_Hall           'I 2y'
_space_group_name_H-M_alt        'I 1 2 1'
_symmetry_space_group_name_Hall  'I 2y'
_symmetry_space_group_name_H-M   'I 1 2 1'
_atom_sites_solution_hydrogens   mixed
_atom_sites_solution_primary     dual
_audit_creation_date             2018-11-05
_audit_creation_method
;
Olex2 1.2
(compiled 2018.05.29 svn.r3508 for OlexSys, GUI svn.r5506)
;
_cell_angle_alpha                90
_cell_angle_beta                 106.036(3)
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   11.7485(3)
_cell_length_b                   26.0007(9)
_cell_length_c                   18.5841(6)
_cell_measurement_reflns_used    7871
_cell_measurement_temperature    150
_cell_measurement_theta_max      26.4830
_cell_measurement_theta_min      1.5550
_cell_volume                     5456.0(3)
_computing_cell_refinement       'CrysAlisPro 1.171.40.14d (Rigaku OD, 2018)'
_computing_data_collection       'CrysAlisPro 1.171.40.14d (Rigaku OD, 2018)'
_computing_data_reduction        'CrysAlisPro 1.171.40.14d (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_temperature      150
_diffrn_detector                 'CCD plate'
_diffrn_measured_fraction_theta_full 1.000
_diffrn_measured_fraction_theta_max 0.903
_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     -1.00  26.00   1.00    6.00    --   19.90  20.00-167.00   27
  2  \w    -65.00 -38.00   1.00    6.00    --   19.90  57.00 -90.00   27
  3  \w    -20.00   7.00   1.00    6.00    --   19.90  57.00 -90.00   27
  4  \w     21.00  90.00   1.00    6.00    --   19.90  57.00 -90.00   69
  5  \w    -70.00 106.00   1.00    6.00    --   19.90  29.00  60.00  176
  6  \w    -69.00  74.00   1.00    6.00    --   19.90  57.00 -60.00  143
  7  \w     64.00 105.00   1.00    6.00    --   19.90  60.00  60.00   41
  8  \w    -61.00 101.00   1.00    6.00    --   19.90  60.00   0.00  162
  9  \w     19.00  78.00   1.00    6.00    --   19.90  60.00  30.00   59
;
_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      0.0624554000
_diffrn_orient_matrix_UB_12      -0.0021040000
_diffrn_orient_matrix_UB_13      0.0136792000
_diffrn_orient_matrix_UB_21      -0.0026558000
_diffrn_orient_matrix_UB_22      0.0093499000
_diffrn_orient_matrix_UB_23      0.0353720000
_diffrn_orient_matrix_UB_31      -0.0060721000
_diffrn_orient_matrix_UB_32      -0.0255367000
_diffrn_orient_matrix_UB_33      0.0118182000
_diffrn_radiation_monochromator  mirror
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0535
_diffrn_reflns_av_unetI/netI     0.0855
_diffrn_reflns_Laue_measured_fraction_full 1.000
_diffrn_reflns_Laue_measured_fraction_max 0.903
_diffrn_reflns_limit_h_max       15
_diffrn_reflns_limit_h_min       -15
_diffrn_reflns_limit_k_max       34
_diffrn_reflns_limit_k_min       -34
_diffrn_reflns_limit_l_max       25
_diffrn_reflns_limit_l_min       -24
_diffrn_reflns_number            34511
_diffrn_reflns_point_group_measured_fraction_full 1.000
_diffrn_reflns_point_group_measured_fraction_max 0.903
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         29.128
_diffrn_reflns_theta_min         1.566
_diffrn_source                   'Rotating-anode X-ray tube (dual wavelength)'
_diffrn_source_type              'Rigaku (Mo) X-ray DW Source'
_exptl_absorpt_coefficient_mu    0.476
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.48307
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
CrysAlisPro 1.171.40.14d (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    1.298
_exptl_crystal_description       plate
_exptl_crystal_F_000             2247
_exptl_crystal_size_max          0.12
_exptl_crystal_size_mid          0.1
_exptl_crystal_size_min          0.06
_refine_diff_density_max         0.741
_refine_diff_density_min         -0.700
_refine_diff_density_rms         0.080
_refine_ls_abs_structure_details
;
 Refined as an inversion twin.
;
_refine_ls_abs_structure_Flack   0.45(3)
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.011
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     639
_refine_ls_number_reflns         12690
_refine_ls_number_restraints     37
_refine_ls_restrained_S_all      1.018
_refine_ls_R_factor_all          0.0813
_refine_ls_R_factor_gt           0.0523
_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^)+(0.0670P)^2^] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1157
_refine_ls_wR_factor_ref         0.1250
_reflns_Friedel_coverage         0.958
_reflns_Friedel_fraction_full    1.000
_reflns_Friedel_fraction_max     0.903
_reflns_number_gt                9512
_reflns_number_total             12690
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            cs9b00918_si_003.cif
_cod_data_source_block           s5188l
_cod_depositor_comments
'Adding full bibliography for 4514406--4514408.cif.'
_cod_original_cell_volume        5455.9(3)
_cod_database_code               4514408
_shelxl_version_number           2014/6
_shelx_estimated_absorpt_t_max   0.972
_shelx_estimated_absorpt_t_min   0.945
_reflns_odcompleteness_completeness 99.98
_reflns_odcompleteness_iscentric 1
_reflns_odcompleteness_theta     26.32
_olex2_refinement_description
;
1. Twinned data refinement
 Scales: 0.55(3)
 0.45(3)
2. 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 O(H,H) groups
3. Restrained distances
 O60-C63
 1.45 with sigma of 0.02
 C64-C63
 1.54 with sigma of 0.02
 C63-C61
 2.4 with sigma of 0.02
4. Uiso/Uaniso restraints and constraints
C62 \\sim C61 \\sim C63 \\sim C64: within 2A with sigma of 0.002 and sigma for
terminal atoms of 0.004
5. Rigid body (RIGU) restrains
 C62, C61, O60, C63, C64
 with sigma for 1-2 distances of 0.002 and sigma for 1-3 distances of 0.002
6. Others
 Sof(O0AA)=Sof(H0AA)=Sof(H0AB)=0.5*(1-FVAR(2))
 Sof(O1)=Sof(H1A)=Sof(H1B)=FVAR(1)
7.a Riding coordinates:
 O1(H1A,H1B), O0AA(H0AA,H0AB)
7.b Ternary CH refined with riding coordinates:
 C47(H47), C46(H46), C53(H53)
7.c Secondary CH2 refined with riding coordinates:
 C29(H29A,H29B), C21(H21A,H21B), C32(H32A,H32B), C30(H30A,H30B), C49(H49A,
 H49B), C23(H23A,H23B), C48(H48A,H48B), C55(H55A,H55B), C54(H54A,H54B),
 C50(H50A,H50B), C58(H58A,H58B), C22(H22A,H22B), C52(H52A,H52B), C24(H24A,H24B),
  C51(H51A,H51B), C56(H56A,H56B), C31(H31A,H31B), C57(H57A,H57B), C61(H61A,
 H61B), C63(H63A,H63B)
7.d Me refined with riding coordinates:
 C64(H64A,H64B,H64C)
7.e Aromatic/amide H refined with riding coordinates:
 C18(H18), C17(H17), C40(H40), C28(H28), C27(H27), C6(H6), C43(H43), C35(H35),
 C34(H34), C36(H36), C12(H12), C16(H16), C10(H10), C41(H41), C44(H44), C38(H38),
  C42(H42), C13(H13), C9(H9), C14(H14), C37(H37), C7(H7), C8(H8), C15(H15)
7.f Idealised Me refined as rotating group:
 C62(H62A,H62B,H62C)
;
_shelx_res_checksum              59450
_shelx_hkl_checksum              47713
_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 1.583
_oxdiff_exptl_absorpt_empirical_full_min 0.632