Facile synthesis of axially chiral styrene-type carboxylic acids via palladium-catalyzed asymmetric C–H activation
Yang, Chi; Wu, Tian-Rui; Li, Yan; Wu, Bing-Bing; Jin, Ruo-Xing; Hu, Duo-Duo; Li, Yuan-Bo; Bian, Kang-Jie; Wang, Xi-Sheng; Chemical Science 12 (2021) 3726–3732; doi:10.1039/D0SC06661C

data_1560125
_publ_section_title
;
 Facile synthesis of axially chiral styrene-type carboxylic acids via
 palladium-catalyzed asymmetric C--H activation
;
_journal_issue                   10
_journal_name_full               'Chemical Science'
_journal_page_first              3726
_journal_page_last               3732
_journal_paper_doi               10.1039/D0SC06661C
_journal_volume                  12
_journal_year                    2021
_chemical_formula_moiety         'C24 H20 O4'
_chemical_formula_sum            'C24 H20 O4'
_chemical_formula_weight         372.40
_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'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     dual
_audit_block_doi                 10.5517/ccdc.csd.cc26nzql
_audit_creation_date             2020-01-18
_audit_creation_method
;
Olex2 1.3
(compiled Nov 21 2019 18:26:39 for OlexSys, GUI svn.r6003)
;
_audit_update_record
;
2020-11-23 deposited with the CCDC.	2021-01-20 downloaded from the CCDC.
;
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_formula_units_Z            8
_cell_length_a                   8.99240(10)
_cell_length_b                   19.5139(2)
_cell_length_c                   23.2425(2)
_cell_measurement_temperature    293(2)
_cell_volume                     4078.52(7)
_computing_molecular_graphics    'Olex2 1.3 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 1.3 (Dolomanov et al., 2009)'
_computing_structure_refinement  'SHELXL 2018/3 (Sheldrick, 2015)'
_computing_structure_solution    'SHELXT  (Sheldrick, 2015)'
_diffrn_ambient_temperature      293(2)
_diffrn_measured_fraction_theta_full 0.999
_diffrn_measured_fraction_theta_max 0.994
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54184
_diffrn_reflns_av_R_equivalents  0.0341
_diffrn_reflns_av_unetI/netI     0.0182
_diffrn_reflns_Laue_measured_fraction_full 0.999
_diffrn_reflns_Laue_measured_fraction_max 0.994
_diffrn_reflns_limit_h_max       10
_diffrn_reflns_limit_h_min       -11
_diffrn_reflns_limit_k_max       24
_diffrn_reflns_limit_k_min       -24
_diffrn_reflns_limit_l_max       28
_diffrn_reflns_limit_l_min       -28
_diffrn_reflns_number            42944
_diffrn_reflns_point_group_measured_fraction_full 0.998
_diffrn_reflns_point_group_measured_fraction_max 0.988
_diffrn_reflns_theta_full        67.684
_diffrn_reflns_theta_max         73.193
_diffrn_reflns_theta_min         3.804
_exptl_absorpt_coefficient_mu    0.664
_exptl_crystal_density_diffrn    1.213
_exptl_crystal_F_000             1568
_refine_diff_density_max         0.403
_refine_diff_density_min         -0.236
_refine_diff_density_rms         0.048
_refine_ls_abs_structure_details
;
 Flack x determined using 2644 quotients [(I+)-(I-)]/[(I+)+(I-)]
 (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259).
;
_refine_ls_abs_structure_Flack   -0.07(8)
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.578
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     509
_refine_ls_number_reflns         8078
_refine_ls_number_restraints     10
_refine_ls_restrained_S_all      1.580
_refine_ls_R_factor_all          0.0754
_refine_ls_R_factor_gt           0.0670
_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^)+(0.1000P)^2^] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1995
_refine_ls_wR_factor_ref         0.2077
_reflns_Friedel_coverage         0.775
_reflns_Friedel_fraction_full    0.998
_reflns_Friedel_fraction_max     0.981
_reflns_number_gt                6953
_reflns_number_total             8078
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            d0sc06661c2.cif
_cod_data_source_block           liyan-yangchi-200115
_cod_depositor_comments
'Adding full bibliography for 1560125--1560126.cif.'
_cod_database_code               1560125
_shelx_shelxl_version_number     2018/3
_olex2_refinement_description
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups
 At 1.5 times of:
  All C(H,H,H) groups
2. Rigid bond restraints
 C102, C123, C104, C105, C109, C110, C107, C108
 with sigma for 1-2 distances of 0.001 and sigma for 1-3 distances of 0.001
3.a Aromatic/amide H refined with riding coordinates:
 C23(H23), C12(H12), C14(H14), C24(H24), C9(H9), C112(H112), C3(H3), C15(H15),
 C117(H117), C7(H7), C118(H118), C4(H4), C116(H116), C109(H109), C16(H16),
 C6(H6), C8(H8), C114(H114), C104(H104), C18(H18), C123(H123), C107(H107),
 C103(H103), C115(H115), C124(H124), C17(H17), C108(H108), C106(H106)
3.b Idealised Me refined as rotating group:
 C22(H22A,H22B,H22C), C28(H28A,H28B,H28C), C122(H12A,H12B,H12C), C128(H12D,
 H12E,H12F)
;
_shelx_res_checksum              38511
_shelx_hkl_checksum              41149
_olex2_submission_special_instructions 'No special instructions were received'