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_1560126
_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_absolute_configuration ad
_chemical_formula_moiety         'C25 H18 O2'
_chemical_formula_sum            'C25 H18 O2'
_chemical_formula_weight         350.39
_space_group_crystal_system      triclinic
_space_group_IT_number           1
_space_group_name_Hall           'P 1'
_space_group_name_H-M_alt        'P 1'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     dual
_audit_creation_date             2020-07-17
_audit_creation_method
;
Olex2 1.3
(compiled 2020.02.04 svn.rd84adfe8 for OlexSys, GUI svn.r6032)
;
_audit_update_record
;
2020-11-23 deposited with the CCDC.	2021-01-20 downloaded from the CCDC.
;
_cell_angle_alpha                87.3760(10)
_cell_angle_beta                 70.785(2)
_cell_angle_gamma                81.6190(10)
_cell_formula_units_Z            2
_cell_length_a                   8.6935(2)
_cell_length_b                   11.1218(2)
_cell_length_c                   12.2142(2)
_cell_measurement_reflns_used    31556
_cell_measurement_temperature    293(2)
_cell_measurement_theta_max      70.1700
_cell_measurement_theta_min      5.4410
_cell_volume                     1103.26(4)
_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 2018/2 (Sheldrick, 2018)'
_diffrn_ambient_temperature      293(2)
_diffrn_measured_fraction_theta_full 0.998
_diffrn_measured_fraction_theta_max 0.989
_diffrn_measurement_device_type  'SuperNova, Dual, Cu at home/near, AtlasS2'
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54184
_diffrn_reflns_av_R_equivalents  0.0270
_diffrn_reflns_av_unetI/netI     0.0128
_diffrn_reflns_Laue_measured_fraction_full 0.998
_diffrn_reflns_Laue_measured_fraction_max 0.989
_diffrn_reflns_limit_h_max       10
_diffrn_reflns_limit_h_min       -10
_diffrn_reflns_limit_k_max       13
_diffrn_reflns_limit_k_min       -13
_diffrn_reflns_limit_l_max       14
_diffrn_reflns_limit_l_min       -14
_diffrn_reflns_number            36949
_diffrn_reflns_point_group_measured_fraction_full 0.954
_diffrn_reflns_point_group_measured_fraction_max 0.937
_diffrn_reflns_theta_full        67.684
_diffrn_reflns_theta_max         69.948
_diffrn_reflns_theta_min         3.833
_exptl_absorpt_coefficient_mu    0.520
_exptl_crystal_density_diffrn    1.055
_exptl_crystal_description       block
_exptl_crystal_F_000             368
_exptl_crystal_size_max          0.4
_exptl_crystal_size_mid          0.4
_exptl_crystal_size_min          0.2
_refine_diff_density_max         0.266
_refine_diff_density_min         -0.467
_refine_diff_density_rms         0.099
_refine_ls_abs_structure_details
;
 Flack x determined using 3579 quotients [(I+)-(I-)]/[(I+)+(I-)]
 (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259).
;
_refine_ls_abs_structure_Flack   0.11(6)
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.079
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     489
_refine_ls_number_reflns         7868
_refine_ls_number_restraints     3
_refine_ls_restrained_S_all      1.078
_refine_ls_R_factor_all          0.0607
_refine_ls_R_factor_gt           0.0603
_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^)+(0.1223P)^2^+0.0646P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1552
_refine_ls_wR_factor_ref         0.1562
_reflns_Friedel_coverage         0.895
_reflns_Friedel_fraction_full    0.910
_reflns_Friedel_fraction_max     0.885
_reflns_number_gt                7749
_reflns_number_total             7868
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            d0sc06661c2.cif
_cod_data_source_block           liyan-200715
_cod_depositor_comments
'Adding full bibliography for 1560125--1560126.cif.'
_cod_database_code               1560126
_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 O(H) groups
2.a Aromatic/amide H refined with riding coordinates:
 C3(H3), C28(H28), C21(H21), C37(H37), C50(H50), C13(H13), C9(H9), C41(H41),
 C32(H32), C31(H31), C34(H34), C5(H5), C30(H30), C33(H33), C44(H44), C12(H12),
 C19(H19), C38(H38), C46(H46), C25(H25), C16(H16), C6(H6), C48(H48), C18(H18),
 C47(H47), C8(H8), C43(H43), C7(H7), C42(H42), C49(H49), C22(H22), C17(H17),
 C23(H23), C24(H24)
2.b Idealised tetrahedral OH refined as rotating group:
 O2(H2), O4(H4)
;
_smtbx_masks_void_probe_radius   1.2
_smtbx_masks_void_truncation_radius 1.2
_shelx_res_checksum              44805
_shelx_hkl_checksum              38503
_shelx_fab_checksum              22765
_olex2_submission_special_instructions 'No special instructions were received'