Enantioselective Palladium/Copper-Catalyzed C-C Bond Activation Synergized with Sonogashira-Type C(sp3)-C(sp) Cross-Coupling Alkynylation
Sun, Fengna; Yang, Wan-Chun; Chen, Xiao-Bing; Sun, Yuli; Cao, Jian; Xu, Zheng; Xu, Li-Wen; Chemical Science  (2019) –; doi:10.1039/C9SC02431J

data_1551853
_publ_section_title
;
 Enantioselective Palladium/Copper-Catalyzed C-C Bond Activation
 Synergized with Sonogashira-Type C(sp3)-C(sp) Cross-Coupling Alkynylation
;
_journal_name_full               'Chemical Science'
_journal_paper_doi               10.1039/C9SC02431J
_journal_year                    2019
_chemical_formula_moiety         'C19 H16 O'
_chemical_formula_sum            'C19 H16 O'
_chemical_formula_weight         260.32
_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             2019-03-28
_audit_creation_method
;
Olex2 1.2
(compiled 2018.05.29 svn.r3508 for OlexSys, GUI svn.r5506)
;
_audit_update_record
;
2019-04-15 deposited with the CCDC.    2019-06-20 downloaded from the CCDC.
;
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_formula_units_Z            8
_cell_length_a                   7.9220(2)
_cell_length_b                   18.8611(4)
_cell_length_c                   19.2017(5)
_cell_measurement_reflns_used    3055
_cell_measurement_temperature    293.15
_cell_measurement_theta_max      70.61
_cell_measurement_theta_min      38.71
_cell_volume                     2869.07(12)
_computing_cell_refinement       'SAINT v8.37A (Bruker, 2015)'
_computing_data_reduction        'SAINT v8.37A (Bruker, 2015)'
_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      293.15
_diffrn_measured_fraction_theta_full 0.959
_diffrn_measured_fraction_theta_max 0.951
_diffrn_measurement_device_type  'Bruker APEX-II CCD'
_diffrn_measurement_method       '\f and \w scans'
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54178
_diffrn_reflns_av_R_equivalents  0.0322
_diffrn_reflns_av_unetI/netI     0.0281
_diffrn_reflns_Laue_measured_fraction_full 0.959
_diffrn_reflns_Laue_measured_fraction_max 0.951
_diffrn_reflns_limit_h_max       9
_diffrn_reflns_limit_h_min       -8
_diffrn_reflns_limit_k_max       20
_diffrn_reflns_limit_k_min       -22
_diffrn_reflns_limit_l_max       22
_diffrn_reflns_limit_l_min       -23
_diffrn_reflns_number            15461
_diffrn_reflns_point_group_measured_fraction_full 0.958
_diffrn_reflns_point_group_measured_fraction_max 0.942
_diffrn_reflns_theta_full        67.679
_diffrn_reflns_theta_max         70.831
_diffrn_reflns_theta_min         5.169
_diffrn_standards_number         0
_exptl_absorpt_coefficient_mu    0.564
_exptl_absorpt_correction_T_max  1.0000
_exptl_absorpt_correction_T_min  0.8893
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
'SADABS-2016/2 (Bruker,2016/2) was used for absorption correction. wR2(int) was 0.0808 before and 0.0345 after correction. The Ratio of minimum to maximum transmission is 0.8893. The \l/2 correction factor is 0.00150.'
_exptl_crystal_colour            colourless
_exptl_crystal_colour_primary    colourless
_exptl_crystal_density_diffrn    1.205
_exptl_crystal_description       block
_exptl_crystal_F_000             1104
_exptl_crystal_size_max          0.15
_exptl_crystal_size_mid          0.15
_exptl_crystal_size_min          0.14
_refine_diff_density_max         0.105
_refine_diff_density_min         -0.096
_refine_diff_density_rms         0.022
_refine_ls_abs_structure_details
;
 Flack x determined using 2134 quotients [(I+)-(I-)]/[(I+)+(I-)]
 (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259).
;
_refine_ls_abs_structure_Flack   0.10(10)
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.049
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     363
_refine_ls_number_reflns         5208
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.049
_refine_ls_R_factor_all          0.0325
_refine_ls_R_factor_gt           0.0317
_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^)+(0.0548P)^2^+0.1323P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0867
_refine_ls_wR_factor_ref         0.0876
_reflns_Friedel_coverage         0.744
_reflns_Friedel_fraction_full    0.957
_reflns_Friedel_fraction_max     0.930
_reflns_number_gt                5090
_reflns_number_total             5208
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            c9sc02431j2.cif
_cod_data_source_block           cu_190326a_0m
_cod_database_code               1551853
_shelx_shelxl_version_number     2014/7
_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
2.a Secondary CH2 refined with riding coordinates:
 C28(H28A,H28B), C31(H31A,H31B), C12(H12A,H12B), C9(H9A,H9B)
2.b Aromatic/amide H refined with riding coordinates:
 C22(H22), C24(H24), C34(H34), C15(H15), C30(H30), C11(H11), C5(H5), C23(H23),
 C3(H3), C19(H19), C18(H18), C38(H38), C35(H35), C36(H36), C17(H17), C16(H16),
 C37(H37), C4(H4)
2.c Idealised Me refined as rotating group:
 C13(H13A,H13B,H13C), C32(H32A,H32B,H32C)
;
_shelx_res_checksum              84702
_olex2_submission_special_instructions 'No special instructions were received'