Carbene-catalyzed enantioselective oxidative coupling of enals and di(hetero)arylmethanes.
Chen, Qiao; Zhu, Tingshun; Majhi, Pankaj Kumar; Mou, Chengli; Chai, Huifang; Zhang, Jingjie; Zhuo, Shitian; Chi, Yonggui Robin; Chemical science 9 (2018) 8711–8715; doi:10.1039/c8sc03480j

data_1549963
_publ_section_title
;
 Carbene-catalyzed enantioselective oxidative coupling of enals and
 di(hetero)arylmethanes.
;
_journal_issue                   46
_journal_name_full               'Chemical science'
_journal_page_first              8711
_journal_page_last               8715
_journal_paper_doi               10.1039/c8sc03480j
_journal_volume                  9
_journal_year                    2018
_chemical_absolute_configuration ad
_chemical_formula_sum            'C23 H16 Cl N3 O3'
_chemical_formula_weight         417.84
_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
_audit_update_record
;
2018-05-15 deposited with the CCDC.
2018-09-17 downloaded from the CCDC.
;
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   11.0105(3)
_cell_length_b                   11.0264(2)
_cell_length_c                   15.8268(3)
_cell_measurement_reflns_used    9919
_cell_measurement_temperature    100.(2)
_cell_measurement_theta_max      30.9696
_cell_measurement_theta_min      2.6142
_cell_volume                     1921.47(7)
_computing_cell_refinement       'SAINT V8.37A (Bruker AXS Inc., 2015)'
_computing_data_collection       'APEX3 (Bruker AXS Inc., 2016)'
_computing_data_reduction        'SAINT V8.37A (Bruker AXS Inc., 2015)'
_computing_molecular_graphics    'XP (Bruker AXS Inc., 2016)'
_computing_publication_material  'APEX3 (Bruker AXS Inc., 2016)'
_computing_structure_refinement  'SHELXL-2014/7 (Sheldrick, 2014)'
_computing_structure_solution    'XS, VERSION 2013/1'
_diffrn_ambient_temperature      100.(2)
_diffrn_detector_area_resol_mean 7.4074
_diffrn_measured_fraction_theta_full 0.996
_diffrn_measured_fraction_theta_max 0.996
_diffrn_measurement_device_type  'Photon II CPADs detector'
_diffrn_measurement_method       'phi and omega scans'
_diffrn_radiation_monochromator  'Multilayer Mirror'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0578
_diffrn_reflns_av_unetI/netI     0.0448
_diffrn_reflns_limit_h_max       15
_diffrn_reflns_limit_h_min       -15
_diffrn_reflns_limit_k_max       15
_diffrn_reflns_limit_k_min       -15
_diffrn_reflns_limit_l_max       22
_diffrn_reflns_limit_l_min       -22
_diffrn_reflns_number            35946
_diffrn_reflns_theta_full        30.98
_diffrn_reflns_theta_max         30.98
_diffrn_reflns_theta_min         2.61
_diffrn_source                   'Incoatec microfocus source'
_diffrn_source_type              'Bruker D8 Quest'
_exptl_absorpt_coefficient_mu    0.231
_exptl_absorpt_correction_T_max  0.94
_exptl_absorpt_correction_T_min  0.78
_exptl_absorpt_correction_type   'Numerical Mu From Formula'
_exptl_absorpt_process_details
;
SADABS-2016/2 - Bruker AXS area detector scaling and absorption correction
;
_exptl_crystal_colour            colourless
_exptl_crystal_density_diffrn    1.444
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       block
_exptl_crystal_F_000             864
_exptl_crystal_size_max          0.439
_exptl_crystal_size_mid          0.421
_exptl_crystal_size_min          0.296
_refine_diff_density_max         0.279
_refine_diff_density_min         -0.269
_refine_ls_abs_structure_details
;

Flack x determined using 2078 quotients [(I+)-(I-)]/[(I+)+(I-)]
(Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259).
;
_refine_ls_abs_structure_Flack   0.02(2)
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.072
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     271
_refine_ls_number_reflns         6089
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.072
_refine_ls_R_factor_all          0.0534
_refine_ls_R_factor_gt           0.0424
_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^)+(0.0236P)^2^+0.8415P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0794
_refine_ls_wR_factor_ref         0.0839
_reflns_number_gt                5383
_reflns_number_total             6089
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            c8sc03480j2.cif
_cod_data_source_block           cyg205m
_cod_depositor_comments
'Adding full bibliography for 1549963--1549964.cif.'
_cod_database_code               1549963
_shelx_res_checksum              87165
_shelx_hkl_checksum              43373