Enantioselective Synthesis of Chiral Oxygen-Containing Heterocycles Using Copper-Catalyzed Aryl C-O Coupling Reactions via Asymmetric Desymmetrization.
Zhang, Yong; Wang, Qiuyan; Wang, Ting; He, Huan; Yang, Wenqiang; Zhang, Xinhao; Cai, Qian; The Journal of organic chemistry 82 (2017) 1458–1463; doi:10.1021/acs.joc.6b02646

data_4032339
_publ_section_title
;
 Enantioselective Synthesis of Chiral Oxygen-Containing Heterocycles Using
 Copper-Catalyzed Aryl C-O Coupling Reactions via Asymmetric
 Desymmetrization.
;
_journal_issue                   3
_journal_name_full               'The Journal of organic chemistry'
_journal_page_first              1458
_journal_page_last               1463
_journal_paper_doi               10.1021/acs.joc.6b02646
_journal_volume                  82
_journal_year                    2017
_chemical_absolute_configuration ad
_chemical_formula_moiety         'C19 H17 N O3'
_chemical_formula_sum            'C20 H17 N0.5 O3'
_chemical_formula_weight         312.34
_chemical_name_systematic
;
 ? 
;
_space_group_crystal_system      monoclinic
_space_group_IT_number           4
_space_group_name_Hall           'P 2yb'
_space_group_name_H-M_alt        'P 1 21 1'
_symmetry_space_group_name_Hall  'P 2yb'
_symmetry_space_group_name_H-M   'P 1 21 1'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_audit_creation_date             2015-03-16
_audit_creation_method
;
Olex2 1.2
(compiled 2014.02.17 svn.r2891 for OlexSys, GUI svn.r4773)
;
_cell_angle_alpha                90.00
_cell_angle_beta                 101.7108(18)
_cell_angle_gamma                90.00
_cell_formula_units_Z            2
_cell_length_a                   5.82677(11)
_cell_length_b                   9.95071(18)
_cell_length_c                   13.6194(3)
_cell_measurement_reflns_used    10566
_cell_measurement_temperature    290(2)
_cell_measurement_theta_max      66.8940
_cell_measurement_theta_min      3.3070
_cell_volume                     773.22(3)
_computing_cell_refinement
;
CrysAlisPro, Agilent Technologies,
Version 1.171.37.31 (release 14-01-2014 CrysAlis171 .NET)
(compiled Jan 14 2014,18:38:05)
;
_computing_data_collection
;
CrysAlisPro, Agilent Technologies,
Version 1.171.37.31 (release 14-01-2014 CrysAlis171 .NET)
(compiled Jan 14 2014,18:38:05)
;
_computing_data_reduction
;
CrysAlisPro, Agilent Technologies,
Version 1.171.37.31 (release 14-01-2014 CrysAlis171 .NET)
(compiled Jan 14 2014,18:38:05)
;
_computing_molecular_graphics    'Olex2 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 (Dolomanov et al., 2009)'
_computing_structure_refinement  'ShelXL (Sheldrick, 2008)'
_computing_structure_solution    'ShelXS (Sheldrick, 2008)'
_diffrn_ambient_environment      air
_diffrn_ambient_temperature      290(2)
_diffrn_detector                 'CCD plate'
_diffrn_detector_area_resol_mean 10.4015
_diffrn_detector_type            Ruby
_diffrn_measured_fraction_theta_full 0.989
_diffrn_measured_fraction_theta_max 0.989
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'Xcalibur, Ruby, Gemini ultra'
_diffrn_measurement_method       '\w scans'
_diffrn_orient_matrix_UB_11      0.0067598000
_diffrn_orient_matrix_UB_12      -0.0392562000
_diffrn_orient_matrix_UB_13      -0.1087945000
_diffrn_orient_matrix_UB_21      -0.1997410000
_diffrn_orient_matrix_UB_22      0.1000130000
_diffrn_orient_matrix_UB_23      -0.0386553000
_diffrn_orient_matrix_UB_31      0.1815077000
_diffrn_orient_matrix_UB_32      0.1115109000
_diffrn_orient_matrix_UB_33      -0.0036184000
_diffrn_radiation_monochromator  mirror
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54184
_diffrn_reflns_av_R_equivalents  0.0290
_diffrn_reflns_av_unetI/netI     0.0211
_diffrn_reflns_limit_h_max       6
_diffrn_reflns_limit_h_min       -6
_diffrn_reflns_limit_k_max       11
_diffrn_reflns_limit_k_min       -11
_diffrn_reflns_limit_l_max       15
_diffrn_reflns_limit_l_min       -16
_diffrn_reflns_number            13369
_diffrn_reflns_theta_full        66.92
_diffrn_reflns_theta_max         66.92
_diffrn_reflns_theta_min         3.31
_diffrn_source                   'sealed X-ray tube'
_diffrn_source_type              'Enhance Ultra (Cu) X-ray Source'
_exptl_absorpt_coefficient_mu    0.726
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.80027
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
CrysAlisPro, Agilent Technologies,
Version 1.171.37.31 (release 14-01-2014 CrysAlis171 .NET)
(compiled Jan 14 2014,18:38:05)
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_crystal_density_diffrn    1.342
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description
;
;
_exptl_crystal_F_000             329
_refine_diff_density_max         0.138
_refine_diff_density_min         -0.146
_refine_diff_density_rms         0.034
_refine_ls_abs_structure_details 'Flack H D (1983), Acta Cryst. A39, 876-881'
_refine_ls_abs_structure_Flack   0.02(17)
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.101
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     209
_refine_ls_number_reflns         2700
_refine_ls_number_restraints     1
_refine_ls_restrained_S_all      1.101
_refine_ls_R_factor_all          0.0308
_refine_ls_R_factor_gt           0.0302
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'calc w=1/[\s^2^(Fo^2^)+(0.0485P)^2^+0.0514P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0782
_refine_ls_wR_factor_ref         0.0796
_reflns_number_gt                2654
_reflns_number_total             2700
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            jo6b02646_si_002.cif
_cod_data_source_block           exp_761
_cod_original_formula_sum        'C20 H17 N0.50 O3'
_cod_database_code               4032339
_reflns_odcompleteness_completeness 98.43
_reflns_odcompleteness_iscentric 1
_reflns_odcompleteness_theta     66.97
_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:
 C12(H12B,H12A), C2(H2A,H2B), C4(H4A,H4B)
2.b Aromatic/amide H refined with riding coordinates:
 C5(H5), C8(H8), C6(H6), C16(H16), C19(H19), C7(H7), C17(H17), C18(H18)
2.c Idealised Me refined as rotating group:
 C11(H11A,H11B,H11C)
;
_olex2_computing_structure_refinement_long 'ShelXL (Sheldrick, 2008)'
_olex2_computing_structure_solution_long 'ShelXS (Sheldrick, 2008)'