Enantioselective synthesis of arylglycine derivatives by direct C-H oxidative cross-coupling
Xiao-Hong Wei; Gang-Wei Wang; Shang-Dong Yang; Chem.Commun. 51 (2015) 832–; doi:10.1039/C4cc07361D

data_7116314
_publ_section_title
;
 Enantioselective synthesis of arylglycine derivatives by direct C-H
 oxidative cross-coupling
;
_journal_name_full               Chem.Commun.
_journal_page_first              832
_journal_paper_doi               10.1039/C4cc07361D
_journal_volume                  51
_journal_year                    2015
_chemical_formula_moiety         'C20 H18 Br N O2'
_chemical_formula_sum            'C20 H18 Br N O2'
_chemical_formula_weight         384.26
_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
_audit_creation_date             2014-05-21
_audit_creation_method
;
Olex2 1.2
(compiled 2014.03.20 svn.r2914 for OlexSys, GUI svn.r4816)
;
_cell_angle_alpha                90
_cell_angle_beta                 104.603(3)
_cell_angle_gamma                90
_cell_formula_units_Z            2
_cell_length_a                   9.6683(3)
_cell_length_b                   5.72898(13)
_cell_length_c                   16.9335(5)
_cell_measurement_reflns_used    3337
_cell_measurement_temperature    294.54(10)
_cell_measurement_theta_max      70.6110
_cell_measurement_theta_min      4.7150
_cell_volume                     907.64(5)
_computing_cell_refinement
;
CrysAlisPro, Agilent Technologies,
Version 1.171.36.28 (release 01-02-2013 CrysAlis171 .NET)
(compiled Feb  1 2013,16:14:44)
;
_computing_data_collection
;
CrysAlisPro, Agilent Technologies,
Version 1.171.36.28 (release 01-02-2013 CrysAlis171 .NET)
(compiled Feb  1 2013,16:14:44)
;
_computing_data_reduction
;
CrysAlisPro, Agilent Technologies,
Version 1.171.36.28 (release 01-02-2013 CrysAlis171 .NET)
(compiled Feb  1 2013,16:14:44)
;
_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_temperature      294.54(10)
_diffrn_detector_area_resol_mean 16.0733
_diffrn_measured_fraction_theta_full 0.990
_diffrn_measured_fraction_theta_max 0.979
_diffrn_measurement_device_type  'SuperNova, Dual, Cu at zero, Eos'
_diffrn_measurement_method       '\w scans'
_diffrn_orient_matrix_UB_11      0.0421831000
_diffrn_orient_matrix_UB_12      -0.0595245000
_diffrn_orient_matrix_UB_13      0.0916875000
_diffrn_orient_matrix_UB_21      -0.1084071000
_diffrn_orient_matrix_UB_22      0.1809258000
_diffrn_orient_matrix_UB_23      0.0150821000
_diffrn_orient_matrix_UB_31      -0.1164959000
_diffrn_orient_matrix_UB_32      -0.1897356000
_diffrn_orient_matrix_UB_33      -0.0143592000
_diffrn_radiation_monochromator  mirror
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54184
_diffrn_reflns_av_R_equivalents  0.0250
_diffrn_reflns_av_unetI/netI     0.0300
_diffrn_reflns_Laue_measured_fraction_full 0.990
_diffrn_reflns_Laue_measured_fraction_max 0.979
_diffrn_reflns_limit_h_max       11
_diffrn_reflns_limit_h_min       -11
_diffrn_reflns_limit_k_max       6
_diffrn_reflns_limit_k_min       -6
_diffrn_reflns_limit_l_max       20
_diffrn_reflns_limit_l_min       -20
_diffrn_reflns_number            6322
_diffrn_reflns_point_group_measured_fraction_full 0.992
_diffrn_reflns_point_group_measured_fraction_max 0.982
_diffrn_reflns_theta_full        67.684
_diffrn_reflns_theta_max         70.637
_diffrn_reflns_theta_min         4.726
_diffrn_source                   'SuperNova (Cu) X-ray Source'
_exptl_absorpt_coefficient_mu    3.171
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.65861
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
CrysAlisPro, Agilent Technologies,
Version 1.171.36.28 (release 01-02-2013 CrysAlis171 .NET)
(compiled Feb  1 2013,16:14:44)
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_crystal_colour            'clear light colourless'
_exptl_crystal_density_diffrn    1.406
_exptl_crystal_description       block
_exptl_crystal_F_000             392
_exptl_crystal_size_max          0.34
_exptl_crystal_size_mid          0.26
_exptl_crystal_size_min          0.17
_refine_diff_density_max         0.382
_refine_diff_density_min         -0.454
_refine_diff_density_rms         0.053
_refine_ls_abs_structure_details
;
 Refined as a perfect inversion twin.
;
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.033
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     218
_refine_ls_number_reflns         3335
_refine_ls_number_restraints     1
_refine_ls_restrained_S_all      1.033
_refine_ls_R_factor_all          0.0418
_refine_ls_R_factor_gt           0.0409
_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^)+(0.0695P)^2^+0.2836P]
 where P=(Fo^2^+2Fc^2^)/3
;
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1099
_refine_ls_wR_factor_ref         0.1113
_reflns_Friedel_coverage         0.812
_reflns_Friedel_fraction_full    0.995
_reflns_Friedel_fraction_max     0.985
_reflns_number_gt                3230
_reflns_number_total             3335
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            c4cc07361d2.cif
_cod_data_source_block           weixh0519
_cod_original_cell_volume        907.64(4)
_cod_database_code               7116314
_shelxl_version_number           2013-2
_reflns_odcompleteness_completeness 91.85
_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, All N(H) groups
 At 1.5 times of:
  All C(H,H,H) groups
2.a Ternary CH refined with riding coordinates:
 C11(H11)
2.b Secondary CH2 refined with riding coordinates:
 C19(H19A,H19B)
2.c Aromatic/amide H refined with riding coordinates:
 N1(H1), C2(H2), C4(H4), C5(H5), C6(H6), C7(H7), C9(H9), C10(H10), C13(H13),
 C14(H14), C16(H16), C17(H17)
2.d Idealised Me refined as rotating group:
 C20(H20A,H20B,H20C)
;
_shelx_res_checksum              33935
_shelx_hkl_checksum              15765