Catalytic Asymmetric Intermolecular Bromoesterification of Unfunctionalized Olefins.
Li, Lijun; Su, Cunxiang; Liu, Xiaoqin; Tian, Hua; Shi, Yian; Organic letters 16 (2014) 3728–; doi:10.1021/ol501542r

data_1516968
_publ_section_title
;
 Catalytic Asymmetric Intermolecular Bromoesterification of
 Unfunctionalized Olefins.
;
_journal_issue                   14
_journal_name_full               'Organic letters'
_journal_page_first              3728
_journal_paper_doi               10.1021/ol501542r
_journal_volume                  16
_journal_year                    2014
_chemical_absolute_configuration ad
_chemical_formula_moiety         'C23 H19 Br O4'
_chemical_formula_sum            'C23 H19 Br O4'
_chemical_formula_weight         439.29
_space_group_crystal_system      triclinic
_space_group_IT_number           1
_space_group_name_Hall           'P 1'
_space_group_name_H-M_alt        'P 1'
_symmetry_space_group_name_Hall  'P 1'
_symmetry_space_group_name_H-M   'P 1'
_atom_sites_solution_hydrogens   geom
_audit_creation_date             2013-12-23
_audit_creation_method
;
Olex2 1.2
(compiled 2013.12.10 svn.r2850 for OlexSys, GUI svn.r4736)
;
_cell_angle_alpha                75.661(9)
_cell_angle_beta                 88.560(11)
_cell_angle_gamma                73.636(7)
_cell_formula_units_Z            2
_cell_length_a                   8.0129(19)
_cell_length_b                   8.8764(18)
_cell_length_c                   14.284(3)
_cell_measurement_reflns_used    3944
_cell_measurement_temperature    173.1500
_cell_measurement_theta_max      32.8503
_cell_measurement_theta_min      1.4732
_cell_volume                     943.3(4)
_computing_cell_refinement       'CrystalClear (Rigaku Inc., 2007)'
_computing_data_collection       'CrystalClear (Rigaku Inc., 2007)'
_computing_data_reduction        'CrystalClear (Rigaku Inc., 2007)'
_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      173.1500
_diffrn_detector_area_resol_mean 28.5714
_diffrn_measured_fraction_theta_full 0.998
_diffrn_measured_fraction_theta_max 0.999
_diffrn_measurement_device
;
Saturn724+ (2x2 bin mode)
;
_diffrn_measurement_device_details
;
AFC10: Fixed Chi 2 circle
;
_diffrn_measurement_device_type  'Saturn724+ CCD'
_diffrn_measurement_method       dtprofit.ref
_diffrn_orient_matrix_type       d*Trek
_diffrn_orient_matrix_UB_11      -0.0145
_diffrn_orient_matrix_UB_12      0.1247
_diffrn_orient_matrix_UB_13      -0.0344
_diffrn_orient_matrix_UB_21      0.1127
_diffrn_orient_matrix_UB_22      -0.0109
_diffrn_orient_matrix_UB_23      0.0435
_diffrn_orient_matrix_UB_31      0.0062
_diffrn_orient_matrix_UB_32      -0.0151
_diffrn_orient_matrix_UB_33      -0.0705
_diffrn_radiation_detector       CCD
_diffrn_radiation_monochromator  'Graphite Monochromator'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0506
_diffrn_reflns_av_unetI/netI     0.0722
_diffrn_reflns_Laue_measured_fraction_full 0.998
_diffrn_reflns_Laue_measured_fraction_max 0.999
_diffrn_reflns_limit_h_max       10
_diffrn_reflns_limit_h_min       -10
_diffrn_reflns_limit_k_max       11
_diffrn_reflns_limit_k_min       -11
_diffrn_reflns_limit_l_max       18
_diffrn_reflns_limit_l_min       -18
_diffrn_reflns_number            16815
_diffrn_reflns_point_group_measured_fraction_full 0.991
_diffrn_reflns_point_group_measured_fraction_max 0.988
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         27.465
_diffrn_reflns_theta_min         2.947
_diffrn_source                   'Sealed Tube'
_diffrn_source_current           30.0000
_diffrn_source_power             1.5000
_diffrn_source_voltage           50.0000
_exptl_absorpt_coefficient_mu    2.206
_exptl_absorpt_correction_T_max  1.0000
_exptl_absorpt_correction_T_min  0.5177
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   'CrystalClear (Rigaku Inc., 2007)'
_exptl_crystal_colour            Colorless
_exptl_crystal_density_diffrn    1.547
_exptl_crystal_description       rod
_exptl_crystal_F_000             448
_exptl_crystal_size_max          0.33
_exptl_crystal_size_mid          0.1
_exptl_crystal_size_min          0.09
_refine_diff_density_max         0.709
_refine_diff_density_min         -0.411
_refine_diff_density_rms         0.069
_refine_ls_abs_structure_details
;
 Flack x determined using 3092 quotients [(I+)-(I-)]/[(I+)+(I-)]
 (Parsons and Flack (2004), Acta Cryst. A60, s61).
;
_refine_ls_abs_structure_Flack   0.005(8)
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.075
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     507
_refine_ls_number_reflns         8556
_refine_ls_number_restraints     3
_refine_ls_restrained_S_all      1.075
_refine_ls_R_factor_all          0.0563
_refine_ls_R_factor_gt           0.0496
_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^)+(0.0351P)^2^] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0966
_refine_ls_wR_factor_ref         0.1017
_reflns_Friedel_coverage         0.978
_reflns_Friedel_fraction_full    0.984
_reflns_Friedel_fraction_max     0.976
_reflns_number_gt                7781
_reflns_number_total             8556
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            ol501542r_si_002.cif
_cod_data_source_block           sa3094
_cod_depositor_comments
'Adding full bibliography for 1516968--1516972.cif.'
_cod_database_code               1516968
_shelxl_version_number           2013-4
_diffrn_number_total             4329
_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 Ternary CH refined with riding coordinates:
 C1A(H1A), C2A(H2A), C1(H1), C2(H2)
2.b Secondary CH2 refined with riding coordinates:
 C3A(H3AA,H3AB), C4A(H4AA,H4AB), C3(H3A,H3B), C4(H4A,H4B)
2.c Aromatic/amide H refined with riding coordinates:
 C7A(H7A), C9A(H9A), C10A(H10A), C15A(H15A), C16A(H16A), C17A(H17A),
 C20A(H20A), C21A(H21A), C22A(H22A), C23A(H23A), C7(H7), C9(H9), C10(H10),
 C15(H15), C16(H16), C17(H17), C20(H20), C21(H21), C22(H22), C23(H23)
2.d Idealised Me refined as rotating group:
 C12A(H12A,H12B,H12C), C12(H12D,H12E,H12F)
;
_shelx_res_checksum              16230
_shelx_hkl_checksum              53786