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_1516970
_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         'C22 H19 Br O2'
_chemical_formula_sum            'C22 H19 Br O2'
_chemical_formula_weight         395.28
_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     iterative
_audit_creation_date             2014-04-08
_audit_creation_method
;
Olex2 1.2
(compiled 2013.12.10 svn.r2850 for OlexSys, GUI svn.r4736)
;
_cell_angle_alpha                90
_cell_angle_beta                 102.07(3)
_cell_angle_gamma                90
_cell_formula_units_Z            2
_cell_length_a                   11.041(2)
_cell_length_b                   6.6793(13)
_cell_length_c                   12.193(2)
_cell_measurement_reflns_used    3053
_cell_measurement_temperature    173.1500
_cell_measurement_theta_max      27.4798
_cell_measurement_theta_min      1.7079
_cell_volume                     879.3(3)
_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  'XL (Sheldrick, 2013)'
_computing_structure_solution
;
'XS (Sheldrick, 2013)'
;
_diffrn_ambient_temperature      173.1500
_diffrn_detector_area_resol_mean 28.5714
_diffrn_measured_fraction_theta_full 0.997
_diffrn_measured_fraction_theta_max 0.996
_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       '\w scans at fixed \c = 45\%'
_diffrn_orient_matrix_type       d*Trek
_diffrn_orient_matrix_UB_11      -0.0422
_diffrn_orient_matrix_UB_12      -0.0321
_diffrn_orient_matrix_UB_13      0.0760
_diffrn_orient_matrix_UB_21      0.0338
_diffrn_orient_matrix_UB_22      0.1267
_diffrn_orient_matrix_UB_23      0.0723
_diffrn_orient_matrix_UB_31      -0.0786
_diffrn_orient_matrix_UB_32      0.0272
_diffrn_orient_matrix_UB_33      -0.0108
_diffrn_radiation_detector       CCD
_diffrn_radiation_monochromator  'Graphite Monochromator'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0631
_diffrn_reflns_av_unetI/netI     0.0594
_diffrn_reflns_Laue_measured_fraction_full 0.997
_diffrn_reflns_Laue_measured_fraction_max 0.996
_diffrn_reflns_limit_h_max       13
_diffrn_reflns_limit_h_min       -14
_diffrn_reflns_limit_k_max       8
_diffrn_reflns_limit_k_min       -8
_diffrn_reflns_limit_l_max       15
_diffrn_reflns_limit_l_min       -15
_diffrn_reflns_number            10230
_diffrn_reflns_point_group_measured_fraction_full 0.996
_diffrn_reflns_point_group_measured_fraction_max 0.993
_diffrn_reflns_theta_full        26.000
_diffrn_reflns_theta_max         27.540
_diffrn_reflns_theta_min         3.417
_diffrn_source                   'Sealed Tube'
_diffrn_source_current           30.0000
_diffrn_source_power             1.5000
_diffrn_source_voltage           50.0000
_exptl_absorpt_coefficient_mu    2.350
_exptl_absorpt_correction_T_max  1.0000
_exptl_absorpt_correction_T_min  0.3390
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   'CrystalClear (Rigaku Inc., 2007)'
_exptl_crystal_colour            Colorless
_exptl_crystal_density_diffrn    1.493
_exptl_crystal_description       block
_exptl_crystal_F_000             404
_exptl_crystal_size_max          0.24
_exptl_crystal_size_mid          0.13
_exptl_crystal_size_min          0.13
_refine_diff_density_max         0.615
_refine_diff_density_min         -0.504
_refine_diff_density_rms         0.076
_refine_ls_abs_structure_details
;
 Flack x determined using 1449 quotients [(I+)-(I-)]/[(I+)+(I-)]
 (Parsons and Flack (2004), Acta Cryst. A60, s61).
;
_refine_ls_abs_structure_Flack   0.046(11)
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.096
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     226
_refine_ls_number_reflns         4021
_refine_ls_number_restraints     42
_refine_ls_restrained_S_all      1.121
_refine_ls_R_factor_all          0.0537
_refine_ls_R_factor_gt           0.0494
_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^)+(0.0536P)^2^+0.2142P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1163
_refine_ls_wR_factor_ref         0.1200
_reflns_Friedel_coverage         0.835
_reflns_Friedel_fraction_full    0.994
_reflns_Friedel_fraction_max     0.989
_reflns_number_gt                3743
_reflns_number_total             4021
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            ol501542r_si_003.cif
_cod_data_source_block           sa3313
_cod_depositor_comments
'Adding full bibliography for 1516968--1516972.cif.'
_cod_database_code               1516970
_shelxl_version_number           2013-4
_diffrn_number_total             2198
_olex2_refinement_description
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups, All C(H,H) groups
2. Restrained distances
 C9-C10 = C9-C8 = C7-C6 = C8-C7 = C11-C10
 1.39 with sigma of 0.01
3. Uiso/Uaniso restraints and constraints
Uanis(C9) \\sim Ueq, Uanis(C8) \\sim Ueq, Uanis(C7) \\sim Ueq, Uanis(C10) \\sim
Ueq, Uanis(C6) \\sim Ueq, Uanis(C11) \\sim Ueq: with sigma of 0.01 and sigma
for terminal atoms of 0.02
4.a Ternary CH refined with riding coordinates:
 C1(H1), C2(H2)
4.b Secondary CH2 refined with riding coordinates:
 C3(H3A,H3B), C4(H4A,H4B), C5(H5A,H5B)
4.c Aromatic/amide H refined with riding coordinates:
 C7(H7), C8(H8), C9(H9), C10(H10), C14(H14), C15(H15), C16(H16), C18(H18),
 C19(H19), C20(H20), C21(H21)
;
_shelx_res_checksum              15927
_shelx_hkl_checksum              57707