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_1516969
_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 rmad
_chemical_formula_moiety         'C10 H11 Br O'
_chemical_formula_sum            'C10 H11 Br O'
_chemical_formula_weight         227.10
_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   mixed
_audit_creation_date             2014-01-23
_audit_creation_method
;
Olex2 1.2
(compiled 2013.12.10 svn.r2850 for OlexSys, GUI svn.r4736)
;
_cell_angle_alpha                90
_cell_angle_beta                 107.296(3)
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   10.488(3)
_cell_length_b                   8.970(2)
_cell_length_c                   10.599(3)
_cell_measurement_reflns_used    3110
_cell_measurement_temperature    173.1500
_cell_measurement_theta_max      27.4820
_cell_measurement_theta_min      2.0338
_cell_volume                     952.0(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  'XL (Sheldrick, 2008)'
_computing_structure_solution
;
'XS (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 0.995
_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      0.0993
_diffrn_orient_matrix_UB_12      0.0014
_diffrn_orient_matrix_UB_13      0.0109
_diffrn_orient_matrix_UB_21      0.0007
_diffrn_orient_matrix_UB_22      -0.1112
_diffrn_orient_matrix_UB_23      0.0073
_diffrn_orient_matrix_UB_31      0.0396
_diffrn_orient_matrix_UB_32      -0.0057
_diffrn_orient_matrix_UB_33      -0.0904
_diffrn_radiation_detector       CCD
_diffrn_radiation_monochromator  'Graphite Monochromator'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0547
_diffrn_reflns_av_unetI/netI     0.0481
_diffrn_reflns_Laue_measured_fraction_full 0.998
_diffrn_reflns_Laue_measured_fraction_max 0.995
_diffrn_reflns_limit_h_max       13
_diffrn_reflns_limit_h_min       -13
_diffrn_reflns_limit_k_max       11
_diffrn_reflns_limit_k_min       -11
_diffrn_reflns_limit_l_max       13
_diffrn_reflns_limit_l_min       -13
_diffrn_reflns_number            11379
_diffrn_reflns_point_group_measured_fraction_full 0.945
_diffrn_reflns_point_group_measured_fraction_max 0.930
_diffrn_reflns_theta_full        26.000
_diffrn_reflns_theta_max         27.481
_diffrn_reflns_theta_min         2.012
_diffrn_source                   'Sealed Tube'
_diffrn_source_current           30.0000
_diffrn_source_power             1.5000
_diffrn_source_voltage           50.0000
_exptl_absorpt_coefficient_mu    4.266
_exptl_absorpt_correction_T_max  1.0000
_exptl_absorpt_correction_T_min  0.2364
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   'CrystalClear (Rigaku Inc., 2007)'
_exptl_crystal_colour            Colorless
_exptl_crystal_density_diffrn    1.584
_exptl_crystal_description       rod
_exptl_crystal_F_000             456
_exptl_crystal_size_max          0.47
_exptl_crystal_size_mid          0.16
_exptl_crystal_size_min          0.06
_refine_diff_density_max         0.543
_refine_diff_density_min         -0.397
_refine_diff_density_rms         0.066
_refine_ls_abs_structure_details
;
 Flack x determined using 1492 quotients [(I+)-(I-)]/[(I+)+(I-)]
 (Parsons and Flack (2004), Acta Cryst. A60, s61).
;
_refine_ls_abs_structure_Flack   0.004(8)
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.081
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     217
_refine_ls_number_reflns         4045
_refine_ls_number_restraints     1
_refine_ls_restrained_S_all      1.081
_refine_ls_R_factor_all          0.0395
_refine_ls_R_factor_gt           0.0368
_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^)+(0.0295P)^2^+0.3295P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0811
_refine_ls_wR_factor_ref         0.0831
_reflns_Friedel_coverage         0.756
_reflns_Friedel_fraction_full    0.884
_reflns_Friedel_fraction_max     0.856
_reflns_number_gt                3833
_reflns_number_total             4045
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            ol501542r_si_005.cif
_cod_data_source_block           sa3188
_cod_depositor_comments
'Adding full bibliography for 1516968--1516972.cif.'
_cod_original_cell_volume        952.1(4)
_cod_database_code               1516969
_shelxl_version_number           2013-4
_diffrn_number_total             2310
_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 O(H) groups
2.a Riding coordinates:
 O1(H1AA), O1A(H1B)
2.b Ternary CH refined with riding coordinates:
 C1(H1), C2(H2), C1A(H1A), C2A(H2A)
2.c Secondary CH2 refined with riding coordinates:
 C9(H9A,H9B), C10(H10C,H10D), C9A(H9AA,H9AB), C10A(H10A,H10B)
2.d Aromatic/amide H refined with riding coordinates:
 C4(H4), C5(H5), C6(H6), C7(H7), C4A(H4A), C5A(H5A), C6A(H6A), C7A(H7A)
;
_shelx_res_checksum              90074
_shelx_hkl_checksum              26025