Enantioselective Synthesis of anti-syn-Trihalides and anti-syn-anti-Tetrahalides via Asymmetric β-Elimination.
Tan, Yu; Luo, Shilong; Li, Dongmei; Zhang, Nan; Jia, Shiqi; Liu, Yidong; Qin, Wenling; Song, Choong Eui; Yan, Hailong; Journal of the American Chemical Society 139 (2017) 6431–6436; doi:10.1021/jacs.7b02076

data_4125982
_publ_section_title
;
 Enantioselective Synthesis of anti-syn-Trihalides and
 anti-syn-anti-Tetrahalides via Asymmetric \b-Elimination.
;
_journal_issue                   18
_journal_name_full               'Journal of the American Chemical Society'
_journal_page_first              6431
_journal_page_last               6436
_journal_paper_doi               10.1021/jacs.7b02076
_journal_volume                  139
_journal_year                    2017
_chemical_absolute_configuration ad
_chemical_formula_moiety         'C16 H13 Br3 O'
_chemical_formula_sum            'C16 H13 Br3 O'
_chemical_formula_weight         460.99
_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
_audit_creation_date             2016-04-06
_audit_creation_method
;
Olex2 1.2-alpha
(compiled 2015.09.16 svn.r3215 for OlexSys, GUI svn.r5097)
;
_cell_angle_alpha                90
_cell_angle_beta                 100.264(5)
_cell_angle_gamma                90
_cell_formula_units_Z            2
_cell_length_a                   6.7844(4)
_cell_length_b                   7.0774(6)
_cell_length_c                   17.2752(10)
_cell_measurement_reflns_used    1041
_cell_measurement_temperature    292(2)
_cell_measurement_theta_max      24.5200
_cell_measurement_theta_min      4.1840
_cell_volume                     816.21(10)
_computing_molecular_graphics    'Olex2 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 (Dolomanov et al., 2009)'
_computing_structure_refinement  'ShelXL (Sheldrick, 2015)'
_computing_structure_solution    'ShelXT (Sheldrick, 2015)'
_diffrn_ambient_temperature      292(2)
_diffrn_detector_area_resol_mean 16.0892
_diffrn_measured_fraction_theta_full 0.997
_diffrn_measured_fraction_theta_max 0.856
_diffrn_measurement_device_type  'SuperNova, Single source at offset, Eos'
_diffrn_measurement_method       '\w scans'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0288
_diffrn_reflns_av_unetI/netI     0.0670
_diffrn_reflns_Laue_measured_fraction_full 0.997
_diffrn_reflns_Laue_measured_fraction_max 0.856
_diffrn_reflns_limit_h_max       8
_diffrn_reflns_limit_h_min       -6
_diffrn_reflns_limit_k_max       7
_diffrn_reflns_limit_k_min       -8
_diffrn_reflns_limit_l_max       21
_diffrn_reflns_limit_l_min       -15
_diffrn_reflns_number            3524
_diffrn_reflns_point_group_measured_fraction_full 0.728
_diffrn_reflns_point_group_measured_fraction_max 0.609
_diffrn_reflns_theta_full        26.000
_diffrn_reflns_theta_max         28.971
_diffrn_reflns_theta_min         3.472
_diffrn_source                   'micro-focus sealed X-ray tube'
_exptl_absorpt_coefficient_mu    7.406
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.42797
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
CrysAlisPro 1.171.38.41k (Rigaku Oxford Diffraction, 2015)
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_crystal_colour            colorless
_exptl_crystal_density_diffrn    1.876
_exptl_crystal_description       block
_exptl_crystal_F_000             444
_exptl_crystal_size_max          0.2
_exptl_crystal_size_mid          0.2
_exptl_crystal_size_min          0.2
_refine_diff_density_max         1.170
_refine_diff_density_min         -0.643
_refine_diff_density_rms         0.135
_refine_ls_abs_structure_details
;
 Flack x determined using 437 quotients [(I+)-(I-)]/[(I+)+(I-)]
 (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259).
;
_refine_ls_abs_structure_Flack   -0.01(3)
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.123
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     181
_refine_ls_number_reflns         2654
_refine_ls_number_restraints     1
_refine_ls_restrained_S_all      1.123
_refine_ls_R_factor_all          0.0716
_refine_ls_R_factor_gt           0.0584
_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^)+(0.0526P)^2^+0.8125P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1273
_refine_ls_wR_factor_ref         0.1421
_reflns_Friedel_coverage         0.320
_reflns_Friedel_fraction_full    0.408
_reflns_Friedel_fraction_max     0.320
_reflns_number_gt                2222
_reflns_number_total             2654
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            ja7b02076_si_002.cif
_cod_data_source_block           20160406-yanhailong-ty770-2
_cod_depositor_comments
'Adding full bibliography for 4125981--4125982.cif.'
_cod_original_cell_volume        816.22(9)
_cod_database_code               4125982
_olex2_refinement_description
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups
2.a Ternary CH refined with riding coordinates:
 C8(H8), C9(H9), C10(H10)
2.b Aromatic/amide H refined with riding coordinates:
 C5(H5), C2(H2), C1(H1), C4(H4), C12(H12), C3(H3), C16(H16), C13(H13),
 C14(H14), C15(H15)
;
_shelx_res_checksum              90071
_shelx_hkl_checksum              39683
_shelx_shelxl_version_number     2014/7
_olex2_submission_special_instructions 'No special instructions were received'