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_4125981
_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_formula_moiety         'C19 H18 Br Cl3 O2'
_chemical_formula_sum            'C19 H18 Br Cl3 O2'
_chemical_formula_weight         464.59
_space_group_crystal_system      monoclinic
_space_group_IT_number           14
_space_group_name_Hall           '-P 2yn'
_space_group_name_H-M_alt        'P 1 21/n 1'
_symmetry_space_group_name_Hall  '-P 2yn'
_symmetry_space_group_name_H-M   'P 1 21/n 1'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     dual
_audit_creation_date             2017-02-21
_audit_creation_method
;
Olex2 1.2-alpha
(compiled 2017.02.06 svn.r3384 for OlexSys, GUI svn.r5312)
;
_cell_angle_alpha                90
_cell_angle_beta                 94.076(5)
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   5.6770(3)
_cell_length_b                   12.7750(5)
_cell_length_c                   27.3695(16)
_cell_measurement_reflns_used    2745
_cell_measurement_temperature    293(2)
_cell_measurement_theta_max      22.8860
_cell_measurement_theta_min      3.8850
_cell_volume                     1979.92(17)
_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      293(2)
_diffrn_detector_area_resol_mean 16.0892
_diffrn_measured_fraction_theta_full 0.998
_diffrn_measured_fraction_theta_max 0.998
_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  0.0423
_diffrn_reflns_av_unetI/netI     0.0616
_diffrn_reflns_Laue_measured_fraction_full 0.998
_diffrn_reflns_Laue_measured_fraction_max 0.998
_diffrn_reflns_limit_h_max       7
_diffrn_reflns_limit_h_min       -7
_diffrn_reflns_limit_k_max       15
_diffrn_reflns_limit_k_min       -15
_diffrn_reflns_limit_l_max       31
_diffrn_reflns_limit_l_min       -34
_diffrn_reflns_number            13318
_diffrn_reflns_point_group_measured_fraction_full 0.998
_diffrn_reflns_point_group_measured_fraction_max 0.998
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         26.372
_diffrn_reflns_theta_min         3.384
_diffrn_source                   'micro-focus sealed X-ray tube'
_exptl_absorpt_coefficient_mu    2.491
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.25156
_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    1.559
_exptl_crystal_description       Block
_exptl_crystal_F_000             936
_exptl_crystal_size_max          0.5
_exptl_crystal_size_mid          0.2
_exptl_crystal_size_min          0.2
_refine_diff_density_max         1.083
_refine_diff_density_min         -0.671
_refine_diff_density_rms         0.088
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.042
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     226
_refine_ls_number_reflns         4042
_refine_ls_number_restraints     7
_refine_ls_restrained_S_all      1.041
_refine_ls_R_factor_all          0.1136
_refine_ls_R_factor_gt           0.0608
_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^)+(0.0834P)^2^+1.2304P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1529
_refine_ls_wR_factor_ref         0.1905
_reflns_Friedel_coverage         0.000
_reflns_number_gt                2351
_reflns_number_total             4042
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            ja7b02076_si_004.cif
_cod_data_source_block           ty-1157
_cod_depositor_comments
'Adding full bibliography for 4125981--4125982.cif.'
_cod_database_code               4125981
_shelx_shelxl_version_number     2014/7
_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. Restrained distances
 C2-C1
 1.534 with sigma of 0.001
3. Uiso/Uaniso restraints and constraints
C2 \\sim C1: within 2A with sigma of 0.007 and sigma for terminal atoms of 0.001
4.a Ternary CH refined with riding coordinates:
 C5(H5), C6(H6), C4(H4), C3(H3)
4.b Secondary CH2 refined with riding coordinates:
 C2(H2A,H2B)
4.c Me refined with riding coordinates:
 C1(H1A,H1B,H1C)
4.d Aromatic/amide H refined with riding coordinates:
 C16(H16), C15(H15), C12(H12), C19(H19), C8(H8), C10(H10), C18(H18), C9(H9),
 C11(H11)
;
_olex2_submission_special_instructions 'No special instructions were received'