Highly Regio- and Enantioselective Vicinal Dihalogenation of Allyl Amides.
Soltanzadeh, Bardia; Jaganathan, Arvind; Yi, Yi; Yi, Hajoon; Staples, Richard J.; Borhan, Babak; Journal of the American Chemical Society 139 (2017) 2132–2135; doi:10.1021/jacs.6b09203

data_4125777
_publ_section_title
;
 Highly Regio- and Enantioselective Vicinal Dihalogenation of Allyl
 Amides.
;
_journal_issue                   6
_journal_name_full               'Journal of the American Chemical Society'
_journal_page_first              2132
_journal_page_last               2135
_journal_paper_doi               10.1021/jacs.6b09203
_journal_volume                  139
_journal_year                    2017
_chemical_formula_moiety         'C13 H16 Br Cl N2 O3'
_chemical_formula_sum            'C13 H16 Br Cl N2 O3'
_chemical_formula_weight         363.64
_space_group_crystal_system      monoclinic
_space_group_IT_number           15
_space_group_name_Hall           '-C 2yc'
_space_group_name_H-M_alt        'C 1 2/c 1'
_symmetry_space_group_name_Hall  '-C 2yc'
_symmetry_space_group_name_H-M   'C 1 2/c 1'
_atom_sites_solution_hydrogens   geom
_audit_creation_date             2016-02-08
_audit_creation_method
;
Olex2 1.2-alpha
(compiled 2016.01.25 svn.r3250 for OlexSys, GUI svn.r5148)
;
_cell_angle_alpha                90
_cell_angle_beta                 104.322(2)
_cell_angle_gamma                90
_cell_formula_units_Z            8
_cell_length_a                   21.628(4)
_cell_length_b                   5.0320(10)
_cell_length_c                   29.519(6)
_cell_measurement_reflns_used    2660
_cell_measurement_temperature    173(2)
_cell_measurement_theta_max      25.03
_cell_measurement_theta_min      2.85
_cell_volume                     3112.8(11)
_computing_cell_refinement       'SAINT v8.34A (Bruker, 2013)'
_computing_data_collection       'COSMO (BRUKER, V1.61, 2009)'
_computing_data_reduction        'SAINT v8.34A (Bruker, 2013)'
_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    'ShelXS (Sheldrick, 2008)'
_diffrn_ambient_temperature      173(2)
_diffrn_detector_area_resol_mean 8.36
_diffrn_measured_fraction_theta_full 0.999
_diffrn_measured_fraction_theta_max 0.994
_diffrn_measurement_device_type  'Bruker APEX-II CCD'
_diffrn_measurement_method       \w
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0875
_diffrn_reflns_av_unetI/netI     0.0810
_diffrn_reflns_Laue_measured_fraction_full 0.999
_diffrn_reflns_Laue_measured_fraction_max 0.994
_diffrn_reflns_limit_h_max       26
_diffrn_reflns_limit_h_min       -26
_diffrn_reflns_limit_k_max       6
_diffrn_reflns_limit_k_min       -5
_diffrn_reflns_limit_l_max       35
_diffrn_reflns_limit_l_min       -35
_diffrn_reflns_number            11646
_diffrn_reflns_point_group_measured_fraction_full 0.999
_diffrn_reflns_point_group_measured_fraction_max 0.994
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         25.412
_diffrn_reflns_theta_min         1.944
_diffrn_source                   'sealed tube'
_diffrn_standards_number         0
_exptl_absorpt_coefficient_mu    2.820
_exptl_absorpt_correction_T_max  0.7452
_exptl_absorpt_correction_T_min  0.6084
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
'SADABS-2014/5 (Bruker,2014/5) was used for absorption correction. wR2(int) was 0.0795 before and 0.0583 after correction. The Ratio of minimum to maximum transmission is 0.8164. The \l/2 correction factor is 0.00150.'
_exptl_crystal_colour            colourless
_exptl_crystal_colour_primary    colourless
_exptl_crystal_density_diffrn    1.552
_exptl_crystal_description       needle
_exptl_crystal_F_000             1472
_exptl_crystal_recrystallization_method 'used as recieved'
_exptl_crystal_size_max          0.298
_exptl_crystal_size_mid          0.064
_exptl_crystal_size_min          0.033
_refine_diff_density_max         1.520
_refine_diff_density_min         -0.747
_refine_diff_density_rms         0.150
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.107
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     182
_refine_ls_number_reflns         2837
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.107
_refine_ls_R_factor_all          0.1253
_refine_ls_R_factor_gt           0.0792
_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^)+(0.1032P)^2^+33.6766P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.2131
_refine_ls_wR_factor_ref         0.2359
_reflns_Friedel_coverage         0.000
_reflns_number_gt                1841
_reflns_number_total             2837
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            ja6b09203_si_003.cif
_cod_data_source_block           bb216a
_cod_database_code               4125777
_shelxl_version_number           2014/6
_shelx_estimated_absorpt_t_max   0.913
_shelx_estimated_absorpt_t_min   0.487
_olex2_refinement_description
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups, All C(H,H) groups, All N(H) groups
 At 1.5 times of:
  All C(H,H,H) groups
2.a Ternary CH refined with riding coordinates:
 C2(H2), C3(H3)
2.b Secondary CH2 refined with riding coordinates:
 C1(H1A,H1B), C4(H4A,H4B), C5(H5A,H5B)
2.c Aromatic/amide H refined with riding coordinates:
 N1(H1), C9(H9), C10(H10), C12(H12), C13(H13)
2.d Idealised Me refined as rotating group:
 C6(H6A,H6B,H6C)
;
_contact_crystallographer_email  staples@chemistry.msu.com
_contact_crystallographer_name   'Richard Staples'
_olex2_diffrn_ambient_temperature_device 'Oxford Cryosystems'
_olex2_exptl_crystal_mounting_method
'The crystal was mounted on a nylon loop with paratone oil'
_olex2_submission_original_sample_id 'Vial 1'
_olex2_submission_special_instructions 'No special instructions were received'