Ritter-enabled catalytic asymmetric chloroamidation of olefins.
Steigerwald, Daniel C.; Soltanzadeh, Bardia; Sarkar, Aritra; Morgenstern, Cecilia C.; Staples, Richard J.; Borhan, Babak; Chemical science 12 (2020) 1834–1842; doi:10.1039/d0sc05224h

data_1559734
_publ_section_title
;
 Ritter-enabled catalytic asymmetric chloroamidation of olefins.
;
_journal_issue                   5
_journal_name_full               'Chemical science'
_journal_page_first              1834
_journal_page_last               1842
_journal_paper_doi               10.1039/d0sc05224h
_journal_volume                  12
_journal_year                    2020
_chemical_absolute_configuration ad
_chemical_formula_moiety         'C15 H20 Br Cl N2 O2'
_chemical_formula_sum            'C15 H20 Br Cl N2 O2'
_chemical_formula_weight         375.69
_space_group_crystal_system      triclinic
_space_group_IT_number           1
_space_group_name_Hall           'P 1'
_space_group_name_H-M_alt        'P 1'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     dual
_audit_creation_date             2019-04-11
_audit_creation_method
;
Olex2 1.2
(compiled 2018.05.29 svn.r3508 for OlexSys, GUI svn.r5506)
;
_audit_update_record
;
2019-04-11 deposited with the CCDC.	2020-11-26 downloaded from the CCDC.
;
_cell_angle_alpha                88.027(2)
_cell_angle_beta                 85.435(2)
_cell_angle_gamma                89.121(2)
_cell_formula_units_Z            2
_cell_length_a                   4.9505(2)
_cell_length_b                   8.5820(3)
_cell_length_c                   19.9420(6)
_cell_measurement_reflns_used    6368
_cell_measurement_temperature    173(2)
_cell_measurement_theta_max      69.60
_cell_measurement_theta_min      4.45
_cell_volume                     843.98(5)
_computing_cell_refinement       'SAINT v8.34A (Bruker, 2013)'
_computing_data_collection       'COSMO (BRUKER, V1.61, 2009)'
_computing_data_reduction        'SAINT V8.38A (?, 2016)'
_computing_molecular_graphics
;
O. V. Dolomanov, L. J. Bourhis, R. J. Gildea, J. A. K. Howard and H. Puschmann,
OLEX2: a complete structure solution, refinement and analysis program.
J. Appl. Cryst. (2009). 42, 339-341.
;
_computing_publication_material
;
O. V. Dolomanov, L. J. Bourhis, R. J. Gildea, J. A. K. Howard and H. Puschmann,
OLEX2: a complete structure solution, refinement and analysis program.
J. Appl. Cryst. (2009). 42, 339-341.
;
_computing_structure_refinement
'SHELXL (Sheldrick, Acta Cryst. A64 2008, 112-122)'
_computing_structure_solution
'SHELXT (Sheldrick, G.M. (2015). Acta Cryst. A71, 3-8)'
_diffrn_ambient_temperature      173(2)
_diffrn_detector_area_resol_mean 8.36
_diffrn_measured_fraction_theta_full 0.976
_diffrn_measured_fraction_theta_max 0.971
_diffrn_measurement_device_type  'Bruker APEX-II CCD'
_diffrn_measurement_method       '\f and \w scans'
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54178
_diffrn_reflns_av_R_equivalents  0.0567
_diffrn_reflns_av_unetI/netI     0.0589
_diffrn_reflns_Laue_measured_fraction_full 0.976
_diffrn_reflns_Laue_measured_fraction_max 0.971
_diffrn_reflns_limit_h_max       6
_diffrn_reflns_limit_h_min       -6
_diffrn_reflns_limit_k_max       9
_diffrn_reflns_limit_k_min       -10
_diffrn_reflns_limit_l_max       24
_diffrn_reflns_limit_l_min       -24
_diffrn_reflns_number            19825
_diffrn_reflns_point_group_measured_fraction_full 0.953
_diffrn_reflns_point_group_measured_fraction_max 0.946
_diffrn_reflns_theta_full        67.679
_diffrn_reflns_theta_max         70.126
_diffrn_reflns_theta_min         2.224
_diffrn_source                   'sealed tube'
_diffrn_standards_number         0
_exptl_absorpt_coefficient_mu    4.824
_exptl_absorpt_correction_T_max  0.1048
_exptl_absorpt_correction_T_min  0.0183
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
'SADABS-2016/2 (Bruker,2016/2) was used for absorption correction. wR2(int) was 0.1005 before and 0.0740 after correction. The Ratio of minimum to maximum transmission is 0.1746. The \l/2 correction factor is Not present.'
_exptl_crystal_colour            colourless
_exptl_crystal_colour_primary    colourless
_exptl_crystal_density_diffrn    1.478
_exptl_crystal_description       needle
_exptl_crystal_F_000             384
_exptl_crystal_recrystallization_method 'used as received'
_exptl_crystal_size_max          0.257
_exptl_crystal_size_mid          0.118
_exptl_crystal_size_min          0.03
_refine_diff_density_max         0.771
_refine_diff_density_min         -0.215
_refine_diff_density_rms         0.082
_refine_ls_abs_structure_details
;
 Flack x determined using 2087 quotients [(I+)-(I-)]/[(I+)+(I-)]
 (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259).
;
_refine_ls_abs_structure_Flack   0.005(16)
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.050
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     383
_refine_ls_number_reflns         6030
_refine_ls_number_restraints     3
_refine_ls_restrained_S_all      1.050
_refine_ls_R_factor_all          0.0586
_refine_ls_R_factor_gt           0.0489
_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^)+(0.0593P)^2^] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1146
_refine_ls_wR_factor_ref         0.1207
_reflns_Friedel_coverage         0.948
_reflns_Friedel_fraction_full    0.930
_reflns_Friedel_fraction_max     0.920
_reflns_number_gt                5104
_reflns_number_total             6030
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            d0sc05224h2.cif
_cod_data_source_block           bb319t
_cod_depositor_comments
;Adding full bibliography for 1559733--1559734.cif.

 Adding full bibliography for 1559733--1559734.cif.
;
_cod_database_code               1559734
_shelx_shelxl_version_number     2018/3
_shelx_estimated_absorpt_t_max   0.869
_shelx_estimated_absorpt_t_min   0.370
_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:
 C2A(H2AA), C3A(H3A), C2B(H2BA), C3B(H3B)
2.b Secondary CH2 refined with riding coordinates:
 C1A(H1AA,H1AB), C4A(H4AA,H4AB), C5A(H5AA,H5AB), C1B(H1BA,H1BB), C4B(H4BA,
 H4BB), C5B(H5BA,H5BB)
2.c Aromatic/amide H refined with riding coordinates:
 N1A(H1A), N2A(H2A), C11A(H11A), C12A(H12A), C14A(H14A), C15A(H15A), N1B(H1B),
 N2B(H2B), C11B(H11B), C12B(H12B), C14B(H14B), C15B(H15B)
2.d Idealised Me refined as rotating group:
 C6A(H6AA,H6AB,H6AC), C8A(H8AA,H8AB,H8AC), C6B(H6BA,H6BB,H6BC), C8B(H8BA,H8BB,
 H8BC)
;
_shelx_res_checksum              35792
_olex2_diffrn_ambient_temperature_device 'Oxford Cryosystems'
_olex2_exptl_crystal_mounting_method
'The crystal was mounted on a MITIGEN holder with paratone oil'
_olex2_submission_original_sample_id 42
_olex2_submission_special_instructions 'No special instructions were received'