Assembly of polysubstituted chiral cyclopropylamines via highly enantioselective Cu-catalyzed three-component cyclopropene alkenylamination.
Zhang, Yu; Li, Yuan; Zhou, Wei; Zhang, Mengru; Zhang, Qian; Jia, Ran; Zhao, Jinbo; Chemical communications (Cambridge, England) 56 (2020) 12250–12253; doi:10.1039/d0cc01060j

data_7127206
_publ_section_title
;
 Assembly of polysubstituted chiral cyclopropylamines via highly
 enantioselective Cu-catalyzed three-component cyclopropene
 alkenylamination.
;
_journal_issue                   81
_journal_name_full               'Chemical communications (Cambridge, England)'
_journal_page_first              12250
_journal_page_last               12253
_journal_paper_doi               10.1039/d0cc01060j
_journal_volume                  56
_journal_year                    2020
_chemical_absolute_configuration ad
_chemical_formula_moiety         'C27 H26 Br N O'
_chemical_formula_sum            'C27 H26 Br N O'
_chemical_formula_weight         460.40
_space_group_crystal_system      orthorhombic
_space_group_IT_number           19
_space_group_name_Hall           'P 2ac 2ab'
_space_group_name_H-M_alt        'P 21 21 21'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     dual
_audit_creation_date             2019-05-23
_audit_creation_method
;
Olex2 1.2
(compiled 2018.05.29 svn.r3508 for OlexSys, GUI svn.r5506)
;
_audit_update_record
;
2020-08-09 deposited with the CCDC.	2020-09-08 downloaded from the CCDC.
;
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   9.6932(5)
_cell_length_b                   10.7179(6)
_cell_length_c                   21.8420(11)
_cell_measurement_reflns_used    9870
_cell_measurement_temperature    293
_cell_measurement_theta_max      69.163
_cell_measurement_theta_min      4.048
_cell_volume                     2269.2(2)
_computing_cell_refinement       'SAINT V8.38A (?, 2016)'
_computing_data_reduction        'SAINT V8.38A (?, 2016)'
_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
_diffrn_measured_fraction_theta_full 0.998
_diffrn_measured_fraction_theta_max 0.993
_diffrn_measurement_device_type  'CCD area detector'
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54178
_diffrn_reflns_av_R_equivalents  0.0352
_diffrn_reflns_av_unetI/netI     0.0301
_diffrn_reflns_Laue_measured_fraction_full 0.998
_diffrn_reflns_Laue_measured_fraction_max 0.993
_diffrn_reflns_limit_h_max       11
_diffrn_reflns_limit_h_min       -7
_diffrn_reflns_limit_k_max       13
_diffrn_reflns_limit_k_min       -12
_diffrn_reflns_limit_l_max       26
_diffrn_reflns_limit_l_min       -26
_diffrn_reflns_number            21847
_diffrn_reflns_point_group_measured_fraction_full 0.994
_diffrn_reflns_point_group_measured_fraction_max 0.982
_diffrn_reflns_theta_full        67.679
_diffrn_reflns_theta_max         69.693
_diffrn_reflns_theta_min         4.048
_exptl_absorpt_coefficient_mu    2.595
_exptl_crystal_colour            'clear whiteish colourless'
_exptl_crystal_colour_lustre     clear
_exptl_crystal_colour_modifier   whiteish
_exptl_crystal_colour_primary    colourless
_exptl_crystal_density_diffrn    1.348
_exptl_crystal_description       cube
_exptl_crystal_F_000             952
_refine_diff_density_max         0.345
_refine_diff_density_min         -0.627
_refine_diff_density_rms         0.051
_refine_ls_abs_structure_details
;
 Flack x determined using 1571 quotients [(I+)-(I-)]/[(I+)+(I-)]
 (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259).
;
_refine_ls_abs_structure_Flack   -0.002(6)
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.072
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     271
_refine_ls_number_reflns         4191
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.072
_refine_ls_R_factor_all          0.0322
_refine_ls_R_factor_gt           0.0282
_refine_ls_shift/su_max          0.001
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'w=1/[\s^2^(Fo^2^)+(0.0264P)^2^+0.8511P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0623
_refine_ls_wR_factor_ref         0.0640
_reflns_Friedel_coverage         0.730
_reflns_Friedel_fraction_full    0.988
_reflns_Friedel_fraction_max     0.968
_reflns_number_gt                3921
_reflns_number_total             4191
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            d0cc01060j2.cif
_cod_data_source_block           zhaojb190523_1_0m_a
_cod_depositor_comments          'Adding full bibliography for 7127206.cif.'
_cod_database_code               7127206
_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
2.a Ternary CH refined with riding coordinates:
 C9(H9), C10(H10)
2.b Secondary CH2 refined with riding coordinates:
 C12(H12A,H12B), C13(H13A,H13B), C14(H14A,H14B), C15(H15A,H15B)
2.c Aromatic/amide H refined with riding coordinates:
 C1(H1), C2(H2), C3(H3), C4(H4), C6(H6), C7(H7), C8(H8), C17(H17), C18(H18),
 C19(H19), C20(H20), C21(H21), C24(H24), C25(H25), C26(H26), C27(H27)
;
_shelx_res_checksum              57236
_shelx_hkl_checksum              23461
_olex2_submission_special_instructions 'No special instructions were received'