Copper-Catalyzed Asymmetric Aminocyanation of Arylcyclopropanes for Synthesis of γ-Amino Nitriles
Yang, Shengbiao; Wang, Lihong; Zhang, Hongwei; Liu, Chunyang; Zhang, Linli; Wang, Xiaomin; Zhang, Ge; Li, Yan; Zhang, Qian; ACS Catalysis 9 (2018) 716–; doi:10.1021/acscatal.8b03768

data_4515484
_publ_section_title
;
 Copper-Catalyzed Asymmetric Aminocyanation of Arylcyclopropanes for
 Synthesis of \g-Amino Nitriles
;
_journal_issue                   1
_journal_name_full               'ACS Catalysis'
_journal_page_first              716
_journal_paper_doi               10.1021/acscatal.8b03768
_journal_volume                  9
_journal_year                    2018
_chemical_absolute_configuration ad
_chemical_formula_moiety         '2(C23 H22 N2 O4 S2)'
_chemical_formula_sum            'C23 H22 N2 O4 S2'
_chemical_formula_weight         454.54
_chemical_name_systematic        YSB-!
_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     direct
_audit_creation_date             2018-03-27
_audit_creation_method
;
Olex2 1.2
(compiled 2016.02.19 svn.r3266 for OlexSys, GUI svn.r5155)
;
_cell_angle_alpha                103.063(5)
_cell_angle_beta                 98.741(5)
_cell_angle_gamma                91.068(5)
_cell_formula_units_Z            2
_cell_length_a                   9.0036(9)
_cell_length_b                   10.9036(11)
_cell_length_c                   11.9944(12)
_cell_measurement_reflns_used    9484
_cell_measurement_temperature    293
_cell_measurement_theta_max      72.133
_cell_measurement_theta_min      3.833
_cell_volume                     1132.0(2)
_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    'ShelXS (Sheldrick, 2008)'
_diffrn_ambient_temperature      298.0
_diffrn_measured_fraction_theta_full 0.992
_diffrn_measured_fraction_theta_max 0.984
_diffrn_measurement_device_type  'CCD Area Detector'
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54184
_diffrn_reflns_av_R_equivalents  0.0364
_diffrn_reflns_av_unetI/netI     0.0522
_diffrn_reflns_Laue_measured_fraction_full 0.992
_diffrn_reflns_Laue_measured_fraction_max 0.984
_diffrn_reflns_limit_h_max       11
_diffrn_reflns_limit_h_min       -10
_diffrn_reflns_limit_k_max       13
_diffrn_reflns_limit_k_min       -13
_diffrn_reflns_limit_l_max       14
_diffrn_reflns_limit_l_min       -14
_diffrn_reflns_number            18234
_diffrn_reflns_point_group_measured_fraction_full 0.934
_diffrn_reflns_point_group_measured_fraction_max 0.914
_diffrn_reflns_theta_full        67.684
_diffrn_reflns_theta_max         72.678
_diffrn_reflns_theta_min         3.833
_exptl_absorpt_coefficient_mu    2.400
_exptl_absorpt_correction_T_max  299
_exptl_absorpt_correction_T_min  290
_exptl_absorpt_correction_type   analytical
_exptl_crystal_colour            'clear light colourless'
_exptl_crystal_colour_lustre     clear
_exptl_crystal_colour_modifier   light
_exptl_crystal_colour_primary    colourless
_exptl_crystal_density_diffrn    1.334
_exptl_crystal_description       cube
_exptl_crystal_F_000             476
_exptl_crystal_preparation       YSB-yoyo
_exptl_crystal_recrystallization_method 'U KNOW~'
_exptl_crystal_size_max          0.3
_exptl_crystal_size_mid          0.28
_exptl_crystal_size_min          0.25
_refine_diff_density_max         0.175
_refine_diff_density_min         -0.258
_refine_diff_density_rms         0.038
_refine_ls_abs_structure_details
;
 Flack x determined using 2749 quotients [(I+)-(I-)]/[(I+)+(I-)]
 (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259).
;
_refine_ls_abs_structure_Flack   0.054(7)
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.044
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     561
_refine_ls_number_reflns         8235
_refine_ls_number_restraints     3
_refine_ls_restrained_S_all      1.044
_refine_ls_R_factor_all          0.0519
_refine_ls_R_factor_gt           0.0391
_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^)+(0.0364P)^2^+0.1578P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0886
_refine_ls_wR_factor_ref         0.0966
_reflns_Friedel_coverage         0.858
_reflns_Friedel_fraction_full    0.877
_reflns_Friedel_fraction_max     0.844
_reflns_number_gt                6868
_reflns_number_total             8235
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            cs8b03768_si_001.cif
_cod_data_source_block           cu_zhangq180326_0m
_cod_database_code               4515484
_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.a Ternary CH refined with riding coordinates:
 C8(H8), C37(H37)
2.b Secondary CH2 refined with riding coordinates:
 C11(H11A,H11B), C10(H10A,H10B), C40(H40A,H40B), C39(H39A,H39B)
2.c Aromatic/amide H refined with riding coordinates:
 C3(H3), C23(H23), C22(H22), C13(H13), C14(H14), C4(H4), C6(H6), C21(H21),
 C5(H5), C15(H15), C17(H17), C20(H20), C19(H19), C16(H16), C34(H34), C33(H33),
 C35(H35), C52(H52), C32(H32), C42(H42), C50(H50), C43(H43), C44(H44), C48(H48),
  C45(H45), C46(H46), C49(H49), C51(H51)
2.d Idealised Me refined as rotating group:
 C1(H1A,H1B,H1C), C30(H30A,H30B,H30C)
;
_shelx_res_checksum              68173
_shelx_hkl_checksum              18118
_shelx_shelxl_version_number     2014/7
_olex2_exptl_crystal_mounting_method 'Who Knows ?'
_olex2_submission_special_instructions 'No special instructions were received'