Asymmetric Nitrone Synthesis via Ligand-Enabled Copper-Catalyzed Cope-Type Hydroamination of Cyclopropene with Oxime.
Li, Zhanyu; Zhao, Jinbo; Sun, Baozhen; Zhou, Tingting; Liu, Mingzhu; Liu, Shuang; Zhang, Mengru; Zhang, Qian; Journal of the American Chemical Society  (2017) –; doi:10.1021/jacs.7b06523

data_4126329
_publ_section_title
;
 Asymmetric Nitrone Synthesis via Ligand-Enabled Copper-Catalyzed
 Cope-Type Hydroamination of Cyclopropene with Oxime.
;
_journal_name_full               'Journal of the American Chemical Society'
_journal_paper_doi               10.1021/jacs.7b06523
_journal_year                    2017
_chemical_absolute_configuration ad
_chemical_formula_moiety         'C27 H23 N O'
_chemical_formula_sum            'C26 H23 N2 O'
_chemical_formula_weight         379.46
_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'
_symmetry_space_group_name_Hall  'P 2ac 2ab'
_symmetry_space_group_name_H-M   'P 21 21 21'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     dual
_audit_creation_date             2017-07-30
_audit_creation_method
;
Olex2 1.2
(compiled 2017.03.28 svn.r3405 for OlexSys, GUI svn.r5335)
;
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   8.7558(3)
_cell_length_b                   11.1462(4)
_cell_length_c                   21.2016(7)
_cell_measurement_reflns_used    9957
_cell_measurement_temperature    293.0
_cell_measurement_theta_max      72.32
_cell_measurement_theta_min      4.48
_cell_volume                     2069.15(12)
_computing_cell_refinement       'SAINT v8.37A (Bruker, 2015)'
_computing_data_reduction        'SAINT v8.37A (Bruker, 2015)'
_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      292.7
_diffrn_measured_fraction_theta_full 0.988
_diffrn_measured_fraction_theta_max 0.987
_diffrn_measurement_device_type  'CCD Area Detector'
_diffrn_measurement_method       'phi and omega scans'
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54178
_diffrn_reflns_av_R_equivalents  0.0361
_diffrn_reflns_av_unetI/netI     0.0195
_diffrn_reflns_Laue_measured_fraction_full 0.988
_diffrn_reflns_Laue_measured_fraction_max 0.987
_diffrn_reflns_limit_h_max       10
_diffrn_reflns_limit_h_min       -10
_diffrn_reflns_limit_k_max       12
_diffrn_reflns_limit_k_min       -13
_diffrn_reflns_limit_l_max       26
_diffrn_reflns_limit_l_min       -26
_diffrn_reflns_number            35129
_diffrn_reflns_point_group_measured_fraction_full 0.990
_diffrn_reflns_point_group_measured_fraction_max 0.988
_diffrn_reflns_theta_full        67.679
_diffrn_reflns_theta_max         72.773
_diffrn_reflns_theta_min         4.170
_exptl_absorpt_coefficient_mu    0.580
_exptl_absorpt_correction_T_max  0.944
_exptl_absorpt_correction_T_min  0.901
_exptl_absorpt_correction_type   analytical
_exptl_absorpt_process_details   ad
_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    1.218
_exptl_crystal_description       cube
_exptl_crystal_F_000             804
_exptl_crystal_size_max          0.2
_exptl_crystal_size_mid          0.15
_exptl_crystal_size_min          0.1
_refine_diff_density_max         0.126
_refine_diff_density_min         -0.124
_refine_diff_density_rms         0.027
_refine_ls_abs_structure_details
;
 Flack x determined using 1580 quotients [(I+)-(I-)]/[(I+)+(I-)]
 (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259).
;
_refine_ls_abs_structure_Flack   0.04(9)
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.067
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     263
_refine_ls_number_reflns         4085
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.067
_refine_ls_R_factor_all          0.0468
_refine_ls_R_factor_gt           0.0430
_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^)+(0.0463P)^2^+0.3577P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1055
_refine_ls_wR_factor_ref         0.1094
_reflns_Friedel_coverage         0.749
_reflns_Friedel_fraction_full    0.993
_reflns_Friedel_fraction_max     0.990
_reflns_number_gt                3822
_reflns_number_total             4085
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            ja7b06523_si_002.cif
_cod_data_source_block           2
_cod_database_code               4126329
_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.a Ternary CH refined with riding coordinates:
 C1(H1)
2.b Secondary CH2 refined with riding coordinates:
 C2(H2A,H2B)
2.c Aromatic/amide H refined with riding coordinates:
 C5(H5), C6(H6), C8(H8), C9(H9), C10(H10), C11(H11), C13(H13), C17(H17),
 C18(H18), C19(H19), C20(H20), C21(H21), C23(H23), C24(H24), C25(H25), C26(H26),
  C27(H27)
2.d Idealised Me refined as rotating group:
 C14(H14A,H14B,H14C)
;
_shelx_res_checksum              90391
_shelx_hkl_checksum              85953
_olex2_submission_special_instructions 'No special instructions were received'