Copper(II)-Mediated Intramolecular Cyclopropanation of Ketene N,X-Acetals (X = S, O, N) under Mild Conditions.
Huang, Fei; Wu, Ping; Yu, Zhengkun; The Journal of organic chemistry  (2020) –; doi:10.1021/acs.joc.0c00093

data_4037986
_publ_section_title
;
 Copper(II)-Mediated Intramolecular Cyclopropanation of Ketene N,X-Acetals
 (X = S, O, N) under Mild Conditions.
;
_journal_name_full               'The Journal of organic chemistry'
_journal_paper_doi               10.1021/acs.joc.0c00093
_journal_year                    2020
_chemical_absolute_configuration unk
_chemical_formula_sum            'C15 H16 N2 O'
_chemical_formula_weight         240.30
_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   mixed
_audit_creation_method           SHELXL-2013
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_formula_units_Z            8
_cell_length_a                   8.4335(10)
_cell_length_b                   17.4528(18)
_cell_length_c                   17.6982(13)
_cell_measurement_reflns_used    3116
_cell_measurement_temperature    293(2)
_cell_measurement_theta_max      27.209
_cell_measurement_theta_min      3.722
_cell_volume                     2605.0(5)
_computing_cell_refinement       'Bruker SMART'
_computing_data_collection       'Bruker SMART'
_computing_data_reduction        'Bruker SAINT'
_computing_molecular_graphics    'Bruker SHELXTL'
_computing_publication_material  'Bruker SHELXTL'
_computing_structure_refinement  'SHELXL-2013 (Sheldrick, 2013)'
_computing_structure_solution    'Bruker SHELXTL'
_diffrn_ambient_temperature      293(2)
_diffrn_measured_fraction_theta_full 0.997
_diffrn_measured_fraction_theta_max 0.997
_diffrn_measurement_device_type  'CCD area detector'
_diffrn_measurement_method       'phi and omega scans'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0266
_diffrn_reflns_av_unetI/netI     0.0409
_diffrn_reflns_Laue_measured_fraction_full 0.997
_diffrn_reflns_Laue_measured_fraction_max 0.997
_diffrn_reflns_limit_h_max       10
_diffrn_reflns_limit_h_min       -10
_diffrn_reflns_limit_k_max       19
_diffrn_reflns_limit_k_min       -21
_diffrn_reflns_limit_l_max       21
_diffrn_reflns_limit_l_min       -16
_diffrn_reflns_number            9606
_diffrn_reflns_point_group_measured_fraction_full 0.984
_diffrn_reflns_point_group_measured_fraction_max 0.980
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         25.998
_diffrn_reflns_theta_min         3.279
_exptl_absorpt_coefficient_mu    0.078
_exptl_absorpt_correction_T_max  1.0000
_exptl_absorpt_correction_T_min  0.9413
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   sadabs
_exptl_crystal_colour            colorless
_exptl_crystal_density_diffrn    1.225
_exptl_crystal_description       prismatic
_exptl_crystal_F_000             1024
_exptl_crystal_size_max          0.200
_exptl_crystal_size_mid          0.160
_exptl_crystal_size_min          0.110
_refine_diff_density_max         0.160
_refine_diff_density_min         -0.156
_refine_diff_density_rms         0.033
_refine_ls_abs_structure_details
; 
 Flack x determined using 1392 quotients [(I+)-(I-)]/[(I+)+(I-)] 
 (Parsons and Flack (2004), Acta Cryst. A60, s61). 
;
_refine_ls_abs_structure_Flack   2.0(8)
_refine_ls_extinction_coef       0.0078(13)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc^2^\l^3^/sin(2\q)]^-1/4^
_refine_ls_extinction_method     SHELXL
_refine_ls_goodness_of_fit_ref   1.059
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     378
_refine_ls_number_reflns         5018
_refine_ls_number_restraints     76
_refine_ls_restrained_S_all      1.070
_refine_ls_R_factor_all          0.0675
_refine_ls_R_factor_gt           0.0468
_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^)+(0.0427P)^2^+0.3692P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0976
_refine_ls_wR_factor_ref         0.1095
_reflns_Friedel_coverage         0.731
_reflns_Friedel_fraction_full    0.966
_reflns_Friedel_fraction_max     0.958
_reflns_number_gt                3891
_reflns_number_total             5018
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            jo0c00093_si_002.cif
_cod_data_source_block           HFC419
_cod_original_cell_volume        2605.0(4)
_cod_database_code               4037986
_shelx_estimated_absorpt_t_min   0.985
_shelx_estimated_absorpt_t_max   0.991
_shelxl_version_number           2013-4
_shelx_res_checksum              44910
_shelx_hkl_checksum              91402