Copper(II)-Catalyzed Reactions of α-Keto Thioesters with Azides via C-C and C-S Bond Cleavages: Synthesis of N-Acylureas and Amides.
Maity, Rajib; Naskar, Sandip; Das, Indrajit; The Journal of organic chemistry 83 (2018) 2114–2124; doi:10.1021/acs.joc.7b03054

data_4035001
_publ_section_title
;
 Copper(II)-Catalyzed Reactions of \a-Keto Thioesters with Azides via C-C
 and C-S Bond Cleavages: Synthesis of N-Acylureas and Amides.
;
_journal_issue                   4
_journal_name_full               'The Journal of organic chemistry'
_journal_page_first              2114
_journal_page_last               2124
_journal_paper_doi               10.1021/acs.joc.7b03054
_journal_volume                  83
_journal_year                    2018
_chemical_formula_moiety         'C10 H10 N2 O2'
_chemical_formula_sum            'C10 H10 N2 O2'
_chemical_formula_weight         190.20
_space_group_crystal_system      orthorhombic
_space_group_IT_number           29
_space_group_name_Hall           'P 2c -2ac'
_space_group_name_H-M_alt        'P c a 21'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     dual
_audit_creation_date             2017-04-17
_audit_creation_method
;
Olex2 1.2
(compiled 2017.03.02 svn.r3394 for OlexSys, GUI svn.r5335)
;
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_formula_units_Z            8
_cell_length_a                   13.755(4)
_cell_length_b                   5.1325(15)
_cell_length_c                   25.638(8)
_cell_measurement_reflns_used    7497
_cell_measurement_temperature    296.15
_cell_measurement_theta_max      25.90
_cell_measurement_theta_min      2.81
_cell_volume                     1810.0(9)
_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      296.15
_diffrn_measured_fraction_theta_full 0.990
_diffrn_measured_fraction_theta_max 0.965
_diffrn_measurement_device_type  'Bruker APEX-II CCD'
_diffrn_measurement_method       '\f and \w scans'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0577
_diffrn_reflns_av_unetI/netI     0.0427
_diffrn_reflns_Laue_measured_fraction_full 0.990
_diffrn_reflns_Laue_measured_fraction_max 0.965
_diffrn_reflns_limit_h_max       16
_diffrn_reflns_limit_h_min       -16
_diffrn_reflns_limit_k_max       6
_diffrn_reflns_limit_k_min       -6
_diffrn_reflns_limit_l_max       31
_diffrn_reflns_limit_l_min       -31
_diffrn_reflns_number            17720
_diffrn_reflns_point_group_measured_fraction_full 0.984
_diffrn_reflns_point_group_measured_fraction_max 0.947
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         26.245
_diffrn_reflns_theta_min         2.962
_diffrn_standards_number         0
_exptl_absorpt_coefficient_mu    0.100
_exptl_absorpt_correction_T_max  0.7454
_exptl_absorpt_correction_T_min  0.5558
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
'SADABS-2014/5 (Bruker,2014/5) was used for absorption correction. wR2(int) was 0.1480 before and 0.0781 after correction. The Ratio of minimum to maximum transmission is 0.7456. The \l/2 correction factor is 0.00150.'
_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    1.396
_exptl_crystal_description       plate
_exptl_crystal_F_000             800
_exptl_crystal_size_max          0.78
_exptl_crystal_size_mid          0.53
_exptl_crystal_size_min          0.1
_refine_diff_density_max         0.865
_refine_diff_density_min         -0.289
_refine_diff_density_rms         0.098
_refine_ls_abs_structure_details
;
 Flack x determined using 1259 quotients [(I+)-(I-)]/[(I+)+(I-)]
 (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259).
;
_refine_ls_abs_structure_Flack   0.1(7)
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.093
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     253
_refine_ls_number_reflns         3473
_refine_ls_number_restraints     1
_refine_ls_restrained_S_all      1.093
_refine_ls_R_factor_all          0.0857
_refine_ls_R_factor_gt           0.0766
_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^)+(0.1250P)^2^+1.0490P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1939
_refine_ls_wR_factor_ref         0.2041
_reflns_Friedel_coverage         0.916
_reflns_Friedel_fraction_full    0.978
_reflns_Friedel_fraction_max     0.928
_reflns_number_gt                3021
_reflns_number_total             3473
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            jo7b03054_si_002.cif
_cod_data_source_block           id_pkm_4a_0m
_cod_database_code               4035001
_shelx_shelxl_version_number     2016/6
_olex2_refinement_description
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups, All N(H) groups, All N(H,H) groups
2.a Aromatic/amide H refined with riding coordinates:
 N1AA(H1AA), N1(H1), C8(H8), C6AA(H6AA), C7AA(H7AA), C4AA(H4AA), C0AA(H0AC),
 C7(H7), C6(H6), C5(H5), C3(H3), C2AA(H2AA), C2(H2), C5AA(H5AA), C1AA(H1AB),
 C1(H1A)
2.b X=CH2 refined with riding coordinates:
 N2(H2A,H2B), N0AA(H0AA,H0AB)
;
_shelx_res_checksum              87567
_shelx_hkl_checksum              47711
_olex2_submission_special_instructions 'No special instructions were received'