Copper-catalyzed decarboxylative ethynyl methylene cyclic carbamates with amines: modular synthesis of 3-aminopyrroles
Chen, Jiadong; Tang, Shengbiao; New Journal of Chemistry 48 (2024) 16996–16999; doi:10.1039/D4NJ03137G

data_7063439
_publ_section_title
;
 Copper-catalyzed decarboxylative ethynyl methylene cyclic carbamates with
 amines: modular synthesis of 3-aminopyrroles
;
_journal_issue                   39
_journal_name_full               'New Journal of Chemistry'
_journal_page_first              16996
_journal_page_last               16999
_journal_paper_doi               10.1039/D4NJ03137G
_journal_volume                  48
_journal_year                    2024
_chemical_formula_moiety         'C25 H24 N2 O3 S'
_chemical_formula_sum            'C25 H24 N2 O3 S'
_chemical_formula_weight         432.52
_space_group_crystal_system      triclinic
_space_group_IT_number           2
_space_group_name_Hall           '-P 1'
_space_group_name_H-M_alt        'P -1'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     dual
_audit_creation_date             2023-11-23
_audit_creation_method
;
Olex2 1.5
(compiled 2023.08.24 svn.re1ec1418 for OlexSys, GUI svn.r6817)
;
_audit_update_record
;
2024-05-21 deposited with the CCDC.	2024-09-10 downloaded from the CCDC.
;
_cell_angle_alpha                70.9370(10)
_cell_angle_beta                 82.2400(10)
_cell_angle_gamma                84.1790(10)
_cell_formula_units_Z            2
_cell_length_a                   9.04750(10)
_cell_length_b                   10.4700(2)
_cell_length_c                   12.6844(2)
_cell_measurement_reflns_used    9822
_cell_measurement_temperature    173.00
_cell_measurement_theta_max      54.985
_cell_measurement_theta_min      5.575
_cell_volume                     1123.16(3)
_computing_cell_refinement       'SAINT V8.40B (?, 2016)'
_computing_data_reduction        'SAINT V8.40B (?, 2016)'
_computing_molecular_graphics    'Olex2 1.5 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 1.5 (Dolomanov et al., 2009)'
_computing_structure_refinement  'SHELXL 2018/3 (Sheldrick, 2015)'
_computing_structure_solution    'SHELXT 2018/2 (Sheldrick, 2018)'
_diffrn_ambient_temperature      173.00
_diffrn_measured_fraction_theta_full 0.988
_diffrn_measured_fraction_theta_max 0.985
_diffrn_measurement_device_type  'Bruker D8 Venture'
_diffrn_measurement_method       '\f and \w scans'
_diffrn_radiation_type           GaK\a
_diffrn_radiation_wavelength     1.34139
_diffrn_reflns_av_R_equivalents  0.0477
_diffrn_reflns_av_unetI/netI     0.0399
_diffrn_reflns_Laue_measured_fraction_full 0.988
_diffrn_reflns_Laue_measured_fraction_max 0.985
_diffrn_reflns_limit_h_max       11
_diffrn_reflns_limit_h_min       -11
_diffrn_reflns_limit_k_max       12
_diffrn_reflns_limit_k_min       -12
_diffrn_reflns_limit_l_max       15
_diffrn_reflns_limit_l_min       -15
_diffrn_reflns_number            17147
_diffrn_reflns_point_group_measured_fraction_full 0.988
_diffrn_reflns_point_group_measured_fraction_max 0.985
_diffrn_reflns_theta_full        53.594
_diffrn_reflns_theta_max         54.991
_diffrn_reflns_theta_min         3.894
_diffrn_source_current           2.86
_diffrn_source_power             0.1995994
_diffrn_source_voltage           69.79
_diffrn_standards_number         0
_exptl_absorpt_coefficient_mu    0.986
_exptl_absorpt_correction_T_max  0.7508
_exptl_absorpt_correction_T_min  0.6246
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
SADABS-2016/2 (Bruker,2016/2) was used for absorption correction.
wR2(int) was 0.1257 before and 0.0608 after correction.
The Ratio of minimum to maximum transmission is 0.8319.
The \l/2 correction factor is Not present.
;
_exptl_crystal_colour            colourless
_exptl_crystal_colour_primary    colourless
_exptl_crystal_density_diffrn    1.279
_exptl_crystal_description       block
_exptl_crystal_F_000             456
_exptl_crystal_size_max          0.17
_exptl_crystal_size_mid          0.17
_exptl_crystal_size_min          0.05
_refine_diff_density_max         0.329
_refine_diff_density_min         -0.436
_refine_diff_density_rms         0.045
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.043
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     283
_refine_ls_number_reflns         4221
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.043
_refine_ls_R_factor_all          0.0504
_refine_ls_R_factor_gt           0.0407
_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^+0.5019P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1005
_refine_ls_wR_factor_ref         0.1067
_reflns_Friedel_coverage         0.000
_reflns_number_gt                3608
_reflns_number_total             4221
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            d4nj03137g2.cif
_cod_data_source_block           231123tsb_cjd_2_54
_cod_depositor_comments          'Adding full bibliography for 7063439.cif.'
_cod_database_code               7063439
_shelx_shelxl_version_number     2018/3
_shelx_estimated_absorpt_t_max   0.952
_shelx_estimated_absorpt_t_min   0.850
_olex2_refinement_description
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups, All N(H) groups
 At 1.5 times of:
  All C(H,H,H) groups
2.a Aromatic/amide H refined with riding coordinates:
 N2(H2), C1(H1), C7(H7), C8(H8), C9(H9), C10(H10), C11(H11), C13(H13),
 C14(H14), C16(H16), C17(H17), C20(H20), C21(H21), C23(H23), C24(H24)
2.b Idealised Me refined as rotating group:
 C5(H5A,H5B,H5C), C18(H18A,H18B,H18C), C25(H25A,H25B,H25C)
;
_shelx_res_checksum              84195
_olex2_submission_special_instructions 'No special instructions were received'