Copper catalyzed five-component domino strategy for the synthesis of nicotinimidamides.
Zhao, Yu; Li, Li; Zhou, Zitong; Chen, Man; Yang, Weiguang; Luo, Hui; Organic & biomolecular chemistry 19 (2021) 3868–3872; doi:10.1039/d1ob00162k

data_7157991
_publ_section_title
;
 Copper catalyzed five-component domino strategy for the synthesis of
 nicotinimidamides.
;
_journal_issue                   17
_journal_name_full               'Organic &amp; biomolecular chemistry'
_journal_page_first              3868
_journal_page_last               3872
_journal_paper_doi               10.1039/d1ob00162k
_journal_volume                  19
_journal_year                    2021
_chemical_formula_moiety         'C21 H21 N3 O2 S'
_chemical_formula_sum            'C21 H21 N3 O2 S'
_chemical_formula_weight         379.46
_space_group_crystal_system      orthorhombic
_space_group_IT_number           33
_space_group_name_Hall           'P 2c -2n'
_space_group_name_H-M_alt        'P n a 21'
_atom_sites_solution_hydrogens   mixed
_audit_block_doi                 10.5517/ccdc.csd.cc26lmq5
_audit_creation_date             2020-11-01
_audit_creation_method
;
Olex2 1.3
(compiled Nov 21 2019 18:26:39 for OlexSys, GUI svn.r6003)
;
_audit_update_record
;
2020-11-11 deposited with the CCDC.	2021-03-26 downloaded from the CCDC.
;
_cell_angle_alpha                90
_cell_angle_beta                 90.000(7)
_cell_angle_gamma                90
_cell_formula_units_Z            8
_cell_length_a                   17.663(6)
_cell_length_b                   7.822(3)
_cell_length_c                   29.714(10)
_cell_measurement_reflns_used    2970
_cell_measurement_temperature    273.15
_cell_measurement_theta_max      22.40
_cell_measurement_theta_min      2.40
_cell_volume                     4105(3)
_computing_cell_refinement       'SAINT v8.34A (Bruker, 2013)'
_computing_data_reduction        'SAINT v8.34A (Bruker, 2013)'
_computing_molecular_graphics    'Olex2 1.3 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 1.3 (Dolomanov et al., 2009)'
_computing_structure_refinement  'SHELXL 2018/3 (Sheldrick, 2015)'
_computing_structure_solution    'SHELXT 2018/2 (Sheldrick, 2018)'
_diffrn_ambient_temperature      273.15
_diffrn_measured_fraction_theta_full 1.000
_diffrn_measured_fraction_theta_max 1.000
_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  0.1035
_diffrn_reflns_av_unetI/netI     0.1299
_diffrn_reflns_Laue_measured_fraction_full 1.000
_diffrn_reflns_Laue_measured_fraction_max 1.000
_diffrn_reflns_limit_h_max       19
_diffrn_reflns_limit_h_min       -21
_diffrn_reflns_limit_k_max       9
_diffrn_reflns_limit_k_min       -9
_diffrn_reflns_limit_l_max       31
_diffrn_reflns_limit_l_min       -35
_diffrn_reflns_number            19436
_diffrn_reflns_point_group_measured_fraction_full 0.967
_diffrn_reflns_point_group_measured_fraction_max 0.967
_diffrn_reflns_theta_full        25.025
_diffrn_reflns_theta_max         25.025
_diffrn_reflns_theta_min         2.306
_diffrn_standards_number         0
_exptl_absorpt_coefficient_mu    0.177
_exptl_absorpt_correction_T_max  0.7456
_exptl_absorpt_correction_T_min  0.6188
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
SADABS-2014/5 (Bruker,2014/5) was used for absorption correction.
wR2(int) was 0.1021 before and 0.0445 after correction.
The Ratio of minimum to maximum transmission is 0.8299.
The \l/2 correction factor is 0.00150.
;
_exptl_crystal_colour            colourless
_exptl_crystal_colour_primary    colourless
_exptl_crystal_density_diffrn    1.228
_exptl_crystal_description       block
_exptl_crystal_F_000             1600
_exptl_crystal_size_max          0.13
_exptl_crystal_size_mid          0.12
_exptl_crystal_size_min          0.1
_refine_diff_density_max         1.110
_refine_diff_density_min         -0.355
_refine_diff_density_rms         0.095
_refine_ls_abs_structure_details
;
 Refined as an inversion twin.
;
_refine_ls_abs_structure_Flack   0.3(3)
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   0.973
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     493
_refine_ls_number_reflns         7015
_refine_ls_number_restraints     1
_refine_ls_restrained_S_all      0.973
_refine_ls_R_factor_all          0.1783
_refine_ls_R_factor_gt           0.0958
_refine_ls_shift/su_max          0.051
_refine_ls_shift/su_mean         0.002
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'w=1/[\s^2^(Fo^2^)+(0.1476P)^2^] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.2247
_refine_ls_wR_factor_ref         0.2679
_reflns_Friedel_coverage         0.895
_reflns_Friedel_fraction_full    0.933
_reflns_Friedel_fraction_max     0.933
_reflns_number_gt                3513
_reflns_number_total             7015
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            d1ob00162k2.cif
_cod_data_source_block           123_sq
_cod_depositor_comments
;
          Adding full bibliography for 7157991.cif.

2024-06-28
Z value and formula fixed to values more according to usual
chemical conventions.                 miguel
;
_cod_original_cell_volume        4105(2)
_cod_original_formula_moiety     '2(C21 H21 N3 O2 S)'
_cod_original_formula_sum        'C42 H42 N6 O4 S2'
_cod_original_formula_units_Z    4
_cod_original_formula_weight     758.93
_cod_database_code               7157991
_shelx_shelxl_version_number     2018/3
_shelx_estimated_absorpt_t_max   0.982
_shelx_estimated_absorpt_t_min   0.977
_olex2_refinement_description
;
1. Twinned data refinement
 Scales: 0.7(3)
 0.3(3)
2. Fixed Uiso
 At 1.2 times of:
  All C(H) groups, All C(H,H) groups, All N(H,H) groups
 At 1.5 times of:
  All C(H,H,H) groups
3.a Rotating group:
 N1(H1A,H1B)
3.b Secondary CH2 refined with riding coordinates:
 C25(H25A,H25B), C23(H23A,H23B)
3.c Aromatic/amide H refined with riding coordinates:
 C8(H8), C48(H48), C49(H49), C56(H56), C15(H15), C29(H29), C40(H40), C42(H42),
 C45(H45), C14(H14), C20(H20), C21(H21), C24(H24), C4(H4), C22(H22), C10(H10),
 C50(H50), C54(H54), C39(H39), C43(H43), C44(H44), C46(H46)
3.d X=CH2 refined with riding coordinates:
 N9(H9A,H9B)
3.e Idealised Me refined as rotating group:
 C17(H17A,H17B,H17C), C51(H51A,H51B,H51C), C36(H36A,H36B,H36C), C41(H41A,H41B,
 H41C)
;
_shelx_res_checksum              40951
_shelx_fab_checksum              12262
_platon_squeeze_void_probe_radius 1.20
_olex2_submission_special_instructions 'No special instructions were received'