Coinage (Au, Ag, Cu) metal-catalyzed (3 + 2) annulation of α-aminoketones and electron-deficient alkynes as a route to 3-EWG-substituted pyrroles
Chikunova, Elena I.; Kotikova, Polina F.; Dar'in, Dmitry V.; Kukushkin, Vadim Yu.; Dubovtsev, Alexey Yu.; Catalysis Science & Technology 14 (2024) 5671–5677; doi:10.1039/D4CY00660G

data_1572224
_publ_section_title
;
 Coinage (Au, Ag, Cu) metal-catalyzed (3 + 2) annulation of
 \a-aminoketones and electron-deficient alkynes as a route to
 3-EWG-substituted pyrroles
;
_journal_issue                   19
_journal_name_full               'Catalysis Science &amp; Technology'
_journal_page_first              5671
_journal_page_last               5677
_journal_paper_doi               10.1039/D4CY00660G
_journal_volume                  14
_journal_year                    2024
_chemical_formula_moiety         'C49 H40 N2 O4 S'
_chemical_formula_sum            'C49 H40 N2 O4 S'
_chemical_formula_weight         752.89
_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   geom
_atom_sites_solution_primary     dual
_audit_creation_date             2023-12-23
_audit_creation_method
;
Olex2 1.5
(compiled 2023.08.24 svn.re1ec1418 for OlexSys, GUI svn.r6817)
;
_audit_update_record
;
2024-01-19 deposited with the CCDC.	2024-08-01 downloaded from the CCDC.
;
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   9.2439(2)
_cell_length_b                   14.8214(4)
_cell_length_c                   28.8605(7)
_cell_measurement_reflns_used    13896
_cell_measurement_temperature    100(2)
_cell_measurement_theta_max      79.5280
_cell_measurement_theta_min      3.0580
_cell_volume                     3954.11(17)
_computing_cell_refinement       'CrysAlisPro 1.171.41.103a (Rigaku OD, 2021)'
_computing_data_collection       'CrysAlisPro 1.171.41.103a (Rigaku OD, 2021)'
_computing_data_reduction        'CrysAlisPro 1.171.41.103a (Rigaku OD, 2021)'
_computing_molecular_graphics    'Olex2 1.5 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 1.5 (Dolomanov et al., 2009)'
_computing_structure_refinement  'SHELXL 2014/7 (Sheldrick, 2015)'
_computing_structure_solution    'SHELXT 2014/5 (Sheldrick, 2014)'
_diffrn_ambient_environment      N~2~
_diffrn_ambient_temperature      100(2)
_diffrn_detector                 'Hybrid Pixel Array Detector'
_diffrn_detector_area_resol_mean 10.0000
_diffrn_detector_type            HyPix
_diffrn_measured_fraction_theta_full 0.998
_diffrn_measured_fraction_theta_max 0.965
_diffrn_measurement_details
;
List of Runs (angles in degrees, time in seconds):

  # Type    Start    End  Width  t~exp~   \w     \q     \k     \f   Frames
  1  \w     21.00  86.00   0.50    0.70    --   47.51-112.00-177.00  130
  2  \w   -134.00 -33.00   0.50    3.00    -- -106.00 159.00 156.00  202
  3  \w     48.00  92.00   0.50    3.00    --  113.25-112.00-177.00   88
  4  \w    101.00 177.00   0.50    3.00    --  113.25  18.00 169.00  152
  5  \w   -107.00 -80.00   0.50    0.70    --  -47.51-125.00 -60.00   54
  6  \w     74.00 119.00   0.50    0.70    --   47.51 125.00-120.00   90
  7  \w    -27.00  25.00   0.50    0.70    --   47.51 -19.00-120.00  104
  8  \w    -27.00  22.00   0.50    0.70    --   47.51 -18.00   0.00   98
  9  \w    -66.00 -36.00   0.50    3.00    -- -106.00  61.00  30.00   60
 10  \w    -65.00 -34.00   0.50    3.00    -- -106.00  61.00  90.00   62
 11  \w     43.00  98.00   0.50    3.00    --  113.25 -94.00 -90.00  110
 12  \w     42.00  70.00   0.50    3.00    --  113.25 -61.00 150.00   56
 13  \w     46.00  71.00   0.50    3.00    --  113.25 -61.00-120.00   50
 14  \w     42.00  68.00   0.50    3.00    --  113.25 -61.00 -90.00   52
 15  \w    123.00 156.00   0.50    3.00    --  113.25  45.00 120.00   66
 16  \w    113.00 157.00   0.50    3.00    --  113.25  61.00-180.00   88
 17  \w     82.00 115.00   0.50    3.00    --  113.25 112.00 -84.00   66
 18  \w   -109.00 -83.50   0.50    0.70    --  -47.51-125.00 150.00   51
;
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type
'XtaLAB Synergy, Single source at home/near, HyPix'
_diffrn_measurement_method       '\w scans'
_diffrn_orient_matrix_type
'CrysAlisPro convention (1999,Acta A55,543-557)'
_diffrn_orient_matrix_UB_11      0.1266103000
_diffrn_orient_matrix_UB_12      0.0674586000
_diffrn_orient_matrix_UB_13      -0.0009902000
_diffrn_orient_matrix_UB_21      -0.1058290000
_diffrn_orient_matrix_UB_22      0.0764838000
_diffrn_orient_matrix_UB_23      -0.0126624000
_diffrn_orient_matrix_UB_31      -0.0231305000
_diffrn_orient_matrix_UB_32      0.0199397000
_diffrn_orient_matrix_UB_33      0.0518278000
_diffrn_radiation_monochromator  mirror
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           'Cu K\a'
_diffrn_radiation_wavelength     1.54184
_diffrn_reflns_av_R_equivalents  0.0317
_diffrn_reflns_av_unetI/netI     0.0350
_diffrn_reflns_Laue_measured_fraction_full 0.998
_diffrn_reflns_Laue_measured_fraction_max 0.965
_diffrn_reflns_limit_h_max       11
_diffrn_reflns_limit_h_min       -11
_diffrn_reflns_limit_k_max       17
_diffrn_reflns_limit_k_min       -18
_diffrn_reflns_limit_l_max       36
_diffrn_reflns_limit_l_min       -27
_diffrn_reflns_number            20406
_diffrn_reflns_point_group_measured_fraction_full 0.972
_diffrn_reflns_point_group_measured_fraction_max 0.912
_diffrn_reflns_theta_full        67.684
_diffrn_reflns_theta_max         80.401
_diffrn_reflns_theta_min         3.062
_diffrn_source                   'micro-focus sealed X-ray tube'
_diffrn_source_type              'PhotonJet (Cu) X-ray Source'
_exptl_absorpt_coefficient_mu    1.109
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.66106
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
CrysAlisPro 1.171.41.103a (Rigaku Oxford Diffraction, 2021)
Empirical absorption correction using spherical harmonics,
implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_crystal_colour            'clear yellowish colourless'
_exptl_crystal_colour_lustre     clear
_exptl_crystal_colour_modifier   yellowish
_exptl_crystal_colour_primary    colourless
_exptl_crystal_density_diffrn    1.265
_exptl_crystal_description       prism
_exptl_crystal_F_000             1584
_exptl_crystal_size_max          0.2
_exptl_crystal_size_mid          0.18
_exptl_crystal_size_min          0.04
_refine_diff_density_max         0.452
_refine_diff_density_min         -0.317
_refine_diff_density_rms         0.040
_refine_ls_abs_structure_details
;
 Flack x determined using 2963 quotients [(I+)-(I-)]/[(I+)+(I-)]
 (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259).
;
_refine_ls_abs_structure_Flack   0.021(8)
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.073
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     507
_refine_ls_number_reflns         7885
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.073
_refine_ls_R_factor_all          0.0372
_refine_ls_R_factor_gt           0.0355
_refine_ls_shift/su_max          0.001
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'w=1/[\s^2^(Fo^2^)+(0.0550P)^2^+0.5484P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0950
_refine_ls_wR_factor_ref         0.0959
_reflns_Friedel_coverage         0.689
_reflns_Friedel_fraction_full    0.938
_reflns_Friedel_fraction_max     0.844
_reflns_number_gt                7537
_reflns_number_total             7885
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            d4cy00660g2.cif
_cod_data_source_block           058-009_bp
_cod_depositor_comments
'Adding full bibliography for 1572223--1572224.cif.'
_cod_database_code               1572224
_shelx_shelxl_version_number     2014/7
_publ_section_exptl
;
Any special experimental details
;
_chemical_oxdiff_formula         'C49 H40 N2 O4 S'
_shelx_estimated_absorpt_t_max   0.957
_shelx_estimated_absorpt_t_min   0.809
_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 Secondary CH2 refined with riding coordinates:
 C11(H01B,H01C), C36(H01I,H01J)
2.b Aromatic/amide H refined with riding coordinates:
 C2(H008), C3(H00B), C25(H00G), C5(H00J), C29(H00N), C46(H00P), C45(H00R),
 C19(H00T), C6(H00U), C23(H00V), C26(H00W), C34(H00X), C10(H00Y), C28(H00Z),
 C41(H010), C13(H011), C47(H012), C17(H013), C22(H015), C16(H016), C42(H017),
 C20(H018), C49(H019), C15(H01A), C43(H01D), C14(H01E), C39(H01F), C40(H01G),
 C48(H01H), C21(H01K)
2.c Idealised Me refined as rotating group:
 C30(H01L,H01M,H01N), C37(H01O,H01P,H01Q)
;
_shelx_res_checksum              39975
_olex2_submission_special_instructions 'No special instructions were received'
_oxdiff_exptl_absorpt_empirical_details
;
Empirical correction (ABSPACK) includes:
- Absorption correction using spherical harmonics
- Frame scaling
;
_oxdiff_exptl_absorpt_empirical_full_max 1.665
_oxdiff_exptl_absorpt_empirical_full_min 0.509