Gold-catalyzed oxidative cyclization of amide-alkynes: access to functionalized γ-lactams.
Zheng, Yi; Zhang, Ting-Ting; Shen, Wen-Bo; Organic & biomolecular chemistry 19 (2021) 9688–9691; doi:10.1039/d1ob01846a

data_7158360
_publ_section_title
;
 Gold-catalyzed oxidative cyclization of amide-alkynes: access to
 functionalized \g-lactams.
;
_journal_issue                   44
_journal_name_full               'Organic &amp; biomolecular chemistry'
_journal_page_first              9688
_journal_page_last               9691
_journal_paper_doi               10.1039/d1ob01846a
_journal_volume                  19
_journal_year                    2021
_chemical_formula_moiety         'C31 H23 Br N2 O5 S'
_chemical_formula_sum            'C31 H23 Br N2 O5 S'
_chemical_formula_weight         615.48
_space_group_crystal_system      monoclinic
_space_group_IT_number           14
_space_group_name_Hall           '-P 2ybc'
_space_group_name_H-M_alt        'P 1 21/c 1'
_atom_sites_solution_hydrogens   mixed
_atom_sites_solution_primary     direct
_audit_creation_date             2020-09-14
_audit_creation_method
;
Olex2 1.2
(compiled 2018.05.29 svn.r3508 for OlexSys, GUI svn.r5506)
;
_audit_update_record
;
2020-12-09 deposited with the CCDC.	2021-10-22 downloaded from the CCDC.
;
_cell_angle_alpha                90
_cell_angle_beta                 101.076(3)
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   10.9570(4)
_cell_length_b                   29.1941(10)
_cell_length_c                   8.9667(3)
_cell_measurement_reflns_used    2574
_cell_measurement_temperature    293(2)
_cell_measurement_theta_max      70.1050
_cell_measurement_theta_min      4.3470
_cell_volume                     2814.84(17)
_computing_cell_refinement       'CrysAlisPro 1.171.40.53 (Rigaku OD, 2019)'
_computing_data_collection       'CrysAlisPro 1.171.40.53 (Rigaku OD, 2019)'
_computing_data_reduction        'CrysAlisPro 1.171.40.53 (Rigaku OD, 2019)'
_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    'ShelXS (Sheldrick, 2008)'
_diffrn_ambient_temperature      293(2)
_diffrn_detector                 'CCD plate'
_diffrn_detector_area_resol_mean 16.2312
_diffrn_detector_type            Eos
_diffrn_measured_fraction_theta_full 0.996
_diffrn_measured_fraction_theta_max 0.996
_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    -60.00  -6.00   0.50    2.00    --  -33.50 -77.00  30.00  108
  2  \w    -99.00 -73.00   0.50    2.00    --  -33.50 -77.00  30.00   52
  3  \w     58.00 103.00   0.50    2.00    --   36.47 178.00-120.00   90
  4  \w      8.00  58.00   0.50    2.00    --   36.47 -37.00  30.00  100
  5  \w    -32.00  31.00   0.50    2.00    --   36.47 -57.00-120.00  126
  6  \w     15.00  74.00   0.50    2.00    --   36.47  37.00  30.00  118
  7  \w    -26.00  32.00   0.50    2.00    --   36.47 -57.00 -90.00  116
  8  \w     22.00  56.00   0.50    2.00    --   36.47 -99.00 150.00   68
  9  \w     24.00  67.00   0.50    2.00    --   36.47 -99.00-180.00   86
 10  \w    -32.00  -7.00   0.50    2.00    --   36.47 -37.00  30.00   50
 11  \w     42.00  74.00   0.50   15.00    --  108.00 -94.00  60.00   64
 12  \w    122.00 170.00   0.50   15.00    --  108.00  45.00   0.00   96
 13  \w     37.00 111.00   0.50   15.00    --  108.00-111.00 -90.00  148
 14  \w     78.00 108.00   0.50   15.00    --  108.00 -94.00  60.00   60
 15  \w    108.00 176.00   0.50   15.00    --  108.00  61.00-150.00  136
 16  \w     50.00 109.00   0.50   15.00    --  108.00 -94.00 -30.00  118
 17  \w    108.00 135.00   0.50   15.00    --  108.00 -77.00  30.00   54
 18  \w     39.00  65.00   0.50   15.00    --  108.00 -77.00  30.00   52
 19  \w     88.00 173.00   0.50   15.00    --  108.00  61.00  90.00  170
 20  \w     37.00 120.00   0.50   15.00    --  108.00 -30.00  60.00  166
;
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'Xcalibur, Eos, Gemini'
_diffrn_measurement_method       '\w scans'
_diffrn_orient_matrix_type
'CrysAlisPro convention (1999,Acta A55,543-557)'
_diffrn_orient_matrix_UB_11      0.0911032000
_diffrn_orient_matrix_UB_12      0.0373635000
_diffrn_orient_matrix_UB_13      0.0741502000
_diffrn_orient_matrix_UB_21      0.0986975000
_diffrn_orient_matrix_UB_22      -0.0369408000
_diffrn_orient_matrix_UB_23      0.0554955000
_diffrn_orient_matrix_UB_31      0.0498978000
_diffrn_orient_matrix_UB_32      0.0048421000
_diffrn_orient_matrix_UB_33      -0.1485620000
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54184
_diffrn_reflns_av_R_equivalents  0.0327
_diffrn_reflns_av_unetI/netI     0.0415
_diffrn_reflns_Laue_measured_fraction_full 0.996
_diffrn_reflns_Laue_measured_fraction_max 0.996
_diffrn_reflns_limit_h_max       13
_diffrn_reflns_limit_h_min       -12
_diffrn_reflns_limit_k_max       34
_diffrn_reflns_limit_k_min       -33
_diffrn_reflns_limit_l_max       8
_diffrn_reflns_limit_l_min       -10
_diffrn_reflns_number            11574
_diffrn_reflns_point_group_measured_fraction_full 0.996
_diffrn_reflns_point_group_measured_fraction_max 0.996
_diffrn_reflns_theta_full        67.068
_diffrn_reflns_theta_max         67.068
_diffrn_reflns_theta_min         4.111
_diffrn_source                   'fine-focus sealed X-ray tube'
_diffrn_source_type              'Enhance (Cu) X-ray Source'
_exptl_absorpt_coefficient_mu    3.046
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.66358
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
CrysAlisPro 1.171.40.53 (Rigaku Oxford Diffraction, 2019)
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_crystal_colour            colourless
_exptl_crystal_colour_primary    colourless
_exptl_crystal_density_diffrn    1.452
_exptl_crystal_description       plate
_exptl_crystal_F_000             1256
_exptl_crystal_size_max          0.2
_exptl_crystal_size_mid          0.09
_exptl_crystal_size_min          0.04
_refine_diff_density_max         0.475
_refine_diff_density_min         -0.686
_refine_diff_density_rms         0.045
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.038
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     366
_refine_ls_number_reflns         5010
_refine_ls_number_restraints     1
_refine_ls_restrained_S_all      1.038
_refine_ls_R_factor_all          0.0727
_refine_ls_R_factor_gt           0.0485
_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^)+(0.0528P)^2^+0.7127P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1186
_refine_ls_wR_factor_ref         0.1328
_reflns_Friedel_coverage         0.000
_reflns_number_gt                3531
_reflns_number_total             5010
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            d1ob01846a2.cif
_cod_data_source_block           202009169
_cod_depositor_comments          'Adding full bibliography for 7158360.cif.'
_cod_original_cell_volume        2814.84(18)
_cod_database_code               7158360
_shelx_shelxl_version_number     2014/7
_chemical_oxdiff_formula         C14H15N2O1S1Br1
_chemical_oxdiff_usercomment     r
_shelx_estimated_absorpt_t_max   0.888
_shelx_estimated_absorpt_t_min   0.581
_reflns_odcompleteness_completeness 99.59
_reflns_odcompleteness_iscentric 1
_reflns_odcompleteness_theta     66.97
_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. Restrained distances
 H2-N2
 0.87 with sigma of 0.02
3.a Secondary CH2 refined with riding coordinates:
 C4(H4A,H4B)
3.b Aromatic/amide H refined with riding coordinates:
 C7(H7), C8(H8), C9(H9), C10(H10), C13(H13), C14(H14), C15(H15), C16(H16),
 C17(H17), C20(H20), C21(H21), C23(H23), C24(H24), C26(H26), C27(H27), C29(H29),
  C30(H30)
3.c Idealised Me refined as rotating group:
 C31(H31A,H31B,H31C)
;
_shelx_res_checksum              17039
_shelx_hkl_checksum              62805
_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 1.768
_oxdiff_exptl_absorpt_empirical_full_min 0.791