Transition-metal-free oxidative cyclization of N-propargyl ynamides: stereospecific construction of linear polycyclic N-heterocycles
Wang, Cai-Ming; Qi, Lin-Jun; Sun, Qing; Zhou, Bo; Zhang, Zhi-Xin; Shi, Zai-Fa; Lin, Shui-Chao; Lu, Xin; Gong, Lei; Ye, Long-Wu; Green Chemistry 20 (2018) 3271–; doi:10.1039/C8GC01534A

data_7230943
_publ_section_title
;
 Transition-metal-free oxidative cyclization of N-propargyl ynamides:
 stereospecific construction of linear polycyclic N-heterocycles
;
_journal_issue                   14
_journal_name_full               'Green Chemistry'
_journal_page_first              3271
_journal_paper_doi               10.1039/C8GC01534A
_journal_volume                  20
_journal_year                    2018
_chemical_formula_moiety         'C25 H23 N O3 S'
_chemical_formula_sum            'C25 H23 N O3 S'
_chemical_formula_weight         417.50
_chemical_name_systematic
(3R,3aS,4R,9aS)-1-(methylsulfonyl)-3,4-diphenyl-3a,4,9,9a-tetrahydro-1H-benzo[f]indol-2(3H)-one
_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'
_symmetry_space_group_name_Hall  '-P 2ybc'
_symmetry_space_group_name_H-M   'P 1 21/c 1'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     iterative
_audit_creation_date             2016-08-05
_audit_creation_method
;
Olex2 1.2
(compiled 2016.02.19 svn.r3266 for OlexSys, GUI svn.r5155)
;
_audit_update_record
;
2017-08-17 deposited with the CCDC.
2018-06-18 downloaded from the CCDC.
;
_cell_angle_alpha                90
_cell_angle_beta                 103.857(8)
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   18.5095(15)
_cell_length_b                   10.9007(8)
_cell_length_c                   10.3745(8)
_cell_measurement_reflns_used    1488
_cell_measurement_temperature    100.00(10)
_cell_measurement_theta_max      65.3310
_cell_measurement_theta_min      4.7290
_cell_volume                     2032.3(3)
_computing_cell_refinement
;
CrysAlisPro, Agilent Technologies,
Version 1.171.37.35 (release 13-08-2014 CrysAlis171 .NET)
(compiled Aug 13 2014,18:06:01)
;
_computing_data_collection
;
CrysAlisPro, Agilent Technologies,
Version 1.171.37.35 (release 13-08-2014 CrysAlis171 .NET)
(compiled Aug 13 2014,18:06:01)
;
_computing_data_reduction
;
CrysAlisPro, Agilent Technologies,
Version 1.171.37.35 (release 13-08-2014 CrysAlis171 .NET)
(compiled Aug 13 2014,18:06:01)
;
_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
;
Superflip (Palatinus & Chapuis, 2007;Palatinus & van der Lee, 2008;
Palatinus et al., 2012)
;
_diffrn_ambient_environment      N~2~
_diffrn_ambient_temperature      100.00(10)
_diffrn_detector                 'CCD plate'
_diffrn_detector_area_resol_mean 10.4741
_diffrn_detector_type            Atlas
_diffrn_measured_fraction_theta_full 0.965
_diffrn_measured_fraction_theta_max 0.965
_diffrn_measurement_details
;
  1 omega  -49.00   33.00   1.0000    3.0000
omega____ theta____ kappa____ phi______ frames
    -      -40.5047   37.0000   60.0000 82

  2 omega  -87.00  -16.00   1.0000    3.0000
omega____ theta____ kappa____ phi______ frames
    -      -40.5047  125.0000   90.0000 71

  3 omega  -94.00  -28.00   1.0000    3.0000
omega____ theta____ kappa____ phi______ frames
    -      -40.5047  125.0000  -30.0000 66

  4 omega   21.00  113.00   1.0000   12.5000
omega____ theta____ kappa____ phi______ frames
    -       91.1609  -61.0000 -180.0000 92

  5 omega   61.00   98.00   1.0000   12.5000
omega____ theta____ kappa____ phi______ frames
    -       91.1609   61.0000  -30.0000 37

  6 omega  131.00  158.00   1.0000   12.5000
omega____ theta____ kappa____ phi______ frames
    -       91.1609   61.0000  -30.0000 27

  7 omega  129.00  178.00   1.0000   12.5000
omega____ theta____ kappa____ phi______ frames
    -       91.1609    0.0000   30.0000 49

  8 omega  109.00  150.00   1.0000   12.5000
omega____ theta____ kappa____ phi______ frames
    -       91.1609  125.0000 -180.0000 41

  9 omega   32.00  105.00   1.0000   12.5000
omega____ theta____ kappa____ phi______ frames
    -       91.1609    0.0000   30.0000 73

 10 omega   13.00   73.00   1.0000   12.5000
omega____ theta____ kappa____ phi______ frames
    -       91.1609  -30.0000 -150.0000 60
;
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'SuperNova, Dual, Cu at zero, Atlas'
_diffrn_measurement_method       '\w scans'
_diffrn_orient_matrix_UB_11      -0.0670602000
_diffrn_orient_matrix_UB_12      -0.0433579000
_diffrn_orient_matrix_UB_13      -0.1090099000
_diffrn_orient_matrix_UB_21      0.0410064000
_diffrn_orient_matrix_UB_22      -0.1207236000
_diffrn_orient_matrix_UB_23      -0.0128781000
_diffrn_orient_matrix_UB_31      -0.0342151000
_diffrn_orient_matrix_UB_32      -0.0594936000
_diffrn_orient_matrix_UB_33      0.1064101000
_diffrn_radiation_monochromator  mirror
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54184
_diffrn_reflns_av_R_equivalents  0.0774
_diffrn_reflns_av_unetI/netI     0.0912
_diffrn_reflns_Laue_measured_fraction_full 0.965
_diffrn_reflns_Laue_measured_fraction_max 0.965
_diffrn_reflns_limit_h_max       21
_diffrn_reflns_limit_h_min       -19
_diffrn_reflns_limit_k_max       11
_diffrn_reflns_limit_k_min       -12
_diffrn_reflns_limit_l_max       12
_diffrn_reflns_limit_l_min       -7
_diffrn_reflns_number            7032
_diffrn_reflns_point_group_measured_fraction_full 0.965
_diffrn_reflns_point_group_measured_fraction_max 0.965
_diffrn_reflns_theta_full        65.949
_diffrn_reflns_theta_max         65.949
_diffrn_reflns_theta_min         4.745
_diffrn_source                   'sealed X-ray tube'
_diffrn_source_type              'SuperNova (Cu) X-ray Source'
_exptl_absorpt_coefficient_mu    1.637
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.87798
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
CrysAlisPro, Agilent Technologies,
Version 1.171.37.35 (release 13-08-2014 CrysAlis171 .NET)
(compiled Aug 13 2014,18:06:01)
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_crystal_colour            'clear colourless'
_exptl_crystal_colour_lustre     clear
_exptl_crystal_colour_primary    colourless
_exptl_crystal_density_diffrn    1.365
_exptl_crystal_description       block
_exptl_crystal_F_000             880
_exptl_crystal_recrystallization_method
'Re-crystallisation from solvent: hexane and ethyl acetate'
_exptl_crystal_size_max          0.2
_exptl_crystal_size_mid          0.15
_exptl_crystal_size_min          0.1
_refine_diff_density_max         0.351
_refine_diff_density_min         -0.429
_refine_diff_density_rms         0.074
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.028
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     272
_refine_ls_number_reflns         3416
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.028
_refine_ls_R_factor_all          0.0881
_refine_ls_R_factor_gt           0.0583
_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^)+(0.0660P)^2^+0.3900P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1418
_refine_ls_wR_factor_ref         0.1675
_reflns_Friedel_coverage         0.000
_reflns_number_gt                2384
_reflns_number_total             3416
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            c8gc01534a2.cif
_cod_data_source_block           exp_1657
_cod_depositor_comments
'Adding full bibliography for 7230942--7230944.cif.'
_cod_database_code               7230943
_reflns_odcompleteness_completeness 99.88
_reflns_odcompleteness_iscentric 1
_reflns_odcompleteness_theta     61.08
_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 Ternary CH refined with riding coordinates:
 C3(H3), C4(H4), C2(H2), C12(H12)
2.b Secondary CH2 refined with riding coordinates:
 C11(H11A,H11B)
2.c Aromatic/amide H refined with riding coordinates:
 C25(H25), C6(H6), C8(H8), C9(H9), C19(H19), C22(H22), C21(H21), C15(H15),
 C23(H23), C7(H7), C24(H24), C18(H18), C16(H16), C17(H17)
2.d Idealised Me refined as rotating group:
 C13(H13A,H13B,H13C)
;
_shelx_shelxl_version_number     2014/7
_olex2_submission_special_instructions 'No special instructions were received'