Copper-Catalyzed Oxidative Cyclization of Alkynes with Sulfonylhydrazides Leading to 2-Sulfonated 9H-pyrrolo[1,2-a]indol-9-ones.
Zhu, Xin-Yu; Li, Ming; Han, Ya-Ping; Chen, Si; Li, Xue-Song; Liang, Yong-Min; The Journal of organic chemistry 82 (2017) 8761–8768; doi:10.1021/acs.joc.7b01497

data_4032814
_publ_section_title
;
 Copper-Catalyzed Oxidative Cyclization of Alkynes with Sulfonylhydrazides
 Leading to 2-Sulfonated 9H-pyrrolo[1,2-a]indol-9-ones.
;
_journal_issue                   16
_journal_name_full               'The Journal of organic chemistry'
_journal_page_first              8761
_journal_page_last               8768
_journal_paper_doi               10.1021/acs.joc.7b01497
_journal_volume                  82
_journal_year                    2017
_chemical_formula_moiety         'C25 H19 N O4 S'
_chemical_formula_sum            'C25 H19 N O4 S'
_chemical_formula_weight         429.47
_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     direct
_audit_creation_date             2017-04-07
_audit_creation_method
;
Olex2 1.2
(compiled 2017.03.28 svn.r3405 for OlexSys, GUI svn.r5335)
;
_cell_angle_alpha                90
_cell_angle_beta                 91.919(5)
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   17.0424(8)
_cell_length_b                   5.8162(3)
_cell_length_c                   21.1265(12)
_cell_measurement_reflns_used    1215
_cell_measurement_temperature    289.86(10)
_cell_measurement_theta_max      22.5720
_cell_measurement_theta_min      4.0000
_cell_volume                     2092.93(19)
_computing_cell_refinement
;
CrysAlisPro, Agilent Technologies,
Version 1.171.36.28 (release 01-02-2013 CrysAlis171 .NET)
(compiled Feb  1 2013,16:14:44)
;
_computing_data_collection
;
CrysAlisPro, Agilent Technologies,
Version 1.171.36.28 (release 01-02-2013 CrysAlis171 .NET)
(compiled Feb  1 2013,16:14:44)
;
_computing_data_reduction
;
CrysAlisPro, Agilent Technologies,
Version 1.171.36.28 (release 01-02-2013 CrysAlis171 .NET)
(compiled Feb  1 2013,16:14:44)
;
_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      289.86(10)
_diffrn_detector_area_resol_mean 16.0733
_diffrn_measured_fraction_theta_full 0.998
_diffrn_measured_fraction_theta_max 0.998
_diffrn_measurement_details
;
  1 omega  -98.00  -64.00   1.0000    5.0000
omega____ theta____ kappa____ phi______ frames
    -      -19.5055  178.0000  -30.0000 34

  2 omega  -47.00   89.00   1.0000    5.0000
omega____ theta____ kappa____ phi______ frames
    -       22.7867    0.0000  -30.0000 136

  3 omega    8.00   61.00   1.0000    5.0000
omega____ theta____ kappa____ phi______ frames
    -       22.7867  -19.0000   60.0000 53
;
_diffrn_measurement_device_type  'SuperNova, Dual, Cu at zero, Eos'
_diffrn_measurement_method       '\w scans'
_diffrn_orient_matrix_UB_11      0.0211995000
_diffrn_orient_matrix_UB_12      0.0108230000
_diffrn_orient_matrix_UB_13      -0.0281913000
_diffrn_orient_matrix_UB_21      0.0194191000
_diffrn_orient_matrix_UB_22      0.0985139000
_diffrn_orient_matrix_UB_23      0.0126207000
_diffrn_orient_matrix_UB_31      0.0300972000
_diffrn_orient_matrix_UB_32      -0.0710636000
_diffrn_orient_matrix_UB_33      0.0132521000
_diffrn_radiation_monochromator  mirror
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0358
_diffrn_reflns_av_unetI/netI     0.0628
_diffrn_reflns_Laue_measured_fraction_full 0.998
_diffrn_reflns_Laue_measured_fraction_max 0.998
_diffrn_reflns_limit_h_max       21
_diffrn_reflns_limit_h_min       -12
_diffrn_reflns_limit_k_max       7
_diffrn_reflns_limit_k_min       -3
_diffrn_reflns_limit_l_max       26
_diffrn_reflns_limit_l_min       -25
_diffrn_reflns_number            7389
_diffrn_reflns_point_group_measured_fraction_full 0.998
_diffrn_reflns_point_group_measured_fraction_max 0.998
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         26.021
_diffrn_reflns_theta_min         3.589
_diffrn_source                   'SuperNova (Mo) X-ray Source'
_exptl_absorpt_coefficient_mu    0.187
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.69734
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
CrysAlisPro, Agilent Technologies,
Version 1.171.36.28 (release 01-02-2013 CrysAlis171 .NET)
(compiled Feb  1 2013,16:14:44)
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_crystal_colour            'clear dark yellow'
_exptl_crystal_colour_lustre     clear
_exptl_crystal_colour_modifier   dark
_exptl_crystal_colour_primary    yellow
_exptl_crystal_density_diffrn    1.363
_exptl_crystal_description       needle
_exptl_crystal_F_000             896
_exptl_crystal_size_max          0.24
_exptl_crystal_size_mid          0.12
_exptl_crystal_size_min          0.11
_refine_diff_density_max         0.223
_refine_diff_density_min         -0.272
_refine_diff_density_rms         0.043
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.044
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     337
_refine_ls_number_reflns         4111
_refine_ls_number_restraints     80
_refine_ls_restrained_S_all      1.071
_refine_ls_R_factor_all          0.1140
_refine_ls_R_factor_gt           0.0633
_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^)+(0.0627P)^2^+0.2908P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1368
_refine_ls_wR_factor_ref         0.1746
_reflns_Friedel_coverage         0.000
_reflns_number_gt                2322
_reflns_number_total             4111
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            jo7b01497_si_002.cif
_cod_data_source_block           zhuxy_1216
_cod_original_cell_volume        2092.91(19)
_cod_database_code               4032814
_shelx_shelxl_version_number     2014/7
_reflns_odcompleteness_completeness 99.68
_reflns_odcompleteness_iscentric 1
_reflns_odcompleteness_theta     26.32
_olex2_refinement_description
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups
 At 1.5 times of:
  All C(H,H,H) groups
2. Restrained distances
 O2-C18
 1.4 with sigma of 0.01
3. Rigid bond restraints
 O2, C18
 with sigma for 1-2 distances of 0.008 and sigma for 1-3 distances of 0.008
4. Uiso/Uaniso restraints and constraints
Uanis(C16) \\sim Ueq, Uanis(C17) \\sim Ueq, Uanis(C17') \\sim Ueq, Uanis(C16')
\\sim Ueq, Uanis(C14') \\sim Ueq, Uanis(C13') \\sim Ueq, Uanis(C13) \\sim Ueq,
Uanis(C14) \\sim Ueq: with sigma of 0.01 and sigma for terminal atoms of 0.02
Uanis(C15) \\sim Ueq: with sigma of 0.01 and sigma for terminal atoms of 0.02
Uanis(O2') \\sim Ueq, Uanis(O2) \\sim Ueq, Uanis(C18') \\sim Ueq, Uanis(C18)
\\sim Ueq: with sigma of 0.01 and sigma for terminal atoms of 0.02
5. Others
 Fixed Sof: O2(0.7) C13(0.75) H13(0.75) C14(0.75) H14(0.75) C16(0.75)
 C17(0.75) H17(0.75) C18(0.7) H18A(0.7) H18B(0.7) H18C(0.7) O2'(0.3) C13'(0.25)
 H13'(0.25) C14'(0.25) H14'(0.25) C16'(0.25) C17'(0.25) H17'(0.25) C18'(0.3)
 H18D(0.3) H18E(0.3) H18F(0.3)
6.a Aromatic/amide H refined with riding coordinates:
 C2(H2), C3(H3), C4(H4), C5(H5), C11(H11), C20(H20), C21(H21), C23(H23),
 C24(H24), C13(H13), C14(H14), C16(H16), C17(H17), C13'(H13'), C14'(H14'),
 C17'(H17')
6.b Idealised Me refined as rotating group:
 C25(H25A,H25B,H25C), C18(H18A,H18B,H18C), C18'(H18D,H18E,H18F)
;
_olex2_date_sample_data_collection 2016-12-16
_olex2_submission_special_instructions 'No special instructions were received'