(3 + 2)-Annulation of p-Quinamine and Aryne: A Strategy To Construct the Multisubstituted Hydrocarbazoles.
Xu, Dengyu; Zhao, Yulong; Song, Dengpeng; Zhong, Zhuliang; Feng, Shangbiao; Xie, Xingang; Wang, Xiaolei; She, Xuegong; Organic letters 19 (2017) 3600–3603; doi:10.1021/acs.orglett.7b01578

data_1546426
_publ_section_title
;
 (3 + 2)-Annulation of p-Quinamine and Aryne: A Strategy To Construct the
 Multisubstituted Hydrocarbazoles.
;
_journal_issue                   13
_journal_name_full               'Organic letters'
_journal_page_first              3600
_journal_page_last               3603
_journal_paper_doi               10.1021/acs.orglett.7b01578
_journal_volume                  19
_journal_year                    2017
_chemical_absolute_configuration unk
_chemical_formula_moiety         'C25 H21 N O3 S'
_chemical_formula_sum            'C25 H21 N O3 S'
_chemical_formula_weight         415.49
_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'
_symmetry_space_group_name_Hall  'P 2ac 2ab'
_symmetry_space_group_name_H-M   'P 21 21 21'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_audit_creation_date             2017-05-10
_audit_creation_method
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Olex2 1.2
(compiled 2017.03.28 svn.r3405 for OlexSys, GUI svn.r5335)
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_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_formula_units_Z            8
_cell_length_a                   9.3259(5)
_cell_length_b                   19.0277(11)
_cell_length_c                   23.1597(9)
_cell_measurement_reflns_used    1518
_cell_measurement_temperature    236(12)
_cell_measurement_theta_max      25.3820
_cell_measurement_theta_min      3.8820
_cell_volume                     4109.7(4)
_computing_cell_refinement
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CrysAlisPro, Agilent Technologies,
Version 1.171.36.28 (release 01-02-2013 CrysAlis171 .NET)
(compiled Feb  1 2013,16:14:44)
;
_computing_data_collection
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CrysAlisPro, Agilent Technologies,
Version 1.171.36.28 (release 01-02-2013 CrysAlis171 .NET)
(compiled Feb  1 2013,16:14:44)
;
_computing_data_reduction
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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      236(12)
_diffrn_detector_area_resol_mean 16.0733
_diffrn_measured_fraction_theta_full 0.997
_diffrn_measured_fraction_theta_max 0.997
_diffrn_measurement_details
;
  1 omega -100.00  -74.00   1.0000   12.0000
omega____ theta____ kappa____ phi______ frames
    -      -19.5055  178.0000   30.0000 26

  2 omega  -38.00   85.00   1.0000   12.0000
omega____ theta____ kappa____ phi______ frames
    -       22.7867  -19.0000   30.0000 123
;
_diffrn_measurement_device_type  'SuperNova, Dual, Cu at zero, Eos'
_diffrn_measurement_method       '\w scans'
_diffrn_orient_matrix_UB_11      0.0237929000
_diffrn_orient_matrix_UB_12      -0.0353984000
_diffrn_orient_matrix_UB_13      -0.0000298000
_diffrn_orient_matrix_UB_21      0.0674848000
_diffrn_orient_matrix_UB_22      0.0108975000
_diffrn_orient_matrix_UB_23      0.0109375000
_diffrn_orient_matrix_UB_31      -0.0258158000
_diffrn_orient_matrix_UB_32      -0.0041963000
_diffrn_orient_matrix_UB_33      0.0286033000
_diffrn_radiation_monochromator  mirror
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0416
_diffrn_reflns_av_unetI/netI     0.1160
_diffrn_reflns_Laue_measured_fraction_full 0.997
_diffrn_reflns_Laue_measured_fraction_max 0.997
_diffrn_reflns_limit_h_max       11
_diffrn_reflns_limit_h_min       -5
_diffrn_reflns_limit_k_max       23
_diffrn_reflns_limit_k_min       -14
_diffrn_reflns_limit_l_max       28
_diffrn_reflns_limit_l_min       -15
_diffrn_reflns_number            10323
_diffrn_reflns_point_group_measured_fraction_full 0.960
_diffrn_reflns_point_group_measured_fraction_max 0.953
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         26.021
_diffrn_reflns_theta_min         3.330
_diffrn_source                   'SuperNova (Mo) X-ray Source'
_exptl_absorpt_coefficient_mu    0.185
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.98870
_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 light colourless'
_exptl_crystal_colour_lustre     clear
_exptl_crystal_colour_modifier   light
_exptl_crystal_colour_primary    colourless
_exptl_crystal_density_diffrn    1.343
_exptl_crystal_description       block
_exptl_crystal_F_000             1744
_exptl_crystal_size_max          0.21
_exptl_crystal_size_mid          0.17
_exptl_crystal_size_min          0.15
_refine_diff_density_max         0.310
_refine_diff_density_min         -0.365
_refine_diff_density_rms         0.052
_refine_ls_abs_structure_details
;
 Flack x determined using 1214 quotients [(I+)-(I-)]/[(I+)+(I-)]
 (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259).
;
_refine_ls_abs_structure_Flack   0.04(9)
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.059
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     543
_refine_ls_number_reflns         7728
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.059
_refine_ls_R_factor_all          0.1186
_refine_ls_R_factor_gt           0.0669
_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^)+(0.0201P)^2^] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0949
_refine_ls_wR_factor_ref         0.1245
_reflns_Friedel_coverage         0.709
_reflns_Friedel_fraction_full    0.913
_reflns_Friedel_fraction_max     0.898
_reflns_number_gt                4697
_reflns_number_total             7728
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            ol7b01578_si_001.cif
_cod_data_source_block           xudy_0508
_cod_depositor_comments          'Adding full bibliography for 1546426.cif.'
_cod_database_code               1546426
_shelx_shelxl_version_number     2014/7
_chemical_oxdiff_formula         'C H O N S'
_reflns_odcompleteness_completeness 99.60
_reflns_odcompleteness_iscentric 1
_reflns_odcompleteness_theta     26.32
_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:
 C7(H7), C33(H33)
2.b Secondary CH2 refined with riding coordinates:
 C8(H8A,H8B), C32(H32A,H32B)
2.c Aromatic/amide H refined with riding coordinates:
 C2(H2), C3(H3), C4(H4), C5(H5), C10(H10), C11(H11), C14(H14), C15(H15),
 C16(H16), C17(H17), C18(H18), C20(H20), C21(H21), C23(H23), C24(H24), C27(H27),
  C28(H28), C29(H29), C30(H30), C35(H35), C36(H36), C39(H39), C40(H40),
 C41(H41), C42(H42), C43(H43), C45(H45), C46(H46), C48(H48), C49(H49)
2.d Idealised Me refined as rotating group:
 C25(H25A,H25B,H25C), C50(H50A,H50B,H50C)
;
_olex2_date_sample_data_collection 2017-05-08
_olex2_submission_special_instructions 'No special instructions were received'