Elemental sulfur accelerated the reactivity of the 3-position of indole for the construction of chromeno[2,3-b]indoles
Liu, Jianming; Yan, Xuyang; Liu, Na; Zhang, Yanyan; Zhao, Shufang; Wang, Xiaopei; Zhuo, Kelei; Yue, Yuanyuan; Organic Chemistry Frontiers 5 (2018) 1034–; doi:10.1039/C7QO01114H

data_1553967
_publ_section_title
;
 Elemental sulfur accelerated the reactivity of the 3-position of indole
 for the construction of chromeno[2,3-b]indoles
;
_journal_issue                   6
_journal_name_full               'Organic Chemistry Frontiers'
_journal_page_first              1034
_journal_paper_doi               10.1039/C7QO01114H
_journal_volume                  5
_journal_year                    2018
_chemical_formula_moiety         'C15 H7 Cl F N O'
_chemical_formula_sum            'C15 H7 Cl F N O'
_chemical_formula_weight         271.68
_space_group_crystal_system      monoclinic
_space_group_IT_number           14
_space_group_name_Hall           '-P 2yn'
_space_group_name_H-M_alt        'P 1 21/n 1'
_symmetry_Int_Tables_number      14
_audit_creation_date             2017-12-05
_audit_creation_method
;
Olex2 1.2-alpha
(compiled 2017.07.20 svn.r3457 for OlexSys, GUI svn.r5381)
;
_audit_update_record
;
2017-12-05 deposited with the CCDC.
2018-01-02 downloaded from the CCDC.
;
_cell_angle_alpha                90
_cell_angle_beta                 107.860(3)
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   8.9388(2)
_cell_length_b                   9.7832(2)
_cell_length_c                   13.5584(3)
_cell_measurement_reflns_used    6598
_cell_measurement_temperature    294.5(7)
_cell_measurement_theta_max      72.2450
_cell_measurement_theta_min      4.5110
_cell_volume                     1128.54(5)
_computing_cell_refinement       'CrysAlisPro 1.171.39.35c (Rigaku OD, 2017)'
_computing_data_collection       'CrysAlisPro 1.171.39.35c (Rigaku OD, 2017)'
_computing_data_reduction        'CrysAlisPro 1.171.39.35c (Rigaku OD, 2017)'
_computing_molecular_graphics    'Olex2 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 (Dolomanov et al., 2009)'
_computing_structure_refinement  'olex2.refine (Bourhis et al., 2015)'
_diffrn_ambient_environment      air
_diffrn_ambient_temperature      294.5(7)
_diffrn_detector                 'CCD plate'
_diffrn_detector_area_resol_mean 8.0528
_diffrn_detector_type            EosS2
_diffrn_measured_fraction_theta_full 0.9777
_diffrn_measured_fraction_theta_max 0.9777
_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   -104.00 -20.00   1.00    1.00    --  -36.29 -57.00-180.00   84
  2  \w    -35.00  66.00   1.00    1.00    --   36.29 -19.00 120.00  101
  3  \w    -31.00  53.00   1.00    1.00    --   36.29 -57.00 -30.00   84
  4  \w     23.00  90.00   1.00    1.00    --   36.29-125.00-150.00   67
  5  \w     23.00  90.00   1.00    1.00    --   36.29-125.00-180.00   67
  6  \w     23.00  90.00   1.00    1.00    --   36.29-125.00 -60.00   67
  7  \w    -31.00  53.00   1.00    1.00    --   36.29 -57.00  30.00   84
  8  \w    -31.00  63.00   1.00    1.00    --   36.29 -77.00-150.00   94
  9  \w    100.00 178.00   1.00    1.00    --  109.31 111.00 -30.00   78
 10  \w     83.00 177.00   1.00    1.00    --  109.31  77.00 150.00   94
 11  \w     39.00 131.00   1.00    1.00    --  109.31 -30.00-180.00   92
 12  \w     39.00 131.00   1.00    1.00    --  109.31 -30.00 -30.00   92
 13  \w     40.00 109.00   1.00    1.00    --  109.31 -95.00-120.00   69
 14  \w    100.00 178.00   1.00    1.00    --  109.31 111.00 -60.00   78
 15  \w     40.00 109.00   1.00    1.00    --  109.31 -95.00  30.00   69
 16  \w     42.00 127.00   1.00    1.00    --  109.31 -61.00  30.00   85
 17  \w    100.00 178.00   1.00    1.00    --  109.31 111.00  60.00   78
 18  \w   -104.00 -10.00   1.00    1.00    --  -36.29 -77.00  30.00   94
 19  \w   -104.00 -20.00   1.00    1.00    --  -36.29 -57.00  90.00   84
 20  \w   -104.00 -10.00   1.00    1.00    --  -36.29 -77.00 -60.00   94
 21  \w     10.00  70.00   1.00    1.00    --   36.29  77.00 150.00   60
 22  \w     10.00 104.00   1.00    1.00    --   36.29  77.00-120.00   94
 23  \w    -35.00  56.00   1.00    1.00    --   36.29 -19.00-150.00   91
;
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'SuperNova, Dual, Cu at home/near, EosS2'
_diffrn_measurement_method       '\w scans'
_diffrn_orient_matrix_type
'CrysAlisPro convention (1999,Acta A55,543-557)'
_diffrn_orient_matrix_UB_11      -0.0384103000
_diffrn_orient_matrix_UB_12      0.0403490000
_diffrn_orient_matrix_UB_13      0.0994086000
_diffrn_orient_matrix_UB_21      -0.0940379000
_diffrn_orient_matrix_UB_22      0.1240894000
_diffrn_orient_matrix_UB_23      -0.0565687000
_diffrn_orient_matrix_UB_31      -0.1499281000
_diffrn_orient_matrix_UB_32      -0.0880923000
_diffrn_orient_matrix_UB_33      -0.0341927000
_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  0.0401
_diffrn_reflns_av_unetI/netI     0.0231
_diffrn_reflns_limit_h_max       8
_diffrn_reflns_limit_h_min       -11
_diffrn_reflns_limit_k_max       9
_diffrn_reflns_limit_k_min       -12
_diffrn_reflns_limit_l_max       16
_diffrn_reflns_limit_l_min       -16
_diffrn_reflns_number            8377
_diffrn_reflns_theta_full        72.5434
_diffrn_reflns_theta_max         72.54
_diffrn_reflns_theta_min         5.28
_diffrn_source                   'micro-focus sealed X-ray tube'
_diffrn_source_type              'SuperNova (Cu) X-ray Source'
_exptl_absorpt_coefficient_mu    3.037
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.23650
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
CrysAlisPro 1.171.39.35c (Rigaku Oxford Diffraction, 2017)
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_crystal_colour            'clear dark red'
_exptl_crystal_colour_lustre     clear
_exptl_crystal_colour_modifier   dark
_exptl_crystal_colour_primary    red
_exptl_crystal_density_diffrn    1.5989
_exptl_crystal_description       block
_exptl_crystal_F_000             555.2061
_exptl_crystal_size_max          0.6
_exptl_crystal_size_mid          0.4
_exptl_crystal_size_min          0.2
_refine_diff_density_max         0.3606
_refine_diff_density_min         -0.8033
_refine_diff_density_rms         0.1570
_refine_ls_d_res_high            0.8081
_refine_ls_d_res_low             8.3822
_refine_ls_goodness_of_fit_ref   1.0470
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_constraints    14
_refine_ls_number_parameters     172
_refine_ls_number_reflns         2190
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.0470
_refine_ls_R_factor_all          0.0585
_refine_ls_R_factor_gt           0.0567
_refine_ls_shift/su_max          0.0000
_refine_ls_shift/su_mean         0.0000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'w=1/[\s^2^(Fo^2^)+(0.1032P)^2^+0.3486P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1410
_refine_ls_wR_factor_ref         0.1433
_reflns_Friedel_coverage         0.0
_reflns_limit_h_max              7
_reflns_limit_h_min              -11
_reflns_limit_k_max              12
_reflns_limit_k_min              0
_reflns_limit_l_max              16
_reflns_limit_l_min              -7
_reflns_number_gt                2067
_reflns_number_total             2190
_reflns_threshold_expression     I>=2u(I)
_cod_data_source_file            c7qo01114h2.cif
_cod_data_source_block           yxy-20171205
_cod_original_sg_symbol_Hall     '-P 2ybc (x-z,y,z)'
_cod_database_code               1553967
_chemical_oxdiff_formula         'C1 H1 O1 F1 Cl1 N1'
_reflns_odcompleteness_completeness 99.95
_reflns_odcompleteness_iscentric 1
_reflns_odcompleteness_theta     66.97
_olex2_refinement_description
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups
2.a Aromatic/amide H refined with riding coordinates:
 C8(H8), C3(H3), C13(H13), C16(H16), C4(H4), C5(H5), C15(H15)
;
_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 2.198
_oxdiff_exptl_absorpt_empirical_full_min 0.645