Copper-Catalyzed Radical Cascade Cyclization To Access 3-Sulfonated Indenones with the AIE Phenomenon.
Sun, Kai; Chen, Xiao-Lan; Li, Shi-Jun; Wei, Dong-Hui; Liu, Xiao-Ceng; Zhang, Yin-Li; Liu, Yan; Fan, Lu-Lu; Qu, Ling-Bo; Yu, Bing; Li, Kai; Sun, Yuan-Qiang; Zhao, Yu-Fen; The Journal of organic chemistry 83 (2018) 14419–14430; doi:10.1021/acs.joc.8b02175

data_4035705
_publ_section_title
;
 Copper-Catalyzed Radical Cascade Cyclization To Access 3-Sulfonated
 Indenones with the AIE Phenomenon.
;
_journal_issue                   23
_journal_name_full               'The Journal of organic chemistry'
_journal_page_first              14419
_journal_page_last               14430
_journal_paper_doi               10.1021/acs.joc.8b02175
_journal_volume                  83
_journal_year                    2018
_chemical_formula_moiety         'C22 H16 O3 S'
_chemical_formula_sum            'C22 H16 O3 S'
_chemical_formula_weight         360.41
_space_group_crystal_system      orthorhombic
_space_group_IT_number           61
_space_group_name_Hall           '-P 2ac 2ab'
_space_group_name_H-M_alt        'P b c a'
_atom_sites_solution_hydrogens   geom
_audit_creation_date             2017-11-17
_audit_creation_method
;
Olex2 1.2
(compiled 2017.08.10 svn.r3458 for OlexSys, GUI svn.r5381)
;
_audit_update_record
;
2018-03-07 deposited with the CCDC.
2018-05-04 downloaded from the CCDC.
;
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_formula_units_Z            8
_cell_length_a                   9.10030(10)
_cell_length_b                   18.7035(2)
_cell_length_c                   20.7543(2)
_cell_measurement_reflns_used    6873
_cell_measurement_temperature    150.00(10)
_cell_measurement_theta_max      73.2240
_cell_measurement_theta_min      4.7150
_cell_volume                     3532.54(6)
_computing_cell_refinement       'CrysAlisPro 1.171.39.27b (Rigaku OD, 2015)'
_computing_data_collection       'CrysAlisPro 1.171.39.27b (Rigaku OD, 2015)'
_computing_data_reduction        'CrysAlisPro 1.171.39.27b (Rigaku OD, 2015)'
_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    'ShelXT (Sheldrick, 2015)'
_diffrn_ambient_environment      N~2~
_diffrn_ambient_temperature      150.00(10)
_diffrn_detector                 'CCD plate'
_diffrn_measured_fraction_theta_full 0.996
_diffrn_measured_fraction_theta_max 1.000
_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     33.00  62.00   0.50    0.50    --    0.00  57.00-120.00   58
  2  \w    -27.00  68.00   0.50    0.50    --    0.00  38.00   0.00  190
  3  \w     27.00 127.00   0.50    0.50    --   98.20 -45.00-180.00  200
  4  \w     71.00 182.00   0.50    0.50    --   98.20  45.00 120.00  222
  5  \w    104.00 184.00   0.50    0.50    --   98.20  30.00   0.00  160
  6  \w    130.00 168.00   0.50    0.50    --   98.20  45.00 -90.00   76
  7  \w     87.00 125.00   0.50    0.50    --   98.20 -61.00   0.00   76
  8  \w     22.00  47.00   0.50    0.50    --   98.20 -61.00   0.00   50
;
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'XtaLAB AFC12 (RINC): Kappa single'
_diffrn_measurement_method       '\w scans'
_diffrn_orient_matrix_type
'CrysAlisPro convention (1999,Acta A55,543-557)'
_diffrn_orient_matrix_UB_11      -0.0831848000
_diffrn_orient_matrix_UB_12      0.0706119000
_diffrn_orient_matrix_UB_13      0.0112201000
_diffrn_orient_matrix_UB_21      0.1082104000
_diffrn_orient_matrix_UB_22      0.0195973000
_diffrn_orient_matrix_UB_23      0.0542696000
_diffrn_orient_matrix_UB_31      0.1001058000
_diffrn_orient_matrix_UB_32      0.0375849000
_diffrn_orient_matrix_UB_33      -0.0494132000
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54184
_diffrn_reflns_av_R_equivalents  0.0278
_diffrn_reflns_av_unetI/netI     0.0263
_diffrn_reflns_Laue_measured_fraction_full 0.996
_diffrn_reflns_Laue_measured_fraction_max 1.000
_diffrn_reflns_limit_h_max       10
_diffrn_reflns_limit_h_min       -10
_diffrn_reflns_limit_k_max       22
_diffrn_reflns_limit_k_min       -22
_diffrn_reflns_limit_l_max       21
_diffrn_reflns_limit_l_min       -24
_diffrn_reflns_number            10851
_diffrn_reflns_point_group_measured_fraction_full 0.996
_diffrn_reflns_point_group_measured_fraction_max 1.000
_diffrn_reflns_theta_full        67.684
_diffrn_reflns_theta_max         67.489
_diffrn_reflns_theta_min         4.260
_diffrn_source                   'fine-focus sealed X-ray tube'
_diffrn_source_type              'Enhance (Cu) X-ray Source'
_exptl_absorpt_coefficient_mu    1.782
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.91817
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
CrysAlisPro 1.171.39.27b (Rigaku Oxford Diffraction, 2015)
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    1.355
_exptl_crystal_description       block
_exptl_crystal_F_000             1504
_exptl_crystal_size_max          0.19
_exptl_crystal_size_mid          0.18
_exptl_crystal_size_min          0.17
_refine_diff_density_max         0.178
_refine_diff_density_min         -0.371
_refine_diff_density_rms         0.042
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.068
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     236
_refine_ls_number_reflns         3177
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.068
_refine_ls_R_factor_all          0.0353
_refine_ls_R_factor_gt           0.0329
_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^)+(0.0475P)^2^+0.9996P]
 where P=(Fo^2^+2Fc^2^)/3
;
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0888
_refine_ls_wR_factor_ref         0.0904
_reflns_Friedel_coverage         0.000
_reflns_number_gt                2934
_reflns_number_total             3177
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            jo8b02175_si_002.cif
_cod_data_source_block           20171116c2-1
_cod_database_code               4035705
_shelxl_version_number           2013-2
_chemical_oxdiff_usercomment     'C H O N'
_shelx_estimated_absorpt_t_max   0.751
_shelx_estimated_absorpt_t_min   0.728
_reflns_odcompleteness_completeness 99.94
_reflns_odcompleteness_iscentric 1
_reflns_odcompleteness_theta     66.97
_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.a Aromatic/amide H refined with riding coordinates:
 C6(H6), C13(H13), C4(H4), C22(H22), C3(H3), C10(H10), C7(H7), C11(H11),
 C12(H12), C18(H18), C21(H21), C19(H19), C20(H20)
2.b Idealised Me refined as rotating group:
 C1(H1A,H1B,H1C)
;
_shelx_res_checksum              81926
_shelx_hkl_checksum              55965
_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 1.502
_oxdiff_exptl_absorpt_empirical_full_min 0.869