Brønsted-Acid-Catalyzed Synthesis of 3-Alkoxy and 3-Sulfamido Indanones via a Tandem Cyclization.
Zhou, Ni-Ni; Ning, Si-Si; Tong, Xiao-Juan; Luo, Ting-Ting; Yang, Jin; Li, Lin-Qiang; Fan, Ming-Jin; Yang, De-Suo; Zhu, Hai-Tao; The Journal of organic chemistry 84 (2019) 8497–8508; doi:10.1021/acs.joc.9b00791

data_4034120
_publ_section_title
;
 Br\/onsted-Acid-Catalyzed Synthesis of 3-Alkoxy and 3-Sulfamido Indanones
 via a Tandem Cyclization.
;
_journal_issue                   13
_journal_name_full               'The Journal of organic chemistry'
_journal_page_first              8497
_journal_page_last               8508
_journal_paper_doi               10.1021/acs.joc.9b00791
_journal_volume                  84
_journal_year                    2019
_chemical_formula_moiety         'C29 H23 N O3 S'
_chemical_formula_sum            'C29 H23 N O3 S'
_chemical_formula_weight         465.54
_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'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_audit_creation_date             2017-06-20
_audit_creation_method
;
Olex2 1.2
(compiled 2017.03.28 svn.r3405 for OlexSys, GUI svn.r5337)
;
_cell_angle_alpha                90.00
_cell_angle_beta                 110.973(7)
_cell_angle_gamma                90.00
_cell_formula_units_Z            4
_cell_length_a                   12.5820(8)
_cell_length_b                   13.6273(6)
_cell_length_c                   15.1251(10)
_cell_measurement_reflns_used    1440
_cell_measurement_temperature    299.42(10)
_cell_measurement_theta_max      22.0610
_cell_measurement_theta_min      3.8600
_cell_volume                     2421.5(3)
_computing_cell_refinement
;
CrysAlisPro, Agilent Technologies,
Version 1.171.37.33 (release 27-03-2014 CrysAlis171 .NET)
(compiled Mar 27 2014,17:12:48)
;
_computing_data_collection
;
CrysAlisPro, Agilent Technologies,
Version 1.171.37.33 (release 27-03-2014 CrysAlis171 .NET)
(compiled Mar 27 2014,17:12:48)
;
_computing_data_reduction
;
CrysAlisPro, Agilent Technologies,
Version 1.171.37.33 (release 27-03-2014 CrysAlis171 .NET)
(compiled Mar 27 2014,17:12:48)
;
_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_environment      air
_diffrn_ambient_temperature      299.42(10)
_diffrn_detector                 'CCD plate'
_diffrn_detector_area_resol_mean 16.0733
_diffrn_detector_type            Eos
_diffrn_measured_fraction_theta_full 0.998
_diffrn_measured_fraction_theta_max 0.998
_diffrn_measurement_details
;
  1 omega   12.00   82.00   1.0000    8.0000
omega____ theta____ kappa____ phi______ frames
    -       22.7867   57.0000  -60.0000 70

  2 omega   -9.00   25.00   1.0000    8.0000
omega____ theta____ kappa____ phi______ frames
    -      -19.5055  -99.0000 -180.0000 34

  3 omega  -40.00   71.00   1.0000    8.0000
omega____ theta____ kappa____ phi______ frames
    -       22.7867   19.0000  -90.0000 111

  4 omega   40.00   65.00   1.0000    8.0000
omega____ theta____ kappa____ phi______ frames
    -       22.7867 -115.0000   22.0000 25
;
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'SuperNova, Dual, Cu at zero, Eos'
_diffrn_measurement_method       '\w scans'
_diffrn_orient_matrix_UB_11      0.0602787000
_diffrn_orient_matrix_UB_12      0.0022222000
_diffrn_orient_matrix_UB_13      0.0193400000
_diffrn_orient_matrix_UB_21      -0.0013232000
_diffrn_orient_matrix_UB_22      -0.0104774000
_diffrn_orient_matrix_UB_23      0.0455621000
_diffrn_orient_matrix_UB_31      0.0028921000
_diffrn_orient_matrix_UB_32      -0.0509162000
_diffrn_orient_matrix_UB_33      -0.0085064000
_diffrn_radiation_monochromator  mirror
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0434
_diffrn_reflns_av_unetI/netI     0.0752
_diffrn_reflns_limit_h_max       15
_diffrn_reflns_limit_h_min       -14
_diffrn_reflns_limit_k_max       16
_diffrn_reflns_limit_k_min       -16
_diffrn_reflns_limit_l_max       18
_diffrn_reflns_limit_l_min       -14
_diffrn_reflns_number            9600
_diffrn_reflns_theta_full        26.02
_diffrn_reflns_theta_max         26.02
_diffrn_reflns_theta_min         3.32
_diffrn_source                   'SuperNova (Mo) X-ray Source'
_exptl_absorpt_coefficient_mu    0.165
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.96950
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
CrysAlisPro, Agilent Technologies,
Version 1.171.37.33 (release 27-03-2014 CrysAlis171 .NET)
(compiled Mar 27 2014,17:12:48)
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_crystal_colour            'clear light yellow'
_exptl_crystal_colour_lustre     clear
_exptl_crystal_colour_modifier   light
_exptl_crystal_colour_primary    yellow
_exptl_crystal_density_diffrn    1.277
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       block
_exptl_crystal_F_000             976
_exptl_crystal_size_max          0.18
_exptl_crystal_size_mid          0.12
_exptl_crystal_size_min          0.07
_refine_diff_density_max         0.195
_refine_diff_density_min         -0.270
_refine_diff_density_rms         0.046
_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     308
_refine_ls_number_reflns         4760
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.068
_refine_ls_R_factor_all          0.1159
_refine_ls_R_factor_gt           0.0637
_refine_ls_shift/su_max          0.001
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'calc w=1/[\s^2^(Fo^2^)+(0.0491P)^2^+0.3982P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1287
_refine_ls_wR_factor_ref         0.1660
_reflns_number_gt                2680
_reflns_number_total             4760
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            jo9b00791_si_003.cif
_cod_data_source_block           wangj_0620
_cod_original_cell_volume        2421.5(2)
_cod_database_code               4034120
_chemical_oxdiff_formula         'C H O S N'
_reflns_odcompleteness_completeness 99.71
_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 N(H) groups
 At 1.5 times of:
  All C(H,H,H) groups
2.a Riding coordinates:
 N1(H1)
2.b Ternary CH refined with riding coordinates:
 C1(H1A)
2.c Aromatic/amide H refined with riding coordinates:
 C3(H3), C4(H4), C5(H5), C6(H6), C12(H12), C13(H13), C14(H14), C15(H15),
 C16(H16), C18(H18), C19(H19), C20(H20), C21(H21), C22(H22), C23(H23), C24(H24),
  C26(H26), C27(H27)
2.d Idealised Me refined as rotating group:
 C29(H29A,H29B,H29C)
;
_olex2_date_sample_data_collection 2017-06-20
_olex2_submission_special_instructions 'No special instructions were received'