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_4034122
_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         'C24 H19 N O2'
_chemical_formula_sum            'C24 H19 N O2'
_chemical_formula_weight         353.40
_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'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_audit_creation_date             2017-10-31
_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                 96.132(7)
_cell_angle_gamma                90.00
_cell_formula_units_Z            4
_cell_length_a                   13.1392(8)
_cell_length_b                   9.4856(5)
_cell_length_c                   15.3103(11)
_cell_measurement_reflns_used    1509
_cell_measurement_temperature    293.35(10)
_cell_measurement_theta_max      24.2820
_cell_measurement_theta_min      3.7690
_cell_volume                     1897.3(2)
_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      293.35(10)
_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  -94.00  -67.00   1.5000   20.0000
omega____ theta____ kappa____ phi______ frames
    -      -19.9742  178.0000  -30.0000 18

  2 omega  -14.00   19.00   1.5000   20.0000
omega____ theta____ kappa____ phi______ frames
    -      -19.9742  -99.0000  -30.0000 22

  3 omega   37.00   82.00   1.5000   20.0000
omega____ theta____ kappa____ phi______ frames
    -       23.4117   57.0000  -30.0000 30

  4 omega   63.00   93.00   1.5000   20.0000
omega____ theta____ kappa____ phi______ frames
    -       23.4117   57.0000  150.0000 20

  5 omega  -45.00   28.50   1.5000   20.0000
omega____ theta____ kappa____ phi______ frames
    -       23.4117  -38.0000   60.0000 49

  6 omega   19.00   94.00   1.5000   20.0000
omega____ theta____ kappa____ phi______ frames
    -       23.4117   38.0000 -120.0000 50
;
_diffrn_measurement_device_type  'SuperNova, Dual, Cu at zero, Eos'
_diffrn_measurement_method       '\w scans'
_diffrn_orient_matrix_UB_11      -0.0400658000
_diffrn_orient_matrix_UB_12      0.0400407000
_diffrn_orient_matrix_UB_13      0.0153640000
_diffrn_orient_matrix_UB_21      -0.0054364000
_diffrn_orient_matrix_UB_22      0.0384271000
_diffrn_orient_matrix_UB_23      -0.0399624000
_diffrn_orient_matrix_UB_31      -0.0362116000
_diffrn_orient_matrix_UB_32      -0.0500681000
_diffrn_orient_matrix_UB_33      -0.0184735000
_diffrn_radiation_monochromator  mirror
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.1005
_diffrn_reflns_av_unetI/netI     0.1090
_diffrn_reflns_limit_h_max       16
_diffrn_reflns_limit_h_min       -15
_diffrn_reflns_limit_k_max       11
_diffrn_reflns_limit_k_min       -6
_diffrn_reflns_limit_l_max       17
_diffrn_reflns_limit_l_min       -18
_diffrn_reflns_number            8133
_diffrn_reflns_theta_full        26.02
_diffrn_reflns_theta_max         26.02
_diffrn_reflns_theta_min         3.43
_diffrn_source                   'SuperNova (Mo) X-ray Source'
_exptl_absorpt_coefficient_mu    0.079
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.44466
_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 yellow'
_exptl_crystal_colour_lustre     clear
_exptl_crystal_colour_modifier   light
_exptl_crystal_colour_primary    yellow
_exptl_crystal_density_diffrn    1.237
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       block
_exptl_crystal_F_000             744
_exptl_crystal_size_max          0.27
_exptl_crystal_size_mid          0.25
_exptl_crystal_size_min          0.24
_refine_diff_density_max         0.180
_refine_diff_density_min         -0.274
_refine_diff_density_rms         0.056
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   0.993
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     245
_refine_ls_number_reflns         3731
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      0.993
_refine_ls_R_factor_all          0.1283
_refine_ls_R_factor_gt           0.0747
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'calc w=1/[\s^2^(Fo^2^)+(0.0708P)^2^+0.0000P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1588
_refine_ls_wR_factor_ref         0.1969
_reflns_number_gt                1965
_reflns_number_total             3731
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            jo9b00791_si_004.cif
_cod_data_source_block           weij_4_2
_cod_original_cell_volume        1897.2(2)
_cod_database_code               4034122
_reflns_odcompleteness_completeness 99.61
_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 Ternary CH refined with riding coordinates:
 C8(H8)
2.b Aromatic/amide H refined with riding coordinates:
 N1(H1), 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)
2.c Idealised Me refined as rotating group:
 C24(H24A,H24B,H24C)
;
_olex2_date_sample_data_collection 2017-10-31
_olex2_submission_special_instructions 'No special instructions were received'