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_4034123
_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         'C22 H15 O2'
_chemical_formula_sum            'C22 H15 O2'
_chemical_formula_weight         311.34
_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
_audit_creation_date             2016-07-11
_audit_creation_method
;
Olex2 1.2
(compiled 2016.02.19 svn.r3266 for OlexSys, GUI svn.r5155)
;
_cell_angle_alpha                90
_cell_angle_beta                 100.897(5)
_cell_angle_gamma                90
_cell_formula_units_Z            8
_cell_length_a                   12.3814(6)
_cell_length_b                   10.2462(6)
_cell_length_c                   26.6255(12)
_cell_measurement_reflns_used    2253
_cell_measurement_temperature    292.82(10)
_cell_measurement_theta_max      21.9250
_cell_measurement_theta_min      3.6900
_cell_volume                     3316.9(3)
_computing_cell_refinement
;
CrysAlisPro, Agilent Technologies,
Version 1.171.37.35 (release 13-08-2014 CrysAlis171 .NET)
(compiled Aug 13 2014,18:06:01)
;
_computing_data_collection
;
CrysAlisPro, Agilent Technologies,
Version 1.171.37.35 (release 13-08-2014 CrysAlis171 .NET)
(compiled Aug 13 2014,18:06:01)
;
_computing_data_reduction
;
CrysAlisPro, Agilent Technologies,
Version 1.171.37.35 (release 13-08-2014 CrysAlis171 .NET)
(compiled Aug 13 2014,18:06:01)
;
_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      292.82(10)
_diffrn_detector                 'CCD plate'
_diffrn_detector_area_resol_mean 16.0733
_diffrn_detector_type            Eos
_diffrn_measured_fraction_theta_full 0.995
_diffrn_measured_fraction_theta_max 0.996
_diffrn_measurement_details
;
  1 omega   38.00   87.50   0.9000    5.0000
omega____ theta____ kappa____ phi______ frames
    -       27.0108   38.0000  -30.0000 55

  2 omega  -20.00    5.20   0.9000    5.0000
omega____ theta____ kappa____ phi______ frames
    -      -23.8858  -99.0000 -180.0000 28

  3 omega  -38.00  109.60   0.9000    5.0000
omega____ theta____ kappa____ phi______ frames
    -       27.0108   19.0000  -90.0000 164

  4 omega   49.00   98.50   0.9000    5.0000
omega____ theta____ kappa____ phi______ frames
    -       27.0108 -178.0000 -180.0000 55
;
_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      -0.0068481000
_diffrn_orient_matrix_UB_12      -0.0545501000
_diffrn_orient_matrix_UB_13      0.0154727000
_diffrn_orient_matrix_UB_21      -0.0492728000
_diffrn_orient_matrix_UB_22      0.0276240000
_diffrn_orient_matrix_UB_23      0.0051746000
_diffrn_orient_matrix_UB_31      -0.0304651000
_diffrn_orient_matrix_UB_32      -0.0324529000
_diffrn_orient_matrix_UB_33      -0.0216804000
_diffrn_radiation_monochromator  mirror
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0460
_diffrn_reflns_av_unetI/netI     0.0763
_diffrn_reflns_Laue_measured_fraction_full 0.995
_diffrn_reflns_Laue_measured_fraction_max 0.996
_diffrn_reflns_limit_h_max       11
_diffrn_reflns_limit_h_min       -15
_diffrn_reflns_limit_k_max       12
_diffrn_reflns_limit_k_min       -12
_diffrn_reflns_limit_l_max       32
_diffrn_reflns_limit_l_min       -24
_diffrn_reflns_number            12866
_diffrn_reflns_point_group_measured_fraction_full 0.995
_diffrn_reflns_point_group_measured_fraction_max 0.996
_diffrn_reflns_theta_full        25.500
_diffrn_reflns_theta_max         26.020
_diffrn_reflns_theta_min         3.278
_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  0.97861
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
CrysAlisPro, Agilent Technologies,
Version 1.171.37.35 (release 13-08-2014 CrysAlis171 .NET)
(compiled Aug 13 2014,18:06:01)
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    1.247
_exptl_crystal_description       block
_exptl_crystal_F_000             1304
_exptl_crystal_size_max          0.21
_exptl_crystal_size_mid          0.15
_exptl_crystal_size_min          0.14
_refine_diff_density_max         0.459
_refine_diff_density_min         -0.222
_refine_diff_density_rms         0.052
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.088
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     455
_refine_ls_number_reflns         6513
_refine_ls_number_restraints     24
_refine_ls_restrained_S_all      1.090
_refine_ls_R_factor_all          0.1774
_refine_ls_R_factor_gt           0.1127
_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^)+(0.0231P)^2^+9.2547P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.2058
_refine_ls_wR_factor_ref         0.2356
_reflns_Friedel_coverage         0.000
_reflns_number_gt                3536
_reflns_number_total             6513
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            jo9b00791_si_005.cif
_cod_data_source_block           weijian0606
_cod_database_code               4034123
_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
 At 1.5 times of:
  All O(H) groups
2. Uiso/Uaniso restraints and constraints
Uanis(O4') \\sim Ueq, Uanis(O4) \\sim Ueq, Uanis(O1') \\sim Ueq, Uanis(O1)
\\sim Ueq: with sigma of 0.01 and sigma for terminal atoms of 0.02
3. Others
 Fixed Sof: O1(0.65) H1(0.65) O1'(0.35) H1'(0.35) O4(0.4) H4A(0.4) O4'(0.6)
 H4'(0.6)
4.a Aromatic/amide H refined with riding coordinates:
 C4(H4), C5(H5), C6(H6), C7(H7), C12(H12), C13(H13), C14(H14), C15(H15),
 C16(H16), C18(H18), C19(H19), C20(H20), C21(H21), C22(H22), C26(H26), C27(H27),
  C28(H28), C29(H29), C34(H34), C35(H35), C36(H36), C37(H37), C38(H38),
 C40(H40), C41(H41), C42(H42), C43(H43), C44(H44)
4.b Idealised tetrahedral OH refined as rotating group:
 O1(H1), O1'(H1'), O4(H4A), O4'(H4')
;
_shelx_res_checksum              12370
_shelx_hkl_checksum              65154
_shelx_shelxl_version_number     2014/7
_olex2_date_sample_data_collection 2016-06-07
_olex2_submission_special_instructions 'No special instructions were received'