Intramolecular Benzannulation of 3-Sulfonyl-2-benzylchromen-4-ones: Synthesis of Sulfonyl Dibenzooxabicyclo[3.3.1]nonanes.
Chang, Meng-Yang; Chen, Han-Yu; Tsai, Yu-Lin; The Journal of organic chemistry 84 (2019) 443–449; doi:10.1021/acs.joc.8b02726

data_4035917
_publ_section_title
;
 Intramolecular Benzannulation of 3-Sulfonyl-2-benzylchromen-4-ones:
 Synthesis of Sulfonyl Dibenzooxabicyclo[3.3.1]nonanes.
;
_journal_issue                   1
_journal_name_full               'The Journal of organic chemistry'
_journal_page_first              443
_journal_page_last               449
_journal_paper_doi               10.1021/acs.joc.8b02726
_journal_volume                  84
_journal_year                    2019
_chemical_formula_sum            'C23 H20 O4 S'
_chemical_formula_weight         392.45
_space_group_crystal_system      triclinic
_space_group_IT_number           2
_space_group_name_Hall           '-P 1'
_space_group_name_H-M_alt        'P -1'
_atom_sites_solution_hydrogens   geom
_audit_creation_method           SHELXL-2014/6
_cell_angle_alpha                71.146(7)
_cell_angle_beta                 75.076(6)
_cell_angle_gamma                85.590(7)
_cell_formula_units_Z            2
_cell_length_a                   7.0055(13)
_cell_length_b                   10.701(2)
_cell_length_c                   13.367(3)
_cell_measurement_reflns_used    3085
_cell_measurement_temperature    100(2)
_cell_measurement_theta_max      26.1371
_cell_measurement_theta_min      3.0093
_cell_volume                     916.3(3)
_computing_cell_refinement       'SAINT V8.34A (Bruker AXS Inc., 2013)'
_computing_data_collection       'Bruker APEX2'
_computing_data_reduction        'SAINT V8.34A (Bruker AXS Inc., 2013)'
_computing_molecular_graphics    'Bruker SHELXTL'
_computing_publication_material  'Bruker SHELXTL'
_computing_structure_refinement  'SHELXL-2014/6 (Sheldrick, 2014)'
_diffrn_ambient_temperature      100(2)
_diffrn_detector_area_resol_mean 8.3333
_diffrn_measured_fraction_theta_full 1.000
_diffrn_measured_fraction_theta_max 0.987
_diffrn_measurement_device_type  'Bruker APEX-II CCD'
_diffrn_measurement_method       '\f and \w scans'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0438
_diffrn_reflns_av_unetI/netI     0.0546
_diffrn_reflns_Laue_measured_fraction_full 1.000
_diffrn_reflns_Laue_measured_fraction_max 0.987
_diffrn_reflns_limit_h_max       8
_diffrn_reflns_limit_h_min       -8
_diffrn_reflns_limit_k_max       13
_diffrn_reflns_limit_k_min       -13
_diffrn_reflns_limit_l_max       16
_diffrn_reflns_limit_l_min       -15
_diffrn_reflns_number            11704
_diffrn_reflns_point_group_measured_fraction_full 1.000
_diffrn_reflns_point_group_measured_fraction_max 0.987
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         26.474
_diffrn_reflns_theta_min         1.661
_exptl_absorpt_coefficient_mu    0.205
_exptl_absorpt_correction_T_max  0.9485
_exptl_absorpt_correction_T_min  0.8824
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   'SADABS V2014/4 (Bruker AXS Inc.)'
_exptl_crystal_colour            Colorless
_exptl_crystal_density_diffrn    1.422
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       Tabullar
_exptl_crystal_F_000             412
_exptl_crystal_size_max          0.12
_exptl_crystal_size_mid          0.11
_exptl_crystal_size_min          0.04
_refine_diff_density_max         0.529
_refine_diff_density_min         -0.423
_refine_diff_density_rms         0.064
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.028
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     254
_refine_ls_number_reflns         3739
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.028
_refine_ls_R_factor_all          0.0782
_refine_ls_R_factor_gt           0.0500
_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^)+(0.0606P)^2^+0.6496P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1189
_refine_ls_wR_factor_ref         0.1321
_reflns_Friedel_coverage         0.000
_reflns_number_gt                2730
_reflns_number_total             3739
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            jo8b02726_si_001.cif
_cod_data_source_block           mo_180527LT_0m
_cod_depositor_comments
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The following automatic conversions were performed:

data item '_exptl_crystal_density_meas' value 'not measured' was
changed to '?' -- the value is perceived as not measured.

Automatic conversion script
Id: cif_fix_values 6909 2019-04-08 15:41:33Z antanas 
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_cod_database_code               4035917
_shelxl_version_number           2014/6
_shelx_res_checksum              65743
_shelx_hkl_checksum              78931