Construction of Sulfonyl Dihydrobenzo[<i>c</i>]xanthen-7-ones Core via NH<sub>4</sub>OAc/PdCl<sub>2</sub>/CuCl<sub>2</sub>-Mediated Double Cyclocondensation of α-Sulfonyl <i>o</i>-Hydroxyacetophenones with 2-Allylbenzaldehydes.
Hsueh, Nai-Chen; Tsai, Min-Chen; Chang, Meng-Yang; Chen, Hsing-Yin; The Journal of organic chemistry  (2019) –; doi:10.1021/acs.joc.9b02387

data_4037670
_publ_section_title
;
 Construction of Sulfonyl Dihydrobenzo[<i>c</i>]xanthen-7-ones Core via
 NH<sub>4</sub>OAc/PdCl<sub>2</sub>/CuCl<sub>2</sub>-Mediated Double
 Cyclocondensation of \a-Sulfonyl <i>o</i>-Hydroxyacetophenones with
 2-Allylbenzaldehydes.
;
_journal_name_full               'The Journal of organic chemistry'
_journal_paper_doi               10.1021/acs.joc.9b02387
_journal_year                    2019
_chemical_absolute_configuration rm
_chemical_formula_sum            'C24 H28 O7 S'
_chemical_formula_weight         460.52
_space_group_crystal_system      orthorhombic
_space_group_IT_number           33
_space_group_name_Hall           'P 2c -2n'
_space_group_name_H-M_alt        'P n a 21'
_atom_sites_solution_hydrogens   mixed
_audit_creation_method           SHELXL-2014/6
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   17.864(4)
_cell_length_b                   15.417(4)
_cell_length_c                   7.9315(18)
_cell_measurement_reflns_used    6576
_cell_measurement_temperature    100(2)
_cell_measurement_theta_max      25.9528
_cell_measurement_theta_min      2.2801
_cell_volume                     2184.4(9)
_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 0.999
_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  0.0569
_diffrn_reflns_av_unetI/netI     0.0517
_diffrn_reflns_Laue_measured_fraction_full 1.000
_diffrn_reflns_Laue_measured_fraction_max 0.999
_diffrn_reflns_limit_h_max       22
_diffrn_reflns_limit_h_min       -22
_diffrn_reflns_limit_k_max       19
_diffrn_reflns_limit_k_min       -19
_diffrn_reflns_limit_l_max       9
_diffrn_reflns_limit_l_min       -8
_diffrn_reflns_number            27261
_diffrn_reflns_point_group_measured_fraction_full 0.966
_diffrn_reflns_point_group_measured_fraction_max 0.963
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         26.357
_diffrn_reflns_theta_min         1.745
_exptl_absorpt_coefficient_mu    0.193
_exptl_absorpt_correction_T_max  0.9485
_exptl_absorpt_correction_T_min  0.6484
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   'SADABS V2014/4 (Bruker AXS Inc.)'
_exptl_crystal_colour            colorless
_exptl_crystal_density_diffrn    1.400
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       columnar
_exptl_crystal_F_000             976
_exptl_crystal_size_max          0.25
_exptl_crystal_size_mid          0.05
_exptl_crystal_size_min          0.03
_refine_diff_density_max         0.277
_refine_diff_density_min         -0.418
_refine_diff_density_rms         0.051
_refine_ls_abs_structure_details
;
 Flack x determined using 1421 quotients [(I+)-(I-)]/[(I+)+(I-)]
 (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259).
;
_refine_ls_abs_structure_Flack   0.10(5)
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.076
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     296
_refine_ls_number_reflns         4298
_refine_ls_number_restraints     1
_refine_ls_restrained_S_all      1.075
_refine_ls_R_factor_all          0.0500
_refine_ls_R_factor_gt           0.0416
_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^)+(0.0462P)^2^+0.3323P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0894
_refine_ls_wR_factor_ref         0.0925
_reflns_Friedel_coverage         0.791
_reflns_Friedel_fraction_full    0.927
_reflns_Friedel_fraction_max     0.920
_reflns_number_gt                3787
_reflns_number_total             4298
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            jo9b02387_si_001.cif
_cod_data_source_block           180120LT
_cod_depositor_comments
;
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 7556 2019-12-06 15:28:31Z antanas 
;
_cod_original_cell_volume        2184.5(9)
_cod_database_code               4037670
_shelxl_version_number           2014/6
_shelx_res_checksum              33368
_shelx_hkl_checksum              80228