Diels-Alder Reaction of 1,3-Diarylbenzo[c]furans with Thiophene S,S-Dioxide/Indenone Derivatives: A Facile Preparation of Substituted Dibenzothiophene S,S-Dioxides and Fluorenones.
Nandakumar, Meganathan; Karunakaran, Jayachandran; Mohanakrishnan, Arasambattu K.; Organic letters 16 (2014) 3068–3071; doi:10.1021/ol501175q

data_1516237
_publ_section_title
;
 Diels-Alder Reaction of 1,3-Diarylbenzo[c]furans with Thiophene
 S,S-Dioxide/Indenone Derivatives: A Facile Preparation of Substituted
 Dibenzothiophene S,S-Dioxides and Fluorenones.
;
_journal_issue                   11
_journal_name_full               'Organic letters'
_journal_page_first              3068
_journal_page_last               3071
_journal_paper_doi               10.1021/ol501175q
_journal_volume                  16
_journal_year                    2014
_chemical_formula_moiety         'C34 H24 O4 S'
_chemical_formula_sum            'C34 H24 O4 S'
_chemical_formula_weight         528.59
_chemical_name_systematic
; 
3,10-bis(4-methoxyphenyl)12$^6^-thiapentacyclo[11.8.0.0^2,11^.0^4,9^.0^15,20^]
henicosa-1(21),2,4(9),5,7,10,13,15(20),16,18-decaene-12,12-dione 
;
_space_group_IT_number           2
_symmetry_cell_setting           triclinic
_symmetry_space_group_name_Hall  '-P 1'
_symmetry_space_group_name_H-M   'P -1'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_audit_creation_method           SHELXL-97
_cell_angle_alpha                78.442(2)
_cell_angle_beta                 68.211(2)
_cell_angle_gamma                80.216(2)
_cell_formula_units_Z            4
_cell_length_a                   13.7369(5)
_cell_length_b                   13.8077(5)
_cell_length_c                   16.4824(6)
_cell_measurement_reflns_used    5915
_cell_measurement_temperature    296(2)
_cell_measurement_theta_max      25.00
_cell_measurement_theta_min      1.35
_cell_volume                     2828.35(18)
_computing_cell_refinement       APEX2
_computing_data_collection       'APEX2 (Bruker, 2008)'
_computing_data_reduction        'SAINT (Bruker, 2008)'
_computing_molecular_graphics    'ORTEP3 (Farrugia, 2012)'
_computing_publication_material
'SHELXL-97 (Sheldrick, 2008) and  PLATON  (Spek, 2009)'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 2008)'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 2008)'
_diffrn_ambient_temperature      296(2)
_diffrn_measured_fraction_theta_full 0.992
_diffrn_measured_fraction_theta_max 0.992
_diffrn_measurement_device_type  'Bruker Axs Kappa ApexII CCD diffractometer'
_diffrn_measurement_method       '\w & \f scans'
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_source         'fine-focus sealed tube'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0389
_diffrn_reflns_av_sigmaI/netI    0.0444
_diffrn_reflns_limit_h_max       16
_diffrn_reflns_limit_h_min       -14
_diffrn_reflns_limit_k_max       16
_diffrn_reflns_limit_k_min       -16
_diffrn_reflns_limit_l_max       19
_diffrn_reflns_limit_l_min       -18
_diffrn_reflns_number            37910
_diffrn_reflns_theta_full        25.00
_diffrn_reflns_theta_max         25.00
_diffrn_reflns_theta_min         1.35
_exptl_absorpt_coefficient_mu    0.151
_exptl_absorpt_correction_T_max  0.963
_exptl_absorpt_correction_T_min  0.949
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   'SADABS (Bruker, 2008)'
_exptl_crystal_colour            colourless
_exptl_crystal_density_diffrn    1.241
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       block
_exptl_crystal_F_000             1104
_exptl_crystal_size_max          0.35
_exptl_crystal_size_mid          0.30
_exptl_crystal_size_min          0.25
_platon_squeeze_details
;
the void in the crystal contains a highly disordered molecule of 
chloroform has been removed from the intensity data using the 
program SQUEEZE in PLATON(Spek, 2004). The electron count from the 
SQUEEZE result confirms the chloroform solvent and is not 
included in the molecular formula.  
;
_refine_diff_density_max         0.245
_refine_diff_density_min         -0.226
_refine_diff_density_rms         0.039
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.039
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     707
_refine_ls_number_reflns         9889
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.039
_refine_ls_R_factor_all          0.0922
_refine_ls_R_factor_gt           0.0536
_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^)+(0.0926P)^2^+0.0656P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1532
_refine_ls_wR_factor_ref         0.1698
_reflns_number_gt                5915
_reflns_number_total             9889
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            ol501175q_si_003.cif
_cod_data_source_block           shelxl
_cod_depositor_comments
;
The following automatic conversions were performed:

'_symmetry_cell_setting' value 'Triclinic' changed to 'triclinic'
according to
/usr/data/users/saulius/crontab/automatic-downloads/rss-feeds/ACS/lib/dictionaries/cif_core.dic
dictionary named 'cif_core.dic' version 2.4.2 from 2011-04-26.

Automatic conversion script
Id: cif_fix_values 2281 2013-09-26 08:29:07Z andrius 

 Adding full bibliography for 1516236--1516238.cif.
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_cod_database_code               1516237