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_1516236
_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         'C49 H36 O5'
_chemical_formula_sum            'C49 H36 O5'
_chemical_formula_weight         704.78
_chemical_name_systematic
; 
3,10,14,21-tetrakis(4-methoxyphenyl)pentacyclo[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-decaen-12-one 
;
_space_group_IT_number           13
_symmetry_cell_setting           monoclinic
_symmetry_space_group_name_Hall  '-P 2yac'
_symmetry_space_group_name_H-M   'P 1 2/n 1'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_audit_creation_method           SHELXL-97
_cell_angle_alpha                90.00
_cell_angle_beta                 93.9470(10)
_cell_angle_gamma                90.00
_cell_formula_units_Z            2
_cell_length_a                   9.7720(4)
_cell_length_b                   12.0351(4)
_cell_length_c                   17.3162(6)
_cell_measurement_reflns_used    6228
_cell_measurement_temperature    296(2)
_cell_measurement_theta_max      23.91
_cell_measurement_theta_min      2.32
_cell_volume                     2031.68(13)
_computing_cell_refinement       'APEX2/SAINT (Bruker, 2008)'
_computing_data_collection       'APEX2 (Bruker, 2008)'
_computing_data_reduction        'SAINT/XPREP (Bruker, 2008)'
_computing_molecular_graphics
'ORTEP3 (Farrugia, 2012) and Mercury (Macrae et al., 2008)'
_computing_publication_material  'PLATON (Spek, 2009)'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 2008)'
_computing_structure_solution    'SIR92 (Altomare et al., 1993)'
_diffrn_ambient_temperature      296(2)
_diffrn_measured_fraction_theta_full 0.996
_diffrn_measured_fraction_theta_max 0.996
_diffrn_measurement_device_type  'bruker axs kappa2 CCD Diffractometer'
_diffrn_measurement_method       '\w and \f scan'
_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  0.0252
_diffrn_reflns_av_sigmaI/netI    0.0198
_diffrn_reflns_limit_h_max       11
_diffrn_reflns_limit_h_min       -11
_diffrn_reflns_limit_k_max       14
_diffrn_reflns_limit_k_min       -14
_diffrn_reflns_limit_l_max       20
_diffrn_reflns_limit_l_min       -20
_diffrn_reflns_number            20614
_diffrn_reflns_theta_full        24.75
_diffrn_reflns_theta_max         24.75
_diffrn_reflns_theta_min         1.69
_exptl_absorpt_coefficient_mu    0.074
_exptl_absorpt_correction_T_max  0.9782
_exptl_absorpt_correction_T_min  0.9047
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   'SADABS (Bruker, 2008)'
_exptl_crystal_colour            orange
_exptl_crystal_density_diffrn    1.152
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       block
_exptl_crystal_F_000             740
_exptl_crystal_size_max          0.35
_exptl_crystal_size_mid          0.30
_exptl_crystal_size_min          0.30
_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         0.130
_refine_diff_density_min         -0.147
_refine_diff_density_rms         0.030
_refine_ls_extinction_coef       0.0041(10)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc^2^\l^3^/sin(2\q)]^-1/4^
_refine_ls_extinction_method     SHELXL
_refine_ls_goodness_of_fit_ref   1.094
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     248
_refine_ls_number_reflns         3474
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.094
_refine_ls_R_factor_all          0.0524
_refine_ls_R_factor_gt           0.0397
_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^)+(0.0692P)^2^+0.1579P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1173
_refine_ls_wR_factor_ref         0.1248
_reflns_number_gt                2664
_reflns_number_total             3474
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            ol501175q_si_004.cif
_cod_data_source_block           shelxl
_cod_depositor_comments
;
The following automatic conversions were performed:

'_symmetry_cell_setting' value 'Monoclinic' changed to 'monoclinic'
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.
;
_cod_original_sg_symbol_H-M      P2/n
_cod_database_code               1516236