Sequential cycloaddition and ring expansion reaction of arynes and methylenebenzothiopheneones: synthesis of a benzo-fused eight-membered ring via sulfonium ylides
Xiao, Peng; Su, Shikuan; Wang, Wei; Cao, Weiguo; Chen, Jie; Li, Jian; Chen, Yali; RSC Advances 9 (2019) 39119–; doi:10.1039/C9RA09332J

data_7239608
_publ_section_title
;
 Sequential cycloaddition and ring expansion reaction of arynes and
 methylenebenzothiopheneones: synthesis of a benzo-fused eight-membered
 ring via sulfonium ylides
;
_journal_issue                   67
_journal_name_full               'RSC Advances'
_journal_page_first              39119
_journal_paper_doi               10.1039/C9RA09332J
_journal_volume                  9
_journal_year                    2019
_chemical_formula_sum            'C27 H26 O4 S Si2'
_chemical_formula_weight         502.72
_space_group_IT_number           14
_space_group_name_Hall           '-P 2yn'
_space_group_name_H-M_alt        'P 1 21/n 1'
_symmetry_cell_setting           monoclinic
_symmetry_space_group_name_H-M   'P 1 21/n 1'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_audit_creation_method           SHELXL-97
_audit_update_record
;
2019-05-10 deposited with the CCDC.	2019-11-18 downloaded from the CCDC.
;
_cell_angle_alpha                90.00
_cell_angle_beta                 99.615(5)
_cell_angle_gamma                90.00
_cell_formula_units_Z            4
_cell_length_a                   10.329(5)
_cell_length_b                   17.205(7)
_cell_length_c                   15.111(7)
_cell_measurement_reflns_used    7327
_cell_measurement_temperature    296(2)
_cell_measurement_theta_max      27.64
_cell_measurement_theta_min      2.32
_cell_volume                     2648(2)
_computing_cell_refinement       'Bruker SAINT'
_computing_data_collection       'Bruker APEX2'
_computing_data_reduction        'Bruker SAINT'
_computing_molecular_graphics    'Bruker SHELXTL'
_computing_publication_material  'Bruker SHELXTL'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 2008)'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 2008)'
_diffrn_ambient_temperature      296(2)
_diffrn_measured_fraction_theta_full 0.997
_diffrn_measured_fraction_theta_max 0.997
_diffrn_measurement_device_type  'Bruker APEX-II CCD'
_diffrn_measurement_method       '\f and \w 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  0.0430
_diffrn_reflns_av_sigmaI/netI    0.0449
_diffrn_reflns_limit_h_max       12
_diffrn_reflns_limit_h_min       -11
_diffrn_reflns_limit_k_max       20
_diffrn_reflns_limit_k_min       -20
_diffrn_reflns_limit_l_max       18
_diffrn_reflns_limit_l_min       -8
_diffrn_reflns_number            13438
_diffrn_reflns_theta_full        25.05
_diffrn_reflns_theta_max         25.05
_diffrn_reflns_theta_min         2.32
_exptl_absorpt_coefficient_mu    0.243
_exptl_absorpt_correction_T_max  0.9621
_exptl_absorpt_correction_T_min  0.9351
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   sadabs
_exptl_crystal_density_diffrn    1.261
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             1056
_exptl_crystal_size_max          0.28
_exptl_crystal_size_mid          0.23
_exptl_crystal_size_min          0.16
_refine_diff_density_max         0.345
_refine_diff_density_min         -0.267
_refine_diff_density_rms         0.050
_refine_ls_extinction_coef       0.0097(9)
_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   1.019
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     312
_refine_ls_number_reflns         4665
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.019
_refine_ls_R_factor_all          0.0468
_refine_ls_R_factor_gt           0.0406
_refine_ls_shift/su_max          0.001
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'calc w=1/[\s^2^(Fo^2^)+(0.0485P)^2^+1.1696P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1072
_refine_ls_wR_factor_ref         0.1133
_reflns_number_gt                4031
_reflns_number_total             4665
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            c9ra09332j2.cif
_cod_data_source_block           190227a_0m
_cod_depositor_comments
;
The following automatic conversions were performed:

data item '_symmetry_cell_setting' value 'Monoclinic' was changed to
'monoclinic' in accordance with the
/home/data/users/saulius/crontab/automatic-downloads/rss-feeds/RSC/lib/dictionaries/cif_core.dic
dictionary named 'cif_core.dic' version 2.4.2 last updated on
2011-04-26.

Automatic conversion script
Id: cif_fix_values 6909 2019-04-08 15:41:33Z antanas 
;
_cod_original_sg_symbol_H-M      P2(1)/n
_cod_database_code               7239608