#------------------------------------------------------------------------------
#$Date: 2019-11-30 06:47:19 +0200 (Sat, 30 Nov 2019) $
#$Revision: 244826 $
#$URL: file:///home/coder/svn-repositories/cod/cif/7/23/96/7239608.cif $
#------------------------------------------------------------------------------
#
# This file is available in the Crystallography Open Database (COD),
# http://www.crystallography.net/
#
# All data on this site have been placed in the public domain by the
# contributors.
#
data_7239608
loop_
_publ_author_name
'Xiao, Peng'
'Su, Shikuan'
'Wang, Wei'
'Cao, Weiguo'
'Chen, Jie'
'Li, Jian'
'Chen, Yali'
_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       'φ and ω 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+0.001xFc²λ³/sin(2θ)]^-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/[σ²(Fo²)+(0.0485P)²+1.1696P] where P=(Fo²+2Fc²)/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
loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'-x+1/2, y+1/2, -z+1/2'
'-x, -y, -z'
'x-1/2, -y-1/2, z-1/2'
loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_symmetry_multiplicity
_atom_site_calc_flag
_atom_site_refinement_flags
Si1 Si 1.25998(5) 0.22017(3) 0.28767(4) 0.04127(17) Uani 1 1 d .
Si2 Si 1.04200(5) 0.13210(3) 0.20226(4) 0.04140(17) Uani 1 1 d .
S1 S 1.01419(5) 0.27864(3) 0.59120(3) 0.04795(17) Uani 1 1 d .
C1 C 0.9304(2) 0.36956(13) 0.57255(15) 0.0523(6) Uani 1 1 d .
C2 C 0.9980(3) 0.43286(16) 0.6165(2) 0.0743(8) Uani 1 1 d .
H2 H 1.0805 0.4256 0.6510 0.089 Uiso 1 1 calc R
C3 C 0.9422(4) 0.50664(17) 0.6087(3) 0.0938(11) Uani 1 1 d .
H3 H 0.9855 0.5479 0.6406 0.113 Uiso 1 1 calc R
C4 C 0.8240(4) 0.51907(17) 0.5544(3) 0.0930(10) Uani 1 1 d .
H4 H 0.7894 0.5690 0.5468 0.112 Uiso 1 1 calc R
C5 C 0.7581(3) 0.45821(14) 0.5118(2) 0.0715(7) Uani 1 1 d .
H5 H 0.6777 0.4672 0.4753 0.086 Uiso 1 1 calc R
C6 C 0.8069(2) 0.38200(12) 0.52081(15) 0.0513(5) Uani 1 1 d .
C7 C 0.7149(2) 0.32178(13) 0.47874(15) 0.0514(5) Uani 1 1 d .
C8 C 0.71518(19) 0.23933(12) 0.50961(14) 0.0436(5) Uani 1 1 d .
H8 H 0.6578 0.2269 0.5488 0.052 Uiso 1 1 calc R
C9 C 0.78880(18) 0.18202(11) 0.48697(13) 0.0388(4) Uani 1 1 d .
C10 C 0.90247(17) 0.19480(10) 0.44034(12) 0.0350(4) Uani 1 1 d .
C11 C 0.90702(17) 0.16206(10) 0.35652(13) 0.0369(4) Uani 1 1 d .
H11 H 0.8362 0.1326 0.3289 0.044 Uiso 1 1 calc R
C12 C 1.01403(17) 0.17220(10) 0.31324(12) 0.0347(4) Uani 1 1 d .
C13 C 1.12310(17) 0.21645(10) 0.35578(12) 0.0362(4) Uani 1 1 d .
C14 C 1.11784(17) 0.24962(11) 0.43921(13) 0.0390(4) Uani 1 1 d .
H14 H 1.1888 0.2787 0.4675 0.047 Uiso 1 1 calc R
C15 C 1.00888(18) 0.24023(11) 0.48092(12) 0.0363(4) Uani 1 1 d .
C16 C 0.75504(19) 0.10127(12) 0.51187(14) 0.0446(5) Uani 1 1 d .
C17 C 0.8197(2) -0.03228(12) 0.51171(16) 0.0520(5) Uani 1 1 d .
H17A H 0.7582 -0.0372 0.5534 0.062 Uiso 1 1 calc R
H17B H 0.9008 -0.0579 0.5377 0.062 Uiso 1 1 calc R
C18 C 0.7641(2) -0.07016(11) 0.42466(15) 0.0470(5) Uani 1 1 d .
C19 C 0.6326(2) -0.08689(17) 0.4039(2) 0.0731(8) Uani 1 1 d .
H19 H 0.5765 -0.0739 0.4437 0.088 Uiso 1 1 calc R
C20 C 0.5839(3) -0.1230(2) 0.3236(3) 0.0974(11) Uani 1 1 d .
H20 H 0.4949 -0.1348 0.3101 0.117 Uiso 1 1 calc R
C21 C 0.6643(3) -0.14183(17) 0.2636(2) 0.0833(9) Uani 1 1 d .
H21 H 0.6303 -0.1658 0.2095 0.100 Uiso 1 1 calc R
C22 C 0.7956(3) -0.12493(17) 0.2839(2) 0.0767(8) Uani 1 1 d .
H22 H 0.8515 -0.1374 0.2437 0.092 Uiso 1 1 calc R
C23 C 0.8443(2) -0.08939(15) 0.36402(18) 0.0636(6) Uani 1 1 d .
H23 H 0.9334 -0.0781 0.3775 0.076 Uiso 1 1 calc R
C24 C 0.9161(2) 0.16158(18) 0.10627(17) 0.0687(7) Uani 1 1 d .
H24A H 0.9079 0.2172 0.1054 0.103 Uiso 1 1 calc R
H24B H 0.8333 0.1386 0.1123 0.103 Uiso 1 1 calc R
H24C H 0.9418 0.1443 0.0513 0.103 Uiso 1 1 calc R
C25 C 1.0597(3) 0.02517(15) 0.2065(2) 0.0765(8) Uani 1 1 d .
H25A H 1.0803 0.0067 0.1506 0.115 Uiso 1 1 calc R
H25B H 0.9788 0.0021 0.2168 0.115 Uiso 1 1 calc R
H25C H 1.1290 0.0111 0.2544 0.115 Uiso 1 1 calc R
C26 C 1.4057(2) 0.16397(17) 0.33904(19) 0.0688(7) Uani 1 1 d .
H26A H 1.3832 0.1099 0.3404 0.103 Uiso 1 1 calc R
H26B H 1.4349 0.1821 0.3991 0.103 Uiso 1 1 calc R
H26C H 1.4746 0.1707 0.3043 0.103 Uiso 1 1 calc R
C27 C 1.3070(2) 0.32026(14) 0.26300(18) 0.0614(6) Uani 1 1 d .
H27A H 1.3689 0.3189 0.2222 0.092 Uiso 1 1 calc R
H27B H 1.3462 0.3453 0.3177 0.092 Uiso 1 1 calc R
H27C H 1.2303 0.3486 0.2363 0.092 Uiso 1 1 calc R
O1 O 0.6235(2) 0.33956(12) 0.42076(15) 0.0871(6) Uani 1 1 d .
O2 O 0.65958(18) 0.08469(10) 0.54290(16) 0.0844(7) Uani 1 1 d .
O3 O 0.84518(13) 0.05013(8) 0.49692(10) 0.0485(4) Uani 1 1 d .
O4 O 1.18320(13) 0.17511(9) 0.19693(9) 0.0470(4) Uani 1 1 d .
loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0106 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
Si Si 0.0817 0.0704 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
S S 0.1246 0.1234 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
O4 Si1 C27 112.04(10)
O4 Si1 C26 110.27(11)
C27 Si1 C26 110.51(12)
O4 Si1 C13 97.88(8)
C27 Si1 C13 112.89(10)
C26 Si1 C13 112.68(11)
O4 Si2 C25 111.43(11)
O4 Si2 C24 110.49(11)
C25 Si2 C24 110.65(14)
O4 Si2 C12 98.50(8)
C25 Si2 C12 111.29(11)
C24 Si2 C12 113.97(11)
C15 S1 C1 103.79(10)
C6 C1 C2 118.9(2)
C6 C1 S1 126.54(16)
C2 C1 S1 114.6(2)
C3 C2 C1 120.2(3)
C4 C3 C2 120.6(3)
C5 C4 C3 119.5(3)
C4 C5 C6 122.3(3)
C1 C6 C5 118.5(2)
C1 C6 C7 126.6(2)
C5 C6 C7 114.8(2)
O1 C7 C6 120.0(2)
O1 C7 C8 115.2(2)
C6 C7 C8 124.4(2)
C9 C8 C7 126.74(19)
C8 C9 C10 123.12(18)
C8 C9 C16 117.30(17)
C10 C9 C16 119.58(16)
C11 C10 C15 118.63(16)
C11 C10 C9 121.42(16)
C15 C10 C9 119.95(17)
C12 C11 C10 121.90(16)
C11 C12 C13 119.22(17)
C11 C12 Si2 128.92(14)
C13 C12 Si2 111.83(13)
C14 C13 C12 118.75(16)
C14 C13 Si1 128.81(14)
C12 C13 Si1 112.43(14)
C15 C14 C13 121.35(17)
C14 C15 C10 120.11(17)
C14 C15 S1 118.68(14)
C10 C15 S1 120.92(14)
O2 C16 O3 123.8(2)
O2 C16 C9 124.24(19)
O3 C16 C9 111.91(16)
O3 C17 C18 109.88(17)
C19 C18 C23 118.7(2)
C19 C18 C17 120.9(2)
C23 C18 C17 120.4(2)
C18 C19 C20 119.8(3)
C21 C20 C19 121.1(3)
C20 C21 C22 119.3(3)
C21 C22 C23 119.6(3)
C18 C23 C22 121.5(2)
C16 O3 C17 117.79(16)
Si2 O4 Si1 118.31(8)
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
Si1 O4 1.6574(15)
Si1 C27 1.844(2)
Si1 C26 1.847(2)
Si1 C13 1.8837(19)
Si2 O4 1.6494(15)
Si2 C25 1.849(3)
Si2 C24 1.850(3)
Si2 C12 1.880(2)
S1 C15 1.785(2)
S1 C1 1.787(3)
C1 C6 1.397(3)
C1 C2 1.400(3)
C2 C3 1.391(4)
C3 C4 1.369(5)
C4 C5 1.351(4)
C5 C6 1.403(3)
C6 C7 1.476(3)
C7 O1 1.215(3)
C7 C8 1.493(3)
C8 C9 1.325(3)
C9 C10 1.483(3)
C9 C16 1.496(3)
C10 C11 1.394(3)
C10 C15 1.403(3)
C11 C12 1.386(3)
C12 C13 1.421(3)
C13 C14 1.393(3)
C14 C15 1.388(3)
C16 O2 1.195(2)
C16 O3 1.328(2)
C17 O3 1.466(2)
C17 C18 1.494(3)
C18 C19 1.372(3)
C18 C23 1.374(3)
C19 C20 1.382(5)
C20 C21 1.367(5)
C21 C22 1.371(4)
C22 C23 1.375(4)
