#------------------------------------------------------------------------------
#$Date: 2017-10-05 10:20:59 +0300 (Thu, 05 Oct 2017) $
#$Revision: 201729 $
#$URL: file:///home/coder/svn-repositories/cod/cif/1/54/75/1547578.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_1547578
loop_
_publ_author_name
'Wang, Ming'
'Chen, Shihao'
'Jiang, Xuefeng'
_publ_section_title
;
 Construction of Functionalized Annulated Sulfone via SO2/I Exchange of
 Cyclic Diaryliodonium Salts.
;
_journal_issue                   18
_journal_name_full               'Organic letters'
_journal_page_first              4916
_journal_page_last               4919
_journal_paper_doi               10.1021/acs.orglett.7b02388
_journal_volume                  19
_journal_year                    2017
_chemical_formula_sum            'C15 H12 O2 S'
_chemical_formula_weight         256.31
_chemical_name_systematic
; 
 ? 
;
_space_group_IT_number           14
_symmetry_cell_setting           monoclinic
_symmetry_space_group_name_Hall  '-P 2ybc'
_symmetry_space_group_name_H-M   'P 1 21/c 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                 101.677(2)
_cell_angle_gamma                90.00
_cell_formula_units_Z            4
_cell_length_a                   11.6687(8)
_cell_length_b                   8.3221(5)
_cell_length_c                   12.6959(8)
_cell_measurement_reflns_used    5948
_cell_measurement_temperature    296(2)
_cell_measurement_theta_max      28.15
_cell_measurement_theta_min      2.94
_cell_volume                     1207.36(13)
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 2008)'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 2008)'
_diffrn_ambient_temperature      296(2)
_diffrn_measured_fraction_theta_full 1.000
_diffrn_measured_fraction_theta_max 1.000
_diffrn_measurement_device_type  'Bruker Apex II CCD'
_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  0.0360
_diffrn_reflns_av_sigmaI/netI    0.0206
_diffrn_reflns_limit_h_max       12
_diffrn_reflns_limit_h_min       -13
_diffrn_reflns_limit_k_max       9
_diffrn_reflns_limit_k_min       -9
_diffrn_reflns_limit_l_max       15
_diffrn_reflns_limit_l_min       -15
_diffrn_reflns_number            13195
_diffrn_reflns_theta_full        25.01
_diffrn_reflns_theta_max         25.01
_diffrn_reflns_theta_min         1.78
_exptl_absorpt_coefficient_mu    0.257
_exptl_absorpt_correction_T_max  0.9384
_exptl_absorpt_correction_T_min  0.8974
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   sadabs
_exptl_crystal_colour            colorless
_exptl_crystal_density_diffrn    1.410
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       block
_exptl_crystal_F_000             536
_exptl_crystal_size_max          0.43
_exptl_crystal_size_mid          0.31
_exptl_crystal_size_min          0.25
_refine_diff_density_max         0.277
_refine_diff_density_min         -0.267
_refine_diff_density_rms         0.040
_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     163
_refine_ls_number_reflns         2120
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.039
_refine_ls_R_factor_all          0.0386
_refine_ls_R_factor_gt           0.0329
_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/[σ²(Fo²)+(0.0482P)²+0.4661P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0870
_refine_ls_wR_factor_ref         0.0920
_reflns_number_gt                1845
_reflns_number_total             2120
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            ol7b02388_si_006.cif
_cod_data_source_block           z
_cod_depositor_comments
;
The following automatic conversions were performed:

'_symmetry_cell_setting' value 'Monoclinic' changed to 'monoclinic'
according to
/home/data/users/saulius/crontab/automatic-downloads/current/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 4973 2017-02-22 13:04:09Z antanas 
;
_cod_original_sg_symbol_H-M      P2(1)/c
_cod_database_code               1547578
loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'-x, y+1/2, -z+1/2'
'-x, -y, -z'
'x, -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
S1 S 0.71534(4) 0.01666(5) 0.36107(3) 0.03591(16) Uani 1 1 d .
O1 O 0.63075(12) 0.07400(17) 0.27082(10) 0.0503(4) Uani 1 1 d .
O2 O 0.81348(11) -0.07241(17) 0.33905(10) 0.0478(3) Uani 1 1 d .
C1 C 0.64656(14) -0.1000(2) 0.44490(13) 0.0337(4) Uani 1 1 d .
C2 C 0.54320(15) -0.1794(2) 0.40133(14) 0.0396(4) Uani 1 1 d .
H2A H 0.5083 -0.1659 0.3293 0.047 Uiso 1 1 calc R
C3 C 0.49301(16) -0.2787(2) 0.46623(16) 0.0436(4) Uani 1 1 d .
H3A H 0.4246 -0.3344 0.4381 0.052 Uiso 1 1 calc R
C4 C 0.54519(16) -0.2945(2) 0.57320(16) 0.0443(4) Uani 1 1 d .
H4A H 0.5113 -0.3611 0.6172 0.053 Uiso 1 1 calc R
C5 C 0.64714(16) -0.2131(2) 0.61623(14) 0.0402(4) Uani 1 1 d .
H5A H 0.6802 -0.2249 0.6889 0.048 Uiso 1 1 calc R
C6 C 0.70090(14) -0.1144(2) 0.55330(13) 0.0328(4) Uani 1 1 d .
C7 C 0.81216(14) -0.0234(2) 0.59493(13) 0.0344(4) Uani 1 1 d .
C8 C 0.81116(14) 0.1462(2) 0.55524(13) 0.0338(4) Uani 1 1 d .
C9 C 0.76675(14) 0.1790(2) 0.44612(13) 0.0339(4) Uani 1 1 d .
C10 C 0.75981(17) 0.3330(2) 0.40475(15) 0.0434(4) Uani 1 1 d .
H10A H 0.7296 0.3508 0.3321 0.052 Uiso 1 1 calc R
C11 C 0.7982(2) 0.4601(2) 0.47251(17) 0.0541(5) Uani 1 1 d .
H11A H 0.7950 0.5645 0.4458 0.065 Uiso 1 1 calc R
C12 C 0.8413(2) 0.4311(2) 0.58015(17) 0.0542(5) Uani 1 1 d .
H12A H 0.8660 0.5168 0.6261 0.065 Uiso 1 1 calc R
C13 C 0.84832(17) 0.2771(2) 0.62064(15) 0.0449(5) Uani 1 1 d .
H13A H 0.8786 0.2607 0.6934 0.054 Uiso 1 1 calc R
C14 C 0.92670(16) -0.1148(3) 0.60371(16) 0.0483(5) Uani 1 1 d .
H14A H 0.9224 -0.2276 0.5841 0.058 Uiso 1 1 calc R
H14B H 0.9930 -0.0574 0.5866 0.058 Uiso 1 1 calc R
C15 C 0.88592(17) -0.0674(3) 0.70268(15) 0.0499(5) Uani 1 1 d .
H15A H 0.9277 0.0184 0.7459 0.060 Uiso 1 1 calc R
H15B H 0.8572 -0.1516 0.7434 0.060 Uiso 1 1 calc R
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'
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
O1 S1 O2 117.54(8)
O1 S1 C1 110.13(8)
O2 S1 C1 108.27(8)
O1 S1 C9 109.21(8)
O2 S1 C9 109.24(8)
C1 S1 C9 101.21(8)
C2 C1 C6 122.38(16)
C2 C1 S1 119.34(13)
C6 C1 S1 118.24(13)
C3 C2 C1 119.15(16)
C3 C2 H2A 120.4
C1 C2 H2A 120.4
C4 C3 C2 119.36(16)
C4 C3 H3A 120.3
C2 C3 H3A 120.3
C3 C4 C5 121.07(17)
C3 C4 H4A 119.5
C5 C4 H4A 119.5
C4 C5 C6 121.21(17)
C4 C5 H5A 119.4
C6 C5 H5A 119.4
C5 C6 C1 116.82(15)
C5 C6 C7 123.84(15)
C1 C6 C7 119.34(15)
C8 C7 C6 114.13(14)
C8 C7 C15 119.92(15)
C6 C7 C15 119.39(15)
C8 C7 C14 116.25(15)
C6 C7 C14 117.21(15)
C15 C7 C14 58.68(13)
C13 C8 C9 116.49(16)
C13 C8 C7 124.01(15)
C9 C8 C7 119.46(15)
C10 C9 C8 122.52(16)
C10 C9 S1 119.56(13)
C8 C9 S1 117.91(13)
C11 C10 C9 119.18(17)
C11 C10 H10A 120.4
C9 C10 H10A 120.4
C12 C11 C10 119.39(18)
C12 C11 H11A 120.3
C10 C11 H11A 120.3
C13 C12 C11 121.03(18)
C13 C12 H12A 119.5
C11 C12 H12A 119.5
C12 C13 C8 121.37(18)
C12 C13 H13A 119.3
C8 C13 H13A 119.3
C15 C14 C7 60.14(12)
C15 C14 H14A 117.8
C7 C14 H14A 117.8
C15 C14 H14B 117.8
C7 C14 H14B 117.8
H14A C14 H14B 114.9
C14 C15 C7 61.18(12)
C14 C15 H15A 117.6
C7 C15 H15A 117.6
C14 C15 H15B 117.6
C7 C15 H15B 117.6
H15A C15 H15B 114.8
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
S1 O1 1.4344(13)
S1 O2 1.4383(14)
S1 C1 1.7507(17)
S1 C9 1.7577(17)
C1 C2 1.388(2)
C1 C6 1.399(2)
C2 C3 1.378(3)
C2 H2A 0.9300
C3 C4 1.378(3)
C3 H3A 0.9300
C4 C5 1.382(3)
C4 H4A 0.9300
C5 C6 1.382(2)
C5 H5A 0.9300
C6 C7 1.503(2)
C7 C8 1.497(2)
C7 C15 1.507(2)
C7 C14 1.522(2)
C8 C13 1.385(2)
C8 C9 1.404(2)
C9 C10 1.381(2)
C10 C11 1.380(3)
C10 H10A 0.9300
C11 C12 1.379(3)
C11 H11A 0.9300
C12 C13 1.377(3)
C12 H12A 0.9300
C13 H13A 0.9300
C14 C15 1.484(3)
C14 H14A 0.9700
C14 H14B 0.9700
C15 H15A 0.9700
C15 H15B 0.9700
loop_
_geom_torsion_atom_site_label_1
_geom_torsion_atom_site_label_2
_geom_torsion_atom_site_label_3
_geom_torsion_atom_site_label_4
_geom_torsion
O1 S1 C1 C2 26.84(17)
O2 S1 C1 C2 -102.92(15)
C9 S1 C1 C2 142.30(15)
O1 S1 C1 C6 -155.58(13)
O2 S1 C1 C6 74.66(15)
C9 S1 C1 C6 -40.12(15)
C6 C1 C2 C3 -1.3(3)
S1 C1 C2 C3 176.19(14)
C1 C2 C3 C4 1.2(3)
C2 C3 C4 C5 -0.3(3)
C3 C4 C5 C6 -0.7(3)
C4 C5 C6 C1 0.6(3)
C4 C5 C6 C7 -179.59(17)
C2 C1 C6 C5 0.4(3)
S1 C1 C6 C5 -177.15(13)
C2 C1 C6 C7 -179.44(16)
S1 C1 C6 C7 3.1(2)
C5 C6 C7 C8 -136.90(17)
C1 C6 C7 C8 42.9(2)
C5 C6 C7 C15 14.7(3)
C1 C6 C7 C15 -165.55(17)
C5 C6 C7 C14 82.3(2)
C1 C6 C7 C14 -97.95(19)
C6 C7 C8 C13 133.57(18)
C15 C7 C8 C13 -17.8(3)
C14 C7 C8 C13 -85.2(2)
C6 C7 C8 C9 -44.2(2)
C15 C7 C8 C9 164.38(16)
C14 C7 C8 C9 97.01(19)
C13 C8 C9 C10 0.0(3)
C7 C8 C9 C10 177.94(17)
C13 C8 C9 S1 -178.47(14)
C7 C8 C9 S1 -0.5(2)
O1 S1 C9 C10 -23.59(17)
O2 S1 C9 C10 106.22(16)
C1 S1 C9 C10 -139.73(15)
O1 S1 C9 C8 154.92(13)
O2 S1 C9 C8 -75.26(15)
C1 S1 C9 C8 38.79(15)
C8 C9 C10 C11 0.3(3)
S1 C9 C10 C11 178.71(16)
C9 C10 C11 C12 -0.8(3)
C10 C11 C12 C13 1.0(4)
C11 C12 C13 C8 -0.8(3)
C9 C8 C13 C12 0.3(3)
C7 C8 C13 C12 -177.58(19)
C8 C7 C14 C15 110.54(17)
C6 C7 C14 C15 -109.46(18)
C8 C7 C15 C14 -104.32(18)
C6 C7 C15 C14 105.76(18)
