#------------------------------------------------------------------------------
#$Date: 2020-10-06 14:42:04 +0300 (Tue, 06 Oct 2020) $
#$Revision: 258102 $
#$URL: file:///home/coder/svn-repositories/cod/cif/7/24/05/7240515.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_7240515
loop_
_publ_author_name
'Chang, Meng-Yang'
'Lai, Kai-Xiang'
'Chang, Yu-Lun'
_publ_section_title
;
 In(OTf)3-catalyzed intramolecular hydroarylation of α-phenylallyl
 β-ketosulfones -- synthesis of sulfonyl 1-benzosuberones and
 1-tetralones
;
_journal_issue                   31
_journal_name_full               'RSC Advances'
_journal_page_first              18231
_journal_page_last               18244
_journal_paper_doi               10.1039/D0RA01962C
_journal_volume                  10
_journal_year                    2020
_chemical_formula_sum            'C25 H24 O5 S'
_chemical_formula_weight         436.50
_space_group_crystal_system      monoclinic
_space_group_IT_number           14
_space_group_name_Hall           '-P 2ybc'
_space_group_name_H-M_alt        'P 1 21/c 1'
_atom_sites_solution_hydrogens   geom
_audit_creation_method           SHELXL-2014/6
_audit_update_record
;
2019-05-13 deposited with the CCDC.	2020-05-06 downloaded from the CCDC.
;
_cell_angle_alpha                90
_cell_angle_beta                 107.381(9)
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   12.2830(19)
_cell_length_b                   19.038(4)
_cell_length_c                   9.2274(14)
_cell_measurement_reflns_used    3328
_cell_measurement_temperature    100(2)
_cell_measurement_theta_max      26.1380
_cell_measurement_theta_min      2.6669
_cell_volume                     2059.2(6)
_computing_cell_refinement       'SAINT V8.34A (Bruker AXS Inc., 2013)'
_computing_data_collection       'Bruker APEX2'
_computing_data_reduction        'SAINT V8.34A (Bruker AXS Inc., 2013)'
_computing_molecular_graphics    'Bruker SHELXTL'
_computing_publication_material  'Bruker SHELXTL'
_computing_structure_refinement  'SHELXL-2014/6 (Sheldrick, 2014)'
_diffrn_ambient_temperature      100(2)
_diffrn_detector_area_resol_mean 8.3333
_diffrn_measured_fraction_theta_full 1.000
_diffrn_measured_fraction_theta_max 0.994
_diffrn_measurement_device_type  'Bruker APEX-II CCD'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0578
_diffrn_reflns_av_unetI/netI     0.0641
_diffrn_reflns_Laue_measured_fraction_full 1.000
_diffrn_reflns_Laue_measured_fraction_max 0.994
_diffrn_reflns_limit_h_max       15
_diffrn_reflns_limit_h_min       -15
_diffrn_reflns_limit_k_max       23
_diffrn_reflns_limit_k_min       -22
_diffrn_reflns_limit_l_max       11
_diffrn_reflns_limit_l_min       -11
_diffrn_reflns_number            14957
_diffrn_reflns_point_group_measured_fraction_full 1.000
_diffrn_reflns_point_group_measured_fraction_max 0.994
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         26.458
_diffrn_reflns_theta_min         1.737
_exptl_absorpt_coefficient_mu    0.194
_exptl_absorpt_correction_T_max  0.7454
_exptl_absorpt_correction_T_min  0.6271
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   'SADABS V2014/4 (Bruker AXS Inc.)'
_exptl_crystal_colour            colorless
_exptl_crystal_density_diffrn    1.408
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       lump
_exptl_crystal_F_000             920
_exptl_crystal_size_max          0.10
_exptl_crystal_size_mid          0.08
_exptl_crystal_size_min          0.08
_refine_diff_density_max         0.441
_refine_diff_density_min         -0.461
_refine_diff_density_rms         0.061
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.034
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     282
_refine_ls_number_reflns         4226
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.034
_refine_ls_R_factor_all          0.0745
_refine_ls_R_factor_gt           0.0471
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'w=1/[σ²(Fo²)+(0.0492P)²+0.4223P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1017
_refine_ls_wR_factor_ref         0.1146
_reflns_Friedel_coverage         0.000
_reflns_number_gt                3042
_reflns_number_total             4226
_reflns_threshold_expression     'I > 2σ(I)'
_cod_data_source_file            d0ra01962c2.cif
_cod_data_source_block           181151LT
_cod_depositor_comments
;
The following automatic conversions were performed:

data item '_exptl_crystal_density_meas' value 'not measured' was
changed to '?' -- the value is perceived as not measured.

Automatic conversion script
Id: cif_fix_values 7556 2019-12-06 15:28:31Z antanas 

 Adding full bibliography for 7240513--7240516.cif.
;
_cod_original_sg_symbol_H-M      'P 21/c'
_cod_database_code               7240515
_shelx_space_group_comment
;
The symmetry employed for this shelxl refinement is uniquely defined
by the following loop, which should always be used as a source of
symmetry information in preference to the above space-group names.
They are only intended as comments.
;
_shelxl_version_number           2014/6
loop_
_space_group_symop_operation_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_site_symmetry_order
_atom_site_calc_flag
_atom_site_refinement_flags_posn
_atom_site_refinement_flags_adp
_atom_site_refinement_flags_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
S1 S 0.37100(4) 0.13047(3) 0.44863(6) 0.01742(16) Uani 1 1 d . . . . .
O1 O 0.27035(13) 0.16715(10) 0.13608(17) 0.0253(4) Uani 1 1 d . . . . .
O2 O -0.20672(12) 0.05429(10) -0.24690(17) 0.0255(4) Uani 1 1 d . . . . .
O3 O -0.01057(12) 0.04572(9) -0.30338(17) 0.0240(4) Uani 1 1 d . . . . .
O4 O 0.41401(12) 0.07319(9) 0.38073(17) 0.0234(4) Uani 1 1 d . . . . .
O5 O 0.42231(12) 0.19851(9) 0.45456(17) 0.0217(4) Uani 1 1 d . . . . .
C1 C 0.39423(18) 0.06908(15) 0.9291(3) 0.0250(6) Uani 1 1 d . . . . .
H1 H 0.3990 0.0561 1.0302 0.030 Uiso 1 1 calc R U . . .
C2 C 0.39585(18) 0.13942(14) 0.8919(3) 0.0220(5) Uani 1 1 d . . . . .
H22 H 0.4026 0.1743 0.9676 0.026 Uiso 1 1 calc R U . . .
C3 C 0.38768(17) 0.15891(13) 0.7447(3) 0.0190(5) Uani 1 1 d . . . . .
H23 H 0.3881 0.2071 0.7178 0.023 Uiso 1 1 calc R U . . .
C4 C 0.37887(16) 0.10640(13) 0.6367(2) 0.0178(5) Uani 1 1 d . . . . .
C5 C 0.21856(17) 0.13756(13) 0.3575(2) 0.0170(5) Uani 1 1 d . . . . .
H4 H 0.1815 0.0934 0.3780 0.020 Uiso 1 1 calc R U . . .
C6 C 0.16709(18) 0.19951(14) 0.4192(3) 0.0229(6) Uani 1 1 d . . . . .
H5 H 0.2161 0.2413 0.4244 0.027 Uiso 1 1 calc R U . . .
H6 H 0.1662 0.1885 0.5237 0.027 Uiso 1 1 calc R U . . .
C7 C 0.04539(18) 0.21702(13) 0.3216(3) 0.0230(5) Uani 1 1 d . . . . .
H7 H 0.0493 0.2434 0.2309 0.028 Uiso 1 1 calc R U . . .
H8 H 0.0097 0.2481 0.3805 0.028 Uiso 1 1 calc R U . . .
C8 C -0.03089(17) 0.15241(13) 0.2694(2) 0.0194(5) Uani 1 1 d . . . . .
H13 H -0.0019 0.1153 0.3481 0.023 Uiso 1 1 calc R U . . .
C9 C -0.15291(17) 0.16812(13) 0.2665(2) 0.0184(5) Uani 1 1 d . . . . .
C10 C -0.19882(18) 0.13662(13) 0.3710(3) 0.0211(5) Uani 1 1 d . . . . .
H9 H -0.1535 0.1050 0.4441 0.025 Uiso 1 1 calc R U . . .
C11 C -0.30971(19) 0.15065(14) 0.3700(3) 0.0239(6) Uani 1 1 d . . . . .
H12 H -0.3394 0.1290 0.4429 0.029 Uiso 1 1 calc R U . . .
C12 C -0.37752(19) 0.19589(14) 0.2636(3) 0.0240(6) Uani 1 1 d . . . . .
H2 H -0.4543 0.2044 0.2611 0.029 Uiso 1 1 calc R U . . .
C13 C 0.38586(18) 0.01760(15) 0.8214(3) 0.0249(6) Uani 1 1 d . . . . .
H3 H 0.3851 -0.0305 0.8484 0.030 Uiso 1 1 calc R U . . .
C14 C 0.37845(17) 0.03618(13) 0.6733(3) 0.0218(5) Uani 1 1 d . . . . .
H24 H 0.3732 0.0011 0.5983 0.026 Uiso 1 1 calc R U . . .
C15 C 0.19658(18) 0.14424(13) 0.1868(2) 0.0181(5) Uani 1 1 d . . . . .
C16 C 0.08404(17) 0.12045(13) 0.0854(2) 0.0181(5) Uani 1 1 d . . . . .
C17 C -0.01978(17) 0.12292(13) 0.1194(2) 0.0181(5) Uani 1 1 d . . . . .
C18 C -0.33201(19) 0.22858(14) 0.1607(3) 0.0257(6) Uani 1 1 d . . . . .
H11 H -0.3774 0.2604 0.0883 0.031 Uiso 1 1 calc R U . . .
C19 C -0.22066(19) 0.21510(14) 0.1629(3) 0.0255(6) Uani 1 1 d . . . . .
H10 H -0.1902 0.2383 0.0925 0.031 Uiso 1 1 calc R U . . .
C20 C -0.11692(18) 0.09991(13) 0.0062(2) 0.0202(5) Uani 1 1 d . . . . .
H21 H -0.1884 0.1010 0.0263 0.024 Uiso 1 1 calc R U . . .
C21 C -0.11331(17) 0.07570(13) -0.1332(2) 0.0181(5) Uani 1 1 d . . . . .
C22 C -0.31607(18) 0.06981(15) -0.2293(3) 0.0278(6) Uani 1 1 d . . . . .
H16 H -0.3261 0.0430 -0.1435 0.042 Uiso 1 1 calc R U . . .
H15 H -0.3760 0.0569 -0.3222 0.042 Uiso 1 1 calc R U . . .
H14 H -0.3210 0.1202 -0.2101 0.042 Uiso 1 1 calc R U . . .
C23 C -0.00843(18) 0.07176(13) -0.1643(2) 0.0195(5) Uani 1 1 d . . . . .
C24 C 0.09841(18) 0.04023(15) -0.3289(3) 0.0256(6) Uani 1 1 d . . . . .
H17 H 0.1344 0.0866 -0.3180 0.038 Uiso 1 1 calc R U . . .
H19 H 0.0885 0.0224 -0.4317 0.038 Uiso 1 1 calc R U . . .
H18 H 0.1469 0.0079 -0.2546 0.038 Uiso 1 1 calc R U . . .
C25 C 0.08810(18) 0.09511(13) -0.0559(2) 0.0194(5) Uani 1 1 d . . . . .
H20 H 0.1591 0.0941 -0.0772 0.023 Uiso 1 1 calc R U . . .
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
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
O5 S1 O4 119.22(9) . . ?
O5 S1 C4 107.57(10) . . ?
O4 S1 C4 108.18(11) . . ?
O5 S1 C5 109.36(10) . . ?
O4 S1 C5 108.54(10) . . ?
C4 S1 C5 102.72(10) . . ?
C21 O2 C22 116.93(18) . . ?
C23 O3 C24 115.10(16) . . ?
C13 C1 C2 120.9(2) . . ?
C13 C1 H1 119.6 . . ?
C2 C1 H1 119.6 . . ?
C3 C2 C1 120.1(2) . . ?
C3 C2 H22 120.0 . . ?
C1 C2 H22 120.0 . . ?
C2 C3 C4 118.5(2) . . ?
C2 C3 H23 120.7 . . ?
C4 C3 H23 120.7 . . ?
C14 C4 C3 121.7(2) . . ?
C14 C4 S1 119.21(18) . . ?
C3 C4 S1 119.07(19) . . ?
C15 C5 C6 110.86(19) . . ?
C15 C5 S1 108.98(14) . . ?
C6 C5 S1 111.71(15) . . ?
C15 C5 H4 108.4 . . ?
C6 C5 H4 108.4 . . ?
S1 C5 H4 108.4 . . ?
C5 C6 C7 112.87(18) . . ?
C5 C6 H5 109.0 . . ?
C7 C6 H5 109.0 . . ?
C5 C6 H6 109.0 . . ?
C7 C6 H6 109.0 . . ?
H5 C6 H6 107.8 . . ?
C6 C7 C8 114.0(2) . . ?
C6 C7 H7 108.8 . . ?
C8 C7 H7 108.8 . . ?
C6 C7 H8 108.8 . . ?
C8 C7 H8 108.8 . . ?
H7 C7 H8 107.6 . . ?
C9 C8 C7 110.7(2) . . ?
C9 C8 C17 114.10(17) . . ?
C7 C8 C17 111.42(18) . . ?
C9 C8 H13 106.7 . . ?
C7 C8 H13 106.7 . . ?
C17 C8 H13 106.7 . . ?
C10 C9 C19 118.1(2) . . ?
C10 C9 C8 120.3(2) . . ?
C19 C9 C8 121.5(2) . . ?
C11 C10 C9 120.9(2) . . ?
C11 C10 H9 119.5 . . ?
C9 C10 H9 119.5 . . ?
C12 C11 C10 120.5(2) . . ?
C12 C11 H12 119.7 . . ?
C10 C11 H12 119.7 . . ?
C11 C12 C18 119.1(2) . . ?
C11 C12 H2 120.5 . . ?
C18 C12 H2 120.5 . . ?
C1 C13 C14 119.8(2) . . ?
C1 C13 H3 120.1 . . ?
C14 C13 H3 120.1 . . ?
C4 C14 C13 119.0(2) . . ?
C4 C14 H24 120.5 . . ?
C13 C14 H24 120.5 . . ?
O1 C15 C16 121.65(19) . . ?
O1 C15 C5 120.35(19) . . ?
C16 C15 C5 117.98(18) . . ?
C17 C16 C25 120.39(19) . . ?
C17 C16 C15 125.8(2) . . ?
C25 C16 C15 113.81(18) . . ?
C20 C17 C16 116.9(2) . . ?
C20 C17 C8 120.04(18) . . ?
C16 C17 C8 123.03(19) . . ?
C12 C18 C19 120.4(2) . . ?
C12 C18 H11 119.8 . . ?
C19 C18 H11 119.8 . . ?
C18 C19 C9 121.0(2) . . ?
C18 C19 H10 119.5 . . ?
C9 C19 H10 119.5 . . ?
C21 C20 C17 122.8(2) . . ?
C21 C20 H21 118.6 . . ?
C17 C20 H21 118.6 . . ?
O2 C21 C20 124.23(19) . . ?
O2 C21 C23 116.04(19) . . ?
C20 C21 C23 119.73(19) . . ?
O2 C22 H16 109.5 . . ?
O2 C22 H15 109.5 . . ?
H16 C22 H15 109.5 . . ?
O2 C22 H14 109.5 . . ?
H16 C22 H14 109.5 . . ?
H15 C22 H14 109.5 . . ?
O3 C23 C25 124.70(19) . . ?
O3 C23 C21 116.72(19) . . ?
C25 C23 C21 118.6(2) . . ?
O3 C24 H17 109.5 . . ?
O3 C24 H19 109.5 . . ?
H17 C24 H19 109.5 . . ?
O3 C24 H18 109.5 . . ?
H17 C24 H18 109.5 . . ?
H19 C24 H18 109.5 . . ?
C23 C25 C16 121.6(2) . . ?
C23 C25 H20 119.2 . . ?
C16 C25 H20 119.2 . . ?
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
S1 O5 1.4343(17) . ?
S1 O4 1.4347(17) . ?
S1 C4 1.769(2) . ?
S1 C5 1.814(2) . ?
O1 C15 1.218(3) . ?
O2 C21 1.365(3) . ?
O2 C22 1.431(3) . ?
O3 C23 1.369(3) . ?
O3 C24 1.431(2) . ?
C1 C13 1.377(4) . ?
C1 C2 1.384(4) . ?
C1 H1 0.9500 . ?
C2 C3 1.382(3) . ?
C2 H22 0.9500 . ?
C3 C4 1.393(3) . ?
C3 H23 0.9500 . ?
C4 C14 1.379(3) . ?
C5 C15 1.522(3) . ?
C5 C6 1.526(3) . ?
C5 H4 1.0000 . ?
C6 C7 1.534(3) . ?
C6 H5 0.9900 . ?
C6 H6 0.9900 . ?
C7 C8 1.534(3) . ?
C7 H7 0.9900 . ?
C7 H8 0.9900 . ?
C8 C9 1.521(3) . ?
C8 C17 1.537(3) . ?
C8 H13 1.0000 . ?
C9 C10 1.390(3) . ?
C9 C19 1.390(3) . ?
C10 C11 1.385(3) . ?
C10 H9 0.9500 . ?
C11 C12 1.382(3) . ?
C11 H12 0.9500 . ?
C12 C18 1.385(3) . ?
C12 H2 0.9500 . ?
C13 C14 1.388(3) . ?
C13 H3 0.9500 . ?
C14 H24 0.9500 . ?
C15 C16 1.490(3) . ?
C16 C17 1.402(3) . ?
C16 C25 1.405(3) . ?
C17 C20 1.401(3) . ?
C18 C19 1.386(3) . ?
C18 H11 0.9500 . ?
C19 H10 0.9500 . ?
C20 C21 1.380(3) . ?
C20 H21 0.9500 . ?
C21 C23 1.403(3) . ?
C22 H16 0.9800 . ?
C22 H15 0.9800 . ?
C22 H14 0.9800 . ?
C23 C25 1.377(3) . ?
C24 H17 0.9800 . ?
C24 H19 0.9800 . ?
C24 H18 0.9800 . ?
C25 H20 0.9500 . ?
