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#$Date: 2023-10-06 03:31:15 +0300 (Fri, 06 Oct 2023) $
#$Revision: 286771 $
#$URL: file:///home/coder/svn-repositories/cod/cif/7/06/26/7062687.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_7062687
loop_
_publ_author_name
'Blé-González, Ever A.'
'Isbel, Stephen R.'
'Ojo, Olatunji S.'
'Hillesheim, Patrick C.'
'Zeller, Matthias'
'Bugarin, Alejandro'
_publ_section_title
;
 Regiodivergent sulfonylation of terminal olefins via dearomative
 rearrangement
;
_journal_issue                   36
_journal_name_full               'New Journal of Chemistry'
_journal_page_first              17020
_journal_page_last               17025
_journal_paper_doi               10.1039/D3NJ03595F
_journal_volume                  47
_journal_year                    2023
_chemical_formula_sum            'C16 H15 Cl O3 S'
_chemical_formula_weight         322.79
_space_group_crystal_system      triclinic
_space_group_IT_number           2
_space_group_name_Hall           '-P 1'
_space_group_name_H-M_alt        'P -1'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     dual
_atom_sites_solution_secondary   difmap
_audit_creation_method           SHELXL-2018/3
_audit_update_record
;
2023-04-30 deposited with the CCDC.	2023-08-21 downloaded from the CCDC.
;
_cell_angle_alpha                91.485(3)
_cell_angle_beta                 95.543(3)
_cell_angle_gamma                108.404(3)
_cell_formula_units_Z            2
_cell_length_a                   7.5988(4)
_cell_length_b                   7.6069(4)
_cell_length_c                   13.6966(7)
_cell_measurement_reflns_used    9831
_cell_measurement_temperature    150(2)
_cell_measurement_theta_max      33.1850
_cell_measurement_theta_min      2.8265
_cell_volume                     746.37(7)
_computing_cell_refinement       'SAINT V8.40B (Bruker, 2020)'
_computing_data_collection       'Apex4 v2022.10-0 (Bruker, 2022)'
_computing_data_reduction        'SAINT V8.40B (Bruker, 2020)'
_computing_structure_refinement
;  
SHELXL-2018/3 (Sheldrick, 2015a, 2018), 
SHELXLE Rev1460 (Hübschle et al., 2011)
;
_computing_structure_solution    'SHELXT (Sheldrick, 2015b)'
_diffrn_ambient_temperature      150(2)
_diffrn_detector_area_resol_mean 7.4074
_diffrn_detector_type
'PhotonII charge-integrating pixel array (CPAD)'
_diffrn_measured_fraction_theta_full 0.994
_diffrn_measured_fraction_theta_max 0.995
_diffrn_measurement_device       'three circle diffractometer'
_diffrn_measurement_device_type  'Bruker AXS D8 Quest'
_diffrn_measurement_method       'omega and phi scans'
_diffrn_radiation_monochromator  'Triumph curved graphite crystal'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0374
_diffrn_reflns_av_unetI/netI     0.0266
_diffrn_reflns_Laue_measured_fraction_full 0.994
_diffrn_reflns_Laue_measured_fraction_max 0.995
_diffrn_reflns_limit_h_max       11
_diffrn_reflns_limit_h_min       -11
_diffrn_reflns_limit_k_max       11
_diffrn_reflns_limit_k_min       -11
_diffrn_reflns_limit_l_max       20
_diffrn_reflns_limit_l_min       -21
_diffrn_reflns_number            32913
_diffrn_reflns_point_group_measured_fraction_full 0.994
_diffrn_reflns_point_group_measured_fraction_max 0.995
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         33.217
_diffrn_reflns_theta_min         3.063
_diffrn_source                   'fine focus sealed tube X-ray source'
_diffrn_source_current           '30 mA'
_diffrn_source_voltage           '50 kV'
_exptl_absorpt_coefficient_mu    0.402
_exptl_absorpt_correction_T_max  0.7465
_exptl_absorpt_correction_T_min  0.6825
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
 SADABS 2016/2: Krause, L., Herbst-Irmer, R., Sheldrick G.M. & Stalke D.,
 J. Appl. Cryst. 48 (2015) 3-10
;
_exptl_crystal_colour            colourless
_exptl_crystal_density_diffrn    1.436
_exptl_crystal_description       plate
_exptl_crystal_F_000             336
_exptl_crystal_size_max          0.320
_exptl_crystal_size_mid          0.270
_exptl_crystal_size_min          0.130
_refine_diff_density_max         2.229
_refine_diff_density_min         -0.542
_refine_diff_density_rms         0.077
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.043
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     191
_refine_ls_number_reflns         5696
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.043
_refine_ls_R_factor_all          0.0649
_refine_ls_R_factor_gt           0.0534
_refine_ls_shift/su_max          0.001
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'w=1/[σ²(Fo²)+(0.0742P)²+0.6132P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1452
_refine_ls_wR_factor_ref         0.1540
_reflns_Friedel_coverage         0.000
_reflns_number_gt                4696
_reflns_number_total             5696
_reflns_threshold_expression     'I > 2σ(I)'
_cod_data_source_file            d3nj03595f2.cif
_cod_data_source_block           AB_03_2_0m
_cod_depositor_comments
'Adding full bibliography for 7062686--7062687.cif.'
_cod_database_code               7062687
_shelx_shelxl_version_number     2018/3
_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.
;
_shelx_estimated_absorpt_t_min   0.882
_shelx_estimated_absorpt_t_max   0.950
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x, -y, -z'
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
Cl1 Cl 0.17908(7) 0.80142(7) 0.93005(3) 0.03737(12) Uani 1 1 d . . . . .
S1 S 0.75314(5) 1.01246(5) 0.62171(3) 0.02368(10) Uani 1 1 d . . . . .
O1 O 0.94110(18) 1.06304(19) 0.66987(10) 0.0332(3) Uani 1 1 d . . . . .
O2 O 0.70506(19) 1.14119(17) 0.55699(10) 0.0307(3) Uani 1 1 d . . . . .
O3 O 0.3566(2) 0.2986(2) 0.90571(10) 0.0371(3) Uani 1 1 d . . . . .
C1 C 0.7057(2) 0.7995(2) 0.54908(12) 0.0267(3) Uani 1 1 d . . . . .
H1A H 0.570044 0.750063 0.527823 0.032 Uiso 1 1 calc R U . . .
H1B H 0.770691 0.826517 0.489278 0.032 Uiso 1 1 calc R U . . .
C2 C 0.7645(2) 0.6520(2) 0.60138(12) 0.0263(3) Uani 1 1 d . . . . .
C3 C 0.9198(3) 0.6195(3) 0.58009(15) 0.0360(4) Uani 1 1 d . . . . .
H3A H 0.960747 0.529494 0.613882 0.043 Uiso 1 1 calc R U . . .
H3B H 0.989239 0.686285 0.531160 0.043 Uiso 1 1 calc R U . . .
C4 C 0.6505(2) 0.5516(2) 0.67722(12) 0.0242(3) Uani 1 1 d . . . . .
C5 C 0.7378(2) 0.5036(2) 0.76260(13) 0.0292(3) Uani 1 1 d . . . . .
H5 H 0.869303 0.529912 0.769615 0.035 Uiso 1 1 calc R U . . .
C6 C 0.6366(3) 0.4188(2) 0.83677(13) 0.0313(3) Uani 1 1 d . . . . .
H6 H 0.698627 0.387774 0.894078 0.038 Uiso 1 1 calc R U . . .
C7 C 0.4433(3) 0.3789(2) 0.82737(13) 0.0288(3) Uani 1 1 d . . . . .
C8 C 0.3528(2) 0.4209(2) 0.74255(13) 0.0283(3) Uani 1 1 d . . . . .
H8 H 0.220774 0.390485 0.734820 0.034 Uiso 1 1 calc R U . . .
C9 C 0.4571(2) 0.5080(2) 0.66881(12) 0.0265(3) Uani 1 1 d . . . . .
H9 H 0.394656 0.538339 0.611417 0.032 Uiso 1 1 calc R U . . .
C10 C 0.1625(3) 0.2725(3) 0.90324(17) 0.0429(5) Uani 1 1 d . . . . .
H10A H 0.141783 0.393207 0.901083 0.064 Uiso 1 1 calc R U . . .
H10B H 0.116154 0.212018 0.962237 0.064 Uiso 1 1 calc R U . . .
H10C H 0.095669 0.194290 0.844702 0.064 Uiso 1 1 calc R U . . .
C11 C 0.5964(2) 0.9627(2) 0.71185(11) 0.0231(3) Uani 1 1 d . . . . .
C12 C 0.6528(2) 0.9199(2) 0.80568(12) 0.0260(3) Uani 1 1 d . . . . .
H12 H 0.778384 0.924405 0.822888 0.031 Uiso 1 1 calc R U . . .
C13 C 0.5242(2) 0.8706(2) 0.87376(12) 0.0274(3) Uani 1 1 d . . . . .
H13 H 0.559789 0.840273 0.937927 0.033 Uiso 1 1 calc R U . . .
C14 C 0.3423(2) 0.8667(2) 0.84580(12) 0.0267(3) Uani 1 1 d . . . . .
C15 C 0.2845(2) 0.9105(3) 0.75307(13) 0.0297(3) Uani 1 1 d . . . . .
H15 H 0.159291 0.907441 0.736253 0.036 Uiso 1 1 calc R U . . .
C16 C 0.4139(2) 0.9588(2) 0.68541(12) 0.0278(3) Uani 1 1 d . . . . .
H16 H 0.377906 0.989128 0.621321 0.033 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'
Cl Cl 0.1484 0.1585 '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
O1 S1 O2 118.34(8) . . ?
O1 S1 C11 108.74(8) . . ?
O2 S1 C11 108.39(8) . . ?
O1 S1 C1 108.52(8) . . ?
O2 S1 C1 106.27(8) . . ?
C11 S1 C1 105.88(8) . . ?
C7 O3 C10 117.08(16) . . ?
C2 C1 S1 114.33(11) . . ?
C2 C1 H1A 108.7 . . ?
S1 C1 H1A 108.7 . . ?
C2 C1 H1B 108.7 . . ?
S1 C1 H1B 108.7 . . ?
H1A C1 H1B 107.6 . . ?
C3 C2 C4 122.29(16) . . ?
C3 C2 C1 119.02(15) . . ?
C4 C2 C1 118.66(15) . . ?
C2 C3 H3A 120.0 . . ?
C2 C3 H3B 120.0 . . ?
H3A C3 H3B 120.0 . . ?
C9 C4 C5 117.64(15) . . ?
C9 C4 C2 122.30(15) . . ?
C5 C4 C2 120.02(15) . . ?
C6 C5 C4 121.43(16) . . ?
C6 C5 H5 119.3 . . ?
C4 C5 H5 119.3 . . ?
C5 C6 C7 119.92(16) . . ?
C5 C6 H6 120.0 . . ?
C7 C6 H6 120.0 . . ?
O3 C7 C8 124.77(17) . . ?
O3 C7 C6 115.38(16) . . ?
C8 C7 C6 119.85(15) . . ?
C7 C8 C9 119.50(16) . . ?
C7 C8 H8 120.3 . . ?
C9 C8 H8 120.3 . . ?
C4 C9 C8 121.63(15) . . ?
C4 C9 H9 119.2 . . ?
C8 C9 H9 119.2 . . ?
O3 C10 H10A 109.5 . . ?
O3 C10 H10B 109.5 . . ?
H10A C10 H10B 109.5 . . ?
O3 C10 H10C 109.5 . . ?
H10A C10 H10C 109.5 . . ?
H10B C10 H10C 109.5 . . ?
C16 C11 C12 121.21(15) . . ?
C16 C11 S1 118.25(12) . . ?
C12 C11 S1 120.48(12) . . ?
C13 C12 C11 119.54(15) . . ?
C13 C12 H12 120.2 . . ?
C11 C12 H12 120.2 . . ?
C12 C13 C14 118.40(14) . . ?
C12 C13 H13 120.8 . . ?
C14 C13 H13 120.8 . . ?
C15 C14 C13 122.71(16) . . ?
C15 C14 Cl1 118.55(14) . . ?
C13 C14 Cl1 118.73(12) . . ?
C14 C15 C16 118.45(16) . . ?
C14 C15 H15 120.8 . . ?
C16 C15 H15 120.8 . . ?
C15 C16 C11 119.69(15) . . ?
C15 C16 H16 120.2 . . ?
C11 C16 H16 120.2 . . ?
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
Cl1 C14 1.7417(17) . ?
S1 O1 1.4426(13) . ?
S1 O2 1.4444(12) . ?
S1 C11 1.7638(17) . ?
S1 C1 1.7952(17) . ?
O3 C7 1.370(2) . ?
O3 C10 1.422(3) . ?
C1 C2 1.506(2) . ?
C1 H1A 0.9900 . ?
C1 H1B 0.9900 . ?
C2 C3 1.337(3) . ?
C2 C4 1.487(2) . ?
C3 H3A 0.9500 . ?
C3 H3B 0.9500 . ?
C4 C9 1.393(2) . ?
C4 C5 1.402(2) . ?
C5 C6 1.382(2) . ?
C5 H5 0.9500 . ?
C6 C7 1.395(3) . ?
C6 H6 0.9500 . ?
C7 C8 1.389(2) . ?
C8 C9 1.395(2) . ?
C8 H8 0.9500 . ?
C9 H9 0.9500 . ?
C10 H10A 0.9800 . ?
C10 H10B 0.9800 . ?
C10 H10C 0.9800 . ?
C11 C16 1.390(2) . ?
C11 C12 1.395(2) . ?
C12 C13 1.389(2) . ?
C12 H12 0.9500 . ?
C13 C14 1.389(2) . ?
C13 H13 0.9500 . ?
C14 C15 1.387(2) . ?
C15 C16 1.388(2) . ?
C15 H15 0.9500 . ?
C16 H16 0.9500 . ?
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
_geom_torsion_site_symmetry_1
_geom_torsion_site_symmetry_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
_geom_torsion_publ_flag
O1 S1 C1 C2 46.17(14) . . . . ?
O2 S1 C1 C2 174.44(12) . . . . ?
C11 S1 C1 C2 -70.42(14) . . . . ?
S1 C1 C2 C3 -103.50(18) . . . . ?
S1 C1 C2 C4 74.68(17) . . . . ?
C3 C2 C4 C9 -146.53(18) . . . . ?
C1 C2 C4 C9 35.3(2) . . . . ?
C3 C2 C4 C5 35.9(2) . . . . ?
C1 C2 C4 C5 -142.23(16) . . . . ?
C9 C4 C5 C6 -1.1(2) . . . . ?
C2 C4 C5 C6 176.61(16) . . . . ?
C4 C5 C6 C7 0.2(3) . . . . ?
C10 O3 C7 C8 -6.1(3) . . . . ?
C10 O3 C7 C6 173.97(17) . . . . ?
C5 C6 C7 O3 -178.66(16) . . . . ?
C5 C6 C7 C8 1.4(3) . . . . ?
O3 C7 C8 C9 178.07(16) . . . . ?
C6 C7 C8 C9 -2.0(3) . . . . ?
C5 C4 C9 C8 0.5(2) . . . . ?
C2 C4 C9 C8 -177.18(15) . . . . ?
C7 C8 C9 C4 1.1(3) . . . . ?
O1 S1 C11 C16 163.27(13) . . . . ?
O2 S1 C11 C16 33.39(15) . . . . ?
C1 S1 C11 C16 -80.29(14) . . . . ?
O1 S1 C11 C12 -19.69(15) . . . . ?
O2 S1 C11 C12 -149.57(13) . . . . ?
C1 S1 C11 C12 96.75(14) . . . . ?
C16 C11 C12 C13 0.7(2) . . . . ?
S1 C11 C12 C13 -176.28(12) . . . . ?
C11 C12 C13 C14 -0.4(2) . . . . ?
C12 C13 C14 C15 -0.2(3) . . . . ?
C12 C13 C14 Cl1 178.99(12) . . . . ?
C13 C14 C15 C16 0.5(3) . . . . ?
Cl1 C14 C15 C16 -178.73(13) . . . . ?
C14 C15 C16 C11 -0.2(3) . . . . ?
C12 C11 C16 C15 -0.4(3) . . . . ?
S1 C11 C16 C15 176.61(13) . . . . ?
