Highly selective catalyst- and additive-free iodosulfonylation of cyclopropenes in water
Peng, Chuxiong; Gu, Fengyan; Lin, Xiaofeng; Ding, Ning; Zhan, Qichen; Cao, Peng; Cao, Tao; Green Chemistry 25 (2023) 671–677; doi:10.1039/D2GC04296G

data_7246014
_publ_section_title
;
 Highly selective catalyst- and additive-free iodosulfonylation of
 cyclopropenes in water
;
_journal_issue                   2
_journal_name_full               'Green Chemistry'
_journal_page_first              671
_journal_page_last               677
_journal_paper_doi               10.1039/D2GC04296G
_journal_volume                  25
_journal_year                    2023
_chemical_absolute_configuration ab
_chemical_formula_moiety         'C20 H19 I O6 S'
_chemical_formula_sum            'C20 H19 I O6 S'
_chemical_formula_weight         514.31
_chemical_name_systematic        1
_space_group_crystal_system      triclinic
_space_group_IT_number           1
_space_group_name_Hall           'P 1'
_space_group_name_H-M_alt        'P 1'
_atom_sites_solution_hydrogens   geom
_audit_creation_date             2022-07-18
_audit_creation_method
;
Olex2 1.2
(compiled 2018.05.29 svn.r3508 for OlexSys, GUI svn.r5506)
;
_audit_update_record
;
2022-07-19 deposited with the CCDC.	2022-12-16 downloaded from the CCDC.
;
_cell_angle_alpha                75.161(12)
_cell_angle_beta                 88.164(11)
_cell_angle_gamma                77.878(12)
_cell_formula_units_Z            1
_cell_length_a                   6.8727(9)
_cell_length_b                   7.4757(10)
_cell_length_c                   10.7012(13)
_cell_measurement_reflns_used    1423
_cell_measurement_temperature    293
_cell_measurement_theta_max      63.2400
_cell_measurement_theta_min      4.2960
_cell_volume                     519.48(12)
_computing_cell_refinement       'CrysAlisPro 1.171.41.89a (Rigaku OD, 2020)'
_computing_data_collection       'CrysAlisPro 1.171.41.89a (Rigaku OD, 2020)'
_computing_data_reduction        'CrysAlisPro 1.171.41.89a (Rigaku OD, 2020)'
_computing_molecular_graphics    'Olex2 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 (Dolomanov et al., 2009)'
_computing_structure_refinement  'ShelXL (Sheldrick, 2015)'
_computing_structure_solution    'SHELXT 2018/2 (Sheldrick, 2018)'
_diffrn_ambient_temperature      293
_diffrn_detector                 'Hybrid Pixel Array Detector'
_diffrn_detector_area_resol_mean 10.0000
_diffrn_measured_fraction_theta_full 0.961
_diffrn_measured_fraction_theta_max 0.961
_diffrn_measurement_details
;
List of Runs (angles in degrees, time in seconds):

  # Type    Start    End  Width  t~exp~   \w     \q     \k     \f   Frames
  1  \w     27.00  67.00   0.50    0.50    --   42.50 -77.00 120.00   80
  2  \w      3.00  69.00   0.50    0.50    --   42.50 -82.00 -60.00  132
  3  \w     19.00  64.00   0.50    0.50    --   42.50  65.00 -60.00   90
  4  \w    105.00 131.00   0.50    0.50    --   42.50   0.00-120.00   52
  5  \w     49.00  92.00   0.50    0.50    --   42.50   0.00-120.00   86
  6  \w    -29.00  -3.00   0.50    0.50    --   42.50   0.00-120.00   52
  7  \w      5.00  66.00   0.50    0.50    --   42.50 -65.00  90.00  122
  8  \w     72.00 130.00   0.50    0.50    --   42.50  65.00 -60.00  116
  9  \w     -6.00  64.00   0.50    0.50    --   42.50 -43.00 -30.00  140
 10  \w     16.00  76.00   0.50    0.50    --   42.50  54.00-120.00  120
 11  \w    -38.00 -10.00   0.50    0.50    --   42.50 -65.00  90.00   56
 12  \w    106.00 131.00   0.50    0.50    --   42.50  65.00-120.00   50
 13  \w     53.00 121.00   0.50    1.50    --   93.70 -82.00 -90.00  136
 14  \w     12.00  55.00   0.50    1.50    --   93.70 -33.00  60.00   86
 15  \w     62.00 111.00   0.50    1.50    --   93.70 -59.00-120.00   98
 16  \w     55.00 111.00   0.50    1.50    --   93.70 -50.00 120.00  112
 17  \w      7.00  54.00   0.50    1.50    --   93.70 -59.00-120.00   94
 18  \w     96.00 121.00   0.50    1.50    --   93.70 -33.00-120.00   50
 19  \w      4.00 183.00   0.50    1.50    --   93.70   0.00-180.00  358
 20  \w     72.00  98.00   0.50    1.50    --   93.70 -82.00 -30.00   52
 21  \w    157.00 182.00   0.50    1.50    --   93.70  82.00-180.00   50
 22  \w     69.00  98.00   0.50    1.50    --   93.70 -82.00  30.00   58
 23  \w      9.00  87.00   0.50    1.50    --   93.70 -33.00-120.00  156
 24  \w     97.00 123.00   0.50    1.50    --   93.70  82.00-180.00   52
 25  \w     70.00 107.00   0.50    1.50    --   93.70  77.00 120.00   74
 26  \w    139.00 182.00   0.50    1.50    --   93.70  77.00 120.00   86
 27  \w     41.00 120.00   0.50    1.50    --   93.70 -82.00  90.00  158
 28  \w     19.00  60.00   0.50    1.50    --   93.70 -82.00  30.00   82
 29  \w      6.00  31.00   0.50    1.50    --   93.70 -82.00  90.00   50
 30  \w     82.00 108.00   0.50    1.50    --   93.70 -82.00-150.00   52
 31  \w    133.00 180.00   0.50    1.50    --   93.70  68.00-180.00   94
 32  \w     74.00 125.00   0.50    1.50    --   93.70 -33.00  60.00  102
 33  \w     15.00  71.00   0.50    1.50    --   93.70 -82.00 150.00  112
 34  \w     75.00 118.00   0.50    1.50    --   93.70 -82.00 150.00   86
 35  \w      7.00  69.00   0.50    1.50    --   93.70 -82.00-120.00  124
;
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'XtaLAB Pro II AFC12 (RINC): Kappa single'
_diffrn_measurement_method       '\w scans'
_diffrn_orient_matrix_type
'CrysAlisPro convention (1999,Acta A55,543-557)'
_diffrn_orient_matrix_UB_11      0.0073277000
_diffrn_orient_matrix_UB_12      -0.0826669000
_diffrn_orient_matrix_UB_13      -0.1183919000
_diffrn_orient_matrix_UB_21      0.0608966000
_diffrn_orient_matrix_UB_22      0.1786133000
_diffrn_orient_matrix_UB_23      -0.0849742000
_diffrn_orient_matrix_UB_31      0.2209822000
_diffrn_orient_matrix_UB_32      -0.0937272000
_diffrn_orient_matrix_UB_33      0.0309017000
_diffrn_radiation_monochromator  mirror
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54184
_diffrn_reflns_av_R_equivalents  0.1062
_diffrn_reflns_av_unetI/netI     0.1442
_diffrn_reflns_Laue_measured_fraction_full 0.961
_diffrn_reflns_Laue_measured_fraction_max 0.961
_diffrn_reflns_limit_h_max       7
_diffrn_reflns_limit_h_min       -7
_diffrn_reflns_limit_k_max       8
_diffrn_reflns_limit_k_min       -8
_diffrn_reflns_limit_l_max       12
_diffrn_reflns_limit_l_min       -12
_diffrn_reflns_number            3424
_diffrn_reflns_point_group_measured_fraction_full 0.579
_diffrn_reflns_point_group_measured_fraction_max 0.579
_diffrn_reflns_theta_full        63.656
_diffrn_reflns_theta_max         63.656
_diffrn_reflns_theta_min         4.275
_diffrn_source                   'micro-focus sealed X-ray tube'
_diffrn_source_type              'Rigaku (Cu) X-ray Source'
_exptl_absorpt_coefficient_mu    13.341
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.33849
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
CrysAlisPro 1.171.41.89a (Rigaku Oxford Diffraction, 2020)
Empirical absorption correction using spherical harmonics,
implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_crystal_colour            'dull light colourless'
_exptl_crystal_colour_lustre     dull
_exptl_crystal_colour_modifier   light
_exptl_crystal_colour_primary    colourless
_exptl_crystal_density_diffrn    1.644
_exptl_crystal_description       block
_exptl_crystal_F_000             256
_exptl_crystal_size_max          0.06
_exptl_crystal_size_mid          0.05
_exptl_crystal_size_min          0.04
_refine_diff_density_max         1.917
_refine_diff_density_min         -1.382
_refine_diff_density_rms         0.199
_refine_ls_abs_structure_details
;
 Refined as an inversion twin.
;
_refine_ls_abs_structure_Flack   0.00(3)
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.056
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     257
_refine_ls_number_reflns         1979
_refine_ls_number_restraints     117
_refine_ls_restrained_S_all      1.028
_refine_ls_R_factor_all          0.1093
_refine_ls_R_factor_gt           0.0875
_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/[\s^2^(Fo^2^)+(0.1839P)^2^] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.2120
_refine_ls_wR_factor_ref         0.2652
_reflns_Friedel_coverage         0.205
_reflns_Friedel_fraction_full    0.197
_reflns_Friedel_fraction_max     0.197
_reflns_number_gt                1636
_reflns_number_total             1979
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            d2gc04296g2.cif
_cod_data_source_block           2j-1-x_auto
_cod_depositor_comments          'Adding full bibliography for 7246014.cif.'
_cod_database_code               7246014
_shelx_shelxl_version_number     2018/3
_shelx_estimated_absorpt_t_max   0.617
_shelx_estimated_absorpt_t_min   0.502
_diffrn_oxdiff_digest_frames
;
01bdac035c64b5589e7d5dbe8d65a69342034185b02
;
_diffrn_oxdiff_digest_hkl
;
01c864c3232f283e816716e0f1e0c57e87bc5f
;
_reflns_odcompleteness_completeness 95.45
_reflns_odcompleteness_iscentric 1
_reflns_odcompleteness_theta     66.97
_olex2_refinement_description
;
1. Twinned data refinement
 Scales: 1.00(3)
 0.00(3)
2. Fixed Uiso
 At 1.2 times of:
  All C(H) groups
 At 1.5 times of:
  All C(H,H,H) groups
3. Uiso/Uaniso restraints and constraints
C1 \\sim C2 \\sim C3 \\sim C4 \\sim C5 \\sim C6 \\sim C7 \\sim C8 \\sim C9
\\sim C10 \\sim C11 \\sim C12 \\sim C13 \\sim C14 \\sim C15 \\sim C16 \\sim C17
\\sim C18 \\sim C19 \\sim C20: within 2A with sigma of 0.004 and sigma for
terminal atoms of 0.008
4.a Ternary CH refined with riding coordinates:
 C8(H8)
4.b Aromatic/amide H refined with riding coordinates:
 C3(H3), C4(H4), C6(H6), C7(H7), C16(H16), C17(H17), C18(H18), C19(H19),
 C20(H20)
4.c Idealised Me refined as rotating group:
 C1(H1A,H1B,H1C), C11(H11A,H11B,H11C), C14(H14A,H14B,H14C)
;
_shelx_res_checksum              80236
_olex2_submission_special_instructions 'No special instructions were received'
_oxdiff_exptl_absorpt_empirical_details
;
Empirical correction (ABSPACK) includes:
- Absorption correction using spherical harmonics
- Frame scaling
;
_oxdiff_exptl_absorpt_empirical_full_max 2.126
_oxdiff_exptl_absorpt_empirical_full_min 0.528