Diastereoselective organophotocatalytic hydrosulfonylation of cyclopropenes
Chandu, Palasetty; Biswas, Sourabh; Garai, Sumit; Sureshkumar, Devarajulu; Green Chemistry 25 (2023) 9086–9091; doi:10.1039/D3GC03303A

data_7247532
_publ_section_title
;
 Diastereoselective organophotocatalytic hydrosulfonylation of
 cyclopropenes
;
_journal_issue                   22
_journal_name_full               'Green Chemistry'
_journal_page_first              9086
_journal_page_last               9091
_journal_paper_doi               10.1039/D3GC03303A
_journal_volume                  25
_journal_year                    2023
_chemical_formula_moiety         'C20 H22 O6 S'
_chemical_formula_sum            'C20 H22 O6 S'
_chemical_formula_weight         390.43
_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
_audit_creation_date             2023-07-31
_audit_creation_method
;
Olex2 1.3-ac4
(compiled 2019.04.23 svn.r3594 for Rigaku Oxford Diffraction, GUI svn.r5739)
;
_audit_update_record
;
2023-07-31 deposited with the CCDC.	2023-10-18 downloaded from the CCDC.
;
_cell_angle_alpha                94.727(2)
_cell_angle_beta                 94.995(3)
_cell_angle_gamma                90.152(2)
_cell_formula_units_Z            4
_cell_length_a                   5.7239(2)
_cell_length_b                   16.0544(4)
_cell_length_c                   20.5787(7)
_cell_measurement_reflns_used    13684
_cell_measurement_temperature    100(5)
_cell_measurement_theta_max      26.8860
_cell_measurement_theta_min      1.9940
_cell_volume                     1877.37(10)
_computing_cell_refinement       'CrysAlisPro 1.171.41.93a (Rigaku OD, 2020)'
_computing_data_collection       'CrysAlisPro 1.171.41.93a (Rigaku OD, 2020)'
_computing_data_reduction        'CrysAlisPro 1.171.41.93a (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 (Sheldrick, 2015)'
_diffrn_ambient_environment      N~2~
_diffrn_ambient_temperature      100(5)
_diffrn_detector                 'Hybrid Pixel Array Detector'
_diffrn_detector_area_resol_mean 10.0000
_diffrn_detector_type            HyPix3000
_diffrn_measured_fraction_theta_full 0.952
_diffrn_measured_fraction_theta_max 0.886
_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    -82.00 -10.00   0.25   16.55    --  -12.09 -25.00 143.00  288
  2  \w      3.00  60.00   0.25   16.55    --  -12.09  25.00 -53.00  228
  3  \w    -57.00 -27.00   0.25   16.55    --   12.13 -25.00 143.00  120
  4  \w    -16.00   9.00   0.25   16.55    --   12.13 -25.00 143.00  100
  5  \w    -28.00  15.00   0.25   16.55    --  -12.09  38.00 -90.00  172
  6  \w    -28.00  56.00   0.25   16.55    --  -12.09  38.00   0.00  336
  7  \w    -77.00 -38.00   0.25   16.55    --  -12.09 -38.00-120.00  156
  8  \w     21.00  55.00   0.25   16.55    --  -12.09  38.00 -90.00  136
  9  \w    -47.00  16.00   0.25   16.55    --  -12.09 -77.00 120.00  252
 10  \w    -23.00  16.00   0.25   16.55    --  -12.09 -99.00 -90.00  156
 11  \w    -23.00  20.00   0.25   16.55    --  -12.09 -99.00 -30.00  172
 12  \w    -15.00  16.00   0.25   16.55    --  -12.09 -99.00-180.00  124
 13  \w    -18.00  21.00   0.25   16.55    --  -12.09 -99.00 -60.00  156
 14  \w    -26.00  50.00   0.25   16.55    --  -12.09  38.00 -30.00  304
 15  \w     58.00  84.00   0.25   16.55    --   12.13  19.00  60.00  104
 16  \w    -62.00   1.00   0.25   16.55    --   12.13 -19.00-150.00  252
 17  \w    -13.00  54.00   0.25   16.55    --   12.13  19.00  60.00  268
 18  \w    -22.00  48.00   0.25   16.55    --   12.13 -99.00  60.00  280
 19  \w     54.00  79.00   0.25   16.55    --   12.13  57.00 -60.00  100
;
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'XtaLAB Synergy, Dualflex, HyPix3000'
_diffrn_measurement_method       '\w scans'
_diffrn_orient_matrix_type
'CrysAlisPro convention (1999,Acta A55,543-557)'
_diffrn_orient_matrix_UB_11      -0.0271282000
_diffrn_orient_matrix_UB_12      -0.0424669000
_diffrn_orient_matrix_UB_13      0.0034144000
_diffrn_orient_matrix_UB_21      -0.0175490000
_diffrn_orient_matrix_UB_22      0.0101760000
_diffrn_orient_matrix_UB_23      0.0334108000
_diffrn_orient_matrix_UB_31      -0.1201285000
_diffrn_orient_matrix_UB_32      0.0076492000
_diffrn_orient_matrix_UB_33      -0.0088006000
_diffrn_radiation_monochromator  mirror
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           'Mo K\a'
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0456
_diffrn_reflns_av_unetI/netI     0.0537
_diffrn_reflns_Laue_measured_fraction_full 0.952
_diffrn_reflns_Laue_measured_fraction_max 0.886
_diffrn_reflns_limit_h_max       7
_diffrn_reflns_limit_h_min       -7
_diffrn_reflns_limit_k_max       20
_diffrn_reflns_limit_k_min       -20
_diffrn_reflns_limit_l_max       25
_diffrn_reflns_limit_l_min       -25
_diffrn_reflns_number            25421
_diffrn_reflns_point_group_measured_fraction_full 0.952
_diffrn_reflns_point_group_measured_fraction_max 0.886
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         27.131
_diffrn_reflns_theta_min         1.994
_diffrn_source                   'micro-focus sealed X-ray tube'
_diffrn_source_type              'PhotonJet (Mo) X-ray Source'
_exptl_absorpt_coefficient_mu    0.207
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.82899
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
CrysAlisPro 1.171.41.93a (Rigaku Oxford Diffraction, 2020)
Empirical absorption correction using spherical harmonics,
implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_crystal_colour            'clear whiteish white'
_exptl_crystal_colour_lustre     clear
_exptl_crystal_colour_modifier   whiteish
_exptl_crystal_colour_primary    white
_exptl_crystal_density_diffrn    1.381
_exptl_crystal_description       needle
_exptl_crystal_F_000             824
_exptl_crystal_size_max          0.7
_exptl_crystal_size_mid          0.2
_exptl_crystal_size_min          0.1
_refine_diff_density_max         2.306
_refine_diff_density_min         -0.842
_refine_diff_density_rms         0.226
_refine_ls_extinction_coef       0.001(2)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc^2^\l^3^/sin(2\q)]^-1/4^
_refine_ls_extinction_method     'SHELXL-2018/3 (Sheldrick 2018)'
_refine_ls_goodness_of_fit_ref   1.103
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     494
_refine_ls_number_reflns         7374
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.103
_refine_ls_R_factor_all          0.1966
_refine_ls_R_factor_gt           0.1794
_refine_ls_shift/su_max          0.011
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'w=1/[\s^2^(Fo^2^)+(0.1636P)^2^+53.8824P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.4517
_refine_ls_wR_factor_ref         0.4613
_reflns_Friedel_coverage         0.000
_reflns_number_gt                5890
_reflns_number_total             7374
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            d3gc03303a2.cif
_cod_data_source_block           pc-sub01_test1
_cod_depositor_comments
;
Adding full bibliography for 7247529--7247533.cif.

2024-12-16
Z value and formula fixed to values more according to usual
chemical conventions.                 miguel
;
_cod_original_formula_sum            'C40 H44 O12 S2'
_cod_original_formula_weight         780.87
_cod_original_formula_moiety         '2(C20 H22 O6 S)'
_cod_original_formula_units_Z            2
_cod_database_code               7247532
_shelx_shelxl_version_number     2018/3
_chemical_oxdiff_formula         'C20 H22 O6 S '
_chemical_oxdiff_usercomment     100K
_reflns_odcompleteness_completeness 93.95
_reflns_odcompleteness_iscentric 1
_reflns_odcompleteness_theta     26.32
_olex2_refinement_description
;
1. Others
 Fixed Uiso: H00F(0.021) H00H(0.024) H00J(0.024) H00K(0.03) H00M(0.029)
 H00P(0.024) H00Q(0.027) H00S(0.029) H00T(0.024) H00U(0.03) H00V(0.024)
 H00Z(0.035) H01A(0.027) H01B(0.027) H012(0.027) H013(0.026) H01M(0.03)
 H01N(0.03) H015(0.031) H016(0.026) H017(0.034) H018(0.032) H019(0.034)
 H01C(0.033) H01O(0.026) H01P(0.031) H01D(0.048) H01E(0.048) H01F(0.048)
 H01Q(0.05) H01R(0.05) H01S(0.05) H01T(0.048) H01U(0.048) H01V(0.048)
 H01G(0.054) H01H(0.054) H01I(0.054) H01W(0.056) H01X(0.056) H01Y(0.056)
 H01J(0.059) H01K(0.059) H01L(0.059)
 Fixed X: H00F(-0.221495) H00H(-0.369956) H00J(0.241982) H00K(0.315375)
 H00M(0.920885) H00P(0.282974) H00Q(0.912723) H00S(0.336569) H00T(0.195665)
 H00U(0.311801) H00V(-0.370817) H00Z(-0.01106) H01A(-0.042905) H01B(0.139114)
 H012(0.296543) H013(0.506553) H01M(0.679347) H01N(0.821835) H015(0.94568)
 H016(0.804487) H017(0.374545) H018(0.357897) H019(-0.35727) H01C(-0.191436)
 H01O(1.009662) H01P(0.603239) H01D(0.284713) H01E(0.32186) H01F(0.542934)
 H01Q(1.07785) H01R(1.10593) H01S(1.328989) H01T(0.671408) H01U(0.650187)
 H01V(0.422696) H01G(0.16954) H01H(0.411196) H01I(0.168399) H01W(0.912102)
 H01X(0.656481) H01Y(0.727037) H01J(0.392467) H01K(0.240622) H01L(0.144987)
 Fixed Y: H00F(0.791357) H00H(0.660514) H00J(0.806781) H00K(0.970836)
 H00M(0.941524) H00P(0.804527) H00Q(0.787263) H00S(0.830804) H00T(0.8463)
 H00U(0.570446) H00V(0.693271) H00Z(0.481202) H01A(0.909781) H01B(0.852882)
 H012(0.706168) H013(0.699135) H01M(0.592861) H01N(0.66019) H015(0.803353)
 H016(0.673788) H017(0.739589) H018(0.919479) H019(0.527034) H01C(0.591785)
 H01O(0.717015) H01P(1.024637) H01D(0.65414) H01E(0.586964) H01F(0.635684)
 H01Q(0.470964) H01R(0.509768) H01S(0.503631) H01T(0.872293) H01U(0.796488)
 H01V(0.827905) H01G(0.96069) H01H(0.996882) H01I(1.019315) H01W(0.94986)
 H01X(0.990158) H01Y(0.929924) H01J(0.601742) H01K(0.535188) H01L(0.569535)
 Fixed Z: H00F(0.689295) H00H(0.70058) H00J(0.161246) H00K(0.306213)
 H00M(0.219103) H00P(0.690553) H00Q(0.046031) H00S(0.333711) H00T(0.917679)
 H00U(0.812169) H00V(0.864969) H00Z(0.793194) H01A(0.748694) H01B(0.7877)
 H012(0.776798) H013(0.330098) H01M(0.265121) H01N(0.231165) H015(0.247507)
 H016(0.101526) H017(0.975426) H018(0.104362) H019(0.738457) H01C(0.926861)
 H01O(0.338447) H01P(0.247414) H01D(0.51193) H01E(0.565108) H01F(0.543491)
 H01Q(0.382282) H01R(0.456742) H01S(0.414857) H01T(0.492375) H01U(0.537447)
 H01V(0.495918) H01G(0.524915) H01H(0.561544) H01I(0.591661) H01W(0.056441)
 H01X(0.055102) H01Y(-0.005834) H01J(1.00508) H01K(0.956592) H01L(1.024442)
;
_shelx_res_checksum              64601
_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 1.916
_oxdiff_exptl_absorpt_empirical_full_min 0.625