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

data_7247530
_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         'C25 H24 O4 S'
_chemical_formula_sum            'C25 H24 O4 S'
_chemical_formula_weight         420.50
_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                84.233(4)
_cell_angle_beta                 68.850(5)
_cell_angle_gamma                83.784(4)
_cell_formula_units_Z            2
_cell_length_a                   9.6633(5)
_cell_length_b                   10.4825(5)
_cell_length_c                   11.2824(7)
_cell_measurement_reflns_used    9064
_cell_measurement_temperature    100.00(13)
_cell_measurement_theta_max      67.9580
_cell_measurement_theta_min      4.1920
_cell_volume                     1057.28(11)
_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      100.00(13)
_diffrn_detector                 'Hybrid Pixel Array Detector'
_diffrn_detector_area_resol_mean 10.0000
_diffrn_detector_type            HyPix3000
_diffrn_measured_fraction_theta_full 0.987
_diffrn_measured_fraction_theta_max 0.983
_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    -31.00  30.00   0.50    0.26    --  -40.33  25.00   0.00  122
  2  \w    -42.00 -15.00   0.50    1.60    --  -82.50  42.00 120.00   54
  3  \w    -45.00 -17.00   0.50    1.60    --  -82.50  42.00 150.00   56
  4  \w    -47.00 -15.00   0.50    1.60    --  -82.50  42.00  90.00   64
  5  \w    -31.00  30.00   0.50    0.26    --  -40.33  25.00 150.00  122
  6  \w    -27.00  64.00   0.50    0.26    --   40.33 -64.00  30.00  182
  7  \w     23.00 106.00   0.50    1.60    --   96.67 -96.00   0.00  166
  8  \w     73.00 101.00   0.50    1.60    --   96.67 -77.00  60.00   56
  9  \w     80.00 111.00   0.50    1.60    --   96.67-145.00 -30.00   62
 10  \w     89.00 127.00   0.50    1.60    --   96.67-145.00   0.00   76
 11  \w     87.00 125.00   0.50    1.60    --   96.67-145.00  90.00   76
 12  \w     41.00  82.00   0.50    1.60    --   96.67 -77.00 -60.00   82
 13  \w     47.00 125.00   0.50    1.60    --   96.67-145.00-120.00  156
 14  \w    102.00 127.00   0.50    1.60    --   96.67-145.00-180.00   50
 15  \w     57.00  86.00   0.50    1.60    --   96.67-145.00-180.00   58
 16  \w     34.00 102.00   0.50    1.60    --   96.67-117.00-120.00  136
 17  \w     45.00  77.00   0.50    1.60    --   96.67-145.00 -30.00   64
 18  \w     24.00 106.00   0.50    1.60    --   96.67 -99.00-128.00  164
 19  \w     28.00  92.00   0.50    1.60    --   96.67 -77.00  30.00  128
 20  \w     44.00  82.00   0.50    1.60    --   96.67-145.00  90.00   76
 21  \w     33.00  59.00   0.50    1.60    --   96.67 -77.00  60.00   52
 22  \w     32.00  65.00   0.50    1.60    --   96.67 -59.00  60.00   66
 23  \w     29.00  54.00   0.50    1.60    --   96.67 -59.00 120.00   50
 24  \w     93.00 120.00   0.50    1.60    --   96.67  17.00  30.00   54
 25  \w     96.00 163.00   0.50    1.60    --   96.67  42.00 -30.00  134
 26  \w    138.00 164.00   0.50    1.60    --   96.67 117.00 -90.00   52
 27  \w    107.00 170.00   0.50    1.60    --   96.67  99.00 -22.00  126
 28  \w    108.00 141.00   0.50    1.60    --   96.67 117.00  60.00   66
 29  \w    103.00 129.00   0.50    1.60    --   96.67 117.00  30.00   52
 30  \w    105.00 158.00   0.50    1.60    --   96.67  96.00  90.00  106
 31  \w     90.00 163.00   0.50    1.60    --   96.67  42.00 120.00  146
 32  \w     84.00 151.00   0.50    1.60    --   96.67  33.00  90.00  134
 33  \w     79.00 164.00   0.50    1.60    --   96.67  59.00   0.00  170
 34  \w    102.00 128.00   0.50    1.60    --   96.67 117.00 -90.00   52
 35  \w     83.00 151.00   0.50    1.60    --   96.67 145.00 -90.00  136
 36  \w     74.00 161.00   0.50    1.60    --   96.67  68.00  30.00  174
 37  \w     85.00 124.00   0.50    1.60    --   96.67  25.00-120.00   78
 38  \w     29.00  68.00   0.50    1.60    --   96.67 -59.00-150.00   78
 39  \w     30.00  56.00   0.50    1.60    --   96.67 -50.00-150.00   52
 40  \w     28.00  97.00   0.50    1.60    --   96.67 -96.00 -60.00  138
 41  \w     -2.00  76.00   0.50    0.26    --   40.33 -99.00-128.00  156
 42  \w    -26.00  57.00   0.50    0.26    --   40.33 -50.00 -30.00  166
 43  \w    -35.00  24.00   0.50    0.26    --   40.33 -12.00   0.00  118
 44  \w    -30.00  31.00   0.50    0.26    --   40.33 -25.00  90.00  122
 45  \w    -30.00  31.00   0.50    0.26    --   40.33 -25.00 120.00  122
 46  \w      9.00  42.00   0.50    0.26    --   40.33  91.00 121.42   66
 47  \w     10.00  43.00   0.50    0.26    --   40.33  87.00  75.86   66
 48  \w    -43.00  26.00   0.50    0.26    --  -40.33  38.00-150.00  138
 49  \w    -30.00  31.00   0.50    0.26    --   40.33 -25.00-180.00  122
 50  \w    -76.00  24.00   0.50    0.26    --  -40.33  99.00 -22.00  200
 51  \w    -57.00 -16.00   0.50    1.60    --  -82.50  50.00   0.00   82
 52  \w    -81.00  -9.00   0.50    1.60    --  -82.50  99.00 -22.00  144
 53  \w    -78.00   4.00   0.50    0.26    --  -40.33 104.00 150.00  164
 54  \w   -108.00 -17.00   0.50    0.26    --  -40.33 -64.00 -90.00  182
 55  \w   -106.00 -25.00   0.50    0.26    --  -40.33 -38.00-180.00  162
 56  \w   -156.00 -85.00   0.50    1.60    --  -82.50 -99.00-128.00  142
 57  \w   -150.00 -66.00   0.50    1.60    --  -82.50 -42.00 120.00  168
;
_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      0.1367700000
_diffrn_orient_matrix_UB_12      0.0183647000
_diffrn_orient_matrix_UB_13      0.0343310000
_diffrn_orient_matrix_UB_21      0.1031844000
_diffrn_orient_matrix_UB_22      -0.0342057000
_diffrn_orient_matrix_UB_23      -0.1347883000
_diffrn_orient_matrix_UB_31      -0.0066718000
_diffrn_orient_matrix_UB_32      0.1429821000
_diffrn_orient_matrix_UB_33      -0.0467267000
_diffrn_radiation_monochromator  mirror
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           'Cu K\a'
_diffrn_radiation_wavelength     1.54184
_diffrn_reflns_av_R_equivalents  0.0564
_diffrn_reflns_av_unetI/netI     0.0421
_diffrn_reflns_Laue_measured_fraction_full 0.987
_diffrn_reflns_Laue_measured_fraction_max 0.983
_diffrn_reflns_limit_h_max       11
_diffrn_reflns_limit_h_min       -11
_diffrn_reflns_limit_k_max       12
_diffrn_reflns_limit_k_min       -11
_diffrn_reflns_limit_l_max       13
_diffrn_reflns_limit_l_min       -13
_diffrn_reflns_number            11810
_diffrn_reflns_point_group_measured_fraction_full 0.987
_diffrn_reflns_point_group_measured_fraction_max 0.983
_diffrn_reflns_theta_full        67.684
_diffrn_reflns_theta_max         68.200
_diffrn_reflns_theta_min         4.211
_diffrn_source                   'micro-focus sealed X-ray tube'
_diffrn_source_type              'PhotonJet (Cu) X-ray Source'
_exptl_absorpt_coefficient_mu    1.598
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.71557
_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            'dull dark brown'
_exptl_crystal_colour_lustre     dull
_exptl_crystal_colour_modifier   dark
_exptl_crystal_colour_primary    brown
_exptl_crystal_density_diffrn    1.321
_exptl_crystal_description       needle
_exptl_crystal_F_000             444
_exptl_crystal_size_max          0.6
_exptl_crystal_size_mid          0.1
_exptl_crystal_size_min          0.1
_refine_diff_density_max         0.955
_refine_diff_density_min         -0.442
_refine_diff_density_rms         0.116
_refine_ls_extinction_coef       0.0029(6)
_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   1.104
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     275
_refine_ls_number_reflns         3800
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.104
_refine_ls_R_factor_all          0.0807
_refine_ls_R_factor_gt           0.0784
_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/[\s^2^(Fo^2^)+(0.0248P)^2^+10.2581P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.2295
_refine_ls_wR_factor_ref         0.2302
_reflns_Friedel_coverage         0.000
_reflns_number_gt                3559
_reflns_number_total             3800
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            d3gc03303a2.cif
_cod_data_source_block           pcf11501_test03
_cod_depositor_comments
'Adding full bibliography for 7247529--7247533.cif.'
_cod_database_code               7247530
_shelx_shelxl_version_number     2018/3
_chemical_oxdiff_formula         'C24 H20 O4 S'
_chemical_oxdiff_usercomment     100K
_shelx_estimated_absorpt_t_max   0.857
_shelx_estimated_absorpt_t_min   0.447
_diffrn_oxdiff_digest_frames
;
01885c34b2e60f8c88563370a15197202e061869a66
;
_diffrn_oxdiff_digest_hkl
;
0154fff7fa591c3325e940017c10a0950d3d64
;
_reflns_odcompleteness_completeness 99.74
_reflns_odcompleteness_iscentric 1
_reflns_odcompleteness_theta     66.97
_olex2_refinement_description
;
1. Others
 Fixed Uiso: H008(0.027) H009(0.021) H00E(0.027) H00F(0.03) H00G(0.025)
 H00H(0.029) H00A(0.033) H00B(0.033) H00C(0.033) H00J(0.028) H00K(0.029)
 H00L(0.037) H00M(0.029) H00N(0.026) H00O(0.027) H00P(0.029) H00Q(0.036)
 H00S(0.036) H00D(0.047) H00I(0.047) H00R(0.047) H00T(0.045) H00U(0.045)
 H00V(0.045)
 Fixed X: H008(0.878195) H009(0.403734) H00E(0.637629) H00F(0.716698)
 H00G(0.142834) H00H(-0.093499) H00A(0.641088) H00B(0.53974) H00C(0.503574)
 H00J(-0.224119) H00K(0.883522) H00L(0.808914) H00M(0.389573) H00N(0.633971)
 H00O(0.107881) H00P(-0.125703) H00Q(0.886596) H00S(0.561695) H00D(1.123417)
 H00I(1.105664) H00R(1.064844) H00T(0.291386) H00U(0.13212) H00V(0.147862)
 Fixed Y: H008(0.400776) H009(0.744352) H00E(0.44446) H00F(0.761796)
 H00G(0.904984) H00H(0.87116) H00A(0.703798) H00B(0.833751) H00C(0.70299)
 H00J(0.706539) H00K(0.357899) H00L(1.121213) H00M(1.051212) H00N(0.49023)
 H00O(0.623604) H00P(0.585111) H00Q(0.904778) H00S(1.193092) H00D(0.365381)
 H00I(0.308328) H00R(0.225604) H00T(0.968648) H00U(1.014755) H00V(0.896108)
 Fixed Z: H008(0.332301) H009(0.412255) H00E(0.035254) H00F(0.278039)
 H00G(0.489648) H00H(0.63832) H00A(0.076138) H00B(0.06994) H00C(0.029043)
 H00J(0.615749) H00K(-0.022096) H00L(0.308474) H00M(0.352144) H00N(0.390526)
 H00O(0.283447) H00P(0.437464) H00Q(0.277183) H00S(0.346656) H00D(0.137146)
 H00I(0.017495) H00R(0.151065) H00T(-0.053423) H00U(0.04589) H00V(-0.038155)
;
_shelx_res_checksum              37431
_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 1.475
_oxdiff_exptl_absorpt_empirical_full_min 0.663