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

data_7247531
_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         'C24 H22 O4 S'
_chemical_formula_sum            'C24 H0.25 O4 S'
_chemical_formula_weight         384.55
_space_group_crystal_system      monoclinic
_space_group_IT_number           14
_space_group_name_Hall           '-P 2yn'
_space_group_name_H-M_alt        'P 1 21/n 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                90
_cell_angle_beta                 99.8670(10)
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   12.50680(10)
_cell_length_b                   10.94440(10)
_cell_length_c                   15.01980(10)
_cell_measurement_reflns_used    15826
_cell_measurement_temperature    100(5)
_cell_measurement_theta_max      68.0240
_cell_measurement_theta_min      2.9890
_cell_volume                     2025.49(3)
_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 0.995
_diffrn_measured_fraction_theta_max 0.993
_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     83.00 164.00   0.50    0.30    --   96.67  33.00 120.00  162
  2  \w     83.00 164.00   0.50    0.30    --   96.67  33.00   0.00  162
  3  \w     83.00 164.00   0.50    0.30    --   96.67  33.00 -30.00  162
  4  \w     75.00 164.00   0.50    0.30    --   96.67  59.00-180.00  178
  5  \w    -31.00  30.00   0.50    0.20    --  -40.33  25.00   0.00  122
  6  \w    -24.00  35.00   0.50    0.20    --  -40.33  12.00  90.00  118
  7  \w    -24.00  35.00   0.50    0.20    --  -40.33  12.00  30.00  118
  8  \w     32.00  90.00   0.50    0.20    --   40.33-123.00 106.00  116
  9  \w     32.00 111.00   0.50    0.30    --   96.67-123.00 106.00  158
 10  \w     30.00 109.00   0.50    0.30    --   96.67-117.00  60.00  158
 11  \w     47.00 108.00   0.50    0.20    --   40.33-151.00 -55.00  122
 12  \w     47.00 130.00   0.50    0.30    --   96.67-151.00 -55.00  166
 13  \w     44.00 127.00   0.50    0.30    --   96.67-145.00 -90.00  166
 14  \w     30.00 109.00   0.50    0.30    --   96.67-117.00   0.00  158
 15  \w     28.00 105.00   0.50    0.30    --   96.67 -77.00  90.00  154
 16  \w     29.00  83.00   0.50    0.30    --   96.67 -68.00 150.00  108
 17  \w     30.00  57.00   0.50    0.30    --   96.67 -50.00 120.00   54
 18  \w     30.00  57.00   0.50    0.30    --   96.67 -50.00 150.00   54
 19  \w     29.00  68.00   0.50    0.30    --   96.67 -59.00  90.00   78
 20  \w     30.00  57.00   0.50    0.30    --   96.67 -50.00  90.00   54
 21  \w     29.00  83.00   0.50    0.30    --   96.67 -68.00   0.00  108
 22  \w     30.00  57.00   0.50    0.30    --   96.67 -50.00 -30.00   54
 23  \w     30.00  57.00   0.50    0.30    --   96.67 -50.00 -60.00   54
 24  \w     30.00  57.00   0.50    0.30    --   96.67 -50.00-180.00   54
 25  \w    -35.00  24.00   0.50    0.20    --   40.33 -12.00-180.00  118
 26  \w    -30.00  31.00   0.50    0.20    --   40.33 -25.00  90.00  122
 27  \w     99.00 164.00   0.50    0.30    --   96.67 117.00  30.00  130
 28  \w     96.00 163.00   0.50    0.30    --   96.67 123.00-172.00  134
 29  \w    -47.00 -15.00   0.50    0.30    --  -82.50  42.00 -30.00   64
 30  \w    -47.00 -15.00   0.50    0.30    --  -82.50  42.00   0.00   64
 31  \w    -47.00 -15.00   0.50    0.30    --  -82.50  42.00  30.00   64
 32  \w    -47.00 -15.00   0.50    0.30    --  -82.50  42.00  90.00   64
 33  \w   -149.00 -74.00   0.50    0.30    --  -82.50-123.00 106.00  150
 34  \w   -108.00 -55.00   0.50    0.20    --  -40.33-151.00 -55.00  106
 35  \w   -149.00 -55.00   0.50    0.30    --  -82.50-151.00 -55.00  188
 36  \w   -109.00 -13.00   0.50    0.20    --  -40.33 -77.00-180.00  192
 37  \w   -109.00 -13.00   0.50    0.20    --  -40.33 -77.00 -60.00  192
 38  \w   -109.00 -13.00   0.50    0.20    --  -40.33 -77.00   0.00  192
 39  \w   -109.00 -13.00   0.50    0.20    --  -40.33 -77.00 120.00  192
 40  \w   -109.00 -13.00   0.50    0.20    --  -40.33 -77.00  90.00  192
 41  \w   -109.00 -13.00   0.50    0.20    --  -40.33 -77.00 -90.00  192
 42  \w   -108.00 -17.00   0.50    0.20    --  -40.33 -64.00-150.00  182
 43  \w   -108.00 -17.00   0.50    0.20    --  -40.33 -64.00  30.00  182
 44  \w    -85.00 -11.00   0.50    0.20    --  -40.33 123.00-172.00  148
 45  \w    -96.00 -19.00   0.50    0.20    --  -40.33 138.00 -90.00  154
;
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'SuperNova Eos'
_diffrn_measurement_method       '\w scans'
_diffrn_orient_matrix_type
'CrysAlisPro convention (1999,Acta A55,543-557)'
_diffrn_orient_matrix_UB_11      -0.0149794000
_diffrn_orient_matrix_UB_12      -0.1172819000
_diffrn_orient_matrix_UB_13      -0.0574648000
_diffrn_orient_matrix_UB_21      -0.0004405000
_diffrn_orient_matrix_UB_22      0.0765639000
_diffrn_orient_matrix_UB_23      -0.0861318000
_diffrn_orient_matrix_UB_31      0.1241481000
_diffrn_orient_matrix_UB_32      -0.0138746000
_diffrn_orient_matrix_UB_33      0.0106398000
_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  0.0521
_diffrn_reflns_av_unetI/netI     0.0256
_diffrn_reflns_Laue_measured_fraction_full 0.995
_diffrn_reflns_Laue_measured_fraction_max 0.993
_diffrn_reflns_limit_h_max       15
_diffrn_reflns_limit_h_min       -11
_diffrn_reflns_limit_k_max       13
_diffrn_reflns_limit_k_min       -13
_diffrn_reflns_limit_l_max       17
_diffrn_reflns_limit_l_min       -18
_diffrn_reflns_number            20242
_diffrn_reflns_point_group_measured_fraction_full 0.995
_diffrn_reflns_point_group_measured_fraction_max 0.993
_diffrn_reflns_theta_full        67.684
_diffrn_reflns_theta_max         68.158
_diffrn_reflns_theta_min         4.258
_diffrn_source                   'micro-focus sealed X-ray tube'
_diffrn_source_type              'PhotonJet (Cu) X-ray Source'
_exptl_absorpt_coefficient_mu    1.648
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.69220
_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 yellowish white'
_exptl_crystal_colour_lustre     clear
_exptl_crystal_colour_modifier   yellowish
_exptl_crystal_colour_primary    white
_exptl_crystal_density_diffrn    1.261
_exptl_crystal_description       block
_exptl_crystal_F_000             769
_exptl_crystal_size_max          0.3
_exptl_crystal_size_mid          0.2
_exptl_crystal_size_min          0.1
_refine_diff_density_max         0.448
_refine_diff_density_min         -0.355
_refine_diff_density_rms         0.045
_refine_ls_extinction_coef       0.0016(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   1.054
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     265
_refine_ls_number_reflns         3664
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.054
_refine_ls_R_factor_all          0.0344
_refine_ls_R_factor_gt           0.0331
_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^)+(0.0509P)^2^+0.7598P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0907
_refine_ls_wR_factor_ref         0.0919
_reflns_Friedel_coverage         0.000
_reflns_number_gt                3462
_reflns_number_total             3664
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            d3gc03303a2.cif
_cod_data_source_block           pcf_08301-test1
_cod_depositor_comments
'Adding full bibliography for 7247529--7247533.cif.'
_cod_database_code               7247531
_shelx_shelxl_version_number     2018/3
_chemical_oxdiff_formula         'C O S H'
_chemical_oxdiff_usercomment     100K
_shelx_estimated_absorpt_t_max   0.853
_shelx_estimated_absorpt_t_min   0.638
_diffrn_oxdiff_digest_frames
;
01cb65f4549cb38eb5c7337c83e7e7be61058602c3c
;
_diffrn_oxdiff_digest_hkl
;
014e070b467db792d582a3b6090b65bf350dfd
;
_reflns_odcompleteness_completeness 99.97
_reflns_odcompleteness_iscentric 1
_reflns_odcompleteness_theta     66.97
_olex2_refinement_description
;
1. Others
 Fixed Uiso: H007(0.024) H009(0.021) H00A(0.021) H00B(0.026) H00E(0.025)
 H00G(0.027) H00H(0.028) H00I(0.024) H00J(0.028) H00K(0.028) H00L(0.029)
 H00M(0.029) H00C(0.039) H00D(0.039) H00F(0.039) H00O(0.027) H00P(0.032)
 H00Q(0.033) H00R(0.033) H00N(0.052) H00S(0.052) H00T(0.052)
 Fixed X: H007(0.63092) H009(0.414665) H00A(0.31814) H00B(0.144381)
 H00E(0.112568) H00G(0.251427) H00H(0.577305) H00I(0.477182) H00J(0.589906)
 H00K(0.745194) H00L(-0.03036) H00M(0.724316) H00C(0.551482) H00D(0.54436)
 H00F(0.444643) H00O(-0.058361) H00P(0.250098) H00Q(0.57679) H00R(0.412321)
 H00N(-0.186416) H00S(-0.188732) H00T(-0.229078)
 Fixed Y: H007(0.532598) H009(0.530838) H00A(0.7696) H00B(0.435195)
 H00E(0.796737) H00G(0.681616) H00H(0.636668) H00I(0.706843) H00J(0.607744)
 H00K(0.436418) H00L(0.4351) H00M(0.473316) H00C(0.979391) H00D(1.041306)
 H00F(1.052697) H00O(0.796606) H00P(0.722545) H00Q(0.683519) H00R(0.721973)
 H00N(0.544953) H00S(0.690962) H00T(0.611099)
 Fixed Z: H007(0.732201) H009(0.664502) H00A(0.682331) H00B(0.672442)
 H00E(0.724727) H00G(0.522337) H00H(0.560645) H00I(0.912405) H00J(1.030722)
 H00K(0.850705) H00L(0.586771) H00M(1.000395) H00C(0.587501) H00D(0.682833)
 H00F(0.600843) H00O(0.633438) H00P(0.369543) H00Q(0.408999) H00R(0.312676)
 H00N(0.509043) H00S(0.514168) H00T(0.5913)
;
_shelx_res_checksum              62342
_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 1.474
_oxdiff_exptl_absorpt_empirical_full_min 0.753