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

data_7247533
_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         'C18 H18 O4 S'
_chemical_formula_sum            'C18 H18 O4 S'
_chemical_formula_weight         330.38
_space_group_crystal_system      monoclinic
_space_group_IT_number           14
_space_group_name_Hall           '-P 2ybc'
_space_group_name_H-M_alt        'P 1 21/c 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                 92.9420(10)
_cell_angle_gamma                90
_cell_formula_units_Z            8
_cell_length_a                   19.6119(2)
_cell_length_b                   16.7818(2)
_cell_length_c                   10.16150(10)
_cell_measurement_reflns_used    12503
_cell_measurement_temperature    100.00(10)
_cell_measurement_theta_max      68.2570
_cell_measurement_theta_min      2.2270
_cell_volume                     3339.98(6)
_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(10)
_diffrn_detector                 'Hybrid Pixel Array Detector'
_diffrn_detector_area_resol_mean 10.0000
_diffrn_detector_type            HyPix3000
_diffrn_measured_fraction_theta_full 0.982
_diffrn_measured_fraction_theta_max 0.978
_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     14.00 110.00   0.50    0.20    --   41.08  77.00   1.00  192
  2  \w    -27.00  68.00   0.50    0.20    --   41.08 -77.00-123.00  190
  3  \w   -151.00 -55.00   0.50    2.22    --  -82.50 -77.00-123.00  192
  4  \w   -105.00 -14.00   0.50    2.22    --  -82.50  77.00   1.00  182
  5  \w     70.00 165.00   0.50    2.22    --   96.67  77.00   1.00  190
  6  \w     28.00 105.00   0.50    2.22    --   96.67 -77.00-123.00  154
  7  \w    -68.00  28.00   0.50    0.20    --  -41.08  77.00   1.00  192
  8  \w    -96.00 -19.00   0.50    0.20    --  -41.08 138.00  30.00  154
  9  \w   -110.00 -14.00   0.50    0.20    --  -41.08 -77.00-123.00  192
 10  \w   -110.00 -14.00   0.50    0.20    --  -41.08 -77.00 -90.00  192
 11  \w    -31.00  29.00   0.50    0.20    --  -41.08  25.00-180.00  120
 12  \w    -24.00  34.00   0.50    0.20    --  -41.08  12.00 120.00  116
 13  \w     41.00 100.00   0.50    0.20    --   41.08-138.00-120.00  118
 14  \w     18.00  79.00   0.50    0.20    --   41.08-104.00 120.00  122
 15  \w    -47.00 -15.00   0.50    2.22    --  -82.50  42.00-120.00   64
 16  \w    -68.00 -14.00   0.50    2.22    --  -82.50  59.00 120.00  108
 17  \w    -47.00 -15.00   0.50    2.22    --  -82.50  42.00-150.00   64
 18  \w     83.00 164.00   0.50    2.22    --   96.67  33.00 -60.00  162
 19  \w     29.00  68.00   0.50    2.22    --   96.67 -59.00-180.00   78
 20  \w     29.00  83.00   0.50    2.22    --   96.67 -68.00  60.00  108
 21  \w     30.00  57.00   0.50    2.22    --   96.67 -50.00 150.00   54
 22  \w     28.00 105.00   0.50    2.22    --   96.67 -77.00  90.00  154
 23  \w     83.00 164.00   0.50    2.22    --   96.67  33.00  30.00  162
 24  \w     29.00  83.00   0.50    2.22    --   96.67 -68.00 150.00  108
 25  \w     29.00  68.00   0.50    2.22    --   96.67 -59.00 -90.00   78
 26  \w     30.00  57.00   0.50    2.22    --   96.67 -50.00 -60.00   54
 27  \w     32.00 109.00   0.50    2.22    --   96.67-117.00  90.00  154
 28  \w     30.00  68.00   0.50    2.22    --   96.67 -59.00-120.00   76
 29  \w     31.00  57.00   0.50    2.22    --   96.67 -50.00  30.00   52
 30  \w     31.00  57.00   0.50    2.22    --   96.67 -50.00 -90.00   52
 31  \w     59.00 105.00   0.50    2.22    --   96.67 -77.00 -90.00   92
 32  \w     30.00  55.00   0.50    2.22    --   96.67 -50.00-180.00   50
 33  \w     33.00  64.00   0.50    2.22    --   96.67 -59.00 -60.00   62
 34  \w    111.00 169.00   0.50    2.22    --   96.67  96.00-120.00  116
 35  \w     86.00 159.00   0.50    2.22    --   96.67  77.00 -30.00  146
 36  \w     31.00  56.00   0.50    2.22    --   96.67 -50.00-120.00   50
;
_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      -0.0659817000
_diffrn_orient_matrix_UB_12      0.0376015000
_diffrn_orient_matrix_UB_13      0.0484343000
_diffrn_orient_matrix_UB_21      -0.0422935000
_diffrn_orient_matrix_UB_22      -0.0666983000
_diffrn_orient_matrix_UB_23      -0.0687135000
_diffrn_orient_matrix_UB_31      0.0068640000
_diffrn_orient_matrix_UB_32      -0.0506271000
_diffrn_orient_matrix_UB_33      0.1263460000
_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  0.0461
_diffrn_reflns_av_unetI/netI     0.0278
_diffrn_reflns_Laue_measured_fraction_full 0.982
_diffrn_reflns_Laue_measured_fraction_max 0.978
_diffrn_reflns_limit_h_max       23
_diffrn_reflns_limit_h_min       -22
_diffrn_reflns_limit_k_max       12
_diffrn_reflns_limit_k_min       -20
_diffrn_reflns_limit_l_max       12
_diffrn_reflns_limit_l_min       -11
_diffrn_reflns_number            21443
_diffrn_reflns_point_group_measured_fraction_full 0.982
_diffrn_reflns_point_group_measured_fraction_max 0.978
_diffrn_reflns_theta_full        67.684
_diffrn_reflns_theta_max         68.153
_diffrn_reflns_theta_min         2.256
_diffrn_source                   'micro-focus sealed X-ray tube'
_diffrn_source_type              'PhotonJet (Cu) X-ray Source'
_exptl_absorpt_coefficient_mu    1.872
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.69862
_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 light white'
_exptl_crystal_colour_lustre     dull
_exptl_crystal_colour_modifier   light
_exptl_crystal_colour_primary    white
_exptl_crystal_density_diffrn    1.314
_exptl_crystal_description       block
_exptl_crystal_F_000             1392
_exptl_crystal_size_max          0.5
_exptl_crystal_size_mid          0.2
_exptl_crystal_size_min          0.1
_refine_diff_density_max         0.414
_refine_diff_density_min         -0.429
_refine_diff_density_rms         0.067
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.132
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     419
_refine_ls_number_reflns         5962
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.132
_refine_ls_R_factor_all          0.0709
_refine_ls_R_factor_gt           0.0589
_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^)+(0.0680P)^2^+5.3066P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1577
_refine_ls_wR_factor_ref         0.1691
_reflns_Friedel_coverage         0.000
_reflns_number_gt                4998
_reflns_number_total             5962
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            d3gc03303a2.cif
_cod_data_source_block           pc-monoester_test01
_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            'C36 H36 O8 S2'
_cod_original_formula_weight         660.77
_cod_original_formula_moiety         '2(C18 H18 O4 S)'
_cod_original_formula_units_Z            4
_cod_database_code               7247533
_shelx_shelxl_version_number     2018/3
_chemical_oxdiff_formula         'C18 H18 O4 S'
_chemical_oxdiff_usercomment     100K
_reflns_odcompleteness_completeness 98.35
_reflns_odcompleteness_iscentric 1
_reflns_odcompleteness_theta     66.97
_olex2_refinement_description
;
1. Others
 Fixed Uiso: H00B(0.036) H00D(0.036) H00E(0.038) H00H(0.039) H00I(0.044)
 H00J(0.04) H00K(0.036) H00L(0.036) H00M(0.041) H00O(0.043) H00R(0.046)
 H00S(0.046) H00T(0.046) H00A(0.055) H00C(0.055) H00F(0.055) H00X(0.051)
 H00Y(0.054) H00Z(0.051) H01A(0.067) H01B(0.067) H01C(0.067) H011(0.057)
 H012(0.054) H013(0.051) H014(0.054) H015(0.052) H016(0.055) H017(0.059)
 H018(0.059) H01G(0.087) H01H(0.087) H01I(0.087) H01D(0.09) H01E(0.09)
 H01F(0.09)
 Fixed X: H00B(0.792308) H00D(0.856472) H00E(0.626998) H00H(0.695022)
 H00I(0.998367) H00J(0.506661) H00K(0.879665) H00L(0.602477) H00M(0.630863)
 H00O(0.536809) H00R(0.893258) H00S(0.660928) H00T(0.807487) H00A(0.635754)
 H00C(0.618047) H00F(0.585737) H00X(1.012878) H00Y(0.786111) H00Z(0.839222)
 H01A(0.613577) H01B(0.673086) H01C(0.598739) H011(0.761644) H012(0.90871)
 H013(0.745861) H014(0.675475) H015(0.559318) H016(0.789182) H017(0.812739)
 H018(0.573819) H01G(0.939822) H01H(0.961495) H01I(1.018378) H01D(0.891567)
 H01E(0.834872) H01F(0.858938)
 Fixed Y: H00B(0.719976) H00D(0.832047) H00E(0.354458) H00H(0.242256)
 H00I(0.687152) H00J(0.145345) H00K(0.788454) H00L(0.300996) H00M(0.096641)
 H00O(0.024149) H00R(0.552963) H00S(-0.024322) H00T(0.959339) H00A(0.742642)
 H00C(0.827439) H00F(0.747955) H00X(0.575256) H00Y(1.090951) H00Z(0.90263)
 H01A(-0.085678) H01B(-0.096951) H01C(-0.132801) H011(0.579802) H012(0.441651)
 H013(0.453589) H014(0.638789) H015(0.441486) H016(1.128587) H017(1.033375)
 H018(0.570022) H01G(0.428304) H01H(0.376555) H01I(0.422974) H01D(0.249223)
 H01E(0.248335) H01F(0.331127)
 Fixed Z: H00B(0.548759) H00D(0.624273) H00E(0.286468) H00H(0.355736)
 H00I(0.280082) H00J(0.607017) H00K(0.351162) H00L(0.552761) H00M(0.308938)
 H00O(0.705402) H00R(0.533784) H00S(0.410069) H00T(0.665793) H00A(0.250145)
 H00C(0.311843) H00F(0.369414) H00X(0.14979) H00Y(0.603388) H00Z(0.286281)
 H01A(0.72994) H01B(0.629535) H01C(0.594573) H011(0.465781) H012(0.401584)
 H013(0.375023) H014(0.5826) H015(0.524276) H016(0.381921) H017(0.224197)
 H018(0.609003) H01G(0.097389) H01H(0.22505) H01I(0.147588) H01D(0.581998)
 H01E(0.689781) H01F(0.629272)
;
_shelx_res_checksum              29992
_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 1.540
_oxdiff_exptl_absorpt_empirical_full_min 0.527