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

data_7247529
_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 H20 O6 S'
_chemical_formula_sum            'C20 H20 O6 S'
_chemical_formula_weight         388.42
_space_group_crystal_system      orthorhombic
_space_group_IT_number           60
_space_group_name_Hall           '-P 2n 2ab'
_space_group_name_H-M_alt        'P b c n'
_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                 90
_cell_angle_gamma                90
_cell_formula_units_Z            8
_cell_length_a                   13.84590(10)
_cell_length_b                   10.37070(10)
_cell_length_c                   26.6399(3)
_cell_measurement_reflns_used    14092
_cell_measurement_temperature    293(2)
_cell_measurement_theta_max      68.0360
_cell_measurement_theta_min      3.2970
_cell_volume                     3825.27(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_temperature      293(2)
_diffrn_detector                 'Hybrid Pixel Array Detector'
_diffrn_detector_area_resol_mean 10.0000
_diffrn_detector_type            HyPix3000
_diffrn_measured_fraction_theta_full 0.997
_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    -26.00  61.00   0.50    0.40    --   40.33 -56.00 -18.00  174
  2  \w     29.00  64.00   0.50    3.00    --   96.67 -56.00 -18.00   70
  3  \w     30.00 108.00   0.50    3.00    --   96.67-117.00  60.00  156
  4  \w     42.00  68.00   0.50    3.00    --   96.67 -68.00  90.00   52
  5  \w     27.00 109.00   0.50    3.00    --   96.67-109.00 109.00  164
  6  \w     22.00  81.00   0.50    0.40    --   40.33-109.00 109.00  118
  7  \w    -24.00  35.00   0.50    0.40    --  -40.33  12.00-120.00  118
  8  \w    -27.00  65.00   0.50    0.40    --   40.33 -68.00-167.00  184
  9  \w     41.00  99.00   0.50    0.40    --   40.33-138.00-120.00  116
 10  \w     36.00 101.00   0.50    3.00    --   96.67-117.00-150.00  130
 11  \w     29.00  83.00   0.50    3.00    --   96.67 -68.00-167.00  108
 12  \w     31.00  57.00   0.50    3.00    --   96.67 -50.00-150.00   52
 13  \w     30.00  56.00   0.50    3.00    --   96.67 -50.00-180.00   52
 14  \w     16.00 108.00   0.50    0.40    --   40.33  68.00 -34.00  184
 15  \w     73.00 165.00   0.50    3.00    --   96.67  68.00 -34.00  184
 16  \w     81.00 160.00   0.50    3.00    --   96.67 145.00 -90.00  158
 17  \w     76.00 164.00   0.50    3.00    --   96.67  56.00 123.00  176
 18  \w     20.00 107.00   0.50    0.40    --   40.33  56.00 123.00  174
 19  \w    -46.00 -16.00   0.50    3.00    --  -82.50  42.00-150.00   60
 20  \w    -64.00  28.00   0.50    0.40    --  -40.33  68.00 -34.00  184
 21  \w    -61.00  28.00   0.50    0.40    --  -40.33  56.00 123.00  178
 22  \w    -64.00 -14.00   0.50    3.00    --  -82.50  56.00 123.00  100
 23  \w   -107.00 -19.00   0.50    0.40    --  -40.33 -56.00 -18.00  176
 24  \w    -81.00   0.00   0.50    0.40    --  -40.33 109.00-154.00  162
 25  \w    -82.00 -13.00   0.50    3.00    --  -82.50 109.00-154.00  138
 26  \w   -152.00 -81.00   0.50    3.00    --  -82.50-109.00 109.00  142
;
_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      -0.0451905000
_diffrn_orient_matrix_UB_12      -0.0219032000
_diffrn_orient_matrix_UB_13      0.0521602000
_diffrn_orient_matrix_UB_21      -0.0596346000
_diffrn_orient_matrix_UB_22      -0.1130939000
_diffrn_orient_matrix_UB_23      -0.0211184000
_diffrn_orient_matrix_UB_31      0.0823386000
_diffrn_orient_matrix_UB_32      -0.0938169000
_diffrn_orient_matrix_UB_33      0.0133153000
_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  0.0389
_diffrn_reflns_av_unetI/netI     0.0237
_diffrn_reflns_Laue_measured_fraction_full 0.997
_diffrn_reflns_Laue_measured_fraction_max 0.993
_diffrn_reflns_limit_h_max       16
_diffrn_reflns_limit_h_min       -11
_diffrn_reflns_limit_k_max       12
_diffrn_reflns_limit_k_min       -12
_diffrn_reflns_limit_l_max       32
_diffrn_reflns_limit_l_min       -32
_diffrn_reflns_number            21551
_diffrn_reflns_point_group_measured_fraction_full 0.997
_diffrn_reflns_point_group_measured_fraction_max 0.993
_diffrn_reflns_theta_full        67.684
_diffrn_reflns_theta_max         68.165
_diffrn_reflns_theta_min         3.318
_diffrn_source                   'micro-focus sealed X-ray tube'
_diffrn_source_type              'PhotonJet (Cu) X-ray Source'
_exptl_absorpt_coefficient_mu    1.800
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.65647
_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            'metallic light yellow'
_exptl_crystal_colour_lustre     metallic
_exptl_crystal_colour_modifier   light
_exptl_crystal_colour_primary    yellow
_exptl_crystal_density_diffrn    1.349
_exptl_crystal_description       block
_exptl_crystal_F_000             1632
_exptl_crystal_size_max          0.3
_exptl_crystal_size_mid          0.2
_exptl_crystal_size_min          0.2
_refine_diff_density_max         0.230
_refine_diff_density_min         -0.355
_refine_diff_density_rms         0.051
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.073
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     247
_refine_ls_number_reflns         3480
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.073
_refine_ls_R_factor_all          0.0432
_refine_ls_R_factor_gt           0.0382
_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^)+(0.0610P)^2^+0.9207P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1069
_refine_ls_wR_factor_ref         0.1114
_reflns_Friedel_coverage         0.000
_reflns_number_gt                3036
_reflns_number_total             3480
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            d3gc03303a2.cif
_cod_data_source_block           pcf18601_test02
_cod_depositor_comments
'Adding full bibliography for 7247529--7247533.cif.'
_cod_database_code               7247529
_shelx_shelxl_version_number     2018/3
_chemical_oxdiff_formula         'C20 H20 O6 S'
_chemical_oxdiff_usercomment     @RT
_shelx_estimated_absorpt_t_max   0.715
_shelx_estimated_absorpt_t_min   0.614
_diffrn_oxdiff_digest_frames
;
01d2b5e092ebfe8d14b1a2522fc47897c7035103cc9
;
_diffrn_oxdiff_digest_hkl
;
01acc818a3015ea6793ea2f4d65e00ffd878cc
;
_reflns_odcompleteness_completeness 99.92
_reflns_odcompleteness_iscentric 1
_reflns_odcompleteness_theta     66.97
_olex2_refinement_description
;
1. Others
 Fixed Uiso: H009(0.047) H00C(0.05) H00E(0.057) H00H(0.065) H00I(0.065)
 H00J(0.071) H00K(0.084) H00A(0.104) H00B(0.104) H00D(0.104) H00F(0.107)
 H00G(0.107) H00L(0.107) H00N(0.085) H00M(0.111) H00O(0.111) H00P(0.111)
 H00Q(0.108) H00R(0.105) H00S(0.112)
 Fixed X: H009(0.750331) H00C(0.79225) H00E(0.639956) H00H(0.475128)
 H00I(0.602564) H00J(0.438461) H00K(0.634852) H00A(1.09461) H00B(1.097039)
 H00D(1.00724) H00F(0.306302) H00G(0.301286) H00L(0.317661) H00N(0.851828)
 H00M(1.117453) H00O(1.041273) H00P(1.100865) H00Q(0.573815) H00R(0.649225)
 H00S(0.78876)
 Fixed Y: H009(0.577719) H00C(0.334865) H00E(0.195223) H00H(0.171429)
 H00I(0.575611) H00J(0.547283) H00K(0.572412) H00A(0.734209) H00B(0.76808)
 H00D(0.806356) H00F(0.300977) H00G(0.421368) H00L(0.283591) H00N(0.408463)
 H00M(0.339448) H00O(0.285138) H00P(0.408909) H00Q(0.649997) H00R(0.60589)
 H00S(0.488039)
 Fixed Z: H009(0.370523) H00C(0.323368) H00E(0.443614) H00H(0.452922)
 H00I(0.422668) H00J(0.430868) H00K(0.304019) H00A(0.281674) H00B(0.339011)
 H00D(0.306414) H00F(0.417193) H00G(0.452685) H00L(0.475351) H00N(0.228916)
 H00M(0.405349) H00O(0.443405) H00P(0.456899) H00Q(0.229343) H00R(0.155115)
 H00S(0.154941)
;
_shelx_res_checksum              48305
_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 1.581
_oxdiff_exptl_absorpt_empirical_full_min 0.779