A Metal-free Four-component Sulfonylation, Giese Cyclization, Selenylation Cascade via Insertion of Sulfur Dioxide
Volla, Chandra; Nair, Akshay Murali; Halder, Indranil; Chemical Communications  (2022) –; doi:10.1039/D2CC02315F

data_7130139
_publ_section_title
;
 A Metal-free Four-component Sulfonylation, Giese Cyclization,
 Selenylation Cascade via Insertion of Sulfur Dioxide
;
_journal_name_full               'Chemical Communications'
_journal_paper_doi               10.1039/D2CC02315F
_journal_year                    2022
_chemical_formula_moiety         'C30 H28 O5 S Se'
_chemical_formula_sum            'C30 H28 O5 S Se'
_chemical_formula_weight         579.54
_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             2021-09-15
_audit_creation_method
;
Olex2 1.3-ac4
(compiled 2019.04.23 svn.r3594 for Rigaku Oxford Diffraction, GUI svn.r5739)
;
_audit_update_record
;
2022-03-28 deposited with the CCDC.	2022-05-23 downloaded from the CCDC.
;
_cell_angle_alpha                90
_cell_angle_beta                 99.657(4)
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   10.4312(4)
_cell_length_b                   9.1608(3)
_cell_length_c                   27.6888(11)
_cell_measurement_reflns_used    5701
_cell_measurement_temperature    150
_cell_measurement_theta_max      29.8550
_cell_measurement_theta_min      2.0240
_cell_volume                     2608.40(17)
_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      150
_diffrn_detector                 'CCD plate'
_diffrn_measured_fraction_theta_full 0.998
_diffrn_measured_fraction_theta_max 0.998
_diffrn_measurement_details
;
List of Runs (angles in degrees, time in seconds):

  # Type    Start    End  Width  t~exp~   \w     \q     \k     \f   Frames
  1  \f    -41.73 150.27   1.00    2.00   6.61  -9.84 -31.50    --   192
  2  \w    -65.46  -0.46   1.00    2.00    --  -19.34  94.56 145.16   65
  3  \w   -100.81  15.19   1.00    2.00    --   -9.84 -59.25 -51.92  116
  4  \w    -60.89   0.11   1.00    2.00    --  -14.77  94.56 -34.84   61
  5  \w    259.19 282.19   1.00    2.00    --   -9.84 -59.25-123.92   23
;
_diffrn_measurement_device       'abstract diffractometer'
_diffrn_measurement_device_type
'Saxi-CrysAlisPro-abstract goniometer imported SAXI images'
_diffrn_measurement_method       '\w and \f scans'
_diffrn_orient_matrix_type
'CrysAlisPro convention (1999,Acta A55,543-557)'
_diffrn_orient_matrix_UB_11      0.0243695000
_diffrn_orient_matrix_UB_12      0.0173167000
_diffrn_orient_matrix_UB_13      0.0248212000
_diffrn_orient_matrix_UB_21      -0.0641717000
_diffrn_orient_matrix_UB_22      0.0141264000
_diffrn_orient_matrix_UB_23      0.0040863000
_diffrn_orient_matrix_UB_31      -0.0064556000
_diffrn_orient_matrix_UB_32      -0.0741240000
_diffrn_orient_matrix_UB_33      0.0065672000
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           'Mo K\a'
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0736
_diffrn_reflns_av_unetI/netI     0.0464
_diffrn_reflns_Laue_measured_fraction_full 0.998
_diffrn_reflns_Laue_measured_fraction_max 0.998
_diffrn_reflns_limit_h_max       12
_diffrn_reflns_limit_h_min       -12
_diffrn_reflns_limit_k_max       10
_diffrn_reflns_limit_k_min       -10
_diffrn_reflns_limit_l_max       32
_diffrn_reflns_limit_l_min       -32
_diffrn_reflns_number            31723
_diffrn_reflns_point_group_measured_fraction_full 0.998
_diffrn_reflns_point_group_measured_fraction_max 0.998
_diffrn_reflns_theta_full        24.997
_diffrn_reflns_theta_max         24.997
_diffrn_reflns_theta_min         2.230
_diffrn_source                   'fine-focus sealed X-ray tube'
_diffrn_source_type              'Enhance (Mo) X-ray Source'
_exptl_absorpt_coefficient_mu    1.559
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.82485
_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            colourless
_exptl_crystal_colour_primary    colourless
_exptl_crystal_density_diffrn    1.476
_exptl_crystal_description       block
_exptl_crystal_F_000             1192
_exptl_crystal_size_max          0.26
_exptl_crystal_size_mid          0.136
_exptl_crystal_size_min          0.056
_refine_diff_density_max         0.294
_refine_diff_density_min         -0.499
_refine_diff_density_rms         0.063
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.038
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     337
_refine_ls_number_reflns         4581
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.038
_refine_ls_R_factor_all          0.0488
_refine_ls_R_factor_gt           0.0355
_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^)+(0.0302P)^2^+1.7107P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0774
_refine_ls_wR_factor_ref         0.0835
_reflns_Friedel_coverage         0.000
_reflns_number_gt                3776
_reflns_number_total             4581
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            d2cc02315f2.cif
_cod_data_source_block           cmrv_ih_503_i_autored
_cod_database_code               7130139
_shelx_shelxl_version_number     2018/3
_shelx_estimated_absorpt_t_max   0.918
_shelx_estimated_absorpt_t_min   0.687
_reflns_odcompleteness_completeness 76.75
_reflns_odcompleteness_iscentric 1
_reflns_odcompleteness_theta     36.74
_olex2_refinement_description
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups, All C(H,H) groups
 At 1.5 times of:
  All C(H,H,H) groups
2.a Ternary CH refined with riding coordinates:
 C008(H008), C009(H009)
2.b Secondary CH2 refined with riding coordinates:
 C00Q(H00D,H00E)
2.c Aromatic/amide H refined with riding coordinates:
 C00H(H00H), C00J(H00J), C00L(H00L), C00N(H00N), C00O(H00O), C00P(H00P),
 C00R(H00R), C00S(H00S), C00T(H00T), C00V(H00V), C00X(H00X), C00Y(H00Y),
 C00Z(H00Z), C010(H010), C011(H011)
2.d Idealised Me refined as rotating group:
 C00F(H00A,H00B,H00C), C00U(H00F,H00G,H00I), C00W(H00K,H00M,H00Q)
;
_shelx_res_checksum              65229
_shelx_hkl_checksum              11845
_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 1.262
_oxdiff_exptl_absorpt_empirical_full_min 0.740