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_7130138
_publ_section_title
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 A Metal-free Four-component Sulfonylation, Giese Cyclization,
 Selenylation Cascade via Insertion of Sulfur Dioxide
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_journal_name_full               'Chemical Communications'
_journal_paper_doi               10.1039/D2CC02315F
_journal_year                    2022
_chemical_formula_moiety         'C33 H34 O5 S Se'
_chemical_formula_sum            'C33 H34 O5 S Se'
_chemical_formula_weight         621.62
_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
_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                 105.641(6)
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   9.9080(18)
_cell_length_b                   20.656(4)
_cell_length_c                   14.699(2)
_cell_measurement_reflns_used    1321
_cell_measurement_temperature    150
_cell_measurement_theta_max      23.351
_cell_measurement_theta_min      2.438
_cell_volume                     2896.9(9)
_computing_cell_refinement       'SAINT V8.40A (?, 2016)'
_computing_data_reduction        'SAINT V8.40A (?, 2016)'
_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 2014/5 (Sheldrick, 2014)'
_diffrn_ambient_temperature      150
_diffrn_measured_fraction_theta_full 0.999
_diffrn_measured_fraction_theta_max 0.996
_diffrn_measurement_device_type  'Bruker D8 quest'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.1055
_diffrn_reflns_av_unetI/netI     0.1025
_diffrn_reflns_Laue_measured_fraction_full 0.999
_diffrn_reflns_Laue_measured_fraction_max 0.996
_diffrn_reflns_limit_h_max       13
_diffrn_reflns_limit_h_min       -13
_diffrn_reflns_limit_k_max       27
_diffrn_reflns_limit_k_min       -24
_diffrn_reflns_limit_l_max       19
_diffrn_reflns_limit_l_min       -17
_diffrn_reflns_number            34089
_diffrn_reflns_point_group_measured_fraction_full 0.999
_diffrn_reflns_point_group_measured_fraction_max 0.996
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         28.269
_diffrn_reflns_theta_min         2.229
_exptl_absorpt_coefficient_mu    1.409
_exptl_absorpt_correction_T_max  1.0000
_exptl_absorpt_correction_T_min  0.8366
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
SADABS-2016/2 (Bruker,2016/2) was used for absorption correction.
wR2(int) was 0.1091 before and 0.0688 after correction.
The Ratio of minimum to maximum transmission is 0.8366.
The \l/2 correction factor is 0.00150.
;
_exptl_crystal_colour            colourless
_exptl_crystal_colour_primary    colourless
_exptl_crystal_density_diffrn    1.425
_exptl_crystal_description       block
_exptl_crystal_F_000             1288
_exptl_crystal_size_max          0.45
_exptl_crystal_size_mid          0.105
_exptl_crystal_size_min          0.03
_refine_diff_density_max         1.315
_refine_diff_density_min         -0.658
_refine_diff_density_rms         0.095
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.014
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     363
_refine_ls_number_reflns         7164
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.014
_refine_ls_R_factor_all          0.1204
_refine_ls_R_factor_gt           0.0560
_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^)+(0.0552P)^2^+2.2791P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1193
_refine_ls_wR_factor_ref         0.1450
_reflns_Friedel_coverage         0.000
_reflns_number_gt                4203
_reflns_number_total             7164
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            d2cc02315f2.cif
_cod_data_source_block           cmrv_an_8_2_8
_cod_original_cell_volume        2897.0(8)
_cod_database_code               7130138
_shelx_shelxl_version_number     2018/3
_shelx_estimated_absorpt_t_max   0.959
_shelx_estimated_absorpt_t_min   0.570
_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:
 C20(H20), C21(H21)
2.b Secondary CH2 refined with riding coordinates:
 C2(H2A,H2B), C3(H3A,H3B), C4(H4A,H4B), C5(H5A,H5B), C7(H7A,H7B)
2.c Aromatic/amide H refined with riding coordinates:
 C10(H10), C11(H11), C14(H14), C15(H15), C16(H16), C18(H18), C19(H19),
 C22(H22), C23(H23), C26(H26), C27(H27), C28(H28), C29(H29), C30(H30), C31(H31),
  C32(H32)
2.d Idealised Me refined as rotating group:
 C1(H1A,H1B,H1C), C13(H13A,H13B,H13C)
;
_shelx_res_checksum              21197
_shelx_hkl_checksum              58892
_olex2_submission_special_instructions 'No special instructions were received'