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_7130140
_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         'C34 H27 Br O5 S Se'
_chemical_formula_sum            'C34 H27 Br O5 S Se'
_chemical_formula_weight         706.48
_space_group_crystal_system      triclinic
_space_group_IT_number           2
_space_group_name_Hall           '-P 1'
_space_group_name_H-M_alt        'P -1'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     dual
_audit_creation_date             2021-10-22
_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                115.650(4)
_cell_angle_beta                 98.002(3)
_cell_angle_gamma                97.217(3)
_cell_formula_units_Z            4
_cell_length_a                   7.7248(2)
_cell_length_b                   20.4230(8)
_cell_length_c                   21.7248(10)
_cell_measurement_reflns_used    6985
_cell_measurement_temperature    150.00(10)
_cell_measurement_theta_max      22.2340
_cell_measurement_theta_min      1.8710
_cell_volume                     2992.5(2)
_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      150.00(10)
_diffrn_detector                 'CCD plate'
_diffrn_measured_fraction_theta_full 1.000
_diffrn_measured_fraction_theta_max 1.000
_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   -349.73  10.27   1.00    5.00   6.61  -9.84 -31.50    --   360
  2  \w    -60.89   0.11   1.00    5.00    --  -14.77  94.56 -34.84   61
  3  \w    -65.46  -0.46   1.00    5.00    --  -19.34  94.56 145.16   65
  4  \w   -100.81  15.19   1.00    5.00    --   -9.84 -59.25 164.08  116
  5  \f    -10.27 349.73   1.00    5.00  81.02  -9.84  31.50    --   360
  6  \w    -65.46  -0.46   1.00    5.00    --  -19.34  94.56  73.16   65
;
_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      -0.0216290000
_diffrn_orient_matrix_UB_12      0.0322558000
_diffrn_orient_matrix_UB_13      -0.0011389000
_diffrn_orient_matrix_UB_21      -0.0329985000
_diffrn_orient_matrix_UB_22      -0.0206484000
_diffrn_orient_matrix_UB_23      -0.0366715000
_diffrn_orient_matrix_UB_31      -0.0862023000
_diffrn_orient_matrix_UB_32      -0.0092099000
_diffrn_orient_matrix_UB_33      0.0054921000
_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  0.1078
_diffrn_reflns_av_unetI/netI     0.0664
_diffrn_reflns_Laue_measured_fraction_full 1.000
_diffrn_reflns_Laue_measured_fraction_max 1.000
_diffrn_reflns_limit_h_max       9
_diffrn_reflns_limit_h_min       -9
_diffrn_reflns_limit_k_max       24
_diffrn_reflns_limit_k_min       -24
_diffrn_reflns_limit_l_max       25
_diffrn_reflns_limit_l_min       -25
_diffrn_reflns_number            83995
_diffrn_reflns_point_group_measured_fraction_full 1.000
_diffrn_reflns_point_group_measured_fraction_max 1.000
_diffrn_reflns_theta_full        24.998
_diffrn_reflns_theta_max         24.998
_diffrn_reflns_theta_min         1.876
_diffrn_source                   'fine-focus sealed X-ray tube'
_diffrn_source_type              'Enhance (Mo) X-ray Source'
_exptl_absorpt_coefficient_mu    2.702
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.75738
_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    1.568
_exptl_crystal_description       block
_exptl_crystal_F_000             1424
_exptl_crystal_size_max          0.19
_exptl_crystal_size_mid          0.123
_exptl_crystal_size_min          0.062
_refine_diff_density_max         0.466
_refine_diff_density_min         -0.665
_refine_diff_density_rms         0.087
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.025
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     759
_refine_ls_number_reflns         10535
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.025
_refine_ls_R_factor_all          0.0685
_refine_ls_R_factor_gt           0.0422
_refine_ls_shift/su_max          0.002
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'w=1/[\s^2^(Fo^2^)+(0.0261P)^2^+1.8156P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0815
_refine_ls_wR_factor_ref         0.0921
_reflns_Friedel_coverage         0.000
_reflns_number_gt                7734
_reflns_number_total             10535
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            d2cc02315f2.cif
_cod_data_source_block           cmrv_ih_8_2_10_autored
_cod_depositor_comments
;

2024-12-16
Z value and formula fixed to values more according to usual
chemical conventions.                 miguel
;
_cod_original_formula_sum            'C68 H54 Br2 O10 S2 Se2'
_cod_original_formula_weight         1412.97
_cod_original_formula_moiety         '2(C34 H27 Br O5 S Se)'
_cod_original_formula_units_Z            2
_cod_database_code               7130140
_shelx_shelxl_version_number     2018/3
_chemical_oxdiff_formula         C25H52N2O2S1
_reflns_odcompleteness_completeness 76.81
_reflns_odcompleteness_iscentric 1
_reflns_odcompleteness_theta     36.76
_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:
 C7(H7), C12(H12), C41(H41), C42(H42)
2.b Secondary CH2 refined with riding coordinates:
 C15(H15A,H15B), C48(H48A,H48B)
2.c Aromatic/amide H refined with riding coordinates:
 C2(H2), C3(H3), C4(H4), C5(H5), C6(H6), C9(H9), C10(H10), C17(H17), C18(H18),
 C20(H20), C21(H21), C23(H23), C24(H24), C25(H25), C26(H26), C27(H27), C29(H29),
  C30(H30), C32(H32), C33(H33), C36(H36), C37(H37), C38(H38), C39(H39),
 C40(H40), C44(H44), C45(H45), C51(H51), C52(H52), C53(H53), C54(H54), C55(H55),
  C57(H57), C58(H58), C60(H60), C61(H61), C63(H63), C64(H64), C66(H66), C67(H67)
2.d Idealised Me refined as rotating group:
 C34(H34A,H34B,H34C), C68(H68A,H68B,H68C)
;
_shelx_res_checksum              43581
_shelx_hkl_checksum              24764
_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 1.266
_oxdiff_exptl_absorpt_empirical_full_min 0.790