Metal- and base-free tandem sulfonylation/cyclization of 1,5-dienes with aryldiazonium salts via the insertion of sulfur dioxide
Wang, Xiaohong; You, Fengzhi; Xiong, Baojian; Chen, Lei; Zhang, Xuemei; Lian, Zhong; RSC Advances 12 (2022) 16745–16750; doi:10.1039/D2RA03034A

data_7245036
_publ_section_title
;
 Metal- and base-free tandem sulfonylation/cyclization of 1,5-dienes with
 aryldiazonium salts via the insertion of sulfur dioxide
;
_journal_issue                   26
_journal_name_full               'RSC Advances'
_journal_page_first              16745
_journal_page_last               16750
_journal_paper_doi               10.1039/D2RA03034A
_journal_volume                  12
_journal_year                    2022
_chemical_formula_moiety         'C25 H23 N O4 S'
_chemical_formula_sum            'C25 H23 N O4 S'
_chemical_formula_weight         433.50
_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     direct
_audit_creation_date             2021-11-25
_audit_creation_method
;
Olex2 1.2
(compiled 2018.05.29 svn.r3508 for OlexSys, GUI svn.r5506)
;
_audit_update_record
;
2021-12-27 deposited with the CCDC.	2022-05-31 downloaded from the CCDC.
;
_cell_angle_alpha                90
_cell_angle_beta                 95.487(3)
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   10.6128(3)
_cell_length_b                   9.0112(3)
_cell_length_c                   22.7652(7)
_cell_measurement_reflns_used    2570
_cell_measurement_temperature    293(2)
_cell_measurement_theta_max      28.6420
_cell_measurement_theta_min      3.3630
_cell_volume                     2167.15(12)
_computing_cell_refinement
;
CrysAlisPro, Agilent Technologies,
Version 1.171.37.34 (release 22-05-2014 CrysAlis171 .NET)
(compiled May 22 2014,16:03:01)
;
_computing_data_collection
;
CrysAlisPro, Agilent Technologies,
Version 1.171.37.34 (release 22-05-2014 CrysAlis171 .NET)
(compiled May 22 2014,16:03:01)
;
_computing_data_reduction
;
CrysAlisPro, Agilent Technologies,
Version 1.171.37.34 (release 22-05-2014 CrysAlis171 .NET)
(compiled May 22 2014,16:03:01)
;
_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    'ShelXS (Sheldrick, 2008)'
_diffrn_ambient_temperature      293.15
_diffrn_detector                 'CCD plate'
_diffrn_detector_area_resol_mean 16.0874
_diffrn_detector_type            Eos
_diffrn_measured_fraction_theta_full 0.999
_diffrn_measured_fraction_theta_max 0.999
_diffrn_measurement_details
;
  1 omega  -34.00   48.80   0.9000   10.0000
omega____ theta____ kappa____ phi______ frames
    -      -15.4773   38.0000   60.0000 92

  2 omega  -24.00   12.00   0.9000   10.0000
omega____ theta____ kappa____ phi______ frames
    -      -15.4773  -99.0000   30.0000 40

  3 omega  -75.00    1.50   0.9000   10.0000
omega____ theta____ kappa____ phi______ frames
    -      -15.4773  -57.0000  -90.0000 85

  4 omega  -12.00   24.00   0.9000   10.0000
omega____ theta____ kappa____ phi______ frames
    -      -15.4773  -99.0000 -180.0000 40
;
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'Xcalibur, Eos'
_diffrn_measurement_method       '\w scans'
_diffrn_orient_matrix_UB_11      0.0211895000
_diffrn_orient_matrix_UB_12      -0.0637056000
_diffrn_orient_matrix_UB_13      0.0163780000
_diffrn_orient_matrix_UB_21      0.0096755000
_diffrn_orient_matrix_UB_22      0.0438577000
_diffrn_orient_matrix_UB_23      0.0259118000
_diffrn_orient_matrix_UB_31      -0.0629703000
_diffrn_orient_matrix_UB_32      -0.0147146000
_diffrn_orient_matrix_UB_33      0.0063003000
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0214
_diffrn_reflns_av_unetI/netI     0.0401
_diffrn_reflns_Laue_measured_fraction_full 0.999
_diffrn_reflns_Laue_measured_fraction_max 0.999
_diffrn_reflns_limit_h_max       13
_diffrn_reflns_limit_h_min       -10
_diffrn_reflns_limit_k_max       11
_diffrn_reflns_limit_k_min       -10
_diffrn_reflns_limit_l_max       28
_diffrn_reflns_limit_l_min       -27
_diffrn_reflns_number            10013
_diffrn_reflns_point_group_measured_fraction_full 0.999
_diffrn_reflns_point_group_measured_fraction_max 0.999
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         26.371
_diffrn_reflns_theta_min         2.971
_diffrn_source                   'Enhance (Mo) X-ray Source'
_exptl_absorpt_coefficient_mu    0.182
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.99472
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
CrysAlisPro, Agilent Technologies,
Version 1.171.37.34 (release 22-05-2014 CrysAlis171 .NET)
(compiled May 22 2014,16:03:01)
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_crystal_density_diffrn    1.329
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       block
_exptl_crystal_F_000             912
_exptl_crystal_size_max          0.35
_exptl_crystal_size_mid          0.3
_exptl_crystal_size_min          0.25
_refine_diff_density_max         0.218
_refine_diff_density_min         -0.348
_refine_diff_density_rms         0.046
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.036
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     283
_refine_ls_number_reflns         4428
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.036
_refine_ls_R_factor_all          0.0766
_refine_ls_R_factor_gt           0.0488
_refine_ls_shift/su_max          0.003
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'w=1/[\s^2^(Fo^2^)+(0.0556P)^2^+0.3535P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1115
_refine_ls_wR_factor_ref         0.1277
_reflns_Friedel_coverage         0.000
_reflns_number_gt                3110
_reflns_number_total             4428
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            d2ra03034a2.cif
_cod_data_source_block           211124_s1_wxh
_cod_original_cell_volume        2167.16(13)
_cod_database_code               7245036
_shelx_shelxl_version_number     2018/3
_chemical_oxdiff_formula         c12h12n2o3
_shelx_estimated_absorpt_t_max   0.956
_shelx_estimated_absorpt_t_min   0.939
_reflns_odcompleteness_completeness 99.75
_reflns_odcompleteness_iscentric 1
_reflns_odcompleteness_theta     26.32
_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 Secondary CH2 refined with riding coordinates:
 C8(H8A,H8B)
2.b Aromatic/amide H refined with riding coordinates:
 C3(H3), C10(H10), C11(H11), C13(H13), C14(H14), C17(H17), C18(H18), C20(H20),
 C21(H21), C22(H22), C23(H23), C25(H25)
2.c Idealised Me refined as rotating group:
 C5(H5A,H5B,H5C), C7(H7A,H7B,H7C), C15(H15A,H15B,H15C)
;
_shelx_res_checksum              64475
_olex2_submission_special_instructions 'No special instructions were received'