Radical cascade cyclization of chalcone skeleton enynes with sulfonylhydrazides: access to <i>meta</i>-sulfonyl-functionalized pyridines.
Ni, Hairui; Zhao, Xinyuan; Yu, Tongyan; Shen, Wei; You, Siliang; Deng, Chao; Organic & biomolecular chemistry 23 (2025) 6570–6575; doi:10.1039/d5ob00792e

data_7160588
_publ_section_title
;
 Radical cascade cyclization of chalcone skeleton enynes with
 sulfonylhydrazides: access to <i>meta</i>-sulfonyl-functionalized
 pyridines.
;
_journal_issue                   27
_journal_name_full               'Organic &amp; biomolecular chemistry'
_journal_page_first              6570
_journal_page_last               6575
_journal_paper_doi               10.1039/d5ob00792e
_journal_volume                  23
_journal_year                    2025
_chemical_formula_moiety         'C30 H21 N O3 S'
_chemical_formula_sum            'C30 H21 N O3 S'
_chemical_formula_weight         475.54
_space_group_crystal_system      orthorhombic
_space_group_IT_number           33
_space_group_name_Hall           'P 2c -2n'
_space_group_name_H-M_alt        'P n a 21'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     dual
_audit_creation_date             2024-07-09
_audit_creation_method
;
Olex2 1.2
(compiled 2018.05.29 svn.r3508 for OlexSys, GUI svn.r5506)
;
_audit_update_record
;
2024-12-04 deposited with the CCDC.	2025-06-10 downloaded from the CCDC.
;
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   11.3681(12)
_cell_length_b                   12.4428(12)
_cell_length_c                   17.3170(19)
_cell_measurement_reflns_used    9869
_cell_measurement_temperature    291(2)
_cell_measurement_theta_max      68.005
_cell_measurement_theta_min      4.375
_cell_volume                     2449.5(4)
_computing_cell_refinement       'SAINT V8.40B (?, 2016)'
_computing_data_reduction        'SAINT V8.40B (?, 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 (Sheldrick, 2015)'
_diffrn_ambient_temperature      291.0
_diffrn_measured_fraction_theta_full 0.998
_diffrn_measured_fraction_theta_max 0.998
_diffrn_measurement_device_type  'CCD area detector'
_diffrn_measurement_method       'phi and omega scans'
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54178
_diffrn_reflns_av_R_equivalents  0.0413
_diffrn_reflns_av_unetI/netI     0.0368
_diffrn_reflns_Laue_measured_fraction_full 0.998
_diffrn_reflns_Laue_measured_fraction_max 0.998
_diffrn_reflns_limit_h_max       13
_diffrn_reflns_limit_h_min       -13
_diffrn_reflns_limit_k_max       14
_diffrn_reflns_limit_k_min       -14
_diffrn_reflns_limit_l_max       17
_diffrn_reflns_limit_l_min       -20
_diffrn_reflns_number            22799
_diffrn_reflns_point_group_measured_fraction_full 0.955
_diffrn_reflns_point_group_measured_fraction_max 0.954
_diffrn_reflns_theta_full        67.679
_diffrn_reflns_theta_max         68.105
_diffrn_reflns_theta_min         4.375
_exptl_absorpt_coefficient_mu    1.431
_exptl_absorpt_correction_T_max  0.7531
_exptl_absorpt_correction_T_min  0.4849
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
SADABS-2016/2 (Bruker,2016/2) was used for absorption correction.
wR2(int) was 0.1457 before and 0.0583 after correction.
The Ratio of minimum to maximum transmission is 0.6439.
The \l/2 correction factor is Not present.
;
_exptl_crystal_colour            colourless
_exptl_crystal_colour_primary    colourless
_exptl_crystal_density_diffrn    1.289
_exptl_crystal_description       block
_exptl_crystal_F_000             992
_exptl_crystal_size_max          0.23
_exptl_crystal_size_mid          0.22
_exptl_crystal_size_min          0.21
_refine_diff_density_max         0.189
_refine_diff_density_min         -0.430
_refine_diff_density_rms         0.065
_refine_ls_abs_structure_details
;
 Flack x determined using 1813 quotients [(I+)-(I-)]/[(I+)+(I-)]
 (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259).
;
_refine_ls_abs_structure_Flack   0.280(5)
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.058
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     316
_refine_ls_number_reflns         4262
_refine_ls_number_restraints     1
_refine_ls_restrained_S_all      1.058
_refine_ls_R_factor_all          0.0392
_refine_ls_R_factor_gt           0.0377
_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^)+(0.0607P)^2^+0.2690P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0959
_refine_ls_wR_factor_ref         0.0966
_reflns_Friedel_coverage         0.845
_reflns_Friedel_fraction_full    0.909
_reflns_Friedel_fraction_max     0.906
_reflns_number_gt                4147
_reflns_number_total             4262
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            d5ob00792e2.cif
_cod_data_source_block           1
_cod_depositor_comments          'Adding full bibliography for 7160588.cif.'
_cod_database_code               7160588
_shelx_shelxl_version_number     2016/6
_shelx_estimated_absorpt_t_max   0.753
_shelx_estimated_absorpt_t_min   0.734
_olex2_refinement_description
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups
2.a Aromatic/amide H refined with riding coordinates:
 C7(H7), C23(H23), C26(H26), C30(H30), C11(H11), C19(H19), C29(H29), C15(H15),
 C22(H22), C1(H1), C28(H28), C5(H5), C20(H20), C21(H21), C13(H13), C14(H14),
 C12(H12), C2(H2), C27(H27), C4(H4), C3(H3)
;
_shelx_res_checksum              90397
_olex2_submission_special_instructions 'No special instructions were received'