Tandem [2+4] annulation/aromatization reaction of yne-enones with <i>o</i>-sulfonamidobenzaldehydes.
Cui, Zhiyang; Sun, Honghao; Jin, Jingrong; Tang, Yi; Wang, Bo; Zhou, Leijie; Zheng, Bing; Zheng, Li; Guo, Hongchao; Chemical communications (Cambridge, England) 62 (2026) 4774–4777; doi:10.1039/d5cc06758h

data_7135336
_publ_section_title
;
 Tandem [2+4] annulation/aromatization reaction of yne-enones with
 <i>o</i>-sulfonamidobenzaldehydes.
;
_journal_issue                   16
_journal_name_full               'Chemical communications (Cambridge, England)'
_journal_page_first              4774
_journal_page_last               4777
_journal_paper_doi               10.1039/d5cc06758h
_journal_volume                  62
_journal_year                    2026
_chemical_formula_moiety         'C25 H18 Br N O'
_chemical_formula_sum            'C25 H18 Br N O'
_chemical_formula_weight         428.31
_chemical_name_systematic        1
_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             2025-04-27
_audit_creation_method
;
Olex2 1.2
(compiled 2018.05.29 svn.r3508 for OlexSys, GUI svn.r5506)
;
_audit_update_record
;
2025-08-16 deposited with the CCDC.	2026-02-05 downloaded from the CCDC.
;
_cell_angle_alpha                106.469(6)
_cell_angle_beta                 105.026(6)
_cell_angle_gamma                103.433(6)
_cell_formula_units_Z            2
_cell_length_a                   9.9195(7)
_cell_length_b                   10.2361(6)
_cell_length_c                   10.9376(8)
_cell_measurement_reflns_used    3235
_cell_measurement_temperature    293
_cell_measurement_theta_max      26.2640
_cell_measurement_theta_min      3.9480
_cell_volume                     970.91(13)
_computing_cell_refinement       'CrysAlisPro 1.171.42.90a (Rigaku OD, 2023)'
_computing_data_collection       'CrysAlisPro 1.171.42.90a (Rigaku OD, 2023)'
_computing_data_reduction        'CrysAlisPro 1.171.42.90a (Rigaku OD, 2023)'
_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      293
_diffrn_detector                 'CCD plate'
_diffrn_detector_area_resol_mean 8.0353
_diffrn_detector_type            EosS2
_diffrn_measured_fraction_theta_full 0.998
_diffrn_measured_fraction_theta_max 0.837
_diffrn_measurement_details
;
List of Runs (angles in degrees, time in seconds):

  # Type    Start    End  Width  t~exp~   \w     \q     \k     \f   Frames
  1  \w     -2.00  86.00   1.00    4.80    --   16.85  37.00  90.00   88
  2  \w    -10.00  42.00   1.00    4.80    --   16.85  77.00-180.00   52
  3  \w    -10.00  42.00   1.00    4.80    --   16.85  77.00 -60.00   52
  4  \w      0.00  84.00   1.00    4.80    --   16.85  57.00  90.00   84
  5  \w    -50.00  34.00   1.00    4.80    --   16.85 -57.00-150.00   84
  6  \w    -55.00  42.00   1.00    4.80    --   16.85 -19.00 -90.00   97
;
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'SuperNova, Single source at offset/far, EosS2'
_diffrn_measurement_method       '\w scans'
_diffrn_orient_matrix_type
'CrysAlisPro convention (1999,Acta A55,543-557)'
_diffrn_orient_matrix_UB_11      -0.0288030000
_diffrn_orient_matrix_UB_12      0.0384438000
_diffrn_orient_matrix_UB_13      0.0458986000
_diffrn_orient_matrix_UB_21      0.0058500000
_diffrn_orient_matrix_UB_22      0.0541102000
_diffrn_orient_matrix_UB_23      -0.0288250000
_diffrn_orient_matrix_UB_31      -0.0727216000
_diffrn_orient_matrix_UB_32      -0.0381358000
_diffrn_orient_matrix_UB_33      -0.0476229000
_diffrn_radiation_monochromator  mirror
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0309
_diffrn_reflns_av_unetI/netI     0.0547
_diffrn_reflns_Laue_measured_fraction_full 0.998
_diffrn_reflns_Laue_measured_fraction_max 0.837
_diffrn_reflns_limit_h_max       13
_diffrn_reflns_limit_h_min       -13
_diffrn_reflns_limit_k_max       13
_diffrn_reflns_limit_k_min       -14
_diffrn_reflns_limit_l_max       15
_diffrn_reflns_limit_l_min       -13
_diffrn_reflns_number            10043
_diffrn_reflns_point_group_measured_fraction_full 0.998
_diffrn_reflns_point_group_measured_fraction_max 0.837
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         29.428
_diffrn_reflns_theta_min         3.299
_diffrn_source                   'micro-focus sealed X-ray tube'
_diffrn_source_type              'SuperNova (Mo) X-ray Source'
_exptl_absorpt_coefficient_mu    2.132
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.49328
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
CrysAlisPro 1.171.42.90a (Rigaku Oxford Diffraction, 2023)
Empirical absorption correction using spherical harmonics,
implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_crystal_colour            'clear light colourless'
_exptl_crystal_colour_lustre     clear
_exptl_crystal_colour_modifier   light
_exptl_crystal_colour_primary    colourless
_exptl_crystal_density_diffrn    1.465
_exptl_crystal_description       block
_exptl_crystal_F_000             436
_exptl_crystal_size_max          0.06
_exptl_crystal_size_mid          0.05
_exptl_crystal_size_min          0.05
_refine_diff_density_max         0.455
_refine_diff_density_min         -0.775
_refine_diff_density_rms         0.074
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.007
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     254
_refine_ls_number_reflns         4509
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.007
_refine_ls_R_factor_all          0.0930
_refine_ls_R_factor_gt           0.0507
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'w=1/[\s^2^(Fo^2^)+(0.0576P)^2^+0.2834P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1099
_refine_ls_wR_factor_ref         0.1318
_reflns_Friedel_coverage         0.000
_reflns_number_gt                2886
_reflns_number_total             4509
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            d5cc06758h2.cif
_cod_data_source_block           0423_auto
_cod_depositor_comments          'Adding full bibliography for 7135336.cif.'
_cod_original_cell_volume        970.91(12)
_cod_database_code               7135336
_shelx_shelxl_version_number     2018/3
_shelx_estimated_absorpt_t_max   0.901
_shelx_estimated_absorpt_t_min   0.883
_reflns_odcompleteness_completeness 99.80
_reflns_odcompleteness_iscentric 1
_reflns_odcompleteness_theta     26.32
_olex2_refinement_description
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups
 At 1.5 times of:
  All C(H,H,H) groups
2.a Aromatic/amide H refined with riding coordinates:
 C7(H7), C18(H18), C13(H13), C15(H15), C16(H16), C14(H14), C21(H21), C3(H3),
 C25(H25), C2(H2), C6(H6), C23(H23), C22(H22), C5(H5), C24(H24)
2.b Idealised Me refined as rotating group:
 C10(H10A,H10B,H10C)
;
_shelx_res_checksum              42914
_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 1.438
_oxdiff_exptl_absorpt_empirical_full_min 0.667