Lewis acid-catalyzed intramolecular cyclization of 7-alkynylcycloheptatrienes with carbonyls: access to 3,4-disubstituted 2,5-dihydropyrroles
Huang, Xiang; Yang, Jin-Ming; Chemical Communications 61 (2025) 9686–9689; doi:10.1039/D5CC01837D

data_7134588
_publ_section_title
;
 Lewis acid-catalyzed intramolecular cyclization of
 7-alkynylcycloheptatrienes with carbonyls: access to 3,4-disubstituted
 2,5-dihydropyrroles
;
_journal_issue                   53
_journal_name_full               'Chemical Communications'
_journal_page_first              9686
_journal_page_last               9689
_journal_paper_doi               10.1039/D5CC01837D
_journal_volume                  61
_journal_year                    2025
_chemical_formula_moiety         'C25 H21 N O2 S'
_chemical_formula_sum            'C25 H21 N O2 S'
_chemical_formula_weight         399.49
_space_group_crystal_system      orthorhombic
_space_group_IT_number           19
_space_group_name_Hall           'P 2ac 2ab'
_space_group_name_H-M_alt        'P 21 21 21'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_audit_creation_date             2024-10-23
_audit_creation_method
;
Olex2 1.5-beta
(compiled 2022.04.07 svn.rca3783a0 for OlexSys, GUI svn.r6439)
;
_audit_update_record
;
2025-01-03 deposited with the CCDC.	2025-05-23 downloaded from the CCDC.
;
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   5.18890(10)
_cell_length_b                   17.9266(5)
_cell_length_c                   21.5874(6)
_cell_measurement_reflns_used    3733
_cell_measurement_temperature    170.00(10)
_cell_measurement_theta_max      73.4840
_cell_measurement_theta_min      4.0530
_cell_volume                     2008.05(9)
_computing_cell_refinement       'CrysAlisPro 1.171.38.43f (Rigaku OD, 2015)'
_computing_data_collection       'CrysAlisPro 1.171.38.43f (Rigaku OD, 2015)'
_computing_data_reduction        'CrysAlisPro 1.171.38.43f (Rigaku OD, 2015)'
_computing_molecular_graphics    'Olex2 1.5-beta (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 1.5-beta (Dolomanov et al., 2009)'
_computing_structure_refinement  'SHELXH-1997  (Sheldrick, 2008)'
_computing_structure_solution    'SHELXS  (Sheldrick, 2008)'
_diffrn_ambient_environment      N~2~
_diffrn_ambient_temperature      170.00(10)
_diffrn_detector                 'CCD plate'
_diffrn_detector_area_resol_mean 5.2684
_diffrn_detector_type            AtlasS2
_diffrn_measured_fraction_theta_full 1.000
_diffrn_measured_fraction_theta_max 0.985
_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    -66.00  33.00   1.00    2.00    --  -41.11  38.00-120.00   99
  2  \w    -96.00  -8.00   1.00    2.00    --  -41.11 125.00  60.00   88
  3  \w    -81.00  15.00   1.00    2.00    --  -41.11  19.00-180.00   96
  4  \w     54.00 130.00   1.00    4.00    --  107.58 -30.00  90.00   76
  5  \w     28.00 109.00   1.00    4.00    --  107.58 -94.00 150.00   81
  6  \w     52.00 106.00   1.00    4.00    --  107.58 -94.00  90.00   54
  7  \w     53.00 105.00   1.00    4.00    --  107.58 -94.00  30.00   52
  8  \w     28.00 135.00   1.00    4.00    --  107.58 -15.00-180.00  107
;
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'SuperNova, Dual, Cu at zero, AtlasS2'
_diffrn_measurement_method       '\w scans'
_diffrn_orient_matrix_type
'CrysAlisPro convention (1999,Acta A55,543-557)'
_diffrn_orient_matrix_UB_11      -0.0138356000
_diffrn_orient_matrix_UB_12      -0.0716158000
_diffrn_orient_matrix_UB_13      -0.0393086000
_diffrn_orient_matrix_UB_21      -0.0104296000
_diffrn_orient_matrix_UB_22      0.0474958000
_diffrn_orient_matrix_UB_23      -0.0594367000
_diffrn_orient_matrix_UB_31      0.2963123000
_diffrn_orient_matrix_UB_32      -0.0016825000
_diffrn_orient_matrix_UB_33      -0.0040071000
_diffrn_radiation_monochromator  mirror
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           'Cu K\a'
_diffrn_radiation_wavelength     1.54184
_diffrn_reflns_av_R_equivalents  0.0371
_diffrn_reflns_av_unetI/netI     0.0541
_diffrn_reflns_Laue_measured_fraction_full 1.000
_diffrn_reflns_Laue_measured_fraction_max 0.985
_diffrn_reflns_limit_h_max       6
_diffrn_reflns_limit_h_min       -2
_diffrn_reflns_limit_k_max       21
_diffrn_reflns_limit_k_min       -22
_diffrn_reflns_limit_l_max       26
_diffrn_reflns_limit_l_min       -22
_diffrn_reflns_number            7771
_diffrn_reflns_point_group_measured_fraction_full 1.000
_diffrn_reflns_point_group_measured_fraction_max 0.974
_diffrn_reflns_theta_full        67.684
_diffrn_reflns_theta_max         73.586
_diffrn_reflns_theta_min         3.204
_diffrn_source                   'micro-focus sealed X-ray tube'
_diffrn_source_type              'SuperNova (Cu) X-ray Source'
_exptl_absorpt_coefficient_mu    1.596
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.71354
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
CrysAlisPro 1.171.38.43f (Rigaku Oxford Diffraction, 2015)
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_crystal_colour            'clear light colourless'
_exptl_crystal_density_diffrn    1.321
_exptl_crystal_description       block
_exptl_crystal_F_000             840
_exptl_crystal_size_max          0.16
_exptl_crystal_size_mid          0.12
_exptl_crystal_size_min          0.11
_refine_diff_density_max         0.239
_refine_diff_density_min         -0.312
_refine_diff_density_rms         0.050
_refine_ls_abs_structure_details
;
 Flack x determined using 1321 quotients [(I+)-(I-)]/[(I+)+(I-)]
 (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259).
;
_refine_ls_abs_structure_Flack   0.003(16)
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.040
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     263
_refine_ls_number_reflns         3959
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.040
_refine_ls_R_factor_all          0.0508
_refine_ls_R_factor_gt           0.0457
_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^)+(0.0621P)^2^] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1135
_refine_ls_wR_factor_ref         0.1194
_reflns_Friedel_coverage         0.688
_reflns_Friedel_fraction_full    1.000
_reflns_Friedel_fraction_max     0.957
_reflns_number_gt                3600
_reflns_number_total             3959
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            d5cc01837d2.cif
_cod_data_source_block           7_72
_cod_depositor_comments
'Adding full bibliography for 7134588--7134589.cif.'
_cod_database_code               7134588
_shelx_shelxl_version_number     2018/3
_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:
 C10(H10A,H10B), C18(H18A,H18B)
2.b Aromatic/amide H refined with riding coordinates:
 C2(H2), C3(H3), C4(H4), C5(H5), C6(H6), C13(H13), C14(H14), C15(H15),
 C16(H16), C17(H17), C20(H20), C21(H21), C22(H22), C24(H24)
2.c Idealised Me refined as rotating group:
 C25(H25A,H25B,H25C)
;
_shelx_res_checksum              76433
_shelx_hkl_checksum              34521
_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
- Detector area scaling
;
_oxdiff_exptl_absorpt_empirical_full_max 1.486
_oxdiff_exptl_absorpt_empirical_full_min 0.524