Substrate-dependent regiodivergence in [3 + 2] annulation reactions of 2-(phenacylethylidene)cyclobutanones with thioureas.
Barranco, Stefano; Pagnanini, Alessio; Cuccu, Federico; Caboni, Pierluigi; Guillot, Régis; Aitken, David J.; Frongia, Angelo; Organic & biomolecular chemistry 22 (2024) 8048–8053; doi:10.1039/d4ob01103a

data_7160137
_publ_section_title
;
 Substrate-dependent regiodivergence in [3 + 2] annulation reactions of
 2-(phenacylethylidene)cyclobutanones with thioureas.
;
_journal_issue                   39
_journal_name_full               'Organic &amp; biomolecular chemistry'
_journal_page_first              8048
_journal_page_last               8053
_journal_paper_doi               10.1039/d4ob01103a
_journal_volume                  22
_journal_year                    2024
_chemical_formula_moiety         'C19 H18 N2 O2 S'
_chemical_formula_sum            'C19 H18 N2 O2 S'
_chemical_formula_weight         338.41
_space_group_crystal_system      monoclinic
_space_group_IT_number           14
_space_group_name_Hall           '-P 2ybc'
_space_group_name_H-M_alt        'P 1 21/c 1'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     difmap
_audit_creation_method           SHELXL-2019/3
_audit_update_record
;
2024-06-10 deposited with the CCDC.	2024-09-06 downloaded from the CCDC.
;
_cell_angle_alpha                90
_cell_angle_beta                 94.1680(10)
_cell_angle_gamma                90
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_cell_length_b                   29.2862(4)
_cell_length_c                   7.77910(10)
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_cell_measurement_temperature    100(1)
_cell_measurement_theta_max      64.97
_cell_measurement_theta_min      5.70
_cell_volume                     3261.44(8)
_computing_cell_refinement       'Bruker SAINT'
_computing_data_collection       'Bruker APEX4'
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_computing_structure_refinement  'SHELXL-2019/2 (Sheldrick, 2019)'
_computing_structure_solution    'SHELXS-97 (Sheldrick 2008)'
_diffrn_ambient_temperature      100(1)
_diffrn_measured_fraction_theta_full 0.977
_diffrn_measured_fraction_theta_max 0.995
_diffrn_measurement_device_type  'Bruker VENTURE PHOTONIII c7'
_diffrn_measurement_method       '\f and \w scans'
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54178
_diffrn_reflns_av_R_equivalents  0.0671
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_diffrn_reflns_Laue_measured_fraction_full 0.977
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_diffrn_reflns_limit_h_min       -16
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_diffrn_reflns_limit_l_max       9
_diffrn_reflns_limit_l_min       -9
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_diffrn_reflns_point_group_measured_fraction_full 0.977
_diffrn_reflns_point_group_measured_fraction_max 0.995
_diffrn_reflns_theta_full        25.000
_diffrn_reflns_theta_max         65.197
_diffrn_reflns_theta_min         4.319
_exptl_absorpt_coefficient_mu    1.875
_exptl_absorpt_correction_T_max  0.9526
_exptl_absorpt_correction_T_min  0.8608
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   'Bruker APEX4'
_exptl_crystal_colour            colorless
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_exptl_crystal_description       plate
_exptl_crystal_F_000             1424
_exptl_crystal_size_max          0.100
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_exptl_crystal_size_min          0.040
_refine_diff_density_max         0.704
_refine_diff_density_min         -0.890
_refine_diff_density_rms         0.075
_refine_ls_extinction_method     none
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_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
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_refine_ls_number_reflns         5541
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.283
_refine_ls_R_factor_all          0.0863
_refine_ls_R_factor_gt           0.0766
_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^)+12.8978P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1637
_refine_ls_wR_factor_ref         0.1649
_reflns_Friedel_coverage         0.000
_reflns_number_gt                5283
_reflns_number_total             5541
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            d4ob01103a2.cif
_cod_data_source_block           5f
_cod_depositor_comments
'Adding full bibliography for 7160135--7160138.cif.'
_cod_original_sg_symbol_H-M      'P 21/c'
_cod_database_code               7160137
_shelx_estimated_absorpt_t_min   0.838
_shelx_estimated_absorpt_t_max   0.930
_shelx_res_checksum              6224