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_7160135
_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         'C16 H20 N2 O2 S'
_chemical_formula_sum            'C16 H20 N2 O2 S'
_chemical_formula_weight         304.40
_space_group_crystal_system      orthorhombic
_space_group_IT_number           61
_space_group_name_Hall           '-P 2ac 2ab'
_space_group_name_H-M_alt        'P b c a'
_atom_sites_solution_hydrogens   mixed
_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
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_cell_angle_gamma                90
_cell_formula_units_Z            8
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_cell_length_b                   11.3000(2)
_cell_length_c                   24.7099(4)
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_cell_measurement_temperature    200(1)
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_cell_volume                     3237.66(10)
_computing_cell_refinement       'Bruker SAINT'
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_computing_data_reduction        'Bruker SAINT'
_computing_structure_refinement  'SHELXL-2019/2 (Sheldrick, 2019)'
_computing_structure_solution    'SHELXS-97 (Sheldrick 2008)'
_diffrn_ambient_temperature      200(1)
_diffrn_measured_fraction_theta_full 0.992
_diffrn_measured_fraction_theta_max 0.992
_diffrn_measurement_device_type  'Bruker VENTURE PHOTON III c7'
_diffrn_measurement_method       '\f and \w scans'
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54178
_diffrn_reflns_av_R_equivalents  0.0389
_diffrn_reflns_av_unetI/netI     0.0218
_diffrn_reflns_Laue_measured_fraction_full 0.992
_diffrn_reflns_Laue_measured_fraction_max 0.992
_diffrn_reflns_limit_h_max       13
_diffrn_reflns_limit_h_min       -13
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_diffrn_reflns_limit_l_max       29
_diffrn_reflns_limit_l_min       -27
_diffrn_reflns_number            23306
_diffrn_reflns_point_group_measured_fraction_full 0.992
_diffrn_reflns_point_group_measured_fraction_max 0.992
_diffrn_reflns_theta_full        65.077
_diffrn_reflns_theta_max         65.076
_diffrn_reflns_theta_min         5.231
_exptl_absorpt_coefficient_mu    1.822
_exptl_absorpt_correction_T_max  0.9526
_exptl_absorpt_correction_T_min  0.8921
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   'Bruker APEX4'
_exptl_crystal_colour            colourless
_exptl_crystal_density_diffrn    1.249
_exptl_crystal_description       plate
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_exptl_crystal_size_max          0.150
_exptl_crystal_size_mid          0.130
_exptl_crystal_size_min          0.040
_refine_diff_density_max         0.225
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_refine_diff_density_rms         0.038
_refine_ls_extinction_method     none
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_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     197
_refine_ls_number_reflns         2731
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.040
_refine_ls_R_factor_all          0.0377
_refine_ls_R_factor_gt           0.0324
_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^)+(0.0438P)^2^+1.2710P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0835
_refine_ls_wR_factor_ref         0.0859
_reflns_Friedel_coverage         0.000
_reflns_number_gt                2453
_reflns_number_total             2731
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            d4ob01103a2.cif
_cod_data_source_block           5o
_cod_depositor_comments
'Adding full bibliography for 7160135--7160138.cif.'
_cod_database_code               7160135
_shelx_estimated_absorpt_t_min   0.776
_shelx_estimated_absorpt_t_max   0.932
_shelx_res_checksum              60615