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_7160136
_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, C H Cl3 '
_chemical_formula_sum            'C20 H19 Cl3 N2 O2 S'
_chemical_formula_weight         457.78
_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                 108.215(4)
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   11.0280(14)
_cell_length_b                   18.344(2)
_cell_length_c                   11.1908(13)
_cell_measurement_reflns_used    9903
_cell_measurement_temperature    200(1)
_cell_measurement_theta_max      29.63
_cell_measurement_theta_min      2.24
_cell_volume                     2150.4(4)
_computing_cell_refinement       'Bruker SAINT'
_computing_data_collection       'Bruker APEX4'
_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 1.000
_diffrn_measured_fraction_theta_max 0.998
_diffrn_measurement_device_type  'Bruker VENTURE PHOTONIII c7'
_diffrn_measurement_method       '\f and \w scans'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0928
_diffrn_reflns_av_unetI/netI     0.0545
_diffrn_reflns_Laue_measured_fraction_full 1.000
_diffrn_reflns_Laue_measured_fraction_max 0.998
_diffrn_reflns_limit_h_max       15
_diffrn_reflns_limit_h_min       -15
_diffrn_reflns_limit_k_max       26
_diffrn_reflns_limit_k_min       -26
_diffrn_reflns_limit_l_max       16
_diffrn_reflns_limit_l_min       -16
_diffrn_reflns_number            86872
_diffrn_reflns_point_group_measured_fraction_full 1.000
_diffrn_reflns_point_group_measured_fraction_max 0.998
_diffrn_reflns_theta_full        25.000
_diffrn_reflns_theta_max         31.060
_diffrn_reflns_theta_min         2.214
_exptl_absorpt_coefficient_mu    0.542
_exptl_absorpt_correction_T_max  0.9462
_exptl_absorpt_correction_T_min  0.8173
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   'Bruker APEX4'
_exptl_crystal_colour            colorless
_exptl_crystal_density_diffrn    1.414
_exptl_crystal_description       needle
_exptl_crystal_F_000             944
_exptl_crystal_size_max          0.120
_exptl_crystal_size_mid          0.030
_exptl_crystal_size_min          0.020
_refine_diff_density_max         0.661
_refine_diff_density_min         -0.530
_refine_diff_density_rms         0.066
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.031
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     291
_refine_ls_number_reflns         6870
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.031
_refine_ls_R_factor_all          0.1044
_refine_ls_R_factor_gt           0.0562
_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^)+(0.0657P)^2^+1.1406P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1331
_refine_ls_wR_factor_ref         0.1618
_reflns_Friedel_coverage         0.000
_reflns_number_gt                4277
_reflns_number_total             6870
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            d4ob01103a2.cif
_cod_data_source_block           5n
_cod_depositor_comments
'Adding full bibliography for 7160135--7160138.cif.'
_cod_original_cell_volume        2150.4(5)
_cod_original_sg_symbol_H-M      'P 21/c'
_cod_database_code               7160136
_shelx_estimated_absorpt_t_min   0.939
_shelx_estimated_absorpt_t_max   0.989
_shelx_res_checksum              10935