Access to thiionized-, selenolized-, and alkylated 5-alkylidene 3-pyrrolin-2-one derivatives <i>via</i> a regioselective oxidative annulation reaction.
Liu, Donghan; Song, Siyu; Chen, Longkun; Zhang, Mingshuai; Liu, Zhuoyuan; Lu, Xihang; Huang, Jiuzhong; Yu, Fuchao; Organic & biomolecular chemistry 21 (2023) 2596–2602; doi:10.1039/d3ob00014a

data_7159221
_publ_section_title
;
 Access to thiionized-, selenolized-, and alkylated 5-alkylidene
 3-pyrrolin-2-one derivatives <i>via</i> a regioselective oxidative
 annulation reaction.
;
_journal_issue                   12
_journal_name_full               'Organic &amp; biomolecular chemistry'
_journal_page_first              2596
_journal_page_last               2602
_journal_paper_doi               10.1039/d3ob00014a
_journal_volume                  21
_journal_year                    2023
_chemical_formula_moiety         'C23 H24 N2 O2'
_chemical_formula_sum            'C23 H24 N2 O2'
_chemical_formula_weight         360.44
_space_group_crystal_system      monoclinic
_space_group_IT_number           15
_space_group_name_Hall           '-C 2yc'
_space_group_name_H-M_alt        'C 1 2/c 1'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     dual
_audit_creation_date             2022-12-10
_audit_creation_method
;
Olex2 1.5
(compiled 2022.04.07 svn.rca3783a0 for OlexSys, GUI svn.r6498)
;
_audit_update_record
;
2022-12-15 deposited with the CCDC.	2023-03-02 downloaded from the CCDC.
;
_cell_angle_alpha                90
_cell_angle_beta                 91.554(4)
_cell_angle_gamma                90
_cell_formula_units_Z            8
_cell_length_a                   32.974(7)
_cell_length_b                   9.2490(18)
_cell_length_c                   15.640(3)
_cell_measurement_reflns_used    2474
_cell_measurement_temperature    296.15
_cell_measurement_theta_max      27.37
_cell_measurement_theta_min      2.29
_cell_volume                     4768.1(16)
_computing_cell_refinement       'SAINT v8.34A (Bruker, 2013)'
_computing_data_reduction        'SAINT v8.34A (Bruker, 2013)'
_computing_molecular_graphics    'Olex2 1.5 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 1.5 (Dolomanov et al., 2009)'
_computing_structure_refinement  'SHELXL 2018/3 (Sheldrick, 2015)'
_computing_structure_solution    'SHELXT 2018/2 (Sheldrick, 2018)'
_diffrn_ambient_temperature      296.15
_diffrn_measured_fraction_theta_full 0.998
_diffrn_measured_fraction_theta_max 0.972
_diffrn_measurement_device_type  'Bruker APEX-II CCD'
_diffrn_measurement_method       '\f and \w scans'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0475
_diffrn_reflns_av_unetI/netI     0.0721
_diffrn_reflns_Laue_measured_fraction_full 0.998
_diffrn_reflns_Laue_measured_fraction_max 0.972
_diffrn_reflns_limit_h_max       40
_diffrn_reflns_limit_h_min       -38
_diffrn_reflns_limit_k_max       11
_diffrn_reflns_limit_k_min       -11
_diffrn_reflns_limit_l_max       20
_diffrn_reflns_limit_l_min       -12
_diffrn_reflns_number            13320
_diffrn_reflns_point_group_measured_fraction_full 0.998
_diffrn_reflns_point_group_measured_fraction_max 0.972
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         27.567
_diffrn_reflns_theta_min         2.641
_diffrn_source_current           30.0
_diffrn_source_power             1.5
_diffrn_source_voltage           50.0
_diffrn_standards_number         0
_exptl_absorpt_coefficient_mu    0.064
_exptl_absorpt_correction_T_max  0.7456
_exptl_absorpt_correction_T_min  0.6250
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
SADABS-2014/5 (Bruker,2014/5) was used for absorption correction.
wR2(int) was 0.1094 before and 0.0382 after correction.
The Ratio of minimum to maximum transmission is 0.8383.
The \l/2 correction factor is 0.00150.
;
_exptl_crystal_density_diffrn    1.004
_exptl_crystal_description       block
_exptl_crystal_F_000             1536
_exptl_crystal_size_max          0.2
_exptl_crystal_size_mid          0.15
_exptl_crystal_size_min          0.1
_refine_diff_density_max         0.266
_refine_diff_density_min         -0.212
_refine_diff_density_rms         0.049
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.030
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     246
_refine_ls_number_reflns         5358
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.030
_refine_ls_R_factor_all          0.1619
_refine_ls_R_factor_gt           0.0876
_refine_ls_shift/su_max          0.004
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'w=1/[\s^2^(Fo^2^)+(0.1226P)^2^+5.6233P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.2455
_refine_ls_wR_factor_ref         0.2864
_reflns_Friedel_coverage         0.000
_reflns_number_gt                2554
_reflns_number_total             5358
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            d3ob00014a2.cif
_cod_data_source_block           221209yfc217_0m
_cod_depositor_comments
'Adding full bibliography for 7159219--7159221.cif.'
_cod_original_cell_volume        4768.0(16)
_cod_database_code               7159221
_shelx_shelxl_version_number     2018/3
_shelx_estimated_absorpt_t_max   0.994
_shelx_estimated_absorpt_t_min   0.987
_olex2_refinement_description
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups, All C(H,H) groups, All N(H) groups
 At 1.5 times of:
  All C(H,H,H) groups
2.a Ternary CH refined with riding coordinates:
 C00G(H00G)
2.b Secondary CH2 refined with riding coordinates:
 C00N(H00F,H00J), C00Q(H00S,H00T), C00R(H00U,H00V)
2.c Aromatic/amide H refined with riding coordinates:
 N003(H003), C009(H009), C00A(H00A), C00B(H00B), C00C(H00C), C00D(H00D),
 C00E(H00E), C00H(H00H), C00I(H00I), C00K(H00K), C00M(H00M)
2.d Idealised Me refined as rotating group:
 C00O(H00L,H00N,H00O), C00P(H00P,H00Q,H00R)
;
_smtbx_masks_void_probe_radius   1.2
_smtbx_masks_void_truncation_radius 1.2
_shelx_res_checksum              80642
_shelx_fab_checksum              60589
_olex2_submission_special_instructions 'No special instructions were received'