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_7159220
_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         'C27 H26 N2 O S'
_chemical_formula_sum            'C27 H26 N2 O S'
_chemical_formula_weight         426.56
_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     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                 105.549(3)
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   11.2145(17)
_cell_length_b                   22.855(4)
_cell_length_c                   9.3203(14)
_cell_measurement_reflns_used    3282
_cell_measurement_temperature    296.15
_cell_measurement_theta_max      27.10
_cell_measurement_theta_min      2.44
_cell_volume                     2301.4(6)
_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 0.975
_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  0.0364
_diffrn_reflns_av_unetI/netI     0.0508
_diffrn_reflns_Laue_measured_fraction_full 0.998
_diffrn_reflns_Laue_measured_fraction_max 0.975
_diffrn_reflns_limit_h_max       14
_diffrn_reflns_limit_h_min       -14
_diffrn_reflns_limit_k_max       28
_diffrn_reflns_limit_k_min       -29
_diffrn_reflns_limit_l_max       9
_diffrn_reflns_limit_l_min       -12
_diffrn_reflns_number            13772
_diffrn_reflns_point_group_measured_fraction_full 0.998
_diffrn_reflns_point_group_measured_fraction_max 0.975
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         27.596
_diffrn_reflns_theta_min         2.594
_diffrn_source_current           30.0
_diffrn_source_power             1.5
_diffrn_source_voltage           50.0
_diffrn_standards_number         0
_exptl_absorpt_coefficient_mu    0.162
_exptl_absorpt_correction_T_max  0.7456
_exptl_absorpt_correction_T_min  0.6810
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
SADABS-2014/5 (Bruker,2014/5) was used for absorption correction.
wR2(int) was 0.0928 before and 0.0323 after correction.
The Ratio of minimum to maximum transmission is 0.9134.
The \l/2 correction factor is 0.00150.
;
_exptl_crystal_density_diffrn    1.231
_exptl_crystal_description       block
_exptl_crystal_F_000             904
_exptl_crystal_size_max          0.2
_exptl_crystal_size_mid          0.15
_exptl_crystal_size_min          0.1
_refine_diff_density_max         0.269
_refine_diff_density_min         -0.350
_refine_diff_density_rms         0.041
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.043
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     284
_refine_ls_number_reflns         5210
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.043
_refine_ls_R_factor_all          0.1013
_refine_ls_R_factor_gt           0.0552
_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^)+(0.0436P)^2^+0.9836P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1101
_refine_ls_wR_factor_ref         0.1301
_reflns_Friedel_coverage         0.000
_reflns_number_gt                3363
_reflns_number_total             5210
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            d3ob00014a2.cif
_cod_data_source_block           221209yfc208_0ma
_cod_depositor_comments
'Adding full bibliography for 7159219--7159221.cif.'
_cod_database_code               7159220
_shelx_shelxl_version_number     2018/3
_shelx_estimated_absorpt_t_max   0.984
_shelx_estimated_absorpt_t_min   0.968
_olex2_refinement_description
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups, All N(H) groups
 At 1.5 times of:
  All C(H,H,H) groups
2.a Aromatic/amide H refined with riding coordinates:
 N003(H003), C007(H007), C00B(H00B), C00D(H00D), C00G(H00G), C00H(H00H),
 C00K(H00K), C00L(H00L), C00M(H00M), C00P(H00P), C00R(H00R), C00S(H00S),
 C00T(H00T), C00U(H00U)
2.b Idealised Me refined as rotating group:
 C00N(H00A,H00C,H00E), C00O(H00F,H00I,H00J), C00Q(H00N,H00O,H00Q), C00V(H00V,
 H00W,H00X)
;
_shelx_res_checksum              99148
_olex2_submission_special_instructions 'No special instructions were received'