EosinY and copper-catalyzed oxidative [2 + 3] annulation of glycine esters with oxiranes and thiiranes under light free conditions.
Chowdhury, Raghunath; Organic & biomolecular chemistry 23 (2025) 4376–4382; doi:10.1039/d5ob00148j

data_7160470
_publ_section_title
;
 EosinY and copper-catalyzed oxidative [2 + 3] annulation of glycine
 esters with oxiranes and thiiranes under light free conditions.
;
_journal_issue                   18
_journal_name_full               'Organic &amp; biomolecular chemistry'
_journal_page_first              4376
_journal_page_last               4382
_journal_paper_doi               10.1039/d5ob00148j
_journal_volume                  23
_journal_year                    2025
_chemical_formula_moiety         'C24 H23 N O3 S'
_chemical_formula_sum            'C24 H23 N O3 S'
_chemical_formula_weight         405.49
_space_group_crystal_system      triclinic
_space_group_IT_number           2
_space_group_name_Hall           '-P 1'
_space_group_name_H-M_alt        'P -1'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     dual
_audit_creation_date             2024-11-11
_audit_creation_method
;
Olex2 1.5-ac6-016
(compiled 2024.01.13 svn.r2f8d729c for Rigaku Oxford Diffraction, GUI svn.r6897)
;
_audit_update_record
;
2025-01-03 deposited with the CCDC.	2025-04-02 downloaded from the CCDC.
;
_cell_angle_alpha                79.676(3)
_cell_angle_beta                 86.767(3)
_cell_angle_gamma                77.991(3)
_cell_formula_units_Z            4
_cell_length_a                   9.7838(10)
_cell_length_b                   11.8694(13)
_cell_length_c                   18.5982(19)
_cell_measurement_reflns_used    9877
_cell_measurement_temperature    168(2)
_cell_measurement_theta_max      24.88
_cell_measurement_theta_min      2.26
_cell_volume                     2077.9(4)
_computing_cell_refinement       'SAINT V8.40A (Bruker, 2019)'
_computing_data_reduction        'SAINT V8.40A (Bruker, 2019)'
_computing_molecular_graphics    'Olex2 1.5-ac6-016 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 1.5-ac6-016 (Dolomanov et al., 2009)'
_computing_structure_refinement  'SHELXL 2018/3 (Sheldrick, 2015)'
_computing_structure_solution    'SHELXT 2014/5 (Sheldrick, 2014)'
_diffrn_ambient_temperature      168.00
_diffrn_measured_fraction_theta_full 0.994
_diffrn_measured_fraction_theta_max 0.994
_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  0.0644
_diffrn_reflns_av_unetI/netI     0.0441
_diffrn_reflns_Laue_measured_fraction_full 0.994
_diffrn_reflns_Laue_measured_fraction_max 0.994
_diffrn_reflns_limit_h_max       11
_diffrn_reflns_limit_h_min       -11
_diffrn_reflns_limit_k_max       14
_diffrn_reflns_limit_k_min       -14
_diffrn_reflns_limit_l_max       22
_diffrn_reflns_limit_l_min       -22
_diffrn_reflns_number            40745
_diffrn_reflns_point_group_measured_fraction_full 0.994
_diffrn_reflns_point_group_measured_fraction_max 0.994
_diffrn_reflns_theta_full        25.120
_diffrn_reflns_theta_max         25.120
_diffrn_reflns_theta_min         1.780
_diffrn_source_current           1.4
_diffrn_source_power             0.07
_diffrn_source_voltage           50.0
_diffrn_standards_number         0
_exptl_absorpt_coefficient_mu    0.181
_exptl_absorpt_correction_T_max  0.7452
_exptl_absorpt_correction_T_min  0.5901
_exptl_absorpt_correction_type   numerical
_exptl_absorpt_process_details
;
SADABS-2016/2 (Bruker,2016/2) was used for absorption correction.
wR2(int) was 0.1643 before and 0.0669 after correction.
The Ratio of minimum to maximum transmission is 0.7919.
The \l/2 correction factor is Not present.
;
_exptl_crystal_colour            colourless
_exptl_crystal_colour_primary    colourless
_exptl_crystal_density_diffrn    1.296
_exptl_crystal_description       needle
_exptl_crystal_F_000             856
_exptl_crystal_size_max          0.45
_exptl_crystal_size_mid          0.297
_exptl_crystal_size_min          0.21
_refine_diff_density_max         0.190
_refine_diff_density_min         -0.252
_refine_diff_density_rms         0.043
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.025
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     525
_refine_ls_number_reflns         7393
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.025
_refine_ls_R_factor_all          0.0551
_refine_ls_R_factor_gt           0.0385
_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^)+(0.0354P)^2^+0.7797P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0876
_refine_ls_wR_factor_ref         0.0955
_reflns_Friedel_coverage         0.000
_reflns_number_gt                5797
_reflns_number_total             7393
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            d5ob00148j2.cif
_cod_data_source_block           barc_rc_3196_0m
_cod_depositor_comments          'Adding full bibliography for 7160470.cif.'
_cod_database_code               7160470
_shelx_shelxl_version_number     2018/3
_shelx_estimated_absorpt_t_max   0.963
_shelx_estimated_absorpt_t_min   0.923
_olex2_refinement_description
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups, All C(H,H) groups
 At 1.5 times of:
  All C(H,H,H) groups
2.a Ternary CH refined with riding coordinates:
 C4(H4), C17(H17), C33(H33), C41(H41)
2.b Secondary CH2 refined with riding coordinates:
 C2(H2A,H2B), C18(H18A,H18B), C39(H39A,H39B), C42(H42A,H42B)
2.c Aromatic/amide H refined with riding coordinates:
 C6(H6), C7(H7), C10(H10), C11(H11), C12(H12), C13(H13), C14(H14), C15(H15),
 C16(H16), C20(H20), C21(H21), C22(H22), C23(H23), C24(H24), C25(H25), C26(H26),
  C27(H27), C30(H30), C31(H31), C35(H35), C36(H36), C37(H37), C43(H43),
 C44(H44), C45(H45), C46(H46), C47(H47), C48(H48)
2.d Idealised Me refined as rotating group:
 C1(H1A,H1B,H1C), C38(H38A,H38B,H38C)
;
_shelx_res_checksum              46317
_olex2_submission_special_instructions 'No special instructions were received'