A metal-free route to substituted imidazolidines via ring-opening cyclization (ROC) of activated aziridines with N-benzylanilines: DA-COP catalyzed photo-oxidative C–H activation
Kumar, Manish; Singh, Bharat; Singh, Sugandha; Verma, Indresh; Kar, Kamal K.; Ghorai, Manas K.; Catalysis Science & Technology 14 (2024) 6411–6419; doi:10.1039/D4CY00808A

data_1572544
_publ_section_title
;
 A metal-free route to substituted imidazolidines via ring-opening
 cyclization (ROC) of activated aziridines with N-benzylanilines: DA-COP
 catalyzed photo-oxidative C--H activation
;
_journal_issue                   21
_journal_name_full               'Catalysis Science &amp; Technology'
_journal_page_first              6411
_journal_page_last               6419
_journal_paper_doi               10.1039/D4CY00808A
_journal_volume                  14
_journal_year                    2024
_chemical_formula_moiety         'C28 H26 N2 O2 S'
_chemical_formula_sum            'C28 H26 N2 O2 S'
_chemical_formula_weight         454.57
_space_group_crystal_system      monoclinic
_space_group_IT_number           14
_space_group_name_Hall           '-P 2yn'
_space_group_name_H-M_alt        'P 1 21/n 1'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     dual
_audit_creation_date             2022-11-12
_audit_creation_method
;
Olex2 1.5
(compiled 2022.04.07 svn.rca3783a0 for OlexSys, GUI svn.r6498)
;
_audit_update_record
;
2023-09-19 deposited with the CCDC.	2024-09-10 downloaded from the CCDC.
;
_cell_angle_alpha                90
_cell_angle_beta                 104.753(2)
_cell_angle_gamma                90
_cell_formula_units_Z            8
_cell_length_a                   18.3937(9)
_cell_length_b                   9.9807(5)
_cell_length_c                   26.3497(13)
_cell_measurement_reflns_used    9909
_cell_measurement_temperature    100
_cell_measurement_theta_max      28.28
_cell_measurement_theta_min      2.34
_cell_volume                     4677.9(4)
_computing_cell_refinement       'SAINT V8.38A (Bruker, 2018)'
_computing_data_reduction        'SAINT V8.38A (Bruker, 2018)'
_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      100(2)
_diffrn_detector                 'CCD area detector'
_diffrn_detector_area_resol_mean 7.9
_diffrn_detector_type            'Bruker SMART CCD 1K area detector'
_diffrn_measured_fraction_theta_full 0.999
_diffrn_measured_fraction_theta_max 0.992
_diffrn_measurement_device       'three-circle diffractometer'
_diffrn_measurement_device_type  'Bruker SMART CCD 1K area detector'
_diffrn_measurement_method       '\w scans'
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0542
_diffrn_reflns_av_unetI/netI     0.0363
_diffrn_reflns_Laue_measured_fraction_full 0.999
_diffrn_reflns_Laue_measured_fraction_max 0.992
_diffrn_reflns_limit_h_max       24
_diffrn_reflns_limit_h_min       -24
_diffrn_reflns_limit_k_max       13
_diffrn_reflns_limit_k_min       -13
_diffrn_reflns_limit_l_max       35
_diffrn_reflns_limit_l_min       -35
_diffrn_reflns_number            74560
_diffrn_reflns_point_group_measured_fraction_full 0.999
_diffrn_reflns_point_group_measured_fraction_max 0.992
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         28.421
_diffrn_reflns_theta_min         2.191
_diffrn_source                   'sealed X-ray tube'
_diffrn_source_current           1.0
_diffrn_source_power             0.05
_diffrn_source_target            Mo
_diffrn_source_voltage           50.0
_diffrn_standards_number         0
_exptl_absorpt_coefficient_mu    0.167
_exptl_absorpt_correction_T_max  0.7457
_exptl_absorpt_correction_T_min  0.7073
_exptl_absorpt_correction_type   empirical
_exptl_absorpt_process_details
;
SADABS-2016/2 (Bruker,2016/2) was used for absorption correction.
wR2(int) was 0.1363 before and 0.0579 after correction.
The Ratio of minimum to maximum transmission is 0.9485.
The \l/2 correction factor is Not present.
;
_exptl_crystal_colour            'clear whiteish white'
_exptl_crystal_colour_lustre     clear
_exptl_crystal_colour_modifier   whiteish
_exptl_crystal_colour_primary    white
_exptl_crystal_density_diffrn    1.291
_exptl_crystal_description       block
_exptl_crystal_F_000             1920
_exptl_crystal_size_max          0.2
_exptl_crystal_size_mid          0.1
_exptl_crystal_size_min          0.05
_refine_diff_density_max         0.361
_refine_diff_density_min         -0.485
_refine_diff_density_rms         0.059
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.077
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     597
_refine_ls_number_reflns         11675
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.077
_refine_ls_R_factor_all          0.0629
_refine_ls_R_factor_gt           0.0462
_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^)+(0.0356P)^2^+4.5890P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1049
_refine_ls_wR_factor_ref         0.1157
_reflns_Friedel_coverage         0.000
_reflns_number_gt                9422
_reflns_number_total             11675
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            d4cy00808a2.cif
_cod_data_source_block           27apra_0m
_cod_depositor_comments          'Adding full bibliography for 1572544.cif.'
_cod_database_code               1572544
_shelx_shelxl_version_number     2018/3
_shelx_estimated_absorpt_t_max   0.992
_shelx_estimated_absorpt_t_min   0.967
_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:
 C2(H2), C1(H1), C37(H37), C36(H36)
2.b Secondary CH2 refined with riding coordinates:
 C3(H3A,H3B), C38(H38A,H38B)
2.c Aromatic/amide H refined with riding coordinates:
 C46(H46), C23(H23), C9(H9), C27(H27), C6(H6), C5(H5), C47(H47), C30(H30),
 C8(H8), C15(H15), C21(H21), C50(H50), C20(H20), C14(H14), C19(H19), C49(H49),
 C26(H26), C31(H31), C24(H24), C11(H11), C41(H41), C42(H42), C17(H17), C48(H48),
  C33(H33), C18(H18), C7(H7), C44(H44), C12(H12), C34(H34), C40(H40), C54(H54),
 C13(H13), C43(H43), C52(H52), C56(H56), C55(H55), C53(H53)
2.d Idealised Me refined as rotating group:
 C28(H28A,H28B,H28C), C35(H35A,H35B,H35C)
;
_shelx_res_checksum              86175
_olex2_submission_special_instructions 'No special instructions were received'