Photo-promoted radical cascade cyclization of 4-(allylamino)-3-cyanocoumarins: access to sulfonylated pyrido[3,2-c]coumarin derivatives
Yang, Luyao; Ying, Jialuo; Zheng, Hao; Xu, Yuyan; Wu, Liping; Chen, Zhiwei; Green Chemistry 27 (2025) 3524–3531; doi:10.1039/D4GC06598K

data_7250085
_publ_section_title
;
 Photo-promoted radical cascade cyclization of
 4-(allylamino)-3-cyanocoumarins: access to sulfonylated
 pyrido[3,2-c]coumarin derivatives
;
_journal_issue                   13
_journal_name_full               'Green Chemistry'
_journal_page_first              3524
_journal_page_last               3531
_journal_paper_doi               10.1039/D4GC06598K
_journal_volume                  27
_journal_year                    2025
_chemical_formula_moiety         'C20 H16 N2 O5 S, C2 H6 O S'
_chemical_formula_sum            'C22 H22 N2 O6 S2'
_chemical_formula_weight         474.53
_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             2024-06-19
_audit_creation_method
;
Olex2 1.5
(compiled 2022.04.07 svn.rca3783a0 for OlexSys, GUI svn.r6498)
;
_audit_update_record
;
2024-07-17 deposited with the CCDC.	2025-02-28 downloaded from the CCDC.
;
_cell_angle_alpha                90
_cell_angle_beta                 110.8250(10)
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   13.8810(5)
_cell_length_b                   11.8967(4)
_cell_length_c                   14.0748(5)
_cell_measurement_reflns_used    9992
_cell_measurement_temperature    170.00
_cell_measurement_theta_max      28.273
_cell_measurement_theta_min      2.308
_cell_volume                     2172.44(13)
_computing_cell_refinement       'SAINT V8.40B (Bruker Nano, Inc., 2019)'
_computing_data_collection       'Bruker Instrument Service vV6.2.14'
_computing_data_reduction        'SAINT V8.40B (Bruker Nano, Inc., 2019)'
_computing_molecular_graphics    'Olex2 1.5 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 1.5 (Dolomanov et al., 2009)'
_computing_structure_refinement  'SHELXL 2019/2 (Sheldrick, 2015)'
_computing_structure_solution    'SHELXT 2018/2 (Sheldrick, 2018)'
_diffrn_ambient_temperature      170.00
_diffrn_measured_fraction_theta_full 0.993
_diffrn_measured_fraction_theta_max 0.988
_diffrn_measurement_device_type  'zju Bruker D8 Venture'
_diffrn_measurement_method       '\w and \f scans'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0392
_diffrn_reflns_av_unetI/netI     0.0342
_diffrn_reflns_Laue_measured_fraction_full 0.993
_diffrn_reflns_Laue_measured_fraction_max 0.988
_diffrn_reflns_limit_h_max       18
_diffrn_reflns_limit_h_min       -18
_diffrn_reflns_limit_k_max       15
_diffrn_reflns_limit_k_min       -15
_diffrn_reflns_limit_l_max       18
_diffrn_reflns_limit_l_min       -18
_diffrn_reflns_number            24965
_diffrn_reflns_point_group_measured_fraction_full 0.993
_diffrn_reflns_point_group_measured_fraction_max 0.988
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         28.306
_diffrn_reflns_theta_min         2.308
_diffrn_source_current           1.4
_diffrn_source_power             0.07
_diffrn_source_voltage           50.0
_exptl_absorpt_coefficient_mu    0.288
_exptl_absorpt_correction_T_max  0.7457
_exptl_absorpt_correction_T_min  0.6955
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
SADABS-2016/2 (Bruker,2016/2) was used for absorption correction.
wR2(int) was 0.1104 before and 0.0595 after correction.
The Ratio of minimum to maximum transmission is 0.9327.
The \l/2 correction factor is Not present.
;
_exptl_crystal_colour            colourless
_exptl_crystal_colour_primary    colourless
_exptl_crystal_density_diffrn    1.451
_exptl_crystal_description       block
_exptl_crystal_F_000             992
_exptl_crystal_size_max          0.39
_exptl_crystal_size_mid          0.32
_exptl_crystal_size_min          0.18
_refine_diff_density_max         0.258
_refine_diff_density_min         -0.387
_refine_diff_density_rms         0.061
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.121
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     292
_refine_ls_number_reflns         5350
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.121
_refine_ls_R_factor_all          0.0702
_refine_ls_R_factor_gt           0.0498
_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^)+(0.0231P)^2^+1.9825P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0951
_refine_ls_wR_factor_ref         0.1055
_reflns_Friedel_coverage         0.000
_reflns_number_gt                4312
_reflns_number_total             5350
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            d4gc06598k2.cif
_cod_data_source_block           240613_yly_1
_cod_depositor_comments          'Adding full bibliography for 7250085.cif.'
_cod_database_code               7250085
_shelx_shelxl_version_number     2019/2
_shelx_estimated_absorpt_t_max   0.950
_shelx_estimated_absorpt_t_min   0.896
_olex2_refinement_description
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups, All C(H,H) groups, All N(H,H) groups
 At 1.5 times of:
  All C(H,H,H) groups
2.a Secondary CH2 refined with riding coordinates:
 C13(H13A,H13B)
2.b Aromatic/amide H refined with riding coordinates:
 C1(H1), C2(H2), C3(H3), C4(H4), C10(H10), C15(H15), C16(H16), C18(H18),
 C19(H19)
2.c X=CH2 refined with riding coordinates:
 N2(H2A,H2B)
2.d Idealised Me refined as rotating group:
 C20(H20A,H20B,H20C), C21(H21A,H21B,H21C), C22(H22A,H22B,H22C)
;
_olex2_submission_special_instructions 'No special instructions were received'