Discovery of intermolecular cascade annulation for dihydrobenzo[<i>b</i>][1,8]naphthyridine-ylidene-pyrrolidinetriones.
Luo, Wenjun; Zheng, Xinghua; Lin, Hehua; Fu, Li; Long, Lipeng; Yu, Daohong; Chen, Zhengwang; Yang, Min; Wang, Zhong-Xia; Chemical science 16 (2025) 4119–4126; doi:10.1039/d4sc07999j

data_1573805
_publ_section_title
;
 Discovery of intermolecular cascade annulation for
 dihydrobenzo[<i>b</i>][1,8]naphthyridine-ylidene-pyrrolidinetriones.
;
_journal_issue                   9
_journal_name_full               'Chemical science'
_journal_page_first              4119
_journal_page_last               4126
_journal_paper_doi               10.1039/d4sc07999j
_journal_volume                  16
_journal_year                    2025
_chemical_formula_moiety         'C30 H20 Br N3 O3'
_chemical_formula_sum            'C30 H20 Br N3 O3'
_chemical_formula_weight         550.40
_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             2023-11-01
_audit_creation_method
;
Olex2 1.5
(compiled 2022.04.07 svn.rca3783a0 for OlexSys, GUI svn.r6498)
;
_audit_update_record
;
2024-10-15 deposited with the CCDC.	2025-01-23 downloaded from the CCDC.
;
_cell_angle_alpha                90
_cell_angle_beta                 108.5050(10)
_cell_angle_gamma                90
_cell_formula_units_Z            8
_cell_length_a                   15.7313(6)
_cell_length_b                   13.6060(5)
_cell_length_c                   24.1199(10)
_cell_measurement_reflns_used    9734
_cell_measurement_temperature    170.00
_cell_measurement_theta_max      60.320
_cell_measurement_theta_min      3.288
_cell_volume                     4895.7(3)
_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 0.998
_diffrn_measured_fraction_theta_max 0.997
_diffrn_measurement_device_type  'zju Bruker D8 Venture'
_diffrn_measurement_method       '\w and \f scans'
_diffrn_radiation_type           GaK\a
_diffrn_radiation_wavelength     1.34139
_diffrn_reflns_av_R_equivalents  0.0362
_diffrn_reflns_av_unetI/netI     0.0289
_diffrn_reflns_Laue_measured_fraction_full 0.998
_diffrn_reflns_Laue_measured_fraction_max 0.997
_diffrn_reflns_limit_h_max       20
_diffrn_reflns_limit_h_min       -20
_diffrn_reflns_limit_k_max       17
_diffrn_reflns_limit_k_min       -16
_diffrn_reflns_limit_l_max       31
_diffrn_reflns_limit_l_min       -31
_diffrn_reflns_number            62961
_diffrn_reflns_point_group_measured_fraction_full 0.998
_diffrn_reflns_point_group_measured_fraction_max 0.997
_diffrn_reflns_theta_full        53.594
_diffrn_reflns_theta_max         60.639
_diffrn_reflns_theta_min         3.288
_diffrn_source_current           3.57
_diffrn_source_power             0.24954300000000001
_diffrn_source_voltage           69.9
_exptl_absorpt_coefficient_mu    1.712
_exptl_absorpt_correction_T_max  0.7519
_exptl_absorpt_correction_T_min  0.6602
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
SADABS-2016/2 (Bruker,2016/2) was used for absorption correction.
wR2(int) was 0.0725 before and 0.0536 after correction.
The Ratio of minimum to maximum transmission is 0.8780.
The \l/2 correction factor is Not present.
;
_exptl_crystal_colour            red
_exptl_crystal_colour_primary    red
_exptl_crystal_density_diffrn    1.493
_exptl_crystal_description       block
_exptl_crystal_F_000             2240
_exptl_crystal_size_max          0.09
_exptl_crystal_size_mid          0.06
_exptl_crystal_size_min          0.04
_refine_diff_density_max         0.428
_refine_diff_density_min         -1.007
_refine_diff_density_rms         0.060
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.069
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     669
_refine_ls_number_reflns         11216
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.069
_refine_ls_R_factor_all          0.0445
_refine_ls_R_factor_gt           0.0366
_refine_ls_shift/su_max          0.003
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'w=1/[\s^2^(Fo^2^)+(0.0395P)^2^+2.8678P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0896
_refine_ls_wR_factor_ref         0.0943
_reflns_Friedel_coverage         0.000
_reflns_number_gt                9479
_reflns_number_total             11216
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            d4sc07999j2.cif
_cod_data_source_block           231031_zxh_1_0m
_cod_depositor_comments          'Adding full bibliography for 1573805.cif.'
_cod_database_code               1573805
_shelx_shelxl_version_number     2019/2
_shelx_estimated_absorpt_t_max   0.935
_shelx_estimated_absorpt_t_min   0.861
_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 Secondary CH2 refined with riding coordinates:
 C29(H29A,H29B), C29A(H29C,H29D)
2.b Aromatic/amide H refined with riding coordinates:
 C1(H1), C2(H2), C3(H3), C4(H4), C7(H7), C11(H11), C14(H14), C15(H15),
 C17(H17), C18(H18), C20(H20), C21(H21), C22(H22), C23(H23), C24(H24), C1A(H1A),
  C2A(H2A), C3A(H3A), C4A(H4A), C7A(H7A), C11A(H11A), C14A(H14A), C15A(H15A),
 C17A(H17A), C18A(H18A), C20A(H20A), C21A(H21A), C22A(H22A), C23A(H23A),
 C24A(H24A)
2.c Idealised Me refined as rotating group:
 C30(H30A,H30B,H30C), C30A(H30D,H30E,H30F)
;
_shelx_res_checksum              64287
_olex2_submission_special_instructions 'No special instructions were received'