Synthesis of benzo[<i>d</i>,<i>e</i>]quinoline-spiro-succinimides <i>via</i> rhodium-catalyzed C-H activation/annulation of 1-naphthylamides with maleimides.
Patel, Raj Naresh; Patel, Dharmik Mahendra; Thakur, Dinesh Gopichand; Rathod, Nileshkumar B.; Patel, Sachinkumar D.; Sonawane, Mahesh A.; Ghosh, Subhash Chandra; Organic & biomolecular chemistry 23 (2025) 6897–6902; doi:10.1039/d5ob00825e

data_7160614
_publ_section_title
;
 Synthesis of benzo[<i>d</i>,<i>e</i>]quinoline-spiro-succinimides
 <i>via</i> rhodium-catalyzed C-H activation/annulation of
 1-naphthylamides with maleimides.
;
_journal_issue                   29
_journal_name_full               'Organic &amp; biomolecular chemistry'
_journal_page_first              6897
_journal_page_last               6902
_journal_paper_doi               10.1039/d5ob00825e
_journal_volume                  23
_journal_year                    2025
_chemical_formula_moiety         'C29 H23 N3 O2'
_chemical_formula_sum            'C29 H23 N3 O2'
_chemical_formula_weight         445.50
_space_group_crystal_system      monoclinic
_space_group_IT_number           4
_space_group_name_Hall           'P 2yb'
_space_group_name_H-M_alt        'P 1 21 1'
_atom_sites_solution_hydrogens   geom
_audit_creation_date             2023-08-10
_audit_creation_method
;
Olex2 1.2
(compiled 2018.05.29 svn.r3508 for OlexSys, GUI svn.r5506)
;
_audit_update_record
;
2023-09-05 deposited with the CCDC.	2025-06-30 downloaded from the CCDC.
;
_cell_angle_alpha                90
_cell_angle_beta                 100.470(2)
_cell_angle_gamma                90
_cell_formula_units_Z            2
_cell_length_a                   11.6874(5)
_cell_length_b                   7.3297(3)
_cell_length_c                   15.2220(7)
_cell_measurement_reflns_used    9960
_cell_measurement_temperature    273(2)
_cell_measurement_theta_max      24.655
_cell_measurement_theta_min      2.422
_cell_volume                     1282.28(10)
_computing_cell_refinement       'SAINT V8.40B (?, 2016)'
_computing_data_reduction        'SAINT V8.40B (?, 2016)'
_computing_molecular_graphics    'Olex2 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 (Dolomanov et al., 2009)'
_computing_structure_refinement  'ShelXL (Sheldrick, 2015)'
_computing_structure_solution    'SHELXT 2018/2 (Sheldrick, 2018)'
_diffrn_ambient_temperature      273.15
_diffrn_measured_fraction_theta_full 0.999
_diffrn_measured_fraction_theta_max 0.999
_diffrn_measurement_device_type  'Bruker D8 QUEST'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0596
_diffrn_reflns_av_unetI/netI     0.0284
_diffrn_reflns_Laue_measured_fraction_full 0.999
_diffrn_reflns_Laue_measured_fraction_max 0.999
_diffrn_reflns_limit_h_max       13
_diffrn_reflns_limit_h_min       -13
_diffrn_reflns_limit_k_max       8
_diffrn_reflns_limit_k_min       -8
_diffrn_reflns_limit_l_max       18
_diffrn_reflns_limit_l_min       -18
_diffrn_reflns_number            43802
_diffrn_reflns_point_group_measured_fraction_full 0.999
_diffrn_reflns_point_group_measured_fraction_max 0.999
_diffrn_reflns_theta_full        24.998
_diffrn_reflns_theta_max         24.998
_diffrn_reflns_theta_min         2.028
_exptl_absorpt_coefficient_mu    0.074
_exptl_absorpt_correction_T_max  0.7455
_exptl_absorpt_correction_T_min  0.6569
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
'SADABS-2016/2 (Bruker,2016/2) was used for absorption correction. wR2(int) was 0.1069 before and 0.0680 after correction. The Ratio of minimum to maximum transmission is 0.8812. The \l/2 correction factor is Not present.'
_exptl_crystal_colour            yellow
_exptl_crystal_colour_primary    yellow
_exptl_crystal_density_diffrn    1.154
_exptl_crystal_description       plate
_exptl_crystal_F_000             468
_exptl_crystal_size_max          0.21
_exptl_crystal_size_mid          0.11
_exptl_crystal_size_min          0.05
_refine_diff_density_max         0.098
_refine_diff_density_min         -0.131
_refine_diff_density_rms         0.027
_refine_ls_abs_structure_details
;
 Flack x determined using 1724 quotients [(I+)-(I-)]/[(I+)+(I-)]
 (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259).
;
_refine_ls_abs_structure_Flack   0.4(5)
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.058
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     310
_refine_ls_number_reflns         4510
_refine_ls_number_restraints     1
_refine_ls_restrained_S_all      1.058
_refine_ls_R_factor_all          0.0391
_refine_ls_R_factor_gt           0.0330
_refine_ls_shift/su_max          0.002
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'w=1/[\s^2^(Fo^2^)+(0.0500P)^2^+0.1030P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0884
_refine_ls_wR_factor_ref         0.0931
_reflns_Friedel_coverage         0.843
_reflns_Friedel_fraction_full    1.000
_reflns_Friedel_fraction_max     1.000
_reflns_number_gt                4027
_reflns_number_total             4510
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            d5ob00825e2.cif
_cod_data_source_block           sgrp_pc_382_0ma_a
_cod_depositor_comments
'Adding full bibliography for 7160614--7160616.cif.'
_cod_database_code               7160614
_shelx_shelxl_version_number     2018/3
_shelx_estimated_absorpt_t_max   0.996
_shelx_estimated_absorpt_t_min   0.985
_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:
 C14(H14A,H14B)
2.b Aromatic/amide H refined with riding coordinates:
 C1(H1), C2(H2), C10(H10), C18(H18), C19(H19), C20(H20), C21(H21), C22(H22),
 C24(H24), C25(H25), C26(H26), C28(H28)
2.c Idealised Me refined as rotating group:
 C12(H12A,H12B,H12C), C13(H13A,H13B,H13C), C29(H29A,H29B,H29C)
;
_shelx_res_checksum              38667
_shelx_fab_checksum              14354
_olex2_submission_special_instructions 'No special instructions were received'