Synthesis of functionalized tetrahydrodibenzo[<i>b</i>,<i>g</i>][1,8]naphthyridin-1(2<i>H</i>)-ones through base-promoted annulation of quinoline-derived dipolarophiles and cyclic enaminones.
Luo, Wenjun; Zheng, Xinghua; Zhang, Fanglian; Luo, Qiuya; Deng, Wen-Ting; Long, Lipeng; Yu, Daohong; Wang, Zhong-Xia; Chen, Zhengwang; Organic & biomolecular chemistry 21 (2023) 9524–9529; doi:10.1039/d3ob01547e

data_7159686
_publ_section_title
;
 Synthesis of functionalized
 tetrahydrodibenzo[<i>b</i>,<i>g</i>][1,8]naphthyridin-1(2<i>H</i>)-ones
 through base-promoted annulation of quinoline-derived dipolarophiles and
 cyclic enaminones.
;
_journal_issue                   48
_journal_name_full               'Organic &amp; biomolecular chemistry'
_journal_page_first              9524
_journal_page_last               9529
_journal_paper_doi               10.1039/d3ob01547e
_journal_volume                  21
_journal_year                    2023
_chemical_formula_moiety         'C33 H32 N2 O3'
_chemical_formula_sum            'C33 H32 N2 O3'
_chemical_formula_weight         504.60
_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             2023-10-18
_audit_creation_method
;
Olex2 1.5
(compiled 2022.04.07 svn.rca3783a0 for OlexSys, GUI svn.r6498)
;
_audit_update_record
;
2023-11-06 deposited with the CCDC.	2023-11-16 downloaded from the CCDC.
;
_cell_angle_alpha                90
_cell_angle_beta                 100.9190(10)
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   11.9232(3)
_cell_length_b                   10.4301(4)
_cell_length_c                   22.0572(8)
_cell_measurement_reflns_used    7134
_cell_measurement_temperature    170.00
_cell_measurement_theta_max      26.017
_cell_measurement_theta_min      2.167
_cell_volume                     2693.38(16)
_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 0.998
_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  0.0771
_diffrn_reflns_av_unetI/netI     0.0488
_diffrn_reflns_Laue_measured_fraction_full 0.998
_diffrn_reflns_Laue_measured_fraction_max 0.998
_diffrn_reflns_limit_h_max       15
_diffrn_reflns_limit_h_min       -15
_diffrn_reflns_limit_k_max       13
_diffrn_reflns_limit_k_min       -13
_diffrn_reflns_limit_l_max       28
_diffrn_reflns_limit_l_min       -28
_diffrn_reflns_number            39856
_diffrn_reflns_point_group_measured_fraction_full 0.998
_diffrn_reflns_point_group_measured_fraction_max 0.998
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         27.508
_diffrn_reflns_theta_min         2.167
_diffrn_source_current           1.4
_diffrn_source_power             0.07
_diffrn_source_voltage           50.0
_exptl_absorpt_coefficient_mu    0.080
_exptl_absorpt_correction_T_max  0.7456
_exptl_absorpt_correction_T_min  0.6931
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
SADABS-2016/2 (Bruker,2016/2) was used for absorption correction.
wR2(int) was 0.1371 before and 0.0684 after correction.
The Ratio of minimum to maximum transmission is 0.9296.
The \l/2 correction factor is Not present.
;
_exptl_crystal_colour            colourless
_exptl_crystal_colour_primary    colourless
_exptl_crystal_density_diffrn    1.244
_exptl_crystal_description       block
_exptl_crystal_F_000             1072
_exptl_crystal_size_max          0.45
_exptl_crystal_size_mid          0.16
_exptl_crystal_size_min          0.1
_refine_diff_density_max         0.243
_refine_diff_density_min         -0.265
_refine_diff_density_rms         0.054
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.173
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     421
_refine_ls_number_reflns         6193
_refine_ls_number_restraints     284
_refine_ls_restrained_S_all      1.155
_refine_ls_R_factor_all          0.1233
_refine_ls_R_factor_gt           0.0875
_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^)+(0.0199P)^2^+3.6774P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1551
_refine_ls_wR_factor_ref         0.1717
_reflns_Friedel_coverage         0.000
_reflns_number_gt                4516
_reflns_number_total             6193
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            d3ob01547e2.cif
_cod_data_source_block           mo_231016_lwj_1_0m
_cod_depositor_comments          'Adding full bibliography for 7159686.cif.'
_cod_database_code               7159686
_shelx_shelxl_version_number     2019/2
_shelx_estimated_absorpt_t_max   0.992
_shelx_estimated_absorpt_t_min   0.965
_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, All O(H) groups
2. Restrained distances
 N2-C27 \\sim N2-C27A
 with sigma of 0.02
 O3-C29 \\sim O3A-C29A
 with sigma of 0.02
 O3-C33 \\sim O3A-C33A
 with sigma of 0.02
 C29-C28 \\sim C29A-C28A
 with sigma of 0.02
 C29-C30 \\sim C29A-C30A
 with sigma of 0.02
 C28-C30 \\sim C28A-C30A
 with sigma of 0.04
 C30-C32 \\sim C30A-C32A
 with sigma of 0.04
 C29-C31 \\sim C29A-C31A
 with sigma of 0.04
 C27-C28 \\sim C27A-C28A
 with sigma of 0.02
 C27-C32 \\sim C27A-C32A
 with sigma of 0.02
 C30-C31 \\sim C30A-C31A
 with sigma of 0.02
 C29-C33 \\sim C29A-C33A
 with sigma of 0.04
 C32-C31 \\sim C32A-C31A
 with sigma of 0.02
 C27-C31 \\sim C27A-C31A
 with sigma of 0.04
 C28-C32 \\sim C28A-C32A
 with sigma of 0.04
 N2-C28 \\sim N2-C28A
 with sigma of 0.04
 N2-C32 \\sim N2-C32A
 with sigma of 0.04
 O3-C28 \\sim O3A-C28A
 with sigma of 0.04
 O3-C30 \\sim O3A-C30A
 with sigma of 0.04
 C29-C27 \\sim C29A-C27A
 with sigma of 0.04
3. Uiso/Uaniso restraints and constraints
N2 \\sim O3 \\sim O3A \\sim C27 \\sim C27A \\sim C28 \\sim C28A \\sim C29 \\sim
C29A \\sim C30 \\sim C30A \\sim C31 \\sim C31A \\sim C32 \\sim C32A \\sim C33
\\sim C33A: within 2A with sigma of 0.01 and sigma for terminal atoms of 0.02
within 2A
4. Others
 Sof(O3A)=Sof(C27A)=Sof(C28A)=Sof(H28A)=Sof(C29A)=Sof(C30A)=Sof(H30A)=
 Sof(C31A)=Sof(H31A)=Sof(C32A)=Sof(H32A)=Sof(C33A)=Sof(H33D)=Sof(H33E)=
 Sof(H33F)=1-FVAR(1)
 Sof(O3)=Sof(C27)=Sof(C28)=Sof(H28)=Sof(C29)=Sof(C30)=Sof(H30)=Sof(C31)=
 Sof(H31)=Sof(C32)=Sof(H32)=Sof(C33)=Sof(H33A)=Sof(H33B)=Sof(H33C)=FVAR(1)
5.a Ternary CH refined with riding coordinates:
 C12(H12), C18(H18)
5.b Secondary CH2 refined with riding coordinates:
 C14(H14A,H14B), C16(H16A,H16B), C17(H17A,H17B)
5.c Aromatic/amide H refined with riding coordinates:
 C1(H1A), C2(H2), C3(H3), C4(H4), C7(H7), C20(H20), C21(H21), C22(H22),
 C23(H23), C24(H24), C28(H28), C28A(H28A), C30(H30), C30A(H30A), C31(H31),
 C31A(H31A), C32(H32), C32A(H32A)
5.d Idealised Me refined as rotating group:
 C25(H25A,H25B,H25C), C26(H26A,H26B,H26C), C33(H33A,H33B,H33C), C33A(H33D,H33E,
 H33F)
5.e Idealised tetrahedral OH refined as rotating group:
 O1(H1)
;
_shelx_res_checksum              22068
_shelx_hkl_checksum              81679
_olex2_submission_special_instructions 'No special instructions were received'