One-pot synthesis of new alkyl 1-naphthoates bearing quinoline, pyranone and cyclohexenone moieties via metal-free sequential addition/oxidation reactions
Mousavi, Seyedeh Hekmat; Mohammadizadeh, Mohammad Reza; Poorsadeghi, Samira; Arimitsu, Satoru; Mohammadsaleh, Fatemeh; Kojya, Genta; Gima, Shinichi; RSC Advances 11 (2021) 36748–36752; doi:10.1039/D1RA07092D

data_7243927
_publ_section_title
;
 One-pot synthesis of new alkyl 1-naphthoates bearing quinoline, pyranone
 and cyclohexenone moieties via metal-free sequential addition/oxidation
 reactions
;
_journal_issue                   58
_journal_name_full               'RSC Advances'
_journal_page_first              36748
_journal_page_last               36752
_journal_paper_doi               10.1039/D1RA07092D
_journal_volume                  11
_journal_year                    2021
_chemical_formula_moiety         'C22 H15 N O5'
_chemical_formula_sum            'C22 H15 N O5'
_chemical_formula_weight         373.35
_space_group_crystal_system      triclinic
_space_group_IT_number           2
_space_group_name_Hall           '-P 1'
_space_group_name_H-M_alt        'P -1'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     iterative
_audit_creation_date             2020-09-17
_audit_creation_method
;
Olex2 1.3
(compiled 2020.02.04 svn.rd84adfe8 for OlexSys, GUI svn.r6032)
;
_audit_update_record
;
2021-09-19 deposited with the CCDC.	2021-11-09 downloaded from the CCDC.
;
_cell_angle_alpha                79.927(2)
_cell_angle_beta                 88.945(2)
_cell_angle_gamma                89.730(2)
_cell_formula_units_Z            4
_cell_length_a                   8.2293(2)
_cell_length_b                   10.0168(3)
_cell_length_c                   21.7870(6)
_cell_measurement_temperature    293(2)
_cell_volume                     1767.94(8)
_computing_molecular_graphics    'Olex2 1.3 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 1.3 (Dolomanov et al., 2009)'
_computing_structure_refinement  'SHELXL 2018/3 (Sheldrick, 2015)'
_computing_structure_solution    'olex2.solve 1.3 (Bourhis et al., 2015)'
_diffrn_ambient_temperature      293(2)
_diffrn_measured_fraction_theta_full 0.986
_diffrn_measured_fraction_theta_max 0.849
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0281
_diffrn_reflns_av_unetI/netI     0.0611
_diffrn_reflns_Laue_measured_fraction_full 0.986
_diffrn_reflns_Laue_measured_fraction_max 0.849
_diffrn_reflns_limit_h_max       11
_diffrn_reflns_limit_h_min       -11
_diffrn_reflns_limit_k_max       13
_diffrn_reflns_limit_k_min       -12
_diffrn_reflns_limit_l_max       27
_diffrn_reflns_limit_l_min       -29
_diffrn_reflns_number            17007
_diffrn_reflns_point_group_measured_fraction_full 0.986
_diffrn_reflns_point_group_measured_fraction_max 0.849
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         31.134
_diffrn_reflns_theta_min         1.899
_exptl_absorpt_coefficient_mu    0.101
_exptl_crystal_density_diffrn    1.403
_exptl_crystal_F_000             776
_refine_diff_density_max         0.362
_refine_diff_density_min         -0.357
_refine_diff_density_rms         0.097
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.044
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     509
_refine_ls_number_reflns         9660
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.044
_refine_ls_R_factor_all          0.0922
_refine_ls_R_factor_gt           0.0573
_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^)+(0.0694P)^2^+0.0719P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1296
_refine_ls_wR_factor_ref         0.1504
_reflns_Friedel_coverage         0.000
_reflns_number_gt                6801
_reflns_number_total             9660
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            d1ra07092d2.cif
_cod_data_source_block           200909irai
_cod_original_cell_volume        1767.95(8)
_cod_database_code               7243927
_shelx_shelxl_version_number     2018/3
_olex2_refinement_description
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups, All N(H) groups
 At 1.5 times of:
  All C(H,H,H) groups, All O(H) groups
2.a Aromatic/amide H refined with riding coordinates:
 N00B(H00B), N00C(H00C), C00W(H00W), C00X(H00X), C00Z(H00Z), C011(H011),
 C013(H013), C014(H014), C015(H015), C016(H016), C017(H017), C018(H018),
 C019(H019), C01A(H01F), C01B(H01B), C01C(H01G), C01D(H01D), C01E(H01H),
 C01G(H01I), C01H(H01J), C01I(H01K), C01J(H01L)
2.b Idealised Me refined as rotating group:
 C01F(H01A,H01C,H01E), C01K(H01M,H01N,H01O)
2.c Idealised tetrahedral OH refined as rotating group:
 O003(H003), O007(H007)
;
_shelx_res_checksum              49642
_olex2_submission_special_instructions 'No special instructions were received'