1,6-Naphthyridin-7(6<i>H</i>)-ones: synthesis and optical properties.
Beghennou, Anissa; Gontard, Geoffrey; Dossmann, Héloïse; Passador, Kévin; Thorimbert, Serge; Corcé, Vincent; Botuha, Candice; Organic & biomolecular chemistry 21 (2023) 2976–2982; doi:10.1039/d3ob00081h

data_7159245
_publ_section_title
;
 1,6-Naphthyridin-7(6<i>H</i>)-ones: synthesis and optical properties.
;
_journal_issue                   14
_journal_name_full               'Organic &amp; biomolecular chemistry'
_journal_page_first              2976
_journal_page_last               2982
_journal_paper_doi               10.1039/d3ob00081h
_journal_volume                  21
_journal_year                    2023
_chemical_formula_moiety         'C14 H11 N2 O, Cl, H2 O'
_chemical_formula_sum            'C14 H13 Cl N2 O2'
_chemical_formula_weight         276.71
_space_group_crystal_system      orthorhombic
_space_group_IT_number           61
_space_group_name_Hall           '-P 2ac 2ab'
_space_group_name_H-M_alt        'P b c a'
_atom_sites_solution_hydrogens   mixed
_atom_sites_solution_primary     dual
_atom_sites_solution_secondary   difmap
_audit_creation_method           SHELXL-2018/3
_audit_update_record
;
2022-07-28 deposited with the CCDC.	2023-03-13 downloaded from the CCDC.
;
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_formula_units_Z            8
_cell_length_a                   7.6114(4)
_cell_length_b                   15.1521(7)
_cell_length_c                   21.9238(11)
_cell_measurement_reflns_used    6230
_cell_measurement_temperature    200(1)
_cell_measurement_theta_max      67.82
_cell_measurement_theta_min      4.04
_cell_volume                     2528.4(2)
_computing_cell_refinement       'Bruker SAINT'
_computing_data_collection       'Bruker APEX2'
_computing_data_reduction        'Bruker SAINT'
_computing_molecular_graphics    'SXGRAPH (Farrugia, 2012)'
_computing_publication_material  'WinGX (Farrugia, 2012)'
_computing_structure_refinement  'SHELXL (Sheldrick, 2015)'
_computing_structure_solution    'SHELXT (Sheldrick, 2015)'
_diffrn_ambient_temperature      200(1)
_diffrn_measured_fraction_theta_full 0.997
_diffrn_measured_fraction_theta_max 0.997
_diffrn_measurement_device_type  'Bruker APEX-II CCD'
_diffrn_measurement_method       '\f and \w scans'
_diffrn_radiation_source         micro-source
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54178
_diffrn_reflns_av_R_equivalents  0.0351
_diffrn_reflns_av_unetI/netI     0.0225
_diffrn_reflns_Laue_measured_fraction_full 0.997
_diffrn_reflns_Laue_measured_fraction_max 0.997
_diffrn_reflns_limit_h_max       6
_diffrn_reflns_limit_h_min       -9
_diffrn_reflns_limit_k_max       18
_diffrn_reflns_limit_k_min       -17
_diffrn_reflns_limit_l_max       26
_diffrn_reflns_limit_l_min       -25
_diffrn_reflns_number            16493
_diffrn_reflns_point_group_measured_fraction_full 0.997
_diffrn_reflns_point_group_measured_fraction_max 0.997
_diffrn_reflns_theta_full        66.500
_diffrn_reflns_theta_max         66.592
_diffrn_reflns_theta_min         4.033
_exptl_absorpt_coefficient_mu    2.677
_exptl_absorpt_correction_T_max  0.950
_exptl_absorpt_correction_T_min  0.497
_exptl_absorpt_correction_type   numerical
_exptl_absorpt_process_details
; 
 SADABS : Krause, L., Herbst-Irmer, R., Sheldrick G.M. & Stalke D.,
 J. Appl. Cryst. 48 (2015) 3-10
;
_exptl_crystal_colour_modifier   reddish
_exptl_crystal_colour_primary    orange
_exptl_crystal_density_diffrn    1.454
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       needle
_exptl_crystal_F_000             1152
_exptl_crystal_size_max          0.350
_exptl_crystal_size_mid          0.050
_exptl_crystal_size_min          0.050
_refine_diff_density_max         0.194
_refine_diff_density_min         -0.285
_refine_diff_density_rms         0.042
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.049
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     175
_refine_ls_number_reflns         2218
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.049
_refine_ls_R_factor_all          0.0353
_refine_ls_R_factor_gt           0.0311
_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^)+(0.0484P)^2^+1.0132P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0850
_refine_ls_wR_factor_ref         0.0881
_reflns_number_gt                1981
_reflns_number_total             2218
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            d3ob00081h2.cif
_cod_data_source_block           anb050
_cod_depositor_comments          'Adding full bibliography for 7159245.cif.'
_cod_database_code               7159245
_shelx_shelxl_version_number     2018/3
_shelx_res_checksum              30259