#------------------------------------------------------------------------------
#$Date: 2023-05-05 06:18:15 +0300 (Fri, 05 May 2023) $
#$Revision: 283454 $
#$URL: file:///home/coder/svn-repositories/cod/cif/7/15/92/7159245.cif $
#------------------------------------------------------------------------------
#
# This file is available in the Crystallography Open Database (COD),
# http://www.crystallography.net/
#
# All data on this site have been placed in the public domain by the
# contributors.
#
data_7159245
loop_
_publ_author_name
'Beghennou, Anissa'
'Gontard, Geoffrey'
'Dossmann, Héloïse'
'Passador, Kévin'
'Thorimbert, Serge'
'Corcé, Vincent'
'Botuha, Candice'
_publ_section_title
;
 1,6-Naphthyridin-7(6H)-ones: synthesis and optical properties.
;
_journal_issue                   14
_journal_name_full               'Organic & 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       'φ and ω 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/[σ²(Fo²)+(0.0484P)²+1.0132P] where P=(Fo²+2Fc²)/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 > 2σ(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_space_group_comment
;
The symmetry employed for this shelxl refinement is uniquely defined
by the following loop, which should always be used as a source of
symmetry information in preference to the above space-group names.
They are only intended as comments.
;
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x+1/2, -y, z+1/2'
'-x, y+1/2, -z+1/2'
'x+1/2, -y+1/2, -z'
'-x, -y, -z'
'x-1/2, y, -z-1/2'
'x, -y-1/2, z-1/2'
'-x-1/2, y-1/2, z'
loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_site_symmetry_order
_atom_site_calc_flag
_atom_site_refinement_flags_posn
_atom_site_refinement_flags_adp
_atom_site_refinement_flags_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
Cl1 Cl 0.52929(6) 0.60616(3) 0.16546(2) 0.03890(15) Uani 1 1 d . . . . .
O1 O 0.04924(14) 0.89979(6) 0.53164(5) 0.0236(2) Uani 1 1 d . . . . .
O2 O 0.65235(19) 0.53278(9) 0.28974(6) 0.0471(3) Uani 1 1 d G . . . .
H2A H 0.624925 0.555327 0.249952 0.057 Uiso 1 1 d G U . . .
H2B H 0.765756 0.557010 0.299096 0.057 Uiso 1 1 d G U . . .
N1 N 0.11291(16) 0.94576(8) 0.43552(5) 0.0237(3) Uani 1 1 d . . . . .
H1 H 0.066197 0.997050 0.445090 0.028 Uiso 1 1 calc R U . . .
N2 N 0.37447(15) 0.71951(7) 0.39234(5) 0.0201(3) Uani 1 1 d . . . . .
H2C H 0.399818 0.680737 0.420898 0.024 Uiso 1 1 calc R U . . .
C1 C 0.12027(18) 0.88184(9) 0.48110(6) 0.0201(3) Uani 1 1 d . . . . .
C2 C 0.20660(18) 0.80166(9) 0.46643(6) 0.0188(3) Uani 1 1 d . . . . .
C3 C 0.27595(18) 0.79264(9) 0.40815(6) 0.0193(3) Uani 1 1 d . . . . .
C4 C 0.25454(19) 0.85791(9) 0.36205(6) 0.0224(3) Uani 1 1 d . . . . .
C5 C 0.1705(2) 0.93564(10) 0.37894(7) 0.0258(3) Uani 1 1 d . . . . .
H5 H 0.154363 0.981477 0.349905 0.031 Uiso 1 1 calc R U . . .
C6 C 0.3184(2) 0.84256(11) 0.30236(7) 0.0277(3) Uani 1 1 d . . . . .
H6 H 0.302532 0.885841 0.271490 0.033 Uiso 1 1 calc R U . . .
C7 C 0.4029(2) 0.76529(11) 0.28926(7) 0.0293(4) Uani 1 1 d . . . . .
H7 H 0.440858 0.752761 0.248900 0.035 Uiso 1 1 calc R U . . .
C8 C 0.4324(2) 0.70503(10) 0.33648(7) 0.0260(3) Uani 1 1 d . . . . .
H8 H 0.495668 0.652350 0.328145 0.031 Uiso 1 1 calc R U . . .
C9 C 0.21332(17) 0.73045(9) 0.51316(6) 0.0194(3) Uani 1 1 d . . . . .
C10 C 0.28006(19) 0.74798(10) 0.57110(6) 0.0247(3) Uani 1 1 d . . . . .
H10 H 0.327423 0.804493 0.580146 0.030 Uiso 1 1 calc R U . . .
C11 C 0.2773(2) 0.68294(12) 0.61548(7) 0.0331(4) Uani 1 1 d . . . . .
H11 H 0.323728 0.694998 0.654831 0.040 Uiso 1 1 calc R U . . .
C12 C 0.2076(2) 0.60068(12) 0.60305(8) 0.0371(4) Uani 1 1 d . . . . .
H12 H 0.202821 0.556990 0.634089 0.044 Uiso 1 1 calc R U . . .
C13 C 0.1450(2) 0.58222(10) 0.54536(8) 0.0323(4) Uani 1 1 d . . . . .
H13 H 0.099941 0.525176 0.536500 0.039 Uiso 1 1 calc R U . . .
C14 C 0.14735(19) 0.64649(10) 0.50015(7) 0.0234(3) Uani 1 1 d . . . . .
H14 H 0.104235 0.633368 0.460508 0.028 Uiso 1 1 calc R U . . .
loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0181 0.0091 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
N N 0.0311 0.0180 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0492 0.0322 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
Cl Cl 0.3639 0.7018 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
C5 N1 C1 125.33(12) . . ?
C8 N2 C3 123.18(12) . . ?
O1 C1 N1 117.56(12) . . ?
O1 C1 C2 125.59(13) . . ?
N1 C1 C2 116.84(12) . . ?
C3 C2 C1 117.97(12) . . ?
C3 C2 C9 123.26(12) . . ?
C1 C2 C9 118.73(12) . . ?
N2 C3 C2 121.05(12) . . ?
N2 C3 C4 116.17(12) . . ?
C2 C3 C4 122.76(13) . . ?
C5 C4 C6 122.92(13) . . ?
C5 C4 C3 116.87(13) . . ?
C6 C4 C3 120.21(13) . . ?
N1 C5 C4 119.98(13) . . ?
C7 C6 C4 119.79(14) . . ?
C6 C7 C8 118.65(14) . . ?
N2 C8 C7 121.64(14) . . ?
C10 C9 C14 119.38(13) . . ?
C10 C9 C2 120.11(13) . . ?
C14 C9 C2 120.48(12) . . ?
C11 C10 C9 119.95(15) . . ?
C12 C11 C10 120.60(15) . . ?
C13 C12 C11 119.74(14) . . ?
C12 C13 C14 120.48(15) . . ?
C13 C14 C9 119.81(14) . . ?
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
O1 C1 1.2624(18) . ?
N1 C5 1.3245(19) . ?
N1 C1 1.3928(18) . ?
N2 C8 1.3200(19) . ?
N2 C3 1.3820(18) . ?
C1 C2 1.418(2) . ?
C2 C3 1.389(2) . ?
C2 C9 1.4887(19) . ?
C3 C4 1.4236(19) . ?
C4 C5 1.391(2) . ?
C4 C6 1.415(2) . ?
C6 C7 1.366(2) . ?
C7 C8 1.399(2) . ?
C9 C10 1.394(2) . ?
C9 C14 1.397(2) . ?
C10 C11 1.385(2) . ?
C11 C12 1.382(3) . ?
C12 C13 1.380(3) . ?
C13 C14 1.390(2) . ?
