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#$Date: 2025-08-23 00:12:46 +0300 (Sat, 23 Aug 2025) $
#$Revision: 301866 $
#$URL: file:///home/coder/svn-repositories/cod/cif/7/23/83/7238340.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_7238340
loop_
_publ_author_name
'Bailey, Andrew James'
'Horton, Peter Neil'
'Grossel, Martin Christopher'
_publ_section_title
;
 Self-assembly into infinite tapes by 2,7-disubstituted-1,8-naphthyridines
 in the solid state
;
_journal_issue                   12
_journal_name_full               CrystEngComm
_journal_page_first              4074
_journal_paper_doi               10.1039/C0CE00243G
_journal_volume                  12
_journal_year                    2010
_chemical_formula_moiety         'C24 H18 N2 O4'
_chemical_formula_sum            'C24 H18 N2 O4'
_chemical_formula_weight         398.40
_chemical_name_systematic
;
dibenzyl 1,8-naphthyridine-2,7-dicarboxylate
;
_space_group_IT_number           15
_space_group_name_Hall           '-C 2yc'
_space_group_name_H-M_alt        'C 1 2/c 1'
_symmetry_cell_setting           monoclinic
_symmetry_space_group_name_H-M   'C 1 2/c 1'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_cell_angle_alpha                90.00
_cell_angle_beta                 93.849(13)
_cell_angle_gamma                90.00
_cell_formula_units_Z            4
_cell_length_a                   35.50(4)
_cell_length_b                   6.307(8)
_cell_length_c                   8.381(10)
_cell_measurement_reflns_used    967
_cell_measurement_temperature    120(2)
_cell_measurement_theta_max      27.95
_cell_measurement_theta_min      3.37
_cell_volume                     1872(4)
_computing_cell_refinement       'Bruker SAINT'
_computing_data_collection       'Bruker APEX2'
_computing_data_reduction        'Bruker SAINT'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 2008)'
_computing_structure_solution    SIR2004
_diffrn_ambient_temperature      120(2)
_diffrn_measured_fraction_theta_full 0.993
_diffrn_measured_fraction_theta_max 0.993
_diffrn_measurement_device_type  'Bruker SMART APEX2 CCD diffractometer'
_diffrn_measurement_method       'fine-slice ω scans'
_diffrn_radiation_monochromator  'silicon 111'
_diffrn_radiation_source         'Daresbury SRS station 9.8'
_diffrn_radiation_type           synchrotron
_diffrn_radiation_wavelength     0.6939
_diffrn_reflns_av_R_equivalents  0.0510
_diffrn_reflns_av_sigmaI/netI    0.0510
_diffrn_reflns_limit_h_max       46
_diffrn_reflns_limit_h_min       -46
_diffrn_reflns_limit_k_max       8
_diffrn_reflns_limit_k_min       -8
_diffrn_reflns_limit_l_max       11
_diffrn_reflns_limit_l_min       -11
_diffrn_reflns_number            8192
_diffrn_reflns_theta_full        28.28
_diffrn_reflns_theta_max         28.28
_diffrn_reflns_theta_min         3.45
_diffrn_standards_decay_%        5
_diffrn_standards_number         0
_exptl_absorpt_coefficient_mu    0.098
_exptl_absorpt_correction_type   none
_exptl_crystal_colour            colourless
_exptl_crystal_density_diffrn    1.413
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       lath
_exptl_crystal_F_000             832
_exptl_crystal_size_max          0.10
_exptl_crystal_size_mid          0.02
_exptl_crystal_size_min          0.005
_refine_diff_density_max         0.357
_refine_diff_density_min         -0.219
_refine_diff_density_rms         0.047
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.033
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     173
_refine_ls_number_reflns         2305
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.033
_refine_ls_R_factor_all          0.0718
_refine_ls_R_factor_gt           0.0486
_refine_ls_shift/su_max          0.001
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'calc w=1/[σ²(Fo²)+(0.0731P)²+0.2853P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1208
_refine_ls_wR_factor_ref         0.1328
_reflns_number_gt                1682
_reflns_number_total             2305
_reflns_threshold_expression     >2σ(I)
_cod_data_source_file            c0ce00243g.txt
_cod_data_source_block           3c
_cod_original_sg_symbol_H-M      'C 2/c'
_cod_database_code               7238340
loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'-x, y, -z+1/2'
'x+1/2, y+1/2, z'
'-x+1/2, y+1/2, -z+1/2'
'-x, -y, -z'
'x, -y, z-1/2'
'-x+1/2, -y+1/2, -z'
'x+1/2, -y+1/2, z-1/2'
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_symmetry_multiplicity
_atom_site_calc_flag
_atom_site_refinement_flags
O9 O 0.60679(3) 0.90138(17) -0.03904(14) 0.0275(3) Uani 1 1 d .
N1 N 0.52554(3) 0.9933(2) 0.17178(15) 0.0235(3) Uani 1 1 d .
O8 O 0.57558(3) 1.20835(17) -0.01119(14) 0.0303(3) Uani 1 1 d .
C5 C 0.5000 0.6513(3) 0.2500 0.0232(4) Uani 1 2 d S
C2 C 0.55058(4) 0.8859(2) 0.09402(19) 0.0233(3) Uani 1 1 d .
C6 C 0.5000 0.8771(3) 0.2500 0.0216(4) Uani 1 2 d S
C4 C 0.52737(4) 0.5447(2) 0.16545(19) 0.0263(4) Uani 1 1 d .
C11 C 0.65825(4) 0.8536(2) -0.20653(19) 0.0255(3) Uani 1 1 d .
C3 C 0.55269(4) 0.6615(2) 0.0871(2) 0.0262(3) Uani 1 1 d .
C10 C 0.63459(5) 1.0138(3) -0.1260(2) 0.0264(4) Uani 1 1 d .
C12 C 0.64412(5) 0.6556(3) -0.2560(2) 0.0282(4) Uani 1 1 d .
C7 C 0.57818(4) 1.0205(2) 0.00965(18) 0.0237(3) Uani 1 1 d .
C13 C 0.66615(5) 0.5177(3) -0.3400(2) 0.0330(4) Uani 1 1 d .
C15 C 0.71666(5) 0.7699(3) -0.3258(2) 0.0364(4) Uani 1 1 d .
C16 C 0.69480(5) 0.9080(3) -0.2409(2) 0.0316(4) Uani 1 1 d .
C14 C 0.70222(5) 0.5754(3) -0.3759(2) 0.0356(4) Uani 1 1 d .
H12 H 0.6185(5) 0.617(3) -0.232(2) 0.029(5) Uiso 1 1 d .
H10A H 0.6199(5) 1.102(3) -0.206(2) 0.037(5) Uiso 1 1 d .
H4 H 0.5279(4) 0.389(3) 0.161(2) 0.027(5) Uiso 1 1 d .
H14 H 0.7160(5) 0.479(3) -0.432(2) 0.038(5) Uiso 1 1 d .
H15 H 0.7424(6) 0.810(3) -0.347(3) 0.047(6) Uiso 1 1 d .
H3 H 0.5722(5) 0.596(3) 0.027(2) 0.032(5) Uiso 1 1 d .
H10B H 0.6502(5) 1.104(3) -0.050(2) 0.035(5) Uiso 1 1 d .
H16 H 0.7046(5) 1.051(3) -0.207(2) 0.033(5) Uiso 1 1 d .
H13 H 0.6565(6) 0.388(3) -0.376(2) 0.043(6) Uiso 1 1 d .
loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0033 0.0016 '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 0.0061 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0106 0.0060 '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
C7 O9 C10 115.56(14) . .
C2 N1 C6 116.79(15) . .
C4 C5 C4 123.1(2) . 2_655
C4 C5 C6 118.44(10) . .
C4 C5 C6 118.44(10) 2_655 .
N1 C2 C3 124.75(14) . .
N1 C2 C7 114.96(15) . .
C3 C2 C7 120.28(14) . .
N1 C6 N1 115.16(19) 2_655 .
N1 C6 C5 122.42(10) 2_655 .
N1 C6 C5 122.42(10) . .
C3 C4 C5 118.90(16) . .
C3 C4 H4 120.6(10) . .
C5 C4 H4 120.5(10) . .
C16 C11 C12 118.69(15) . .
C16 C11 C10 118.98(15) . .
C12 C11 C10 122.24(16) . .
C4 C3 C2 118.70(15) . .
C4 C3 H3 122.2(11) . .
C2 C3 H3 119.1(11) . .
O9 C10 C11 108.46(15) . .
O9 C10 H10A 105.6(11) . .
C11 C10 H10A 110.9(11) . .
O9 C10 H10B 109.1(11) . .
C11 C10 H10B 111.5(11) . .
H10A C10 H10B 111.0(15) . .
C13 C12 C11 120.37(17) . .
C13 C12 H12 120.6(10) . .
C11 C12 H12 119.1(10) . .
O8 C7 O9 123.91(15) . .
O8 C7 C2 125.29(14) . .
O9 C7 C2 110.79(15) . .
C14 C13 C12 120.33(18) . .
C14 C13 H13 119.1(12) . .
C12 C13 H13 120.6(13) . .
C14 C15 C16 120.07(18) . .
C14 C15 H15 120.5(12) . .
C16 C15 H15 119.4(12) . .
C11 C16 C15 120.73(17) . .
C11 C16 H16 118.3(10) . .
C15 C16 H16 120.9(10) . .
C15 C14 C13 119.80(16) . .
C15 C14 H14 122.5(12) . .
C13 C14 H14 117.7(12) . .
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
O9 C7 1.348(2) .
O9 C10 1.450(2) .
N1 C2 1.323(2) .
N1 C6 1.3671(19) .
O8 C7 1.200(2) .
C5 C4 1.411(2) .
C5 C4 1.411(2) 2_655
C5 C6 1.424(3) .
C2 C3 1.419(3) .
C2 C7 1.508(2) .
C6 N1 1.3671(19) 2_655
C4 C3 1.364(2) .
C4 H4 0.982(18) .
C11 C16 1.391(3) .
C11 C12 1.398(3) .
C11 C10 1.503(2) .
C3 H3 0.976(18) .
C10 H10A 0.990(19) .
C10 H10B 0.993(19) .
C12 C13 1.392(3) .
C12 H12 0.977(17) .
C13 C14 1.383(3) .
C13 H13 0.93(2) .
C15 C14 1.384(3) .
C15 C16 1.394(3) .
C15 H15 0.98(2) .
C16 H16 1.003(19) .
C14 H14 0.926(19) .
loop_
_geom_torsion_atom_site_label_1
_geom_torsion_atom_site_label_2
_geom_torsion_atom_site_label_3
_geom_torsion_atom_site_label_4
_geom_torsion
_geom_torsion_site_symmetry_1
_geom_torsion_site_symmetry_4
C6 N1 C2 C3 -0.2(2) . .
C6 N1 C2 C7 -179.97(11) . .
C2 N1 C6 N1 -179.65(15) . 2_655
C2 N1 C6 C5 0.35(15) . .
C4 C5 C6 N1 179.78(10) . 2_655
C4 C5 C6 N1 -0.22(10) 2_655 2_655
C4 C5 C6 N1 -0.22(10) . .
C4 C5 C6 N1 179.78(10) 2_655 .
C4 C5 C4 C3 179.95(17) 2_655 .
C6 C5 C4 C3 -0.05(17) . .
C5 C4 C3 C2 0.2(2) . .
N1 C2 C3 C4 0.0(3) . .
C7 C2 C3 C4 179.69(15) . .
C7 O9 C10 C11 -165.66(13) . .
C16 C11 C10 O9 -154.15(15) . .
C12 C11 C10 O9 29.4(2) . .
C16 C11 C12 C13 -0.9(2) . .
C10 C11 C12 C13 175.55(16) . .
C10 O9 C7 O8 -2.2(2) . .
C10 O9 C7 C2 178.33(13) . .
N1 C2 C7 O8 -11.5(2) . .
C3 C2 C7 O8 168.71(16) . .
N1 C2 C7 O9 167.95(13) . .
C3 C2 C7 O9 -11.8(2) . .
C11 C12 C13 C14 -0.2(3) . .
C12 C11 C16 C15 1.3(3) . .
C10 C11 C16 C15 -175.26(16) . .
C14 C15 C16 C11 -0.6(3) . .
C16 C15 C14 C13 -0.6(3) . .
C12 C13 C14 C15 1.0(3) . .
loop_
_cod_related_entry_id
_cod_related_entry_database
_cod_related_entry_code
1 PubChem 168340349
