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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/7/23/83/7238341.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_7238341
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         'C22 H16 N4 O4'
_chemical_formula_sum            'C22 H16 N4 O4'
_chemical_formula_weight         400.39
_space_group_IT_number           18
_space_group_name_Hall           'P 2 2ab'
_space_group_name_H-M_alt        'P 21 21 2'
_symmetry_cell_setting           orthorhombic
_symmetry_space_group_name_H-M   'P 21 21 2'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_cell_angle_alpha                90.00
_cell_angle_beta                 90.00
_cell_angle_gamma                90.00
_cell_formula_units_Z            2
_cell_length_a                   5.0497(3)
_cell_length_b                   28.8108(15)
_cell_length_c                   6.3242(4)
_cell_measurement_reflns_used    8993
_cell_measurement_temperature    120(2)
_cell_measurement_theta_max      27.48
_cell_measurement_theta_min      2.91
_cell_volume                     920.08(9)
_computing_cell_refinement
'DENZO (Otwinowski & Minor, 1997) & COLLECT (Hooft, R.W.W., 1998)'
_computing_data_collection       'COLLECT (Hooft, R.W.W., 1998)'
_computing_data_reduction
'DENZO (Otwinowski & Minor, 1997) & COLLECT (Hooft, R.W.W., 1998)'
_computing_molecular_graphics    'CAMERON (Watkin, et al., 1993)'
_computing_publication_material  'WINGX (Farrugia, 1998)'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 2008)'
_computing_structure_solution    SIR2004
_diffrn_ambient_temperature      120(2)
_diffrn_detector_area_resol_mean 9.091
_diffrn_measured_fraction_theta_full 0.994
_diffrn_measured_fraction_theta_max 0.994
_diffrn_measurement_device_type  'Bruker-Nonius CCD camera on κ-goniostat'
_diffrn_measurement_method       'φ & ω scans to fill the asymmetric unit'
_diffrn_radiation_monochromator  '10cm confocal mirrors'
_diffrn_radiation_source         'Bruker Nonius FR591 Rotating Anode'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0770
_diffrn_reflns_av_sigmaI/netI    0.0675
_diffrn_reflns_limit_h_max       6
_diffrn_reflns_limit_h_min       -6
_diffrn_reflns_limit_k_max       37
_diffrn_reflns_limit_k_min       -35
_diffrn_reflns_limit_l_max       8
_diffrn_reflns_limit_l_min       -7
_diffrn_reflns_number            5825
_diffrn_reflns_theta_full        27.49
_diffrn_reflns_theta_max         27.49
_diffrn_reflns_theta_min         3.30
_diffrn_standards_number         0
_exptl_absorpt_coefficient_mu    0.102
_exptl_absorpt_correction_T_max  0.7297
_exptl_absorpt_correction_T_min  0.5325
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
SADABS V2.10 (Sheldrick, G.M., 2003)
;
_exptl_crystal_colour            'Clear Colourless'
_exptl_crystal_density_diffrn    1.445
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       Needle
_exptl_crystal_F_000             416
_exptl_crystal_size_max          0.12
_exptl_crystal_size_mid          0.04
_exptl_crystal_size_min          0.04
_refine_diff_density_max         0.420
_refine_diff_density_min         -0.329
_refine_diff_density_rms         0.085
_refine_ls_abs_structure_details 'Flack H D (1983), Acta Cryst. A39, 876-881'
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.831
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     137
_refine_ls_number_reflns         1285
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.831
_refine_ls_R_factor_all          0.1268
_refine_ls_R_factor_gt           0.0854
_refine_ls_shift/su_max          0.003
_refine_ls_shift/su_mean         0.001
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'calc w=1/[σ²(Fo²)+(0.0100P)²+0.0000P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1211
_refine_ls_wR_factor_ref         0.1296
_reflns_number_gt                937
_reflns_number_total             1285
_reflns_threshold_expression     >2σ(I)
_cod_data_source_file            c0ce00243g.txt
_cod_data_source_block           3d
_cod_original_sg_symbol_H-M      P2(1)2(1)2
_cod_database_code               7238341
loop_
_chemical_name_systematic
;
di-2-(pyridyl)methyl 1,8-naphthyridine-2,7-dicarboxylate
;
loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'-x, -y, z'
'x+1/2, -y+1/2, -z'
'-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_symmetry_multiplicity
_atom_site_calc_flag
_atom_site_refinement_flags
O8 O -0.4933(6) -0.08807(9) -1.6593(4) 0.0299(8) Uani 1 1 d .
O9 O -0.6887(6) -0.10674(9) -1.3534(5) 0.0241(8) Uani 1 1 d .
N1 N -0.1675(7) -0.02716(11) -1.4431(5) 0.0191(9) Uani 1 1 d .
N12 N -1.2062(8) -0.19182(12) -1.4078(6) 0.0267(10) Uani 1 1 d .
C2 C -0.3364(9) -0.05350(14) -1.3369(7) 0.0219(10) Uani 1 1 d .
C3 C -0.3518(9) -0.05516(14) -1.1158(7) 0.0217(11) Uani 1 1 d .
H3 H -0.4753 -0.0743 -1.0504 0.026 Uiso 1 1 calc R
C4 C -0.1840(8) -0.02840(14) -0.9959(7) 0.0231(10) Uani 1 1 d .
H4 H -0.1915 -0.0290 -0.8489 0.028 Uiso 1 1 calc R
C5 C 0.0000 0.0000 -1.1030(9) 0.0186(14) Uani 1 2 d S
C6 C 0.0000 0.0000 -1.3262(10) 0.0198(14) Uani 1 2 d S
C7 C -0.5093(9) -0.08370(14) -1.4718(7) 0.0224(10) Uani 1 1 d .
C10 C -0.8610(9) -0.13805(14) -1.4690(6) 0.0234(11) Uani 1 1 d .
H10A H -0.7559 -0.1607 -1.5450 0.028 Uiso 1 1 calc R
H10B H -0.9652 -0.1207 -1.5709 0.028 Uiso 1 1 calc R
C11 C -1.0409(9) -0.16214(13) -1.3153(7) 0.0214(11) Uani 1 1 d .
C13 C -1.3814(10) -0.21395(15) -1.2814(8) 0.0290(13) Uani 1 1 d .
H13 H -1.4987 -0.2348 -1.3434 0.035 Uiso 1 1 calc R
C14 C -1.3959(10) -0.20729(14) -1.0649(8) 0.0265(13) Uani 1 1 d .
H14 H -1.5217 -0.2230 -0.9846 0.032 Uiso 1 1 calc R
C15 C -1.2206(9) -0.17704(14) -0.9702(7) 0.0240(11) Uani 1 1 d .
H15 H -1.2243 -0.1721 -0.8250 0.029 Uiso 1 1 calc R
C16 C -1.0379(10) -0.15416(14) -1.0979(7) 0.0244(11) Uani 1 1 d .
H16 H -0.9155 -0.1338 -1.0390 0.029 Uiso 1 1 calc R
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 0.0000 '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 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0106 0.0000 '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
C7 O9 C10 115.4(3) .
C2 N1 C6 116.8(4) .
C11 N12 C13 117.0(4) .
N1 C2 C3 124.2(4) .
N1 C2 C7 114.7(4) .
C3 C2 C7 121.1(4) .
C4 C3 C2 119.8(4) .
C4 C3 H3 120.1 .
C2 C3 H3 120.1 .
C3 C4 C5 117.8(4) .
C3 C4 H4 121.1 .
C5 C4 H4 121.1 .
C4 C5 C4 122.6(6) 2
C4 C5 C6 118.7(3) 2
C4 C5 C6 118.7(3) .
N1 C6 N1 114.6(5) 2
N1 C6 C5 122.7(3) 2
N1 C6 C5 122.7(3) .
O8 C7 O9 123.0(4) .
O8 C7 C2 125.9(4) .
O9 C7 C2 111.1(3) .
O9 C10 C11 108.9(3) .
O9 C10 H10A 109.9 .
C11 C10 H10A 109.9 .
O9 C10 H10B 109.9 .
C11 C10 H10B 109.9 .
H10A C10 H10B 108.3 .
N12 C11 C16 123.1(4) .
N12 C11 C10 113.1(4) .
C16 C11 C10 123.8(4) .
N12 C13 C14 123.6(5) .
N12 C13 H13 118.2 .
C14 C13 H13 118.2 .
C15 C14 C13 118.9(5) .
C15 C14 H14 120.6 .
C13 C14 H14 120.6 .
C14 C15 C16 118.2(4) .
C14 C15 H15 120.9 .
C16 C15 H15 120.9 .
C15 C16 C11 119.1(5) .
C15 C16 H16 120.4 .
C11 C16 H16 120.4 .
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
O8 C7 1.195(5) .
O9 C7 1.350(5) .
O9 C10 1.451(4) .
N1 C2 1.325(5) .
N1 C6 1.369(4) .
N12 C11 1.331(5) .
N12 C13 1.352(6) .
C2 C3 1.401(6) .
C2 C7 1.499(6) .
C3 C4 1.374(5) .
C3 H3 0.9300 .
C4 C5 1.412(5) .
C4 H4 0.9300 .
C5 C4 1.412(5) 2
C5 C6 1.411(8) .
C6 N1 1.369(4) 2
C10 C11 1.501(5) .
C10 H10A 0.9700 .
C10 H10B 0.9700 .
C11 C16 1.394(6) .
C13 C14 1.385(6) .
C13 H13 0.9300 .
C14 C15 1.379(6) .
C14 H14 0.9300 .
C15 C16 1.392(6) .
C15 H15 0.9300 .
C16 H16 0.9300 .
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 -0.3(6) . .
C6 N1 C2 C7 -178.1(3) . .
N1 C2 C3 C4 -0.2(7) . .
C7 C2 C3 C4 177.5(4) . .
C2 C3 C4 C5 -0.1(6) . .
C3 C4 C5 C4 -179.1(4) . 2
C3 C4 C5 C6 0.9(4) . .
C2 N1 C6 N1 -178.9(4) . 2
C2 N1 C6 C5 1.1(4) . .
C4 C5 C6 N1 -1.4(3) 2 2
C4 C5 C6 N1 178.6(3) . 2
C4 C5 C6 N1 178.6(3) 2 .
C4 C5 C6 N1 -1.4(3) . .
C10 O9 C7 O8 0.8(6) . .
C10 O9 C7 C2 -178.3(3) . .
N1 C2 C7 O8 5.6(7) . .
C3 C2 C7 O8 -172.3(4) . .
N1 C2 C7 O9 -175.4(3) . .
C3 C2 C7 O9 6.7(6) . .
C7 O9 C10 C11 177.9(3) . .
C13 N12 C11 C16 1.6(7) . .
C13 N12 C11 C10 -177.9(4) . .
O9 C10 C11 N12 -179.8(4) . .
O9 C10 C11 C16 0.8(6) . .
C11 N12 C13 C14 -0.1(7) . .
N12 C13 C14 C15 -1.0(7) . .
C13 C14 C15 C16 0.6(6) . .
C14 C15 C16 C11 0.8(6) . .
N12 C11 C16 C15 -1.9(7) . .
C10 C11 C16 C15 177.5(4) . .
loop_
_cod_related_entry_id
_cod_related_entry_database
_cod_related_entry_code
1 PubChem 168340350
