#------------------------------------------------------------------------------
#$Date: 2025-08-18 16:30:32 +0300 (Mon, 18 Aug 2025) $
#$Revision: 301775 $
#$URL: file:///home/coder/svn-repositories/cod/cif/1/50/68/1506882.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_1506882
loop_
_publ_author_name
'Wu, Zong-Quan'
'Jiang, Xi-Kui'
'Zhu, Shi-Zheng'
'Li, Zhan-Ting'
_publ_section_title
;
 Hydrogen bond-induced rigid oligoanthranilamide ribbons that are planar
 and straight.
;
_journal_issue                   2
_journal_name_full               'Organic letters'
_journal_page_first              229
_journal_page_last               232
_journal_paper_doi               10.1021/ol036108b
_journal_volume                  6
_journal_year                    2004
_chemical_formula_sum            'C26 H24 N2 O8'
_chemical_formula_weight         492.47
_space_group_IT_number           14
_symmetry_cell_setting           monoclinic
_symmetry_space_group_name_Hall  '-P 2yn'
_symmetry_space_group_name_H-M   'P 1 21/n 1'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_audit_creation_method           SHELXL-97
_cell_angle_alpha                90.00
_cell_angle_beta                 91.477(3)
_cell_angle_gamma                90.00
_cell_formula_units_Z            2
_cell_length_a                   4.0457(6)
_cell_length_b                   9.8264(16)
_cell_length_c                   28.394(4)
_cell_measurement_reflns_used    943
_cell_measurement_temperature    293(2)
_cell_measurement_theta_max      43.064
_cell_measurement_theta_min      4.387
_cell_volume                     1128.4(3)
_computing_cell_refinement       'Bruker SMART'
_computing_data_collection       'Bruker SMART'
_computing_data_reduction        'Bruker SHELXTL'
_computing_molecular_graphics    'Bruker SHELXTL'
_computing_publication_material  'Bruker SHELXTL'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 1990)'
_diffrn_ambient_temperature      293(2)
_diffrn_measured_fraction_theta_full 0.936
_diffrn_measured_fraction_theta_max 0.936
_diffrn_measurement_device_type  'CCD area detector'
_diffrn_measurement_method       'phi and omega scans'
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_source         'fine-focus sealed tube'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.1174
_diffrn_reflns_av_sigmaI/netI    0.1189
_diffrn_reflns_limit_h_max       5
_diffrn_reflns_limit_h_min       -5
_diffrn_reflns_limit_k_max       11
_diffrn_reflns_limit_k_min       -12
_diffrn_reflns_limit_l_max       36
_diffrn_reflns_limit_l_min       -35
_diffrn_reflns_number            6691
_diffrn_reflns_theta_full        28.29
_diffrn_reflns_theta_max         28.29
_diffrn_reflns_theta_min         2.19
_exptl_absorpt_coefficient_mu    0.109
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.47443
_exptl_absorpt_correction_type   sadabs
_exptl_crystal_colour            colourless
_exptl_crystal_density_diffrn    1.449
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             516
_exptl_crystal_size_max          0.455
_exptl_crystal_size_mid          0.216
_exptl_crystal_size_min          0.047
_refine_diff_density_max         0.298
_refine_diff_density_min         -0.200
_refine_diff_density_rms         0.054
_refine_ls_extinction_coef       0.017(3)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc²λ³/sin(2θ)]^-1/4^
_refine_ls_extinction_method     SHELXL
_refine_ls_goodness_of_fit_ref   0.839
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     212
_refine_ls_number_reflns         2625
_refine_ls_number_restraints     4
_refine_ls_restrained_S_all      0.839
_refine_ls_R_factor_all          0.1085
_refine_ls_R_factor_gt           0.0569
_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)+(0.0470P)²+0.0000P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1249
_refine_ls_wR_factor_ref         0.1397
_reflns_number_gt                1331
_reflns_number_total             2625
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            ol036108bsi20031028_092815.cif
_cod_data_source_block           cd23211
_cod_depositor_comments
;
The following automatic conversions were performed:

'_symmetry_cell_setting' value 'Monoclinic' changed to 'monoclinic'
according to /home/saulius/struct/CIF-dictionaries/cif_core.dic
dictionary named 'cif_core.dic' version 2.4.1 from 2010-06-29.

Automatic conversion script
Id: cif_fix_values 1715 2011-07-08 13:25:40Z adriana 
;
_cod_original_sg_symbol_H-M      P2(1)/n
_cod_database_code               1506882
loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'-x+1/2, y+1/2, -z+1/2'
'-x, -y, -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
N1 N 0.3108(5) 0.69747(18) 0.88774(6) 0.0423(5) Uani 1 1 d D
O1 O 0.2920(4) 0.25669(15) 1.03671(5) 0.0529(5) Uani 1 1 d .
O2 O 0.1545(6) 0.47668(16) 0.88155(6) 0.0748(7) Uani 1 1 d .
O3 O 0.4880(6) 0.96213(17) 0.90616(6) 0.0749(7) Uani 1 1 d .
O4 O 0.5343(4) 1.09382(15) 0.84380(5) 0.0554(5) Uani 1 1 d .
C1 C 0.3966(6) 0.3761(2) 1.01750(7) 0.0384(6) Uani 1 1 d .
C2 C 0.3074(6) 0.4162(2) 0.97245(8) 0.0393(6) Uani 1 1 d .
C3 C 0.4085(6) 0.5401(2) 0.95357(7) 0.0358(6) Uani 1 1 d .
C4 C 0.2798(6) 0.5680(2) 0.90414(8) 0.0417(6) Uani 1 1 d .
C5 C 0.1992(5) 0.7491(2) 0.84403(7) 0.0356(5) Uani 1 1 d .
C6 C 0.0240(6) 0.6695(3) 0.81141(8) 0.0463(7) Uani 1 1 d .
C7 C -0.0785(7) 0.7220(3) 0.76854(9) 0.0512(7) Uani 1 1 d .
C8 C -0.0030(7) 0.8538(3) 0.75606(9) 0.0527(7) Uani 1 1 d .
C9 C 0.1666(6) 0.9330(3) 0.78782(8) 0.0466(6) Uani 1 1 d .
C10 C 0.2674(5) 0.8856(2) 0.83210(7) 0.0370(6) Uani 1 1 d .
C11 C 0.1252(9) 0.1593(3) 1.00780(11) 0.0546(8) Uani 1 1 d .
C12 C 0.4385(6) 0.9801(2) 0.86486(8) 0.0422(6) Uani 1 1 d .
C13 C 0.7003(9) 1.1960(3) 0.87229(11) 0.0623(9) Uani 1 1 d D
H1 H 0.171(5) 0.3644(19) 0.9545(7) 0.029(5) Uiso 1 1 d .
H2 H -0.039(6) 0.583(2) 0.8183(8) 0.047(7) Uiso 1 1 d .
H3 H -0.210(6) 0.671(2) 0.7481(8) 0.052(7) Uiso 1 1 d .
H4 H -0.062(5) 0.884(2) 0.7253(7) 0.040(6) Uiso 1 1 d .
H5 H 0.203(6) 1.025(2) 0.7801(8) 0.059(7) Uiso 1 1 d .
H6 H 0.104(7) 0.087(3) 1.0317(10) 0.095(10) Uiso 1 1 d .
H7 H 0.276(6) 0.126(3) 0.9832(9) 0.071(9) Uiso 1 1 d .
H8 H -0.078(7) 0.195(3) 0.9922(9) 0.071(9) Uiso 1 1 d .
H11 H 0.858(7) 1.223(3) 0.8500(9) 0.112(13) Uiso 1 1 d D
H10 H 0.540(7) 1.252(3) 0.8868(10) 0.119(14) Uiso 1 1 d D
H9 H 0.842(7) 1.162(3) 0.8985(9) 0.105(12) Uiso 1 1 d D
H12 H 0.429(5) 0.757(2) 0.9078(8) 0.060(7) Uiso 1 1 d 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
C4 N1 C5 127.55(18) . .
C4 N1 H12 115.1(14) . .
C5 N1 H12 117.3(15) . .
C1 O1 C11 119.71(18) . .
C12 O4 C13 118.0(2) . .
O1 C1 C2 122.70(19) . .
O1 C1 C3 116.65(19) . 3_667
C2 C1 C3 120.6(2) . 3_667
C1 C2 C3 122.3(2) . .
C1 C2 H1 120.4(12) . .
C3 C2 H1 117.3(12) . .
C1 C3 C2 117.11(19) 3_667 .
C1 C3 C4 128.14(19) 3_667 .
C2 C3 C4 114.72(19) . .
O2 C4 N1 123.6(2) . .
O2 C4 C3 119.29(19) . .
N1 C4 C3 117.08(18) . .
C6 C5 N1 122.1(2) . .
C6 C5 C10 118.2(2) . .
N1 C5 C10 119.64(19) . .
C7 C6 C5 121.0(2) . .
C7 C6 H2 117.5(14) . .
C5 C6 H2 121.4(14) . .
C6 C7 C8 121.0(3) . .
C6 C7 H3 120.5(15) . .
C8 C7 H3 118.4(14) . .
C9 C8 C7 118.5(2) . .
C9 C8 H4 122.5(13) . .
C7 C8 H4 118.9(13) . .
C8 C9 C10 122.5(2) . .
C8 C9 H5 118.3(14) . .
C10 C9 H5 119.1(14) . .
C9 C10 C5 118.7(2) . .
C9 C10 C12 118.7(2) . .
C5 C10 C12 122.57(19) . .
O1 C11 H6 97.9(16) . .
O1 C11 H7 109.6(16) . .
H6 C11 H7 108(2) . .
O1 C11 H8 113.5(15) . .
H6 C11 H8 118(2) . .
H7 C11 H8 109(2) . .
O3 C12 O4 121.4(2) . .
O3 C12 C10 126.1(2) . .
O4 C12 C10 112.53(19) . .
O4 C13 H11 98(2) . .
O4 C13 H10 109(2) . .
H11 C13 H10 127(3) . .
O4 C13 H9 116.1(19) . .
H11 C13 H9 102(3) . .
H10 C13 H9 105(3) . .
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
N1 C4 1.362(3) .
N1 C5 1.404(3) .
N1 H12 0.940(16) .
O1 C1 1.366(2) .
O1 C11 1.420(3) .
O2 C4 1.207(2) .
O3 C12 1.197(3) .
O4 C12 1.330(3) .
O4 C13 1.444(3) .
C1 C2 1.378(3) .
C1 C3 1.393(3) 3_667
C2 C3 1.395(3) .
C2 H1 0.901(19) .
C3 C1 1.393(3) 3_667
C3 C4 1.509(3) .
C5 C6 1.392(3) .
C5 C10 1.412(3) .
C6 C7 1.376(3) .
C6 H2 0.91(2) .
C7 C8 1.379(4) .
C7 H3 0.92(2) .
C8 C9 1.363(3) .
C8 H4 0.948(19) .
C9 C10 1.392(3) .
C9 H5 0.94(2) .
C10 C12 1.474(3) .
C11 H6 0.99(3) .
C11 H7 1.00(3) .
C11 H8 0.99(3) .
C13 H11 0.946(18) .
C13 H10 0.953(18) .
C13 H9 0.987(17) .
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
C11 O1 C1 C2 9.5(4) . .
C11 O1 C1 C3 -172.7(2) . 3_667
O1 C1 C2 C3 178.3(2) . .
C3 C1 C2 C3 0.6(4) 3_667 .
C1 C2 C3 C1 -0.6(4) . 3_667
C1 C2 C3 C4 -178.6(2) . .
C5 N1 C4 O2 2.1(4) . .
C5 N1 C4 C3 -177.3(2) . .
C1 C3 C4 O2 169.3(3) 3_667 .
C2 C3 C4 O2 -13.0(3) . .
C1 C3 C4 N1 -11.2(4) 3_667 .
C2 C3 C4 N1 166.5(2) . .
C4 N1 C5 C6 2.4(4) . .
C4 N1 C5 C10 -177.0(2) . .
N1 C5 C6 C7 -179.1(2) . .
C10 C5 C6 C7 0.4(4) . .
C5 C6 C7 C8 1.8(4) . .
C6 C7 C8 C9 -2.2(4) . .
C7 C8 C9 C10 0.4(4) . .
C8 C9 C10 C5 1.8(4) . .
C8 C9 C10 C12 -177.7(2) . .
C6 C5 C10 C9 -2.1(3) . .
N1 C5 C10 C9 177.4(2) . .
C6 C5 C10 C12 177.3(2) . .
N1 C5 C10 C12 -3.3(3) . .
C13 O4 C12 O3 -0.1(4) . .
C13 O4 C12 C10 179.0(2) . .
C9 C10 C12 O3 166.2(3) . .
C5 C10 C12 O3 -13.2(4) . .
C9 C10 C12 O4 -12.9(3) . .
C5 C10 C12 O4 167.7(2) . .
loop_
_cod_related_entry_id
_cod_related_entry_database
_cod_related_entry_code
1 PubChem 12080457
