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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/7/23/53/7235305.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_7235305
loop_
_publ_author_name
'Pandeeswar, M.'
'Khare, Harshavardhan'
'Ramakumar, Suryanarayanarao'
'Govindaraju, T.'
_publ_section_title
;
 Biomimetic molecular organization of naphthalene diimide in the solid
 state: tunable (chiro-) optical, viscoelastic and nanoscale properties
;
_journal_issue                   39
_journal_name_full               'RSC Adv.'
_journal_page_first              20154
_journal_paper_doi               10.1039/C3RA47257D
_journal_volume                  4
_journal_year                    2014
_chemical_formula_moiety         'C18 H14 N2 O4'
_chemical_formula_sum            'C18 H14 N2 O4'
_chemical_formula_weight         322.31
_space_group_crystal_system      monoclinic
_space_group_IT_number           14
_space_group_name_Hall           '-P 2ybc'
_space_group_name_H-M_alt        'P 1 21/c 1'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_audit_creation_method           SHELXL-2013
_cell_angle_alpha                90
_cell_angle_beta                 90.214(4)
_cell_angle_gamma                90
_cell_formula_units_Z            2
_cell_length_a                   4.8667(3)
_cell_length_b                   7.7561(4)
_cell_length_c                   18.3813(12)
_cell_measurement_reflns_used    2380
_cell_measurement_temperature    100(2)
_cell_measurement_theta_max      30.494
_cell_measurement_theta_min      2.216
_cell_volume                     693.83(7)
_computing_cell_refinement       'SAINTPLUS (BRUKER-AXS)'
_computing_data_collection       'KAPPA APEX II (BRUKER-AXS)'
_computing_data_reduction        'SAINTPLUS (BRUKER-AXS)'
_computing_structure_refinement  'SHELXL-2013 (Sheldrick, 2013)'
_computing_structure_solution    'SHELXL-2013 (Sheldrick, 2013)'
_diffrn_ambient_temperature      100(2)
_diffrn_measured_fraction_theta_full 0.962
_diffrn_measured_fraction_theta_max 0.883
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0361
_diffrn_reflns_av_unetI/netI     0.0444
_diffrn_reflns_Laue_measured_fraction_full 0.962
_diffrn_reflns_Laue_measured_fraction_max 0.883
_diffrn_reflns_limit_h_max       6
_diffrn_reflns_limit_h_min       -5
_diffrn_reflns_limit_k_max       11
_diffrn_reflns_limit_k_min       -11
_diffrn_reflns_limit_l_max       26
_diffrn_reflns_limit_l_min       -21
_diffrn_reflns_number            7676
_diffrn_reflns_point_group_measured_fraction_full 0.962
_diffrn_reflns_point_group_measured_fraction_max 0.883
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         30.543
_diffrn_reflns_theta_min         2.216
_exptl_absorpt_coefficient_mu    0.111
_exptl_absorpt_correction_T_max  0.7442
_exptl_absorpt_correction_T_min  0.6442
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   'SADABS (Bruker, 2008)'
_exptl_crystal_colour            colorless
_exptl_crystal_density_diffrn    1.543
_exptl_crystal_description       needle
_exptl_crystal_F_000             336
_exptl_crystal_size_max          0.300
_exptl_crystal_size_mid          0.120
_exptl_crystal_size_min          0.040
_refine_diff_density_max         0.497
_refine_diff_density_min         -0.273
_refine_diff_density_rms         0.063
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.053
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     109
_refine_ls_number_reflns         1863
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.053
_refine_ls_R_factor_all          0.0732
_refine_ls_R_factor_gt           0.0472
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
;
 w=1/[σ²(Fo²)+(0.0635P)²+0.1505P]
 where P=(Fo²+2Fc²)/3
;
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1130
_refine_ls_wR_factor_ref         0.1257
_reflns_Friedel_coverage         0.000
_reflns_number_gt                1346
_reflns_number_total             1863
_reflns_threshold_expression     'I > 2σ(I)'
_cod_data_source_file            c3ra47257d1.cif
_cod_data_source_block           50sd
_cod_original_sg_symbol_H-M      'P 21/c'
_cod_database_code               7235305
_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.
;
_shelx_estimated_absorpt_t_min   0.967
_shelx_estimated_absorpt_t_max   0.996
_shelxl_version_number           2013-2
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x, y+1/2, -z+1/2'
'-x, -y, -z'
'x, -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_site_symmetry_order
_atom_site_calc_flag
_atom_site_refinement_flags_posn
_atom_site_refinement_flags_adp
N1 N 0.1483(2) 0.33079(15) 0.37535(7) 0.0133(3) Uani 1 1 d . .
O2 O 0.4920(2) 0.16929(13) 0.32821(6) 0.0191(3) Uani 1 1 d . .
C4 C -0.1201(3) 0.22164(18) 0.47785(8) 0.0122(3) Uani 1 1 d . .
O1 O -0.2004(2) 0.49065(13) 0.42179(6) 0.0181(3) Uani 1 1 d . .
C2 C 0.0297(3) 0.06611(18) 0.47510(8) 0.0113(3) Uani 1 1 d . .
C5 C 0.2382(3) 0.04117(18) 0.42318(8) 0.0120(3) Uani 1 1 d . .
C6 C -0.0659(3) 0.35873(18) 0.42406(8) 0.0129(3) Uani 1 1 d . .
C3 C 0.3795(3) -0.11260(19) 0.42070(8) 0.0142(3) Uani 1 1 d . .
H3 H 0.5182 -0.1294 0.3852 0.017 Uiso 1 1 calc R U
C7 C 0.3067(3) 0.18130(18) 0.37216(8) 0.0130(3) Uani 1 1 d . .
C1 C -0.3199(3) 0.24438(19) 0.52966(9) 0.0141(3) Uani 1 1 d . .
H1 H -0.4181 0.3501 0.5318 0.017 Uiso 1 1 calc R U
C8 C 0.1992(3) 0.46240(19) 0.31894(9) 0.0161(3) Uani 1 1 d . .
H8A H 0.3995 0.4740 0.3111 0.019 Uiso 1 1 calc R U
H8B H 0.1282 0.5752 0.3357 0.019 Uiso 1 1 calc R U
C9 C 0.0608(3) 0.4139(2) 0.24803(9) 0.0201(4) Uani 1 1 d . .
H9A H 0.0979 0.5029 0.2115 0.030 Uiso 1 1 calc R U
H9B H -0.1379 0.4045 0.2555 0.030 Uiso 1 1 calc R U
H9C H 0.1328 0.3030 0.2311 0.030 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 0.0033 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
C6 N1 C7 124.86(12) . .
C6 N1 C8 118.13(11) . .
C7 N1 C8 116.82(11) . .
C1 C4 C2 120.10(13) . .
C1 C4 C6 120.00(12) . .
C2 C4 C6 119.89(12) . .
C2 C2 C5 119.45(15) 3_556 .
C2 C2 C4 119.53(15) 3_556 .
C5 C2 C4 121.02(13) . .
C3 C5 C2 120.14(13) . .
C3 C5 C7 120.20(12) . .
C2 C5 C7 119.65(12) . .
O1 C6 N1 120.86(13) . .
O1 C6 C4 122.13(12) . .
N1 C6 C4 117.01(12) . .
C5 C3 C1 120.36(12) . 3_556
C5 C3 H3 119.8 . .
C1 C3 H3 119.8 3_556 .
O2 C7 N1 120.21(13) . .
O2 C7 C5 122.40(13) . .
N1 C7 C5 117.38(11) . .
C4 C1 C3 120.41(13) . 3_556
C4 C1 H1 119.8 . .
C3 C1 H1 119.8 3_556 .
N1 C8 C9 110.99(12) . .
N1 C8 H8A 109.4 . .
C9 C8 H8A 109.4 . .
N1 C8 H8B 109.4 . .
C9 C8 H8B 109.4 . .
H8A C8 H8B 108.0 . .
C8 C9 H9A 109.5 . .
C8 C9 H9B 109.5 . .
H9A C9 H9B 109.5 . .
C8 C9 H9C 109.5 . .
H9A C9 H9C 109.5 . .
H9B C9 H9C 109.5 . .
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
N1 C6 1.3935(17) .
N1 C7 1.3939(18) .
N1 C8 1.4765(19) .
O2 C7 1.2164(16) .
C4 C1 1.3751(18) .
C4 C2 1.4105(19) .
C4 C6 1.476(2) .
O1 C6 1.2154(17) .
C2 C2 1.406(3) 3_556
C2 C5 1.4088(18) .
C5 C3 1.378(2) .
C5 C7 1.475(2) .
C3 C1 1.401(2) 3_556
C3 H3 0.9500 .
C1 C3 1.401(2) 3_556
C1 H1 0.9500 .
C8 C9 1.512(2) .
C8 H8A 0.9900 .
C8 H8B 0.9900 .
C9 H9A 0.9800 .
C9 H9B 0.9800 .
C9 H9C 0.9800 .
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
C1 C4 C2 C2 1.0(3) . 3_556
C6 C4 C2 C2 -177.78(16) . 3_556
C1 C4 C2 C5 -179.01(14) . .
C6 C4 C2 C5 2.2(2) . .
C2 C2 C5 C3 0.9(3) 3_556 .
C4 C2 C5 C3 -179.07(14) . .
C2 C2 C5 C7 -178.28(17) 3_556 .
C4 C2 C5 C7 1.7(2) . .
C7 N1 C6 O1 -177.55(14) . .
C8 N1 C6 O1 -2.6(2) . .
C7 N1 C6 C4 2.5(2) . .
C8 N1 C6 C4 177.39(13) . .
C1 C4 C6 O1 -3.0(2) . .
C2 C4 C6 O1 175.74(14) . .
C1 C4 C6 N1 176.96(13) . .
C2 C4 C6 N1 -4.3(2) . .
C2 C5 C3 C1 -0.9(2) . 3_556
C7 C5 C3 C1 178.33(14) . 3_556
C6 N1 C7 O2 -179.15(13) . .
C8 N1 C7 O2 5.9(2) . .
C6 N1 C7 C5 1.4(2) . .
C8 N1 C7 C5 -173.64(13) . .
C3 C5 C7 O2 -2.2(2) . .
C2 C5 C7 O2 177.00(14) . .
C3 C5 C7 N1 177.28(14) . .
C2 C5 C7 N1 -3.5(2) . .
C2 C4 C1 C3 -1.1(2) . 3_556
C6 C4 C1 C3 177.71(14) . 3_556
C6 N1 C8 C9 -96.41(15) . .
C7 N1 C8 C9 78.93(16) . .
loop_
_cod_related_entry_id
_cod_related_entry_database
_cod_related_entry_code
1 PubChem 16717773
