#------------------------------------------------------------------------------
#$Date: 2025-08-04 10:03:09 +0300 (Mon, 04 Aug 2025) $
#$Revision: 301442 $
#$URL: file:///home/coder/svn-repositories/cod/cif/7/05/65/7056529.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_7056529
loop_
_publ_author_name
'Baruah, Jubaraj Bikash'
'Tarai, Arup'
_publ_section_title
;
 Competing phenol-imidazole and phenol-phenol interactions in flexible
 supramolecular environment of
 N,N'-bis(3-imidazol-1-yl-propyl)naphthalenediimide causing domain
 expansion
;
_journal_issue                   19
_journal_name_full               'New J. Chem.'
_journal_page_first              10750
_journal_page_last               10760
_journal_paper_doi               10.1039/C7NJ02322G
_journal_volume                  41
_journal_year                    2017
_chemical_formula_moiety         'C26 H24 N6 O4, 2(C6 H3 N2 O5)'
_chemical_formula_sum            'C38 H30 N10 O14'
_chemical_formula_weight         850.72
_space_group_crystal_system      triclinic
_space_group_IT_number           2
_space_group_name_Hall           '-P 1'
_space_group_name_H-M_alt        'P -1'
_symmetry_space_group_name_Hall  '-P 1'
_symmetry_space_group_name_H-M   'P -1'
_atom_sites_solution_hydrogens   mixed
_audit_creation_method           SHELXL-2014/7
_audit_update_record
;
2017-08-11 deposited with the CCDC.
2017-08-21 downloaded from the CCDC.
;
_cell_angle_alpha                106.232(14)
_cell_angle_beta                 108.621(15)
_cell_angle_gamma                105.345(9)
_cell_formula_units_Z            1
_cell_length_a                   8.3794(12)
_cell_length_b                   10.8125(17)
_cell_length_c                   12.123(3)
_cell_measurement_reflns_used    1083
_cell_measurement_temperature    296(2)
_cell_measurement_theta_max      18.38
_cell_measurement_theta_min      2.23
_cell_volume                     920.7(4)
_computing_cell_refinement       'Bruker SMART'
_computing_data_collection       'Bruker SMART'
_computing_data_reduction        'Bruker SAINT'
_computing_molecular_graphics    'Bruker SHELXTL'
_computing_publication_material  'Bruker SHELXTL'
_computing_structure_refinement  'SHELXL-2014/7 (Sheldrick, 2014)'
_computing_structure_solution    'Bruker SHELXTL'
_diffrn_ambient_temperature      296(2)
_diffrn_measured_fraction_theta_full 0.962
_diffrn_measured_fraction_theta_max 0.962
_diffrn_measurement_device_type  'CCD area detector'
_diffrn_measurement_method       'phi and omega scans'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0352
_diffrn_reflns_av_unetI/netI     0.0431
_diffrn_reflns_Laue_measured_fraction_full 0.962
_diffrn_reflns_Laue_measured_fraction_max 0.962
_diffrn_reflns_limit_h_max       9
_diffrn_reflns_limit_h_min       -9
_diffrn_reflns_limit_k_max       12
_diffrn_reflns_limit_k_min       -12
_diffrn_reflns_limit_l_max       13
_diffrn_reflns_limit_l_min       -14
_diffrn_reflns_number            7823
_diffrn_reflns_point_group_measured_fraction_full 0.962
_diffrn_reflns_point_group_measured_fraction_max 0.962
_diffrn_reflns_theta_full        25.048
_diffrn_reflns_theta_max         25.048
_diffrn_reflns_theta_min         1.933
_exptl_absorpt_coefficient_mu    0.120
_exptl_absorpt_correction_T_max  0.987
_exptl_absorpt_correction_T_min  0.970
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   multi-scan
_exptl_crystal_colour            Yellow
_exptl_crystal_density_diffrn    1.534
_exptl_crystal_description       Block
_exptl_crystal_F_000             440
_exptl_crystal_size_max          0.33
_exptl_crystal_size_mid          0.21
_exptl_crystal_size_min          0.11
_refine_diff_density_max         0.263
_refine_diff_density_min         -0.208
_refine_diff_density_rms         0.050
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.081
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     284
_refine_ls_number_reflns         3131
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.081
_refine_ls_R_factor_all          0.1025
_refine_ls_R_factor_gt           0.0542
_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)+(0.0100P)²+0.8000P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0921
_refine_ls_wR_factor_ref         0.1134
_reflns_Friedel_coverage         0.000
_reflns_number_gt                1731
_reflns_number_total             3131
_reflns_threshold_expression     'I > 2σ(I)'
_cod_data_source_file            c7nj02322g2.cif
_cod_data_source_block           L(dnp)2
_cod_original_cell_volume        920.7(3)
_cod_database_code               7056529
#BEGIN Tags that were not found in dictionaries:
_shelx_shelxl_version_number     2014/7
_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.
;
#END Tags that were not found in dictionaries
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x, -y, -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
O1 O 0.9410(3) 0.2610(2) 0.3610(2) 0.0718(8) Uani 1 1 d . .
O2 O 1.2857(3) 0.1543(2) 0.1566(2) 0.0655(7) Uani 1 1 d . .
N2 N 1.1124(3) 0.2109(2) 0.2571(2) 0.0512(7) Uani 1 1 d . .
N1 N 0.6504(4) -0.1278(3) 0.1755(3) 0.0655(9) Uani 1 1 d . .
N3 N 0.3679(4) -0.2442(3) 0.0430(3) 0.0709(9) Uani 1 1 d . .
C7 C 1.0894(4) 0.2911(3) 0.3578(3) 0.0528(9) Uani 1 1 d . .
C8 C 1.2529(4) 0.4140(3) 0.4588(3) 0.0469(8) Uani 1 1 d . .
C9 C 1.2402(4) 0.4999(3) 0.5601(3) 0.0531(9) Uani 1 1 d . .
H9 H 1.1282 0.4813 0.5648 0.064 Uiso 1 1 calc R U
C16 C 1.4222(4) 0.4414(3) 0.4513(3) 0.0434(8) Uani 1 1 d . .
C18 C 1.2778(4) 0.2328(3) 0.2466(3) 0.0522(9) Uani 1 1 d . .
C15 C 0.9535(4) 0.0880(3) 0.1533(3) 0.0615(10) Uani 1 1 d . .
H15A H 0.9579 0.0824 0.0731 0.074 Uiso 1 1 calc R U
H15B H 0.8423 0.1004 0.1512 0.074 Uiso 1 1 calc R U
C14 C 0.9469(5) -0.0472(4) 0.1669(4) 0.0752(12) Uani 1 1 d . .
H14A H 0.8882 -0.1213 0.0826 0.090 Uiso 1 1 calc R U
H14B H 1.0715 -0.0402 0.2055 0.090 Uiso 1 1 calc R U
C13 C 0.8520(5) -0.0891(4) 0.2416(4) 0.0785(12) Uani 1 1 d . .
H13B H 0.9012 -0.0126 0.3236 0.094 Uiso 1 1 calc R U
H13A H 0.8737 -0.1683 0.2559 0.094 Uiso 1 1 calc R U
C12 C 0.5565(5) -0.0486(4) 0.2028(4) 0.0731(11) Uani 1 1 d . .
H12 H 0.6052 0.0400 0.2672 0.088 Uiso 1 1 calc R U
C11 C 0.3806(5) -0.1209(4) 0.1206(4) 0.0758(12) Uani 1 1 d . .
H11 H 0.2848 -0.0918 0.1173 0.091 Uiso 1 1 calc R U
C10 C 0.5347(5) -0.2451(4) 0.0790(4) 0.0729(11) Uani 1 1 d . .
H10 H 0.5646 -0.3178 0.0415 0.087 Uiso 1 1 calc R U
O4 O 0.0224(4) 0.3434(3) 0.0200(3) 0.0896(9) Uani 1 1 d . .
O5 O 0.3105(4) 0.4387(3) 0.0748(3) 0.0951(10) Uani 1 1 d . .
O6 O 0.7081(4) 0.8381(3) 0.4486(3) 0.1059(11) Uani 1 1 d . .
O7 O 0.6047(4) 0.9273(3) 0.5810(3) 0.1072(11) Uani 1 1 d . .
O3 O -0.1274(3) 0.4682(3) 0.1584(3) 0.0932(10) Uani 1 1 d . .
N4 N 0.1733(4) 0.4362(3) 0.0930(3) 0.0710(9) Uani 1 1 d . .
N5 N 0.5820(5) 0.8439(3) 0.4774(4) 0.0848(11) Uani 1 1 d . .
C3 C 0.1919(5) 0.5462(3) 0.2017(3) 0.0586(9) Uani 1 1 d . .
C2 C 0.3691(5) 0.6418(4) 0.2826(3) 0.0644(10) Uani 1 1 d . .
H2 H 0.4671 0.6338 0.2651 0.077 Uiso 1 1 calc R U
C1 C 0.3968(5) 0.7484(4) 0.3891(3) 0.0662(11) Uani 1 1 d . .
C6 C 0.2502(6) 0.7642(4) 0.4139(4) 0.0747(12) Uani 1 1 d . .
H6 H 0.2710 0.8385 0.4851 0.090 Uiso 1 1 calc R U
C5 C 0.0790(5) 0.6718(4) 0.3345(4) 0.0747(11) Uani 1 1 d . .
H5 H -0.0165 0.6856 0.3523 0.090 Uiso 1 1 calc R U
C4 C 0.0358(5) 0.5536(4) 0.2243(4) 0.0661(10) Uani 1 1 d . .
C17 C 1.4400(4) 0.3555(3) 0.3483(3) 0.0447(8) Uani 1 1 d . .
C19 C 1.6060(4) 0.3849(3) 0.3435(3) 0.0544(9) Uani 1 1 d . .
H19 H 1.6167 0.3275 0.2754 0.065 Uiso 1 1 calc R U
H3 H 0.262(5) -0.313(4) -0.022(4) 0.096(14) 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'
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'
H H 0.0000 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
_geom_angle_site_symmetry_3
C7 N2 C18 125.4(2) . .
C7 N2 C15 119.0(3) . .
C18 N2 C15 115.6(3) . .
C10 N1 C12 108.0(3) . .
C10 N1 C13 125.3(3) . .
C12 N1 C13 126.6(3) . .
C10 N3 C11 107.5(3) . .
C10 N3 H3 128(2) . .
C11 N3 H3 125(2) . .
O1 C7 N2 120.7(3) . .
O1 C7 C8 122.4(3) . .
N2 C7 C8 116.8(3) . .
C9 C8 C16 120.0(3) . .
C9 C8 C7 120.3(3) . .
C16 C8 C7 119.8(3) . .
C8 C9 C19 120.6(3) . 2_866
C8 C9 H9 119.7 . .
C19 C9 H9 119.7 2_866 .
C8 C16 C17 121.5(2) . .
C8 C16 C16 119.3(3) . 2_866
C17 C16 C16 119.2(3) . 2_866
O2 C18 N2 120.7(3) . .
O2 C18 C17 122.2(3) . .
N2 C18 C17 117.2(3) . .
N2 C15 C14 113.0(3) . .
N2 C15 H15A 109.0 . .
C14 C15 H15A 109.0 . .
N2 C15 H15B 109.0 . .
C14 C15 H15B 109.0 . .
H15A C15 H15B 107.8 . .
C13 C14 C15 116.6(3) . .
C13 C14 H14A 108.1 . .
C15 C14 H14A 108.1 . .
C13 C14 H14B 108.1 . .
C15 C14 H14B 108.1 . .
H14A C14 H14B 107.3 . .
C14 C13 N1 111.5(3) . .
C14 C13 H13B 109.3 . .
N1 C13 H13B 109.3 . .
C14 C13 H13A 109.3 . .
N1 C13 H13A 109.3 . .
H13B C13 H13A 108.0 . .
C11 C12 N1 107.6(3) . .
C11 C12 H12 126.2 . .
N1 C12 H12 126.2 . .
C12 C11 N3 107.4(3) . .
C12 C11 H11 126.3 . .
N3 C11 H11 126.3 . .
N1 C10 N3 109.5(3) . .
N1 C10 H10 125.3 . .
N3 C10 H10 125.3 . .
O4 N4 O5 121.5(3) . .
O4 N4 C3 119.8(3) . .
O5 N4 C3 118.7(3) . .
O6 N5 O7 123.2(4) . .
O6 N5 C1 119.4(4) . .
O7 N5 C1 117.4(4) . .
C2 C3 C4 122.9(3) . .
C2 C3 N4 115.6(3) . .
C4 C3 N4 121.4(3) . .
C1 C2 C3 118.6(4) . .
C1 C2 H2 120.7 . .
C3 C2 H2 120.7 . .
C2 C1 C6 121.1(3) . .
C2 C1 N5 118.9(4) . .
C6 C1 N5 120.0(4) . .
C5 C6 C1 119.9(4) . .
C5 C6 H6 120.1 . .
C1 C6 H6 120.1 . .
C6 C5 C4 123.5(4) . .
C6 C5 H5 118.2 . .
C4 C5 H5 118.2 . .
O3 C4 C5 119.5(4) . .
O3 C4 C3 126.6(3) . .
C5 C4 C3 113.8(3) . .
C19 C17 C16 120.2(3) . .
C19 C17 C18 120.5(3) . .
C16 C17 C18 119.3(3) . .
C17 C19 C9 120.7(3) . 2_866
C17 C19 H19 119.6 . .
C9 C19 H19 119.6 2_866 .
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
O1 C7 1.216(3) .
O2 C18 1.214(3) .
N2 C7 1.388(4) .
N2 C18 1.396(4) .
N2 C15 1.477(3) .
N1 C10 1.308(4) .
N1 C12 1.352(4) .
N1 C13 1.498(4) .
N3 C10 1.328(4) .
N3 C11 1.354(4) .
N3 H3 0.92(4) .
C7 C8 1.482(4) .
C8 C9 1.371(4) .
C8 C16 1.409(4) .
C9 C19 1.398(4) 2_866
C9 H9 0.9300 .
C16 C17 1.409(4) .
C16 C16 1.416(5) 2_866
C18 C17 1.480(4) .
C15 C14 1.505(5) .
C15 H15A 0.9700 .
C15 H15B 0.9700 .
C14 C13 1.468(5) .
C14 H14A 0.9700 .
C14 H14B 0.9700 .
C13 H13B 0.9700 .
C13 H13A 0.9700 .
C12 C11 1.340(5) .
C12 H12 0.9300 .
C11 H11 0.9300 .
C10 H10 0.9300 .
O4 N4 1.228(3) .
O5 N4 1.233(4) .
O6 N5 1.225(4) .
O7 N5 1.245(4) .
O3 C4 1.258(4) .
N4 C3 1.438(4) .
N5 C1 1.447(5) .
C3 C2 1.388(4) .
C3 C4 1.438(5) .
C2 C1 1.373(5) .
C2 H2 0.9300 .
C1 C6 1.395(5) .
C6 C5 1.343(5) .
C6 H6 0.9300 .
C5 C4 1.429(5) .
C5 H5 0.9300 .
C17 C19 1.366(4) .
C19 C9 1.398(4) 2_866
C19 H19 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
C18 N2 C7 O1 -177.2(3) . .
C15 N2 C7 O1 0.1(5) . .
C18 N2 C7 C8 3.2(5) . .
C15 N2 C7 C8 -179.5(3) . .
O1 C7 C8 C9 -0.9(5) . .
N2 C7 C8 C9 178.7(3) . .
O1 C7 C8 C16 178.4(3) . .
N2 C7 C8 C16 -2.0(5) . .
C16 C8 C9 C19 0.1(5) . 2_866
C7 C8 C9 C19 179.3(3) . 2_866
C9 C8 C16 C17 -179.8(3) . .
C7 C8 C16 C17 0.9(5) . .
C9 C8 C16 C16 -0.3(6) . 2_866
C7 C8 C16 C16 -179.6(4) . 2_866
C7 N2 C18 O2 177.7(3) . .
C15 N2 C18 O2 0.2(5) . .
C7 N2 C18 C17 -3.0(5) . .
C15 N2 C18 C17 179.6(3) . .
C7 N2 C15 C14 -97.9(4) . .
C18 N2 C15 C14 79.7(4) . .
N2 C15 C14 C13 88.2(4) . .
C15 C14 C13 N1 68.4(4) . .
C10 N1 C13 C14 76.2(5) . .
C12 N1 C13 C14 -102.8(4) . .
C10 N1 C12 C11 0.1(5) . .
C13 N1 C12 C11 179.2(4) . .
N1 C12 C11 N3 -0.1(5) . .
C10 N3 C11 C12 0.0(5) . .
C12 N1 C10 N3 0.0(5) . .
C13 N1 C10 N3 -179.2(3) . .
C11 N3 C10 N1 0.0(5) . .
O4 N4 C3 C2 176.4(3) . .
O5 N4 C3 C2 -4.4(5) . .
O4 N4 C3 C4 -2.7(5) . .
O5 N4 C3 C4 176.5(4) . .
C4 C3 C2 C1 0.0(6) . .
N4 C3 C2 C1 -179.1(3) . .
C3 C2 C1 C6 -2.4(6) . .
C3 C2 C1 N5 176.7(3) . .
O6 N5 C1 C2 8.4(6) . .
O7 N5 C1 C2 -170.4(4) . .
O6 N5 C1 C6 -172.5(4) . .
O7 N5 C1 C6 8.7(5) . .
C2 C1 C6 C5 1.9(6) . .
N5 C1 C6 C5 -177.2(4) . .
C1 C6 C5 C4 1.1(6) . .
C6 C5 C4 O3 176.5(4) . .
C6 C5 C4 C3 -3.2(6) . .
C2 C3 C4 O3 -177.0(4) . .
N4 C3 C4 O3 2.0(6) . .
C2 C3 C4 C5 2.7(6) . .
N4 C3 C4 C5 -178.3(3) . .
C8 C16 C17 C19 179.9(3) . .
C16 C16 C17 C19 0.4(6) 2_866 .
C8 C16 C17 C18 -0.7(5) . .
C16 C16 C17 C18 179.8(4) 2_866 .
O2 C18 C17 C19 0.4(5) . .
N2 C18 C17 C19 -179.0(3) . .
O2 C18 C17 C16 -179.1(3) . .
N2 C18 C17 C16 1.6(5) . .
C16 C17 C19 C9 -0.2(5) . 2_866
C18 C17 C19 C9 -179.6(3) . 2_866
