#------------------------------------------------------------------------------
#$Date: 2025-08-04 10:03:09 +0300 (Mon, 04 Aug 2025) $
#$Revision: 301442 $
#$URL: file:///home/coder/svn-repositories/cod/cif/7/05/65/7056530.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_7056530
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 H22 N6 O4, 2(C7 H7 N O3)'
_chemical_formula_sum            'C40 H36 N8 O10'
_chemical_formula_weight         788.77
_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                101.512(8)
_cell_angle_beta                 98.485(8)
_cell_angle_gamma                108.836(10)
_cell_formula_units_Z            1
_cell_length_a                   9.2173(10)
_cell_length_b                   10.4784(11)
_cell_length_c                   11.2283(9)
_cell_measurement_reflns_used    1200
_cell_measurement_temperature    296(2)
_cell_measurement_theta_max      22.30
_cell_measurement_theta_min      3.74
_cell_volume                     979.11(19)
_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 0.998
_diffrn_measured_fraction_theta_max 0.998
_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  0.0374
_diffrn_reflns_av_unetI/netI     0.0825
_diffrn_reflns_Laue_measured_fraction_full 0.998
_diffrn_reflns_Laue_measured_fraction_max 0.998
_diffrn_reflns_limit_h_max       10
_diffrn_reflns_limit_h_min       -11
_diffrn_reflns_limit_k_max       12
_diffrn_reflns_limit_k_min       -12
_diffrn_reflns_limit_l_max       13
_diffrn_reflns_limit_l_min       -13
_diffrn_reflns_number            5965
_diffrn_reflns_point_group_measured_fraction_full 0.998
_diffrn_reflns_point_group_measured_fraction_max 0.998
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         25.249
_diffrn_reflns_theta_min         3.184
_exptl_absorpt_coefficient_mu    0.098
_exptl_absorpt_correction_T_max  0.989
_exptl_absorpt_correction_T_min  0.976
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   multi-scan
_exptl_crystal_colour            Brown
_exptl_crystal_density_diffrn    1.338
_exptl_crystal_description       Block
_exptl_crystal_F_000             412
_exptl_crystal_size_max          0.33
_exptl_crystal_size_mid          0.21
_exptl_crystal_size_min          0.11
_refine_diff_density_max         0.633
_refine_diff_density_min         -0.216
_refine_diff_density_rms         0.055
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.010
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     268
_refine_ls_number_reflns         3537
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.010
_refine_ls_R_factor_all          0.1413
_refine_ls_R_factor_gt           0.0715
_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+2.1000P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1449
_refine_ls_wR_factor_ref         0.1833
_reflns_Friedel_coverage         0.000
_reflns_number_gt                1749
_reflns_number_total             3537
_reflns_threshold_expression     'I > 2σ(I)'
_cod_data_source_file            c7nj02322g2.cif
_cod_data_source_block           L(dhpa)2
_cod_original_cell_volume        979.11(18)
_cod_database_code               7056530
#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
O4 O 0.5703(4) 0.7942(4) 0.6655(3) 0.0666(10) Uani 1 1 d . .
N2 N 0.7343(4) 0.8433(4) 0.8534(3) 0.0505(10) Uani 1 1 d . .
O2 O 0.1560(5) 0.7326(4) 0.0313(4) 0.0701(11) Uani 1 1 d . .
O5 O 0.8858(4) 0.8725(4) 1.0422(3) 0.0798(12) Uani 1 1 d . .
O1 O 0.4183(5) 0.5653(5) -0.1501(3) 0.0847(12) Uani 1 1 d . .
H1 H 0.3586 0.5374 -0.2193 0.127 Uiso 1 1 calc R U
N1 N 0.8652(5) 0.5710(4) 0.5778(4) 0.0615(11) Uani 1 1 d . .
C17 C 0.6023(6) 0.8451(5) 0.7776(4) 0.0502(12) Uani 1 1 d . .
C19 C 0.5462(5) 0.9676(4) 0.9710(4) 0.0397(10) Uani 1 1 d . .
O3 O 0.0931(5) 0.8672(5) 0.2386(3) 0.0844(12) Uani 1 1 d . .
H3 H 0.0483 0.8466 0.1649 0.127 Uiso 1 1 calc R U
N4 N 0.3469(5) 0.6208(4) -0.0620(4) 0.0638(12) Uani 1 1 d . .
C20 C 0.6773(5) 0.9578(4) 1.0430(4) 0.0441(11) Uani 1 1 d . .
C18 C 0.5041(5) 0.9130(4) 0.8399(4) 0.0432(11) Uani 1 1 d . .
C9 C 0.3765(5) 0.9237(5) 0.7716(4) 0.0512(12) Uani 1 1 d . .
H9 H 0.3498 0.8875 0.6853 0.061 Uiso 1 1 calc R U
C8 C 0.2845(5) 0.9884(5) 0.8289(4) 0.0512(12) Uani 1 1 d . .
H8 H 0.1975 0.9953 0.7809 0.061 Uiso 1 1 calc R U
C16 C 0.7749(6) 0.8885(5) 0.9831(4) 0.0539(12) Uani 1 1 d . .
C3 C 0.2535(6) 0.7547(5) 0.1430(4) 0.0586(14) Uani 1 1 d . .
N3 N 0.7672(6) 0.5255(5) 0.3761(4) 0.0782(14) Uani 1 1 d . .
C2 C 0.3830(6) 0.7151(5) 0.1565(4) 0.0577(13) Uani 1 1 d . .
C15 C 0.8354(6) 0.7805(5) 0.7916(5) 0.0596(13) Uani 1 1 d . .
H15A H 0.9428 0.8241 0.8409 0.071 Uiso 1 1 calc R U
H15B H 0.8346 0.7990 0.7103 0.071 Uiso 1 1 calc R U
C1 C 0.4279(6) 0.6489(5) 0.0490(5) 0.0633(14) Uani 1 1 d . .
H1A H 0.5176 0.6262 0.0613 0.076 Uiso 1 1 calc R U
C4 C 0.2184(7) 0.8246(5) 0.2484(5) 0.0632(14) Uani 1 1 d . .
C10 C 0.7504(7) 0.4863(6) 0.4787(5) 0.0748(16) Uani 1 1 d . .
H10 H 0.6680 0.4085 0.4823 0.090 Uiso 1 1 calc R U
C11 C 0.8994(8) 0.6419(7) 0.4114(6) 0.0863(19) Uani 1 1 d . .
H11 H 0.9413 0.6944 0.3586 0.104 Uiso 1 1 calc R U
C14 C 0.7817(6) 0.6259(5) 0.7757(5) 0.0638(14) Uani 1 1 d . .
H14A H 0.6725 0.5829 0.7302 0.077 Uiso 1 1 calc R U
H14B H 0.7876 0.6076 0.8573 0.077 Uiso 1 1 calc R U
C13 C 0.8802(7) 0.5594(6) 0.7061(5) 0.0701(15) Uani 1 1 d . .
H13A H 0.9899 0.6046 0.7502 0.084 Uiso 1 1 calc R U
H13B H 0.8474 0.4615 0.7054 0.084 Uiso 1 1 calc R U
C6 C 0.4392(8) 0.8135(6) 0.3784(5) 0.0786(18) Uani 1 1 d . .
H6 H 0.5025 0.8342 0.4575 0.094 Uiso 1 1 calc R U
C7 C 0.4757(7) 0.7434(6) 0.2758(5) 0.0720(16) Uani 1 1 d . .
H7 H 0.5616 0.7152 0.2862 0.086 Uiso 1 1 calc R U
C5 C 0.3119(7) 0.8525(6) 0.3647(5) 0.0738(17) Uani 1 1 d . .
H5 H 0.2880 0.8984 0.4346 0.089 Uiso 1 1 calc R U
C12 C 0.9613(7) 0.6704(7) 0.5345(6) 0.0808(18) Uani 1 1 d . .
H12 H 1.0525 0.7442 0.5808 0.097 Uiso 1 1 calc R U
H2 H 0.186(7) 0.689(6) -0.020(5) 0.08(2) 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
C17 N2 C16 125.5(4) . .
C17 N2 C15 117.2(4) . .
C16 N2 C15 117.3(4) . .
C10 N1 C12 105.8(5) . .
C10 N1 C13 126.7(5) . .
C12 N1 C13 127.5(5) . .
O4 C17 N2 120.9(4) . .
O4 C17 C18 122.2(4) . .
N2 C17 C18 116.9(4) . .
C20 C19 C19 119.9(5) . 2_677
C20 C19 C18 121.1(4) . .
C19 C19 C18 119.0(5) 2_677 .
C1 N4 O1 111.1(4) . .
C8 C20 C19 119.9(4) 2_677 .
C8 C20 C16 119.6(4) 2_677 .
C19 C20 C16 120.4(4) . .
C9 C18 C19 120.2(4) . .
C9 C18 C17 120.5(4) . .
C19 C18 C17 119.3(4) . .
C18 C9 C8 120.9(4) . .
C20 C8 C9 120.0(4) 2_677 .
O5 C16 N2 120.8(5) . .
O5 C16 C20 122.8(4) . .
N2 C16 C20 116.5(4) . .
O2 C3 C2 124.1(5) . .
O2 C3 C4 116.2(5) . .
C2 C3 C4 119.8(4) . .
C10 N3 C11 104.9(5) . .
C3 C2 C7 119.4(5) . .
C3 C2 C1 121.4(4) . .
C7 C2 C1 119.2(5) . .
N2 C15 C14 112.2(4) . .
N4 C1 C2 121.5(5) . .
O3 C4 C5 118.6(5) . .
O3 C4 C3 121.4(5) . .
C5 C4 C3 119.9(5) . .
N3 C10 N1 112.4(5) . .
C12 C11 N3 110.0(6) . .
C15 C14 C13 112.5(4) . .
N1 C13 C14 112.3(4) . .
C5 C6 C7 120.7(5) . .
C6 C7 C2 119.7(5) . .
C6 C5 C4 120.5(6) . .
C11 C12 N1 106.9(5) . .
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
O4 C17 1.215(5) .
N2 C17 1.386(6) .
N2 C16 1.391(6) .
N2 C15 1.479(6) .
O2 C3 1.360(5) .
O5 C16 1.212(5) .
O1 N4 1.399(5) .
N1 C10 1.341(6) .
N1 C12 1.357(7) .
N1 C13 1.460(6) .
C17 C18 1.489(6) .
C19 C20 1.395(6) .
C19 C19 1.404(8) 2_677
C19 C18 1.414(5) .
O3 C4 1.364(6) .
N4 C1 1.279(6) .
C20 C8 1.382(6) 2_677
C20 C16 1.481(6) .
C18 C9 1.356(6) .
C9 C8 1.397(6) .
C8 C20 1.382(6) 2_677
C3 C2 1.383(7) .
C3 C4 1.401(7) .
N3 C10 1.312(6) .
N3 C11 1.354(7) .
C2 C7 1.397(6) .
C2 C1 1.452(7) .
C15 C14 1.497(6) .
C4 C5 1.373(7) .
C11 C12 1.348(8) .
C14 C13 1.523(7) .
C6 C5 1.360(8) .
C6 C7 1.384(8) .
