Competing phenol-imidazole and phenol-phenol interactions in flexible supramolecular environment of N,N'-bis(3-imidazol-1-yl-propyl)naphthalenediimide causing domain expansion
Baruah, Jubaraj Bikash; Tarai, Arup; New J. Chem. 41 (2017) 10750–10760; doi:10.1039/C7NJ02322G

data_7056531
_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, C6 H6 O2'
_chemical_formula_sum            'C32 H28 N6 O6'
_chemical_formula_weight         592.60
_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   geom
_audit_creation_date             2017-07-12
_audit_creation_method
;
Olex2 1.2-dev
(compiled 2017.07.04 svn.r3433 for OlexSys, GUI svn.r5356)
;
_audit_update_record
;
2017-08-11 deposited with the CCDC.
2017-08-21 downloaded from the CCDC.
;
_cell_angle_alpha                86.803(4)
_cell_angle_beta                 88.439(3)
_cell_angle_gamma                69.925(4)
_cell_formula_units_Z            2
_cell_length_a                   9.4179(5)
_cell_length_b                   9.5207(5)
_cell_length_c                   16.3424(8)
_cell_measurement_reflns_used    1204
_cell_measurement_temperature    296(2)
_cell_measurement_theta_max      22.30
_cell_measurement_theta_min      2.28
_cell_volume                     1374.12(13)
_computing_data_collection       'Bruker SMART'
_computing_molecular_graphics    'Olex2 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 (Dolomanov et al., 2009)'
_computing_structure_refinement  'ShelXL (Sheldrick, 2015)'
_computing_structure_solution    'Bruker SHELXTL'
_diffrn_ambient_temperature      296.15
_diffrn_measured_fraction_theta_full 0.980
_diffrn_measured_fraction_theta_max 0.980
_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  0.0477
_diffrn_reflns_av_unetI/netI     0.1091
_diffrn_reflns_Laue_measured_fraction_full 0.980
_diffrn_reflns_Laue_measured_fraction_max 0.980
_diffrn_reflns_limit_h_max       11
_diffrn_reflns_limit_h_min       -11
_diffrn_reflns_limit_k_max       11
_diffrn_reflns_limit_k_min       -11
_diffrn_reflns_limit_l_max       19
_diffrn_reflns_limit_l_min       -19
_diffrn_reflns_number            14271
_diffrn_reflns_point_group_measured_fraction_full 0.980
_diffrn_reflns_point_group_measured_fraction_max 0.980
_diffrn_reflns_theta_full        24.999
_diffrn_reflns_theta_max         24.999
_diffrn_reflns_theta_min         1.248
_exptl_absorpt_coefficient_mu    0.102
_exptl_absorpt_correction_T_max  0.987
_exptl_absorpt_correction_T_min  0.975
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   multi-scan
_exptl_crystal_colour            Brown
_exptl_crystal_density_diffrn    1.432
_exptl_crystal_description       Block
_exptl_crystal_F_000             620
_exptl_crystal_size_max          0.31
_exptl_crystal_size_mid          0.21
_exptl_crystal_size_min          0.13
_refine_diff_density_max         0.259
_refine_diff_density_min         -0.226
_refine_diff_density_rms         0.048
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.049
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     471
_refine_ls_number_reflns         4740
_refine_ls_number_restraints     102
_refine_ls_restrained_S_all      1.042
_refine_ls_R_factor_all          0.1039
_refine_ls_R_factor_gt           0.0621
_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/[\s^2^(Fo^2^)+(0.0525P)^2^+0.3233P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1604
_refine_ls_wR_factor_ref         0.1959
_reflns_Friedel_coverage         0.000
_reflns_number_gt                2872
_reflns_number_total             4740
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            c7nj02322g2.cif
_cod_data_source_block           L(cat)
_cod_database_code               7056531
_shelx_shelxl_version_number     2014/7
_olex2_refinement_description
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups, All C(H,H) groups
 At 1.5 times of:
  All O(H) groups
2. Rigid body (RIGU) restrains
 N1A, C13B, H13E, H13F, C14B, H14E, H14F, C15B, H15E, H15F, N3B, C12B, H12B,
 C10B, H10B, C11B, H11B
 with sigma for 1-2 distances of 0.004 and sigma for 1-3 distances of 0.004
 N3A, C12A, H12A, C10A, H10A, C11A, H11A, C13A, H13C, H13D, C14A, H14C, H14D,
 C15A, H15C, H15D, N1B
 with sigma for 1-2 distances of 0.004 and sigma for 1-3 distances of 0.004
3. Others
 Fixed Sof: N3A(0.6) C12A(0.6) H12A(0.6) C10A(0.6) H10A(0.6) N1A(0.4)
 C11A(0.6) H11A(0.6) C13A(0.6) H13C(0.6) H13D(0.6) C14A(0.6) H14C(0.6)
 H14D(0.6) C15A(0.6) H15C(0.6) H15D(0.6) C13B(0.4) H13E(0.4) H13F(0.4)
 C14B(0.4) H14E(0.4) H14F(0.4) C15B(0.4) H15E(0.4) H15F(0.4) N3B(0.4) C12B(0.4)
 H12B(0.4) C10B(0.4) H10B(0.4) N1B(0.6) C11B(0.4) H11B(0.4)
4.a Secondary CH2 refined with riding coordinates:
 C15(H15A,H15B), C14(H14A,H14B), C13(H13A,H13B), C13A(H13C,H13D), C14A(H14C,
 H14D), C15A(H15C,H15D), C13B(H13E,H13F), C14B(H14E,H14F), C15B(H15E,H15F)
4.b Aromatic/amide H refined with riding coordinates:
 C24(H24), C18(H18), C23(H23), C19(H19), C12(H12), C10(H10), C12A(H12A),
 C10A(H10A), C11(H11), C11A(H11A), C2(H2), C5(H5), C4(H4), C3(H3), C12B(H12B),
 C10B(H10B), C11B(H11B)
4.c Idealised tetrahedral OH refined as rotating group:
 O2(H2A), O1(H1)
;
_shelx_res_checksum              77678
_olex2_submission_special_instructions 'No special instructions were received'