#------------------------------------------------------------------------------
#$Date: 2016-10-04 00:56:32 +0300 (Tue, 04 Oct 2016) $
#$Revision: 186880 $
#$URL: file:///home/coder/svn-repositories/cod/cif/4/51/39/4513964.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_4513964
loop_
_publ_author_name
'Kalita, Anamika'
'Hussain, Sameer'
'Malik, Akhtar Hussain'
'Barman, Ujjwol'
'Goswami, Namami'
'Iyer, Parameswar Krishnan'
_publ_section_title
;
 Anion-Exchange Induced Strong π-π Interactions in Single Crystalline
 Naphthalene Diimide for Nitroexplosive Sensing: An Electronic Prototype
 for Visual on-Site Detection.
;
_journal_issue                   38
_journal_name_full               'ACS applied materials & interfaces'
_journal_page_first              25326
_journal_page_last               25336
_journal_paper_doi               10.1021/acsami.6b08751
_journal_volume                  8
_journal_year                    2016
_chemical_formula_sum            'C40 H32 N12 O18'
_chemical_formula_weight         968.78
_chemical_name_systematic
; 
 ? 
;
_space_group_IT_number           2
_symmetry_cell_setting           triclinic
_symmetry_space_group_name_Hall  '-P 1'
_symmetry_space_group_name_H-M   'P -1'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_audit_creation_method           SHELXL-97
_cell_angle_alpha                101.167(5)
_cell_angle_beta                 98.645(5)
_cell_angle_gamma                119.207(3)
_cell_formula_units_Z            1
_cell_length_a                   10.2706(6)
_cell_length_b                   10.4147(6)
_cell_length_c                   11.7961(12)
_cell_measurement_reflns_used    3079
_cell_measurement_temperature    296(2)
_cell_measurement_theta_max      25.50
_cell_measurement_theta_min      1.84
_cell_volume                     1035.40(15)
_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  'Bruker SHELXTL'
_computing_structure_solution    'Bruker SHELXTL'
_diffrn_ambient_temperature      296(2)
_diffrn_measured_fraction_theta_full 0.959
_diffrn_measured_fraction_theta_max 0.959
_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  0.0607
_diffrn_reflns_av_sigmaI/netI    0.1048
_diffrn_reflns_limit_h_max       10
_diffrn_reflns_limit_h_min       -12
_diffrn_reflns_limit_k_max       12
_diffrn_reflns_limit_k_min       -12
_diffrn_reflns_limit_l_max       14
_diffrn_reflns_limit_l_min       -14
_diffrn_reflns_number            13415
_diffrn_reflns_theta_full        25.50
_diffrn_reflns_theta_max         25.50
_diffrn_reflns_theta_min         1.84
_exptl_absorpt_coefficient_mu    0.126
_exptl_crystal_colour            Yellow
_exptl_crystal_density_diffrn    1.554
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       Block
_exptl_crystal_F_000             462
_exptl_crystal_size_max          0.30
_exptl_crystal_size_mid          0.25
_exptl_crystal_size_min          0.23
_refine_diff_density_max         0.528
_refine_diff_density_min         -0.460
_refine_diff_density_rms         0.054
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.118
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     317
_refine_ls_number_reflns         3709
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.118
_refine_ls_R_factor_all          0.1776
_refine_ls_R_factor_gt           0.0745
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'calc w=1/[σ²(Fo²)+(0.1000P)²+0.0000P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1980
_refine_ls_wR_factor_ref         0.2414
_reflns_number_gt                1596
_reflns_number_total             3709
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            am6b08751_si_002.cif
_cod_data_source_block           NDMI
_cod_depositor_comments
;
The following automatic conversions were performed:

'_symmetry_cell_setting' value 'Triclinic' changed to 'triclinic'
according to
/usr/data/users/saulius/crontab/automatic-downloads/current/ACS/lib/dictionaries/cif_core.dic
dictionary named 'cif_core.dic' version 2.4.2 from 2011-04-26.

Automatic conversion script
Id: cif_fix_values 4268 2015-11-12 08:31:59Z antanas 
;
_cod_original_cell_volume        1035.40(14)
_cod_original_sg_symbol_H-M      P-1
_cod_database_code               4513964
loop_
_symmetry_equiv_pos_as_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_symmetry_multiplicity
_atom_site_calc_flag
_atom_site_refinement_flags
N3 N 0.3215(5) 0.8077(4) 0.1869(3) 0.0564(10) Uani 1 1 d .
N2 N 0.1514(5) 1.0071(5) -0.0451(3) 0.0546(10) Uani 1 1 d .
N1 N 0.2074(5) 1.2123(5) -0.0941(4) 0.0554(10) Uani 1 1 d .
N5 N 0.7686(6) 0.7631(5) 0.4911(5) 0.0687(12) Uani 1 1 d .
N4 N 0.3704(8) 0.6694(6) 0.7140(5) 0.0951(16) Uani 1 1 d .
N6 N 0.2197(7) 0.4747(5) 0.2761(5) 0.0843(15) Uani 1 1 d .
C10 C 0.4639(5) 0.9618(5) 0.4378(4) 0.0474(12) Uani 1 1 d .
C9 C 0.2999(6) 0.8785(5) 0.3913(4) 0.0500(12) Uani 1 1 d .
C11 C 0.5595(6) 0.9698(5) 0.3597(4) 0.0519(12) Uani 1 1 d .
C15 C 0.6102(6) 0.7060(5) 0.4981(4) 0.0535(12) Uani 1 1 d .
C13 C 0.4164(6) 0.6620(5) 0.6030(5) 0.0556(13) Uani 1 1 d .
C7 C 0.2501(6) 0.7300(5) 0.0558(4) 0.0676(14) Uani 1 1 d .
H7A H 0.1437 0.6460 0.0411 0.081 Uiso 1 1 calc R
H7B H 0.3068 0.6859 0.0252 0.081 Uiso 1 1 calc R
C12 C 0.4844(6) 0.8856(6) 0.2294(5) 0.0610(14) Uani 1 1 d .
C8 C 0.2246(6) 0.8006(5) 0.2611(4) 0.0549(13) Uani 1 1 d .
C17 C 0.3434(7) 0.5641(5) 0.3895(4) 0.0625(14) Uani 1 1 d .
C14 C 0.5821(7) 0.7338(5) 0.6148(4) 0.0578(13) Uani 1 1 d .
C16 C 0.4960(7) 0.6259(5) 0.3913(4) 0.0617(14) Uani 1 1 d .
H16 H 0.5218 0.6133 0.3194 0.074 Uiso 1 1 calc R
C5 C 0.1530(6) 0.9036(5) 0.0235(4) 0.0622(13) Uani 1 1 d .
H5A H 0.0473 0.8183 0.0090 0.075 Uiso 1 1 calc R
H5B H 0.1942 0.9600 0.1090 0.075 Uiso 1 1 calc R
C4 C 0.2394(6) 1.1604(7) -0.0066(4) 0.0597(13) Uani 1 1 d .
H4 H 0.3112 1.2209 0.0689 0.072 Uiso 1 1 calc R
C3 C 0.0608(5) 0.9605(6) -0.1602(4) 0.0590(13) Uani 1 1 d .
H3 H -0.0117 0.8591 -0.2083 0.071 Uiso 1 1 calc R
C2 C 0.0962(6) 1.0887(6) -0.1905(4) 0.0570(13) Uani 1 1 d .
H2 H 0.0530 1.0928 -0.2639 0.068 Uiso 1 1 calc R
C6 C 0.2505(6) 0.8409(6) -0.0119(4) 0.0650(14) Uani 1 1 d .
H6A H 0.3567 0.9263 0.0045 0.078 Uiso 1 1 calc R
H6B H 0.2109 0.7873 -0.0979 0.078 Uiso 1 1 calc R
C18 C 0.3022(6) 0.5824(5) 0.4977(5) 0.0624(14) Uani 1 1 d .
H18 H 0.1984 0.5406 0.4964 0.075 Uiso 1 1 calc R
C1 C 0.2790(7) 1.3746(6) -0.0918(5) 0.0886(18) Uani 1 1 d .
H1A H 0.3186 1.4401 -0.0099 0.133 Uiso 1 1 calc R
H1B H 0.2024 1.3878 -0.1362 0.133 Uiso 1 1 calc R
H1C H 0.3628 1.4018 -0.1279 0.133 Uiso 1 1 calc R
O1 O 0.0849(4) 0.7308(4) 0.2163(3) 0.0712(10) Uani 1 1 d .
O2 O 0.5600(4) 0.8811(4) 0.1593(3) 0.0838(12) Uani 1 1 d .
O5 O 0.6857(4) 0.8075(4) 0.7132(3) 0.0912(12) Uani 1 1 d .
O8 O 0.2588(6) 0.4581(5) 0.1831(4) 0.1141(16) Uani 1 1 d .
O9 O 0.0862(6) 0.4213(5) 0.2790(4) 0.1177(17) Uani 1 1 d .
O6 O 0.8723(5) 0.8147(6) 0.5775(4) 0.136(2) Uani 1 1 d .
O7 O 0.7900(5) 0.7504(6) 0.3927(4) 0.1375(19) Uani 1 1 d .
O4 O 0.4439(8) 0.7151(13) 0.8014(5) 0.302(7) Uani 1 1 d .
O3 O 0.2434(8) 0.6355(9) 0.7074(6) 0.216(4) Uani 1 1 d .
C19 C 0.2124(6) 0.8730(5) 0.4698(5) 0.0573(13) Uani 1 1 d .
H19 H 0.1045 0.8186 0.4398 0.069 Uiso 1 1 calc R
C20 C 0.7184(6) 1.0527(6) 0.4066(4) 0.0603(14) Uani 1 1 d .
H20 H 0.7805 1.0594 0.3554 0.072 Uiso 1 1 calc R
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
C12 N3 C8 124.1(4) . .
C12 N3 C7 117.0(4) . .
C8 N3 C7 118.9(4) . .
C4 N2 C3 108.8(4) . .
C4 N2 C5 125.7(4) . .
C3 N2 C5 125.5(4) . .
C4 N1 C2 108.6(4) . .
C4 N1 C1 127.0(5) . .
C2 N1 C1 124.4(4) . .
O6 N5 O7 120.3(5) . .
O6 N5 C15 121.4(5) . .
O7 N5 C15 118.2(5) . .
O4 N4 O3 115.1(7) . .
O4 N4 C13 126.3(7) . .
O3 N4 C13 118.2(7) . .
O9 N6 O8 124.4(6) . .
O9 N6 C17 118.4(6) . .
O8 N6 C17 117.2(6) . .
C10 C10 C9 120.6(5) 2_676 .
C10 C10 C11 118.6(5) 2_676 .
C9 C10 C11 120.8(4) . .
C19 C9 C10 118.8(4) . .
C19 C9 C8 120.6(4) . .
C10 C9 C8 120.6(4) . .
C20 C11 C10 119.8(4) . .
C20 C11 C12 121.2(4) . .
C10 C11 C12 119.0(4) . .
C16 C15 C14 124.1(5) . .
C16 C15 N5 116.1(5) . .
C14 C15 N5 119.8(4) . .
C18 C13 C14 125.1(5) . .
C18 C13 N4 117.6(5) . .
C14 C13 N4 117.2(5) . .
N3 C7 C6 112.1(4) . .
O2 C12 N3 120.0(5) . .
O2 C12 C11 121.8(5) . .
N3 C12 C11 118.1(4) . .
O1 C8 N3 119.5(5) . .
O1 C8 C9 123.2(4) . .
N3 C8 C9 117.3(4) . .
C16 C17 C18 120.8(5) . .
C16 C17 N6 120.7(6) . .
C18 C17 N6 118.5(6) . .
O5 C14 C15 124.7(5) . .
O5 C14 C13 123.9(5) . .
C15 C14 C13 111.4(4) . .
C15 C16 C17 120.1(5) . .
N2 C5 C6 111.4(4) . .
N1 C4 N2 108.2(4) . .
C2 C3 N2 107.0(4) . .
C3 C2 N1 107.5(4) . .
C5 C6 C7 112.2(4) . .
C13 C18 C17 118.6(5) . .
C9 C19 C20 121.5(5) . 2_676
C11 C20 C19 120.7(4) . 2_676
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
N3 C12 1.405(6) .
N3 C8 1.406(6) .
N3 C7 1.476(5) .
N2 C4 1.326(5) .
N2 C3 1.367(5) .
N2 C5 1.473(5) .
N1 C4 1.325(5) .
N1 C2 1.364(5) .
N1 C1 1.470(5) .
N5 O6 1.168(5) .
N5 O7 1.209(5) .
N5 C15 1.457(6) .
N4 O4 1.041(6) .
N4 O3 1.158(7) .
N4 C13 1.458(7) .
N6 O9 1.211(6) .
N6 O8 1.234(6) .
N6 C17 1.457(7) .
C10 C10 1.408(8) 2_676
C10 C9 1.415(6) .
C10 C11 1.429(6) .
C9 C19 1.375(6) .
C9 C8 1.470(6) .
C11 C20 1.372(6) .
C11 C12 1.479(7) .
C15 C16 1.362(6) .
C15 C14 1.452(6) .
C13 C18 1.349(6) .
C13 C14 1.457(7) .
C7 C6 1.526(6) .
C12 O2 1.226(5) .
C8 O1 1.213(5) .
C17 C16 1.368(7) .
C17 C18 1.411(7) .
C14 O5 1.247(5) .
C5 C6 1.504(6) .
C3 C2 1.339(6) .
C19 C20 1.394(6) 2_676
C20 C19 1.394(6) 2_676
