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#$Date: 2025-08-19 21:30:04 +0200 (Tue 19 de Aug de 2025) $
#$Revision: 301811 $
#$URL: svn://www.crystallography.net/cod/cif/4/00/13/4001368.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_4001368
loop_
_publ_author_name
'Jones, Brooks A.'
'Facchetti, Antonio'
'Marks, Tobin J.'
'Wasielewski, Michael R.'
_publ_section_title
;
 Cyanonaphthalene Diimide Semiconductors for Air-Stable, Flexible, and
 Optically Transparent n-Channel Field-Effect Transistors
;
_journal_issue                   11
_journal_name_full               'Chemistry of Materials'
_journal_page_first              2703
_journal_paper_doi               10.1021/cm0704579
_journal_volume                  19
_journal_year                    2007
_chemical_formula_moiety         'C30 H36 Br2 N2 O4'
_chemical_formula_sum            'C30 H36 Br2 N2 O4'
_chemical_formula_weight         648.43
_chemical_name_common            ndi-8br2
_chemical_name_systematic
N,N'-bis(n-octyl)-2,6-dibromonaphthalene-1,4:5,8-tetracarboxylicdiimide
_space_group_IT_number           2
_symmetry_cell_setting           triclinic
_symmetry_Int_Tables_number      2
_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                86.392(3)
_cell_angle_beta                 83.962(3)
_cell_angle_gamma                88.200(3)
_cell_formula_units_Z            1
_cell_length_a                   4.6807(8)
_cell_length_b                   8.3340(13)
_cell_length_c                   18.206(3)
_cell_measurement_temperature    153(2)
_cell_volume                     704.6(2)
_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-97 (Sheldrick, 1997)'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 1990)'
_diffrn_ambient_temperature      153(2)
_diffrn_measured_fraction_theta_full 0.880
_diffrn_measured_fraction_theta_max 0.880
_diffrn_measurement_device_type  'CCD Area Detector'
_diffrn_measurement_method       'phi and omega scans'
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0930
_diffrn_reflns_av_sigmaI/netI    0.0871
_diffrn_reflns_limit_h_max       6
_diffrn_reflns_limit_h_min       -6
_diffrn_reflns_limit_k_max       11
_diffrn_reflns_limit_k_min       -11
_diffrn_reflns_limit_l_max       23
_diffrn_reflns_limit_l_min       -23
_diffrn_reflns_number            6473
_diffrn_reflns_theta_full        28.81
_diffrn_reflns_theta_max         28.81
_diffrn_reflns_theta_min         1.13
_diffrn_source                   'fine-focus sealed tube'
_exptl_absorpt_coefficient_mu    2.914
_exptl_absorpt_correction_T_max  0.90703
_exptl_absorpt_correction_T_min  0.57167
_exptl_absorpt_correction_type   integration
_exptl_crystal_colour            colorless
_exptl_crystal_density_diffrn    1.528
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       needle
_exptl_crystal_F_000             332
_exptl_crystal_recrystallization_method evaporation
_exptl_crystal_size_max          0.600
_exptl_crystal_size_mid          0.066
_exptl_crystal_size_min          0.034
_refine_diff_density_max         1.285
_refine_diff_density_min         -0.857
_refine_diff_density_rms         0.117
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.002
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     173
_refine_ls_number_reflns         3256
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.002
_refine_ls_R_factor_all          0.0501
_refine_ls_R_factor_gt           0.0399
_refine_ls_shift/su_max          0.001
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'calc w=1/[σ²(Fo²)+(0.0479P)²+0.0000P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0969
_refine_ls_wR_factor_ref         0.1019
_reflns_number_gt                2727
_reflns_number_total             3256
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            cm0704579si20070215_041147.cif
_cod_data_source_block           facendi2
_cod_database_code               4001368
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
Br1 Br 0.29656(6) 1.13362(3) 0.165941(15) 0.02121(11) Uani 1 1 d .
O1 O 1.2045(4) 0.5216(2) 0.06312(11) 0.0220(4) Uani 1 1 d .
O2 O 0.4321(4) 0.7898(2) 0.17135(12) 0.0237(5) Uani 1 1 d .
N1 N 0.8225(5) 0.6579(3) 0.11893(13) 0.0161(5) Uani 1 1 d .
C1 C 1.0570(6) 0.6454(3) 0.06646(15) 0.0169(5) Uani 1 1 d .
C2 C 0.6449(6) 0.7964(3) 0.12783(15) 0.0171(5) Uani 1 1 d .
C3 C 0.7296(6) 0.9429(3) 0.08096(14) 0.0150(5) Uani 1 1 d .
C4 C 0.9596(6) 0.9337(3) 0.02410(14) 0.0145(5) Uani 1 1 d .
C5 C 1.1202(6) 0.7864(3) 0.01552(14) 0.0150(5) Uani 1 1 d .
C6 C 0.5877(6) 1.0915(3) 0.08910(15) 0.0155(5) Uani 1 1 d .
C7 C 0.6585(6) 1.2238(3) 0.04044(15) 0.0169(5) Uani 1 1 d .
H7A H 0.5528 1.3222 0.0459 0.020 Uiso 1 1 calc R
C8 C 0.7495(6) 0.5178(3) 0.16968(15) 0.0184(5) Uani 1 1 d .
H8A H 0.8411 0.4201 0.1483 0.022 Uiso 1 1 calc R
H8B H 0.5388 0.5044 0.1745 0.022 Uiso 1 1 calc R
C9 C 0.8459(7) 0.5333(4) 0.24602(16) 0.0228(6) Uani 1 1 d .
H9A H 0.7626 0.6338 0.2665 0.027 Uiso 1 1 calc R
H9B H 1.0578 0.5403 0.2417 0.027 Uiso 1 1 calc R
C10 C 0.7534(7) 0.3909(4) 0.29867(16) 0.0245(6) Uani 1 1 d .
H10A H 0.5428 0.3804 0.3001 0.029 Uiso 1 1 calc R
H10B H 0.8454 0.2916 0.2791 0.029 Uiso 1 1 calc R
C11 C 0.8296(7) 0.4049(4) 0.37685(17) 0.0283(7) Uani 1 1 d .
H11A H 1.0408 0.4118 0.3757 0.034 Uiso 1 1 calc R
H11B H 0.7427 0.5059 0.3959 0.034 Uiso 1 1 calc R
C12 C 0.7289(8) 0.2653(4) 0.42943(18) 0.0308(7) Uani 1 1 d .
H12A H 0.8175 0.1646 0.4105 0.037 Uiso 1 1 calc R
H12B H 0.5180 0.2577 0.4300 0.037 Uiso 1 1 calc R
C13 C 0.8010(8) 0.2789(4) 0.50827(17) 0.0317(7) Uani 1 1 d .
H13A H 1.0124 0.2825 0.5079 0.038 Uiso 1 1 calc R
H13B H 0.7184 0.3816 0.5265 0.038 Uiso 1 1 calc R
C14 C 0.6910(9) 0.1423(5) 0.56157(19) 0.0399(9) Uani 1 1 d .
H14A H 0.7719 0.0395 0.5431 0.048 Uiso 1 1 calc R
H14B H 0.4794 0.1394 0.5623 0.048 Uiso 1 1 calc R
C15 C 0.7657(11) 0.1551(6) 0.6400(2) 0.0509(11) Uani 1 1 d .
H15A H 0.6730 0.0689 0.6722 0.076 Uiso 1 1 calc R
H15B H 0.6979 0.2596 0.6577 0.076 Uiso 1 1 calc R
H15C H 0.9745 0.1449 0.6408 0.076 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'
Br Br -0.2901 2.4595 '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
C1 N1 C2 124.8(2) .
C1 N1 C8 118.6(2) .
C2 N1 C8 116.6(2) .
O1 C1 N1 120.9(3) .
O1 C1 C5 121.9(2) .
N1 C1 C5 117.2(2) .
O2 C2 N1 119.2(3) .
O2 C2 C3 123.6(2) .
N1 C2 C3 117.2(2) .
C6 C3 C4 117.5(2) .
C6 C3 C2 122.8(2) .
C4 C3 C2 119.7(2) .
C4 C4 C3 122.2(3) 2_775
C4 C4 C5 118.1(3) 2_775
C3 C4 C5 119.7(2) .
C7 C5 C4 119.9(2) 2_775
C7 C5 C1 119.1(2) 2_775
C4 C5 C1 120.9(2) .
C3 C6 C7 121.3(2) .
C3 C6 Br1 124.1(2) .
C7 C6 Br1 114.54(18) .
C5 C7 C6 120.9(2) 2_775
N1 C8 C9 112.7(2) .
C8 C9 C10 111.6(3) .
C11 C10 C9 113.7(3) .
C12 C11 C10 113.4(3) .
C11 C12 C13 113.9(3) .
C14 C13 C12 114.0(3) .
C13 C14 C15 113.9(4) .
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
Br1 C6 1.889(3) .
O1 C1 1.225(3) .
O2 C2 1.206(3) .
N1 C1 1.383(3) .
N1 C2 1.409(3) .
N1 C8 1.468(4) .
C1 C5 1.468(4) .
C2 C3 1.485(4) .
C3 C6 1.396(3) .
C3 C4 1.417(4) .
C4 C4 1.403(5) 2_775
C4 C5 1.427(3) .
C5 C7 1.379(4) 2_775
C6 C7 1.396(4) .
C7 C5 1.379(4) 2_775
C8 C9 1.520(4) .
C9 C10 1.522(4) .
C10 C11 1.516(4) .
C11 C12 1.514(5) .
C12 C13 1.521(5) .
C13 C14 1.515(5) .
C14 C15 1.516(5) .
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
C2 N1 C1 O1 178.6(3) . .
C8 N1 C1 O1 -1.4(4) . .
C2 N1 C1 C5 -1.4(4) . .
C8 N1 C1 C5 178.7(2) . .
C1 N1 C2 O2 173.9(3) . .
C8 N1 C2 O2 -6.1(4) . .
C1 N1 C2 C3 -4.7(4) . .
C8 N1 C2 C3 175.3(2) . .
O2 C2 C3 C6 7.5(4) . .
N1 C2 C3 C6 -173.9(2) . .
O2 C2 C3 C4 -171.1(3) . .
N1 C2 C3 C4 7.5(4) . .
C6 C3 C4 C4 -1.7(5) . 2_775
C2 C3 C4 C4 177.0(3) . 2_775
C6 C3 C4 C5 177.2(2) . .
C2 C3 C4 C5 -4.1(4) . .
C4 C4 C5 C7 -2.0(5) 2_775 2_775
C3 C4 C5 C7 179.0(2) . 2_775
C4 C4 C5 C1 176.8(3) 2_775 .
C3 C4 C5 C1 -2.1(4) . .
O1 C1 C5 C7 3.9(4) . 2_775
N1 C1 C5 C7 -176.2(2) . 2_775
O1 C1 C5 C4 -175.0(3) . .
N1 C1 C5 C4 5.0(4) . .
C4 C3 C6 C7 3.6(4) . .
C2 C3 C6 C7 -175.0(2) . .
C4 C3 C6 Br1 -174.86(19) . .
C2 C3 C6 Br1 6.5(4) . .
C3 C6 C7 C5 -2.8(4) . 2_775
Br1 C6 C7 C5 175.9(2) . 2_775
C1 N1 C8 C9 102.1(3) . .
C2 N1 C8 C9 -77.9(3) . .
N1 C8 C9 C10 176.9(2) . .
C8 C9 C10 C11 -176.7(3) . .
C9 C10 C11 C12 178.2(3) . .
C10 C11 C12 C13 -179.3(3) . .
C11 C12 C13 C14 177.9(3) . .
C12 C13 C14 C15 179.4(3) . .
loop_
_cod_related_entry_id
_cod_related_entry_database
_cod_related_entry_code
1 PubChem 71623604
