#------------------------------------------------------------------------------
#$Date: 2025-08-22 10:56:18 +0200 (Fri 22 de Aug de 2025) $
#$Revision: 301860 $
#$URL: svn://www.crystallography.net/cod/cif/7/12/14/7121471.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_7121471
loop_
_publ_author_name
'Nakazato, Takumi'
'Kamatsuka, Takuto'
'Inoue, Junichi'
'Sakurai, Tsuneaki'
'Seki, Shu'
'Shinokubo, Hiroshi'
'Miyake, Yoshihiro'
_publ_section_title
;
 The reductive aromatization of naphthalene diimide: a versatile platform
 for 2,7-diazapyrenes.
;
_journal_issue                   41
_journal_name_full               'Chemical communications (Cambridge, England)'
_journal_page_first              5177
_journal_page_last               5180
_journal_paper_doi               10.1039/c8cc01937a
_journal_volume                  54
_journal_year                    2018
_chemical_formula_sum            'C54 H56 N2'
_chemical_formula_weight         733.00
_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_method           SHELXL-2014
_audit_update_record
;
2018-01-15 deposited with the CCDC.
2018-04-05 downloaded from the CCDC.
;
_cell_angle_alpha                96.970(2)
_cell_angle_beta                 98.026(2)
_cell_angle_gamma                100.566(2)
_cell_formula_units_Z            1
_cell_length_a                   7.2956(4)
_cell_length_b                   10.3483(6)
_cell_length_c                   14.0315(7)
_cell_measurement_temperature    101(2)
_cell_volume                     1019.36(10)
_computing_structure_refinement  'SHELXL-2014 (Sheldrick, 2014)'
_diffrn_ambient_temperature      101(2)
_diffrn_measured_fraction_theta_full 0.962
_diffrn_measured_fraction_theta_max 0.833
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0215
_diffrn_reflns_av_unetI/netI     0.0473
_diffrn_reflns_Laue_measured_fraction_full 0.962
_diffrn_reflns_Laue_measured_fraction_max 0.833
_diffrn_reflns_limit_h_max       9
_diffrn_reflns_limit_h_min       -9
_diffrn_reflns_limit_k_max       11
_diffrn_reflns_limit_k_min       -13
_diffrn_reflns_limit_l_max       16
_diffrn_reflns_limit_l_min       -17
_diffrn_reflns_number            7579
_diffrn_reflns_point_group_measured_fraction_full 0.962
_diffrn_reflns_point_group_measured_fraction_max 0.833
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         27.495
_diffrn_reflns_theta_min         2.322
_exptl_absorpt_coefficient_mu    0.068
_exptl_crystal_density_diffrn    1.194
_exptl_crystal_F_000             394
_exptl_crystal_size_max          0.460
_exptl_crystal_size_mid          0.170
_exptl_crystal_size_min          0.040
_refine_diff_density_max         0.360
_refine_diff_density_min         -0.279
_refine_diff_density_rms         0.051
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.042
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     259
_refine_ls_number_reflns         3906
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.042
_refine_ls_R_factor_all          0.0551
_refine_ls_R_factor_gt           0.0463
_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)+(0.0502P)²+0.5690P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1191
_refine_ls_wR_factor_ref         0.1253
_reflns_Friedel_coverage         0.000
_reflns_number_gt                3391
_reflns_number_total             3906
_reflns_threshold_expression     'I > 2σ(I)'
_cod_data_source_file            c8cc01937a2.cif
_cod_data_source_block           nakazato_161104_1_0m_a
_cod_depositor_comments
'Adding full bibliography for 7121471--7121473.cif.'
_cod_database_code               7121471
_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.
;
_shelx_estimated_absorpt_t_min   0.969
_shelx_estimated_absorpt_t_max   0.997
_shelxl_version_number           2014-3
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
N001 N 0.56799(16) 0.36095(12) 0.56409(8) 0.0163(3) Uani 1 1 d . .
C002 C 0.66980(19) 0.47648(14) 0.61440(10) 0.0159(3) Uani 1 1 d . .
C003 C 0.91229(18) 0.47136(14) 0.51402(10) 0.0145(3) Uani 1 1 d . .
C004 C 0.63089(19) 0.29769(14) 0.49003(10) 0.0157(3) Uani 1 1 d . .
C005 C 0.59343(19) 0.52880(14) 0.70076(10) 0.0154(3) Uani 1 1 d . .
C006 C 0.83581(19) 0.54361(14) 0.58560(10) 0.0151(3) Uani 1 1 d . .
C007 C 0.32407(19) 0.55826(14) 0.77771(10) 0.0173(3) Uani 1 1 d . .
H19 H 0.1908 0.5423 0.7747 0.021 Uiso 1 1 calc R U
C008 C 0.49306(19) 0.18247(14) 0.43134(10) 0.0159(3) Uani 1 1 d . .
C009 C 0.90698(19) 0.26619(14) 0.40537(10) 0.0167(3) Uani 1 1 d . .
H27 H 0.8503 0.1760 0.3807 0.020 Uiso 1 1 calc R U
C00A C 0.70974(19) 0.59959(14) 0.78491(10) 0.0174(3) Uani 1 1 d . .
H20 H 0.8430 0.6125 0.7888 0.021 Uiso 1 1 calc R U
C00B C 0.6354(2) 0.65194(14) 0.86354(10) 0.0174(3) Uani 1 1 d . .
H21 H 0.7187 0.6999 0.9200 0.021 Uiso 1 1 calc R U
C00C C 0.39808(19) 0.50473(14) 0.69977(10) 0.0171(3) Uani 1 1 d . .
H22 H 0.3154 0.4512 0.6452 0.020 Uiso 1 1 calc R U
C00D C 0.20353(19) -0.02026(14) 0.31675(11) 0.0178(3) Uani 1 1 d . .
C00E C 0.81434(19) 0.34202(14) 0.46850(10) 0.0150(3) Uani 1 1 d . .
C00F C 0.3375(2) 0.05763(15) 0.27487(11) 0.0199(3) Uani 1 1 d . .
H23 H 0.3315 0.0425 0.2063 0.024 Uiso 1 1 calc R U
C00G C 1.07399(19) 0.32011(14) 0.37988(10) 0.0162(3) Uani 1 1 d . .
H28 H 1.1323 0.2666 0.3384 0.019 Uiso 1 1 calc R U
C00H C 0.4795(2) 0.15681(14) 0.33050(10) 0.0184(3) Uani 1 1 d . .
H24 H 0.5686 0.2079 0.2994 0.022 Uiso 1 1 calc R U
C00I C 0.2203(2) 0.00406(14) 0.41848(11) 0.0188(3) Uani 1 1 d . .
H25 H 0.1334 -0.0489 0.4497 0.023 Uiso 1 1 calc R U
C00J C 0.44005(19) 0.63511(14) 0.86077(10) 0.0161(3) Uani 1 1 d . .
C00K C 0.3515(2) 0.70112(15) 0.94175(10) 0.0188(3) Uani 1 1 d . .
C00L C 0.0477(2) -0.13120(15) 0.25561(11) 0.0211(3) Uani 1 1 d . .
C00M C 0.36107(19) 0.10376(15) 0.47451(10) 0.0180(3) Uani 1 1 d . .
H26 H 0.3678 0.1187 0.5432 0.022 Uiso 1 1 calc R U
C00N C 0.2595(2) 0.81043(16) 0.90178(12) 0.0263(4) Uani 1 1 d . .
H1 H 0.1982 0.8520 0.9517 0.039 Uiso 1 1 calc R U
H2 H 0.1648 0.7710 0.8440 0.039 Uiso 1 1 calc R U
H3 H 0.3568 0.8778 0.8842 0.039 Uiso 1 1 calc R U
C00O C 0.1995(2) 0.59807(16) 0.97224(11) 0.0253(4) Uani 1 1 d . .
H4 H 0.2571 0.5273 0.9963 0.038 Uiso 1 1 calc R U
H5 H 0.1007 0.5598 0.9160 0.038 Uiso 1 1 calc R U
H6 H 0.1437 0.6413 1.0238 0.038 Uiso 1 1 calc R U
C00P C 0.4976(2) 0.76385(19) 1.03206(12) 0.0309(4) Uani 1 1 d . .
H7 H 0.4345 0.8027 1.0823 0.046 Uiso 1 1 calc R U
H8 H 0.5923 0.8336 1.0150 0.046 Uiso 1 1 calc R U
H9 H 0.5598 0.6955 1.0568 0.046 Uiso 1 1 calc R U
C00Q C 0.0173(3) -0.11370(19) 0.14805(13) 0.0360(4) Uani 1 1 d . .
H10 H -0.0817 -0.1867 0.1113 0.054 Uiso 1 1 calc R U
H11 H 0.1353 -0.1144 0.1223 0.054 Uiso 1 1 calc R U
H12 H -0.0212 -0.0288 0.1418 0.054 Uiso 1 1 calc R U
C00R C 0.1105(3) -0.26355(17) 0.26119(15) 0.0408(5) Uani 1 1 d . .
H13 H 0.1172 -0.2831 0.3281 0.061 Uiso 1 1 calc R U
H14 H 0.2353 -0.2578 0.2418 0.061 Uiso 1 1 calc R U
H15 H 0.0191 -0.3346 0.2173 0.061 Uiso 1 1 calc R U
C00S C -0.1399(3) -0.1363(2) 0.29180(16) 0.0537(7) Uani 1 1 d . .
H16 H -0.2359 -0.2076 0.2509 0.081 Uiso 1 1 calc R U
H17 H -0.1790 -0.0511 0.2886 0.081 Uiso 1 1 calc R U
H18 H -0.1258 -0.1536 0.3593 0.081 Uiso 1 1 calc R U
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'
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
C004 N001 C002 120.65(12) . .
N001 C002 C006 121.92(12) . .
N001 C002 C005 115.02(12) . .
C006 C002 C005 123.05(12) . .
C006 C003 C00E 120.11(12) . .
C006 C003 C003 120.33(16) . 2_766
C00E C003 C003 119.55(15) . 2_766
N001 C004 C00E 121.61(12) . .
N001 C004 C008 115.16(12) . .
C00E C004 C008 123.20(12) . .
C00A C005 C00C 117.71(12) . .
C00A C005 C002 122.41(12) . .
C00C C005 C002 119.86(12) . .
C003 C006 C002 116.84(13) . .
C003 C006 C00G 118.09(12) . 2_766
C002 C006 C00G 125.00(13) . 2_766
C00C C007 C00J 121.91(13) . .
C00C C007 H19 119.0 . .
C00J C007 H19 119.0 . .
C00H C008 C00M 117.83(13) . .
C00H C008 C004 121.15(12) . .
C00M C008 C004 120.76(12) . .
C00G C009 C00E 121.59(13) . .
C00G C009 H27 119.2 . .
C00E C009 H27 119.2 . .
C005 C00A C00B 121.52(13) . .
C005 C00A H20 119.2 . .
C00B C00A H20 119.2 . .
C00A C00B C00J 121.03(13) . .
C00A C00B H21 119.5 . .
C00J C00B H21 119.5 . .
C007 C00C C005 120.59(13) . .
C007 C00C H22 119.7 . .
C005 C00C H22 119.7 . .
C00F C00D C00I 116.99(13) . .
C00F C00D C00L 122.02(13) . .
C00I C00D C00L 120.96(13) . .
C004 C00E C003 116.88(12) . .
C004 C00E C009 124.89(13) . .
C003 C00E C009 118.22(12) . .
C00H C00F C00D 121.85(13) . .
C00H C00F H23 119.1 . .
C00D C00F H23 119.1 . .
C009 C00G C006 121.26(13) . 2_766
C009 C00G H28 119.4 . .
C006 C00G H28 119.4 2_766 .
C00F C00H C008 120.92(13) . .
C00F C00H H24 119.5 . .
C008 C00H H24 119.5 . .
C00M C00I C00D 121.45(13) . .
C00M C00I H25 119.3 . .
C00D C00I H25 119.3 . .
C00B C00J C007 117.05(12) . .
C00B C00J C00K 122.91(12) . .
C007 C00J C00K 119.99(12) . .
C00P C00K C00J 112.27(12) . .
C00P C00K C00O 108.11(13) . .
C00J C00K C00O 110.17(12) . .
C00P C00K C00N 108.87(13) . .
C00J C00K C00N 108.09(12) . .
C00O C00K C00N 109.28(12) . .
C00S C00L C00R 109.79(16) . .
C00S C00L C00Q 108.09(15) . .
C00R C00L C00Q 107.19(14) . .
C00S C00L C00D 111.74(13) . .
C00R C00L C00D 108.15(13) . .
C00Q C00L C00D 111.78(13) . .
C00I C00M C008 120.93(13) . .
C00I C00M H26 119.5 . .
C008 C00M H26 119.5 . .
C00K C00N H1 109.5 . .
C00K C00N H2 109.5 . .
H1 C00N H2 109.5 . .
C00K C00N H3 109.5 . .
H1 C00N H3 109.5 . .
H2 C00N H3 109.5 . .
C00K C00O H4 109.5 . .
C00K C00O H5 109.5 . .
H4 C00O H5 109.5 . .
C00K C00O H6 109.5 . .
H4 C00O H6 109.5 . .
H5 C00O H6 109.5 . .
C00K C00P H7 109.5 . .
C00K C00P H8 109.5 . .
H7 C00P H8 109.5 . .
C00K C00P H9 109.5 . .
H7 C00P H9 109.5 . .
H8 C00P H9 109.5 . .
C00L C00Q H10 109.5 . .
C00L C00Q H11 109.5 . .
H10 C00Q H11 109.5 . .
C00L C00Q H12 109.5 . .
H10 C00Q H12 109.5 . .
H11 C00Q H12 109.5 . .
C00L C00R H13 109.5 . .
C00L C00R H14 109.5 . .
H13 C00R H14 109.5 . .
C00L C00R H15 109.5 . .
H13 C00R H15 109.5 . .
H14 C00R H15 109.5 . .
C00L C00S H16 109.5 . .
C00L C00S H17 109.5 . .
H16 C00S H17 109.5 . .
C00L C00S H18 109.5 . .
H16 C00S H18 109.5 . .
H17 C00S H18 109.5 . .
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
N001 C004 1.3405(18) .
N001 C002 1.3426(18) .
C002 C006 1.417(2) .
C002 C005 1.4872(19) .
C003 C006 1.4164(19) .
C003 C00E 1.4227(19) .
C003 C003 1.436(3) 2_766
C004 C00E 1.4193(19) .
C004 C008 1.4839(19) .
C005 C00A 1.390(2) .
C005 C00C 1.3989(19) .
C006 C00G 1.4357(19) 2_766
C007 C00C 1.3864(19) .
C007 C00J 1.400(2) .
C007 H19 0.9500 .
C008 C00H 1.394(2) .
C008 C00M 1.397(2) .
C009 C00G 1.358(2) .
C009 C00E 1.4319(19) .
C009 H27 0.9500 .
C00A C00B 1.3908(19) .
C00A H20 0.9500 .
C00B C00J 1.3982(19) .
C00B H21 0.9500 .
C00C H22 0.9500 .
C00D C00F 1.392(2) .
C00D C00I 1.403(2) .
C00D C00L 1.5350(19) .
C00F C00H 1.388(2) .
C00F H23 0.9500 .
C00G C006 1.4357(19) 2_766
C00G H28 0.9500 .
C00H H24 0.9500 .
C00I C00M 1.388(2) .
C00I H25 0.9500 .
C00J C00K 1.5343(18) .
C00K C00P 1.527(2) .
C00K C00O 1.536(2) .
C00K C00N 1.540(2) .
C00L C00S 1.519(2) .
C00L C00R 1.529(2) .
C00L C00Q 1.532(2) .
C00M H26 0.9500 .
C00N H1 0.9800 .
C00N H2 0.9800 .
C00N H3 0.9800 .
C00O H4 0.9800 .
C00O H5 0.9800 .
C00O H6 0.9800 .
C00P H7 0.9800 .
C00P H8 0.9800 .
C00P H9 0.9800 .
C00Q H10 0.9800 .
C00Q H11 0.9800 .
C00Q H12 0.9800 .
C00R H13 0.9800 .
C00R H14 0.9800 .
C00R H15 0.9800 .
C00S H16 0.9800 .
C00S H17 0.9800 .
C00S H18 0.9800 .
loop_
_cod_related_entry_id
_cod_related_entry_database
_cod_related_entry_code
1 PubChem 138980815
