#------------------------------------------------------------------------------
#$Date: 2022-11-08 10:31:19 +0200 (Tue, 08 Nov 2022) $
#$Revision: 279077 $
#$URL: file:///home/coder/svn-repositories/cod/cif/8/10/59/8105998.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_8105998
loop_
_publ_author_name
'Kirste, Matthias'
'Brietzke, Thomas'
'Holdt, Hans-Jürgen'
'Schilde, Uwe'
_publ_section_title
;
 The crystal structure of 1,12-diazaperylene, C18H10N2
;
_journal_issue                   6
_journal_name_full
'Zeitschrift für Kristallographie - New Crystal Structures'
_journal_page_first              1255
_journal_page_last               1257
_journal_paper_doi               10.1515/ncrs-2019-0385
_journal_volume                  234
_journal_year                    2019
_chemical_formula_moiety         'C18 H10 N2'
_chemical_formula_sum            'C18 H10 N2'
_chemical_formula_weight         254.28
_chemical_melting_point          532.0(10)
_chemical_name_systematic
;
 1,12-diazaperylene
;
_space_group_crystal_system      monoclinic
_space_group_IT_number           14
_space_group_name_Hall           '-P 2ybc'
_space_group_name_H-M_alt        'P 1 21/c 1'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_audit_creation_method           SHELXL-2014/7
_cell_angle_alpha                90
_cell_angle_beta                 105.363(8)
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   7.9297(9)
_cell_length_b                   11.4021(14)
_cell_length_c                   13.3572(15)
_cell_measurement_reflns_used    11943
_cell_measurement_temperature    210(2)
_cell_measurement_theta_max      31.88
_cell_measurement_theta_min      2.67
_cell_volume                     1164.5(2)
_computing_cell_refinement       'X-AREA (Stoe, 2015)'
_computing_data_collection       'X-AREA (Stoe, 2015)'
_computing_data_reduction        'X-RED (Stoe, 2015)'
_computing_molecular_graphics
;
 ORTEP-3 for Windows (Farrugia, 2012)
;
_computing_publication_material
; 
 SHELXL-2014/7 (Sheldrick, 2014)
;
_computing_structure_refinement  'SHELXL-2014/7 (Sheldrick, 2014)'
_computing_structure_solution    'SHELXS-2013/1 (Sheldrick, 2013)'
_diffrn_ambient_temperature      210(2)
_diffrn_detector                 'Pilatus 200K'
_diffrn_measured_fraction_theta_full 0.997
_diffrn_measured_fraction_theta_max 0.997
_diffrn_measurement_details
; 
 2842 frames, exposure time = 25 s per frame,
 detector distance = 60 mm, Δω = 0.5 °
;
_diffrn_measurement_device       '4-circle goniometer'
_diffrn_measurement_device_type  'STOE StadiVari'
_diffrn_measurement_method       'rotation method'
_diffrn_radiation_collimation    '0.3 mm diameter'
_diffrn_radiation_monochromator  'graded multilayer mirror'
_diffrn_radiation_source         'Genix Microfocus'
_diffrn_radiation_type           'Mo K\a'
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0547
_diffrn_reflns_av_unetI/netI     0.0454
_diffrn_reflns_Laue_measured_fraction_full 0.997
_diffrn_reflns_Laue_measured_fraction_max 0.997
_diffrn_reflns_limit_h_max       9
_diffrn_reflns_limit_h_min       -9
_diffrn_reflns_limit_k_max       13
_diffrn_reflns_limit_k_min       -13
_diffrn_reflns_limit_l_max       15
_diffrn_reflns_limit_l_min       -15
_diffrn_reflns_number            20040
_diffrn_reflns_point_group_measured_fraction_full 0.997
_diffrn_reflns_point_group_measured_fraction_max 0.997
_diffrn_reflns_theta_full        24.997
_diffrn_reflns_theta_max         24.997
_diffrn_reflns_theta_min         3.163
_diffrn_source_current           1.000
_diffrn_source_voltage           50
_exptl_absorpt_coefficient_mu    0.087
_exptl_absorpt_correction_T_max  0.9966
_exptl_absorpt_correction_T_min  0.9966
_exptl_absorpt_correction_type   sphere
_exptl_absorpt_process_details   'X-Area (Stoe, 2015)'
_exptl_crystal_colour            yellow
_exptl_crystal_density_diffrn    1.450
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       'flat needle'
_exptl_crystal_F_000             528
_exptl_crystal_size_max          0.30
_exptl_crystal_size_mid          0.08
_exptl_crystal_size_min          0.03
_exptl_crystal_size_rad          0.0549
_refine_diff_density_max         0.157
_refine_diff_density_min         -0.124
_refine_diff_density_rms         0.027
_refine_ls_extinction_coef       0.013(3)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc²λ³/sin(2θ)]^-1/4^
_refine_ls_extinction_method     'SHELXL-2014/7 (Sheldrick 2014'
_refine_ls_goodness_of_fit_ref   0.801
_refine_ls_hydrogen_treatment    refU
_refine_ls_matrix_type           full
_refine_ls_number_parameters     192
_refine_ls_number_reflns         2051
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      0.801
_refine_ls_R_factor_all          0.0619
_refine_ls_R_factor_gt           0.0325
_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)+(0.044P)²+0.1246P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0703
_refine_ls_wR_factor_ref         0.0774
_reflns_number_gt                1229
_reflns_number_total             2051
_reflns_threshold_expression     'I > 2σ(I)'
_cod_data_source_file            suppl_ncrs-2019-0385_suppl.cif
_cod_data_source_block           k12p
_cod_depositor_comments
;
The following automatic conversions were performed:

data item '_chemical_melting_point' value '531-533' was changed to
'532.0(10)' -- the average value was taken and precision was
estimated.

Automatic conversion script
Id: cif_fix_values 8738 2021-04-28 16:35:53Z antanas 
;
_cod_original_sg_symbol_H-M      'P 21/c'
_cod_database_code               8105998
_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   0.974
_shelx_estimated_absorpt_t_max   0.997
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x, y+1/2, -z+1/2'
'-x, -y, -z'
'x, -y-1/2, z-1/2'
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
_atom_site_refinement_flags_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
C1 C 0.9113(2) 1.03165(14) 0.25918(12) 0.0448(4) Uani 1 1 d . . . . .
H1 H 1.0266 1.0505 0.2957 0.045(4) Uiso 1 1 calc R . . . .
C2 C 0.7818(2) 1.10273(14) 0.27236(11) 0.0422(4) Uani 1 1 d . . . . .
H2 H 0.8081 1.1692 0.3153 0.053(5) Uiso 1 1 calc R . . . .
C3 C 0.4638(2) 1.14306(14) 0.23109(11) 0.0421(4) Uani 1 1 d . . . . .
H3 H 0.4827 1.2116 0.2717 0.054(5) Uiso 1 1 calc R . . . .
C4 C 0.2987(2) 1.10912(14) 0.18233(12) 0.0451(4) Uani 1 1 d . . . . .
H4 H 0.2037 1.1539 0.1906 0.051(5) Uiso 1 1 calc R . . . .
C5 C 0.2670(2) 1.00865(14) 0.11996(11) 0.0396(4) Uani 1 1 d . . . . .
H5 H 0.1509 0.9865 0.0883 0.050(5) Uiso 1 1 calc R . . . .
C6 C 0.2102(2) 0.80169(14) -0.02114(12) 0.0428(4) Uani 1 1 d . . . . .
H6 H 0.1108 0.8418 -0.0135 0.048(5) Uiso 1 1 calc R . . . .
C7 C 0.1888(2) 0.70620(15) -0.08899(13) 0.0520(5) Uani 1 1 d . . . . .
H7 H 0.0757 0.6849 -0.1275 0.054(5) Uiso 1 1 calc R . . . .
C8 C 0.3279(2) 0.64386(15) -0.10020(12) 0.0507(5) Uani 1 1 d . . . . .
H8 H 0.3108 0.5797 -0.1460 0.057(5) Uiso 1 1 calc R . . . .
C9 C 0.6489(2) 0.61343(14) -0.04973(13) 0.0495(4) Uani 1 1 d . . . . .
H9 H 0.6392 0.5471 -0.0927 0.060(5) Uiso 1 1 calc R . . . .
C10 C 0.8073(2) 0.65045(15) 0.00631(12) 0.0499(5) Uani 1 1 d . . . . .
H10 H 0.9055 0.6074 0.0007 0.054(5) Uiso 1 1 calc R . . . .
C11 C 0.69583(18) 0.80484(12) 0.07775(10) 0.0313(3) Uani 1 1 d . . . . .
C12 C 0.72404(17) 0.90830(12) 0.14686(10) 0.0302(3) Uani 1 1 d . . . . .
C13 C 0.57669(17) 0.97427(12) 0.15639(10) 0.0284(3) Uani 1 1 d . . . . .
C14 C 0.40181(17) 0.94130(13) 0.10382(10) 0.0296(3) Uani 1 1 d . . . . .
C15 C 0.37367(18) 0.83850(12) 0.03483(10) 0.0310(3) Uani 1 1 d . . . . .
C16 C 0.52216(18) 0.77376(12) 0.02340(10) 0.0308(3) Uani 1 1 d . . . . .
C17 C 0.4982(2) 0.67485(13) -0.04340(11) 0.0390(4) Uani 1 1 d . . . . .
C18 C 0.60749(19) 1.07544(13) 0.22087(10) 0.0338(4) Uani 1 1 d . . . . .
N1 N 0.88720(15) 0.93566(12) 0.19737(9) 0.0406(3) Uani 1 1 d . . . . .
N2 N 0.83589(16) 0.74497(11) 0.07003(10) 0.0419(3) Uani 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'
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
N1 C1 C2 124.95(14) . .
N1 C1 H1 117.5 . .
C2 C1 H1 117.5 . .
C1 C2 C18 118.98(15) . .
C1 C2 H2 120.5 . .
C18 C2 H2 120.5 . .
C4 C3 C18 119.94(15) . .
C4 C3 H3 120.0 . .
C18 C3 H3 120.0 . .
C3 C4 C5 121.22(15) . .
C3 C4 H4 119.4 . .
C5 C4 H4 119.4 . .
C14 C5 C4 121.62(15) . .
C14 C5 H5 119.2 . .
C4 C5 H5 119.2 . .
C15 C6 C7 121.57(16) . .
C15 C6 H6 119.2 . .
C7 C6 H6 119.2 . .
C8 C7 C6 121.22(16) . .
C8 C7 H7 119.4 . .
C6 C7 H7 119.4 . .
C7 C8 C17 120.14(16) . .
C7 C8 H8 119.9 . .
C17 C8 H8 119.9 . .
C10 C9 C17 119.49(16) . .
C10 C9 H9 120.3 . .
C17 C9 H9 120.3 . .
C9 C10 N2 125.00(16) . .
C9 C10 H10 117.5 . .
N2 C10 H10 117.5 . .
N2 C11 C16 123.25(14) . .
N2 C11 C12 117.81(13) . .
C16 C11 C12 118.94(13) . .
N1 C12 C13 122.87(13) . .
N1 C12 C11 118.07(13) . .
C13 C12 C11 119.06(12) . .
C18 C13 C12 118.01(12) . .
C18 C13 C14 119.99(13) . .
C12 C13 C14 122.00(13) . .
C5 C14 C13 117.93(14) . .
C5 C14 C15 123.12(13) . .
C13 C14 C15 118.94(13) . .
C6 C15 C16 117.82(14) . .
C6 C15 C14 123.15(14) . .
C16 C15 C14 119.02(13) . .
C17 C16 C11 118.02(13) . .
C17 C16 C15 119.98(13) . .
C11 C16 C15 122.01(13) . .
C9 C17 C8 123.47(16) . .
C9 C17 C16 117.31(15) . .
C8 C17 C16 119.22(15) . .
C2 C18 C3 123.07(15) . .
C2 C18 C13 117.70(14) . .
C3 C18 C13 119.23(14) . .
C12 N1 C1 117.45(13) . .
C11 N2 C10 116.93(14) . .
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
C1 N1 1.354(2) .
C1 C2 1.356(2) .
C1 H1 0.9400 .
C2 C18 1.406(2) .
C2 H2 0.9400 .
C3 C4 1.355(2) .
C3 C18 1.412(2) .
C3 H3 0.9400 .
C4 C5 1.399(2) .
C4 H4 0.9400 .
C5 C14 1.379(2) .
C5 H5 0.9400 .
C6 C15 1.379(2) .
C6 C7 1.398(2) .
C6 H6 0.9400 .
C7 C8 1.354(2) .
C7 H7 0.9400 .
C8 C17 1.407(2) .
C8 H8 0.9400 .
C9 C10 1.349(2) .
C9 C17 1.407(2) .
C9 H9 0.9400 .
C10 N2 1.355(2) .
C10 H10 0.9400 .
C11 N2 1.3307(17) .
C11 C16 1.4211(19) .
C11 C12 1.478(2) .
C12 N1 1.3282(17) .
C12 C13 1.4234(19) .
C13 C18 1.4214(19) .
C13 C14 1.4288(19) .
C14 C15 1.471(2) .
C15 C16 1.432(2) .
C16 C17 1.4192(19) .
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_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
N1 C1 C2 C18 1.6(2) . . . .
C18 C3 C4 C5 -1.1(2) . . . .
C3 C4 C5 C14 -1.3(2) . . . .
C15 C6 C7 C8 1.9(2) . . . .
C6 C7 C8 C17 -0.2(2) . . . .
C17 C9 C10 N2 -0.3(2) . . . .
N2 C11 C12 N1 -0.06(19) . . . .
C16 C11 C12 N1 179.69(12) . . . .
N2 C11 C12 C13 179.79(12) . . . .
C16 C11 C12 C13 -0.45(18) . . . .
N1 C12 C13 C18 1.71(19) . . . .
C11 C12 C13 C18 -178.14(12) . . . .
N1 C12 C13 C14 -178.05(13) . . . .
C11 C12 C13 C14 2.10(18) . . . .
C4 C5 C14 C13 2.5(2) . . . .
C4 C5 C14 C15 -176.96(13) . . . .
C18 C13 C14 C5 -1.53(19) . . . .
C12 C13 C14 C5 178.23(13) . . . .
C18 C13 C14 C15 177.99(12) . . . .
C12 C13 C14 C15 -2.25(18) . . . .
C7 C6 C15 C16 -1.6(2) . . . .
C7 C6 C15 C14 177.54(13) . . . .
C5 C14 C15 C6 1.2(2) . . . .
C13 C14 C15 C6 -178.33(13) . . . .
C5 C14 C15 C16 -179.75(13) . . . .
C13 C14 C15 C16 0.75(18) . . . .
N2 C11 C16 C17 -0.9(2) . . . .
C12 C11 C16 C17 179.34(12) . . . .
N2 C11 C16 C15 178.73(13) . . . .
C12 C11 C16 C15 -1.01(19) . . . .
C6 C15 C16 C17 -0.36(19) . . . .
C14 C15 C16 C17 -179.49(13) . . . .
C6 C15 C16 C11 179.99(13) . . . .
C14 C15 C16 C11 0.86(19) . . . .
C10 C9 C17 C8 178.94(15) . . . .
C10 C9 C17 C16 -0.4(2) . . . .
C7 C8 C17 C9 179.07(15) . . . .
C7 C8 C17 C16 -1.6(2) . . . .
C11 C16 C17 C9 0.93(19) . . . .
C15 C16 C17 C9 -178.73(13) . . . .
C11 C16 C17 C8 -178.40(13) . . . .
C15 C16 C17 C8 1.9(2) . . . .
C1 C2 C18 C3 178.97(14) . . . .
C1 C2 C18 C13 -0.6(2) . . . .
C4 C3 C18 C2 -177.45(14) . . . .
C4 C3 C18 C13 2.1(2) . . . .
C12 C13 C18 C2 -0.95(19) . . . .
C14 C13 C18 C2 178.82(12) . . . .
C12 C13 C18 C3 179.50(12) . . . .
C14 C13 C18 C3 -0.7(2) . . . .
C13 C12 N1 C1 -0.8(2) . . . .
C11 C12 N1 C1 179.02(13) . . . .
C2 C1 N1 C12 -0.9(2) . . . .
C16 C11 N2 C10 0.3(2) . . . .
C12 C11 N2 C10 -179.99(13) . . . .
C9 C10 N2 C11 0.4(2) . . . .
