#------------------------------------------------------------------------------
#$Date: 2016-02-18 16:37:37 +0100 (jue 18 de feb de 2016) $
#$Revision: 176729 $
#$URL: svn://www.crystallography.net/cod/cif/1/51/32/1513255.cif $
#------------------------------------------------------------------------------
#
# This file is available in the Crystallography Open Database (COD),
# http://www.crystallography.net/. The original data for this entry
# were provided the Crystal Eye server at
# http://wwmm.ch.cam.ac.uk/crystaleye/, created by Nick Day at the
# Peter Murray-Rust laboratory.
#
# The file may be used within the scientific community so long as
# proper attribution is given to the journal article from which the
# data were obtained.
#
data_1513255
loop_
_publ_author_name
'Richards, Gary J.'
'Hill, Jonathan P.'
'Okamoto, Ken'
'Shundo, Atsuomi'
'Akada, Misaho'
'Elsegood, Mark R. J.'
'Mori, Toshiyuki'
'Ariga, Katsuhiko'
_publ_section_title
;
 Diverse Self-Assembly in Soluble Oligoazaacenes: A Microscopy
 Study†
;
_journal_issue                   15
_journal_name_full               Langmuir
_journal_page_first              8408
_journal_page_last               8413
_journal_paper_doi               10.1021/la8041633
_journal_volume                  25
_journal_year                    2009
_chemical_formula_moiety         'C20 H8 N6'
_chemical_formula_sum            'C20 H8 N6'
_chemical_formula_weight         332.32
_chemical_name_systematic
;
 ?
;
_space_group_IT_number           14
_symmetry_cell_setting           monoclinic
_symmetry_space_group_name_Hall  '-P 2yn'
_symmetry_space_group_name_H-M   'P 1 21/n 1'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_audit_creation_method           SHELXL-97
_cell_angle_alpha                90.00
_cell_angle_beta                 99.945(3)
_cell_angle_gamma                90.00
_cell_formula_units_Z            4
_cell_length_a                   9.3164(17)
_cell_length_b                   7.0649(13)
_cell_length_c                   23.684(4)
_cell_measurement_reflns_used    1593
_cell_measurement_temperature    150(2)
_cell_measurement_theta_max      24.34
_cell_measurement_theta_min      3.01
_cell_volume                     1535.4(5)
_computing_cell_refinement       'Bruker SAINT'
_computing_data_collection       'Bruker APEX 2'
_computing_data_reduction        'Bruker SAINT'
_computing_molecular_graphics    'Bruker SHELXTL'
_computing_publication_material  'Bruker SHELXTL and local programs'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 2008)'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 2008)'
_diffrn_ambient_temperature      150(2)
_diffrn_measured_fraction_theta_full 0.999
_diffrn_measured_fraction_theta_max 0.999
_diffrn_measurement_device_type  'Bruker APEX 2 CCD diffractometer'
_diffrn_measurement_method       'ω rotation with narrow frames'
_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  0.0651
_diffrn_reflns_av_sigmaI/netI    0.0597
_diffrn_reflns_limit_h_max       11
_diffrn_reflns_limit_h_min       -11
_diffrn_reflns_limit_k_max       8
_diffrn_reflns_limit_k_min       -8
_diffrn_reflns_limit_l_max       29
_diffrn_reflns_limit_l_min       -29
_diffrn_reflns_number            13123
_diffrn_reflns_theta_full        26.45
_diffrn_reflns_theta_max         26.45
_diffrn_reflns_theta_min         1.75
_diffrn_standards_decay_%        0
_diffrn_standards_number         0
_exptl_absorpt_coefficient_mu    0.092
_exptl_absorpt_correction_T_max  0.998
_exptl_absorpt_correction_T_min  0.953
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   'SADABS v2008/1, Sheldrick, G.M., (2008)'
_exptl_crystal_colour            'dark orange'
_exptl_crystal_density_diffrn    1.438
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       lath
_exptl_crystal_F_000             680
_exptl_crystal_size_max          0.53
_exptl_crystal_size_mid          0.08
_exptl_crystal_size_min          0.02
_refine_diff_density_max         0.142
_refine_diff_density_min         -0.148
_refine_diff_density_rms         0.034
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   0.942
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     235
_refine_ls_number_reflns         3155
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      0.942
_refine_ls_R_factor_all          0.1235
_refine_ls_R_factor_gt           0.0449
_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)+(0.0515P)²+0.0000P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0917
_refine_ls_wR_factor_ref         0.1201
_reflns_number_gt                1491
_reflns_number_total             3155
_reflns_threshold_expression     I>2σ(I)
_cod_data_source_file            la8041633sup1.cif
_cod_data_source_block           jph1
_cod_original_sg_symbol_H-M      P2(1)/n
_cod_database_code               1513255
loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'-x+1/2, y+1/2, -z+1/2'
'-x, -y, -z'
'x-1/2, -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_symmetry_multiplicity
_atom_site_calc_flag
_atom_site_refinement_flags
C1 C 0.7094(2) 0.7728(4) -0.05412(9) 0.0473(6) Uani 1 1 d .
C2 C 0.6304(3) 0.6051(4) -0.05547(10) 0.0545(7) Uani 1 1 d .
H2 H 0.5787 0.5773 -0.0252 0.065 Uiso 1 1 calc R
C3 C 0.6262(3) 0.4787(4) -0.10009(10) 0.0587(7) Uani 1 1 d .
H3 H 0.5721 0.3645 -0.1006 0.070 Uiso 1 1 calc R
C4 C 0.7018(3) 0.5201(4) -0.14422(10) 0.0631(8) Uani 1 1 d .
H4 H 0.6986 0.4341 -0.1752 0.076 Uiso 1 1 calc R
C5 C 0.7810(3) 0.6841(4) -0.14343(10) 0.0603(8) Uani 1 1 d .
H5 H 0.8329 0.7090 -0.1738 0.072 Uiso 1 1 calc R
C6 C 0.7872(3) 0.8159(4) -0.09868(9) 0.0498(7) Uani 1 1 d .
C7 C 0.8712(2) 0.9920(4) -0.09720(9) 0.0496(7) Uani 1 1 d .
C8 C 0.9522(3) 1.0407(4) -0.14006(10) 0.0588(7) Uani 1 1 d .
H8 H 0.9504 0.9593 -0.1721 0.071 Uiso 1 1 calc R
C9 C 1.0337(3) 1.2038(5) -0.13643(10) 0.0631(8) Uani 1 1 d .
H9 H 1.0865 1.2338 -0.1662 0.076 Uiso 1 1 calc R
C10 C 1.0400(3) 1.3247(4) -0.09028(10) 0.0598(7) Uani 1 1 d .
H10 H 1.0977 1.4363 -0.0877 0.072 Uiso 1 1 calc R
C11 C 0.9610(3) 1.2804(4) -0.04800(9) 0.0539(7) Uani 1 1 d .
H11 H 0.9648 1.3628 -0.0161 0.065 Uiso 1 1 calc R
C12 C 0.8758(2) 1.1179(4) -0.05092(9) 0.0467(6) Uani 1 1 d .
C13 C 0.7932(2) 1.0781(4) -0.00547(9) 0.0436(6) Uani 1 1 d .
N1 N 0.79630(19) 1.2050(3) 0.03627(7) 0.0457(5) Uani 1 1 d .
C14 C 0.7187(2) 1.1606(4) 0.07775(9) 0.0434(6) Uani 1 1 d .
N2 N 0.72489(19) 1.2882(3) 0.12097(7) 0.0451(5) Uani 1 1 d .
C15 C 0.6500(2) 1.2435(4) 0.16133(8) 0.0422(6) Uani 1 1 d .
C16 C 0.5689(2) 1.0737(4) 0.16040(9) 0.0440(6) Uani 1 1 d .
N3 N 0.56113(19) 0.9487(3) 0.11854(7) 0.0447(5) Uani 1 1 d .
C17 C 0.6373(2) 0.9924(4) 0.07631(8) 0.0419(6) Uani 1 1 d .
N4 N 0.63070(19) 0.8653(3) 0.03297(7) 0.0451(5) Uani 1 1 d .
C18 C 0.7100(2) 0.9065(4) -0.00691(9) 0.0444(6) Uani 1 1 d .
C19 C 0.6536(2) 1.3776(4) 0.20798(10) 0.0501(7) Uani 1 1 d .
N5 N 0.6557(2) 1.4834(3) 0.24450(9) 0.0655(7) Uani 1 1 d .
C20 C 0.4914(3) 1.0264(4) 0.20659(9) 0.0491(6) Uani 1 1 d .
N6 N 0.4304(2) 0.9886(3) 0.24292(8) 0.0677(7) 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
C2 C1 C6 120.2(2)
C2 C1 C18 119.9(2)
C6 C1 C18 119.8(2)
C3 C2 C1 120.9(2)
C2 C3 C4 119.3(3)
C5 C4 C3 120.6(3)
C4 C5 C6 121.5(2)
C5 C6 C1 117.5(3)
C5 C6 C7 122.2(2)
C1 C6 C7 120.3(2)
C12 C7 C8 117.3(3)
C12 C7 C6 120.0(2)
C8 C7 C6 122.7(2)
C9 C8 C7 121.3(2)
C8 C9 C10 121.0(2)
C11 C10 C9 118.7(3)
C10 C11 C12 121.6(2)
C11 C12 C7 120.1(2)
C11 C12 C13 119.6(2)
C7 C12 C13 120.4(2)
N1 C13 C18 121.9(2)
N1 C13 C12 118.2(2)
C18 C13 C12 119.9(2)
C13 N1 C14 115.9(2)
N1 C14 N2 115.8(2)
N1 C14 C17 122.1(2)
N2 C14 C17 122.13(19)
C15 N2 C14 115.4(2)
N2 C15 C16 122.7(2)
N2 C15 C19 116.8(2)
C16 C15 C19 120.48(19)
N3 C16 C15 122.6(2)
N3 C16 C20 116.2(2)
C15 C16 C20 121.2(2)
C16 N3 C17 115.7(2)
N4 C17 N3 116.5(2)
N4 C17 C14 122.07(19)
N3 C17 C14 121.5(2)
C18 N4 C17 115.8(2)
N4 C18 C13 122.2(2)
N4 C18 C1 118.2(2)
C13 C18 C1 119.6(2)
N5 C19 C15 179.6(3)
N6 C20 C16 179.8(3)
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
C1 C2 1.392(3)
C1 C6 1.413(3)
C1 C18 1.463(3)
C2 C3 1.379(3)
C3 C4 1.389(3)
C4 C5 1.372(4)
C5 C6 1.405(3)
C6 C7 1.467(3)
C7 C12 1.406(3)
C7 C8 1.408(3)
C8 C9 1.374(4)
C9 C10 1.380(4)
C10 C11 1.377(3)
C11 C12 1.391(3)
C12 C13 1.455(3)
C13 N1 1.331(3)
C13 C18 1.436(3)
N1 C14 1.353(3)
C14 N2 1.358(3)
C14 C17 1.406(3)
N2 C15 1.316(2)
C15 C16 1.415(3)
C15 C19 1.451(3)
C16 N3 1.320(3)
C16 C20 1.450(3)
N3 C17 1.358(3)
C17 N4 1.357(3)
N4 C18 1.328(3)
C19 N5 1.140(3)
C20 N6 1.142(3)
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
C6 C1 C2 C3 -0.2(3)
C18 C1 C2 C3 178.8(2)
C1 C2 C3 C4 -0.1(4)
C2 C3 C4 C5 0.5(4)
C3 C4 C5 C6 -0.7(4)
C4 C5 C6 C1 0.5(3)
C4 C5 C6 C7 -179.9(2)
C2 C1 C6 C5 0.0(3)
C18 C1 C6 C5 -179.0(2)
C2 C1 C6 C7 -179.7(2)
C18 C1 C6 C7 1.4(3)
C5 C6 C7 C12 -178.9(2)
C1 C6 C7 C12 0.7(3)
C5 C6 C7 C8 -0.5(3)
C1 C6 C7 C8 179.1(2)
C12 C7 C8 C9 0.7(3)
C6 C7 C8 C9 -177.8(2)
C7 C8 C9 C10 0.6(4)
C8 C9 C10 C11 -0.9(4)
C9 C10 C11 C12 -0.1(3)
C10 C11 C12 C7 1.4(3)
C10 C11 C12 C13 -179.4(2)
C8 C7 C12 C11 -1.7(3)
C6 C7 C12 C11 176.8(2)
C8 C7 C12 C13 179.1(2)
C6 C7 C12 C13 -2.3(3)
C11 C12 C13 N1 3.4(3)
C7 C12 C13 N1 -177.4(2)
C11 C12 C13 C18 -177.3(2)
C7 C12 C13 C18 1.9(3)
C18 C13 N1 C14 1.2(3)
C12 C13 N1 C14 -179.48(18)
C13 N1 C14 N2 178.51(19)
C13 N1 C14 C17 -1.2(3)
N1 C14 N2 C15 -179.56(19)
C17 C14 N2 C15 0.1(3)
C14 N2 C15 C16 0.4(3)
C14 N2 C15 C19 -179.6(2)
N2 C15 C16 N3 -0.9(3)
C19 C15 C16 N3 179.2(2)
N2 C15 C16 C20 178.0(2)
C19 C15 C16 C20 -1.9(3)
C15 C16 N3 C17 0.6(3)
C20 C16 N3 C17 -178.33(19)
C16 N3 C17 N4 179.90(19)
C16 N3 C17 C14 0.0(3)
N1 C14 C17 N4 -0.6(3)
N2 C14 C17 N4 179.7(2)
N1 C14 C17 N3 179.31(19)
N2 C14 C17 N3 -0.4(3)
N3 C17 N4 C18 -177.60(18)
C14 C17 N4 C18 2.3(3)
C17 N4 C18 C13 -2.3(3)
C17 N4 C18 C1 178.82(19)
N1 C13 C18 N4 0.6(3)
C12 C13 C18 N4 -178.73(19)
N1 C13 C18 C1 179.43(19)
C12 C13 C18 C1 0.2(3)
C2 C1 C18 N4 -1.8(3)
C6 C1 C18 N4 177.15(19)
C2 C1 C18 C13 179.3(2)
C6 C1 C18 C13 -1.8(3)
