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#$Date: 2016-03-21 01:21:50 +0200 (Mon, 21 Mar 2016) $
#$Revision: 178377 $
#$URL: svn://www.crystallography.net/cod/cif/4/00/10/4001008.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_4001008
loop_
_publ_author_name
'Tang, Qin'
'Zhang, Dieqing'
'Wang, Shenglong'
'Ke, Ning'
'Xu, Jianbin'
'Yu, Jimmy C.'
'Miao, Qian'
_publ_section_title
;
 A Meaningful Analogue of Pentacene: Charge Transport, Polymorphs, and
 Electronic Structures of Dihydrodiazapentacene
;
_journal_issue                   7
_journal_name_full               'Chemistry of Materials'
_journal_page_first              1400
_journal_paper_doi               10.1021/cm9001916
_journal_volume                  21
_journal_year                    2009
_chemical_formula_sum            'C20 H14 N2'
_chemical_formula_weight         282.33
_chemical_name_systematic
; 
 6,13-dihydro-6,13-diazapentacene 
;
_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                87.439(8)
_cell_angle_beta                 84.837(8)
_cell_angle_gamma                86.219(8)
_cell_formula_units_Z            2
_cell_length_a                   5.752(2)
_cell_length_b                   8.880(4)
_cell_length_c                   13.167(5)
_cell_measurement_temperature    296(2)
_cell_volume                     667.8(5)
_computing_cell_refinement       'BRUKER KAPPA APEXII DUO DIFFRACTOMETER'
_computing_data_collection       'BRUKER KAPPA APEXII DUO DIFFRACTOMETER'
_computing_data_reduction        'BRUKER KAPPA APEXII DUO DIFFRACTOMETER'
_computing_molecular_graphics    'SIEMENS SHELXTL'
_computing_publication_material  'SIEMENS SHELXTL'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 1990)'
_diffrn_ambient_temperature      296(2)
_diffrn_measured_fraction_theta_full 0.987
_diffrn_measured_fraction_theta_max 0.987
_diffrn_measurement_device_type  'BRUKER KAPPA APEXII DUO DIFFRACTOMETER'
_diffrn_measurement_method       'OMEGA SCAN'
_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  0.0254
_diffrn_reflns_av_sigmaI/netI    0.0244
_diffrn_reflns_limit_h_max       6
_diffrn_reflns_limit_h_min       -6
_diffrn_reflns_limit_k_max       10
_diffrn_reflns_limit_k_min       -9
_diffrn_reflns_limit_l_max       15
_diffrn_reflns_limit_l_min       -15
_diffrn_reflns_number            8832
_diffrn_reflns_theta_full        24.99
_diffrn_reflns_theta_max         24.99
_diffrn_reflns_theta_min         1.55
_exptl_absorpt_coefficient_mu    0.083
_exptl_absorpt_correction_T_max  1.0000
_exptl_absorpt_correction_T_min  0.712202
_exptl_absorpt_correction_type   multi-scan
_exptl_crystal_colour            green
_exptl_crystal_density_diffrn    1.404
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       block
_exptl_crystal_F_000             296
_exptl_crystal_size_max          0.40
_exptl_crystal_size_mid          0.30
_exptl_crystal_size_min          0.20
_refine_diff_density_max         0.198
_refine_diff_density_min         -0.178
_refine_diff_density_rms         0.042
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.052
_refine_ls_hydrogen_treatment    riding
_refine_ls_matrix_type           full
_refine_ls_number_parameters     199
_refine_ls_number_reflns         2330
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.052
_refine_ls_R_factor_all          0.0793
_refine_ls_R_factor_gt           0.0559
_refine_ls_shift/su_max          0.005
_refine_ls_shift/su_mean         0.001
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'calc w=1/[σ²(Fo²)+(0.0763P)²+0.4131P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1549
_refine_ls_wR_factor_ref         0.1869
_reflns_number_gt                1524
_reflns_number_total             2330
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            cm9001916_si_002.cif
_cod_data_source_block           6-13-DHDAP
_cod_depositor_comments
;
The following automatic conversions were performed:

'_symmetry_cell_setting' value 'Triclinic' changed to 'triclinic'
according to /home/saulius/struct/CIF-dictionaries/cif_core.dic
dictionary named 'cif_core.dic' version 2.4.2 from 2011-04-26.

Automatic conversion script
Id: cif_fix_values 1715 2011-07-08 13:25:40Z adriana 
;
_cod_original_sg_symbol_H-M      P-1
_cod_database_code               4001008
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
C1 C 0.1157(3) 0.0986(2) 0.55761(15) 0.0341(5) Uani 1 1 d .
C2 C 0.2257(3) 0.1925(2) 0.61450(15) 0.0370(5) Uani 1 1 d .
H2A H 0.3678 0.2289 0.5882 0.044 Uiso 1 1 calc R
C3 C 0.1295(4) 0.2358(2) 0.71204(16) 0.0367(5) Uani 1 1 d .
C4 C 0.2433(4) 0.3290(3) 0.77320(17) 0.0453(6) Uani 1 1 d .
H4A H 0.3858 0.3660 0.7483 0.054 Uiso 1 1 calc R
C5 C 0.1482(5) 0.3660(3) 0.86829(18) 0.0538(7) Uani 1 1 d .
H5A H 0.2266 0.4270 0.9076 0.065 Uiso 1 1 calc R
C6 C -0.0676(5) 0.3120(3) 0.90682(19) 0.0556(7) Uani 1 1 d .
H6A H -0.1318 0.3372 0.9717 0.067 Uiso 1 1 calc R
C7 C -0.1835(4) 0.2223(3) 0.84906(17) 0.0476(6) Uani 1 1 d .
H7A H -0.3268 0.1875 0.8750 0.057 Uiso 1 1 calc R
C8 C -0.0894(4) 0.1818(2) 0.75091(15) 0.0368(5) Uani 1 1 d .
C9 C -0.2024(3) 0.0864(2) 0.68993(15) 0.0362(5) Uani 1 1 d .
H9A H -0.3468 0.0517 0.7144 0.043 Uiso 1 1 calc R
C10 C -0.1050(3) 0.0445(2) 0.59658(15) 0.0341(5) Uani 1 1 d .
C11 C 0.3862(5) 0.1914(3) 0.10357(19) 0.0554(7) Uani 1 1 d .
H11 H 0.3146 0.1704 0.0456 0.066 Uiso 1 1 calc R
C12 C 0.2792(4) 0.2921(3) 0.17091(18) 0.0493(6) Uani 1 1 d .
H12A H 0.1353 0.3396 0.1581 0.059 Uiso 1 1 calc R
C13 C 0.3829(4) 0.3251(2) 0.25931(16) 0.0379(5) Uani 1 1 d .
C14 C 0.2775(4) 0.4304(2) 0.33014(16) 0.0378(5) Uani 1 1 d .
H14A H 0.1320 0.4775 0.3193 0.045 Uiso 1 1 calc R
C15 C 0.3851(3) 0.4643(2) 0.41395(15) 0.0342(5) Uani 1 1 d .
C16 C 0.3923(3) 0.6083(2) 0.56797(15) 0.0351(5) Uani 1 1 d .
C17 C 0.2899(3) 0.7121(2) 0.63428(16) 0.0370(5) Uani 1 1 d .
H17A H 0.1466 0.7606 0.6214 0.044 Uiso 1 1 calc R
C18 C 0.3970(3) 0.7475(2) 0.72239(16) 0.0371(5) Uani 1 1 d .
C19 C 0.2908(4) 0.8513(2) 0.79319(17) 0.0451(6) Uani 1 1 d .
H19A H 0.1471 0.9003 0.7816 0.054 Uiso 1 1 calc R
C20 C 0.3959(4) 0.8805(3) 0.87826(18) 0.0524(6) Uani 1 1 d .
H20 H 0.3228 0.9484 0.9245 0.063 Uiso 1 1 calc R
N1 N 0.2117(3) 0.0517(2) 0.46302(13) 0.0417(5) Uani 1 1 d .
H1 H 0.3447 0.0839 0.4398 0.050 Uiso 1 1 calc R
N2 N 0.2862(3) 0.5693(2) 0.48294(14) 0.0419(5) Uani 1 1 d .
H2B H 0.1518 0.6126 0.4724 0.050 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'
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
C2 C1 N1 122.28(18) . .
C2 C1 C10 119.5(2) . .
N1 C1 C10 118.21(18) . .
C1 C2 C3 121.74(19) . .
C4 C3 C2 122.7(2) . .
C4 C3 C8 118.6(2) . .
C2 C3 C8 118.78(19) . .
C5 C4 C3 121.2(2) . .
C4 C5 C6 120.2(2) . .
C7 C6 C5 120.1(2) . .
C6 C7 C8 121.1(2) . .
C7 C8 C9 122.5(2) . .
C7 C8 C3 118.9(2) . .
C9 C8 C3 118.57(19) . .
C10 C9 C8 121.68(19) . .
C9 C10 N1 122.25(18) . 2_556
C9 C10 C1 119.71(19) . .
N1 C10 C1 118.04(19) 2_556 .
C12 C11 C20 120.0(2) . 2_666
C11 C12 C13 121.2(2) . .
C12 C13 C18 118.8(2) . 2_666
C12 C13 C14 122.5(2) . .
C18 C13 C14 118.69(19) 2_666 .
C15 C14 C13 121.43(19) . .
C14 C15 N2 122.10(19) . .
C14 C15 C16 119.8(2) . 2_666
N2 C15 C16 118.06(19) . 2_666
C17 C16 N2 122.09(19) . .
C17 C16 C15 119.6(2) . 2_666
N2 C16 C15 118.28(19) . 2_666
C16 C17 C18 121.47(19) . .
C19 C18 C13 118.8(2) . 2_666
C19 C18 C17 122.2(2) . .
C13 C18 C17 118.93(19) 2_666 .
C20 C19 C18 120.9(2) . .
C19 C20 C11 120.4(2) . 2_666
C1 N1 C10 123.75(17) . 2_556
C15 N2 C16 123.66(18) . .
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
C1 C2 1.367(3) .
C1 N1 1.386(3) .
C1 C10 1.431(3) .
C2 C3 1.411(3) .
C3 C4 1.409(3) .
C3 C8 1.421(3) .
C4 C5 1.365(3) .
C5 C6 1.404(4) .
C6 C7 1.369(3) .
C7 C8 1.408(3) .
C8 C9 1.419(3) .
C9 C10 1.361(3) .
C10 N1 1.392(3) 2_556
C11 C12 1.365(3) .
C11 C20 1.404(4) 2_666
C12 C13 1.405(3) .
C13 C18 1.418(3) 2_666
C13 C14 1.419(3) .
C14 C15 1.367(3) .
C15 N2 1.390(3) .
C15 C16 1.429(3) 2_666
C16 C17 1.366(3) .
C16 N2 1.390(3) .
C16 C15 1.429(3) 2_666
C17 C18 1.418(3) .
C18 C19 1.411(3) .
C18 C13 1.418(3) 2_666
C19 C20 1.362(3) .
C20 C11 1.404(4) 2_666
N1 C10 1.392(3) 2_556
