#------------------------------------------------------------------------------
#$Date: 2016-02-18 17:37:37 +0200 (Thu, 18 Feb 2016) $
#$Revision: 176729 $
#$URL: svn://www.crystallography.net/cod/cif/1/50/35/1503591.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_1503591
loop_
_publ_author_name
'Fan, Jian'
'Zhang, Lei'
'Briseno, Alejandro L.'
'Wudl, Fred'
_publ_section_title
;
 Synthesis and characterization of 7,8,15,16-tetraazaterrylene.
;
_journal_issue                   4
_journal_name_full               'Organic letters'
_journal_page_first              1024
_journal_page_last               1026
_journal_paper_doi               10.1021/ol203285n
_journal_volume                  14
_journal_year                    2012
_chemical_formula_sum            'C26 H12 N4'
_chemical_formula_weight         380.40
_chemical_name_systematic
; 
 ? 
;
_space_group_IT_number           14
_symmetry_cell_setting           monoclinic
_symmetry_space_group_name_Hall  '-P 2ybc'
_symmetry_space_group_name_H-M   'P 1 21/c 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                 93.947(14)
_cell_angle_gamma                90.00
_cell_formula_units_Z            2
_cell_length_a                   3.7429(8)
_cell_length_b                   15.815(3)
_cell_length_c                   13.990(3)
_cell_measurement_temperature    100(2)
_cell_volume                     826.2(3)
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 2008)'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 2008)'
_diffrn_ambient_temperature      100(2)
_diffrn_measured_fraction_theta_full 0.986
_diffrn_measured_fraction_theta_max 0.986
_diffrn_measurement_device_type  'Bruker Kappa APEX II'
_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  0.0283
_diffrn_reflns_av_sigmaI/netI    0.0368
_diffrn_reflns_limit_h_max       4
_diffrn_reflns_limit_h_min       -5
_diffrn_reflns_limit_k_max       20
_diffrn_reflns_limit_k_min       -21
_diffrn_reflns_limit_l_max       13
_diffrn_reflns_limit_l_min       -18
_diffrn_reflns_number            4513
_diffrn_reflns_theta_full        28.46
_diffrn_reflns_theta_max         28.46
_diffrn_reflns_theta_min         1.95
_exptl_absorpt_coefficient_mu    0.093
_exptl_absorpt_correction_T_max  0.7457
_exptl_absorpt_correction_T_min  0.6344
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   sadabs
_exptl_crystal_colour            dark-red
_exptl_crystal_density_diffrn    1.529
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       needle
_exptl_crystal_F_000             392
_exptl_crystal_size_max          0.35
_exptl_crystal_size_mid          0.05
_exptl_crystal_size_min          0.05
_refine_diff_density_max         0.558
_refine_diff_density_min         -0.177
_refine_diff_density_rms         0.063
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.043
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     136
_refine_ls_number_reflns         2042
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.043
_refine_ls_R_factor_all          0.0571
_refine_ls_R_factor_gt           0.0443
_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)+(0.0835P)²+0.0546P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1219
_refine_ls_wR_factor_ref         0.1313
_reflns_number_gt                1604
_reflns_number_total             2042
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            ol203285n_si_001.cif
_cod_data_source_block           f08162011_0m
_cod_original_sg_symbol_H-M      P2(1)/c
_cod_database_code               1503591
loop_
_symmetry_equiv_pos_as_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_symmetry_multiplicity
_atom_site_calc_flag
_atom_site_refinement_flags
C1 C 0.1888(3) 0.50576(7) 0.88221(7) 0.0135(2) Uani 1 1 d .
C2 C 0.2684(3) 0.57091(7) 0.81304(8) 0.0147(2) Uani 1 1 d .
C3 C 0.3987(3) 0.55075(7) 0.72590(8) 0.0178(3) Uani 1 1 d .
H3 H 0.4364 0.4932 0.7100 0.021 Uiso 1 1 calc R
C4 C 0.4758(3) 0.61419(8) 0.66080(8) 0.0200(3) Uani 1 1 d .
H4 H 0.5627 0.5993 0.6008 0.024 Uiso 1 1 calc R
C5 C 0.4269(3) 0.69771(8) 0.68282(8) 0.0198(3) Uani 1 1 d .
H5 H 0.4848 0.7402 0.6385 0.024 Uiso 1 1 calc R
C6 C 0.2915(3) 0.72106(7) 0.77070(8) 0.0166(3) Uani 1 1 d .
C7 C 0.2391(3) 0.80699(7) 0.79400(9) 0.0195(3) Uani 1 1 d .
H7 H 0.2971 0.8498 0.7500 0.023 Uiso 1 1 calc R
C8 C 0.1062(3) 0.82909(7) 0.87887(9) 0.0205(3) Uani 1 1 d .
H8 H 0.0739 0.8871 0.8937 0.025 Uiso 1 1 calc R
C9 C 0.0172(3) 0.76695(7) 0.94425(8) 0.0177(3) Uani 1 1 d .
H9 H -0.0771 0.7832 1.0029 0.021 Uiso 1 1 calc R
C10 C 0.0646(3) 0.68203(7) 0.92466(8) 0.0145(3) Uani 1 1 d .
C11 C 0.2069(3) 0.65719(7) 0.83696(8) 0.0140(3) Uani 1 1 d .
C12 C -0.0294(3) 0.61612(7) 0.99120(8) 0.0135(2) Uani 1 1 d .
C13 C 0.0406(3) 0.53108(7) 0.96788(7) 0.0125(2) Uani 1 1 d .
N1 N 0.2602(2) 0.42484(6) 0.86516(7) 0.0164(2) Uani 1 1 d .
N2 N 0.1794(3) 0.36393(6) 0.92835(7) 0.0166(2) 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
N1 C1 C13 121.29(10) .
N1 C1 C2 120.49(10) .
C13 C1 C2 118.21(10) .
C3 C2 C11 120.00(10) .
C3 C2 C1 121.55(10) .
C11 C2 C1 118.44(10) .
C2 C3 C4 120.70(11) .
C2 C3 H3 119.7 .
C4 C3 H3 119.7 .
C5 C4 C3 120.53(11) .
C5 C4 H4 119.7 .
C3 C4 H4 119.7 .
C4 C5 C6 120.61(10) .
C4 C5 H5 119.7 .
C6 C5 H5 119.7 .
C5 C6 C7 121.08(10) .
C5 C6 C11 119.46(10) .
C7 C6 C11 119.46(10) .
C8 C7 C6 120.77(11) .
C8 C7 H7 119.6 .
C6 C7 H7 119.6 .
C7 C8 C9 120.46(11) .
C7 C8 H8 119.8 .
C9 C8 H8 119.8 .
C10 C9 C8 120.83(11) .
C10 C9 H9 119.6 .
C8 C9 H9 119.6 .
C9 C10 C11 119.88(10) .
C9 C10 C12 121.85(10) .
C11 C10 C12 118.28(10) .
C6 C11 C10 118.59(10) .
C6 C11 C2 118.66(10) .
C10 C11 C2 122.74(10) .
N2 C12 C13 121.14(10) 3_567
N2 C12 C10 120.38(10) 3_567
C13 C12 C10 118.48(10) .
C13 C13 C12 118.36(12) 3_567
C13 C13 C1 117.88(12) 3_567
C12 C13 C1 123.76(10) .
C1 N1 N2 120.62(9) .
C12 N2 N1 120.63(9) 3_567
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
C1 N1 1.3323(14) .
C1 C13 1.4128(15) .
C1 C2 1.4582(15) .
C2 C3 1.3811(15) .
C2 C11 1.4275(15) .
C3 C4 1.3984(16) .
C3 H3 0.9500 .
C4 C5 1.3715(17) .
C4 H4 0.9500 .
C5 C6 1.4109(17) .
C5 H5 0.9500 .
C6 C7 1.4144(16) .
C6 C11 1.4214(15) .
C7 C8 1.3640(17) .
C7 H7 0.9500 .
C8 C9 1.3984(16) .
C8 H8 0.9500 .
C9 C10 1.3848(16) .
C9 H9 0.9500 .
C10 C11 1.4259(16) .
C10 C12 1.4567(15) .
C12 N2 1.3299(14) 3_567
C12 C13 1.4127(15) .
C13 C13 1.380(2) 3_567
N1 N2 1.3556(13) .
N2 C12 1.3299(14) 3_567
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
N1 C1 C2 C3 3.95(17) . .
C13 C1 C2 C3 -177.11(10) . .
N1 C1 C2 C11 -176.35(9) . .
C13 C1 C2 C11 2.59(16) . .
C11 C2 C3 C4 0.76(16) . .
C1 C2 C3 C4 -179.55(10) . .
C2 C3 C4 C5 0.71(17) . .
C3 C4 C5 C6 -1.25(18) . .
C4 C5 C6 C7 -179.81(10) . .
C4 C5 C6 C11 0.29(17) . .
C5 C6 C7 C8 179.64(11) . .
C11 C6 C7 C8 -0.46(17) . .
C6 C7 C8 C9 -0.40(17) . .
C7 C8 C9 C10 0.55(18) . .
C8 C9 C10 C11 0.18(17) . .
C8 C9 C10 C12 -179.39(10) . .
C5 C6 C11 C10 -178.94(9) . .
C7 C6 C11 C10 1.16(16) . .
C5 C6 C11 C2 1.15(16) . .
C7 C6 C11 C2 -178.75(9) . .
C9 C10 C11 C6 -1.02(16) . .
C12 C10 C11 C6 178.56(9) . .
C9 C10 C11 C2 178.88(10) . .
C12 C10 C11 C2 -1.53(16) . .
C3 C2 C11 C6 -1.67(16) . .
C1 C2 C11 C6 178.63(9) . .
C3 C2 C11 C10 178.42(10) . .
C1 C2 C11 C10 -1.28(16) . .
C9 C10 C12 N2 2.93(17) . 3_567
C11 C10 C12 N2 -176.65(9) . 3_567
C9 C10 C12 C13 -177.44(10) . .
C11 C10 C12 C13 2.98(16) . .
N2 C12 C13 C13 -1.93(19) 3_567 3_567
C10 C12 C13 C13 178.45(11) . 3_567
N2 C12 C13 C1 177.93(10) 3_567 .
C10 C12 C13 C1 -1.69(17) . .
N1 C1 C13 C13 -2.34(19) . 3_567
C2 C1 C13 C13 178.73(11) . 3_567
N1 C1 C13 C12 177.80(10) . .
C2 C1 C13 C12 -1.13(17) . .
C13 C1 N1 N2 2.52(17) . .
C2 C1 N1 N2 -178.57(9) . .
C1 N1 N2 C12 -0.39(16) . 3_567
