#------------------------------------------------------------------------------
#$Date: 2016-02-18 17:37:37 +0200 (Thu, 18 Feb 2016) $
#$Revision: 176729 $
#$URL: svn://www.crystallography.net/cod/cif/1/51/75/1517549.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_1517549
loop_
_publ_author_name
'Tang, Ruizhi'
'Zhang, Fan'
'Fu, Yubin'
'Xu, Qing'
'Wang, Xinyang'
'Zhuang, Xiaodong'
'Wu, Dongqing'
'Giannakopoulos, Angelos'
'Beljonne, David'
'Feng, Xinliang'
_publ_section_title
;
 Efficient approach to electron-deficient 1,2,7,8-tetraazaperylene
 derivatives.
;
_journal_issue                   18
_journal_name_full               'Organic letters'
_journal_page_first              4726
_journal_page_last               4729
_journal_paper_doi               10.1021/ol502109y
_journal_volume                  16
_journal_year                    2014
_chemical_formula_sum            'C26 H28 N4'
_chemical_formula_weight         396.52
_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                 105.4830(10)
_cell_angle_gamma                90.00
_cell_formula_units_Z            2
_cell_length_a                   4.7073(2)
_cell_length_b                   28.2422(10)
_cell_length_c                   8.1072(3)
_cell_measurement_temperature    296(2)
_cell_volume                     1038.69(7)
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 2008)'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 2008)'
_diffrn_ambient_temperature      296(2)
_diffrn_measured_fraction_theta_full 0.998
_diffrn_measured_fraction_theta_max 0.998
_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  0.0212
_diffrn_reflns_av_sigmaI/netI    0.0134
_diffrn_reflns_limit_h_max       5
_diffrn_reflns_limit_h_min       -5
_diffrn_reflns_limit_k_max       33
_diffrn_reflns_limit_k_min       -33
_diffrn_reflns_limit_l_max       9
_diffrn_reflns_limit_l_min       -9
_diffrn_reflns_number            11999
_diffrn_reflns_theta_full        25.01
_diffrn_reflns_theta_max         25.01
_diffrn_reflns_theta_min         2.70
_exptl_absorpt_coefficient_mu    0.076
_exptl_absorpt_correction_T_max  0.9879
_exptl_absorpt_correction_T_min  0.9673
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   sadabs
_exptl_crystal_colour            colorless
_exptl_crystal_density_diffrn    1.268
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       block
_exptl_crystal_F_000             424
_exptl_crystal_size_max          0.44
_exptl_crystal_size_mid          0.39
_exptl_crystal_size_min          0.16
_refine_diff_density_max         0.145
_refine_diff_density_min         -0.129
_refine_diff_density_rms         0.028
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.040
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     136
_refine_ls_number_reflns         1838
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.040
_refine_ls_R_factor_all          0.0442
_refine_ls_R_factor_gt           0.0344
_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)+(0.0481P)²+0.2082P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0907
_refine_ls_wR_factor_ref         0.0999
_reflns_number_gt                1497
_reflns_number_total             1838
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            ol502109y_si_002.cif
_cod_data_source_block           z
_cod_depositor_comments
;
The following automatic conversions were performed:

'_symmetry_cell_setting' value 'Monoclinic' changed to 'monoclinic'
according to
/home/saulius/struct/COD-crude-data--automatic-downloads/rss-feeds/ACS/lib/dictionaries/cif_core.dic
dictionary named 'cif_core.dic' version 2.4.2 from 2011-04-26.

Automatic conversion script
Id: cif_fix_values 2281 2013-09-26 08:29:07Z andrius 

 Adding full bibliography for 1517549.cif.
;
_cod_original_sg_symbol_H-M      P2(1)/c
_cod_database_code               1517549
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
N1 N 0.5985(2) 0.42221(4) 1.22578(15) 0.0459(3) Uani 1 1 d .
N2 N 0.4271(2) 0.45828(4) 1.25929(13) 0.0433(3) Uani 1 1 d .
C1 C 0.3539(3) 0.42658(4) 0.92471(16) 0.0350(3) Uani 1 1 d .
C2 C 0.3125(3) 0.41153(4) 0.75398(17) 0.0415(3) Uani 1 1 d .
H2A H 0.4314 0.3878 0.7287 0.050 Uiso 1 1 calc R
C3 C 0.0978(3) 0.43176(4) 0.62582(16) 0.0437(3) Uani 1 1 d .
H3A H 0.0715 0.4215 0.5137 0.052 Uiso 1 1 calc R
C4 C -0.0828(3) 0.46755(4) 0.66035(16) 0.0394(3) Uani 1 1 d .
H4A H -0.2301 0.4804 0.5714 0.047 Uiso 1 1 calc R
C5 C -0.0452(3) 0.48406(4) 0.82465(15) 0.0324(3) Uani 1 1 d .
C6 C 0.1757(3) 0.46317(4) 0.95905(14) 0.0315(3) Uani 1 1 d .
C7 C 0.2256(3) 0.47770(4) 1.13297(15) 0.0328(3) Uani 1 1 d .
C8 C 0.5652(3) 0.40686(4) 1.06862(16) 0.0385(3) Uani 1 1 d .
C9 C 0.7530(3) 0.36502(4) 1.05233(18) 0.0449(3) Uani 1 1 d .
H9A H 0.9217 0.3636 1.1518 0.054 Uiso 1 1 calc R
H9B H 0.8258 0.3690 0.9520 0.054 Uiso 1 1 calc R
C10 C 0.5799(3) 0.31869(4) 1.03709(19) 0.0471(4) Uani 1 1 d .
H10A H 0.4854 0.3171 1.1296 0.056 Uiso 1 1 calc R
H10B H 0.4259 0.3189 0.9302 0.056 Uiso 1 1 calc R
C11 C 0.7666(3) 0.27462(4) 1.04261(19) 0.0482(4) Uani 1 1 d .
H11A H 0.8661 0.2766 0.9523 0.058 Uiso 1 1 calc R
H11B H 0.9166 0.2737 1.1511 0.058 Uiso 1 1 calc R
C12 C 0.5915(4) 0.22919(5) 1.0218(2) 0.0563(4) Uani 1 1 d .
H12A H 0.4481 0.2294 0.9108 0.068 Uiso 1 1 calc R
H12B H 0.4840 0.2281 1.1085 0.068 Uiso 1 1 calc R
C13 C 0.7778(5) 0.18483(5) 1.0359(2) 0.0714(5) Uani 1 1 d .
H13A H 0.6528 0.1574 1.0220 0.107 Uiso 1 1 calc R
H13B H 0.9178 0.1839 1.1464 0.107 Uiso 1 1 calc R
H13C H 0.8806 0.1851 0.9484 0.107 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_3
C8 N1 N2 120.86(11) .
C7 N2 N1 119.70(11) .
C6 C1 C2 118.86(11) .
C6 C1 C8 116.58(11) .
C2 C1 C8 124.57(12) .
C3 C2 C1 120.04(12) .
C3 C2 H2A 120.0 .
C1 C2 H2A 120.0 .
C2 C3 C4 121.10(12) .
C2 C3 H3A 119.5 .
C4 C3 H3A 119.5 .
C5 C4 C3 120.73(12) .
C5 C4 H4A 119.6 .
C3 C4 H4A 119.6 .
C4 C5 C6 118.74(11) .
C4 C5 C7 122.79(11) 3_567
C6 C5 C7 118.47(10) 3_567
C1 C6 C5 120.51(11) .
C1 C6 C7 117.24(11) .
C5 C6 C7 122.24(11) .
N2 C7 C6 122.97(11) .
N2 C7 C5 117.75(11) 3_567
C6 C7 C5 119.28(11) 3_567
N1 C8 C1 122.64(12) .
N1 C8 C9 115.08(11) .
C1 C8 C9 122.18(11) .
C8 C9 C10 111.52(11) .
C8 C9 H9A 109.3 .
C10 C9 H9A 109.3 .
C8 C9 H9B 109.3 .
C10 C9 H9B 109.3 .
H9A C9 H9B 108.0 .
C11 C10 C9 114.06(11) .
C11 C10 H10A 108.7 .
C9 C10 H10A 108.7 .
C11 C10 H10B 108.7 .
C9 C10 H10B 108.7 .
H10A C10 H10B 107.6 .
C12 C11 C10 113.53(12) .
C12 C11 H11A 108.9 .
C10 C11 H11A 108.9 .
C12 C11 H11B 108.9 .
C10 C11 H11B 108.9 .
H11A C11 H11B 107.7 .
C11 C12 C13 113.99(14) .
C11 C12 H12A 108.8 .
C13 C12 H12A 108.8 .
C11 C12 H12B 108.8 .
C13 C12 H12B 108.8 .
H12A C12 H12B 107.6 .
C12 C13 H13A 109.5 .
C12 C13 H13B 109.5 .
H13A C13 H13B 109.5 .
C12 C13 H13C 109.5 .
H13A C13 H13C 109.5 .
H13B C13 H13C 109.5 .
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
N1 C8 1.3151(17) .
N1 N2 1.3710(15) .
N2 C7 1.3153(16) .
C1 C6 1.4050(17) .
C1 C2 1.4108(17) .
C1 C8 1.4288(17) .
C2 C3 1.3662(19) .
C2 H2A 0.9300 .
C3 C4 1.3964(18) .
C3 H3A 0.9300 .
C4 C5 1.3773(17) .
C4 H4A 0.9300 .
C5 C6 1.4182(17) .
C5 C7 1.4703(17) 3_567
C6 C7 1.4264(16) .
C7 C5 1.4704(17) 3_567
C8 C9 1.5023(17) .
C9 C10 1.5290(17) .
C9 H9A 0.9700 .
C9 H9B 0.9700 .
C10 C11 1.5175(18) .
C10 H10A 0.9700 .
C10 H10B 0.9700 .
C11 C12 1.5096(19) .
C11 H11A 0.9700 .
C11 H11B 0.9700 .
C12 C13 1.516(2) .
C12 H12A 0.9700 .
C12 H12B 0.9700 .
C13 H13A 0.9600 .
C13 H13B 0.9600 .
C13 H13C 0.9600 .
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
C8 N1 N2 C7 0.33(18) . .
C6 C1 C2 C3 -1.40(18) . .
C8 C1 C2 C3 177.99(12) . .
C1 C2 C3 C4 0.3(2) . .
C2 C3 C4 C5 1.3(2) . .
C3 C4 C5 C6 -1.63(18) . .
C3 C4 C5 C7 178.77(11) . 3_567
C2 C1 C6 C5 1.01(17) . .
C8 C1 C6 C5 -178.43(10) . .
C2 C1 C6 C7 -179.48(11) . .
C8 C1 C6 C7 1.08(16) . .
C4 C5 C6 C1 0.49(17) . .
C7 C5 C6 C1 -179.88(10) 3_567 .
C4 C5 C6 C7 -179.00(11) . .
C7 C5 C6 C7 0.62(18) 3_567 .
N1 N2 C7 C6 -0.38(18) . .
N1 N2 C7 C5 179.40(10) . 3_567
C1 C6 C7 N2 -0.36(18) . .
C5 C6 C7 N2 179.15(11) . .
C1 C6 C7 C5 179.86(10) . 3_567
C5 C6 C7 C5 -0.63(18) . 3_567
N2 N1 C8 C1 0.48(19) . .
N2 N1 C8 C9 -175.95(11) . .
C6 C1 C8 N1 -1.19(18) . .
C2 C1 C8 N1 179.40(12) . .
C6 C1 C8 C9 174.99(11) . .
C2 C1 C8 C9 -4.42(19) . .
N1 C8 C9 C10 98.74(14) . .
C1 C8 C9 C10 -77.71(16) . .
C8 C9 C10 C11 -172.74(12) . .
C9 C10 C11 C12 -178.16(13) . .
C10 C11 C12 C13 -177.11(13) . .
