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#$Date: 2016-03-26 03:21:29 +0200 (Sat, 26 Mar 2016) $
#$Revision: 180179 $
#$URL: svn://www.crystallography.net/cod/cif/7/10/75/7107585.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_7107585
loop_
_publ_author_name
'Yinque Liu'
'Fan Zhang'
'Chunyang He'
'Dongqing Wu'
'Xiaodong Zhuang'
'Minzhao Xue'
'Xinliang Feng'
_publ_section_title
;
 Efficient synthesis and physical properties of novel H-shaped
 2,3,7,8-tetraazaanthracene-based conjugated molecules
;
_journal_name_full               Chem.Commun.
_journal_page_first              4166
_journal_paper_doi               10.1039/c2cc00015f
_journal_volume                  48
_journal_year                    2012
_chemical_formula_sum            'C50 H62 N4 S4'
_chemical_formula_weight         847.28
_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                 104.922(2)
_cell_angle_gamma                90.00
_cell_formula_units_Z            2
_cell_length_a                   6.3583(3)
_cell_length_b                   41.420(2)
_cell_length_c                   8.9592(5)
_cell_measurement_temperature    173(2)
_cell_volume                     2279.9(2)
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 2008)'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 2008)'
_diffrn_ambient_temperature      173(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  0.0456
_diffrn_reflns_av_sigmaI/netI    0.0289
_diffrn_reflns_limit_h_max       7
_diffrn_reflns_limit_h_min       -7
_diffrn_reflns_limit_k_max       49
_diffrn_reflns_limit_k_min       -49
_diffrn_reflns_limit_l_max       10
_diffrn_reflns_limit_l_min       -10
_diffrn_reflns_number            26363
_diffrn_reflns_theta_full        25.01
_diffrn_reflns_theta_max         25.01
_diffrn_reflns_theta_min         1.97
_exptl_absorpt_coefficient_mu    0.247
_exptl_absorpt_correction_T_max  0.9476
_exptl_absorpt_correction_T_min  0.9032
_exptl_absorpt_correction_type   multi-scan
_exptl_crystal_colour            colorless
_exptl_crystal_density_diffrn    1.234
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       block
_exptl_crystal_F_000             908
_exptl_crystal_size_max          0.42
_exptl_crystal_size_mid          0.35
_exptl_crystal_size_min          0.22
_refine_diff_density_max         1.266
_refine_diff_density_min         -0.662
_refine_diff_density_rms         0.077
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.154
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     262
_refine_ls_number_reflns         4035
_refine_ls_number_restraints     1
_refine_ls_restrained_S_all      1.155
_refine_ls_R_factor_all          0.0890
_refine_ls_R_factor_gt           0.0794
_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)+(0.0331P)²+8.3390P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1683
_refine_ls_wR_factor_ref         0.1734
_reflns_number_gt                3533
_reflns_number_total             4035
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            c2cc00015f.txt
_cod_data_source_block           z
_cod_original_cell_volume        2280.0(2)
_cod_original_sg_symbol_H-M      P2(1)/c
_cod_database_code               7107585
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
S1 S 0.43218(17) -0.10261(3) -0.13626(13) 0.0320(3) Uani 1 1 d .
S2 S 0.79120(15) 0.02805(2) 0.39091(11) 0.0254(3) Uani 1 1 d .
N1 N 0.5021(5) -0.04823(8) 0.0838(4) 0.0251(7) Uani 1 1 d .
N2 N 0.5697(5) -0.02214(8) 0.1779(4) 0.0252(7) Uani 1 1 d .
C1 C 1.110(2) -0.2617(4) -0.074(2) 0.281(12) Uani 1 1 d U
H1A H 1.1902 -0.2774 -0.1208 0.422 Uiso 1 1 calc R
H1B H 1.0581 -0.2722 0.0072 0.422 Uiso 1 1 calc R
H1C H 1.2071 -0.2438 -0.0302 0.422 Uiso 1 1 calc R
C2 C 0.917(3) -0.2487(4) -0.1983(19) 0.228(8) Uani 1 1 d U
H2A H 0.9692 -0.2373 -0.2788 0.274 Uiso 1 1 calc R
H2B H 0.8235 -0.2669 -0.2480 0.274 Uiso 1 1 calc R
C3 C 0.800(2) -0.2285(2) -0.1350(12) 0.163(6) Uani 1 1 d .
H3A H 0.9011 -0.2123 -0.0737 0.195 Uiso 1 1 calc R
H3B H 0.7384 -0.2409 -0.0621 0.195 Uiso 1 1 calc R
C4 C 0.6083(12) -0.20978(15) -0.2488(8) 0.076(2) Uani 1 1 d .
H4A H 0.6628 -0.1999 -0.3322 0.091 Uiso 1 1 calc R
H4B H 0.4924 -0.2253 -0.2968 0.091 Uiso 1 1 calc R
C5 C 0.5126(9) -0.18366(12) -0.1683(6) 0.0495(13) Uani 1 1 d .
H5A H 0.6319 -0.1695 -0.1116 0.059 Uiso 1 1 calc R
H5B H 0.4467 -0.1939 -0.0913 0.059 Uiso 1 1 calc R
C6 C 0.3420(9) -0.16307(12) -0.2755(6) 0.0483(13) Uani 1 1 d .
H6A H 0.4027 -0.1547 -0.3592 0.058 Uiso 1 1 calc R
H6B H 0.2153 -0.1768 -0.3236 0.058 Uiso 1 1 calc R
C7 C 0.2655(7) -0.13515(10) -0.1970(5) 0.0348(10) Uani 1 1 d .
C8 C 0.0711(7) -0.13091(10) -0.1620(5) 0.0360(10) Uani 1 1 d .
H8A H -0.0432 -0.1463 -0.1861 0.043 Uiso 1 1 calc R
C9 C 0.0554(6) -0.10150(10) -0.0866(5) 0.0297(9) Uani 1 1 d .
H9A H -0.0696 -0.0951 -0.0544 0.036 Uiso 1 1 calc R
C10 C 0.2394(6) -0.08320(9) -0.0647(4) 0.0249(8) Uani 1 1 d .
C11 C 0.2950(6) -0.05201(9) 0.0139(4) 0.0227(8) Uani 1 1 d .
C12 C 0.1367(6) -0.02694(9) 0.0083(4) 0.0209(8) Uani 1 1 d .
C13 C 0.2088(6) 0.00069(9) 0.1010(4) 0.0209(8) Uani 1 1 d .
C14 C 0.4289(6) -0.00004(9) 0.1976(4) 0.0214(8) Uani 1 1 d .
C15 C 0.5130(6) 0.02288(9) 0.3212(4) 0.0220(8) Uani 1 1 d .
C16 C 0.4063(6) 0.03991(10) 0.4100(5) 0.0269(9) Uani 1 1 d .
H16A H 0.2524 0.0399 0.3926 0.032 Uiso 1 1 calc R
C17 C 0.5465(6) 0.05739(10) 0.5295(5) 0.0280(9) Uani 1 1 d .
H17A H 0.4963 0.0705 0.6002 0.034 Uiso 1 1 calc R
C18 C 0.7599(6) 0.05384(10) 0.5345(4) 0.0260(9) Uani 1 1 d .
C19 C 0.9495(7) 0.07000(10) 0.6420(5) 0.0312(9) Uani 1 1 d .
H19A H 1.0702 0.0543 0.6733 0.037 Uiso 1 1 calc R
H19B H 0.9073 0.0768 0.7362 0.037 Uiso 1 1 calc R
C20 C 1.0295(7) 0.09934(10) 0.5705(5) 0.0314(9) Uani 1 1 d .
H20A H 0.9032 0.1132 0.5233 0.038 Uiso 1 1 calc R
H20B H 1.0941 0.0920 0.4869 0.038 Uiso 1 1 calc R
C21 C 1.1972(8) 0.11932(11) 0.6853(5) 0.0391(11) Uani 1 1 d .
H21A H 1.1303 0.1280 0.7652 0.047 Uiso 1 1 calc R
H21B H 1.3203 0.1053 0.7373 0.047 Uiso 1 1 calc R
C22 C 1.2824(12) 0.14708(15) 0.6069(7) 0.0718(19) Uani 1 1 d .
H22A H 1.3533 0.1380 0.5300 0.086 Uiso 1 1 calc R
H22B H 1.1568 0.1601 0.5500 0.086 Uiso 1 1 calc R
C23 C 1.4418(13) 0.1692(2) 0.7127(10) 0.095(3) Uani 1 1 d .
H23A H 1.4536 0.1894 0.6569 0.114 Uiso 1 1 calc R
H23B H 1.3847 0.1747 0.8023 0.114 Uiso 1 1 calc R
C24 C 1.6414(14) 0.1562(2) 0.7644(10) 0.117(3) Uani 1 1 d .
H24A H 1.7353 0.1713 0.8359 0.176 Uiso 1 1 calc R
H24B H 1.7035 0.1521 0.6768 0.176 Uiso 1 1 calc R
H24C H 1.6310 0.1359 0.8181 0.176 Uiso 1 1 calc R
C25 C 0.0712(6) 0.02726(9) 0.0904(4) 0.0223(8) Uani 1 1 d .
H25A H 0.1203 0.0458 0.1516 0.027 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'
S S 0.1246 0.1234 '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
C7 S1 C10 92.5(2) .
C18 S2 C15 92.42(19) .
C11 N1 N2 120.3(3) .
C14 N2 N1 120.8(3) .
C2 C1 H1A 109.5 .
C2 C1 H1B 109.5 .
H1A C1 H1B 109.5 .
C2 C1 H1C 109.5 .
H1A C1 H1C 109.5 .
H1B C1 H1C 109.5 .
C3 C2 C1 110.0(15) .
C3 C2 H2A 109.7 .
C1 C2 H2A 109.7 .
C3 C2 H2B 109.7 .
C1 C2 H2B 109.7 .
H2A C2 H2B 108.2 .
C2 C3 C4 117.0(10) .
C2 C3 H3A 108.0 .
C4 C3 H3A 108.0 .
C2 C3 H3B 108.0 .
C4 C3 H3B 108.0 .
H3A C3 H3B 107.3 .
C5 C4 C3 112.5(6) .
C5 C4 H4A 109.1 .
C3 C4 H4A 109.1 .
C5 C4 H4B 109.1 .
C3 C4 H4B 109.1 .
H4A C4 H4B 107.8 .
C4 C5 C6 114.3(5) .
C4 C5 H5A 108.7 .
C6 C5 H5A 108.7 .
C4 C5 H5B 108.7 .
C6 C5 H5B 108.7 .
H5A C5 H5B 107.6 .
C7 C6 C5 113.8(4) .
C7 C6 H6A 108.8 .
C5 C6 H6A 108.8 .
C7 C6 H6B 108.8 .
C5 C6 H6B 108.8 .
H6A C6 H6B 107.7 .
C8 C7 C6 129.1(4) .
C8 C7 S1 110.4(3) .
C6 C7 S1 120.5(4) .
C7 C8 C9 113.7(4) .
C7 C8 H8A 123.2 .
C9 C8 H8A 123.2 .
C10 C9 C8 112.7(4) .
C10 C9 H9A 123.7 .
C8 C9 H9A 123.7 .
C9 C10 C11 130.4(4) .
C9 C10 S1 110.7(3) .
C11 C10 S1 118.8(3) .
N1 C11 C12 122.5(4) .
N1 C11 C10 114.9(3) .
C12 C11 C10 122.5(3) .
C25 C12 C13 119.5(3) 3
C25 C12 C11 123.9(4) 3
C13 C12 C11 116.3(3) .
C25 C13 C12 119.6(3) .
C25 C13 C14 123.5(3) .
C12 C13 C14 116.8(3) .
N2 C14 C13 121.3(3) .
N2 C14 C15 115.2(3) .
C13 C14 C15 123.6(3) .
C16 C15 C14 129.8(3) .
C16 C15 S2 109.9(3) .
C14 C15 S2 119.8(3) .
C15 C16 C17 113.4(3) .
C15 C16 H16A 123.3 .
C17 C16 H16A 123.3 .
C18 C17 C16 113.8(4) .
C18 C17 H17A 123.1 .
C16 C17 H17A 123.1 .
C17 C18 C19 127.5(4) .
C17 C18 S2 110.5(3) .
C19 C18 S2 122.0(3) .
C18 C19 C20 112.8(3) .
C18 C19 H19A 109.0 .
C20 C19 H19A 109.0 .
C18 C19 H19B 109.0 .
C20 C19 H19B 109.0 .
H19A C19 H19B 107.8 .
C19 C20 C21 113.7(4) .
C19 C20 H20A 108.8 .
C21 C20 H20A 108.8 .
C19 C20 H20B 108.8 .
C21 C20 H20B 108.8 .
H20A C20 H20B 107.7 .
C22 C21 C20 111.8(4) .
C22 C21 H21A 109.3 .
C20 C21 H21A 109.3 .
C22 C21 H21B 109.3 .
C20 C21 H21B 109.3 .
H21A C21 H21B 107.9 .
C23 C22 C21 115.6(6) .
C23 C22 H22A 108.4 .
C21 C22 H22A 108.4 .
C23 C22 H22B 108.4 .
C21 C22 H22B 108.4 .
H22A C22 H22B 107.5 .
C24 C23 C22 113.4(7) .
C24 C23 H23A 108.9 .
C22 C23 H23A 108.9 .
C24 C23 H23B 108.9 .
C22 C23 H23B 108.9 .
H23A C23 H23B 107.7 .
C23 C24 H24A 109.5 .
C23 C24 H24B 109.5 .
H24A C24 H24B 109.5 .
C23 C24 H24C 109.5 .
H24A C24 H24C 109.5 .
H24B C24 H24C 109.5 .
C12 C25 C13 120.9(4) 3
C12 C25 H25A 119.5 3
C13 C25 H25A 119.5 .
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
S1 C7 1.714(5) .
S1 C10 1.722(4) .
S2 C18 1.723(4) .
S2 C15 1.731(4) .
N1 C11 1.313(5) .
N1 N2 1.370(4) .
N2 C14 1.323(5) .
C1 C2 1.527(17) .
C1 H1A 0.9800 .
C1 H1B 0.9800 .
C1 H1C 0.9800 .
C2 C3 1.338(16) .
C2 H2A 0.9900 .
C2 H2B 0.9900 .
C3 C4 1.577(11) .
C3 H3A 0.9900 .
C3 H3B 0.9900 .
C4 C5 1.512(7) .
C4 H4A 0.9900 .
C4 H4B 0.9900 .
C5 C6 1.513(7) .
C5 H5A 0.9900 .
C5 H5B 0.9900 .
C6 C7 1.498(6) .
C6 H6A 0.9900 .
C6 H6B 0.9900 .
C7 C8 1.363(7) .
C8 C9 1.409(6) .
C8 H8A 0.9500 .
C9 C10 1.365(6) .
C9 H9A 0.9500 .
C10 C11 1.470(5) .
C11 C12 1.438(5) .
C12 C25 1.388(5) 3
C12 C13 1.419(5) .
C13 C25 1.394(5) .
C13 C14 1.444(5) .
C14 C15 1.452(5) .
C15 C16 1.367(5) .
C16 C17 1.405(6) .
C16 H16A 0.9500 .
C17 C18 1.354(6) .
C17 H17A 0.9500 .
C18 C19 1.494(5) .
C19 C20 1.521(6) .
C19 H19A 0.9900 .
C19 H19B 0.9900 .
C20 C21 1.522(6) .
C20 H20A 0.9900 .
C20 H20B 0.9900 .
C21 C22 1.518(7) .
C21 H21A 0.9900 .
C21 H21B 0.9900 .
C22 C23 1.505(8) .
C22 H22A 0.9900 .
C22 H22B 0.9900 .
C23 C24 1.345(10) .
C23 H23A 0.9900 .
C23 H23B 0.9900 .
C24 H24A 0.9800 .
C24 H24B 0.9800 .
C24 H24C 0.9800 .
C25 C12 1.388(5) 3
C25 H25A 0.9500 .
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
C11 N1 N2 C14 -1.3(5) . .
C1 C2 C3 C4 173.4(11) . .
C2 C3 C4 C5 -170.5(13) . .
C3 C4 C5 C6 174.6(7) . .
C4 C5 C6 C7 -173.9(5) . .
C5 C6 C7 C8 -107.7(6) . .
C5 C6 C7 S1 71.8(6) . .
C10 S1 C7 C8 -0.3(3) . .
C10 S1 C7 C6 -179.9(4) . .
C6 C7 C8 C9 179.7(4) . .
S1 C7 C8 C9 0.1(5) . .
C7 C8 C9 C10 0.2(5) . .
C8 C9 C10 C11 -177.0(4) . .
C8 C9 C10 S1 -0.5(5) . .
C7 S1 C10 C9 0.5(3) . .
C7 S1 C10 C11 177.5(3) . .
N2 N1 C11 C12 11.6(5) . .
N2 N1 C11 C10 -171.3(3) . .
C9 C10 C11 N1 146.9(4) . .
S1 C10 C11 N1 -29.4(5) . .
C9 C10 C11 C12 -36.0(6) . .
S1 C10 C11 C12 147.7(3) . .
N1 C11 C12 C25 165.6(4) . 3
C10 C11 C12 C25 -11.3(6) . 3
N1 C11 C12 C13 -8.7(5) . .
C10 C11 C12 C13 174.4(3) . .
C25 C12 C13 C25 -0.7(6) 3 .
C11 C12 C13 C25 173.8(3) . .
C25 C12 C13 C14 -178.1(3) 3 .
C11 C12 C13 C14 -3.5(5) . .
N1 N2 C14 C13 -11.3(5) . .
N1 N2 C14 C15 168.9(3) . .
C25 C13 C14 N2 -163.9(4) . .
C12 C13 C14 N2 13.3(5) . .
C25 C13 C14 C15 15.9(6) . .
C12 C13 C14 C15 -166.9(3) . .
N2 C14 C15 C16 -152.5(4) . .
C13 C14 C15 C16 27.7(6) . .
N2 C14 C15 S2 19.3(5) . .
C13 C14 C15 S2 -160.5(3) . .
C18 S2 C15 C16 -1.6(3) . .
C18 S2 C15 C14 -174.9(3) . .
C14 C15 C16 C17 173.9(4) . .
S2 C15 C16 C17 1.4(4) . .
C15 C16 C17 C18 -0.5(5) . .
C16 C17 C18 C19 177.3(4) . .
C16 C17 C18 S2 -0.8(5) . .
C15 S2 C18 C17 1.3(3) . .
C15 S2 C18 C19 -176.8(3) . .
C17 C18 C19 C20 -98.2(5) . .
S2 C18 C19 C20 79.7(4) . .
C18 C19 C20 C21 170.5(4) . .
C19 C20 C21 C22 176.4(5) . .
C20 C21 C22 C23 177.3(6) . .
C21 C22 C23 C24 75.0(10) . .
C12 C13 C25 C12 0.7(6) . 3
C14 C13 C25 C12 177.9(3) . 3
