#------------------------------------------------------------------------------
#$Date: 2016-02-18 17:37:37 +0200 (Thu, 18 Feb 2016) $
#$Revision: 176729 $
#$URL: svn://www.crystallography.net/cod/cif/1/50/36/1503604.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_1503604
loop_
_publ_author_name
'He, Zikai'
'Liu, Danqing'
'Mao, Renxin'
'Tang, Qin'
'Miao, Qian'
_publ_section_title
;
 Hydrogen-bonded dihydrotetraazapentacenes.
;
_journal_issue                   4
_journal_name_full               'Organic letters'
_journal_page_first              1050
_journal_page_last               1053
_journal_paper_doi               10.1021/ol203404q
_journal_volume                  14
_journal_year                    2012
_chemical_formula_sum            'C40 H52 N4 Si2'
_chemical_formula_weight         645.04
_chemical_name_systematic
; 
 6,13-bis((triisopropylsilyl)ethynyl)-5,14-dihydro-1,4,5,14-tetraazapentacene 
;
_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                78.243(2)
_cell_angle_beta                 89.120(2)
_cell_angle_gamma                79.670(2)
_cell_formula_units_Z            1
_cell_length_a                   7.5446(5)
_cell_length_b                   7.8619(6)
_cell_length_c                   16.9040(12)
_cell_measurement_reflns_used    299
_cell_measurement_temperature    293(2)
_cell_measurement_theta_max      15
_cell_measurement_theta_min      15
_cell_volume                     965.48(12)
_computing_cell_refinement       'BRUKER KAPPA APEXII DUO DIFFRACTOMEMTER'
_computing_data_collection       'BRUKER KAPPA APEXII DUO DIFFRACTOMEMTER'
_computing_data_reduction        'BRUKER KAPPA APEXII DUO DIFFRACTOMEMTER'
_computing_molecular_graphics    'SIEMENS SHETXTL'
_computing_publication_material  'SIEMENS SHETXTL'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 2008)'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 2008)'
_diffrn_ambient_temperature      293(2)
_diffrn_measured_fraction_theta_full 0.972
_diffrn_measured_fraction_theta_max 0.972
_diffrn_measurement_device_type  'BRUKER KAPPA APEXII DUO DIFFRACTOMEMTER'
_diffrn_measurement_method       'PHI & 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  0.0756
_diffrn_reflns_av_sigmaI/netI    0.0650
_diffrn_reflns_limit_h_max       9
_diffrn_reflns_limit_h_min       -9
_diffrn_reflns_limit_k_max       9
_diffrn_reflns_limit_k_min       -10
_diffrn_reflns_limit_l_max       22
_diffrn_reflns_limit_l_min       -21
_diffrn_reflns_number            16201
_diffrn_reflns_theta_full        27.79
_diffrn_reflns_theta_max         27.79
_diffrn_reflns_theta_min         2.46
_exptl_absorpt_coefficient_mu    0.123
_exptl_absorpt_correction_T_max  0.7278
_exptl_absorpt_correction_T_min  0.6293
_exptl_absorpt_correction_type   multi-scan
_exptl_crystal_colour            yellow
_exptl_crystal_density_diffrn    1.109
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       block
_exptl_crystal_F_000             348
_exptl_crystal_size_max          0.50
_exptl_crystal_size_mid          0.40
_exptl_crystal_size_min          0.30
_refine_diff_density_max         0.369
_refine_diff_density_min         -0.222
_refine_diff_density_rms         0.051
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.062
_refine_ls_hydrogen_treatment    riding
_refine_ls_matrix_type           full
_refine_ls_number_parameters     232
_refine_ls_number_reflns         4437
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.062
_refine_ls_R_factor_all          0.0945
_refine_ls_R_factor_gt           0.0705
_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)+(0.1163P)²+0.2197P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1986
_refine_ls_wR_factor_ref         0.2208
_reflns_number_gt                3210
_reflns_number_total             4437
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            ol203404q_si_003.cif
_cod_data_source_block           TIPS-1,4,5,14-DHTAP
_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 2.4.1 from 2010-06-29.

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               1503604
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
Si1 Si 0.29241(9) 0.74118(10) 0.18069(3) 0.0588(3) Uani 1 1 d .
C1 C -0.3920(4) 1.2218(4) 0.5300(2) 0.0745(8) Uani 1 1 d .
C2 C -0.3342(4) 1.2707(4) 0.4523(2) 0.0769(8) Uani 1 1 d .
C4 C -0.1935(3) 0.9811(3) 0.45490(13) 0.0493(5) Uani 1 1 d .
C6 C -0.0453(3) 0.6780(3) 0.45810(11) 0.0430(5) Uani 1 1 d .
C7 C 0.0619(2) 0.5511(3) 0.42070(10) 0.0416(4) Uani 1 1 d .
C8 C 0.1067(2) 0.3737(3) 0.46145(11) 0.0424(5) Uani 1 1 d .
C10 C 0.2535(3) 0.0700(3) 0.46500(13) 0.0488(5) Uani 1 1 d .
C12 C 0.1297(3) 0.6064(3) 0.34186(11) 0.0456(5) Uani 1 1 d .
C13 C 0.1890(3) 0.6570(3) 0.27701(13) 0.0554(6) Uani 1 1 d .
C14 C 0.0970(13) 1.0790(7) 0.1917(5) 0.299(7) Uani 1 1 d .
H14A H 0.0449 1.0013 0.2331 0.449 Uiso 1 1 calc R
H14B H 0.0073 1.1366 0.1506 0.449 Uiso 1 1 calc R
H14C H 0.1403 1.1661 0.2148 0.449 Uiso 1 1 calc R
C15 C 0.2307(9) 0.9880(6) 0.1598(3) 0.151(2) Uani 1 1 d .
H15 H 0.3135 0.9944 0.2028 0.181 Uiso 1 1 calc R
C16 C 0.3450(10) 1.0788(6) 0.0956(4) 0.183(3) Uani 1 1 d .
H16A H 0.4439 0.9937 0.0834 0.274 Uiso 1 1 calc R
H16B H 0.3905 1.1692 0.1154 0.274 Uiso 1 1 calc R
H16C H 0.2727 1.1310 0.0477 0.274 Uiso 1 1 calc R
C17 C 0.0028(7) 0.6637(10) 0.0964(3) 0.172(3) Uani 1 1 d .
H17A H -0.0416 0.6317 0.1499 0.259 Uiso 1 1 calc R
H17B H -0.0297 0.5877 0.0634 0.259 Uiso 1 1 calc R
H17C H -0.0491 0.7840 0.0734 0.259 Uiso 1 1 calc R
C18 C 0.1987(5) 0.6450(6) 0.10030(17) 0.0935(10) Uani 1 1 d .
H18 H 0.2396 0.5175 0.1183 0.112 Uiso 1 1 calc R
C19 C 0.2832(6) 0.6859(7) 0.0191(2) 0.1260(16) Uani 1 1 d .
H19A H 0.4118 0.6678 0.0260 0.189 Uiso 1 1 calc R
H19B H 0.2390 0.8066 -0.0063 0.189 Uiso 1 1 calc R
H19C H 0.2529 0.6093 -0.0142 0.189 Uiso 1 1 calc R
C20 C 0.6269(6) 0.7235(9) 0.2589(3) 0.169(3) Uani 1 1 d .
H20A H 0.5991 0.8502 0.2490 0.253 Uiso 1 1 calc R
H20B H 0.7552 0.6858 0.2591 0.253 Uiso 1 1 calc R
H20C H 0.5810 0.6757 0.3103 0.253 Uiso 1 1 calc R
C21 C 0.5397(4) 0.6578(6) 0.19203(18) 0.0974(12) Uani 1 1 d .
H21 H 0.5945 0.7028 0.1409 0.117 Uiso 1 1 calc R
C22 C 0.5845(7) 0.4577(8) 0.2077(3) 0.153(2) Uani 1 1 d .
H22A H 0.5308 0.4164 0.1658 0.229 Uiso 1 1 calc R
H22B H 0.5381 0.4097 0.2590 0.229 Uiso 1 1 calc R
H22C H 0.7128 0.4204 0.2082 0.229 Uiso 1 1 calc R
H1 H -0.458(5) 1.286(5) 0.557(2) 0.096(11) Uiso 1 1 d .
H2 H -0.349(5) 1.397(5) 0.420(2) 0.103(11) Uiso 1 1 d .
N3 N -0.2347(4) 1.1507(3) 0.41458(17) 0.0655(6) Uani 0.50 1 d P
C5 C -0.0915(3) 0.8526(3) 0.41911(12) 0.0509(5) Uani 0.50 1 d P
N5 N -0.0915(3) 0.8526(3) 0.41911(12) 0.0509(5) Uani 0.50 1 d P
C9 C 0.2085(3) 0.2455(3) 0.42600(11) 0.0491(5) Uani 0.50 1 d P
N9 N 0.2085(3) 0.2455(3) 0.42600(11) 0.0491(5) Uani 0.50 1 d P
N11 N 0.3528(3) -0.0515(4) 0.42774(16) 0.0647(6) Uani 0.50 1 d P
H5 H -0.049(3) 0.884(3) 0.3682(17) 0.059(7) Uiso 1 1 d .
H9 H 0.251(4) 0.290(3) 0.3755(17) 0.064(7) Uiso 1 1 d .
C3 C -0.2347(4) 1.1507(3) 0.41458(17) 0.0655(6) Uani 0.50 1 d P
H3 H -0.201(9) 1.179(9) 0.371(4) 0.08(2) Uiso 0.50 1 d P
C11 C 0.3528(3) -0.0515(4) 0.42774(16) 0.0647(6) Uani 0.50 1 d P
H11 H 0.407(7) -0.016(6) 0.380(3) 0.051(12) Uiso 0.50 1 d P
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'
Si Si 0.0817 0.0704 '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
C13 Si1 C21 107.59(13) . .
C13 Si1 C15 107.31(15) . .
C21 Si1 C15 113.5(2) . .
C13 Si1 C18 107.37(12) . .
C21 Si1 C18 108.98(17) . .
C15 Si1 C18 111.8(3) . .
C11 C1 N11 0.0(3) 2_566 2_566
C11 C1 C2 122.0(3) 2_566 .
N11 C1 C2 122.0(3) 2_566 .
C11 C1 H1 111(3) 2_566 .
N11 C1 H1 111(3) 2_566 .
C2 C1 H1 127(3) . .
N3 C2 C1 121.0(3) . .
N3 C2 H2 113(2) . .
C1 C2 H2 125(2) . .
N3 C4 C5 120.8(2) . .
N3 C4 C10 120.7(2) . 2_566
C5 C4 C10 118.5(2) . 2_566
C5 C6 C7 121.53(17) . .
C5 C6 C8 118.66(18) . 2_566
C7 C6 C8 119.81(19) . 2_566
C8 C7 C6 120.55(16) . .
C8 C7 C12 120.24(17) . .
C6 C7 C12 119.18(18) . .
C9 C8 C7 122.00(17) . .
C9 C8 C6 118.37(19) . 2_566
C7 C8 C6 119.63(18) . 2_566
N11 C10 C9 120.9(2) . .
N11 C10 C4 120.4(2) . 2_566
C9 C10 C4 118.75(19) . 2_566
C13 C12 C7 177.7(2) . .
C12 C13 Si1 175.9(2) . .
C15 C14 H14A 109.5 . .
C15 C14 H14B 109.5 . .
H14A C14 H14B 109.5 . .
C15 C14 H14C 109.5 . .
H14A C14 H14C 109.5 . .
H14B C14 H14C 109.5 . .
C14 C15 C16 120.9(4) . .
C14 C15 Si1 125.5(4) . .
C16 C15 Si1 113.4(3) . .
C14 C15 H15 91.2 . .
C16 C15 H15 91.2 . .
Si1 C15 H15 91.2 . .
C15 C16 H16A 109.5 . .
C15 C16 H16B 109.5 . .
H16A C16 H16B 109.5 . .
C15 C16 H16C 109.5 . .
H16A C16 H16C 109.5 . .
H16B C16 H16C 109.5 . .
C18 C17 H17A 109.5 . .
C18 C17 H17B 109.5 . .
H17A C17 H17B 109.5 . .
C18 C17 H17C 109.5 . .
H17A C17 H17C 109.5 . .
H17B C17 H17C 109.5 . .
C17 C18 C19 113.9(3) . .
C17 C18 Si1 116.0(3) . .
C19 C18 Si1 114.3(2) . .
C17 C18 H18 103.5 . .
C19 C18 H18 103.5 . .
Si1 C18 H18 103.5 . .
C18 C19 H19A 109.5 . .
C18 C19 H19B 109.5 . .
H19A C19 H19B 109.5 . .
C18 C19 H19C 109.5 . .
H19A C19 H19C 109.5 . .
H19B C19 H19C 109.5 . .
C21 C20 H20A 109.5 . .
C21 C20 H20B 109.5 . .
H20A C20 H20B 109.5 . .
C21 C20 H20C 109.5 . .
H20A C20 H20C 109.5 . .
H20B C20 H20C 109.5 . .
C22 C21 C20 109.3(4) . .
C22 C21 Si1 112.0(3) . .
C20 C21 Si1 112.7(3) . .
C22 C21 H21 107.5 . .
C20 C21 H21 107.5 . .
Si1 C21 H21 107.5 . .
C21 C22 H22A 109.5 . .
C21 C22 H22B 109.5 . .
H22A C22 H22B 109.5 . .
C21 C22 H22C 109.5 . .
H22A C22 H22C 109.5 . .
H22B C22 H22C 109.5 . .
C4 N3 C2 118.4(3) . .
C4 N3 H3 121(5) . .
C2 N3 H3 121(5) . .
C6 C5 C4 122.86(19) . .
C6 C5 H5 117.6(16) . .
C4 C5 H5 119.5(16) . .
C8 C9 C10 122.88(18) . .
C8 C9 H9 113.8(16) . .
C10 C9 H9 123.2(16) . .
C10 N11 C1 117.5(3) . 2_566
C10 N11 H11 120(3) . .
C1 N11 H11 121(3) 2_566 .
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
Si1 C13 1.845(2) .
Si1 C21 1.862(3) .
Si1 C15 1.873(4) .
Si1 C18 1.886(3) .
C1 C11 1.366(4) 2_566
C1 N11 1.366(4) 2_566
C1 C2 1.377(5) .
C1 H1 0.84(3) .
C2 N3 1.356(4) .
C2 H2 1.02(4) .
C4 N3 1.351(3) .
C4 C5 1.391(3) .
C4 C10 1.423(3) 2_566
C6 C5 1.381(3) .
C6 C7 1.415(3) .
C6 C8 1.433(3) 2_566
C7 C8 1.407(3) .
C7 C12 1.432(2) .
C8 C9 1.385(3) .
C8 C6 1.433(3) 2_566
C10 N11 1.358(3) .
C10 C9 1.386(3) .
C10 C4 1.423(3) 2_566
C12 C13 1.196(3) .
C14 C15 1.305(6) .
C14 H14A 0.9600 .
C14 H14B 0.9600 .
C14 H14C 0.9600 .
C15 C16 1.518(5) .
C15 H15 0.9800 .
C16 H16A 0.9600 .
C16 H16B 0.9600 .
C16 H16C 0.9600 .
C17 C18 1.460(6) .
C17 H17A 0.9600 .
C17 H17B 0.9600 .
C17 H17C 0.9600 .
C18 C19 1.504(4) .
C18 H18 0.9800 .
C19 H19A 0.9600 .
C19 H19B 0.9600 .
C19 H19C 0.9600 .
C20 C21 1.537(5) .
C20 H20A 0.9600 .
C20 H20B 0.9600 .
C20 H20C 0.9600 .
C21 C22 1.517(7) .
C21 H21 0.9800 .
C22 H22A 0.9600 .
C22 H22B 0.9600 .
C22 H22C 0.9600 .
N3 H3 0.78(7) .
C5 H5 0.92(3) .
C9 H9 0.93(3) .
N11 C1 1.366(4) 2_566
N11 H11 0.91(5) .
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 C1 C2 N3 -0.2(5) 2_566 .
N11 C1 C2 N3 -0.2(5) 2_566 .
C5 C6 C7 C8 -179.72(18) . .
C8 C6 C7 C8 0.9(3) 2_566 .
C5 C6 C7 C12 2.5(3) . .
C8 C6 C7 C12 -176.90(17) 2_566 .
C6 C7 C8 C9 178.80(18) . .
C12 C7 C8 C9 -3.4(3) . .
C6 C7 C8 C6 -0.9(3) . 2_566
C12 C7 C8 C6 176.88(17) . 2_566
C8 C7 C12 C13 -124(6) . .
C6 C7 C12 C13 53(6) . .
C7 C12 C13 Si1 24(8) . .
C21 Si1 C13 C12 51(3) . .
C15 Si1 C13 C12 -72(3) . .
C18 Si1 C13 C12 168(3) . .
C13 Si1 C15 C14 -19.8(9) . .
C21 Si1 C15 C14 -138.5(8) . .
C18 Si1 C15 C14 97.7(9) . .
C13 Si1 C15 C16 164.4(5) . .
C21 Si1 C15 C16 45.7(6) . .
C18 Si1 C15 C16 -78.1(5) . .
C13 Si1 C18 C17 50.3(4) . .
C21 Si1 C18 C17 166.5(4) . .
C15 Si1 C18 C17 -67.2(4) . .
C13 Si1 C18 C19 -174.2(3) . .
C21 Si1 C18 C19 -57.9(4) . .
C15 Si1 C18 C19 68.4(4) . .
C13 Si1 C21 C22 62.2(3) . .
C15 Si1 C21 C22 -179.2(3) . .
C18 Si1 C21 C22 -53.9(3) . .
C13 Si1 C21 C20 -61.6(4) . .
C15 Si1 C21 C20 57.0(4) . .
C18 Si1 C21 C20 -177.7(3) . .
C5 C4 N3 C2 -179.9(2) . .
C10 C4 N3 C2 0.2(4) 2_566 .
C1 C2 N3 C4 0.0(4) . .
C7 C6 C5 C4 -178.63(18) . .
C8 C6 C5 C4 0.8(3) 2_566 .
N3 C4 C5 C6 179.6(2) . .
C10 C4 C5 C6 -0.4(3) 2_566 .
C7 C8 C9 C10 -179.75(18) . .
C6 C8 C9 C10 -0.1(3) 2_566 .
N11 C10 C9 C8 179.60(19) . .
C4 C10 C9 C8 -0.3(3) 2_566 .
C9 C10 N11 C1 179.9(2) . 2_566
C4 C10 N11 C1 -0.1(3) 2_566 2_566
