#------------------------------------------------------------------------------
#$Date: 2016-02-18 17:37:37 +0200 (Thu, 18 Feb 2016) $
#$Revision: 176729 $
#$URL: svn://www.crystallography.net/cod/cif/1/50/83/1508347.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_1508347
loop_
_publ_author_name
'He, Zikai'
'Mao, Renxin'
'Liu, Danqing'
'Miao, Qian'
_publ_section_title
;
 Highly electron-deficient hexaazapentacenes and their dihydro precursors.
;
_journal_issue                   16
_journal_name_full               'Organic letters'
_journal_page_first              4190
_journal_page_last               4193
_journal_paper_doi               10.1021/ol301854z
_journal_volume                  14
_journal_year                    2012
_chemical_formula_sum            'C38 H50 N6 Si2'
_chemical_formula_weight         647.02
_chemical_name_systematic
; 
 1,8-bis((triisopropylsilyl)ethynyl)-6,13-dihydro-5,6,7,12,13,14-hexaazapentacene 
;
_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                100.107(9)
_cell_angle_beta                 93.769(9)
_cell_angle_gamma                107.794(10)
_cell_formula_units_Z            2
_cell_length_a                   12.635(5)
_cell_length_b                   12.882(5)
_cell_length_c                   14.664(6)
_cell_measurement_reflns_used    32
_cell_measurement_temperature    296(2)
_cell_measurement_theta_max      15
_cell_measurement_theta_min      15
_cell_volume                     2219.1(15)
_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, 2008)'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 2008)'
_diffrn_ambient_temperature      296(2)
_diffrn_measured_fraction_theta_full 0.982
_diffrn_measured_fraction_theta_max 0.982
_diffrn_measurement_device_type  'BRUKER KAPPA APEXII DUO DIFFRACTOMETER'
_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  0.1995
_diffrn_reflns_av_sigmaI/netI    0.3386
_diffrn_reflns_limit_h_max       15
_diffrn_reflns_limit_h_min       -14
_diffrn_reflns_limit_k_max       15
_diffrn_reflns_limit_k_min       -15
_diffrn_reflns_limit_l_max       17
_diffrn_reflns_limit_l_min       -17
_diffrn_reflns_number            24609
_diffrn_reflns_theta_full        25.25
_diffrn_reflns_theta_max         25.25
_diffrn_reflns_theta_min         1.42
_exptl_absorpt_coefficient_mu    0.109
_exptl_absorpt_correction_T_max  0.7456
_exptl_absorpt_correction_T_min  0.5489
_exptl_absorpt_correction_type   multi-scan
_exptl_crystal_colour            yellow
_exptl_crystal_density_diffrn    0.968
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       block
_exptl_crystal_F_000             696
_exptl_crystal_size_max          0.40
_exptl_crystal_size_mid          0.30
_exptl_crystal_size_min          0.20
_platon_squeeze_details
;
;
_refine_diff_density_max         0.249
_refine_diff_density_min         -0.229
_refine_diff_density_rms         0.053
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   0.755
_refine_ls_hydrogen_treatment    riding
_refine_ls_matrix_type           full
_refine_ls_number_parameters     415
_refine_ls_number_reflns         7904
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      0.755
_refine_ls_R_factor_all          0.2634
_refine_ls_R_factor_gt           0.0817
_refine_ls_shift/su_max          0.001
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'calc w=1/[σ²(Fo²)+(0.0590P)²+0.0000P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1702
_refine_ls_wR_factor_ref         0.2238
_reflns_number_gt                2021
_reflns_number_total             7904
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            ol301854z_si_002.cif
_cod_data_source_block           1,8-TIPS-DHHAP
_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 1891 2012-01-12 08:04:46Z andrius 
;
_cod_original_sg_symbol_H-M      P-1
_cod_database_code               1508347
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 0.07073(15) -0.05831(16) 0.28767(13) 0.0655(6) Uani 1 1 d .
N1 N -0.0451(4) 0.2896(4) 0.4003(3) 0.0463(13) Uani 1 1 d .
N2 N 0.0850(4) 0.4594(4) 0.4770(3) 0.0468(13) Uani 1 1 d .
H2A H 0.1382 0.4342 0.4610 0.056 Uiso 1 1 calc R
N3 N 0.2181(4) 0.6188(4) 0.5590(3) 0.0477(13) Uani 1 1 d .
C1 C -0.3803(5) 0.1036(6) 0.3098(5) 0.100(3) Uani 1 1 d .
H1A H -0.4549 0.0631 0.2876 0.120 Uiso 1 1 calc R
C2 C -0.2969(5) 0.0543(5) 0.2936(5) 0.088(2) Uani 1 1 d .
H2AA H -0.3161 -0.0192 0.2614 0.106 Uiso 1 1 calc R
C3 C -0.1853(5) 0.1154(5) 0.3256(4) 0.0580(17) Uani 1 1 d .
C4 C -0.1566(5) 0.2269(5) 0.3725(4) 0.0479(16) Uani 1 1 d .
C5 C -0.0241(5) 0.3913(5) 0.4476(4) 0.0394(14) Uani 1 1 d .
C6 C 0.1130(5) 0.5639(4) 0.5297(4) 0.0363(14) Uani 1 1 d .
C7 C 0.2422(5) 0.7255(5) 0.6101(4) 0.0556(17) Uani 1 1 d .
C8 C 0.3522(5) 0.7878(5) 0.6412(5) 0.081(2) Uani 1 1 d .
H8A H 0.4083 0.7564 0.6291 0.097 Uiso 1 1 calc R
C9 C -0.0991(5) 0.0620(5) 0.3114(4) 0.0601(18) Uani 1 1 d .
C10 C -0.0354(5) 0.0114(5) 0.3000(4) 0.0624(18) Uani 1 1 d .
C11 C 0.0421(8) -0.1624(8) 0.3623(6) 0.121(3) Uani 1 1 d .
H11A H 0.0791 -0.1166 0.4234 0.145 Uiso 1 1 calc R
C12 C -0.0711(10) -0.2154(9) 0.3834(8) 0.207(6) Uani 1 1 d .
H12A H -0.0685 -0.2649 0.4247 0.311 Uiso 1 1 calc R
H12B H -0.1185 -0.2568 0.3265 0.311 Uiso 1 1 calc R
H12C H -0.1005 -0.1593 0.4127 0.311 Uiso 1 1 calc R
C13 C 0.1087(10) -0.2483(9) 0.3459(7) 0.191(5) Uani 1 1 d .
H13A H 0.1032 -0.2873 0.3964 0.286 Uiso 1 1 calc R
H13B H 0.1860 -0.2092 0.3431 0.286 Uiso 1 1 calc R
H13C H 0.0773 -0.3007 0.2881 0.286 Uiso 1 1 calc R
C14 C 0.0610(6) -0.1234(6) 0.1609(4) 0.078(2) Uani 1 1 d .
H14A H 0.1212 -0.1563 0.1546 0.094 Uiso 1 1 calc R
C15 C -0.0495(9) -0.2160(8) 0.1227(6) 0.153(4) Uani 1 1 d .
H15A H -0.0482 -0.2463 0.0583 0.230 Uiso 1 1 calc R
H15B H -0.1104 -0.1862 0.1279 0.230 Uiso 1 1 calc R
H15C H -0.0595 -0.2737 0.1580 0.230 Uiso 1 1 calc R
C16 C 0.0770(8) -0.0406(7) 0.0991(5) 0.132(4) Uani 1 1 d .
H16A H 0.0726 -0.0778 0.0355 0.198 Uiso 1 1 calc R
H16B H 0.1491 0.0153 0.1177 0.198 Uiso 1 1 calc R
H16C H 0.0195 -0.0062 0.1043 0.198 Uiso 1 1 calc R
C17 C 0.2103(6) 0.0612(7) 0.3224(6) 0.108(3) Uani 1 1 d .
H17A H 0.2102 0.1113 0.2792 0.129 Uiso 1 1 calc R
C18 C 0.3092(7) 0.0259(9) 0.3086(8) 0.211(6) Uani 1 1 d .
H18A H 0.3757 0.0897 0.3249 0.317 Uiso 1 1 calc R
H18B H 0.3045 -0.0091 0.2444 0.317 Uiso 1 1 calc R
H18C H 0.3120 -0.0261 0.3476 0.317 Uiso 1 1 calc R
C19 C 0.2189(8) 0.1311(8) 0.4204(6) 0.157(4) Uani 1 1 d .
H19A H 0.2898 0.1896 0.4344 0.236 Uiso 1 1 calc R
H19B H 0.2129 0.0845 0.4655 0.236 Uiso 1 1 calc R
H19C H 0.1594 0.1630 0.4226 0.236 Uiso 1 1 calc R
Si1' Si 0.69171(16) 0.30932(17) 0.05035(14) 0.0717(7) Uani 1 1 d .
N1' N 0.5911(4) 0.4799(4) 0.4647(3) 0.0525(14) Uani 1 1 d .
H1'A H 0.6479 0.4655 0.4430 0.063 Uiso 1 1 calc R
N2' N 0.4878(4) 0.3912(4) 0.3228(3) 0.0410(12) Uani 1 1 d .
N3' N 0.2961(4) 0.4242(4) 0.3966(3) 0.0486(13) Uani 1 1 d .
C1' C 0.6062(4) 0.5390(5) 0.5558(4) 0.0408(15) Uani 1 1 d .
C2' C 0.4915(5) 0.4428(4) 0.4070(4) 0.0417(15) Uani 1 1 d .
C3' C 0.3851(5) 0.3552(5) 0.2675(4) 0.0469(16) Uani 1 1 d .
C4' C 0.3761(5) 0.2998(5) 0.1734(4) 0.0482(16) Uani 1 1 d .
C5' C 0.2736(5) 0.2624(5) 0.1200(4) 0.0615(18) Uani 1 1 d .
H5'A H 0.2668 0.2287 0.0574 0.074 Uiso 1 1 calc R
C6' C 0.1789(5) 0.2747(5) 0.1592(4) 0.0622(18) Uani 1 1 d .
H6'A H 0.1096 0.2466 0.1224 0.075 Uiso 1 1 calc R
C7' C 0.1850(5) 0.3255(5) 0.2478(4) 0.0613(18) Uani 1 1 d .
H7'A H 0.1205 0.3326 0.2714 0.074 Uiso 1 1 calc R
C8' C 0.2881(5) 0.3681(5) 0.3055(4) 0.0490(16) Uani 1 1 d .
C9' C 0.4757(5) 0.2939(5) 0.1333(4) 0.0559(17) Uani 1 1 d .
C10' C 0.5588(5) 0.2946(5) 0.0984(4) 0.0641(19) Uani 1 1 d .
C11' C 0.7976(7) 0.3567(11) 0.1520(7) 0.146(4) Uani 1 1 d .
H11B H 0.7782 0.2961 0.1863 0.175 Uiso 1 1 calc R
C12' C 0.7992(8) 0.4599(8) 0.2232(7) 0.159(4) Uani 1 1 d .
H12D H 0.8589 0.4764 0.2730 0.238 Uiso 1 1 calc R
H12E H 0.7290 0.4456 0.2482 0.238 Uiso 1 1 calc R
H12F H 0.8107 0.5222 0.1931 0.238 Uiso 1 1 calc R
C13' C 0.9193(7) 0.3610(13) 0.1223(8) 0.252(7) Uani 1 1 d .
H13D H 0.9735 0.3851 0.1771 0.378 Uiso 1 1 calc R
H13E H 0.9403 0.4122 0.0813 0.378 Uiso 1 1 calc R
H13F H 0.9166 0.2881 0.0908 0.378 Uiso 1 1 calc R
C14' C 0.7033(9) 0.4058(9) -0.0313(7) 0.148(4) Uani 1 1 d .
H14B H 0.6493 0.3471 -0.0789 0.178 Uiso 1 1 calc R
C15' C 0.7985(8) 0.4089(9) -0.0935(7) 0.185(5) Uani 1 1 d .
H15D H 0.7936 0.4528 -0.1392 0.278 Uiso 1 1 calc R
H15E H 0.7910 0.3344 -0.1246 0.278 Uiso 1 1 calc R
H15F H 0.8698 0.4413 -0.0553 0.278 Uiso 1 1 calc R
C16' C 0.6466(13) 0.4714(14) -0.0371(12) 0.341(13) Uani 1 1 d .
H16D H 0.6426 0.4849 -0.0994 0.511 Uiso 1 1 calc R
H16E H 0.6822 0.5406 0.0064 0.511 Uiso 1 1 calc R
H16F H 0.5723 0.4381 -0.0227 0.511 Uiso 1 1 calc R
C17' C 0.6847(9) 0.1669(8) -0.0158(8) 0.132(4) Uani 1 1 d .
H17B H 0.7531 0.1771 -0.0459 0.159 Uiso 1 1 calc R
C18' C 0.5826(12) 0.1159(9) -0.0970(8) 0.200(6) Uani 1 1 d .
H18D H 0.5821 0.0436 -0.1280 0.300 Uiso 1 1 calc R
H18E H 0.5904 0.1639 -0.1411 0.300 Uiso 1 1 calc R
H18F H 0.5137 0.1093 -0.0710 0.300 Uiso 1 1 calc R
C19' C 0.6865(11) 0.0876(9) 0.0507(9) 0.223(7) Uani 1 1 d .
H19D H 0.6776 0.0148 0.0150 0.335 Uiso 1 1 calc R
H19E H 0.6264 0.0834 0.0881 0.335 Uiso 1 1 calc R
H19F H 0.7568 0.1151 0.0905 0.335 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'
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
C10 Si1 C11 107.2(3) . .
C10 Si1 C14 108.2(3) . .
C11 Si1 C14 112.4(4) . .
C10 Si1 C17 104.0(3) . .
C11 Si1 C17 115.9(4) . .
C14 Si1 C17 108.5(4) . .
C5 N1 C4 117.0(4) . .
C6 N2 C5 123.6(4) . .
C6 N3 C7 116.7(4) . .
C8 C1 C2 120.1(6) 2_566 .
C3 C2 C1 119.9(6) . .
C2 C3 C4 119.8(5) . .
C2 C3 C9 119.5(5) . .
C4 C3 C9 120.6(5) . .
N1 C4 C3 120.0(5) . .
N1 C4 C7 120.6(5) . 2_566
C3 C4 C7 119.4(6) . 2_566
N1 C5 N2 120.4(4) . .
N1 C5 C6 121.6(5) . 2_566
N2 C5 C6 118.0(5) . 2_566
N3 C6 N2 119.0(4) . .
N3 C6 C5 122.7(5) . 2_566
N2 C6 C5 118.3(5) . 2_566
C8 C7 N3 118.9(5) . .
C8 C7 C4 119.9(5) . 2_566
N3 C7 C4 121.2(5) . 2_566
C7 C8 C1 120.8(5) . 2_566
C10 C9 C3 175.0(6) . .
C9 C10 Si1 175.9(6) . .
C12 C11 C13 111.3(9) . .
C12 C11 Si1 121.9(7) . .
C13 C11 Si1 114.9(6) . .
C16 C14 C15 107.3(7) . .
C16 C14 Si1 112.9(5) . .
C15 C14 Si1 113.9(5) . .
C18 C17 C19 112.5(8) . .
C18 C17 Si1 113.7(6) . .
C19 C17 Si1 112.7(5) . .
C11' Si1' C10' 104.7(3) . .
C11' Si1' C14' 115.9(5) . .
C10' Si1' C14' 107.3(4) . .
C11' Si1' C17' 111.2(5) . .
C10' Si1' C17' 107.5(3) . .
C14' Si1' C17' 109.8(5) . .
C2' N1' C1' 124.1(4) . .
C2' N2' C3' 116.5(4) . .
C1' N3' C8' 116.8(5) 2_666 .
N3' C1' N1' 120.1(4) 2_666 .
N3' C1' C2' 122.7(5) 2_666 2_666
N1' C1' C2' 117.3(5) . 2_666
N2' C2' N1' 118.9(5) . .
N2' C2' C1' 122.6(5) . 2_666
N1' C2' C1' 118.5(5) . 2_666
N2' C3' C4' 119.2(5) . .
N2' C3' C8' 120.7(5) . .
C4' C3' C8' 120.0(6) . .
C5' C4' C3' 118.8(5) . .
C5' C4' C9' 121.2(5) . .
C3' C4' C9' 119.7(5) . .
C4' C5' C6' 120.3(6) . .
C7' C6' C5' 122.0(6) . .
C6' C7' C8' 120.5(5) . .
N3' C8' C7' 121.0(5) . .
N3' C8' C3' 120.5(5) . .
C7' C8' C3' 118.4(5) . .
C10' C9' C4' 176.2(7) . .
C9' C10' Si1' 174.6(6) . .
C12' C11' C13' 113.6(9) . .
C12' C11' Si1' 117.7(7) . .
C13' C11' Si1' 111.0(7) . .
C16' C14' C15' 118.8(9) . .
C16' C14' Si1' 127.1(8) . .
C15' C14' Si1' 114.0(7) . .
C19' C17' C18' 112.6(10) . .
C19' C17' Si1' 111.4(7) . .
C18' C17' Si1' 112.5(7) . .
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
Si1 C10 1.830(6) .
Si1 C11 1.843(8) .
Si1 C14 1.880(6) .
Si1 C17 1.920(8) .
N1 C5 1.309(6) .
N1 C4 1.384(6) .
N2 C6 1.358(6) .
N2 C5 1.381(6) .
N3 C6 1.301(6) .
N3 C7 1.377(6) .
C1 C8 1.383(8) 2_566
C1 C2 1.400(7) .
C2 C3 1.390(7) .
C3 C4 1.404(7) .
C3 C9 1.463(7) .
C4 C7 1.413(6) 2_566
C5 C6 1.442(6) 2_566
C6 C5 1.442(6) 2_566
C7 C8 1.374(7) .
C7 C4 1.413(6) 2_566
C8 C1 1.383(8) 2_566
C9 C10 1.183(6) .
C11 C12 1.463(11) .
C11 C13 1.579(10) .
C14 C16 1.493(9) .
C14 C15 1.526(10) .
C17 C18 1.470(9) .
C17 C19 1.534(9) .
Si1' C11' 1.818(10) .
Si1' C10' 1.833(6) .
Si1' C14' 1.853(9) .
Si1' C17' 1.892(9) .
N1' C2' 1.370(6) .
N1' C1' 1.386(6) .
N2' C2' 1.287(6) .
N2' C3' 1.385(6) .
N3' C1' 1.284(6) 2_666
N3' C8' 1.384(6) .
C1' N3' 1.284(6) 2_666
C1' C2' 1.448(6) 2_666
C2' C1' 1.448(6) 2_666
C3' C4' 1.417(7) .
C3' C8' 1.422(6) .
C4' C5' 1.370(7) .
C4' C9' 1.441(7) .
C5' C6' 1.401(7) .
C6' C7' 1.333(7) .
C7' C8' 1.403(7) .
C9' C10' 1.196(6) .
C11' C12' 1.533(11) .
C11' C13' 1.613(10) .
C14' C16' 1.274(11) .
C14' C15' 1.552(10) .
C17' C19' 1.535(12) .
C17' C18' 1.586(13) .
loop_
_platon_squeeze_void_nr
_platon_squeeze_void_average_x
_platon_squeeze_void_average_y
_platon_squeeze_void_average_z
_platon_squeeze_void_volume
_platon_squeeze_void_count_electrons
1 0.500 1.000 0.500 444.1 101.2
