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#$URL: file:///home/coder/svn-repositories/cod/cif/1/55/59/1555913.cif $
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# 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.
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data_1555913
loop_
_publ_author_name
'Granger, Devin B.'
'Mei, Yaochuan'
'Thorley, Karl J.'
'Parkin, Sean R.'
'Jurchescu, Oana D.'
'Anthony, John E.'
_publ_section_title
;
 Synthesis and Electrical Properties of Derivatives of
 1,4-bis(trialkylsilylethynyl)benzo[2,3-b:5,6-b']diindolizines.
;
_journal_issue                   23
_journal_name_full               'Organic letters'
_journal_page_first              6050
_journal_page_last               6053
_journal_paper_doi               10.1021/acs.orglett.6b02991
_journal_volume                  18
_journal_year                    2016
_chemical_formula_moiety         'C34 H40 N2 Si2'
_chemical_formula_sum            'C34 H40 N2 Si2'
_chemical_formula_weight         532.86
_space_group_crystal_system      monoclinic
_space_group_IT_number           14
_space_group_name_Hall           '-P 2ybc'
_space_group_name_H-M_alt        'P 1 21/c 1'
_atom_sites_solution_hydrogens   difmap
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_audit_creation_method           'SHELXL-2014/7 and CIFFIX'
_cell_angle_alpha                90
_cell_angle_beta                 113.100(8)
_cell_angle_gamma                90
_cell_formula_units_Z            2
_cell_length_a                   6.5947(8)
_cell_length_b                   32.761(3)
_cell_length_c                   7.6610(12)
_cell_measurement_reflns_used    3026
_cell_measurement_temperature    240(2)
_cell_measurement_theta_max      67.09
_cell_measurement_theta_min      2.70
_cell_volume                     1522.4(3)
_computing_cell_refinement       'APEX2 (Bruker-AXS, 2006)'
_computing_data_collection       'APEX2 (Bruker-AXS, 2006)'
_computing_data_reduction        'APEX2 (Bruker-AXS, 2006)'
_computing_molecular_graphics    'XP in SHELXTL (Sheldrick, 2008)'
_computing_publication_material
'SHELX (Sheldrick, 2008) and CIFFIX (Parkin, 2013)'
_computing_structure_refinement  'SHELXL-2014/7 (Sheldrick, 2015b)'
_computing_structure_solution    'SHELXT (Sheldrick, 2015a)'
_diffrn_ambient_temperature      240(2)
_diffrn_detector_area_resol_mean 5.6
_diffrn_measured_fraction_theta_full 1.000
_diffrn_measured_fraction_theta_max 0.999
_diffrn_measurement_device_type  'Bruker X8 Proteum diffractometer'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54178
_diffrn_reflns_av_R_equivalents  0.0881
_diffrn_reflns_av_unetI/netI     0.0556
_diffrn_reflns_Laue_measured_fraction_full 1.000
_diffrn_reflns_Laue_measured_fraction_max 0.999
_diffrn_reflns_limit_h_max       7
_diffrn_reflns_limit_h_min       -7
_diffrn_reflns_limit_k_max       39
_diffrn_reflns_limit_k_min       -39
_diffrn_reflns_limit_l_max       9
_diffrn_reflns_limit_l_min       -3
_diffrn_reflns_number            19539
_diffrn_reflns_point_group_measured_fraction_full 1.000
_diffrn_reflns_point_group_measured_fraction_max 0.999
_diffrn_reflns_theta_full        67.679
_diffrn_reflns_theta_max         68.335
_diffrn_reflns_theta_min         2.697
_diffrn_source                   'fine-focus rotating anode'
_exptl_absorpt_coefficient_mu    1.231
_exptl_absorpt_correction_T_max  0.942
_exptl_absorpt_correction_T_min  0.532
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   'SADABS (Krause et al., 2015)'
_exptl_crystal_colour            blue-red
_exptl_crystal_density_diffrn    1.162
_exptl_crystal_description       rod
_exptl_crystal_F_000             572
_exptl_crystal_size_max          0.160
_exptl_crystal_size_mid          0.030
_exptl_crystal_size_min          0.030
_refine_diff_density_max         0.327
_refine_diff_density_min         -0.310
_refine_diff_density_rms         0.057
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.272
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     175
_refine_ls_number_reflns         2781
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.272
_refine_ls_R_factor_all          0.1093
_refine_ls_R_factor_gt           0.0848
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'w=1/[σ²(Fo²)+(0.1150P)²+0.7180P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.2605
_refine_ls_wR_factor_ref         0.2861
_reflns_Friedel_coverage         0.000
_reflns_number_gt                1865
_reflns_number_total             2781
_reflns_threshold_expression     'I > 2σ(I)'
_cod_data_source_file            ol6b02991_si_008.cif
_cod_data_source_block           x15128
_cod_original_sg_symbol_H-M      'P 21/c'
_cod_database_code               1555913
_shelx_shelxl_version_number     2014/7
_shelx_space_group_comment
; 
The symmetry employed for this shelxl refinement is uniquely defined 
by the following loop, which should always be used as a source of 
symmetry information in preference to the above space-group names. 
They are only intended as comments. 
;
_shelx_estimated_absorpt_t_min   0.827
_shelx_estimated_absorpt_t_max   0.964
_exptl_absorpt_special_details
; 
In addition to absorption, multi-scan techniques also correct other slowly 
varying changes in scale factor over reciprocal space, such as those caused 
by x-ray beam inhomogeneity, goniometer imperfection, crystal decomposition, 
crystal longer than the x-ray beam cross section, absorption by the crystal 
mount etc.  These account, by and large, for much of the difference between 
estimated values of Tmin and Tmax and the _exptl_absorpt_correction_ values. 
;
loop_
_space_group_symop_operation_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_site_symmetry_order
_atom_site_calc_flag
_atom_site_refinement_flags_posn
_atom_site_refinement_flags_adp
Si1 Si 0.6856(2) 0.33715(4) 0.86398(17) 0.0699(5) Uani 1 1 d . .
C1 C 0.5525(7) 0.46135(13) 0.6032(6) 0.064(1) Uani 1 1 d . .
C2 C 0.5982(7) 0.49872(13) 0.6942(6) 0.0659(10) Uani 1 1 d . .
N3 N 0.6954(6) 0.50779(11) 0.8873(5) 0.0631(8) Uani 1 1 d . .
C4 C 0.7722(7) 0.48123(14) 1.0410(6) 0.0688(11) Uani 1 1 d . .
H4A H 0.7632 0.4528 1.0217 0.083 Uiso 1 1 calc R U
C5 C 0.8597(7) 0.49675(15) 1.2180(6) 0.0720(11) Uani 1 1 d . .
H5A H 0.9116 0.4791 1.3230 0.086 Uiso 1 1 calc R U
C6 C 0.8738(7) 0.53936(15) 1.2467(6) 0.0724(11) Uani 1 1 d . .
H6A H 0.9366 0.5497 1.3709 0.087 Uiso 1 1 calc R U
C7 C 0.7997(7) 0.56514(15) 1.1007(6) 0.0707(11) Uani 1 1 d . .
H7A H 0.8090 0.5934 1.1232 0.085 Uiso 1 1 calc R U
C8 C 0.7065(7) 0.55032(14) 0.9110(6) 0.065(1) Uani 1 1 d . .
C9 C 0.6189(8) 0.56811(13) 0.7376(6) 0.0696(11) Uani 1 1 d . .
H9A H 0.6066 0.5963 0.7137 0.083 Uiso 1 1 calc R U
C10 C 0.5492(7) 0.53698(13) 0.5988(6) 0.0695(11) Uani 1 1 d . .
C11 C 0.6008(7) 0.42246(13) 0.6935(6) 0.0633(10) Uani 1 1 d . .
C12 C 0.6362(7) 0.38877(14) 0.7625(6) 0.0674(10) Uani 1 1 d . .
C13 C 0.4704(9) 0.30354(15) 0.6902(6) 0.0803(13) Uani 1 1 d . .
H13A H 0.4904 0.2756 0.7395 0.096 Uiso 1 1 calc R U
H13B H 0.3243 0.3129 0.6783 0.096 Uiso 1 1 calc R U
C14 C 0.4794(10) 0.30341(17) 0.4938(8) 0.0960(16) Uani 1 1 d . .
H14A H 0.3677 0.2850 0.4109 0.144 Uiso 1 1 calc R U
H14B H 0.6238 0.2943 0.5045 0.144 Uiso 1 1 calc R U
H14C H 0.4523 0.3308 0.4413 0.144 Uiso 1 1 calc R U
C15 C 0.9668(8) 0.32049(15) 0.8937(7) 0.0818(13) Uani 1 1 d . .
H15A H 0.9815 0.3235 0.7719 0.098 Uiso 1 1 calc R U
H15B H 1.0749 0.3387 0.9850 0.098 Uiso 1 1 calc R U
C16 C 1.0216(11) 0.27686(17) 0.9612(8) 0.0996(17) Uani 1 1 d . .
H16A H 1.1608 0.2691 0.9554 0.149 Uiso 1 1 calc R U
H16B H 0.9060 0.2589 0.8805 0.149 Uiso 1 1 calc R U
H16C H 1.0331 0.2746 1.0910 0.149 Uiso 1 1 calc R U
C17 C 0.6615(9) 0.33735(14) 1.0970(7) 0.0797(13) Uani 1 1 d . .
H17A H 0.5171 0.3486 1.0796 0.096 Uiso 1 1 calc R U
H17B H 0.6660 0.3090 1.1398 0.096 Uiso 1 1 calc R U
C18 C 0.8399(10) 0.36173(18) 1.2539(7) 0.0970(16) Uani 1 1 d . .
H18A H 0.8093 0.3614 1.3678 0.145 Uiso 1 1 calc R U
H18B H 0.8403 0.3897 1.2122 0.145 Uiso 1 1 calc R U
H18C H 0.9829 0.3495 1.2808 0.145 Uiso 1 1 calc R U
loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0181 0.0091 '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 0.0311 0.0180 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
Si Si 0.2541 0.3302 '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
C12 Si1 C17 109.7(2) .
C12 Si1 C15 108.9(2) .
C17 Si1 C15 110.0(2) .
C12 Si1 C13 106.3(2) .
C17 Si1 C13 111.0(2) .
C15 Si1 C13 110.8(2) .
C2 C1 C11 125.7(4) .
C2 C1 C10 115.5(4) 3_666
C11 C1 C10 118.8(4) 3_666
C1 C2 N3 130.0(4) .
C1 C2 C10 124.1(4) .
N3 C2 C10 105.9(4) .
C4 N3 C2 128.9(4) .
C4 N3 C8 121.9(4) .
C2 N3 C8 109.1(3) .
C5 C4 N3 119.1(4) .
C5 C4 H4A 120.5 .
N3 C4 H4A 120.5 .
C4 C5 C6 120.4(4) .
C4 C5 H5A 119.8 .
C6 C5 H5A 119.8 .
C7 C6 C5 121.1(4) .
C7 C6 H6A 119.5 .
C5 C6 H6A 119.5 .
C6 C7 C8 120.7(5) .
C6 C7 H7A 119.7 .
C8 C7 H7A 119.7 .
C9 C8 N3 108.6(4) .
C9 C8 C7 134.6(4) .
N3 C8 C7 116.8(4) .
C8 C9 C10 108.4(4) .
C8 C9 H9A 125.8 .
C10 C9 H9A 125.8 .
C9 C10 C2 107.9(4) .
C9 C10 C1 131.6(4) 3_666
C2 C10 C1 120.5(4) 3_666
C12 C11 C1 177.2(5) .
C11 C12 Si1 179.0(4) .
C14 C13 Si1 112.9(3) .
C14 C13 H13A 109.0 .
Si1 C13 H13A 109.0 .
C14 C13 H13B 109.0 .
Si1 C13 H13B 109.0 .
H13A C13 H13B 107.8 .
C13 C14 H14A 109.5 .
C13 C14 H14B 109.5 .
H14A C14 H14B 109.5 .
C13 C14 H14C 109.5 .
H14A C14 H14C 109.5 .
H14B C14 H14C 109.5 .
C16 C15 Si1 114.3(4) .
C16 C15 H15A 108.7 .
Si1 C15 H15A 108.7 .
C16 C15 H15B 108.7 .
Si1 C15 H15B 108.7 .
H15A C15 H15B 107.6 .
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 Si1 115.3(4) .
C18 C17 H17A 108.5 .
Si1 C17 H17A 108.5 .
C18 C17 H17B 108.5 .
Si1 C17 H17B 108.5 .
H17A C17 H17B 107.5 .
C17 C18 H18A 109.5 .
C17 C18 H18B 109.5 .
H18A C18 H18B 109.5 .
C17 C18 H18C 109.5 .
H18A C18 H18C 109.5 .
H18B C18 H18C 109.5 .
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
Si1 C12 1.836(5) .
Si1 C17 1.853(5) .
Si1 C15 1.860(5) .
Si1 C13 1.875(5) .
C1 C2 1.382(6) .
C1 C11 1.425(6) .
C1 C10 1.426(6) 3_666
C2 N3 1.394(5) .
C2 C10 1.423(6) .
N3 C4 1.390(5) .
N3 C8 1.403(6) .
C4 C5 1.348(6) .
C4 H4A 0.9400 .
C5 C6 1.411(6) .
C5 H5A 0.9400 .
C6 C7 1.332(6) .
C6 H6A 0.9400 .
C7 C8 1.423(6) .
C7 H7A 0.9400 .
C8 C9 1.355(6) .
C9 C10 1.414(6) .
C9 H9A 0.9400 .
C10 C1 1.426(6) 3_666
C11 C12 1.206(6) .
C13 C14 1.529(7) .
C13 H13A 0.9800 .
C13 H13B 0.9800 .
C14 H14A 0.9700 .
C14 H14B 0.9700 .
C14 H14C 0.9700 .
C15 C16 1.515(7) .
C15 H15A 0.9800 .
C15 H15B 0.9800 .
C16 H16A 0.9700 .
C16 H16B 0.9700 .
C16 H16C 0.9700 .
C17 C18 1.536(7) .
C17 H17A 0.9800 .
C17 H17B 0.9800 .
C18 H18A 0.9700 .
C18 H18B 0.9700 .
C18 H18C 0.9700 .
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 -0.9(7) . .
C10 C1 C2 N3 -180.0(4) 3_666 .
C11 C1 C2 C10 179.4(4) . .
C10 C1 C2 C10 0.3(7) 3_666 .
C1 C2 N3 C4 -0.2(7) . .
C10 C2 N3 C4 179.5(4) . .
C1 C2 N3 C8 -179.8(4) . .
C10 C2 N3 C8 0.0(4) . .
C2 N3 C4 C5 -179.4(4) . .
C8 N3 C4 C5 0.1(6) . .
N3 C4 C5 C6 -0.2(6) . .
C4 C5 C6 C7 0.6(7) . .
C5 C6 C7 C8 -0.8(7) . .
C4 N3 C8 C9 -179.6(4) . .
C2 N3 C8 C9 -0.1(5) . .
C4 N3 C8 C7 -0.2(6) . .
C2 N3 C8 C7 179.4(4) . .
C6 C7 C8 C9 179.8(5) . .
C6 C7 C8 N3 0.6(6) . .
N3 C8 C9 C10 0.1(5) . .
C7 C8 C9 C10 -179.1(5) . .
C8 C9 C10 C2 -0.2(5) . .
C8 C9 C10 C1 -179.9(5) . 3_666
C1 C2 C10 C9 179.9(4) . .
N3 C2 C10 C9 0.1(5) . .
C1 C2 C10 C1 -0.3(7) . 3_666
N3 C2 C10 C1 179.9(4) . 3_666
C12 Si1 C13 C14 59.0(4) . .
C17 Si1 C13 C14 178.3(4) . .
C15 Si1 C13 C14 -59.2(4) . .
C12 Si1 C15 C16 -175.1(4) . .
C17 Si1 C15 C16 64.6(4) . .
C13 Si1 C15 C16 -58.5(4) . .
C12 Si1 C17 C18 -66.7(4) . .
C15 Si1 C17 C18 53.1(4) . .
C13 Si1 C17 C18 176.1(4) . .
loop_
_cod_related_entry_id
_cod_related_entry_database
_cod_related_entry_code
1 PubChem 168305532
