#------------------------------------------------------------------------------
#$Date: 2025-08-18 23:06:14 +0200 (Mon 18 de Aug de 2025) $
#$Revision: 301780 $
#$URL: svn://www.crystallography.net/cod/cif/1/55/44/1554427.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_1554427
loop_
_publ_author_name
'Ozdemir, Resul'
'Park, Sangyun'
'Deneme, İbrahim'
'Park, Yonghan'
'Zorlu, Yunus'
'Alidagi, Husniye Ardic'
'Harmandar, Kevser'
'Kim, Choongik'
'Usta, Hakan'
_publ_section_title
;
 Triisopropylsilylethynyl-substituted indenofluorenes: carbonyl versus
 dicyanovinylene functionalization in one-dimensional molecular crystals
 and solution-processed n-channel OFETs
;
_journal_issue                   20
_journal_name_full               'Organic Chemistry Frontiers'
_journal_page_first              2912
_journal_paper_doi               10.1039/C8QO00856F
_journal_volume                  5
_journal_year                    2018
_chemical_formula_moiety         'C42 H50 O2 Si2'
_chemical_formula_sum            'C42 H50 O2 Si2'
_chemical_formula_weight         643.00
_chemical_name_common            'Organic Compound'
_space_group_crystal_system      triclinic
_space_group_IT_number           2
_space_group_name_Hall           '-P 1'
_space_group_name_H-M_alt        'P -1'
_atom_sites_solution_hydrogens   geom
_audit_block_doi                 10.5517/ccdc.csd.cc207h2v
_audit_update_record
;
2018-07-06 deposited with the CCDC.
2018-09-05 downloaded from the CCDC.
;
_cell_angle_alpha                94.036(5)
_cell_angle_beta                 92.577(5)
_cell_angle_gamma                114.867(4)
_cell_formula_units_Z            1
_cell_length_a                   7.6019(6)
_cell_length_b                   7.7795(7)
_cell_length_c                   17.7908(15)
_cell_measurement_reflns_used    125
_cell_measurement_temperature    296.(2)
_cell_measurement_theta_max      22.8899
_cell_measurement_theta_min      3.0335
_cell_volume                     948.98(14)
_computing_cell_refinement       'APEX2 v2014.11-0 (Bruker AXS)'
_computing_data_collection
'Bruker Instrument Service v2013.12.0.0 (Bruker AXS)'
_computing_data_reduction        'SAINT V8.34A (Bruker AXS)'
_computing_molecular_graphics    'MERCURY (Macrae et al., 2006)'
_computing_publication_material
'PLATON V1.16 (Spek, 2009), SHELXTL V6.14 (Bruker AXS)'
_computing_structure_refinement  'SHELXTL V6.14 (Bruker AXS)'
_computing_structure_solution    'SHELXTL V6.14 (Bruker AXS)'
_diffrn_ambient_temperature      296.(2)
_diffrn_detector_area_resol_mean 8.3333
_diffrn_measured_fraction_theta_full 0.987
_diffrn_measured_fraction_theta_max 0.987
_diffrn_measurement_device_type
'Bruker APEX II QUAZAR three-circle diffractometer'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_radiation_monochromator  'multilayer QUAZAR mirrors'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0573
_diffrn_reflns_av_unetI/netI     0.0487
_diffrn_reflns_limit_h_max       9
_diffrn_reflns_limit_h_min       -9
_diffrn_reflns_limit_k_max       9
_diffrn_reflns_limit_k_min       -9
_diffrn_reflns_limit_l_max       21
_diffrn_reflns_limit_l_min       -21
_diffrn_reflns_number            13766
_diffrn_reflns_theta_full        25.00
_diffrn_reflns_theta_max         25.00
_diffrn_reflns_theta_min         2.96
_diffrn_source                   'microfocus sealed tube'
_diffrn_source_type              ImuS
_exptl_absorpt_coefficient_mu    0.126
_exptl_absorpt_correction_T_max  1.00
_exptl_absorpt_correction_T_min  0.63
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   'SADABS V2014/5 (Bruker AXS)'
_exptl_crystal_colour            red
_exptl_crystal_density_diffrn    1.125
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       plate
_exptl_crystal_F_000             346
_exptl_crystal_size_max          0.467
_exptl_crystal_size_mid          0.358
_exptl_crystal_size_min          0.038
_refine_diff_density_max         0.978
_refine_diff_density_min         -0.381
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.078
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     214
_refine_ls_number_reflns         3303
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.078
_refine_ls_R_factor_all          0.0982
_refine_ls_R_factor_gt           0.0860
_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)+(0.1844P)²+0.3694P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.2596
_refine_ls_wR_factor_ref         0.2746
_reflns_number_gt                2677
_reflns_number_total             3303
_reflns_threshold_expression     'I > 2σ(I)'
_cod_data_source_file            c8qo00856f2.cif
_cod_data_source_block           I
_cod_database_code               1554427
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x, -y, -z'
loop_
_atom_site_type_symbol
_atom_site_label
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_calc_flag
_atom_site_refinement_flags_adp
_atom_site_refinement_flags_posn
_atom_site_occupancy
C C1 0.7272(5) 0.9046(5) 0.2577(2) 0.0621(9) Uani d . . 1
C C2 0.7265(5) 0.7978(5) 0.30350(19) 0.0549(8) Uani d . . 1
C C3 0.7119(4) 0.6545(4) 0.35229(16) 0.0472(7) Uani d . . 1
C C4 0.5288(4) 0.5377(4) 0.37605(17) 0.0459(7) Uani d . . 1
H H4 0.4211 0.5622 0.3654 0.055 Uiso calc U R 1
C C5 0.5133(4) 0.3883(4) 0.41496(15) 0.0408(7) Uani d . . 1
C C6 0.3357(4) 0.2387(4) 0.44296(16) 0.0418(7) Uani d . . 1
C C7 0.4045(4) 0.1025(4) 0.47560(15) 0.0376(6) Uani d . . 1
C C8 0.2954(4) -0.0628(4) 0.50750(15) 0.0398(7) Uani d . . 1
H H8 0.1632 -0.1024 0.5126 0.048 Uiso calc U R 1
C C9 0.6047(4) 0.1670(4) 0.46827(14) 0.0377(7) Uani d . . 1
C C10 0.6715(4) 0.3447(4) 0.43131(15) 0.0399(7) Uani d . . 1
C C11 0.8544(4) 0.4633(4) 0.41109(16) 0.0462(7) Uani d . . 1
H H11 0.9623 0.4405 0.4235 0.055 Uiso calc U R 1
C C12 0.8716(4) 0.6160(4) 0.37199(17) 0.0488(8) Uani d . . 1
H H12 0.9935 0.6962 0.3582 0.059 Uiso calc U R 1
C C13 0.5339(8) 1.1513(8) 0.2145(3) 0.0950(15) Uani d . . 1
H H13 0.6115 1.2564 0.2528 0.114 Uiso calc U R 1
C C14 0.4675(14) 1.2406(16) 0.1519(6) 0.187(4) Uani d . . 1
H H14A 0.4279 1.1549 0.1065 0.281 Uiso calc U R 1
H H14B 0.5729 1.3581 0.1427 0.281 Uiso calc U R 1
H H14C 0.3598 1.2649 0.1671 0.281 Uiso calc U R 1
C C15 0.3593(7) 1.0204(8) 0.2529(3) 0.0969(15) Uani d . . 1
H H15A 0.2923 1.0915 0.2732 0.145 Uiso calc U R 1
H H15B 0.4024 0.9675 0.2931 0.145 Uiso calc U R 1
H H15C 0.2728 0.9194 0.2166 0.145 Uiso calc U R 1
C C16 0.9538(8) 1.2335(7) 0.1673(3) 0.0881(13) Uani d . . 1
H H16 1.0329 1.1639 0.1566 0.106 Uiso calc U R 1
C C17 0.9581(11) 1.3395(11) 0.0996(4) 0.146(3) Uani d . . 1
H H17A 0.8932 1.4204 0.109 0.218 Uiso calc U R 1
H H17B 0.8931 1.2502 0.0563 0.218 Uiso calc U R 1
H H17C 1.0906 1.4156 0.0901 0.218 Uiso calc U R 1
C C18 1.0481(7) 1.3607(8) 0.2385(3) 0.0990(16) Uani d . . 1
H H18A 1.1814 1.441 0.2316 0.149 Uiso calc U R 1
H H18B 1.0427 1.2845 0.2793 0.149 Uiso calc U R 1
H H18C 0.9807 1.4382 0.2502 0.149 Uiso calc U R 1
C C19 0.6273(11) 0.8885(8) 0.0928(3) 0.117(2) Uani d . . 1
H H19 0.6184 0.9648 0.0525 0.14 Uiso calc U R 1
C C20 0.7550(19) 0.7994(14) 0.0705(4) 0.204(5) Uani d . . 1
H H20A 0.7313 0.6922 0.0988 0.306 Uiso calc U R 1
H H20B 0.8883 0.8901 0.0807 0.306 Uiso calc U R 1
H H20C 0.7292 0.7574 0.0175 0.306 Uiso calc U R 1
C C21 0.4230(14) 0.7215(10) 0.0958(5) 0.172(4) Uani d . . 1
H H21A 0.3955 0.6319 0.0521 0.258 Uiso calc U R 1
H H21B 0.3262 0.7704 0.0965 0.258 Uiso calc U R 1
H H21C 0.4214 0.6592 0.1407 0.258 Uiso calc U R 1
O O1 0.1739(3) 0.2297(3) 0.43947(14) 0.0584(7) Uani d . . 1
Si Si1 0.69929(15) 1.04317(13) 0.18294(5) 0.0566(4) Uani d . . 1
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'
O O 0.0106 0.0060 '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_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle
C2 C1 Si1 . . 172.8(3)
C1 C2 C3 . . 173.9(4)
C12 C3 C4 . . 118.7(3)
C12 C3 C2 . . 121.9(3)
C4 C3 C2 . . 119.2(3)
C5 C4 C3 . . 118.4(3)
C5 C4 H4 . . 120.8
C3 C4 H4 . . 120.8
C4 C5 C10 . . 122.6(3)
C4 C5 C6 . . 128.9(3)
C10 C5 C6 . . 108.3(2)
O1 C6 C5 . . 127.3(3)
O1 C6 C7 . . 127.8(3)
C5 C6 C7 . . 104.9(2)
C8 C7 C9 . . 123.0(3)
C8 C7 C6 . . 127.9(2)
C9 C7 C6 . . 109.1(2)
C7 C8 C9 . 2_656 116.2(2)
C7 C8 H8 . . 121.9
C9 C8 H8 2_656 . 121.9
C8 C9 C7 2_656 . 120.7(2)
C8 C9 C10 2_656 . 131.1(2)
C7 C9 C10 . . 108.1(2)
C11 C10 C5 . . 119.5(3)
C11 C10 C9 . . 131.0(3)
C5 C10 C9 . . 109.5(2)
C12 C11 C10 . . 118.1(3)
C12 C11 H11 . . 120.9
C10 C11 H11 . . 120.9
C11 C12 C3 . . 122.5(3)
C11 C12 H12 . . 118.8
C3 C12 H12 . . 118.8
C15 C13 C14 . . 109.9(5)
C15 C13 Si1 . . 115.0(4)
C14 C13 Si1 . . 113.3(4)
C15 C13 H13 . . 106.0
C14 C13 H13 . . 106.0
Si1 C13 H13 . . 106.0
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
C13 C15 H15A . . 109.5
C13 C15 H15B . . 109.5
H15A C15 H15B . . 109.5
C13 C15 H15C . . 109.5
H15A C15 H15C . . 109.5
H15B C15 H15C . . 109.5
C18 C16 C17 . . 113.6(5)
C18 C16 Si1 . . 111.0(3)
C17 C16 Si1 . . 114.0(4)
C18 C16 H16 . . 105.8
C17 C16 H16 . . 105.8
Si1 C16 H16 . . 105.8
C16 C17 H17A . . 109.5
C16 C17 H17B . . 109.5
H17A C17 H17B . . 109.5
C16 C17 H17C . . 109.5
H17A C17 H17C . . 109.5
H17B C17 H17C . . 109.5
C16 C18 H18A . . 109.5
C16 C18 H18B . . 109.5
H18A C18 H18B . . 109.5
C16 C18 H18C . . 109.5
H18A C18 H18C . . 109.5
H18B C18 H18C . . 109.5
C20 C19 C21 . . 105.6(7)
C20 C19 Si1 . . 116.8(6)
C21 C19 Si1 . . 110.2(5)
C20 C19 H19 . . 108.0
C21 C19 H19 . . 108.0
Si1 C19 H19 . . 108.0
C19 C20 H20A . . 109.5
C19 C20 H20B . . 109.5
H20A C20 H20B . . 109.5
C19 C20 H20C . . 109.5
H20A C20 H20C . . 109.5
H20B C20 H20C . . 109.5
C19 C21 H21A . . 109.5
C19 C21 H21B . . 109.5
H21A C21 H21B . . 109.5
C19 C21 H21C . . 109.5
H21A C21 H21C . . 109.5
H21B C21 H21C . . 109.5
C1 Si1 C19 . . 108.1(2)
C1 Si1 C13 . . 107.70(19)
C19 Si1 C13 . . 117.6(3)
C1 Si1 C16 . . 107.9(2)
C19 Si1 C16 . . 103.0(3)
C13 Si1 C16 . . 112.1(2)
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_site_symmetry_2
_geom_bond_distance
C1 C2 . 1.203(5)
C1 Si1 . 1.828(4)
C2 C3 . 1.432(4)
C3 C12 . 1.403(5)
C3 C4 . 1.409(4)
C4 C5 . 1.360(4)
C4 H4 . 0.93
C5 C10 . 1.404(4)
C5 C6 . 1.499(4)
C6 O1 . 1.200(3)
C6 C7 . 1.503(4)
C7 C8 . 1.382(4)
C7 C9 . 1.404(4)
C8 C9 2_656 1.399(4)
C8 H8 . 0.93
C9 C8 2_656 1.399(4)
C9 C10 . 1.473(4)
C10 C11 . 1.388(4)
C11 C12 . 1.380(4)
C11 H11 . 0.93
C12 H12 . 0.93
C13 C15 . 1.519(7)
C13 C14 . 1.527(8)
C13 Si1 . 1.868(5)
C13 H13 . 0.98
C14 H14A . 0.96
C14 H14B . 0.96
C14 H14C . 0.96
C15 H15A . 0.96
C15 H15B . 0.96
C15 H15C . 0.96
C16 C18 . 1.497(7)
C16 C17 . 1.502(7)
C16 Si1 . 1.926(5)
C16 H16 . 0.98
C17 H17A . 0.96
C17 H17B . 0.96
C17 H17C . 0.96
C18 H18A . 0.96
C18 H18B . 0.96
C18 H18C . 0.96
C19 C20 . 1.464(10)
C19 C21 . 1.556(10)
C19 Si1 . 1.847(5)
C19 H19 . 0.98
C20 H20A . 0.96
C20 H20B . 0.96
C20 H20C . 0.96
C21 H21A . 0.96
C21 H21B . 0.96
C21 H21C . 0.96
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_site_symmetry_1
_geom_torsion_site_symmetry_4
_geom_torsion
C12 C3 C4 C5 . . -2.2(4)
C2 C3 C4 C5 . . 172.4(3)
C3 C4 C5 C10 . . -0.9(4)
C3 C4 C5 C6 . . -176.7(3)
C4 C5 C6 O1 . . -4.4(5)
C10 C5 C6 O1 . . 179.4(3)
C4 C5 C6 C7 . . 175.2(3)
C10 C5 C6 C7 . . -1.1(3)
O1 C6 C7 C8 . . 0.9(5)
C5 C6 C7 C8 . . -178.6(3)
O1 C6 C7 C9 . . -179.9(3)
C5 C6 C7 C9 . . 0.6(3)
C9 C7 C8 C9 . 2_656 -0.9(4)
C6 C7 C8 C9 . 2_656 178.2(3)
C8 C7 C9 C8 . 2_656 1.0(4)
C6 C7 C9 C8 . 2_656 -178.3(2)
C8 C7 C9 C10 . . 179.4(2)
C6 C7 C9 C10 . . 0.1(3)
C4 C5 C10 C11 . . 3.7(4)
C6 C5 C10 C11 . . -179.8(2)
C4 C5 C10 C9 . . -175.4(3)
C6 C5 C10 C9 . . 1.2(3)
C8 C9 C10 C11 2_656 . -1.6(5)
C7 C9 C10 C11 . . -179.7(3)
C8 C9 C10 C5 2_656 . 177.3(3)
C7 C9 C10 C5 . . -0.8(3)
C5 C10 C11 C12 . . -3.1(4)
C9 C10 C11 C12 . . 175.7(3)
C10 C11 C12 C3 . . 0.0(5)
C4 C3 C12 C11 . . 2.7(5)
C2 C3 C12 C11 . . -171.7(3)
C20 C19 Si1 C1 . . -55.6(6)
C21 C19 Si1 C1 . . 64.9(6)
C20 C19 Si1 C13 . . -177.7(6)
C21 C19 Si1 C13 . . -57.3(6)
C20 C19 Si1 C16 . . 58.5(6)
C21 C19 Si1 C16 . . 179.0(5)
C15 C13 Si1 C1 . . -41.7(5)
C14 C13 Si1 C1 . . -169.3(6)
C15 C13 Si1 C19 . . 80.7(5)
C14 C13 Si1 C19 . . -46.9(7)
C15 C13 Si1 C16 . . -160.3(4)
C14 C13 Si1 C16 . . 72.1(6)
loop_
_cod_related_entry_id
_cod_related_entry_database
_cod_related_entry_code
1 PubChem 168304449
