#------------------------------------------------------------------------------
#$Date: 2025-08-18 23:06:14 +0200 (Mon 18 de Aug de 2025) $
#$Revision: 301780 $
#$URL: svn://www.crystallography.net/cod/cif/1/55/44/1554428.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_1554428
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         'C48 H50 N4 Si2'
_chemical_formula_sum            'C48 H50 N4 Si2'
_chemical_formula_weight         739.10
_chemical_name_common            'Organic Compound'
_space_group_crystal_system      monoclinic
_space_group_IT_number           15
_space_group_name_Hall           '-C 2yc'
_space_group_name_H-M_alt        'C 1 2/c 1'
_atom_sites_solution_hydrogens   geom
_audit_block_doi                 10.5517/ccdc.csd.cc207h3w
_audit_update_record
;
2018-07-06 deposited with the CCDC.
2018-09-05 downloaded from the CCDC.
;
_cell_angle_alpha                90
_cell_angle_beta                 102.874(8)
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   39.755(5)
_cell_length_b                   10.0294(12)
_cell_length_c                   11.4351(14)
_cell_measurement_reflns_used    2806
_cell_measurement_temperature    296.(2)
_cell_measurement_theta_max      23.4121
_cell_measurement_theta_min      2.5710
_cell_volume                     4444.8(10)
_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 0.996
_diffrn_measured_fraction_theta_max 0.996
_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  0.0967
_diffrn_reflns_av_unetI/netI     0.0833
_diffrn_reflns_limit_h_max       47
_diffrn_reflns_limit_h_min       -37
_diffrn_reflns_limit_k_max       11
_diffrn_reflns_limit_k_min       -11
_diffrn_reflns_limit_l_max       10
_diffrn_reflns_limit_l_min       -13
_diffrn_reflns_number            16272
_diffrn_reflns_theta_full        25.03
_diffrn_reflns_theta_max         25.03
_diffrn_reflns_theta_min         2.10
_diffrn_source                   'microfocus sealed tube'
_diffrn_source_type              ImuS
_exptl_absorpt_coefficient_mu    0.115
_exptl_absorpt_correction_T_max  1.00
_exptl_absorpt_correction_T_min  0.72
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   'SADABS V2014/5 (Bruker AXS)'
_exptl_crystal_colour            purple
_exptl_crystal_density_diffrn    1.104
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       plate
_exptl_crystal_F_000             1576
_exptl_crystal_size_max          0.410
_exptl_crystal_size_mid          0.320
_exptl_crystal_size_min          0.032
_refine_diff_density_max         0.414
_refine_diff_density_min         -0.234
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.016
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     250
_refine_ls_number_reflns         3918
_refine_ls_number_restraints     19
_refine_ls_restrained_S_all      1.034
_refine_ls_R_factor_all          0.2020
_refine_ls_R_factor_gt           0.1097
_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)+(0.1917P)²+6.5584P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.3031
_refine_ls_wR_factor_ref         0.3730
_reflns_number_gt                1782
_reflns_number_total             3918
_reflns_threshold_expression     'I > 2σ(I)'
_cod_data_source_file            c8qo00856f2.cif
_cod_data_source_block           I_CCDC1
_cod_original_cell_volume        4444.8(9)
_cod_database_code               1554428
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x, y, -z+1/2'
'x+1/2, y+1/2, z'
'-x+1/2, y+1/2, -z+1/2'
'-x, -y, -z'
'x, -y, z-1/2'
'-x+1/2, -y+1/2, -z'
'x+1/2, -y+1/2, z-1/2'
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 0.2590(3) 0.227(2) 0.2308(18) 0.289(11) Uani d . . 1
H H1A 0.2567 0.1314 0.2276 0.434 Uiso calc U R 1
H H1B 0.259 0.2603 0.1522 0.434 Uiso calc U R 1
H H1C 0.2401 0.2649 0.2587 0.434 Uiso calc U R 1
C C2 0.2907(4) 0.229(2) 0.4398(12) 0.258(7) Uani d U D 1
H H2A 0.2726 0.2785 0.4639 0.387 Uiso calc U R 1
H H2B 0.3125 0.2535 0.49 0.387 Uiso calc U R 1
H H2C 0.2868 0.1355 0.4475 0.387 Uiso calc U R 1
C C3 0.2907(3) 0.2614(16) 0.3111(11) 0.200(6) Uani d U D 1
H H3 0.2894 0.359 0.3108 0.24 Uiso calc U R 1
C C4 0.3380(3) 0.5009(14) 0.1847(12) 0.190(5) Uani d . . 1
H H4A 0.3411 0.5585 0.1208 0.285 Uiso calc U R 1
H H4B 0.3568 0.5134 0.2529 0.285 Uiso calc U R 1
H H4C 0.3166 0.522 0.2064 0.285 Uiso calc U R 1
C C5 0.3373(3) 0.3553(13) 0.1432(9) 0.151(4) Uani d . . 1
H H5 0.3608 0.3384 0.1333 0.181 Uiso calc U R 1
C C6 0.3162(5) 0.3347(18) 0.0269(11) 0.275(10) Uani d . . 1
H H6A 0.2928 0.359 0.0269 0.412 Uiso calc U R 1
H H6B 0.317 0.2425 0.0053 0.412 Uiso calc U R 1
H H6C 0.3244 0.3889 -0.0301 0.412 Uiso calc U R 1
C C7 0.3316(4) -0.0448(15) 0.3051(14) 0.225(6) Uani d U . 1
H H7A 0.3502 -0.1076 0.3133 0.338 Uiso calc U R 1
H H7B 0.31 -0.0911 0.2833 0.338 Uiso calc U R 1
H H7C 0.3331 0.0006 0.38 0.338 Uiso calc U R 1
C C8 0.3342(3) 0.0572(11) 0.2073(10) 0.141(3) Uani d U . 1
H H8 0.3152 0.0419 0.1376 0.169 Uiso calc U R 1
C C9 0.3652(3) 0.0239(13) 0.1771(13) 0.202(5) Uani d U . 1
H H9A 0.3833 0.021 0.2484 0.303 Uiso calc U R 1
H H9B 0.3706 0.0897 0.1232 0.303 Uiso calc U R 1
H H9C 0.363 -0.0618 0.1388 0.303 Uiso calc U R 1
C C10 0.36740(19) 0.2651(7) 0.3870(7) 0.090(2) Uani d . . 1
C C11 0.39035(19) 0.2908(7) 0.4719(7) 0.088(2) Uani d . . 1
C C12 0.41605(16) 0.3205(6) 0.5773(6) 0.0772(17) Uani d . . 1
C C13 0.43281(17) 0.2166(6) 0.6500(7) 0.0845(19) Uani d . . 1
H H13 0.4289 0.1289 0.6242 0.101 Uiso calc U R 1
C C14 0.45490(17) 0.2419(5) 0.7582(6) 0.0767(18) Uani d . . 1
H H14 0.4654 0.172 0.8062 0.092 Uiso calc U R 1
C C15 0.46134(13) 0.3704(5) 0.7944(5) 0.0627(15) Uani d . . 1
C C16 0.48231(13) 0.4246(5) 0.9045(5) 0.0626(15) Uani d . . 1
C C17 0.48029(13) 0.5653(5) 0.9008(5) 0.0614(15) Uani d . . 1
C C18 0.45851(13) 0.6027(5) 0.7844(5) 0.0649(15) Uani d . . 1
C C19 0.44622(14) 0.4767(5) 0.7209(6) 0.0640(15) Uani d . . 1
C C20 0.4630(2) 0.8431(7) 0.8092(8) 0.119(3) Uani d . . 1
C C21 0.45148(15) 0.7298(5) 0.7424(6) 0.0754(18) Uani d . . 1
C C22 0.43310(18) 0.7551(6) 0.6208(8) 0.087(2) Uani d . . 1
C C23 0.50218(14) 0.3589(5) 1.0040(6) 0.0682(16) Uani d . . 1
H H23 0.5036 0.2663 1.0061 0.082 Uiso calc U R 1
C C24 0.42347(14) 0.4517(6) 0.6129(6) 0.0718(16) Uani d . . 1
H H007 0.4133 0.5218 0.5646 0.086 Uiso calc U R 1
N N1 0.4192(2) 0.7822(7) 0.5250(7) 0.127(3) Uani d . . 1
N N2 0.4729(3) 0.9357(7) 0.8629(9) 0.188(5) Uani d . . 1
Si Si1 0.33115(5) 0.2316(2) 0.26221(18) 0.0916(8) 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'
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_site_symmetry_1
_geom_angle
C3 C1 H1A . 109.5
C3 C1 H1B . 109.5
H1A C1 H1B . 109.5
C3 C1 H1C . 109.5
H1A C1 H1C . 109.5
H1B C1 H1C . 109.5
C3 C2 H2A . 109.5
C3 C2 H2B . 109.5
H2A C2 H2B . 109.5
C3 C2 H2C . 109.5
H2A C2 H2C . 109.5
H2B C2 H2C . 109.5
C1 C3 C2 . 112.6(13)
C1 C3 Si1 . 118.0(11)
C2 C3 Si1 . 116.9(9)
C1 C3 H3 . 101.9
C2 C3 H3 . 101.9
Si1 C3 H3 . 101.9
C5 C4 H4A . 109.5
C5 C4 H4B . 109.5
H4A C4 H4B . 109.5
C5 C4 H4C . 109.5
H4A C4 H4C . 109.5
H4B C4 H4C . 109.5
C6 C5 C4 . 113.2(11)
C6 C5 Si1 . 115.6(11)
C4 C5 Si1 . 113.4(8)
C6 C5 H5 . 104.3
C4 C5 H5 . 104.3
Si1 C5 H5 . 104.3
C5 C6 H6A . 109.5
C5 C6 H6B . 109.5
H6A C6 H6B . 109.5
C5 C6 H6C . 109.5
H6A C6 H6C . 109.5
H6B C6 H6C . 109.5
C8 C7 H7A . 109.5
C8 C7 H7B . 109.5
H7A C7 H7B . 109.5
C8 C7 H7C . 109.5
H7A C7 H7C . 109.5
H7B C7 H7C . 109.5
C9 C8 C7 . 103.1(11)
C9 C8 Si1 . 115.7(8)
C7 C8 Si1 . 111.0(9)
C9 C8 H8 . 108.9
C7 C8 H8 . 108.9
Si1 C8 H8 . 108.9
C8 C9 H9A . 109.5
C8 C9 H9B . 109.5
H9A C9 H9B . 109.5
C8 C9 H9C . 109.5
H9A C9 H9C . 109.5
H9B C9 H9C . 109.5
C11 C10 Si1 . 176.9(7)
C10 C11 C12 . 176.4(8)
C24 C12 C13 . 119.2(6)
C24 C12 C11 . 120.7(6)
C13 C12 C11 . 120.1(6)
C14 C13 C12 . 121.3(6)
C14 C13 H13 . 119.3
C12 C13 H13 . 119.3
C15 C14 C13 . 119.3(6)
C15 C14 H14 . 120.3
C13 C14 H14 . 120.3
C14 C15 C19 . 120.6(6)
C14 C15 C16 . 130.7(5)
C19 C15 C16 . 108.7(5)
C23 C16 C17 . 120.9(5)
C23 C16 C15 . 129.8(5)
C17 C16 C15 . 109.3(5)
C23 C17 C16 5_667 120.7(5)
C23 C17 C18 5_667 131.8(5)
C16 C17 C18 . 107.5(5)
C21 C18 C17 . 126.1(5)
C21 C18 C19 . 127.0(6)
C17 C18 C19 . 106.9(4)
C24 C19 C15 . 120.3(5)
C24 C19 C18 . 132.1(5)
C15 C19 C18 . 107.6(5)
N2 C20 C21 . 178.6(12)
C18 C21 C20 . 123.6(6)
C18 C21 C22 . 121.5(6)
C20 C21 C22 . 114.8(5)
N1 C22 C21 . 176.3(8)
C17 C23 C16 5_667 118.4(5)
C17 C23 H23 5_667 120.8
C16 C23 H23 . 120.8
C19 C24 C12 . 119.2(5)
C19 C24 H007 . 120.4
C12 C24 H007 . 120.4
C10 Si1 C3 . 109.0(4)
C10 Si1 C8 . 109.7(4)
C3 Si1 C8 . 112.3(6)
C10 Si1 C5 . 103.7(5)
C3 Si1 C5 . 111.8(6)
C8 Si1 C5 . 110.0(5)
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_site_symmetry_2
_geom_bond_distance
C1 C3 . 1.425(15)
C1 H1A . 0.96
C1 H1B . 0.96
C1 H1C . 0.96
C2 C3 . 1.506(9)
C2 H2A . 0.96
C2 H2B . 0.96
C2 H2C . 0.96
C3 Si1 . 1.843(11)
C3 H3 . 0.98
C4 C5 . 1.534(16)
C4 H4A . 0.96
C4 H4B . 0.96
C4 H4C . 0.96
C5 C6 . 1.420(16)
C5 Si1 . 1.897(11)
C5 H5 . 0.98
C6 H6A . 0.96
C6 H6B . 0.96
C6 H6C . 0.96
C7 C8 . 1.536(16)
C7 H7A . 0.96
C7 H7B . 0.96
C7 H7C . 0.96
C8 C9 . 1.393(14)
C8 Si1 . 1.871(10)
C8 H8 . 0.98
C9 H9A . 0.96
C9 H9B . 0.96
C9 H9C . 0.96
C10 C11 . 1.202(9)
C10 Si1 . 1.819(8)
C11 C12 . 1.427(10)
C12 C24 . 1.390(8)
C12 C13 . 1.404(9)
C13 C14 . 1.372(9)
C13 H13 . 0.93
C14 C15 . 1.361(7)
C14 H14 . 0.93
C15 C19 . 1.407(7)
C15 C16 . 1.451(8)
C16 C23 . 1.397(8)
C16 C17 . 1.413(7)
C17 C23 5_667 1.383(8)
C17 C18 . 1.466(8)
C18 C21 . 1.369(7)
C18 C19 . 1.484(8)
C19 C24 . 1.382(8)
C20 N2 . 1.135(10)
C20 C21 . 1.389(10)
C21 C22 . 1.443(10)
C22 N1 . 1.145(9)
C23 C17 5_667 1.383(8)
C23 H23 . 0.93
C24 H007 . 0.93
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
C24 C12 C13 C14 . . 3.5(10)
C11 C12 C13 C14 . . -173.0(6)
C12 C13 C14 C15 . . -1.6(10)
C13 C14 C15 C19 . . -1.5(9)
C13 C14 C15 C16 . . 177.6(6)
C14 C15 C16 C23 . . 0.8(10)
C19 C15 C16 C23 . . -180.0(5)
C14 C15 C16 C17 . . -178.9(6)
C19 C15 C16 C17 . . 0.3(6)
C23 C16 C17 C23 . 5_667 -0.4(9)
C15 C16 C17 C23 . 5_667 179.4(5)
C23 C16 C17 C18 . . 178.4(5)
C15 C16 C17 C18 . . -1.9(6)
C23 C17 C18 C21 5_667 . 2.2(10)
C16 C17 C18 C21 . . -176.4(6)
C23 C17 C18 C19 5_667 . -178.8(5)
C16 C17 C18 C19 . . 2.7(6)
C14 C15 C19 C24 . . 2.7(8)
C16 C15 C19 C24 . . -176.6(5)
C14 C15 C19 C18 . . -179.3(5)
C16 C15 C19 C18 . . 1.4(6)
C21 C18 C19 C24 . . -5.8(10)
C17 C18 C19 C24 . . 175.2(6)
C21 C18 C19 C15 . . 176.6(6)
C17 C18 C19 C15 . . -2.5(6)
C17 C18 C21 C20 . . -3.6(11)
C19 C18 C21 C20 . . 177.6(7)
C17 C18 C21 C22 . . 172.4(6)
C19 C18 C21 C22 . . -6.5(10)
C17 C16 C23 C17 . 5_667 0.4(9)
C15 C16 C23 C17 . 5_667 -179.3(5)
C15 C19 C24 C12 . . -0.7(8)
C18 C19 C24 C12 . . -178.1(6)
C13 C12 C24 C19 . . -2.3(9)
C11 C12 C24 C19 . . 174.2(6)
C1 C3 Si1 C10 . . -173.1(13)
C2 C3 Si1 C10 . . -33.8(14)
C1 C3 Si1 C8 . . -51.4(15)
C2 C3 Si1 C8 . . 87.9(13)
C1 C3 Si1 C5 . . 72.9(15)
C2 C3 Si1 C5 . . -147.8(12)
C9 C8 Si1 C10 . . -54.1(11)
C7 C8 Si1 C10 . . 63.0(10)
C9 C8 Si1 C3 . . -175.4(10)
C7 C8 Si1 C3 . . -58.3(10)
C9 C8 Si1 C5 . . 59.3(11)
C7 C8 Si1 C5 . . 176.4(9)
C6 C5 Si1 C10 . . 168.6(10)
C4 C5 Si1 C10 . . -58.3(9)
C6 C5 Si1 C3 . . -74.2(12)
C4 C5 Si1 C3 . . 59.0(10)
C6 C5 Si1 C8 . . 51.4(12)
C4 C5 Si1 C8 . . -175.5(8)
loop_
_cod_related_entry_id
_cod_related_entry_database
_cod_related_entry_code
1 PubChem 168304450
