#------------------------------------------------------------------------------
#$Date: 2019-11-02 07:41:09 +0200 (Sat, 02 Nov 2019) $
#$Revision: 220984 $
#$URL: file:///home/coder/svn-repositories/cod/cif/4/12/78/4127812.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_4127812
loop_
_publ_author_name
'Wang, Jinlian'
'Chu, Ming'
'Fan, Jian-Xun'
'Lau, Tsz-Ki'
'Ren, Ai-Min'
'Lu, Xinhui'
'Miao, Qian'
_publ_section_title
;
 Crystal Engineering of Biphenylene-Containing Acenes for High-Mobility
 Organic Semiconductors.
;
_journal_issue                   8
_journal_name_full               'Journal of the American Chemical Society'
_journal_page_first              3589
_journal_page_last               3596
_journal_paper_doi               10.1021/jacs.8b12671
_journal_volume                  141
_journal_year                    2019
_chemical_formula_sum            'C60 H66 Si2'
_chemical_formula_weight         843.30
_chemical_name_systematic
5,9,14,18-tetramethyl-7,16-bis(triisopropylethynyl)bisnaphtho[2',3':3,4]cyclobut[1,2-b:1',2'-i]anthracene
_space_group_crystal_system      monoclinic
_space_group_IT_number           14
_space_group_name_Hall           '-P 2yn'
_space_group_name_H-M_alt        'P 1 21/n 1'
_symmetry_space_group_name_Hall  '-P 2yn'
_symmetry_space_group_name_H-M   'P 1 21/n 1'
_atom_sites_solution_hydrogens   geom
_audit_creation_method           SHELXL-2014/6
_cell_angle_alpha                90
_cell_angle_beta                 93.3748(13)
_cell_angle_gamma                90
_cell_formula_units_Z            2
_cell_length_a                   8.4074(2)
_cell_length_b                   22.0519(5)
_cell_length_c                   13.4051(3)
_cell_measurement_reflns_used    100
_cell_measurement_temperature    296(2)
_cell_measurement_theta_max      15
_cell_measurement_theta_min      15
_cell_volume                     2480.98(10)
_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    'BRUKER SHELXTL'
_computing_publication_material  'BRUKER SHELXTL'
_computing_structure_refinement  'SHELXL-2014/6 (Sheldrick, 2014)'
_diffrn_ambient_temperature      296(2)
_diffrn_measured_fraction_theta_full 1.000
_diffrn_measured_fraction_theta_max 1.000
_diffrn_measurement_device_type  'BRUKER KAPPA APEXII DUO DIFFRACTOMETER'
_diffrn_measurement_method       'PHI & OMEGA SCAN'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0544
_diffrn_reflns_av_unetI/netI     0.0340
_diffrn_reflns_Laue_measured_fraction_full 1.000
_diffrn_reflns_Laue_measured_fraction_max 1.000
_diffrn_reflns_limit_h_max       10
_diffrn_reflns_limit_h_min       -10
_diffrn_reflns_limit_k_max       26
_diffrn_reflns_limit_k_min       -26
_diffrn_reflns_limit_l_max       16
_diffrn_reflns_limit_l_min       -15
_diffrn_reflns_number            27394
_diffrn_reflns_point_group_measured_fraction_full 1.000
_diffrn_reflns_point_group_measured_fraction_max 1.000
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         25.249
_diffrn_reflns_theta_min         1.780
_exptl_absorpt_coefficient_mu    0.109
_exptl_absorpt_correction_T_max  0.7456
_exptl_absorpt_correction_T_min  0.6926
_exptl_absorpt_correction_type   multi-scan
_exptl_crystal_colour            red
_exptl_crystal_density_diffrn    1.129
_exptl_crystal_description       block
_exptl_crystal_F_000             908
_exptl_crystal_size_max          0.500
_exptl_crystal_size_mid          0.400
_exptl_crystal_size_min          0.200
_refine_diff_density_max         0.423
_refine_diff_density_min         -0.346
_refine_diff_density_rms         0.047
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.036
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     280
_refine_ls_number_reflns         4493
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.036
_refine_ls_R_factor_all          0.0890
_refine_ls_R_factor_gt           0.0626
_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)+(0.0851P)²+2.1778P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1711
_refine_ls_wR_factor_ref         0.1942
_reflns_Friedel_coverage         0.000
_reflns_number_gt                3209
_reflns_number_total             4493
_reflns_threshold_expression     'I > 2σ(I)'
_cod_data_source_file            ja8b12671_si_002.cif
_cod_data_source_block           1b
_cod_database_code               4127812
_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   0.948
_shelx_estimated_absorpt_t_max   0.979
_shelxl_version_number           2014/6
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x+1/2, y+1/2, -z+1/2'
'-x, -y, -z'
'x-1/2, -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 0.93073(11) 0.14973(4) 0.63828(6) 0.0555(3) Uani 1 1 d . .
C1 C 0.8767(3) 0.00283(11) 1.06883(19) 0.0359(6) Uani 1 1 d . .
C2 C 0.7544(3) 0.00655(12) 1.1393(2) 0.0412(6) Uani 1 1 d . .
H2A H 0.7639 -0.0137 1.2002 0.049 Uiso 1 1 calc R U
C3 C 0.6256(3) 0.04064(12) 1.1131(2) 0.0420(6) Uani 1 1 d . .
C4 C 0.4674(3) 0.06503(13) 1.1403(2) 0.0457(7) Uani 1 1 d . .
C5 C 0.3567(3) 0.06604(13) 1.2094(2) 0.0487(7) Uani 1 1 d . .
C6 C 0.2156(3) 0.10109(14) 1.1805(2) 0.0503(7) Uani 1 1 d . .
C7 C 0.0890(4) 0.10471(16) 1.2446(3) 0.0630(9) Uani 1 1 d . .
H7A H 0.0988 0.0853 1.3063 0.076 Uiso 1 1 calc R U
C8 C -0.0479(4) 0.13598(18) 1.2187(3) 0.0731(11) Uani 1 1 d . .
H8A H -0.1296 0.1376 1.2625 0.088 Uiso 1 1 calc R U
C9 C -0.0645(4) 0.16500(18) 1.1279(3) 0.0725(11) Uani 1 1 d . .
H9A H -0.1580 0.1860 1.1104 0.087 Uiso 1 1 calc R U
C10 C 0.0553(4) 0.16340(15) 1.0626(3) 0.0610(9) Uani 1 1 d . .
H10A H 0.0421 0.1835 1.0017 0.073 Uiso 1 1 calc R U
C11 C 0.1986(3) 0.13164(13) 1.0865(2) 0.0477(7) Uani 1 1 d . .
C12 C 0.3229(3) 0.12955(13) 1.0159(2) 0.0469(7) Uani 1 1 d . .
C13 C 0.4507(3) 0.09592(13) 1.0462(2) 0.0441(6) Uani 1 1 d . .
C14 C 0.6085(3) 0.07191(12) 1.0187(2) 0.0425(6) Uani 1 1 d . .
C15 C 0.7193(3) 0.06979(12) 0.9503(2) 0.0416(6) Uani 1 1 d . .
H15A H 0.7055 0.0901 0.8896 0.050 Uiso 1 1 calc R U
C16 C 0.8601(3) 0.03457(11) 0.97542(19) 0.0361(6) Uani 1 1 d . .
C17 C 0.3771(4) 0.03245(18) 1.3066(3) 0.0717(10) Uani 1 1 d . .
H17A H 0.2854 0.0391 1.3447 0.108 Uiso 1 1 calc R U
H17B H 0.3881 -0.0101 1.2937 0.108 Uiso 1 1 calc R U
H17C H 0.4707 0.0469 1.3436 0.108 Uiso 1 1 calc R U
C18 C 0.3097(4) 0.16015(16) 0.9165(3) 0.0616(9) Uani 1 1 d . .
H18A H 0.2104 0.1817 0.9092 0.092 Uiso 1 1 calc R U
H18B H 0.3963 0.1882 0.9118 0.092 Uiso 1 1 calc R U
H18C H 0.3138 0.1303 0.8646 0.092 Uiso 1 1 calc R U
C19 C 0.9834(3) 0.03118(11) 0.90863(19) 0.0365(6) Uani 1 1 d . .
C20 C 0.9683(3) 0.06542(12) 0.8176(2) 0.0410(6) Uani 1 1 d . .
C21 C 0.9555(3) 0.09640(14) 0.7434(2) 0.0491(7) Uani 1 1 d . .
C22 C 1.1300(6) 0.1593(3) 0.5856(5) 0.129(2) Uani 1 1 d . .
H22A H 1.1728 0.1870 0.6377 0.154 Uiso 1 1 calc R U
C23 C 1.2479(7) 0.1177(4) 0.5979(6) 0.190(4) Uani 1 1 d . .
H23A H 1.2286 0.0924 0.6543 0.284 Uiso 1 1 calc R U
H23B H 1.2503 0.0931 0.5389 0.284 Uiso 1 1 calc R U
H23C H 1.3483 0.1380 0.6093 0.284 Uiso 1 1 calc R U
C24 C 1.1335(6) 0.2050(3) 0.5006(4) 0.1172(18) Uani 1 1 d . .
H24A H 1.0425 0.2312 0.5019 0.176 Uiso 1 1 calc R U
H24B H 1.2291 0.2287 0.5083 0.176 Uiso 1 1 calc R U
H24C H 1.1312 0.1838 0.4379 0.176 Uiso 1 1 calc R U
C25 C 0.7712(5) 0.11599(17) 0.5491(3) 0.0737(10) Uani 1 1 d . .
H25A H 0.6860 0.1029 0.5911 0.088 Uiso 1 1 calc R U
C26 C 0.6936(6) 0.1605(2) 0.4743(3) 0.0986(15) Uani 1 1 d . .
H26A H 0.6603 0.1960 0.5088 0.148 Uiso 1 1 calc R U
H26B H 0.7688 0.1717 0.4264 0.148 Uiso 1 1 calc R U
H26C H 0.6026 0.1417 0.4404 0.148 Uiso 1 1 calc R U
C27 C 0.8257(7) 0.0590(2) 0.4974(3) 0.1073(16) Uani 1 1 d . .
H27A H 0.8741 0.0318 0.5462 0.161 Uiso 1 1 calc R U
H27B H 0.7356 0.0396 0.4637 0.161 Uiso 1 1 calc R U
H27C H 0.9018 0.0696 0.4497 0.161 Uiso 1 1 calc R U
C28 C 0.8561(5) 0.22312(16) 0.6887(3) 0.0747(11) Uani 1 1 d . .
H28A H 0.8280 0.2489 0.6308 0.090 Uiso 1 1 calc R U
C29 C 0.9780(7) 0.2584(2) 0.7549(4) 0.130(2) Uani 1 1 d . .
H29A H 1.0735 0.2640 0.7201 0.195 Uiso 1 1 calc R U
H29B H 0.9347 0.2973 0.7708 0.195 Uiso 1 1 calc R U
H29C H 1.0024 0.2362 0.8155 0.195 Uiso 1 1 calc R U
C30 C 0.7042(7) 0.2140(2) 0.7431(4) 0.1110(18) Uani 1 1 d . .
H30A H 0.6283 0.1919 0.7011 0.167 Uiso 1 1 calc R U
H30B H 0.7281 0.1917 0.8036 0.167 Uiso 1 1 calc R U
H30C H 0.6604 0.2528 0.7590 0.167 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 0.0033 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'
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
C21 Si1 C22 107.38(17) . .
C21 Si1 C28 107.53(15) . .
C22 Si1 C28 111.4(3) . .
C21 Si1 C25 106.04(15) . .
C22 Si1 C25 115.0(3) . .
C28 Si1 C25 109.07(17) . .
C19 C1 C16 118.9(2) 3_757 .
C19 C1 C2 120.5(2) 3_757 .
C16 C1 C2 120.6(2) . .
C3 C2 C1 117.1(2) . .
C2 C3 C14 122.2(2) . .
C2 C3 C4 147.9(3) . .
C14 C3 C4 89.9(2) . .
C5 C4 C13 124.0(3) . .
C5 C4 C3 146.0(3) . .
C13 C4 C3 89.9(2) . .
C4 C5 C6 114.3(3) . .
C4 C5 C17 122.6(3) . .
C6 C5 C17 123.0(3) . .
C7 C6 C11 118.1(3) . .
C7 C6 C5 120.2(3) . .
C11 C6 C5 121.7(3) . .
C8 C7 C6 121.8(4) . .
C7 C8 C9 119.9(3) . .
C10 C9 C8 120.8(3) . .
C9 C10 C11 121.0(4) . .
C10 C11 C6 118.3(3) . .
C10 C11 C12 120.3(3) . .
C6 C11 C12 121.4(3) . .
C13 C12 C11 114.3(3) . .
C13 C12 C18 122.3(3) . .
C11 C12 C18 123.3(3) . .
C12 C13 C4 124.2(3) . .
C12 C13 C14 145.5(3) . .
C4 C13 C14 90.4(2) . .
C15 C14 C3 123.0(2) . .
C15 C14 C13 147.1(3) . .
C3 C14 C13 89.8(2) . .
C14 C15 C16 116.8(2) . .
C19 C16 C1 119.4(2) . .
C19 C16 C15 120.3(2) . .
C1 C16 C15 120.3(2) . .
C16 C19 C1 121.7(2) . 3_757
C16 C19 C20 118.7(2) . .
C1 C19 C20 119.5(2) 3_757 .
C21 C20 C19 177.2(3) . .
C20 C21 Si1 174.4(3) . .
C23 C22 C24 119.6(4) . .
C23 C22 Si1 122.9(4) . .
C24 C22 Si1 114.5(4) . .
C27 C25 C26 111.2(3) . .
C27 C25 Si1 113.1(3) . .
C26 C25 Si1 115.0(3) . .
C30 C28 C29 109.9(4) . .
C30 C28 Si1 111.5(3) . .
C29 C28 Si1 114.9(3) . .
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
Si1 C21 1.838(3) .
Si1 C22 1.869(4) .
Si1 C28 1.876(4) .
Si1 C25 1.895(4) .
C1 C19 1.413(3) 3_757
C1 C16 1.434(3) .
C1 C2 1.439(3) .
C2 C3 1.348(4) .
C3 C14 1.440(4) .
C3 C4 1.499(4) .
C4 C5 1.351(4) .
C4 C13 1.433(4) .
C5 C6 1.449(4) .
C5 C17 1.500(4) .
C6 C7 1.410(4) .
C6 C11 1.428(4) .
C7 C8 1.369(5) .
C8 C9 1.376(6) .
C9 C10 1.373(5) .
C10 C11 1.414(4) .
C11 C12 1.452(4) .
C12 C13 1.348(4) .
C12 C18 1.491(4) .
C13 C14 1.495(4) .
C14 C15 1.346(4) .
C15 C16 1.439(4) .
C16 C19 1.411(3) .
C19 C1 1.413(3) 3_757
C19 C20 1.435(4) .
C20 C21 1.206(4) .
C22 C23 1.354(7) .
C22 C24 1.522(6) .
C25 C27 1.519(6) .
C25 C26 1.523(5) .
C28 C30 1.521(6) .
C28 C29 1.529(6) .
