#------------------------------------------------------------------------------
#$Date: 2019-11-02 07:40:40 +0200 (Sat, 02 Nov 2019) $
#$Revision: 220982 $
#$URL: file:///home/coder/svn-repositories/cod/cif/4/12/78/4127810.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_4127810
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            'C66 H82'
_chemical_formula_weight         875.31
_chemical_name_systematic
5,9,14,18-tetraoctyl-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                 100.3132(13)
_cell_angle_gamma                90
_cell_formula_units_Z            2
_cell_length_a                   18.5667(8)
_cell_length_b                   5.4401(2)
_cell_length_c                   26.2707(10)
_cell_measurement_reflns_used    109
_cell_measurement_temperature    296(2)
_cell_measurement_theta_max      15
_cell_measurement_theta_min      15
_cell_volume                     2610.59(18)
_computing_cell_refinement       'BRUKER D8VENTURE DIFFRACTOMETER'
_computing_data_collection       'BRUKER D8VENTURE DIFFRACTOMETER'
_computing_data_reduction        'BRUKER D8VENTURE 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 0.999
_diffrn_measured_fraction_theta_max 0.999
_diffrn_measurement_device_type  'BRUKER D8VENTURE DIFFRACTOMETER'
_diffrn_measurement_method       'PHI & OMEGA SCAN'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0852
_diffrn_reflns_av_unetI/netI     0.0524
_diffrn_reflns_Laue_measured_fraction_full 0.999
_diffrn_reflns_Laue_measured_fraction_max 0.999
_diffrn_reflns_limit_h_max       22
_diffrn_reflns_limit_h_min       -22
_diffrn_reflns_limit_k_max       6
_diffrn_reflns_limit_k_min       -6
_diffrn_reflns_limit_l_max       31
_diffrn_reflns_limit_l_min       -31
_diffrn_reflns_number            44940
_diffrn_reflns_point_group_measured_fraction_full 0.999
_diffrn_reflns_point_group_measured_fraction_max 0.999
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         25.250
_diffrn_reflns_theta_min         2.230
_exptl_absorpt_coefficient_mu    0.062
_exptl_absorpt_correction_T_max  0.7456
_exptl_absorpt_correction_T_min  0.6540
_exptl_absorpt_correction_type   multi-scan
_exptl_crystal_colour            yellow
_exptl_crystal_density_diffrn    1.114
_exptl_crystal_description       block
_exptl_crystal_F_000             956
_exptl_crystal_size_max          0.400
_exptl_crystal_size_mid          0.300
_exptl_crystal_size_min          0.200
_refine_diff_density_max         0.289
_refine_diff_density_min         -0.297
_refine_diff_density_rms         0.045
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.019
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     298
_refine_ls_number_reflns         4731
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.019
_refine_ls_R_factor_all          0.1222
_refine_ls_R_factor_gt           0.0712
_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)+(0.0981P)²+1.3749P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1742
_refine_ls_wR_factor_ref         0.2024
_reflns_Friedel_coverage         0.000
_reflns_number_gt                2938
_reflns_number_total             4731
_reflns_threshold_expression     'I > 2σ(I)'
_cod_data_source_file            ja8b12671_si_006.cif
_cod_data_source_block           2c
_cod_database_code               4127810
_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   0.976
_shelx_estimated_absorpt_t_max   0.988
_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
C1 C 0.54949(15) 0.3209(5) 0.02073(10) 0.0403(7) Uani 1 1 d . .
H1 H 0.5827 0.2000 0.0346 0.048 Uiso 1 1 calc R U
C2 C 0.48055(14) 0.3207(4) 0.03436(9) 0.0357(6) Uani 1 1 d . .
C3 C 0.46122(14) 0.1444(5) 0.07025(10) 0.0387(6) Uani 1 1 d . .
H3A H 0.4939 0.0231 0.0846 0.046 Uiso 1 1 calc R U
C4 C 0.39406(14) 0.1612(5) 0.08233(9) 0.0357(6) Uani 1 1 d . .
C5 C 0.34024(14) 0.0640(5) 0.11395(9) 0.0352(6) Uani 1 1 d . .
C6 C 0.32864(14) -0.0988(4) 0.15057(9) 0.0351(6) Uani 1 1 d . .
C7 C 0.25633(14) -0.0834(4) 0.16423(9) 0.0338(6) Uani 1 1 d . .
C8 C 0.23578(15) -0.2466(5) 0.20085(10) 0.0404(7) Uani 1 1 d . .
H8A H 0.2693 -0.3636 0.2162 0.048 Uiso 1 1 calc R U
C9 C 0.16817(15) -0.2378(5) 0.21440(10) 0.0447(7) Uani 1 1 d . .
H9A H 0.1562 -0.3489 0.2385 0.054 Uiso 1 1 calc R U
C10 C 0.11744(15) -0.0645(5) 0.19252(10) 0.0433(7) Uani 1 1 d . .
H10A H 0.0716 -0.0584 0.2020 0.052 Uiso 1 1 calc R U
C11 C 0.13495(14) 0.0984(5) 0.15678(9) 0.0392(6) Uani 1 1 d . .
H11A H 0.1005 0.2149 0.1425 0.047 Uiso 1 1 calc R U
C12 C 0.20363(13) 0.0947(4) 0.14099(9) 0.0332(6) Uani 1 1 d . .
C13 C 0.21908(13) 0.2678(4) 0.10229(9) 0.0332(6) Uani 1 1 d . .
C14 C 0.28703(14) 0.2437(4) 0.09045(9) 0.0338(6) Uani 1 1 d . .
C15 C 0.34152(14) 0.3427(5) 0.05948(9) 0.0362(6) Uani 1 1 d . .
C16 C 0.35709(14) 0.5132(5) 0.02593(10) 0.0397(7) Uani 1 1 d . .
H16A H 0.3228 0.6306 0.0119 0.048 Uiso 1 1 calc R U
C17 C 0.42863(14) 0.5067(5) 0.01269(9) 0.0356(6) Uani 1 1 d . .
C18 C 0.38339(15) -0.2820(5) 0.17754(10) 0.0440(7) Uani 1 1 d . .
H18A H 0.3884 -0.2560 0.2145 0.053 Uiso 1 1 calc R U
H18B H 0.3633 -0.4454 0.1702 0.053 Uiso 1 1 calc R U
C19 C 0.45833(16) -0.2777(5) 0.16403(11) 0.0499(8) Uani 1 1 d . .
H19A H 0.4792 -0.1153 0.1714 0.060 Uiso 1 1 calc R U
H19B H 0.4541 -0.3062 0.1272 0.060 Uiso 1 1 calc R U
C20 C 0.51020(16) -0.4670(5) 0.19300(12) 0.0541(8) Uani 1 1 d . .
H20A H 0.5161 -0.4347 0.2298 0.065 Uiso 1 1 calc R U
H20B H 0.4886 -0.6290 0.1867 0.065 Uiso 1 1 calc R U
C21 C 0.58458(19) -0.4662(6) 0.17743(14) 0.0699(10) Uani 1 1 d . .
H21A H 0.5780 -0.4894 0.1403 0.084 Uiso 1 1 calc R U
H21B H 0.6064 -0.3055 0.1851 0.084 Uiso 1 1 calc R U
C22 C 0.6372(2) -0.6564(8) 0.20291(19) 0.1010(14) Uani 1 1 d . .
H22A H 0.6165 -0.8176 0.1938 0.121 Uiso 1 1 calc R U
H22B H 0.6420 -0.6386 0.2401 0.121 Uiso 1 1 calc R U
C23 C 0.7133(3) -0.6457(12) 0.1888(2) 0.1274(19) Uani 1 1 d . .
H23A H 0.7325 -0.4814 0.1963 0.153 Uiso 1 1 calc R U
H23B H 0.7447 -0.7581 0.2114 0.153 Uiso 1 1 calc R U
C24 C 0.7191(3) -0.7057(12) 0.1343(3) 0.1333(19) Uani 1 1 d . .
H24A H 0.7672 -0.6564 0.1285 0.160 Uiso 1 1 calc R U
H24B H 0.6833 -0.6087 0.1113 0.160 Uiso 1 1 calc R U
C25 C 0.7078(4) -0.9706(11) 0.1198(3) 0.165(3) Uani 1 1 d . .
H25A H 0.7125 -0.9926 0.0843 0.248 Uiso 1 1 calc R U
H25B H 0.7439 -1.0686 0.1415 0.248 Uiso 1 1 calc R U
H25C H 0.6598 -1.0208 0.1244 0.248 Uiso 1 1 calc R U
C26 C 0.16181(14) 0.4500(5) 0.07861(9) 0.0360(6) Uani 1 1 d . .
H26A H 0.1497 0.5525 0.1061 0.043 Uiso 1 1 calc R U
H26B H 0.1180 0.3598 0.0638 0.043 Uiso 1 1 calc R U
C27 C 0.18204(14) 0.6161(5) 0.03719(10) 0.0370(6) Uani 1 1 d . .
H27A H 0.1961 0.5155 0.0101 0.044 Uiso 1 1 calc R U
H27B H 0.2241 0.7146 0.0521 0.044 Uiso 1 1 calc R U
C28 C 0.12030(14) 0.7855(5) 0.01352(10) 0.0411(7) Uani 1 1 d . .
H28A H 0.0773 0.6872 0.0005 0.049 Uiso 1 1 calc R U
H28B H 0.1082 0.8925 0.0403 0.049 Uiso 1 1 calc R U
C29 C 0.13836(15) 0.9417(5) -0.03004(11) 0.0468(7) Uani 1 1 d . .
H29A H 0.1512 0.8340 -0.0564 0.056 Uiso 1 1 calc R U
H29B H 0.1811 1.0406 -0.0168 0.056 Uiso 1 1 calc R U
C30 C 0.07739(16) 1.1111(5) -0.05506(11) 0.0496(7) Uani 1 1 d . .
H30A H 0.0676 1.2293 -0.0295 0.060 Uiso 1 1 calc R U
H30B H 0.0333 1.0145 -0.0655 0.060 Uiso 1 1 calc R U
C31 C 0.09377(18) 1.2496(6) -0.10180(12) 0.0602(9) Uani 1 1 d . .
H31A H 0.1397 1.3367 -0.0918 0.072 Uiso 1 1 calc R U
H31B H 0.1002 1.1313 -0.1282 0.072 Uiso 1 1 calc R U
C32 C 0.03602(18) 1.4307(6) -0.12481(12) 0.0630(9) Uani 1 1 d . .
H32A H 0.0346 1.5629 -0.1002 0.076 Uiso 1 1 calc R U
H32B H -0.0112 1.3494 -0.1301 0.076 Uiso 1 1 calc R U
C33 C 0.0476(2) 1.5397(8) -0.17534(15) 0.0950(13) Uani 1 1 d . .
H33A H 0.0088 1.6531 -0.1877 0.142 Uiso 1 1 calc R U
H33B H 0.0937 1.6246 -0.1703 0.142 Uiso 1 1 calc R U
H33C H 0.0478 1.4108 -0.2003 0.142 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'
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
C2 C1 C17 123.3(2) . 3_665
C1 C2 C3 121.3(2) . .
C1 C2 C17 118.6(2) . .
C3 C2 C17 120.0(2) . .
C4 C3 C2 117.5(2) . .
C3 C4 C15 122.4(2) . .
C3 C4 C5 147.4(2) . .
C15 C4 C5 90.2(2) . .
C6 C5 C14 124.2(2) . .
C6 C5 C4 145.9(2) . .
C14 C5 C4 89.84(19) . .
C5 C6 C7 114.2(2) . .
C5 C6 C18 126.0(2) . .
C7 C6 C18 119.8(2) . .
C8 C7 C12 117.9(2) . .
C8 C7 C6 120.5(2) . .
C12 C7 C6 121.6(2) . .
C9 C8 C7 121.9(3) . .
C8 C9 C10 120.3(3) . .
C11 C10 C9 119.8(3) . .
C10 C11 C12 122.0(3) . .
C11 C12 C7 118.0(2) . .
C11 C12 C13 119.9(2) . .
C7 C12 C13 122.1(2) . .
C14 C13 C12 114.0(2) . .
C14 C13 C26 125.8(2) . .
C12 C13 C26 120.2(2) . .
C13 C14 C5 123.9(2) . .
C13 C14 C15 146.1(2) . .
C5 C14 C15 89.92(19) . .
C16 C15 C4 122.4(2) . .
C16 C15 C14 147.5(2) . .
C4 C15 C14 90.00(19) . .
C15 C16 C17 117.3(2) . .
C1 C17 C16 121.6(2) 3_665 .
C1 C17 C2 118.1(2) 3_665 .
C16 C17 C2 120.3(2) . .
C19 C18 C6 117.1(2) . .
C18 C19 C20 113.8(2) . .
C21 C20 C19 113.0(2) . .
C22 C21 C20 115.6(3) . .
C21 C22 C23 115.1(4) . .
C24 C23 C22 117.0(5) . .
C23 C24 C25 115.0(6) . .
C13 C26 C27 116.3(2) . .
C26 C27 C28 113.0(2) . .
C29 C28 C27 113.5(2) . .
C28 C29 C30 114.9(2) . .
C29 C30 C31 114.2(2) . .
C32 C31 C30 114.8(3) . .
C31 C32 C33 114.2(3) . .
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
C1 C2 1.390(4) .
C1 C17 1.394(3) 3_665
C2 C3 1.435(3) .
C2 C17 1.442(3) .
C3 C4 1.344(3) .
C4 C15 1.441(3) .
C4 C5 1.505(3) .
C5 C6 1.353(3) .
C5 C14 1.447(3) .
C6 C7 1.453(3) .
C6 C18 1.507(4) .
C7 C8 1.411(3) .
C7 C12 1.433(4) .
C8 C9 1.366(4) .
C9 C10 1.383(4) .
C10 C11 1.372(4) .
C11 C12 1.410(3) .
C12 C13 1.451(3) .
C13 C14 1.359(3) .
C13 C26 1.505(3) .
C14 C15 1.507(3) .
C15 C16 1.346(3) .
C16 C17 1.432(3) .
C17 C1 1.394(3) 3_665
C18 C19 1.496(4) .
C19 C20 1.518(4) .
C20 C21 1.509(4) .
C21 C22 1.496(5) .
C22 C23 1.525(6) .
C23 C24 1.493(7) .
C24 C25 1.496(8) .
C26 C27 1.513(3) .
C27 C28 1.515(3) .
C28 C29 1.511(4) .
C29 C30 1.515(4) .
C30 C31 1.517(4) .
C31 C32 1.501(4) .
C32 C33 1.504(5) .
