#------------------------------------------------------------------------------
#$Date: 2017-01-05 03:58:28 +0200 (Thu, 05 Jan 2017) $
#$Revision: 189859 $
#$URL: file:///home/coder/svn-repositories/cod/cif/4/12/54/4125402.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_4125402
loop_
_publ_author_name
'Frederickson, Conerd K.'
'Zakharov, Lev N.'
'Haley, Michael M.'
_publ_section_title
;
 Modulating Paratropicity Strength in Diareno-Fused Antiaromatics.
;
_journal_issue                   51
_journal_name_full               'Journal of the American Chemical Society'
_journal_page_first              16827
_journal_page_last               16838
_journal_paper_doi               10.1021/jacs.6b11397
_journal_volume                  138
_journal_year                    2016
_chemical_formula_sum            'C50 H56 Si2'
_chemical_formula_weight         713.12
_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'
_symmetry_space_group_name_Hall  '-P 2ybc'
_symmetry_space_group_name_H-M   'P 1 21/c 1'
_atom_sites_solution_hydrogens   geom
_audit_creation_method           SHELXL-2014/7
_cell_angle_alpha                90
_cell_angle_beta                 104.610(4)
_cell_angle_gamma                90
_cell_formula_units_Z            2
_cell_length_a                   8.0881(5)
_cell_length_b                   25.6677(15)
_cell_length_c                   10.3505(6)
_cell_measurement_reflns_used    1133
_cell_measurement_temperature    173(2)
_cell_measurement_theta_max      46.36
_cell_measurement_theta_min      3.44
_cell_volume                     2079.3(2)
_computing_cell_refinement       'Bruker SAINT'
_computing_data_collection       'Bruker APEX2'
_computing_data_reduction        'Bruker SAINT'
_computing_molecular_graphics    'Bruker SHELXTL'
_computing_publication_material  'Bruker SHELXTL'
_computing_structure_refinement  'SHELXL-2014/7 (Sheldrick, 2014)'
_computing_structure_solution    'SHELXS-97 (Sheldrick 2008)'
_diffrn_ambient_temperature      173(2)
_diffrn_measured_fraction_theta_full 0.955
_diffrn_measured_fraction_theta_max 0.955
_diffrn_measurement_device_type  'Bruker Apex-II CCD'
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54178
_diffrn_reflns_av_R_equivalents  0.0824
_diffrn_reflns_av_unetI/netI     0.1060
_diffrn_reflns_Laue_measured_fraction_full 0.955
_diffrn_reflns_Laue_measured_fraction_max 0.955
_diffrn_reflns_limit_h_max       9
_diffrn_reflns_limit_h_min       -9
_diffrn_reflns_limit_k_max       19
_diffrn_reflns_limit_k_min       -30
_diffrn_reflns_limit_l_max       11
_diffrn_reflns_limit_l_min       -12
_diffrn_reflns_number            11489
_diffrn_reflns_point_group_measured_fraction_full 0.955
_diffrn_reflns_point_group_measured_fraction_max 0.955
_diffrn_reflns_theta_full        66.909
_diffrn_reflns_theta_max         66.909
_diffrn_reflns_theta_min         3.444
_diffrn_source                   'Incoatec I\mS'
_exptl_absorpt_coefficient_mu    1.007
_exptl_absorpt_correction_T_max  0.7528
_exptl_absorpt_correction_T_min  0.6133
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   SADABS
_exptl_crystal_colour            dark-blue
_exptl_crystal_density_diffrn    1.139
_exptl_crystal_description       needle
_exptl_crystal_F_000             768
_exptl_crystal_size_max          0.160
_exptl_crystal_size_mid          0.030
_exptl_crystal_size_min          0.020
_refine_diff_density_max         0.236
_refine_diff_density_min         -0.189
_refine_diff_density_rms         0.046
_refine_ls_extinction_coef       0.0023(4)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc²λ³/sin(2θ)]^-1/4^
_refine_ls_extinction_method     'SHELXL-2014/7 (Sheldrick 2014'
_refine_ls_goodness_of_fit_ref   1.053
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     236
_refine_ls_number_reflns         3535
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.053
_refine_ls_R_factor_all          0.1168
_refine_ls_R_factor_gt           0.0627
_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)+(0.0454P)²] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1389
_refine_ls_wR_factor_ref         0.1628
_reflns_Friedel_coverage         0.000
_reflns_number_gt                2041
_reflns_number_total             3535
_reflns_threshold_expression     'I > 2σ(I)'
_cod_data_source_file            ja6b11397_si_003.cif
_cod_data_source_block           cu_mhr157_0m
_cod_database_code               4125402
_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   0.855
_shelx_estimated_absorpt_t_max   0.980
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 0.15824(13) 0.67455(3) 0.46389(10) 0.0494(3) Uani 1 1 d . .
C1 C -0.0517(4) 0.52533(11) 0.1065(3) 0.0454(8) Uani 1 1 d . .
H1A H -0.0838 0.5431 0.1769 0.055 Uiso 1 1 calc R U
C2 C 0.0907(5) 0.54282(11) 0.0604(3) 0.0474(8) Uani 1 1 d . .
C3 C 0.1407(4) 0.51706(12) -0.0486(3) 0.0438(8) Uani 1 1 d . .
C4 C 0.2951(4) 0.54411(12) -0.0637(3) 0.0466(8) Uani 1 1 d . .
C5 C 0.3337(5) 0.58350(12) 0.0326(4) 0.0510(9) Uani 1 1 d . .
C6 C 0.2040(4) 0.58238(11) 0.1096(3) 0.0473(9) Uani 1 1 d . .
C7 C 0.4779(5) 0.61466(13) 0.0484(4) 0.0585(10) Uani 1 1 d . .
H7A H 0.5009 0.6412 0.1145 0.070 Uiso 1 1 calc R U
C8 C 0.5861(5) 0.60691(13) -0.0316(4) 0.0605(10) Uani 1 1 d . .
H8A H 0.6858 0.6278 -0.0199 0.073 Uiso 1 1 calc R U
C9 C 0.5511(5) 0.56781(13) -0.1325(4) 0.0571(10) Uani 1 1 d . .
C10 C 0.4044(5) 0.53591(12) -0.1495(4) 0.0500(9) Uani 1 1 d . .
C11 C 0.3750(5) 0.49724(14) -0.2530(4) 0.0580(10) Uani 1 1 d . .
H11A H 0.2753 0.4762 -0.2688 0.070 Uiso 1 1 calc R U
C12 C 0.4887(5) 0.49048(15) -0.3287(4) 0.0647(11) Uani 1 1 d . .
H12A H 0.4687 0.4642 -0.3954 0.078 Uiso 1 1 calc R U
C13 C 0.6348(5) 0.52176(15) -0.3098(4) 0.0681(12) Uani 1 1 d . .
H13A H 0.7127 0.5165 -0.3636 0.082 Uiso 1 1 calc R U
C14 C 0.6658(5) 0.55968(15) -0.2149(4) 0.0641(11) Uani 1 1 d . .
H14A H 0.7647 0.5809 -0.2034 0.077 Uiso 1 1 calc R U
C15 C 0.2032(5) 0.61415(12) 0.2213(4) 0.0518(9) Uani 1 1 d . .
C16 C 0.1955(5) 0.63865(12) 0.3179(4) 0.0526(9) Uani 1 1 d . .
C17 C 0.3590(5) 0.71153(12) 0.5421(4) 0.0551(9) Uani 1 1 d . .
H17A H 0.3352 0.7334 0.6152 0.066 Uiso 1 1 calc R U
C18 C 0.4105(5) 0.74826(14) 0.4430(4) 0.0697(12) Uani 1 1 d . .
H18A H 0.3145 0.7712 0.4031 0.105 Uiso 1 1 calc R U
H18B H 0.5086 0.7693 0.4896 0.105 Uiso 1 1 calc R U
H18C H 0.4415 0.7278 0.3726 0.105 Uiso 1 1 calc R U
C19 C 0.5076(5) 0.67544(16) 0.6051(5) 0.0862(14) Uani 1 1 d . .
H19A H 0.4734 0.6520 0.6686 0.129 Uiso 1 1 calc R U
H19B H 0.5388 0.6548 0.5352 0.129 Uiso 1 1 calc R U
H19C H 0.6059 0.6963 0.6521 0.129 Uiso 1 1 calc R U
C20 C -0.0207(5) 0.72096(13) 0.3905(4) 0.0559(9) Uani 1 1 d . .
H20A H 0.0172 0.7403 0.3192 0.067 Uiso 1 1 calc R U
C21 C -0.0539(6) 0.76280(15) 0.4860(4) 0.0807(14) Uani 1 1 d . .
H21A H 0.0542 0.7797 0.5305 0.121 Uiso 1 1 calc R U
H21B H -0.1329 0.7889 0.4356 0.121 Uiso 1 1 calc R U
H21C H -0.1042 0.7467 0.5530 0.121 Uiso 1 1 calc R U
C22 C -0.1864(5) 0.69380(15) 0.3191(4) 0.0770(13) Uani 1 1 d . .
H22A H -0.1620 0.6672 0.2586 0.115 Uiso 1 1 calc R U
H22B H -0.2375 0.6773 0.3852 0.115 Uiso 1 1 calc R U
H22C H -0.2662 0.7195 0.2678 0.115 Uiso 1 1 calc R U
C23 C 0.1153(5) 0.62354(13) 0.5827(4) 0.0599(10) Uani 1 1 d . .
H23A H 0.2281 0.6064 0.6208 0.072 Uiso 1 1 calc R U
C24 C 0.0633(6) 0.64625(14) 0.7018(4) 0.0720(12) Uani 1 1 d . .
H24A H 0.1423 0.6743 0.7409 0.108 Uiso 1 1 calc R U
H24B H -0.0530 0.6602 0.6728 0.108 Uiso 1 1 calc R U
H24C H 0.0671 0.6189 0.7686 0.108 Uiso 1 1 calc R U
C25 C -0.0048(6) 0.57943(15) 0.5183(5) 0.0867(15) Uani 1 1 d . .
H25A H 0.0319 0.5655 0.4418 0.130 Uiso 1 1 calc R U
H25B H -0.0015 0.5516 0.5838 0.130 Uiso 1 1 calc R U
H25C H -0.1216 0.5929 0.4880 0.130 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'
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_1
C16 Si1 C17 107.52(17) .
C16 Si1 C20 104.58(17) .
C17 Si1 C20 110.34(16) .
C16 Si1 C23 106.28(15) .
C17 Si1 C23 110.53(17) .
C20 Si1 C23 116.95(18) .
C3 C1 C2 119.2(3) 3_565
C3 C1 H1A 120.4 3_565
C2 C1 H1A 120.4 .
C6 C2 C1 128.8(3) .
C6 C2 C3 109.5(3) .
C1 C2 C3 121.6(3) .
C1 C3 C2 119.2(3) 3_565
C1 C3 C4 134.5(3) 3_565
C2 C3 C4 106.1(3) .
C5 C4 C10 119.4(3) .
C5 C4 C3 108.0(3) .
C10 C4 C3 132.6(3) .
C7 C5 C4 122.0(3) .
C7 C5 C6 129.8(3) .
C4 C5 C6 108.1(3) .
C2 C6 C15 126.0(3) .
C2 C6 C5 108.2(3) .
C15 C6 C5 125.6(3) .
C8 C7 C5 119.6(4) .
C8 C7 H7A 120.2 .
C5 C7 H7A 120.2 .
C7 C8 C9 120.6(4) .
C7 C8 H8A 119.7 .
C9 C8 H8A 119.7 .
C10 C9 C8 120.2(3) .
C10 C9 C14 119.5(4) .
C8 C9 C14 120.2(4) .
C9 C10 C4 118.2(3) .
C9 C10 C11 117.9(3) .
C4 C10 C11 123.9(3) .
C12 C11 C10 120.6(4) .
C12 C11 H11A 119.7 .
C10 C11 H11A 119.7 .
C11 C12 C13 121.0(4) .
C11 C12 H12A 119.5 .
C13 C12 H12A 119.5 .
C14 C13 C12 120.4(4) .
C14 C13 H13A 119.8 .
C12 C13 H13A 119.8 .
C13 C14 C9 120.5(4) .
C13 C14 H14A 119.8 .
C9 C14 H14A 119.8 .
C16 C15 C6 175.7(4) .
C15 C16 Si1 173.7(4) .
C18 C17 C19 110.1(3) .
C18 C17 Si1 112.0(3) .
C19 C17 Si1 112.3(2) .
C18 C17 H17A 107.4 .
C19 C17 H17A 107.4 .
Si1 C17 H17A 107.4 .
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 .
C17 C19 H19A 109.5 .
C17 C19 H19B 109.5 .
H19A C19 H19B 109.5 .
C17 C19 H19C 109.5 .
H19A C19 H19C 109.5 .
H19B C19 H19C 109.5 .
C22 C20 C21 111.0(3) .
C22 C20 Si1 113.5(2) .
C21 C20 Si1 115.3(3) .
C22 C20 H20A 105.4 .
C21 C20 H20A 105.4 .
Si1 C20 H20A 105.4 .
C20 C21 H21A 109.5 .
C20 C21 H21B 109.5 .
H21A C21 H21B 109.5 .
C20 C21 H21C 109.5 .
H21A C21 H21C 109.5 .
H21B C21 H21C 109.5 .
C20 C22 H22A 109.5 .
C20 C22 H22B 109.5 .
H22A C22 H22B 109.5 .
C20 C22 H22C 109.5 .
H22A C22 H22C 109.5 .
H22B C22 H22C 109.5 .
C24 C23 C25 111.3(3) .
C24 C23 Si1 113.4(2) .
C25 C23 Si1 115.4(3) .
C24 C23 H23A 105.2 .
C25 C23 H23A 105.2 .
Si1 C23 H23A 105.2 .
C23 C24 H24A 109.5 .
C23 C24 H24B 109.5 .
H24A C24 H24B 109.5 .
C23 C24 H24C 109.5 .
H24A C24 H24C 109.5 .
H24B C24 H24C 109.5 .
C23 C25 H25A 109.5 .
C23 C25 H25B 109.5 .
H25A C25 H25B 109.5 .
C23 C25 H25C 109.5 .
H25A C25 H25C 109.5 .
H25B C25 H25C 109.5 .
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
Si1 C16 1.859(4) .
Si1 C17 1.879(4) .
Si1 C20 1.880(4) .
Si1 C23 1.888(4) .
C1 C3 1.358(4) 3_565
C1 C2 1.426(4) .
C1 H1A 0.9500 .
C2 C6 1.377(4) .
C2 C3 1.450(4) .
C3 C1 1.358(4) 3_565
C3 C4 1.471(4) .
C4 C5 1.399(4) .
C4 C10 1.418(4) .
C5 C7 1.390(5) .
C5 C6 1.469(5) .
C6 C15 1.415(4) .
C7 C8 1.362(5) .
C7 H7A 0.9500 .
C8 C9 1.424(5) .
C8 H8A 0.9500 .
C9 C10 1.416(5) .
C9 C14 1.425(5) .
C10 C11 1.436(5) .
C11 C12 1.361(5) .
C11 H11A 0.9500 .
C12 C13 1.401(5) .
C12 H12A 0.9500 .
C13 C14 1.361(5) .
C13 H13A 0.9500 .
C14 H14A 0.9500 .
C15 C16 1.196(4) .
C17 C18 1.527(5) .
C17 C19 1.527(5) .
C17 H17A 1.0000 .
C18 H18A 0.9800 .
C18 H18B 0.9800 .
C18 H18C 0.9800 .
C19 H19A 0.9800 .
C19 H19B 0.9800 .
C19 H19C 0.9800 .
C20 C22 1.526(5) .
C20 C21 1.528(5) .
C20 H20A 1.0000 .
C21 H21A 0.9800 .
C21 H21B 0.9800 .
C21 H21C 0.9800 .
C22 H22A 0.9800 .
C22 H22B 0.9800 .
C22 H22C 0.9800 .
C23 C24 1.515(5) .
C23 C25 1.531(5) .
C23 H23A 1.0000 .
C24 H24A 0.9800 .
C24 H24B 0.9800 .
C24 H24C 0.9800 .
C25 H25A 0.9800 .
C25 H25B 0.9800 .
C25 H25C 0.9800 .
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
C3 C1 C2 C6 -175.5(3) 3_565 .
C3 C1 C2 C3 1.2(6) 3_565 .
C6 C2 C3 C1 176.1(3) . 3_565
C1 C2 C3 C1 -1.2(6) . 3_565
C6 C2 C3 C4 -0.2(4) . .
C1 C2 C3 C4 -177.5(3) . .
C1 C3 C4 C5 -175.1(4) 3_565 .
C2 C3 C4 C5 0.4(4) . .
C1 C3 C4 C10 2.3(7) 3_565 .
C2 C3 C4 C10 177.8(3) . .
C10 C4 C5 C7 -0.9(5) . .
C3 C4 C5 C7 176.9(3) . .
C10 C4 C5 C6 -178.2(3) . .
C3 C4 C5 C6 -0.4(4) . .
C1 C2 C6 C15 1.1(6) . .
C3 C2 C6 C15 -175.9(3) . .
C1 C2 C6 C5 177.0(3) . .
C3 C2 C6 C5 0.0(4) . .
C7 C5 C6 C2 -176.8(4) . .
C4 C5 C6 C2 0.3(4) . .
C7 C5 C6 C15 -0.9(6) . .
C4 C5 C6 C15 176.2(3) . .
C4 C5 C7 C8 -0.1(6) . .
C6 C5 C7 C8 176.6(4) . .
C5 C7 C8 C9 1.1(6) . .
C7 C8 C9 C10 -1.0(6) . .
C7 C8 C9 C14 -179.4(3) . .
C8 C9 C10 C4 0.0(5) . .
C14 C9 C10 C4 178.4(3) . .
C8 C9 C10 C11 179.8(3) . .
C14 C9 C10 C11 -1.8(5) . .
C5 C4 C10 C9 0.9(5) . .
C3 C4 C10 C9 -176.2(3) . .
C5 C4 C10 C11 -178.9(3) . .
C3 C4 C10 C11 4.0(6) . .
C9 C10 C11 C12 2.3(5) . .
C4 C10 C11 C12 -177.9(3) . .
C10 C11 C12 C13 -1.5(6) . .
C11 C12 C13 C14 0.0(6) . .
C12 C13 C14 C9 0.6(6) . .
C10 C9 C14 C13 0.3(5) . .
C8 C9 C14 C13 178.8(4) . .
C16 Si1 C17 C18 57.0(3) . .
C20 Si1 C17 C18 -56.5(3) . .
C23 Si1 C17 C18 172.6(2) . .
C16 Si1 C17 C19 -67.4(3) . .
C20 Si1 C17 C19 179.1(3) . .
C23 Si1 C17 C19 48.2(3) . .
C16 Si1 C20 C22 61.9(3) . .
C17 Si1 C20 C22 177.3(3) . .
C23 Si1 C20 C22 -55.3(3) . .
C16 Si1 C20 C21 -168.5(3) . .
C17 Si1 C20 C21 -53.2(3) . .
C23 Si1 C20 C21 74.3(3) . .
C16 Si1 C23 C24 -173.9(3) . .
C17 Si1 C23 C24 69.8(3) . .
C20 Si1 C23 C24 -57.6(3) . .
C16 Si1 C23 C25 -43.7(3) . .
C17 Si1 C23 C25 -160.1(3) . .
C20 Si1 C23 C25 72.6(3) . .
