#------------------------------------------------------------------------------
#$Date: 2017-01-05 03:58:19 +0200 (Thu, 05 Jan 2017) $
#$Revision: 189858 $
#$URL: file:///home/coder/svn-repositories/cod/cif/4/12/54/4125401.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_4125401
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
_chemical_name_systematic
;
 ?
;
_space_group_crystal_system      triclinic
_space_group_IT_number           2
_space_group_name_Hall           '-P 1'
_space_group_name_H-M_alt        'P -1'
_symmetry_space_group_name_Hall  '-P 1'
_symmetry_space_group_name_H-M   'P -1'
_atom_sites_solution_hydrogens   geom
_audit_creation_method           SHELXL-2013
_cell_angle_alpha                102.909(3)
_cell_angle_beta                 99.460(3)
_cell_angle_gamma                101.377(3)
_cell_formula_units_Z            1
_cell_length_a                   8.0412(3)
_cell_length_b                   11.6390(5)
_cell_length_c                   11.9019(5)
_cell_measurement_reflns_used    4507
_cell_measurement_temperature    173(2)
_cell_measurement_theta_max      66.58
_cell_measurement_theta_min      3.90
_cell_volume                     1038.80(8)
_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-2013 (Sheldrick 2013)'
_computing_structure_solution    'SHELXS-97 (Sheldrick 2008)'
_diffrn_ambient_temperature      173(2)
_diffrn_measured_fraction_theta_full 0.973
_diffrn_measured_fraction_theta_max 0.995
_diffrn_measurement_device_type  'Bruker APEX-II CCD'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54178
_diffrn_reflns_av_R_equivalents  0.0665
_diffrn_reflns_av_unetI/netI     0.0593
_diffrn_reflns_Laue_measured_fraction_full 0.973
_diffrn_reflns_Laue_measured_fraction_max 0.995
_diffrn_reflns_limit_h_max       9
_diffrn_reflns_limit_h_min       -9
_diffrn_reflns_limit_k_max       13
_diffrn_reflns_limit_k_min       -13
_diffrn_reflns_limit_l_max       14
_diffrn_reflns_limit_l_min       -14
_diffrn_reflns_number            13264
_diffrn_reflns_point_group_measured_fraction_full 0.973
_diffrn_reflns_point_group_measured_fraction_max 0.995
_diffrn_reflns_theta_full        67.679
_diffrn_reflns_theta_max         66.646
_diffrn_reflns_theta_min         3.904
_exptl_absorpt_coefficient_mu    1.008
_exptl_absorpt_correction_T_max  0.7528
_exptl_absorpt_correction_T_min  0.6613
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   SADABS
_exptl_crystal_colour            colorless
_exptl_crystal_density_diffrn    1.140
_exptl_crystal_description       cut-block
_exptl_crystal_F_000             384
_exptl_crystal_size_max          0.130
_exptl_crystal_size_mid          0.100
_exptl_crystal_size_min          0.050
_refine_diff_density_max         0.361
_refine_diff_density_min         -0.311
_refine_diff_density_rms         0.057
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.042
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     235
_refine_ls_number_reflns         3666
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.042
_refine_ls_R_factor_all          0.0559
_refine_ls_R_factor_gt           0.0477
_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)+(0.0803P)²+0.1519P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1292
_refine_ls_wR_factor_ref         0.1370
_reflns_Friedel_coverage         0.000
_reflns_number_gt                3115
_reflns_number_total             3666
_reflns_threshold_expression     'I > 2σ(I)'
_cod_data_source_file            ja6b11397_si_002.cif
_cod_data_source_block           cu_mh144_0m
_cod_database_code               4125401
_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   0.880
_shelx_estimated_absorpt_t_max   0.951
_shelxl_version_number           2013-4
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x, -y, -z'
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 0.26193(6) 0.16665(4) 0.34486(4) 0.02267(17) Uani 1 1 d . .
C1 C 0.5531(2) 0.45090(15) 0.09754(16) 0.0242(4) Uani 1 1 d . .
H1A H 0.5859 0.4179 0.1616 0.029 Uiso 1 1 calc R U
C2 C 0.3775(2) 0.42241(15) 0.03510(16) 0.0236(4) Uani 1 1 d . .
C3 C 0.3266(2) 0.47245(15) -0.06203(16) 0.0233(4) Uani 1 1 d . .
C4 C 0.1390(2) 0.42623(15) -0.10379(16) 0.0242(4) Uani 1 1 d . .
C5 C 0.0786(2) 0.35032(16) -0.03516(16) 0.0241(4) Uani 1 1 d . .
C6 C 0.2289(2) 0.34818(16) 0.05183(16) 0.0243(4) Uani 1 1 d . .
C7 C 0.0225(3) 0.44844(17) -0.19388(17) 0.0289(4) Uani 1 1 d . .
H7A H 0.0636 0.5004 -0.2399 0.035 Uiso 1 1 calc R U
C8 C -0.1508(3) 0.39415(18) -0.21424(17) 0.0321(4) Uani 1 1 d . .
H8A H -0.2294 0.4090 -0.2751 0.039 Uiso 1 1 calc R U
C9 C -0.2164(3) 0.31640(17) -0.14710(18) 0.0297(4) Uani 1 1 d . .
C10 C -0.1014(2) 0.29322(16) -0.05475(17) 0.0274(4) Uani 1 1 d . .
C11 C -0.1714(3) 0.21633(18) 0.01134(18) 0.0327(4) Uani 1 1 d . .
H11A H -0.0962 0.2003 0.0732 0.039 Uiso 1 1 calc R U
C12 C -0.3465(3) 0.1645(2) -0.0126(2) 0.0402(5) Uani 1 1 d . .
H12A H -0.3913 0.1134 0.0330 0.048 Uiso 1 1 calc R U
C13 C -0.4599(3) 0.1865(2) -0.1040(2) 0.0407(5) Uani 1 1 d . .
H13A H -0.5808 0.1498 -0.1206 0.049 Uiso 1 1 calc R U
C14 C -0.3961(3) 0.26085(19) -0.1690(2) 0.0373(5) Uani 1 1 d . .
H14A H -0.4740 0.2756 -0.2303 0.045 Uiso 1 1 calc R U
C15 C 0.2322(2) 0.28488(16) 0.14055(17) 0.0258(4) Uani 1 1 d . .
C16 C 0.2411(2) 0.23401(17) 0.21884(18) 0.0294(4) Uani 1 1 d . .
C17 C 0.5016(2) 0.20062(19) 0.40935(19) 0.0328(5) Uani 1 1 d . .
H17A H 0.5159 0.1742 0.4840 0.039 Uiso 1 1 calc R U
C18 C 0.5943(3) 0.1290(3) 0.3267(2) 0.0544(7) Uani 1 1 d . .
H18A H 0.7186 0.1488 0.3628 0.082 Uiso 1 1 calc R U
H18B H 0.5786 0.1506 0.2513 0.082 Uiso 1 1 calc R U
H18C H 0.5451 0.0418 0.3129 0.082 Uiso 1 1 calc R U
C19 C 0.5887(3) 0.3368(2) 0.4410(2) 0.0466(6) Uani 1 1 d . .
H19A H 0.7130 0.3502 0.4741 0.070 Uiso 1 1 calc R U
H19B H 0.5352 0.3813 0.4994 0.070 Uiso 1 1 calc R U
H19C H 0.5734 0.3660 0.3697 0.070 Uiso 1 1 calc R U
C20 C 0.1399(2) 0.23775(17) 0.45446(18) 0.0294(4) Uani 1 1 d . .
H20A H 0.0251 0.1787 0.4403 0.035 Uiso 1 1 calc R U
C21 C 0.1004(3) 0.3567(2) 0.4373(3) 0.0501(6) Uani 1 1 d . .
H21A H 0.0375 0.3879 0.4965 0.075 Uiso 1 1 calc R U
H21B H 0.0288 0.3419 0.3580 0.075 Uiso 1 1 calc R U
H21C H 0.2095 0.4164 0.4463 0.075 Uiso 1 1 calc R U
C22 C 0.2303(3) 0.2546(2) 0.5832(2) 0.0454(6) Uani 1 1 d . .
H22A H 0.1628 0.2915 0.6361 0.068 Uiso 1 1 calc R U
H22B H 0.3473 0.3077 0.5997 0.068 Uiso 1 1 calc R U
H22C H 0.2387 0.1754 0.5958 0.068 Uiso 1 1 calc R U
C23 C 0.1655(2) -0.00202(16) 0.28861(19) 0.0305(4) Uani 1 1 d . .
H23A H 0.2323 -0.0352 0.2305 0.037 Uiso 1 1 calc R U
C24 C -0.0243(3) -0.03249(19) 0.2241(2) 0.0439(6) Uani 1 1 d . .
H24A H -0.0688 -0.1209 0.1965 0.066 Uiso 1 1 calc R U
H24B H -0.0334 0.0024 0.1563 0.066 Uiso 1 1 calc R U
H24C H -0.0928 0.0015 0.2780 0.066 Uiso 1 1 calc R U
C25 C 0.1888(3) -0.06322(19) 0.3899(2) 0.0451(6) Uani 1 1 d . .
H25A H 0.1381 -0.1509 0.3593 0.068 Uiso 1 1 calc R U
H25B H 0.1301 -0.0293 0.4507 0.068 Uiso 1 1 calc R U
H25C H 0.3129 -0.0486 0.4242 0.068 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 106.00(9) .
C16 Si1 C23 108.52(9) .
C17 Si1 C23 111.04(9) .
C16 Si1 C20 108.72(9) .
C17 Si1 C20 112.15(9) .
C23 Si1 C20 110.23(8) .
C3 C1 C2 117.55(16) 2_665
C3 C1 H1A 121.2 2_665
C2 C1 H1A 121.2 .
C6 C2 C1 130.01(17) .
C6 C2 C3 108.45(16) .
C1 C2 C3 121.54(16) .
C1 C3 C2 120.91(17) 2_665
C1 C3 C4 132.12(17) 2_665
C2 C3 C4 106.96(15) .
C5 C4 C7 120.62(17) .
C5 C4 C3 108.56(16) .
C7 C4 C3 130.81(17) .
C4 C5 C10 121.18(17) .
C4 C5 C6 107.51(16) .
C10 C5 C6 131.30(17) .
C2 C6 C15 123.30(17) .
C2 C6 C5 108.52(16) .
C15 C6 C5 128.18(17) .
C8 C7 C4 119.05(18) .
C8 C7 H7A 120.5 .
C4 C7 H7A 120.5 .
C7 C8 C9 121.86(18) .
C7 C8 H8A 119.1 .
C9 C8 H8A 119.1 .
C8 C9 C14 121.30(19) .
C8 C9 C10 120.20(18) .
C14 C9 C10 118.49(19) .
C11 C10 C9 118.70(18) .
C11 C10 C5 124.22(18) .
C9 C10 C5 117.08(18) .
C12 C11 C10 120.9(2) .
C12 C11 H11A 119.5 .
C10 C11 H11A 119.5 .
C11 C12 C13 120.5(2) .
C11 C12 H12A 119.7 .
C13 C12 H12A 119.7 .
C14 C13 C12 119.9(2) .
C14 C13 H13A 120.1 .
C12 C13 H13A 120.1 .
C13 C14 C9 121.5(2) .
C13 C14 H14A 119.3 .
C9 C14 H14A 119.3 .
C16 C15 C6 177.4(2) .
C15 C16 Si1 176.16(18) .
C18 C17 C19 110.02(19) .
C18 C17 Si1 111.58(15) .
C19 C17 Si1 112.29(14) .
C18 C17 H17A 107.6 .
C19 C17 H17A 107.6 .
Si1 C17 H17A 107.6 .
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 .
C21 C20 C22 110.42(19) .
C21 C20 Si1 113.98(15) .
C22 C20 Si1 112.54(14) .
C21 C20 H20A 106.4 .
C22 C20 H20A 106.4 .
Si1 C20 H20A 106.4 .
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 111.56(18) .
C24 C23 Si1 112.37(13) .
C25 C23 Si1 110.37(14) .
C24 C23 H23A 107.4 .
C25 C23 H23A 107.4 .
Si1 C23 H23A 107.4 .
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 1.840(2) .
Si1 C17 1.881(2) .
Si1 C23 1.8827(19) .
Si1 C20 1.899(2) .
C1 C3 1.368(2) 2_665
C1 C2 1.420(3) .
C1 H1A 0.9500 .
C2 C6 1.401(3) .
C2 C3 1.443(2) .
C3 C1 1.368(2) 2_665
C3 C4 1.458(3) .
C4 C5 1.403(3) .
C4 C7 1.408(3) .
C5 C10 1.425(3) .
C5 C6 1.465(3) .
C6 C15 1.416(3) .
C7 C8 1.369(3) .
C7 H7A 0.9500 .
C8 C9 1.417(3) .
C8 H8A 0.9500 .
C9 C14 1.417(3) .
C9 C10 1.426(3) .
C10 C11 1.414(3) .
C11 C12 1.372(3) .
C11 H11A 0.9500 .
C12 C13 1.404(3) .
C12 H12A 0.9500 .
C13 C14 1.365(3) .
C13 H13A 0.9500 .
C14 H14A 0.9500 .
C15 C16 1.210(3) .
C17 C18 1.529(3) .
C17 C19 1.534(3) .
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 C21 1.529(3) .
C20 C22 1.535(3) .
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 1.525(3) .
C23 C25 1.535(3) .
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 -179.70(18) 2_665 .
C3 C1 C2 C3 -0.2(3) 2_665 .
C6 C2 C3 C1 179.80(16) . 2_665
C1 C2 C3 C1 0.2(3) . 2_665
C6 C2 C3 C4 0.46(19) . .
C1 C2 C3 C4 -179.12(16) . .
C1 C3 C4 C5 -179.65(19) 2_665 .
C2 C3 C4 C5 -0.42(19) . .
C1 C3 C4 C7 -1.1(3) 2_665 .
C2 C3 C4 C7 178.15(18) . .
C7 C4 C5 C10 0.3(3) . .
C3 C4 C5 C10 179.05(16) . .
C7 C4 C5 C6 -178.53(16) . .
C3 C4 C5 C6 0.21(19) . .
C1 C2 C6 C15 -0.3(3) . .
C3 C2 C6 C15 -179.85(16) . .
C1 C2 C6 C5 179.19(17) . .
C3 C2 C6 C5 -0.3(2) . .
C4 C5 C6 C2 0.1(2) . .
C10 C5 C6 C2 -178.60(18) . .
C4 C5 C6 C15 179.56(17) . .
C10 C5 C6 C15 0.9(3) . .
C5 C4 C7 C8 -0.5(3) . .
C3 C4 C7 C8 -178.89(18) . .
C4 C7 C8 C9 0.1(3) . .
C7 C8 C9 C14 179.94(18) . .
C7 C8 C9 C10 0.4(3) . .
C8 C9 C10 C11 179.28(17) . .
C14 C9 C10 C11 -0.3(3) . .
C8 C9 C10 C5 -0.6(3) . .
C14 C9 C10 C5 179.90(17) . .
C4 C5 C10 C11 -179.62(17) . .
C6 C5 C10 C11 -1.1(3) . .
C4 C5 C10 C9 0.2(3) . .
C6 C5 C10 C9 178.73(17) . .
C9 C10 C11 C12 0.1(3) . .
C5 C10 C11 C12 179.95(19) . .
C10 C11 C12 C13 0.3(3) . .
C11 C12 C13 C14 -0.6(3) . .
C12 C13 C14 C9 0.4(3) . .
C8 C9 C14 C13 -179.55(19) . .
C10 C9 C14 C13 0.0(3) . .
C16 Si1 C17 C18 -69.28(18) . .
C23 Si1 C17 C18 48.39(19) . .
C20 Si1 C17 C18 172.22(16) . .
C16 Si1 C17 C19 54.78(18) . .
C23 Si1 C17 C19 172.44(15) . .
C20 Si1 C17 C19 -63.73(18) . .
C16 Si1 C20 C21 -17.48(18) . .
C17 Si1 C20 C21 99.41(17) . .
C23 Si1 C20 C21 -136.31(16) . .
C16 Si1 C20 C22 -144.21(15) . .
C17 Si1 C20 C22 -27.33(17) . .
C23 Si1 C20 C22 96.96(16) . .
C16 Si1 C23 C24 -57.82(17) . .
C17 Si1 C23 C24 -173.94(15) . .
C20 Si1 C23 C24 61.14(18) . .
C16 Si1 C23 C25 176.96(14) . .
C17 Si1 C23 C25 60.84(17) . .
C20 Si1 C23 C25 -64.08(16) . .
