#------------------------------------------------------------------------------
#$Date: 2016-03-21 04:01:44 +0200 (Mon, 21 Mar 2016) $
#$Revision: 178456 $
#$URL: svn://www.crystallography.net/cod/cif/4/02/77/4027746.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_4027746
loop_
_publ_author_name
'Bharat Kumar'
'Benjamin T. King'
_publ_section_title
;
 Synthesis of
 1,8,9,16-Tetrakis(trimethylsilyl)tetra-cata-tetrabenzoquadrannulene
;
_journal_name_full               'Journal of Organic Chemistry'
_journal_page_first              10617
_journal_page_last               10622
_journal_paper_doi               10.1021/jo3015648
_journal_volume                  77
_journal_year                    2012
_chemical_formula_sum            'C40 H48 O2 Si4'
_chemical_formula_weight         673.14
_chemical_name_systematic
; 
 ? 
;
_space_group_IT_number           14
_symmetry_cell_setting           monoclinic
_symmetry_space_group_name_Hall  '-P 2yn'
_symmetry_space_group_name_H-M   'P 1 21/n 1'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_audit_creation_method           SHELXL-97
_cell_angle_alpha                90.00
_cell_angle_beta                 85.780(2)
_cell_angle_gamma                90.00
_cell_formula_units_Z            2
_cell_length_a                   10.4606(13)
_cell_length_b                   12.1928(16)
_cell_length_c                   16.305(2)
_cell_measurement_temperature    296(2)
_cell_volume                     2074.0(5)
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 2008)'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 2008)'
_diffrn_ambient_temperature      296(2)
_diffrn_measured_fraction_theta_full 0.997
_diffrn_measured_fraction_theta_max 0.997
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_source         'fine-focus sealed tube'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.1704
_diffrn_reflns_av_sigmaI/netI    0.1409
_diffrn_reflns_limit_h_max       13
_diffrn_reflns_limit_h_min       -13
_diffrn_reflns_limit_k_max       15
_diffrn_reflns_limit_k_min       -15
_diffrn_reflns_limit_l_max       21
_diffrn_reflns_limit_l_min       -21
_diffrn_reflns_number            22408
_diffrn_reflns_theta_full        27.52
_diffrn_reflns_theta_max         27.52
_diffrn_reflns_theta_min         2.09
_exptl_absorpt_coefficient_mu    0.172
_exptl_absorpt_correction_T_max  0.9842
_exptl_absorpt_correction_T_min  0.9320
_exptl_absorpt_correction_type   multi-scan
_exptl_crystal_density_diffrn    1.052
_exptl_crystal_F_000             688
_exptl_crystal_size_max          0.41
_exptl_crystal_size_mid          0.15
_exptl_crystal_size_min          0.09
_refine_diff_density_max         0.801
_refine_diff_density_min         -0.724
_refine_diff_density_rms         0.076
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.027
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     204
_refine_ls_number_reflns         4763
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.027
_refine_ls_R_factor_all          0.2397
_refine_ls_R_factor_gt           0.1046
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'calc w=1/[σ²(Fo²)+(0.1415P)²+1.5462P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.2479
_refine_ls_wR_factor_ref         0.3198
_reflns_number_gt                1935
_reflns_number_total             4763
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            jo3015648_si_002.cif
_cod_data_source_block           b_108_0ma
_cod_database_code               4027746
loop_
_symmetry_equiv_pos_as_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_symmetry_multiplicity
_atom_site_calc_flag
_atom_site_refinement_flags
_atom_site_disorder_assembly
_atom_site_disorder_group
Si1 Si 0.7378(2) 1.40416(15) 0.40176(12) 0.0674(7) Uani 1 1 d . . .
Si2 Si 1.22528(17) 0.69258(16) 0.23164(11) 0.0584(6) Uani 1 1 d . . .
C14 C 0.7737(6) 1.2574(5) 0.4075(4) 0.0537(16) Uani 1 1 d . B .
C13 C 0.8040(6) 1.1629(5) 0.4117(3) 0.0499(15) Uani 1 1 d . . .
C8 C 0.8405(5) 1.0480(5) 0.4232(3) 0.0456(15) Uani 1 1 d . . .
C7 C 1.1013(6) 0.9779(4) 0.4954(3) 0.0467(16) Uani 1 1 d . . .
H7 H 1.1627 0.9842 0.4472 0.056 Uiso 1 1 calc R . .
C6 C 0.9773(6) 0.9159(4) 0.4814(3) 0.0443(15) Uani 1 1 d . . .
H6 H 0.9589 0.8528 0.5176 0.053 Uiso 1 1 calc R . .
O1 O 0.9431(4) 1.0137(3) 0.3628(2) 0.0491(11) Uani 1 1 d . . .
C5 C 0.9494(6) 0.8992(5) 0.3923(3) 0.0485(15) Uani 1 1 d . A .
C11 C 1.0432(6) 0.8353(5) 0.3407(3) 0.0505(16) Uani 1 1 d . . .
C12 C 1.1169(6) 0.7791(5) 0.2989(3) 0.0526(16) Uani 1 1 d . A .
C10 C 0.7428(6) 0.9597(5) 0.4121(3) 0.0486(16) Uani 1 1 d . . .
C9 C 0.8121(6) 0.8653(5) 0.3922(3) 0.0513(16) Uani 1 1 d . A .
C4 C 0.7543(7) 0.7673(6) 0.3807(4) 0.0620(19) Uani 1 1 d . . .
H4 H 0.8019 0.7041 0.3689 0.074 Uiso 1 1 calc R B .
C3 C 0.6201(8) 0.7653(6) 0.3873(4) 0.070(2) Uani 1 1 d . B .
H3 H 0.5770 0.7001 0.3782 0.084 Uiso 1 1 calc R . .
C2 C 0.5510(7) 0.8596(6) 0.4072(4) 0.0660(19) Uani 1 1 d . . .
H2 H 0.4620 0.8564 0.4120 0.079 Uiso 1 1 calc R B .
C1 C 0.6106(7) 0.9583(5) 0.4201(4) 0.0573(17) Uani 1 1 d . B .
H1 H 0.5636 1.0213 0.4337 0.069 Uiso 1 1 calc R . .
C15 C 1.3673(12) 0.7837(11) 0.1866(8) 0.067(4) Uiso 0.523(8) 1 d P A 1
H15A H 1.4119 0.8138 0.2308 0.101 Uiso 0.523(8) 1 calc PR A 1
H15B H 1.3345 0.8423 0.1549 0.101 Uiso 0.523(8) 1 calc PR A 1
H15C H 1.4252 0.7399 0.1520 0.101 Uiso 0.523(8) 1 calc PR A 1
C16 C 1.3031(14) 0.5920(12) 0.2942(9) 0.085(5) Uiso 0.523(8) 1 d P A 1
H16A H 1.3506 0.6293 0.3340 0.128 Uiso 0.523(8) 1 calc PR A 1
H16B H 1.3603 0.5477 0.2595 0.128 Uiso 0.523(8) 1 calc PR A 1
H16C H 1.2392 0.5461 0.3221 0.128 Uiso 0.523(8) 1 calc PR A 1
C17 C 1.1380(15) 0.6301(14) 0.1594(10) 0.091(5) Uiso 0.523(8) 1 d P A 1
H17A H 1.1937 0.5852 0.1241 0.136 Uiso 0.523(8) 1 calc PR A 1
H17B H 1.0992 0.6851 0.1271 0.136 Uiso 0.523(8) 1 calc PR A 1
H17C H 1.0724 0.5853 0.1865 0.136 Uiso 0.523(8) 1 calc PR A 1
C18 C 1.3752(14) 0.7018(13) 0.2634(10) 0.080(5) Uiso 0.477(8) 1 d P A 2
H18A H 1.4324 0.6573 0.2287 0.119 Uiso 0.477(8) 1 calc PR A 2
H18B H 1.3752 0.6766 0.3192 0.119 Uiso 0.477(8) 1 calc PR A 2
H18C H 1.4032 0.7768 0.2603 0.119 Uiso 0.477(8) 1 calc PR A 2
C19 C 1.1659(15) 0.5415(12) 0.2430(9) 0.074(5) Uiso 0.477(8) 1 d P A 2
H19A H 1.0815 0.5357 0.2240 0.111 Uiso 0.477(8) 1 calc PR A 2
H19B H 1.1637 0.5201 0.2997 0.111 Uiso 0.477(8) 1 calc PR A 2
H19C H 1.2234 0.4943 0.2108 0.111 Uiso 0.477(8) 1 calc PR A 2
C20 C 1.1872(16) 0.7259(14) 0.1228(9) 0.083(5) Uiso 0.477(8) 1 d P A 2
H20A H 1.0979 0.7128 0.1168 0.125 Uiso 0.477(8) 1 calc PR A 2
H20B H 1.2378 0.6804 0.0850 0.125 Uiso 0.477(8) 1 calc PR A 2
H20C H 1.2065 0.8016 0.1113 0.125 Uiso 0.477(8) 1 calc PR A 2
C21 C 0.5552(11) 1.4111(10) 0.3851(8) 0.100(4) Uiso 0.729(11) 1 d P B 1
H21A H 0.5069 1.3834 0.4330 0.150 Uiso 0.729(11) 1 calc PR B 1
H21B H 0.5377 1.3675 0.3382 0.150 Uiso 0.729(11) 1 calc PR B 1
H21C H 0.5312 1.4858 0.3759 0.150 Uiso 0.729(11) 1 calc PR B 1
C22 C 0.7949(14) 1.4553(11) 0.3079(8) 0.099(4) Uiso 0.729(11) 1 d P B 1
H22A H 0.7692 1.4080 0.2650 0.148 Uiso 0.729(11) 1 calc PR B 1
H22B H 0.8868 1.4590 0.3057 0.148 Uiso 0.729(11) 1 calc PR B 1
H22C H 0.7607 1.5274 0.3007 0.148 Uiso 0.729(11) 1 calc PR B 1
C23 C 0.7669(10) 1.4718(8) 0.4956(6) 0.071(3) Uiso 0.729(11) 1 d P B 1
H23A H 0.7248 1.4327 0.5410 0.107 Uiso 0.729(11) 1 calc PR B 1
H23B H 0.7340 1.5453 0.4946 0.107 Uiso 0.729(11) 1 calc PR B 1
H23C H 0.8574 1.4740 0.5018 0.107 Uiso 0.729(11) 1 calc PR B 1
C24 C 0.585(3) 1.441(2) 0.4613(19) 0.085(10) Uiso 0.271(11) 1 d P B 2
H24A H 0.5695 1.5181 0.4566 0.128 Uiso 0.271(11) 1 calc PR B 2
H24B H 0.5901 1.4220 0.5181 0.128 Uiso 0.271(11) 1 calc PR B 2
H24C H 0.5151 1.4011 0.4398 0.128 Uiso 0.271(11) 1 calc PR B 2
C25 C 0.875(3) 1.469(2) 0.3192(17) 0.071(8) Uiso 0.271(11) 1 d P B 2
H25A H 0.8615 1.5462 0.3138 0.106 Uiso 0.271(11) 1 calc PR B 2
H25B H 0.8705 1.4340 0.2667 0.106 Uiso 0.271(11) 1 calc PR B 2
H25C H 0.9587 1.4563 0.3386 0.106 Uiso 0.271(11) 1 calc PR B 2
C26 C 0.869(3) 1.461(2) 0.4663(18) 0.081(9) Uiso 0.271(11) 1 d P B 2
H26A H 0.8616 1.5399 0.4693 0.121 Uiso 0.271(11) 1 calc PR B 2
H26B H 0.9516 1.4421 0.4410 0.121 Uiso 0.271(11) 1 calc PR B 2
H26C H 0.8591 1.4311 0.5207 0.121 Uiso 0.271(11) 1 calc PR B 2
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'
O O 0.0106 0.0060 '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
C22 Si1 C23 121.7(6) . .
C22 Si1 C14 109.9(5) . .
C23 Si1 C14 111.0(4) . .
C22 Si1 C24 127.3(11) . .
C23 Si1 C24 68.7(10) . .
C14 Si1 C24 112.3(9) . .
C22 Si1 C26 98.0(11) . .
C23 Si1 C26 35.7(9) . .
C14 Si1 C26 99.8(9) . .
C24 Si1 C26 104.4(13) . .
C22 Si1 C21 98.1(7) . .
C23 Si1 C21 109.3(5) . .
C14 Si1 C21 104.9(4) . .
C24 Si1 C21 41.4(9) . .
C26 Si1 C21 143.8(10) . .
C22 Si1 C25 25.4(8) . .
C23 Si1 C25 103.2(9) . .
C14 Si1 C25 105.7(8) . .
C24 Si1 C25 141.5(12) . .
C26 Si1 C25 74.0(13) . .
C21 Si1 C25 122.6(10) . .
C18 Si2 C17 142.2(8) . .
C18 Si2 C16 54.0(7) . .
C17 Si2 C16 111.5(8) . .
C18 Si2 C12 108.8(6) . .
C17 Si2 C12 109.0(6) . .
C16 Si2 C12 109.3(5) . .
C18 Si2 C20 122.5(8) . .
C17 Si2 C20 45.0(7) . .
C16 Si2 C20 143.4(7) . .
C12 Si2 C20 105.7(5) . .
C18 Si2 C19 109.3(7) . .
C17 Si2 C19 57.7(7) . .
C16 Si2 C19 57.6(6) . .
C12 Si2 C19 107.8(5) . .
C20 Si2 C19 101.8(7) . .
C18 Si2 C15 51.8(6) . .
C17 Si2 C15 114.9(7) . .
C16 Si2 C15 103.6(6) . .
C12 Si2 C15 108.3(4) . .
C20 Si2 C15 74.5(6) . .
C19 Si2 C15 143.3(6) . .
C13 C14 Si1 176.5(6) . .
C14 C13 C8 176.0(6) . .
O1 C8 C13 111.8(4) . .
O1 C8 C10 100.7(4) . .
C13 C8 C10 118.8(5) . .
O1 C8 C7 101.8(4) . 3_776
C13 C8 C7 115.5(5) . 3_776
C10 C8 C7 105.9(5) . 3_776
C6 C7 C8 114.9(4) . 3_776
C6 C7 C6 90.5(4) . 3_776
C8 C7 C6 101.3(4) 3_776 3_776
C6 C7 H7 115.5 . .
C8 C7 H7 115.5 3_776 .
C6 C7 H7 115.5 3_776 .
C5 C6 C7 115.6(4) . .
C5 C6 C7 102.0(4) . 3_776
C7 C6 C7 89.5(4) . 3_776
C5 C6 H6 115.4 . .
C7 C6 H6 115.4 . .
C7 C6 H6 115.4 3_776 .
C8 O1 C5 95.7(4) . .
C11 C5 O1 111.0(4) . .
C11 C5 C9 117.0(5) . .
O1 C5 C9 101.2(4) . .
C11 C5 C6 117.0(5) . .
O1 C5 C6 101.6(4) . .
C9 C5 C6 106.9(4) . .
C12 C11 C5 177.2(7) . .
C11 C12 Si2 177.7(6) . .
C1 C10 C9 121.0(6) . .
C1 C10 C8 133.1(5) . .
C9 C10 C8 105.9(5) . .
C4 C9 C10 122.2(6) . .
C4 C9 C5 132.9(5) . .
C10 C9 C5 104.9(6) . .
C9 C4 C3 117.3(6) . .
C9 C4 H4 121.4 . .
C3 C4 H4 121.4 . .
C2 C3 C4 120.4(7) . .
C2 C3 H3 119.8 . .
C4 C3 H3 119.8 . .
C1 C2 C3 121.8(7) . .
C1 C2 H2 119.1 . .
C3 C2 H2 119.1 . .
C2 C1 C10 117.3(6) . .
C2 C1 H1 121.4 . .
C10 C1 H1 121.4 . .
Si2 C15 H15A 109.5 . .
Si2 C15 H15B 109.5 . .
H15A C15 H15B 109.5 . .
Si2 C15 H15C 109.5 . .
H15A C15 H15C 109.5 . .
H15B C15 H15C 109.5 . .
Si2 C16 H16A 109.5 . .
Si2 C16 H16B 109.5 . .
H16A C16 H16B 109.5 . .
Si2 C16 H16C 109.5 . .
H16A C16 H16C 109.5 . .
H16B C16 H16C 109.5 . .
Si2 C17 H17A 109.5 . .
Si2 C17 H17B 109.5 . .
H17A C17 H17B 109.5 . .
Si2 C17 H17C 109.5 . .
H17A C17 H17C 109.5 . .
H17B C17 H17C 109.5 . .
Si2 C18 H18A 109.5 . .
Si2 C18 H18B 109.5 . .
H18A C18 H18B 109.5 . .
Si2 C18 H18C 109.5 . .
H18A C18 H18C 109.5 . .
H18B C18 H18C 109.5 . .
Si2 C19 H19A 109.5 . .
Si2 C19 H19B 109.5 . .
H19A C19 H19B 109.5 . .
Si2 C19 H19C 109.5 . .
H19A C19 H19C 109.5 . .
H19B C19 H19C 109.5 . .
Si2 C20 H20A 109.5 . .
Si2 C20 H20B 109.5 . .
H20A C20 H20B 109.5 . .
Si2 C20 H20C 109.5 . .
H20A C20 H20C 109.5 . .
H20B C20 H20C 109.5 . .
Si1 C21 H21A 109.5 . .
Si1 C21 H21B 109.5 . .
H21A C21 H21B 109.5 . .
Si1 C21 H21C 109.5 . .
H21A C21 H21C 109.5 . .
H21B C21 H21C 109.5 . .
Si1 C22 H22A 109.5 . .
Si1 C22 H22B 109.5 . .
H22A C22 H22B 109.5 . .
Si1 C22 H22C 109.5 . .
H22A C22 H22C 109.5 . .
H22B C22 H22C 109.5 . .
Si1 C23 H23A 109.5 . .
Si1 C23 H23B 109.5 . .
H23A C23 H23B 109.5 . .
Si1 C23 H23C 109.5 . .
H23A C23 H23C 109.5 . .
H23B C23 H23C 109.5 . .
Si1 C24 H24A 109.5 . .
Si1 C24 H24B 109.5 . .
H24A C24 H24B 109.5 . .
Si1 C24 H24C 109.5 . .
H24A C24 H24C 109.5 . .
H24B C24 H24C 109.5 . .
Si1 C25 H25A 109.5 . .
Si1 C25 H25B 109.5 . .
H25A C25 H25B 109.5 . .
Si1 C25 H25C 109.5 . .
H25A C25 H25C 109.5 . .
H25B C25 H25C 109.5 . .
Si1 C26 H26A 109.5 . .
Si1 C26 H26B 109.5 . .
H26A C26 H26B 109.5 . .
Si1 C26 H26C 109.5 . .
H26A C26 H26C 109.5 . .
H26B C26 H26C 109.5 . .
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
Si1 C22 1.718(12) .
Si1 C23 1.785(10) .
Si1 C14 1.832(6) .
Si1 C24 1.87(3) .
Si1 C26 1.92(3) .
Si1 C21 1.950(12) .
Si1 C25 2.05(3) .
Si2 C18 1.691(15) .
Si2 C17 1.721(15) .
Si2 C16 1.825(14) .
Si2 C12 1.848(6) .
Si2 C20 1.892(15) .
Si2 C19 1.948(15) .
Si2 C15 1.955(13) .
C14 C13 1.199(8) .
C13 C8 1.468(8) .
C8 O1 1.463(6) .
C8 C10 1.503(9) .
C8 C7 1.534(7) 3_776
C7 C6 1.533(8) .
C7 C8 1.534(7) 3_776
C7 C6 1.565(7) 3_776
C7 H7 0.9800 .
C6 C5 1.517(8) .
C6 C7 1.565(7) 3_776
C6 H6 0.9800 .
O1 C5 1.479(6) .
C5 C11 1.468(7) .
C5 C9 1.495(9) .
C11 C12 1.205(7) .
C10 C1 1.380(9) .
C10 C9 1.386(8) .
C9 C4 1.359(9) .
C4 C3 1.401(10) .
C4 H4 0.9300 .
C3 C2 1.384(9) .
C3 H3 0.9300 .
C2 C1 1.378(9) .
C2 H2 0.9300 .
C1 H1 0.9300 .
C15 H15A 0.9600 .
C15 H15B 0.9600 .
C15 H15C 0.9600 .
C16 H16A 0.9600 .
C16 H16B 0.9600 .
C16 H16C 0.9600 .
C17 H17A 0.9600 .
C17 H17B 0.9600 .
C17 H17C 0.9600 .
C18 H18A 0.9600 .
C18 H18B 0.9600 .
C18 H18C 0.9600 .
C19 H19A 0.9600 .
C19 H19B 0.9600 .
C19 H19C 0.9600 .
C20 H20A 0.9600 .
C20 H20B 0.9600 .
C20 H20C 0.9600 .
C21 H21A 0.9600 .
C21 H21B 0.9600 .
C21 H21C 0.9600 .
C22 H22A 0.9600 .
C22 H22B 0.9600 .
C22 H22C 0.9600 .
C23 H23A 0.9600 .
C23 H23B 0.9600 .
C23 H23C 0.9600 .
C24 H24A 0.9600 .
C24 H24B 0.9600 .
C24 H24C 0.9600 .
C25 H25A 0.9600 .
C25 H25B 0.9600 .
C25 H25C 0.9600 .
C26 H26A 0.9600 .
C26 H26B 0.9600 .
C26 H26C 0.9600 .
