#------------------------------------------------------------------------------
#$Date: 2016-03-21 04:01:44 +0200 (Mon, 21 Mar 2016) $
#$Revision: 178456 $
#$URL: svn://www.crystallography.net/cod/cif/4/02/77/4027750.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_4027750
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_moiety         'C32 H44 O4 Si4, 2 (C2 H2 Cl2)'
_chemical_formula_sum            'C34 H48 Cl4 O4 Si4'
_chemical_formula_weight         774.86
_chemical_name_systematic
; 
 ? 
;
_space_group_IT_number           2
_symmetry_cell_setting           triclinic
_symmetry_space_group_name_Hall  '-P 1'
_symmetry_space_group_name_H-M   'P -1'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_audit_creation_method           SHELXL-97
_cell_angle_alpha                119.31
_cell_angle_beta                 101.93
_cell_angle_gamma                100.7470(10)
_cell_formula_units_Z            1
_cell_length_a                   10.63860(10)
_cell_length_b                   10.78470(10)
_cell_length_c                   10.85840(10)
_cell_measurement_reflns_used    373
_cell_measurement_temperature    296(2)
_cell_measurement_theta_max      32.247
_cell_measurement_theta_min      2.181
_cell_volume                     1000.636(18)
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 2008)'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 2008)'
_diffrn_ambient_temperature      296(2)
_diffrn_measured_fraction_theta_full 0.975
_diffrn_measured_fraction_theta_max 0.975
_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  0.0231
_diffrn_reflns_av_sigmaI/netI    0.0212
_diffrn_reflns_limit_h_max       13
_diffrn_reflns_limit_h_min       -13
_diffrn_reflns_limit_k_max       13
_diffrn_reflns_limit_k_min       -13
_diffrn_reflns_limit_l_max       13
_diffrn_reflns_limit_l_min       -14
_diffrn_reflns_number            16929
_diffrn_reflns_theta_full        27.48
_diffrn_reflns_theta_max         27.48
_diffrn_reflns_theta_min         2.08
_exptl_absorpt_coefficient_mu    0.450
_exptl_absorpt_correction_T_max  0.7464
_exptl_absorpt_correction_T_min  0.6918
_exptl_absorpt_correction_type   multi-scan
_exptl_crystal_colour            yellow
_exptl_crystal_density_diffrn    1.286
_exptl_crystal_description       Block
_exptl_crystal_F_000             408
_exptl_crystal_size_max          0.263
_exptl_crystal_size_mid          0.178
_exptl_crystal_size_min          0.095
_refine_diff_density_max         0.617
_refine_diff_density_min         -0.549
_refine_diff_density_rms         0.053
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.040
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     214
_refine_ls_number_reflns         4476
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.040
_refine_ls_R_factor_all          0.0355
_refine_ls_R_factor_gt           0.0304
_refine_ls_shift/su_max          0.001
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'calc w=1/[σ²(Fo²)+(0.0360P)²+0.5920P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0761
_refine_ls_wR_factor_ref         0.0805
_reflns_number_gt                3987
_reflns_number_total             4476
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            jo3015648_si_006.cif
_cod_data_source_block           bharat_046_0m
_cod_database_code               4027750
loop_
_symmetry_equiv_pos_as_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_symmetry_multiplicity
_atom_site_calc_flag
_atom_site_refinement_flags
Si1 Si 0.31248(4) 0.75062(4) 0.49899(4) 0.01522(9) Uani 1 1 d .
Si2 Si 0.75587(4) 0.77920(4) 1.14485(4) 0.01512(9) Uani 1 1 d .
Cl2 Cl 0.94440(4) 0.40394(5) 0.09244(6) 0.04066(12) Uani 1 1 d .
Cl1 Cl 0.70212(5) 0.40029(6) 0.17922(6) 0.04081(12) Uani 1 1 d .
C9 C 0.58886(14) 0.97438(15) 1.01901(14) 0.0141(3) Uani 1 1 d .
C5 C 0.52489(13) 0.91990(15) 0.76186(14) 0.0138(3) Uani 1 1 d .
C10 C 0.73452(13) 0.88739(14) 0.87944(15) 0.0138(3) Uani 1 1 d .
C8 C 0.50198(13) 0.97009(15) 0.89366(15) 0.0143(3) Uani 1 1 d .
C7 C 0.64917(13) 0.88369(15) 0.75613(15) 0.0142(3) Uani 1 1 d .
C6 C 0.69915(13) 0.92893(15) 1.01325(15) 0.0134(3) Uani 1 1 d .
C1 C 0.85500(14) 0.85261(15) 0.86941(16) 0.0169(3) Uani 1 1 d .
H1 H 0.9109 0.8541 0.9486 0.020 Uiso 1 1 calc R
C4 C 0.68869(14) 0.84507(16) 0.62923(15) 0.0176(3) Uani 1 1 d .
H4 H 0.6337 0.8415 0.5481 0.021 Uiso 1 1 calc R
C2 C 0.89107(14) 0.81661(16) 0.74449(17) 0.0205(3) Uani 1 1 d .
H2 H 0.9713 0.7949 0.7402 0.025 Uiso 1 1 calc R
C12 C 0.28384(15) 0.77930(18) 0.34201(16) 0.0219(3) Uani 1 1 d .
H12A H 0.2593 0.8683 0.3709 0.033 Uiso 1 1 calc R
H12B H 0.2115 0.6934 0.2548 0.033 Uiso 1 1 calc R
H12C H 0.3659 0.7911 0.3189 0.033 Uiso 1 1 calc R
C3 C 0.80733(15) 0.81257(17) 0.62361(16) 0.0204(3) Uani 1 1 d .
H3 H 0.8320 0.7879 0.5393 0.024 Uiso 1 1 calc R
C13 C 0.16044(16) 0.73826(18) 0.55657(17) 0.0249(3) Uani 1 1 d .
H13A H 0.1807 0.7304 0.6423 0.037 Uiso 1 1 calc R
H13B H 0.0854 0.6508 0.4748 0.037 Uiso 1 1 calc R
H13C H 0.1365 0.8272 0.5824 0.037 Uiso 1 1 calc R
C11 C 0.36304(17) 0.58222(17) 0.45572(17) 0.0244(3) Uani 1 1 d .
H11A H 0.4354 0.5834 0.4156 0.037 Uiso 1 1 calc R
H11B H 0.2860 0.4923 0.3829 0.037 Uiso 1 1 calc R
H11C H 0.3939 0.5838 0.5462 0.037 Uiso 1 1 calc R
C16 C 0.69995(17) 0.60140(17) 0.95672(17) 0.0237(3) Uani 1 1 d .
H16A H 0.6196 0.5952 0.8913 0.036 Uiso 1 1 calc R
H16B H 0.6800 0.5167 0.9665 0.036 Uiso 1 1 calc R
H16C H 0.7713 0.6003 0.9151 0.036 Uiso 1 1 calc R
C14 C 0.62185(18) 0.77428(19) 1.22912(19) 0.0276(3) Uani 1 1 d .
H14A H 0.6484 0.8677 1.3247 0.041 Uiso 1 1 calc R
H14B H 0.6103 0.6922 1.2431 0.041 Uiso 1 1 calc R
H14C H 0.5374 0.7604 1.1632 0.041 Uiso 1 1 calc R
C15 C 0.92459(17) 0.81706(19) 1.27054(19) 0.0286(3) Uani 1 1 d .
H15A H 0.9915 0.8219 1.2242 0.043 Uiso 1 1 calc R
H15B H 0.9202 0.7374 1.2878 0.043 Uiso 1 1 calc R
H15C H 0.9497 0.9115 1.3648 0.043 Uiso 1 1 calc R
C17 C 0.78018(18) 0.2951(2) 0.0560(2) 0.0335(4) Uani 1 1 d .
H17A H 0.7860 0.2113 0.0655 0.040 Uiso 1 1 calc R
H17B H 0.7238 0.2537 -0.0468 0.040 Uiso 1 1 calc R
O1 O 0.44267(10) 0.90734(11) 0.63857(10) 0.0153(2) Uani 1 1 d .
O2 O 0.78117(9) 0.92666(11) 1.12664(10) 0.01503(19) Uani 1 1 d .
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'
Cl Cl 0.1484 0.1585 '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_3
O1 Si1 C12 103.04(6) .
O1 Si1 C11 109.39(6) .
C12 Si1 C11 113.01(7) .
O1 Si1 C13 109.96(6) .
C12 Si1 C13 111.59(7) .
C11 Si1 C13 109.65(8) .
O2 Si2 C15 103.35(7) .
O2 Si2 C14 109.77(6) .
C15 Si2 C14 112.13(8) .
O2 Si2 C16 109.51(6) .
C15 Si2 C16 112.93(8) .
C14 Si2 C16 109.00(8) .
C6 C9 C8 122.61(12) .
C6 C9 C8 147.29(13) 2_677
C8 C9 C8 90.02(11) 2_677
C8 C5 O1 124.64(12) .
C8 C5 C7 116.51(12) .
O1 C5 C7 118.79(11) .
C1 C10 C7 118.70(12) .
C1 C10 C6 120.68(12) .
C7 C10 C6 120.62(12) .
C5 C8 C9 122.53(12) .
C5 C8 C9 147.39(13) 2_677
C9 C8 C9 89.98(11) 2_677
C4 C7 C10 118.70(12) .
C4 C7 C5 120.61(12) .
C10 C7 C5 120.68(12) .
C9 C6 O2 124.56(12) .
C9 C6 C10 116.57(12) .
O2 C6 C10 118.80(11) .
C2 C1 C10 121.10(13) .
C2 C1 H1 119.4 .
C10 C1 H1 119.4 .
C3 C4 C7 121.05(13) .
C3 C4 H4 119.5 .
C7 C4 H4 119.5 .
C1 C2 C3 120.20(13) .
C1 C2 H2 119.9 .
C3 C2 H2 119.9 .
Si1 C12 H12A 109.5 .
Si1 C12 H12B 109.5 .
H12A C12 H12B 109.5 .
Si1 C12 H12C 109.5 .
H12A C12 H12C 109.5 .
H12B C12 H12C 109.5 .
C4 C3 C2 120.25(13) .
C4 C3 H3 119.9 .
C2 C3 H3 119.9 .
Si1 C13 H13A 109.5 .
Si1 C13 H13B 109.5 .
H13A C13 H13B 109.5 .
Si1 C13 H13C 109.5 .
H13A C13 H13C 109.5 .
H13B C13 H13C 109.5 .
Si1 C11 H11A 109.5 .
Si1 C11 H11B 109.5 .
H11A C11 H11B 109.5 .
Si1 C11 H11C 109.5 .
H11A C11 H11C 109.5 .
H11B C11 H11C 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 C14 H14A 109.5 .
Si2 C14 H14B 109.5 .
H14A C14 H14B 109.5 .
Si2 C14 H14C 109.5 .
H14A C14 H14C 109.5 .
H14B C14 H14C 109.5 .
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 .
Cl2 C17 Cl1 112.52(10) .
Cl2 C17 H17A 109.1 .
Cl1 C17 H17A 109.1 .
Cl2 C17 H17B 109.1 .
Cl1 C17 H17B 109.1 .
H17A C17 H17B 107.8 .
C5 O1 Si1 124.26(8) .
C6 O2 Si2 124.49(8) .
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
Si1 O1 1.6804(10) .
Si1 C12 1.8522(15) .
Si1 C11 1.8553(15) .
Si1 C13 1.8558(16) .
Si2 O2 1.6766(10) .
Si2 C15 1.8493(16) .
Si2 C14 1.8524(16) .
Si2 C16 1.8551(15) .
Cl2 C17 1.7554(18) .
Cl1 C17 1.7580(19) .
C9 C6 1.3549(19) .
C9 C8 1.4530(18) .
C9 C8 1.4935(18) 2_677
C5 C8 1.3549(18) .
C5 O1 1.3674(15) .
C5 C7 1.4517(18) .
C10 C1 1.4115(18) .
C10 C7 1.4319(19) .
C10 C6 1.4509(18) .
C8 C9 1.4935(18) 2_677
C7 C4 1.4113(18) .
C6 O2 1.3679(16) .
C1 C2 1.376(2) .
C1 H1 0.9300 .
C4 C3 1.377(2) .
C4 H4 0.9300 .
C2 C3 1.402(2) .
C2 H2 0.9300 .
C12 H12A 0.9600 .
C12 H12B 0.9600 .
C12 H12C 0.9600 .
C3 H3 0.9300 .
C13 H13A 0.9600 .
C13 H13B 0.9600 .
C13 H13C 0.9600 .
C11 H11A 0.9600 .
C11 H11B 0.9600 .
C11 H11C 0.9600 .
C16 H16A 0.9600 .
C16 H16B 0.9600 .
C16 H16C 0.9600 .
C14 H14A 0.9600 .
C14 H14B 0.9600 .
C14 H14C 0.9600 .
C15 H15A 0.9600 .
C15 H15B 0.9600 .
C15 H15C 0.9600 .
C17 H17A 0.9700 .
C17 H17B 0.9700 .
