#------------------------------------------------------------------------------
#$Date: 2015-11-06 07:00:16 +0200 (Fri, 06 Nov 2015) $
#$Revision: 170092 $
#$URL: svn://www.crystallography.net/cod/cif/4/03/15/4031542.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_4031542
loop_
_publ_author_name
'Kaleta, Jiří'
'Kaletová, Eva'
'Císařová, Ivana'
'Teat, Simon J.'
'Michl, Josef'
_publ_section_title
;
 Synthesis of Triptycene-Based Molecular Rotors for Langmuir-Blodgett
 Monolayers.
;
_journal_issue                   20
_journal_name_full               'The Journal of organic chemistry'
_journal_page_first              10134
_journal_page_last               10150
_journal_paper_doi               10.1021/acs.joc.5b01753
_journal_volume                  80
_journal_year                    2015
_chemical_compound_source        'synthesized by dr. Jiri Kaleta'
_chemical_formula_moiety         'C58 H42 Si2, 2(C H2 Cl2)'
_chemical_formula_sum            'C60 H46 Cl4 Si2'
_chemical_formula_weight         964.95
_chemical_name_systematic
; 
 ? 
;
_space_group_IT_number           2
_space_group_name_Hall           '-P 1'
_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                94.119(2)
_cell_angle_beta                 102.2186(19)
_cell_angle_gamma                111.0808(18)
_cell_formula_units_Z            1
_cell_length_a                   9.0476(4)
_cell_length_b                   11.7771(6)
_cell_length_c                   13.5039(7)
_cell_measurement_reflns_used    9974
_cell_measurement_temperature    150(2)
_cell_measurement_theta_max      27.4997
_cell_measurement_theta_min      2.2406
_cell_volume                     1294.80(11)
_computing_cell_refinement       'SAINT V8.34A (Bruker AXS Inc., 2013)'
_computing_data_collection       'Bruker Instrument Service v2014.5.0.0'
_computing_data_reduction        'SAINT V8.34A (Bruker AXS Inc., 2013)'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_computing_structure_solution    'SHELXL-2014 (Sheldrick, 2014)'
_diffrn_ambient_temperature      150(2)
_diffrn_measured_fraction_theta_full 0.999
_diffrn_measured_fraction_theta_max 0.999
_diffrn_measurement_device_type  'Bruker APEX-II CCD'
_diffrn_measurement_method       'φ and ω scans'
_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  0.0140
_diffrn_reflns_av_sigmaI/netI    0.0128
_diffrn_reflns_limit_h_max       11
_diffrn_reflns_limit_h_min       -10
_diffrn_reflns_limit_k_max       15
_diffrn_reflns_limit_k_min       -15
_diffrn_reflns_limit_l_max       17
_diffrn_reflns_limit_l_min       -17
_diffrn_reflns_number            22644
_diffrn_reflns_theta_full        27.50
_diffrn_reflns_theta_max         27.50
_diffrn_reflns_theta_min         1.56
_diffrn_standards_number         0
_exptl_absorpt_coefficient_mu    0.313
_exptl_absorpt_correction_T_max  0.8360
_exptl_absorpt_correction_T_min  0.7802
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   'SADABS V2014/3 (Bruker AXS Inc.)'
_exptl_crystal_colour            colourless
_exptl_crystal_density_diffrn    1.238
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       prism
_exptl_crystal_F_000             502
_exptl_crystal_size_max          0.84
_exptl_crystal_size_mid          0.72
_exptl_crystal_size_min          0.59
_refine_diff_density_max         1.006
_refine_diff_density_min         -0.634
_refine_diff_density_rms         0.050
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.029
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     323
_refine_ls_number_reflns         5951
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.029
_refine_ls_R_factor_all          0.0490
_refine_ls_R_factor_gt           0.0451
_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)+(0.0514P)²+1.0074P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1149
_refine_ls_wR_factor_ref         0.1181
_reflns_number_gt                5394
_reflns_number_total             5951
_reflns_threshold_expression     I>2σ(I)
_cod_data_source_file            jo5b01753_si_010.cif
_cod_data_source_block           JK561
_cod_depositor_comments
'Adding full bibliography for 4031540--4031548.cif.'
_cod_database_code               4031542
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
_atom_site_disorder_assembly
_atom_site_disorder_group
C1 C 0.4764(2) -0.45880(14) 0.02380(13) 0.0275(3) Uani 1 1 d . . .
C2 C 0.4356(2) -0.38494(14) 0.06571(13) 0.0264(3) Uani 1 1 d . . .
C3 C 0.39093(19) -0.29829(14) 0.11006(12) 0.0247(3) Uani 1 1 d . . .
C4 C 0.35300(18) -0.22047(13) 0.14688(12) 0.0228(3) Uani 1 1 d . . .
C5 C 0.30736(17) -0.12120(12) 0.18409(11) 0.0199(3) Uani 1 1 d . . .
C6 C 0.42352(17) 0.00708(13) 0.17228(11) 0.0198(3) Uani 1 1 d . . .
C7 C 0.55931(18) 0.03153(14) 0.13316(12) 0.0246(3) Uani 1 1 d . . .
H7 H 0.5893 -0.0336 0.1110 0.030 Uiso 1 1 calc R . .
C8 C 0.65168(19) 0.15319(15) 0.12668(13) 0.0285(3) Uani 1 1 d . . .
H8 H 0.7445 0.1709 0.0993 0.034 Uiso 1 1 calc R . .
C9 C 0.60887(19) 0.24850(14) 0.15996(13) 0.0277(3) Uani 1 1 d . . .
H9 H 0.6726 0.3310 0.1552 0.033 Uiso 1 1 calc R . .
C10 C 0.47275(18) 0.22391(13) 0.20037(12) 0.0237(3) Uani 1 1 d . . .
H10 H 0.4441 0.2892 0.2238 0.028 Uiso 1 1 calc R . .
C11 C 0.37990(17) 0.10287(13) 0.20578(11) 0.0200(3) Uani 1 1 d . . .
C12 C 0.22477(18) 0.05906(13) 0.24574(11) 0.0207(3) Uani 1 1 d . . .
C13 C 0.26015(18) -0.01511(13) 0.33047(11) 0.0211(3) Uani 1 1 d . . .
C14 C 0.2479(2) 0.00422(14) 0.43031(12) 0.0266(3) Uani 1 1 d . . .
H14 H 0.2153 0.0680 0.4521 0.032 Uiso 1 1 calc R . .
C15 C 0.2841(2) -0.07150(15) 0.49841(13) 0.0316(4) Uani 1 1 d . . .
H15 H 0.2758 -0.0592 0.5670 0.038 Uiso 1 1 calc R . .
C16 C 0.3322(2) -0.16423(15) 0.46695(13) 0.0303(3) Uani 1 1 d . . .
H16 H 0.3582 -0.2142 0.5144 0.036 Uiso 1 1 calc R . .
C17 C 0.34279(19) -0.18494(14) 0.36591(12) 0.0256(3) Uani 1 1 d . . .
H17 H 0.3749 -0.2491 0.3442 0.031 Uiso 1 1 calc R . .
C18 C 0.30584(18) -0.11068(13) 0.29811(11) 0.0207(3) Uani 1 1 d . . .
C19 C 0.09080(17) -0.03842(13) 0.15879(11) 0.0202(3) Uani 1 1 d . . .
C20 C -0.06248(18) -0.03859(14) 0.11622(12) 0.0236(3) Uani 1 1 d . . .
H20 H -0.0920 0.0266 0.1388 0.028 Uiso 1 1 calc R . .
C21 C -0.17315(19) -0.13567(15) 0.03966(12) 0.0268(3) Uani 1 1 d . . .
H21 H -0.2788 -0.1367 0.0102 0.032 Uiso 1 1 calc R . .
C22 C -0.12990(19) -0.23071(15) 0.00621(12) 0.0276(3) Uani 1 1 d . . .
H22 H -0.2058 -0.2960 -0.0464 0.033 Uiso 1 1 calc R . .
C23 C 0.02460(19) -0.23084(13) 0.04954(12) 0.0240(3) Uani 1 1 d . . .
H23 H 0.0540 -0.2962 0.0271 0.029 Uiso 1 1 calc R . .
C24 C 0.13443(17) -0.13458(13) 0.12564(11) 0.0200(3) Uani 1 1 d . . .
C25 C 0.18068(19) 0.16102(14) 0.27824(12) 0.0243(3) Uani 1 1 d . . .
C26 C 0.1499(2) 0.24895(14) 0.30113(13) 0.0280(3) Uani 1 1 d . . .
C27 C 0.3023(3) 0.49998(17) 0.42804(17) 0.0438(5) Uani 1 1 d . . .
H27A H 0.3296 0.4609 0.4871 0.066 Uiso 1 1 calc R . .
H27B H 0.2837 0.5733 0.4513 0.066 Uiso 1 1 calc R . .
H27C H 0.3930 0.5240 0.3949 0.066 Uiso 1 1 calc R . .
C28 C -0.0607(2) 0.34730(18) 0.39487(14) 0.0357(4) Uani 1 1 d . . .
H28A H -0.1564 0.2818 0.3481 0.054 Uiso 1 1 calc R . .
H28B H -0.0869 0.4198 0.4088 0.054 Uiso 1 1 calc R . .
H28C H -0.0314 0.3180 0.4594 0.054 Uiso 1 1 calc R . .
C29 C 0.0733(2) 0.45381(16) 0.21447(14) 0.0353(4) Uani 1 1 d . . .
H29A H 0.1680 0.4728 0.1850 0.053 Uiso 1 1 calc R . .
H29B H 0.0546 0.5293 0.2300 0.053 Uiso 1 1 calc R . .
H29C H -0.0239 0.3931 0.1651 0.053 Uiso 1 1 calc R . .
Si1 Si 0.11391(5) 0.38945(4) 0.33490(3) 0.02379(11) Uani 1 1 d . . .
C1S C 0.8504(3) 0.7345(2) 0.28646(19) 0.0459(5) Uani 0.9296(15) 1 d P A 1
H1S1 H 0.9674 0.7626 0.3235 0.055 Uiso 0.9296(15) 1 calc PR A 1
H1S2 H 0.8447 0.7425 0.2134 0.055 Uiso 0.9296(15) 1 calc PR A 1
Cl1S Cl 0.75022(11) 0.57889(6) 0.29545(6) 0.0730(3) Uani 0.9296(15) 1 d P A 1
Cl2S Cl 0.76592(10) 0.82960(8) 0.33712(6) 0.0754(3) Uani 0.9296(15) 1 d P A 1
C2S C 0.753(5) 0.697(3) 0.269(3) 0.0459(5) Uani 0.0704(15) 1 d P A 2
H2S1 H 0.7424 0.7685 0.3050 0.055 Uiso 0.0704(15) 1 calc PR A 2
H2S2 H 0.7361 0.7039 0.1949 0.055 Uiso 0.0704(15) 1 calc PR A 2
Cl3S Cl 0.9528(8) 0.6989(7) 0.3180(7) 0.048(2) Uani 0.0704(15) 1 d P A 2
Cl4S Cl 0.6044(10) 0.5635(11) 0.2833(8) 0.090(5) Uani 0.0704(15) 1 d P A 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'
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
C2 C1 C1 179.4(2) 2_645
C1 C2 C3 177.59(17) .
C4 C3 C2 178.19(17) .
C3 C4 C5 175.32(16) .
C4 C5 C18 114.97(12) .
C4 C5 C6 112.63(12) .
C18 C5 C6 105.17(11) .
C4 C5 C24 112.66(12) .
C18 C5 C24 104.95(11) .
C6 C5 C24 105.62(11) .
C7 C6 C11 120.61(13) .
C7 C6 C5 126.01(12) .
C11 C6 C5 113.38(12) .
C6 C7 C8 119.08(14) .
C6 C7 H7 120.5 .
C8 C7 H7 120.5 .
C9 C8 C7 120.46(14) .
C9 C8 H8 119.8 .
C7 C8 H8 119.8 .
C8 C9 C10 120.43(14) .
C8 C9 H9 119.8 .
C10 C9 H9 119.8 .
C11 C10 C9 119.11(14) .
C11 C10 H10 120.4 .
C9 C10 H10 120.4 .
C10 C11 C6 120.29(13) .
C10 C11 C12 126.01(12) .
C6 C11 C12 113.70(12) .
C25 C12 C13 114.78(12) .
C25 C12 C11 112.35(12) .
C13 C12 C11 105.11(11) .
C25 C12 C19 113.60(12) .
C13 C12 C19 104.27(11) .
C11 C12 C19 105.84(11) .
C14 C13 C18 120.34(14) .
C14 C13 C12 125.89(13) .
C18 C13 C12 113.76(12) .
C13 C14 C15 118.99(14) .
C13 C14 H14 120.5 .
C15 C14 H14 120.5 .
C16 C15 C14 120.61(15) .
C16 C15 H15 119.7 .
C14 C15 H15 119.7 .
C15 C16 C17 120.54(15) .
C15 C16 H16 119.7 .
C17 C16 H16 119.7 .
C18 C17 C16 118.97(14) .
C18 C17 H17 120.5 .
C16 C17 H17 120.5 .
C17 C18 C13 120.52(13) .
C17 C18 C5 126.31(13) .
C13 C18 C5 113.16(12) .
C20 C19 C24 120.47(13) .
C20 C19 C12 125.78(12) .
C24 C19 C12 113.72(12) .
C19 C20 C21 119.19(14) .
C19 C20 H20 120.4 .
C21 C20 H20 120.4 .
C22 C21 C20 120.47(14) .
C22 C21 H21 119.8 .
C20 C21 H21 119.8 .
C21 C22 C23 120.34(14) .
C21 C22 H22 119.8 .
C23 C22 H22 119.8 .
C24 C23 C22 119.21(14) .
C24 C23 H23 120.4 .
C22 C23 H23 120.4 .
C23 C24 C19 120.32(13) .
C23 C24 C5 126.41(13) .
C19 C24 C5 113.24(12) .
C26 C25 C12 175.95(17) .
C25 C26 Si1 176.73(15) .
Si1 C27 H27A 109.5 .
Si1 C27 H27B 109.5 .
H27A C27 H27B 109.5 .
Si1 C27 H27C 109.5 .
H27A C27 H27C 109.5 .
H27B C27 H27C 109.5 .
Si1 C28 H28A 109.5 .
Si1 C28 H28B 109.5 .
H28A C28 H28B 109.5 .
Si1 C28 H28C 109.5 .
H28A C28 H28C 109.5 .
H28B C28 H28C 109.5 .
Si1 C29 H29A 109.5 .
Si1 C29 H29B 109.5 .
H29A C29 H29B 109.5 .
Si1 C29 H29C 109.5 .
H29A C29 H29C 109.5 .
H29B C29 H29C 109.5 .
C26 Si1 C28 108.33(8) .
C26 Si1 C27 107.72(9) .
C28 Si1 C27 110.05(10) .
C26 Si1 C29 107.47(8) .
C28 Si1 C29 112.64(8) .
C27 Si1 C29 110.46(9) .
Cl2S C1S Cl1S 112.81(14) .
Cl2S C1S H1S1 109.0 .
Cl1S C1S H1S1 109.0 .
Cl2S C1S H1S2 109.0 .
Cl1S C1S H1S2 109.0 .
H1S1 C1S H1S2 107.8 .
Cl4S C2S Cl3S 111.3(19) .
Cl4S C2S H2S1 109.4 .
Cl3S C2S H2S1 109.4 .
Cl4S C2S H2S2 109.4 .
Cl3S C2S H2S2 109.4 .
H2S1 C2S H2S2 108.0 .
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
C1 C2 1.209(2) .
C1 C1 1.364(3) 2_645
C2 C3 1.369(2) .
C3 C4 1.199(2) .
C4 C5 1.4631(18) .
C5 C18 1.539(2) .
C5 C6 1.5414(19) .
C5 C24 1.542(2) .
C6 C7 1.383(2) .
C6 C11 1.3984(19) .
C7 C8 1.395(2) .
C7 H7 0.9500 .
C8 C9 1.388(2) .
C8 H8 0.9500 .
C9 C10 1.396(2) .
C9 H9 0.9500 .
C10 C11 1.387(2) .
C10 H10 0.9500 .
C11 C12 1.5385(19) .
C12 C25 1.4618(19) .
C12 C13 1.538(2) .
C12 C19 1.539(2) .
C13 C14 1.385(2) .
C13 C18 1.4033(19) .
C14 C15 1.396(2) .
C14 H14 0.9500 .
C15 C16 1.384(2) .
C15 H15 0.9500 .
C16 C17 1.398(2) .
C16 H16 0.9500 .
C17 C18 1.382(2) .
C17 H17 0.9500 .
C19 C20 1.384(2) .
C19 C24 1.4008(18) .
C20 C21 1.395(2) .
C20 H20 0.9500 .
C21 C22 1.388(2) .
C21 H21 0.9500 .
C22 C23 1.397(2) .
C22 H22 0.9500 .
C23 C24 1.385(2) .
C23 H23 0.9500 .
C25 C26 1.201(2) .
C26 Si1 1.8424(16) .
C27 Si1 1.8554(19) .
C27 H27A 0.9800 .
C27 H27B 0.9800 .
C27 H27C 0.9800 .
C28 Si1 1.8533(18) .
C28 H28A 0.9800 .
C28 H28B 0.9800 .
C28 H28C 0.9800 .
C29 Si1 1.8651(18) .
C29 H29A 0.9800 .
C29 H29B 0.9800 .
C29 H29C 0.9800 .
C1S Cl2S 1.741(2) .
C1S Cl1S 1.755(2) .
C1S H1S1 0.9900 .
C1S H1S2 0.9900 .
C2S Cl4S 1.71(3) .
C2S Cl3S 1.78(4) .
C2S H2S1 0.9900 .
C2S H2S2 0.9900 .
