#------------------------------------------------------------------------------
#$Date: 2016-03-21 03:07:09 +0200 (Mon, 21 Mar 2016) $
#$Revision: 178421 $
#$URL: svn://www.crystallography.net/cod/cif/4/02/42/4024211.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_4024211
loop_
_publ_author_name
'Cameron L. Hilton'
'Christopher R. Jamison'
'Hannah K. Zane'
'Benjamin T. King'
_publ_section_title
;
A Triphenylene-Based Triptycene with Large Free Volume Synthesized by
Zirconium-Mediated Biphenylation
;
_journal_name_full               'Journal of Organic Chemistry'
_journal_page_first              405
_journal_page_last               407
_journal_paper_doi               10.1021/jo801643u
_journal_volume                  74
_journal_year                    2009
_chemical_formula_sum            'C28 H24 Br6'
_chemical_formula_weight         839.93
_chemical_name_systematic
; 
  2,3,6,7,12,13-hexabromo-9,10-dibutyltriptycene  
;
_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                106.1940(10)
_cell_angle_beta                 91.6170(10)
_cell_angle_gamma                106.4090(10)
_cell_formula_units_Z            2
_cell_length_a                   9.3770(2)
_cell_length_b                   10.8057(2)
_cell_length_c                   14.9048(3)
_cell_measurement_reflns_used    534
_cell_measurement_temperature    100(2)
_cell_measurement_theta_max      33.0
_cell_measurement_theta_min      1.2
_cell_volume                     1381.82(5)
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 1990)'
_diffrn_ambient_temperature      100(2)
_diffrn_measured_fraction_theta_full 0.977
_diffrn_measured_fraction_theta_max 0.977
_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  0.0245
_diffrn_reflns_av_sigmaI/netI    0.0286
_diffrn_reflns_limit_h_max       13
_diffrn_reflns_limit_h_min       -13
_diffrn_reflns_limit_k_max       15
_diffrn_reflns_limit_k_min       -14
_diffrn_reflns_limit_l_max       19
_diffrn_reflns_limit_l_min       -20
_diffrn_reflns_number            25253
_diffrn_reflns_theta_full        30.00
_diffrn_reflns_theta_max         30.00
_diffrn_reflns_theta_min         2.06
_exptl_absorpt_coefficient_mu    8.733
_exptl_absorpt_correction_T_max  0.5720
_exptl_absorpt_correction_T_min  0.3102
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   SADABS
_exptl_crystal_colour            colorless
_exptl_crystal_density_diffrn    2.019
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       rod
_exptl_crystal_F_000             804
_exptl_crystal_size_max          0.17
_exptl_crystal_size_mid          0.08
_exptl_crystal_size_min          0.07
_refine_diff_density_max         0.670
_refine_diff_density_min         -0.445
_refine_diff_density_rms         0.108
_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     309
_refine_ls_number_reflns         7870
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.042
_refine_ls_R_factor_all          0.0365
_refine_ls_R_factor_gt           0.0242
_refine_ls_shift/su_max          0.002
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'calc w=1/[σ²(Fo²)+(0.0308P)²+0.0721P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0533
_refine_ls_wR_factor_ref         0.0568
_reflns_number_gt                6466
_reflns_number_total             7870
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            jo801643u_si_003.cif
_cod_data_source_block           ch247_0m
_cod_original_sg_symbol_H-M      P-1
_cod_database_code               4024211
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
Br1 Br 0.17948(2) 0.45456(2) 0.593802(16) 0.02032(6) Uani 1 1 d . . .
Br2 Br 0.51502(2) 0.70033(2) 0.653742(15) 0.02087(6) Uani 1 1 d . . .
Br3 Br 0.74503(2) 0.41063(2) 0.021742(15) 0.01508(5) Uani 1 1 d . . .
Br4 Br 0.40848(2) 0.17727(2) -0.040663(15) 0.01377(5) Uani 1 1 d . . .
Br5 Br -0.05349(2) 0.81898(2) 0.118427(16) 0.01688(5) Uani 1 1 d . . .
Br6 Br 0.29419(2) 1.03428(2) 0.143122(16) 0.01731(5) Uani 1 1 d . . .
C1 C 0.2074(2) 0.4915(2) 0.41421(15) 0.0133(4) Uani 1 1 d . . .
H1 H 0.1111 0.4264 0.3983 0.016 Uiso 1 1 calc R . .
C2 C 0.2786(2) 0.5347(2) 0.50571(15) 0.0140(4) Uani 1 1 d . . .
C3 C 0.4182(2) 0.6307(2) 0.52913(15) 0.0141(4) Uani 1 1 d . . .
C4 C 0.4890(2) 0.6831(2) 0.46172(15) 0.0129(4) Uani 1 1 d . . .
H4 H 0.5859 0.7472 0.4778 0.015 Uiso 1 1 calc R . .
C5 C 0.5996(2) 0.5484(2) 0.16300(14) 0.0119(4) Uani 1 1 d . . .
H5 H 0.6949 0.6150 0.1809 0.014 Uiso 1 1 calc R . .
C6 C 0.5801(2) 0.4321(2) 0.08815(14) 0.0116(4) Uani 1 1 d . . .
C7 C 0.4408(2) 0.3360(2) 0.06146(14) 0.0104(4) Uani 1 1 d . . .
C8 C 0.3196(2) 0.3533(2) 0.11043(14) 0.0113(4) Uani 1 1 d . . .
H8 H 0.2243 0.2868 0.0921 0.014 Uiso 1 1 calc R . .
C9 C 0.4814(2) 0.6949(2) 0.29008(14) 0.0104(4) Uani 1 1 d . . .
C10 C 0.2144(2) 0.5045(2) 0.24278(14) 0.0104(4) Uani 1 1 d . . .
C11 C 0.0944(2) 0.6663(2) 0.19104(14) 0.0120(4) Uani 1 1 d . . .
H11 H -0.0024 0.6022 0.1797 0.014 Uiso 1 1 calc R . .
C12 C 0.1151(2) 0.7877(2) 0.17066(14) 0.0117(4) Uani 1 1 d . . .
C13 C 0.2562(2) 0.8808(2) 0.18570(15) 0.0120(4) Uani 1 1 d . . .
C14 C 0.3772(2) 0.8575(2) 0.22781(14) 0.0116(4) Uani 1 1 d . . .
H14 H 0.4730 0.9234 0.2411 0.014 Uiso 1 1 calc R . .
C15 C 0.2779(2) 0.5439(2) 0.34678(14) 0.0116(4) Uani 1 1 d . . .
C16 C 0.4188(2) 0.6422(2) 0.37084(14) 0.0106(4) Uani 1 1 d . . .
C17 C 0.3391(2) 0.4680(2) 0.18594(14) 0.0097(4) Uani 1 1 d . . .
C18 C 0.4795(2) 0.5667(2) 0.21131(14) 0.0106(4) Uani 1 1 d . . .
C19 C 0.2156(2) 0.6394(2) 0.22803(14) 0.0103(4) Uani 1 1 d . . .
C20 C 0.3570(2) 0.7385(2) 0.24991(14) 0.0106(4) Uani 1 1 d . . .
C21 C 0.6360(2) 0.8018(2) 0.31656(15) 0.0127(4) Uani 1 1 d . . .
H21A H 0.6697 0.8226 0.2586 0.015 Uiso 1 1 calc R . .
H21B H 0.7069 0.7607 0.3385 0.015 Uiso 1 1 calc R . .
C22 C 0.6493(2) 0.9366(2) 0.39201(15) 0.0141(4) Uani 1 1 d . . .
H22A H 0.6362 1.0031 0.3608 0.017 Uiso 1 1 calc R . .
H22B H 0.5683 0.9222 0.4327 0.017 Uiso 1 1 calc R . .
C23 C 0.8005(2) 0.9937(2) 0.45280(16) 0.0186(5) Uani 1 1 d . . .
H23A H 0.8136 0.9266 0.4834 0.022 Uiso 1 1 calc R . .
H23B H 0.8811 1.0081 0.4119 0.022 Uiso 1 1 calc R . .
C24 C 0.8164(3) 1.1265(2) 0.52823(18) 0.0271(6) Uani 1 1 d . . .
H24A H 0.8090 1.1949 0.4983 0.041 Uiso 1 1 calc R . .
H24B H 0.9138 1.1569 0.5661 0.041 Uiso 1 1 calc R . .
H24C H 0.7365 1.1133 0.5688 0.041 Uiso 1 1 calc R . .
C25 C 0.0601(2) 0.3979(2) 0.21561(15) 0.0127(4) Uani 1 1 d . . .
H25A H 0.0266 0.3868 0.1495 0.015 Uiso 1 1 calc R . .
H25B H -0.0108 0.4342 0.2549 0.015 Uiso 1 1 calc R . .
C26 C 0.0468(2) 0.2561(2) 0.22485(16) 0.0155(4) Uani 1 1 d . . .
H26A H 0.0611 0.1972 0.1639 0.019 Uiso 1 1 calc R . .
H26B H 0.1275 0.2641 0.2724 0.019 Uiso 1 1 calc R . .
C27 C -0.1046(2) 0.1901(2) 0.25353(17) 0.0209(5) Uani 1 1 d . . .
H27A H -0.1059 0.1011 0.2600 0.025 Uiso 1 1 calc R . .
H27B H -0.1170 0.2472 0.3157 0.025 Uiso 1 1 calc R . .
C28 C -0.2357(2) 0.1705(3) 0.1826(2) 0.0286(6) Uani 1 1 d . . .
H28A H -0.2445 0.2589 0.1831 0.043 Uiso 1 1 calc R . .
H28B H -0.3284 0.1174 0.1997 0.043 Uiso 1 1 calc R . .
H28C H -0.2186 0.1226 0.1196 0.043 Uiso 1 1 calc R . .
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'
Br Br -0.2901 2.4595 '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
_geom_angle_publ_flag
C15 C1 C2 119.55(19) . . ?
C3 C2 C1 120.17(19) . . ?
C3 C2 Br1 122.25(16) . . ?
C1 C2 Br1 117.56(15) . . ?
C2 C3 C4 120.36(19) . . ?
C2 C3 Br2 121.94(16) . . ?
C4 C3 Br2 117.65(15) . . ?
C16 C4 C3 120.03(19) . . ?
C18 C5 C6 119.62(18) . . ?
C7 C6 C5 120.10(18) . . ?
C7 C6 Br3 120.96(16) . . ?
C5 C6 Br3 118.91(14) . . ?
C6 C7 C8 120.52(19) . . ?
C6 C7 Br4 121.57(15) . . ?
C8 C7 Br4 117.91(15) . . ?
C17 C8 C7 119.58(18) . . ?
C16 C9 C21 114.52(16) . . ?
C16 C9 C20 105.64(15) . . ?
C21 C9 C20 115.48(16) . . ?
C16 C9 C18 104.37(16) . . ?
C21 C9 C18 113.35(16) . . ?
C20 C9 C18 102.11(15) . . ?
C19 C10 C25 113.11(15) . . ?
C19 C10 C17 102.91(16) . . ?
C25 C10 C17 115.45(17) . . ?
C19 C10 C15 103.75(16) . . ?
C25 C10 C15 114.94(17) . . ?
C17 C10 C15 105.29(15) . . ?
C19 C11 C12 119.66(18) . . ?
C13 C12 C11 120.44(17) . . ?
C13 C12 Br5 121.39(15) . . ?
C11 C12 Br5 118.15(14) . . ?
C12 C13 C14 120.08(19) . . ?
C12 C13 Br6 121.71(15) . . ?
C14 C13 Br6 118.07(15) . . ?
C20 C14 C13 119.72(18) . . ?
C1 C15 C16 120.20(19) . . ?
C1 C15 C10 125.45(18) . . ?
C16 C15 C10 114.35(18) . . ?
C4 C16 C15 119.63(19) . . ?
C4 C16 C9 125.68(18) . . ?
C15 C16 C9 114.69(17) . . ?
C8 C17 C18 119.70(18) . . ?
C8 C17 C10 125.33(17) . . ?
C18 C17 C10 114.81(17) . . ?
C5 C18 C17 120.45(19) . . ?
C5 C18 C9 125.23(18) . . ?
C17 C18 C9 114.19(17) . . ?
C11 C19 C20 119.78(18) . . ?
C11 C19 C10 125.59(17) . . ?
C20 C19 C10 114.52(16) . . ?
C14 C20 C19 120.05(17) . . ?
C14 C20 C9 125.46(17) . . ?
C19 C20 C9 114.26(17) . . ?
C9 C21 C22 117.65(16) . . ?
C23 C22 C21 111.92(16) . . ?
C24 C23 C22 113.05(18) . . ?
C10 C25 C26 117.56(16) . . ?
C27 C26 C25 112.52(17) . . ?
C28 C27 C26 112.7(2) . . ?
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
Br1 C2 1.894(2) . ?
Br2 C3 1.892(2) . ?
Br3 C6 1.8940(19) . ?
Br4 C7 1.891(2) . ?
Br5 C12 1.8965(18) . ?
Br6 C13 1.883(2) . ?
C1 C15 1.383(3) . ?
C1 C2 1.393(3) . ?
C2 C3 1.384(3) . ?
C3 C4 1.383(3) . ?
C4 C16 1.384(3) . ?
C5 C18 1.386(3) . ?
C5 C6 1.391(3) . ?
C6 C7 1.384(3) . ?
C7 C8 1.397(3) . ?
C8 C17 1.385(3) . ?
C9 C16 1.534(3) . ?
C9 C21 1.536(3) . ?
C9 C20 1.539(3) . ?
C9 C18 1.541(3) . ?
C10 C19 1.531(3) . ?
C10 C25 1.533(3) . ?
C10 C17 1.539(3) . ?
C10 C15 1.541(3) . ?
C11 C19 1.387(3) . ?
C11 C12 1.390(3) . ?
C12 C13 1.385(3) . ?
C13 C14 1.398(3) . ?
C14 C20 1.379(3) . ?
C15 C16 1.403(3) . ?
C17 C18 1.402(3) . ?
C19 C20 1.411(3) . ?
C21 C22 1.542(3) . ?
C22 C23 1.528(3) . ?
C23 C24 1.521(3) . ?
C25 C26 1.547(3) . ?
C26 C27 1.530(3) . ?
C27 C28 1.526(3) . ?
