#------------------------------------------------------------------------------
#$Date: 2016-03-21 03:07:09 +0200 (Mon, 21 Mar 2016) $
#$Revision: 178421 $
#$URL: svn://www.crystallography.net/cod/cif/4/02/42/4024213.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_4024213
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_moiety         'C20 H8 Br6, C3 H6 O'
_chemical_formula_sum            'C23 H14 Br6 O'
_chemical_formula_weight         785.80
_chemical_name_systematic
; 
 2,3,6,7,12,13-hexabromotriptycene 
;
_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                71.3190(10)
_cell_angle_beta                 83.6040(10)
_cell_angle_gamma                83.1500(10)
_cell_formula_units_Z            2
_cell_length_a                   9.3588(3)
_cell_length_b                   10.6539(3)
_cell_length_c                   12.7806(4)
_cell_measurement_reflns_used    341
_cell_measurement_temperature    100(2)
_cell_measurement_theta_max      33.3
_cell_measurement_theta_min      1.2
_cell_volume                     1194.94(6)
_computing_cell_refinement       'Bruker SMART'
_computing_data_collection       'Bruker SMART'
_computing_data_reduction        'Bruker SAINT'
_computing_molecular_graphics    'Bruker SHELXTL'
_computing_publication_material  'Bruker SHELXTL'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 1990)'
_diffrn_ambient_temperature      100(2)
_diffrn_measured_fraction_theta_full 0.978
_diffrn_measured_fraction_theta_max 0.978
_diffrn_measurement_device_type  'CCD area detector'
_diffrn_measurement_method       'phi and omega 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  0.0281
_diffrn_reflns_av_sigmaI/netI    0.0325
_diffrn_reflns_limit_h_max       13
_diffrn_reflns_limit_h_min       -14
_diffrn_reflns_limit_k_max       16
_diffrn_reflns_limit_k_min       -15
_diffrn_reflns_limit_l_max       19
_diffrn_reflns_limit_l_min       -18
_diffrn_reflns_number            27432
_diffrn_reflns_theta_full        32.65
_diffrn_reflns_theta_max         32.65
_diffrn_reflns_theta_min         1.69
_exptl_absorpt_coefficient_mu    10.094
_exptl_absorpt_correction_T_max  0.3055
_exptl_absorpt_correction_T_min  0.1517
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   'SADABS V2.10 (Sheldrick, G.M., 2003)'
_exptl_crystal_colour            color
_exptl_crystal_density_diffrn    2.184
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       block
_exptl_crystal_F_000             740
_exptl_crystal_size_max          0.30
_exptl_crystal_size_mid          0.28
_exptl_crystal_size_min          0.15
_refine_diff_density_max         1.008
_refine_diff_density_min         -1.056
_refine_diff_density_rms         0.188
_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     273
_refine_ls_number_reflns         8557
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.040
_refine_ls_R_factor_all          0.0523
_refine_ls_R_factor_gt           0.0333
_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)+(0.0381P)²+1.9872P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0746
_refine_ls_wR_factor_ref         0.0830
_reflns_number_gt                6721
_reflns_number_total             8557
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            jo801643u_si_005.cif
_cod_data_source_block           ch229_0m
_cod_original_sg_symbol_H-M      p-1
_cod_database_code               4024213
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 0.83117(3) 0.42010(3) 0.68045(2) 0.01845(6) Uani 1 1 d . . .
Br2 Br 1.12915(3) 0.26860(3) 0.58401(2) 0.01769(6) Uani 1 1 d . . .
Br3 Br 0.50309(3) 0.76471(3) -0.05230(2) 0.02032(6) Uani 1 1 d . . .
Br4 Br 0.80716(3) 0.62166(3) -0.14922(2) 0.01967(6) Uani 1 1 d . . .
Br5 Br 0.54169(3) -0.17832(3) 0.29033(2) 0.02200(6) Uani 1 1 d . . .
Br6 Br 0.24760(3) -0.02774(3) 0.39385(2) 0.02138(6) Uani 1 1 d . . .
C1 C 0.5559(3) 0.2361(2) 0.33642(19) 0.0127(4) Uani 1 1 d . . .
C2 C 0.6793(3) 0.1737(2) 0.29461(18) 0.0120(4) Uani 1 1 d . . .
C3 C 0.9556(3) 0.2712(2) 0.41525(19) 0.0134(4) Uani 1 1 d . . .
H3 H 1.0395 0.2287 0.3877 0.016 Uiso 1 1 calc R . .
C4 C 0.8064(3) 0.2595(2) 0.26010(19) 0.0121(4) Uani 1 1 d . . .
H4 H 0.8948 0.2151 0.2307 0.014 Uiso 1 1 calc R . .
C5 C 0.9572(3) 0.3081(2) 0.51085(19) 0.0134(4) Uani 1 1 d . . .
C6 C 0.8300(3) 0.2977(2) 0.36176(19) 0.0119(4) Uani 1 1 d . . .
C7 C 0.6754(3) 0.0502(2) 0.28241(19) 0.0138(4) Uani 1 1 d . . .
H7 H 0.7585 0.0079 0.2536 0.017 Uiso 1 1 calc R . .
C8 C 0.5512(3) 0.5614(2) 0.1488(2) 0.0139(4) Uani 1 1 d . . .
H8 H 0.4663 0.6027 0.1765 0.017 Uiso 1 1 calc R . .
C9 C 0.6232(3) 0.4491(2) 0.21687(19) 0.0123(4) Uani 1 1 d . . .
C10 C 0.7476(3) 0.3869(2) 0.17598(19) 0.0125(4) Uani 1 1 d . . .
C11 C 0.7062(3) 0.3607(2) 0.40236(19) 0.0124(4) Uani 1 1 d . . .
C12 C 0.7084(3) 0.3976(2) 0.4963(2) 0.0142(4) Uani 1 1 d . . .
H12 H 0.6247 0.4409 0.5234 0.017 Uiso 1 1 calc R . .
C13 C 0.4295(3) 0.1742(2) 0.36823(19) 0.0142(4) Uani 1 1 d . . .
H13 H 0.3470 0.2157 0.3985 0.017 Uiso 1 1 calc R . .
C14 C 0.7293(3) 0.5528(2) -0.00143(19) 0.0138(4) Uani 1 1 d . . .
C15 C 0.8019(3) 0.4384(2) 0.06701(19) 0.0130(4) Uani 1 1 d . . .
H15 H 0.8865 0.3971 0.0392 0.016 Uiso 1 1 calc R . .
C16 C 0.6055(3) 0.6131(2) 0.03873(19) 0.0140(4) Uani 1 1 d . . .
C17 C 0.8351(3) 0.3703(2) 0.55084(19) 0.0139(4) Uani 1 1 d . . .
C18 C 0.4246(3) 0.0502(3) 0.3553(2) 0.0148(4) Uani 1 1 d . . .
C19 C 0.5465(3) -0.0118(2) 0.3132(2) 0.0146(4) Uani 1 1 d . . .
C20 C 0.5764(3) 0.3755(2) 0.33666(19) 0.0130(4) Uani 1 1 d . . .
H20 H 0.4881 0.4199 0.3661 0.016 Uiso 1 1 calc R . .
C22 C 0.9081(4) 0.9065(4) 0.9597(3) 0.0328(7) Uani 1 1 d . . .
C21 C 0.8794(5) 0.8126(5) 1.0731(4) 0.0510(11) Uani 1 1 d . . .
H21A H 0.9587 0.7420 1.0893 0.076 Uiso 1 1 calc R . .
H21B H 0.7887 0.7732 1.0771 0.076 Uiso 1 1 calc R . .
H21C H 0.8719 0.8608 1.1274 0.076 Uiso 1 1 calc R . .
C23 C 0.7971(5) 1.0198(5) 0.9162(5) 0.0604(13) Uani 1 1 d . . .
H23A H 0.7763 1.0710 0.9685 0.091 Uiso 1 1 calc R . .
H23B H 0.7084 0.9849 0.9075 0.091 Uiso 1 1 calc R . .
H23C H 0.8339 1.0776 0.8443 0.091 Uiso 1 1 calc R . .
O1 O 1.0193(3) 0.8933(3) 0.9054(2) 0.0439(7) 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'
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
C13 C1 C2 120.8(2) . . ?
C13 C1 C20 125.8(2) . . ?
C2 C1 C20 113.3(2) . . ?
C7 C2 C1 120.4(2) . . ?
C7 C2 C4 126.3(2) . . ?
C1 C2 C4 113.2(2) . . ?
C6 C3 C5 118.9(2) . . ?
C10 C4 C6 106.01(19) . . ?
C10 C4 C2 104.18(19) . . ?
C6 C4 C2 105.63(18) . . ?
C17 C5 C3 120.6(2) . . ?
C17 C5 Br2 121.23(18) . . ?
C3 C5 Br2 118.21(19) . . ?
C3 C6 C11 120.5(2) . . ?
C3 C6 C4 126.2(2) . . ?
C11 C6 C4 113.3(2) . . ?
C2 C7 C19 118.8(2) . . ?
C9 C8 C16 118.8(2) . . ?
C8 C9 C10 120.8(2) . . ?
C8 C9 C20 126.1(2) . . ?
C10 C9 C20 113.0(2) . . ?
C15 C10 C9 120.4(2) . . ?
C15 C10 C4 126.0(2) . . ?
C9 C10 C4 113.5(2) . . ?
C12 C11 C6 120.4(2) . . ?
C12 C11 C20 126.2(2) . . ?
C6 C11 C20 113.3(2) . . ?
C11 C12 C17 119.1(2) . . ?
C1 C13 C18 119.0(2) . . ?
C16 C14 C15 120.8(2) . . ?
C16 C14 Br4 121.57(18) . . ?
C15 C14 Br4 117.62(19) . . ?
C10 C15 C14 118.7(2) . . ?
C14 C16 C8 120.5(2) . . ?
C14 C16 Br3 121.77(18) . . ?
C8 C16 Br3 117.68(19) . . ?
C5 C17 C12 120.4(2) . . ?
C5 C17 Br1 122.14(19) . . ?
C12 C17 Br1 117.43(18) . . ?
C13 C18 C19 120.4(2) . . ?
C13 C18 Br6 117.73(19) . . ?
C19 C18 Br6 121.89(19) . . ?
C18 C19 C7 120.6(2) . . ?
C18 C19 Br5 121.38(19) . . ?
C7 C19 Br5 117.96(19) . . ?
C11 C20 C1 105.85(19) . . ?
C11 C20 C9 106.32(19) . . ?
C1 C20 C9 104.51(19) . . ?
O1 C22 C21 120.8(4) . . ?
O1 C22 C23 120.8(4) . . ?
C21 C22 C23 118.4(4) . . ?
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 C17 1.890(2) . ?
Br2 C5 1.887(2) . ?
Br3 C16 1.886(2) . ?
Br4 C14 1.889(2) . ?
Br5 C19 1.894(2) . ?
Br6 C18 1.887(2) . ?
C1 C13 1.382(3) . ?
C1 C2 1.403(3) . ?
C1 C20 1.521(3) . ?
C2 C7 1.379(3) . ?
C2 C4 1.527(3) . ?
C3 C6 1.380(3) . ?
C3 C5 1.400(3) . ?
C4 C10 1.523(3) . ?
C4 C6 1.525(3) . ?
C5 C17 1.383(4) . ?
C6 C11 1.402(3) . ?
C7 C19 1.401(3) . ?
C8 C9 1.383(3) . ?
C8 C16 1.398(3) . ?
C9 C10 1.404(3) . ?
C9 C20 1.521(3) . ?
C10 C15 1.385(3) . ?
C11 C12 1.380(3) . ?
C11 C20 1.518(3) . ?
C12 C17 1.396(4) . ?
C13 C18 1.389(4) . ?
C14 C16 1.385(4) . ?
C14 C15 1.401(3) . ?
C18 C19 1.392(4) . ?
C22 O1 1.204(4) . ?
C22 C21 1.491(6) . ?
C22 C23 1.498(6) . ?
