#------------------------------------------------------------------------------
#$Date: 2016-03-21 03:07:09 +0200 (Mon, 21 Mar 2016) $
#$Revision: 178421 $
#$URL: svn://www.crystallography.net/cod/cif/4/02/42/4024212.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_4024212
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 H30'
_chemical_formula_weight         366.52
_chemical_name_common            9,10-dibutyltriptycene
_chemical_name_systematic
; 
 9,10-dibutyl-9,10(1,2-dibenzo)anthracene 
;
_space_group_IT_number           15
_symmetry_cell_setting           monoclinic
_symmetry_space_group_name_Hall  '-C 2yc'
_symmetry_space_group_name_H-M   'C 1 2/c 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                 122.3650(10)
_cell_angle_gamma                90.00
_cell_formula_units_Z            4
_cell_length_a                   20.3011(5)
_cell_length_b                   8.4982(2)
_cell_length_c                   13.5289(3)
_cell_measurement_reflns_used    362
_cell_measurement_temperature    100(2)
_cell_measurement_theta_max      31.5
_cell_measurement_theta_min      1.6
_cell_volume                     1971.46(8)
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 1990)'
_diffrn_ambient_temperature      100(2)
_diffrn_measured_fraction_theta_full 0.999
_diffrn_measured_fraction_theta_max 0.999
_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  0.0285
_diffrn_reflns_av_sigmaI/netI    0.0237
_diffrn_reflns_limit_h_max       30
_diffrn_reflns_limit_h_min       -29
_diffrn_reflns_limit_k_max       12
_diffrn_reflns_limit_k_min       -12
_diffrn_reflns_limit_l_max       20
_diffrn_reflns_limit_l_min       -20
_diffrn_reflns_number            16150
_diffrn_reflns_theta_full        32.63
_diffrn_reflns_theta_max         32.63
_diffrn_reflns_theta_min         2.38
_exptl_absorpt_coefficient_mu    0.069
_exptl_absorpt_correction_T_max  0.9885
_exptl_absorpt_correction_T_min  0.9716
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   SADABS
_exptl_crystal_colour            colorless
_exptl_crystal_density_diffrn    1.235
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       block
_exptl_crystal_F_000             792
_exptl_crystal_size_max          0.42
_exptl_crystal_size_mid          0.29
_exptl_crystal_size_min          0.17
_refine_diff_density_max         0.479
_refine_diff_density_min         -0.407
_refine_diff_density_rms         0.095
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.050
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     128
_refine_ls_number_reflns         3598
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.050
_refine_ls_R_factor_all          0.0504
_refine_ls_R_factor_gt           0.0455
_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)+(0.0803P)²+0.8137P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1226
_refine_ls_wR_factor_ref         0.1295
_reflns_number_gt                3197
_reflns_number_total             3598
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            jo801643u_si_004.cif
_cod_data_source_block           ch241_0m
_cod_original_sg_symbol_H-M      C2/c
_cod_database_code               4024212
loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'-x, y, -z+1/2'
'x+1/2, y+1/2, z'
'-x+1/2, y+1/2, -z+1/2'
'-x, -y, -z'
'x, -y, z-1/2'
'-x+1/2, -y+1/2, -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
C001 C 0.05466(4) 0.83409(8) 0.22355(6) 0.01261(13) Uani 1 1 d . . .
C002 C -0.02140(4) 0.74963(8) 0.13327(6) 0.01299(14) Uani 1 1 d . . .
C003 C 0.07890(4) 0.74927(8) 0.33848(6) 0.01300(14) Uani 1 1 d . . .
C004 C 0.03032(4) 0.99890(8) 0.23920(6) 0.01305(14) Uani 1 1 d . . .
C005 C 0.11980(4) 0.83250(9) 0.19815(6) 0.01502(14) Uani 1 1 d . . .
H00A H 0.1335 0.7212 0.1961 0.018 Uiso 1 1 calc R . .
H00B H 0.1663 0.8827 0.2653 0.018 Uiso 1 1 calc R . .
C006 C 0.16381(4) 0.59693(9) 0.51169(7) 0.01758(15) Uani 1 1 d . . .
H006 H 0.2122 0.5454 0.5614 0.021 Uiso 1 1 calc R . .
C007 C 0.10500(4) 0.91233(10) 0.08572(7) 0.01758(15) Uani 1 1 d . . .
H00C H 0.0788 0.8369 0.0199 0.021 Uiso 1 1 calc R . .
H00D H 0.0697 1.0033 0.0669 0.021 Uiso 1 1 calc R . .
C008 C 0.10706(4) 0.59608(9) 0.53934(7) 0.01807(15) Uani 1 1 d . . .
H008 H 0.1168 0.5439 0.6081 0.022 Uiso 1 1 calc R . .
C009 C 0.14976(4) 0.67357(8) 0.41075(7) 0.01540(14) Uani 1 1 d . . .
H009 H 0.1885 0.6739 0.3916 0.018 Uiso 1 1 calc R . .
C010 C 0.03208(5) 1.28323(9) 0.24437(7) 0.01954(16) Uani 1 1 d . . .
H010 H 0.0549 1.3800 0.2429 0.023 Uiso 1 1 calc R . .
C011 C -0.03550(4) 0.67169(9) 0.03350(6) 0.01577(14) Uani 1 1 d . . .
H011 H 0.0034 0.6697 0.0147 0.019 Uiso 1 1 calc R . .
C012 C 0.18101(4) 0.96875(9) 0.09900(7) 0.01837(15) Uani 1 1 d . . .
H01A H 0.1685 1.0239 0.0265 0.022 Uiso 1 1 calc R . .
H01B H 0.2065 1.0454 0.1641 0.022 Uiso 1 1 calc R . .
C013 C 0.06309(4) 1.14067(9) 0.23527(7) 0.01673(15) Uani 1 1 d . . .
H013 H 0.1065 1.1408 0.2264 0.020 Uiso 1 1 calc R . .
C014 C 0.23779(5) 0.83526(11) 0.12280(9) 0.02531(18) Uani 1 1 d . . .
H01C H 0.2544 0.7866 0.1983 0.038 Uiso 1 1 calc R . .
H01D H 0.2835 0.8771 0.1247 0.038 Uiso 1 1 calc R . .
H01E H 0.2121 0.7563 0.0606 0.038 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'
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
C005 C001 C003 112.03(6) . . ?
C005 C001 C004 114.71(5) . . ?
C003 C001 C004 103.92(5) . . ?
C005 C001 C002 115.90(6) . . ?
C003 C001 C002 103.06(5) . . ?
C004 C001 C002 105.91(5) . . ?
C011 C002 C003 119.53(6) . 2 ?
C011 C002 C001 126.18(6) . . ?
C003 C002 C001 114.23(6) 2 . ?
C009 C003 C002 120.38(6) . 2 ?
C009 C003 C001 125.39(6) . . ?
C002 C003 C001 114.22(6) 2 . ?
C013 C004 C004 119.78(4) . 2 ?
C013 C004 C001 126.04(6) . . ?
C004 C004 C001 114.17(3) 2 . ?
C001 C005 C007 118.76(6) . . ?
C008 C006 C009 120.06(7) . . ?
C012 C007 C005 111.72(6) . . ?
C006 C008 C011 120.38(7) . 2 ?
C003 C009 C006 119.72(7) . . ?
C010 C010 C013 120.08(4) 2 . ?
C002 C011 C008 119.93(7) . 2 ?
C014 C012 C007 113.10(7) . . ?
C004 C013 C010 119.94(7) . . ?
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
C001 C005 1.5342(9) . ?
C001 C003 1.5363(10) . ?
C001 C004 1.5371(10) . ?
C001 C002 1.5402(10) . ?
C002 C011 1.3890(10) . ?
C002 C003 1.4093(9) 2 ?
C003 C009 1.3905(10) . ?
C003 C002 1.4093(9) 2 ?
C004 C013 1.3910(10) . ?
C004 C004 1.4093(13) 2 ?
C005 C007 1.5410(10) . ?
C006 C008 1.3888(10) . ?
C006 C009 1.3977(10) . ?
C007 C012 1.5319(10) . ?
C008 C011 1.4006(10) 2 ?
C010 C010 1.3898(15) 2 ?
C010 C013 1.4008(11) . ?
C011 C008 1.4006(10) 2 ?
C012 C014 1.5239(11) . ?
