#------------------------------------------------------------------------------
#$Date: 2016-03-21 04:06:11 +0200 (Mon, 21 Mar 2016) $
#$Revision: 178458 $
#$URL: svn://www.crystallography.net/cod/cif/4/02/79/4027918.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_4027918
loop_
_publ_author_name
'Tao Wang'
'Yu-Fei Zhang'
'Qin-Qing Hou'
'Wen-Rong Xu'
'Xiao-Ping Cao'
'Hak-Fun Chow'
'Dietmar Kuck'
_publ_section_title
;
 C3-Symmetrical Tribenzotriquinacene Derivatives: Optical Resolution
 through Cryptophane Synthesis and Supramolecular Self-Assembly into
 Nanotubes
;
_journal_name_full               'Journal of Organic Chemistry'
_journal_page_first              1062
_journal_page_last               1069
_journal_paper_doi               10.1021/jo302470v
_journal_volume                  78
_journal_year                    2013
_chemical_formula_sum            'C20 H20 O2.67'
_chemical_formula_weight         303.03
_chemical_name_systematic
; 
 ? 
;
_space_group_IT_number           147
_symmetry_cell_setting           trigonal
_symmetry_space_group_name_Hall  '-P 3'
_symmetry_space_group_name_H-M   'P -3'
_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                 90.00
_cell_angle_gamma                120.00
_cell_formula_units_Z            3
_cell_length_a                   11.9000(9)
_cell_length_b                   11.9000(9)
_cell_length_c                   9.9832(7)
_cell_measurement_reflns_used    1703
_cell_measurement_temperature    296(2)
_cell_measurement_theta_max      27.56
_cell_measurement_theta_min      2.84
_cell_volume                     1224.32(16)
_computing_cell_refinement       'Bruker SAINT'
_computing_data_collection       'Bruker APEX2'
_computing_data_reduction        'Bruker SAINT'
_computing_molecular_graphics    'Bruker SHELXTL'
_computing_publication_material  'Bruker SHELXTL'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 2008)'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 2008)'
_diffrn_ambient_temperature      296(2)
_diffrn_measured_fraction_theta_full 0.999
_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  0.0269
_diffrn_reflns_av_sigmaI/netI    0.0226
_diffrn_reflns_limit_h_max       13
_diffrn_reflns_limit_h_min       -14
_diffrn_reflns_limit_k_max       14
_diffrn_reflns_limit_k_min       -14
_diffrn_reflns_limit_l_max       12
_diffrn_reflns_limit_l_min       -5
_diffrn_reflns_number            6426
_diffrn_reflns_theta_full        25.48
_diffrn_reflns_theta_max         25.48
_diffrn_reflns_theta_min         1.98
_exptl_absorpt_coefficient_mu    0.081
_exptl_absorpt_correction_T_max  0.9754
_exptl_absorpt_correction_T_min  0.9723
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   SADABS
_exptl_crystal_colour            colorless
_exptl_crystal_density_diffrn    1.233
_exptl_crystal_description       block
_exptl_crystal_F_000             484
_exptl_crystal_size_max          0.35
_exptl_crystal_size_mid          0.33
_exptl_crystal_size_min          0.31
_refine_diff_density_max         0.562
_refine_diff_density_min         -0.204
_refine_diff_density_rms         0.055
_refine_ls_extinction_coef       0.005(7)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc²λ³/sin(2θ)]^-1/4^
_refine_ls_extinction_method     SHELXL
_refine_ls_goodness_of_fit_ref   1.076
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     113
_refine_ls_number_reflns         1524
_refine_ls_number_restraints     1
_refine_ls_restrained_S_all      1.077
_refine_ls_R_factor_all          0.0715
_refine_ls_R_factor_gt           0.0592
_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)+(0.1180P)²+0.4270P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1851
_refine_ls_wR_factor_ref         0.1970
_reflns_number_gt                1211
_reflns_number_total             1524
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            jo302470v_si_005.cif
_cod_data_source_block           p-3
_cod_database_code               4027918
loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'-y, x-y, z'
'-x+y, -x, z'
'-x, -y, -z'
'y, -x+y, -z'
'x-y, x, -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
C1 C 0.5448(2) 0.14495(19) 0.69411(19) 0.0325(5) Uani 1 1 d .
C2 C 0.4497(2) 0.0397(2) 0.7654(2) 0.0402(6) Uani 1 1 d .
H2 H 0.3645 0.0229 0.7657 0.048 Uiso 1 1 calc R
C3 C 0.52649(19) 0.24011(19) 0.60885(19) 0.0333(6) Uani 1 1 d .
C4 C 0.49867(19) 0.32920(19) 0.69447(19) 0.0321(5) Uani 1 1 d .
C5 C 0.3852(2) 0.2962(2) 0.7645(2) 0.0364(6) Uani 1 1 d .
H5 H 0.3169 0.2110 0.7637 0.044 Uiso 1 1 calc R
C6 C 0.3738(2) 0.3907(2) 0.8361(2) 0.0370(6) Uani 1 1 d .
C7 C 0.4776(2) 0.5172(2) 0.8359(2) 0.0408(6) Uani 1 1 d .
H7 H 0.4713 0.5808 0.8839 0.049 Uiso 1 1 calc R
C8 C 0.2507(2) 0.3627(2) 0.9053(3) 0.0491(7) Uani 1 1 d .
H8A H 0.2710 0.4265 0.9755 0.059 Uiso 1 1 calc R
H8B H 0.1942 0.3714 0.8414 0.059 Uiso 1 1 calc R
C11 C 0.6667 0.3333 0.5482(3) 0.0338(8) Uani 1 3 d S
C12 C 0.6667 0.3333 0.3956(4) 0.0509(11) Uani 1 3 d S
H12A H 0.7508 0.3972 0.3635 0.076 Uiso 0.33 1 calc PR
H12B H 0.6028 0.3536 0.3635 0.076 Uiso 0.33 1 calc PR
H12C H 0.6464 0.2492 0.3635 0.076 Uiso 0.33 1 calc PR
C13 C 0.4165(2) 0.1662(2) 0.5070(2) 0.0491(7) Uani 1 1 d .
H13A H 0.3368 0.1126 0.5539 0.074 Uiso 1 1 calc R
H13B H 0.4369 0.1128 0.4518 0.074 Uiso 1 1 calc R
H13C H 0.4073 0.2272 0.4519 0.074 Uiso 1 1 calc R
C16 C 0.8886(13) 0.9329(15) 0.629(2) 0.143(6) Uani 0.33 1 d PD
O1 O 0.18547(19) 0.23905(19) 0.9612(2) 0.0747(8) Uani 1 1 d .
H1 H 0.1115 0.2210 0.9813 0.112 Uiso 1 1 calc R
O2 O 1.0000 1.0000 0.6880(16) 0.265(5) Uani 1 3 d SD
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'
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
C4 C1 C2 119.92(19) 2_655 .
C4 C1 C3 113.01(18) 2_655 .
C2 C1 C3 127.05(19) . .
C7 C2 C1 119.5(2) 2_655 .
C7 C2 H2 120.2 2_655 .
C1 C2 H2 120.2 . .
C1 C3 C4 111.56(15) . .
C1 C3 C13 110.04(17) . .
C4 C3 C13 110.48(17) . .
C1 C3 C11 104.02(15) . .
C4 C3 C11 104.21(15) . .
C13 C3 C11 116.29(19) . .
C1 C4 C5 120.50(19) 3_665 .
C1 C4 C3 112.29(17) 3_665 .
C5 C4 C3 127.18(18) . .
C4 C5 C6 120.14(19) . .
C4 C5 H5 119.9 . .
C6 C5 H5 119.9 . .
C7 C6 C5 118.67(19) . .
C7 C6 C8 118.79(19) . .
C5 C6 C8 122.4(2) . .
C2 C7 C6 121.2(2) 3_665 .
C2 C7 H7 119.4 3_665 .
C6 C7 H7 119.4 . .
O1 C8 C6 112.72(18) . .
O1 C8 H8A 109.0 . .
C6 C8 H8A 109.0 . .
O1 C8 H8B 109.0 . .
C6 C8 H8B 109.0 . .
H8A C8 H8B 107.8 . .
C12 C11 C3 112.37(13) . 3_665
C12 C11 C3 112.37(13) . .
C3 C11 C3 106.42(14) 3_665 .
C12 C11 C3 112.37(13) . 2_655
C3 C11 C3 106.42(14) 3_665 2_655
C3 C11 C3 106.42(14) . 2_655
C11 C12 H12A 109.5 . .
C11 C12 H12B 109.5 . .
H12A C12 H12B 109.5 . .
C11 C12 H12C 109.5 . .
H12A C12 H12C 109.5 . .
H12B C12 H12C 109.5 . .
C3 C13 H13A 109.5 . .
C3 C13 H13B 109.5 . .
H13A C13 H13B 109.5 . .
C3 C13 H13C 109.5 . .
H13A C13 H13C 109.5 . .
H13B C13 H13C 109.5 . .
O2 C16 C16 39.4(8) . 3_675
O2 C16 C16 39.4(8) . 2_765
C16 C16 C16 59.999(4) 3_675 2_765
C8 O1 H1 109.5 . .
C16 O2 C16 101.2(16) 3_675 2_765
C16 O2 C16 101.2(16) 3_675 .
C16 O2 C16 101.2(16) 2_765 .
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
C1 C4 1.377(3) 2_655
C1 C2 1.393(3) .
C1 C3 1.517(3) .
C2 C7 1.383(3) 2_655
C2 H2 0.9300 .
C3 C4 1.522(3) .
C3 C13 1.539(3) .
C3 C11 1.590(2) .
C4 C1 1.377(3) 3_665
C4 C5 1.391(3) .
C5 C6 1.395(3) .
C5 H5 0.9300 .
C6 C7 1.391(3) .
C6 C8 1.498(3) .
C7 C2 1.383(3) 3_665
C7 H7 0.9300 .
C8 O1 1.392(3) .
C8 H8A 0.9700 .
C8 H8B 0.9700 .
C11 C12 1.524(5) .
C11 C3 1.590(2) 3_665
C11 C3 1.590(2) 2_655
C12 H12A 0.9600 .
C12 H12B 0.9600 .
C12 H12C 0.9600 .
C13 H13A 0.9600 .
C13 H13B 0.9600 .
C13 H13C 0.9600 .
C16 O2 1.295(2) .
C16 C16 2.00(2) 3_675
C16 C16 2.00(2) 2_765
O1 H1 0.8200 .
O2 C16 1.295(2) 3_675
O2 C16 1.295(2) 2_765
loop_
_geom_torsion_atom_site_label_1
_geom_torsion_atom_site_label_2
_geom_torsion_atom_site_label_3
_geom_torsion_atom_site_label_4
_geom_torsion
_geom_torsion_site_symmetry_1
_geom_torsion_site_symmetry_4
C4 C1 C2 C7 -0.2(3) 2_655 2_655
C3 C1 C2 C7 178.40(18) . 2_655
C4 C1 C3 C4 -110.6(2) 2_655 .
C2 C1 C3 C4 70.8(2) . .
C4 C1 C3 C13 126.45(19) 2_655 .
C2 C1 C3 C13 -52.2(3) . .
C4 C1 C3 C11 1.2(2) 2_655 .
C2 C1 C3 C11 -177.5(2) . .
C1 C3 C4 C1 110.4(2) . 3_665
C13 C3 C4 C1 -126.86(19) . 3_665
C11 C3 C4 C1 -1.2(2) . 3_665
C1 C3 C4 C5 -71.6(2) . .
C13 C3 C4 C5 51.1(3) . .
C11 C3 C4 C5 176.7(2) . .
C1 C4 C5 C6 -0.5(3) 3_665 .
C3 C4 C5 C6 -178.34(18) . .
C4 C5 C6 C7 -0.1(3) . .
C4 C5 C6 C8 175.62(19) . .
C5 C6 C7 C2 0.6(3) . 3_665
C8 C6 C7 C2 -175.3(2) . 3_665
C7 C6 C8 O1 -147.8(2) . .
C5 C6 C8 O1 36.5(3) . .
C1 C3 C11 C12 121.51(11) . .
C4 C3 C11 C12 -121.49(11) . .
C13 C3 C11 C12 0.36(19) . .
C1 C3 C11 C3 -115.09(12) . 3_665
C4 C3 C11 C3 1.9(2) . 3_665
C13 C3 C11 C3 123.8(2) . 3_665
C1 C3 C11 C3 -1.9(2) . 2_655
C4 C3 C11 C3 115.11(12) . 2_655
C13 C3 C11 C3 -123.0(2) . 2_655
C16 C16 O2 C16 104(3) 2_765 3_675
C16 C16 O2 C16 -104(3) 3_675 2_765
