#------------------------------------------------------------------------------
#$Date: 2016-03-21 03:52:55 +0200 (Mon, 21 Mar 2016) $
#$Revision: 178448 $
#$URL: svn://www.crystallography.net/cod/cif/4/02/69/4026925.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_4026925
loop_
_publ_author_name
'Wen-Xue Niu'
'Er-Qun Yang'
'Zi-Fa Shi'
'Xiao-Ping Cao'
'Dietmar Kuck'
_publ_section_title
;
 Single-wing Extended Tribenzotriquinacenes via Bowl-shaped Dehydrobenzene
 and Isobenzofuran Tribenzotriquinacene Derivatives
;
_journal_name_full               'Journal of Organic Chemistry'
_journal_page_first              1422
_journal_page_last               1434
_journal_paper_doi               10.1021/jo2022668
_journal_volume                  77
_journal_year                    2012
_chemical_absolute_configuration none
_chemical_formula_sum            'C30 H26'
_chemical_formula_weight         386.51
_chemical_name_systematic
; 
 ? 
;
_space_group_IT_number           19
_symmetry_cell_setting           orthorhombic
_symmetry_space_group_name_Hall  'P 2ac 2ab'
_symmetry_space_group_name_H-M   'P 21 21 21'
_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                90.00
_cell_formula_units_Z            4
_cell_length_a                   10.927(3)
_cell_length_b                   12.053(3)
_cell_length_c                   16.003(4)
_cell_measurement_reflns_used    3454
_cell_measurement_temperature    296(2)
_cell_measurement_theta_max      21.88
_cell_measurement_theta_min      2.55
_cell_volume                     2107.6(9)
_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 1.000
_diffrn_measured_fraction_theta_max 1.000
_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  0.0300
_diffrn_reflns_av_sigmaI/netI    0.0321
_diffrn_reflns_limit_h_max       6
_diffrn_reflns_limit_h_min       -13
_diffrn_reflns_limit_k_max       14
_diffrn_reflns_limit_k_min       -14
_diffrn_reflns_limit_l_max       19
_diffrn_reflns_limit_l_min       -18
_diffrn_reflns_number            11517
_diffrn_reflns_theta_full        26.00
_diffrn_reflns_theta_max         26.00
_diffrn_reflns_theta_min         2.12
_exptl_absorpt_coefficient_mu    0.069
_exptl_absorpt_correction_T_max  0.9824
_exptl_absorpt_correction_T_min  0.9744
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   SADABS
_exptl_crystal_colour            colorless
_exptl_crystal_density_diffrn    1.218
_exptl_crystal_description       block
_exptl_crystal_F_000             824
_exptl_crystal_size_max          0.38
_exptl_crystal_size_mid          0.35
_exptl_crystal_size_min          0.26
_refine_diff_density_max         0.108
_refine_diff_density_min         -0.106
_refine_diff_density_rms         0.029
_refine_ls_abs_structure_details 'Flack H D (1983), Acta Cryst. A39, 876-881'
_refine_ls_abs_structure_Flack   -2(8)
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.036
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     275
_refine_ls_number_reflns         4141
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.036
_refine_ls_R_factor_all          0.0513
_refine_ls_R_factor_gt           0.0369
_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)+(0.0411P)²+0.0934P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0805
_refine_ls_wR_factor_ref         0.0877
_reflns_number_gt                3304
_reflns_number_total             4141
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            jo2022668_si_002.cif
_cod_data_source_block           p212121
_cod_original_cell_volume        2107.7(9)
_cod_database_code               4026925
loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'-x+1/2, -y, z+1/2'
'-x, y+1/2, -z+1/2'
'x+1/2, -y+1/2, -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 0.82730(16) -0.03997(15) 0.91223(11) 0.0463(4) Uani 1 1 d .
H1 H 0.8496 -0.0272 0.8570 0.056 Uiso 1 1 calc R
C2 C 0.91138(16) -0.09253(13) 0.96700(11) 0.0449(4) Uani 1 1 d .
C3 C 1.03342(17) -0.12035(15) 0.94231(14) 0.0591(5) Uani 1 1 d .
H3 H 1.0588 -0.1067 0.8878 0.071 Uiso 1 1 calc R
C4 C 1.11346(19) -0.16702(16) 0.99826(17) 0.0697(6) Uani 1 1 d .
H4 H 1.1931 -0.1832 0.9817 0.084 Uiso 1 1 calc R
C5 C 1.07622(19) -0.19046(17) 1.07998(17) 0.0690(6) Uani 1 1 d .
H5 H 1.1310 -0.2228 1.1172 0.083 Uiso 1 1 calc R
C6 C 0.96015(18) -0.16626(16) 1.10559(14) 0.0607(5) Uani 1 1 d .
H6 H 0.9363 -0.1839 1.1598 0.073 Uiso 1 1 calc R
C7 C 0.87466(16) -0.11431(13) 1.05062(11) 0.0456(4) Uani 1 1 d .
C8 C 0.75587(16) -0.08226(15) 1.07651(11) 0.0461(4) Uani 1 1 d .
H8 H 0.7302 -0.0979 1.1307 0.055 Uiso 1 1 calc R
C9 C 0.67802(15) -0.02836(14) 1.02277(10) 0.0390(4) Uani 1 1 d .
C10 C 0.71376(14) -0.00762(13) 0.93936(10) 0.0392(4) Uani 1 1 d .
C11 C 0.61486(15) 0.05149(14) 0.88979(10) 0.0413(4) Uani 1 1 d .
C12 C 0.65130(14) 0.16931(14) 0.86499(10) 0.0401(4) Uani 1 1 d .
C13 C 0.74180(16) 0.20091(17) 0.80836(11) 0.0514(5) Uani 1 1 d .
H13 H 0.7898 0.1473 0.7824 0.062 Uiso 1 1 calc R
C14 C 0.76004(18) 0.31226(19) 0.79081(13) 0.0591(5) Uani 1 1 d .
H14 H 0.8211 0.3335 0.7536 0.071 Uiso 1 1 calc R
C15 C 0.68721(19) 0.39231(17) 0.82879(13) 0.0592(5) Uani 1 1 d .
H15 H 0.6981 0.4668 0.8157 0.071 Uiso 1 1 calc R
C16 C 0.59907(18) 0.36157(15) 0.88578(12) 0.0542(5) Uani 1 1 d .
H16 H 0.5512 0.4154 0.9116 0.065 Uiso 1 1 calc R
C17 C 0.58165(14) 0.24993(14) 0.90478(10) 0.0412(4) Uani 1 1 d .
C18 C 0.49321(15) 0.19969(14) 0.96778(10) 0.0418(4) Uani 1 1 d .
C19 C 0.53673(14) 0.21911(14) 1.05717(10) 0.0411(4) Uani 1 1 d .
C20 C 0.54922(16) 0.31971(15) 1.09852(12) 0.0516(5) Uani 1 1 d .
H20 H 0.5317 0.3858 1.0709 0.062 Uiso 1 1 calc R
C21 C 0.58787(17) 0.32149(17) 1.18114(12) 0.0573(5) Uani 1 1 d .
H21 H 0.5970 0.3889 1.2087 0.069 Uiso 1 1 calc R
C22 C 0.6127(2) 0.22380(18) 1.22248(12) 0.0608(5) Uani 1 1 d .
H22 H 0.6367 0.2253 1.2782 0.073 Uiso 1 1 calc R
C23 C 0.60199(19) 0.12324(17) 1.18103(11) 0.0568(5) Uani 1 1 d .
H23 H 0.6198 0.0575 1.2089 0.068 Uiso 1 1 calc R
C24 C 0.56466(14) 0.12025(14) 1.09790(10) 0.0423(4) Uani 1 1 d .
C25 C 0.55172(15) 0.01922(14) 1.04202(10) 0.0420(4) Uani 1 1 d .
C26 C 0.50521(15) 0.06903(14) 0.95488(10) 0.0427(4) Uani 1 1 d .
C27 C 0.58311(19) -0.01572(17) 0.81015(11) 0.0568(5) Uani 1 1 d .
H27A H 0.5192 0.0214 0.7800 0.085 Uiso 1 1 calc R
H27B H 0.5561 -0.0886 0.8258 0.085 Uiso 1 1 calc R
H27C H 0.6544 -0.0216 0.7754 0.085 Uiso 1 1 calc R
C28 C 0.36379(16) 0.24995(17) 0.95728(13) 0.0580(5) Uani 1 1 d .
H28A H 0.3667 0.3281 0.9685 0.087 Uiso 1 1 calc R
H28B H 0.3085 0.2149 0.9957 0.087 Uiso 1 1 calc R
H28C H 0.3359 0.2380 0.9011 0.087 Uiso 1 1 calc R
C29 C 0.46857(17) -0.06948(16) 1.08233(12) 0.0576(5) Uani 1 1 d .
H29A H 0.5046 -0.0945 1.1337 0.086 Uiso 1 1 calc R
H29B H 0.4598 -0.1311 1.0448 0.086 Uiso 1 1 calc R
H29C H 0.3896 -0.0380 1.0935 0.086 Uiso 1 1 calc R
C30 C 0.38510(18) 0.01604(18) 0.92500(13) 0.0634(5) Uani 1 1 d .
H30A H 0.3964 -0.0625 0.9185 0.095 Uiso 1 1 calc R
H30B H 0.3618 0.0479 0.8724 0.095 Uiso 1 1 calc R
H30C H 0.3220 0.0296 0.9655 0.095 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
C10 C1 C2 121.15(16)
C10 C1 H1 119.4
C2 C1 H1 119.4
C1 C2 C7 118.76(15)
C1 C2 C3 122.52(17)
C7 C2 C3 118.67(17)
C4 C3 C2 120.7(2)
C4 C3 H3 119.7
C2 C3 H3 119.7
C3 C4 C5 120.5(2)
C3 C4 H4 119.8
C5 C4 H4 119.8
C6 C5 C4 120.5(2)
C6 C5 H5 119.7
C4 C5 H5 119.7
C5 C6 C7 121.1(2)
C5 C6 H6 119.4
C7 C6 H6 119.4
C8 C7 C2 118.93(16)
C8 C7 C6 122.62(17)
C2 C7 C6 118.45(16)
C9 C8 C7 120.91(16)
C9 C8 H8 119.5
C7 C8 H8 119.5
C8 C9 C10 120.27(15)
C8 C9 C25 127.72(15)
C10 C9 C25 111.97(14)
C1 C10 C9 119.93(16)
C1 C10 C11 127.74(16)
C9 C10 C11 112.33(14)
C10 C11 C12 112.74(13)
C10 C11 C27 110.11(15)
C12 C11 C27 109.32(14)
C10 C11 C26 104.75(12)
C12 C11 C26 103.96(13)
C27 C11 C26 115.88(14)
C17 C12 C13 119.70(16)
C17 C12 C11 112.87(14)
C13 C12 C11 127.43(16)
C14 C13 C12 119.90(18)
C14 C13 H13 120.1
C12 C13 H13 120.1
C13 C14 C15 120.07(18)
C13 C14 H14 120.0
C15 C14 H14 120.0
C16 C15 C14 120.20(19)
C16 C15 H15 119.9
C14 C15 H15 119.9
C15 C16 C17 120.01(18)
C15 C16 H16 120.0
C17 C16 H16 120.0
C12 C17 C16 120.07(15)
C12 C17 C18 111.91(15)
C16 C17 C18 128.01(16)
C17 C18 C19 111.23(14)
C17 C18 C28 110.64(14)
C19 C18 C28 109.06(14)
C17 C18 C26 104.78(13)
C19 C18 C26 104.32(13)
C28 C18 C26 116.61(15)
C20 C19 C24 120.20(16)
C20 C19 C18 127.71(15)
C24 C19 C18 112.09(15)
C19 C20 C21 119.83(18)
C19 C20 H20 120.1
C21 C20 H20 120.1
C22 C21 C20 120.28(19)
C22 C21 H21 119.9
C20 C21 H21 119.9
C21 C22 C23 120.05(18)
C21 C22 H22 120.0
C23 C22 H22 120.0
C22 C23 C24 120.30(18)
C22 C23 H23 119.9
C24 C23 H23 119.9
C23 C24 C19 119.32(17)
C23 C24 C25 127.69(16)
C19 C24 C25 112.98(14)
C24 C25 C9 109.65(13)
C24 C25 C29 111.36(14)
C9 C25 C29 110.87(14)
C24 C25 C26 104.00(13)
C9 C25 C26 104.61(13)
C29 C25 C26 115.90(14)
C30 C26 C18 112.39(14)
C30 C26 C25 112.74(14)
C18 C26 C25 106.49(13)
C30 C26 C11 112.45(14)
C18 C26 C11 106.03(12)
C25 C26 C11 106.23(12)
C11 C27 H27A 109.5
C11 C27 H27B 109.5
H27A C27 H27B 109.5
C11 C27 H27C 109.5
H27A C27 H27C 109.5
H27B C27 H27C 109.5
C18 C28 H28A 109.5
C18 C28 H28B 109.5
H28A C28 H28B 109.5
C18 C28 H28C 109.5
H28A C28 H28C 109.5
H28B C28 H28C 109.5
C25 C29 H29A 109.5
C25 C29 H29B 109.5
H29A C29 H29B 109.5
C25 C29 H29C 109.5
H29A C29 H29C 109.5
H29B C29 H29C 109.5
C26 C30 H30A 109.5
C26 C30 H30B 109.5
H30A C30 H30B 109.5
C26 C30 H30C 109.5
H30A C30 H30C 109.5
H30B C30 H30C 109.5
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
C1 C10 1.371(2)
C1 C2 1.419(2)
C1 H1 0.9300
C2 C7 1.422(2)
C2 C3 1.431(2)
C3 C4 1.372(3)
C3 H3 0.9300
C4 C5 1.398(3)
C4 H4 0.9300
C5 C6 1.364(3)
C5 H5 0.9300
C6 C7 1.428(3)
C6 H6 0.9300
C7 C8 1.416(2)
C8 C9 1.373(2)
C8 H8 0.9300
C9 C10 1.413(2)
C9 C25 1.526(2)
C10 C11 1.518(2)
C11 C12 1.527(2)
C11 C27 1.549(2)
C11 C26 1.602(2)
C12 C17 1.389(2)
C12 C13 1.394(2)
C13 C14 1.386(3)
C13 H13 0.9300
C14 C15 1.391(3)
C14 H14 0.9300
C15 C16 1.377(3)
C15 H15 0.9300
C16 C17 1.393(2)
C16 H16 0.9300
C17 C18 1.522(2)
C18 C19 1.526(2)
C18 C28 1.548(2)
C18 C26 1.594(2)
C19 C20 1.388(2)
C19 C24 1.392(2)
C20 C21 1.388(3)
C20 H20 0.9300
C21 C22 1.378(3)
C21 H21 0.9300
C22 C23 1.387(3)
C22 H22 0.9300
C23 C24 1.392(2)
C23 H23 0.9300
C24 C25 1.517(2)
C25 C29 1.544(2)
C25 C26 1.601(2)
C26 C30 1.536(3)
C27 H27A 0.9600
C27 H27B 0.9600
C27 H27C 0.9600
C28 H28A 0.9600
C28 H28B 0.9600
C28 H28C 0.9600
C29 H29A 0.9600
C29 H29B 0.9600
C29 H29C 0.9600
C30 H30A 0.9600
C30 H30B 0.9600
C30 H30C 0.9600
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
C10 C1 C2 C7 1.8(2)
C10 C1 C2 C3 -175.57(16)
C1 C2 C3 C4 177.31(18)
C7 C2 C3 C4 -0.1(3)
C2 C3 C4 C5 1.4(3)
C3 C4 C5 C6 -0.7(3)
C4 C5 C6 C7 -1.4(3)
C1 C2 C7 C8 -0.4(2)
C3 C2 C7 C8 177.10(15)
C1 C2 C7 C6 -179.41(16)
C3 C2 C7 C6 -1.9(2)
C5 C6 C7 C8 -176.28(18)
C5 C6 C7 C2 2.7(3)
C2 C7 C8 C9 -1.7(3)
C6 C7 C8 C9 177.29(18)
C7 C8 C9 C10 2.4(3)
C7 C8 C9 C25 -175.14(16)
C2 C1 C10 C9 -1.2(2)
C2 C1 C10 C11 178.48(16)
C8 C9 C10 C1 -0.9(2)
C25 C9 C10 C1 176.94(15)
C8 C9 C10 C11 179.35(15)
C25 C9 C10 C11 -2.75(19)
C1 C10 C11 C12 -66.5(2)
C9 C10 C11 C12 113.13(16)
C1 C10 C11 C27 55.8(2)
C9 C10 C11 C27 -124.50(15)
C1 C10 C11 C26 -178.93(16)
C9 C10 C11 C26 0.74(18)
C10 C11 C12 C17 -112.75(15)
C27 C11 C12 C17 124.43(16)
C26 C11 C12 C17 0.12(17)
C10 C11 C12 C13 68.2(2)
C27 C11 C12 C13 -54.6(2)
C26 C11 C12 C13 -178.92(15)
C17 C12 C13 C14 -1.3(2)
C11 C12 C13 C14 177.65(17)
C12 C13 C14 C15 -0.8(3)
C13 C14 C15 C16 1.9(3)
C14 C15 C16 C17 -0.8(3)
C13 C12 C17 C16 2.4(2)
C11 C12 C17 C16 -176.70(15)
C13 C12 C17 C18 -176.64(14)
C11 C12 C17 C18 4.24(18)
C15 C16 C17 C12 -1.4(3)
C15 C16 C17 C18 177.52(16)
C12 C17 C18 C19 105.51(16)
C16 C17 C18 C19 -73.5(2)
C12 C17 C18 C28 -133.11(16)
C16 C17 C18 C28 47.9(2)
C12 C17 C18 C26 -6.64(18)
C16 C17 C18 C26 174.39(16)
C17 C18 C19 C20 64.7(2)
C28 C18 C19 C20 -57.6(2)
C26 C18 C19 C20 177.09(16)
C17 C18 C19 C24 -115.75(15)
C28 C18 C19 C24 121.94(15)
C26 C18 C19 C24 -3.32(17)
C24 C19 C20 C21 -1.0(2)
C18 C19 C20 C21 178.57(17)
C19 C20 C21 C22 -0.6(3)
C20 C21 C22 C23 1.6(3)
C21 C22 C23 C24 -0.8(3)
C22 C23 C24 C19 -0.8(3)
C22 C23 C24 C25 177.88(17)
C20 C19 C24 C23 1.7(2)
C18 C19 C24 C23 -177.92(16)
C20 C19 C24 C25 -177.16(14)
C18 C19 C24 C25 3.21(19)
C23 C24 C25 C9 -68.9(2)
C19 C24 C25 C9 109.83(16)
C23 C24 C25 C29 54.2(2)
C19 C24 C25 C29 -127.09(16)
C23 C24 C25 C26 179.66(17)
C19 C24 C25 C26 -1.58(17)
C8 C9 C25 C24 70.2(2)
C10 C9 C25 C24 -107.54(16)
C8 C9 C25 C29 -53.2(2)
C10 C9 C25 C29 129.09(16)
C8 C9 C25 C26 -178.83(17)
C10 C9 C25 C26 3.47(17)
C17 C18 C26 C30 -116.90(15)
C19 C18 C26 C30 126.10(15)
C28 C18 C26 C30 5.8(2)
C17 C18 C26 C25 119.18(13)
C19 C18 C26 C25 2.19(16)
C28 C18 C26 C25 -118.13(15)
C17 C18 C26 C11 6.33(16)
C19 C18 C26 C11 -110.66(13)
C28 C18 C26 C11 129.02(15)
C24 C25 C26 C30 -124.23(15)
C9 C25 C26 C30 120.74(16)
C29 C25 C26 C30 -1.7(2)
C24 C25 C26 C18 -0.52(15)
C9 C25 C26 C18 -115.56(14)
C29 C25 C26 C18 122.04(15)
C24 C25 C26 C11 112.19(13)
C9 C25 C26 C11 -2.84(16)
C29 C25 C26 C11 -125.24(15)
C10 C11 C26 C30 -122.37(15)
C12 C11 C26 C30 119.12(15)
C27 C11 C26 C30 -0.9(2)
C10 C11 C26 C18 114.42(14)
C12 C11 C26 C18 -4.09(15)
C27 C11 C26 C18 -124.05(16)
C10 C11 C26 C25 1.39(16)
C12 C11 C26 C25 -117.12(13)
C27 C11 C26 C25 122.91(15)
