#------------------------------------------------------------------------------
#$Date: 2016-03-21 17:25:37 +0200 (Mon, 21 Mar 2016) $
#$Revision: 178782 $
#$URL: svn://www.crystallography.net/cod/cif/4/10/36/4103683.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_4103683
loop_
_publ_author_name
'Kaiyan Lou'
'Allan M. Prior'
'Bernard Wiredu'
'John Desper'
'Duy H. Hua'
_publ_section_title
;
 Synthesis of Cyclododeciptycene Quinones
;
_journal_name_full               'Journal of the American Chemical Society'
_journal_page_first              17635
_journal_page_last               17641
_journal_paper_doi               10.1021/ja1088309
_journal_volume                  132
_journal_year                    2010
_chemical_formula_moiety
;
(C88 H48 O12) (C2 H5 O)
;
_chemical_formula_sum            'C90 H53 O13'
_chemical_formula_weight         1342.32
_chemical_name_systematic
;
 ?
;
_space_group_IT_number           230
_symmetry_cell_setting           cubic
_symmetry_space_group_name_Hall  '-I 4bd 2c 3'
_symmetry_space_group_name_H-M   'I a -3 d'
_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            16
_cell_length_a                   33.0333(17)
_cell_length_b                   33.0333(17)
_cell_length_c                   33.0333(17)
_cell_measurement_reflns_used    3743
_cell_measurement_temperature    100(2)
_cell_measurement_theta_max      15.90
_cell_measurement_theta_min      2.47
_cell_volume                     36046(3)
_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      100(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  0.1821
_diffrn_reflns_av_sigmaI/netI    0.0400
_diffrn_reflns_limit_h_max       33
_diffrn_reflns_limit_h_min       -33
_diffrn_reflns_limit_k_max       33
_diffrn_reflns_limit_k_min       -33
_diffrn_reflns_limit_l_max       33
_diffrn_reflns_limit_l_min       -33
_diffrn_reflns_number            91091
_diffrn_reflns_theta_full        20.80
_diffrn_reflns_theta_max         20.80
_diffrn_reflns_theta_min         2.31
_exptl_absorpt_coefficient_mu    0.066
_exptl_absorpt_correction_type   none
_exptl_crystal_colour            Orange
_exptl_crystal_density_diffrn    0.989
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       Triangular
_exptl_crystal_F_000             11152
_exptl_crystal_size_max          0.24
_exptl_crystal_size_mid          0.20
_exptl_crystal_size_min          0.10
_refine_diff_density_max         0.673
_refine_diff_density_min         -0.261
_refine_diff_density_rms         0.088
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.768
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     172
_refine_ls_number_reflns         1580
_refine_ls_number_restraints     78
_refine_ls_restrained_S_all      1.738
_refine_ls_R_factor_all          0.1561
_refine_ls_R_factor_gt           0.1065
_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)+(0.1000P)²+0.0000P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.2727
_refine_ls_wR_factor_ref         0.2986
_reflns_number_gt                924
_reflns_number_total             1580
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            ja1088309_si_002.cif
_cod_data_source_block           dh0608a
_cod_database_code               4103683
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'
'z, x, y'
'z+1/2, -x+1/2, -y'
'-z+1/2, -x, y+1/2'
'-z, x+1/2, -y+1/2'
'y, z, x'
'-y, z+1/2, -x+1/2'
'y+1/2, -z+1/2, -x'
'-y+1/2, -z, x+1/2'
'y+3/4, x+1/4, -z+1/4'
'-y+3/4, -x+3/4, -z+3/4'
'y+1/4, -x+1/4, z+3/4'
'-y+1/4, x+3/4, z+1/4'
'x+3/4, z+1/4, -y+1/4'
'-x+1/4, z+3/4, y+1/4'
'-x+3/4, -z+3/4, -y+3/4'
'x+1/4, -z+1/4, y+3/4'
'z+3/4, y+1/4, -x+1/4'
'z+1/4, -y+1/4, x+3/4'
'-z+1/4, y+3/4, x+1/4'
'-z+3/4, -y+3/4, -x+3/4'
'x+1/2, y+1/2, z+1/2'
'-x+1, -y+1/2, z+1'
'-x+1/2, y+1, -z+1'
'x+1, -y+1, -z+1/2'
'z+1/2, x+1/2, y+1/2'
'z+1, -x+1, -y+1/2'
'-z+1, -x+1/2, y+1'
'-z+1/2, x+1, -y+1'
'y+1/2, z+1/2, x+1/2'
'-y+1/2, z+1, -x+1'
'y+1, -z+1, -x+1/2'
'-y+1, -z+1/2, x+1'
'y+5/4, x+3/4, -z+3/4'
'-y+5/4, -x+5/4, -z+5/4'
'y+3/4, -x+3/4, z+5/4'
'-y+3/4, x+5/4, z+3/4'
'x+5/4, z+3/4, -y+3/4'
'-x+3/4, z+5/4, y+3/4'
'-x+5/4, -z+5/4, -y+5/4'
'x+3/4, -z+3/4, y+5/4'
'z+5/4, y+3/4, -x+3/4'
'z+3/4, -y+3/4, x+5/4'
'-z+3/4, y+5/4, x+3/4'
'-z+5/4, -y+5/4, -x+5/4'
'-x, -y, -z'
'x-1/2, y, -z-1/2'
'x, -y-1/2, z-1/2'
'-x-1/2, y-1/2, z'
'-z, -x, -y'
'-z-1/2, x-1/2, y'
'z-1/2, x, -y-1/2'
'z, -x-1/2, y-1/2'
'-y, -z, -x'
'y, -z-1/2, x-1/2'
'-y-1/2, z-1/2, x'
'y-1/2, z, -x-1/2'
'-y-3/4, -x-1/4, z-1/4'
'y-3/4, x-3/4, z-3/4'
'-y-1/4, x-1/4, -z-3/4'
'y-1/4, -x-3/4, -z-1/4'
'-x-3/4, -z-1/4, y-1/4'
'x-1/4, -z-3/4, -y-1/4'
'x-3/4, z-3/4, y-3/4'
'-x-1/4, z-1/4, -y-3/4'
'-z-3/4, -y-1/4, x-1/4'
'-z-1/4, y-1/4, -x-3/4'
'z-1/4, -y-3/4, -x-1/4'
'z-3/4, y-3/4, x-3/4'
'-x+1/2, -y+1/2, -z+1/2'
'x, y+1/2, -z'
'x+1/2, -y, z'
'-x, y, z+1/2'
'-z+1/2, -x+1/2, -y+1/2'
'-z, x, y+1/2'
'z, x+1/2, -y'
'z+1/2, -x, y'
'-y+1/2, -z+1/2, -x+1/2'
'y+1/2, -z, x'
'-y, z, x+1/2'
'y, z+1/2, -x'
'-y-1/4, -x+1/4, z+1/4'
'y-1/4, x-1/4, z-1/4'
'-y+1/4, x+1/4, -z-1/4'
'y+1/4, -x-1/4, -z+1/4'
'-x-1/4, -z+1/4, y+1/4'
'x+1/4, -z-1/4, -y+1/4'
'x-1/4, z-1/4, y-1/4'
'-x+1/4, z+1/4, -y-1/4'
'-z-1/4, -y+1/4, x+1/4'
'-z+1/4, y+1/4, -x-1/4'
'z+1/4, -y-1/4, -x+1/4'
'z-1/4, y-1/4, x-1/4'
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
O1S O 0.7303(9) 0.3026(10) 0.7520(11) 0.035(6) Uiso 0.110(7) 1 d PD A -1
C1S C 0.7669(11) 0.2780(14) 0.7454(11) 0.035(6) Uiso 0.110(7) 1 d PD A -1
H1A H 0.7671 0.2556 0.7653 0.042 Uiso 0.110(7) 1 calc PR A -1
H1B H 0.7910 0.2950 0.7505 0.042 Uiso 0.110(7) 1 calc PR A -1
C2S C 0.7698(15) 0.2604(15) 0.7028(11) 0.035(6) Uiso 0.110(7) 1 d PD A -1
H2A H 0.7531 0.2764 0.6843 0.053 Uiso 0.110(7) 1 calc PR A -1
H2B H 0.7603 0.2323 0.7031 0.053 Uiso 0.110(7) 1 calc PR A -1
H2C H 0.7981 0.2611 0.6938 0.053 Uiso 0.110(7) 1 calc PR A -1
O3S O 0.6959(17) 0.275(2) 0.755(2) 0.035(6) Uiso 0.056(7) 1 d PD A -2
C3S C 0.7368(17) 0.264(2) 0.742(3) 0.035(6) Uiso 0.056(7) 1 d PD A -2
H3A H 0.7533 0.2559 0.7655 0.042 Uiso 0.056(7) 1 calc PR A -2
H3B H 0.7499 0.2876 0.7289 0.042 Uiso 0.056(7) 1 calc PR A -2
C4S C 0.735(3) 0.229(2) 0.712(3) 0.035(6) Uiso 0.056(7) 1 d PD A -2
H4A H 0.7201 0.2375 0.6873 0.053 Uiso 0.056(7) 1 calc PR A -2
H4B H 0.7207 0.2059 0.7240 0.053 Uiso 0.056(7) 1 calc PR A -2
H4C H 0.7623 0.2207 0.7041 0.053 Uiso 0.056(7) 1 calc PR A -2
C11 C 0.6186(2) 0.2794(2) 0.6574(3) 0.083(2) Uani 1 1 d . B .
H11A H 0.6014 0.2968 0.6751 0.099 Uiso 1 1 calc R . .
C12 C 0.6604(2) 0.2973(2) 0.6484(2) 0.075(2) Uani 1 1 d U . .
C13 C 0.6744(3) 0.3359(3) 0.6638(2) 0.085(2) Uani 1 1 d U B .
O13 O 0.65225(15) 0.35706(15) 0.68764(18) 0.0948(18) Uani 1 1 d . . .
C14 C 0.7140(2) 0.3478(2) 0.6522(2) 0.070(2) Uani 1 1 d U . .
C15 C 0.7374(2) 0.3243(3) 0.6284(2) 0.079(2) Uani 1 1 d U B .
C16 C 0.7246(2) 0.2847(3) 0.6133(2) 0.077(2) Uani 1 1 d U . .
O16 O 0.74723(14) 0.26284(16) 0.59134(14) 0.0804(16) Uani 1 1 d . B .
C17 C 0.6840(2) 0.2732(2) 0.6244(2) 0.074(2) Uani 1 1 d U B .
C18 C 0.6648(2) 0.2338(2) 0.6124(2) 0.075(2) Uani 1 1 d . . .
H18A H 0.6821 0.2163 0.5947 0.090 Uiso 1 1 calc R B .
C21 C 0.6001(3) 0.2705(2) 0.6169(3) 0.085(2) Uani 1 1 d U . .
C22 C 0.5620(3) 0.2842(3) 0.6050(3) 0.105(3) Uani 1 1 d U B .
H22A H 0.5465 0.3013 0.6222 0.127 Uiso 1 1 calc R . .
C23 C 0.5480(3) 0.2727(3) 0.5691(4) 0.116(4) Uani 1 1 d U . .
H23A H 0.5223 0.2823 0.5605 0.140 Uiso 1 1 calc R B .
C24 C 0.5698(3) 0.2471(3) 0.5437(3) 0.106(3) Uani 1 1 d U B .
H24A H 0.5587 0.2391 0.5184 0.127 Uiso 1 1 calc R . .
C25 C 0.6109(3) 0.2322(3) 0.5562(3) 0.100(3) Uani 1 1 d U . .
H25A H 0.6268 0.2148 0.5397 0.120 Uiso 1 1 calc R B .
C26 C 0.6237(3) 0.2456(2) 0.5934(3) 0.081(2) Uani 1 1 d U B .
C73 C 0.6298(7) 0.3828(6) 0.6727(8) 0.0948(18) Uani 0.33 1 d P B -1
H73A H 0.6154 0.3971 0.6943 0.142 Uiso 0.33 1 calc PR B -1
H73B H 0.6102 0.3695 0.6548 0.142 Uiso 0.33 1 calc PR B -1
H73C H 0.6460 0.4021 0.6571 0.142 Uiso 0.33 1 calc PR B -1
C76 C 0.7764(6) 0.2343(6) 0.6150(6) 0.0804(16) Uani 0.33 1 d P B -2
H76A H 0.7921 0.2181 0.5957 0.121 Uiso 0.33 1 calc PR B -2
H76B H 0.7606 0.2164 0.6325 0.121 Uiso 0.33 1 calc PR B -2
H76C H 0.7948 0.2506 0.6316 0.121 Uiso 0.33 1 calc PR B -2
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
O1S C1S C2S 114(2) . .
O1S C1S H1A 108.9 . .
C2S C1S H1A 108.9 . .
O1S C1S H1B 108.9 . .
C2S C1S H1B 108.9 . .
H1A C1S H1B 107.7 . .
C1S C2S H2A 109.5 . .
C1S C2S H2B 109.5 . .
H2A C2S H2B 109.5 . .
C1S C2S H2C 109.5 . .
H2A C2S H2C 109.5 . .
H2B C2S H2C 109.5 . .
O3S C3S C4S 110(2) . .
O3S C3S H3A 109.7 . .
C4S C3S H3A 109.7 . .
O3S C3S H3B 109.7 . .
C4S C3S H3B 109.7 . .
H3A C3S H3B 108.2 . .
C3S C4S H4A 109.5 . .
C3S C4S H4B 109.5 . .
H4A C4S H4B 109.5 . .
C3S C4S H4C 109.5 . .
H4A C4S H4C 109.5 . .
H4B C4S H4C 109.5 . .
C21 C11 C12 105.8(6) . .
C21 C11 C15 105.0(6) . 79_546
C12 C11 C15 103.5(6) . 79_546
C21 C11 H11A 113.8 . .
C12 C11 H11A 113.8 . .
C15 C11 H11A 113.8 79_546 .
C17 C12 C13 122.2(7) . .
C17 C12 C11 113.7(7) . .
C13 C12 C11 124.1(7) . .
O13 C13 C14 122.7(8) . .
O13 C13 C12 120.9(7) . .
C14 C13 C12 116.4(7) . .
C73 O13 C13 118.3(13) . .
C15 C14 C13 121.7(7) . .
C15 C14 C18 114.2(7) . 82_565
C13 C14 C18 124.1(7) . 82_565
C14 C15 C16 123.3(7) . .
C14 C15 C11 114.2(7) . 82_565
C16 C15 C11 122.6(7) . 82_565
O16 C16 C17 123.0(8) . .
O16 C16 C15 122.3(7) . .
C17 C16 C15 114.7(8) . .
C16 O16 C76 115.0(9) . .
C12 C17 C16 121.7(7) . .
C12 C17 C18 114.6(7) . .
C16 C17 C18 123.6(8) . .
C17 C18 C14 105.1(6) . 79_546
C17 C18 C26 105.0(6) . .
C14 C18 C26 102.6(6) 79_546 .
C17 C18 H18A 114.3 . .
C14 C18 H18A 114.3 79_546 .
C26 C18 H18A 114.3 . .
C26 C21 C22 123.3(9) . .
C26 C21 C11 112.8(7) . .
C22 C21 C11 123.8(9) . .
C23 C22 C21 118.2(11) . .
C23 C22 H22A 120.9 . .
C21 C22 H22A 120.9 . .
C22 C23 C24 122.1(11) . .
C22 C23 H23A 118.9 . .
C24 C23 H23A 118.9 . .
C23 C24 C25 120.0(9) . .
C23 C24 H24A 120.0 . .
C25 C24 H24A 120.0 . .
C26 C25 C24 114.9(9) . .
C26 C25 H25A 122.6 . .
C24 C25 H25A 122.6 . .
C25 C26 C21 121.4(8) . .
C25 C26 C18 123.6(9) . .
C21 C26 C18 115.0(8) . .
O13 C73 H73A 109.5 . .
O13 C73 H73B 109.5 . .
H73A C73 H73B 109.5 . .
O13 C73 H73C 109.5 . .
H73A C73 H73C 109.5 . .
H73B C73 H73C 109.5 . .
O16 C76 H76A 109.5 . .
O16 C76 H76B 109.5 . .
H76A C76 H76B 109.5 . .
O16 C76 H76C 109.5 . .
H76A C76 H76C 109.5 . .
H76B C76 H76C 109.5 . .
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
O1S C1S 1.47(2) .
C1S C2S 1.53(2) .
C1S H1A 0.9900 .
C1S H1B 0.9900 .
C2S H2A 0.9800 .
C2S H2B 0.9800 .
C2S H2C 0.9800 .
O3S C3S 1.47(2) .
C3S C4S 1.53(2) .
C3S H3A 0.9900 .
C3S H3B 0.9900 .
C4S H4A 0.9800 .
C4S H4B 0.9800 .
C4S H4C 0.9800 .
C11 C21 1.499(10) .
C11 C12 1.530(9) .
C11 C15 1.547(9) 79_546
C11 H11A 1.0000 .
C12 C17 1.366(9) .
C12 C13 1.448(10) .
C13 O13 1.284(8) .
C13 C14 1.418(10) .
O13 C73 1.23(2) .
C14 C15 1.349(9) .
C14 C18 1.526(9) 82_565
C15 C16 1.462(10) .
C15 C11 1.547(9) 82_565
C16 O16 1.266(8) .
C16 C17 1.442(9) .
O16 C76 1.56(2) .
C17 C18 1.502(9) .
C18 C14 1.526(9) 79_546
C18 C26 1.543(10) .
C18 H18A 1.0000 .
C21 C26 1.374(10) .
C21 C22 1.392(10) .
C22 C23 1.331(11) .
C22 H22A 0.9500 .
C23 C24 1.391(12) .
C23 H23A 0.9500 .
C24 C25 1.503(11) .
C24 H24A 0.9500 .
C25 C26 1.373(10) .
C25 H25A 0.9500 .
C73 H73A 0.9800 .
C73 H73B 0.9800 .
C73 H73C 0.9800 .
C76 H76A 0.9800 .
C76 H76B 0.9800 .
C76 H76C 0.9800 .
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
C21 C11 C12 C17 -54.8(8) . .
C15 C11 C12 C17 55.4(9) 79_546 .
C21 C11 C12 C13 125.6(8) . .
C15 C11 C12 C13 -124.3(8) 79_546 .
C17 C12 C13 O13 -177.2(7) . .
C11 C12 C13 O13 2.5(11) . .
C17 C12 C13 C14 0.7(11) . .
C11 C12 C13 C14 -179.6(7) . .
C14 C13 O13 C73 89.9(15) . .
C12 C13 O13 C73 -92.3(14) . .
O13 C13 C14 C15 177.3(7) . .
C12 C13 C14 C15 -0.5(11) . .
O13 C13 C14 C18 -3.1(11) . 82_565
C12 C13 C14 C18 179.0(6) . 82_565
C13 C14 C15 C16 -1.2(11) . .
C18 C14 C15 C16 179.2(6) 82_565 .
C13 C14 C15 C11 179.4(6) . 82_565
C18 C14 C15 C11 -0.3(9) 82_565 82_565
C14 C15 C16 O16 -179.1(7) . .
C11 C15 C16 O16 0.3(11) 82_565 .
C14 C15 C16 C17 2.6(10) . .
C11 C15 C16 C17 -178.0(6) 82_565 .
C17 C16 O16 C76 -94.5(11) . .
C15 C16 O16 C76 87.4(11) . .
C13 C12 C17 C16 0.8(11) . .
C11 C12 C17 C16 -178.9(6) . .
C13 C12 C17 C18 178.2(6) . .
C11 C12 C17 C18 -1.5(9) . .
O16 C16 C17 C12 179.4(7) . .
C15 C16 C17 C12 -2.4(10) . .
O16 C16 C17 C18 2.2(11) . .
C15 C16 C17 C18 -179.5(6) . .
C12 C17 C18 C14 -54.0(8) . 79_546
C16 C17 C18 C14 123.3(7) . 79_546
C12 C17 C18 C26 53.8(8) . .
C16 C17 C18 C26 -128.9(7) . .
C12 C11 C21 C26 55.9(8) . .
C15 C11 C21 C26 -53.2(8) 79_546 .
C12 C11 C21 C22 -127.1(7) . .
C15 C11 C21 C22 123.8(8) 79_546 .
C26 C21 C22 C23 -0.2(12) . .
C11 C21 C22 C23 -176.9(8) . .
C21 C22 C23 C24 1.1(14) . .
C22 C23 C24 C25 -1.2(13) . .
C23 C24 C25 C26 0.4(10) . .
C24 C25 C26 C21 0.5(10) . .
C24 C25 C26 C18 179.6(6) . .
C22 C21 C26 C25 -0.6(12) . .
C11 C21 C26 C25 176.4(6) . .
C22 C21 C26 C18 -179.8(6) . .
C11 C21 C26 C18 -2.8(9) . .
C17 C18 C26 C25 128.6(7) . .
C14 C18 C26 C25 -121.8(7) 79_546 .
C17 C18 C26 C21 -52.2(8) . .
C14 C18 C26 C21 57.4(8) 79_546 .
