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#$Date: 2022-09-14 21:32:59 +0300 (Wed, 14 Sep 2022) $
#$Revision: 277840 $
#$URL: file:///home/coder/svn-repositories/cod/cif/4/02/21/4022144.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_4022144
loop_
_publ_author_name
'Sergiy V. Rosokha'
'Jay K. Kochi'
_publ_section_title
;
 The Question of Aromaticity in Open-Shell Cations and Anions as
 Ion-Radical Offsprings of Polycyclic Aromatic and Antiaromatic Hydrocarbons
;
_journal_name_full               'Journal of Organic Chemistry'
_journal_page_first              9357
_journal_page_last               9365
_journal_paper_doi               10.1021/jo061695a
_journal_volume                  71
_journal_year                    2006
_chemical_formula_moiety         'C20 H40 K O8, C10 H8'
_chemical_formula_sum            'C30 H48 K O8'
_chemical_formula_weight         575.78
_chemical_name_systematic
; 
 ? 
;
_space_group_IT_number           2
_space_group_name_Hall           '-P 1'
_space_group_name_H-M_alt        'P -1'
_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                95.20(8)
_cell_angle_beta                 106.50(5)
_cell_angle_gamma                113.31(8)
_cell_formula_units_Z            1
_cell_length_a                   8.134(6)
_cell_length_b                   9.116(8)
_cell_length_c                   12.165(11)
_cell_measurement_reflns_used    602
_cell_measurement_temperature    173(2)
_cell_measurement_theta_max      24.20
_cell_measurement_theta_min      2.75
_cell_volume                     772.9(11)
_computing_cell_refinement       'SAINT (Bruker, 2003)'
_computing_data_collection       'SMART (Bruker, 2003)'
_computing_data_reduction        'SAINT & SADABS (Bruker, 2003)'
_computing_molecular_graphics    'XP (Bruker, 1999)'
_computing_publication_material  'SHELXL, XCIF (Bruker, 1999)'
_computing_structure_refinement  SHELXTL
_computing_structure_solution    'SHELXTL (Bruker, 2003)'
_diffrn_ambient_temperature      173(2)
_diffrn_measured_fraction_theta_full 0.996
_diffrn_measured_fraction_theta_max 0.984
_diffrn_measurement_device       'Bruker SMART'
_diffrn_measurement_method       'omega-scan, full sphere'
_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  0.143
_diffrn_reflns_av_sigmaI/netI    0.3221
_diffrn_reflns_limit_h_max       11
_diffrn_reflns_limit_h_min       -11
_diffrn_reflns_limit_k_max       12
_diffrn_reflns_limit_k_min       -12
_diffrn_reflns_limit_l_max       16
_diffrn_reflns_limit_l_min       -16
_diffrn_reflns_number            11162
_diffrn_reflns_theta_full        29.00
_diffrn_reflns_theta_max         29.19
_diffrn_reflns_theta_min         1.79
_diffrn_standards_decay_%        0
_diffrn_standards_interval_count 0
_diffrn_standards_interval_time  0
_diffrn_standards_number         0
_exptl_absorpt_coefficient_mu    0.218
_exptl_absorpt_correction_type   none
_exptl_crystal_colour            black
_exptl_crystal_density_diffrn    1.237
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       plate
_exptl_crystal_F_000             311
_exptl_crystal_size_max          0.20
_exptl_crystal_size_mid          0.10
_exptl_crystal_size_min          0.05
_refine_diff_density_max         0.355
_refine_diff_density_min         -0.490
_refine_diff_density_rms         0.070
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   0.698
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     178
_refine_ls_number_reflns         4119
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      0.698
_refine_ls_R_factor_all          0.2108
_refine_ls_R_factor_gt           0.0625
_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)+(0.0000P)²+0.0000P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0752
_refine_ls_wR_factor_ref         0.1048
_reflns_number_gt                1273
_reflns_number_total             4119
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            jo061695asi20060815_022927.cif
_cod_database_code               4022144
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
K1 K 0.5000 0.5000 0.5000 0.0304(3) Uani 1 2 d S
O11 O 0.5574(3) 0.2144(2) 0.46399(18) 0.0311(6) Uani 1 1 d .
O12 O 0.8563(3) 0.5131(3) 0.61686(19) 0.0344(6) Uani 1 1 d .
O13 O 0.7622(3) 0.7632(2) 0.68377(18) 0.0310(6) Uani 1 1 d .
O31 O 0.3386(3) 0.4043(3) 0.6659(2) 0.0439(7) Uani 1 1 d .
C1 C 1.0732(4) 1.2156(4) 0.9831(3) 0.0324(9) Uani 1 1 d .
H1A H 1.1841 1.3073 0.9849 0.039 Uiso 1 1 calc R
C2 C 0.9024(5) 1.2288(4) 0.9612(3) 0.0373(9) Uani 1 1 d .
H2A H 0.8986 1.3291 0.9489 0.045 Uiso 1 1 calc R
C3 C 0.7383(5) 1.0966(4) 0.9572(3) 0.0362(9) Uani 1 1 d .
H3A H 0.6223 1.1061 0.9434 0.043 Uiso 1 1 calc R
C4 C 0.7446(4) 0.9490(4) 0.9736(3) 0.0332(9) Uani 1 1 d .
H4A H 0.6305 0.8581 0.9687 0.040 Uiso 1 1 calc R
C11 C 0.7552(4) 0.2556(4) 0.4934(3) 0.0371(9) Uani 1 1 d .
H11A H 0.8046 0.3152 0.4369 0.045 Uiso 1 1 calc R
H11B H 0.7732 0.1542 0.4885 0.045 Uiso 1 1 calc R
C12 C 0.8628(5) 0.3611(4) 0.6158(3) 0.0416(10) Uani 1 1 d .
H12A H 0.8046 0.3068 0.6712 0.050 Uiso 1 1 calc R
H12B H 0.9972 0.3780 0.6410 0.050 Uiso 1 1 calc R
C13 C 0.9538(4) 0.6211(4) 0.7308(3) 0.0354(9) Uani 1 1 d .
H13A H 1.0868 0.6350 0.7615 0.042 Uiso 1 1 calc R
H13B H 0.8892 0.5743 0.7858 0.042 Uiso 1 1 calc R
C14 C 0.9538(4) 0.7824(4) 0.7224(3) 0.0346(9) Uani 1 1 d .
H14A H 1.0272 0.8603 0.8003 0.042 Uiso 1 1 calc R
H14B H 1.0159 0.8278 0.6660 0.042 Uiso 1 1 calc R
C15 C 0.7544(4) 0.9157(4) 0.6825(3) 0.0321(9) Uani 1 1 d .
H15A H 0.8064 0.9660 0.6236 0.039 Uiso 1 1 calc R
H15B H 0.8321 0.9918 0.7609 0.039 Uiso 1 1 calc R
C16 C 0.5512(4) 0.8861(4) 0.6518(3) 0.0344(9) Uani 1 1 d .
H16A H 0.4981 0.8313 0.7089 0.041 Uiso 1 1 calc R
H16B H 0.5438 0.9922 0.6562 0.041 Uiso 1 1 calc R
C31 C 0.4355(5) 0.4806(4) 0.7885(3) 0.0399(10) Uani 1 1 d .
H31A H 0.3493 0.5034 0.8232 0.048 Uiso 1 1 calc R
H31B H 0.5487 0.5852 0.8008 0.048 Uiso 1 1 calc R
C32 C 0.4950(4) 0.3594(4) 0.8436(3) 0.0410(10) Uani 1 1 d .
H32A H 0.6175 0.3700 0.8369 0.049 Uiso 1 1 calc R
H32B H 0.5068 0.3733 0.9276 0.049 Uiso 1 1 calc R
C33 C 0.3316(5) 0.1978(4) 0.7705(3) 0.0491(11) Uani 1 1 d .
H33A H 0.3731 0.1093 0.7696 0.059 Uiso 1 1 calc R
H33B H 0.2245 0.1667 0.8008 0.059 Uiso 1 1 calc R
C34 C 0.2752(5) 0.2301(4) 0.6509(3) 0.0464(11) Uani 1 1 d .
H34A H 0.3358 0.1919 0.6021 0.056 Uiso 1 1 calc R
H34B H 0.1348 0.1713 0.6112 0.056 Uiso 1 1 calc R
C5 C 0.9144(4) 0.9299(4) 0.9972(3) 0.0270(8) 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'
K K 0.2009 0.2494 '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
O31 K1 O31 180.000(1) 2_666 .
O31 K1 O13 82.75(11) 2_666 2_666
O31 K1 O13 97.25(11) . 2_666
O31 K1 O13 97.25(11) 2_666 .
O31 K1 O13 82.75(11) . .
O13 K1 O13 180.0 2_666 .
O31 K1 O12 82.34(9) 2_666 .
O31 K1 O12 97.66(9) . .
O13 K1 O12 119.31(10) 2_666 .
O13 K1 O12 60.69(10) . .
O31 K1 O12 97.66(9) 2_666 2_666
O31 K1 O12 82.34(9) . 2_666
O13 K1 O12 60.69(10) 2_666 2_666
O13 K1 O12 119.31(10) . 2_666
O12 K1 O12 180.0 . 2_666
O31 K1 O11 87.00(9) 2_666 .
O31 K1 O11 93.00(9) . .
O13 K1 O11 60.19(9) 2_666 .
O13 K1 O11 119.81(9) . .
O12 K1 O11 60.55(11) . .
O12 K1 O11 119.45(11) 2_666 .
O31 K1 O11 93.00(9) 2_666 2_666
O31 K1 O11 87.00(9) . 2_666
O13 K1 O11 119.81(9) 2_666 2_666
O13 K1 O11 60.19(9) . 2_666
O12 K1 O11 119.45(11) . 2_666
O12 K1 O11 60.55(11) 2_666 2_666
O11 K1 O11 180.000(1) . 2_666
C16 O11 C11 111.5(2) 2_666 .
C16 O11 K1 112.67(18) 2_666 .
C11 O11 K1 111.14(19) . .
C12 O12 C13 112.5(2) . .
C12 O12 K1 116.1(2) . .
C13 O12 K1 114.02(19) . .
C15 O13 C14 112.1(2) . .
C15 O13 K1 117.87(19) . .
C14 O13 K1 116.56(19) . .
C31 O31 C34 108.8(3) . .
C31 O31 K1 122.50(19) . .
C34 O31 K1 107.7(2) . .
C2 C1 C5 121.8(3) . 2_777
C2 C1 H1A 119.1 . .
C5 C1 H1A 119.1 2_777 .
C3 C2 C1 120.3(3) . .
C3 C2 H2A 119.9 . .
C1 C2 H2A 119.9 . .
C2 C3 C4 119.4(3) . .
C2 C3 H3A 120.3 . .
C4 C3 H3A 120.3 . .
C3 C4 C5 122.4(3) . .
C3 C4 H4A 118.8 . .
C5 C4 H4A 118.8 . .
O11 C11 C12 109.4(3) . .
O11 C11 H11A 109.8 . .
C12 C11 H11A 109.8 . .
O11 C11 H11B 109.8 . .
C12 C11 H11B 109.8 . .
H11A C11 H11B 108.2 . .
O12 C12 C11 108.7(3) . .
O12 C12 H12A 109.9 . .
C11 C12 H12A 109.9 . .
O12 C12 H12B 109.9 . .
C11 C12 H12B 109.9 . .
H12A C12 H12B 108.3 . .
O12 C13 C14 109.1(3) . .
O12 C13 H13A 109.9 . .
C14 C13 H13A 109.9 . .
O12 C13 H13B 109.9 . .
C14 C13 H13B 109.9 . .
H13A C13 H13B 108.3 . .
O13 C14 C13 109.7(3) . .
O13 C14 H14A 109.7 . .
C13 C14 H14A 109.7 . .
O13 C14 H14B 109.7 . .
C13 C14 H14B 109.7 . .
H14A C14 H14B 108.2 . .
O13 C15 C16 108.5(3) . .
O13 C15 H15A 110.0 . .
C16 C15 H15A 110.0 . .
O13 C15 H15B 110.0 . .
C16 C15 H15B 110.0 . .
H15A C15 H15B 108.4 . .
O11 C16 C15 109.8(3) 2_666 .
O11 C16 H16A 109.7 2_666 .
C15 C16 H16A 109.7 . .
O11 C16 H16B 109.7 2_666 .
C15 C16 H16B 109.7 . .
H16A C16 H16B 108.2 . .
O31 C31 C32 105.5(3) . .
O31 C31 H31A 110.6 . .
C32 C31 H31A 110.6 . .
O31 C31 H31B 110.6 . .
C32 C31 H31B 110.6 . .
H31A C31 H31B 108.8 . .
C33 C32 C31 101.8(3) . .
C33 C32 H32A 111.4 . .
C31 C32 H32A 111.4 . .
C33 C32 H32B 111.4 . .
C31 C32 H32B 111.4 . .
H32A C32 H32B 109.3 . .
C34 C33 C32 103.5(3) . .
C34 C33 H33A 111.1 . .
C32 C33 H33A 111.1 . .
C34 C33 H33B 111.1 . .
C32 C33 H33B 111.1 . .
H33A C33 H33B 109.0 . .
O31 C34 C33 107.2(3) . .
O31 C34 H34A 110.3 . .
C33 C34 H34A 110.3 . .
O31 C34 H34B 110.3 . .
C33 C34 H34B 110.3 . .
H34A C34 H34B 108.5 . .
C1 C5 C4 123.9(3) 2_777 .
C1 C5 C5 118.5(4) 2_777 2_777
C4 C5 C5 117.5(4) . 2_777
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
K1 O31 2.734(3) 2_666
K1 O31 2.734(3) .
K1 O13 2.752(5) 2_666
K1 O13 2.752(5) .
K1 O12 2.791(3) .
K1 O12 2.791(3) 2_666
K1 O11 2.839(3) .
K1 O11 2.839(3) 2_666
O11 C16 1.422(4) 2_666
O11 C11 1.424(3) .
O12 C12 1.407(4) .
O12 C13 1.425(4) .
O13 C15 1.418(4) .
O13 C14 1.426(4) .
O31 C31 1.429(4) .
O31 C34 1.438(4) .
C1 C2 1.394(4) .
C1 C5 1.406(4) 2_777
C1 H1A 0.9500 .
C2 C3 1.385(4) .
C2 H2A 0.9500 .
C3 C4 1.396(4) .
C3 H3A 0.9500 .
C4 C5 1.412(4) .
C4 H4A 0.9500 .
C11 C12 1.498(5) .
C11 H11A 0.9900 .
C11 H11B 0.9900 .
C12 H12A 0.9900 .
C12 H12B 0.9900 .
C13 C14 1.484(4) .
C13 H13A 0.9900 .
C13 H13B 0.9900 .
C14 H14A 0.9900 .
C14 H14B 0.9900 .
C15 C16 1.491(4) .
C15 H15A 0.9900 .
C15 H15B 0.9900 .
C16 O11 1.422(4) 2_666
C16 H16A 0.9900 .
C16 H16B 0.9900 .
C31 C32 1.510(4) .
C31 H31A 0.9900 .
C31 H31B 0.9900 .
C32 C33 1.506(4) .
C32 H32A 0.9900 .
C32 H32B 0.9900 .
C33 C34 1.490(4) .
C33 H33A 0.9900 .
C33 H33B 0.9900 .
C34 H34A 0.9900 .
C34 H34B 0.9900 .
C5 C1 1.406(4) 2_777
C5 C5 1.449(5) 2_777
