#------------------------------------------------------------------------------
#$Date: 2019-11-23 18:41:10 +0200 (Sat, 23 Nov 2019) $
#$Revision: 234479 $
#$URL: file:///home/coder/svn-repositories/cod/cif/4/03/62/4036265.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_4036265
loop_
_publ_author_name
'Naoda, Koji'
'Mori, Hirotaka'
'Oh, Juwon'
'Park, Kyu Hyung'
'Kim, Dongho'
'Osuka, Atsuhiro'
_publ_section_title
;
 5,20-Di(pyridin-2-yl)-[28]hexaphyrin(1.1.1.1.1.1): A Stable Hückel
 Antiaromatic Hexaphyrin Stabilized by Intramolecular Hydrogen Bonding and
 Protonation-Induced Conformational Twist To Gain Möbius Aromaticity.
;
_journal_issue                   23
_journal_name_full               'The Journal of organic chemistry'
_journal_page_first              11726
_journal_page_last               11733
_journal_paper_doi               10.1021/acs.joc.5b01348
_journal_volume                  80
_journal_year                    2015
_chemical_formula_moiety
'C32 H13 F10 N4, (C H3 O3 S), (C H4 O3 S), 2(C H2 Cl2)'
_chemical_formula_sum            'C36 H24 Cl4 F10 N4 O6 S2'
_chemical_formula_weight         1004.51
_space_group_IT_number           14
_space_group_name_Hall           '-P 2ybc'
_space_group_name_H-M_alt        'P 1 21/c 1'
_symmetry_cell_setting           monoclinic
_symmetry_Int_Tables_number      14
_symmetry_space_group_name_Hall  '-P 2ybc'
_symmetry_space_group_name_H-M   'P 1 21/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                 114.461(3)
_cell_angle_gamma                90.00
_cell_formula_units_Z            4
_cell_length_a                   14.108(3)
_cell_length_b                   24.897(5)
_cell_length_c                   15.092(3)
_cell_measurement_reflns_used    3978
_cell_measurement_temperature    93(2)
_cell_measurement_theta_max      68.3
_cell_measurement_theta_min      25.2
_cell_volume                     4825.2(17)
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 1990)'
_diffrn_ambient_temperature      93(2)
_diffrn_detector_area_resol_mean 5.8140
_diffrn_measured_fraction_theta_full 0.986
_diffrn_measured_fraction_theta_max 0.986
_diffrn_measurement_device_type  'Rigaku XtaLAB P200'
_diffrn_measurement_method       ω
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_source         'fine-focus sealed tube'
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54187
_diffrn_reflns_av_R_equivalents  0.0446
_diffrn_reflns_av_sigmaI/netI    0.0372
_diffrn_reflns_limit_h_max       16
_diffrn_reflns_limit_h_min       -16
_diffrn_reflns_limit_k_max       29
_diffrn_reflns_limit_k_min       -28
_diffrn_reflns_limit_l_max       17
_diffrn_reflns_limit_l_min       -17
_diffrn_reflns_number            30745
_diffrn_reflns_theta_full        64.99
_diffrn_reflns_theta_max         64.99
_diffrn_reflns_theta_min         6.53
_exptl_absorpt_coefficient_mu    3.784
_exptl_absorpt_correction_T_max  0.9282
_exptl_absorpt_correction_T_min  0.1956
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   'REQAB (Rigaku, 1998)'
_exptl_crystal_colour            blue
_exptl_crystal_density_diffrn    1.383
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       prims
_exptl_crystal_F_000             2024
_exptl_crystal_size_max          0.64
_exptl_crystal_size_mid          0.04
_exptl_crystal_size_min          0.02
_platon_squeeze_details
;
;
_refine_diff_density_max         1.379
_refine_diff_density_min         -1.081
_refine_diff_density_rms         0.129
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.016
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     636
_refine_ls_number_reflns         8098
_refine_ls_number_restraints     144
_refine_ls_restrained_S_all      1.008
_refine_ls_R_factor_all          0.1130
_refine_ls_R_factor_gt           0.0961
_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)+(0.1450P)²+23.2197P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.2547
_refine_ls_wR_factor_ref         0.2699
_reflns_number_gt                6237
_reflns_number_total             8098
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            jo5b01348_si_003.cif
_cod_data_source_block           50521n
_cod_original_sg_symbol_H-M      'P 21/c'
_cod_database_code               4036265
loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'-x, y+1/2, -z+1/2'
'-x, -y, -z'
'x, -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
O1 O 0.5339(3) 0.64198(17) 0.9190(3) 0.0458(10) Uani 1 1 d . . .
O2 O 0.5152(3) 0.56750(15) 0.8108(3) 0.0297(8) Uani 1 1 d . . .
O3 O 0.4655(3) 0.55713(16) 0.9454(3) 0.0373(9) Uani 1 1 d . . .
O4 O 0.0959(3) 0.5335(2) 0.8537(4) 0.0548(13) Uani 1 1 d . . .
H22 H 0.1452 0.5551 0.8806 0.082 Uiso 1 1 calc R . .
O5 O 0.1625(4) 0.5078(2) 0.7381(4) 0.0616(14) Uani 1 1 d . . .
O6 O 0.2070(6) 0.4574(4) 0.8792(8) 0.155(5) Uani 1 1 d . . .
S1 S 0.47448(9) 0.59338(5) 0.87401(9) 0.0281(3) Uani 1 1 d . . .
S2 S 0.12877(11) 0.49186(6) 0.81079(12) 0.0395(4) Uani 1 1 d . . .
Cl1 Cl 0.1481(3) 0.4559(2) 0.4349(4) 0.1577(16) Uani 1 1 d . . .
Cl2 Cl 0.0418(6) 0.3831(2) 0.5025(5) 0.210(3) Uani 1 1 d . . .
Cl3 Cl 0.33421(17) 0.33160(12) 0.54389(17) 0.0885(7) Uani 1 1 d . . .
Cl4 Cl 0.55121(17) 0.30181(13) 0.6110(2) 0.1011(9) Uani 1 1 d . . .
F1 F 0.6734(2) 0.69455(12) 0.8063(2) 0.0353(7) Uani 1 1 d . . .
F2 F 0.4718(3) 0.71626(15) 0.6929(3) 0.0532(10) Uani 1 1 d . . .
F3 F 0.3605(2) 0.65014(17) 0.5447(3) 0.0547(10) Uani 1 1 d . . .
F4 F 0.4521(3) 0.56142(16) 0.5075(2) 0.0514(9) Uani 1 1 d . . .
F5 F 0.6513(2) 0.53923(13) 0.6206(2) 0.0381(7) Uani 1 1 d . . .
N1 N 0.9610(3) 0.63764(15) 0.8434(3) 0.0198(8) Uani 1 1 d . . .
H1 H 0.9901 0.6157 0.8930 0.024 Uiso 1 1 calc R . .
N2 N 0.7134(3) 0.52712(15) 0.8418(3) 0.0194(8) Uani 1 1 d . . .
H2 H 0.6486 0.5385 0.8194 0.023 Uiso 1 1 calc R . .
N3 N 0.8013(3) 0.38333(15) 1.0233(3) 0.0199(8) Uani 1 1 d . . .
N4 N 0.4938(3) 0.44885(16) 0.8622(3) 0.0223(9) Uani 1 1 d . . .
H3 H 0.5143 0.4456 0.9255 0.027 Uiso 1 1 calc R . .
C1 C 1.0115(4) 0.67818(19) 0.8179(4) 0.0243(10) Uani 1 1 d . . .
C2 C 0.9377(4) 0.7023(2) 0.7334(4) 0.0365(13) Uani 1 1 d . . .
H4 H 0.9505 0.7313 0.6987 0.044 Uiso 1 1 calc R . .
C3 C 0.8444(4) 0.6770(2) 0.7096(4) 0.0358(13) Uani 1 1 d . . .
H5 H 0.7812 0.6852 0.6554 0.043 Uiso 1 1 calc R . .
C4 C 0.8580(4) 0.63705(19) 0.7788(3) 0.0222(10) Uani 1 1 d . . .
C5 C 0.7790(3) 0.6017(2) 0.7816(3) 0.0221(10) Uani 1 1 d . . .
C6 C 0.7945(3) 0.55546(18) 0.8353(3) 0.0175(9) Uani 1 1 d . . .
C7 C 0.8862(3) 0.52250(18) 0.8834(3) 0.0205(9) Uani 1 1 d . . .
H6 H 0.9549 0.5314 0.8919 0.025 Uiso 1 1 calc R . .
C8 C 0.8572(3) 0.47711(18) 0.9140(3) 0.0202(9) Uani 1 1 d . . .
H7 H 0.9019 0.4483 0.9475 0.024 Uiso 1 1 calc R . .
C9 C 0.7469(3) 0.47962(19) 0.8873(3) 0.0192(9) Uani 1 1 d . . .
C10 C 0.6772(3) 0.44010(19) 0.8934(3) 0.0209(10) Uani 1 1 d . . .
C11 C 0.7066(3) 0.39385(19) 0.9499(3) 0.0196(9) Uani 1 1 d . . .
C12 C 0.6426(4) 0.3470(2) 0.9379(4) 0.0254(10) Uani 1 1 d . . .
H23 H 0.5725 0.3431 0.8918 0.030 Uiso 1 1 calc R . .
C13 C 0.6990(4) 0.3098(2) 1.0033(4) 0.0268(11) Uani 1 1 d . . .
H24 H 0.6753 0.2752 1.0114 0.032 Uiso 1 1 calc R . .
C14 C 0.8012(4) 0.33144(18) 1.0587(3) 0.0212(10) Uani 1 1 d . A .
C15 C 0.8826(3) 0.30545(19) 1.1313(3) 0.0223(10) Uani 1 1 d . . .
C16 C 0.6698(4) 0.61634(19) 0.7180(3) 0.0229(10) Uani 1 1 d . . .
C17 C 0.6209(4) 0.6614(2) 0.7326(4) 0.0282(11) Uani 1 1 d . . .
C18 C 0.5176(4) 0.6726(2) 0.6749(4) 0.0364(13) Uani 1 1 d . . .
C19 C 0.4610(4) 0.6394(2) 0.6009(4) 0.0361(13) Uani 1 1 d . . .
C20 C 0.5066(4) 0.5943(2) 0.5826(4) 0.0364(13) Uani 1 1 d . . .
C21 C 0.6091(4) 0.5829(2) 0.6403(3) 0.0265(11) Uani 1 1 d . . .
C22 C 0.5659(3) 0.44654(19) 0.8252(3) 0.0214(10) Uani 1 1 d . . .
C23 C 0.5328(4) 0.4500(2) 0.7248(4) 0.0265(11) Uani 1 1 d . . .
H8 H 0.5818 0.4476 0.6968 0.032 Uiso 1 1 calc R . .
C24 C 0.4291(4) 0.4570(2) 0.6665(4) 0.0303(11) Uani 1 1 d . . .
H9 H 0.4064 0.4599 0.5980 0.036 Uiso 1 1 calc R . .
C25 C 0.3571(4) 0.4598(2) 0.7071(4) 0.0357(13) Uani 1 1 d . . .
H10 H 0.2850 0.4643 0.6671 0.043 Uiso 1 1 calc R . .
C26 C 0.3926(4) 0.4558(2) 0.8068(4) 0.0289(11) Uani 1 1 d . . .
H11 H 0.3448 0.4581 0.8362 0.035 Uiso 1 1 calc R . .
C33 C 0.0346(13) 0.4037(10) 0.4046(9) 0.189(10) Uani 1 1 d . . .
H12 H -0.0336 0.4210 0.3676 0.227 Uiso 1 1 calc R . .
H13 H 0.0430 0.3737 0.3652 0.227 Uiso 1 1 calc R . .
C34 C 0.4288(6) 0.2822(4) 0.6017(7) 0.079(3) Uani 1 1 d . . .
H14 H 0.4324 0.2754 0.6677 0.094 Uiso 1 1 calc R . .
H15 H 0.4083 0.2483 0.5643 0.094 Uiso 1 1 calc R . .
C35 C 0.3481(4) 0.6149(3) 0.7989(4) 0.0407(14) Uani 1 1 d . . .
H16 H 0.3509 0.6396 0.7495 0.061 Uiso 1 1 calc R . .
H17 H 0.3177 0.6334 0.8383 0.061 Uiso 1 1 calc R . .
H18 H 0.3051 0.5838 0.7668 0.061 Uiso 1 1 calc R . .
C36 C 0.0183(9) 0.4502(4) 0.7574(11) 0.116(5) Uani 1 1 d . . .
H19 H 0.0350 0.4197 0.7254 0.174 Uiso 1 1 calc R . .
H20 H -0.0391 0.4708 0.7091 0.174 Uiso 1 1 calc R . .
H21 H -0.0024 0.4370 0.8079 0.174 Uiso 1 1 calc R . .
C27 C 0.8545(15) 0.2491(6) 1.1535(15) 0.025(4) Uani 0.57(5) 1 d PGU A 1
C28 C 0.8662(15) 0.2041(8) 1.1043(14) 0.036(4) Uani 0.57(5) 1 d PGU A 1
C29 C 0.8410(13) 0.1535(7) 1.1269(16) 0.046(5) Uani 0.57(5) 1 d PGU A 1
C30 C 0.8041(9) 0.1478(7) 1.199(2) 0.048(5) Uani 0.57(5) 1 d PGU A 1
C31 C 0.7924(12) 0.1927(8) 1.248(2) 0.048(6) Uani 0.57(5) 1 d PGU A 1
C32 C 0.8176(15) 0.2434(7) 1.2254(18) 0.042(5) Uani 0.57(5) 1 d PGU A 1
F6 F 0.807(2) 0.2859(13) 1.278(2) 0.080(7) Uani 0.57(5) 1 d P A 1
F7 F 0.7609(18) 0.1876(11) 1.320(3) 0.088(8) Uani 0.57(5) 1 d P A 1
F8 F 0.7778(13) 0.0996(8) 1.220(3) 0.089(7) Uani 0.57(5) 1 d P A 1
F9 F 0.848(2) 0.1113(8) 1.077(2) 0.086(7) Uani 0.57(5) 1 d P A 1
F10 F 0.9022(18) 0.2091(7) 1.0361(13) 0.044(3) Uani 0.57(5) 1 d P A 1
C41 C 0.860(2) 0.2555(9) 1.1737(16) 0.028(6) Uani 0.43(5) 1 d PGU A 2
C42 C 0.853(2) 0.2073(10) 1.1250(16) 0.029(5) Uani 0.43(5) 1 d PGU A 2
C43 C 0.8218(17) 0.1608(8) 1.1562(17) 0.038(6) Uani 0.43(5) 1 d PGU A 2
C44 C 0.7968(12) 0.1624(10) 1.2360(18) 0.035(6) Uani 0.43(5) 1 d PGU A 2
C45 C 0.8031(12) 0.2106(11) 1.2847(16) 0.045(6) Uani 0.43(5) 1 d PGU A 2
C46 C 0.8344(17) 0.2571(9) 1.2536(16) 0.034(5) Uani 0.43(5) 1 d PGU A 2
F10A F 0.8728(17) 0.2039(8) 1.0474(18) 0.035(4) Uani 0.43(5) 1 d P A 2
F13 F 0.7719(15) 0.1153(12) 1.265(2) 0.071(7) Uani 0.43(5) 1 d P A 2
F14 F 0.822(2) 0.1130(10) 1.111(2) 0.066(6) Uani 0.43(5) 1 d P A 2
F11 F 0.8375(18) 0.2989(13) 1.2943(18) 0.045(5) Uani 0.43(5) 1 d P A 2
F12 F 0.7830(15) 0.2101(13) 1.3614(16) 0.069(6) Uani 0.43(5) 1 d P A 2
loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0181 0.0091 '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'
F F 0.0727 0.0534 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
N N 0.0311 0.0180 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0492 0.0322 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
S S 0.3331 0.5567 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
Cl Cl 0.3639 0.7018 '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
S2 O4 H22 109.5 . .
O3 S1 O2 113.1(2) . .
O3 S1 O1 112.2(2) . .
O2 S1 O1 111.4(2) . .
O3 S1 C35 107.0(3) . .
O2 S1 C35 106.5(2) . .
O1 S1 C35 106.3(3) . .
O4 S2 O5 115.6(3) . .
O4 S2 O6 114.3(5) . .
O5 S2 O6 108.5(3) . .
O4 S2 C36 104.3(3) . .
O5 S2 C36 109.1(5) . .
O6 S2 C36 104.3(7) . .
C4 N1 C1 109.1(4) . .
C4 N1 H1 125.5 . .
C1 N1 H1 125.5 . .
C9 N2 C6 110.9(4) . .
C9 N2 H2 124.5 . .
C6 N2 H2 124.5 . .
C11 N3 C14 109.4(4) . .
C26 N4 C22 122.8(4) . .
C26 N4 H3 118.6 . .
C22 N4 H3 118.6 . .
N1 C1 C2 107.0(4) . .
N1 C1 C15 127.3(4) . 3_767
C2 C1 C15 125.6(4) . 3_767
C3 C2 C1 108.2(5) . .
C3 C2 H4 125.9 . .
C1 C2 H4 125.9 . .
C2 C3 C4 108.3(5) . .
C2 C3 H5 125.9 . .
C4 C3 H5 125.9 . .
N1 C4 C3 107.5(4) . .
N1 C4 C5 126.3(4) . .
C3 C4 C5 126.2(4) . .
C6 C5 C4 126.6(4) . .
C6 C5 C16 117.2(4) . .
C4 C5 C16 116.3(4) . .
C5 C6 N2 122.4(4) . .
C5 C6 C7 131.5(4) . .
N2 C6 C7 105.6(4) . .
C8 C7 C6 108.2(4) . .
C8 C7 H6 125.9 . .
C6 C7 H6 125.9 . .
C7 C8 C9 108.3(4) . .
C7 C8 H7 125.8 . .
C9 C8 H7 125.8 . .
N2 C9 C10 122.2(4) . .
N2 C9 C8 106.9(4) . .
C10 C9 C8 130.5(4) . .
C11 C10 C9 125.1(4) . .
C11 C10 C22 118.4(4) . .
C9 C10 C22 116.2(4) . .
N3 C11 C10 127.0(4) . .
N3 C11 C12 107.4(4) . .
C10 C11 C12 125.6(4) . .
C13 C12 C11 108.4(4) . .
C13 C12 H23 125.8 . .
C11 C12 H23 125.8 . .
C12 C13 C14 108.3(4) . .
C12 C13 H24 125.9 . .
C14 C13 H24 125.9 . .
C15 C14 N3 127.3(4) . .
C15 C14 C13 126.2(4) . .
N3 C14 C13 106.4(4) . .
C14 C15 C1 129.4(4) . 3_767
C14 C15 C41 118.3(11) . .
C1 C15 C41 111.9(11) 3_767 .
C14 C15 C27 113.5(9) . .
C1 C15 C27 116.9(8) 3_767 .
C41 C15 C27 12.2(14) . .
C17 C16 C21 116.3(4) . .
C17 C16 C5 123.3(4) . .
C21 C16 C5 120.4(4) . .
F1 C17 C16 119.6(4) . .
F1 C17 C18 118.4(5) . .
C16 C17 C18 122.0(5) . .
F2 C18 C19 119.4(5) . .
F2 C18 C17 120.3(5) . .
C19 C18 C17 120.3(5) . .
F3 C19 C18 120.5(5) . .
F3 C19 C20 119.6(5) . .
C18 C19 C20 119.9(5) . .
F4 C20 C21 119.3(5) . .
F4 C20 C19 120.8(5) . .
C21 C20 C19 119.9(5) . .
F5 C21 C20 118.6(5) . .
F5 C21 C16 119.7(4) . .
C20 C21 C16 121.6(5) . .
N4 C22 C23 118.5(4) . .
N4 C22 C10 118.6(4) . .
C23 C22 C10 122.9(4) . .
C24 C23 C22 119.7(5) . .
C24 C23 H8 120.2 . .
C22 C23 H8 120.2 . .
C23 C24 C25 120.3(5) . .
C23 C24 H9 119.8 . .
C25 C24 H9 119.8 . .
C26 C25 C24 118.4(5) . .
C26 C25 H10 120.8 . .
C24 C25 H10 120.8 . .
N4 C26 C25 120.3(5) . .
N4 C26 H11 119.9 . .
C25 C26 H11 119.9 . .
Cl2 C33 Cl1 106.0(9) . .
Cl2 C33 H12 110.5 . .
Cl1 C33 H12 110.5 . .
Cl2 C33 H13 110.5 . .
Cl1 C33 H13 110.5 . .
H12 C33 H13 108.7 . .
Cl4 C34 Cl3 111.5(6) . .
Cl4 C34 H14 109.3 . .
Cl3 C34 H14 109.3 . .
Cl4 C34 H15 109.3 . .
Cl3 C34 H15 109.3 . .
H14 C34 H15 108.0 . .
S1 C35 H16 109.5 . .
S1 C35 H17 109.5 . .
H16 C35 H17 109.5 . .
S1 C35 H18 109.5 . .
H16 C35 H18 109.5 . .
H17 C35 H18 109.5 . .
S2 C36 H19 109.5 . .
S2 C36 H20 109.5 . .
H19 C36 H20 109.5 . .
S2 C36 H21 109.5 . .
H19 C36 H21 109.5 . .
H20 C36 H21 109.5 . .
C28 C27 C32 120.0 . .
C28 C27 C15 121.5(11) . .
C32 C27 C15 118.5(11) . .
F10 C28 C27 120.4(14) . .
F10 C28 C29 119.6(14) . .
C27 C28 C29 120.0 . .
F9 C29 C30 120.0(14) . .
F9 C29 C28 119.9(14) . .
C30 C29 C28 120.0 . .
F8 C30 C29 120.4(12) . .
F8 C30 C31 119.6(12) . .
C29 C30 C31 120.0 . .
F7 C31 C30 120.6(11) . .
F7 C31 C32 119.4(11) . .
C30 C31 C32 120.0 . .
F6 C32 C31 117.2(12) . .
F6 C32 C27 122.7(13) . .
C31 C32 C27 120.0 . .
C42 C41 C46 120.0 . .
C42 C41 C15 118.0(14) . .
C46 C41 C15 121.7(14) . .
F10A C42 C41 122.4(17) . .
F10A C42 C43 117.6(17) . .
C41 C42 C43 120.0 . .
F14 C43 C44 120.9(15) . .
F14 C43 C42 119.0(15) . .
C44 C43 C42 120.0 . .
F13 C44 C43 116.9(14) . .
F13 C44 C45 123.0(14) . .
C43 C44 C45 120.0 . .
F12 C45 C46 121.7(14) . .
F12 C45 C44 118.3(14) . .
C46 C45 C44 120.0 . .
F11 C46 C45 119.9(16) . .
F11 C46 C41 120.1(16) . .
C45 C46 C41 120.0 . .
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
O1 S1 1.469(4) .
O2 S1 1.452(4) .
O3 S1 1.450(4) .
O4 S2 1.398(4) .
O4 H22 0.8400 .
O5 S2 1.421(5) .
O6 S2 1.441(7) .
S1 C35 1.755(5) .
S2 C36 1.765(9) .
Cl1 C33 1.96(2) .
Cl2 C33 1.527(15) .
Cl3 C34 1.758(11) .
Cl4 C34 1.743(8) .
F1 C17 1.337(6) .
F2 C18 1.348(7) .
F3 C19 1.344(6) .
F4 C20 1.351(7) .
F5 C21 1.331(6) .
N1 C4 1.374(6) .
N1 C1 1.379(6) .
N1 H1 0.8800 .
N2 C9 1.351(6) .
N2 C6 1.382(6) .
N2 H2 0.8800 .
N3 C11 1.362(6) .
N3 C14 1.398(6) .
N4 C26 1.333(6) .
N4 C22 1.350(6) .
N4 H3 0.8800 .
C1 C2 1.405(7) .
C1 C15 1.427(7) 3_767
C2 C3 1.367(8) .
C2 H4 0.9500 .
C3 C4 1.396(7) .
C3 H5 0.9500 .
C4 C5 1.434(7) .
C5 C6 1.373(7) .
C5 C16 1.484(6) .
C6 C7 1.448(6) .
C7 C8 1.347(7) .
C7 H6 0.9500 .
C8 C9 1.437(6) .
C8 H7 0.9500 .
C9 C10 1.421(6) .
C10 C11 1.390(7) .
C10 C22 1.487(6) .
C11 C12 1.439(7) .
C12 C13 1.348(7) .
C12 H23 0.9500 .
C13 C14 1.439(7) .
C13 H24 0.9500 .
C14 C15 1.377(7) .
C15 C1 1.427(7) 3_767
C15 C41 1.495(15) .
C15 C27 1.533(12) .
C16 C17 1.381(7) .
C16 C21 1.404(7) .
C17 C18 1.382(7) .
C18 C19 1.353(9) .
C19 C20 1.377(9) .
C20 C21 1.374(7) .
C22 C23 1.391(7) .
C23 C24 1.370(7) .
C23 H8 0.9500 .
C24 C25 1.389(8) .
C24 H9 0.9500 .
C25 C26 1.379(8) .
C25 H10 0.9500 .
C26 H11 0.9500 .
C33 H12 0.9900 .
C33 H13 0.9900 .
C34 H14 0.9900 .
C34 H15 0.9900 .
C35 H16 0.9800 .
C35 H17 0.9800 .
C35 H18 0.9800 .
C36 H19 0.9800 .
C36 H20 0.9800 .
C36 H21 0.9800 .
C27 C28 1.3900 .
C27 C32 1.3900 .
C28 F10 1.329(16) .
C28 C29 1.3900 .
C29 F9 1.32(2) .
C29 C30 1.3900 .
C30 F8 1.332(18) .
C30 C31 1.3900 .
C31 F7 1.339(19) .
C31 C32 1.3900 .
C32 F6 1.37(3) .
C41 C42 1.3900 .
C41 C46 1.3900 .
C42 F10A 1.31(2) .
C42 C43 1.3900 .
C43 F14 1.37(3) .
C43 C44 1.3900 .
C44 F13 1.35(2) .
C44 C45 1.3900 .
C45 F12 1.30(2) .
C45 C46 1.3900 .
C46 F11 1.20(4) .
loop_
_geom_hbond_atom_site_label_D
_geom_hbond_atom_site_label_H
_geom_hbond_atom_site_label_A
_geom_hbond_distance_DH
_geom_hbond_distance_HA
_geom_hbond_distance_DA
_geom_hbond_angle_DHA
_geom_hbond_site_symmetry_A
O4 H22 N3 0.84 2.03 2.759(6) 145.0 3_667
N1 H1 N3 0.88 2.68 3.159(5) 115.4 3_767
N2 H2 O2 0.88 1.97 2.823(5) 162.8 .
N4 H3 O3 0.88 1.85 2.721(5) 170.0 3_667
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 N1 C1 C2 -1.6(6) . .
C4 N1 C1 C15 176.2(5) . 3_767
N1 C1 C2 C3 0.8(7) . .
C15 C1 C2 C3 -177.1(5) 3_767 .
C1 C2 C3 C4 0.4(7) . .
C1 N1 C4 C3 1.8(6) . .
C1 N1 C4 C5 -178.4(5) . .
C2 C3 C4 N1 -1.4(6) . .
C2 C3 C4 C5 178.9(5) . .
N1 C4 C5 C6 -14.7(8) . .
C3 C4 C5 C6 165.0(5) . .
N1 C4 C5 C16 166.9(4) . .
C3 C4 C5 C16 -13.4(8) . .
C4 C5 C6 N2 172.6(4) . .
C16 C5 C6 N2 -9.0(7) . .
C4 C5 C6 C7 -16.5(8) . .
C16 C5 C6 C7 161.9(5) . .
C9 N2 C6 C5 171.5(4) . .
C9 N2 C6 C7 -1.4(5) . .
C5 C6 C7 C8 -171.0(5) . .
N2 C6 C7 C8 1.1(5) . .
C6 C7 C8 C9 -0.4(5) . .
C6 N2 C9 C10 -172.5(4) . .
C6 N2 C9 C8 1.2(5) . .
C7 C8 C9 N2 -0.5(5) . .
C7 C8 C9 C10 172.5(5) . .
N2 C9 C10 C11 -170.7(4) . .
C8 C9 C10 C11 17.2(8) . .
N2 C9 C10 C22 16.4(6) . .
C8 C9 C10 C22 -155.7(5) . .
C14 N3 C11 C10 -177.0(4) . .
C14 N3 C11 C12 0.4(5) . .
C9 C10 C11 N3 14.9(8) . .
C22 C10 C11 N3 -172.4(4) . .
C9 C10 C11 C12 -162.1(5) . .
C22 C10 C11 C12 10.6(7) . .
N3 C11 C12 C13 0.0(5) . .
C10 C11 C12 C13 177.5(5) . .
C11 C12 C13 C14 -0.5(6) . .
C11 N3 C14 C15 178.6(5) . .
C11 N3 C14 C13 -0.7(5) . .
C12 C13 C14 C15 -178.6(5) . .
C12 C13 C14 N3 0.7(5) . .
N3 C14 C15 C1 -6.6(9) . 3_767
C13 C14 C15 C1 172.6(5) . 3_767
N3 C14 C15 C41 166.1(12) . .
C13 C14 C15 C41 -14.7(14) . .
N3 C14 C15 C27 178.6(10) . .
C13 C14 C15 C27 -2.2(11) . .
C6 C5 C16 C17 114.2(5) . .
C4 C5 C16 C17 -67.2(6) . .
C6 C5 C16 C21 -63.4(6) . .
C4 C5 C16 C21 115.1(5) . .
C21 C16 C17 F1 178.7(4) . .
C5 C16 C17 F1 1.0(7) . .
C21 C16 C17 C18 0.9(7) . .
C5 C16 C17 C18 -176.9(5) . .
F1 C17 C18 F2 0.4(8) . .
C16 C17 C18 F2 178.3(5) . .
F1 C17 C18 C19 -178.4(5) . .
C16 C17 C18 C19 -0.6(8) . .
F2 C18 C19 F3 1.1(8) . .
C17 C18 C19 F3 179.9(5) . .
F2 C18 C19 C20 -179.1(5) . .
C17 C18 C19 C20 -0.3(8) . .
F3 C19 C20 F4 1.6(8) . .
C18 C19 C20 F4 -178.2(5) . .
F3 C19 C20 C21 -179.5(5) . .
C18 C19 C20 C21 0.7(8) . .
F4 C20 C21 F5 -0.6(7) . .
C19 C20 C21 F5 -179.5(5) . .
F4 C20 C21 C16 178.6(5) . .
C19 C20 C21 C16 -0.4(8) . .
C17 C16 C21 F5 178.7(4) . .
C5 C16 C21 F5 -3.5(7) . .
C17 C16 C21 C20 -0.4(7) . .
C5 C16 C21 C20 177.4(5) . .
C26 N4 C22 C23 -1.9(7) . .
C26 N4 C22 C10 178.4(4) . .
C11 C10 C22 N4 62.1(6) . .
C9 C10 C22 N4 -124.5(5) . .
C11 C10 C22 C23 -117.6(5) . .
C9 C10 C22 C23 55.8(6) . .
N4 C22 C23 C24 1.5(7) . .
C10 C22 C23 C24 -178.8(5) . .
C22 C23 C24 C25 -0.9(8) . .
C23 C24 C25 C26 0.5(9) . .
C22 N4 C26 C25 1.5(8) . .
C24 C25 C26 N4 -0.8(8) . .
C14 C15 C27 C28 89.2(10) . .
C1 C15 C27 C28 -86.3(12) 3_767 .
C41 C15 C27 C28 -155(9) . .
C14 C15 C27 C32 -91.5(10) . .
C1 C15 C27 C32 93.0(11) 3_767 .
C41 C15 C27 C32 24(8) . .
C32 C27 C28 F10 -179.4(17) . .
C15 C27 C28 F10 -0.1(14) . .
C32 C27 C28 C29 0.0 . .
C15 C27 C28 C29 179.3(15) . .
F10 C28 C29 F9 -3.6(18) . .
C27 C28 C29 F9 177.0(16) . .
F10 C28 C29 C30 179.5(17) . .
C27 C28 C29 C30 0.0 . .
F9 C29 C30 F8 1.7(18) . .
C28 C29 C30 F8 178.7(14) . .
F9 C29 C30 C31 -177.0(16) . .
C28 C29 C30 C31 0.0 . .
F8 C30 C31 F7 4.0(16) . .
C29 C30 C31 F7 -177.3(14) . .
F8 C30 C31 C32 -178.7(14) . .
C29 C30 C31 C32 0.0 . .
F7 C31 C32 F6 -0.7(17) . .
C30 C31 C32 F6 -178.1(15) . .
F7 C31 C32 C27 177.4(14) . .
C30 C31 C32 C27 0.0 . .
C28 C27 C32 F6 178.0(16) . .
C15 C27 C32 F6 -1.4(17) . .
C28 C27 C32 C31 0.0 . .
C15 C27 C32 C31 -179.4(14) . .
C14 C15 C41 C42 83.5(14) . .
C1 C15 C41 C42 -102.6(11) 3_767 .
C27 C15 C41 C42 14(8) . .
C14 C15 C41 C46 -90.0(14) . .
C1 C15 C41 C46 83.9(16) 3_767 .
C27 C15 C41 C46 -160(9) . .
C46 C41 C42 F10A 178(2) . .
C15 C41 C42 F10A 4.1(17) . .
C46 C41 C42 C43 0.0 . .
C15 C41 C42 C43 -174(2) . .
F10A C42 C43 F14 6(2) . .
C41 C42 C43 F14 -176.1(18) . .
F10A C42 C43 C44 -178(2) . .
C41 C42 C43 C44 0.0 . .
F14 C43 C44 F13 -1(2) . .
C42 C43 C44 F13 -176.8(16) . .
F14 C43 C44 C45 176.0(19) . .
C42 C43 C44 C45 0.0 . .
F13 C44 C45 F12 -1(2) . .
C43 C44 C45 F12 -177.3(18) . .
F13 C44 C45 C46 176.6(18) . .
C43 C44 C45 C46 0.0 . .
F12 C45 C46 F11 -5(2) . .
C44 C45 C46 F11 178(2) . .
F12 C45 C46 C41 177.2(19) . .
C44 C45 C46 C41 0.0 . .
C42 C41 C46 F11 -178(2) . .
C15 C41 C46 F11 -5(2) . .
C42 C41 C46 C45 0.0 . .
C15 C41 C46 C45 173(2) . .
loop_
_platon_squeeze_void_nr
_platon_squeeze_void_average_x
_platon_squeeze_void_average_y
_platon_squeeze_void_average_z
_platon_squeeze_void_volume
_platon_squeeze_void_count_electrons
_platon_squeeze_void_content
1 -0.191 0.750 -0.081 411 129 ' '
2 0.191 0.250 0.450 411 129 ' '
3 0.232 0.936 0.094 21 2 ' '
4 0.232 0.564 0.594 21 2 ' '
5 0.768 0.436 0.406 21 2 ' '
6 0.768 0.064 0.906 21 2 ' '
