#------------------------------------------------------------------------------
#$Date: 2016-03-26 14:47:02 +0200 (Sat, 26 Mar 2016) $
#$Revision: 180276 $
#$URL: svn://www.crystallography.net/cod/cif/7/11/62/7116249.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_7116249
loop_
_publ_author_name
'Reyes-Gutiérrez, Paul E'
'Jirásek, Michael'
'Severa, Lukáš'
'Novotná, Pavlína'
'Koval, Dušan'
'Sázelová, Petra'
'Vávra, Jan'
'Meyer, Andreas'
'Císařová, Ivana'
'Šaman, David'
'Pohl, Radek'
'Štěpánek, Petr'
'Slavíček, Petr'
'Coe, Benjamin J.'
'Hájek, Miroslav'
'Kašička, Václav'
'Urbanová, Marie'
'Teplý, Filip'
_publ_section_title
;
 Functional helquats: helical cationic dyes with marked, switchable
 chiroptical properties in the visible region.
;
_journal_issue                   9
_journal_name_full
'Chemical communications (Cambridge, England)'
_journal_page_first              1583
_journal_page_last               1586
_journal_paper_doi               10.1039/c4cc08967g
_journal_volume                  51
_journal_year                    2015
_chemical_absolute_configuration ad
_chemical_compound_source        'synthesized by the authors'
_chemical_formula_moiety         'C42 H44 N4, 2(ClO4)'
_chemical_formula_sum            'C42 H44 Cl2 N4 O8'
_chemical_formula_weight         803.71
_chemical_name_systematic
; 
 ? 
;
_space_group_IT_number           94
_space_group_name_Hall           'P 4n 2n'
_symmetry_cell_setting           tetragonal
_symmetry_space_group_name_Hall  'P 4n 2n'
_symmetry_space_group_name_H-M   'P 42 21 2'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_audit_creation_method           SHELXL-97
_audit_update_record
;
2014-06-12 deposited with the CCDC.
2014-12-15 downloaded from the CCDC.
;
_cell_angle_alpha                90.00
_cell_angle_beta                 90.00
_cell_angle_gamma                90.00
_cell_formula_units_Z            4
_cell_length_a                   13.3242(4)
_cell_length_b                   13.3242(4)
_cell_length_c                   24.3016(9)
_cell_measurement_reflns_used    4342
_cell_measurement_temperature    150(2)
_cell_measurement_theta_max      24.7018
_cell_measurement_theta_min      2.2685
_cell_volume                     4314.4(2)
_computing_cell_refinement       'SAINT V8.27B (Bruker AXS Inc., 2012)'
_computing_data_collection       'Bruker Instrument Service v2012.12.0.0'
_computing_data_reduction        'SAINT V8.27B (Bruker AXS Inc., 2012)'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 2008)'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 2008)'
_diffrn_ambient_temperature      150(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  0.0651
_diffrn_reflns_av_sigmaI/netI    0.0638
_diffrn_reflns_limit_h_max       16
_diffrn_reflns_limit_h_min       -12
_diffrn_reflns_limit_k_max       16
_diffrn_reflns_limit_k_min       -13
_diffrn_reflns_limit_l_max       30
_diffrn_reflns_limit_l_min       -30
_diffrn_reflns_number            24485
_diffrn_reflns_theta_full        26.05
_diffrn_reflns_theta_max         26.05
_diffrn_reflns_theta_min         1.68
_diffrn_standards_number         0
_exptl_absorpt_coefficient_mu    0.204
_exptl_absorpt_correction_T_max  0.97
_exptl_absorpt_correction_T_min  0.79
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   'SADABS V2012/1 (Bruker AXS Inc.)'
_exptl_crystal_colour            'dark red'
_exptl_crystal_density_diffrn    1.237
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       plate
_exptl_crystal_F_000             1688
_exptl_crystal_size_max          0.443
_exptl_crystal_size_mid          0.199
_exptl_crystal_size_min          0.132
_refine_diff_density_max         1.134
_refine_diff_density_min         -0.528
_refine_diff_density_rms         0.138
_refine_ls_abs_structure_details 'Flack H D (1983), Acta Cryst. A39, 876-881'
_refine_ls_abs_structure_Flack   0.1(3)
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.266
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     263
_refine_ls_number_reflns         4285
_refine_ls_number_restraints     10
_refine_ls_restrained_S_all      1.283
_refine_ls_R_factor_all          0.1721
_refine_ls_R_factor_gt           0.1219
_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)+(0.2000P)²+0.0000P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.3303
_refine_ls_wR_factor_ref         0.3585
_reflns_number_gt                2512
_reflns_number_total             4285
_reflns_threshold_expression     I>2σ(I)
_cod_data_source_file            c4cc08967g2.cif
_cod_data_source_block           ls935_teply
_cod_depositor_comments
'Adding full bibliography for 7116236--7116249.cif.'
_cod_database_code               7116249
loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'-y+1/2, x+1/2, z+1/2'
'-x, -y, z'
'y+1/2, -x+1/2, z+1/2'
'x+1/2, -y+1/2, -z+1/2'
'y, x, -z'
'-x+1/2, y+1/2, -z+1/2'
'-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 0.1039(5) 0.5786(5) -0.0662(2) 0.0419(14) Uani 1 1 d .
H1 H 0.0549 0.6291 -0.0726 0.050 Uiso 1 1 calc R
C2 C 0.1653(4) 0.5857(4) -0.0192(3) 0.0425(14) Uani 1 1 d .
C3 C 0.2367(5) 0.5127(6) -0.0141(3) 0.0570(18) Uani 1 1 d .
H3 H 0.2833 0.5167 0.0154 0.068 Uiso 1 1 calc R
C4 C 0.2432(6) 0.4344(5) -0.0499(3) 0.0536(17) Uani 1 1 d .
H4 H 0.2922 0.3837 -0.0443 0.064 Uiso 1 1 calc R
N5 N 0.1804(4) 0.4283(4) -0.0934(2) 0.0463(13) Uani 1 1 d .
C6 C 0.1897(5) 0.3418(5) -0.1318(3) 0.0537(16) Uani 1 1 d .
H6A H 0.1218 0.3197 -0.1430 0.064 Uiso 1 1 calc R
H6B H 0.2224 0.2852 -0.1125 0.064 Uiso 1 1 calc R
C7 C 0.2493(5) 0.3675(6) -0.1821(3) 0.063(2) Uani 1 1 d .
H7A H 0.2387 0.3154 -0.2106 0.076 Uiso 1 1 calc R
H7B H 0.3216 0.3688 -0.1729 0.076 Uiso 1 1 calc R
C8 C 0.2170(6) 0.4710(7) -0.2049(3) 0.073(2) Uani 1 1 d .
H8A H 0.2488 0.5243 -0.1825 0.087 Uiso 1 1 calc R
H8B H 0.2422 0.4779 -0.2430 0.087 Uiso 1 1 calc R
C9 C 0.1060(5) 0.4868(6) -0.2049(3) 0.0582(18) Uani 1 1 d .
C10 C 0.0502(6) 0.4918(7) -0.2542(3) 0.0632(19) Uani 1 1 d .
H10 H 0.0840 0.4835 -0.2883 0.076 Uiso 1 1 calc R
C11 C 0.0518(4) 0.4927(5) -0.1553(2) 0.0429(14) Uani 1 1 d .
C12 C 0.1127(4) 0.5003(5) -0.1035(2) 0.0421(14) Uani 1 1 d .
C13 C 0.1514(5) 0.6701(5) 0.0169(2) 0.0498(16) Uani 1 1 d .
H13 H 0.1020 0.7186 0.0075 0.060 Uiso 1 1 calc R
C14 C 0.2052(5) 0.6844(5) 0.0638(3) 0.0494(16) Uani 1 1 d .
H14 H 0.2524 0.6341 0.0736 0.059 Uiso 1 1 calc R
C15 C 0.1961(5) 0.7701(5) 0.1002(3) 0.0473(16) Uani 1 1 d .
C16 C 0.2510(5) 0.7730(5) 0.1498(2) 0.0474(15) Uani 1 1 d .
H16 H 0.2924 0.7176 0.1593 0.057 Uiso 1 1 calc R
C17 C 0.2461(5) 0.8529(5) 0.1846(2) 0.0521(17) Uani 1 1 d .
H17 H 0.2842 0.8521 0.2177 0.062 Uiso 1 1 calc R
C18 C 0.1868(5) 0.9354(5) 0.1726(3) 0.0541(17) Uani 1 1 d .
C19 C 0.1357(5) 0.9359(6) 0.1234(3) 0.0600(18) Uani 1 1 d .
H19 H 0.0976 0.9934 0.1136 0.072 Uiso 1 1 calc R
C20 C 0.1383(5) 0.8546(5) 0.0880(3) 0.0520(16) Uani 1 1 d .
H20 H 0.1003 0.8564 0.0549 0.062 Uiso 1 1 calc R
C21 C 0.2248(7) 1.0150(7) 0.2628(3) 0.080(3) Uani 1 1 d .
H21A H 0.1874 0.9655 0.2845 0.121 Uiso 1 1 calc R
H21B H 0.2194 1.0810 0.2804 0.121 Uiso 1 1 calc R
H21C H 0.2956 0.9951 0.2609 0.121 Uiso 1 1 calc R
C22 C 0.1134(6) 1.1005(6) 0.1974(4) 0.074(2) Uani 1 1 d .
H22A H 0.1216 1.1246 0.1596 0.111 Uiso 1 1 calc R
H22B H 0.1264 1.1557 0.2231 0.111 Uiso 1 1 calc R
H22C H 0.0447 1.0759 0.2026 0.111 Uiso 1 1 calc R
N1 N 0.1835(5) 1.0199(5) 0.2077(2) 0.0708(18) Uani 1 1 d .
Cl1 Cl 0.0000 0.0000 0.38876(13) 0.0741(11) Uani 0.80 2 d SPD
O11 O 0.0185(12) 0.0783(12) 0.3541(6) 0.087(4) Uiso 0.40 1 d P
O21 O -0.0978(5) 0.0332(10) 0.4044(5) 0.071(4) Uiso 0.40 1 d PD
O31 O 0.0537(16) -0.0146(19) 0.4325(9) 0.137(7) Uiso 0.40 1 d P
O41 O 0.0492(12) 0.0940(6) 0.3817(7) 0.093(5) Uiso 0.40 1 d PD
Cl2 Cl 0.15519(18) 0.15519(18) 0.0000 0.0967(14) Uani 0.80 2 d SPD
O12 O 0.2257(14) 0.2257(14) 0.0000 0.105(10) Uiso 0.40 2 d SP
O22 O 0.1135(12) 0.1699(13) 0.0534(3) 0.092(5) Uiso 0.40 1 d PD
O32 O 0.2367(8) 0.0970(9) 0.0212(6) 0.080(4) Uiso 0.40 1 d PD
O42 O 0.189(4) 0.2559(13) 0.0035(16) 0.113(12) Uiso 0.20 1 d PD
O52 O 0.0793(17) 0.0793(17) 0.0000 0.122(9) Uiso 0.40 2 d SP
O62 O 0.0717(10) 0.1236(16) 0.0318(8) 0.050(5) Uiso 0.20 1 d PD
Cl3 Cl 0.1389(6) 0.4005(7) 0.1185(3) 0.083(3) Uiso 0.20 1 d PD
O13 O 0.1363(6) 0.3335(7) 0.1651(3) 0.037 Uiso 0.20 1 d PRD
O23 O 0.0629(6) 0.3702(7) 0.0798(3) 0.060(6) Uiso 0.20 1 d PRD
O33 O 0.1189(6) 0.5006(7) 0.1365(3) 0.066(6) Uiso 0.20 1 d PRD
O43 O 0.2357(6) 0.3954(7) 0.0935(3) 0.141(15) Uiso 0.20 1 d PRD
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'
Cl Cl 0.1484 0.1585 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
N N 0.0061 0.0033 '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
C12 C1 C2 122.1(6) . .
C12 C1 H1 119.0 . .
C2 C1 H1 119.0 . .
C3 C2 C1 115.5(6) . .
C3 C2 C13 126.2(6) . .
C1 C2 C13 118.2(6) . .
C4 C3 C2 122.1(6) . .
C4 C3 H3 118.9 . .
C2 C3 H3 118.9 . .
N5 C4 C3 120.5(6) . .
N5 C4 H4 119.8 . .
C3 C4 H4 119.8 . .
C12 N5 C4 121.3(6) . .
C12 N5 C6 119.6(5) . .
C4 N5 C6 119.1(6) . .
N5 C6 C7 112.3(5) . .
N5 C6 H6A 109.1 . .
C7 C6 H6A 109.1 . .
N5 C6 H6B 109.1 . .
C7 C6 H6B 109.1 . .
H6A C6 H6B 107.9 . .
C6 C7 C8 110.3(6) . .
C6 C7 H7A 109.6 . .
C8 C7 H7A 109.6 . .
C6 C7 H7B 109.6 . .
C8 C7 H7B 109.6 . .
H7A C7 H7B 108.1 . .
C9 C8 C7 113.6(6) . .
C9 C8 H8A 108.8 . .
C7 C8 H8A 108.8 . .
C9 C8 H8B 108.8 . .
C7 C8 H8B 108.8 . .
H8A C8 H8B 107.7 . .
C11 C9 C10 117.0(6) . .
C11 C9 C8 121.1(7) . .
C10 C9 C8 121.9(6) . .
C10 C10 C9 121.8(4) 3_565 .
C10 C10 H10 119.1 3_565 .
C9 C10 H10 119.1 . .
C11 C11 C9 121.1(4) 3_565 .
C11 C11 C12 121.7(3) 3_565 .
C9 C11 C12 116.4(5) . .
N5 C12 C1 118.4(5) . .
N5 C12 C11 118.1(6) . .
C1 C12 C11 123.6(6) . .
C14 C13 C2 123.6(6) . .
C14 C13 H13 118.2 . .
C2 C13 H13 118.2 . .
C13 C14 C15 125.3(7) . .
C13 C14 H14 117.4 . .
C15 C14 H14 117.4 . .
C20 C15 C16 116.5(6) . .
C20 C15 C14 123.5(6) . .
C16 C15 C14 120.0(6) . .
C17 C16 C15 121.8(6) . .
C17 C16 H16 119.1 . .
C15 C16 H16 119.1 . .
C16 C17 C18 121.2(6) . .
C16 C17 H17 119.4 . .
C18 C17 H17 119.4 . .
C19 C18 C17 118.0(6) . .
C19 C18 N1 120.3(7) . .
C17 C18 N1 121.6(6) . .
C18 C19 C20 121.6(7) . .
C18 C19 H19 119.2 . .
C20 C19 H19 119.2 . .
C19 C20 C15 120.9(6) . .
C19 C20 H20 119.6 . .
C15 C20 H20 119.6 . .
N1 C21 H21A 109.5 . .
N1 C21 H21B 109.5 . .
H21A C21 H21B 109.5 . .
N1 C21 H21C 109.5 . .
H21A C21 H21C 109.5 . .
H21B C21 H21C 109.5 . .
N1 C22 H22A 109.5 . .
N1 C22 H22B 109.5 . .
H22A C22 H22B 109.5 . .
N1 C22 H22C 109.5 . .
H22A C22 H22C 109.5 . .
H22B C22 H22C 109.5 . .
C18 N1 C22 120.6(7) . .
C18 N1 C21 120.6(7) . .
C22 N1 C21 116.0(7) . .
O31 Cl1 O31 70(2) 3 .
O31 Cl1 O11 119.5(12) 3 .
O31 Cl1 O11 121.5(12) . .
O31 Cl1 O11 121.5(12) 3 3
O31 Cl1 O11 119.5(12) . 3
O11 Cl1 O11 103.6(14) . 3
O31 Cl1 O41 102.7(13) 3 .
O31 Cl1 O41 88.7(13) . .
O11 Cl1 O41 33.9(8) . .
O11 Cl1 O41 133.0(12) 3 .
O31 Cl1 O41 88.7(13) 3 3
O31 Cl1 O41 102.7(13) . 3
O11 Cl1 O41 133.0(12) . 3
O11 Cl1 O41 33.9(8) 3 3
O41 Cl1 O41 166.2(15) . 3
O31 Cl1 O21 109.4(13) 3 3
O31 Cl1 O21 39.8(10) . 3
O11 Cl1 O21 103.7(9) . 3
O11 Cl1 O21 95.3(9) 3 3
O41 Cl1 O21 83.4(9) . 3
O41 Cl1 O21 100.3(9) 3 3
O31 Cl1 O21 39.8(10) 3 .
O31 Cl1 O21 109.4(13) . .
O11 Cl1 O21 95.3(9) . .
O11 Cl1 O21 103.7(9) 3 .
O41 Cl1 O21 100.3(9) . .
O41 Cl1 O21 83.4(9) 3 .
O21 Cl1 O21 149.1(11) 3 .
O41 O11 Cl1 77.2(11) . .
O31 O21 Cl1 62.5(13) 3 .
O21 O31 Cl1 77.7(15) 3 .
O21 O31 O31 132.6(14) 3 3
Cl1 O31 O31 55.1(10) . 3
O11 O41 Cl1 69.0(11) . .
O12 Cl2 O62 139.8(10) . .
O12 Cl2 O62 139.8(10) . 6
O62 Cl2 O62 80.4(19) . 6
O12 Cl2 O42 27(2) . .
O62 Cl2 O42 120(2) . .
O62 Cl2 O42 150.4(19) 6 .
O12 Cl2 O42 27(2) . 6
O62 Cl2 O42 150.4(19) . 6
O62 Cl2 O42 120(2) 6 6
O42 Cl2 O42 53(4) . 6
O12 Cl2 O22 100.3(7) . 6
O62 Cl2 O22 119.3(14) . 6
O62 Cl2 O22 40.4(9) 6 6
O42 Cl2 O22 112.3(18) . 6
O42 Cl2 O22 86.5(18) 6 6
O12 Cl2 O22 100.3(7) . .
O62 Cl2 O22 40.4(9) . .
O62 Cl2 O22 119.3(14) 6 .
O42 Cl2 O22 86.5(18) . .
O42 Cl2 O22 112.3(18) 6 .
O22 Cl2 O22 159.5(15) 6 .
O12 Cl2 O52 180.0(18) . .
O62 Cl2 O52 40.2(10) . .
O62 Cl2 O52 40.2(10) 6 .
O42 Cl2 O52 153(2) . .
O42 Cl2 O52 153(2) 6 .
O22 Cl2 O52 79.7(7) 6 .
O22 Cl2 O52 79.7(7) . .
O12 Cl2 O32 81.2(6) . .
O62 Cl2 O32 103.7(10) . .
O62 Cl2 O32 89.8(11) 6 .
O42 Cl2 O32 104(2) . .
O42 Cl2 O32 58.5(19) 6 .
O22 Cl2 O32 90.8(9) 6 .
O22 Cl2 O32 92.4(9) . .
O52 Cl2 O32 98.8(6) . .
O12 Cl2 O32 81.2(6) . 6
O62 Cl2 O32 89.8(11) . 6
O62 Cl2 O32 103.7(10) 6 6
O42 Cl2 O32 58.5(19) . 6
O42 Cl2 O32 104(2) 6 6
O22 Cl2 O32 92.4(9) 6 6
O22 Cl2 O32 90.8(9) . 6
O52 Cl2 O32 98.8(6) . 6
O32 Cl2 O32 162.3(13) . 6
O42 O12 O42 169(7) . 6
O42 O12 Cl2 85(3) . .
O42 O12 Cl2 85(3) 6 .
O42 O12 O32 129(4) . .
O42 O12 O32 42(3) 6 .
Cl2 O12 O32 51.9(8) . .
O42 O12 O32 42(3) . 6
O42 O12 O32 129(4) 6 6
Cl2 O12 O32 51.9(8) . 6
O32 O12 O32 103.7(16) . 6
O62 O22 Cl2 69.4(5) . .
O42 O32 Cl2 60.3(10) 6 .
O42 O32 O12 17.9(14) 6 .
Cl2 O32 O12 47.0(7) . .
O12 O42 O42 5(3) . 6
O12 O42 O32 120(3) . 6
O42 O42 O32 116(3) 6 6
O12 O42 Cl2 69(2) . .
O42 O42 Cl2 63(2) 6 .
O32 O42 Cl2 61.2(10) 6 .
O62 O52 O62 139(4) . 6
O62 O52 Cl2 69.3(18) . .
O62 O52 Cl2 69.3(18) 6 .
O52 O62 O22 138(2) . .
O52 O62 Cl2 70.5(19) . .
O22 O62 Cl2 70.2(5) . .
O43 Cl3 O33 110.1 . .
O43 Cl3 O23 110.1 . .
O33 Cl3 O23 109.3 . .
O43 Cl3 O13 109.0 . .
O33 Cl3 O13 109.5 . .
O23 Cl3 O13 108.8 . .
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
C1 C12 1.387(9) .
C1 C2 1.409(8) .
C1 H1 0.9500 .
C2 C3 1.366(9) .
C2 C13 1.439(9) .
C3 C4 1.361(9) .
C3 H3 0.9500 .
C4 N5 1.349(8) .
C4 H4 0.9500 .
N5 C12 1.340(8) .
N5 C6 1.489(8) .
C6 C7 1.497(9) .
C6 H6A 0.9900 .
C6 H6B 0.9900 .
C7 C8 1.548(11) .
C7 H7A 0.9900 .
C7 H7B 0.9900 .
C8 C9 1.494(11) .
C8 H8A 0.9900 .
C8 H8B 0.9900 .
C9 C11 1.407(8) .
C9 C10 1.412(9) .
C10 C10 1.355(15) 3_565
C10 H10 0.9500 .
C11 C11 1.394(12) 3_565
C11 C12 1.501(8) .
C13 C14 1.359(8) .
C13 H13 0.9500 .
C14 C15 1.449(9) .
C14 H14 0.9500 .
C15 C20 1.396(9) .
C15 C16 1.411(9) .
C16 C17 1.360(9) .
C16 H16 0.9500 .
C17 C18 1.384(10) .
C17 H17 0.9500 .
C18 C19 1.377(10) .
C18 N1 1.413(9) .
C19 C20 1.384(10) .
C19 H19 0.9500 .
C20 H20 0.9500 .
C21 N1 1.450(9) .
C21 H21A 0.9800 .
C21 H21B 0.9800 .
C21 H21C 0.9800 .
C22 N1 1.445(11) .
C22 H22A 0.9800 .
C22 H22B 0.9800 .
C22 H22C 0.9800 .
Cl1 O31 1.30(2) 3
Cl1 O31 1.30(2) .
Cl1 O11 1.364(15) .
Cl1 O11 1.364(15) 3
Cl1 O41 1.424(3) .
Cl1 O41 1.424(3) 3
Cl1 O21 1.428(3) 3
Cl1 O21 1.428(3) .
O11 O41 0.814(18) .
O21 O31 0.94(2) 3
O31 O21 0.94(2) 3
O31 O31 1.48(4) 3
Cl2 O12 1.33(3) .
Cl2 O62 1.418(3) .
Cl2 O62 1.418(3) 6
Cl2 O42 1.419(3) .
Cl2 O42 1.419(3) 6
Cl2 O22 1.425(3) 6
Cl2 O22 1.425(3) .
Cl2 O52 1.43(3) .
Cl2 O32 1.431(3) .
Cl2 O32 1.431(3) 6
O12 O42 0.64(5) .
O12 O42 0.64(5) 6
O12 O32 1.80(2) .
O12 O32 1.80(2) 6
O22 O62 0.98(2) .
O32 O42 1.39(4) 6
O42 O42 1.27(9) 6
O42 O32 1.39(4) 6
O52 O62 0.98(2) .
O52 O62 0.98(2) 6
Cl3 O43 1.4273 .
Cl3 O33 1.4284 .
Cl3 O23 1.4394 .
Cl3 O13 1.4416 .
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
C12 C1 C2 C3 2.7(9) . .
C12 C1 C2 C13 179.5(5) . .
C1 C2 C3 C4 -4.6(9) . .
C13 C2 C3 C4 178.9(6) . .
C2 C3 C4 N5 2.4(11) . .
C3 C4 N5 C12 2.3(10) . .
C3 C4 N5 C6 179.8(6) . .
C12 N5 C6 C7 79.7(7) . .
C4 N5 C6 C7 -97.9(7) . .
N5 C6 C7 C8 -44.3(8) . .
C6 C7 C8 C9 -42.6(9) . .
C7 C8 C9 C11 65.9(10) . .
C7 C8 C9 C10 -111.1(9) . .
C11 C9 C10 C10 4.2(15) . 3_565
C8 C9 C10 C10 -178.7(10) . 3_565
C10 C9 C11 C11 -2.8(12) . 3_565
C8 C9 C11 C11 -179.9(8) . 3_565
C10 C9 C11 C12 -172.6(7) . .
C8 C9 C11 C12 10.3(10) . .
C4 N5 C12 C1 -4.1(9) . .
C6 N5 C12 C1 178.4(5) . .
C4 N5 C12 C11 174.7(5) . .
C6 N5 C12 C11 -2.9(8) . .
C2 C1 C12 N5 1.5(9) . .
C2 C1 C12 C11 -177.2(5) . .
C11 C11 C12 N5 133.8(8) 3_565 .
C9 C11 C12 N5 -56.4(8) . .
C11 C11 C12 C1 -47.5(10) 3_565 .
C9 C11 C12 C1 122.3(7) . .
C3 C2 C13 C14 -4.5(10) . .
C1 C2 C13 C14 179.1(6) . .
C2 C13 C14 C15 177.6(6) . .
C13 C14 C15 C20 -7.4(10) . .
C13 C14 C15 C16 175.4(6) . .
C20 C15 C16 C17 1.4(9) . .
C14 C15 C16 C17 178.7(6) . .
C15 C16 C17 C18 0.0(10) . .
C16 C17 C18 C19 -2.4(10) . .
C16 C17 C18 N1 -178.1(6) . .
C17 C18 C19 C20 3.5(10) . .
N1 C18 C19 C20 179.3(6) . .
C18 C19 C20 C15 -2.2(10) . .
C16 C15 C20 C19 -0.3(9) . .
C14 C15 C20 C19 -177.5(6) . .
C19 C18 N1 C22 10.9(10) . .
C17 C18 N1 C22 -173.5(6) . .
C19 C18 N1 C21 171.0(7) . .
C17 C18 N1 C21 -13.4(10) . .
O31 Cl1 O11 O41 67(2) 3 .
O31 Cl1 O11 O41 -16(3) . .
O11 Cl1 O11 O41 -154(2) 3 .
O41 Cl1 O11 O41 -173.5(9) 3 .
O21 Cl1 O11 O41 -55(2) 3 .
O21 Cl1 O11 O41 100.6(18) . .
O31 Cl1 O21 O31 -5(3) . 3
O11 Cl1 O21 O31 -131(2) . 3
O11 Cl1 O21 O31 123(2) 3 3
O41 Cl1 O21 O31 -98(2) . 3
O41 Cl1 O21 O31 96(2) 3 3
O21 Cl1 O21 O31 -3.2(19) 3 3
O31 Cl1 O31 O21 175(3) 3 3
O11 Cl1 O31 O21 -72(2) . 3
O11 Cl1 O31 O21 59(2) 3 3
O41 Cl1 O31 O21 -81.3(19) . 3
O41 Cl1 O31 O21 90.9(19) 3 3
O21 Cl1 O31 O21 178.3(10) . 3
O11 Cl1 O31 O31 112.9(16) . 3
O11 Cl1 O31 O31 -115.5(16) 3 3
O41 Cl1 O31 O31 104.1(17) . 3
O41 Cl1 O31 O31 -83.7(18) 3 3
O21 Cl1 O31 O31 -175(3) 3 3
O21 Cl1 O31 O31 4(2) . 3
O31 Cl1 O41 O11 -125(2) 3 .
O31 Cl1 O41 O11 166(2) . .
O11 Cl1 O41 O11 36(3) 3 .
O41 Cl1 O41 O11 20.4(17) 3 .
O21 Cl1 O41 O11 126.9(19) 3 .
O21 Cl1 O41 O11 -84.1(18) . .
O62 Cl2 O12 O42 -50(4) . .
O62 Cl2 O12 O42 130(4) 6 .
O42 Cl2 O12 O42 180.0 6 .
O22 Cl2 O12 O42 120(4) 6 .
O22 Cl2 O12 O42 -60(4) . .
O52 Cl2 O12 O42 -172(4) . .
O32 Cl2 O12 O42 -151(4) . .
O32 Cl2 O12 O42 29(4) 6 .
O62 Cl2 O12 O42 130(4) . 6
O62 Cl2 O12 O42 -50(4) 6 6
O42 Cl2 O12 O42 -180.0 . 6
O22 Cl2 O12 O42 -60(4) 6 6
O22 Cl2 O12 O42 120(4) . 6
O52 Cl2 O12 O42 8(4) . 6
O32 Cl2 O12 O42 29(4) . 6
O32 Cl2 O12 O42 -151(4) 6 6
O62 Cl2 O12 O32 100.9(14) . .
O62 Cl2 O12 O32 -79.1(14) 6 .
O42 Cl2 O12 O32 151(4) . .
O42 Cl2 O12 O32 -29(4) 6 .
O22 Cl2 O12 O32 -89.2(9) 6 .
O22 Cl2 O12 O32 90.8(9) . .
O52 Cl2 O12 O32 -21.4(6) . .
O32 Cl2 O12 O32 180.0 6 .
O62 Cl2 O12 O32 -79.1(14) . 6
O62 Cl2 O12 O32 100.9(14) 6 6
O42 Cl2 O12 O32 -29(4) . 6
O42 Cl2 O12 O32 151(4) 6 6
O22 Cl2 O12 O32 90.8(9) 6 6
O22 Cl2 O12 O32 -89.2(9) . 6
O52 Cl2 O12 O32 158.6(6) . 6
O32 Cl2 O12 O32 180.0 . 6
O12 Cl2 O22 O62 170.0(16) . .
O62 Cl2 O22 O62 -17(3) 6 .
O42 Cl2 O22 O62 147(3) . .
O42 Cl2 O22 O62 -165(3) 6 .
O22 Cl2 O22 O62 -10.0(16) 6 .
O52 Cl2 O22 O62 -10.0(16) . .
O32 Cl2 O22 O62 -108.6(17) . .
O32 Cl2 O22 O62 88.8(18) 6 .
O12 Cl2 O32 O42 -15(2) . 6
O62 Cl2 O32 O42 -154(2) . 6
O62 Cl2 O32 O42 126(2) 6 6
O42 Cl2 O32 O42 -28(4) . 6
O22 Cl2 O32 O42 85(2) 6 6
O22 Cl2 O32 O42 -115(2) . 6
O52 Cl2 O32 O42 165(2) . 6
O32 Cl2 O32 O42 -15(2) 6 6
O62 Cl2 O32 O12 -139.3(10) . .
O62 Cl2 O32 O12 140.7(10) 6 .
O42 Cl2 O32 O12 -13.0(17) . .
O42 Cl2 O32 O12 15(2) 6 .
O22 Cl2 O32 O12 100.3(7) 6 .
O22 Cl2 O32 O12 -100.0(8) . .
O52 Cl2 O32 O12 180.0 . .
O32 Cl2 O32 O12 0.013(1) 6 .
O42 O12 O32 O42 172(5) . 6
Cl2 O12 O32 O42 134(5) . 6
O32 O12 O32 O42 134(5) 6 6
O42 O12 O32 Cl2 38(5) . .
O42 O12 O32 Cl2 -134(5) 6 .
O32 O12 O32 Cl2 0.0 6 .
Cl2 O12 O42 O42 -0.028(18) . 6
O32 O12 O42 O42 -29(3) . 6
O32 O12 O42 O42 35(3) 6 6
O42 O12 O42 O32 -35(3) 6 6
Cl2 O12 O42 O32 -35(3) . 6
O32 O12 O42 O32 -64(6) . 6
O42 O12 O42 Cl2 0.03(2) 6 .
O32 O12 O42 Cl2 -29(3) . .
O32 O12 O42 Cl2 35(3) 6 .
O62 Cl2 O42 O12 145(3) . .
O62 Cl2 O42 O12 -87(6) 6 .
O42 Cl2 O42 O12 -0.003(2) 6 .
O22 Cl2 O42 O12 -67(4) 6 .
O22 Cl2 O42 O12 121(3) . .
O52 Cl2 O42 O12 180.0 . .
O32 Cl2 O42 O12 30(3) . .
O32 Cl2 O42 O12 -146(4) 6 .
O12 Cl2 O42 O42 0.003(3) . 6
O62 Cl2 O42 O42 145(3) . 6
O62 Cl2 O42 O42 -87(6) 6 6
O22 Cl2 O42 O42 -67(4) 6 6
O22 Cl2 O42 O42 121(3) . 6
O52 Cl2 O42 O42 180.003(2) . 6
O32 Cl2 O42 O42 30(3) . 6
O32 Cl2 O42 O42 -146(4) 6 6
O12 Cl2 O42 O32 146(4) . 6
O62 Cl2 O42 O32 -69.1(19) . 6
O62 Cl2 O42 O32 59(5) 6 6
O42 Cl2 O42 O32 146(4) 6 6
O22 Cl2 O42 O32 78.5(19) 6 6
O22 Cl2 O42 O32 -93.0(14) . 6
O52 Cl2 O42 O32 -34(4) . 6
O32 Cl2 O42 O32 175.4(7) . 6
O12 Cl2 O52 O62 122.3(13) . .
O62 Cl2 O52 O62 -180.0 6 .
O42 Cl2 O52 O62 -50(4) . .
O42 Cl2 O52 O62 130(4) 6 .
O22 Cl2 O52 O62 -169.9(15) 6 .
O22 Cl2 O52 O62 10.1(15) . .
O32 Cl2 O52 O62 100.9(14) . .
O32 Cl2 O52 O62 -79.1(14) 6 .
O12 Cl2 O52 O62 -57.7(13) . 6
O62 Cl2 O52 O62 180.0 . 6
O42 Cl2 O52 O62 130(4) . 6
O42 Cl2 O52 O62 -50(4) 6 6
O22 Cl2 O52 O62 10.0(15) 6 6
O22 Cl2 O52 O62 -170.0(15) . 6
O32 Cl2 O52 O62 -79.1(14) . 6
O32 Cl2 O52 O62 100.9(14) 6 6
O62 O52 O62 O22 -22(3) 6 .
Cl2 O52 O62 O22 -22(3) . .
O62 O52 O62 Cl2 -0.009(3) 6 .
Cl2 O22 O62 O52 22(3) . .
O12 Cl2 O62 O52 180.000(2) . .
O62 Cl2 O62 O52 0.004(2) 6 .
O42 Cl2 O62 O52 157(2) . .
O42 Cl2 O62 O52 -136(4) 6 .
O22 Cl2 O62 O52 11.4(17) 6 .
O22 Cl2 O62 O52 -165(2) . .
O32 Cl2 O62 O52 -87.4(12) . .
O32 Cl2 O62 O52 104.0(12) 6 .
O12 Cl2 O62 O22 -15(2) . .
O62 Cl2 O62 O22 165(2) 6 .
O42 Cl2 O62 O22 -39(3) . .
O42 Cl2 O62 O22 28(5) 6 .
O22 Cl2 O62 O22 176.0(7) 6 .
O52 Cl2 O62 O22 165(2) . .
O32 Cl2 O62 O22 77.2(17) . .
O32 Cl2 O62 O22 -91.4(17) 6 .
