#------------------------------------------------------------------------------
#$Date: 2022-03-23 12:12:14 +0200 (Wed, 23 Mar 2022) $
#$Revision: 273928 $
#$URL: file:///home/coder/svn-repositories/cod/cif/8/10/48/8104845.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_8104845
loop_
_publ_author_name
'Liu, Xiao-jing'
'Li, Zhuang-yu'
'Liu, E'
'Jian, Fang-fang'
'Liang, Tong-ling'
_publ_section_title
;
 Crystal structure of 1,3-bis(octyl)benzimidazolium perchlorate
 C23H39ClN2O4
;
_journal_issue                   2
_journal_name_full
'Zeitschrift für Kristallographie - New Crystal Structures'
_journal_page_first              405
_journal_page_last               407
_journal_paper_doi               10.1515/ncrs-2020-0421
_journal_volume                  236
_journal_year                    2021
_chemical_formula_moiety         'Cl O4, C23 H39 N2'
_chemical_formula_sum            'C23 H39 Cl N2 O4'
_chemical_formula_weight         443.01
_space_group_crystal_system      triclinic
_space_group_IT_number           2
_space_group_name_Hall           '-P 1'
_space_group_name_H-M_alt        'P -1'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_cell_angle_alpha                99.088(4)
_cell_angle_beta                 94.422(4)
_cell_angle_gamma                107.146(4)
_cell_formula_units_Z            2
_cell_length_a                   9.0752(19)
_cell_length_b                   9.542(2)
_cell_length_c                   16.049(3)
_cell_measurement_reflns_used    5947
_cell_measurement_temperature    293(2)
_cell_measurement_theta_max      28.29
_cell_measurement_theta_min      2.37
_cell_volume                     1300.0(5)
_computing_structure_refinement  'SHELXL-2014/7 (Sheldrick, 2014)'
_computing_structure_solution    'SIR2004  (Burla et al.,  2007)'
_diffrn_ambient_temperature      293
_diffrn_detector                 area
_diffrn_measured_fraction_theta_full 0.9940
_diffrn_measured_fraction_theta_max 0.9210
_diffrn_measurement_device_type  Nonius-CAD4
_diffrn_measurement_method       'ω scans'
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_type           'Mo K\a'
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0204
_diffrn_reflns_av_unetI/netI     0.0498
_diffrn_reflns_Laue_measured_fraction_full 0.9940
_diffrn_reflns_Laue_measured_fraction_max 0.9210
_diffrn_reflns_limit_h_max       11
_diffrn_reflns_limit_h_min       -11
_diffrn_reflns_limit_k_max       12
_diffrn_reflns_limit_k_min       -11
_diffrn_reflns_limit_l_max       11
_diffrn_reflns_limit_l_min       -21
_diffrn_reflns_number            8404
_diffrn_reflns_point_group_measured_fraction_full 0.9940
_diffrn_reflns_point_group_measured_fraction_max 0.9210
_diffrn_reflns_theta_full        25.2417
_diffrn_reflns_theta_max         28.29
_diffrn_reflns_theta_min         2.37
_diffrn_source_current           30.0
_diffrn_source_power             1.5
_diffrn_source_voltage           50.0
_exptl_absorpt_coefficient_mu    0.175
_exptl_absorpt_correction_T_max  0.1988
_exptl_absorpt_correction_T_min  0.1937
_exptl_absorpt_correction_type   analytical
_exptl_absorpt_process_details   SADABS
_exptl_crystal_colour            'clear light colourless'
_exptl_crystal_colour_lustre     clear
_exptl_crystal_colour_modifier   light
_exptl_crystal_colour_primary    colourless
_exptl_crystal_density_diffrn    1.132
_exptl_crystal_description       block
_exptl_crystal_F_000             480.509
_exptl_crystal_size_max          0.25
_exptl_crystal_size_mid          0.2
_exptl_crystal_size_min          0.15
_refine_diff_density_max         0.222
_refine_diff_density_min         -0.307
_refine_diff_density_rms         0.038
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.034
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     373
_refine_ls_number_reflns         5947
_refine_ls_number_restraints     733
_refine_ls_restrained_S_all      1.089
_refine_ls_R_factor_all          0.1429
_refine_ls_R_factor_gt           0.0646
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'w=1/[σ²(Fo²)+(0.1145P)²+0.0276P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1854
_refine_ls_wR_factor_ref         0.2298
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_full    .
_reflns_Friedel_fraction_max     .
_reflns_limit_h_max              11
_reflns_limit_h_min              -11
_reflns_limit_k_max              11
_reflns_limit_k_min              -12
_reflns_limit_l_max              21
_reflns_limit_l_min              0
_reflns_number_gt                2714
_reflns_number_total             5947
_reflns_threshold_expression     'I > 2σ(I)'
_cod_data_source_file            suppl_j_ncrs-2020-0421_suppl.cif
_cod_data_source_block           QJ0887
_cod_database_code               8104845
_shelx_space_group_comment
;
The symmetry employed for this shelxl refinement is uniquely defined
by the following loop, which should always be used as a source of
symmetry information in preference to the above space-group names.
They are only intended as comments.
;
loop_
_space_group_symop_operation_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_site_symmetry_order
_atom_site_calc_flag
_atom_site_refinement_flags_posn
_atom_site_refinement_flags_adp
_atom_site_refinement_flags_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
Cl1 Cl 0.11794(9) 0.36195(8) 0.43769(5) 0.0830(3) Uani 1 1 d D U . . .
O1A O 0.2678(6) 0.3893(9) 0.4090(6) 0.086(2) Uani 0.590(14) 1 d D U P A 1
O2A O 0.1425(6) 0.4166(7) 0.5346(2) 0.0786(17) Uani 0.590(14) 1 d D U P A 1
O3A O 0.0295(8) 0.2068(5) 0.4219(5) 0.103(2) Uani 0.590(14) 1 d D U P A 1
O4A O 0.0274(11) 0.4494(10) 0.4012(5) 0.120(3) Uani 0.590(14) 1 d D U P A 1
O1B O 0.2847(6) 0.4020(13) 0.4420(8) 0.080(3) Uani 0.410(14) 1 d D U P A 2
O2B O 0.0689(18) 0.3615(13) 0.5239(6) 0.135(4) Uani 0.410(14) 1 d D U P A 2
O3B O 0.0414(11) 0.2170(7) 0.3841(8) 0.098(3) Uani 0.410(14) 1 d D U P A 2
O4B O 0.0645(11) 0.4778(9) 0.4016(6) 0.085(3) Uani 0.410(14) 1 d D U P A 2
C1 C -0.0990(9) 0.6626(9) -0.1933(4) 0.224(3) Uani 1 1 d . U . . .
H1A H -0.0925 0.7179 -0.2387 0.336 Uiso 1 1 calc R U . . .
H1B H -0.2049 0.6025 -0.1943 0.336 Uiso 1 1 calc R U . . .
H1C H -0.0343 0.5992 -0.2005 0.336 Uiso 1 1 calc R U . . .
C2 C -0.0472(8) 0.7649(7) -0.1131(4) 0.180(2) Uani 1 1 d . U . . .
H2B H -0.1120 0.8297 -0.1077 0.216 Uiso 1 1 calc R U . . .
H2C H 0.0583 0.8272 -0.1142 0.216 Uiso 1 1 calc R U . . .
C3 C -0.0493(7) 0.6957(6) -0.0352(3) 0.1489(17) Uani 1 1 d . U . . .
H3A H -0.1547 0.6329 -0.0342 0.179 Uiso 1 1 calc R U . . .
H3B H 0.0158 0.6312 -0.0404 0.179 Uiso 1 1 calc R U . . .
C4 C 0.0037(6) 0.8015(5) 0.0478(3) 0.1358(15) Uani 1 1 d . U . . .
H4A H -0.0596 0.8678 0.0523 0.163 Uiso 1 1 calc R U . . .
H4B H 0.1101 0.8623 0.0474 0.163 Uiso 1 1 calc R U . . .
C5 C -0.0025(5) 0.7331(5) 0.1253(3) 0.1231(13) Uani 1 1 d . U . . .
H5A H 0.0583 0.6646 0.1201 0.148 Uiso 1 1 calc R U . . .
H5B H -0.1094 0.6747 0.1266 0.148 Uiso 1 1 calc R U . . .
C6 C 0.0556(4) 0.8409(4) 0.2090(2) 0.1064(11) Uani 1 1 d . U . . .
H6A H 0.1628 0.8990 0.2081 0.128 Uiso 1 1 calc R U . . .
H6B H -0.0050 0.9096 0.2145 0.128 Uiso 1 1 calc R U . . .
C7 C 0.0474(4) 0.7692(4) 0.2847(2) 0.0951(10) Uani 1 1 d . U . . .
H7A H 0.1035 0.6968 0.2775 0.114 Uiso 1 1 calc R U . . .
H7B H -0.0606 0.7149 0.2867 0.114 Uiso 1 1 calc R U . . .
C8 C 0.1118(3) 0.8739(3) 0.3690(2) 0.0826(9) Uani 1 1 d . U . . .
H8A H 0.0561 0.9465 0.3772 0.099 Uiso 1 1 calc R U . . .
H8B H 0.0952 0.8174 0.4145 0.099 Uiso 1 1 calc R U . . .
N9 N 0.2798(2) 0.9533(2) 0.37379(13) 0.0630(6) Uani 1 1 d . U . . .
C10 C 0.3417(3) 1.0955(3) 0.37025(18) 0.0713(7) Uani 1 1 d . U . . .
H10 H 0.2856 1.1612 0.3635 0.086 Uiso 1 1 calc R U . . .
N11 N 0.4955(3) 1.1313(2) 0.37766(13) 0.0677(6) Uani 1 1 d . U . . .
C12 C 0.5381(3) 1.0058(3) 0.38752(16) 0.0609(6) Uani 1 1 d . U . . .
C13 C 0.3991(3) 0.8920(3) 0.38527(15) 0.0578(6) Uani 1 1 d . U . . .
C14 C 0.6810(3) 0.9826(4) 0.40122(18) 0.0777(8) Uani 1 1 d . U . . .
H14 H 0.7740 1.0583 0.4031 0.093 Uiso 1 1 calc R U . . .
C15 C 0.6779(4) 0.8430(4) 0.4118(2) 0.0889(9) Uani 1 1 d . U . . .
H15 H 0.7716 0.8233 0.4212 0.107 Uiso 1 1 calc R U . . .
C16 C 0.5396(4) 0.7289(4) 0.4091(2) 0.0862(9) Uani 1 1 d . U . . .
H16 H 0.5435 0.6353 0.4165 0.103 Uiso 1 1 calc R U . . .
C17 C 0.3984(4) 0.7508(3) 0.39579(18) 0.0736(8) Uani 1 1 d . U . . .
H17 H 0.3060 0.6743 0.3939 0.088 Uiso 1 1 calc R U . . .
C18A C 0.6046(4) 1.2818(3) 0.3781(2) 0.0926(10) Uani 0.704(8) 1 d D U P B 1
H18A H 0.6927 1.3031 0.4216 0.111 Uiso 0.704(8) 1 calc R U P B 1
H18B H 0.5525 1.3562 0.3920 0.111 Uiso 0.704(8) 1 calc R U P B 1
C19A C 0.6612(6) 1.2920(8) 0.2939(3) 0.106(2) Uani 0.704(8) 1 d D U P B 1
H19A H 0.7359 1.3903 0.2980 0.127 Uiso 0.704(8) 1 calc R U P B 1
H19B H 0.7159 1.2193 0.2818 0.127 Uiso 0.704(8) 1 calc R U P B 1
C20A C 0.5392(10) 1.2670(15) 0.2207(4) 0.128(3) Uani 0.704(8) 1 d D U P B 1
H20A H 0.4804 1.3361 0.2328 0.154 Uiso 0.704(8) 1 calc R U P B 1
H20B H 0.4679 1.1662 0.2129 0.154 Uiso 0.704(8) 1 calc R U P B 1
C21A C 0.6126(11) 1.2896(15) 0.1385(4) 0.152(4) Uani 0.704(8) 1 d D U P B 1
H21A H 0.6753 1.3932 0.1443 0.182 Uiso 0.704(8) 1 calc R U P B 1
H21B H 0.6804 1.2282 0.1299 0.182 Uiso 0.704(8) 1 calc R U P B 1
C22A C 0.4917(10) 1.2494(15) 0.0631(4) 0.161(4) Uani 0.704(8) 1 d D U P B 1
H22A H 0.4238 1.3107 0.0718 0.194 Uiso 0.704(8) 1 calc R U P B 1
H22B H 0.4289 1.1458 0.0573 0.194 Uiso 0.704(8) 1 calc R U P B 1
C23A C 0.5640(12) 1.2717(15) -0.0188(4) 0.163(4) Uani 0.704(8) 1 d D U P B 1
H23A H 0.6244 1.3758 -0.0140 0.196 Uiso 0.704(8) 1 calc R U P B 1
H23B H 0.6335 1.2121 -0.0272 0.196 Uiso 0.704(8) 1 calc R U P B 1
C24A C 0.4398(11) 1.2268(19) -0.0938(5) 0.228(6) Uani 0.704(8) 1 d D U P B 1
H24A H 0.3701 1.2863 -0.0858 0.273 Uiso 0.704(8) 1 calc R U P B 1
H24B H 0.3795 1.1226 -0.0991 0.273 Uiso 0.704(8) 1 calc R U P B 1
C25A C 0.5144(13) 1.2503(19) -0.1730(5) 0.210(5) Uani 0.704(8) 1 d D U P B 1
H25A H 0.4353 1.2216 -0.2212 0.315 Uiso 0.704(8) 1 calc R U P B 1
H25B H 0.5731 1.3537 -0.1675 0.315 Uiso 0.704(8) 1 calc R U P B 1
H25C H 0.5825 1.1904 -0.1808 0.315 Uiso 0.704(8) 1 calc R U P B 1
C18B C 0.6046(4) 1.2818(3) 0.3781(2) 0.0926(10) Uani 0.296(8) 1 d D U P B 2
H18C H 0.7101 1.2778 0.3869 0.111 Uiso 0.296(8) 1 calc R U P B 2
H18D H 0.5915 1.3508 0.4261 0.111 Uiso 0.296(8) 1 calc R U P B 2
C19B C 0.586(2) 1.3424(12) 0.2994(4) 0.095(4) Uani 0.296(8) 1 d D U P B 2
H19C H 0.6641 1.4391 0.3057 0.114 Uiso 0.296(8) 1 calc R U P B 2
H19D H 0.4848 1.3583 0.2946 0.114 Uiso 0.296(8) 1 calc R U P B 2
C20B C 0.598(3) 1.247(2) 0.2186(5) 0.134(8) Uani 0.296(8) 1 d D U P B 2
H20C H 0.5274 1.1466 0.2139 0.160 Uiso 0.296(8) 1 calc R U P B 2
H20D H 0.7027 1.2420 0.2187 0.160 Uiso 0.296(8) 1 calc R U P B 2
C21B C 0.555(4) 1.314(2) 0.1426(6) 0.161(9) Uani 0.296(8) 1 d D U P B 2
H21C H 0.4510 1.3216 0.1439 0.194 Uiso 0.296(8) 1 calc R U P B 2
H21D H 0.6265 1.4144 0.1475 0.194 Uiso 0.296(8) 1 calc R U P B 2
C22B C 0.562(4) 1.222(3) 0.0600(7) 0.189(10) Uani 0.296(8) 1 d D U P B 2
H22C H 0.4992 1.1193 0.0574 0.226 Uiso 0.296(8) 1 calc R U P B 2
H22D H 0.6689 1.2230 0.0560 0.226 Uiso 0.296(8) 1 calc R U P B 2
C23B C 0.504(5) 1.281(4) -0.0149(7) 0.217(14) Uani 0.296(8) 1 d D U P B 2
H23C H 0.3946 1.2709 -0.0142 0.260 Uiso 0.296(8) 1 calc R U P B 2
H23D H 0.5605 1.3866 -0.0093 0.260 Uiso 0.296(8) 1 calc R U P B 2
C24B C 0.526(3) 1.197(4) -0.0975(8) 0.226(12) Uani 0.296(8) 1 d D U P B 2
H24C H 0.5002 1.0916 -0.0957 0.272 Uiso 0.296(8) 1 calc R U P B 2
H24D H 0.6342 1.2329 -0.1071 0.272 Uiso 0.296(8) 1 calc R U P B 2
C25B C 0.423(4) 1.220(6) -0.1683(10) 0.29(2) Uani 0.296(8) 1 d D U P B 2
H25D H 0.4364 1.1668 -0.2216 0.438 Uiso 0.296(8) 1 calc R U P B 2
H25E H 0.3163 1.1841 -0.1586 0.438 Uiso 0.296(8) 1 calc R U P B 2
H25F H 0.4499 1.3249 -0.1700 0.438 Uiso 0.296(8) 1 calc R U P 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'
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
O3A Cl1 O1A 113.1(3) . .
O1B Cl1 O3B 111.7(4) . .
O3A Cl1 O4A 110.5(4) . .
O1A Cl1 O4A 111.6(3) . .
O1B Cl1 O2B 111.1(5) . .
O3B Cl1 O2B 109.3(4) . .
O1B Cl1 O4B 108.8(4) . .
O3B Cl1 O4B 108.8(4) . .
O2B Cl1 O4B 107.0(4) . .
O3A Cl1 O2A 106.9(3) . .
O1A Cl1 O2A 108.1(3) . .
O4A Cl1 O2A 106.2(3) . .
C2 C1 H1A 109.5 . .
C2 C1 H1B 109.5 . .
H1A C1 H1B 109.5 . .
C2 C1 H1C 109.5 . .
H1A C1 H1C 109.5 . .
H1B C1 H1C 109.5 . .
C1 C2 C3 116.1(6) . .
C1 C2 H2B 108.3 . .
C3 C2 H2B 108.3 . .
C1 C2 H2C 108.3 . .
C3 C2 H2C 108.3 . .
H2B C2 H2C 107.4 . .
C4 C3 C2 116.1(5) . .
C4 C3 H3A 108.3 . .
C2 C3 H3A 108.3 . .
C4 C3 H3B 108.3 . .
C2 C3 H3B 108.3 . .
H3A C3 H3B 107.4 . .
C3 C4 C5 116.1(4) . .
C3 C4 H4A 108.3 . .
C5 C4 H4A 108.3 . .
C3 C4 H4B 108.3 . .
C5 C4 H4B 108.3 . .
H4A C4 H4B 107.4 . .
C4 C5 C6 115.8(4) . .
C4 C5 H5A 108.3 . .
C6 C5 H5A 108.3 . .
C4 C5 H5B 108.3 . .
C6 C5 H5B 108.3 . .
H5A C5 H5B 107.4 . .
C7 C6 C5 114.4(3) . .
C7 C6 H6A 108.7 . .
C5 C6 H6A 108.7 . .
C7 C6 H6B 108.7 . .
C5 C6 H6B 108.7 . .
H6A C6 H6B 107.6 . .
C6 C7 C8 115.5(3) . .
C6 C7 H7A 108.4 . .
C8 C7 H7A 108.4 . .
C6 C7 H7B 108.4 . .
C8 C7 H7B 108.4 . .
H7A C7 H7B 107.5 . .
N9 C8 C7 112.0(2) . .
N9 C8 H8A 109.2 . .
C7 C8 H8A 109.2 . .
N9 C8 H8B 109.2 . .
C7 C8 H8B 109.2 . .
H8A C8 H8B 107.9 . .
C10 N9 C13 108.5(2) . .
C10 N9 C8 125.7(2) . .
C13 N9 C8 125.8(2) . .
N9 C10 N11 110.2(2) . .
N9 C10 H10 124.9 . .
N11 C10 H10 124.9 . .
C10 N11 C12 108.9(2) . .
C10 N11 C18B 125.6(3) . .
C12 N11 C18B 125.5(2) . .
C10 N11 C18A 125.6(3) . .
C12 N11 C18A 125.5(2) . .
C14 C12 N11 132.8(3) . .
C14 C12 C13 121.5(3) . .
N11 C12 C13 105.6(2) . .
C17 C13 N9 132.0(2) . .
C17 C13 C12 121.2(3) . .
N9 C13 C12 106.8(2) . .
C15 C14 C12 116.4(3) . .
C15 C14 H14 121.8 . .
C12 C14 H14 121.8 . .
C14 C15 C16 122.4(3) . .
C14 C15 H15 118.8 . .
C16 C15 H15 118.8 . .
C17 C16 C15 121.7(3) . .
C17 C16 H16 119.2 . .
C15 C16 H16 119.2 . .
C16 C17 C13 116.9(3) . .
C16 C17 H17 121.6 . .
C13 C17 H17 121.6 . .
N11 C18A C19A 111.3(3) . .
N11 C18A H18A 109.4 . .
C19A C18A H18A 109.4 . .
N11 C18A H18B 109.4 . .
C19A C18A H18B 109.4 . .
H18A C18A H18B 108.0 . .
C20A C19A C18A 115.7(4) . .
C20A C19A H19A 108.4 . .
C18A C19A H19A 108.4 . .
C20A C19A H19B 108.4 . .
C18A C19A H19B 108.4 . .
H19A C19A H19B 107.4 . .
C19A C20A C21A 110.8(6) . .
C19A C20A H20A 109.5 . .
C21A C20A H20A 109.5 . .
C19A C20A H20B 109.5 . .
C21A C20A H20B 109.5 . .
H20A C20A H20B 108.1 . .
C22A C21A C20A 111.5(7) . .
C22A C21A H21A 109.3 . .
C20A C21A H21A 109.3 . .
C22A C21A H21B 109.3 . .
C20A C21A H21B 109.3 . .
H21A C21A H21B 108.0 . .
C21A C22A C23A 111.7(6) . .
C21A C22A H22A 109.3 . .
C23A C22A H22A 109.3 . .
C21A C22A H22B 109.3 . .
C23A C22A H22B 109.3 . .
H22A C22A H22B 107.9 . .
C24A C23A C22A 110.5(7) . .
C24A C23A H23A 109.6 . .
C22A C23A H23A 109.6 . .
C24A C23A H23B 109.6 . .
C22A C23A H23B 109.6 . .
H23A C23A H23B 108.1 . .
C23A C24A C25A 109.2(7) . .
C23A C24A H24A 109.8 . .
C25A C24A H24A 109.8 . .
C23A C24A H24B 109.8 . .
C25A C24A H24B 109.8 . .
H24A C24A H24B 108.3 . .
C24A C25A H25A 109.5 . .
C24A C25A H25B 109.5 . .
H25A C25A H25B 109.5 . .
C24A C25A H25C 109.5 . .
H25A C25A H25C 109.5 . .
H25B C25A H25C 109.5 . .
N11 C18B C19B 115.1(6) . .
N11 C18B H18C 108.5 . .
C19B C18B H18C 108.5 . .
N11 C18B H18D 108.5 . .
C19B C18B H18D 108.5 . .
H18C C18B H18D 107.5 . .
C18B C19B C20B 115.6(6) . .
C18B C19B H19C 108.4 . .
C20B C19B H19C 108.4 . .
C18B C19B H19D 108.4 . .
C20B C19B H19D 108.4 . .
H19C C19B H19D 107.5 . .
C19B C20B C21B 109.4(8) . .
C19B C20B H20C 109.8 . .
C21B C20B H20C 109.8 . .
C19B C20B H20D 109.8 . .
C21B C20B H20D 109.8 . .
H20C C20B H20D 108.2 . .
C22B C21B C20B 111.7(8) . .
C22B C21B H21C 109.3 . .
C20B C21B H21C 109.3 . .
C22B C21B H21D 109.3 . .
C20B C21B H21D 109.3 . .
H21C C21B H21D 107.9 . .
C21B C22B C23B 110.9(8) . .
C21B C22B H22C 109.5 . .
C23B C22B H22C 109.5 . .
C21B C22B H22D 109.5 . .
C23B C22B H22D 109.5 . .
H22C C22B H22D 108.0 . .
C24B C23B C22B 110.5(9) . .
C24B C23B H23C 109.6 . .
C22B C23B H23C 109.6 . .
C24B C23B H23D 109.6 . .
C22B C23B H23D 109.6 . .
H23C C23B H23D 108.1 . .
C23B C24B C25B 108.9(9) . .
C23B C24B H24C 109.9 . .
C25B C24B H24C 109.9 . .
C23B C24B H24D 109.9 . .
C25B C24B H24D 109.9 . .
H24C C24B H24D 108.3 . .
C24B C25B H25D 109.5 . .
C24B C25B H25E 109.5 . .
H25D C25B H25E 109.5 . .
C24B C25B H25F 109.5 . .
H25D C25B H25F 109.5 . .
H25E C25B H25F 109.5 . .
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
Cl1 O3A 1.431(4) .
Cl1 O1A 1.434(4) .
Cl1 O1B 1.441(5) .
Cl1 O3B 1.450(5) .
Cl1 O4A 1.483(4) .
Cl1 O2B 1.485(5) .
Cl1 O4B 1.506(5) .
Cl1 O2A 1.537(3) .
C1 C2 1.439(7) .
C1 H1A 0.9600 .
C1 H1B 0.9600 .
C1 H1C 0.9600 .
C2 C3 1.502(7) .
C2 H2B 0.9700 .
C2 H2C 0.9700 .
C3 C4 1.488(6) .
C3 H3A 0.9700 .
C3 H3B 0.9700 .
C4 C5 1.490(5) .
C4 H4A 0.9700 .
C4 H4B 0.9700 .
C5 C6 1.509(5) .
C5 H5A 0.9700 .
C5 H5B 0.9700 .
C6 C7 1.481(5) .
C6 H6A 0.9700 .
C6 H6B 0.9700 .
C7 C8 1.509(4) .
C7 H7A 0.9700 .
C7 H7B 0.9700 .
C8 N9 1.478(3) .
C8 H8A 0.9700 .
C8 H8B 0.9700 .
N9 C10 1.319(3) .
N9 C13 1.388(3) .
C10 N11 1.326(3) .
C10 H10 0.9300 .
N11 C12 1.390(3) .
N11 C18B 1.484(3) .
N11 C18A 1.484(3) .
C12 C14 1.385(4) .
C12 C13 1.395(3) .
C13 C17 1.383(4) .
C14 C15 1.362(4) .
C14 H14 0.9300 .
C15 C16 1.391(4) .
C15 H15 0.9300 .
C16 C17 1.364(4) .
C16 H16 0.9300 .
C17 H17 0.9300 .
C18A C19A 1.489(5) .
C18A H18A 0.9700 .
C18A H18B 0.9700 .
C19A C20A 1.489(6) .
C19A H19A 0.9700 .
C19A H19B 0.9700 .
C20A C21A 1.540(6) .
C20A H20A 0.9700 .
C20A H20B 0.9700 .
C21A C22A 1.489(6) .
C21A H21A 0.9700 .
C21A H21B 0.9700 .
C22A C23A 1.531(6) .
C22A H22A 0.9700 .
C22A H22B 0.9700 .
C23A C24A 1.498(7) .
C23A H23A 0.9700 .
C23A H23B 0.9700 .
C24A C25A 1.503(7) .
C24A H24A 0.9700 .
C24A H24B 0.9700 .
C25A H25A 0.9600 .
C25A H25B 0.9600 .
C25A H25C 0.9600 .
C18B C19B 1.487(5) .
C18B H18C 0.9700 .
C18B H18D 0.9700 .
C19B C20B 1.492(6) .
C19B H19C 0.9700 .
C19B H19D 0.9700 .
C20B C21B 1.538(6) .
C20B H20C 0.9700 .
C20B H20D 0.9700 .
C21B C22B 1.490(7) .
C21B H21C 0.9700 .
C21B H21D 0.9700 .
C22B C23B 1.529(7) .
C22B H22C 0.9700 .
C22B H22D 0.9700 .
C23B C24B 1.498(7) .
C23B H23C 0.9700 .
C23B H23D 0.9700 .
C24B C25B 1.503(7) .
C24B H24C 0.9700 .
C24B H24D 0.9700 .
C25B H25D 0.9600 .
C25B H25E 0.9600 .
C25B H25F 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
_geom_torsion_site_symmetry_1
_geom_torsion_site_symmetry_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
C1 C2 C3 C4 -179.7(5) . . . .
C2 C3 C4 C5 178.4(5) . . . .
C3 C4 C5 C6 178.3(4) . . . .
C4 C5 C6 C7 179.8(4) . . . .
C5 C6 C7 C8 177.2(3) . . . .
C6 C7 C8 N9 -62.5(4) . . . .
C7 C8 N9 C10 106.9(3) . . . .
C7 C8 N9 C13 -75.1(3) . . . .
C13 N9 C10 N11 0.8(3) . . . .
C8 N9 C10 N11 179.1(2) . . . .
N9 C10 N11 C12 -0.6(3) . . . .
N9 C10 N11 C18B -178.9(2) . . . .
N9 C10 N11 C18A -178.9(2) . . . .
C10 N11 C12 C14 -176.9(3) . . . .
C18B N11 C12 C14 1.4(4) . . . .
C18A N11 C12 C14 1.4(4) . . . .
C10 N11 C12 C13 0.2(3) . . . .
C18B N11 C12 C13 178.4(2) . . . .
C18A N11 C12 C13 178.4(2) . . . .
C10 N9 C13 C17 177.5(3) . . . .
C8 N9 C13 C17 -0.8(4) . . . .
C10 N9 C13 C12 -0.7(3) . . . .
C8 N9 C13 C12 -179.0(2) . . . .
C14 C12 C13 C17 -0.7(4) . . . .
N11 C12 C13 C17 -178.1(2) . . . .
C14 C12 C13 N9 177.8(2) . . . .
N11 C12 C13 N9 0.3(3) . . . .
N11 C12 C14 C15 177.0(3) . . . .
C13 C12 C14 C15 0.4(4) . . . .
C12 C14 C15 C16 0.0(5) . . . .
C14 C15 C16 C17 -0.2(5) . . . .
C15 C16 C17 C13 -0.1(4) . . . .
N9 C13 C17 C16 -177.5(3) . . . .
C12 C13 C17 C16 0.5(4) . . . .
C10 N11 C18A C19A -101.2(4) . . . .
C12 N11 C18A C19A 80.8(4) . . . .
N11 C18A C19A C20A 61.0(9) . . . .
C18A C19A C20A C21A 176.6(8) . . . .
C19A C20A C21A C22A 174.0(9) . . . .
C20A C21A C22A C23A 180.0(9) . . . .
C21A C22A C23A C24A 178.6(11) . . . .
C22A C23A C24A C25A 179.9(11) . . . .
C10 N11 C18B C19B -60.8(7) . . . .
C12 N11 C18B C19B 121.2(6) . . . .
N11 C18B C19B C20B -56(2) . . . .
C18B C19B C20B C21B 172.9(17) . . . .
C19B C20B C21B C22B -179(2) . . . .
C20B C21B C22B C23B 174(3) . . . .
C21B C22B C23B C24B 174(3) . . . .
C22B C23B C24B C25B 161(3) . . . .
