#------------------------------------------------------------------------------
#$Date: 2025-06-02 21:20:34 +0300 (Mon, 02 Jun 2025) $
#$Revision: 299904 $
#$URL: file:///home/coder/svn-repositories/cod/cif/1/56/96/1569687.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_1569687
loop_
_publ_author_name
'Lončarić, Doroteja'
'Movahedifar, Fahimeh'
'Štoček, Jakub Radek'
'Dračínský, Martin'
'Cvačka, Josef'
'Guan, Shanshan'
'Bythell, Benjamin J.'
'Císařová, Ivana'
'Masson, Eric'
'Kaleta, Jiří'
_publ_section_title
;
 Solvent-controlled formation of alkali and alkali-earth-secured
 cucurbituril/guest trimers.
;
_journal_issue                   35
_journal_name_full               'Chemical science'
_journal_page_first              9258
_journal_page_last               9266
_journal_paper_doi               10.1039/d3sc02032k
_journal_volume                  14
_journal_year                    2023
_chemical_compound_source        'synthesized by the authors'
_chemical_formula_moiety         'C22 H26 N, 0.5(C2 H3 N), Cl, H2 O'
_chemical_formula_sum            'C23 H29.5 Cl N1.5 O'
_chemical_formula_weight         378.43
_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   mixed
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_audit_creation_method           SHELXL-2018/3
_audit_update_record
;
2022-11-23 deposited with the CCDC.	2023-08-08 downloaded from the CCDC.
;
_cell_angle_alpha                105.878(2)
_cell_angle_beta                 105.252(2)
_cell_angle_gamma                108.949(2)
_cell_formula_units_Z            4
_cell_length_a                   10.1283(6)
_cell_length_b                   15.0534(8)
_cell_length_c                   15.6108(9)
_cell_measurement_reflns_used    9503
_cell_measurement_temperature    120(2)
_cell_measurement_theta_max      27.4859
_cell_measurement_theta_min      2.2035
_cell_volume                     1996.7(2)
_computing_cell_refinement       'SAINT V8.40B (Bruker AXS LLC, 2019)'
_computing_data_collection       'Bruker Instrument Service vV6.2.15'
_computing_data_reduction        'SAINT V8.40B (Bruker AXS LLC, 2019)'
_computing_structure_refinement  'SHELXL-2018/3 (Sheldrick, 2018)'
_computing_structure_solution    'SHELXT 2018/2 (Sheldrick, 2018)'
_diffrn_ambient_temperature      120(2)
_diffrn_measured_fraction_theta_full 0.994
_diffrn_measured_fraction_theta_max 0.995
_diffrn_measurement_device_type  'Bruker D8 VENTURE Kappa Duo PHOTONIII CMOS'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_radiation_monochromator  'Quazar Mo multilayer optic'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0205
_diffrn_reflns_av_unetI/netI     0.0106
_diffrn_reflns_Laue_measured_fraction_full 0.994
_diffrn_reflns_Laue_measured_fraction_max 0.995
_diffrn_reflns_limit_h_max       13
_diffrn_reflns_limit_h_min       -13
_diffrn_reflns_limit_k_max       19
_diffrn_reflns_limit_k_min       -19
_diffrn_reflns_limit_l_max       20
_diffrn_reflns_limit_l_min       -20
_diffrn_reflns_number            101272
_diffrn_reflns_point_group_measured_fraction_full 0.994
_diffrn_reflns_point_group_measured_fraction_max 0.995
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         27.506
_diffrn_reflns_theta_min         2.203
_diffrn_source                   'I\mS  micro-focus sealed tube'
_exptl_absorpt_coefficient_mu    0.205
_exptl_absorpt_correction_T_max  0.96
_exptl_absorpt_correction_T_min  0.92
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
Krause, L., Herbst-Irmer, R., Sheldrick, G. M., Stalke, D. (2015).
"Comparison of silver and molybdenum microfocus X-ray sources for
single-crystal structure determination"
J. Appl. Cryst. 48, 3-10.
doi:10.1107/S1600576714022985
;
_exptl_crystal_colour            colourless-yellow
_exptl_crystal_density_diffrn    1.259
_exptl_crystal_description       prism
_exptl_crystal_F_000             812
_exptl_crystal_size_max          0.394
_exptl_crystal_size_mid          0.325
_exptl_crystal_size_min          0.216
_refine_diff_density_max         0.352
_refine_diff_density_min         -0.306
_refine_diff_density_rms         0.040
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.043
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     481
_refine_ls_number_reflns         9120
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.043
_refine_ls_R_factor_all          0.0336
_refine_ls_R_factor_gt           0.0325
_refine_ls_shift/su_max          0.001
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'w=1/[σ²(Fo²)+(0.0427P)²+0.8823P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0890
_refine_ls_wR_factor_ref         0.0901
_reflns_Friedel_coverage         0.000
_reflns_number_gt                8704
_reflns_number_total             9120
_reflns_threshold_expression     'I > 2σ(I)'
_cod_data_source_file            d3sc02032k2.cif
_cod_data_source_block           mo_dl077_kaleta
_cod_depositor_comments
;
Adding full bibliography for 1569684--1569687.cif.

2025-06-02
Z value and formula fixed to values more according to usual
chemical conventions.                 miguel
;
_cod_original_formula_sum            'C46 H59 Cl2 N3 O2'
_cod_original_formula_weight         756.86
_cod_original_formula_moiety         '2(C22 H26 N), C2 H3 N, 2(Cl), 2(H2 O)'
_cod_original_formula_units_Z            2
_cod_database_code               1569687
_shelx_shelxl_version_number     2018/3
_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.
;
_shelx_estimated_absorpt_t_min   0.924
_shelx_estimated_absorpt_t_max   0.957
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 0.00560(3) 0.33797(2) 0.38441(2) 0.02742(7) Uani 1 1 d . . . . .
Cl2 Cl 0.24960(3) 0.36022(2) 0.76021(2) 0.02321(7) Uani 1 1 d . . . . .
C1A C 0.32488(11) -0.07258(8) 0.70975(7) 0.01708(19) Uani 1 1 d . . . . .
H1A H 0.240596 -0.105423 0.728726 0.020 Uiso 1 1 calc R U . . .
C2A C 0.44398(12) 0.02397(8) 0.79775(7) 0.0183(2) Uani 1 1 d . . . . .
H2A H 0.401580 0.075070 0.812798 0.022 Uiso 1 1 calc R U . . .
C3A C 0.48258(13) -0.00889(9) 0.88289(8) 0.0228(2) Uani 1 1 d . . . . .
H3AA H 0.557029 0.051726 0.942074 0.027 Uiso 1 1 calc R U . . .
H3AB H 0.389969 -0.039356 0.894592 0.027 Uiso 1 1 calc R U . . .
C4A C 0.54824(12) -0.08689(9) 0.86086(8) 0.0224(2) Uani 1 1 d . . . . .
H4A H 0.571976 -0.108112 0.916277 0.027 Uiso 1 1 calc R U . . .
C5A C 0.43142(13) -0.18013(9) 0.76949(8) 0.0250(2) Uani 1 1 d . . . . .
H5AA H 0.338082 -0.211530 0.780138 0.030 Uiso 1 1 calc R U . . .
H5AB H 0.472081 -0.231520 0.754844 0.030 Uiso 1 1 calc R U . . .
C6A C 0.39387(12) -0.14839(8) 0.68381(8) 0.0205(2) Uani 1 1 d . . . . .
H6A H 0.318219 -0.209792 0.624314 0.025 Uiso 1 1 calc R U . . .
C7A C 0.59098(12) 0.07206(8) 0.78282(8) 0.0206(2) Uani 1 1 d . . . . .
H7AA H 0.569797 0.095133 0.729204 0.025 Uiso 1 1 calc R U . . .
H7AB H 0.665891 0.132368 0.842117 0.025 Uiso 1 1 calc R U . . .
C8A C 0.65611(12) -0.00611(9) 0.75934(8) 0.0221(2) Uani 1 1 d . . . . .
H8A H 0.750474 0.025297 0.748557 0.026 Uiso 1 1 calc R U . . .
C9A C 0.53797(13) -0.09882(9) 0.66733(8) 0.0237(2) Uani 1 1 d . . . . .
H9AA H 0.513645 -0.076845 0.613216 0.028 Uiso 1 1 calc R U . . .
H9AB H 0.579562 -0.149154 0.649960 0.028 Uiso 1 1 calc R U . . .
C10A C 0.69275(12) -0.03957(9) 0.84386(8) 0.0237(2) Uani 1 1 d . . . . .
H10A H 0.734641 -0.090211 0.828957 0.028 Uiso 1 1 calc R U . . .
H10B H 0.769682 0.020190 0.902965 0.028 Uiso 1 1 calc R U . . .
N11A N 0.25747(9) -0.05144(7) 0.62310(6) 0.01626(17) Uani 1 1 d . . . . .
C12A C 0.15426(12) -0.13282(8) 0.54145(8) 0.0192(2) Uani 1 1 d . . . . .
H12A H 0.125288 -0.199500 0.541451 0.023 Uiso 1 1 calc R U . . .
C13A C 0.09050(12) -0.12082(8) 0.45844(7) 0.0190(2) Uani 1 1 d . . . . .
H13A H 0.019488 -0.179359 0.401833 0.023 Uiso 1 1 calc R U . . .
C14A C 0.12870(11) -0.02362(8) 0.45615(7) 0.01570(19) Uani 1 1 d . . . . .
C15A C 0.22855(12) 0.05914(8) 0.54372(7) 0.0188(2) Uani 1 1 d . . . . .
H15A H 0.254047 0.126866 0.546965 0.023 Uiso 1 1 calc R U . . .
C16A C 0.29027(12) 0.04367(8) 0.62520(7) 0.0188(2) Uani 1 1 d . . . . .
H16A H 0.357048 0.100963 0.683832 0.023 Uiso 1 1 calc R U . . .
C17A C 0.06490(11) -0.00923(8) 0.36689(7) 0.01560(19) Uani 1 1 d . . . . .
C18A C -0.04309(12) -0.09243(8) 0.28202(8) 0.0201(2) Uani 1 1 d . . . . .
H18A H -0.078651 -0.159169 0.281887 0.024 Uiso 1 1 calc R U . . .
C19A C -0.09849(12) -0.07803(8) 0.19812(8) 0.0217(2) Uani 1 1 d . . . . .
H19A H -0.172354 -0.135315 0.141364 0.026 Uiso 1 1 calc R U . . .
C20A C -0.04836(12) 0.01840(8) 0.19519(7) 0.0191(2) Uani 1 1 d . . . . .
C21A C 0.05539(13) 0.10135(8) 0.28043(8) 0.0223(2) Uani 1 1 d . . . . .
H21A H 0.088376 0.168226 0.280795 0.027 Uiso 1 1 calc R U . . .
C22A C 0.11139(13) 0.08808(8) 0.36479(8) 0.0209(2) Uani 1 1 d . . . . .
H22A H 0.182361 0.145910 0.421991 0.025 Uiso 1 1 calc R U . . .
C23A C -0.10279(14) 0.03242(10) 0.10249(8) 0.0257(2) Uani 1 1 d . . . . .
H23A H -0.122033 0.093528 0.115586 0.039 Uiso 1 1 calc R U . . .
H23B H -0.196482 -0.027522 0.056608 0.039 Uiso 1 1 calc R U . . .
H23C H -0.025293 0.040390 0.074930 0.039 Uiso 1 1 calc R U . . .
C1B C 0.64085(12) 0.54336(8) 0.79196(7) 0.01720(19) Uani 1 1 d . . . . .
H1B H 0.590446 0.467916 0.773416 0.021 Uiso 1 1 calc R U . . .
C2B C 0.60878(12) 0.59510(8) 0.87905(7) 0.0193(2) Uani 1 1 d . . . . .
H2B H 0.498327 0.578090 0.858348 0.023 Uiso 1 1 calc R U . . .
C3B C 0.65440(13) 0.55261(9) 0.95535(8) 0.0236(2) Uani 1 1 d . . . . .
H3BA H 0.633082 0.582991 1.011964 0.028 Uiso 1 1 calc R U . . .
H3BB H 0.594319 0.477638 0.928108 0.028 Uiso 1 1 calc R U . . .
C4B C 0.82321(13) 0.57788(9) 0.98685(8) 0.0230(2) Uani 1 1 d . . . . .
H4B H 0.852163 0.549307 1.035844 0.028 Uiso 1 1 calc R U . . .
C5B C 0.85437(14) 0.53041(9) 0.89840(8) 0.0249(2) Uani 1 1 d . . . . .
H5BA H 0.794662 0.455342 0.869890 0.030 Uiso 1 1 calc R U . . .
H5BB H 0.962989 0.545108 0.918344 0.030 Uiso 1 1 calc R U . . .
C6B C 0.81125(12) 0.57457(8) 0.82230(8) 0.0192(2) Uani 1 1 d . . . . .
H6B H 0.833409 0.544393 0.765242 0.023 Uiso 1 1 calc R U . . .
C7B C 0.70047(13) 0.71124(8) 0.92136(8) 0.0217(2) Uani 1 1 d . . . . .
H7BA H 0.672891 0.738269 0.871578 0.026 Uiso 1 1 calc R U . . .
H7BB H 0.676734 0.743214 0.976188 0.026 Uiso 1 1 calc R U . . .
C8B C 0.86996(12) 0.73791(8) 0.95600(8) 0.0217(2) Uani 1 1 d . . . . .
H8B H 0.929369 0.813828 0.985036 0.026 Uiso 1 1 calc R U . . .
C9B C 0.90447(12) 0.69143(9) 0.86881(8) 0.0219(2) Uani 1 1 d . . . . .
H9BA H 1.013770 0.708024 0.889823 0.026 Uiso 1 1 calc R U . . .
H9BB H 0.879197 0.720950 0.820784 0.026 Uiso 1 1 calc R U . . .
C10B C 0.91458(13) 0.69412(9) 1.03122(8) 0.0237(2) Uani 1 1 d . . . . .
H10C H 1.024124 0.711437 1.052547 0.028 Uiso 1 1 calc R U . . .
H10D H 0.894296 0.724443 1.088333 0.028 Uiso 1 1 calc R U . . .
N11B N 0.57179(10) 0.56493(6) 0.70617(6) 0.01619(17) Uani 1 1 d . . . . .
C12B C 0.65012(12) 0.60524(8) 0.65766(7) 0.0181(2) Uani 1 1 d . . . . .
H12B H 0.754199 0.619113 0.675934 0.022 Uiso 1 1 calc R U . . .
C13B C 0.58140(12) 0.62655(8) 0.58211(7) 0.0184(2) Uani 1 1 d . . . . .
H13B H 0.639500 0.656335 0.550122 0.022 Uiso 1 1 calc R U . . .
C14B C 0.42715(11) 0.60503(7) 0.55159(7) 0.01616(19) Uani 1 1 d . . . . .
C15B C 0.34733(12) 0.55664(8) 0.59915(8) 0.0204(2) Uani 1 1 d . . . . .
H15B H 0.241329 0.536628 0.578876 0.025 Uiso 1 1 calc R U . . .
C16B C 0.42105(12) 0.53790(8) 0.67484(8) 0.0195(2) Uani 1 1 d . . . . .
H16B H 0.364629 0.505061 0.706026 0.023 Uiso 1 1 calc R U . . .
C17B C 0.35292(11) 0.63086(8) 0.47317(7) 0.01681(19) Uani 1 1 d . . . . .
C18B C 0.43302(12) 0.67159(8) 0.42178(8) 0.0208(2) Uani 1 1 d . . . . .
H18B H 0.534796 0.680559 0.436145 0.025 Uiso 1 1 calc R U . . .
C19B C 0.36495(13) 0.69893(9) 0.35013(8) 0.0223(2) Uani 1 1 d . . . . .
H19B H 0.420880 0.726308 0.315975 0.027 Uiso 1 1 calc R U . . .
C20B C 0.21592(12) 0.68690(8) 0.32742(8) 0.0201(2) Uani 1 1 d . . . . .
C21B C 0.13589(12) 0.64505(8) 0.37766(8) 0.0211(2) Uani 1 1 d . . . . .
H21B H 0.033741 0.635429 0.362541 0.025 Uiso 1 1 calc R U . . .
C22B C 0.20245(12) 0.61710(8) 0.44944(8) 0.0201(2) Uani 1 1 d . . . . .
H22B H 0.145519 0.588514 0.482558 0.024 Uiso 1 1 calc R U . . .
C23B C 0.14453(14) 0.71877(10) 0.25094(9) 0.0267(2) Uani 1 1 d . . . . .
H23D H 0.034587 0.678126 0.222746 0.040 Uiso 1 1 calc R U . . .
H23E H 0.184814 0.707607 0.200330 0.040 Uiso 1 1 calc R U . . .
H23F H 0.167697 0.791339 0.279928 0.040 Uiso 1 1 calc R U . . .
N1S N 0.63941(19) 0.29175(14) 1.01507(11) 0.0629(4) Uani 1 1 d . . . . .
C1S C 0.71907(16) 0.34434(11) 1.09246(10) 0.0360(3) Uani 1 1 d . . . . .
C2S C 0.82045(16) 0.41275(11) 1.19120(10) 0.0347(3) Uani 1 1 d . . . . .
H2S1 H 0.796748 0.471468 1.210604 0.052 Uiso 1 1 calc R U . . .
H2S2 H 0.925302 0.436585 1.195751 0.052 Uiso 1 1 calc R U . . .
H2S3 H 0.807822 0.376416 1.233960 0.052 Uiso 1 1 calc R U . . .
O1W O 0.21499(9) 0.29581(6) 0.54293(6) 0.02707(18) Uani 1 1 d . . . . .
H11W H 0.156409 0.316878 0.511613 0.041 Uiso 1 1 d R U . . .
H12W H 0.214509 0.316978 0.601413 0.041 Uiso 1 1 d R U . . .
O2W O 0.47020(11) 0.25638(7) 0.80812(7) 0.0326(2) Uani 1 1 d . . . . .
H21W H 0.416313 0.290828 0.805547 0.049 Uiso 1 1 d R U . . .
H22W H 0.513813 0.275126 0.870547 0.049 Uiso 1 1 d R U . . .
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
_geom_angle_publ_flag
N11A C1A C2A 113.57(8) . . ?
N11A C1A C6A 110.86(8) . . ?
C2A C1A C6A 109.53(8) . . ?
N11A C1A H1A 107.5 . . ?
C2A C1A H1A 107.5 . . ?
C6A C1A H1A 107.5 . . ?
C1A C2A C7A 112.36(8) . . ?
C1A C2A C3A 106.77(9) . . ?
C7A C2A C3A 107.92(8) . . ?
C1A C2A H2A 109.9 . . ?
C7A C2A H2A 109.9 . . ?
C3A C2A H2A 109.9 . . ?
C4A C3A C2A 110.40(9) . . ?
C4A C3A H3AA 109.6 . . ?
C2A C3A H3AA 109.6 . . ?
C4A C3A H3AB 109.6 . . ?
C2A C3A H3AB 109.6 . . ?
H3AA C3A H3AB 108.1 . . ?
C5A C4A C3A 108.81(9) . . ?
C5A C4A C10A 109.15(10) . . ?
C3A C4A C10A 109.74(9) . . ?
C5A C4A H4A 109.7 . . ?
C3A C4A H4A 109.7 . . ?
C10A C4A H4A 109.7 . . ?
C4A C5A C6A 110.17(9) . . ?
C4A C5A H5AA 109.6 . . ?
C6A C5A H5AA 109.6 . . ?
C4A C5A H5AB 109.6 . . ?
C6A C5A H5AB 109.6 . . ?
H5AA C5A H5AB 108.1 . . ?
C9A C6A C5A 110.01(9) . . ?
C9A C6A C1A 111.10(9) . . ?
C5A C6A C1A 106.66(9) . . ?
C9A C6A H6A 109.7 . . ?
C5A C6A H6A 109.7 . . ?
C1A C6A H6A 109.7 . . ?
C8A C7A C2A 110.11(9) . . ?
C8A C7A H7AA 109.6 . . ?
C2A C7A H7AA 109.6 . . ?
C8A C7A H7AB 109.6 . . ?
C2A C7A H7AB 109.6 . . ?
H7AA C7A H7AB 108.2 . . ?
C7A C8A C9A 108.65(9) . . ?
C7A C8A C10A 109.47(9) . . ?
C9A C8A C10A 109.89(9) . . ?
C7A C8A H8A 109.6 . . ?
C9A C8A H8A 109.6 . . ?
C10A C8A H8A 109.6 . . ?
C6A C9A C8A 109.92(9) . . ?
C6A C9A H9AA 109.7 . . ?
C8A C9A H9AA 109.7 . . ?
C6A C9A H9AB 109.7 . . ?
C8A C9A H9AB 109.7 . . ?
H9AA C9A H9AB 108.2 . . ?
C4A C10A C8A 109.55(9) . . ?
C4A C10A H10A 109.8 . . ?
C8A C10A H10A 109.8 . . ?
C4A C10A H10B 109.8 . . ?
C8A C10A H10B 109.8 . . ?
H10A C10A H10B 108.2 . . ?
C16A N11A C12A 119.32(9) . . ?
C16A N11A C1A 123.23(9) . . ?
C12A N11A C1A 117.38(8) . . ?
N11A C12A C13A 121.26(10) . . ?
N11A C12A H12A 119.4 . . ?
C13A C12A H12A 119.4 . . ?
C12A C13A C14A 120.97(10) . . ?
C12A C13A H13A 119.5 . . ?
C14A C13A H13A 119.5 . . ?
C13A C14A C15A 116.10(9) . . ?
C13A C14A C17A 121.83(9) . . ?
C15A C14A C17A 122.07(9) . . ?
C16A C15A C14A 120.97(10) . . ?
C16A C15A H15A 119.5 . . ?
C14A C15A H15A 119.5 . . ?
N11A C16A C15A 121.14(9) . . ?
N11A C16A H16A 119.4 . . ?
C15A C16A H16A 119.4 . . ?
C22A C17A C18A 118.04(9) . . ?
C22A C17A C14A 120.84(9) . . ?
C18A C17A C14A 121.12(9) . . ?
C19A C18A C17A 120.42(10) . . ?
C19A C18A H18A 119.8 . . ?
C17A C18A H18A 119.8 . . ?
C18A C19A C20A 121.52(10) . . ?
C18A C19A H19A 119.2 . . ?
C20A C19A H19A 119.2 . . ?
C19A C20A C21A 117.89(10) . . ?
C19A C20A C23A 121.09(10) . . ?
C21A C20A C23A 121.01(10) . . ?
C22A C21A C20A 121.14(10) . . ?
C22A C21A H21A 119.4 . . ?
C20A C21A H21A 119.4 . . ?
C21A C22A C17A 120.93(10) . . ?
C21A C22A H22A 119.5 . . ?
C17A C22A H22A 119.5 . . ?
C20A C23A H23A 109.5 . . ?
C20A C23A H23B 109.5 . . ?
H23A C23A H23B 109.5 . . ?
C20A C23A H23C 109.5 . . ?
H23A C23A H23C 109.5 . . ?
H23B C23A H23C 109.5 . . ?
N11B C1B C6B 113.95(8) . . ?
N11B C1B C2B 110.86(8) . . ?
C6B C1B C2B 109.55(8) . . ?
N11B C1B H1B 107.4 . . ?
C6B C1B H1B 107.4 . . ?
C2B C1B H1B 107.4 . . ?
C7B C2B C3B 109.80(9) . . ?
C7B C2B C1B 110.85(9) . . ?
C3B C2B C1B 107.37(9) . . ?
C7B C2B H2B 109.6 . . ?
C3B C2B H2B 109.6 . . ?
C1B C2B H2B 109.6 . . ?
C4B C3B C2B 109.81(9) . . ?
C4B C3B H3BA 109.7 . . ?
C2B C3B H3BA 109.7 . . ?
C4B C3B H3BB 109.7 . . ?
C2B C3B H3BB 109.7 . . ?
H3BA C3B H3BB 108.2 . . ?
C3B C4B C10B 109.02(9) . . ?
C3B C4B C5B 109.06(9) . . ?
C10B C4B C5B 110.02(10) . . ?
C3B C4B H4B 109.6 . . ?
C10B C4B H4B 109.6 . . ?
C5B C4B H4B 109.6 . . ?
C4B C5B C6B 110.14(9) . . ?
C4B C5B H5BA 109.6 . . ?
C6B C5B H5BA 109.6 . . ?
C4B C5B H5BB 109.6 . . ?
C6B C5B H5BB 109.6 . . ?
H5BA C5B H5BB 108.1 . . ?
C1B C6B C9B 112.45(9) . . ?
C1B C6B C5B 105.92(9) . . ?
C9B C6B C5B 108.55(9) . . ?
C1B C6B H6B 109.9 . . ?
C9B C6B H6B 109.9 . . ?
C5B C6B H6B 109.9 . . ?
C8B C7B C2B 109.84(9) . . ?
C8B C7B H7BA 109.7 . . ?
C2B C7B H7BA 109.7 . . ?
C8B C7B H7BB 109.7 . . ?
C2B C7B H7BB 109.7 . . ?
H7BA C7B H7BB 108.2 . . ?
C7B C8B C9B 108.50(9) . . ?
C7B C8B C10B 110.65(9) . . ?
C9B C8B C10B 109.06(9) . . ?
C7B C8B H8B 109.5 . . ?
C9B C8B H8B 109.5 . . ?
C10B C8B H8B 109.5 . . ?
C8B C9B C6B 110.01(9) . . ?
C8B C9B H9BA 109.7 . . ?
C6B C9B H9BA 109.7 . . ?
C8B C9B H9BB 109.7 . . ?
C6B C9B H9BB 109.7 . . ?
H9BA C9B H9BB 108.2 . . ?
C4B C10B C8B 109.53(9) . . ?
C4B C10B H10C 109.8 . . ?
C8B C10B H10C 109.8 . . ?
C4B C10B H10D 109.8 . . ?
C8B C10B H10D 109.8 . . ?
H10C C10B H10D 108.2 . . ?
C12B N11B C16B 119.04(9) . . ?
C12B N11B C1B 123.97(9) . . ?
C16B N11B C1B 116.94(8) . . ?
N11B C12B C13B 121.03(9) . . ?
N11B C12B H12B 119.5 . . ?
C13B C12B H12B 119.5 . . ?
C12B C13B C14B 121.17(9) . . ?
C12B C13B H13B 119.4 . . ?
C14B C13B H13B 119.4 . . ?
C15B C14B C13B 116.11(9) . . ?
C15B C14B C17B 121.98(9) . . ?
C13B C14B C17B 121.90(9) . . ?
C16B C15B C14B 120.58(10) . . ?
C16B C15B H15B 119.7 . . ?
C14B C15B H15B 119.7 . . ?
N11B C16B C15B 121.80(10) . . ?
N11B C16B H16B 119.1 . . ?
C15B C16B H16B 119.1 . . ?
C22B C17B C18B 118.42(9) . . ?
C22B C17B C14B 121.07(9) . . ?
C18B C17B C14B 120.50(9) . . ?
C19B C18B C17B 120.59(10) . . ?
C19B C18B H18B 119.7 . . ?
C17B C18B H18B 119.7 . . ?
C18B C19B C20B 121.12(10) . . ?
C18B C19B H19B 119.4 . . ?
C20B C19B H19B 119.4 . . ?
C21B C20B C19B 118.16(10) . . ?
C21B C20B C23B 121.27(10) . . ?
C19B C20B C23B 120.56(10) . . ?
C22B C21B C20B 121.35(10) . . ?
C22B C21B H21B 119.3 . . ?
C20B C21B H21B 119.3 . . ?
C21B C22B C17B 120.34(10) . . ?
C21B C22B H22B 119.8 . . ?
C17B C22B H22B 119.8 . . ?
C20B C23B H23D 109.5 . . ?
C20B C23B H23E 109.5 . . ?
H23D C23B H23E 109.5 . . ?
C20B C23B H23F 109.5 . . ?
H23D C23B H23F 109.5 . . ?
H23E C23B H23F 109.5 . . ?
N1S C1S C2S 179.19(17) . . ?
C1S C2S H2S1 109.5 . . ?
C1S C2S H2S2 109.5 . . ?
H2S1 C2S H2S2 109.5 . . ?
C1S C2S H2S3 109.5 . . ?
H2S1 C2S H2S3 109.5 . . ?
H2S2 C2S H2S3 109.5 . . ?
H11W O1W H12W 103.3 . . ?
H21W O2W H22W 101.3 . . ?
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
C1A N11A 1.5126(12) . ?
C1A C2A 1.5336(14) . ?
C1A C6A 1.5390(14) . ?
C1A H1A 1.0000 . ?
C2A C7A 1.5395(15) . ?
C2A C3A 1.5414(14) . ?
C2A H2A 1.0000 . ?
C3A C4A 1.5315(16) . ?
C3A H3AA 0.9900 . ?
C3A H3AB 0.9900 . ?
C4A C5A 1.5305(16) . ?
C4A C10A 1.5332(16) . ?
C4A H4A 1.0000 . ?
C5A C6A 1.5369(15) . ?
C5A H5AA 0.9900 . ?
C5A H5AB 0.9900 . ?
C6A C9A 1.5325(16) . ?
C6A H6A 1.0000 . ?
C7A C8A 1.5328(15) . ?
C7A H7AA 0.9900 . ?
C7A H7AB 0.9900 . ?
C8A C9A 1.5352(16) . ?
C8A C10A 1.5362(15) . ?
C8A H8A 1.0000 . ?
C9A H9AA 0.9900 . ?
C9A H9AB 0.9900 . ?
C10A H10A 0.9900 . ?
C10A H10B 0.9900 . ?
N11A C16A 1.3494(13) . ?
N11A C12A 1.3531(13) . ?
C12A C13A 1.3756(14) . ?
C12A H12A 0.9500 . ?
C13A C14A 1.4001(14) . ?
C13A H13A 0.9500 . ?
C14A C15A 1.4023(14) . ?
C14A C17A 1.4794(13) . ?
C15A C16A 1.3788(14) . ?
C15A H15A 0.9500 . ?
C16A H16A 0.9500 . ?
C17A C22A 1.3982(14) . ?
C17A C18A 1.4000(14) . ?
C18A C19A 1.3875(14) . ?
C18A H18A 0.9500 . ?
C19A C20A 1.3917(15) . ?
C19A H19A 0.9500 . ?
C20A C21A 1.3918(15) . ?
C20A C23A 1.5052(14) . ?
C21A C22A 1.3857(15) . ?
C21A H21A 0.9500 . ?
C22A H22A 0.9500 . ?
C23A H23A 0.9800 . ?
C23A H23B 0.9800 . ?
C23A H23C 0.9800 . ?
C1B N11B 1.5104(12) . ?
C1B C6B 1.5314(14) . ?
C1B C2B 1.5420(14) . ?
C1B H1B 1.0000 . ?
C2B C7B 1.5317(15) . ?
C2B C3B 1.5364(14) . ?
C2B H2B 1.0000 . ?
C3B C4B 1.5306(16) . ?
C3B H3BA 0.9900 . ?
C3B H3BB 0.9900 . ?
C4B C10B 1.5316(16) . ?
C4B C5B 1.5338(16) . ?
C4B H4B 1.0000 . ?
C5B C6B 1.5466(14) . ?
C5B H5BA 0.9900 . ?
C5B H5BB 0.9900 . ?
C6B C9B 1.5412(15) . ?
C6B H6B 1.0000 . ?
C7B C8B 1.5315(15) . ?
C7B H7BA 0.9900 . ?
C7B H7BB 0.9900 . ?
C8B C9B 1.5338(16) . ?
C8B C10B 1.5347(14) . ?
C8B H8B 1.0000 . ?
C9B H9BA 0.9900 . ?
C9B H9BB 0.9900 . ?
C10B H10C 0.9900 . ?
C10B H10D 0.9900 . ?
N11B C12B 1.3513(13) . ?
N11B C16B 1.3529(13) . ?
C12B C13B 1.3778(14) . ?
C12B H12B 0.9500 . ?
C13B C14B 1.4028(14) . ?
C13B H13B 0.9500 . ?
C14B C15B 1.4017(14) . ?
C14B C17B 1.4769(14) . ?
C15B C16B 1.3742(14) . ?
C15B H15B 0.9500 . ?
C16B H16B 0.9500 . ?
C17B C22B 1.3995(14) . ?
C17B C18B 1.4022(15) . ?
C18B C19B 1.3880(15) . ?
C18B H18B 0.9500 . ?
C19B C20B 1.3938(15) . ?
C19B H19B 0.9500 . ?
C20B C21B 1.3937(15) . ?
C20B C23B 1.5043(14) . ?
C21B C22B 1.3898(15) . ?
C21B H21B 0.9500 . ?
C22B H22B 0.9500 . ?
C23B H23D 0.9800 . ?
C23B H23E 0.9800 . ?
C23B H23F 0.9800 . ?
N1S C1S 1.134(2) . ?
C1S C2S 1.450(2) . ?
C2S H2S1 0.9800 . ?
C2S H2S2 0.9800 . ?
C2S H2S3 0.9800 . ?
O1W H11W 0.8637 . ?
O1W H12W 0.8827 . ?
O2W H21W 0.8673 . ?
O2W H22W 0.8755 . ?
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
_geom_hbond_publ_flag
O1W H11W Cl1 0.86 2.33 3.1618(9) 161.0 . yes
O1W H12W Cl2 0.88 2.28 3.1499(9) 168.5 . yes
O2W H21W Cl2 0.87 2.32 3.1661(10) 166.6 . yes
O2W H22W N1S 0.88 2.18 3.0349(18) 165.9 . yes
