#------------------------------------------------------------------------------
#$Date: 2017-06-29 11:01:09 +0300 (Thu, 29 Jun 2017) $
#$Revision: 198233 $
#$URL: file:///home/coder/svn-repositories/cod/cif/7/20/50/7205067.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_7205067
loop_
_publ_author_name
'Luciawati, Fera'
'Higham, Luke T.'
'Strauss, Christopher R.'
'Scott, Janet L.'
_publ_section_title
;
 Horning-crown diamine complexes and salts: proton transfer mediated by
 solid-state intermolecular hydrogen bonding
;
_journal_issue                   1
_journal_name_full               CrystEngComm
_journal_page_first              167
_journal_paper_doi               10.1039/c003571h
_journal_volume                  13
_journal_year                    2011
_chemical_formula_moiety         'C44 H40 O6,C3 H10 N2,C1 H Cl3'
_chemical_formula_sum            'C48 H51 Cl3 N2 O6'
_chemical_formula_weight         858.26
_chemical_name_common
;
(3,4:9,10:18,19:24,25-tetrabenzo-5,8,20,23-tetraoxa-tricyclo
(25.3.1.112,16)dotriaconta-1(30),3,9,12,14,16(32),18, 24,27(31), 28-
decaene-31,32-diol) propylenediamine inclusion complex
;
_chemical_name_systematic
;
(3,4:9,10:18,19:24,25-tetrabenzo-5,8,20,23-tetraoxa-tricyclo
[25.3.1.112,16]dotriaconta-1(30),3,9,12,14,16(32),18, 24,27(31),
28-decaene-31,32-diol) propylenediamine inclusion complex
;
_space_group_IT_number           2
_space_group_name_Hall           '-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                113.964(1)
_cell_angle_beta                 93.672(1)
_cell_angle_gamma                108.788(1)
_cell_formula_units_Z            2
_cell_length_a                   12.6805(2)
_cell_length_b                   13.8085(3)
_cell_length_c                   14.8731(3)
_cell_measurement_temperature    123(2)
_cell_volume                     2195.08(8)
_computing_cell_refinement       'Nonius collect'
_computing_data_collection       'Nonius collect'
_computing_data_reduction        'Nonius collect'
_computing_molecular_graphics    X-seed
_computing_publication_material  ciftab
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 1990)'
_diffrn_ambient_temperature      123(2)
_diffrn_measured_fraction_theta_full 0.980
_diffrn_measured_fraction_theta_max 0.980
_diffrn_measurement_device_type  'Enraf Nonius Kappa CCD'
_diffrn_measurement_method       'phi and omega 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  0.0000
_diffrn_reflns_av_sigmaI/netI    0.1075
_diffrn_reflns_limit_h_max       16
_diffrn_reflns_limit_h_min       0
_diffrn_reflns_limit_k_max       17
_diffrn_reflns_limit_k_min       -18
_diffrn_reflns_limit_l_max       19
_diffrn_reflns_limit_l_min       -19
_diffrn_reflns_number            10317
_diffrn_reflns_theta_full        27.92
_diffrn_reflns_theta_max         27.92
_diffrn_reflns_theta_min         1.94
_exptl_absorpt_coefficient_mu    0.260
_exptl_absorpt_correction_type   none
_exptl_crystal_colour            colourless
_exptl_crystal_density_diffrn    1.299
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       needles
_exptl_crystal_F_000             904
_exptl_crystal_size_max          0.40
_exptl_crystal_size_mid          0.17
_exptl_crystal_size_min          0.10
_refine_diff_density_max         0.617
_refine_diff_density_min         -0.669
_refine_diff_density_rms         0.063
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.017
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     556
_refine_ls_number_reflns         10317
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.017
_refine_ls_R_factor_all          0.1350
_refine_ls_R_factor_gt           0.0555
_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)+(0.0586P)²+0.0000P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1105
_refine_ls_wR_factor_ref         0.1340
_reflns_number_gt                5653
_reflns_number_total             10317
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            C003571H.TXT
_cod_data_source_block           1b
_cod_original_cell_volume        2195.08(7)
_cod_database_code               7205067
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
_atom_site_disorder_assembly
_atom_site_disorder_group
O1 O 0.33850(13) 0.93906(14) 0.42153(11) 0.0238(4) Uani 1 1 d . . .
H1O H 0.396(2) 0.953(2) 0.3955(18) 0.037(8) Uiso 1 1 d . . .
C1 C 0.24728(18) 0.84173(19) 0.36042(15) 0.0177(5) Uani 1 1 d . . .
O2 O 0.56923(13) 0.76987(14) 0.20049(11) 0.0255(4) Uani 1 1 d . . .
C2 C 0.25468(18) 0.7517(2) 0.27531(15) 0.0195(5) Uani 1 1 d . . .
O3 O 0.23190(13) 1.14442(13) 0.64628(10) 0.0235(4) Uani 1 1 d . . .
C3 C 0.36722(19) 0.7531(2) 0.24839(16) 0.0225(5) Uani 1 1 d . . .
H3A H 0.3640 0.6735 0.2189 0.027 Uiso 1 1 calc R . .
H3B H 0.4275 0.7980 0.3115 0.027 Uiso 1 1 calc R . .
C4 C 0.40301(18) 0.80210(19) 0.17507(15) 0.0188(5) Uani 1 1 d . . .
C5 C 0.50895(18) 0.80672(19) 0.15021(15) 0.0192(5) Uani 1 1 d . . .
C6 C 0.67868(18) 0.7708(2) 0.18234(15) 0.0237(6) Uani 1 1 d . . .
H6A H 0.7268 0.8457 0.1867 0.028 Uiso 1 1 calc R . .
H6B H 0.6705 0.7098 0.1144 0.028 Uiso 1 1 calc R . .
C7 C 0.26909(19) 1.2498(2) 0.73767(15) 0.0238(6) Uani 1 1 d . . .
H7A H 0.2034 1.2715 0.7559 0.029 Uiso 1 1 calc R . .
H7B H 0.3260 1.3123 0.7292 0.029 Uiso 1 1 calc R . .
C8 C 0.18929(17) 1.14310(19) 0.55839(15) 0.0177(5) Uani 1 1 d . . .
C9 C 0.14259(18) 1.03443(19) 0.47462(15) 0.0174(5) Uani 1 1 d . . .
C10 C 0.13972(18) 0.92961(19) 0.48502(15) 0.0186(5) Uani 1 1 d . . .
H10A H 0.0694 0.9003 0.5071 0.022 Uiso 1 1 calc R . .
H10B H 0.2058 0.9524 0.5387 0.022 Uiso 1 1 calc R . .
C11 C 0.14276(18) 0.83365(19) 0.38969(15) 0.0169(5) Uani 1 1 d . . .
C12 C 0.04525(18) 0.7376(2) 0.32941(15) 0.0204(5) Uani 1 1 d . . .
H12 H -0.0260 0.7317 0.3480 0.024 Uiso 1 1 calc R . .
C13 C 0.05013(19) 0.6500(2) 0.24263(15) 0.0229(5) Uani 1 1 d . . .
H13 H -0.0176 0.5857 0.2011 0.027 Uiso 1 1 calc R . .
C14 C 0.15436(19) 0.65709(19) 0.21694(15) 0.0222(5) Uani 1 1 d . . .
H14 H 0.1577 0.5961 0.1583 0.027 Uiso 1 1 calc R . .
C15 C 0.33766(19) 0.8400(2) 0.13042(15) 0.0239(6) Uani 1 1 d . . .
H15 H 0.2663 0.8387 0.1471 0.029 Uiso 1 1 calc R . .
C16 C 0.3739(2) 0.8800(2) 0.06149(17) 0.0310(6) Uani 1 1 d . . .
H16 H 0.3281 0.9068 0.0321 0.037 Uiso 1 1 calc R . .
C17 C 0.4770(2) 0.8807(2) 0.03585(17) 0.0292(6) Uani 1 1 d . . .
H17 H 0.5010 0.9061 -0.0127 0.035 Uiso 1 1 calc R . .
C18 C 0.54530(19) 0.8446(2) 0.08049(15) 0.0239(6) Uani 1 1 d . . .
H18 H 0.6165 0.8458 0.0634 0.029 Uiso 1 1 calc R . .
C19 C 0.19030(18) 1.2403(2) 0.55029(16) 0.0217(5) Uani 1 1 d . . .
H19 H 0.2233 1.3135 0.6074 0.026 Uiso 1 1 calc R . .
C20 C 0.1430(2) 1.2299(2) 0.45860(17) 0.0259(6) Uani 1 1 d . . .
H20 H 0.1430 1.2960 0.4530 0.031 Uiso 1 1 calc R . .
C21 C 0.0958(2) 1.1238(2) 0.37550(17) 0.0294(6) Uani 1 1 d . . .
H21 H 0.0625 1.1163 0.3128 0.035 Uiso 1 1 calc R . .
C22 C 0.0975(2) 1.0281(2) 0.38440(16) 0.0269(6) Uani 1 1 d . . .
H22 H 0.0665 0.9556 0.3264 0.032 Uiso 1 1 calc R . .
O1' O 0.42442(14) 0.54669(15) 0.63229(11) 0.0251(4) Uani 1 1 d . . .
H1'O H 0.495(3) 0.587(3) 0.625(2) 0.067(10) Uiso 1 1 d . . .
C1' C 0.42121(18) 0.55068(19) 0.72507(15) 0.0183(5) Uani 1 1 d . . .
O2' O 0.15241(13) 0.56009(13) 0.51595(10) 0.0234(4) Uani 1 1 d . . .
C2' C 0.31805(17) 0.54776(18) 0.75581(15) 0.0173(5) Uani 1 1 d . . .
O3' O 0.81718(11) 0.56219(13) 0.68785(10) 0.0223(4) Uani 1 1 d . . .
C3' C 0.22014(18) 0.53978(19) 0.68611(16) 0.0197(5) Uani 1 1 d . . .
H3'1 H 0.1477 0.5020 0.7012 0.024 Uiso 1 1 calc R . .
H3'2 H 0.2196 0.4897 0.6158 0.024 Uiso 1 1 calc R . .
C4' C 0.22255(17) 0.65289(19) 0.69223(15) 0.0180(5) Uani 1 1 d . . .
C5' C 0.18408(18) 0.6594(2) 0.60515(15) 0.0193(5) Uani 1 1 d . . .
C6' C 0.10680(19) 0.5617(2) 0.42589(15) 0.0220(5) Uani 1 1 d . . .
H6'1 H 0.1637 0.6208 0.4135 0.026 Uiso 1 1 calc R . .
H6'2 H 0.0371 0.5793 0.4325 0.026 Uiso 1 1 calc R . .
C7' C 0.92108(18) 0.5553(2) 0.65937(15) 0.0213(5) Uani 1 1 d . . .
H7'1 H 0.9756 0.5678 0.7175 0.026 Uiso 1 1 calc R . .
H7'2 H 0.9567 0.6149 0.6377 0.026 Uiso 1 1 calc R . .
C8' C 0.82207(18) 0.66491(19) 0.76000(14) 0.0181(5) Uani 1 1 d . . .
C9' C 0.71939(18) 0.66269(19) 0.79217(15) 0.0188(5) Uani 1 1 d . . .
C10' C 0.61976(18) 0.5484(2) 0.75080(16) 0.0226(5) Uani 1 1 d . . .
H10C H 0.6026 0.5143 0.6761 0.027 Uiso 1 1 calc R . .
H10D H 0.6437 0.4967 0.7701 0.027 Uiso 1 1 calc R . .
C11' C 0.51122(18) 0.55184(19) 0.78521(15) 0.0195(5) Uani 1 1 d . . .
C12' C 0.49776(19) 0.55393(19) 0.87852(16) 0.0228(5) Uani 1 1 d . . .
H12' H 0.5584 0.5549 0.9202 0.027 Uiso 1 1 calc R . .
C13' C 0.39905(19) 0.5546(2) 0.91146(16) 0.0230(5) Uani 1 1 d . . .
H13' H 0.3924 0.5578 0.9758 0.028 Uiso 1 1 calc R . .
C14' C 0.30894(18) 0.55061(19) 0.84980(16) 0.0209(5) Uani 1 1 d . . .
H14' H 0.2402 0.5498 0.8720 0.025 Uiso 1 1 calc R . .
C15' C 0.25575(19) 0.7505(2) 0.78371(17) 0.0255(6) Uani 1 1 d . . .
H15' H 0.2828 0.7481 0.8435 0.031 Uiso 1 1 calc R . .
C16' C 0.2505(2) 0.8518(2) 0.79003(17) 0.0312(6) Uani 1 1 d . . .
H16' H 0.2747 0.9180 0.8535 0.037 Uiso 1 1 calc R . .
C17' C 0.2099(2) 0.8561(2) 0.70394(17) 0.0288(6) Uani 1 1 d . . .
H17' H 0.2045 0.9248 0.7083 0.035 Uiso 1 1 calc R . .
C18' C 0.17691(19) 0.7598(2) 0.61084(17) 0.0233(5) Uani 1 1 d . . .
H18' H 0.1496 0.7627 0.5514 0.028 Uiso 1 1 calc R . .
C19' C 0.91898(19) 0.7657(2) 0.80110(15) 0.0232(5) Uani 1 1 d . . .
H19' H 0.9887 0.7660 0.7811 0.028 Uiso 1 1 calc R . .
C20' C 0.9128(2) 0.8661(2) 0.87167(16) 0.0276(6) Uani 1 1 d . . .
H20' H 0.9787 0.9353 0.8997 0.033 Uiso 1 1 calc R . .
C21' C 0.8129(2) 0.8668(2) 0.90139(17) 0.0303(6) Uani 1 1 d . . .
H21' H 0.8090 0.9362 0.9486 0.036 Uiso 1 1 calc R . .
C22' C 0.7169(2) 0.7645(2) 0.86171(16) 0.0263(6) Uani 1 1 d . . .
H22' H 0.6481 0.7651 0.8832 0.032 Uiso 1 1 calc R . .
N1 N 0.53504(18) 0.03903(19) 0.38533(17) 0.0305(5) Uani 1 1 d . . .
H1NA H 0.549(2) 0.032(2) 0.330(2) 0.036(8) Uiso 1 1 d . . .
H1NB H 0.590(3) 0.020(3) 0.415(2) 0.056(9) Uiso 1 1 d . . .
C1G C 0.5433(2) 0.1564(2) 0.45051(17) 0.0291(6) Uani 1 1 d . . .
H1G1 H 0.6239 0.2102 0.4690 0.035 Uiso 1 1 calc R . .
H1G2 H 0.5198 0.1596 0.5135 0.035 Uiso 1 1 calc R . .
C2G C 0.4692(2) 0.1937(2) 0.39901(17) 0.0311(6) Uani 1 1 d . . .
H2G1 H 0.3915 0.1329 0.3692 0.037 Uiso 1 1 calc R . .
H2G2 H 0.5016 0.2053 0.3437 0.037 Uiso 1 1 calc R . .
C3G C 0.4618(2) 0.3042(2) 0.47359(17) 0.0309(6) Uani 1 1 d . . .
H3G1 H 0.4210 0.2900 0.5243 0.037 Uiso 1 1 calc R . .
H3G2 H 0.5399 0.3619 0.5096 0.037 Uiso 1 1 calc R . .
N2 N 0.40172(19) 0.3499(2) 0.42321(17) 0.0306(5) Uani 1 1 d . . .
H2NB H 0.385(2) 0.404(2) 0.4675(18) 0.031(8) Uiso 1 1 d . . .
H2NA H 0.333(2) 0.294(3) 0.382(2) 0.049(9) Uiso 1 1 d . . .
C1Z C -0.0605(2) 0.7088(2) 0.00399(17) 0.0360(7) Uani 1 1 d . . .
H1Z H -0.0959 0.7246 -0.0479 0.043 Uiso 1 1 calc R . .
Cl1 Cl -0.16684(6) 0.60346(6) 0.01969(5) 0.0415(2) Uani 1 1 d . . .
Cl2 Cl 0.04811(6) 0.66075(7) -0.04021(5) 0.0526(2) Uani 1 1 d . . .
Cl3 Cl -0.00202(8) 0.83648(7) 0.11634(5) 0.0643(3) 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'
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'
Cl Cl 0.1484 0.1585 '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
O1 C1 C2 123.52(19) . . ?
O1 C1 C11 115.58(18) . . ?
C2 C1 C11 120.86(19) . . ?
C5 O2 C6 119.41(17) . . ?
C14 C2 C1 118.23(19) . . ?
C14 C2 C3 119.85(19) . . ?
C1 C2 C3 121.9(2) . . ?
C8 O3 C7 118.28(18) . . ?
C2 C3 C4 116.3(2) . . ?
C15 C4 C5 118.1(2) . . ?
C15 C4 C3 124.35(19) . . ?
C5 C4 C3 117.5(2) . . ?
O2 C5 C18 124.9(2) . . ?
O2 C5 C4 113.84(19) . . ?
C18 C5 C4 121.2(2) . . ?
O2 C6 C7 105.98(17) . 2_676 ?
O3 C7 C6 106.49(19) . 2_676 ?
O3 C8 C19 124.00(19) . . ?
O3 C8 C9 115.0(2) . . ?
C19 C8 C9 121.0(2) . . ?
C22 C9 C8 117.3(2) . . ?
C22 C9 C10 122.17(19) . . ?
C8 C9 C10 120.47(19) . . ?
C9 C10 C11 114.56(17) . . ?
C12 C11 C1 118.73(18) . . ?
C12 C11 C10 122.07(19) . . ?
C1 C11 C10 119.20(19) . . ?
C13 C12 C11 121.1(2) . . ?
C14 C13 C12 119.5(2) . . ?
C13 C14 C2 121.44(19) . . ?
C4 C15 C16 121.3(2) . . ?
C17 C16 C15 119.6(2) . . ?
C18 C17 C16 120.4(2) . . ?
C17 C18 C5 119.3(2) . . ?
C20 C19 C8 119.7(2) . . ?
C21 C20 C19 120.2(2) . . ?
C20 C21 C22 119.4(2) . . ?
C9 C22 C21 122.3(2) . . ?
O1' C1' C11' 123.19(18) . . ?
O1' C1' C2' 115.79(19) . . ?
C11' C1' C2' 120.94(19) . . ?
C5' O2' C6' 117.35(17) . . ?
C14' C2' C1' 118.6(2) . . ?
C14' C2' C3' 121.96(18) . . ?
C1' C2' C3' 119.45(18) . . ?
C8' O3' C7' 117.83(16) . . ?
C2' C3' C4' 115.65(18) . . ?
C15' C4' C5' 118.0(2) . . ?
C15' C4' C3' 121.6(2) . . ?
C5' C4' C3' 120.36(19) . . ?
O2' C5' C18' 123.2(2) . . ?
O2' C5' C4' 115.8(2) . . ?
C18' C5' C4' 121.0(2) . . ?
O2' C6' C7' 106.86(19) . 2_666 ?
O3' C7' C6' 108.21(17) . 2_666 ?
O3' C8' C19' 124.38(19) . . ?
O3' C8' C9' 114.84(18) . . ?
C19' C8' C9' 120.78(19) . . ?
C22' C9' C8' 117.9(2) . . ?
C22' C9' C10' 123.87(19) . . ?
C8' C9' C10' 118.25(19) . . ?
C11' C10' C9' 115.89(18) . . ?
C1' C11' C12' 118.31(19) . . ?
C1' C11' C10' 121.58(19) . . ?
C12' C11' C10' 120.1(2) . . ?
C13' C12' C11' 121.7(2) . . ?
C12' C13' C14' 119.4(2) . . ?
C13' C14' C2' 120.96(19) . . ?
C4' C15' C16' 121.5(2) . . ?
C17' C16' C15' 119.9(2) . . ?
C16' C17' C18' 120.0(2) . . ?
C5' C18' C17' 119.7(2) . . ?
C20' C19' C8' 119.3(2) . . ?
C21' C20' C19' 120.9(2) . . ?
C20' C21' C22' 119.4(2) . . ?
C9' C22' C21' 121.7(2) . . ?
N1 C1G C2G 111.93(19) . . ?
C1G C2G C3G 110.67(19) . . ?
N2 C3G C2G 111.77(19) . . ?
Cl1 C1Z Cl3 111.31(13) . . ?
Cl1 C1Z Cl2 110.76(16) . . ?
Cl3 C1Z Cl2 110.19(14) . . ?
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
O1 C1 1.357(3) . ?
C1 C2 1.403(3) . ?
C1 C11 1.406(3) . ?
O2 C5 1.375(3) . ?
O2 C6 1.428(2) . ?
C2 C14 1.395(3) . ?
C2 C3 1.503(3) . ?
O3 C8 1.373(3) . ?
O3 C7 1.434(2) . ?
C3 C4 1.522(3) . ?
C4 C15 1.375(3) . ?
C4 C5 1.405(3) . ?
C5 C18 1.381(3) . ?
C6 C7 1.494(3) 2_676 ?
C7 C6 1.494(3) 2_676 ?
C8 C19 1.392(3) . ?
C8 C9 1.403(3) . ?
C9 C22 1.382(3) . ?
C9 C10 1.506(3) . ?
C10 C11 1.510(3) . ?
C11 C12 1.388(3) . ?
C12 C13 1.386(3) . ?
C13 C14 1.384(3) . ?
C15 C16 1.387(3) . ?
C16 C17 1.384(3) . ?
C17 C18 1.383(3) . ?
C19 C20 1.386(3) . ?
C20 C21 1.379(3) . ?
C21 C22 1.387(3) . ?
O1' C1' 1.362(2) . ?
C1' C11' 1.396(3) . ?
C1' C2' 1.407(3) . ?
O2' C5' 1.378(3) . ?
O2' C6' 1.436(3) . ?
C2' C14' 1.396(3) . ?
C2' C3' 1.511(3) . ?
O3' C8' 1.366(2) . ?
O3' C7' 1.430(2) . ?
C3' C4' 1.517(3) . ?
C4' C15' 1.385(3) . ?
C4' C5' 1.402(3) . ?
C5' C18' 1.388(3) . ?
C6' C7' 1.501(3) 2_666 ?
C7' C6' 1.501(3) 2_666 ?
C8' C19' 1.390(3) . ?
C8' C9' 1.411(3) . ?
C9' C22' 1.378(3) . ?
C9' C10' 1.514(3) . ?
C10' C11' 1.507(3) . ?
C11' C12' 1.399(3) . ?
C12' C13' 1.375(3) . ?
C13' C14' 1.390(3) . ?
C15' C16' 1.386(4) . ?
C16' C17' 1.380(3) . ?
C17' C18' 1.390(3) . ?
C19' C20' 1.388(3) . ?
C20' C21' 1.370(3) . ?
C21' C22' 1.395(3) . ?
N1 C1G 1.476(3) . ?
C1G C2G 1.509(3) . ?
C2G C3G 1.516(3) . ?
C3G N2 1.469(3) . ?
C1Z Cl1 1.744(3) . ?
C1Z Cl3 1.748(2) . ?
C1Z Cl2 1.766(3) . ?
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
_geom_torsion_publ_flag
O1 C1 C2 C14 -178.5(2) . . . . ?
C11 C1 C2 C14 3.9(3) . . . . ?
O1 C1 C2 C3 3.8(3) . . . . ?
C11 C1 C2 C3 -173.8(2) . . . . ?
C14 C2 C3 C4 89.4(3) . . . . ?
C1 C2 C3 C4 -93.0(3) . . . . ?
C2 C3 C4 C15 -2.6(3) . . . . ?
C2 C3 C4 C5 178.68(19) . . . . ?
C6 O2 C5 C18 0.8(3) . . . . ?
C6 O2 C5 C4 -179.69(18) . . . . ?
C15 C4 C5 O2 178.41(19) . . . . ?
C3 C4 C5 O2 -2.8(3) . . . . ?
C15 C4 C5 C18 -2.1(3) . . . . ?
C3 C4 C5 C18 176.7(2) . . . . ?
C5 O2 C6 C7 168.47(18) . . . 2_676 ?
C8 O3 C7 C6 -174.45(17) . . . 2_676 ?
C7 O3 C8 C19 6.7(3) . . . . ?
C7 O3 C8 C9 -172.98(17) . . . . ?
O3 C8 C9 C22 179.40(19) . . . . ?
C19 C8 C9 C22 -0.3(3) . . . . ?
O3 C8 C9 C10 1.0(3) . . . . ?
C19 C8 C9 C10 -178.64(19) . . . . ?
C22 C9 C10 C11 29.8(3) . . . . ?
C8 C9 C10 C11 -151.91(19) . . . . ?
O1 C1 C11 C12 178.5(2) . . . . ?
C2 C1 C11 C12 -3.7(3) . . . . ?
O1 C1 C11 C10 -1.1(3) . . . . ?
C2 C1 C11 C10 176.6(2) . . . . ?
C9 C10 C11 C12 -102.2(2) . . . . ?
C9 C10 C11 C1 77.5(3) . . . . ?
C1 C11 C12 C13 0.9(3) . . . . ?
C10 C11 C12 C13 -179.5(2) . . . . ?
C11 C12 C13 C14 1.7(4) . . . . ?
C12 C13 C14 C2 -1.4(4) . . . . ?
C1 C2 C14 C13 -1.3(3) . . . . ?
C3 C2 C14 C13 176.4(2) . . . . ?
C5 C4 C15 C16 1.0(3) . . . . ?
C3 C4 C15 C16 -177.7(2) . . . . ?
C4 C15 C16 C17 0.9(4) . . . . ?
C15 C16 C17 C18 -1.7(4) . . . . ?
C16 C17 C18 C5 0.7(3) . . . . ?
O2 C5 C18 C17 -179.3(2) . . . . ?
C4 C5 C18 C17 1.3(3) . . . . ?
O3 C8 C19 C20 -178.62(19) . . . . ?
C9 C8 C19 C20 1.0(3) . . . . ?
C8 C19 C20 C21 -0.5(3) . . . . ?
C19 C20 C21 C22 -0.7(3) . . . . ?
C8 C9 C22 C21 -1.0(3) . . . . ?
C10 C9 C22 C21 177.3(2) . . . . ?
C20 C21 C22 C9 1.5(4) . . . . ?
O1' C1' C2' C14' 179.47(19) . . . . ?
C11' C1' C2' C14' 2.5(3) . . . . ?
O1' C1' C2' C3' 0.4(3) . . . . ?
C11' C1' C2' C3' -176.5(2) . . . . ?
C14' C2' C3' C4' 95.8(2) . . . . ?
C1' C2' C3' C4' -85.2(2) . . . . ?
C2' C3' C4' C15' -39.7(3) . . . . ?
C2' C3' C4' C5' 144.32(19) . . . . ?
C6' O2' C5' C18' -1.9(3) . . . . ?
C6' O2' C5' C4' 176.76(18) . . . . ?
C15' C4' C5' O2' 179.78(18) . . . . ?
C3' C4' C5' O2' -4.1(3) . . . . ?
C15' C4' C5' C18' -1.5(3) . . . . ?
C3' C4' C5' C18' 174.62(19) . . . . ?
C5' O2' C6' C7' -179.75(16) . . . 2_666 ?
C8' O3' C7' C6' -175.52(18) . . . 2_666 ?
C7' O3' C8' C19' 6.0(3) . . . . ?
C7' O3' C8' C9' -173.58(19) . . . . ?
O3' C8' C9' C22' -177.26(19) . . . . ?
C19' C8' C9' C22' 3.1(3) . . . . ?
O3' C8' C9' C10' 4.5(3) . . . . ?
C19' C8' C9' C10' -175.1(2) . . . . ?
C22' C9' C10' C11' 3.8(3) . . . . ?
C8' C9' C10' C11' -178.1(2) . . . . ?
O1' C1' C11' C12' -178.9(2) . . . . ?
C2' C1' C11' C12' -2.1(3) . . . . ?
O1' C1' C11' C10' -0.1(3) . . . . ?
C2' C1' C11' C10' 176.6(2) . . . . ?
C9' C10' C11' C1' 99.0(2) . . . . ?
C9' C10' C11' C12' -82.3(3) . . . . ?
C1' C11' C12' C13' 0.1(3) . . . . ?
C10' C11' C12' C13' -178.6(2) . . . . ?
C11' C12' C13' C14' 1.4(3) . . . . ?
C12' C13' C14' C2' -1.0(3) . . . . ?
C1' C2' C14' C13' -0.9(3) . . . . ?
C3' C2' C14' C13' 178.1(2) . . . . ?
C5' C4' C15' C16' 0.6(3) . . . . ?
C3' C4' C15' C16' -175.5(2) . . . . ?
C4' C15' C16' C17' 0.9(4) . . . . ?
C15' C16' C17' C18' -1.5(4) . . . . ?
O2' C5' C18' C17' 179.57(19) . . . . ?
C4' C5' C18' C17' 1.0(3) . . . . ?
C16' C17' C18' C5' 0.6(3) . . . . ?
O3' C8' C19' C20' 177.8(2) . . . . ?
C9' C8' C19' C20' -2.6(3) . . . . ?
C8' C19' C20' C21' 0.3(4) . . . . ?
C19' C20' C21' C22' 1.4(4) . . . . ?
C8' C9' C22' C21' -1.4(3) . . . . ?
C10' C9' C22' C21' 176.7(2) . . . . ?
C20' C21' C22' C9' -0.8(4) . . . . ?
N1 C1G C2G C3G 169.30(19) . . . . ?
C1G C2G C3G N2 173.09(19) . . . . ?
