#------------------------------------------------------------------------------
#$Date: 2017-06-29 11:01:09 +0300 (Thu, 29 Jun 2017) $
#$Revision: 198233 $
#$URL: file:///home/coder/svn-repositories/cod/cif/7/20/50/7205068.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_7205068
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 H39 O6,C4 H13 N2,C1 H1 Cl3'
_chemical_formula_sum            'C49 H53 Cl3 N2 O6'
_chemical_formula_weight         872.28
_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) butylenediamine hemi-salt
;
_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) butylenediamine hemi-salt
;
_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                114.863(1)
_cell_angle_beta                 91.742(1)
_cell_angle_gamma                109.327(1)
_cell_formula_units_Z            2
_cell_length_a                   12.8654(2)
_cell_length_b                   14.0595(2)
_cell_length_c                   14.5748(3)
_cell_measurement_temperature    123(2)
_cell_volume                     2212.46(7)
_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 0.981
_diffrn_measured_fraction_theta_max 0.981
_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  0.1196
_diffrn_reflns_av_sigmaI/netI    0.1693
_diffrn_reflns_limit_h_max       16
_diffrn_reflns_limit_h_min       -16
_diffrn_reflns_limit_k_max       18
_diffrn_reflns_limit_k_min       -18
_diffrn_reflns_limit_l_max       19
_diffrn_reflns_limit_l_min       -19
_diffrn_reflns_number            36591
_diffrn_reflns_theta_full        27.95
_diffrn_reflns_theta_max         27.95
_diffrn_reflns_theta_min         2.54
_exptl_absorpt_coefficient_mu    0.259
_exptl_absorpt_correction_type   none
_exptl_crystal_colour            colourless
_exptl_crystal_density_diffrn    1.309
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       needles
_exptl_crystal_F_000             920
_exptl_crystal_size_max          0.48
_exptl_crystal_size_mid          0.35
_exptl_crystal_size_min          0.25
_refine_diff_density_max         0.616
_refine_diff_density_min         -0.809
_refine_diff_density_rms         0.071
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.023
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     585
_refine_ls_number_reflns         10438
_refine_ls_number_restraints     20
_refine_ls_restrained_S_all      1.050
_refine_ls_R_factor_all          0.2151
_refine_ls_R_factor_gt           0.0772
_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)+(0.0952P)²+0.0000P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1640
_refine_ls_wR_factor_ref         0.2137
_reflns_number_gt                4440
_reflns_number_total             10438
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            C003571H.TXT
_cod_data_source_block           1c
_cod_original_cell_volume        2212.46(9)
_cod_database_code               7205068
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 0.0655(2) 0.4695(2) 0.37051(18) 0.0368(7) Uani 1 1 d . . .
H1O H -0.019(4) 0.423(4) 0.373(4) 0.083(16) Uiso 1 1 d . . .
C1 C 0.0805(3) 0.4598(3) 0.2752(3) 0.0264(8) Uani 1 1 d . . .
O2 O 0.34929(19) 0.44672(19) 0.49263(18) 0.0295(6) Uani 1 1 d . . .
C2 C 0.1846(3) 0.4594(3) 0.2500(3) 0.0255(8) Uani 1 1 d . . .
O3 O -0.31370(18) 0.4401(2) 0.29542(19) 0.0309(6) Uani 1 1 d . . .
C3 C 0.2735(3) 0.4681(3) 0.3267(3) 0.0297(9) Uani 1 1 d . . .
H3A H 0.2602 0.5081 0.3968 0.036 Uiso 1 1 calc R . .
H3B H 0.3475 0.5161 0.3224 0.036 Uiso 1 1 calc R . .
C4 C 0.2804(3) 0.3571(3) 0.3144(3) 0.0260(8) Uani 1 1 d . . .
C5 C 0.3237(3) 0.3517(3) 0.4008(3) 0.0254(8) Uani 1 1 d . . .
C6 C 0.3958(3) 0.4462(3) 0.5834(3) 0.0295(9) Uani 1 1 d . . .
H6A H 0.4667 0.4330 0.5751 0.035 Uiso 1 1 calc R . .
H6B H 0.3423 0.3852 0.5953 0.035 Uiso 1 1 calc R . .
C7 C -0.4175(3) 0.4407(3) 0.3276(3) 0.0303(9) Uani 1 1 d . . .
H7A H -0.4489 0.3801 0.3485 0.036 Uiso 1 1 calc R . .
H7B H -0.4726 0.4267 0.2699 0.036 Uiso 1 1 calc R . .
C8 C -0.3121(3) 0.3388(3) 0.2250(3) 0.0269(8) Uani 1 1 d . . .
C9 C -0.2083(3) 0.3434(3) 0.1951(3) 0.0271(9) Uani 1 1 d . . .
C10 C -0.1132(3) 0.4585(3) 0.2342(3) 0.0306(9) Uani 1 1 d . . .
H10C H -0.1359 0.5031 0.2060 0.037 Uiso 1 1 calc R . .
H10D H -0.1031 0.4987 0.3103 0.037 Uiso 1 1 calc R . .
C11 C -0.0018(3) 0.4560(3) 0.2075(3) 0.0262(8) Uani 1 1 d . . .
C12 C 0.0224(3) 0.4509(3) 0.1131(3) 0.0300(9) Uani 1 1 d . . .
H12 H -0.0329 0.4478 0.0659 0.036 Uiso 1 1 calc R . .
C13 C 0.1244(3) 0.4503(3) 0.0864(3) 0.0328(9) Uani 1 1 d . . .
H13 H 0.1392 0.4465 0.0218 0.039 Uiso 1 1 calc R . .
C14 C 0.2043(3) 0.4554(3) 0.1554(3) 0.0303(9) Uani 1 1 d . . .
H14 H 0.2750 0.4563 0.1378 0.036 Uiso 1 1 calc R . .
C15 C 0.2518(3) 0.2627(3) 0.2194(3) 0.0342(9) Uani 1 1 d . . .
H15 H 0.2203 0.2643 0.1605 0.041 Uiso 1 1 calc R . .
C16 C 0.2679(3) 0.1657(3) 0.2082(3) 0.0373(10) Uani 1 1 d . . .
H16 H 0.2482 0.1019 0.1423 0.045 Uiso 1 1 calc R . .
C17 C 0.3130(3) 0.1632(3) 0.2939(3) 0.0347(10) Uani 1 1 d . . .
H17 H 0.3251 0.0975 0.2867 0.042 Uiso 1 1 calc R . .
C18 C 0.3406(3) 0.2550(3) 0.3897(3) 0.0308(9) Uani 1 1 d . . .
H18 H 0.3711 0.2523 0.4484 0.037 Uiso 1 1 calc R . .
C19 C -0.4034(3) 0.2365(3) 0.1860(3) 0.0315(9) Uani 1 1 d . . .
H19 H -0.4739 0.2341 0.2051 0.038 Uiso 1 1 calc R . .
C20 C -0.3911(3) 0.1379(3) 0.1192(3) 0.0392(10) Uani 1 1 d . . .
H20 H -0.4534 0.0677 0.0926 0.047 Uiso 1 1 calc R . .
C21 C -0.2894(3) 0.1403(3) 0.0907(3) 0.0399(10) Uani 1 1 d . . .
H21 H -0.2813 0.0722 0.0454 0.048 Uiso 1 1 calc R . .
C22 C -0.1991(3) 0.2430(3) 0.1288(3) 0.0341(10) Uani 1 1 d . . .
H22 H -0.1291 0.2444 0.1089 0.041 Uiso 1 1 calc R . .
O1' O -0.15355(18) -0.08457(19) 0.41390(18) 0.0309(6) Uani 1 1 d . . .
C1' C -0.2488(3) -0.1704(3) 0.3586(3) 0.0249(8) Uani 1 1 d . . .
O2' O -0.2602(2) 0.1460(2) 0.64509(18) 0.0342(6) Uani 1 1 d . . .
C2' C -0.3519(3) -0.1703(3) 0.3894(3) 0.0246(8) Uani 1 1 d . . .
O3' O 0.06879(19) -0.2355(2) 0.19874(19) 0.0347(6) Uani 1 1 d . . .
C3' C -0.3523(3) -0.0706(3) 0.4858(3) 0.0251(8) Uani 1 1 d . . .
H3'1 H -0.2856 -0.0455 0.5384 0.030 Uiso 1 1 calc R . .
H3'2 H -0.4197 -0.0965 0.5132 0.030 Uiso 1 1 calc R . .
C4' C -0.3515(3) 0.0306(3) 0.4717(3) 0.0245(8) Uani 1 1 d . . .
C5' C -0.3074(3) 0.1390(3) 0.5550(3) 0.0258(8) Uani 1 1 d . . .
C6' C -0.2285(3) 0.2500(3) 0.7372(3) 0.0330(9) Uani 1 1 d . . .
H6'1 H -0.2951 0.2689 0.7554 0.040 Uiso 1 1 calc R . .
H6'2 H -0.1736 0.3124 0.7281 0.040 Uiso 1 1 calc R . .
C7' C 0.1768(3) -0.2331(3) 0.1798(3) 0.0321(9) Uani 1 1 d . . .
H7'1 H 0.2232 -0.1594 0.1829 0.039 Uiso 1 1 calc R . .
H7'2 H 0.1707 -0.2942 0.1108 0.039 Uiso 1 1 calc R . .
C8' C 0.0114(3) -0.1971(3) 0.1511(3) 0.0286(9) Uani 1 1 d . . .
C9' C -0.0971(3) -0.2081(3) 0.1729(3) 0.0260(8) Uani 1 1 d . . .
C10' C -0.1420(3) -0.2705(3) 0.2356(3) 0.0295(9) Uani 1 1 d . . .
H10A H -0.1531 -0.3510 0.1942 0.035 Uiso 1 1 calc R . .
H10B H -0.0839 -0.2390 0.2979 0.035 Uiso 1 1 calc R . .
C11' C -0.2498(3) -0.2654(3) 0.2692(3) 0.0251(8) Uani 1 1 d . . .
C12' C -0.3513(3) -0.3555(3) 0.2133(3) 0.0289(9) Uani 1 1 d . . .
H12' H -0.3513 -0.4192 0.1536 0.035 Uiso 1 1 calc R . .
C13' C -0.4522(3) -0.3536(3) 0.2433(3) 0.0305(9) Uani 1 1 d . . .
H13' H -0.5210 -0.4149 0.2043 0.037 Uiso 1 1 calc R . .
C14' C -0.4509(3) -0.2605(3) 0.3312(3) 0.0287(9) Uani 1 1 d . . .
H14' H -0.5198 -0.2589 0.3520 0.034 Uiso 1 1 calc R . .
C15' C -0.3995(3) 0.0196(3) 0.3795(3) 0.0325(9) Uani 1 1 d . . .
H15' H -0.4293 -0.0532 0.3215 0.039 Uiso 1 1 calc R . .
C16' C -0.4055(3) 0.1118(3) 0.3694(3) 0.0375(10) Uani 1 1 d . . .
H16' H -0.4392 0.1016 0.3053 0.045 Uiso 1 1 calc R . .
C17' C -0.3624(3) 0.2180(3) 0.4528(3) 0.0345(10) Uani 1 1 d . . .
H17' H -0.3674 0.2811 0.4466 0.041 Uiso 1 1 calc R . .
C18' C -0.3114(3) 0.2328(3) 0.5459(3) 0.0297(9) Uani 1 1 d . . .
H18' H -0.2795 0.3062 0.6030 0.036 Uiso 1 1 calc R . .
C19' C 0.0539(3) -0.1484(3) 0.0883(3) 0.0323(9) Uani 1 1 d . . .
H19' H 0.1268 -0.1414 0.0739 0.039 Uiso 1 1 calc R . .
C20' C -0.0115(3) -0.1100(3) 0.0471(3) 0.0424(11) Uani 1 1 d . . .
H20' H 0.0163 -0.0782 0.0025 0.051 Uiso 1 1 calc R . .
C21' C -0.1159(3) -0.1168(3) 0.0693(3) 0.0427(11) Uani 1 1 d . . .
H21' H -0.1593 -0.0885 0.0414 0.051 Uiso 1 1 calc R . .
C22' C -0.1577(3) -0.1655(3) 0.1328(3) 0.0337(9) Uani 1 1 d . . .
H22' H -0.2295 -0.1693 0.1488 0.040 Uiso 1 1 calc R . .
Cl1A Cl -0.4318(3) -0.3230(3) -0.0482(2) 0.0594(10) Uiso 0.50 1 d PD A 5
Cl2A Cl -0.4641(4) -0.1395(3) 0.1014(3) 0.0473(10) Uiso 0.35 1 d PD A 5
Cl3A Cl -0.6450(3) -0.3630(5) 0.0176(3) 0.0422(11) Uiso 0.35 1 d PD A 5
Cl2B Cl -0.5197(8) -0.1574(5) 0.1098(6) 0.066(3) Uiso 0.15 1 d PD B 6
Cl3B Cl -0.6418(6) -0.3906(6) 0.0309(7) 0.053(3) Uiso 0.15 1 d PD C 6
Cl1C Cl -0.4334(2) -0.3524(2) -0.0418(2) 0.0418(8) Uiso 0.50 1 d PD D 2
Cl2C Cl -0.4239(2) -0.1237(2) 0.08901(19) 0.0507(8) Uiso 0.50 1 d PD D 2
Cl3C Cl -0.6261(3) -0.3199(3) 0.0332(3) 0.0629(10) Uiso 0.50 1 d P D 2
N1 N -0.1144(3) 0.3570(3) 0.4072(3) 0.0421(9) Uani 1 1 d . . .
H1NA H -0.116(3) 0.400(3) 0.476(3) 0.037(11) Uiso 1 1 d . . .
H1NB H -0.185(5) 0.330(4) 0.364(4) 0.10(2) Uiso 1 1 d . . .
N2 N 0.0503(3) 0.0053(4) 0.3898(3) 0.0423(10) Uani 1 1 d . . .
H2NC H -0.037(4) -0.043(4) 0.394(4) 0.086(16) Uiso 1 1 d . . .
H2NB H 0.069(3) -0.037(3) 0.346(3) 0.034(13) Uiso 1 1 d . . .
H2NA H 0.104(4) 0.037(3) 0.454(4) 0.053(13) Uiso 1 1 d . . .
C1G C -0.0973(4) 0.2533(5) 0.3920(4) 0.0363(13) Uani 0.80 1 d P E 3
H1G1 H -0.0879 0.2130 0.3204 0.044 Uiso 0.80 1 calc PR E 3
H1G2 H -0.1635 0.2021 0.4038 0.044 Uiso 0.80 1 calc PR E 3
C2G C 0.0075(5) 0.2863(5) 0.4681(4) 0.0439(14) Uani 0.80 1 d P E 3
H2G1 H 0.0744 0.3258 0.4474 0.053 Uiso 0.80 1 calc PR E 3
H2G2 H 0.0038 0.3402 0.5374 0.053 Uiso 0.80 1 calc PR E 3
C3G C 0.0213(5) 0.1870(5) 0.4742(5) 0.0411(17) Uani 0.80 1 d P E 3
H3G1 H -0.0467 0.1463 0.4928 0.049 Uiso 0.80 1 calc PR E 3
H3G2 H 0.0859 0.2156 0.5302 0.049 Uiso 0.80 1 calc PR E 3
C4G C 0.0400(6) 0.1046(8) 0.3756(7) 0.0372(18) Uani 0.80 1 d P E 3
H4G1 H 0.1096 0.1434 0.3575 0.045 Uiso 0.80 1 calc PR E 3
H4G2 H -0.0237 0.0757 0.3187 0.045 Uiso 0.80 1 calc PR E 3
C5G C -0.5025(6) -0.2863(5) 0.0539(8) 0.069(5) Uiso 0.50 1 d PD A 5
H5G H -0.4718 -0.3005 0.1087 0.083 Uiso 0.50 1 calc PR A 5
C1G' C -0.055(3) 0.306(2) 0.463(2) 0.055(7) Uiso 0.20 1 d P E 4
H1G3 H 0.0119 0.3674 0.5152 0.066 Uiso 0.20 1 calc PR E 4
H1G4 H -0.1078 0.2709 0.4980 0.066 Uiso 0.20 1 calc PR E 4
C2G' C -0.022(2) 0.223(2) 0.385(2) 0.064(7) Uiso 0.20 1 d P E 4
H2G3 H 0.0416 0.2612 0.3609 0.077 Uiso 0.20 1 calc PR E 4
H2G4 H -0.0856 0.1722 0.3257 0.077 Uiso 0.20 1 calc PR E 4
C3G' C 0.014(3) 0.147(3) 0.428(3) 0.047(9) Uiso 0.20 1 d P E 4
H3G3 H 0.0769 0.1976 0.4883 0.056 Uiso 0.20 1 calc PR E 4
H3G4 H -0.0500 0.1073 0.4513 0.056 Uiso 0.20 1 calc PR E 4
C4G' C 0.047(4) 0.068(4) 0.351(4) 0.064(15) Uiso 0.20 1 d P E 4
H4G3 H -0.0085 0.0265 0.2857 0.077 Uiso 0.20 1 calc PR E 4
H4G4 H 0.1217 0.1053 0.3392 0.077 Uiso 0.20 1 calc PR E 4
C5G' C -0.4794(9) -0.2668(5) 0.0608(6) 0.036(3) Uiso 0.50 1 d PD D 2
H5G' H -0.4553 -0.2726 0.1235 0.043 Uiso 0.50 1 calc PR D 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'
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 C11 121.7(3) . . ?
O1 C1 C2 117.0(3) . . ?
C11 C1 C2 121.2(3) . . ?
C5 O2 C6 117.9(3) . . ?
C14 C2 C1 118.2(3) . . ?
C14 C2 C3 121.9(3) . . ?
C1 C2 C3 119.9(3) . . ?
C8 O3 C7 117.6(2) . . ?
C2 C3 C4 116.8(3) . . ?
C15 C4 C5 118.3(3) . . ?
C15 C4 C3 122.2(3) . . ?
C5 C4 C3 119.4(3) . . ?
O2 C5 C18 123.9(3) . . ?
O2 C5 C4 115.8(3) . . ?
C18 C5 C4 120.4(3) . . ?
O2 C6 C7 107.4(3) . 2_566 ?
O3 C7 C6 108.5(3) . 2_566 ?
O3 C8 C19 124.2(3) . . ?
O3 C8 C9 115.2(3) . . ?
C19 C8 C9 120.6(3) . . ?
C22 C9 C8 118.2(3) . . ?
C22 C9 C10 123.2(3) . . ?
C8 C9 C10 118.6(3) . . ?
C11 C10 C9 115.6(3) . . ?
C12 C11 C1 118.0(3) . . ?
C12 C11 C10 120.1(3) . . ?
C1 C11 C10 121.9(3) . . ?
C13 C12 C11 121.8(3) . . ?
C14 C13 C12 118.8(3) . . ?
C13 C14 C2 122.0(3) . . ?
C4 C15 C16 121.5(4) . . ?
C17 C16 C15 119.3(4) . . ?
C18 C17 C16 120.6(4) . . ?
C17 C18 C5 120.0(4) . . ?
C20 C19 C8 119.5(3) . . ?
C21 C20 C19 120.8(3) . . ?
C20 C21 C22 119.4(4) . . ?
C9 C22 C21 121.5(4) . . ?
O1' C1' C2' 120.4(3) . . ?
O1' C1' C11' 121.1(3) . . ?
C2' C1' C11' 118.5(3) . . ?
C5' O2' C6' 118.7(3) . . ?
C14' C2' C1' 119.9(3) . . ?
C14' C2' C3' 120.9(3) . . ?
C1' C2' C3' 119.3(3) . . ?
C8' O3' C7' 119.7(3) . . ?
C2' C3' C4' 115.4(3) . . ?
C15' C4' C5' 117.4(3) . . ?
C15' C4' C3' 122.4(3) . . ?
C5' C4' C3' 120.1(3) . . ?
O2' C5' C4' 115.4(3) . . ?
O2' C5' C18' 123.2(3) . . ?
C4' C5' C18' 121.4(3) . . ?
O2' C6' C7' 106.5(3) . 2_556 ?
O3' C7' C6' 106.2(3) . 2_556 ?
O3' C8' C19' 124.5(3) . . ?
O3' C8' C9' 114.4(3) . . ?
C19' C8' C9' 121.0(4) . . ?
C22' C9' C8' 118.1(3) . . ?
C22' C9' C10' 123.6(3) . . ?
C8' C9' C10' 118.3(3) . . ?
C11' C10' C9' 116.0(3) . . ?
C12' C11' C1' 119.9(3) . . ?
C12' C11' C10' 119.9(3) . . ?
C1' C11' C10' 120.2(3) . . ?
C13' C12' C11' 121.1(3) . . ?
C12' C13' C14' 118.9(3) . . ?
C2' C14' C13' 121.7(3) . . ?
C4' C15' C16' 122.1(3) . . ?
C17' C16' C15' 119.7(4) . . ?
C16' C17' C18' 119.9(4) . . ?
C17' C18' C5' 119.6(3) . . ?
C20' C19' C8' 118.9(4) . . ?
C21' C20' C19' 121.3(4) . . ?
C20' C21' C22' 119.4(4) . . ?
C9' C22' C21' 121.3(4) . . ?
C1G N1 C1G' 37.1(10) . . ?
C4G' N2 C4G 18(2) . . ?
N1 C1G C2G 108.6(5) . . ?
C3G C2G C1G 113.4(4) . . ?
C2G C3G C4G 113.9(6) . . ?
C3G C4G N2 109.5(5) . . ?
Cl3A C5G Cl1A 112.9(5) . . ?
Cl3A C5G Cl2A 114.4(5) . . ?
Cl1A C5G Cl2A 103.9(4) . . ?
C2G' C1G' N1 108(2) . . ?
C1G' C2G' C3G' 112(3) . . ?
C4G' C3G' C2G' 111(4) . . ?
N2 C4G' C3G' 102(4) . . ?
Cl1C C5G' Cl3C 108.6(5) . . ?
Cl1C C5G' Cl2C 113.7(5) . . ?
Cl3C C5G' Cl2C 110.7(5) . . ?
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 1.363(4) . ?
C1 C11 1.398(5) . ?
C1 C2 1.400(5) . ?
O2 C5 1.365(4) . ?
O2 C6 1.439(4) . ?
C2 C14 1.390(5) . ?
C2 C3 1.512(5) . ?
O3 C8 1.368(4) . ?
O3 C7 1.431(4) . ?
C3 C4 1.529(5) . ?
C4 C15 1.383(5) . ?
C4 C5 1.401(5) . ?
C5 C18 1.392(5) . ?
C6 C7 1.496(5) 2_566 ?
C7 C6 1.496(5) 2_566 ?
C8 C19 1.389(5) . ?
C8 C9 1.406(5) . ?
C9 C22 1.384(5) . ?
C9 C10 1.520(5) . ?
C10 C11 1.504(5) . ?
C11 C12 1.398(5) . ?
C12 C13 1.381(5) . ?
C13 C14 1.380(5) . ?
C15 C16 1.391(5) . ?
C16 C17 1.380(5) . ?
C17 C18 1.376(5) . ?
C19 C20 1.384(5) . ?
C20 C21 1.379(5) . ?
C21 C22 1.385(5) . ?
O1' C1' 1.323(4) . ?
C1' C2' 1.414(5) . ?
C1' C11' 1.417(5) . ?
O2' C5' 1.380(4) . ?
O2' C6' 1.424(4) . ?
C2' C14' 1.382(5) . ?
C2' C3' 1.512(5) . ?
O3' C8' 1.366(4) . ?
O3' C7' 1.417(4) . ?
C3' C4' 1.517(5) . ?
C4' C15' 1.387(5) . ?
C4' C5' 1.396(5) . ?
C5' C18' 1.397(5) . ?
C6' C7' 1.503(5) 2_556 ?
C7' C6' 1.503(5) 2_556 ?
C8' C19' 1.384(5) . ?
C8' C9' 1.414(5) . ?
C9' C22' 1.372(5) . ?
C9' C10' 1.520(5) . ?
C10' C11' 1.499(5) . ?
C11' C12' 1.395(5) . ?
C12' C13' 1.387(5) . ?
C13' C14' 1.389(5) . ?
C15' C16' 1.391(5) . ?
C16' C17' 1.378(5) . ?
C17' C18' 1.391(5) . ?
C19' C20' 1.379(5) . ?
C20' C21' 1.374(6) . ?
C21' C22' 1.391(5) . ?
Cl1A C5G 1.748(6) . ?
Cl2A C5G 1.757(6) . ?
Cl3A C5G 1.719(7) . ?
Cl1C C5G' 1.746(6) . ?
Cl2C C5G' 1.750(6) . ?
Cl3C C5G' 1.746(11) . ?
N1 C1G 1.471(6) . ?
N1 C1G' 1.60(3) . ?
N2 C4G' 1.24(5) . ?
N2 C4G 1.541(10) . ?
C1G C2G 1.525(7) . ?
C2G C3G 1.503(8) . ?
C3G C4G 1.507(11) . ?
C1G' C2G' 1.44(4) . ?
C2G' C3G' 1.61(4) . ?
C3G' C4G' 1.40(5) . ?
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 -176.7(3) . . . . ?
C11 C1 C2 C14 0.2(5) . . . . ?
O1 C1 C2 C3 0.7(5) . . . . ?
C11 C1 C2 C3 177.6(3) . . . . ?
C14 C2 C3 C4 -86.8(4) . . . . ?
C1 C2 C3 C4 95.9(4) . . . . ?
C2 C3 C4 C15 30.3(5) . . . . ?
C2 C3 C4 C5 -153.8(3) . . . . ?
C6 O2 C5 C18 -0.5(4) . . . . ?
C6 O2 C5 C4 -179.0(3) . . . . ?
C15 C4 C5 O2 -179.3(3) . . . . ?
C3 C4 C5 O2 4.6(4) . . . . ?
C15 C4 C5 C18 2.1(5) . . . . ?
C3 C4 C5 C18 -174.0(3) . . . . ?
C5 O2 C6 C7 179.3(3) . . . 2_566 ?
C8 O3 C7 C6 170.4(3) . . . 2_566 ?
C7 O3 C8 C19 -2.5(5) . . . . ?
C7 O3 C8 C9 179.1(3) . . . . ?
O3 C8 C9 C22 176.3(3) . . . . ?
C19 C8 C9 C22 -2.2(5) . . . . ?
O3 C8 C9 C10 -5.6(5) . . . . ?
C19 C8 C9 C10 175.9(3) . . . . ?
C22 C9 C10 C11 -7.6(5) . . . . ?
C8 C9 C10 C11 174.4(3) . . . . ?
O1 C1 C11 C12 177.3(3) . . . . ?
C2 C1 C11 C12 0.5(5) . . . . ?
O1 C1 C11 C10 -2.2(5) . . . . ?
C2 C1 C11 C10 -178.9(3) . . . . ?
C9 C10 C11 C12 85.9(4) . . . . ?
C9 C10 C11 C1 -94.7(4) . . . . ?
C1 C11 C12 C13 -0.5(5) . . . . ?
C10 C11 C12 C13 179.0(3) . . . . ?
C11 C12 C13 C14 -0.3(5) . . . . ?
C12 C13 C14 C2 1.0(5) . . . . ?
C1 C2 C14 C13 -0.9(5) . . . . ?
C3 C2 C14 C13 -178.3(3) . . . . ?
C5 C4 C15 C16 -1.8(5) . . . . ?
C3 C4 C15 C16 174.2(3) . . . . ?
C4 C15 C16 C17 0.4(5) . . . . ?
C15 C16 C17 C18 0.7(5) . . . . ?
C16 C17 C18 C5 -0.4(5) . . . . ?
O2 C5 C18 C17 -179.5(3) . . . . ?
C4 C5 C18 C17 -1.1(5) . . . . ?
O3 C8 C19 C20 -176.6(3) . . . . ?
C9 C8 C19 C20 1.7(5) . . . . ?
C8 C19 C20 C21 -0.2(6) . . . . ?
C19 C20 C21 C22 -0.7(6) . . . . ?
C8 C9 C22 C21 1.2(6) . . . . ?
C10 C9 C22 C21 -176.8(3) . . . . ?
C20 C21 C22 C9 0.2(6) . . . . ?
O1' C1' C2' C14' -179.8(3) . . . . ?
C11' C1' C2' C14' -1.4(5) . . . . ?
O1' C1' C2' C3' 0.4(5) . . . . ?
C11' C1' C2' C3' 178.8(3) . . . . ?
C14' C2' C3' C4' -96.7(4) . . . . ?
C1' C2' C3' C4' 83.1(4) . . . . ?
C2' C3' C4' C15' 29.8(5) . . . . ?
C2' C3' C4' C5' -154.1(3) . . . . ?
C6' O2' C5' C4' -170.8(3) . . . . ?
C6' O2' C5' C18' 9.3(5) . . . . ?
C15' C4' C5' O2' -179.9(3) . . . . ?
C3' C4' C5' O2' 3.8(4) . . . . ?
C15' C4' C5' C18' 0.0(5) . . . . ?
C3' C4' C5' C18' -176.3(3) . . . . ?
C5' O2' C6' C7' -178.1(3) . . . 2_556 ?
C8' O3' C7' C6' 165.1(3) . . . 2_556 ?
C7' O3' C8' C19' -4.0(5) . . . . ?
C7' O3' C8' C9' 177.6(3) . . . . ?
O3' C8' C9' C22' 176.3(3) . . . . ?
C19' C8' C9' C22' -2.2(5) . . . . ?
O3' C8' C9' C10' -6.1(4) . . . . ?
C19' C8' C9' C10' 175.4(3) . . . . ?
C22' C9' C10' C11' -10.9(5) . . . . ?
C8' C9' C10' C11' 171.6(3) . . . . ?
O1' C1' C11' C12' 179.0(3) . . . . ?
C2' C1' C11' C12' 0.7(5) . . . . ?
O1' C1' C11' C10' 0.1(5) . . . . ?
C2' C1' C11' C10' -178.2(3) . . . . ?
C9' C10' C11' C12' 98.5(4) . . . . ?
C9' C10' C11' C1' -82.7(4) . . . . ?
C1' C11' C12' C13' 0.4(5) . . . . ?
C10' C11' C12' C13' 179.3(3) . . . . ?
C11' C12' C13' C14' -0.7(5) . . . . ?
C1' C2' C14' C13' 1.2(5) . . . . ?
C3' C2' C14' C13' -179.1(3) . . . . ?
C12' C13' C14' C2' -0.1(5) . . . . ?
C5' C4' C15' C16' -0.8(5) . . . . ?
C3' C4' C15' C16' 175.4(3) . . . . ?
C4' C15' C16' C17' 0.3(6) . . . . ?
C15' C16' C17' C18' 1.1(5) . . . . ?
C16' C17' C18' C5' -1.9(5) . . . . ?
O2' C5' C18' C17' -178.8(3) . . . . ?
C4' C5' C18' C17' 1.3(5) . . . . ?
O3' C8' C19' C20' -178.1(3) . . . . ?
C9' C8' C19' C20' 0.2(5) . . . . ?
C8' C19' C20' C21' 1.6(6) . . . . ?
C19' C20' C21' C22' -1.3(6) . . . . ?
C8' C9' C22' C21' 2.5(5) . . . . ?
C10' C9' C22' C21' -175.0(3) . . . . ?
C20' C21' C22' C9' -0.8(6) . . . . ?
C1G' N1 C1G C2G -21.8(16) . . . . ?
N1 C1G C2G C3G 168.9(4) . . . . ?
C1G C2G C3G C4G 64.7(7) . . . . ?
C2G C3G C4G N2 -178.7(5) . . . . ?
C4G' N2 C4G C3G -179(8) . . . . ?
C1G N1 C1G' C2G' 32.4(15) . . . . ?
N1 C1G' C2G' C3G' -167.7(19) . . . . ?
C1G' C2G' C3G' C4G' -179(3) . . . . ?
C4G N2 C4G' C3G' -7(5) . . . . ?
C2G' C3G' C4G' N2 -168(3) . . . . ?
