#------------------------------------------------------------------------------
#$Date: 2016-02-16 22:30:59 +0200 (Tue, 16 Feb 2016) $
#$Revision: 176467 $
#$URL: svn://www.crystallography.net/cod/cif/4/02/32/4023224.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_4023224
loop_
_publ_author_name
'Clément Bonnot'
'Jean-Claude Chambron'
'Enrique Espinosa'
'Roland Graff'
_publ_section_title
;
 The in, out Asymmetric Pseudo-Triple Helical Form of a D_3h_
 Diaza-Macropentacycle
;
_journal_name_full               'Journal of Organic Chemistry'
_journal_page_first              868
_journal_page_last               881
_journal_paper_doi               10.1021/jo701984z
_journal_volume                  73
_journal_year                    2008
_chemical_formula_moiety         'C44.75 H56.75 Cl0.50 N2.75 O6.50 S4'
_chemical_formula_sum            'C44.75 H56.75 Cl0.5 N2.75 O6.5 S4'
_chemical_formula_weight         883.14
_chemical_name_systematic
;
 ?
;
_space_group_IT_number           2
_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                90.004(1)
_cell_angle_beta                 95.224(1)
_cell_angle_gamma                108.017(1)
_cell_formula_units_Z            2
_cell_length_a                   9.6679(2)
_cell_length_b                   12.5864(2)
_cell_length_c                   19.7850(5)
_cell_measurement_reflns_used    16611
_cell_measurement_temperature    115(2)
_cell_measurement_theta_max      27.36
_cell_measurement_theta_min      2.63
_cell_volume                     2278.94(8)
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_diffrn_ambient_temperature      115(2)
_diffrn_measured_fraction_theta_full 0.994
_diffrn_measured_fraction_theta_max 0.994
_diffrn_measurement_device       '95mm CCD camera on κ-goniostat'
_diffrn_measurement_device_type  KappaCCD
_diffrn_measurement_method       CCD
_diffrn_orient_matrix_type       'by Nonius Collect from scalepack cell'
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_source         'fine-focus sealed tube'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71069
_diffrn_reflns_av_R_equivalents  0.0433
_diffrn_reflns_av_sigmaI/netI    0.0924
_diffrn_reflns_limit_h_max       12
_diffrn_reflns_limit_h_min       -10
_diffrn_reflns_limit_k_max       16
_diffrn_reflns_limit_k_min       -16
_diffrn_reflns_limit_l_max       25
_diffrn_reflns_limit_l_min       -25
_diffrn_reflns_number            16611
_diffrn_reflns_theta_full        27.36
_diffrn_reflns_theta_max         27.36
_diffrn_reflns_theta_min         2.63
_exptl_absorpt_coefficient_mu    0.288
_exptl_absorpt_correction_type   none
_exptl_crystal_colour            colourless
_exptl_crystal_density_diffrn    1.287
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       prism
_exptl_crystal_F_000             938
_exptl_crystal_size_max          0.25
_exptl_crystal_size_mid          0.10
_exptl_crystal_size_min          0.08
_refine_diff_density_max         0.660
_refine_diff_density_min         -0.775
_refine_diff_density_rms         0.069
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.063
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     552
_refine_ls_number_reflns         10287
_refine_ls_number_restraints     36
_refine_ls_restrained_S_all      1.064
_refine_ls_R_factor_all          0.1128
_refine_ls_R_factor_gt           0.0560
_refine_ls_shift/su_max          0.004
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'calc w=1/[σ²(Fo²)+(0.0697P)²+0.0000P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1299
_refine_ls_wR_factor_ref         0.1498
_reflns_number_gt                6216
_reflns_number_total             10287
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            jo701984z-File003.cif
_cod_data_source_block           cbo001
_cod_depositor_comments
;
The following automatic conversions were performed:
'_symmetry_cell_setting' value 'Triclinic' changed to 'triclinic'
according to '/home/saulius/struct/CIF-dictionaries/cif_core.dic'
dictionary named 'cif_core.dic' version 2.4.1 from
2010-06-29.

'_exptl_absorpt_correction_type' value 'None' changed to
'none' according to '/home/saulius/struct/CIF-dictionaries/cif_core.dic'
dictionary named 'cif_core.dic' version 2.4.1 from 2010-06-29.

Automatic conversion script
Id: cif_fix_enum 1527 2010-12-29 10:47:43Z saulius 
;
_cod_original_formula_sum        'C44.75 H56.75 Cl0.50 N2.75 O6.50 S4'
_cod_database_code               4023224
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
S1 S 0.59931(7) 0.03791(6) 0.86879(4) 0.02592(18) Uani 1 1 d . . .
S2 S 0.60934(8) -0.22650(6) 0.72564(4) 0.02947(19) Uani 1 1 d . . .
S3 S 0.07056(8) 0.13520(6) 0.76782(4) 0.02699(18) Uani 1 1 d . . .
S4 S 0.00012(8) -0.40063(6) 0.61719(4) 0.02640(18) Uani 1 1 d . . .
N1 N 0.1475(2) -0.29985(18) 0.64129(11) 0.0239(5) Uani 1 1 d . . .
N2 N 0.1621(2) 0.04504(17) 0.77541(11) 0.0230(5) Uani 1 1 d . . .
O20 O 0.8955(2) -0.06584(17) 0.57528(11) 0.0388(5) Uani 1 1 d . . .
O31 O -0.07436(19) 0.07448(17) 0.73973(10) 0.0355(5) Uani 1 1 d . . .
O32 O 0.0916(2) 0.19230(17) 0.83211(10) 0.0407(5) Uani 1 1 d . . .
O41 O 0.0436(2) -0.48420(16) 0.58371(10) 0.0352(5) Uani 1 1 d . . .
O42 O -0.0995(2) -0.34984(17) 0.58261(10) 0.0337(5) Uani 1 1 d . . .
O43 O 0.5468(2) -0.20970(17) 1.02391(10) 0.0365(5) Uani 1 1 d . . .
C1 C 0.6513(3) -0.0723(2) 0.82872(13) 0.0269(6) Uani 1 1 d . . .
H1A H 0.7587 -0.0485 0.8279 0.0425(12) Uiso 1 1 calc R . .
H1B H 0.6227 -0.1404 0.8559 0.0425(12) Uiso 1 1 calc R . .
C2 C 0.5789(3) -0.0993(2) 0.75660(14) 0.0303(7) Uani 1 1 d . . .
H2A H 0.6210 -0.0365 0.7269 0.0425(12) Uiso 1 1 calc R . .
H2B H 0.4727 -0.1107 0.7559 0.0425(12) Uiso 1 1 calc R . .
C3 C 0.5500(3) -0.2213(2) 0.63771(13) 0.0237(6) Uani 1 1 d . . .
C4 C 0.6502(3) -0.1716(2) 0.59098(14) 0.0256(6) Uani 1 1 d . . .
C5 C 0.6041(3) -0.1658(2) 0.52285(14) 0.0252(6) Uani 1 1 d . . .
H5 H 0.6740 -0.1316 0.4923 0.0425(12) Uiso 1 1 calc R . .
C6 C 0.4571(3) -0.2094(2) 0.49857(13) 0.0224(6) Uani 1 1 d . . .
C7 C 0.3590(3) -0.2601(2) 0.54549(14) 0.0244(6) Uani 1 1 d . . .
H7 H 0.2586 -0.2914 0.5297 0.0425(12) Uiso 1 1 calc R . .
C8 C 0.4008(3) -0.2669(2) 0.61380(13) 0.0222(6) Uani 1 1 d . . .
C9 C 0.2843(3) -0.3225(2) 0.66126(14) 0.0272(7) Uani 1 1 d . . .
H9A H 0.2671 -0.4042 0.6602 0.0425(12) Uiso 1 1 calc R . .
H9B H 0.3198 -0.2940 0.7084 0.0425(12) Uiso 1 1 calc R . .
C10 C 0.1496(3) -0.1831(2) 0.64624(14) 0.0256(6) Uani 1 1 d . . .
H10A H 0.0674 -0.1743 0.6156 0.0425(12) Uiso 1 1 calc R . .
H10B H 0.2412 -0.1354 0.6294 0.0425(12) Uiso 1 1 calc R . .
C11 C 0.1391(3) -0.1396(2) 0.71709(13) 0.0246(6) Uani 1 1 d . . .
H11A H 0.0414 -0.1767 0.7323 0.0425(12) Uiso 1 1 calc R . .
H11B H 0.2139 -0.1541 0.7502 0.0425(12) Uiso 1 1 calc R . .
C12 C 0.1648(3) -0.0150(2) 0.71131(14) 0.0260(6) Uani 1 1 d . . .
H12A H 0.2609 0.0190 0.6937 0.0425(12) Uiso 1 1 calc R . .
H12B H 0.0893 -0.0033 0.6775 0.0425(12) Uiso 1 1 calc R . .
C13 C 0.2976(3) 0.0734(2) 0.82072(14) 0.0273(7) Uani 1 1 d . . .
H13A H 0.3094 0.1436 0.8464 0.0425(12) Uiso 1 1 calc R . .
H13B H 0.3817 0.0861 0.7933 0.0425(12) Uiso 1 1 calc R . .
C14 C 0.2979(3) -0.0190(2) 0.87043(13) 0.0223(6) Uani 1 1 d . . .
C15 C 0.1657(3) -0.0819(2) 0.89332(13) 0.0247(6) Uani 1 1 d . . .
H15 H 0.0791 -0.0667 0.8758 0.0425(12) Uiso 1 1 calc R . .
C16 C 0.1538(3) -0.1656(2) 0.94042(13) 0.0242(6) Uani 1 1 d . A .
C17 C 0.2824(3) -0.1828(2) 0.96709(13) 0.0231(6) Uani 1 1 d . . .
H17 H 0.2781 -0.2389 0.9997 0.0425(12) Uiso 1 1 calc R . .
C18 C 0.4185(3) -0.1200(2) 0.94733(13) 0.0207(6) Uani 1 1 d . . .
C19 C 0.4265(3) -0.0399(2) 0.89674(13) 0.0211(6) Uani 1 1 d . . .
C20 C 0.8079(3) -0.1197(2) 0.61279(15) 0.0315(7) Uani 1 1 d . . .
H20 H 0.8424 -0.1289 0.6582 0.0425(12) Uiso 1 1 calc R . .
C21 C 0.4002(3) -0.2019(2) 0.42457(14) 0.0266(6) Uani 1 1 d . . .
C22 C 0.3346(4) -0.3198(3) 0.39417(16) 0.0435(8) Uani 1 1 d . . .
H22A H 0.4110 -0.3559 0.3941 0.0425(12) Uiso 1 1 calc R . .
H22B H 0.2928 -0.3165 0.3475 0.0425(12) Uiso 1 1 calc R . .
H22C H 0.2577 -0.3630 0.4214 0.0425(12) Uiso 1 1 calc R . .
C23 C 0.5205(3) -0.1360(3) 0.38228(15) 0.0369(8) Uani 1 1 d . . .
H23A H 0.5600 -0.0588 0.4002 0.0425(12) Uiso 1 1 calc R . .
H23B H 0.4801 -0.1362 0.3350 0.0425(12) Uiso 1 1 calc R . .
H23C H 0.5987 -0.1706 0.3845 0.0425(12) Uiso 1 1 calc R . .
C24 C 0.2818(3) -0.1444(3) 0.42214(16) 0.0462(9) Uani 1 1 d . . .
H24A H 0.1987 -0.1903 0.4448 0.0425(12) Uiso 1 1 calc R . .
H24B H 0.2495 -0.1351 0.3747 0.0425(12) Uiso 1 1 calc R . .
H24C H 0.3215 -0.0710 0.4453 0.0425(12) Uiso 1 1 calc R . .
C25 C -0.0789(3) -0.4617(2) 0.69061(14) 0.0243(6) Uani 1 1 d . . .
C26 C -0.1933(3) -0.4313(2) 0.71360(14) 0.0280(7) Uani 1 1 d . . .
H26 H -0.2249 -0.3743 0.6921 0.0425(12) Uiso 1 1 calc R . .
C27 C -0.2605(3) -0.4855(2) 0.76847(14) 0.0312(7) Uani 1 1 d . . .
H27 H -0.3381 -0.4642 0.7844 0.0425(12) Uiso 1 1 calc R . .
C28 C -0.2185(3) -0.5692(2) 0.80065(15) 0.0329(7) Uani 1 1 d . . .
C29 C -0.1022(3) -0.5970(2) 0.77762(15) 0.0352(7) Uani 1 1 d . . .
H29 H -0.0698 -0.6532 0.7997 0.0425(12) Uiso 1 1 calc R . .
C30 C -0.0323(3) -0.5436(2) 0.72265(15) 0.0329(7) Uani 1 1 d . . .
H30 H 0.0469 -0.5636 0.7073 0.0425(12) Uiso 1 1 calc R . .
C31 C -0.2970(4) -0.6294(3) 0.85827(17) 0.0501(9) Uani 1 1 d . . .
H31A H -0.2481 -0.5922 0.9014 0.0425(12) Uiso 1 1 calc R . .
H31B H -0.2960 -0.7070 0.8577 0.0425(12) Uiso 1 1 calc R . .
H31C H -0.3983 -0.6282 0.8533 0.0425(12) Uiso 1 1 calc R . .
C32 C 0.1521(3) 0.2314(2) 0.70658(14) 0.0244(6) Uani 1 1 d . . .
C33 C 0.0985(3) 0.2115(2) 0.63881(14) 0.0256(6) Uani 1 1 d . . .
H33 H 0.0164 0.1484 0.6255 0.0425(12) Uiso 1 1 calc R . .
C34 C 0.1655(3) 0.2842(2) 0.59081(14) 0.0279(7) Uani 1 1 d . . .
H34 H 0.1279 0.2712 0.5445 0.0425(12) Uiso 1 1 calc R . .
C35 C 0.2879(3) 0.3767(2) 0.60930(15) 0.0297(7) Uani 1 1 d . . .
C36 C 0.3398(3) 0.3938(2) 0.67740(15) 0.0308(7) Uani 1 1 d . . .
H36 H 0.4227 0.4563 0.6907 0.0425(12) Uiso 1 1 calc R . .
C37 C 0.2738(3) 0.3223(2) 0.72658(15) 0.0282(7) Uani 1 1 d . . .
H37 H 0.3111 0.3350 0.7730 0.0425(12) Uiso 1 1 calc R . .
C38 C 0.3589(3) 0.4532(2) 0.55573(15) 0.0368(8) Uani 1 1 d . . .
H38A H 0.4457 0.5108 0.5765 0.0425(12) Uiso 1 1 calc R . .
H38B H 0.2898 0.4888 0.5342 0.0425(12) Uiso 1 1 calc R . .
H38C H 0.3876 0.4101 0.5214 0.0425(12) Uiso 1 1 calc R . .
C39 C 0.0037(3) -0.2331(3) 0.96105(15) 0.0333(7) Uani 1 1 d . . .
C40A C -0.0920(5) -0.2932(4) 0.8994(2) 0.0497(14) Uani 0.761(5) 1 d PU A 1
H40A H -0.1895 -0.3336 0.9124 0.0425(12) Uiso 0.761(5) 1 calc PR A 1
H40B H -0.0488 -0.3464 0.8807 0.0425(12) Uiso 0.761(5) 1 calc PR A 1
H40C H -0.0998 -0.2387 0.8650 0.0425(12) Uiso 0.761(5) 1 calc PR A 1
C41A C -0.0682(5) -0.1518(4) 0.9928(2) 0.0457(13) Uani 0.761(5) 1 d PU A 1
H41A H -0.1639 -0.1946 1.0066 0.0425(12) Uiso 0.761(5) 1 calc PR A 1
H41B H -0.0803 -0.0975 0.9590 0.0425(12) Uiso 0.761(5) 1 calc PR A 1
H41C H -0.0054 -0.1122 1.0325 0.0425(12) Uiso 0.761(5) 1 calc PR A 1
C42A C 0.0130(4) -0.3169(4) 1.0159(2) 0.0454(14) Uani 0.761(5) 1 d PU A 1
H42A H 0.0713 -0.2768 1.0566 0.0425(12) Uiso 0.761(5) 1 calc PR A 1
H42B H 0.0593 -0.3695 0.9991 0.0425(12) Uiso 0.761(5) 1 calc PR A 1
H42C H -0.0855 -0.3580 1.0273 0.0425(12) Uiso 0.761(5) 1 calc PR A 1
C40B C -0.0114(15) -0.3680(11) 0.9465(8) 0.044(4) Uani 0.239(5) 1 d PU A 2
H40D H 0.0705 -0.3856 0.9716 0.0425(12) Uiso 0.239(5) 1 calc PR A 2
H40E H -0.0100 -0.3815 0.8978 0.0425(12) Uiso 0.239(5) 1 calc PR A 2
H40F H -0.1036 -0.4157 0.9615 0.0425(12) Uiso 0.239(5) 1 calc PR A 2
C41B C -0.0016(15) -0.2118(13) 1.0302(7) 0.047(4) Uani 0.239(5) 1 d PU A 2
H41D H 0.0694 -0.2395 1.0572 0.0425(12) Uiso 0.239(5) 1 calc PR A 2
H41E H -0.0999 -0.2498 1.0430 0.0425(12) Uiso 0.239(5) 1 calc PR A 2
H41F H 0.0221 -0.1311 1.0386 0.0425(12) Uiso 0.239(5) 1 calc PR A 2
C42B C -0.1211(13) -0.2216(13) 0.9151(7) 0.036(4) Uani 0.239(5) 1 d PU A 2
H42D H -0.1287 -0.1463 0.9209 0.0425(12) Uiso 0.239(5) 1 calc PR A 2
H42E H -0.2117 -0.2770 0.9262 0.0425(12) Uiso 0.239(5) 1 calc PR A 2
H42F H -0.1050 -0.2337 0.8679 0.0425(12) Uiso 0.239(5) 1 calc PR A 2
C43 C 0.55211(17) -0.13565(13) 0.98367(8) 0.0252(6) Uani 1 1 d . . .
H43 H 0.6449 -0.0861 0.9752 0.0425(12) Uiso 1 1 calc R . .
Cl1 Cl 0.62740(17) 0.58003(13) 0.07108(8) 0.0357(7) Uiso 0.25 1 d PR B 1
Cl2 Cl 0.57700(17) 0.37903(13) 0.15378(8) 0.0426(8) Uiso 0.25 1 d PR B 1
C50 C 0.64722(17) 0.44506(13) 0.07864(8) 0.086(6) Uiso 0.25 1 d PR B 1
H50A H 0.7520 0.4512 0.0796 0.0425(12) Uiso 0.25 1 calc PR C 1
H50B H 0.5949 0.3981 0.0384 0.0425(12) Uiso 0.25 1 calc PR D 1
C60 C 0.70350(17) 0.40203(13) 0.16528(8) 0.070(2) Uiso 0.50 1 d PR E 2
H60A H 0.6616 0.4323 0.2011 0.0425(12) Uiso 0.50 1 calc PR F 2
H60B H 0.8054 0.4084 0.1800 0.0425(12) Uiso 0.50 1 calc PR G 2
H60C H 0.6474 0.3232 0.1560 0.0425(12) Uiso 0.50 1 calc PR H 2
N61 N 0.69760(17) 0.46633(13) 0.10218(8) 0.094(3) Uiso 0.50 1 d PR E 2
H61 H 0.7777 0.5077 0.0857 0.0425(12) Uiso 0.50 1 calc PR I 2
C62 C 0.56644(17) 0.45836(13) 0.07221(8) 0.060(2) Uiso 0.50 1 d PR E 2
H62 H 0.4789 0.4160 0.0902 0.0425(12) Uiso 0.50 1 calc PR J 2
O63 O 0.56644(17) 0.51896(13) 0.01001(8) 0.135(3) Uiso 0.50 1 d PR E 2
N70 N 0.58086(17) 0.43492(13) 0.10690(8) 0.054(3) Uiso 0.25 1 d PR K 3
H70A H 0.5290(8) 0.4642(6) 0.1324(4) 0.043 Uiso 0.25 1 d P L 3
C71 C 0.7374(8) 0.4575(6) 0.1353(4) 0.025(2) Uiso 0.25 1 d PR K 3
H71A H 0.7950 0.4458 0.0994 0.0425(12) Uiso 0.25 1 calc PR L 3
H71B H 0.7422 0.4065 0.1722 0.0425(12) Uiso 0.25 1 calc PR L 3
H71C H 0.7768 0.5349 0.1528 0.0425(12) Uiso 0.25 1 calc PR L 3
C72 C 0.5917(8) 0.4896(6) 0.0368(4) 0.025(2) Uiso 0.25 1 d PR K 3
H72A H 0.5959 0.5680 0.0420 0.0425(12) Uiso 0.25 1 calc PR L 3
H72B H 0.5058 0.4499 0.0061 0.0425(12) Uiso 0.25 1 calc PR L 3
H72C H 0.6803 0.4857 0.0179 0.0425(12) Uiso 0.25 1 calc PR L 3
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'
S S 0.1246 0.1234 '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
C19 S1 C1 101.15(12) . . ?
C3 S2 C2 99.06(12) . . ?
O32 S3 O31 119.58(13) . . ?
O32 S3 N2 106.74(12) . . ?
O31 S3 N2 106.70(12) . . ?
O32 S3 C32 109.18(13) . . ?
O31 S3 C32 107.43(13) . . ?
N2 S3 C32 106.50(12) . . ?
O41 S4 O42 120.79(12) . . ?
O41 S4 N1 107.20(11) . . ?
O42 S4 N1 106.48(12) . . ?
O41 S4 C25 106.68(12) . . ?
O42 S4 C25 107.10(12) . . ?
N1 S4 C25 108.06(12) . . ?
C9 N1 C10 116.8(2) . . ?
C9 N1 S4 120.81(18) . . ?
C10 N1 S4 122.37(18) . . ?
C13 N2 C12 115.1(2) . . ?
C13 N2 S3 118.92(18) . . ?
C12 N2 S3 114.46(17) . . ?
C2 C1 S1 111.62(19) . . ?
C2 C1 H1A 109.3 . . ?
S1 C1 H1A 109.3 . . ?
C2 C1 H1B 109.3 . . ?
S1 C1 H1B 109.3 . . ?
H1A C1 H1B 108.0 . . ?
C1 C2 S2 108.79(19) . . ?
C1 C2 H2A 109.9 . . ?
S2 C2 H2A 109.9 . . ?
C1 C2 H2B 109.9 . . ?
S2 C2 H2B 109.9 . . ?
H2A C2 H2B 108.3 . . ?
C4 C3 C8 118.5(2) . . ?
C4 C3 S2 120.9(2) . . ?
C8 C3 S2 120.6(2) . . ?
C5 C4 C3 121.0(2) . . ?
C5 C4 C20 117.5(3) . . ?
C3 C4 C20 121.4(3) . . ?
C4 C5 C6 121.2(3) . . ?
C4 C5 H5 119.4 . . ?
C6 C5 H5 119.4 . . ?
C5 C6 C7 117.1(3) . . ?
C5 C6 C21 123.2(2) . . ?
C7 C6 C21 119.7(2) . . ?
C8 C7 C6 123.3(2) . . ?
C8 C7 H7 118.4 . . ?
C6 C7 H7 118.4 . . ?
C7 C8 C3 118.8(2) . . ?
C7 C8 C9 119.2(2) . . ?
C3 C8 C9 121.9(2) . . ?
N1 C9 C8 111.2(2) . . ?
N1 C9 H9A 109.4 . . ?
C8 C9 H9A 109.4 . . ?
N1 C9 H9B 109.4 . . ?
C8 C9 H9B 109.4 . . ?
H9A C9 H9B 108.0 . . ?
N1 C10 C11 116.0(2) . . ?
N1 C10 H10A 108.3 . . ?
C11 C10 H10A 108.3 . . ?
N1 C10 H10B 108.3 . . ?
C11 C10 H10B 108.3 . . ?
H10A C10 H10B 107.4 . . ?
C12 C11 C10 106.3(2) . . ?
C12 C11 H11A 110.5 . . ?
C10 C11 H11A 110.5 . . ?
C12 C11 H11B 110.5 . . ?
C10 C11 H11B 110.5 . . ?
H11A C11 H11B 108.7 . . ?
N2 C12 C11 115.2(2) . . ?
N2 C12 H12A 108.5 . . ?
C11 C12 H12A 108.5 . . ?
N2 C12 H12B 108.5 . . ?
C11 C12 H12B 108.5 . . ?
H12A C12 H12B 107.5 . . ?
N2 C13 C14 111.7(2) . . ?
N2 C13 H13A 109.3 . . ?
C14 C13 H13A 109.3 . . ?
N2 C13 H13B 109.3 . . ?
C14 C13 H13B 109.3 . . ?
H13A C13 H13B 107.9 . . ?
C15 C14 C19 118.6(2) . . ?
C15 C14 C13 118.6(2) . . ?
C19 C14 C13 122.7(2) . . ?
C16 C15 C14 123.5(2) . . ?
C16 C15 H15 118.3 . . ?
C14 C15 H15 118.3 . . ?
C17 C16 C15 117.0(2) . . ?
C17 C16 C39 122.9(2) . . ?
C15 C16 C39 120.1(2) . . ?
C16 C17 C18 121.9(2) . . ?
C16 C17 H17 119.1 . . ?
C18 C17 H17 119.1 . . ?
C17 C18 C19 119.9(2) . . ?
C17 C18 C43 118.3(2) . . ?
C19 C18 C43 121.7(2) . . ?
C14 C19 C18 119.0(2) . . ?
C14 C19 S1 120.5(2) . . ?
C18 C19 S1 120.5(2) . . ?
O20 C20 C4 123.3(3) . . ?
O20 C20 H20 118.4 . . ?
C4 C20 H20 118.4 . . ?
C22 C21 C23 109.0(2) . . ?
C22 C21 C24 109.3(3) . . ?
C23 C21 C24 108.5(2) . . ?
C22 C21 C6 108.6(2) . . ?
C23 C21 C6 112.3(2) . . ?
C24 C21 C6 109.2(2) . . ?
C21 C22 H22A 109.5 . . ?
C21 C22 H22B 109.5 . . ?
H22A C22 H22B 109.5 . . ?
C21 C22 H22C 109.5 . . ?
H22A C22 H22C 109.5 . . ?
H22B C22 H22C 109.5 . . ?
C21 C23 H23A 109.5 . . ?
C21 C23 H23B 109.5 . . ?
H23A C23 H23B 109.5 . . ?
C21 C23 H23C 109.5 . . ?
H23A C23 H23C 109.5 . . ?
H23B C23 H23C 109.5 . . ?
C21 C24 H24A 109.5 . . ?
C21 C24 H24B 109.5 . . ?
H24A C24 H24B 109.5 . . ?
C21 C24 H24C 109.5 . . ?
H24A C24 H24C 109.5 . . ?
H24B C24 H24C 109.5 . . ?
C30 C25 C26 120.2(3) . . ?
C30 C25 S4 119.9(2) . . ?
C26 C25 S4 119.7(2) . . ?
C27 C26 C25 118.9(3) . . ?
C27 C26 H26 120.5 . . ?
C25 C26 H26 120.5 . . ?
C28 C27 C26 122.2(3) . . ?
C28 C27 H27 118.9 . . ?
C26 C27 H27 118.9 . . ?
C27 C28 C29 117.9(3) . . ?
C27 C28 C31 121.0(3) . . ?
C29 C28 C31 121.1(3) . . ?
C28 C29 C30 121.1(3) . . ?
C28 C29 H29 119.5 . . ?
C30 C29 H29 119.5 . . ?
C25 C30 C29 119.6(3) . . ?
C25 C30 H30 120.2 . . ?
C29 C30 H30 120.2 . . ?
C28 C31 H31A 109.5 . . ?
C28 C31 H31B 109.5 . . ?
H31A C31 H31B 109.5 . . ?
C28 C31 H31C 109.5 . . ?
H31A C31 H31C 109.5 . . ?
H31B C31 H31C 109.5 . . ?
C33 C32 C37 120.9(2) . . ?
C33 C32 S3 119.5(2) . . ?
C37 C32 S3 119.6(2) . . ?
C34 C33 C32 119.4(3) . . ?
C34 C33 H33 120.3 . . ?
C32 C33 H33 120.3 . . ?
C33 C34 C35 121.1(3) . . ?
C33 C34 H34 119.5 . . ?
C35 C34 H34 119.5 . . ?
C36 C35 C34 118.2(3) . . ?
C36 C35 C38 122.2(3) . . ?
C34 C35 C38 119.7(3) . . ?
C35 C36 C37 121.8(3) . . ?
C35 C36 H36 119.1 . . ?
C37 C36 H36 119.1 . . ?
C36 C37 C32 118.6(3) . . ?
C36 C37 H37 120.7 . . ?
C32 C37 H37 120.7 . . ?
C35 C38 H38A 109.5 . . ?
C35 C38 H38B 109.5 . . ?
H38A C38 H38B 109.5 . . ?
C35 C38 H38C 109.5 . . ?
H38A C38 H38C 109.5 . . ?
H38B C38 H38C 109.5 . . ?
C41B C39 C42B 115.4(8) . . ?
C40A C39 C42A 110.0(3) . . ?
C41B C39 C16 108.9(6) . . ?
C42B C39 C16 114.1(5) . . ?
C40A C39 C16 109.7(3) . . ?
C42A C39 C16 112.6(3) . . ?
C40A C39 C41A 109.6(3) . . ?
C42A C39 C41A 105.8(3) . . ?
C16 C39 C41A 109.0(3) . . ?
C41B C39 C40B 110.9(8) . . ?
C42B C39 C40B 101.1(8) . . ?
C16 C39 C40B 105.9(5) . . ?
C39 C40A H40A 109.5 . . ?
C39 C40A H40B 109.5 . . ?
C39 C40A H40C 109.5 . . ?
C39 C41A H41A 109.5 . . ?
C39 C41A H41B 109.5 . . ?
C39 C41A H41C 109.5 . . ?
C39 C42A H42A 109.5 . . ?
C39 C42A H42B 109.5 . . ?
C39 C42A H42C 109.5 . . ?
C39 C40B H40D 109.5 . . ?
C39 C40B H40E 109.5 . . ?
H40D C40B H40E 109.5 . . ?
C39 C40B H40F 109.5 . . ?
H40D C40B H40F 109.5 . . ?
H40E C40B H40F 109.5 . . ?
C39 C41B H41D 109.5 . . ?
C39 C41B H41E 109.5 . . ?
H41D C41B H41E 109.5 . . ?
C39 C41B H41F 109.5 . . ?
H41D C41B H41F 109.5 . . ?
H41E C41B H41F 109.5 . . ?
C39 C42B H42D 109.5 . . ?
C39 C42B H42E 109.5 . . ?
H42D C42B H42E 109.5 . . ?
C39 C42B H42F 109.5 . . ?
H42D C42B H42F 109.5 . . ?
H42E C42B H42F 109.5 . . ?
O43 C43 C18 122.34(18) . . ?
O43 C43 H43 118.8 . . ?
C18 C43 H43 118.8 . . ?
Cl1 C50 Cl2 111.9 . . ?
Cl1 C50 H50A 109.2 . . ?
Cl2 C50 H50A 109.2 . . ?
Cl1 C50 H50B 109.2 . . ?
Cl2 C50 H50B 109.2 . . ?
H50A C50 H50B 107.9 . . ?
N61 C60 H60A 109.5 . . ?
N61 C60 H60B 109.5 . . ?
H60A C60 H60B 109.5 . . ?
N61 C60 H60C 109.5 . . ?
H60A C60 H60C 109.5 . . ?
H60B C60 H60C 109.5 . . ?
C62 N61 C60 117.0 . . ?
C62 N61 H61 121.5 . . ?
C60 N61 H61 121.5 . . ?
N61 C62 O63 115.0 . . ?
N61 C62 H62 122.5 . . ?
O63 C62 H62 122.5 . . ?
C71 N70 C72 104.2(5) . . ?
C71 N70 H70A 113.7(7) . . ?
C72 N70 H70A 109.9(7) . . ?
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
S1 C19 1.792(3) . ?
S1 C1 1.819(3) . ?
S2 C3 1.789(3) . ?
S2 C2 1.830(3) . ?
S3 O32 1.428(2) . ?
S3 O31 1.432(2) . ?
S3 N2 1.641(2) . ?
S3 C32 1.772(3) . ?
S4 O41 1.430(2) . ?
S4 O42 1.437(2) . ?
S4 N1 1.620(2) . ?
S4 C25 1.767(3) . ?
N1 C9 1.458(3) . ?
N1 C10 1.466(3) . ?
N2 C13 1.464(3) . ?
N2 C12 1.482(3) . ?
O20 C20 1.219(3) . ?
O43 C43 1.218(2) . ?
C1 C2 1.521(4) . ?
C1 H1A 0.9900 . ?
C1 H1B 0.9900 . ?
C2 H2A 0.9900 . ?
C2 H2B 0.9900 . ?
C3 C4 1.405(4) . ?
C3 C8 1.413(4) . ?
C4 C5 1.390(4) . ?
C4 C20 1.484(4) . ?
C5 C6 1.395(4) . ?
C5 H5 0.9500 . ?
C6 C7 1.398(4) . ?
C6 C21 1.530(4) . ?
C7 C8 1.386(4) . ?
C7 H7 0.9500 . ?
C8 C9 1.531(4) . ?
C9 H9A 0.9900 . ?
C9 H9B 0.9900 . ?
C10 C11 1.529(4) . ?
C10 H10A 0.9900 . ?
C10 H10B 0.9900 . ?
C11 C12 1.516(4) . ?
C11 H11A 0.9900 . ?
C11 H11B 0.9900 . ?
C12 H12A 0.9900 . ?
C12 H12B 0.9900 . ?
C13 C14 1.524(3) . ?
C13 H13A 0.9900 . ?
C13 H13B 0.9900 . ?
C14 C15 1.395(3) . ?
C14 C19 1.403(4) . ?
C15 C16 1.391(4) . ?
C15 H15 0.9500 . ?
C16 C17 1.385(4) . ?
C16 C39 1.530(4) . ?
C17 C18 1.400(3) . ?
C17 H17 0.9500 . ?
C18 C19 1.411(4) . ?
C18 C43 1.487(3) . ?
C20 H20 0.9500 . ?
C21 C22 1.521(4) . ?
C21 C23 1.523(4) . ?
C21 C24 1.529(4) . ?
C22 H22A 0.9800 . ?
C22 H22B 0.9800 . ?
C22 H22C 0.9800 . ?
C23 H23A 0.9800 . ?
C23 H23B 0.9800 . ?
C23 H23C 0.9800 . ?
C24 H24A 0.9800 . ?
C24 H24B 0.9800 . ?
C24 H24C 0.9800 . ?
C25 C30 1.380(4) . ?
C25 C26 1.389(4) . ?
C26 C27 1.386(4) . ?
C26 H26 0.9500 . ?
C27 C28 1.378(4) . ?
C27 H27 0.9500 . ?
C28 C29 1.389(4) . ?
C28 C31 1.500(4) . ?
C29 C30 1.394(4) . ?
C29 H29 0.9500 . ?
C30 H30 0.9500 . ?
C31 H31A 0.9800 . ?
C31 H31B 0.9800 . ?
C31 H31C 0.9800 . ?
C32 C33 1.387(4) . ?
C32 C37 1.390(4) . ?
C33 C34 1.380(4) . ?
C33 H33 0.9500 . ?
C34 C35 1.400(4) . ?
C34 H34 0.9500 . ?
C35 C36 1.387(4) . ?
C35 C38 1.499(4) . ?
C36 C37 1.387(4) . ?
C36 H36 0.9500 . ?
C37 H37 0.9500 . ?
C38 H38A 0.9800 . ?
C38 H38B 0.9800 . ?
C38 H38C 0.9800 . ?
C39 C41B 1.402(14) . ?
C39 C42B 1.487(13) . ?
C39 C40A 1.509(5) . ?
C39 C42A 1.529(5) . ?
C39 C41A 1.563(5) . ?
C39 C40B 1.681(13) . ?
C40A H40A 0.9800 . ?
C40A H40B 0.9800 . ?
C40A H40C 0.9800 . ?
C41A H41A 0.9800 . ?
C41A H41B 0.9800 . ?
C41A H41C 0.9800 . ?
C42A H42A 0.9800 . ?
C42A H42B 0.9800 . ?
C42A H42C 0.9800 . ?
C40B H40D 0.9800 . ?
C40B H40E 0.9800 . ?
C40B H40F 0.9800 . ?
C41B H41D 0.9800 . ?
C41B H41E 0.9800 . ?
C41B H41F 0.9800 . ?
C42B H42D 0.9800 . ?
C42B H42E 0.9800 . ?
C42B H42F 0.9800 . ?
C43 H43 0.9500 . ?
Cl1 C50 1.7723 . ?
Cl2 C50 1.7880 . ?
Cl2 H70A 1.347(8) . ?
C50 H50A 0.9900 . ?
C50 H50B 0.9900 . ?
C60 N61 1.4941 . ?
C60 H60A 0.9800 . ?
C60 H60B 0.9800 . ?
C60 H60C 0.9800 . ?
N61 C62 1.3245 . ?
N61 H61 0.8800 . ?
C62 O63 1.4479 . ?
C62 H62 0.9500 . ?
C62 H70A 1.284(8) . ?
N70 C71 1.505(8) . ?
N70 C72 1.546(8) . ?
N70 H70A 0.895(8) . ?
C71 H71A 0.9800 . ?
C71 H71B 0.9800 . ?
C71 H71C 0.9800 . ?
C72 H72A 0.9800 . ?
C72 H72B 0.9800 . ?
C72 H72C 0.9800 . ?
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
O41 S4 N1 C9 -32.6(2) . . . . ?
O42 S4 N1 C9 -163.16(19) . . . . ?
C25 S4 N1 C9 82.1(2) . . . . ?
O41 S4 N1 C10 149.4(2) . . . . ?
O42 S4 N1 C10 18.8(2) . . . . ?
C25 S4 N1 C10 -96.0(2) . . . . ?
O32 S3 N2 C13 -32.8(2) . . . . ?
O31 S3 N2 C13 -161.74(18) . . . . ?
C32 S3 N2 C13 83.7(2) . . . . ?
O32 S3 N2 C12 -174.38(17) . . . . ?
O31 S3 N2 C12 56.7(2) . . . . ?
C32 S3 N2 C12 -57.8(2) . . . . ?
C19 S1 C1 C2 82.2(2) . . . . ?
S1 C1 C2 S2 -169.81(14) . . . . ?
C3 S2 C2 C1 -168.4(2) . . . . ?
C2 S2 C3 C4 93.8(2) . . . . ?
C2 S2 C3 C8 -86.0(2) . . . . ?
C8 C3 C4 C5 0.9(4) . . . . ?
S2 C3 C4 C5 -179.0(2) . . . . ?
C8 C3 C4 C20 178.6(2) . . . . ?
S2 C3 C4 C20 -1.3(4) . . . . ?
C3 C4 C5 C6 -0.2(4) . . . . ?
C20 C4 C5 C6 -178.0(2) . . . . ?
C4 C5 C6 C7 -0.8(4) . . . . ?
C4 C5 C6 C21 178.0(2) . . . . ?
C5 C6 C7 C8 1.1(4) . . . . ?
C21 C6 C7 C8 -177.8(2) . . . . ?
C6 C7 C8 C3 -0.4(4) . . . . ?
C6 C7 C8 C9 179.0(2) . . . . ?
C4 C3 C8 C7 -0.6(4) . . . . ?
S2 C3 C8 C7 179.3(2) . . . . ?
C4 C3 C8 C9 -179.9(2) . . . . ?
S2 C3 C8 C9 -0.1(3) . . . . ?
C10 N1 C9 C8 -64.7(3) . . . . ?
S4 N1 C9 C8 117.2(2) . . . . ?
C7 C8 C9 N1 -35.2(3) . . . . ?
C3 C8 C9 N1 144.1(2) . . . . ?
C9 N1 C10 C11 -80.2(3) . . . . ?
S4 N1 C10 C11 97.9(3) . . . . ?
N1 C10 C11 C12 172.2(2) . . . . ?
C13 N2 C12 C11 80.9(3) . . . . ?
S3 N2 C12 C11 -136.0(2) . . . . ?
C10 C11 C12 N2 -178.9(2) . . . . ?
C12 N2 C13 C14 -90.2(3) . . . . ?
S3 N2 C13 C14 128.4(2) . . . . ?
N2 C13 C14 C15 -32.9(3) . . . . ?
N2 C13 C14 C19 150.4(2) . . . . ?
C19 C14 C15 C16 -0.9(4) . . . . ?
C13 C14 C15 C16 -177.7(2) . . . . ?
C14 C15 C16 C17 2.5(4) . . . . ?
C14 C15 C16 C39 -178.0(3) . . . . ?
C15 C16 C17 C18 -0.6(4) . . . . ?
C39 C16 C17 C18 179.9(3) . . . . ?
C16 C17 C18 C19 -2.8(4) . . . . ?
C16 C17 C18 C43 173.7(2) . . . . ?
C15 C14 C19 C18 -2.6(4) . . . . ?
C13 C14 C19 C18 174.1(2) . . . . ?
C15 C14 C19 S1 179.7(2) . . . . ?
C13 C14 C19 S1 -3.6(4) . . . . ?
C17 C18 C19 C14 4.4(4) . . . . ?
C43 C18 C19 C14 -171.9(2) . . . . ?
C17 C18 C19 S1 -177.87(19) . . . . ?
C43 C18 C19 S1 5.8(3) . . . . ?
C1 S1 C19 C14 -116.6(2) . . . . ?
C1 S1 C19 C18 65.8(2) . . . . ?
C5 C4 C20 O20 5.6(4) . . . . ?
C3 C4 C20 O20 -172.1(3) . . . . ?
C5 C6 C21 C22 117.2(3) . . . . ?
C7 C6 C21 C22 -64.0(3) . . . . ?
C5 C6 C21 C23 -3.4(4) . . . . ?
C7 C6 C21 C23 175.4(2) . . . . ?
C5 C6 C21 C24 -123.8(3) . . . . ?
C7 C6 C21 C24 55.0(3) . . . . ?
O41 S4 C25 C30 29.9(3) . . . . ?
O42 S4 C25 C30 160.5(2) . . . . ?
N1 S4 C25 C30 -85.1(2) . . . . ?
O41 S4 C25 C26 -146.6(2) . . . . ?
O42 S4 C25 C26 -15.9(3) . . . . ?
N1 S4 C25 C26 98.5(2) . . . . ?
C30 C25 C26 C27 -0.8(4) . . . . ?
S4 C25 C26 C27 175.6(2) . . . . ?
C25 C26 C27 C28 -0.6(4) . . . . ?
C26 C27 C28 C29 1.7(5) . . . . ?
C26 C27 C28 C31 -177.7(3) . . . . ?
C27 C28 C29 C30 -1.5(5) . . . . ?
C31 C28 C29 C30 177.9(3) . . . . ?
C26 C25 C30 C29 1.0(4) . . . . ?
S4 C25 C30 C29 -175.5(2) . . . . ?
C28 C29 C30 C25 0.2(5) . . . . ?
O32 S3 C32 C33 -153.4(2) . . . . ?
O31 S3 C32 C33 -22.3(3) . . . . ?
N2 S3 C32 C33 91.7(2) . . . . ?
O32 S3 C32 C37 30.2(2) . . . . ?
O31 S3 C32 C37 161.3(2) . . . . ?
N2 S3 C32 C37 -84.7(2) . . . . ?
C37 C32 C33 C34 -1.2(4) . . . . ?
S3 C32 C33 C34 -177.6(2) . . . . ?
C32 C33 C34 C35 0.9(4) . . . . ?
C33 C34 C35 C36 -0.4(4) . . . . ?
C33 C34 C35 C38 179.3(3) . . . . ?
C34 C35 C36 C37 0.0(4) . . . . ?
C38 C35 C36 C37 -179.6(3) . . . . ?
C35 C36 C37 C32 -0.3(4) . . . . ?
C33 C32 C37 C36 0.9(4) . . . . ?
S3 C32 C37 C36 177.3(2) . . . . ?
C17 C16 C39 C41B 63.8(8) . . . . ?
C15 C16 C39 C41B -115.7(7) . . . . ?
C17 C16 C39 C42B -165.7(7) . . . . ?
C15 C16 C39 C42B 14.8(8) . . . . ?
C17 C16 C39 C40A -120.4(4) . . . . ?
C15 C16 C39 C40A 60.2(4) . . . . ?
C17 C16 C39 C42A 2.5(4) . . . . ?
C15 C16 C39 C42A -177.0(3) . . . . ?
C17 C16 C39 C41A 119.6(3) . . . . ?
C15 C16 C39 C41A -59.8(4) . . . . ?
C17 C16 C39 C40B -55.5(6) . . . . ?
C15 C16 C39 C40B 125.0(6) . . . . ?
C17 C18 C43 O43 8.9(3) . . . . ?
C19 C18 C43 O43 -174.7(2) . . . . ?
C60 N61 C62 O63 -177.9 . . . . ?
