##############################################################################
#                                                                            #
# This CIF contains the data in a paper accepted for publication in          #
# Acta Crystallographica Section E. It conforms to the requirements of       #
# Notes for Authors for Acta Crystallographica Section E, and has been       #
# peer reviewed under the auspices of the IUCr Commission on Journals.       #
#                                                                            #
# Full details of the Crystallographic Information File format               #
# are given in the paper "The Crystallographic Information File (CIF):       #
# a New Standard Archive File for Crystallography" by S. R. Hall, F. H.      #
# Allen and I. D. Brown [Acta Cryst. (1991), A47, 655-685].                  #
#                                                                            #
# The current version of the core CIF dictionary is obtainable from          #
# ftp://ftp.iucr.org/pub/cif_core.dic.                                       #
#                                                                            #
# Software is freely available for graphical display of the structure(s)     #
# in this CIF. For information consult the CIF software page                 #
# http://www.iucr.org/resources/cif/software.                                #
#                                                                            #
# This file may be used for bona fide research purposes within the           #
# scientific community so long as proper attribution is given to the journal # 
# article from which it was obtained.                                        #
#                                                                            #
##############################################################################
data_global
_audit_creation_method     'manual editing of SHELXL template'
_journal_date_recd_electronic     2011-07-20
_journal_date_accepted     2011-08-09
_journal_name_full     'Acta Crystallographica, Section E'
_journal_year     2011
_journal_volume     67
_journal_issue      9
_journal_page_first     o2360
_journal_page_last     o2361
_journal_paper_category     QO
_journal_coeditor_code     LH5292
loop_
    _publ_contact_author_name
    _publ_contact_author_address
    _publ_contact_author_email
    'Gabriele Schatte'
; Saskatchewan Structural Sciences Centre
  University of Saskatchewan
  Saskatoon, Saskatchewan
  Canada S7N 5C9
;
 'gabriele.schatte@usask.ca'
    'Ramaswami Sammynaiken'
; Saskatchewan Structural Sciences Centre
  University of Saskatchewan
  Saskatoon, Saskatchewan
  Canada S7N 5C9
;
 'r.sammynaiken@usask.ca'
_publ_section_title
;
Cyclolinopeptide K butanol disolvate monohydrate
;
loop_
    _publ_author_name
    _publ_author_footnote
    _publ_author_address
    'Jadhav, Pramodkumar' .
;  College of Agriculture & Bioresources
  University of Saskatchewan
  Saskatoon, Saskatchewan
  Canada S7N 5A8
;
    'Schatte, Gabriele' .
; Saskatchewan Structural Sciences Centre
  University of Saskatchewan
  Saskatoon, Saskatchewan
  Canada S7N 5C9
;
    'Labiuk, Shaunivan' .
; Canadian Light Source Inc.
  University of Saskatchewan
  Saskatoon, Saskatchewan
  Canada S7N 0X4
;
    'Burnett, Peta-Gaye' .
; College of Agriculture & Bioresources
  University of Saskatchewan
  Saskatoon, Saskatchewan
  Canada S7N 5A8
;
    'Li, Bonnie' .
; College of Agriculture & Bioresources
  University of Saskatchewan
  Saskatoon, Saskatchewan
  Canada S7N 5A8
;
    'Okinyo-Owiti, Denis' .
; College of Agriculture & Bioresources
  University of Saskatchewan
  Saskatoon, Saskatchewan
  Canada S7N 5A8
;
    'Reaney, Martin' .
; College of Agriculture & Bioresources
  University of Saskatchewan
  Saskatoon, Saskatchewan
  Canada S7N 5A8
;
    'Grochulski, Pawel' .
; Canadian Light Source Inc.
  University of Saskatchewan
  Saskatoon, Saskatchewan
  Canada S7N 0X4
;
    'Fodje, Michel' .
; Canadian Light Source Inc.
  University of Saskatchewan
  Saskatoon, Saskatchewan
  Canada S7N 0X4
;
    'Sammynaiken, Ramaswami' .
; Saskatchewan Structural Sciences Centre
  University of Saskatchewan
  Saskatoon, Saskatchewan
  Canada S7N 5C9
;
_publ_section_synopsis     .
data_I
_chemical_name_systematic
;
Cyclolinopeptide K butanol disolvate monohydrate
;
_chemical_name_common
;
cyclo-(Metsulfone-Leu-Ile-Pro-Pro-Phe-Phe-Val-Ile)
;
_chemical_formula_moiety     'C56 H83 N9 O11 S, 2(C4 H10 O), H2 O'
_chemical_formula_sum     'C64 H105 N9 O14 S'
_chemical_formula_iupac     'C56 H83 N9 O11 S, 2C4 H10 O, H2 O'
_chemical_formula_weight     1256.63
_chemical_melting_point     ?
_symmetry_cell_setting     orthorhombic
_symmetry_space_group_name_H-M     'P 21 21 21'
_symmetry_space_group_name_Hall     'P 2ac 2ab'
loop_
    _symmetry_equiv_pos_as_xyz
    'x, y, z'
    '-x+1/2, -y, z+1/2'
    'x+1/2, -y+1/2, -z'
    '-x, y+1/2, -z+1/2'
_cell_length_a     11.402(9)
_cell_length_b     23.521(9)
_cell_length_c     25.440(7)
_cell_angle_alpha     90.00
_cell_angle_beta     90.00
_cell_angle_gamma     90.00
_cell_volume     6823(6)
_cell_formula_units_Z     4
_cell_measurement_reflns_used     9870
_cell_measurement_theta_min     2.41
_cell_measurement_theta_max     26.49
_cell_measurement_temperature     100(2)
_exptl_crystal_description     rod
_exptl_crystal_colour     colourless
_exptl_crystal_size_max     0.15
_exptl_crystal_size_mid     0.12
_exptl_crystal_size_min     0.10
_exptl_crystal_density_diffrn     1.223
_exptl_crystal_density_meas     ?
_exptl_crystal_density_method     'not measured'
_exptl_crystal_F_000     2720
_exptl_absorpt_coefficient_mu     0.115
_exptl_absorpt_correction_type     multi-scan
_exptl_absorpt_process_details     '(SADABS; Bruker, 2008)'
_exptl_absorpt_correction_T_min     0.9829
_exptl_absorpt_correction_T_max     0.9886
_exptl_special_details
;
;
_diffrn_ambient_temperature     100(2)
_diffrn_radiation_type     synchrotron
_diffrn_radiation_wavelength     0.68878
_diffrn_radiation_source     'Beamline 081B-1 at the CLS'
_diffrn_radiation_monochromator     'double crystal Si(111)'
_diffrn_measurement_device_type
;
300mm 16K Rayonix MX300 HE CCD detector with
an ACCEL MD2 microdiffractometer
;
_diffrn_measurement_method     'CCD rotation images, ω scans'
_diffrn_detector_area_resol_mean     13.8
_diffrn_reflns_number     549120
_diffrn_reflns_av_R_equivalents     0.0683
_diffrn_reflns_av_sigmaI/netI     0.0185
_diffrn_reflns_theta_min     1.14
_diffrn_reflns_theta_max     26.56
_diffrn_reflns_theta_full     26.56
_diffrn_measured_fraction_theta_max     0.999
_diffrn_measured_fraction_theta_full     0.999
_diffrn_reflns_limit_h_min     -14
_diffrn_reflns_limit_h_max     14
_diffrn_reflns_limit_k_min     -30
_diffrn_reflns_limit_k_max     30
_diffrn_reflns_limit_l_min     -33
_diffrn_reflns_limit_l_max     33
_refine_special_details
;
Refinement of F² against ALL reflections. The weighted R-factor
wR and goodness of fit S are based on F², conventional
R-factors R are based on F, with F set to zero for
negative F². The threshold expression of F² >
σ(F²) is used only for calculating R-factors(gt) etc.
and is not relevant to the choice of reflections for refinement.
R-factors based on F² are statistically about twice as large
as those based on F, and R- factors based on ALL data will be
even larger.
;
_reflns_number_total     15641
_reflns_number_gt     14786
_reflns_threshold_expression     I>2σ(I)
_refine_ls_structure_factor_coef     Fsqd
_refine_ls_matrix_type     full
_refine_ls_R_factor_all     0.0414
_refine_ls_R_factor_gt     0.0389
_refine_ls_wR_factor_gt     0.0964
_refine_ls_wR_factor_ref     0.0976
_refine_ls_goodness_of_fit_ref     1.072
_refine_ls_restrained_S_all     1.072
_refine_ls_number_reflns     15641
_refine_ls_number_parameters     888
_refine_ls_number_restraints     0
_refine_ls_hydrogen_treatment     mixed
_refine_ls_weighting_scheme     calc
_refine_ls_weighting_details
        'calc w=1/[σ²(Fo²)+(0.0428P)²+3.32078P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_hydrogens     geom
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary     difmap
_refine_ls_shift/su_max     0.001
_refine_ls_shift/su_mean     0.000
_refine_diff_density_max     0.676
_refine_diff_density_min     -0.268
_refine_ls_extinction_method     'SHELXL97 (Sheldrick, 2008)'
_refine_ls_extinction_coef     0.0066(3)
_refine_ls_extinction_expression
                                  'Fc^*^=kFc[1+0.001xFc²λ³/sin(2θ)]^-1/4^'
_refine_ls_abs_structure_details     'Flack (1983), 7070 Friedel pairs'
_refine_ls_abs_structure_Flack     0.13(5)
loop_
    _atom_type_symbol
    _atom_type_description
    _atom_type_scat_dispersion_real
    _atom_type_scat_dispersion_imag
    _atom_type_scat_source
    'C' 'C' 0.0181 0.0091
                         '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'
    'K' 'K' 0.3868 1.0657
                         'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
    'O' 'O' 0.0492 0.0322
                         'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
_computing_data_collection
;
MXDC (Canadian Light Source, 2007)
;
_computing_cell_refinement
;
SAINT (Bruker, 2008)
;
_computing_data_reduction
;
SAINT (Bruker, 2008)
;
_computing_structure_solution
;
SIR2004 (Burla et al., 2005)
;
_computing_structure_refinement     'SHELXL97 (Sheldrick, 2008)'
_computing_molecular_graphics
;
CAMERON (Watkin et al., 1993) and SHELXTL (Sheldrick,
2008)
;
_computing_publication_material     'publCIF (Westrip, 2010)'
loop_
    _atom_site_type_symbol
    _atom_site_label
    _atom_site_fract_x
    _atom_site_fract_y
    _atom_site_fract_z
    _atom_site_U_iso_or_equiv
    _atom_site_adp_type
    _atom_site_calc_flag
    _atom_site_refinement_flags
    _atom_site_occupancy
    _atom_site_symmetry_multiplicity
    _atom_site_disorder_assembly
    _atom_site_disorder_group
    S S1 -0.06845(4) 0.127042(18) 0.090277(17) 0.02233(9) Uani d . 1 1 . .
    O O1 -0.17707(11) 0.11209(5) 0.06398(5) 0.0271(3) Uani d . 1 1 . .
    O O2 -0.07595(14) 0.16630(6) 0.13357(6) 0.0354(3) Uani d . 1 1 . .
    O O3 -0.08897(10) 0.29370(5) -0.04562(5) 0.0195(2) Uani d . 1 1 . .
    O O4 -0.13526(13) 0.43495(7) -0.08748(6) 0.0363(3) Uani d . 1 1 . .
    O O5 -0.00833(10) 0.52881(5) 0.04376(5) 0.0217(2) Uani d . 1 1 . .
    O O6 -0.23894(11) 0.60979(5) 0.08609(5) 0.0254(3) Uani d . 1 1 . .
    O O7 0.14169(11) 0.73331(5) 0.00361(5) 0.0235(3) Uani d . 1 1 . .
    O O8 0.39874(10) 0.61559(5) 0.04670(5) 0.0236(3) Uani d . 1 1 . .
    O O9 0.46130(11) 0.48642(5) -0.00112(5) 0.0241(3) Uani d . 1 1 . .
    O O10 0.49071(11) 0.35178(5) 0.09127(5) 0.0249(3) Uani d . 1 1 . .
    O O11 0.07474(10) 0.33509(5) 0.06117(5) 0.0205(2) Uani d . 1 1 . .
    N N1 0.17591(13) 0.26283(6) 0.02387(6) 0.0181(3) Uani d . 1 1 . .
    H H1D 0.236(2) 0.2415(11) 0.0257(10) 0.039(7) Uiso d . 1 1 . .
    N N2 0.08840(13) 0.33307(6) -0.05879(6) 0.0182(3) Uani d . 1 1 . .
    H H2D 0.159(2) 0.3328(9) -0.0533(9) 0.027(6) Uiso d . 1 1 . .
    N N3 -0.04192(13) 0.41929(6) -0.01064(6) 0.0191(3) Uani d . 1 1 . .
    H H3D 0.013(2) 0.3973(11) 0.0051(10) 0.040(7) Uiso d . 1 1 . .
    N N4 -0.17491(12) 0.54896(6) 0.00023(6) 0.0187(3) Uani d . 1 1 . .
    N N5 -0.12916(13) 0.68641(6) 0.06591(6) 0.0192(3) Uani d . 1 1 . .
    N N6 0.10867(13) 0.67134(6) 0.07003(6) 0.0198(3) Uani d . 1 1 . .
    H H6D 0.058(2) 0.6570(10) 0.0901(10) 0.035(6) Uiso d . 1 1 . .
    N N7 0.22187(13) 0.57544(6) 0.03130(6) 0.0187(3) Uani d . 1 1 . .
    H H7D 0.149(2) 0.5777(9) 0.0358(8) 0.020(5) Uiso d . 1 1 . .
    N N8 0.35439(13) 0.48453(6) 0.07367(6) 0.0194(3) Uani d . 1 1 . .
    H H8D 0.289(2) 0.4905(9) 0.0850(9) 0.023(5) Uiso d . 1 1 . .
    N N9 0.29706(13) 0.37135(6) 0.09964(6) 0.0184(3) Uani d . 1 1 . .
    H H9D 0.2520(19) 0.3925(9) 0.1032(8) 0.018(5) Uiso d . 1 1 . .
    C C1 0.07734(15) 0.24387(7) -0.00892(6) 0.0181(3) Uani d . 1 1 . .
    H H1 0.1088(18) 0.2196(9) -0.0359(8) 0.021(5) Uiso d . 1 1 . .
    C C2 -0.01456(15) 0.21152(7) 0.02323(7) 0.0193(3) Uani d . 1 1 . .
    H H2A -0.0383 0.2350 0.0537 0.023 Uiso calc R 1 1 . .
    H H2B -0.0849 0.2051 0.0012 0.023 Uiso calc R 1 1 . .
    C C3 0.03106(15) 0.15447(7) 0.04287(7) 0.0199(3) Uani d . 1 1 . .
    H H3A 0.1095 0.1594 0.0589 0.024 Uiso calc R 1 1 . .
    H H3B 0.0383 0.1276 0.0131 0.024 Uiso calc R 1 1 . .
    C C4 0.00104(19) 0.06480(8) 0.11222(7) 0.0286(4) Uani d . 1 1 . .
    H H4A 0.0806 0.0739 0.1241 0.034 Uiso calc R 1 1 . .
    H H4B 0.0050 0.0373 0.0834 0.034 Uiso calc R 1 1 . .
    H H4C -0.0437 0.0485 0.1414 0.034 Uiso calc R 1 1 . .
    C C5 0.01818(14) 0.29271(7) -0.03886(6) 0.0173(3) Uani d . 1 1 . .
    C C6 0.04216(15) 0.37934(7) -0.09113(7) 0.0202(3) Uani d . 1 1 . .
    H H6 0.1004(17) 0.4084(8) -0.0936(8) 0.016(5) Uiso d . 1 1 . .
    C C7 0.00408(17) 0.35989(8) -0.14566(7) 0.0271(4) Uani d . 1 1 . .
    H H7A -0.0394 0.3913 -0.1628 0.033 Uiso calc R 1 1 . .
    H H7B -0.0507 0.3275 -0.1417 0.033 Uiso calc R 1 1 . .
    C C8 0.10494(19) 0.34175(8) -0.18180(7) 0.0302(4) Uani d . 1 1 . .
    H H8 0.1546 0.3132 -0.1630 0.036 Uiso calc R 1 1 . .
    C C9 0.0533(3) 0.31392(14) -0.23131(10) 0.0657(9) Uani d . 1 1 . .
    H H9A 0.0068 0.3420 -0.2507 0.079 Uiso calc R 1 1 . .
    H H9B 0.0031 0.2820 -0.2211 0.079 Uiso calc R 1 1 . .
    H H9C 0.1172 0.3001 -0.2537 0.079 Uiso calc R 1 1 . .
    C C10 0.18107(19) 0.39122(9) -0.19816(8) 0.0329(4) Uani d . 1 1 . .
    H H10A 0.1328 0.4197 -0.2161 0.039 Uiso calc R 1 1 . .
    H H10B 0.2425 0.3778 -0.2221 0.039 Uiso calc R 1 1 . .
    H H10C 0.2172 0.4082 -0.1670 0.039 Uiso calc R 1 1 . .
    C C11 -0.05535(16) 0.41260(7) -0.06280(7) 0.0222(3) Uani d . 1 1 . .
    C C12 -0.13120(15) 0.44886(7) 0.02026(7) 0.0196(3) Uani d . 1 1 . .
    H H12 -0.2079(16) 0.4453(8) 0.0012(7) 0.011(4) Uiso d . 1 1 . .
    C C13 -0.14060(15) 0.42277(7) 0.07553(7) 0.0214(3) Uani d . 1 1 . .
    H H13 -0.0595 0.4167 0.0894 0.026 Uiso calc R 1 1 . .
    C C14 -0.20542(18) 0.46237(8) 0.11314(8) 0.0291(4) Uani d . 1 1 . .
    H H14A -0.1622 0.4982 0.1163 0.035 Uiso calc R 1 1 . .
    H H14B -0.2114 0.4444 0.1478 0.035 Uiso calc R 1 1 . .
    H H14C -0.2843 0.4699 0.0995 0.035 Uiso calc R 1 1 . .
    C C15 -0.20159(16) 0.36443(7) 0.07129(7) 0.0241(4) Uani d . 1 1 . .
    H H15A -0.2856 0.3705 0.0631 0.029 Uiso calc R 1 1 . .
    H H15B -0.1665 0.3430 0.0417 0.029 Uiso calc R 1 1 . .
    C C16 -0.1920(2) 0.32872(9) 0.12116(8) 0.0334(4) Uani d . 1 1 . .
    H H16A -0.1092 0.3240 0.1305 0.040 Uiso calc R 1 1 . .
    H H16B -0.2273 0.2913 0.1151 0.040 Uiso calc R 1 1 . .
    H H16C -0.2333 0.3479 0.1499 0.040 Uiso calc R 1 1 . .
    C C17 -0.10061(14) 0.51252(7) 0.02211(6) 0.0185(3) Uani d . 1 1 . .
    C C18 -0.28831(15) 0.53559(7) -0.02517(8) 0.0242(4) Uani d . 1 1 . .
    H H18A -0.3384 0.5124 -0.0017 0.029 Uiso calc R 1 1 . .
    H H18B -0.2763 0.5149 -0.0586 0.029 Uiso calc R 1 1 . .
    C C19 -0.34284(15) 0.59379(7) -0.03497(8) 0.0255(4) Uani d . 1 1 . .
    H H19A -0.3925 0.6055 -0.0049 0.031 Uiso calc R 1 1 . .
    H H19B -0.3911 0.5936 -0.0673 0.031 Uiso calc R 1 1 . .
    C C20 -0.23707(15) 0.63339(7) -0.04102(7) 0.0232(3) Uani d . 1 1 . .
    H H20A -0.2586 0.6733 -0.0334 0.028 Uiso calc R 1 1 . .
    H H20B -0.2038 0.6311 -0.0769 0.028 Uiso calc R 1 1 . .
    C C21 -0.15010(14) 0.61022(7) 0.00013(7) 0.0183(3) Uani d . 1 1 . .
    H H21 -0.0659(18) 0.6162(8) -0.0107(8) 0.020(5) Uiso d . 1 1 . .
    C C22 -0.17600(14) 0.63503(7) 0.05464(7) 0.0191(3) Uani d . 1 1 . .
    C C23 -0.16410(17) 0.71832(8) 0.11377(7) 0.0248(4) Uani d . 1 1 . .
    H H23A -0.1416 0.6974 0.1460 0.030 Uiso calc R 1 1 . .
    H H23B -0.2497 0.7252 0.1143 0.030 Uiso calc R 1 1 . .
    C C24 -0.09648(17) 0.77413(7) 0.10923(7) 0.0261(4) Uani d . 1 1 . .
    H H24A -0.0194 0.7714 0.1269 0.031 Uiso calc R 1 1 . .
    H H24B -0.1414 0.8060 0.1248 0.031 Uiso calc R 1 1 . .
    C C25 -0.08167(16) 0.78212(7) 0.04989(7) 0.0231(3) Uani d . 1 1 . .
    H H25A -0.0147 0.8075 0.0419 0.028 Uiso calc R 1 1 . .
    H H25B -0.1537 0.7980 0.0339 0.028 Uiso calc R 1 1 . .
    C C26 -0.05830(15) 0.72114(7) 0.03017(7) 0.0200(3) Uani d . 1 1 . .
    H H26 -0.0833(18) 0.7144(8) -0.0064(8) 0.021(5) Uiso d . 1 1 . .
    C C27 0.07336(15) 0.70872(7) 0.03343(7) 0.0195(3) Uani d . 1 1 . .
    C C28 0.23268(14) 0.66436(7) 0.08197(7) 0.0194(3) Uani d . 1 1 . .
    H H28 0.2752(17) 0.6983(8) 0.0714(7) 0.013(4) Uiso d . 1 1 . .
    C C29 0.25020(17) 0.65554(7) 0.14107(7) 0.0241(4) Uani d . 1 1 . .
    H H29A 0.2097 0.6202 0.1520 0.029 Uiso calc R 1 1 . .
    H H29B 0.3349 0.6508 0.1484 0.029 Uiso calc R 1 1 . .
    C C30 0.20363(16) 0.70476(8) 0.17311(7) 0.0249(4) Uani d . 1 1 . .
    C C31 0.24759(19) 0.75914(9) 0.16578(8) 0.0320(4) Uani d . 1 1 . .
    H H31 0.3056 0.7657 0.1397 0.038 Uiso calc . 1 1 . .
    C C32 0.2071(2) 0.80423(9) 0.19648(10) 0.0423(5) Uani d . 1 1 . .
    H H32 0.2362 0.8416 0.1907 0.051 Uiso calc . 1 1 . .
    C C33 0.1246(2) 0.79445(11) 0.23530(9) 0.0452(6) Uani d . 1 1 . .
    H H33 0.0982 0.8249 0.2567 0.054 Uiso calc . 1 1 . .
    C C34 0.0809(2) 0.74078(12) 0.24280(9) 0.0473(6) Uani d . 1 1 . .
    H H34 0.0248 0.7341 0.2697 0.057 Uiso calc . 1 1 . .
    C C35 0.11831(19) 0.69604(9) 0.21119(8) 0.0353(5) Uani d . 1 1 . .
    H H35 0.0853 0.6593 0.2157 0.042 Uiso calc . 1 1 . .
    C C36 0.29122(15) 0.61622(7) 0.05117(7) 0.0202(3) Uani d . 1 1 . .
    C C37 0.27005(15) 0.53101(7) -0.00266(7) 0.0196(3) Uani d . 1 1 . .
    H H37 0.2069(18) 0.5028(8) -0.0056(8) 0.016(5) Uiso d . 1 1 . .
    C C38 0.30238(16) 0.55437(8) -0.05705(7) 0.0240(4) Uani d . 1 1 . .
    H H38A 0.3555 0.5873 -0.0527 0.029 Uiso calc R 1 1 . .
    H H38B 0.3453 0.5247 -0.0769 0.029 Uiso calc R 1 1 . .
    C C39 0.19690(15) 0.57258(7) -0.08839(7) 0.0221(3) Uani d . 1 1 . .
    C C40 0.1399(2) 0.53331(8) -0.11996(8) 0.0338(4) Uani d . 1 1 . .
    H H40 0.1677 0.4953 -0.1212 0.041 Uiso calc . 1 1 . .
    C C41 0.0432(2) 0.54846(10) -0.14979(10) 0.0432(5) Uani d . 1 1 . .
    H H41 0.0048 0.5208 -0.1709 0.052 Uiso calc . 1 1 . .
    C C42 0.00256(19) 0.60398(9) -0.14873(8) 0.0356(4) Uani d . 1 1 . .
    H H42 -0.0632 0.6147 -0.1694 0.043 Uiso calc . 1 1 . .
    C C43 0.05820(18) 0.64371(8) -0.11743(8) 0.0294(4) Uani d . 1 1 . .
    H H43 0.0309 0.6819 -0.1166 0.035 Uiso calc . 1 1 . .
    C C44 0.15384(16) 0.62784(7) -0.08726(7) 0.0244(3) Uani d . 1 1 . .
    H H44 0.1907 0.6552 -0.0654 0.029 Uiso calc . 1 1 . .
    C C45 0.37290(15) 0.49933(7) 0.02332(7) 0.0192(3) Uani d . 1 1 . .
    C C46 0.43758(15) 0.44978(7) 0.10252(6) 0.0193(3) Uani d . 1 1 . .
    H H46 0.5132(19) 0.4548(9) 0.0867(8) 0.020(5) Uiso d . 1 1 . .
    C C47 0.44064(16) 0.46801(8) 0.16082(7) 0.0245(4) Uani d . 1 1 . .
    H H47 0.3592 0.4651 0.1752 0.029 Uiso calc R 1 1 . .
    C C48 0.4794(2) 0.53018(9) 0.16478(9) 0.0382(5) Uani d . 1 1 . .
    H H48A 0.4822 0.5415 0.2018 0.046 Uiso calc R 1 1 . .
    H H48B 0.4234 0.5543 0.1459 0.046 Uiso calc R 1 1 . .
    H H48C 0.5574 0.5345 0.1491 0.046 Uiso calc R 1 1 . .
    C C49 0.52034(17) 0.43021(8) 0.19405(7) 0.0276(4) Uani d . 1 1 . .
    H H49A 0.6017 0.4347 0.1824 0.033 Uiso calc R 1 1 . .
    H H49B 0.4966 0.3904 0.1900 0.033 Uiso calc R 1 1 . .
    H H49C 0.5139 0.4412 0.2311 0.033 Uiso calc R 1 1 . .
    C C50 0.41129(14) 0.38636(7) 0.09661(6) 0.0188(3) Uani d . 1 1 . .
    C C51 0.26020(15) 0.31211(7) 0.10027(6) 0.0175(3) Uani d . 1 1 . .
    H H51 0.3301(17) 0.2884(8) 0.0892(8) 0.015(4) Uiso d . 1 1 . .
    C C52 0.21596(15) 0.29313(7) 0.15511(6) 0.0202(3) Uani d . 1 1 . .
    H H52 0.1436 0.3154 0.1636 0.024 Uiso calc R 1 1 . .
    C C53 0.18312(18) 0.23028(8) 0.15318(7) 0.0266(4) Uani d . 1 1 . .
    H H53A 0.2479 0.2085 0.1378 0.032 Uiso calc R 1 1 . .
    H H53B 0.1127 0.2254 0.1316 0.032 Uiso calc R 1 1 . .
    H H53C 0.1676 0.2166 0.1889 0.032 Uiso calc R 1 1 . .
    C C54 0.30799(17) 0.30602(8) 0.19729(7) 0.0265(4) Uani d . 1 1 . .
    H H54A 0.3815 0.2860 0.1881 0.032 Uiso calc R 1 1 . .
    H H54B 0.3247 0.3473 0.1969 0.032 Uiso calc R 1 1 . .
    C C55 0.2724(2) 0.28895(10) 0.25270(8) 0.0367(5) Uani d . 1 1 . .
    H H55A 0.1925 0.3022 0.2597 0.044 Uiso calc R 1 1 . .
    H H55B 0.3265 0.3062 0.2781 0.044 Uiso calc R 1 1 . .
    H H55C 0.2754 0.2475 0.2560 0.044 Uiso calc R 1 1 . .
    C C56 0.16265(14) 0.30451(7) 0.05998(6) 0.0168(3) Uani d . 1 1 . .
    O O60 0.12773(12) 0.47775(6) 0.12012(5) 0.0297(3) Uani d . 1 1 . .
    H H60 0.079(3) 0.4921(13) 0.0981(12) 0.057(8) Uiso d . 1 1 . .
    C C61 0.1074(2) 0.49805(9) 0.17215(8) 0.0353(4) Uani d . 1 1 . .
    H H61A 0.0341 0.5206 0.1728 0.042 Uiso calc R 1 1 . .
    H H61B 0.1727 0.5233 0.1828 0.042 Uiso calc R 1 1 . .
    C C62 0.09782(19) 0.44943(9) 0.21069(8) 0.0328(4) Uani d . 1 1 . .
    H H62A 0.1664 0.4241 0.2063 0.039 Uiso calc R 1 1 . .
    H H62B 0.0265 0.4271 0.2026 0.039 Uiso calc R 1 1 . .
    C C63 0.0921(2) 0.46934(10) 0.26723(9) 0.0410(5) Uani d . 1 1 . .
    H H63A 0.1635 0.4917 0.2751 0.049 Uiso calc R 1 1 . .
    H H63B 0.0238 0.4950 0.2713 0.049 Uiso calc R 1 1 . .
    C C64 0.0819(3) 0.42177(10) 0.30675(9) 0.0476(6) Uani d . 1 1 . .
    H H64A 0.0121 0.3990 0.2990 0.057 Uiso calc R 1 1 . .
    H H64B 0.0753 0.4378 0.3422 0.057 Uiso calc R 1 1 . .
    H H64C 0.1518 0.3976 0.3048 0.057 Uiso calc R 1 1 . .
    O O70A 0.1247(2) 0.09480(8) 0.31769(7) 0.0434(6) Uani d P 0.863(4) 1 A 1
    H H70A 0.1276 0.1154 0.3446 0.052 Uiso calc PR 0.863(4) 1 A 1
    C C71A 0.1982(3) 0.11838(12) 0.27765(10) 0.0463(8) Uani d P 0.863(4) 1 A 1
    H H71A 0.2799 0.1210 0.2907 0.056 Uiso calc PR 0.863(4) 1 A 1
    H H71B 0.1712 0.1572 0.2688 0.056 Uiso calc PR 0.863(4) 1 A 1
    O O70B 0.2098(14) 0.0817(5) 0.3176(4) 0.0434(6) Uani d P 0.137(4) 1 A 2
    H H70B 0.2402 0.0965 0.3444 0.052 Uiso calc PR 0.137(4) 1 A 2
    C C71B 0.266(2) 0.1064(8) 0.2685(7) 0.0463(8) Uani d P 0.137(4) 1 A 2
    H H71C 0.2609 0.1484 0.2679 0.056 Uiso calc PR 0.137(4) 1 A 2
    H H71D 0.3491 0.0947 0.2652 0.056 Uiso calc PR 0.137(4) 1 A 2
    C C72 0.1942(2) 0.08097(10) 0.22855(9) 0.0414(5) Uani d . 1 1 . .
    H H72A 0.1115 0.0774 0.2171 0.050 Uiso calc R 1 1 A 1
    H H72B 0.2378 0.1003 0.2001 0.050 Uiso calc R 1 1 A 1
    C C73 0.2445(3) 0.02210(11) 0.23559(10) 0.0499(6) Uani d . 1 1 A .
    H H73A 0.2037 0.0032 0.2652 0.060 Uiso calc R 1 1 . .
    H H73B 0.3284 0.0255 0.2451 0.060 Uiso calc R 1 1 . .
    C C74 0.2337(2) -0.01505(10) 0.18712(11) 0.0489(6) Uani d . 1 1 . .
    H H74A 0.1507 -0.0199 0.1782 0.059 Uiso calc R 1 1 A .
    H H74B 0.2688 -0.0523 0.1942 0.059 Uiso calc R 1 1 . .
    H H74C 0.2747 0.0030 0.1577 0.059 Uiso calc R 1 1 . .
    O O80 0.48874(14) 0.21728(6) 0.41673(6) 0.0350(3) Uani d . 1 1 . .
    H H80A 0.439(3) 0.2245(14) 0.4479(14) 0.075(10) Uiso d . 1 1 . .
    H H80B 0.506(3) 0.1789(13) 0.4284(12) 0.058(8) Uiso d . 1 1 . .
_geom_special_details
;
All e.s.d.'s (except the e.s.d. in the dihedral angle between two l.s. planes)
are estimated using the full covariance matrix. The cell e.s.d.'s are taken
into account individually in the estimation of e.s.d.'s in distances, angles
and torsion angles; correlations between e.s.d.'s in cell parameters are only
used when they are defined by crystal symmetry. An approximate (isotropic)
treatment of cell e.s.d.'s is used for estimating e.s.d.'s involving l.s.
planes.
;
loop_
    _geom_bond_atom_site_label_1
    _geom_bond_atom_site_label_2
    _geom_bond_site_symmetry_2
    _geom_bond_distance
    _geom_bond_publ_flag
    S1 O2 . 1.4398(14) ?
    S1 O1 . 1.4509(16) ?
    S1 C4 . 1.756(2) ?
    S1 C3 . 1.7772(18) ?
    O3 C5 . 1.234(2) ?
    O4 C11 . 1.225(2) ?
    O5 C17 . 1.248(2) ?
    O6 C22 . 1.228(2) ?
    O7 C27 . 1.231(2) ?
    O8 C36 . 1.231(2) ?
    O9 C45 . 1.223(2) ?
    O10 C50 . 1.225(2) ?
    O11 C56 . 1.234(2) ?
    N1 C56 . 1.352(2) ?
    N1 C1 . 1.469(2) ?
    N1 H1D . 0.85(3) ?
    N2 C5 . 1.341(2) ?
    N2 C6 . 1.463(2) ?
    N2 H2D . 0.81(2) ?
    N3 C11 . 1.345(2) ?
    N3 C12 . 1.462(2) ?
    N3 H3D . 0.91(3) ?
    N4 C17 . 1.327(2) ?
    N4 C21 . 1.468(2) ?
    N4 C18 . 1.479(2) ?
    N5 C22 . 1.352(2) ?
    N5 C26 . 1.465(2) ?
    N5 C23 . 1.485(2) ?
    N6 C27 . 1.343(2) ?
    N6 C28 . 1.456(2) ?
    N6 H6D . 0.84(3) ?
    N7 C36 . 1.342(2) ?
    N7 C37 . 1.463(2) ?
    N7 H7D . 0.84(2) ?
    N8 C45 . 1.344(2) ?
    N8 C46 . 1.452(2) ?
    N8 H8D . 0.82(2) ?
    N9 C50 . 1.352(2) ?
    N9 C51 . 1.455(2) ?
    N9 H9D . 0.72(2) ?
    C1 C2 . 1.532(2) ?
    C1 C5 . 1.535(2) ?
    C1 H1 . 0.96(2) ?
    C2 C3 . 1.523(2) ?
    C2 H2A . 0.9900 ?
    C2 H2B . 0.9900 ?
    C3 H3A . 0.9900 ?
    C3 H3B . 0.9900 ?
    C4 H4A . 0.9800 ?
    C4 H4B . 0.9800 ?
    C4 H4C . 0.9800 ?
    C6 C7 . 1.524(2) ?
    C6 C11 . 1.539(2) ?
    C6 H6 . 0.95(2) ?
    C7 C8 . 1.533(3) ?
    C7 H7A . 0.9900 ?
    C7 H7B . 0.9900 ?
    C8 C10 . 1.510(3) ?
    C8 C9 . 1.537(3) ?
    C8 H8 . 1.0000 ?
    C9 H9A . 0.9800 ?
    C9 H9B . 0.9800 ?
    C9 H9C . 0.9800 ?
    C10 H10A . 0.9800 ?
    C10 H10B . 0.9800 ?
    C10 H10C . 0.9800 ?
    C12 C13 . 1.538(2) ?
    C12 C17 . 1.538(2) ?
    C12 H12 . 1.003(19) ?
    C13 C14 . 1.526(2) ?
    C13 C15 . 1.542(2) ?
    C13 H13 . 1.0000 ?
    C14 H14A . 0.9800 ?
    C14 H14B . 0.9800 ?
    C14 H14C . 0.9800 ?
    C15 C16 . 1.525(3) ?
    C15 H15A . 0.9900 ?
    C15 H15B . 0.9900 ?
    C16 H16A . 0.9800 ?
    C16 H16B . 0.9800 ?
    C16 H16C . 0.9800 ?
    C18 C19 . 1.524(2) ?
    C18 H18A . 0.9900 ?
    C18 H18B . 0.9900 ?
    C19 C20 . 1.532(3) ?
    C19 H19A . 0.9900 ?
    C19 H19B . 0.9900 ?
    C20 C21 . 1.542(2) ?
    C20 H20A . 0.9900 ?
    C20 H20B . 0.9900 ?
    C21 C22 . 1.533(2) ?
    C21 H21 . 1.01(2) ?
    C23 C24 . 1.527(3) ?
    C23 H23A . 0.9900 ?
    C23 H23B . 0.9900 ?
    C24 C25 . 1.531(3) ?
    C24 H24A . 0.9900 ?
    C24 H24B . 0.9900 ?
    C25 C26 . 1.543(2) ?
    C25 H25A . 0.9900 ?
    C25 H25B . 0.9900 ?
    C26 C27 . 1.532(3) ?
    C26 H26 . 0.99(2) ?
    C28 C36 . 1.530(2) ?
    C28 C29 . 1.531(2) ?
    C28 H28 . 0.97(2) ?
    C29 C30 . 1.512(3) ?
    C29 H29A . 0.9900 ?
    C29 H29B . 0.9900 ?
    C30 C31 . 1.386(3) ?
    C30 C35 . 1.388(3) ?
    C31 C32 . 1.396(3) ?
    C31 H31 . 0.9500 ?
    C32 C33 . 1.384(4) ?
    C32 H32 . 0.9500 ?
    C33 C34 . 1.370(4) ?
    C33 H33 . 0.9500 ?
    C34 C35 . 1.391(3) ?
    C34 H34 . 0.9500 ?
    C35 H35 . 0.9500 ?
    C37 C38 . 1.534(2) ?
    C37 C45 . 1.538(2) ?
    C37 H37 . 0.98(2) ?
    C38 C39 . 1.505(3) ?
    C38 H38A . 0.9900 ?
    C38 H38B . 0.9900 ?
    C39 C40 . 1.386(3) ?
    C39 C44 . 1.390(3) ?
    C40 C41 . 1.385(3) ?
    C40 H40 . 0.9500 ?
    C41 C42 . 1.386(3) ?
    C41 H41 . 0.9500 ?
    C42 C43 . 1.382(3) ?
    C42 H42 . 0.9500 ?
    C43 C44 . 1.385(3) ?
    C43 H43 . 0.9500 ?
    C44 H44 . 0.9500 ?
    C46 C50 . 1.529(2) ?
    C46 C47 . 1.544(2) ?
    C46 H46 . 0.96(2) ?
    C47 C49 . 1.527(3) ?
    C47 C48 . 1.531(3) ?
    C47 H47 . 1.0000 ?
    C48 H48A . 0.9800 ?
    C48 H48B . 0.9800 ?
    C48 H48C . 0.9800 ?
    C49 H49A . 0.9800 ?
    C49 H49B . 0.9800 ?
    C49 H49C . 0.9800 ?
    C51 C56 . 1.523(2) ?
    C51 C52 . 1.549(2) ?
    C51 H51 . 1.01(2) ?
    C52 C53 . 1.526(2) ?
    C52 C54 . 1.531(3) ?
    C52 H52 . 1.0000 ?
    C53 H53A . 0.9800 ?
    C53 H53B . 0.9800 ?
    C53 H53C . 0.9800 ?
    C54 C55 . 1.521(3) ?
    C54 H54A . 0.9900 ?
    C54 H54B . 0.9900 ?
    C55 H55A . 0.9800 ?
    C55 H55B . 0.9800 ?
    C55 H55C . 0.9800 ?
    O60 C61 . 1.426(3) ?
    O60 H60 . 0.86(3) ?
    C61 C62 . 1.510(3) ?
    C61 H61A . 0.9900 ?
    C61 H61B . 0.9900 ?
    C62 C63 . 1.514(3) ?
    C62 H62A . 0.9900 ?
    C62 H62B . 0.9900 ?
    C63 C64 . 1.509(3) ?
    C63 H63A . 0.9900 ?
    C63 H63B . 0.9900 ?
    C64 H64A . 0.9800 ?
    C64 H64B . 0.9800 ?
    C64 H64C . 0.9800 ?
    O70A C71A . 1.431(3) ?
    O70A H70A . 0.8400 ?
    C71A C72 . 1.529(4) ?
    C71A H71A . 0.9900 ?
    C71A H71B . 0.9900 ?
    O70B C71B . 1.52(2) ?
    O70B H70B . 0.8400 ?
    C71B C72 . 1.436(19) ?
    C71B H71C . 0.9900 ?
    C71B H71D . 0.9900 ?
    C72 C73 . 1.509(3) ?
    C72 H72A . 0.9900 ?
    C72 H72B . 0.9900 ?
    C73 C74 . 1.516(4) ?
    C73 H73A . 0.9900 ?
    C73 H73B . 0.9900 ?
    C74 H74A . 0.9800 ?
    C74 H74B . 0.9800 ?
    C74 H74C . 0.9800 ?
    O80 H80A . 0.99(4) ?
    O80 H80B . 0.97(3) ?
loop_
    _geom_angle_atom_site_label_1
    _geom_angle_atom_site_label_2
    _geom_angle_atom_site_label_3
    _geom_angle_site_symmetry_1
    _geom_angle_site_symmetry_3
    _geom_angle
    _geom_angle_publ_flag
    O2 S1 O1 . . 117.22(9) ?
    O2 S1 C4 . . 108.57(10) ?
    O1 S1 C4 . . 109.25(9) ?
    O2 S1 C3 . . 108.92(8) ?
    O1 S1 C3 . . 108.67(9) ?
    C4 S1 C3 . . 103.32(10) ?
    C56 N1 C1 . . 121.36(14) ?
    C56 N1 H1D . . 118.7(17) ?
    C1 N1 H1D . . 118.0(17) ?
    C5 N2 C6 . . 121.61(15) ?
    C5 N2 H2D . . 121.1(16) ?
    C6 N2 H2D . . 117.3(16) ?
    C11 N3 C12 . . 120.45(15) ?
    C11 N3 H3D . . 116.6(16) ?
    C12 N3 H3D . . 121.1(16) ?
    C17 N4 C21 . . 120.75(14) ?
    C17 N4 C18 . . 127.14(14) ?
    C21 N4 C18 . . 112.10(13) ?
    C22 N5 C26 . . 125.77(14) ?
    C22 N5 C23 . . 121.32(15) ?
    C26 N5 C23 . . 112.02(13) ?
    C27 N6 C28 . . 120.66(15) ?
    C27 N6 H6D . . 118.5(17) ?
    C28 N6 H6D . . 119.7(17) ?
    C36 N7 C37 . . 120.78(15) ?
    C36 N7 H7D . . 119.1(14) ?
    C37 N7 H7D . . 119.8(14) ?
    C45 N8 C46 . . 121.69(15) ?
    C45 N8 H8D . . 115.9(16) ?
    C46 N8 H8D . . 121.2(16) ?
    C50 N9 C51 . . 121.94(15) ?
    C50 N9 H9D . . 120.9(17) ?
    C51 N9 H9D . . 117.0(17) ?
    N1 C1 C2 . . 111.78(14) ?
    N1 C1 C5 . . 113.02(13) ?
    C2 C1 C5 . . 109.65(14) ?
    N1 C1 H1 . . 107.4(12) ?
    C2 C1 H1 . . 110.0(12) ?
    C5 C1 H1 . . 104.7(12) ?
    C3 C2 C1 . . 112.28(14) ?
    C3 C2 H2A . . 109.1 ?
    C1 C2 H2A . . 109.1 ?
    C3 C2 H2B . . 109.1 ?
    C1 C2 H2B . . 109.1 ?
    H2A C2 H2B . . 107.9 ?
    C2 C3 S1 . . 108.93(12) ?
    C2 C3 H3A . . 109.9 ?
    S1 C3 H3A . . 109.9 ?
    C2 C3 H3B . . 109.9 ?
    S1 C3 H3B . . 109.9 ?
    H3A C3 H3B . . 108.3 ?
    S1 C4 H4A . . 109.5 ?
    S1 C4 H4B . . 109.5 ?
    H4A C4 H4B . . 109.5 ?
    S1 C4 H4C . . 109.5 ?
    H4A C4 H4C . . 109.5 ?
    H4B C4 H4C . . 109.5 ?
    O3 C5 N2 . . 121.66(16) ?
    O3 C5 C1 . . 121.24(15) ?
    N2 C5 C1 . . 117.06(15) ?
    N2 C6 C7 . . 113.03(14) ?
    N2 C6 C11 . . 112.05(14) ?
    C7 C6 C11 . . 111.91(15) ?
    N2 C6 H6 . . 108.6(12) ?
    C7 C6 H6 . . 110.6(12) ?
    C11 C6 H6 . . 99.8(12) ?
    C6 C7 C8 . . 114.57(16) ?
    C6 C7 H7A . . 108.6 ?
    C8 C7 H7A . . 108.6 ?
    C6 C7 H7B . . 108.6 ?
    C8 C7 H7B . . 108.6 ?
    H7A C7 H7B . . 107.6 ?
    C10 C8 C7 . . 112.46(17) ?
    C10 C8 C9 . . 108.81(18) ?
    C7 C8 C9 . . 108.83(19) ?
    C10 C8 H8 . . 108.9 ?
    C7 C8 H8 . . 108.9 ?
    C9 C8 H8 . . 108.9 ?
    C8 C9 H9A . . 109.5 ?
    C8 C9 H9B . . 109.5 ?
    H9A C9 H9B . . 109.5 ?
    C8 C9 H9C . . 109.5 ?
    H9A C9 H9C . . 109.5 ?
    H9B C9 H9C . . 109.5 ?
    C8 C10 H10A . . 109.5 ?
    C8 C10 H10B . . 109.5 ?
    H10A C10 H10B . . 109.5 ?
    C8 C10 H10C . . 109.5 ?
    H10A C10 H10C . . 109.5 ?
    H10B C10 H10C . . 109.5 ?
    O4 C11 N3 . . 122.69(17) ?
    O4 C11 C6 . . 121.04(16) ?
    N3 C11 C6 . . 116.06(15) ?
    N3 C12 C13 . . 110.50(14) ?
    N3 C12 C17 . . 108.76(13) ?
    C13 C12 C17 . . 112.12(14) ?
    N3 C12 H12 . . 107.9(11) ?
    C13 C12 H12 . . 110.3(11) ?
    C17 C12 H12 . . 107.1(10) ?
    C14 C13 C12 . . 111.31(15) ?
    C14 C13 C15 . . 111.63(15) ?
    C12 C13 C15 . . 108.82(14) ?
    C14 C13 H13 . . 108.3 ?
    C12 C13 H13 . . 108.3 ?
    C15 C13 H13 . . 108.3 ?
    C13 C14 H14A . . 109.5 ?
    C13 C14 H14B . . 109.5 ?
    H14A C14 H14B . . 109.5 ?
    C13 C14 H14C . . 109.5 ?
    H14A C14 H14C . . 109.5 ?
    H14B C14 H14C . . 109.5 ?
    C16 C15 C13 . . 113.53(16) ?
    C16 C15 H15A . . 108.9 ?
    C13 C15 H15A . . 108.9 ?
    C16 C15 H15B . . 108.9 ?
    C13 C15 H15B . . 108.9 ?
    H15A C15 H15B . . 107.7 ?
    C15 C16 H16A . . 109.5 ?
    C15 C16 H16B . . 109.5 ?
    H16A C16 H16B . . 109.5 ?
    C15 C16 H16C . . 109.5 ?
    H16A C16 H16C . . 109.5 ?
    H16B C16 H16C . . 109.5 ?
    O5 C17 N4 . . 121.67(15) ?
    O5 C17 C12 . . 120.22(15) ?
    N4 C17 C12 . . 118.10(15) ?
    N4 C18 C19 . . 103.72(14) ?
    N4 C18 H18A . . 111.0 ?
    C19 C18 H18A . . 111.0 ?
    N4 C18 H18B . . 111.0 ?
    C19 C18 H18B . . 111.0 ?
    H18A C18 H18B . . 109.0 ?
    C18 C19 C20 . . 103.97(14) ?
    C18 C19 H19A . . 111.0 ?
    C20 C19 H19A . . 111.0 ?
    C18 C19 H19B . . 111.0 ?
    C20 C19 H19B . . 111.0 ?
    H19A C19 H19B . . 109.0 ?
    C19 C20 C21 . . 102.90(14) ?
    C19 C20 H20A . . 111.2 ?
    C21 C20 H20A . . 111.2 ?
    C19 C20 H20B . . 111.2 ?
    C21 C20 H20B . . 111.2 ?
    H20A C20 H20B . . 109.1 ?
    N4 C21 C22 . . 109.56(13) ?
    N4 C21 C20 . . 102.95(13) ?
    C22 C21 C20 . . 110.84(13) ?
    N4 C21 H21 . . 108.6(11) ?
    C22 C21 H21 . . 112.2(11) ?
    C20 C21 H21 . . 112.2(11) ?
    O6 C22 N5 . . 121.66(16) ?
    O6 C22 C21 . . 121.19(15) ?
    N5 C22 C21 . . 117.13(14) ?
    N5 C23 C24 . . 103.72(14) ?
    N5 C23 H23A . . 111.0 ?
    C24 C23 H23A . . 111.0 ?
    N5 C23 H23B . . 111.0 ?
    C24 C23 H23B . . 111.0 ?
    H23A C23 H23B . . 109.0 ?
    C23 C24 C25 . . 103.64(14) ?
    C23 C24 H24A . . 111.0 ?
    C25 C24 H24A . . 111.0 ?
    C23 C24 H24B . . 111.0 ?
    C25 C24 H24B . . 111.0 ?
    H24A C24 H24B . . 109.0 ?
    C24 C25 C26 . . 103.04(14) ?
    C24 C25 H25A . . 111.2 ?
    C26 C25 H25A . . 111.2 ?
    C24 C25 H25B . . 111.2 ?
    C26 C25 H25B . . 111.2 ?
    H25A C25 H25B . . 109.1 ?
    N5 C26 C27 . . 113.61(14) ?
    N5 C26 C25 . . 102.78(14) ?
    C27 C26 C25 . . 109.21(14) ?
    N5 C26 H26 . . 109.7(12) ?
    C27 C26 H26 . . 107.6(12) ?
    C25 C26 H26 . . 114.0(12) ?
    O7 C27 N6 . . 123.03(16) ?
    O7 C27 C26 . . 119.81(15) ?
    N6 C27 C26 . . 117.15(15) ?
    N6 C28 C36 . . 113.61(14) ?
    N6 C28 C29 . . 110.30(14) ?
    C36 C28 C29 . . 110.23(14) ?
    N6 C28 H28 . . 109.5(11) ?
    C36 C28 H28 . . 104.4(11) ?
    C29 C28 H28 . . 108.5(11) ?
    C30 C29 C28 . . 112.32(14) ?
    C30 C29 H29A . . 109.1 ?
    C28 C29 H29A . . 109.1 ?
    C30 C29 H29B . . 109.1 ?
    C28 C29 H29B . . 109.1 ?
    H29A C29 H29B . . 107.9 ?
    C31 C30 C35 . . 118.92(18) ?
    C31 C30 C29 . . 120.46(17) ?
    C35 C30 C29 . . 120.60(18) ?
    C30 C31 C32 . . 120.4(2) ?
    C30 C31 H31 . . 119.8 ?
    C32 C31 H31 . . 119.8 ?
    C33 C32 C31 . . 119.9(2) ?
    C33 C32 H32 . . 120.1 ?
    C31 C32 H32 . . 120.1 ?
    C34 C33 C32 . . 120.0(2) ?
    C34 C33 H33 . . 120.0 ?
    C32 C33 H33 . . 120.0 ?
    C33 C34 C35 . . 120.3(2) ?
    C33 C34 H34 . . 119.8 ?
    C35 C34 H34 . . 119.8 ?
    C30 C35 C34 . . 120.4(2) ?
    C30 C35 H35 . . 119.8 ?
    C34 C35 H35 . . 119.8 ?
    O8 C36 N7 . . 122.91(16) ?
    O8 C36 C28 . . 119.37(15) ?
    N7 C36 C28 . . 117.70(15) ?
    N7 C37 C38 . . 111.54(14) ?
    N7 C37 C45 . . 112.25(14) ?
    C38 C37 C45 . . 112.20(14) ?
    N7 C37 H37 . . 104.6(11) ?
    C38 C37 H37 . . 110.5(11) ?
    C45 C37 H37 . . 105.3(11) ?
    C39 C38 C37 . . 112.82(15) ?
    C39 C38 H38A . . 109.0 ?
    C37 C38 H38A . . 109.0 ?
    C39 C38 H38B . . 109.0 ?
    C37 C38 H38B . . 109.0 ?
    H38A C38 H38B . . 107.8 ?
    C40 C39 C44 . . 118.00(17) ?
    C40 C39 C38 . . 119.48(17) ?
    C44 C39 C38 . . 122.51(16) ?
    C41 C40 C39 . . 121.30(19) ?
    C41 C40 H40 . . 119.3 ?
    C39 C40 H40 . . 119.3 ?
    C40 C41 C42 . . 119.86(19) ?
    C40 C41 H41 . . 120.1 ?
    C42 C41 H41 . . 120.1 ?
    C43 C42 C41 . . 119.66(19) ?
    C43 C42 H42 . . 120.2 ?
    C41 C42 H42 . . 120.2 ?
    C42 C43 C44 . . 119.90(18) ?
    C42 C43 H43 . . 120.1 ?
    C44 C43 H43 . . 120.1 ?
    C43 C44 C39 . . 121.27(17) ?
    C43 C44 H44 . . 119.4 ?
    C39 C44 H44 . . 119.4 ?
    O9 C45 N8 . . 123.35(16) ?
    O9 C45 C37 . . 122.02(16) ?
    N8 C45 C37 . . 114.53(15) ?
    N8 C46 C50 . . 111.81(14) ?
    N8 C46 C47 . . 110.13(14) ?
    C50 C46 C47 . . 111.71(14) ?
    N8 C46 H46 . . 107.8(12) ?
    C50 C46 H46 . . 104.8(12) ?
    C47 C46 H46 . . 110.4(13) ?
    C49 C47 C48 . . 110.37(16) ?
    C49 C47 C46 . . 112.55(15) ?
    C48 C47 C46 . . 109.58(16) ?
    C49 C47 H47 . . 108.1 ?
    C48 C47 H47 . . 108.1 ?
    C46 C47 H47 . . 108.1 ?
    C47 C48 H48A . . 109.5 ?
    C47 C48 H48B . . 109.5 ?
    H48A C48 H48B . . 109.5 ?
    C47 C48 H48C . . 109.5 ?
    H48A C48 H48C . . 109.5 ?
    H48B C48 H48C . . 109.5 ?
    C47 C49 H49A . . 109.5 ?
    C47 C49 H49B . . 109.5 ?
    H49A C49 H49B . . 109.5 ?
    C47 C49 H49C . . 109.5 ?
    H49A C49 H49C . . 109.5 ?
    H49B C49 H49C . . 109.5 ?
    O10 C50 N9 . . 123.05(16) ?
    O10 C50 C46 . . 120.92(15) ?
    N9 C50 C46 . . 115.99(15) ?
    N9 C51 C56 . . 108.42(13) ?
    N9 C51 C52 . . 112.31(13) ?
    C56 C51 C52 . . 109.55(14) ?
    N9 C51 H51 . . 107.2(11) ?
    C56 C51 H51 . . 108.9(11) ?
    C52 C51 H51 . . 110.4(11) ?
    C53 C52 C54 . . 112.50(15) ?
    C53 C52 C51 . . 109.27(14) ?
    C54 C52 C51 . . 110.55(14) ?
    C53 C52 H52 . . 108.1 ?
    C54 C52 H52 . . 108.1 ?
    C51 C52 H52 . . 108.1 ?
    C52 C53 H53A . . 109.5 ?
    C52 C53 H53B . . 109.5 ?
    H53A C53 H53B . . 109.5 ?
    C52 C53 H53C . . 109.5 ?
    H53A C53 H53C . . 109.5 ?
    H53B C53 H53C . . 109.5 ?
    C55 C54 C52 . . 114.49(16) ?
    C55 C54 H54A . . 108.6 ?
    C52 C54 H54A . . 108.6 ?
    C55 C54 H54B . . 108.6 ?
    C52 C54 H54B . . 108.6 ?
    H54A C54 H54B . . 107.6 ?
    C54 C55 H55A . . 109.5 ?
    C54 C55 H55B . . 109.5 ?
    H55A C55 H55B . . 109.5 ?
    C54 C55 H55C . . 109.5 ?
    H55A C55 H55C . . 109.5 ?
    H55B C55 H55C . . 109.5 ?
    O11 C56 N1 . . 122.02(15) ?
    O11 C56 C51 . . 120.54(15) ?
    N1 C56 C51 . . 117.44(14) ?
    C61 O60 H60 . . 111(2) ?
    O60 C61 C62 . . 111.15(17) ?
    O60 C61 H61A . . 109.4 ?
    C62 C61 H61A . . 109.4 ?
    O60 C61 H61B . . 109.4 ?
    C62 C61 H61B . . 109.4 ?
    H61A C61 H61B . . 108.0 ?
    C61 C62 C63 . . 112.68(18) ?
    C61 C62 H62A . . 109.1 ?
    C63 C62 H62A . . 109.1 ?
    C61 C62 H62B . . 109.1 ?
    C63 C62 H62B . . 109.1 ?
    H62A C62 H62B . . 107.8 ?
    C64 C63 C62 . . 114.02(19) ?
    C64 C63 H63A . . 108.7 ?
    C62 C63 H63A . . 108.7 ?
    C64 C63 H63B . . 108.7 ?
    C62 C63 H63B . . 108.7 ?
    H63A C63 H63B . . 107.6 ?
    C63 C64 H64A . . 109.5 ?
    C63 C64 H64B . . 109.5 ?
    H64A C64 H64B . . 109.5 ?
    C63 C64 H64C . . 109.5 ?
    H64A C64 H64C . . 109.5 ?
    H64B C64 H64C . . 109.5 ?
    C71A O70A H70A . . 109.5 ?
    O70A C71A C72 . . 109.9(2) ?
    O70A C71A H71A . . 109.7 ?
    C72 C71A H71A . . 109.7 ?
    O70A C71A H71B . . 109.7 ?
    C72 C71A H71B . . 109.7 ?
    H71A C71A H71B . . 108.2 ?
    C71B O70B H70B . . 109.5 ?
    C72 C71B O70B . . 100.5(13) ?
    C72 C71B H71C . . 111.7 ?
    O70B C71B H71C . . 111.7 ?
    C72 C71B H71D . . 111.7 ?
    O70B C71B H71D . . 111.7 ?
    H71C C71B H71D . . 109.4 ?
    C71B C72 C73 . . 94.6(10) ?
    C73 C72 C71A . . 114.8(2) ?
    C71B C72 H72A . . 141.9 ?
    C73 C72 H72A . . 108.6 ?
    C71A C72 H72A . . 108.6 ?
    C71B C72 H72B . . 92.3 ?
    C73 C72 H72B . . 108.6 ?
    C71A C72 H72B . . 108.6 ?
    H72A C72 H72B . . 107.5 ?
    C72 C73 C74 . . 113.7(2) ?
    C72 C73 H73A . . 108.8 ?
    C74 C73 H73A . . 108.8 ?
    C72 C73 H73B . . 108.8 ?
    C74 C73 H73B . . 108.8 ?
    H73A C73 H73B . . 107.7 ?
    C73 C74 H74A . . 109.5 ?
    C73 C74 H74B . . 109.5 ?
    H74A C74 H74B . . 109.5 ?
    C73 C74 H74C . . 109.5 ?
    H74A C74 H74C . . 109.5 ?
    H74B C74 H74C . . 109.5 ?
    H80A O80 H80B . . 92(2) ?
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_site_symmetry_1
    _geom_torsion_site_symmetry_2
    _geom_torsion_site_symmetry_3
    _geom_torsion_site_symmetry_4
    _geom_torsion
    _geom_torsion_publ_flag
    C56 N1 C1 C2 . . . . -69.93(18) ?
    C56 N1 C1 C5 . . . . 54.3(2) ?
    N1 C1 C2 C3 . . . . -68.07(17) ?
    C5 C1 C2 C3 . . . . 165.78(13) ?
    C1 C2 C3 S1 . . . . 168.11(11) ?
    O2 S1 C3 C2 . . . . -60.58(14) ?
    O1 S1 C3 C2 . . . . 68.19(13) ?
    C4 S1 C3 C2 . . . . -175.86(12) ?
    C6 N2 C5 O3 . . . . -2.1(2) ?
    C6 N2 C5 C1 . . . . 175.65(14) ?
    N1 C1 C5 O3 . . . . -142.96(15) ?
    C2 C1 C5 O3 . . . . -17.5(2) ?
    N1 C1 C5 N2 . . . . 39.23(19) ?
    C2 C1 C5 N2 . . . . 164.67(14) ?
    C5 N2 C6 C7 . . . . -71.9(2) ?
    C5 N2 C6 C11 . . . . 55.7(2) ?
    N2 C6 C7 C8 . . . . -68.8(2) ?
    C11 C6 C7 C8 . . . . 163.58(15) ?
    C6 C7 C8 C10 . . . . -68.9(2) ?
    C6 C7 C8 C9 . . . . 170.50(19) ?
    C12 N3 C11 O4 . . . . 7.0(3) ?
    C12 N3 C11 C6 . . . . -178.29(14) ?
    N2 C6 C11 O4 . . . . -149.19(17) ?
    C7 C6 C11 O4 . . . . -21.0(2) ?
    N2 C6 C11 N3 . . . . 36.0(2) ?
    C7 C6 C11 N3 . . . . 164.14(15) ?
    C11 N3 C12 C13 . . . . 146.05(15) ?
    C11 N3 C12 C17 . . . . -90.48(18) ?
    N3 C12 C13 C14 . . . . 163.62(14) ?
    C17 C12 C13 C14 . . . . 42.1(2) ?
    N3 C12 C13 C15 . . . . -72.95(18) ?
    C17 C12 C13 C15 . . . . 165.55(14) ?
    C14 C13 C15 C16 . . . . -69.6(2) ?
    C12 C13 C15 C16 . . . . 167.21(15) ?
    C21 N4 C17 O5 . . . . 0.8(2) ?
    C18 N4 C17 O5 . . . . -178.07(16) ?
    C21 N4 C17 C12 . . . . -179.28(14) ?
    C18 N4 C17 C12 . . . . 1.8(3) ?
    N3 C12 C17 O5 . . . . -63.5(2) ?
    C13 C12 C17 O5 . . . . 59.0(2) ?
    N3 C12 C17 N4 . . . . 116.64(17) ?
    C13 C12 C17 N4 . . . . -120.86(17) ?
    C17 N4 C18 C19 . . . . 171.41(16) ?
    C21 N4 C18 C19 . . . . -7.56(19) ?
    N4 C18 C19 C20 . . . . 28.20(18) ?
    C18 C19 C20 C21 . . . . -38.05(18) ?
    C17 N4 C21 C22 . . . . -77.03(19) ?
    C18 N4 C21 C22 . . . . 102.01(16) ?
    C17 N4 C21 C20 . . . . 164.98(15) ?
    C18 N4 C21 C20 . . . . -15.97(18) ?
    C19 C20 C21 N4 . . . . 32.78(16) ?
    C19 C20 C21 C22 . . . . -84.29(16) ?
    C26 N5 C22 O6 . . . . -176.63(16) ?
    C23 N5 C22 O6 . . . . -8.3(2) ?
    C26 N5 C22 C21 . . . . 1.7(2) ?
    C23 N5 C22 C21 . . . . 170.00(15) ?
    N4 C21 C22 O6 . . . . -19.1(2) ?
    C20 C21 C22 O6 . . . . 93.81(19) ?
    N4 C21 C22 N5 . . . . 162.59(14) ?
    C20 C21 C22 N5 . . . . -84.48(18) ?
    C22 N5 C23 C24 . . . . -176.92(15) ?
    C26 N5 C23 C24 . . . . -7.11(19) ?
    N5 C23 C24 C25 . . . . 28.18(18) ?
    C23 C24 C25 C26 . . . . -38.51(18) ?
    C22 N5 C26 C27 . . . . -89.54(19) ?
    C23 N5 C26 C27 . . . . 101.19(17) ?
    C22 N5 C26 C25 . . . . 152.60(16) ?
    C23 N5 C26 C25 . . . . -16.67(18) ?
    C24 C25 C26 N5 . . . . 33.60(17) ?
    C24 C25 C26 C27 . . . . -87.33(17) ?
    C28 N6 C27 O7 . . . . 9.6(2) ?
    C28 N6 C27 C26 . . . . -169.37(14) ?
    N5 C26 C27 O7 . . . . 176.69(14) ?
    C25 C26 C27 O7 . . . . -69.2(2) ?
    N5 C26 C27 N6 . . . . -4.3(2) ?
    C25 C26 C27 N6 . . . . 109.82(17) ?
    C27 N6 C28 C36 . . . . -94.07(18) ?
    C27 N6 C28 C29 . . . . 141.59(16) ?
    N6 C28 C29 C30 . . . . -59.00(19) ?
    C36 C28 C29 C30 . . . . 174.75(15) ?
    C28 C29 C30 C31 . . . . -59.7(2) ?
    C28 C29 C30 C35 . . . . 121.90(19) ?
    C35 C30 C31 C32 . . . . 0.4(3) ?
    C29 C30 C31 C32 . . . . -178.02(19) ?
    C30 C31 C32 C33 . . . . 1.5(3) ?
    C31 C32 C33 C34 . . . . -1.4(4) ?
    C32 C33 C34 C35 . . . . -0.6(4) ?
    C31 C30 C35 C34 . . . . -2.4(3) ?
    C29 C30 C35 C34 . . . . 176.02(19) ?
    C33 C34 C35 C30 . . . . 2.6(4) ?
    C37 N7 C36 O8 . . . . -7.5(3) ?
    C37 N7 C36 C28 . . . . 174.28(14) ?
    N6 C28 C36 O8 . . . . 160.55(16) ?
    C29 C28 C36 O8 . . . . -75.1(2) ?
    N6 C28 C36 N7 . . . . -21.2(2) ?
    C29 C28 C36 N7 . . . . 103.17(18) ?
    C36 N7 C37 C38 . . . . -72.1(2) ?
    C36 N7 C37 C45 . . . . 54.8(2) ?
    N7 C37 C38 C39 . . . . -67.15(19) ?
    C45 C37 C38 C39 . . . . 165.93(14) ?
    C37 C38 C39 C40 . . . . -88.6(2) ?
    C37 C38 C39 C44 . . . . 91.7(2) ?
    C44 C39 C40 C41 . . . . 0.3(3) ?
    C38 C39 C40 C41 . . . . -179.4(2) ?
    C39 C40 C41 C42 . . . . 0.6(4) ?
    C40 C41 C42 C43 . . . . -0.7(4) ?
    C41 C42 C43 C44 . . . . -0.2(3) ?
    C42 C43 C44 C39 . . . . 1.1(3) ?
    C40 C39 C44 C43 . . . . -1.2(3) ?
    C38 C39 C44 C43 . . . . 178.52(17) ?
    C46 N8 C45 O9 . . . . -2.3(2) ?
    C46 N8 C45 C37 . . . . 174.08(14) ?
    N7 C37 C45 O9 . . . . -138.38(16) ?
    C38 C37 C45 O9 . . . . -11.8(2) ?
    N7 C37 C45 N8 . . . . 45.15(19) ?
    C38 C37 C45 N8 . . . . 171.69(14) ?
    C45 N8 C46 C50 . . . . -89.61(19) ?
    C45 N8 C46 C47 . . . . 145.58(15) ?
    N8 C46 C47 C49 . . . . 175.97(15) ?
    C50 C46 C47 C49 . . . . 51.1(2) ?
    N8 C46 C47 C48 . . . . -60.82(19) ?
    C50 C46 C47 C48 . . . . 174.31(15) ?
    C51 N9 C50 O10 . . . . 4.2(3) ?
    C51 N9 C50 C46 . . . . -173.40(14) ?
    N8 C46 C50 O10 . . . . 140.00(16) ?
    C47 C46 C50 O10 . . . . -96.07(19) ?
    N8 C46 C50 N9 . . . . -42.4(2) ?
    C47 C46 C50 N9 . . . . 81.56(18) ?
    C50 N9 C51 C56 . . . . -131.06(16) ?
    C50 N9 C51 C52 . . . . 107.76(17) ?
    N9 C51 C52 C53 . . . . -178.01(14) ?
    C56 C51 C52 C53 . . . . 61.46(18) ?
    N9 C51 C52 C54 . . . . -53.68(19) ?
    C56 C51 C52 C54 . . . . -174.22(14) ?
    C53 C52 C54 C55 . . . . -57.6(2) ?
    C51 C52 C54 C55 . . . . 179.91(16) ?
    C1 N1 C56 O11 . . . . -12.7(2) ?
    C1 N1 C56 C51 . . . . 166.44(14) ?
    N9 C51 C56 O11 . . . . -53.7(2) ?
    C52 C51 C56 O11 . . . . 69.17(19) ?
    N9 C51 C56 N1 . . . . 127.18(15) ?
    C52 C51 C56 N1 . . . . -109.94(16) ?
    O60 C61 C62 C63 . . . . 172.53(18) ?
    C61 C62 C63 C64 . . . . 179.8(2) ?
    O70B C71B C72 C73 . . . . -72.0(13) ?
    O70B C71B C72 C71A . . . . 58.0(13) ?
    O70A C71A C72 C71B . . . . -122.2(14) ?
    O70A C71A C72 C73 . . . . -65.0(4) ?
    C71B C72 C73 C74 . . . . -155.3(9) ?
    C71A C72 C73 C74 . . . . 177.1(2) ?
loop_
    _geom_hbond_atom_site_label_D
    _geom_hbond_atom_site_label_H
    _geom_hbond_atom_site_label_A
    _geom_hbond_site_symmetry_A
    _geom_hbond_distance_DH
    _geom_hbond_distance_HA
    _geom_hbond_distance_DA
    _geom_hbond_angle_DHA
    _geom_hbond_publ_flag
    N1 H1D O3 3_555 0.85(3) 2.21(3) 3.043(3) 163(2) y
    N2 H2D O1 3_555 0.81(2) 2.29(2) 2.972(3) 141(2) y
    N3 H3D O11 . 0.91(3) 2.16(3) 3.005(2) 154(2) y
    N7 H7D O5 . 0.84(2) 2.14(2) 2.862(3) 144(2) y
    N8 H8D O60 . 0.82(2) 2.07(2) 2.847(2) 161(2) y
    N9 H9D O60 . 0.72(2) 2.49(2) 3.203(2) 169(2) y
    O60 H60 O5 . 0.86(3) 1.91(3) 2.761(2) 170(3) y
    O70A H70A O6 4_545 0.84 2.18 2.795(2) 130 y
    O80 H80A O7 2_565 0.99(4) 1.95(4) 2.906(2) 159(3) y
    O80 H80B O8 4_645 0.97(3) 1.95(3) 2.869(2) 157(3) y
