##############################################################################
#                                                                            #
# This CIF contains the data in a paper accepted for publication in          #
# Acta Crystallographica Section C. It conforms to the requirements of       #
# Notes for Authors for Acta Crystallographica Section C, 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     ' SHELXL97 (Sheldrick, 2008)'
_journal_date_recd_electronic     2011-06-23
_journal_date_accepted     2011-07-11
_journal_name_full     'Acta Crystallographica, Section C'
_journal_year     2011
_journal_volume     67
_journal_issue      8
_journal_page_first     o334
_journal_page_last     o336
_journal_paper_category     FO
_journal_coeditor_code     FG3225
_publ_contact_author_name     'Dr Graham Smith'
_publ_contact_author_address
;
Faculty of Science and Technology
Queensland University of Technology
GPO Box 2434
Brisbane
Queensland 4001
Australia
;
_publ_contact_author_email     g.smith@qut.edu.au
_publ_contact_author_fax     '61 7 3138 1804'
_publ_contact_author_phone     '61 7 3300 2667'
_publ_section_title
;
2,3-Dimethoxy-10-oxostrychnidinium 2-(2,4,6-trinitroanilino)benzoate
monohydrate: a 1:1 proton-transfer salt of brucine with
o-picraminobenzoic acid
;
loop_
    _publ_author_name
    _publ_author_address
    'Graham Smith'
;
Faculty of Science and Technology
Queensland University of Technology
GPO Box 2434
Brisbane
Queensland 4001
Australia
;
    'Urs D. Wermuth'
;
Faculty of Science and Technology
Queensland University of Technology
GPO Box 2434
Brisbane
Queensland 4001
Australia
;
data_I
_audit_creation_method     SHELXL97
_chemical_name_systematic
;
2,3-Dimethoxy-10-oxostrychnidinium 2-(2,4,6-trinitroanilino)benzoate monohydrate
;
_chemical_name_common     'brucinium 2-(picramino)benzoate monohydrate'
_chemical_formula_moiety     'C23 H27 N2 O4 +, C13 H7 N4 O8 -, H2 O'
_chemical_formula_sum     'C36 H36 N6 O13'
_chemical_formula_iupac     'C23 H27 N2 O4 +, C13 H7 N4 O8 -, H2 O'
_chemical_formula_weight     760.71
_chemical_melting_point     474
_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     12.4407(3)
_cell_length_b     19.1542(5)
_cell_length_c     14.6744(4)
_cell_angle_alpha     90.00
_cell_angle_beta     90.00
_cell_angle_gamma     90.00
_cell_volume     3496.79(16)
_cell_formula_units_Z     4
_cell_measurement_reflns_used     5473
_cell_measurement_theta_min     3.22
_cell_measurement_theta_max     28.66
_cell_measurement_temperature     173(2)
_exptl_crystal_description     prism
_exptl_crystal_colour     orange--red
_exptl_crystal_size_max     0.35
_exptl_crystal_size_mid     0.15
_exptl_crystal_size_min     0.12
_exptl_crystal_density_diffrn     1.445
_exptl_crystal_density_meas     ?
_exptl_crystal_density_method     'not measured'
_exptl_crystal_F_000     1592
_exptl_absorpt_coefficient_mu     0.112
_exptl_absorpt_correction_type     multi-scan
_exptl_absorpt_process_details     '(CrysAlis PRO; Oxford Diffraction, 2010)'
_exptl_absorpt_correction_T_min     0.911
_exptl_absorpt_correction_T_max     0.980
_exptl_special_details
;
;
_diffrn_ambient_temperature     173(2)
_diffrn_radiation_type     MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_source     'Enhance(Mo) X-ray source'
_diffrn_radiation_monochromator     'graphite'
_diffrn_measurement_device_type     'Oxford Gemini-S CCD area-detector'
_diffrn_measurement_method     ω
_diffrn_detector_area_resol_mean     16.077
_diffrn_reflns_number     12634
_diffrn_reflns_av_R_equivalents     0.0313
_diffrn_reflns_av_sigmaI/netI     0.0544
_diffrn_reflns_theta_min     3.22
_diffrn_reflns_theta_max     28.72
_diffrn_reflns_theta_full     26.00
_diffrn_measured_fraction_theta_max     0.897
_diffrn_measured_fraction_theta_full     0.997
_diffrn_reflns_limit_h_min     -15
_diffrn_reflns_limit_h_max     16
_diffrn_reflns_limit_k_min     -15
_diffrn_reflns_limit_k_max     24
_diffrn_reflns_limit_l_min     -10
_diffrn_reflns_limit_l_max     19
_diffrn_standards_number     0
_diffrn_standards_interval_count     .
_diffrn_standards_interval_time     .
_diffrn_standards_decay_%     ?
_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     4487
_reflns_number_gt     3291
_reflns_threshold_expression     I>2σ(I)
_refine_ls_structure_factor_coef     Fsqd
_refine_ls_matrix_type     full
_refine_ls_R_factor_all     0.0643
_refine_ls_R_factor_gt     0.0434
_refine_ls_wR_factor_gt     0.1034
_refine_ls_wR_factor_ref     0.1088
_refine_ls_goodness_of_fit_ref     0.960
_refine_ls_restrained_S_all     0.960
_refine_ls_number_reflns     4487
_refine_ls_number_parameters     506
_refine_ls_number_restraints     0
_refine_ls_hydrogen_treatment     constr
_refine_ls_weighting_scheme     calc
_refine_ls_weighting_details
               'calc w = 1/[σ²(Fo²)+(0.0670P)²] 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     0.00
_refine_ls_shift/su_mean     0.00
_refine_diff_density_max     0.582
_refine_diff_density_min     -0.199
_refine_ls_extinction_method     none
_refine_ls_extinction_coef     ?
_refine_ls_abs_structure_details     ?
_refine_ls_abs_structure_Flack     ?
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 0.0000
                         '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 0.0000
                         'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
    'O' 'O' 0.0106 0.0000
                         'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
_computing_data_collection     'CrysAlis PRO (Oxford Diffraction, 2010)'
_computing_cell_refinement     'CrysAlis PRO (Oxford Diffraction, 2010)'
_computing_data_reduction     'CrysAlis PRO (Oxford Diffraction, 2010)'
_computing_structure_solution     'SIR92 (Altomare et al., 1994)'
_computing_structure_refinement
                      'SHELXL97 (Sheldrick, 2008) within WinGX (Farrugia, 1999)'
_computing_molecular_graphics     'PLATON (Spek, 2009)'
_computing_publication_material     'PLATON (Spek, 2009)'
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_thermal_displace_type
    _atom_site_calc_flag
    _atom_site_refinement_flags
    _atom_site_occupancy
    O O2 0.43311(17) 0.76601(11) 0.13182(15) 0.0281(7) Uani . . 1.000
    O O3 0.54210(18) 0.88045(11) 0.13700(17) 0.0322(7) Uani . . 1.000
    O O24 1.13073(17) 0.63667(11) 0.10356(18) 0.0326(7) Uani . . 1.000
    O O25 0.94682(19) 0.84959(10) 0.11056(17) 0.0331(7) Uani . . 1.000
    N N9 0.8737(2) 0.74233(13) 0.08799(18) 0.0224(7) Uani . . 1.000
    N N19 0.7968(2) 0.50747(13) 0.06583(18) 0.0241(8) Uani . . 1.000
    C C1 0.5940(2) 0.69516(15) 0.1099(2) 0.0215(8) Uani . . 1.000
    C C2 0.5424(2) 0.75837(16) 0.1225(2) 0.0241(9) Uani . . 1.000
    C C3 0.6016(3) 0.82112(15) 0.1245(2) 0.0243(9) Uani . . 1.000
    C C4 0.7128(2) 0.82058(16) 0.1131(2) 0.0233(9) Uani . . 1.000
    C C5 0.7633(2) 0.75610(16) 0.0998(2) 0.0213(8) Uani . . 1.000
    C C6 0.7057(2) 0.69462(15) 0.0984(2) 0.0215(8) Uani . . 1.000
    C C7 0.7773(2) 0.63375(15) 0.0744(2) 0.0206(8) Uani . . 1.000
    C C8 0.8914(2) 0.66543(14) 0.0880(2) 0.0208(8) Uani . . 1.000
    C C10 0.9571(3) 0.78597(15) 0.1077(2) 0.0244(9) Uani . . 1.000
    C C11 1.0656(2) 0.75091(16) 0.1238(2) 0.0245(9) Uani . . 1.000
    C C12 1.0667(2) 0.67642(16) 0.1652(2) 0.0253(9) Uani . . 1.000
    C C13 0.9507(2) 0.64873(15) 0.1765(2) 0.0207(8) Uani . . 1.000
    C C14 0.9343(2) 0.57309(16) 0.2070(2) 0.0243(9) Uani . . 1.000
    C C15 0.8125(2) 0.56377(17) 0.2203(2) 0.0254(9) Uani . . 1.000
    C C16 0.7572(2) 0.56638(15) 0.1289(2) 0.0218(9) Uani . . 1.000
    C C17 0.7629(2) 0.60873(16) -0.0243(2) 0.0239(9) Uani . . 1.000
    C C18 0.8216(3) 0.53983(16) -0.0256(2) 0.0268(10) Uani . . 1.000
    C C20 0.8909(2) 0.46751(15) 0.1057(2) 0.0272(9) Uani . . 1.000
    C C21 0.9743(2) 0.51825(16) 0.1389(2) 0.0271(9) Uani . . 1.000
    C C22 1.0754(3) 0.51547(17) 0.1088(3) 0.0347(10) Uani . . 1.000
    C C23 1.1585(3) 0.56752(18) 0.1356(3) 0.0408(13) Uani . . 1.000
    C C25 0.3698(3) 0.70430(17) 0.1254(3) 0.0310(10) Uani . . 1.000
    C C26 0.5997(3) 0.94476(17) 0.1464(3) 0.0405(13) Uani . . 1.000
    O O2A 0.70810(19) 0.38946(13) -0.00247(18) 0.0394(8) Uani . . 1.000
    O O3A 0.5401(2) 0.42006(14) -0.03672(19) 0.0514(9) Uani . . 1.000
    O O21A 0.7589(2) 0.15589(15) 0.00324(19) 0.0447(9) Uani . . 1.000
    O O22A 0.7869(2) 0.07097(13) -0.0925(2) 0.0585(12) Uani . . 1.000
    O O41A 1.1443(2) 0.06880(13) -0.2137(2) 0.0496(10) Uani . . 1.000
    O O42A 1.23433(19) 0.16523(14) -0.22799(19) 0.0414(9) Uani . . 1.000
    O O61A 1.0688(2) 0.38010(13) -0.1700(2) 0.0620(10) Uani . . 1.000
    O O62A 0.9226(2) 0.39008(13) -0.0948(2) 0.0534(9) Uani . . 1.000
    N N1A 0.7865(2) 0.28354(13) -0.09923(18) 0.0257(8) Uani . . 1.000
    N N21A 0.8024(2) 0.13002(15) -0.0637(2) 0.0377(10) Uani . . 1.000
    N N41A 1.1537(2) 0.13260(16) -0.2063(2) 0.0354(10) Uani . . 1.000
    N N61A 0.9899(2) 0.35466(15) -0.1339(2) 0.0329(9) Uani . . 1.000
    C C1A 0.6792(2) 0.26329(16) -0.1132(2) 0.0234(9) Uani . . 1.000
    C C2A 0.5974(3) 0.30770(16) -0.0813(2) 0.0254(9) Uani . . 1.000
    C C3A 0.4906(3) 0.2865(2) -0.0945(2) 0.0342(11) Uani . . 1.000
    C C4A 0.4641(3) 0.22466(19) -0.1356(2) 0.0343(11) Uani . . 1.000
    C C5A 0.5454(3) 0.18486(18) -0.1736(2) 0.0318(10) Uani . . 1.000
    C C6A 0.6513(3) 0.20464(17) -0.1650(2) 0.0265(9) Uani . . 1.000
    C C11A 0.8777(2) 0.24640(16) -0.1138(2) 0.0238(9) Uani . . 1.000
    C C21A 0.8847(3) 0.17189(16) -0.1116(2) 0.0280(9) Uani . . 1.000
    C C22A 0.6174(3) 0.37806(17) -0.0369(2) 0.0304(10) Uani . . 1.000
    C C31A 0.9717(3) 0.13470(17) -0.1424(2) 0.0298(10) Uani . . 1.000
    C C41A 1.0618(3) 0.17046(17) -0.1701(2) 0.0271(9) Uani . . 1.000
    C C51A 1.0671(2) 0.24219(17) -0.1630(2) 0.0258(9) Uani . . 1.000
    C C61A 0.9782(3) 0.27870(16) -0.1351(2) 0.0242(9) Uani . . 1.000
    O O1W 0.5011(3) 0.54468(17) 0.0418(3) 0.0557(13) Uani . . 0.730
    O O2W 0.3660(11) 0.5033(7) -0.1388(9) 0.034(3) Uiso . . 0.170
    O O3W 0.5694(16) 0.5455(10) -0.1653(14) 0.023(5) Uiso . . 0.100
    H H1 0.55510 0.65370 0.10900 0.0260 Uiso calc R 1.000
    H H4 0.75220 0.86180 0.11420 0.0280 Uiso calc R 1.000
    H H8 0.93690 0.65280 0.03600 0.0250 Uiso calc R 1.000
    H H12 1.10200 0.67770 0.22490 0.0300 Uiso calc R 1.000
    H H13 0.91730 0.67780 0.22360 0.0250 Uiso calc R 1.000
    H H14 0.97050 0.56600 0.26550 0.0290 Uiso calc R 1.000
    H H16 0.67970 0.56100 0.13820 0.0260 Uiso calc R 1.000
    H H19 0.74170 0.47690 0.05800 0.0290 Uiso . R 1.000
    H H22 1.09470 0.47960 0.06940 0.0420 Uiso calc R 1.000
    H H111 1.10720 0.78090 0.16370 0.0290 Uiso calc R 1.000
    H H112 1.10300 0.74900 0.06590 0.0290 Uiso calc R 1.000
    H H151 0.79820 0.51930 0.24950 0.0310 Uiso calc R 1.000
    H H152 0.78490 0.60060 0.25920 0.0310 Uiso calc R 1.000
    H H171 0.68750 0.60270 -0.03910 0.0290 Uiso calc R 1.000
    H H172 0.79470 0.64140 -0.06700 0.0290 Uiso calc R 1.000
    H H181 0.89830 0.54680 -0.03290 0.0320 Uiso calc R 1.000
    H H182 0.79580 0.51050 -0.07480 0.0320 Uiso calc R 1.000
    H H201 0.86650 0.43860 0.15590 0.0330 Uiso calc R 1.000
    H H202 0.92180 0.43720 0.05960 0.0330 Uiso calc R 1.000
    H H231 1.16520 0.56820 0.20150 0.0490 Uiso calc R 1.000
    H H232 1.22740 0.55390 0.11030 0.0490 Uiso calc R 1.000
    H H251 0.29540 0.71590 0.13370 0.0460 Uiso calc R 1.000
    H H252 0.39170 0.67190 0.17160 0.0460 Uiso calc R 1.000
    H H253 0.37960 0.68360 0.06640 0.0460 Uiso calc R 1.000
    H H261 0.55020 0.98170 0.16010 0.0610 Uiso calc R 1.000
    H H262 0.63660 0.95500 0.09060 0.0610 Uiso calc R 1.000
    H H263 0.65100 0.94060 0.19500 0.0610 Uiso calc R 1.000
    H H1A 0.79280 0.32320 -0.06630 0.0310 Uiso . R 1.000
    H H3A 0.43560 0.31560 -0.07460 0.0410 Uiso calc R 1.000
    H H4A 0.39300 0.20970 -0.13790 0.0410 Uiso calc R 1.000
    H H5A 0.52840 0.14430 -0.20530 0.0380 Uiso calc R 1.000
    H H6A 0.70480 0.17880 -0.19380 0.0320 Uiso calc R 1.000
    H H31A 0.96980 0.08620 -0.14460 0.0360 Uiso calc R 1.000
    H H51A 1.13050 0.26560 -0.17700 0.0310 Uiso calc R 1.000
    H H11W 0.51340 0.50280 0.01730 0.0670 Uiso . . 0.730
    H H12W 0.48440 0.57580 -0.00170 0.0670 Uiso . . 0.730
    H H21W 0.41730 0.47820 -0.10960 0.0410 Uiso . . 0.170
    H H22W 0.39130 0.54720 -0.13060 0.0410 Uiso . . 0.170
    H H31W 0.56050 0.50890 -0.12720 0.0280 Uiso . . 0.100
    H H32W 0.52750 0.58190 -0.14620 0.0280 Uiso . . 0.100
_geom_special_details
;
Bond distances, angles etc. have been calculated using the rounded
fractional coordinates. All su's are estimated from the variances of the
(full) variance-covariance matrix. The cell e.s.d.'s are taken into account in
the estimation of distances, angles and torsion angles
;
loop_
    _geom_bond_atom_site_label_1
    _geom_bond_atom_site_label_2
    _geom_bond_site_symmetry_1
    _geom_bond_site_symmetry_2
    _geom_bond_distance
    _geom_bond_publ_flag
    O2 C2 . . 1.374(3) no
    O2 C25 . . 1.424(4) no
    O3 C3 . . 1.369(4) no
    O3 C26 . . 1.432(4) no
    O24 C12 . . 1.426(4) no
    O24 C23 . . 1.447(4) no
    O25 C10 . . 1.226(3) no
    O2A C22A . . 1.256(4) no
    O3A C22A . . 1.254(4) no
    O21A N21A . . 1.226(4) no
    O22A N21A . . 1.223(4) no
    O41A N41A . . 1.232(4) no
    O42A N41A . . 1.224(4) no
    O61A N61A . . 1.217(4) no
    O62A N61A . . 1.221(4) no
    O1W H11W . . 0.8900 no
    O1W H12W . . 0.9000 no
    O2W H22W . . 0.9100 no
    O2W H21W . . 0.9100 no
    O3W H31W . . 0.9000 no
    O3W H32W . . 0.9100 no
    N9 C5 . . 1.409(4) no
    N9 C8 . . 1.489(4) no
    N9 C10 . . 1.363(4) no
    N19 C18 . . 1.510(4) no
    N19 C20 . . 1.516(4) no
    N19 C16 . . 1.540(4) no
    N19 H19 . . 0.9100 no
    N1A C1A . . 1.405(4) no
    N1A C11A . . 1.356(4) no
    N21A C21A . . 1.478(4) no
    N41A C41A . . 1.454(4) no
    N61A C61A . . 1.462(4) no
    N1A H1A . . 0.9000 no
    C1 C2 . . 1.383(4) no
    C1 C6 . . 1.400(4) no
    C2 C3 . . 1.410(4) no
    C3 C4 . . 1.394(4) no
    C4 C5 . . 1.399(4) no
    C5 C6 . . 1.379(4) no
    C6 C7 . . 1.509(4) no
    C7 C16 . . 1.539(4) no
    C7 C8 . . 1.557(4) no
    C7 C17 . . 1.536(4) no
    C8 C13 . . 1.528(4) no
    C10 C11 . . 1.526(4) no
    C11 C12 . . 1.551(4) no
    C12 C13 . . 1.546(4) no
    C13 C14 . . 1.530(4) no
    C14 C21 . . 1.533(4) no
    C14 C15 . . 1.538(4) no
    C15 C16 . . 1.508(4) no
    C17 C18 . . 1.508(4) no
    C20 C21 . . 1.503(4) no
    C21 C22 . . 1.334(5) no
    C22 C23 . . 1.489(5) no
    C1 H1 . . 0.9300 no
    C4 H4 . . 0.9300 no
    C8 H8 . . 0.9800 no
    C11 H112 . . 0.9700 no
    C11 H111 . . 0.9700 no
    C12 H12 . . 0.9800 no
    C13 H13 . . 0.9800 no
    C14 H14 . . 0.9800 no
    C15 H152 . . 0.9700 no
    C15 H151 . . 0.9700 no
    C16 H16 . . 0.9800 no
    C17 H172 . . 0.9700 no
    C17 H171 . . 0.9700 no
    C18 H181 . . 0.9700 no
    C18 H182 . . 0.9700 no
    C20 H202 . . 0.9700 no
    C20 H201 . . 0.9700 no
    C22 H22 . . 0.9300 no
    C23 H232 . . 0.9700 no
    C23 H231 . . 0.9700 no
    C25 H251 . . 0.9600 no
    C25 H252 . . 0.9600 no
    C25 H253 . . 0.9600 no
    C26 H263 . . 0.9600 no
    C26 H261 . . 0.9600 no
    C26 H262 . . 0.9600 no
    C1A C2A . . 1.407(4) no
    C1A C6A . . 1.400(4) no
    C2A C3A . . 1.403(5) no
    C2A C22A . . 1.518(4) no
    C3A C4A . . 1.370(5) no
    C4A C5A . . 1.384(5) no
    C5A C6A . . 1.377(5) no
    C11A C21A . . 1.430(4) no
    C11A C61A . . 1.430(4) no
    C21A C31A . . 1.372(5) no
    C31A C41A . . 1.375(5) no
    C41A C51A . . 1.380(5) no
    C51A C61A . . 1.371(4) no
    C3A H3A . . 0.9300 no
    C4A H4A . . 0.9300 no
    C5A H5A . . 0.9300 no
    C6A H6A . . 0.9300 no
    C31A H31A . . 0.9300 no
    C51A H51A . . 0.9300 no
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_2
    _geom_angle_site_symmetry_3
    _geom_angle
    _geom_angle_publ_flag
    C2 O2 C25 . . . 116.9(2) no
    C3 O3 C26 . . . 117.2(3) no
    C12 O24 C23 . . . 114.6(3) no
    H11W O1W H12W . . . 110.00 no
    H21W O2W H22W . . . 101.00 no
    H31W O3W H32W . . . 109.00 no
    C8 N9 C10 . . . 119.6(2) no
    C5 N9 C10 . . . 126.9(3) no
    C5 N9 C8 . . . 109.2(2) no
    C16 N19 C18 . . . 107.4(2) no
    C16 N19 C20 . . . 112.6(2) no
    C18 N19 C20 . . . 113.1(2) no
    C18 N19 H19 . . . 108.00 no
    C20 N19 H19 . . . 108.00 no
    C16 N19 H19 . . . 108.00 no
    C1A N1A C11A . . . 128.8(3) no
    O22A N21A C21A . . . 116.5(3) no
    O21A N21A C21A . . . 117.9(3) no
    O21A N21A O22A . . . 125.5(3) no
    O41A N41A C41A . . . 116.9(3) no
    O42A N41A C41A . . . 119.0(3) no
    O41A N41A O42A . . . 124.1(3) no
    O61A N61A O62A . . . 122.4(3) no
    O62A N61A C61A . . . 119.4(3) no
    O61A N61A C61A . . . 118.3(3) no
    C1A N1A H1A . . . 113.00 no
    C11A N1A H1A . . . 117.00 no
    C2 C1 C6 . . . 118.9(3) no
    O2 C2 C1 . . . 124.5(3) no
    O2 C2 C3 . . . 115.1(3) no
    C1 C2 C3 . . . 120.4(3) no
    O3 C3 C4 . . . 124.0(3) no
    O3 C3 C2 . . . 115.4(3) no
    C2 C3 C4 . . . 120.7(3) no
    C3 C4 C5 . . . 118.0(3) no
    N9 C5 C4 . . . 128.3(3) no
    N9 C5 C6 . . . 110.2(2) no
    C4 C5 C6 . . . 121.5(2) no
    C5 C6 C7 . . . 110.9(2) no
    C1 C6 C5 . . . 120.5(3) no
    C1 C6 C7 . . . 128.3(3) no
    C6 C7 C17 . . . 113.1(2) no
    C8 C7 C17 . . . 110.4(2) no
    C6 C7 C16 . . . 115.5(2) no
    C6 C7 C8 . . . 102.0(2) no
    C8 C7 C16 . . . 114.1(2) no
    C16 C7 C17 . . . 102.1(2) no
    N9 C8 C13 . . . 106.2(2) no
    N9 C8 C7 . . . 104.5(2) no
    C7 C8 C13 . . . 117.9(2) no
    O25 C10 C11 . . . 121.6(3) no
    O25 C10 N9 . . . 122.5(3) no
    N9 C10 C11 . . . 115.9(2) no
    C10 C11 C12 . . . 118.3(2) no
    O24 C12 C11 . . . 104.3(2) no
    C11 C12 C13 . . . 110.5(2) no
    O24 C12 C13 . . . 114.0(2) no
    C12 C13 C14 . . . 118.7(2) no
    C8 C13 C12 . . . 106.7(2) no
    C8 C13 C14 . . . 112.5(2) no
    C15 C14 C21 . . . 108.8(2) no
    C13 C14 C21 . . . 114.5(2) no
    C13 C14 C15 . . . 106.2(2) no
    C14 C15 C16 . . . 109.4(2) no
    C7 C16 C15 . . . 114.6(2) no
    N19 C16 C15 . . . 111.4(2) no
    N19 C16 C7 . . . 104.5(2) no
    C7 C17 C18 . . . 103.2(2) no
    N19 C18 C17 . . . 104.4(2) no
    N19 C20 C21 . . . 109.4(2) no
    C14 C21 C22 . . . 123.3(3) no
    C20 C21 C22 . . . 121.2(3) no
    C14 C21 C20 . . . 115.5(2) no
    C21 C22 C23 . . . 122.7(3) no
    O24 C23 C22 . . . 111.2(3) no
    C2 C1 H1 . . . 121.00 no
    C6 C1 H1 . . . 121.00 no
    C3 C4 H4 . . . 121.00 no
    C5 C4 H4 . . . 121.00 no
    N9 C8 H8 . . . 109.00 no
    C13 C8 H8 . . . 109.00 no
    C7 C8 H8 . . . 109.00 no
    C12 C11 H111 . . . 108.00 no
    C10 C11 H111 . . . 108.00 no
    H111 C11 H112 . . . 107.00 no
    C10 C11 H112 . . . 108.00 no
    C12 C11 H112 . . . 108.00 no
    C11 C12 H12 . . . 109.00 no
    O24 C12 H12 . . . 109.00 no
    C13 C12 H12 . . . 109.00 no
    C12 C13 H13 . . . 106.00 no
    C14 C13 H13 . . . 106.00 no
    C8 C13 H13 . . . 106.00 no
    C15 C14 H14 . . . 109.00 no
    C21 C14 H14 . . . 109.00 no
    C13 C14 H14 . . . 109.00 no
    C14 C15 H151 . . . 110.00 no
    H151 C15 H152 . . . 108.00 no
    C16 C15 H152 . . . 110.00 no
    C14 C15 H152 . . . 110.00 no
    C16 C15 H151 . . . 110.00 no
    C15 C16 H16 . . . 109.00 no
    C7 C16 H16 . . . 109.00 no
    N19 C16 H16 . . . 109.00 no
    C7 C17 H171 . . . 111.00 no
    H171 C17 H172 . . . 109.00 no
    C7 C17 H172 . . . 111.00 no
    C18 C17 H171 . . . 111.00 no
    C18 C17 H172 . . . 111.00 no
    N19 C18 H181 . . . 111.00 no
    C17 C18 H182 . . . 111.00 no
    C17 C18 H181 . . . 111.00 no
    N19 C18 H182 . . . 111.00 no
    H181 C18 H182 . . . 109.00 no
    H201 C20 H202 . . . 108.00 no
    C21 C20 H201 . . . 110.00 no
    C21 C20 H202 . . . 110.00 no
    N19 C20 H202 . . . 110.00 no
    N19 C20 H201 . . . 110.00 no
    C23 C22 H22 . . . 119.00 no
    C21 C22 H22 . . . 119.00 no
    H231 C23 H232 . . . 108.00 no
    C22 C23 H232 . . . 109.00 no
    O24 C23 H231 . . . 109.00 no
    O24 C23 H232 . . . 109.00 no
    C22 C23 H231 . . . 109.00 no
    H251 C25 H252 . . . 110.00 no
    O2 C25 H251 . . . 109.00 no
    H252 C25 H253 . . . 110.00 no
    O2 C25 H253 . . . 109.00 no
    O2 C25 H252 . . . 109.00 no
    H251 C25 H253 . . . 109.00 no
    H261 C26 H262 . . . 110.00 no
    H262 C26 H263 . . . 109.00 no
    H261 C26 H263 . . . 109.00 no
    O3 C26 H263 . . . 109.00 no
    O3 C26 H262 . . . 109.00 no
    O3 C26 H261 . . . 109.00 no
    C2A C1A C6A . . . 119.1(3) no
    N1A C1A C2A . . . 118.2(3) no
    N1A C1A C6A . . . 122.4(3) no
    C1A C2A C22A . . . 124.2(3) no
    C3A C2A C22A . . . 118.1(3) no
    C1A C2A C3A . . . 117.7(3) no
    C2A C3A C4A . . . 122.6(3) no
    C3A C4A C5A . . . 118.6(3) no
    C4A C5A C6A . . . 120.7(3) no
    C1A C6A C5A . . . 120.5(3) no
    N1A C11A C61A . . . 122.6(3) no
    N1A C11A C21A . . . 124.8(3) no
    C21A C11A C61A . . . 112.6(3) no
    C11A C21A C31A . . . 124.0(3) no
    N21A C21A C11A . . . 120.7(3) no
    N21A C21A C31A . . . 114.9(3) no
    O2A C22A C2A . . . 118.3(3) no
    O3A C22A C2A . . . 116.4(3) no
    O2A C22A O3A . . . 125.2(3) no
    C21A C31A C41A . . . 118.8(3) no
    N41A C41A C31A . . . 120.0(3) no
    C31A C41A C51A . . . 120.9(3) no
    N41A C41A C51A . . . 119.1(3) no
    C41A C51A C61A . . . 119.5(3) no
    N61A C61A C11A . . . 121.0(3) no
    N61A C61A C51A . . . 115.5(3) no
    C11A C61A C51A . . . 123.4(3) no
    C4A C3A H3A . . . 119.00 no
    C2A C3A H3A . . . 119.00 no
    C3A C4A H4A . . . 121.00 no
    C5A C4A H4A . . . 121.00 no
    C4A C5A H5A . . . 120.00 no
    C6A C5A H5A . . . 120.00 no
    C5A C6A H6A . . . 120.00 no
    C1A C6A H6A . . . 120.00 no
    C21A C31A H31A . . . 121.00 no
    C41A C31A H31A . . . 121.00 no
    C41A C51A H51A . . . 120.00 no
    C61A C51A H51A . . . 120.00 no
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
    C25 O2 C2 C1 . . . . -1.8(4) no
    C25 O2 C2 C3 . . . . 176.8(3) no
    C26 O3 C3 C2 . . . . 175.4(3) no
    C26 O3 C3 C4 . . . . -5.4(4) no
    C23 O24 C12 C11 . . . . 170.2(2) no
    C23 O24 C12 C13 . . . . -69.2(3) no
    C12 O24 C23 C22 . . . . 89.1(4) no
    C8 N9 C5 C4 . . . . 172.9(3) no
    C8 N9 C5 C6 . . . . -6.0(3) no
    C10 N9 C5 C4 . . . . 16.5(5) no
    C10 N9 C5 C6 . . . . -162.4(3) no
    C5 N9 C8 C7 . . . . 15.1(3) no
    C5 N9 C8 C13 . . . . -110.2(2) no
    C10 N9 C8 C7 . . . . 173.5(3) no
    C10 N9 C8 C13 . . . . 48.2(3) no
    C5 N9 C10 O25 . . . . -24.3(5) no
    C5 N9 C10 C11 . . . . 157.2(3) no
    C8 N9 C10 O25 . . . . -178.5(3) no
    C8 N9 C10 C11 . . . . 3.0(4) no
    C18 N19 C16 C7 . . . . -8.4(3) no
    C18 N19 C16 C15 . . . . -132.6(3) no
    C20 N19 C16 C7 . . . . 116.8(2) no
    C20 N19 C16 C15 . . . . -7.5(3) no
    C16 N19 C18 C17 . . . . -18.3(3) no
    C20 N19 C18 C17 . . . . -143.2(2) no
    C16 N19 C20 C21 . . . . -48.6(3) no
    C18 N19 C20 C21 . . . . 73.4(3) no
    C1A N1A C11A C61A . . . . 152.2(3) no
    C11A N1A C1A C2A . . . . 171.4(3) no
    C11A N1A C1A C6A . . . . -15.0(5) no
    C1A N1A C11A C21A . . . . -26.5(5) no
    O21A N21A C21A C11A . . . . -31.2(4) no
    O21A N21A C21A C31A . . . . 141.2(3) no
    O22A N21A C21A C11A . . . . 151.7(3) no
    O22A N21A C21A C31A . . . . -35.8(4) no
    O42A N41A C41A C51A . . . . 1.4(4) no
    O41A N41A C41A C31A . . . . 2.7(4) no
    O41A N41A C41A C51A . . . . -178.1(3) no
    O42A N41A C41A C31A . . . . -177.8(3) no
    O61A N61A C61A C51A . . . . 11.1(4) no
    O62A N61A C61A C11A . . . . 17.0(4) no
    O61A N61A C61A C11A . . . . -165.2(3) no
    O62A N61A C61A C51A . . . . -166.8(3) no
    C6 C1 C2 O2 . . . . 178.0(3) no
    C2 C1 C6 C5 . . . . 0.1(4) no
    C2 C1 C6 C7 . . . . -173.2(3) no
    C6 C1 C2 C3 . . . . -0.6(4) no
    C1 C2 C3 O3 . . . . 179.7(3) no
    O2 C2 C3 O3 . . . . 1.1(4) no
    O2 C2 C3 C4 . . . . -178.1(3) no
    C1 C2 C3 C4 . . . . 0.5(4) no
    C2 C3 C4 C5 . . . . -0.1(4) no
    O3 C3 C4 C5 . . . . -179.2(3) no
    C3 C4 C5 N9 . . . . -179.1(3) no
    C3 C4 C5 C6 . . . . -0.4(4) no
    N9 C5 C6 C7 . . . . -6.3(3) no
    N9 C5 C6 C1 . . . . 179.3(3) no
    C4 C5 C6 C1 . . . . 0.3(5) no
    C4 C5 C6 C7 . . . . 174.8(3) no
    C5 C6 C7 C16 . . . . 139.3(3) no
    C1 C6 C7 C8 . . . . -171.1(3) no
    C1 C6 C7 C16 . . . . -46.8(4) no
    C1 C6 C7 C17 . . . . 70.3(4) no
    C5 C6 C7 C17 . . . . -103.5(3) no
    C5 C6 C7 C8 . . . . 15.0(3) no
    C6 C7 C8 C13 . . . . 100.1(3) no
    C16 C7 C8 N9 . . . . -142.7(2) no
    C16 C7 C8 C13 . . . . -25.2(3) no
    C17 C7 C8 N9 . . . . 103.0(3) no
    C17 C7 C8 C13 . . . . -139.5(3) no
    C6 C7 C16 N19 . . . . 154.3(2) no
    C6 C7 C8 N9 . . . . -17.5(3) no
    C8 C7 C16 N19 . . . . -88.0(3) no
    C8 C7 C16 C15 . . . . 34.2(3) no
    C17 C7 C16 N19 . . . . 31.2(2) no
    C17 C7 C16 C15 . . . . 153.3(2) no
    C6 C7 C17 C18 . . . . -167.8(2) no
    C8 C7 C17 C18 . . . . 78.7(3) no
    C6 C7 C16 C15 . . . . -83.6(3) no
    C16 C7 C17 C18 . . . . -43.0(3) no
    N9 C8 C13 C12 . . . . -72.2(3) no
    N9 C8 C13 C14 . . . . 155.9(2) no
    C7 C8 C13 C12 . . . . 171.1(2) no
    C7 C8 C13 C14 . . . . 39.3(3) no
    O25 C10 C11 C12 . . . . 150.7(3) no
    N9 C10 C11 C12 . . . . -30.8(4) no
    C10 C11 C12 O24 . . . . 127.0(3) no
    C10 C11 C12 C13 . . . . 4.1(4) no
    O24 C12 C13 C8 . . . . -71.7(3) no
    O24 C12 C13 C14 . . . . 56.6(3) no
    C11 C12 C13 C8 . . . . 45.4(3) no
    C11 C12 C13 C14 . . . . 173.7(2) no
    C8 C13 C14 C15 . . . . -59.5(3) no
    C8 C13 C14 C21 . . . . 60.6(3) no
    C12 C13 C14 C21 . . . . -65.0(3) no
    C12 C13 C14 C15 . . . . 174.9(2) no
    C21 C14 C15 C16 . . . . -54.7(3) no
    C13 C14 C21 C20 . . . . -121.7(3) no
    C13 C14 C21 C22 . . . . 57.1(4) no
    C15 C14 C21 C20 . . . . -3.0(3) no
    C15 C14 C21 C22 . . . . 175.7(3) no
    C13 C14 C15 C16 . . . . 69.1(3) no
    C14 C15 C16 N19 . . . . 60.9(3) no
    C14 C15 C16 C7 . . . . -57.4(3) no
    C7 C17 C18 N19 . . . . 38.0(3) no
    N19 C20 C21 C14 . . . . 55.1(3) no
    N19 C20 C21 C22 . . . . -123.8(3) no
    C20 C21 C22 C23 . . . . 176.0(3) no
    C14 C21 C22 C23 . . . . -2.7(6) no
    C21 C22 C23 O24 . . . . -63.6(5) no
    N1A C1A C2A C3A . . . . -179.1(3) no
    N1A C1A C2A C22A . . . . 3.3(4) no
    C6A C1A C2A C3A . . . . 7.0(4) no
    C6A C1A C2A C22A . . . . -170.6(3) no
    N1A C1A C6A C5A . . . . 177.1(3) no
    C2A C1A C6A C5A . . . . -9.4(5) no
    C1A C2A C3A C4A . . . . 0.9(5) no
    C22A C2A C3A C4A . . . . 178.6(3) no
    C1A C2A C22A O2A . . . . -21.5(5) no
    C1A C2A C22A O3A . . . . 159.4(3) no
    C3A C2A C22A O2A . . . . 160.9(3) no
    C3A C2A C22A O3A . . . . -18.2(4) no
    C2A C3A C4A C5A . . . . -6.6(5) no
    C3A C4A C5A C6A . . . . 4.3(5) no
    C4A C5A C6A C1A . . . . 3.7(5) no
    N1A C11A C21A N21A . . . . -20.7(5) no
    N1A C11A C21A C31A . . . . 167.6(3) no
    C61A C11A C21A N21A . . . . 160.5(3) no
    C61A C11A C21A C31A . . . . -11.2(4) no
    N1A C11A C61A N61A . . . . 5.8(4) no
    N1A C11A C61A C51A . . . . -170.1(3) no
    C21A C11A C61A N61A . . . . -175.3(3) no
    C21A C11A C61A C51A . . . . 8.7(4) no
    N21A C21A C31A C41A . . . . -166.4(3) no
    C11A C21A C31A C41A . . . . 5.8(5) no
    C21A C31A C41A N41A . . . . -177.7(3) no
    C21A C31A C41A C51A . . . . 3.2(5) no
    N41A C41A C51A C61A . . . . 175.4(3) no
    C31A C41A C51A C61A . . . . -5.5(5) no
    C41A C51A C61A N61A . . . . -177.2(3) no
    C41A C51A C61A C11A . . . . -1.0(5) no
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
    N19 H19 O2A . 0.91 1.94 2.708(4) 141 yes
    N1A H1A O2A . 0.90 1.90 2.662(3) 141 yes
    N1A H1A O62A . 0.90 2.10 2.653(4) 118 yes
    O1W H11W O3A . 0.89 1.80 2.695(4) 177 yes
    O1W H12W O25 3_465 0.90 2.19 3.091(4) 178 yes
    O2W H21W O3A . 0.91 2.17 3.079(14) 179 yes
    O2W H22W O25 3_465 0.91 2.11 3.020(14) 179 yes
    O3W H31W O3A . 0.90 2.17 3.08(2) 179 yes
    O3W H32W O25 3_465 0.91 1.73 2.65(2) 179 yes
    C1 H1 O1W . 0.93 2.41 3.263(4) 153 no
    C4A H4A O42A 1_455 0.93 2.53 3.364(4) 150 no
    C20 H202 O62A . 0.97 2.44 3.319(4) 150 no
