#------------------------------------------------------------------------------
#$Date: 2016-02-20 22:30:07 +0200 (Sat, 20 Feb 2016) $
#$Revision: 176789 $
#$URL: svn://www.crystallography.net/cod/cif/2/22/96/2229665.cif $
#------------------------------------------------------------------------------
#
# This file is available in the Crystallography Open Database (COD),
# http://www.crystallography.net/. The original data for this entry
# were provided by IUCr Journals, http://journals.iucr.org/.
#
# The file may be used within the scientific community so long as
# proper attribution is given to the journal article from which the
# data were obtained.
#
data_2229665
loop_
_publ_author_name
'Xie, Zhi-Xiong'
'Zhao, Sheng-Yin'
_publ_section_title
;
 1-(2-Hydroxyethyl)-3-[(2-hydroxyethyl)amino]-4-(1H-indol-3-yl)-1H-pyrrole-2,5-dione
;
_journal_coeditor_code           HB5807
_journal_issue                   4
_journal_name_full               'Acta Crystallographica Section E'
_journal_page_first              o854
_journal_paper_doi               10.1107/S1600536811007677
_journal_volume                  67
_journal_year                    2011
_chemical_formula_iupac          'C16 H17 N3 O4'
_chemical_formula_moiety         'C16 H17 N3 O4'
_chemical_formula_sum            'C16 H17 N3 O4'
_chemical_formula_weight         315.33
_chemical_name_systematic
;
1-(2-Hydroxyethyl)-3-[(2-hydroxyethyl)amino]-4-(1H-indol-3-yl)-1H-
pyrrole-2,5-dione
;
_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                90.0120(10)
_cell_angle_beta                 110.295(2)
_cell_angle_gamma                102.187(2)
_cell_formula_units_Z            8
_cell_length_a                   13.0276(10)
_cell_length_b                   14.8150(11)
_cell_length_c                   17.8893(14)
_cell_measurement_reflns_used    3141
_cell_measurement_temperature    293(2)
_cell_measurement_theta_max      45.43
_cell_measurement_theta_min      4.87
_cell_volume                     3155.2(4)
_computing_cell_refinement       'SAINT (Bruker, 2003)'
_computing_data_collection       'SMART (Bruker, 2003)'
_computing_data_reduction        'SAINT (Bruker, 2003)'
_computing_molecular_graphics    'SHELXTL (Sheldrick, 2008)'
_computing_publication_material  'SHELXTL (Sheldrick, 2008)'
_computing_structure_refinement  'SHELXL97 (Sheldrick, 2008)'
_computing_structure_solution    'SHELXS97 (Sheldrick, 2008)'
_diffrn_ambient_temperature      293(2)
_diffrn_measured_fraction_theta_full 0.983
_diffrn_measured_fraction_theta_max 0.983
_diffrn_measurement_device_type  'Bruker SMART CCD'
_diffrn_measurement_method       ω
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_source         'fine-focus sealed tube'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0351
_diffrn_reflns_av_sigmaI/netI    0.0878
_diffrn_reflns_limit_h_max       8
_diffrn_reflns_limit_h_min       -16
_diffrn_reflns_limit_k_max       18
_diffrn_reflns_limit_k_min       -18
_diffrn_reflns_limit_l_max       22
_diffrn_reflns_limit_l_min       -22
_diffrn_reflns_number            17464
_diffrn_reflns_theta_full        26.00
_diffrn_reflns_theta_max         26.00
_diffrn_reflns_theta_min         1.22
_exptl_absorpt_coefficient_mu    0.097
_exptl_absorpt_correction_T_max  1.000
_exptl_absorpt_correction_T_min  0.594
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   '(SADABS; Bruker, 2003)'
_exptl_crystal_colour            red
_exptl_crystal_density_diffrn    1.328
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       prism
_exptl_crystal_F_000             1328
_exptl_crystal_size_max          0.43
_exptl_crystal_size_mid          0.33
_exptl_crystal_size_min          0.27
_refine_diff_density_max         0.180
_refine_diff_density_min         -0.184
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   0.885
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     893
_refine_ls_number_reflns         12193
_refine_ls_number_restraints     13
_refine_ls_restrained_S_all      0.886
_refine_ls_R_factor_all          0.0920
_refine_ls_R_factor_gt           0.0468
_refine_ls_shift/su_max          0.002
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'calc w=1/[σ²(Fo²)+(0.0246P)²] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0820
_refine_ls_wR_factor_ref         0.0979
_reflns_number_gt                6708
_reflns_number_total             12193
_reflns_threshold_expression     I>2σ(I)
_cod_data_source_file            hb5807.cif
_cod_data_source_block           I
_cod_database_code               2229665
_cod_database_fobs_code          2229665
loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'-x, -y, -z'
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_disorder_assembly
_atom_site_disorder_group
O O1 0.01888(14) 0.90744(12) 0.80210(9) 0.0565(5) Uani d . 1 . .
O O2 0.29635(13) 0.85115(12) 0.72416(9) 0.0504(5) Uani d . 1 . .
O O3 0.04854(17) 0.83153(15) 0.57712(11) 0.0565(6) Uani d . 1 . .
O O4 0.15970(17) 0.77882(16) 1.08999(12) 0.0692(6) Uani d D 1 . .
O O5 0.95648(14) 0.59360(11) 0.28315(9) 0.0535(5) Uani d . 1 . .
O O6 0.67689(14) 0.66239(12) 0.07237(9) 0.0513(5) Uani d . 1 . .
O O7 0.94607(17) 0.67135(14) 0.05474(11) 0.0538(5) Uani d D 1 . .
O O8 0.84197(16) 0.71019(15) 0.51014(12) 0.0638(6) Uani d D 1 . .
O O9 0.07500(14) 0.42150(11) 0.14849(9) 0.0545(5) Uani d . 1 . .
O O10 0.27077(13) 0.32299(11) 0.38483(9) 0.0452(4) Uani d . 1 . .
O O11 -0.03045(15) 0.43298(14) 0.37925(10) 0.0511(5) Uani d D 1 . .
O O12 0.03693(16) 0.11914(13) 0.04475(11) 0.0539(5) Uani d D 1 . .
O O13 0.07026(14) 0.90731(11) 0.37576(10) 0.0518(5) Uani d . 1 . .
O O14 0.28453(13) 0.81144(11) 0.25196(9) 0.0451(4) Uani d . 1 . .
O O15 -0.03425(16) 0.92783(14) 0.10409(10) 0.0547(5) Uani d D 1 . .
O O16 0.03196(16) 0.62001(13) 0.47197(11) 0.0551(5) Uani d D 1 . .
N N1 0.14842(15) 0.89266(13) 0.74548(10) 0.0372(5) Uani d . 1 . .
N N2 0.11889(18) 0.78733(15) 0.91611(12) 0.0465(6) Uani d . 1 . .
N N3 0.47775(18) 0.70845(14) 0.96808(12) 0.0434(6) Uani d . 1 . .
N N4 0.82676(16) 0.61586(13) 0.16343(11) 0.0388(5) Uani d . 1 . .
N N5 0.86558(18) 0.71354(15) 0.35412(12) 0.0455(6) Uani d D 1 . .
N N6 0.50460(18) 0.79428(15) 0.23571(13) 0.0466(6) Uani d D 1 . .
N N7 0.15305(15) 0.37924(13) 0.27663(11) 0.0392(5) Uani d . 1 . .
N N8 0.19072(18) 0.29920(14) 0.10367(12) 0.0425(5) Uani d D 1 . .
N N9 0.50170(18) 0.18774(15) 0.26645(13) 0.0460(6) Uani d D 1 . .
N N10 0.15776(15) 0.86570(13) 0.29283(11) 0.0385(5) Uani d . 1 . .
N N11 0.19009(17) 0.79605(14) 0.48792(12) 0.0422(5) Uani d D 1 . .
N N12 0.51134(18) 0.68804(15) 0.49777(13) 0.0451(6) Uani d D 1 . .
C C1 0.0978(2) 0.87718(16) 0.80078(13) 0.0370(6) Uani d . 1 . .
C C2 0.15798(19) 0.81481(15) 0.85866(13) 0.0333(6) Uani d . 1 . .
C C3 0.24264(18) 0.79819(15) 0.83623(13) 0.0330(6) Uani d . 1 . .
C C4 0.23771(19) 0.84653(16) 0.76469(14) 0.0371(6) Uani d . 1 . .
C C5 0.33199(18) 0.74941(15) 0.87521(13) 0.0325(6) Uani d . 1 . .
C C6 0.41135(19) 0.77124(16) 0.95001(13) 0.0396(6) Uani d . 1 . .
H H6 0.4191 0.8218 0.9839 0.048 Uiso calc R 1 . .
C C7 0.44387(19) 0.64506(16) 0.90381(14) 0.0370(6) Uani d . 1 . .
C C8 0.35307(18) 0.66880(15) 0.84379(13) 0.0313(5) Uani d . 1 . .
C C9 0.30427(19) 0.61489(16) 0.77103(14) 0.0411(6) Uani d . 1 . .
H H9 0.2443 0.6291 0.7300 0.049 Uiso calc R 1 . .
C C10 0.3471(2) 0.54000(16) 0.76140(16) 0.0496(7) Uani d . 1 . .
H H10 0.3161 0.5039 0.7130 0.060 Uiso calc R 1 . .
C C11 0.4362(2) 0.51745(17) 0.82295(17) 0.0538(7) Uani d . 1 . .
H H11 0.4623 0.4658 0.8149 0.065 Uiso calc R 1 . .
C C12 0.4857(2) 0.56879(17) 0.89430(15) 0.0470(7) Uani d . 1 . .
H H12 0.5452 0.5535 0.9350 0.056 Uiso calc R 1 . .
C C13 0.1222(2) 0.95368(16) 0.68137(13) 0.0449(7) Uani d . 1 . .
H H13A 0.1871 0.9734 0.6656 0.054 Uiso calc R 1 . .
H H13B 0.1066 1.0085 0.7009 0.054 Uiso calc R 1 . .
C C14 0.0232(2) 0.90832(18) 0.60956(14) 0.0564(8) Uani d . 1 . .
H H14A -0.0420 0.8873 0.6248 0.068 Uiso calc R 1 . .
H H14B 0.0060 0.9526 0.5697 0.068 Uiso calc R 1 . .
C C15 0.1534(2) 0.71408(16) 0.96736(13) 0.0446(7) Uani d . 1 . .
H H15A 0.1938 0.6811 0.9445 0.054 Uiso calc R 1 . .
H H15B 0.0867 0.6703 0.9677 0.054 Uiso calc R 1 . .
C C16 0.2259(2) 0.7482(2) 1.05170(14) 0.0603(8) Uani d . 1 . .
H H16A 0.2576 0.6988 1.0796 0.072 Uiso calc R 1 . .
H H16B 0.2872 0.7989 1.0524 0.072 Uiso calc R 1 . .
C C17 0.8788(2) 0.62661(16) 0.24387(14) 0.0383(6) Uani d . 1 . .
C C18 0.82312(19) 0.68873(15) 0.27522(13) 0.0338(6) Uani d . 1 . .
C C19 0.73717(18) 0.70832(15) 0.21321(13) 0.0327(6) Uani d . 1 . .
C C20 0.73834(19) 0.66356(16) 0.14114(14) 0.0376(6) Uani d . 1 . .
C C21 0.64887(18) 0.75675(15) 0.21160(13) 0.0340(6) Uani d . 1 . .
C C22 0.57272(19) 0.73278(16) 0.24882(13) 0.0411(6) Uani d . 1 . .
H H22 0.5679 0.6819 0.2788 0.049 Uiso calc R 1 . .
C C23 0.5339(2) 0.85913(16) 0.18788(14) 0.0399(6) Uani d . 1 . .
C C24 0.62425(19) 0.83761(16) 0.17098(13) 0.0353(6) Uani d . 1 . .
C C25 0.6702(2) 0.89384(16) 0.12269(14) 0.0448(7) Uani d . 1 . .
H H25 0.7300 0.8812 0.1108 0.054 Uiso calc R 1 . .
C C26 0.6254(2) 0.96828(17) 0.09301(15) 0.0578(8) Uani d . 1 . .
H H26 0.6545 1.0057 0.0600 0.069 Uiso calc R 1 . .
C C27 0.5366(3) 0.98819(18) 0.11196(17) 0.0637(9) Uani d . 1 . .
H H27 0.5088 1.0395 0.0918 0.076 Uiso calc R 1 . .
C C28 0.4897(2) 0.93519(18) 0.15875(15) 0.0539(8) Uani d . 1 . .
H H28 0.4306 0.9491 0.1708 0.065 Uiso calc R 1 . .
C C29 0.8468(2) 0.55311(17) 0.11019(14) 0.0490(7) Uani d . 1 . .
H H29A 0.7846 0.5426 0.0595 0.059 Uiso calc R 1 . .
H H29B 0.8495 0.4940 0.1332 0.059 Uiso calc R 1 . .
C C30 0.9545(2) 0.58963(18) 0.09541(15) 0.0553(8) Uani d . 1 . .
H H30A 1.0171 0.6031 0.1459 0.066 Uiso calc R 1 . .
H H30B 0.9676 0.5435 0.0634 0.066 Uiso calc R 1 . .
C C31 0.83718(19) 0.78606(16) 0.39233(13) 0.0440(7) Uani d . 1 . .
H H31A 0.7932 0.8196 0.3514 0.053 Uiso calc R 1 . .
H H31B 0.9058 0.8294 0.4243 0.053 Uiso calc R 1 . .
C C32 0.7726(2) 0.75013(19) 0.44452(15) 0.0561(8) Uani d . 1 . .
H H32A 0.7490 0.8003 0.4642 0.067 Uiso calc R 1 . .
H H32B 0.7060 0.7038 0.4141 0.067 Uiso calc R 1 . .
C C33 0.13398(19) 0.37915(16) 0.19553(14) 0.0392(6) Uani d . 1 . .
C C34 0.20150(18) 0.31586(15) 0.17965(13) 0.0335(6) Uani d . 1 . .
C C35 0.26342(18) 0.28810(15) 0.25086(12) 0.0310(5) Uani d . 1 . .
C C36 0.23384(18) 0.32799(16) 0.31208(14) 0.0356(6) Uani d . 1 . .
C C37 0.35094(18) 0.23509(15) 0.26947(13) 0.0321(6) Uani d . 1 . .
C C38 0.43740(19) 0.25097(16) 0.24109(13) 0.0395(6) Uani d . 1 . .
H H38 0.4505 0.2982 0.2090 0.047 Uiso calc R 1 . .
C C39 0.4593(2) 0.13065(16) 0.31364(14) 0.0396(6) Uani d . 1 . .
C C40 0.36477(18) 0.15878(15) 0.31827(12) 0.0317(6) Uani d . 1 . .
C C41 0.3088(2) 0.11198(16) 0.36590(13) 0.0415(6) Uani d . 1 . .
H H41 0.2459 0.1288 0.3699 0.050 Uiso calc R 1 . .
C C42 0.3489(2) 0.04011(17) 0.40695(14) 0.0536(7) Uani d . 1 . .
H H42 0.3140 0.0096 0.4402 0.064 Uiso calc R 1 . .
C C43 0.4413(2) 0.01276(18) 0.39907(16) 0.0573(8) Uani d . 1 . .
H H43 0.4652 -0.0368 0.4262 0.069 Uiso calc R 1 . .
C C44 0.4973(2) 0.05634(18) 0.35303(15) 0.0521(7) Uani d . 1 . .
H H44 0.5584 0.0374 0.3480 0.062 Uiso calc R 1 . .
C C45 0.11261(18) 0.43681(16) 0.32088(14) 0.0424(6) Uani d . 1 . .
H H45A 0.1077 0.4950 0.2965 0.051 Uiso calc R 1 . .
H H45B 0.1655 0.4505 0.3754 0.051 Uiso calc R 1 . .
C C46 -0.00130(19) 0.38894(16) 0.32173(14) 0.0451(7) Uani d . 1 . .
H H46A -0.0574 0.3888 0.2692 0.054 Uiso calc R 1 . .
H H46B -0.0011 0.3250 0.3334 0.054 Uiso calc R 1 . .
C C47 0.2206(2) 0.22208(17) 0.07274(14) 0.0439(7) Uani d . 1 . .
H H47A 0.3002 0.2254 0.0996 0.053 Uiso calc R 1 . .
H H47B 0.2067 0.2268 0.0161 0.053 Uiso calc R 1 . .
C C48 0.1548(2) 0.13003(17) 0.08450(14) 0.0489(7) Uani d . 1 . .
H H48A 0.1791 0.0807 0.0644 0.059 Uiso calc R 1 . .
H H48B 0.1705 0.1246 0.1412 0.059 Uiso calc R 1 . .
C C49 0.1340(2) 0.86713(16) 0.36197(14) 0.0383(6) Uani d . 1 . .
C C50 0.20470(18) 0.80888(15) 0.41787(13) 0.0332(6) Uani d . 1 . .
C C51 0.27068(18) 0.78090(15) 0.38135(13) 0.0313(6) Uani d . 1 . .
C C52 0.24286(19) 0.81751(15) 0.30282(13) 0.0354(6) Uani d . 1 . .
C C53 0.36095(18) 0.73141(15) 0.41251(13) 0.0314(5) Uani d . 1 . .
C C54 0.44338(19) 0.74950(16) 0.48690(13) 0.0399(6) Uani d . 1 . .
H H54 0.4518 0.7966 0.5244 0.048 Uiso calc R 1 . .
C C55 0.47595(19) 0.62988(16) 0.42986(14) 0.0382(6) Uani d . 1 . .
C C56 0.38155(18) 0.65533(15) 0.37388(13) 0.0336(6) Uani d . 1 . .
C C57 0.3320(2) 0.60708(16) 0.29817(14) 0.0419(6) Uani d . 1 . .
H H57 0.2707 0.6231 0.2598 0.050 Uiso calc R 1 . .
C C58 0.3747(2) 0.53610(17) 0.28139(16) 0.0519(7) Uani d . 1 . .
H H58 0.3423 0.5043 0.2310 0.062 Uiso calc R 1 . .
C C59 0.4657(2) 0.51040(17) 0.33818(19) 0.0589(8) Uani d . 1 . .
H H59 0.4920 0.4611 0.3252 0.071 Uiso calc R 1 . .
C C60 0.5177(2) 0.55631(17) 0.41323(17) 0.0526(7) Uani d . 1 . .
H H60 0.5782 0.5388 0.4512 0.063 Uiso calc R 1 . .
C C61 0.11773(19) 0.92236(16) 0.22703(13) 0.0419(6) Uani d . 1 . .
H H61A 0.1654 0.9280 0.1952 0.050 Uiso calc R 1 . .
H H61B 0.1229 0.9840 0.2484 0.050 Uiso calc R 1 . .
C C62 -0.00267(19) 0.88101(16) 0.17422(13) 0.0458(7) Uani d . 1 . .
H H62A -0.0107 0.8161 0.1600 0.055 Uiso calc R 1 . .
H H62B -0.0521 0.8851 0.2034 0.055 Uiso calc R 1 . .
C C63 0.2175(2) 0.71998(17) 0.53710(13) 0.0447(7) Uani d . 1 . .
H H63A 0.2026 0.7276 0.5860 0.054 Uiso calc R 1 . .
H H63B 0.2968 0.7214 0.5516 0.054 Uiso calc R 1 . .
C C64 0.1493(2) 0.62799(17) 0.49328(14) 0.0490(7) Uani d . 1 . .
H H64A 0.1660 0.6200 0.4452 0.059 Uiso calc R 1 . .
H H64B 0.1712 0.5788 0.5268 0.059 Uiso calc R 1 . .
H H2 0.076(2) 0.8158(18) 0.9294(16) 0.090(11) Uiso d . 1 . .
H H3 -0.011(3) 0.790(2) 0.5591(19) 0.110(15) Uiso d . 1 . .
H H4 0.197(2) 0.800(2) 1.1362(12) 0.115(14) Uiso d D 1 . .
H H5 0.9167(16) 0.6879(14) 0.3791(12) 0.049(8) Uiso d D 1 . .
H H7 1.0115(17) 0.7078(19) 0.0656(18) 0.108(14) Uiso d D 1 . .
H H15 -0.028(2) 0.9853(12) 0.1074(17) 0.091(12) Uiso d D 1 . .
H H16 0.023(2) 0.602(2) 0.5139(13) 0.101(13) Uiso d D 1 . .
H H3A 0.5346(18) 0.7095(15) 1.0115(13) 0.052(8) Uiso d . 1 . .
H H6A 0.4477(16) 0.7952(16) 0.2469(14) 0.058(9) Uiso d D 1 . .
H H8A 0.811(3) 0.698(2) 0.5447(16) 0.135(16) Uiso d D 1 . .
H H9A 0.5621(17) 0.1857(18) 0.2545(15) 0.080(10) Uiso d D 1 . .
H H11A -0.033(3) 0.4887(15) 0.366(2) 0.154(17) Uiso d D 1 . .
H H12A 0.027(2) 0.107(2) -0.0032(11) 0.093(12) Uiso d D 1 . .
H H8B 0.1419(16) 0.3246(14) 0.0672(11) 0.048(7) Uiso d D 1 . .
H H11B 0.1432(18) 0.8233(16) 0.4995(14) 0.069(9) Uiso d D 1 . .
H H12B 0.5704(15) 0.6903(15) 0.5382(11) 0.049(8) Uiso d D 1 . .
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'
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
C14 O3 H3 . . 108(2) ?
C16 O4 H4 . . 111(2) ?
C30 O7 H7 . . 111(2) ?
C32 O8 H8A . . 111(2) ?
C46 O11 H11A . . 107(2) ?
C48 O12 H12A . . 104(2) ?
C62 O15 H15 . . 120(2) ?
C64 O16 H16 . . 100(2) ?
C1 N1 C4 . . 109.12(19) ?
C1 N1 C13 . . 125.62(19) ?
C4 N1 C13 . . 125.0(2) ?
C2 N2 C15 . . 123.8(2) ?
C2 N2 H2 . . 121.5(19) ?
C15 N2 H2 . . 114.3(19) ?
C6 N3 C7 . . 108.72(19) ?
C6 N3 H3A . . 126.6(15) ?
C7 N3 H3A . . 124.6(15) ?
C17 N4 C20 . . 109.35(18) ?
C17 N4 C29 . . 124.79(19) ?
C20 N4 C29 . . 125.17(19) ?
C18 N5 C31 . . 124.7(2) ?
C18 N5 H5 . . 113.3(16) ?
C31 N5 H5 . . 121.6(16) ?
C22 N6 C23 . . 109.1(2) ?
C22 N6 H6A . . 132.4(18) ?
C23 N6 H6A . . 118.1(17) ?
C33 N7 C36 . . 109.16(18) ?
C33 N7 C45 . . 125.60(18) ?
C36 N7 C45 . . 124.32(19) ?
C34 N8 C47 . . 125.5(2) ?
C34 N8 H8B . . 116.7(14) ?
C47 N8 H8B . . 114.6(14) ?
C38 N9 C39 . . 108.7(2) ?
C38 N9 H9A . . 124.7(18) ?
C39 N9 H9A . . 126.6(18) ?
C49 N10 C52 . . 109.52(19) ?
C49 N10 C61 . . 124.06(19) ?
C52 N10 C61 . . 125.21(19) ?
C50 N11 C63 . . 125.1(2) ?
C50 N11 H11B . . 118.9(16) ?
C63 N11 H11B . . 113.3(17) ?
C54 N12 C55 . . 109.22(19) ?
C54 N12 H12B . . 124.6(15) ?
C55 N12 H12B . . 125.8(15) ?
O1 C1 N1 . . 126.0(2) ?
O1 C1 C2 . . 127.2(2) ?
N1 C1 C2 . . 106.81(19) ?
N2 C2 C3 . . 134.6(2) ?
N2 C2 C1 . . 117.1(2) ?
C3 C2 C1 . . 108.3(2) ?
C2 C3 C4 . . 106.90(19) ?
C2 C3 C5 . . 130.7(2) ?
C4 C3 C5 . . 122.2(2) ?
O2 C4 N1 . . 121.1(2) ?
O2 C4 C3 . . 130.0(2) ?
N1 C4 C3 . . 108.9(2) ?
C6 C5 C8 . . 105.93(19) ?
C6 C5 C3 . . 126.5(2) ?
C8 C5 C3 . . 127.6(2) ?
C5 C6 N3 . . 110.5(2) ?
C5 C6 H6 . . 124.7 ?
N3 C6 H6 . . 124.7 ?
N3 C7 C12 . . 129.6(2) ?
N3 C7 C8 . . 107.84(19) ?
C12 C7 C8 . . 122.6(2) ?
C9 C8 C7 . . 118.9(2) ?
C9 C8 C5 . . 134.2(2) ?
C7 C8 C5 . . 106.97(19) ?
C10 C9 C8 . . 118.4(2) ?
C10 C9 H9 . . 120.8 ?
C8 C9 H9 . . 120.8 ?
C9 C10 C11 . . 121.2(2) ?
C9 C10 H10 . . 119.4 ?
C11 C10 H10 . . 119.4 ?
C12 C11 C10 . . 121.8(2) ?
C12 C11 H11 . . 119.1 ?
C10 C11 H11 . . 119.1 ?
C11 C12 C7 . . 117.2(2) ?
C11 C12 H12 . . 121.4 ?
C7 C12 H12 . . 121.4 ?
N1 C13 C14 . . 112.7(2) ?
N1 C13 H13A . . 109.1 ?
C14 C13 H13A . . 109.1 ?
N1 C13 H13B . . 109.1 ?
C14 C13 H13B . . 109.1 ?
H13A C13 H13B . . 107.8 ?
O3 C14 C13 . . 109.3(2) ?
O3 C14 H14A . . 109.8 ?
C13 C14 H14A . . 109.8 ?
O3 C14 H14B . . 109.8 ?
C13 C14 H14B . . 109.8 ?
H14A C14 H14B . . 108.3 ?
N2 C15 C16 . . 114.1(2) ?
N2 C15 H15A . . 108.7 ?
C16 C15 H15A . . 108.7 ?
N2 C15 H15B . . 108.7 ?
C16 C15 H15B . . 108.7 ?
H15A C15 H15B . . 107.6 ?
O4 C16 C15 . . 108.7(2) ?
O4 C16 H16A . . 110.0 ?
C15 C16 H16A . . 110.0 ?
O4 C16 H16B . . 110.0 ?
C15 C16 H16B . . 110.0 ?
H16A C16 H16B . . 108.3 ?
O5 C17 N4 . . 126.8(2) ?
O5 C17 C18 . . 126.4(2) ?
N4 C17 C18 . . 106.73(19) ?
N5 C18 C19 . . 133.9(2) ?
N5 C18 C17 . . 117.3(2) ?
C19 C18 C17 . . 108.8(2) ?
C18 C19 C20 . . 106.70(19) ?
C18 C19 C21 . . 131.2(2) ?
C20 C19 C21 . . 121.95(19) ?
O6 C20 N4 . . 122.2(2) ?
O6 C20 C19 . . 129.5(2) ?
N4 C20 C19 . . 108.30(19) ?
C22 C21 C24 . . 106.0(2) ?
C22 C21 C19 . . 126.2(2) ?
C24 C21 C19 . . 127.8(2) ?
C21 C22 N6 . . 110.4(2) ?
C21 C22 H22 . . 124.8 ?
N6 C22 H22 . . 124.8 ?
N6 C23 C28 . . 130.4(3) ?
N6 C23 C24 . . 107.4(2) ?
C28 C23 C24 . . 122.2(3) ?
C25 C24 C23 . . 118.9(2) ?
C25 C24 C21 . . 134.0(2) ?
C23 C24 C21 . . 107.1(2) ?
C26 C25 C24 . . 118.9(3) ?
C26 C25 H25 . . 120.6 ?
C24 C25 H25 . . 120.6 ?
C25 C26 C27 . . 120.6(3) ?
C25 C26 H26 . . 119.7 ?
C27 C26 H26 . . 119.7 ?
C28 C27 C26 . . 122.2(3) ?
C28 C27 H27 . . 118.9 ?
C26 C27 H27 . . 118.9 ?
C27 C28 C23 . . 117.2(3) ?
C27 C28 H28 . . 121.4 ?
C23 C28 H28 . . 121.4 ?
N4 C29 C30 . . 112.8(2) ?
N4 C29 H29A . . 109.0 ?
C30 C29 H29A . . 109.0 ?
N4 C29 H29B . . 109.0 ?
C30 C29 H29B . . 109.0 ?
H29A C29 H29B . . 107.8 ?
O7 C30 C29 . . 108.9(2) ?
O7 C30 H30A . . 109.9 ?
C29 C30 H30A . . 109.9 ?
O7 C30 H30B . . 109.9 ?
C29 C30 H30B . . 109.9 ?
H30A C30 H30B . . 108.3 ?
N5 C31 C32 . . 113.1(2) ?
N5 C31 H31A . . 109.0 ?
C32 C31 H31A . . 109.0 ?
N5 C31 H31B . . 109.0 ?
C32 C31 H31B . . 109.0 ?
H31A C31 H31B . . 107.8 ?
O8 C32 C31 . . 109.1(2) ?
O8 C32 H32A . . 109.9 ?
C31 C32 H32A . . 109.9 ?
O8 C32 H32B . . 109.9 ?
C31 C32 H32B . . 109.9 ?
H32A C32 H32B . . 108.3 ?
O9 C33 N7 . . 126.2(2) ?
O9 C33 C34 . . 128.0(2) ?
N7 C33 C34 . . 105.74(19) ?
N8 C34 C35 . . 134.2(2) ?
N8 C34 C33 . . 117.10(19) ?
C35 C34 C33 . . 108.75(19) ?
C34 C35 C36 . . 106.81(19) ?
C34 C35 C37 . . 130.6(2) ?
C36 C35 C37 . . 122.42(19) ?
O10 C36 N7 . . 121.5(2) ?
O10 C36 C35 . . 129.2(2) ?
N7 C36 C35 . . 109.28(19) ?
C38 C37 C40 . . 106.50(19) ?
C38 C37 C35 . . 124.5(2) ?
C40 C37 C35 . . 129.0(2) ?
N9 C38 C37 . . 110.3(2) ?
N9 C38 H38 . . 124.9 ?
C37 C38 H38 . . 124.9 ?
N9 C39 C44 . . 129.3(2) ?
N9 C39 C40 . . 108.3(2) ?
C44 C39 C40 . . 122.4(3) ?
C41 C40 C39 . . 118.8(2) ?
C41 C40 C37 . . 135.0(2) ?
C39 C40 C37 . . 106.2(2) ?
C42 C41 C40 . . 118.6(2) ?
C42 C41 H41 . . 120.7 ?
C40 C41 H41 . . 120.7 ?
C41 C42 C43 . . 120.8(3) ?
C41 C42 H42 . . 119.6 ?
C43 C42 H42 . . 119.6 ?
C44 C43 C42 . . 122.1(2) ?
C44 C43 H43 . . 118.9 ?
C42 C43 H43 . . 118.9 ?
C43 C44 C39 . . 117.2(3) ?
C43 C44 H44 . . 121.4 ?
C39 C44 H44 . . 121.4 ?
N7 C45 C46 . . 111.06(19) ?
N7 C45 H45A . . 109.4 ?
C46 C45 H45A . . 109.4 ?
N7 C45 H45B . . 109.4 ?
C46 C45 H45B . . 109.4 ?
H45A C45 H45B . . 108.0 ?
O11 C46 C45 . . 111.87(19) ?
O11 C46 H46A . . 109.2 ?
C45 C46 H46A . . 109.2 ?
O11 C46 H46B . . 109.2 ?
C45 C46 H46B . . 109.2 ?
H46A C46 H46B . . 107.9 ?
N8 C47 C48 . . 112.0(2) ?
N8 C47 H47A . . 109.2 ?
C48 C47 H47A . . 109.2 ?
N8 C47 H47B . . 109.2 ?
C48 C47 H47B . . 109.2 ?
H47A C47 H47B . . 107.9 ?
O12 C48 C47 . . 112.37(19) ?
O12 C48 H48A . . 109.1 ?
C47 C48 H48A . . 109.1 ?
O12 C48 H48B . . 109.1 ?
C47 C48 H48B . . 109.1 ?
H48A C48 H48B . . 107.9 ?
O13 C49 N10 . . 127.0(2) ?
O13 C49 C50 . . 126.6(2) ?
N10 C49 C50 . . 106.34(19) ?
N11 C50 C51 . . 135.2(2) ?
N11 C50 C49 . . 116.7(2) ?
C51 C50 C49 . . 108.1(2) ?
C50 C51 C52 . . 107.10(19) ?
C50 C51 C53 . . 129.9(2) ?
C52 C51 C53 . . 122.75(19) ?
O14 C52 N10 . . 122.5(2) ?
O14 C52 C51 . . 128.7(2) ?
N10 C52 C51 . . 108.79(19) ?
C54 C53 C56 . . 106.44(19) ?
C54 C53 C51 . . 125.21(19) ?
C56 C53 C51 . . 128.4(2) ?
N12 C54 C53 . . 110.0(2) ?
N12 C54 H54 . . 125.0 ?
C53 C54 H54 . . 125.0 ?
N12 C55 C60 . . 130.0(2) ?
N12 C55 C56 . . 107.84(19) ?
C60 C55 C56 . . 122.1(2) ?
C57 C56 C55 . . 118.5(2) ?
C57 C56 C53 . . 135.0(2) ?
C55 C56 C53 . . 106.50(19) ?
C58 C57 C56 . . 119.2(2) ?
C58 C57 H57 . . 120.4 ?
C56 C57 H57 . . 120.4 ?
C57 C58 C59 . . 121.4(2) ?
C57 C58 H58 . . 119.3 ?
C59 C58 H58 . . 119.3 ?
C60 C59 C58 . . 121.5(2) ?
C60 C59 H59 . . 119.3 ?
C58 C59 H59 . . 119.3 ?
C59 C60 C55 . . 117.3(2) ?
C59 C60 H60 . . 121.4 ?
C55 C60 H60 . . 121.4 ?
N10 C61 C62 . . 111.7(2) ?
N10 C61 H61A . . 109.3 ?
C62 C61 H61A . . 109.3 ?
N10 C61 H61B . . 109.3 ?
C62 C61 H61B . . 109.3 ?
H61A C61 H61B . . 107.9 ?
O15 C62 C61 . . 111.0(2) ?
O15 C62 H62A . . 109.4 ?
C61 C62 H62A . . 109.4 ?
O15 C62 H62B . . 109.4 ?
C61 C62 H62B . . 109.4 ?
H62A C62 H62B . . 108.0 ?
N11 C63 C64 . . 111.08(19) ?
N11 C63 H63A . . 109.4 ?
C64 C63 H63A . . 109.4 ?
N11 C63 H63B . . 109.4 ?
C64 C63 H63B . . 109.4 ?
H63A C63 H63B . . 108.0 ?
O16 C64 C63 . . 112.60(19) ?
O16 C64 H64A . . 109.1 ?
C63 C64 H64A . . 109.1 ?
O16 C64 H64B . . 109.1 ?
C63 C64 H64B . . 109.1 ?
H64A C64 H64B . . 107.8 ?
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
O1 C1 . 1.212(2) ?
O2 C4 . 1.215(3) ?
O3 C14 . 1.426(3) ?
O3 H3 . 0.84(3) ?
O4 C16 . 1.412(3) ?
O4 H4 . 0.822(17) ?
O5 C17 . 1.214(2) ?
O6 C20 . 1.211(2) ?
O7 C30 . 1.417(3) ?
O7 H7 . 0.864(17) ?
O8 C32 . 1.427(3) ?
O8 H8A . 0.846(18) ?
O9 C33 . 1.203(2) ?
O10 C36 . 1.229(2) ?
O11 C46 . 1.416(3) ?
O11 H11A . 0.866(18) ?
O12 C48 . 1.423(3) ?
O12 H12A . 0.836(16) ?
O13 C49 . 1.207(2) ?
O14 C52 . 1.222(2) ?
O15 C62 . 1.410(3) ?
O15 H15 . 0.838(16) ?
O16 C64 . 1.420(3) ?
O16 H16 . 0.831(17) ?
N1 C1 . 1.362(3) ?
N1 C4 . 1.413(2) ?
N1 C13 . 1.452(3) ?
N2 C2 . 1.326(3) ?
N2 C15 . 1.463(3) ?
N2 H2 . 0.86(3) ?
N3 C6 . 1.365(3) ?
N3 C7 . 1.368(3) ?
N3 H3A . 0.87(2) ?
N4 C17 . 1.354(3) ?
N4 C20 . 1.418(3) ?
N4 C29 . 1.454(3) ?
N5 C18 . 1.344(3) ?
N5 C31 . 1.450(3) ?
N5 H5 . 0.829(15) ?
N6 C22 . 1.367(3) ?
N6 C23 . 1.368(3) ?
N6 H6A . 0.835(15) ?
N7 C33 . 1.384(3) ?
N7 C36 . 1.400(2) ?
N7 C45 . 1.453(2) ?
N8 C34 . 1.334(3) ?
N8 C47 . 1.449(3) ?
N8 H8B . 0.886(15) ?
N9 C38 . 1.361(3) ?
N9 C39 . 1.364(3) ?
N9 H9A . 0.890(16) ?
N10 C49 . 1.376(3) ?
N10 C52 . 1.403(2) ?
N10 C61 . 1.457(3) ?
N11 C50 . 1.339(3) ?
N11 C63 . 1.457(3) ?
N11 H11B . 0.878(15) ?
N12 C54 . 1.368(3) ?
N12 C55 . 1.369(3) ?
N12 H12B . 0.848(15) ?
C1 C2 . 1.511(3) ?
C2 C3 . 1.364(3) ?
C3 C4 . 1.455(3) ?
C3 C5 . 1.468(3) ?
C5 C6 . 1.365(3) ?
C5 C8 . 1.436(3) ?
C6 H6 . 0.9300 ?
C7 C12 . 1.388(3) ?
C7 C8 . 1.404(3) ?
C8 C9 . 1.396(3) ?
C9 C10 . 1.378(3) ?
C9 H9 . 0.9300 ?
C10 C11 . 1.395(3) ?
C10 H10 . 0.9300 ?
C11 C12 . 1.358(3) ?
C11 H11 . 0.9300 ?
C12 H12 . 0.9300 ?
C13 C14 . 1.500(3) ?
C13 H13A . 0.9700 ?
C13 H13B . 0.9700 ?
C14 H14A . 0.9700 ?
C14 H14B . 0.9700 ?
C15 C16 . 1.495(3) ?
C15 H15A . 0.9700 ?
C15 H15B . 0.9700 ?
C16 H16A . 0.9700 ?
C16 H16B . 0.9700 ?
C17 C18 . 1.500(3) ?
C18 C19 . 1.358(3) ?
C19 C20 . 1.456(3) ?
C19 C21 . 1.471(3) ?
C21 C22 . 1.365(3) ?
C21 C24 . 1.438(3) ?
C22 H22 . 0.9300 ?
C23 C28 . 1.392(3) ?
C23 C24 . 1.409(3) ?
C24 C25 . 1.395(3) ?
C25 C26 . 1.377(3) ?
C25 H25 . 0.9300 ?
C26 C27 . 1.399(3) ?
C26 H26 . 0.9300 ?
C27 C28 . 1.358(4) ?
C27 H27 . 0.9300 ?
C28 H28 . 0.9300 ?
C29 C30 . 1.506(3) ?
C29 H29A . 0.9700 ?
C29 H29B . 0.9700 ?
C30 H30A . 0.9700 ?
C30 H30B . 0.9700 ?
C31 C32 . 1.490(3) ?
C31 H31A . 0.9700 ?
C31 H31B . 0.9700 ?
C32 H32A . 0.9700 ?
C32 H32B . 0.9700 ?
C33 C34 . 1.502(3) ?
C34 C35 . 1.368(3) ?
C35 C36 . 1.444(3) ?
C35 C37 . 1.464(3) ?
C37 C38 . 1.366(3) ?
C37 C40 . 1.432(3) ?
C38 H38 . 0.9300 ?
C39 C44 . 1.393(3) ?
C39 C40 . 1.409(3) ?
C40 C41 . 1.399(3) ?
C41 C42 . 1.384(3) ?
C41 H41 . 0.9300 ?
C42 C43 . 1.399(3) ?
C42 H42 . 0.9300 ?
C43 C44 . 1.358(4) ?
C43 H43 . 0.9300 ?
C44 H44 . 0.9300 ?
C45 C46 . 1.509(3) ?
C45 H45A . 0.9700 ?
C45 H45B . 0.9700 ?
C46 H46A . 0.9700 ?
C46 H46B . 0.9700 ?
C47 C48 . 1.507(3) ?
C47 H47A . 0.9700 ?
C47 H47B . 0.9700 ?
C48 H48A . 0.9700 ?
C48 H48B . 0.9700 ?
C49 C50 . 1.513(3) ?
C50 C51 . 1.370(3) ?
C51 C52 . 1.459(3) ?
C51 C53 . 1.463(3) ?
C53 C54 . 1.372(3) ?
C53 C56 . 1.441(3) ?
C54 H54 . 0.9300 ?
C55 C60 . 1.391(3) ?
C55 C56 . 1.414(3) ?
C56 C57 . 1.400(3) ?
C57 C58 . 1.367(3) ?
C57 H57 . 0.9300 ?
C58 C59 . 1.392(3) ?
C58 H58 . 0.9300 ?
C59 C60 . 1.378(3) ?
C59 H59 . 0.9300 ?
C60 H60 . 0.9300 ?
C61 C62 . 1.515(3) ?
C61 H61A . 0.9700 ?
C61 H61B . 0.9700 ?
C62 H62A . 0.9700 ?
C62 H62B . 0.9700 ?
C63 C64 . 1.505(3) ?
C63 H63A . 0.9700 ?
C63 H63B . 0.9700 ?
C64 H64A . 0.9700 ?
C64 H64B . 0.9700 ?
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
N2 H2 O12 2_566 0.86(3) 2.09(3) 2.950(3) 177(3)
O3 H3 O8 1_455 0.84(3) 1.93(3) 2.762(3) 172(3)
O4 H4 O14 1_556 0.822(17) 1.972(19) 2.770(2) 163(3)
N5 H5 O16 1_655 0.829(15) 2.222(16) 3.027(3) 164(2)
O7 H7 O4 1_654 0.864(17) 1.893(18) 2.755(3) 175(3)
O15 H15 O1 2_576 0.838(16) 2.22(2) 2.893(2) 137(3)
O15 H15 O12 1_565 0.838(16) 2.42(2) 3.097(3) 139(3)
O16 H16 O11 2_566 0.831(17) 1.958(18) 2.780(3) 170(3)
N3 H3A O6 1_556 0.87(2) 2.06(2) 2.840(2) 149(2)
N6 H6A O14 . 0.835(15) 2.221(16) 3.042(3) 168(2)
O8 H8A O10 2_666 0.846(18) 1.903(18) 2.746(3) 173(3)
N9 H9A O2 2_666 0.890(16) 1.945(19) 2.760(2) 152(2)
O11 H11A O5 1_455 0.866(18) 2.13(2) 2.935(2) 154(3)
O11 H11A O16 . 0.866(18) 2.51(3) 3.033(3) 120(3)
O12 H12A O15 2_565 0.836(16) 1.915(17) 2.739(2) 168(3)
N8 H8B O7 2_665 0.886(15) 2.090(17) 2.867(3) 145.9(18)
N11 H11B O3 . 0.878(15) 2.17(2) 2.945(3) 147(2)
N12 H12B O10 2_666 0.848(15) 2.101(16) 2.925(2) 164(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
C4 N1 C1 O1 . . . . 179.4(2) ?
C13 N1 C1 O1 . . . . 4.7(4) ?
C4 N1 C1 C2 . . . . -1.2(2) ?
C13 N1 C1 C2 . . . . -175.9(2) ?
C15 N2 C2 C3 . . . . -9.9(4) ?
C15 N2 C2 C1 . . . . 168.2(2) ?
O1 C1 C2 N2 . . . . 2.2(4) ?
N1 C1 C2 N2 . . . . -177.1(2) ?
O1 C1 C2 C3 . . . . -179.2(2) ?
N1 C1 C2 C3 . . . . 1.4(2) ?
N2 C2 C3 C4 . . . . 177.2(3) ?
C1 C2 C3 C4 . . . . -1.0(2) ?
N2 C2 C3 C5 . . . . -7.8(4) ?
C1 C2 C3 C5 . . . . 173.9(2) ?
C1 N1 C4 O2 . . . . -179.2(2) ?
C13 N1 C4 O2 . . . . -4.4(3) ?
C1 N1 C4 C3 . . . . 0.6(2) ?
C13 N1 C4 C3 . . . . 175.3(2) ?
C2 C3 C4 O2 . . . . -179.9(2) ?
C5 C3 C4 O2 . . . . 4.6(4) ?
C2 C3 C4 N1 . . . . 0.3(2) ?
C5 C3 C4 N1 . . . . -175.19(19) ?
C2 C3 C5 C6 . . . . -58.8(4) ?
C4 C3 C5 C6 . . . . 115.5(3) ?
C2 C3 C5 C8 . . . . 120.0(3) ?
C4 C3 C5 C8 . . . . -65.7(3) ?
C8 C5 C6 N3 . . . . -1.8(3) ?
C3 C5 C6 N3 . . . . 177.2(2) ?
C7 N3 C6 C5 . . . . 1.4(3) ?
C6 N3 C7 C12 . . . . -179.8(3) ?
C6 N3 C7 C8 . . . . -0.3(3) ?
N3 C7 C8 C9 . . . . 179.0(2) ?
C12 C7 C8 C9 . . . . -1.4(4) ?
N3 C7 C8 C5 . . . . -0.9(3) ?
C12 C7 C8 C5 . . . . 178.8(2) ?
C6 C5 C8 C9 . . . . -178.2(3) ?
C3 C5 C8 C9 . . . . 2.8(4) ?
C6 C5 C8 C7 . . . . 1.6(3) ?
C3 C5 C8 C7 . . . . -177.4(2) ?
C7 C8 C9 C10 . . . . 0.4(3) ?
C5 C8 C9 C10 . . . . -179.8(3) ?
C8 C9 C10 C11 . . . . 0.8(4) ?
C9 C10 C11 C12 . . . . -1.1(4) ?
C10 C11 C12 C7 . . . . 0.2(4) ?
N3 C7 C12 C11 . . . . -179.4(3) ?
C8 C7 C12 C11 . . . . 1.1(4) ?
C1 N1 C13 C14 . . . . -83.0(3) ?
C4 N1 C13 C14 . . . . 103.1(3) ?
N1 C13 C14 O3 . . . . -62.8(3) ?
C2 N2 C15 C16 . . . . 108.6(3) ?
N2 C15 C16 O4 . . . . 70.6(3) ?
C20 N4 C17 O5 . . . . 178.5(2) ?
C29 N4 C17 O5 . . . . 7.6(4) ?
C20 N4 C17 C18 . . . . -2.5(3) ?
C29 N4 C17 C18 . . . . -173.3(2) ?
C31 N5 C18 C19 . . . . -11.6(4) ?
C31 N5 C18 C17 . . . . 167.7(2) ?
O5 C17 C18 N5 . . . . 2.7(4) ?
N4 C17 C18 N5 . . . . -176.3(2) ?
O5 C17 C18 C19 . . . . -177.8(2) ?
N4 C17 C18 C19 . . . . 3.1(3) ?
N5 C18 C19 C20 . . . . 176.9(3) ?
C17 C18 C19 C20 . . . . -2.4(3) ?
N5 C18 C19 C21 . . . . -8.3(5) ?
C17 C18 C19 C21 . . . . 172.4(2) ?
C17 N4 C20 O6 . . . . -177.9(2) ?
C29 N4 C20 O6 . . . . -7.1(4) ?
C17 N4 C20 C19 . . . . 1.0(3) ?
C29 N4 C20 C19 . . . . 171.9(2) ?
C18 C19 C20 O6 . . . . 179.8(3) ?
C21 C19 C20 O6 . . . . 4.4(4) ?
C18 C19 C20 N4 . . . . 1.0(3) ?
C21 C19 C20 N4 . . . . -174.4(2) ?
C18 C19 C21 C22 . . . . -57.9(4) ?
C20 C19 C21 C22 . . . . 116.2(3) ?
C18 C19 C21 C24 . . . . 122.4(3) ?
C20 C19 C21 C24 . . . . -63.4(3) ?
C24 C21 C22 N6 . . . . -1.5(3) ?
C19 C21 C22 N6 . . . . 178.8(2) ?
C23 N6 C22 C21 . . . . 1.2(3) ?
C22 N6 C23 C28 . . . . -179.7(2) ?
C22 N6 C23 C24 . . . . -0.4(3) ?
N6 C23 C24 C25 . . . . 180.0(2) ?
C28 C23 C24 C25 . . . . -0.7(3) ?
N6 C23 C24 C21 . . . . -0.5(2) ?
C28 C23 C24 C21 . . . . 178.8(2) ?
C22 C21 C24 C25 . . . . -179.3(3) ?
C19 C21 C24 C25 . . . . 0.4(4) ?
C22 C21 C24 C23 . . . . 1.2(2) ?
C19 C21 C24 C23 . . . . -179.1(2) ?
C23 C24 C25 C26 . . . . -0.2(3) ?
C21 C24 C25 C26 . . . . -179.6(2) ?
C24 C25 C26 C27 . . . . 1.0(4) ?
C25 C26 C27 C28 . . . . -1.0(4) ?
C26 C27 C28 C23 . . . . 0.1(4) ?
N6 C23 C28 C27 . . . . 179.9(3) ?
C24 C23 C28 C27 . . . . 0.8(4) ?
C17 N4 C29 C30 . . . . -77.1(3) ?
C20 N4 C29 C30 . . . . 113.5(3) ?
N4 C29 C30 O7 . . . . -64.3(3) ?
C18 N5 C31 C32 . . . . 112.1(3) ?
N5 C31 C32 O8 . . . . 65.4(3) ?
C36 N7 C33 O9 . . . . -174.9(2) ?
C45 N7 C33 O9 . . . . -5.6(4) ?
C36 N7 C33 C34 . . . . 5.2(2) ?
C45 N7 C33 C34 . . . . 174.5(2) ?
C47 N8 C34 C35 . . . . 19.5(4) ?
C47 N8 C34 C33 . . . . -161.0(2) ?
O9 C33 C34 N8 . . . . -4.4(4) ?
N7 C33 C34 N8 . . . . 175.5(2) ?
O9 C33 C34 C35 . . . . 175.1(3) ?
N7 C33 C34 C35 . . . . -4.9(3) ?
N8 C34 C35 C36 . . . . -177.8(3) ?
C33 C34 C35 C36 . . . . 2.7(3) ?
N8 C34 C35 C37 . . . . 6.9(5) ?
C33 C34 C35 C37 . . . . -172.6(2) ?
C33 N7 C36 O10 . . . . 175.0(2) ?
C45 N7 C36 O10 . . . . 5.5(4) ?
C33 N7 C36 C35 . . . . -3.7(3) ?
C45 N7 C36 C35 . . . . -173.2(2) ?
C34 C35 C36 O10 . . . . -178.2(2) ?
C37 C35 C36 O10 . . . . -2.4(4) ?
C34 C35 C36 N7 . . . . 0.4(3) ?
C37 C35 C36 N7 . . . . 176.3(2) ?
C34 C35 C37 C38 . . . . 45.4(4) ?
C36 C35 C37 C38 . . . . -129.3(2) ?
C34 C35 C37 C40 . . . . -134.2(3) ?
C36 C35 C37 C40 . . . . 51.1(3) ?
C39 N9 C38 C37 . . . . -1.4(3) ?
C40 C37 C38 N9 . . . . 2.2(3) ?
C35 C37 C38 N9 . . . . -177.46(19) ?
C38 N9 C39 C44 . . . . -179.7(2) ?
C38 N9 C39 C40 . . . . 0.0(3) ?
N9 C39 C40 C41 . . . . -178.0(2) ?
C44 C39 C40 C41 . . . . 1.8(3) ?
N9 C39 C40 C37 . . . . 1.3(2) ?
C44 C39 C40 C37 . . . . -179.0(2) ?
C38 C37 C40 C41 . . . . 177.0(2) ?
C35 C37 C40 C41 . . . . -3.4(4) ?
C38 C37 C40 C39 . . . . -2.1(2) ?
C35 C37 C40 C39 . . . . 177.5(2) ?
C39 C40 C41 C42 . . . . 0.3(3) ?
C37 C40 C41 C42 . . . . -178.7(2) ?
C40 C41 C42 C43 . . . . -2.0(3) ?
C41 C42 C43 C44 . . . . 1.7(4) ?
C42 C43 C44 C39 . . . . 0.3(4) ?
N9 C39 C44 C43 . . . . 177.6(2) ?
C40 C39 C44 C43 . . . . -2.1(4) ?
C33 N7 C45 C46 . . . . 89.9(3) ?
C36 N7 C45 C46 . . . . -102.2(2) ?
N7 C45 C46 O11 . . . . 166.08(18) ?
C34 N8 C47 C48 . . . . 60.6(3) ?
N8 C47 C48 O12 . . . . 60.5(3) ?
C52 N10 C49 O13 . . . . 175.2(2) ?
C61 N10 C49 O13 . . . . 7.2(4) ?
C52 N10 C49 C50 . . . . -4.3(2) ?
C61 N10 C49 C50 . . . . -172.23(19) ?
C63 N11 C50 C51 . . . . -22.0(4) ?
C63 N11 C50 C49 . . . . 157.6(2) ?
O13 C49 C50 N11 . . . . 4.3(4) ?
N10 C49 C50 N11 . . . . -176.2(2) ?
O13 C49 C50 C51 . . . . -176.0(2) ?
N10 C49 C50 C51 . . . . 3.5(2) ?
N11 C50 C51 C52 . . . . 178.3(3) ?
C49 C50 C51 C52 . . . . -1.3(2) ?
N11 C50 C51 C53 . . . . -7.0(4) ?
C49 C50 C51 C53 . . . . 173.4(2) ?
C49 N10 C52 O14 . . . . -175.1(2) ?
C61 N10 C52 O14 . . . . -7.4(3) ?
C49 N10 C52 C51 . . . . 3.6(3) ?
C61 N10 C52 C51 . . . . 171.4(2) ?
C50 C51 C52 O14 . . . . 177.4(2) ?
C53 C51 C52 O14 . . . . 2.2(4) ?
C50 C51 C52 N10 . . . . -1.3(2) ?
C53 C51 C52 N10 . . . . -176.44(19) ?
C50 C51 C53 C54 . . . . -43.0(4) ?
C52 C51 C53 C54 . . . . 130.9(3) ?
C50 C51 C53 C56 . . . . 136.3(3) ?
C52 C51 C53 C56 . . . . -49.8(3) ?
C55 N12 C54 C53 . . . . 1.3(3) ?
C56 C53 C54 N12 . . . . -1.9(3) ?
C51 C53 C54 N12 . . . . 177.6(2) ?
C54 N12 C55 C60 . . . . -179.2(3) ?
C54 N12 C55 C56 . . . . -0.2(3) ?
N12 C55 C56 C57 . . . . 178.2(2) ?
C60 C55 C56 C57 . . . . -2.8(4) ?
N12 C55 C56 C53 . . . . -0.9(3) ?
C60 C55 C56 C53 . . . . 178.1(2) ?
C54 C53 C56 C57 . . . . -177.2(3) ?
C51 C53 C56 C57 . . . . 3.4(4) ?
C54 C53 C56 C55 . . . . 1.7(3) ?
C51 C53 C56 C55 . . . . -177.7(2) ?
C55 C56 C57 C58 . . . . 1.3(4) ?
C53 C56 C57 C58 . . . . -180.0(3) ?
C56 C57 C58 C59 . . . . 0.5(4) ?
C57 C58 C59 C60 . . . . -1.0(4) ?
C58 C59 C60 C55 . . . . -0.4(4) ?
N12 C55 C60 C59 . . . . -178.9(3) ?
C56 C55 C60 C59 . . . . 2.3(4) ?
C49 N10 C61 C62 . . . . -80.2(3) ?
C52 N10 C61 C62 . . . . 113.8(2) ?
N10 C61 C62 O15 . . . . -170.44(18) ?
C50 N11 C63 C64 . . . . -61.8(3) ?
N11 C63 C64 O16 . . . . -60.6(3) ?
