##############################################################################
###                                                                        ###
###           Full Paper (Acta Crystallographica Section C)                ###
###                                                                        ###
##############################################################################
#                                                                            #
# This CIF contains the data in a paper accepted for publication in Acta     #
# Crystallographica Section C. It conforms to the editorial and technical    #
# requirements of Notes for Authors for 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. The current version number is 2.4.    #
#                                                                            #
# Software is freely available for graphical display of the structure(s) in  #
# this CIF.  For information consult the CIF home page http://www.iucr.org/  #
# cif/home.html                                                              #
#                                                                            #
# 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.                                        #
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##############################################################################
data_global
_audit_creation_method     'by CrystalStructure 3.8'
_journal_date_recd_electronic     2008-03-31
_journal_date_accepted     2008-04-11
_journal_name_full     'Acta Crystallographica, Section C'
_journal_year     2008
_journal_volume     64
_journal_issue      5
_journal_page_first     o290
_journal_page_last     o292
_journal_paper_category     FO
_journal_coeditor_code     SQ3139
_publ_contact_author_name     'Ram, Thaimattam'
_publ_contact_author_address
;
Centre for Excellence in Polymorphism & Particle Engineering
Dr Reddy's Laboratories Ltd
IPDO Innovation Plaza
Bachupally
Hyderabad
India
;
_publ_contact_author_email     ramthaimattam@drreddys.com
_publ_contact_author_fax     '91-40-44346285'
_publ_contact_author_phone     '91-40-44346150'
_publ_section_title
;
Desvenlafaxine succinate monohydrate
;
_publ_section_title_footnote
;
DRL IPDOIPM Communication No. 00121.
;
loop_
    _publ_author_name
    _publ_author_footnote
    _publ_author_address
    'Venu, Nalivela' .
;
Centre for Excellence in Polymorphism and Particle Engineering
Dr Reddy's Laboratories Ltd
IPDO Innovation Plaza
Bachupally
Hyderabad
India
;
    'Srikanth, Bukkapattanam R.' .
;
Department of Analytical Research
Dr Reddy's Laboratories Ltd
Discovery Research
Miyapur
Hyderabad
India
;
    'Ram, Thaimattam' .
;
Centre for Excellence in Polymorphism and Particle Engineering
Dr Reddy's Laboratories Ltd
IPDO Innovation Plaza
Bachupally
Hyderabad
India
;
    'Devarakonda, Surya' .
;
Centre for Excellence in Polymorphism and Particle Engineering
Dr Reddy's Laboratories Ltd
IPDO Innovation Plaza
Bachupally
Hyderabad
India
;
data_I
_chemical_name_systematic
;
[2-(1-hydroxycyclohexyl)-2-(4-hydroxyphenyl)ethyl]dimethylammonium
3-carboxypropanoate monohydrate
;
_chemical_name_common
;
Desvenlafaxine succinate monohydrate
;
_chemical_formula_moiety     'C16 H26 N O2 +, C4 H5 O4 -, H2 O'
_chemical_formula_sum     'C20 H33 N O7'
_chemical_formula_iupac     'C16 H26 N O2 +, C4 H5 O4 -, H2 O'
_chemical_formula_weight     399.48
_chemical_melting_point     ?
_symmetry_cell_setting     triclinic
_symmetry_space_group_name_H-M     'P -1'
_symmetry_space_group_name_Hall     '-P 1'
loop_
    _symmetry_equiv_pos_site_id
    _symmetry_equiv_pos_as_xyz
    1 '+X,+Y,+Z'
    2 '-X,-Y,-Z'
_cell_length_a     6.542(5)
_cell_length_b     9.324(8)
_cell_length_c     17.631(14)
_cell_angle_alpha     77.594(17)
_cell_angle_beta     84.00(2)
_cell_angle_gamma     89.39(2)
_cell_volume     1044.5(15)
_cell_formula_units_Z     2
_cell_measurement_reflns_used     3898
_cell_measurement_theta_min     1.2
_cell_measurement_theta_max     28.7
_cell_measurement_temperature     298
_exptl_crystal_description     'block'
_exptl_crystal_colour     'colorless'
_exptl_crystal_size_max     0.50
_exptl_crystal_size_mid     0.30
_exptl_crystal_size_min     0.12
_exptl_crystal_density_diffrn     1.270
_exptl_crystal_density_meas     ?
_exptl_crystal_density_method     'not measured'
_exptl_crystal_F_000     432.00
_exptl_absorpt_coefficient_mu     0.095
_exptl_absorpt_correction_type     multi-scan
_exptl_absorpt_process_details     '(Jacobson, 1998)'
_exptl_absorpt_correction_T_min     0.964
_exptl_absorpt_correction_T_max     0.989
_diffrn_radiation_type     'Mo K\a'
_diffrn_radiation_wavelength     0.71070
_diffrn_measurement_device_type     'Rigaku Mercury'
_diffrn_measurement_method     ω
_diffrn_detector_area_resol_mean     7.31
_diffrn_reflns_number     11016
_diffrn_reflns_av_R_equivalents     0.045
_diffrn_reflns_theta_max     29.30
_diffrn_reflns_theta_full     26.00
_diffrn_measured_fraction_theta_max     0.827
_diffrn_measured_fraction_theta_full     0.976
_diffrn_reflns_limit_h_min     -8
_diffrn_reflns_limit_h_max     6
_diffrn_reflns_limit_k_min     -12
_diffrn_reflns_limit_k_max     12
_diffrn_reflns_limit_l_min     -22
_diffrn_reflns_limit_l_max     22
_refine_special_details
;
Refinement was performed using reflections with F² > 0.5
σ(F²). The weighted R-factor (wR) and goodness of fit
(S) are based on F². R-factor (gt) are based on
F. The threshold expression of F² > 2.0 σ(F²) is
used only for calculating R-factor (gt).
;
_reflns_number_total     3995
_reflns_number_gt     2265
_reflns_threshold_expression     F²>2σ(F²)
_refine_ls_structure_factor_coef     Fsqd
_refine_ls_R_factor_gt     0.0650
_refine_ls_wR_factor_ref     0.1005
_refine_ls_goodness_of_fit_ref     1.253
_refine_ls_number_reflns     3875
_refine_ls_number_parameters     299
_refine_ls_hydrogen_treatment     mixed
_refine_ls_weighting_scheme     calc
_refine_ls_weighting_details
;
Chebychev polynomial with 3 parameters: 4182.1300    5759.2800    1682.9900
[Carruthers, J. R. & Watkin, D. J. (1979). Acta Cryst. A35, 698--699]
;
_refine_ls_shift/su_max     0.0000
_refine_diff_density_max     0.36
_refine_diff_density_min     -0.34
_refine_ls_extinction_method
;Larson, A. C. (1970). Crystallographic Computing, edited by F. R. Ahmed, p.
 291-294. Munksgaard: Copenhagen.
;
_refine_ls_extinction_coef      41E1(2)
loop_
    _atom_type_symbol
    _atom_type_description
    _atom_type_scat_dispersion_real
    _atom_type_scat_dispersion_imag
    _atom_type_scat_source
    'C' 'C' 0.003 0.002
;
International Tables for Crystallography
(1992, Vol. C, Tables 4.2.6.8 and 6.1.1.4)
;
    'H' 'H' 0.000 0.000
;
International Tables for Crystallography
(1992, Vol. C, Table 6.1.1.4)
;
    'N' 'N' 0.006 0.003
;
International Tables for Crystallography
(1992, Vol. C, Tables 4.2.6.8 and 6.1.1.4)
;
    'O' 'O' 0.011 0.006
;
International Tables for Crystallography
(1992, Vol. C, Tables 4.2.6.8 and 6.1.1.4)
;
_computing_data_collection     'CrystalClear (Rigaku, 1999)'
_computing_cell_refinement     'CrystalClear (Rigaku, 1999)'
_computing_data_reduction     'CrystalStructure (Rigaku/MSC, 2004)'
_computing_structure_solution     'SIR2004 (Burla et al.,  2005)'
_computing_structure_refinement     'CRYSTALS (Betteridge et al.,  2003)'
_computing_molecular_graphics
;
ORTEPIII (Burnett & Johnson, 1996), X-SEED (Barbour, 2001)
and Mercury (Macrae et al.,  2006
;
_computing_publication_material     'CrystalStructure (Rigaku/MSC, 2004)'
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 O1 0.3698(3) 0.8465(2) 0.18421(13) 0.0558(7) Uani . . 1.000
    O O2 0.0718(3) 0.04218(18) 0.16404(11) 0.0443(6) Uani . . 1.000
    N N1 0.2141(3) 0.1799(2) 0.36417(13) 0.0483(8) Uani . . 1.000
    C C1 0.1866(4) 0.4083(2) 0.21436(14) 0.0374(8) Uani . . 1.000
    C C2 0.0427(4) 0.5173(2) 0.21364(15) 0.0416(8) Uani . . 1.000
    C C3 0.0986(4) 0.6638(2) 0.20413(15) 0.0424(8) Uani . . 1.000
    C C4 0.3048(4) 0.7023(2) 0.19388(15) 0.0422(8) Uani . . 1.000
    C C5 0.4512(4) 0.5960(2) 0.19441(16) 0.0467(9) Uani . . 1.000
    C C6 0.3923(4) 0.4499(2) 0.20530(15) 0.0446(9) Uani . . 1.000
    C C7 0.1178(4) 0.2495(2) 0.22566(15) 0.0412(8) Uani . . 1.000
    C C8 0.1227(3) 0.1966(2) 0.14596(15) 0.0374(8) Uani . . 1.000
    C C9 0.3308(4) 0.2116(3) 0.09773(15) 0.0447(9) Uani . . 1.000
    C C10 0.3262(4) 0.1621(3) 0.02144(17) 0.0584(11) Uani . . 1.000
    C C11 0.1667(5) 0.2455(4) -0.02677(18) 0.0714(11) Uani . . 1.000
    C C12 -0.0456(5) 0.2316(3) 0.01962(18) 0.0653(12) Uani . . 1.000
    C C13 -0.0377(4) 0.2802(2) 0.09704(16) 0.0495(9) Uani . . 1.000
    C C14 0.2282(4) 0.1421(2) 0.28475(15) 0.0458(9) Uani . . 1.000
    C C15 0.3259(5) 0.0671(3) 0.41607(18) 0.0654(11) Uani . . 1.000
    C C16 0.0015(5) 0.1928(3) 0.39983(18) 0.0619(11) Uani . . 1.000
    O O3 0.2483(3) 0.4888(2) 0.39876(12) 0.0591(8) Uani . . 1.000
    O O4 0.5369(3) 0.3750(2) 0.37900(14) 0.0642(8) Uani . . 1.000
    O O5 1.1001(3) 0.7299(2) 0.40258(14) 0.0662(8) Uani . . 1.000
    O O6 0.8204(3) 0.8619(2) 0.38551(14) 0.0655(8) Uani . . 1.000
    C C17 0.4458(4) 0.4846(3) 0.39106(16) 0.0458(9) Uani . . 1.000
    C C18 0.5596(4) 0.6220(2) 0.39617(18) 0.0493(9) Uani . . 1.000
    C C19 0.7874(3) 0.6023(2) 0.39817(16) 0.0445(8) Uani . . 1.000
    C C20 0.9061(4) 0.7418(3) 0.39506(17) 0.0478(10) Uani . . 1.000
    O O7 0.6943(3) 0.9781(2) 0.24101(16) 0.0718(10) Uani . . 1.000
    H H1 0.265(4) 0.916(3) 0.1776(16) 0.0658 Uiso d . 1.000
    H H2 -0.09900 0.49100 0.22020 0.0510 Uiso calc R 1.000
    H H3 -0.00320 0.73720 0.20430 0.0520 Uiso calc R 1.000
    H H5 0.59260 0.62310 0.18770 0.0560 Uiso calc R 1.000
    H H6 0.49460 0.37650 0.20660 0.0540 Uiso calc R 1.000
    H H7 -0.02240 0.24520 0.24660 0.0500 Uiso calc R 1.000
    H H11 0.282(4) 0.270(3) 0.3644(16) 0.0604 Uiso d . 1.000
    H H21 -0.056(4) 0.028(2) 0.1848(15) 0.0479 Uiso d . 1.000
    H H91 0.37260 0.31190 0.08550 0.0540 Uiso calc R 1.000
    H H92 0.42760 0.15480 0.12760 0.0540 Uiso calc R 1.000
    H H101 0.45800 0.17500 -0.00760 0.0700 Uiso calc R 1.000
    H H102 0.28900 0.06090 0.03360 0.0700 Uiso calc R 1.000
    H H111 0.20620 0.34620 -0.04070 0.0870 Uiso calc R 1.000
    H H112 0.16100 0.20860 -0.07270 0.0870 Uiso calc R 1.000
    H H121 -0.08820 0.13160 0.03100 0.0810 Uiso calc R 1.000
    H H122 -0.14130 0.28970 -0.01030 0.0810 Uiso calc R 1.000
    H H131 -0.16870 0.26440 0.12650 0.0600 Uiso calc R 1.000
    H H132 -0.00420 0.38200 0.08530 0.0600 Uiso calc R 1.000
    H H141 0.36890 0.14260 0.26490 0.0560 Uiso calc R 1.000
    H H142 0.17140 0.04650 0.29060 0.0550 Uiso calc R 1.000
    H H151 0.23340 -0.01030 0.44150 0.0790 Uiso calc R 1.000
    H H152 0.38140 0.10940 0.45410 0.0790 Uiso calc R 1.000
    H H153 0.43420 0.02950 0.38600 0.0790 Uiso calc R 1.000
    H H161 -0.04150 0.29150 0.38450 0.0760 Uiso calc R 1.000
    H H162 -0.00220 0.16690 0.45510 0.0760 Uiso calc R 1.000
    H H163 -0.08800 0.12950 0.38280 0.0760 Uiso calc R 1.000
    H H31 0.172(5) 0.603(4) 0.400(2) 0.0979 Uiso d . 1.000
    H H181 0.50590 0.65310 0.44210 0.0600 Uiso calc R 1.000
    H H182 0.53930 0.69650 0.35160 0.0600 Uiso calc R 1.000
    H H191 0.80860 0.53510 0.44540 0.0540 Uiso calc R 1.000
    H H192 0.83820 0.56170 0.35500 0.0540 Uiso calc R 1.000
    H H71 0.735(6) 0.958(4) 0.292(2) 0.1089 Uiso d . 1.000
    H H72 0.638(5) 0.918(4) 0.225(2) 0.0796 Uiso d . 1.000
_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
    O1 C4 . . 1.384(3) no
    O2 C8 . . 1.441(3) no
    O1 H1 . . 0.94(3) no
    O2 H21 . . 0.88(3) no
    O3 C17 . . 1.286(3) no
    O4 C17 . . 1.224(4) no
    O5 C20 . . 1.291(3) no
    O6 C20 . . 1.234(4) no
    O3 H31 . . 1.18(4) no
    O5 H31 . 1_655 1.28(4) no
    O7 H71 . . 0.94(4) no
    O7 H72 . . 0.79(4) no
    N1 C16 . . 1.480(4) no
    N1 C14 . . 1.509(4) no
    N1 C15 . . 1.479(4) no
    N1 H11 . . 0.96(3) no
    C1 C6 . . 1.388(4) no
    C1 C2 . . 1.377(3) no
    C1 C7 . . 1.518(3) no
    C2 C3 . . 1.388(3) no
    C3 C4 . . 1.383(4) no
    C4 C5 . . 1.370(3) no
    C5 C6 . . 1.387(3) no
    C7 C14 . . 1.518(4) no
    C7 C8 . . 1.583(4) no
    C8 C13 . . 1.528(4) no
    C8 C9 . . 1.519(4) no
    C9 C10 . . 1.516(4) no
    C10 C11 . . 1.517(5) no
    C11 C12 . . 1.528(5) no
    C12 C13 . . 1.534(4) no
    C2 H2 . . 0.9500 no
    C3 H3 . . 0.9500 no
    C5 H5 . . 0.9500 no
    C6 H6 . . 0.9500 no
    C7 H7 . . 0.9500 no
    C9 H92 . . 0.9500 no
    C9 H91 . . 0.9500 no
    C10 H101 . . 0.9500 no
    C10 H102 . . 0.9500 no
    C11 H112 . . 0.9500 no
    C11 H111 . . 0.9500 no
    C12 H122 . . 0.9500 no
    C12 H121 . . 0.9500 no
    C13 H132 . . 0.9500 no
    C13 H131 . . 0.9500 no
    C14 H142 . . 0.9500 no
    C14 H141 . . 0.9500 no
    C15 H153 . . 0.9500 no
    C15 H152 . . 0.9500 no
    C15 H151 . . 0.9500 no
    C16 H161 . . 0.9500 no
    C16 H162 . . 0.9500 no
    C16 H163 . . 0.9500 no
    C17 C18 . . 1.513(4) no
    C18 C19 . . 1.503(4) no
    C19 C20 . . 1.510(4) no
    C18 H181 . . 0.9500 no
    C18 H182 . . 0.9500 no
    C19 H192 . . 0.9500 no
    C19 H191 . . 0.9500 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
    C4 O1 H1 . . . 114.7(17) no
    C8 O2 H21 . . . 110.2(13) no
    C17 O3 H31 . . . 117.4(17) no
    C20 O5 H31 . . 1_655 114.1(15) no
    H71 O7 H72 . . . 121(3) no
    C15 N1 C16 . . . 110.2(2) no
    C14 N1 C16 . . . 114.3(2) no
    C14 N1 C15 . . . 108.22(19) no
    C15 N1 H11 . . . 104.2(16) no
    C14 N1 H11 . . . 113.7(17) no
    C16 N1 H11 . . . 105.8(16) no
    C2 C1 C7 . . . 120.0(2) no
    C6 C1 C7 . . . 122.5(2) no
    C2 C1 C6 . . . 117.48(19) no
    C1 C2 C3 . . . 122.0(2) no
    C2 C3 C4 . . . 119.3(2) no
    O1 C4 C3 . . . 121.9(2) no
    C3 C4 C5 . . . 120.0(2) no
    O1 C4 C5 . . . 118.2(2) no
    C4 C5 C6 . . . 119.9(2) no
    C1 C6 C5 . . . 121.4(2) no
    C8 C7 C14 . . . 111.01(17) no
    C1 C7 C14 . . . 114.4(2) no
    C1 C7 C8 . . . 112.78(19) no
    O2 C8 C7 . . . 107.97(19) no
    O2 C8 C9 . . . 105.90(18) no
    C7 C8 C13 . . . 109.48(18) no
    O2 C8 C13 . . . 109.06(17) no
    C9 C8 C13 . . . 109.5(2) no
    C7 C8 C9 . . . 114.77(19) no
    C8 C9 C10 . . . 112.7(2) no
    C9 C10 C11 . . . 111.2(2) no
    C10 C11 C12 . . . 111.2(3) no
    C11 C12 C13 . . . 110.7(3) no
    C8 C13 C12 . . . 112.4(2) no
    N1 C14 C7 . . . 113.58(18) no
    C1 C2 H2 . . . 119.00 no
    C3 C2 H2 . . . 119.00 no
    C4 C3 H3 . . . 120.00 no
    C2 C3 H3 . . . 121.00 no
    C4 C5 H5 . . . 120.00 no
    C6 C5 H5 . . . 121.00 no
    C1 C6 H6 . . . 119.00 no
    C5 C6 H6 . . . 120.00 no
    C14 C7 H7 . . . 106.00 no
    C1 C7 H7 . . . 106.00 no
    C8 C7 H7 . . . 106.00 no
    C10 C9 H92 . . . 109.00 no
    C8 C9 H92 . . . 109.00 no
    C10 C9 H91 . . . 108.00 no
    C8 C9 H91 . . . 109.00 no
    H91 C9 H92 . . . 109.00 no
    C11 C10 H101 . . . 110.00 no
    C11 C10 H102 . . . 108.00 no
    C9 C10 H101 . . . 110.00 no
    C9 C10 H102 . . . 108.00 no
    H101 C10 H102 . . . 109.00 no
    C10 C11 H112 . . . 110.00 no
    H111 C11 H112 . . . 110.00 no
    C10 C11 H111 . . . 108.00 no
    C12 C11 H112 . . . 109.00 no
    C12 C11 H111 . . . 109.00 no
    C11 C12 H121 . . . 109.00 no
    C13 C12 H122 . . . 110.00 no
    C13 C12 H121 . . . 108.00 no
    H121 C12 H122 . . . 109.00 no
    C11 C12 H122 . . . 110.00 no
    C12 C13 H131 . . . 109.00 no
    C12 C13 H132 . . . 108.00 no
    C8 C13 H132 . . . 109.00 no
    C8 C13 H131 . . . 109.00 no
    H131 C13 H132 . . . 109.00 no
    C7 C14 H141 . . . 108.00 no
    N1 C14 H142 . . . 108.00 no
    H141 C14 H142 . . . 109.00 no
    N1 C14 H141 . . . 109.00 no
    C7 C14 H142 . . . 109.00 no
    N1 C15 H151 . . . 109.00 no
    H151 C15 H153 . . . 110.00 no
    N1 C15 H153 . . . 110.00 no
    H151 C15 H152 . . . 109.00 no
    N1 C15 H152 . . . 110.00 no
    H152 C15 H153 . . . 109.00 no
    N1 C16 H163 . . . 110.00 no
    H161 C16 H162 . . . 109.00 no
    H162 C16 H163 . . . 109.00 no
    N1 C16 H162 . . . 110.00 no
    N1 C16 H161 . . . 109.00 no
    H161 C16 H163 . . . 109.00 no
    O3 C17 O4 . . . 121.4(3) no
    O4 C17 C18 . . . 121.7(2) no
    O3 C17 C18 . . . 116.9(2) no
    C17 C18 C19 . . . 113.85(19) no
    C18 C19 C20 . . . 114.53(18) no
    O6 C20 C19 . . . 121.1(2) no
    O5 C20 C19 . . . 117.3(2) no
    O5 C20 O6 . . . 121.7(3) no
    C17 C18 H182 . . . 109.00 no
    C19 C18 H181 . . . 108.00 no
    C17 C18 H181 . . . 109.00 no
    H181 C18 H182 . . . 110.00 no
    C19 C18 H182 . . . 107.00 no
    C18 C19 H191 . . . 108.00 no
    C18 C19 H192 . . . 108.00 no
    C20 C19 H192 . . . 109.00 no
    H191 C19 H192 . . . 109.00 no
    C20 C19 H191 . . . 108.00 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
    C15 N1 C14 C7 . . . . 179.6(2) no
    C16 N1 C14 C7 . . . . 56.5(3) no
    C6 C1 C2 C3 . . . . 0.1(4) no
    C7 C1 C2 C3 . . . . 179.5(2) no
    C2 C1 C6 C5 . . . . -1.2(4) no
    C7 C1 C6 C5 . . . . 179.5(2) no
    C2 C1 C7 C8 . . . . 98.4(3) no
    C2 C1 C7 C14 . . . . -133.5(2) no
    C6 C1 C7 C8 . . . . -82.3(3) no
    C6 C1 C7 C14 . . . . 45.8(3) no
    C1 C2 C3 C4 . . . . 1.0(4) no
    C2 C3 C4 O1 . . . . -179.9(2) no
    C2 C3 C4 C5 . . . . -1.0(4) no
    O1 C4 C5 C6 . . . . 178.9(2) no
    C3 C4 C5 C6 . . . . -0.1(4) no
    C4 C5 C6 C1 . . . . 1.2(4) no
    C1 C7 C8 O2 . . . . 175.20(19) no
    C1 C7 C8 C9 . . . . 57.4(3) no
    C1 C7 C8 C13 . . . . -66.2(3) no
    C14 C7 C8 O2 . . . . 45.4(2) no
    C14 C7 C8 C9 . . . . -72.5(3) no
    C14 C7 C8 C13 . . . . 164.0(2) no
    C1 C7 C14 N1 . . . . 55.7(3) no
    C8 C7 C14 N1 . . . . -175.30(18) no
    O2 C8 C9 C10 . . . . 62.1(3) no
    C7 C8 C9 C10 . . . . -179.0(2) no
    C13 C8 C9 C10 . . . . -55.4(3) no
    O2 C8 C13 C12 . . . . -60.6(3) no
    C7 C8 C13 C12 . . . . -178.5(2) no
    C9 C8 C13 C12 . . . . 54.9(3) no
    C8 C9 C10 C11 . . . . 56.5(3) no
    C9 C10 C11 C12 . . . . -55.4(3) no
    C10 C11 C12 C13 . . . . 54.8(3) no
    C11 C12 C13 C8 . . . . -55.3(3) no
    O3 C17 C18 C19 . . . . 171.7(2) no
    O4 C17 C18 C19 . . . . -9.3(4) no
    C17 C18 C19 C20 . . . . 174.1(2) no
    C18 C19 C20 O5 . . . . 174.9(3) no
    C18 C19 C20 O6 . . . . -5.3(4) 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
    O1 H1 O2 1_565 0.94(3) 1.72(3) 2.655(4) 179(3) yes
    O2 H21 O7 1_445 0.88(3) 1.83(3) 2.698(4) 171(2) yes
    O7 H72 O1 . 0.79(4) 2.13(3) 2.836(4) 149(3) yes
    O3 H31 O5 1_455 1.18(4) 1.28(4) 2.450(3) 176(3) yes
    N1 H11 O3 . 0.96(3) 2.25(3) 3.085(4) 145(2) yes
    N1 H11 O4 . 0.96(3) 2.01(3) 2.870(4) 149(2) yes
    O7 H71 O6 . 0.94(4) 1.84(4) 2.753(4) 162(3) yes
    C10 H102 O2 . 0.9500 2.5500 2.881(4) 101.00 no
    C14 H142 O2 . 0.9500 2.4000 2.788(4) 104.00 no
    C16 H163 O6 1_445 0.9500 2.5600 3.386(5) 145.00 yes
    C14 H141 O7 1_545 0.9500 2.6600 3.485(4) 145.00 yes
