##############################################################################
#                                                                            #
# 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_I
_audit_creation_method
;
Olex2 1.2
(compiled 2015.09.30 svn.r3233 for OlexSys, GUI svn.r5103)
;
_journal_data_validation_number     ?
_journal_date_recd_electronic     2017-05-31
_journal_date_accepted     2017-06-07
_journal_name_full     'Acta Crystallographica, Section E'
_journal_year     2017
_journal_volume     73
_journal_issue      7
_journal_page_first     1013
_journal_page_last     1020
_journal_paper_category     GO
_journal_paper_doi     10.1107/S205698901700843X
_journal_coeditor_code     JJ2196
_publ_contact_author_name
;
Alexander Y Nazarenko
;
_publ_contact_author_address
;
Chemistry Department, SUNY Buffalo State,
1300 Elmwood Ave
Buffalo, NY 14222
USA
;
_publ_contact_author_email     'nazareay@buffalostate.edu'
_publ_contact_author_fax     ?
_publ_contact_author_phone     '1-716-878-5923'
_publ_section_title
;
Crystal structure of naltrexone chloride solvates with ethanol, propan-2-ol, and
2-methylpropan-2-ol
;
_publ_section_title_footnote     .
loop_
    _publ_author_name
    _publ_author_footnote
    _publ_author_address
    'Menze, Aveary R.' .
;
Chemistry Department, SUNY Buffalo State,
1300 Elmwood Ave
Buffalo, NY 14222
USA
;
    'Sinnott, Jefferson P.' .
;
Chemistry Department, SUNY Buffalo State,
1300 Elmwood Ave
Buffalo, NY 14222
USA
;
    'Nazarenko, Alexander Y.' .
;
Chemistry Department, SUNY Buffalo State,
1300 Elmwood Ave
Buffalo, NY 14222
USA
;
_publ_section_synopsis
;
Naltrexone [systematic name:
17-(cyclopropylmethyl)-4,5α-epoxy-3,14-dihydroxymorphinan-6-one] is an opioid
receptor competitive antagonist that has been widely used to prevent relapse
in opioid- and alcohol-dependent subjects. Its chloride salt forms
non-isomorphic solvates with ethanol
(C₂₀H₂₄O₄⁺\\cdotCl⁻\\cdotC₂H₅OH) (I), propan-2-ol
(C₂₀H₂₄O₄⁺\\cdotCl⁻\\cdotC₃H₇OH) (II), and 2-methylpropan-2-ol
(C₂₀H₂₄O₄⁺\\cdotCl⁻\\cdotC₄H₉OH) (III). In all these structures,
the alcohol molecules occupy infinite solvent-filled channels. All three
compounds described are attractive crystalline forms for unambiguous
identification of naltrexone chloride after isolation from a pharmaceutical
form.
;
_chemical_name_systematic
;
17-(Cyclopropylmethyl)-3,14-dihydroxy-4,5a-epoxymorphinan-6-one
hydrochloride ethanol monosolvate
;
_chemical_name_common     'Naltrexone chloride ethanol solvate'
_chemical_formula_moiety     'C20 H24 N O4 +, Cl -, C2 H6 O'
_chemical_formula_sum     'C22 H30 Cl N O5'
_chemical_formula_iupac     'C20 H24 N O4 +, Cl -, C2 H6 O'
_chemical_formula_weight     423.92
_chemical_melting_point     ?
_shelx_space_group_comment
;
The symmetry employed for this shelxl refinement is uniquely defined
by the following loop, which should always be used as a source of
symmetry information in preference to the above space-group names.
They are only intended as comments.
;
_space_group_crystal_system     monoclinic
_space_group_name_H-M_alt     'P 21'
_space_group_name_Hall     'P 2yb'
loop_
    _space_group_symop_operation_xyz
    'x, y, z'
    '-x, y+1/2, -z'
_cell_length_a     8.6885(7)
_cell_length_b     7.9478(6)
_cell_length_c     15.3417(10)
_cell_angle_alpha     90
_cell_angle_beta     103.908(2)
_cell_angle_gamma     90
_cell_volume     1028.35(13)
_cell_formula_units_Z     2
_cell_measurement_reflns_used     3107
_cell_measurement_theta_min     2.91
_cell_measurement_theta_max     26.36
_cell_measurement_temperature     173(2)
_exptl_crystal_description     'needle'
_exptl_crystal_colour     colourless
_exptl_crystal_size_max     0.564
_exptl_crystal_size_mid     0.129
_exptl_crystal_size_min     0.062
_exptl_crystal_density_diffrn     1.369
_exptl_crystal_density_meas     ?
_exptl_crystal_density_method     ?
_exptl_crystal_F_000     452
_exptl_absorpt_coefficient_mu     0.220
_exptl_absorpt_correction_type     multi-scan
_exptl_absorpt_process_details
;
(SADABS; Bruker, 2015)
;
_shelx_estimated_absorpt_T_min     ?
_shelx_estimated_absorpt_T_max     ?
_exptl_absorpt_correction_T_min     0.8907
_exptl_absorpt_correction_T_max     1.0000
_diffrn_ambient_temperature     173
_diffrn_radiation_type     MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_measurement_device_type     'Bruker PHOTON-100 CMOS'
_diffrn_measurement_method     'φ and ω scans'
_diffrn_detector_area_resol_mean     ?
_diffrn_reflns_number     33845
_diffrn_reflns_av_R_equivalents     0.0424
_diffrn_reflns_theta_min     2.905
_diffrn_reflns_theta_max     29.848
_diffrn_reflns_theta_full     26.000
_diffrn_measured_fraction_theta_max     0.996
_diffrn_measured_fraction_theta_full     0.998
_diffrn_reflns_limit_h_min     -12
_diffrn_reflns_limit_h_max     12
_diffrn_reflns_limit_k_min     -10
_diffrn_reflns_limit_k_max     11
_diffrn_reflns_limit_l_min     -21
_diffrn_reflns_limit_l_max     21
_diffrn_standards_number     0
_refine_special_details     ?
_reflns_number_total     5866
_reflns_number_gt     5008
_reflns_threshold_expression     'I > 2σ(I)'
_refine_ls_structure_factor_coef     Fsqd
_refine_ls_matrix_type     full
_refine_ls_R_factor_all     0.0531
_refine_ls_R_factor_gt     0.0381
_refine_ls_wR_factor_gt     0.0769
_refine_ls_wR_factor_ref     0.0824
_refine_ls_goodness_of_fit_ref     1.028
_refine_ls_restrained_S_all     1.028
_refine_ls_number_reflns     5866
_refine_ls_number_parameters     305
_refine_ls_number_restraints     10
_refine_ls_hydrogen_treatment     mixed
_refine_ls_weighting_scheme     calc
_refine_ls_weighting_details
              'w=1/[σ²(Fo²)+(0.0403P)²+0.1718P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_hydrogens     mixed
_atom_sites_solution_primary     ?
_atom_sites_solution_secondary     ?
_refine_ls_shift/su_max     0.000
_refine_ls_shift/su_mean     0.000
_refine_diff_density_max     0.323
_refine_diff_density_min     -0.238
_refine_ls_extinction_method     none
_refine_ls_extinction_coef     .
_refine_ls_abs_structure_details
;
Flack x determined using 2015 quotients
[(I⁺)-(I⁻)]/[(I⁺)+(I⁻)]
(Parsons et al., 2013)
;
_refine_ls_abs_structure_Flack     -0.017(18)
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'
    'Cl' 'Cl' 0.1484 0.1585
                         'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
_computing_data_collection
;
APEX2 (Bruker, 2013)
;
_computing_cell_refinement
;
SAINT (Bruker, 2013)
;
_computing_data_reduction
;
SAINT (Bruker, 2013)
;
_computing_structure_solution
;
SHELXT (Sheldrick, 2015a)
;
_computing_structure_refinement
;
SHELXL2014 (Sheldrick, 2015b)
;
_computing_molecular_graphics
;
OLEX2 (Dolomanov et al.,  2009) and Mercury (Macrae et
al.,  2006)
;
_computing_publication_material
;
OLEX2 (Dolomanov et al.,  2009) and 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_adp_type
    _atom_site_calc_flag
    _atom_site_occupancy
    _atom_site_disorder_assembly
    _atom_site_disorder_group
    O O1 0.8998(2) 0.8845(2) 0.08336(11) 0.0259(4) Uani d 1 . .
    O O2 0.64317(17) 0.68560(19) 0.04754(10) 0.0203(3) Uani d 1 . .
    O O3 0.42853(18) 0.8802(2) 0.12744(11) 0.0223(3) Uani d 1 . .
    H H3 0.401(3) 0.943(3) 0.1618(14) 0.033 Uiso calc 1 . .
    O O4 1.03919(19) 0.29776(19) 0.11509(10) 0.0190(3) Uani d 1 . .
    H H4 1.129(4) 0.273(3) 0.1404(13) 0.029 Uiso calc 1 . .
    N N1 0.8634(2) 0.1391(2) 0.20958(11) 0.0163(3) Uani d 1 . .
    H H1 0.923(3) 0.101(3) 0.1776(17) 0.020 Uiso d 1 . .
    C C1 0.6310(3) 0.5970(3) 0.31115(15) 0.0210(5) Uani d 1 . .
    H H1A 0.6326(3) 0.5760(7) 0.3709(19) 0.025 Uiso calc 1 . .
    C C2 0.5273(3) 0.7163(3) 0.26364(15) 0.0214(5) Uani d 1 . .
    H H2 0.456(2) 0.7737(17) 0.2936(9) 0.026 Uiso calc 1 . .
    C C3 0.5215(2) 0.7569(3) 0.17401(15) 0.0190(4) Uani d 1 . .
    C C4 0.6221(2) 0.6658(3) 0.13365(13) 0.0170(4) Uani d 1 . .
    C C5 0.7949(2) 0.6061(3) 0.04998(14) 0.0170(4) Uani d 1 . .
    H H5 0.7973(3) 0.5645(12) -0.0074(16) 0.020 Uiso calc 1 . .
    C C6 0.9275(3) 0.7348(3) 0.08214(14) 0.0184(4) Uani d 1 . .
    C C7 1.0886(3) 0.6620(3) 0.11905(15) 0.0238(4) Uani d 1 . .
    H H7A 1.1658(16) 0.7513(18) 0.1360(4) 0.029 Uiso calc 1 . .
    H H7B 1.1194(7) 0.5929(14) 0.0741(9) 0.029 Uiso calc 1 . .
    C C8 1.0822(3) 0.5547(3) 0.20189(15) 0.0192(4) Uani d 1 . .
    H H8A 1.186(2) 0.5160(8) 0.2306(6) 0.023 Uiso calc 1 . .
    H H8B 1.0434(8) 0.6210(13) 0.2440(8) 0.023 Uiso calc 1 . .
    C C9 0.9473(2) 0.2976(3) 0.25188(13) 0.0149(4) Uani d 1 . .
    H H9 1.052(3) 0.2645(9) 0.2875(9) 0.018 Uiso calc 1 . .
    C C10 0.8594(2) 0.3851(3) 0.31563(14) 0.0177(4) Uani d 1 . .
    H H10A 0.8098(9) 0.2985(16) 0.3456(6) 0.021 Uiso calc 1 . .
    H H10B 0.9375(14) 0.4451(11) 0.3623(9) 0.021 Uiso calc 1 . .
    C C11 0.7335(2) 0.5080(3) 0.26984(14) 0.0165(4) Uani d 1 . .
    C C12 0.7207(2) 0.5434(3) 0.18062(14) 0.0157(4) Uani d 1 . .
    C C13 0.8071(2) 0.4592(3) 0.11827(13) 0.0144(4) Uani d 1 . .
    C C14 0.9728(2) 0.4048(3) 0.17174(13) 0.0145(4) Uani d 1 . .
    C C15 0.7130(2) 0.3023(3) 0.07757(14) 0.0175(4) Uani d 1 . .
    H H15A 0.609(2) 0.3349(7) 0.0464(6) 0.021 Uiso calc 1 . .
    H H15B 0.7633(10) 0.2520(10) 0.0356(8) 0.021 Uiso calc 1 . .
    C C16 0.7020(2) 0.1746(3) 0.14941(14) 0.0197(4) Uani d 1 . .
    H H16A 0.6339(13) 0.2165(8) 0.1845(7) 0.024 Uiso calc 1 . .
    H H16B 0.6575(9) 0.0730(19) 0.1217(5) 0.024 Uiso calc 1 . .
    C C17 0.8565(3) -0.0007(3) 0.27469(15) 0.0217(5) Uani d 1 . .
    H H17A 0.7851(15) 0.0308(7) 0.3109(7) 0.026 Uiso calc 1 . .
    H H17B 0.8148(9) -0.100(2) 0.2417(7) 0.026 Uiso calc 1 . .
    C C18 1.0151(3) -0.0406(3) 0.33484(16) 0.0248(5) Uani d 1 . .
    H H18 1.100(3) -0.0555(5) 0.3062(9) 0.030 Uiso calc 1 . .
    C C19 1.0167(4) -0.1523(4) 0.41391(19) 0.0374(6) Uani d 1 . .
    H H19A 0.917(2) -0.1882(10) 0.4233(3) 0.045 Uiso calc 1 . .
    H H19B 1.100(2) -0.233(2) 0.4301(4) 0.045 Uiso calc 1 . .
    C C20 1.0588(4) 0.0293(4) 0.42825(17) 0.0360(6) Uani d 1 . .
    H H20A 1.166(3) 0.0567(8) 0.4528(6) 0.043 Uiso calc 1 . .
    H H20B 0.9850(17) 0.1009(17) 0.4460(5) 0.043 Uiso calc 1 . .
    O O5 0.6227(2) 1.1314(4) 0.42038(13) 0.0522(6) Uani d 1 . .
    H H5A 0.5552 1.1465 0.3717 0.078 Uiso calc 0.66(3) A 1
    H H5B 0.5546 1.1413 0.3715 0.078 Uiso calc 0.34(3) A 2
    C C21 0.5677(11) 1.0028(15) 0.4713(7) 0.046(2) Uani d 0.66(3) A 1
    H H21A 0.5584(11) 0.888(5) 0.4362(15) 0.055 Uiso calc 0.66(3) A 1
    H H21B 0.454(4) 1.0348(19) 0.4790(7) 0.055 Uiso calc 0.66(3) A 1
    C C21A 0.557(3) 1.049(5) 0.4808(19) 0.086(9) Uani d 0.34(3) A 2
    H H21C 0.4644 0.9830 0.4484 0.103 Uiso calc 0.34(3) A 2
    H H21D 0.5208 1.1316 0.5196 0.103 Uiso calc 0.34(3) A 2
    C C22 0.6769(13) 0.9820(15) 0.5609(6) 0.0408(19) Uani d 0.66(3) A 1
    H H22A 0.781(4) 0.955(5) 0.5540(6) 0.061 Uiso calc 0.66(3) A 1
    H H22B 0.640(3) 0.893(4) 0.5925(16) 0.061 Uiso calc 0.66(3) A 1
    H H22C 0.681(4) 1.085(4) 0.5942(15) 0.061 Uiso calc 0.66(3) A 1
    C C22A 0.673(3) 0.937(3) 0.5356(18) 0.054(5) Uani d 0.34(3) A 2
    H H22D 0.7009 0.8489 0.4978 0.081 Uiso calc 0.34(3) A 2
    H H22E 0.6272 0.8862 0.5819 0.081 Uiso calc 0.34(3) A 2
    H H22F 0.7676 1.0014 0.5642 0.081 Uiso calc 0.34(3) A 2
    Cl Cl01 0.34066(7) 1.14944(8) 0.24667(4) 0.03172(15) Uani d 1 . .
_geom_special_details
;
 All esds (except the esd in the dihedral angle between two l.s. planes)
 are estimated using the full covariance matrix.  The cell esds are taken
 into account individually in the estimation of esds in distances, angles
 and torsion angles; correlations between esds in cell parameters are only
 used when they are defined by crystal symmetry.  An approximate (isotropic)
 treatment of cell esds is used for estimating esds 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
    O1 C6 . 1.215(3) ?
    O2 C4 . 1.386(2) ?
    O2 C5 . 1.454(2) ?
    O3 H3 . 0.80(3) ?
    O3 C3 . 1.359(3) ?
    O4 H4 . 0.81(3) ?
    O4 C14 . 1.433(2) ?
    N1 H1 . 0.85(3) ?
    N1 C9 . 1.521(3) ?
    N1 C16 . 1.509(3) ?
    N1 C17 . 1.505(3) ?
    C1 H1A . 0.93(3) ?
    C1 C2 . 1.388(3) ?
    C1 C11 . 1.402(3) ?
    C2 H2 . 0.97(3) ?
    C2 C3 . 1.402(3) ?
    C3 C4 . 1.390(3) ?
    C4 C12 . 1.379(3) ?
    C5 H5 . 0.95(3) ?
    C5 C6 . 1.531(3) ?
    C5 C13 . 1.555(3) ?
    C6 C7 . 1.494(3) ?
    C7 H7A . 0.968(19) ?
    C7 H7B . 0.968(19) ?
    C7 C8 . 1.543(3) ?
    C8 H8A . 0.956(18) ?
    C8 H8B . 0.956(18) ?
    C8 C14 . 1.524(3) ?
    C9 H9 . 0.98(2) ?
    C9 C10 . 1.543(3) ?
    C9 C14 . 1.555(3) ?
    C10 H10A . 0.983(18) ?
    C10 H10B . 0.983(18) ?
    C10 C11 . 1.509(3) ?
    C11 C12 . 1.376(3) ?
    C12 C13 . 1.507(3) ?
    C13 C14 . 1.538(3) ?
    C13 C15 . 1.539(3) ?
    C15 H15A . 0.949(18) ?
    C15 H15B . 0.949(18) ?
    C15 C16 . 1.518(3) ?
    C16 H16A . 0.950(18) ?
    C16 H16B . 0.950(18) ?
    C17 H17A . 0.960(19) ?
    C17 H17B . 0.960(19) ?
    C17 C18 . 1.497(3) ?
    C18 H18 . 0.95(3) ?
    C18 C19 . 1.500(3) ?
    C18 C20 . 1.498(4) ?
    C19 H19A . 0.96(2) ?
    C19 H19B . 0.96(2) ?
    C19 C20 . 1.492(4) ?
    C20 H20A . 0.95(2) ?
    C20 H20B . 0.95(2) ?
    O5 H5A . 0.8400 ?
    O5 H5B . 0.8400 ?
    O5 C21 . 1.437(10) ?
    O5 C21A . 1.37(2) ?
    C21 H21A . 1.05(4) ?
    C21 H21B . 1.05(4) ?
    C21 C22 . 1.480(13) ?
    C21A H21C . 0.9900 ?
    C21A H21D . 0.9900 ?
    C21A C22A . 1.44(4) ?
    C22 H22A . 0.96(3) ?
    C22 H22B . 0.96(3) ?
    C22 H22C . 0.96(3) ?
    C22A H22D . 0.9800 ?
    C22A H22E . 0.9800 ?
    C22A H22F . 0.9800 ?
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
    C4 O2 C5 . . 104.64(15) ?
    C3 O3 H3 . . 109.5 ?
    C14 O4 H4 . . 109.5 ?
    C9 N1 H1 . . 104.3(17) ?
    C16 N1 H1 . . 108.6(17) ?
    C16 N1 C9 . . 112.68(17) ?
    C17 N1 H1 . . 104.2(17) ?
    C17 N1 C9 . . 114.83(15) ?
    C17 N1 C16 . . 111.38(16) ?
    C2 C1 H1A . . 119.7 ?
    C2 C1 C11 . . 120.7(2) ?
    C11 C1 H1A . . 119.7 ?
    C1 C2 H2 . . 118.7 ?
    C1 C2 C3 . . 122.6(2) ?
    C3 C2 H2 . . 118.7 ?
    O3 C3 C2 . . 123.96(19) ?
    O3 C3 C4 . . 119.97(19) ?
    C4 C3 C2 . . 116.1(2) ?
    O2 C4 C3 . . 127.38(19) ?
    C12 C4 O2 . . 111.74(17) ?
    C12 C4 C3 . . 120.84(19) ?
    O2 C5 H5 . . 110.5 ?
    O2 C5 C6 . . 109.01(16) ?
    O2 C5 C13 . . 104.95(15) ?
    C6 C5 H5 . . 110.5 ?
    C6 C5 C13 . . 111.12(17) ?
    C13 C5 H5 . . 110.5 ?
    O1 C6 C5 . . 121.5(2) ?
    O1 C6 C7 . . 123.0(2) ?
    C7 C6 C5 . . 115.32(18) ?
    C6 C7 H7A . . 110.1 ?
    C6 C7 H7B . . 110.1 ?
    C6 C7 C8 . . 108.08(17) ?
    H7A C7 H7B . . 108.4 ?
    C8 C7 H7A . . 110.1 ?
    C8 C7 H7B . . 110.1 ?
    C7 C8 H8A . . 109.9 ?
    C7 C8 H8B . . 109.9 ?
    H8A C8 H8B . . 108.3 ?
    C14 C8 C7 . . 108.99(18) ?
    C14 C8 H8A . . 109.9 ?
    C14 C8 H8B . . 109.9 ?
    N1 C9 H9 . . 107.5 ?
    N1 C9 C10 . . 112.62(16) ?
    N1 C9 C14 . . 105.16(15) ?
    C10 C9 H9 . . 107.5 ?
    C10 C9 C14 . . 116.16(17) ?
    C14 C9 H9 . . 107.5 ?
    C9 C10 H10A . . 108.7 ?
    C9 C10 H10B . . 108.7 ?
    H10A C10 H10B . . 107.6 ?
    C11 C10 C9 . . 114.23(17) ?
    C11 C10 H10A . . 108.7 ?
    C11 C10 H10B . . 108.7 ?
    C1 C11 C10 . . 125.78(18) ?
    C12 C11 C1 . . 115.99(19) ?
    C12 C11 C10 . . 118.16(18) ?
    C4 C12 C13 . . 108.85(17) ?
    C11 C12 C4 . . 123.76(19) ?
    C11 C12 C13 . . 127.38(19) ?
    C12 C13 C5 . . 97.49(16) ?
    C12 C13 C14 . . 109.36(16) ?
    C12 C13 C15 . . 108.69(16) ?
    C14 C13 C5 . . 118.28(16) ?
    C14 C13 C15 . . 109.06(16) ?
    C15 C13 C5 . . 113.06(17) ?
    O4 C14 C8 . . 109.61(16) ?
    O4 C14 C9 . . 107.99(16) ?
    O4 C14 C13 . . 107.76(16) ?
    C8 C14 C9 . . 112.67(16) ?
    C8 C14 C13 . . 112.20(17) ?
    C13 C14 C9 . . 106.39(16) ?
    C13 C15 H15A . . 109.3 ?
    C13 C15 H15B . . 109.3 ?
    H15A C15 H15B . . 108.0 ?
    C16 C15 C13 . . 111.55(17) ?
    C16 C15 H15A . . 109.3 ?
    C16 C15 H15B . . 109.3 ?
    N1 C16 C15 . . 110.95(16) ?
    N1 C16 H16A . . 109.4 ?
    N1 C16 H16B . . 109.4 ?
    C15 C16 H16A . . 109.4 ?
    C15 C16 H16B . . 109.4 ?
    H16A C16 H16B . . 108.0 ?
    N1 C17 H17A . . 109.0 ?
    N1 C17 H17B . . 109.0 ?
    H17A C17 H17B . . 107.8 ?
    C18 C17 N1 . . 112.82(18) ?
    C18 C17 H17A . . 109.0 ?
    C18 C17 H17B . . 109.0 ?
    C17 C18 H18 . . 116.2 ?
    C17 C18 C19 . . 116.9(2) ?
    C17 C18 C20 . . 119.7(2) ?
    C19 C18 H18 . . 116.2 ?
    C20 C18 H18 . . 116.2 ?
    C20 C18 C19 . . 59.68(18) ?
    C18 C19 H19A . . 117.8 ?
    C18 C19 H19B . . 117.8 ?
    H19A C19 H19B . . 114.9 ?
    C20 C19 C18 . . 60.09(17) ?
    C20 C19 H19A . . 117.8 ?
    C20 C19 H19B . . 117.8 ?
    C18 C20 H20A . . 117.7 ?
    C18 C20 H20B . . 117.7 ?
    C19 C20 C18 . . 60.23(18) ?
    C19 C20 H20A . . 117.7 ?
    C19 C20 H20B . . 117.7 ?
    H20A C20 H20B . . 114.9 ?
    C21 O5 H5A . . 109.5 ?
    C21A O5 H5B . . 109.5 ?
    O5 C21 H21A . . 109.4 ?
    O5 C21 H21B . . 109.4 ?
    O5 C21 C22 . . 111.2(7) ?
    H21A C21 H21B . . 108.0 ?
    C22 C21 H21A . . 109.4 ?
    C22 C21 H21B . . 109.4 ?
    O5 C21A H21C . . 109.6 ?
    O5 C21A H21D . . 109.6 ?
    O5 C21A C22A . . 110(2) ?
    H21C C21A H21D . . 108.1 ?
    C22A C21A H21C . . 109.6 ?
    C22A C21A H21D . . 109.6 ?
    C21 C22 H22A . . 109.5 ?
    C21 C22 H22B . . 109.5 ?
    C21 C22 H22C . . 109.5 ?
    H22A C22 H22B . . 109.5 ?
    H22A C22 H22C . . 109.5 ?
    H22B C22 H22C . . 109.5 ?
    C21A C22A H22D . . 109.5 ?
    C21A C22A H22E . . 109.5 ?
    C21A C22A H22F . . 109.5 ?
    H22D C22A H22E . . 109.5 ?
    H22D C22A H22F . . 109.5 ?
    H22E C22A H22F . . 109.5 ?
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
    O1 C6 C7 C8 . . . . 113.2(2) ?
    O2 C4 C12 C11 . . . . 174.46(19) ?
    O2 C4 C12 C13 . . . . -5.8(2) ?
    O2 C5 C6 O1 . . . . -15.5(3) ?
    O2 C5 C6 C7 . . . . 159.27(16) ?
    O2 C5 C13 C12 . . . . -33.70(19) ?
    O2 C5 C13 C14 . . . . -150.48(16) ?
    O2 C5 C13 C15 . . . . 80.3(2) ?
    O3 C3 C4 O2 . . . . 0.7(3) ?
    O3 C3 C4 C12 . . . . 178.14(19) ?
    N1 C9 C10 C11 . . . . -87.3(2) ?
    N1 C9 C14 O4 . . . . -48.3(2) ?
    N1 C9 C14 C8 . . . . -169.51(16) ?
    N1 C9 C14 C13 . . . . 67.15(19) ?
    N1 C17 C18 C19 . . . . 167.9(2) ?
    N1 C17 C18 C20 . . . . 99.2(3) ?
    C1 C2 C3 O3 . . . . -175.7(2) ?
    C1 C2 C3 C4 . . . . 2.4(3) ?
    C1 C11 C12 C4 . . . . 4.1(3) ?
    C1 C11 C12 C13 . . . . -175.5(2) ?
    C2 C1 C11 C10 . . . . 175.2(2) ?
    C2 C1 C11 C12 . . . . -1.7(3) ?
    C2 C3 C4 O2 . . . . -177.5(2) ?
    C2 C3 C4 C12 . . . . -0.1(3) ?
    C3 C4 C12 C11 . . . . -3.3(3) ?
    C3 C4 C12 C13 . . . . 176.38(19) ?
    C4 O2 C5 C6 . . . . -86.73(19) ?
    C4 O2 C5 C13 . . . . 32.4(2) ?
    C4 C12 C13 C5 . . . . 24.1(2) ?
    C4 C12 C13 C14 . . . . 147.62(17) ?
    C4 C12 C13 C15 . . . . -93.4(2) ?
    C5 O2 C4 C3 . . . . 160.5(2) ?
    C5 O2 C4 C12 . . . . -17.1(2) ?
    C5 C6 C7 C8 . . . . -61.5(2) ?
    C5 C13 C14 O4 . . . . -80.7(2) ?
    C5 C13 C14 C8 . . . . 40.0(2) ?
    C5 C13 C14 C9 . . . . 163.64(16) ?
    C5 C13 C15 C16 . . . . -169.37(17) ?
    C6 C5 C13 C12 . . . . 83.98(18) ?
    C6 C5 C13 C14 . . . . -32.8(2) ?
    C6 C5 C13 C15 . . . . -161.98(16) ?
    C6 C7 C8 C14 . . . . 65.5(2) ?
    C7 C8 C14 O4 . . . . 64.8(2) ?
    C7 C8 C14 C9 . . . . -174.96(17) ?
    C7 C8 C14 C13 . . . . -54.9(2) ?
    C9 N1 C16 C15 . . . . 55.4(2) ?
    C9 N1 C17 C18 . . . . -51.0(2) ?
    C9 C10 C11 C1 . . . . 176.4(2) ?
    C9 C10 C11 C12 . . . . -6.8(3) ?
    C10 C9 C14 O4 . . . . -173.55(16) ?
    C10 C9 C14 C8 . . . . 65.3(2) ?
    C10 C9 C14 C13 . . . . -58.1(2) ?
    C10 C11 C12 C4 . . . . -173.06(19) ?
    C10 C11 C12 C13 . . . . 7.3(3) ?
    C11 C1 C2 C3 . . . . -1.5(3) ?
    C11 C12 C13 C5 . . . . -156.2(2) ?
    C11 C12 C13 C14 . . . . -32.7(3) ?
    C11 C12 C13 C15 . . . . 86.3(2) ?
    C12 C13 C14 O4 . . . . 169.02(16) ?
    C12 C13 C14 C8 . . . . -70.2(2) ?
    C12 C13 C14 C9 . . . . 53.4(2) ?
    C12 C13 C15 C16 . . . . -62.3(2) ?
    C13 C5 C6 O1 . . . . -130.7(2) ?
    C13 C5 C6 C7 . . . . 44.1(2) ?
    C13 C15 C16 N1 . . . . -50.5(2) ?
    C14 C9 C10 C11 . . . . 34.0(2) ?
    C14 C13 C15 C16 . . . . 56.9(2) ?
    C15 C13 C14 O4 . . . . 50.3(2) ?
    C15 C13 C14 C8 . . . . 171.03(17) ?
    C15 C13 C14 C9 . . . . -65.34(19) ?
    C16 N1 C9 C10 . . . . 64.0(2) ?
    C16 N1 C9 C14 . . . . -63.42(19) ?
    C16 N1 C17 C18 . . . . 179.37(18) ?
    C17 N1 C9 C10 . . . . -65.0(2) ?
    C17 N1 C9 C14 . . . . 167.63(16) ?
    C17 N1 C16 C15 . . . . -173.89(17) ?
    C17 C18 C19 C20 . . . . -110.3(3) ?
    C17 C18 C20 C19 . . . . 105.6(3) ?
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
    N1 H1 O1 1_545 0.85(3) 2.23(2) 2.870(2) 133(2)
    O3 H3 Cl01 . 0.80(2) 2.23(2) 3.0297(17) 171(2)
    O4 H4 Cl01 1_645 0.81(3) 2.36(3) 3.1279(17) 159(3)
    O5 H5A Cl01 . 0.84 2.33 3.160(2) 169
data_II
_audit_creation_method
;
Olex2 1.2
(compiled 2017.03.28 svn.r3405 for OlexSys, GUI svn.r5335)
;
_chemical_name_systematic
;
17-(Cyclopropylmethyl)-3,14-dihydroxy-4,5a-epoxymorphinan-6-one
hydrochloride propan-2-ol monosolvate
;
_chemical_name_common     'naltrexone chloride i-propanol solvate'
_chemical_formula_moiety     'C20 H24 N O4 +, Cl -, C3 H8 O'
_chemical_formula_sum     'C23 H32 Cl N O5'
_chemical_formula_iupac     'C20 H24 N O4 +, Cl -, C3 H8 O'
_chemical_formula_weight     437.94
_chemical_melting_point     ?
_shelx_space_group_comment
;
The symmetry employed for this shelxl refinement is uniquely defined
by the following loop, which should always be used as a source of
symmetry information in preference to the above space-group names.
They are only intended as comments.
;
_space_group_crystal_system     orthorhombic
_space_group_name_H-M_alt     'P 21 21 21'
_space_group_name_Hall     'P 2ac 2ab'
loop_
    _space_group_symop_operation_xyz
    'x, y, z'
    '-x+1/2, -y, z+1/2'
    '-x, y+1/2, -z+1/2'
    'x+1/2, -y+1/2, -z'
_cell_length_a     8.0297(10)
_cell_length_b     15.5449(17)
_cell_length_c     17.560(4)
_cell_angle_alpha     90
_cell_angle_beta     90
_cell_angle_gamma     90
_cell_volume     2191.9(6)
_cell_formula_units_Z     4
_cell_measurement_reflns_used     9935
_cell_measurement_theta_min     2.86
_cell_measurement_theta_max     27.26
_cell_measurement_temperature     173(2)
_exptl_crystal_description     block
_exptl_crystal_colour     colourless
_exptl_crystal_size_max     0.2
_exptl_crystal_size_mid     0.16
_exptl_crystal_size_min     0.15
_exptl_crystal_density_diffrn     1.327
_exptl_crystal_density_meas     ?
_exptl_crystal_density_method     ?
_exptl_crystal_F_000     936
_exptl_absorpt_coefficient_mu     0.209
_exptl_absorpt_correction_type     multi-scan
_exptl_absorpt_process_details
;
(SADABS; Bruker, 2015)
;
_shelx_estimated_absorpt_T_min     ?
_shelx_estimated_absorpt_T_max     ?
_exptl_absorpt_correction_T_min     0.9249
_exptl_absorpt_correction_T_max     0.9858
_diffrn_ambient_temperature     173
_diffrn_radiation_type     MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_measurement_device_type     'Bruker PHOTON-100 CMOS'
_diffrn_measurement_method     'φ and ω scans'
_diffrn_detector_area_resol_mean     ?
_diffrn_reflns_number     48846
_diffrn_reflns_av_R_equivalents     0.0432
_diffrn_reflns_theta_min     2.789
_diffrn_reflns_theta_max     28.226
_diffrn_reflns_theta_full     26.000
_diffrn_measured_fraction_theta_max     0.992
_diffrn_measured_fraction_theta_full     0.998
_diffrn_reflns_limit_h_min     -10
_diffrn_reflns_limit_h_max     10
_diffrn_reflns_limit_k_min     -20
_diffrn_reflns_limit_k_max     19
_diffrn_reflns_limit_l_min     -23
_diffrn_reflns_limit_l_max     22
_diffrn_standards_number     0
_refine_special_details     ?
_reflns_number_total     5327
_reflns_number_gt     4481
_reflns_threshold_expression     'I > 2σ(I)'
_refine_ls_structure_factor_coef     Fsqd
_refine_ls_matrix_type     full
_refine_ls_R_factor_all     0.0632
_refine_ls_R_factor_gt     0.0454
_refine_ls_wR_factor_gt     0.1052
_refine_ls_wR_factor_ref     0.1124
_refine_ls_goodness_of_fit_ref     1.085
_refine_ls_restrained_S_all     1.088
_refine_ls_number_reflns     5327
_refine_ls_number_parameters     313
_refine_ls_number_restraints     16
_refine_ls_hydrogen_treatment     mixed
_refine_ls_weighting_scheme     calc
_refine_ls_weighting_details
              'w=1/[σ²(Fo²)+(0.0589P)²+0.6347P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_hydrogens     mixed
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary     ?
_refine_ls_shift/su_max     0.000
_refine_ls_shift/su_mean     0.000
_refine_diff_density_max     0.326
_refine_diff_density_min     -0.339
_refine_ls_extinction_method     none
_refine_ls_extinction_coef     .
_refine_ls_abs_structure_details
;
Flack x determined using 1682 quotients
[(I⁺)-(I⁻)]/[(I⁺)+(I⁻)]
(Parsons et al., 2013)
;
_refine_ls_abs_structure_Flack     -0.028(18)
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'
    'Cl' 'Cl' 0.1484 0.1585
                         'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
_computing_data_collection
;
APEX2 (Bruker, 2013)
;
_computing_cell_refinement
;
SAINT (Bruker, 2013)
;
_computing_data_reduction
;
SAINT (Bruker, 2013)
;
_computing_structure_solution
;
SHELXT (Sheldrick, 2015a)
;
_computing_structure_refinement
;
SHELXL2014 (Sheldrick, 2015b)
;
_computing_molecular_graphics
;
OLEX2 (Dolomanov et al.,  2009)
;
_computing_publication_material
;
OLEX2 (Dolomanov et al.,  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_adp_type
    _atom_site_calc_flag
    _atom_site_occupancy
    _atom_site_disorder_assembly
    _atom_site_disorder_group
    Cl Cl1 0.47836(9) 0.21061(5) 0.49145(4) 0.02955(19) Uani d 1 . .
    O O1 0.6306(3) 0.63086(16) 0.64326(15) 0.0468(7) Uani d 1 . .
    O O2 0.3209(3) 0.61657(13) 0.70324(11) 0.0291(5) Uani d 1 . .
    O O3 0.3306(3) 0.67460(13) 0.86078(13) 0.0334(5) Uani d 1 . .
    H H3 0.366(6) 0.6819(6) 0.900(2) 0.050 Uiso calc 1 . .
    O O4 0.3504(3) 0.38140(14) 0.55436(11) 0.0264(5) Uani d 1 . .
    H H4 0.390(4) 0.335(3) 0.5370(11) 0.040 Uiso calc 1 . .
    N N1 0.1648(3) 0.29790(15) 0.66310(13) 0.0211(5) Uani d 1 . .
    H H1 0.1568(4) 0.2926(3) 0.614(2) 0.025 Uiso calc 1 . .
    C C1 0.3664(4) 0.4365(2) 0.87554(18) 0.0340(7) Uani d 1 . .
    H H1A 0.3784(7) 0.3966(19) 0.9112(17) 0.041 Uiso calc 1 . .
    C C2 0.3557(4) 0.5228(2) 0.89661(18) 0.0332(7) Uani d 1 . .
    H H2 0.3587(4) 0.5365(6) 0.947(2) 0.040 Uiso calc 1 . .
    C C3 0.3405(4) 0.58920(19) 0.84301(17) 0.0270(6) Uani d 1 . .
    C C4 0.3334(4) 0.56354(18) 0.76731(16) 0.0238(6) Uani d 1 . .
    C C5 0.3665(4) 0.56083(18) 0.63904(16) 0.0268(6) Uani d 1 . .
    H H5 0.3063 0.5798 0.5921 0.032 Uiso calc 1 . .
    C C6 0.5551(4) 0.5665(2) 0.62618(17) 0.0297(7) Uani d 1 . .
    C C7 0.6358(4) 0.4886(2) 0.59096(19) 0.0329(7) Uani d 1 . .
    H H7A 0.754(3) 0.4958(3) 0.59106(19) 0.040 Uiso calc 1 . .
    H H7B 0.6002(10) 0.4832(2) 0.5393(15) 0.040 Uiso calc 1 . .
    C C8 0.5905(4) 0.4063(2) 0.6348(2) 0.0297(7) Uani d 1 . .
    H H8A 0.6445(16) 0.3595(13) 0.6134(6) 0.036 Uiso calc 1 . .
    H H8B 0.6246(11) 0.4112(2) 0.6850(14) 0.036 Uiso calc 1 . .
    C C9 0.3481(3) 0.31327(17) 0.67995(16) 0.0225(6) Uani d 1 . .
    H H9 0.410(2) 0.2633(18) 0.6615(7) 0.027 Uiso calc 1 . .
    C C10 0.3822(4) 0.32180(19) 0.76624(17) 0.0281(6) Uani d 1 . .
    H H10A 0.3107(19) 0.2836(11) 0.7926(7) 0.034 Uiso calc 1 . .
    H H10B 0.493(3) 0.3042(5) 0.7759(3) 0.034 Uiso calc 1 . .
    C C11 0.3584(4) 0.41151(19) 0.79858(16) 0.0260(6) Uani d 1 . .
    C C12 0.3361(4) 0.47756(18) 0.74739(15) 0.0225(6) Uani d 1 . .
    C C13 0.3061(3) 0.46997(18) 0.66287(15) 0.0221(6) Uani d 1 . .
    C C14 0.4028(4) 0.39240(18) 0.63174(16) 0.0224(6) Uani d 1 . .
    C C15 0.1182(4) 0.45591(18) 0.64836(16) 0.0241(6) Uani d 1 . .
    H H15A 0.0585(16) 0.5021(12) 0.6684(5) 0.029 Uiso calc 1 . .
    H H15B 0.0987(7) 0.45401(18) 0.5961(14) 0.029 Uiso calc 1 . .
    C C16 0.0577(4) 0.37308(19) 0.68449(17) 0.0256(6) Uani d 1 . .
    H H16A 0.0577(4) 0.3791(2) 0.7357(14) 0.031 Uiso calc 1 . .
    H H16B -0.048(3) 0.3628(3) 0.6695(4) 0.031 Uiso calc 1 . .
    C C17 0.0959(4) 0.21569(19) 0.69674(16) 0.0268(6) Uani d 1 . .
    H H17A 0.0837(5) 0.2231(3) 0.7508(14) 0.032 Uiso calc 1 . .
    H H17B -0.013(3) 0.2055(3) 0.6758(5) 0.032 Uiso calc 1 . .
    C C18 0.2021(4) 0.1386(2) 0.68222(18) 0.0295(7) Uani d 1 . .
    H H18 0.304(5) 0.1384(2) 0.7058(11) 0.035 Uiso calc 1 . .
    C C19 0.1196(4) 0.0523(2) 0.6740(2) 0.0366(8) Uani d 1 . .
    H H19A 0.1726(17) 0.0060(15) 0.6936(7) 0.044 Uiso calc 1 . .
    H H19B 0.007(4) 0.0503(2) 0.6769(2) 0.044 Uiso calc 1 . .
    C C20 0.1953(4) 0.0949(2) 0.6060(2) 0.0338(7) Uani d 1 . .
    H H20A 0.126(2) 0.1168(7) 0.5707(11) 0.041 Uiso calc 1 . .
    H H20B 0.290(3) 0.0727(7) 0.5874(6) 0.041 Uiso calc 1 . .
    O O5 0.1923(4) 0.7903(2) 0.67974(16) 0.0566(7) Uani d 0.822(9) A 1
    C C21 0.1900(8) 0.7764(6) 0.5993(3) 0.0505(15) Uani d 0.822(9) A 1
    H H21 0.2936 0.7453 0.5837 0.061 Uiso calc 0.822(9) A 1
    C C22 0.0361(8) 0.7211(4) 0.5788(3) 0.0660(17) Uani d 0.822(9) A 1
    H H22A 0.0335 0.7113 0.5237 0.099 Uiso calc 0.822(9) A 1
    H H22B 0.0427 0.6658 0.6053 0.099 Uiso calc 0.822(9) A 1
    H H22C -0.0654 0.7514 0.5944 0.099 Uiso calc 0.822(9) A 1
    C C23 0.1858(10) 0.8624(3) 0.5619(3) 0.072(2) Uani d 0.822(9) A 1
    H H23A 0.1842 0.8551 0.5065 0.108 Uiso calc 0.822(9) A 1
    H H23B 0.0857 0.8934 0.5780 0.108 Uiso calc 0.822(9) A 1
    H H23C 0.2849 0.8953 0.5766 0.108 Uiso calc 0.822(9) A 1
    H H5A 0.225(9) 0.735(3) 0.704(4) 0.108 Uiso d 0.822(9) A 1
    O O5A 0.1923(4) 0.7903(2) 0.67974(16) 0.0566(7) Uani d 0.178(9) A 2
    C C21A 0.141(4) 0.779(3) 0.6008(12) 0.0505(15) Uani d 0.178(9) A 2
    H H21A 0.1050 0.7173 0.5967 0.061 Uiso calc 0.178(9) A 2
    C C22A -0.014(4) 0.832(3) 0.5812(19) 0.107(14) Uani d 0.178(9) A 2
    H H22D -0.0443 0.8230 0.5278 0.160 Uiso calc 0.178(9) A 2
    H H22E -0.1066 0.8151 0.6141 0.160 Uiso calc 0.178(9) A 2
    H H22F 0.0104 0.8936 0.5893 0.160 Uiso calc 0.178(9) A 2
    C C23A 0.275(4) 0.790(4) 0.543(2) 0.16(3) Uani d 0.178(9) A 2
    H H23D 0.2281 0.7805 0.4917 0.242 Uiso calc 0.178(9) A 2
    H H23E 0.3209 0.8478 0.5461 0.242 Uiso calc 0.178(9) A 2
    H H23F 0.3633 0.7474 0.5519 0.242 Uiso calc 0.178(9) A 2
    H H5AA 0.225(9) 0.735(3) 0.704(4) 0.242 Uiso d 0.178(9) A 2
_geom_special_details
;
 All esds (except the esd in the dihedral angle between two l.s. planes)
 are estimated using the full covariance matrix.  The cell esds are taken
 into account individually in the estimation of esds in distances, angles
 and torsion angles; correlations between esds in cell parameters are only
 used when they are defined by crystal symmetry.  An approximate (isotropic)
 treatment of cell esds is used for estimating esds 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
    O1 C6 . 1.208(4) ?
    O2 C4 . 1.398(3) ?
    O2 C5 . 1.468(3) ?
    O3 H3 . 0.76(4) ?
    O3 C3 . 1.366(4) ?
    O4 H4 . 0.84(4) ?
    O4 C14 . 1.433(3) ?
    N1 H1 . 0.86(3) ?
    N1 C9 . 1.520(4) ?
    N1 C16 . 1.499(4) ?
    N1 C17 . 1.513(4) ?
    C1 H1A . 0.89(4) ?
    C1 C2 . 1.394(5) ?
    C1 C11 . 1.408(4) ?
    C2 H2 . 0.91(4) ?
    C2 C3 . 1.403(5) ?
    C3 C4 . 1.389(4) ?
    C4 C12 . 1.382(4) ?
    C5 H5 . 1.0000 ?
    C5 C6 . 1.534(5) ?
    C5 C13 . 1.551(4) ?
    C6 C7 . 1.506(4) ?
    C7 H7A . 0.95(3) ?
    C7 H7B . 0.95(3) ?
    C7 C8 . 1.537(5) ?
    C8 H8A . 0.93(3) ?
    C8 H8B . 0.93(3) ?
    C8 C14 . 1.523(4) ?
    C9 H9 . 0.98(3) ?
    C9 C10 . 1.545(4) ?
    C9 C14 . 1.557(4) ?
    C10 H10A . 0.95(3) ?
    C10 H10B . 0.95(3) ?
    C10 C11 . 1.518(4) ?
    C11 C12 . 1.376(4) ?
    C12 C13 . 1.508(4) ?
    C13 C14 . 1.535(4) ?
    C13 C15 . 1.545(4) ?
    C15 H15A . 0.93(2) ?
    C15 H15B . 0.93(2) ?
    C15 C16 . 1.515(4) ?
    C16 H16A . 0.90(2) ?
    C16 H16B . 0.90(2) ?
    C17 H17A . 0.96(2) ?
    C17 H17B . 0.96(2) ?
    C17 C18 . 1.493(4) ?
    C18 H18 . 0.91(4) ?
    C18 C19 . 1.502(5) ?
    C18 C20 . 1.502(5) ?
    C19 H19A . 0.90(3) ?
    C19 H19B . 0.90(3) ?
    C19 C20 . 1.495(5) ?
    C20 H20A . 0.90(3) ?
    C20 H20B . 0.90(3) ?
    O5 C21 . 1.429(6) ?
    O5 H5A . 0.99(3) ?
    C21 H21 . 1.0000 ?
    C21 C22 . 1.547(10) ?
    C21 C23 . 1.490(10) ?
    C22 H22A . 0.9800 ?
    C22 H22B . 0.9800 ?
    C22 H22C . 0.9800 ?
    C23 H23A . 0.9800 ?
    C23 H23B . 0.9800 ?
    C23 H23C . 0.9800 ?
    O5A C21A . 1.46(2) ?
    O5A H5AA . 0.99(3) ?
    C21A H21A . 1.0000 ?
    C21A C22A . 1.54(3) ?
    C21A C23A . 1.49(2) ?
    C22A H22D . 0.9800 ?
    C22A H22E . 0.9800 ?
    C22A H22F . 0.9800 ?
    C23A H23D . 0.9800 ?
    C23A H23E . 0.9800 ?
    C23A H23F . 0.9800 ?
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
    C4 O2 C5 . . 104.6(2) ?
    C3 O3 H3 . . 109.5 ?
    C14 O4 H4 . . 109.5 ?
    C9 N1 H1 . . 106.3 ?
    C16 N1 H1 . . 106.3 ?
    C16 N1 C9 . . 112.6(2) ?
    C16 N1 C17 . . 110.6(2) ?
    C17 N1 H1 . . 106.3 ?
    C17 N1 C9 . . 114.3(2) ?
    C2 C1 H1A . . 119.4 ?
    C2 C1 C11 . . 121.1(3) ?
    C11 C1 H1A . . 119.4 ?
    C1 C2 H2 . . 118.8 ?
    C1 C2 C3 . . 122.4(3) ?
    C3 C2 H2 . . 118.8 ?
    O3 C3 C2 . . 124.6(3) ?
    O3 C3 C4 . . 119.7(3) ?
    C4 C3 C2 . . 115.7(3) ?
    C3 C4 O2 . . 127.1(3) ?
    C12 C4 O2 . . 111.6(2) ?
    C12 C4 C3 . . 121.3(3) ?
    O2 C5 H5 . . 109.8 ?
    O2 C5 C6 . . 109.0(2) ?
    O2 C5 C13 . . 104.6(2) ?
    C6 C5 H5 . . 109.8 ?
    C6 C5 C13 . . 113.6(2) ?
    C13 C5 H5 . . 109.8 ?
    O1 C6 C5 . . 120.4(3) ?
    O1 C6 C7 . . 123.5(3) ?
    C7 C6 C5 . . 116.1(3) ?
    C6 C7 H7A . . 109.4 ?
    C6 C7 H7B . . 109.4 ?
    C6 C7 C8 . . 111.2(3) ?
    H7A C7 H7B . . 108.0 ?
    C8 C7 H7A . . 109.4 ?
    C8 C7 H7B . . 109.4 ?
    C7 C8 H8A . . 109.8 ?
    C7 C8 H8B . . 109.8 ?
    H8A C8 H8B . . 108.2 ?
    C14 C8 C7 . . 109.5(3) ?
    C14 C8 H8A . . 109.8 ?
    C14 C8 H8B . . 109.8 ?
    N1 C9 H9 . . 107.7 ?
    N1 C9 C10 . . 112.1(2) ?
    N1 C9 C14 . . 107.0(2) ?
    C10 C9 H9 . . 107.7 ?
    C10 C9 C14 . . 114.5(2) ?
    C14 C9 H9 . . 107.7 ?
    C9 C10 H10A . . 108.5 ?
    C9 C10 H10B . . 108.5 ?
    H10A C10 H10B . . 107.5 ?
    C11 C10 C9 . . 115.0(2) ?
    C11 C10 H10A . . 108.5 ?
    C11 C10 H10B . . 108.5 ?
    C1 C11 C10 . . 127.3(3) ?
    C12 C11 C1 . . 115.3(3) ?
    C12 C11 C10 . . 117.2(2) ?
    C4 C12 C13 . . 108.8(2) ?
    C11 C12 C4 . . 123.9(3) ?
    C11 C12 C13 . . 127.2(3) ?
    C12 C13 C5 . . 98.3(2) ?
    C12 C13 C14 . . 109.3(2) ?
    C12 C13 C15 . . 109.2(2) ?
    C14 C13 C5 . . 117.4(2) ?
    C14 C13 C15 . . 108.9(2) ?
    C15 C13 C5 . . 112.9(2) ?
    O4 C14 C8 . . 109.9(3) ?
    O4 C14 C9 . . 109.8(2) ?
    O4 C14 C13 . . 106.4(2) ?
    C8 C14 C9 . . 111.9(2) ?
    C8 C14 C13 . . 112.1(2) ?
    C13 C14 C9 . . 106.5(2) ?
    C13 C15 H15A . . 109.4 ?
    C13 C15 H15B . . 109.4 ?
    H15A C15 H15B . . 108.0 ?
    C16 C15 C13 . . 111.4(2) ?
    C16 C15 H15A . . 109.4 ?
    C16 C15 H15B . . 109.4 ?
    N1 C16 C15 . . 111.9(2) ?
    N1 C16 H16A . . 109.2 ?
    N1 C16 H16B . . 109.2 ?
    C15 C16 H16A . . 109.2 ?
    C15 C16 H16B . . 109.2 ?
    H16A C16 H16B . . 107.9 ?
    N1 C17 H17A . . 108.8 ?
    N1 C17 H17B . . 108.8 ?
    H17A C17 H17B . . 107.7 ?
    C18 C17 N1 . . 113.8(2) ?
    C18 C17 H17A . . 108.8 ?
    C18 C17 H17B . . 108.8 ?
    C17 C18 H18 . . 115.7 ?
    C17 C18 C19 . . 118.7(3) ?
    C17 C18 C20 . . 119.6(3) ?
    C19 C18 H18 . . 115.7 ?
    C20 C18 H18 . . 115.7 ?
    C20 C18 C19 . . 59.7(2) ?
    C18 C19 H19A . . 117.8 ?
    C18 C19 H19B . . 117.8 ?
    H19A C19 H19B . . 114.9 ?
    C20 C19 C18 . . 60.2(2) ?
    C20 C19 H19A . . 117.8 ?
    C20 C19 H19B . . 117.8 ?
    C18 C20 H20A . . 117.8 ?
    C18 C20 H20B . . 117.8 ?
    C19 C20 C18 . . 60.2(2) ?
    C19 C20 H20A . . 117.8 ?
    C19 C20 H20B . . 117.8 ?
    H20A C20 H20B . . 114.9 ?
    C21 O5 H5A . . 107(4) ?
    O5 C21 H21 . . 109.4 ?
    O5 C21 C22 . . 108.9(5) ?
    O5 C21 C23 . . 107.5(6) ?
    C22 C21 H21 . . 109.4 ?
    C23 C21 H21 . . 109.4 ?
    C23 C21 C22 . . 112.2(5) ?
    C21 C22 H22A . . 109.5 ?
    C21 C22 H22B . . 109.5 ?
    C21 C22 H22C . . 109.5 ?
    H22A C22 H22B . . 109.5 ?
    H22A C22 H22C . . 109.5 ?
    H22B C22 H22C . . 109.5 ?
    C21 C23 H23A . . 109.5 ?
    C21 C23 H23B . . 109.5 ?
    C21 C23 H23C . . 109.5 ?
    H23A C23 H23B . . 109.5 ?
    H23A C23 H23C . . 109.5 ?
    H23B C23 H23C . . 109.5 ?
    C21A O5A H5AA . . 112(5) ?
    O5A C21A H21A . . 105.5 ?
    O5A C21A C22A . . 112(3) ?
    O5A C21A C23A . . 116(3) ?
    C22A C21A H21A . . 105.5 ?
    C23A C21A H21A . . 105.5 ?
    C23A C21A C22A . . 112(3) ?
    C21A C22A H22D . . 109.5 ?
    C21A C22A H22E . . 109.5 ?
    C21A C22A H22F . . 109.5 ?
    H22D C22A H22E . . 109.5 ?
    H22D C22A H22F . . 109.5 ?
    H22E C22A H22F . . 109.5 ?
    C21A C23A H23D . . 109.5 ?
    C21A C23A H23E . . 109.5 ?
    C21A C23A H23F . . 109.5 ?
    H23D C23A H23E . . 109.5 ?
    H23D C23A H23F . . 109.5 ?
    H23E C23A H23F . . 109.5 ?
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
    O1 C6 C7 C8 . . . . 128.6(3) ?
    O2 C4 C12 C11 . . . . 175.7(3) ?
    O2 C4 C12 C13 . . . . -6.0(3) ?
    O2 C5 C6 O1 . . . . -28.1(4) ?
    O2 C5 C6 C7 . . . . 152.6(2) ?
    O2 C5 C13 C12 . . . . -33.5(3) ?
    O2 C5 C13 C14 . . . . -150.4(2) ?
    O2 C5 C13 C15 . . . . 81.5(3) ?
    O3 C3 C4 O2 . . . . 1.8(5) ?
    O3 C3 C4 C12 . . . . -177.3(3) ?
    N1 C9 C10 C11 . . . . -85.6(3) ?
    N1 C9 C14 O4 . . . . -49.3(3) ?
    N1 C9 C14 C8 . . . . -171.7(2) ?
    N1 C9 C14 C13 . . . . 65.5(3) ?
    N1 C17 C18 C19 . . . . -148.5(3) ?
    N1 C17 C18 C20 . . . . -79.0(3) ?
    C1 C2 C3 O3 . . . . -179.6(3) ?
    C1 C2 C3 C4 . . . . 1.2(5) ?
    C1 C11 C12 C4 . . . . 4.6(5) ?
    C1 C11 C12 C13 . . . . -173.5(3) ?
    C2 C1 C11 C10 . . . . 174.6(3) ?
    C2 C1 C11 C12 . . . . -1.3(5) ?
    C2 C3 C4 O2 . . . . -179.0(3) ?
    C2 C3 C4 C12 . . . . 2.0(4) ?
    C3 C4 C12 C11 . . . . -5.1(5) ?
    C3 C4 C12 C13 . . . . 173.2(3) ?
    C4 O2 C5 C6 . . . . -90.0(3) ?
    C4 O2 C5 C13 . . . . 31.9(3) ?
    C4 C12 C13 C5 . . . . 24.2(3) ?
    C4 C12 C13 C14 . . . . 147.2(2) ?
    C4 C12 C13 C15 . . . . -93.7(3) ?
    C5 O2 C4 C3 . . . . 164.1(3) ?
    C5 O2 C4 C12 . . . . -16.7(3) ?
    C5 C6 C7 C8 . . . . -52.1(4) ?
    C5 C13 C14 O4 . . . . -77.4(3) ?
    C5 C13 C14 C8 . . . . 42.9(4) ?
    C5 C13 C14 C9 . . . . 165.5(2) ?
    C5 C13 C15 C16 . . . . -170.2(2) ?
    C6 C5 C13 C12 . . . . 85.2(3) ?
    C6 C5 C13 C14 . . . . -31.7(3) ?
    C6 C5 C13 C15 . . . . -159.7(2) ?
    C6 C7 C8 C14 . . . . 61.6(4) ?
    C7 C8 C14 O4 . . . . 61.7(3) ?
    C7 C8 C14 C9 . . . . -176.1(2) ?
    C7 C8 C14 C13 . . . . -56.5(3) ?
    C9 N1 C16 C15 . . . . 53.8(3) ?
    C9 N1 C17 C18 . . . . -47.9(3) ?
    C9 C10 C11 C1 . . . . 174.0(3) ?
    C9 C10 C11 C12 . . . . -10.2(4) ?
    C10 C9 C14 O4 . . . . -174.2(2) ?
    C10 C9 C14 C8 . . . . 63.5(3) ?
    C10 C9 C14 C13 . . . . -59.3(3) ?
    C10 C11 C12 C4 . . . . -171.7(3) ?
    C10 C11 C12 C13 . . . . 10.2(4) ?
    C11 C1 C2 C3 . . . . -1.5(5) ?
    C11 C12 C13 C5 . . . . -157.5(3) ?
    C11 C12 C13 C14 . . . . -34.5(4) ?
    C11 C12 C13 C15 . . . . 84.6(4) ?
    C12 C13 C14 O4 . . . . 171.8(2) ?
    C12 C13 C14 C8 . . . . -67.9(3) ?
    C12 C13 C14 C9 . . . . 54.7(3) ?
    C12 C13 C15 C16 . . . . -61.9(3) ?
    C13 C5 C6 O1 . . . . -144.3(3) ?
    C13 C5 C6 C7 . . . . 36.4(4) ?
    C13 C15 C16 N1 . . . . -50.9(3) ?
    C14 C9 C10 C11 . . . . 36.5(4) ?
    C14 C13 C15 C16 . . . . 57.4(3) ?
    C15 C13 C14 O4 . . . . 52.5(3) ?
    C15 C13 C14 C8 . . . . 172.8(3) ?
    C15 C13 C14 C9 . . . . -64.5(3) ?
    C16 N1 C9 C10 . . . . 65.5(3) ?
    C16 N1 C9 C14 . . . . -60.9(3) ?
    C16 N1 C17 C18 . . . . -176.2(2) ?
    C17 N1 C9 C10 . . . . -61.7(3) ?
    C17 N1 C9 C14 . . . . 171.9(2) ?
    C17 N1 C16 C15 . . . . -177.1(2) ?
    C17 C18 C19 C20 . . . . 109.4(3) ?
    C17 C18 C20 C19 . . . . -108.0(3) ?
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
    N1 H1 Cl1 4_456 0.87(3) 2.34(3) 3.102(3) 146.3(7)
    O3 H3 Cl1 3_656 0.75(4) 2.32(4) 3.066(3) 169(4)
    O4 H4 Cl1 . 0.85(4) 2.21(4) 3.054(2) 177(3)
    O5 H5A O2 . 1.00(6) 2.00(5) 2.921(4) 154(6)
data_III
_audit_creation_method
;
Olex2 1.2
(compiled 2017.03.28 svn.r3405 for OlexSys, GUI svn.r5335)
;
_chemical_name_systematic
;
17-(Cyclopropylmethyl)-3,14-dihydroxy-4,5a-epoxymorphinan-6-one hydrochloride
2-methylpropan-2-ol monosolvate
;
_chemical_name_common     'naltrexone chloride t-butanol solvate'
_chemical_formula_moiety     'C20 H24 N O4 +, Cl -C4 H10 O'
_chemical_formula_sum     'C24 H34 Cl N O5'
_chemical_formula_iupac     'C20 H24 N O4 +, Cl -C4 H10 O'
_chemical_formula_weight     451.97
_chemical_melting_point     ?
_shelx_space_group_comment
;
The symmetry employed for this shelxl refinement is uniquely defined
by the following loop, which should always be used as a source of
symmetry information in preference to the above space-group names.
They are only intended as comments.
;
_space_group_crystal_system     monoclinic
_space_group_name_H-M_alt     'P 21'
_space_group_name_Hall     'P 2yb'
loop_
    _space_group_symop_operation_xyz
    'x, y, z'
    '-x, y+1/2, -z'
_cell_length_a     8.8487(4)
_cell_length_b     17.3281(9)
_cell_length_c     15.5702(8)
_cell_angle_alpha     90
_cell_angle_beta     92.702(2)
_cell_angle_gamma     90
_cell_volume     2384.7(2)
_cell_formula_units_Z     4
_cell_measurement_reflns_used     9282
_cell_measurement_theta_min     3.82
_cell_measurement_theta_max     72.01
_cell_measurement_temperature     173(2)
_exptl_crystal_description     'block'
_exptl_crystal_colour     colourless
_exptl_crystal_size_max     0.26
_exptl_crystal_size_mid     0.223
_exptl_crystal_size_min     0.195
_exptl_crystal_density_diffrn     1.259
_exptl_crystal_density_meas     ?
_exptl_crystal_density_method     ?
_exptl_crystal_F_000     968
_exptl_absorpt_coefficient_mu     1.696
_exptl_absorpt_correction_type     multi-scan
_exptl_absorpt_process_details
;
(TWINABS; Bruker, 2012)
;
_shelx_estimated_absorpt_T_min     0.667
_shelx_estimated_absorpt_T_max     0.733
_exptl_absorpt_correction_T_min     ?
_exptl_absorpt_correction_T_max     ?
_diffrn_ambient_temperature     173
_diffrn_radiation_type     CuK\a
_diffrn_radiation_wavelength     1.54178
_diffrn_measurement_device_type     'Bruker PHOTON-100 CMOS'
_diffrn_measurement_method     'φ and ω scans'
_diffrn_detector_area_resol_mean     ?
_diffrn_reflns_number     9642
_diffrn_reflns_av_R_equivalents     ?
_diffrn_reflns_theta_min     2.841
_diffrn_reflns_theta_max     74.589
_diffrn_reflns_theta_full     67.679
_diffrn_measured_fraction_theta_max     0.996
_diffrn_measured_fraction_theta_full     0.999
_diffrn_reflns_limit_h_min     -11
_diffrn_reflns_limit_h_max     11
_diffrn_reflns_limit_k_min     -21
_diffrn_reflns_limit_k_max     21
_diffrn_reflns_limit_l_min     0
_diffrn_reflns_limit_l_max     19
_diffrn_standards_number     0
_refine_special_details
;
 Refined as a 2-component twin.
;
_reflns_number_total     9642
_reflns_number_gt     8820
_reflns_threshold_expression     'I > 2σ(I)'
_refine_ls_structure_factor_coef     Fsqd
_refine_ls_matrix_type     full
_refine_ls_R_factor_all     0.0387
_refine_ls_R_factor_gt     0.0332
_refine_ls_wR_factor_gt     0.0763
_refine_ls_wR_factor_ref     0.0791
_refine_ls_goodness_of_fit_ref     1.044
_refine_ls_restrained_S_all     1.044
_refine_ls_number_reflns     9642
_refine_ls_number_parameters     581
_refine_ls_number_restraints     1
_refine_ls_hydrogen_treatment     mixed
_refine_ls_weighting_scheme     calc
_refine_ls_weighting_details
              'w=1/[σ²(Fo²)+(0.0369P)²+0.2646P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_hydrogens     mixed
_atom_sites_solution_primary     dual
_atom_sites_solution_secondary     ?
_refine_ls_shift/su_max     0.000
_refine_ls_shift/su_mean     0.000
_refine_diff_density_max     0.195
_refine_diff_density_min     -0.166
_refine_ls_extinction_method     none
_refine_ls_extinction_coef     .
_refine_ls_abs_structure_details
;
Flack x determined using 3828 quotients
[(I⁺)-(I⁻)]/[(I⁺)+(I⁻)]
(Parsons et al., 2013)
;
_refine_ls_abs_structure_Flack     -0.004(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'
    'N' 'N' 0.0311 0.0180
                         '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'
    'Cl' 'Cl' 0.3639 0.7018
                         'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
_computing_data_collection
;
APEX2 (Bruker, 2013)
;
_computing_cell_refinement
;
SAINT (Bruker, 2013)
;
_computing_data_reduction
;
SAINT (Bruker, 2013)
;
_computing_structure_solution
;
SHELXT (Sheldrick, 2015a)
;
_computing_structure_refinement
;
SHELXL2014 (Sheldrick, 2015b)
;
_computing_molecular_graphics
;
OLEX2 (Dolomanov et al.,  2009)
;
_computing_publication_material
;
OLEX2 (Dolomanov et al.,  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_adp_type
    _atom_site_calc_flag
    _atom_site_occupancy
    _atom_site_disorder_assembly
    _atom_site_disorder_group
    Cl Cl1 0.66572(8) 0.25519(4) 0.26921(4) 0.03945(16) Uani d 1 . .
    Cl Cl2 -0.15527(8) 0.59450(4) -0.23882(4) 0.03721(15) Uani d 1 . .
    O O101 0.4508(3) 0.37330(15) -0.11407(14) 0.0567(6) Uani d 1 . .
    O O102 0.1647(3) 0.32376(12) -0.09967(11) 0.0398(5) Uani d 1 . .
    O O103 -0.0224(3) 0.44419(12) -0.17614(12) 0.0409(5) Uani d 1 . .
    H H103 -0.077(5) 0.485(2) -0.1889(6) 0.061 Uiso calc 1 . .
    O O104 0.3849(2) 0.24407(11) 0.15125(12) 0.0363(4) Uani d 1 . .
    H H104 0.466(4) 0.2502(3) 0.184(2) 0.054 Uiso calc 1 . .
    N N101 0.1251(3) 0.28034(14) 0.22373(13) 0.0325(5) Uani d 1 . .
    H H101 0.182(2) 0.2418(16) 0.2306(3) 0.039 Uiso calc 1 . .
    C C101 -0.0057(4) 0.49220(17) 0.05622(18) 0.0392(7) Uani d 1 . .
    H H10A -0.0398 0.5315 0.0932 0.047 Uiso calc 1 . .
    C C102 -0.0447(4) 0.49543(17) -0.03114(18) 0.0388(7) Uani d 1 . .
    H H102 -0.1084 0.5361 -0.0520 0.047 Uiso calc 1 . .
    C C103 0.0063(3) 0.44113(16) -0.08976(17) 0.0345(6) Uani d 1 . .
    C C104 0.0958(3) 0.38254(16) -0.05536(16) 0.0340(6) Uani d 1 . .
    C C105 0.2807(4) 0.29429(17) -0.03854(17) 0.0381(7) Uani d 1 . .
    H H105 0.2992 0.2383 -0.0495 0.046 Uiso calc 1 . .
    C C106 0.4274(4) 0.34060(18) -0.04789(18) 0.0426(7) Uani d 1 . .
    C C107 0.5333(4) 0.3442(2) 0.02958(19) 0.0467(8) Uani d 1 . .
    H H10B 0.6185 0.3793 0.0182 0.056 Uiso calc 1 . .
    H H10C 0.5753 0.2923 0.0421 0.056 Uiso calc 1 . .
    C C108 0.4500(4) 0.37357(18) 0.10733(18) 0.0404(7) Uani d 1 . .
    H H10D 0.5220 0.3783 0.1577 0.049 Uiso calc 1 . .
    H H10E 0.4067 0.4252 0.0946 0.049 Uiso calc 1 . .
    C C109 0.2282(3) 0.34699(16) 0.20183(16) 0.0334(6) Uani d 1 . .
    H H109 0.2988 0.3561 0.2529 0.040 Uiso calc 1 . .
    C C110 0.1418(4) 0.42301(17) 0.18302(17) 0.0389(7) Uani d 1 . .
    H H11A 0.0552 0.4259 0.2209 0.047 Uiso calc 1 . .
    H H11B 0.2099 0.4669 0.1978 0.047 Uiso calc 1 . .
    C C111 0.0831(3) 0.43183(16) 0.09051(17) 0.0349(6) Uani d 1 . .
    C C112 0.1276(3) 0.37784(16) 0.03185(17) 0.0318(6) Uani d 1 . .
    C C113 0.2135(3) 0.30510(15) 0.05051(16) 0.0323(6) Uani d 1 . .
    C C114 0.3243(3) 0.31769(16) 0.12767(17) 0.0332(6) Uani d 1 . .
    C C115 0.1007(3) 0.24068(16) 0.07105(17) 0.0364(6) Uani d 1 . .
    H H11C 0.0276 0.2337 0.0215 0.044 Uiso calc 1 . .
    H H11D 0.1561 0.1915 0.0803 0.044 Uiso calc 1 . .
    C C116 0.0155(3) 0.26007(18) 0.15079(17) 0.0371(6) Uani d 1 . .
    H H11E -0.0534 0.3041 0.1385 0.045 Uiso calc 1 . .
    H H11F -0.0464 0.2152 0.1670 0.045 Uiso calc 1 . .
    C C117 0.0460(3) 0.28935(18) 0.30721(17) 0.0365(6) Uani d 1 . .
    H H11G -0.0190 0.3358 0.3037 0.044 Uiso calc 1 . .
    H H11H -0.0200 0.2441 0.3153 0.044 Uiso calc 1 . .
    C C118 0.1548(4) 0.29650(17) 0.38299(17) 0.0382(6) Uani d 1 . .
    H H118 0.2136 0.3457 0.3873 0.046 Uiso calc 1 . .
    C C119 0.2336(4) 0.22618(18) 0.41855(19) 0.0466(8) Uani d 1 . .
    H H11I 0.2121 0.1763 0.3895 0.056 Uiso calc 1 . .
    H H11J 0.3386 0.2322 0.4424 0.056 Uiso calc 1 . .
    C C120 0.1099(5) 0.2623(2) 0.46651(19) 0.0528(9) Uani d 1 . .
    H H12A 0.1385 0.2907 0.5200 0.063 Uiso calc 1 . .
    H H12B 0.0120 0.2347 0.4671 0.063 Uiso calc 1 . .
    O O1 0.0294(3) 0.47448(14) 0.37422(13) 0.0511(6) Uani d 1 . .
    O O2 0.3248(2) 0.51172(11) 0.40399(11) 0.0368(4) Uani d 1 . .
    O O3 0.5194(3) 0.39454(13) 0.34376(12) 0.0436(5) Uani d 1 . .
    H H3 0.570(5) 0.355(2) 0.3345(7) 0.065 Uiso calc 1 . .
    O O4 0.1098(2) 0.60254(11) 0.64191(12) 0.0358(4) Uani d 1 . .
    H H4 0.036(4) 0.5974(3) 0.675(2) 0.054 Uiso calc 1 . .
    N N1 0.3739(3) 0.56903(14) 0.72755(13) 0.0324(5) Uani d 1 . .
    H H1 0.310(4) 0.6157(19) 0.731(2) 0.039 Uiso d 1 . .
    C C1 0.5082(4) 0.35396(17) 0.57788(19) 0.0402(7) Uani d 1 . .
    H H1A 0.5453 0.3171 0.6188 0.048 Uiso calc 1 . .
    C C2 0.5475(3) 0.34791(18) 0.49230(19) 0.0403(7) Uani d 1 . .
    H H2 0.6140 0.3078 0.4767 0.048 Uiso calc 1 . .
    C C3 0.4921(3) 0.39885(17) 0.42884(17) 0.0355(6) Uani d 1 . .
    C C4 0.3974(3) 0.45702(16) 0.45557(17) 0.0326(6) Uani d 1 . .
    C C5 0.2118(3) 0.54665(16) 0.45837(16) 0.0345(6) Uani d 1 . .
    H H5 0.1983 0.6025 0.4435 0.041 Uiso calc 1 . .
    C C6 0.0611(4) 0.50333(16) 0.44294(18) 0.0369(6) Uani d 1 . .
    C C7 -0.0406(4) 0.49965(19) 0.51721(19) 0.0422(7) Uani d 1 . .
    H H7A -0.1257 0.4641 0.5030 0.051 Uiso calc 1 . .
    H H7B -0.0834 0.5515 0.5273 0.051 Uiso calc 1 . .
    C C8 0.0453(3) 0.47173(17) 0.59927(18) 0.0366(6) Uani d 1 . .
    H H8A -0.0252 0.4675 0.6466 0.044 Uiso calc 1 . .
    H H8B 0.0889 0.4200 0.5894 0.044 Uiso calc 1 . .
    C C9 0.2696(3) 0.50184(16) 0.70365(16) 0.0331(6) Uani d 1 . .
    H H9 0.2003 0.4946 0.7519 0.040 Uiso calc 1 . .
    C C10 0.3548(4) 0.42536(17) 0.69254(17) 0.0381(7) Uani d 1 . .
    H H10F 0.4407 0.4233 0.7355 0.046 Uiso calc 1 . .
    H H10G 0.2859 0.3821 0.7048 0.046 Uiso calc 1 . .
    C C11 0.4147(3) 0.41385(16) 0.60374(17) 0.0349(6) Uani d 1 . .
    C C12 0.3663(3) 0.46504(15) 0.54039(16) 0.0310(6) Uani d 1 . .
    C C13 0.2796(3) 0.53846(15) 0.55069(16) 0.0310(6) Uani d 1 . .
    C C14 0.1716(3) 0.52858(15) 0.62424(16) 0.0314(6) Uani d 1 . .
    C C15 0.3919(3) 0.60404(16) 0.57368(16) 0.0343(6) Uani d 1 . .
    H H15A 0.4629 0.6101 0.5269 0.041 Uiso calc 1 . .
    H H15B 0.3357 0.6531 0.5790 0.041 Uiso calc 1 . .
    C C16 0.4808(3) 0.58751(18) 0.65763(16) 0.0360(6) Uani d 1 . .
    H H16A 0.5498 0.5434 0.6498 0.043 Uiso calc 1 . .
    H H16B 0.5429 0.6331 0.6745 0.043 Uiso calc 1 . .
    C C17 0.4593(3) 0.56109(18) 0.81328(17) 0.0376(6) Uani d 1 . .
    H H17A 0.5250 0.5149 0.8120 0.045 Uiso calc 1 . .
    H H17B 0.5252 0.6067 0.8228 0.045 Uiso calc 1 . .
    C C18 0.3563(4) 0.55394(17) 0.88672(17) 0.0389(7) Uani d 1 . .
    H H18 0.2991 0.5044 0.8905 0.047 Uiso calc 1 . .
    C C19 0.4090(4) 0.5899(2) 0.97063(18) 0.0524(8) Uani d 1 . .
    H H19A 0.3863 0.5624 1.0242 0.063 Uiso calc 1 . .
    H H19B 0.5066 0.6180 0.9727 0.063 Uiso calc 1 . .
    C C20 0.2796(4) 0.62445(19) 0.9190(2) 0.0472(8) Uani d 1 . .
    H H20A 0.2972 0.6739 0.8892 0.057 Uiso calc 1 . .
    H H20B 0.1769 0.6183 0.9407 0.057 Uiso calc 1 . .
    O O5 0.4669(3) 0.57652(18) 0.25608(17) 0.0659(8) Uani d 1 . .
    H H5A 0.4432(18) 0.545(3) 0.297(3) 0.099 Uiso calc 1 . .
    C C21 0.6265(4) 0.5937(3) 0.2645(2) 0.0548(9) Uani d 1 . .
    C C22 0.6449(5) 0.6660(3) 0.2117(3) 0.0857(16) Uani d 1 . .
    H H22A 0.5998 0.6579 0.1537 0.129 Uiso calc 1 . .
    H H22B 0.7527 0.6778 0.2082 0.129 Uiso calc 1 . .
    H H22C 0.5940 0.7091 0.2390 0.129 Uiso calc 1 . .
    C C23 0.7149(5) 0.5272(3) 0.2279(3) 0.0768(13) Uani d 1 . .
    H H23A 0.6925 0.4797 0.2589 0.115 Uiso calc 1 . .
    H H23B 0.8234 0.5382 0.2344 0.115 Uiso calc 1 . .
    H H23C 0.6858 0.5209 0.1668 0.115 Uiso calc 1 . .
    C C24 0.6731(4) 0.6062(3) 0.3577(2) 0.0644(10) Uani d 1 . .
    H H24A 0.6150 0.6491 0.3805 0.097 Uiso calc 1 . .
    H H24B 0.7813 0.6184 0.3630 0.097 Uiso calc 1 . .
    H H24C 0.6534 0.5592 0.3904 0.097 Uiso calc 1 . .
    O O6 0.2828(3) 0.69659(15) 0.32281(17) 0.0634(7) Uani d 1 . .
    H H6 0.3391 0.6639 0.3005 0.095 Uiso calc 1 . .
    C C31 0.1740(4) 0.7253(2) 0.2583(2) 0.0490(8) Uani d 1 . .
    C C32 0.0606(6) 0.7709(3) 0.3054(3) 0.0751(12) Uani d 1 . .
    H H32A 0.0103 0.7371 0.3457 0.113 Uiso calc 1 . .
    H H32B -0.0149 0.7927 0.2642 0.113 Uiso calc 1 . .
    H H32C 0.1121 0.8128 0.3373 0.113 Uiso calc 1 . .
    C C33 0.2538(5) 0.7753(3) 0.1944(3) 0.0766(13) Uani d 1 . .
    H H33A 0.2990 0.8201 0.2242 0.115 Uiso calc 1 . .
    H H33B 0.1806 0.7929 0.1494 0.115 Uiso calc 1 . .
    H H33C 0.3334 0.7452 0.1683 0.115 Uiso calc 1 . .
    C C34 0.1000(5) 0.6567(3) 0.2120(3) 0.0744(12) Uani d 1 . .
    H H34A 0.1780 0.6253 0.1861 0.112 Uiso calc 1 . .
    H H34B 0.0281 0.6752 0.1668 0.112 Uiso calc 1 . .
    H H34C 0.0464 0.6253 0.2532 0.112 Uiso calc 1 . .
_geom_special_details
;
 All esds (except the esd in the dihedral angle between two l.s. planes)
 are estimated using the full covariance matrix.  The cell esds are taken
 into account individually in the estimation of esds in distances, angles
 and torsion angles; correlations between esds in cell parameters are only
 used when they are defined by crystal symmetry.  An approximate (isotropic)
 treatment of cell esds is used for estimating esds 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
    O101 C106 . 1.203(4) ?
    O102 C104 . 1.387(3) ?
    O102 C105 . 1.459(3) ?
    O103 H103 . 0.87(4) ?
    O103 C103 . 1.358(3) ?
    O104 H104 . 0.87(4) ?
    O104 C114 . 1.425(3) ?
    N101 H101 . 0.84(3) ?
    N101 C109 . 1.520(4) ?
    N101 C116 . 1.500(3) ?
    N101 C117 . 1.513(3) ?
    C101 H10A . 0.9500 ?
    C101 C102 . 1.388(4) ?
    C101 C111 . 1.399(4) ?
    C102 H102 . 0.9500 ?
    C102 C103 . 1.400(4) ?
    C103 C104 . 1.380(4) ?
    C104 C112 . 1.376(4) ?
    C105 H105 . 1.0000 ?
    C105 C106 . 1.539(5) ?
    C105 C113 . 1.545(4) ?
    C106 C107 . 1.494(4) ?
    C107 H10B . 0.9900 ?
    C107 H10C . 0.9900 ?
    C107 C108 . 1.533(4) ?
    C108 H10D . 0.9900 ?
    C108 H10E . 0.9900 ?
    C108 C114 . 1.520(4) ?
    C109 H109 . 1.0000 ?
    C109 C110 . 1.544(4) ?
    C109 C114 . 1.551(4) ?
    C110 H11A . 0.9900 ?
    C110 H11B . 0.9900 ?
    C110 C111 . 1.516(4) ?
    C111 C112 . 1.378(4) ?
    C112 C113 . 1.493(4) ?
    C113 C114 . 1.530(4) ?
    C113 C115 . 1.541(4) ?
    C115 H11C . 0.9900 ?
    C115 H11D . 0.9900 ?
    C115 C116 . 1.520(4) ?
    C116 H11E . 0.9900 ?
    C116 H11F . 0.9900 ?
    C117 H11G . 0.9900 ?
    C117 H11H . 0.9900 ?
    C117 C118 . 1.492(4) ?
    C118 H118 . 1.0000 ?
    C118 C119 . 1.497(4) ?
    C118 C120 . 1.500(4) ?
    C119 H11I . 0.9900 ?
    C119 H11J . 0.9900 ?
    C119 C120 . 1.491(5) ?
    C120 H12A . 0.9900 ?
    C120 H12B . 0.9900 ?
    O1 C6 . 1.202(3) ?
    O2 C4 . 1.381(3) ?
    O2 C5 . 1.471(3) ?
    O3 H3 . 0.84(4) ?
    O3 C3 . 1.360(3) ?
    O4 H4 . 0.86(4) ?
    O4 C14 . 1.425(3) ?
    N1 H1 . 0.99(3) ?
    N1 C9 . 1.521(4) ?
    N1 C16 . 1.510(3) ?
    N1 C17 . 1.509(3) ?
    C1 H1A . 0.9500 ?
    C1 C2 . 1.397(4) ?
    C1 C11 . 1.398(4) ?
    C2 H2 . 0.9500 ?
    C2 C3 . 1.396(4) ?
    C3 C4 . 1.387(4) ?
    C4 C12 . 1.369(4) ?
    C5 H5 . 1.0000 ?
    C5 C6 . 1.539(4) ?
    C5 C13 . 1.538(4) ?
    C6 C7 . 1.500(4) ?
    C7 H7A . 0.9900 ?
    C7 H7B . 0.9900 ?
    C7 C8 . 1.534(4) ?
    C8 H8A . 0.9900 ?
    C8 H8B . 0.9900 ?
    C8 C14 . 1.526(4) ?
    C9 H9 . 1.0000 ?
    C9 C10 . 1.538(4) ?
    C9 C14 . 1.548(4) ?
    C10 H10F . 0.9900 ?
    C10 H10G . 0.9900 ?
    C10 C11 . 1.517(4) ?
    C11 C12 . 1.380(4) ?
    C12 C13 . 1.498(4) ?
    C13 C14 . 1.535(4) ?
    C13 C15 . 1.541(4) ?
    C15 H15A . 0.9900 ?
    C15 H15B . 0.9900 ?
    C15 C16 . 1.521(4) ?
    C16 H16A . 0.9900 ?
    C16 H16B . 0.9900 ?
    C17 H17A . 0.9900 ?
    C17 H17B . 0.9900 ?
    C17 C18 . 1.500(4) ?
    C18 H18 . 1.0000 ?
    C18 C19 . 1.502(4) ?
    C18 C20 . 1.496(4) ?
    C19 H19A . 0.9900 ?
    C19 H19B . 0.9900 ?
    C19 C20 . 1.493(5) ?
    C20 H20A . 0.9900 ?
    C20 H20B . 0.9900 ?
    O5 H5A . 0.87(5) ?
    O5 C21 . 1.443(4) ?
    C21 C22 . 1.512(6) ?
    C21 C23 . 1.518(6) ?
    C21 C24 . 1.506(5) ?
    C22 H22A . 0.9800 ?
    C22 H22B . 0.9800 ?
    C22 H22C . 0.9800 ?
    C23 H23A . 0.9800 ?
    C23 H23B . 0.9800 ?
    C23 H23C . 0.9800 ?
    C24 H24A . 0.9800 ?
    C24 H24B . 0.9800 ?
    C24 H24C . 0.9800 ?
    O6 H6 . 0.8400 ?
    O6 C31 . 1.447(4) ?
    C31 C32 . 1.497(5) ?
    C31 C33 . 1.519(5) ?
    C31 C34 . 1.522(5) ?
    C32 H32A . 0.9800 ?
    C32 H32B . 0.9800 ?
    C32 H32C . 0.9800 ?
    C33 H33A . 0.9800 ?
    C33 H33B . 0.9800 ?
    C33 H33C . 0.9800 ?
    C34 H34A . 0.9800 ?
    C34 H34B . 0.9800 ?
    C34 H34C . 0.9800 ?
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
    C104 O102 C105 . . 104.2(2) ?
    C103 O103 H103 . . 109.5 ?
    C114 O104 H104 . . 109.5 ?
    C109 N101 H101 . . 105.7 ?
    C116 N101 H101 . . 105.7 ?
    C116 N101 C109 . . 112.4(2) ?
    C116 N101 C117 . . 111.4(2) ?
    C117 N101 H101 . . 105.7 ?
    C117 N101 C109 . . 114.9(2) ?
    C102 C101 H10A . . 119.6 ?
    C102 C101 C111 . . 120.9(3) ?
    C111 C101 H10A . . 119.6 ?
    C101 C102 H102 . . 118.7 ?
    C101 C102 C103 . . 122.6(3) ?
    C103 C102 H102 . . 118.7 ?
    O103 C103 C102 . . 124.6(2) ?
    O103 C103 C104 . . 119.4(3) ?
    C104 C103 C102 . . 116.0(2) ?
    C103 C104 O102 . . 127.2(2) ?
    C112 C104 O102 . . 111.9(2) ?
    C112 C104 C103 . . 120.9(3) ?
    O102 C105 H105 . . 110.1 ?
    O102 C105 C106 . . 109.1(2) ?
    O102 C105 C113 . . 104.7(2) ?
    C106 C105 H105 . . 110.1 ?
    C106 C105 C113 . . 112.5(2) ?
    C113 C105 H105 . . 110.1 ?
    O101 C106 C105 . . 120.5(3) ?
    O101 C106 C107 . . 123.0(3) ?
    C107 C106 C105 . . 116.5(2) ?
    C106 C107 H10B . . 109.6 ?
    C106 C107 H10C . . 109.6 ?
    C106 C107 C108 . . 110.2(3) ?
    H10B C107 H10C . . 108.1 ?
    C108 C107 H10B . . 109.6 ?
    C108 C107 H10C . . 109.6 ?
    C107 C108 H10D . . 109.7 ?
    C107 C108 H10E . . 109.7 ?
    H10D C108 H10E . . 108.2 ?
    C114 C108 C107 . . 109.7(3) ?
    C114 C108 H10D . . 109.7 ?
    C114 C108 H10E . . 109.7 ?
    N101 C109 H109 . . 107.5 ?
    N101 C109 C110 . . 113.2(2) ?
    N101 C109 C114 . . 105.9(2) ?
    C110 C109 H109 . . 107.5 ?
    C110 C109 C114 . . 114.9(2) ?
    C114 C109 H109 . . 107.5 ?
    C109 C110 H11A . . 108.7 ?
    C109 C110 H11B . . 108.7 ?
    H11A C110 H11B . . 107.6 ?
    C111 C110 C109 . . 114.3(2) ?
    C111 C110 H11A . . 108.7 ?
    C111 C110 H11B . . 108.7 ?
    C101 C111 C110 . . 126.8(2) ?
    C112 C111 C101 . . 115.3(2) ?
    C112 C111 C110 . . 117.7(3) ?
    C104 C112 C111 . . 124.2(3) ?
    C104 C112 C113 . . 108.7(2) ?
    C111 C112 C113 . . 127.1(2) ?
    C112 C113 C105 . . 98.1(2) ?
    C112 C113 C114 . . 109.5(2) ?
    C112 C113 C115 . . 108.9(2) ?
    C114 C113 C105 . . 117.6(3) ?
    C114 C113 C115 . . 109.7(2) ?
    C115 C113 C105 . . 112.2(2) ?
    O104 C114 C108 . . 110.7(2) ?
    O104 C114 C109 . . 108.3(2) ?
    O104 C114 C113 . . 107.1(2) ?
    C108 C114 C109 . . 112.3(2) ?
    C108 C114 C113 . . 112.1(2) ?
    C113 C114 C109 . . 106.2(2) ?
    C113 C115 H11C . . 109.4 ?
    C113 C115 H11D . . 109.4 ?
    H11C C115 H11D . . 108.0 ?
    C116 C115 C113 . . 111.1(2) ?
    C116 C115 H11C . . 109.4 ?
    C116 C115 H11D . . 109.4 ?
    N101 C116 C115 . . 110.0(2) ?
    N101 C116 H11E . . 109.7 ?
    N101 C116 H11F . . 109.7 ?
    C115 C116 H11E . . 109.7 ?
    C115 C116 H11F . . 109.7 ?
    H11E C116 H11F . . 108.2 ?
    N101 C117 H11G . . 109.1 ?
    N101 C117 H11H . . 109.1 ?
    H11G C117 H11H . . 107.9 ?
    C118 C117 N101 . . 112.4(2) ?
    C118 C117 H11G . . 109.1 ?
    C118 C117 H11H . . 109.1 ?
    C117 C118 H118 . . 116.0 ?
    C117 C118 C119 . . 119.8(3) ?
    C117 C118 C120 . . 117.7(3) ?
    C119 C118 H118 . . 116.0 ?
    C119 C118 C120 . . 59.7(2) ?
    C120 C118 H118 . . 116.0 ?
    C118 C119 H11I . . 117.7 ?
    C118 C119 H11J . . 117.7 ?
    H11I C119 H11J . . 114.9 ?
    C120 C119 C118 . . 60.3(2) ?
    C120 C119 H11I . . 117.7 ?
    C120 C119 H11J . . 117.7 ?
    C118 C120 H12A . . 117.8 ?
    C118 C120 H12B . . 117.8 ?
    C119 C120 C118 . . 60.1(2) ?
    C119 C120 H12A . . 117.8 ?
    C119 C120 H12B . . 117.8 ?
    H12A C120 H12B . . 114.9 ?
    C4 O2 C5 . . 104.94(19) ?
    C3 O3 H3 . . 109.5 ?
    C14 O4 H4 . . 109.5 ?
    C9 N1 H1 . . 107.4(19) ?
    C16 N1 H1 . . 104.0(18) ?
    C16 N1 C9 . . 112.3(2) ?
    C17 N1 H1 . . 106.9(18) ?
    C17 N1 C9 . . 114.8(2) ?
    C17 N1 C16 . . 110.7(2) ?
    C2 C1 H1A . . 119.8 ?
    C2 C1 C11 . . 120.5(3) ?
    C11 C1 H1A . . 119.8 ?
    C1 C2 H2 . . 118.9 ?
    C3 C2 C1 . . 122.2(3) ?
    C3 C2 H2 . . 118.9 ?
    O3 C3 C2 . . 125.6(3) ?
    O3 C3 C4 . . 118.0(2) ?
    C4 C3 C2 . . 116.3(2) ?
    O2 C4 C3 . . 126.5(2) ?
    C12 C4 O2 . . 112.5(2) ?
    C12 C4 C3 . . 121.0(3) ?
    O2 C5 H5 . . 110.0 ?
    O2 C5 C6 . . 108.5(2) ?
    O2 C5 C13 . . 104.7(2) ?
    C6 C5 H5 . . 110.0 ?
    C13 C5 H5 . . 110.0 ?
    C13 C5 C6 . . 113.4(2) ?
    O1 C6 C5 . . 120.4(3) ?
    O1 C6 C7 . . 123.0(3) ?
    C7 C6 C5 . . 116.6(2) ?
    C6 C7 H7A . . 109.4 ?
    C6 C7 H7B . . 109.4 ?
    C6 C7 C8 . . 111.3(2) ?
    H7A C7 H7B . . 108.0 ?
    C8 C7 H7A . . 109.4 ?
    C8 C7 H7B . . 109.4 ?
    C7 C8 H8A . . 109.7 ?
    C7 C8 H8B . . 109.7 ?
    H8A C8 H8B . . 108.2 ?
    C14 C8 C7 . . 109.7(2) ?
    C14 C8 H8A . . 109.7 ?
    C14 C8 H8B . . 109.7 ?
    N1 C9 H9 . . 107.3 ?
    N1 C9 C10 . . 113.1(2) ?
    N1 C9 C14 . . 106.1(2) ?
    C10 C9 H9 . . 107.3 ?
    C10 C9 C14 . . 115.3(2) ?
    C14 C9 H9 . . 107.3 ?
    C9 C10 H10F . . 108.7 ?
    C9 C10 H10G . . 108.7 ?
    H10F C10 H10G . . 107.6 ?
    C11 C10 C9 . . 114.2(2) ?
    C11 C10 H10F . . 108.7 ?
    C11 C10 H10G . . 108.7 ?
    C1 C11 C10 . . 126.7(3) ?
    C12 C11 C1 . . 116.1(2) ?
    C12 C11 C10 . . 117.2(3) ?
    C4 C12 C11 . . 123.7(3) ?
    C4 C12 C13 . . 108.5(2) ?
    C11 C12 C13 . . 127.8(2) ?
    C5 C13 C15 . . 111.6(2) ?
    C12 C13 C5 . . 99.1(2) ?
    C12 C13 C14 . . 109.0(2) ?
    C12 C13 C15 . . 108.9(2) ?
    C14 C13 C5 . . 118.6(2) ?
    C14 C13 C15 . . 109.1(2) ?
    O4 C14 C8 . . 110.3(2) ?
    O4 C14 C9 . . 108.7(2) ?
    O4 C14 C13 . . 107.5(2) ?
    C8 C14 C9 . . 112.7(2) ?
    C8 C14 C13 . . 110.9(2) ?
    C13 C14 C9 . . 106.5(2) ?
    C13 C15 H15A . . 109.4 ?
    C13 C15 H15B . . 109.4 ?
    H15A C15 H15B . . 108.0 ?
    C16 C15 C13 . . 111.3(2) ?
    C16 C15 H15A . . 109.4 ?
    C16 C15 H15B . . 109.4 ?
    N1 C16 C15 . . 110.1(2) ?
    N1 C16 H16A . . 109.6 ?
    N1 C16 H16B . . 109.6 ?
    C15 C16 H16A . . 109.6 ?
    C15 C16 H16B . . 109.6 ?
    H16A C16 H16B . . 108.2 ?
    N1 C17 H17A . . 109.1 ?
    N1 C17 H17B . . 109.1 ?
    H17A C17 H17B . . 107.8 ?
    C18 C17 N1 . . 112.6(2) ?
    C18 C17 H17A . . 109.1 ?
    C18 C17 H17B . . 109.1 ?
    C17 C18 H18 . . 116.3 ?
    C17 C18 C19 . . 117.0(3) ?
    C19 C18 H18 . . 116.3 ?
    C20 C18 C17 . . 119.3(3) ?
    C20 C18 H18 . . 116.3 ?
    C20 C18 C19 . . 59.7(2) ?
    C18 C19 H19A . . 117.8 ?
    C18 C19 H19B . . 117.8 ?
    H19A C19 H19B . . 114.9 ?
    C20 C19 C18 . . 59.9(2) ?
    C20 C19 H19A . . 117.8 ?
    C20 C19 H19B . . 117.8 ?
    C18 C20 H20A . . 117.7 ?
    C18 C20 H20B . . 117.7 ?
    C19 C20 C18 . . 60.3(2) ?
    C19 C20 H20A . . 117.7 ?
    C19 C20 H20B . . 117.7 ?
    H20A C20 H20B . . 114.9 ?
    C21 O5 H5A . . 109.5 ?
    O5 C21 C22 . . 104.5(3) ?
    O5 C21 C23 . . 109.2(4) ?
    O5 C21 C24 . . 109.8(3) ?
    C22 C21 C23 . . 110.7(3) ?
    C24 C21 C22 . . 112.0(4) ?
    C24 C21 C23 . . 110.4(3) ?
    C21 C22 H22A . . 109.5 ?
    C21 C22 H22B . . 109.5 ?
    C21 C22 H22C . . 109.5 ?
    H22A C22 H22B . . 109.5 ?
    H22A C22 H22C . . 109.5 ?
    H22B C22 H22C . . 109.5 ?
    C21 C23 H23A . . 109.5 ?
    C21 C23 H23B . . 109.5 ?
    C21 C23 H23C . . 109.5 ?
    H23A C23 H23B . . 109.5 ?
    H23A C23 H23C . . 109.5 ?
    H23B C23 H23C . . 109.5 ?
    C21 C24 H24A . . 109.5 ?
    C21 C24 H24B . . 109.5 ?
    C21 C24 H24C . . 109.5 ?
    H24A C24 H24B . . 109.5 ?
    H24A C24 H24C . . 109.5 ?
    H24B C24 H24C . . 109.5 ?
    C31 O6 H6 . . 109.5 ?
    O6 C31 C32 . . 106.3(3) ?
    O6 C31 C33 . . 109.7(3) ?
    O6 C31 C34 . . 108.5(3) ?
    C32 C31 C33 . . 111.3(3) ?
    C32 C31 C34 . . 111.2(3) ?
    C33 C31 C34 . . 109.8(4) ?
    C31 C32 H32A . . 109.5 ?
    C31 C32 H32B . . 109.5 ?
    C31 C32 H32C . . 109.5 ?
    H32A C32 H32B . . 109.5 ?
    H32A C32 H32C . . 109.5 ?
    H32B C32 H32C . . 109.5 ?
    C31 C33 H33A . . 109.5 ?
    C31 C33 H33B . . 109.5 ?
    C31 C33 H33C . . 109.5 ?
    H33A C33 H33B . . 109.5 ?
    H33A C33 H33C . . 109.5 ?
    H33B C33 H33C . . 109.5 ?
    C31 C34 H34A . . 109.5 ?
    C31 C34 H34B . . 109.5 ?
    C31 C34 H34C . . 109.5 ?
    H34A C34 H34B . . 109.5 ?
    H34A C34 H34C . . 109.5 ?
    H34B C34 H34C . . 109.5 ?
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
    O101 C106 C107 C108 . . . . 124.1(3) ?
    O102 C104 C112 C111 . . . . 175.1(3) ?
    O102 C104 C112 C113 . . . . -6.0(3) ?
    O102 C105 C106 O101 . . . . -23.8(4) ?
    O102 C105 C106 C107 . . . . 154.2(2) ?
    O102 C105 C113 C112 . . . . -33.9(3) ?
    O102 C105 C113 C114 . . . . -151.0(2) ?
    O102 C105 C113 C115 . . . . 80.3(3) ?
    O103 C103 C104 O102 . . . . 0.6(5) ?
    O103 C103 C104 C112 . . . . 179.8(3) ?
    N101 C109 C110 C111 . . . . -86.3(3) ?
    N101 C109 C114 O104 . . . . -48.8(3) ?
    N101 C109 C114 C108 . . . . -171.4(2) ?
    N101 C109 C114 C113 . . . . 65.9(2) ?
    N101 C117 C118 C119 . . . . -76.9(3) ?
    N101 C117 C118 C120 . . . . -146.1(3) ?
    C101 C102 C103 O103 . . . . -176.5(3) ?
    C101 C102 C103 C104 . . . . 1.4(5) ?
    C101 C111 C112 C104 . . . . 3.0(5) ?
    C101 C111 C112 C113 . . . . -175.6(3) ?
    C102 C101 C111 C110 . . . . 176.2(3) ?
    C102 C101 C111 C112 . . . . 0.3(5) ?
    C102 C103 C104 O102 . . . . -177.4(3) ?
    C102 C103 C104 C112 . . . . 1.8(4) ?
    C103 C104 C112 C111 . . . . -4.2(5) ?
    C103 C104 C112 C113 . . . . 174.6(3) ?
    C104 O102 C105 C106 . . . . -88.5(3) ?
    C104 O102 C105 C113 . . . . 32.1(3) ?
    C104 C112 C113 C105 . . . . 24.4(3) ?
    C104 C112 C113 C114 . . . . 147.5(2) ?
    C104 C112 C113 C115 . . . . -92.5(3) ?
    C105 O102 C104 C103 . . . . 162.4(3) ?
    C105 O102 C104 C112 . . . . -16.9(3) ?
    C105 C106 C107 C108 . . . . -53.9(3) ?
    C105 C113 C114 O104 . . . . -78.5(3) ?
    C105 C113 C114 C108 . . . . 43.1(3) ?
    C105 C113 C114 C109 . . . . 166.0(2) ?
    C105 C113 C115 C116 . . . . -169.7(2) ?
    C106 C105 C113 C112 . . . . 84.4(3) ?
    C106 C105 C113 C114 . . . . -32.6(3) ?
    C106 C105 C113 C115 . . . . -161.3(2) ?
    C106 C107 C108 C114 . . . . 62.1(3) ?
    C107 C108 C114 O104 . . . . 62.9(3) ?
    C107 C108 C114 C109 . . . . -176.0(2) ?
    C107 C108 C114 C113 . . . . -56.6(3) ?
    C109 N101 C116 C115 . . . . 57.1(3) ?
    C109 N101 C117 C118 . . . . -60.2(3) ?
    C109 C110 C111 C101 . . . . 176.2(3) ?
    C109 C110 C111 C112 . . . . -8.0(4) ?
    C110 C109 C114 O104 . . . . -174.6(2) ?
    C110 C109 C114 C108 . . . . 62.9(3) ?
    C110 C109 C114 C113 . . . . -59.8(3) ?
    C110 C111 C112 C104 . . . . -173.4(3) ?
    C110 C111 C112 C113 . . . . 8.0(5) ?
    C111 C101 C102 C103 . . . . -2.4(5) ?
    C111 C112 C113 C105 . . . . -156.8(3) ?
    C111 C112 C113 C114 . . . . -33.7(4) ?
    C111 C112 C113 C115 . . . . 86.3(3) ?
    C112 C113 C114 O104 . . . . 170.8(2) ?
    C112 C113 C114 C108 . . . . -67.6(3) ?
    C112 C113 C114 C109 . . . . 55.3(3) ?
    C112 C113 C115 C116 . . . . -62.2(3) ?
    C113 C105 C106 O101 . . . . -139.6(3) ?
    C113 C105 C106 C107 . . . . 38.5(3) ?
    C113 C115 C116 N101 . . . . -52.1(3) ?
    C114 C109 C110 C111 . . . . 35.6(4) ?
    C114 C113 C115 C116 . . . . 57.6(3) ?
    C115 C113 C114 O104 . . . . 51.4(3) ?
    C115 C113 C114 C108 . . . . 173.0(2) ?
    C115 C113 C114 C109 . . . . -64.1(3) ?
    C116 N101 C109 C110 . . . . 62.6(3) ?
    C116 N101 C109 C114 . . . . -64.2(3) ?
    C116 N101 C117 C118 . . . . 170.5(2) ?
    C117 N101 C109 C110 . . . . -66.3(3) ?
    C117 N101 C109 C114 . . . . 166.9(2) ?
    C117 N101 C116 C115 . . . . -172.2(2) ?
    C117 C118 C119 C120 . . . . -106.7(3) ?
    C117 C118 C120 C119 . . . . 110.0(3) ?
    O1 C6 C7 C8 . . . . 129.6(3) ?
    O2 C4 C12 C11 . . . . 174.5(3) ?
    O2 C4 C12 C13 . . . . -7.9(3) ?
    O2 C5 C6 O1 . . . . -30.2(4) ?
    O2 C5 C6 C7 . . . . 149.9(2) ?
    O2 C5 C13 C12 . . . . -31.2(3) ?
    O2 C5 C13 C14 . . . . -148.7(2) ?
    O2 C5 C13 C15 . . . . 83.3(3) ?
    O3 C3 C4 O2 . . . . 0.8(4) ?
    O3 C3 C4 C12 . . . . -179.4(3) ?
    N1 C9 C10 C11 . . . . -85.1(3) ?
    N1 C9 C14 O4 . . . . -49.5(3) ?
    N1 C9 C14 C8 . . . . -172.1(2) ?
    N1 C9 C14 C13 . . . . 66.1(3) ?
    N1 C17 C18 C19 . . . . -145.7(3) ?
    N1 C17 C18 C20 . . . . -76.9(4) ?
    C1 C2 C3 O3 . . . . -176.7(3) ?
    C1 C2 C3 C4 . . . . 1.0(4) ?
    C1 C11 C12 C4 . . . . 4.0(4) ?
    C1 C11 C12 C13 . . . . -173.1(3) ?
    C2 C1 C11 C10 . . . . 176.1(3) ?
    C2 C1 C11 C12 . . . . -0.2(4) ?
    C2 C3 C4 O2 . . . . -177.2(3) ?
    C2 C3 C4 C12 . . . . 2.6(4) ?
    C3 C4 C12 C11 . . . . -5.4(5) ?
    C3 C4 C12 C13 . . . . 172.3(3) ?
    C4 O2 C5 C6 . . . . -93.1(2) ?
    C4 O2 C5 C13 . . . . 28.3(3) ?
    C4 C12 C13 C5 . . . . 24.1(3) ?
    C4 C12 C13 C14 . . . . 148.6(2) ?
    C4 C12 C13 C15 . . . . -92.5(3) ?
    C5 O2 C4 C3 . . . . 166.5(3) ?
    C5 O2 C4 C12 . . . . -13.3(3) ?
    C5 C6 C7 C8 . . . . -50.4(3) ?
    C5 C13 C14 O4 . . . . -77.4(3) ?
    C5 C13 C14 C8 . . . . 43.3(3) ?
    C5 C13 C14 C9 . . . . 166.2(2) ?
    C5 C13 C15 C16 . . . . -169.0(2) ?
    C6 C5 C13 C12 . . . . 86.9(3) ?
    C6 C5 C13 C14 . . . . -30.6(3) ?
    C6 C5 C13 C15 . . . . -158.6(2) ?
    C6 C7 C8 C14 . . . . 62.0(3) ?
    C7 C8 C14 O4 . . . . 61.7(3) ?
    C7 C8 C14 C9 . . . . -176.6(2) ?
    C7 C8 C14 C13 . . . . -57.4(3) ?
    C9 N1 C16 C15 . . . . 56.5(3) ?
    C9 N1 C17 C18 . . . . -59.8(3) ?
    C9 C10 C11 C1 . . . . 173.3(3) ?
    C9 C10 C11 C12 . . . . -10.4(4) ?
    C10 C9 C14 O4 . . . . -175.5(2) ?
    C10 C9 C14 C8 . . . . 61.9(3) ?
    C10 C9 C14 C13 . . . . -59.9(3) ?
    C10 C11 C12 C4 . . . . -172.6(3) ?
    C10 C11 C12 C13 . . . . 10.2(4) ?
    C11 C1 C2 C3 . . . . -2.2(5) ?
    C11 C12 C13 C5 . . . . -158.4(3) ?
    C11 C12 C13 C14 . . . . -33.9(4) ?
    C11 C12 C13 C15 . . . . 85.0(3) ?
    C12 C13 C14 O4 . . . . 170.5(2) ?
    C12 C13 C14 C8 . . . . -68.8(3) ?
    C12 C13 C14 C9 . . . . 54.1(3) ?
    C12 C13 C15 C16 . . . . -60.7(3) ?
    C13 C5 C6 O1 . . . . -146.1(3) ?
    C13 C5 C6 C7 . . . . 34.0(3) ?
    C13 C15 C16 N1 . . . . -52.5(3) ?
    C14 C9 C10 C11 . . . . 37.2(4) ?
    C14 C13 C15 C16 . . . . 58.1(3) ?
    C15 C13 C14 O4 . . . . 51.8(3) ?
    C15 C13 C14 C8 . . . . 172.4(2) ?
    C15 C13 C14 C9 . . . . -64.6(3) ?
    C16 N1 C9 C10 . . . . 63.9(3) ?
    C16 N1 C9 C14 . . . . -63.4(3) ?
    C16 N1 C17 C18 . . . . 171.8(2) ?
    C17 N1 C9 C10 . . . . -63.6(3) ?
    C17 N1 C9 C14 . . . . 169.1(2) ?
    C17 N1 C16 C15 . . . . -173.8(2) ?
    C17 C18 C19 C20 . . . . 109.8(3) ?
    C17 C18 C20 C19 . . . . -106.0(3) ?
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
    N1 H1 Cl1 2_656 0.99(3) 2.43(3) 3.245(3) 140(3)
    O3 H3 Cl1 . 0.84(4) 2.20(3) 2.999(2) 162(2)
    O4 H4 Cl2 1_556 0.86(3) 2.21(3) 3.063(2) 175.3(8)
    O5 H5A O2 . 0.87(5) 2.09(3) 2.902(3) 154(4)
    O6 H6 O5 . 0.84 2.03 2.867(4) 174
    N101 H101 Cl2 2_545 0.84(2) 2.57(2) 3.239(3) 137.8(18)
    O103 H103 Cl2 . 0.87(4) 2.15(3) 3.002(2) 164(3)
    O104 H104 Cl1 . 0.87(3) 2.16(3) 3.026(2) 175.0(9)
