##############################################################################
###                                                                        ###
###        Electronic paper (Acta Crystallographica Section E)             ###
###                                                                        ###
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#                                                                            #
# 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 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. 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/  #
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data_global
_audit_creation_method     SHELXL-97
_journal_date_recd_electronic     2010-02-06
_journal_date_accepted     2010-03-08
_journal_name_full     'Acta Crystallographica, Section E'
_journal_year     2010
_journal_volume     66
_journal_issue      4
_journal_page_first     o933
_journal_page_last     o933
_journal_paper_category     QO
_journal_coeditor_code     FB2184
_publ_contact_author
;
    Masood Parvez
    Department of Chemistry
    University of Calgary
    2500 University Drive N.W.
    Calgary, Alberta, Canada T2N 1N4
;
_publ_contact_author_email     ' parvez@ucalgary.ca '
_publ_contact_author_fax     ' (403)289-9488 '
_publ_contact_author_phone     ' (403)220-5348 '
_publ_section_title
;
(20S)-20-Acetamido-18-chloro-5α-pregnan-3β-yl acetate
;
loop_
    _publ_author_name
    _publ_author_address
    'Benn, Michael'
; Department of Chemistry
The University of Calgary
2500 University Drive NW
Calgary
Alberta
Canada T2N 1N4
;
    'Vohra, Kanwal Nain'
;
Department of Chemistry
The University of Calgary
2500 University Drive NW
Calgary
Alberta
Canada T2N 1N4
;
    'Parvez, Masood'
;
Department of Chemistry
The University of Calgary
2500 University Drive NW
Calgary
Alberta
Canada T2N 1N4
;
data_I
_chemical_name_systematic
;
(20S)-20-Acetamido-18-chloro-5α-pregnan-3β-yl acetate
;
_chemical_name_common     ?
_chemical_formula_moiety     'C25 H40 Cl N O3'
_chemical_formula_sum     'C25 H40 Cl N O3'
_chemical_formula_iupac     'C25 H40 Cl N O3'
_chemical_formula_weight     438.03
_chemical_melting_point     ?
_chemical_melting_point_gt     504
_chemical_melting_point_lt     505
_symmetry_cell_setting     monoclinic
_symmetry_space_group_name_H-M     'P 21'
_symmetry_space_group_name_Hall     'P 2yb'
loop_
    _symmetry_equiv_pos_as_xyz
    'x, y, z'
    '-x, y+1/2, -z'
_cell_length_a     7.6604(4)
_cell_length_b     9.7796(4)
_cell_length_c     16.8301(8)
_cell_angle_alpha     90.00
_cell_angle_beta     96.398(2)
_cell_angle_gamma     90.00
_cell_volume     1252.98(10)
_cell_formula_units_Z     2
_cell_measurement_reflns_used     2542
_cell_measurement_theta_min     1.0
_cell_measurement_theta_max     27.5
_cell_measurement_temperature     173(2)
_exptl_crystal_description     'plate'
_exptl_crystal_colour     'colorless'
_exptl_crystal_size_max     0.28
_exptl_crystal_size_mid     0.12
_exptl_crystal_size_min     0.04
_exptl_crystal_density_diffrn     1.161
_exptl_crystal_density_meas     ?
_exptl_crystal_density_method     'not measured'
_exptl_crystal_F_000     476
_exptl_absorpt_coefficient_mu     0.177
_exptl_absorpt_correction_type     'multi-scan'
_exptl_absorpt_process_details     '(SORTAV; Blessing, 1997)'
_exptl_absorpt_correction_T_min     0.952
_exptl_absorpt_correction_T_max     0.993
_exptl_special_details
;
¹H-NMR (400 MHz, CDCl₃  ref. res. H  δH 7.25 ppm)
δH  5.30 (1H, br d, J = 9.1 Hz),
4.63 (1H, m) 3.60 (1H, d, J =11.9 Hz), 3.49 (1H, d,
J = 11.9 Hz), 1.99 (3H, s), 1.91 (3H, s),
1.23 (3H, d, J = 6.3 Hz) and 0.78 (3H, s);
¹³C-NMR (100 MHz, CDCl~3,~ ref  77.0 ppm) δC 170.7 s, 168.7 s,
73.5 d, 57.5 d, 57.0 d, 54.0 d, 45.9 s, 44.6 d, 45.5 t, 36.6 t,
35.7 d, 35.4 s, 35.0 s, 33.8 t, 31.7 t, 28.3 t, 27.3 t, 26.2 t,
23.4 q, 23.3 t, 22.2 q, 21.4 q, 20.7 t, 12.2 q;
LRCIMS (NH₃) m/z  438 (100) and 440 (30)
(M+1 ³⁵Cl and ³⁷Cl resp.).
;
_diffrn_ambient_temperature     173(2)
_diffrn_radiation_type     MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_source     'fine-focus sealed tube'
_diffrn_radiation_monochromator     graphite
_diffrn_measurement_device_type
                         'Nonius diffractometer with Bruker APEXII CCD detector'
_diffrn_measurement_method     'φ and ω scans'
_diffrn_detector_area_resol_mean     ?
_diffrn_reflns_number     9843
_diffrn_reflns_av_R_equivalents     0.035
_diffrn_reflns_av_sigmaI/netI     0.032
_diffrn_reflns_theta_min     2.4
_diffrn_reflns_theta_max     27.5
_diffrn_reflns_theta_full     27.50
_diffrn_measured_fraction_theta_max     0.979
_diffrn_measured_fraction_theta_full     0.979
_diffrn_reflns_limit_h_min     -9
_diffrn_reflns_limit_h_max     9
_diffrn_reflns_limit_k_min     -12
_diffrn_reflns_limit_k_max     11
_diffrn_reflns_limit_l_min     -21
_diffrn_reflns_limit_l_max     21
_diffrn_standards_number     0
_diffrn_standards_interval_count     .
_diffrn_standards_interval_time     .
_diffrn_standards_decay_%     ?
_refine_special_details
;
The following three reflections in the low angle range were deemed to be
obstructed by the beam stop and were omitted: 1 1 0, -1 -1 1, 1 0 1
;
_reflns_number_total     5254
_reflns_number_gt     4999
_reflns_threshold_expression     I>2σ(I)
_refine_ls_structure_factor_coef     Fsqd
_refine_ls_matrix_type     full
_refine_ls_R_factor_all     0.0617
_refine_ls_R_factor_gt     0.0570
_refine_ls_wR_factor_gt     0.1492
_refine_ls_wR_factor_ref     0.1540
_refine_ls_goodness_of_fit_ref     1.131
_refine_ls_restrained_S_all     1.131
_refine_ls_number_reflns     5254
_refine_ls_number_parameters     275
_refine_ls_number_restraints     1
_refine_ls_number_constraints     144
_refine_ls_hydrogen_treatment     constr
_refine_ls_weighting_scheme     calc
_refine_ls_weighting_details
         'calc w=1/[σ²(Fo²)+(0.0472P)²+1.6304P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_hydrogens     difmap
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary     difmap
_refine_ls_shift/su_max     0.002
_refine_ls_shift/su_mean     0.000
_refine_diff_density_max     0.735
_refine_diff_density_min     -0.248
_refine_ls_extinction_method     none
_refine_ls_extinction_coef     ?
_refine_ls_abs_structure_details     'Flack (1983), 2026  Friedel pairs'
_refine_ls_abs_structure_Flack     0.04(9)
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'
    'Cl' 'Cl' 0.1484 0.1585
                         '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'
_computing_data_collection     'COLLECT (Hooft, 1998)'
_computing_cell_refinement     'DENZO (Otwinowski & Minor, 1997)'
_computing_data_reduction     'SCALEPACK (Otwinowski & Minor, 1997)'
_computing_structure_solution     'SHELXS97 (Sheldrick, 2008)'
_computing_structure_refinement     'SHELXL97 (Sheldrick, 2008)'
_computing_molecular_graphics     'ORTEP-3 for Windows (Farrugia, 1997)'
_computing_publication_material     'SHELXL97 (Sheldrick, 2008)'
loop_
    _atom_site_type_symbol
    _atom_site_label
    _atom_site_fract_x
    _atom_site_fract_y
    _atom_site_fract_z
    _atom_site_U_iso_or_equiv
    _atom_site_adp_type
    _atom_site_calc_flag
    _atom_site_refinement_flags
    _atom_site_occupancy
    _atom_site_disorder_assembly
    _atom_site_disorder_group
    Cl Cl1 1.18745(9) 0.31045(8) 0.26306(5) 0.03388(19) Uani d . 1 . .
    O O1 0.9823(4) 0.2298(2) 0.50569(17) 0.0451(7) Uani d . 1 . .
    O O2 0.5711(3) 0.1751(3) -0.28266(16) 0.0413(6) Uani d . 1 . .
    O O3 0.3432(5) 0.0304(4) -0.3034(2) 0.0787(12) Uani d . 1 . .
    N N1 0.9983(4) 0.0176(3) 0.45452(16) 0.0289(6) Uani d . 1 . .
    H H1 0.9844 -0.0703 0.4629 0.035 Uiso calc R 1 . .
    C C1 0.8523(4) 0.1056(3) -0.0897(2) 0.0306(7) Uani d . 1 . .
    H H1A 0.9793 0.1224 -0.0749 0.037 Uiso calc R 1 . .
    H H1B 0.8311 0.0065 -0.0840 0.037 Uiso calc R 1 . .
    C C2 0.8040(5) 0.1465(4) -0.1774(2) 0.0344(8) Uani d . 1 . .
    H H2A 0.8354 0.2434 -0.1850 0.041 Uiso calc R 1 . .
    H H2B 0.8708 0.0897 -0.2122 0.041 Uiso calc R 1 . .
    C C3 0.6078(5) 0.1265(4) -0.2005(2) 0.0352(8) Uani d . 1 . .
    H H3 0.5792 0.0269 -0.1985 0.042 Uiso calc R 1 . .
    C C4 0.4980(4) 0.2047(4) -0.1458(2) 0.0338(7) Uani d . 1 . .
    H H4A 0.3718 0.1854 -0.1610 0.041 Uiso calc R 1 . .
    H H4B 0.5170 0.3041 -0.1515 0.041 Uiso calc R 1 . .
    C C5 0.5500(4) 0.1618(3) -0.0587(2) 0.0295(7) Uani d . 1 . .
    H H5 0.5291 0.0610 -0.0562 0.035 Uiso calc R 1 . .
    C C6 0.4329(4) 0.2282(4) -0.0015(2) 0.0355(8) Uani d . 1 . .
    H H6A 0.4516 0.3284 -0.0009 0.043 Uiso calc R 1 . .
    H H6B 0.3081 0.2106 -0.0208 0.043 Uiso calc R 1 . .
    C C7 0.4737(4) 0.1720(4) 0.0828(2) 0.0315(7) Uani d . 1 . .
    H H7A 0.4423 0.0738 0.0830 0.038 Uiso calc R 1 . .
    H H7B 0.4009 0.2203 0.1189 0.038 Uiso calc R 1 . .
    C C8 0.6672(4) 0.1886(3) 0.11419(19) 0.0246(6) Uani d . 1 . .
    H H8 0.6944 0.2883 0.1200 0.030 Uiso calc R 1 . .
    C C9 0.7875(4) 0.1252(3) 0.0557(2) 0.0260(6) Uani d . 1 . .
    H H9 0.7579 0.0256 0.0521 0.031 Uiso calc R 1 . .
    C C10 0.7475(4) 0.1843(3) -0.0313(2) 0.0268(6) Uani d . 1 . .
    C C11 0.9805(4) 0.1340(3) 0.0888(2) 0.0255(6) Uani d . 1 . .
    H H11A 1.0156 0.2313 0.0939 0.031 Uiso calc R 1 . .
    H H11B 1.0528 0.0901 0.0508 0.031 Uiso calc R 1 . .
    C C12 1.0170(4) 0.0640(3) 0.17103(19) 0.0250(6) Uani d . 1 . .
    H H12A 0.9898 -0.0347 0.1655 0.030 Uiso calc R 1 . .
    H H12B 1.1431 0.0734 0.1908 0.030 Uiso calc R 1 . .
    C C13 0.9056(4) 0.1278(3) 0.23165(19) 0.0233(6) Uani d . 1 . .
    C C14 0.7098(4) 0.1199(3) 0.1952(2) 0.0276(6) Uani d . 1 . .
    H H14 0.6841 0.0206 0.1861 0.033 Uiso calc R 1 . .
    C C15 0.6082(4) 0.1624(4) 0.2641(2) 0.0336(8) Uani d . 1 . .
    H H15A 0.4895 0.1211 0.2584 0.040 Uiso calc R 1 . .
    H H15B 0.5967 0.2631 0.2665 0.040 Uiso calc R 1 . .
    C C16 0.7211(4) 0.1070(4) 0.3397(2) 0.0365(8) Uani d . 1 . .
    H H16A 0.7466 0.1811 0.3793 0.044 Uiso calc R 1 . .
    H H16B 0.6577 0.0330 0.3646 0.044 Uiso calc R 1 . .
    C C17 0.8935(4) 0.0516(3) 0.3123(2) 0.0281(7) Uani d . 1 . .
    H H17 0.8746 -0.0474 0.2994 0.034 Uiso calc R 1 . .
    C C18 0.9533(4) 0.2805(3) 0.2470(2) 0.0271(7) Uani d . 1 . .
    H H18A 0.8994 0.3123 0.2945 0.032 Uiso calc R 1 . .
    H H18B 0.9027 0.3353 0.2006 0.032 Uiso calc R 1 . .
    C C19 0.7999(4) 0.3366(3) -0.0322(2) 0.0318(7) Uani d . 1 . .
    H H19A 0.7475 0.3852 0.0103 0.038 Uiso calc R 1 . .
    H H19B 0.7573 0.3767 -0.0841 0.038 Uiso calc R 1 . .
    H H19C 0.9281 0.3447 -0.0232 0.038 Uiso calc R 1 . .
    C C20 1.0498(4) 0.0609(3) 0.3773(2) 0.0297(7) Uani d . 1 . .
    H H20 1.0877 0.1587 0.3821 0.036 Uiso calc R 1 . .
    C C21 1.2082(5) -0.0250(4) 0.3594(2) 0.0396(9) Uani d . 1 . .
    H H21A 1.2517 0.0086 0.3104 0.047 Uiso calc R 1 . .
    H H21B 1.1726 -0.1208 0.3523 0.047 Uiso calc R 1 . .
    H H21C 1.3014 -0.0175 0.4041 0.047 Uiso calc R 1 . .
    C C22 0.9714(5) 0.1050(4) 0.5129(2) 0.0334(7) Uani d . 1 . .
    C C23 0.9265(6) 0.0419(5) 0.5896(2) 0.0460(10) Uani d . 1 . .
    H H23A 0.8899 -0.0532 0.5798 0.055 Uiso calc R 1 . .
    H H23B 0.8306 0.0934 0.6094 0.055 Uiso calc R 1 . .
    H H23C 1.0300 0.0443 0.6295 0.055 Uiso calc R 1 . .
    C C24 0.4371(6) 0.1165(5) -0.3278(3) 0.0534(11) Uani d . 1 . .
    C C25 0.4187(7) 0.1767(7) -0.4111(3) 0.0714(16) Uani d . 1 . .
    H H25A 0.4139 0.1028 -0.4506 0.086 Uiso calc R 1 . .
    H H25B 0.5198 0.2356 -0.4172 0.086 Uiso calc R 1 . .
    H H25C 0.3105 0.2308 -0.4195 0.086 Uiso calc R 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
    Cl1 C18 . 1.808(3) ?
    O1 C22 . 1.230(4) ?
    O2 C24 . 1.336(5) ?
    O2 C3 . 1.459(4) ?
    O3 C24 . 1.208(6) ?
    N1 C22 . 1.335(5) ?
    N1 C20 . 1.462(4) ?
    N1 H1 . 0.8800 ?
    C1 C2 . 1.534(5) ?
    C1 C10 . 1.542(4) ?
    C1 H1A . 0.9900 ?
    C1 H1B . 0.9900 ?
    C2 C3 . 1.522(5) ?
    C2 H2A . 0.9900 ?
    C2 H2B . 0.9900 ?
    C3 C4 . 1.522(5) ?
    C3 H3 . 1.0000 ?
    C4 C5 . 1.533(5) ?
    C4 H4A . 0.9900 ?
    C4 H4B . 0.9900 ?
    C5 C6 . 1.531(5) ?
    C5 C10 . 1.547(4) ?
    C5 H5 . 1.0000 ?
    C6 C7 . 1.521(5) ?
    C6 H6A . 0.9900 ?
    C6 H6B . 0.9900 ?
    C7 C8 . 1.526(4) ?
    C7 H7A . 0.9900 ?
    C7 H7B . 0.9900 ?
    C8 C14 . 1.521(4) ?
    C8 C9 . 1.550(4) ?
    C8 H8 . 1.0000 ?
    C9 C11 . 1.524(4) ?
    C9 C10 . 1.573(5) ?
    C9 H9 . 1.0000 ?
    C10 C19 . 1.543(4) ?
    C11 C12 . 1.541(4) ?
    C11 H11A . 0.9900 ?
    C11 H11B . 0.9900 ?
    C12 C13 . 1.534(4) ?
    C12 H12A . 0.9900 ?
    C12 H12B . 0.9900 ?
    C13 C18 . 1.552(4) ?
    C13 C14 . 1.558(4) ?
    C13 C17 . 1.560(4) ?
    C14 C15 . 1.525(5) ?
    C14 H14 . 1.0000 ?
    C15 C16 . 1.554(5) ?
    C15 H15A . 0.9900 ?
    C15 H15B . 0.9900 ?
    C16 C17 . 1.544(4) ?
    C16 H16A . 0.9900 ?
    C16 H16B . 0.9900 ?
    C17 C20 . 1.532(5) ?
    C17 H17 . 1.0000 ?
    C18 H18A . 0.9900 ?
    C18 H18B . 0.9900 ?
    C19 H19A . 0.9800 ?
    C19 H19B . 0.9800 ?
    C19 H19C . 0.9800 ?
    C20 C21 . 1.533(5) ?
    C20 H20 . 1.0000 ?
    C21 H21A . 0.9800 ?
    C21 H21B . 0.9800 ?
    C21 H21C . 0.9800 ?
    C22 C23 . 1.505(5) ?
    C23 H23A . 0.9800 ?
    C23 H23B . 0.9800 ?
    C23 H23C . 0.9800 ?
    C24 C25 . 1.513(7) ?
    C25 H25A . 0.9800 ?
    C25 H25B . 0.9800 ?
    C25 H25C . 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
    C24 O2 C3 . . 117.0(3) ?
    C22 N1 C20 . . 123.2(3) ?
    C22 N1 H1 . . 118.4 ?
    C20 N1 H1 . . 118.4 ?
    C2 C1 C10 . . 113.3(3) ?
    C2 C1 H1A . . 108.9 ?
    C10 C1 H1A . . 108.9 ?
    C2 C1 H1B . . 108.9 ?
    C10 C1 H1B . . 108.9 ?
    H1A C1 H1B . . 107.7 ?
    C3 C2 C1 . . 109.8(3) ?
    C3 C2 H2A . . 109.7 ?
    C1 C2 H2A . . 109.7 ?
    C3 C2 H2B . . 109.7 ?
    C1 C2 H2B . . 109.7 ?
    H2A C2 H2B . . 108.2 ?
    O2 C3 C4 . . 110.4(3) ?
    O2 C3 C2 . . 106.3(3) ?
    C4 C3 C2 . . 112.2(3) ?
    O2 C3 H3 . . 109.3 ?
    C4 C3 H3 . . 109.3 ?
    C2 C3 H3 . . 109.3 ?
    C3 C4 C5 . . 109.8(3) ?
    C3 C4 H4A . . 109.7 ?
    C5 C4 H4A . . 109.7 ?
    C3 C4 H4B . . 109.7 ?
    C5 C4 H4B . . 109.7 ?
    H4A C4 H4B . . 108.2 ?
    C6 C5 C4 . . 112.1(3) ?
    C6 C5 C10 . . 112.0(3) ?
    C4 C5 C10 . . 112.8(3) ?
    C6 C5 H5 . . 106.5 ?
    C4 C5 H5 . . 106.5 ?
    C10 C5 H5 . . 106.5 ?
    C7 C6 C5 . . 111.0(3) ?
    C7 C6 H6A . . 109.4 ?
    C5 C6 H6A . . 109.4 ?
    C7 C6 H6B . . 109.4 ?
    C5 C6 H6B . . 109.4 ?
    H6A C6 H6B . . 108.0 ?
    C6 C7 C8 . . 112.1(3) ?
    C6 C7 H7A . . 109.2 ?
    C8 C7 H7A . . 109.2 ?
    C6 C7 H7B . . 109.2 ?
    C8 C7 H7B . . 109.2 ?
    H7A C7 H7B . . 107.9 ?
    C14 C8 C7 . . 111.5(3) ?
    C14 C8 C9 . . 108.0(2) ?
    C7 C8 C9 . . 111.1(3) ?
    C14 C8 H8 . . 108.7 ?
    C7 C8 H8 . . 108.7 ?
    C9 C8 H8 . . 108.7 ?
    C11 C9 C8 . . 111.5(3) ?
    C11 C9 C10 . . 113.6(3) ?
    C8 C9 C10 . . 112.1(2) ?
    C11 C9 H9 . . 106.4 ?
    C8 C9 H9 . . 106.4 ?
    C10 C9 H9 . . 106.4 ?
    C1 C10 C19 . . 108.7(3) ?
    C1 C10 C5 . . 107.5(3) ?
    C19 C10 C5 . . 112.4(3) ?
    C1 C10 C9 . . 110.4(3) ?
    C19 C10 C9 . . 109.9(3) ?
    C5 C10 C9 . . 107.9(2) ?
    C9 C11 C12 . . 112.0(2) ?
    C9 C11 H11A . . 109.2 ?
    C12 C11 H11A . . 109.2 ?
    C9 C11 H11B . . 109.2 ?
    C12 C11 H11B . . 109.2 ?
    H11A C11 H11B . . 107.9 ?
    C13 C12 C11 . . 110.9(2) ?
    C13 C12 H12A . . 109.4 ?
    C11 C12 H12A . . 109.4 ?
    C13 C12 H12B . . 109.4 ?
    C11 C12 H12B . . 109.4 ?
    H12A C12 H12B . . 108.0 ?
    C12 C13 C18 . . 111.4(2) ?
    C12 C13 C14 . . 107.5(3) ?
    C18 C13 C14 . . 108.2(2) ?
    C12 C13 C17 . . 118.4(3) ?
    C18 C13 C17 . . 110.5(3) ?
    C14 C13 C17 . . 99.9(2) ?
    C8 C14 C15 . . 119.0(3) ?
    C8 C14 C13 . . 115.6(3) ?
    C15 C14 C13 . . 103.7(3) ?
    C8 C14 H14 . . 105.8 ?
    C15 C14 H14 . . 105.8 ?
    C13 C14 H14 . . 105.8 ?
    C14 C15 C16 . . 104.1(3) ?
    C14 C15 H15A . . 110.9 ?
    C16 C15 H15A . . 110.9 ?
    C14 C15 H15B . . 110.9 ?
    C16 C15 H15B . . 110.9 ?
    H15A C15 H15B . . 109.0 ?
    C17 C16 C15 . . 107.1(3) ?
    C17 C16 H16A . . 110.3 ?
    C15 C16 H16A . . 110.3 ?
    C17 C16 H16B . . 110.3 ?
    C15 C16 H16B . . 110.3 ?
    H16A C16 H16B . . 108.5 ?
    C20 C17 C16 . . 113.1(3) ?
    C20 C17 C13 . . 118.4(3) ?
    C16 C17 C13 . . 103.2(3) ?
    C20 C17 H17 . . 107.2 ?
    C16 C17 H17 . . 107.2 ?
    C13 C17 H17 . . 107.2 ?
    C13 C18 Cl1 . . 113.1(2) ?
    C13 C18 H18A . . 109.0 ?
    Cl1 C18 H18A . . 109.0 ?
    C13 C18 H18B . . 109.0 ?
    Cl1 C18 H18B . . 109.0 ?
    H18A C18 H18B . . 107.8 ?
    C10 C19 H19A . . 109.5 ?
    C10 C19 H19B . . 109.5 ?
    H19A C19 H19B . . 109.5 ?
    C10 C19 H19C . . 109.5 ?
    H19A C19 H19C . . 109.5 ?
    H19B C19 H19C . . 109.5 ?
    N1 C20 C17 . . 110.5(3) ?
    N1 C20 C21 . . 108.3(3) ?
    C17 C20 C21 . . 113.5(3) ?
    N1 C20 H20 . . 108.1 ?
    C17 C20 H20 . . 108.1 ?
    C21 C20 H20 . . 108.1 ?
    C20 C21 H21A . . 109.5 ?
    C20 C21 H21B . . 109.5 ?
    H21A C21 H21B . . 109.5 ?
    C20 C21 H21C . . 109.5 ?
    H21A C21 H21C . . 109.5 ?
    H21B C21 H21C . . 109.5 ?
    O1 C22 N1 . . 123.0(3) ?
    O1 C22 C23 . . 121.0(3) ?
    N1 C22 C23 . . 115.9(3) ?
    C22 C23 H23A . . 109.5 ?
    C22 C23 H23B . . 109.5 ?
    H23A C23 H23B . . 109.5 ?
    C22 C23 H23C . . 109.5 ?
    H23A C23 H23C . . 109.5 ?
    H23B C23 H23C . . 109.5 ?
    O3 C24 O2 . . 123.7(4) ?
    O3 C24 C25 . . 126.1(4) ?
    O2 C24 C25 . . 110.2(4) ?
    C24 C25 H25A . . 109.5 ?
    C24 C25 H25B . . 109.5 ?
    H25A C25 H25B . . 109.5 ?
    C24 C25 H25C . . 109.5 ?
    H25A C25 H25C . . 109.5 ?
    H25B C25 H25C . . 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
    C10 C1 C2 C3 . . . . -56.6(4) ?
    C24 O2 C3 C4 . . . . -87.3(4) ?
    C24 O2 C3 C2 . . . . 150.8(4) ?
    C1 C2 C3 O2 . . . . 176.6(3) ?
    C1 C2 C3 C4 . . . . 55.9(4) ?
    O2 C3 C4 C5 . . . . -174.9(3) ?
    C2 C3 C4 C5 . . . . -56.5(4) ?
    C3 C4 C5 C6 . . . . -175.1(3) ?
    C3 C4 C5 C10 . . . . 57.4(4) ?
    C4 C5 C6 C7 . . . . 173.7(3) ?
    C10 C5 C6 C7 . . . . -58.5(4) ?
    C5 C6 C7 C8 . . . . 55.8(4) ?
    C6 C7 C8 C14 . . . . -174.6(3) ?
    C6 C7 C8 C9 . . . . -54.0(4) ?
    C14 C8 C9 C11 . . . . -54.2(3) ?
    C7 C8 C9 C11 . . . . -176.8(3) ?
    C14 C8 C9 C10 . . . . 177.2(2) ?
    C7 C8 C9 C10 . . . . 54.6(3) ?
    C2 C1 C10 C19 . . . . -66.1(4) ?
    C2 C1 C10 C5 . . . . 55.9(4) ?
    C2 C1 C10 C9 . . . . 173.3(3) ?
    C6 C5 C10 C1 . . . . 176.3(3) ?
    C4 C5 C10 C1 . . . . -56.1(3) ?
    C6 C5 C10 C19 . . . . -64.0(4) ?
    C4 C5 C10 C19 . . . . 63.5(4) ?
    C6 C5 C10 C9 . . . . 57.3(3) ?
    C4 C5 C10 C9 . . . . -175.2(3) ?
    C11 C9 C10 C1 . . . . 59.9(3) ?
    C8 C9 C10 C1 . . . . -172.7(3) ?
    C11 C9 C10 C19 . . . . -60.1(3) ?
    C8 C9 C10 C19 . . . . 67.4(3) ?
    C11 C9 C10 C5 . . . . 177.0(3) ?
    C8 C9 C10 C5 . . . . -55.5(3) ?
    C8 C9 C11 C12 . . . . 57.1(3) ?
    C10 C9 C11 C12 . . . . -175.1(2) ?
    C9 C11 C12 C13 . . . . -58.1(3) ?
    C11 C12 C13 C18 . . . . -63.2(3) ?
    C11 C12 C13 C14 . . . . 55.1(3) ?
    C11 C12 C13 C17 . . . . 167.1(3) ?
    C7 C8 C14 C15 . . . . -57.0(4) ?
    C9 C8 C14 C15 . . . . -179.4(3) ?
    C7 C8 C14 C13 . . . . 178.5(3) ?
    C9 C8 C14 C13 . . . . 56.2(3) ?
    C12 C13 C14 C8 . . . . -57.2(3) ?
    C18 C13 C14 C8 . . . . 63.2(3) ?
    C17 C13 C14 C8 . . . . 178.7(3) ?
    C12 C13 C14 C15 . . . . 170.8(3) ?
    C18 C13 C14 C15 . . . . -68.9(3) ?
    C17 C13 C14 C15 . . . . 46.6(3) ?
    C8 C14 C15 C16 . . . . -163.5(3) ?
    C13 C14 C15 C16 . . . . -33.4(3) ?
    C14 C15 C16 C17 . . . . 7.1(4) ?
    C15 C16 C17 C20 . . . . 150.9(3) ?
    C15 C16 C17 C13 . . . . 21.7(4) ?
    C12 C13 C17 C20 . . . . 76.9(4) ?
    C18 C13 C17 C20 . . . . -53.2(4) ?
    C14 C13 C17 C20 . . . . -167.0(3) ?
    C12 C13 C17 C16 . . . . -157.3(3) ?
    C18 C13 C17 C16 . . . . 72.6(3) ?
    C14 C13 C17 C16 . . . . -41.2(3) ?
    C12 C13 C18 Cl1 . . . . -46.1(3) ?
    C14 C13 C18 Cl1 . . . . -164.0(2) ?
    C17 C13 C18 Cl1 . . . . 87.6(3) ?
    C22 N1 C20 C17 . . . . -104.7(4) ?
    C22 N1 C20 C21 . . . . 130.3(3) ?
    C16 C17 C20 N1 . . . . 43.4(4) ?
    C13 C17 C20 N1 . . . . 164.2(3) ?
    C16 C17 C20 C21 . . . . 165.3(3) ?
    C13 C17 C20 C21 . . . . -73.9(4) ?
    C20 N1 C22 O1 . . . . 2.3(6) ?
    C20 N1 C22 C23 . . . . -177.5(3) ?
    C3 O2 C24 O3 . . . . 2.7(7) ?
    C3 O2 C24 C25 . . . . -179.1(4) ?
loop_
    _geom_hbond_atom_site_label_D
    _geom_hbond_atom_site_label_H
    _geom_hbond_atom_site_label_A
    _geom_hbond_site_symmetry_A
    _geom_hbond_distance_DH
    _geom_hbond_distance_HA
    _geom_hbond_distance_DA
    _geom_hbond_angle_DHA
    _geom_hbond_publ_flag
    N1 H1 O1 2_746 0.88 2.03 2.893(4) 165.3 y
    C23 H23C O3 1_656 0.98 2.54 3.487(6) 162.8 y
    C12 H12B Cl1 . 0.99 2.62 3.076(3) 108.0 y
    C20 H20 Cl1 . 1.00 2.67 3.349(3) 125.1 y
    C20 H20 O1 . 1.00 2.42 2.812(4) 102.8 y
