##############################################################################
###                                                                        ###
###           Full Paper (Acta Crystallographica Section C)                ###
###                                                                        ###
##############################################################################
#                                                                            #
# This CIF contains the data in a paper accepted for publication in Acta     #
# Crystallographica Section C. It conforms to the editorial and technical    #
# requirements of Notes for Authors for Section C, and has been peer         #
# reviewed under the auspices of the IUCr Commission on Journals.            #
#                                                                            #
# Full details of the Crystallographic Information File format               #
# are given in the paper "The Crystallographic Information File (CIF):       #
# a New Standard Archive File for Crystallography" by S. R. Hall, F. H.      #
# Allen and I. D. Brown [Acta Cryst. (1991), A47, 655-685].                  #
#                                                                            #
# The current version of the core CIF dictionary is obtainable from          #
# ftp://ftp.iucr.org/pub/cif_core.dic. The current version number is 2.1.    #
#                                                                            #
# Software is freely available for graphical display of the structure(s) in  #
# this CIF.  For information consult the CIF home page http://www.iucr.org/  #
# cif/home.html                                                              #
#                                                                            #
#            Copyright International Union of Crystallography                #
#                                                                            #
##############################################################################
data_I
_audit_creation_method     SHELXL97
_chemical_name_systematic
;
3β-(1-Allyl-1-pyrrolidinio)-16-(2-pyridylmethylene)androst-5-ene-17β-ol
bromide hemihydrate
;
_chemical_name_common     ?
_chemical_formula_moiety     'C32 H45 Br N2 O , 0.5H2 O'
_chemical_formula_sum     'C32 H46 Br N2 O1.5'
_chemical_formula_iupac     'C32 H45 Br N2 O , 0.5H2 O'
_chemical_formula_weight     562.61
_symmetry_cell_setting     monoclinic
_symmetry_space_group_name_H-M     C2
_symmetry_space_group_name_Hall     'C 2y'
loop_
    _symmetry_equiv_pos_as_xyz
    'x, y, z'
    '-x, y, -z'
    'x+1/2, y+1/2, z'
    '-x+1/2, y+1/2, -z'
_cell_length_a     21.054(4)
_cell_length_b     9.3083(18)
_cell_length_c     15.551(4)
_cell_angle_alpha     90
_cell_angle_beta     106.15(2)
_cell_angle_gamma     90
_cell_volume     2927.4(11)
_cell_formula_units_Z     4
_cell_measurement_reflns_used     25
_cell_measurement_theta_min     10
_cell_measurement_theta_max     15
_cell_measurement_temperature     293(2)
_exptl_crystal_description     plate
_exptl_crystal_colour     white
_exptl_crystal_size_max     0.20
_exptl_crystal_size_mid     0.17
_exptl_crystal_size_min     0.17
_exptl_crystal_density_diffrn     1.277
_exptl_crystal_density_meas     'not measured'
_exptl_crystal_density_method     'not measured'
_exptl_crystal_F_000     1196
_exptl_absorpt_coefficient_mu     1.433
_exptl_absorpt_correction_type     '\y scan'
_exptl_absorpt_process_details     '(North et al., 1968)'
_exptl_absorpt_correction_T_min     0.763
_exptl_absorpt_correction_T_max     0.793
_exptl_special_details
;
 ?
;
_diffrn_ambient_temperature     293(2)
_diffrn_radiation_type     'Mo K\a'
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_source     'fine-focus sealed tube'
_diffrn_radiation_monochromator     'graphite'
_diffrn_measurement_device_type     'Enraf-Nonius CAD-4'
_diffrn_measurement_method     ω/2θ
_diffrn_detector_area_resol_mean     ?
_diffrn_reflns_number     2835
_diffrn_reflns_av_R_equivalents     0.013
_diffrn_reflns_av_sigmaI/netI     0.031
_diffrn_reflns_theta_min     2.01
_diffrn_reflns_theta_max     25.00
_diffrn_reflns_theta_full     25.00
_diffrn_reflns_limit_h_min     0
_diffrn_reflns_limit_h_max     24
_diffrn_reflns_limit_k_min     0
_diffrn_reflns_limit_k_max     11
_diffrn_reflns_limit_l_min     -18
_diffrn_reflns_limit_l_max     17
_diffrn_standards_number     2
_diffrn_standards_interval_count     ?
_diffrn_standards_interval_time     120
_diffrn_standards_decay_%     0
_refine_special_details
;
 Refinement of F² against ALL reflections.  The weighted R-factor wR and
 goodness of fit S are based on F², conventional R-factors R are based
 on F, with F set to zero for negative F². The threshold expression of
 F² > 2sigma(F²) is used only for calculating R-factors(gt) etc. and is
 not relevant to the choice of reflections for refinement.  R-factors based
 on F² are statistically about twice as large as those based on F, and R-
 factors based on ALL data will be even larger.
;
_reflns_number_total     2751
_reflns_number_gt     2100
_reflns_threshold_expression     I>2σ(I)
_refine_ls_structure_factor_coef     Fsqd
_refine_ls_matrix_type     full
_refine_ls_R_factor_all     0.062
_refine_ls_R_factor_gt     0.034
_refine_ls_wR_factor_gt     0.072
_refine_ls_wR_factor_ref     0.089
_refine_ls_goodness_of_fit_ref     1.075
_refine_ls_restrained_S_all     1.075
_refine_ls_number_reflns     2751
_refine_ls_number_parameters     336
_refine_ls_number_restraints     4
_refine_ls_hydrogen_treatment     mixed
_refine_ls_weighting_scheme     calc
_refine_ls_weighting_details
           ' w = 1/[σ²(Fo²)+(0.0413P)²+2.1207P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_hydrogens     geom
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary     difmap
_refine_ls_shift/su_max     <0.001
_refine_ls_shift/su_mean     0.000
_refine_diff_density_max     0.29
_refine_diff_density_min     -0.23
_refine_ls_extinction_method     none
_refine_ls_extinction_coef     ?
_refine_ls_abs_structure_details     'Flack (1983) How many Friedels?'
_refine_ls_abs_structure_Flack     -0.002(12)
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'
    'Br' 'Br' -0.3740 2.4560
                         'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
_computing_data_collection     'CAD-4 EXPRESS (Enraf-Nonius, 1994)'
_computing_cell_refinement     'CAD-4 EXPRESS'
_computing_data_reduction     'MolEN (Fair, 1990)'
_computing_structure_solution     'DIRDIF99 (Beurskens et al., 1999)'
_computing_structure_refinement     'SHELXL97 (Sheldrick, 1997)'
_computing_molecular_graphics     'ZORTEP (Zsolnai, 1997)'
_computing_publication_material     'SHELXL97'
loop_
    _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
    _atom_site_type_symbol
    C1 0.0921(2) 0.2900(6) 0.6058(3) 0.0429(11) Uani d . 1 . . C
    H1A 0.0506 0.2931 0.5590 0.051 Uiso calc R 1 . . H
    H1B 0.1090 0.1926 0.6084 0.051 Uiso calc R 1 . . H
    C2 0.0791(2) 0.3259(6) 0.6955(3) 0.0473(12) Uani d . 1 . . C
    H2A 0.0616 0.4227 0.6939 0.057 Uiso calc R 1 . . H
    H2B 0.0468 0.2598 0.7070 0.057 Uiso calc R 1 . . H
    C3 0.1437(2) 0.3138(5) 0.7689(3) 0.0396(11) Uani d . 1 . . C
    H3 0.1620 0.2182 0.7643 0.048 Uiso calc R 1 . . H
    C4 0.1926(2) 0.4242(5) 0.7512(3) 0.0428(11) Uani d . 1 . . C
    H4A 0.1755 0.5202 0.7542 0.051 Uiso calc R 1 . . H
    H4B 0.2344 0.4160 0.7971 0.051 Uiso calc R 1 . . H
    C5 0.2036(2) 0.4006(5) 0.6603(3) 0.0364(10) Uani d . 1 . . C
    C6 0.2648(2) 0.3911(5) 0.6524(3) 0.0402(11) Uani d . 1 . . C
    H6 0.2996 0.3947 0.7045 0.048 Uiso calc R 1 . . H
    C7 0.2816(2) 0.3752(6) 0.5656(3) 0.0430(12) Uani d . 1 . . C
    H7A 0.2990 0.2794 0.5625 0.052 Uiso calc R 1 . . H
    H7B 0.3161 0.4433 0.5641 0.052 Uiso calc R 1 . . H
    C8 0.22291(19) 0.3993(5) 0.4840(3) 0.0351(10) Uani d . 1 . . C
    H8 0.2149 0.5027 0.4755 0.042 Uiso calc R 1 . . H
    C9 0.16032(19) 0.3267(5) 0.4986(2) 0.0371(10) Uani d . 1 . . C
    H9 0.1725 0.2265 0.5143 0.045 Uiso calc R 1 . . H
    C10 0.1417(2) 0.3925(5) 0.5803(3) 0.0374(11) Uani d . 1 . . C
    C11 0.1027(2) 0.3219(7) 0.4127(3) 0.0494(12) Uani d . 1 . . C
    H11A 0.0682 0.2607 0.4227 0.059 Uiso calc R 1 . . H
    H11B 0.0846 0.4179 0.4000 0.059 Uiso calc R 1 . . H
    C12 0.1221(2) 0.2667(6) 0.3309(3) 0.0474(12) Uani d . 1 . . C
    H12A 0.1343 0.1661 0.3395 0.057 Uiso calc R 1 . . H
    H12B 0.0844 0.2741 0.2784 0.057 Uiso calc R 1 . . H
    C13 0.1795(2) 0.3512(5) 0.3154(3) 0.0382(10) Uani d . 1 . . C
    C14 0.23666(19) 0.3374(5) 0.4013(3) 0.0356(10) Uani d . 1 . . C
    H14 0.2432 0.2341 0.4124 0.043 Uiso calc R 1 . . H
    C15 0.2974(2) 0.3899(6) 0.3737(3) 0.0439(11) Uani d . 1 . . C
    H15A 0.3012 0.4937 0.3778 0.053 Uiso calc R 1 . . H
    H15B 0.3377 0.3471 0.4110 0.053 Uiso calc R 1 . . H
    C16 0.2833(2) 0.3397(5) 0.2775(3) 0.0442(11) Uani d . 1 . . C
    C17 0.2121(2) 0.2845(5) 0.2485(3) 0.0449(11) Uani d . 1 . . C
    H17 0.2135 0.1803 0.2578 0.054 Uiso calc R 1 . . H
    C18 0.1600(2) 0.5075(8) 0.2884(3) 0.0514(11) Uani d . 1 . . C
    H18A 0.1975 0.5576 0.2793 0.077 Uiso calc R 1 . . H
    H18B 0.1459 0.5538 0.3350 0.077 Uiso calc R 1 . . H
    H18C 0.1246 0.5086 0.2339 0.077 Uiso calc R 1 . . H
    C19 0.1117(2) 0.5415(6) 0.5600(3) 0.0529(15) Uani d . 1 . . C
    H19A 0.0728 0.5362 0.5101 0.079 Uiso calc R 1 . . H
    H19B 0.1432 0.6048 0.5456 0.079 Uiso calc R 1 . . H
    H19C 0.1001 0.5776 0.6114 0.079 Uiso calc R 1 . . H
    C20 0.3233(2) 0.3344(6) 0.2254(3) 0.0478(12) Uani d . 1 . . C
    H20 0.3038 0.3063 0.1666 0.057 Uiso calc R 1 . . H
    C21 0.3940(3) 0.3666(5) 0.2477(3) 0.0523(13) Uani d . 1 . . C
    C22 0.4291(3) 0.3459(7) 0.1857(4) 0.0692(16) Uani d . 1 . . C
    H22 0.4070 0.3171 0.1279 0.083 Uiso calc R 1 . . H
    C23 0.4967(3) 0.3676(8) 0.2089(6) 0.091(2) Uani d . 1 . . C
    H23 0.5207 0.3524 0.1677 0.109 Uiso calc R 1 . . H
    C24 0.5270(3) 0.4116(9) 0.2930(6) 0.095(2) Uani d . 1 . . C
    H24 0.5725 0.4262 0.3111 0.114 Uiso calc R 1 . . H
    C25 0.4900(3) 0.4344(9) 0.3514(5) 0.095(2) Uani d . 1 . . C
    H25 0.5116 0.4650 0.4090 0.114 Uiso calc R 1 . . H
    N26 0.4249(2) 0.4155(6) 0.3305(3) 0.0713(14) Uani d . 1 . . N
    O27 0.17983(18) 0.3102(4) 0.1567(2) 0.0548(9) Uani d D 1 . . O
    H27 0.167(3) 0.231(3) 0.138(3) 0.060 Uiso d D 1 . . H
    N28 0.13579(18) 0.3287(5) 0.8641(2) 0.0409(9) Uani d . 1 . . N
    C29 0.0840(3) 0.2230(7) 0.8782(3) 0.0566(14) Uani d . 1 . . C
    H29A 0.0678 0.1623 0.8260 0.068 Uiso calc R 1 . . H
    H29B 0.1025 0.1625 0.9299 0.068 Uiso calc R 1 . . H
    C30 0.0292(3) 0.3158(9) 0.8929(4) 0.082(2) Uani d . 1 . . C
    H30A -0.0030 0.3379 0.8365 0.098 Uiso calc R 1 . . H
    H30B 0.0070 0.2683 0.9320 0.098 Uiso calc R 1 . . H
    C31 0.0632(3) 0.4480(8) 0.9354(4) 0.084(2) Uani d . 1 . . C
    H31A 0.0858 0.4320 0.9981 0.101 Uiso calc R 1 . . H
    H31B 0.0322 0.5268 0.9304 0.101 Uiso calc R 1 . . H
    C32 0.1118(2) 0.4776(7) 0.8822(3) 0.0526(14) Uani d . 1 . . C
    H32A 0.1483 0.5360 0.9164 0.063 Uiso calc R 1 . . H
    H32B 0.0905 0.5266 0.8266 0.063 Uiso calc R 1 . . H
    C33 0.2020(2) 0.3001(6) 0.9335(3) 0.0471(12) Uani d . 1 . . C
    H33A 0.2333 0.3736 0.9281 0.057 Uiso calc R 1 . . H
    H33B 0.1960 0.3073 0.9929 0.057 Uiso calc R 1 . . H
    C34 0.2299(3) 0.1567(6) 0.9232(3) 0.0553(13) Uani d . 1 . . C
    H34 0.2053 0.0755 0.9278 0.066 Uiso calc R 1 . . H
    C35 0.2872(3) 0.1390(7) 0.9080(3) 0.0629(15) Uani d . 1 . . C
    H35A 0.3127 0.2185 0.9031 0.076 Uiso calc R 1 . . H
    H35B 0.3025 0.0469 0.9020 0.076 Uiso calc R 1 . . H
    Br 0.12664(3) -0.00156(7) 0.08584(3) 0.0677(2) Uani d . 1 . . Br
    O1W 0.5000 0.2660(8) 0.0000 0.104(2) Uani d SD 1 . . O
    H1W 0.5354(9) 0.319(4) 0.021(5) 0.115 Uiso d D 1 . . H
_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
    C1 C2 . 1.532(6) ?
    C1 C10 . 1.544(6) ?
    C1 H1A . 0.9700 ?
    C1 H1B . 0.9700 ?
    C2 C3 . 1.518(6) ?
    C2 H2A . 0.9700 ?
    C2 H2B . 0.9700 ?
    C3 C4 . 1.531(6) ?
    C3 N28 . 1.543(5) ?
    C3 H3 . 0.9800 ?
    C4 C5 . 1.511(6) ?
    C4 H4A . 0.9700 ?
    C4 H4B . 0.9700 ?
    C5 C6 . 1.331(6) ?
    C5 C10 . 1.533(6) ?
    C6 C7 . 1.494(6) ?
    C6 H6 . 0.9300 ?
    C7 C8 . 1.522(6) ?
    C7 H7A . 0.9700 ?
    C7 H7B . 0.9700 ?
    C8 C14 . 1.510(6) ?
    C8 C9 . 1.553(6) ?
    C8 H8 . 0.9800 ?
    C9 C11 . 1.535(5) ?
    C9 C10 . 1.557(6) ?
    C9 H9 . 0.9800 ?
    C10 C19 . 1.520(7) ?
    C11 C12 . 1.528(6) ?
    C11 H11A . 0.9700 ?
    C11 H11B . 0.9700 ?
    C12 C13 . 1.516(6) ?
    C12 H12A . 0.9700 ?
    C12 H12B . 0.9700 ?
    C13 C17 . 1.530(6) ?
    C13 C14 . 1.534(5) ?
    C13 C18 . 1.537(9) ?
    C14 C15 . 1.537(6) ?
    C14 H14 . 0.9800 ?
    C15 C16 . 1.516(6) ?
    C15 H15A . 0.9700 ?
    C15 H15B . 0.9700 ?
    C16 C20 . 1.321(6) ?
    C16 C17 . 1.529(6) ?
    C17 O27 . 1.420(5) ?
    C17 H17 . 0.9800 ?
    C18 H18A . 0.9600 ?
    C18 H18B . 0.9600 ?
    C18 H18C . 0.9600 ?
    C19 H19A . 0.9600 ?
    C19 H19B . 0.9600 ?
    C19 H19C . 0.9600 ?
    C20 C21 . 1.463(7) ?
    C20 H20 . 0.9300 ?
    C21 N26 . 1.351(7) ?
    C21 C22 . 1.381(7) ?
    C22 C23 . 1.384(8) ?
    C22 H22 . 0.9300 ?
    C23 C24 . 1.349(10) ?
    C23 H23 . 0.9300 ?
    C24 C25 . 1.367(9) ?
    C24 H24 . 0.9300 ?
    C25 N26 . 1.329(7) ?
    C25 H25 . 0.9300 ?
    O27 H27 . 0.81(2) ?
    N28 C32 . 1.528(7) ?
    N28 C29 . 1.529(7) ?
    N28 C33 . 1.530(6) ?
    C29 C30 . 1.510(8) ?
    C29 H29A . 0.9700 ?
    C29 H29B . 0.9700 ?
    C30 C31 . 1.483(10) ?
    C30 H30A . 0.9700 ?
    C30 H30B . 0.9700 ?
    C31 C32 . 1.510(8) ?
    C31 H31A . 0.9700 ?
    C31 H31B . 0.9700 ?
    C32 H32A . 0.9700 ?
    C32 H32B . 0.9700 ?
    C33 C34 . 1.486(8) ?
    C33 H33A . 0.9700 ?
    C33 H33B . 0.9700 ?
    C34 C35 . 1.301(7) ?
    C34 H34 . 0.9300 ?
    C35 H35A . 0.9300 ?
    C35 H35B . 0.9300 ?
    O1W H1W . 0.88(2) ?
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
    C2 C1 C10 . . 113.8(4) ?
    C2 C1 H1A . . 108.8 ?
    C10 C1 H1A . . 108.8 ?
    C2 C1 H1B . . 108.8 ?
    C10 C1 H1B . . 108.8 ?
    H1A C1 H1B . . 107.7 ?
    C3 C2 C1 . . 108.5(4) ?
    C3 C2 H2A . . 110.0 ?
    C1 C2 H2A . . 110.0 ?
    C3 C2 H2B . . 110.0 ?
    C1 C2 H2B . . 110.0 ?
    H2A C2 H2B . . 108.4 ?
    C2 C3 C4 . . 108.8(4) ?
    C2 C3 N28 . . 113.6(3) ?
    C4 C3 N28 . . 111.7(4) ?
    C2 C3 H3 . . 107.5 ?
    C4 C3 H3 . . 107.5 ?
    N28 C3 H3 . . 107.5 ?
    C5 C4 C3 . . 110.8(4) ?
    C5 C4 H4A . . 109.5 ?
    C3 C4 H4A . . 109.5 ?
    C5 C4 H4B . . 109.5 ?
    C3 C4 H4B . . 109.5 ?
    H4A C4 H4B . . 108.1 ?
    C6 C5 C4 . . 120.1(4) ?
    C6 C5 C10 . . 123.3(4) ?
    C4 C5 C10 . . 116.7(4) ?
    C5 C6 C7 . . 124.7(4) ?
    C5 C6 H6 . . 117.7 ?
    C7 C6 H6 . . 117.7 ?
    C6 C7 C8 . . 113.4(3) ?
    C6 C7 H7A . . 108.9 ?
    C8 C7 H7A . . 108.9 ?
    C6 C7 H7B . . 108.9 ?
    C8 C7 H7B . . 108.9 ?
    H7A C7 H7B . . 107.7 ?
    C14 C8 C7 . . 110.5(3) ?
    C14 C8 C9 . . 109.3(3) ?
    C7 C8 C9 . . 109.8(3) ?
    C14 C8 H8 . . 109.1 ?
    C7 C8 H8 . . 109.1 ?
    C9 C8 H8 . . 109.1 ?
    C11 C9 C8 . . 112.5(3) ?
    C11 C9 C10 . . 113.9(3) ?
    C8 C9 C10 . . 111.4(4) ?
    C11 C9 H9 . . 106.1 ?
    C8 C9 H9 . . 106.1 ?
    C10 C9 H9 . . 106.1 ?
    C19 C10 C5 . . 109.6(4) ?
    C19 C10 C1 . . 110.2(4) ?
    C5 C10 C1 . . 107.8(3) ?
    C19 C10 C9 . . 111.9(4) ?
    C5 C10 C9 . . 109.3(3) ?
    C1 C10 C9 . . 107.9(4) ?
    C12 C11 C9 . . 113.9(4) ?
    C12 C11 H11A . . 108.8 ?
    C9 C11 H11A . . 108.8 ?
    C12 C11 H11B . . 108.8 ?
    C9 C11 H11B . . 108.8 ?
    H11A C11 H11B . . 107.7 ?
    C13 C12 C11 . . 111.5(4) ?
    C13 C12 H12A . . 109.3 ?
    C11 C12 H12A . . 109.3 ?
    C13 C12 H12B . . 109.3 ?
    C11 C12 H12B . . 109.3 ?
    H12A C12 H12B . . 108.0 ?
    C12 C13 C17 . . 115.2(4) ?
    C12 C13 C14 . . 106.6(3) ?
    C17 C13 C14 . . 99.5(3) ?
    C12 C13 C18 . . 111.8(4) ?
    C17 C13 C18 . . 109.5(4) ?
    C14 C13 C18 . . 113.7(4) ?
    C8 C14 C13 . . 114.8(3) ?
    C8 C14 C15 . . 119.2(4) ?
    C13 C14 C15 . . 104.1(3) ?
    C8 C14 H14 . . 105.9 ?
    C13 C14 H14 . . 105.9 ?
    C15 C14 H14 . . 105.9 ?
    C16 C15 C14 . . 103.1(3) ?
    C16 C15 H15A . . 111.1 ?
    C14 C15 H15A . . 111.1 ?
    C16 C15 H15B . . 111.1 ?
    C14 C15 H15B . . 111.1 ?
    H15A C15 H15B . . 109.1 ?
    C20 C16 C15 . . 129.3(4) ?
    C20 C16 C17 . . 123.1(4) ?
    C15 C16 C17 . . 107.6(4) ?
    O27 C17 C16 . . 113.3(4) ?
    O27 C17 C13 . . 115.8(4) ?
    C16 C17 C13 . . 104.6(4) ?
    O27 C17 H17 . . 107.6 ?
    C16 C17 H17 . . 107.6 ?
    C13 C17 H17 . . 107.6 ?
    C13 C18 H18A . . 109.5 ?
    C13 C18 H18B . . 109.5 ?
    H18A C18 H18B . . 109.5 ?
    C13 C18 H18C . . 109.5 ?
    H18A C18 H18C . . 109.5 ?
    H18B C18 H18C . . 109.5 ?
    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 ?
    C16 C20 C21 . . 128.8(5) ?
    C16 C20 H20 . . 115.6 ?
    C21 C20 H20 . . 115.6 ?
    N26 C21 C22 . . 120.2(5) ?
    N26 C21 C20 . . 118.9(4) ?
    C22 C21 C20 . . 120.8(5) ?
    C21 C22 C23 . . 120.6(6) ?
    C21 C22 H22 . . 119.7 ?
    C23 C22 H22 . . 119.7 ?
    C24 C23 C22 . . 118.0(6) ?
    C24 C23 H23 . . 121.0 ?
    C22 C23 H23 . . 121.0 ?
    C23 C24 C25 . . 119.3(6) ?
    C23 C24 H24 . . 120.4 ?
    C25 C24 H24 . . 120.4 ?
    N26 C25 C24 . . 123.8(7) ?
    N26 C25 H25 . . 118.1 ?
    C24 C25 H25 . . 118.1 ?
    C25 N26 C21 . . 117.9(5) ?
    C17 O27 H27 . . 104(4) ?
    C32 N28 C29 . . 105.8(4) ?
    C32 N28 C33 . . 108.1(4) ?
    C29 N28 C33 . . 109.5(4) ?
    C32 N28 C3 . . 112.8(4) ?
    C29 N28 C3 . . 110.6(4) ?
    C33 N28 C3 . . 109.9(3) ?
    C30 C29 N28 . . 105.0(5) ?
    C30 C29 H29A . . 110.7 ?
    N28 C29 H29A . . 110.7 ?
    C30 C29 H29B . . 110.7 ?
    N28 C29 H29B . . 110.7 ?
    H29A C29 H29B . . 108.8 ?
    C31 C30 C29 . . 104.4(5) ?
    C31 C30 H30A . . 110.9 ?
    C29 C30 H30A . . 110.9 ?
    C31 C30 H30B . . 110.9 ?
    C29 C30 H30B . . 110.9 ?
    H30A C30 H30B . . 108.9 ?
    C30 C31 C32 . . 103.0(5) ?
    C30 C31 H31A . . 111.2 ?
    C32 C31 H31A . . 111.2 ?
    C30 C31 H31B . . 111.2 ?
    C32 C31 H31B . . 111.2 ?
    H31A C31 H31B . . 109.1 ?
    C31 C32 N28 . . 104.2(5) ?
    C31 C32 H32A . . 110.9 ?
    N28 C32 H32A . . 110.9 ?
    C31 C32 H32B . . 110.9 ?
    N28 C32 H32B . . 110.9 ?
    H32A C32 H32B . . 108.9 ?
    C34 C33 N28 . . 113.0(4) ?
    C34 C33 H33A . . 109.0 ?
    N28 C33 H33A . . 109.0 ?
    C34 C33 H33B . . 109.0 ?
    N28 C33 H33B . . 109.0 ?
    H33A C33 H33B . . 107.8 ?
    C35 C34 C33 . . 123.2(5) ?
    C35 C34 H34 . . 118.4 ?
    C33 C34 H34 . . 118.4 ?
    C34 C35 H35A . . 120.0 ?
    C34 C35 H35B . . 120.0 ?
    H35A C35 H35B . . 120.0 ?
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 . . . . -61.2(6) ?
    C1 C2 C3 C4 . . . . 62.2(5) ?
    C1 C2 C3 N28 . . . . -172.7(4) ?
    C2 C3 C4 C5 . . . . -58.0(5) ?
    N28 C3 C4 C5 . . . . 175.7(4) ?
    C3 C4 C5 C6 . . . . -129.1(5) ?
    C3 C4 C5 C10 . . . . 52.4(6) ?
    C4 C5 C6 C7 . . . . -176.9(5) ?
    C10 C5 C6 C7 . . . . 1.6(8) ?
    C5 C6 C7 C8 . . . . 11.1(7) ?
    C6 C7 C8 C14 . . . . -162.1(4) ?
    C6 C7 C8 C9 . . . . -41.5(6) ?
    C14 C8 C9 C11 . . . . -47.7(5) ?
    C7 C8 C9 C11 . . . . -169.1(4) ?
    C14 C8 C9 C10 . . . . -177.0(4) ?
    C7 C8 C9 C10 . . . . 61.6(5) ?
    C6 C5 C10 C19 . . . . -105.8(5) ?
    C4 C5 C10 C19 . . . . 72.7(5) ?
    C6 C5 C10 C1 . . . . 134.2(5) ?
    C4 C5 C10 C1 . . . . -47.3(6) ?
    C6 C5 C10 C9 . . . . 17.2(6) ?
    C4 C5 C10 C9 . . . . -164.3(4) ?
    C2 C1 C10 C19 . . . . -68.2(5) ?
    C2 C1 C10 C5 . . . . 51.3(5) ?
    C2 C1 C10 C9 . . . . 169.3(4) ?
    C11 C9 C10 C19 . . . . -54.8(5) ?
    C8 C9 C10 C19 . . . . 73.6(4) ?
    C11 C9 C10 C5 . . . . -176.4(4) ?
    C8 C9 C10 C5 . . . . -48.0(5) ?
    C11 C9 C10 C1 . . . . 66.6(5) ?
    C8 C9 C10 C1 . . . . -164.9(4) ?
    C8 C9 C11 C12 . . . . 48.2(6) ?
    C10 C9 C11 C12 . . . . 176.1(4) ?
    C9 C11 C12 C13 . . . . -54.3(6) ?
    C11 C12 C13 C17 . . . . 167.3(4) ?
    C11 C12 C13 C14 . . . . 57.9(5) ?
    C11 C12 C13 C18 . . . . -66.9(5) ?
    C7 C8 C14 C13 . . . . 177.9(4) ?
    C9 C8 C14 C13 . . . . 57.0(5) ?
    C7 C8 C14 C15 . . . . -57.7(5) ?
    C9 C8 C14 C15 . . . . -178.6(4) ?
    C12 C13 C14 C8 . . . . -62.1(5) ?
    C17 C13 C14 C8 . . . . 177.8(4) ?
    C18 C13 C14 C8 . . . . 61.5(5) ?
    C12 C13 C14 C15 . . . . 165.9(4) ?
    C17 C13 C14 C15 . . . . 45.8(4) ?
    C18 C13 C14 C15 . . . . -70.5(5) ?
    C8 C14 C15 C16 . . . . -163.9(4) ?
    C13 C14 C15 C16 . . . . -34.5(5) ?
    C14 C15 C16 C20 . . . . -167.6(5) ?
    C14 C15 C16 C17 . . . . 9.3(5) ?
    C20 C16 C17 O27 . . . . -36.6(7) ?
    C15 C16 C17 O27 . . . . 146.3(4) ?
    C20 C16 C17 C13 . . . . -163.7(5) ?
    C15 C16 C17 C13 . . . . 19.2(5) ?
    C12 C13 C17 O27 . . . . 81.6(5) ?
    C14 C13 C17 O27 . . . . -164.9(4) ?
    C18 C13 C17 O27 . . . . -45.4(5) ?
    C12 C13 C17 C16 . . . . -152.9(4) ?
    C14 C13 C17 C16 . . . . -39.3(4) ?
    C18 C13 C17 C16 . . . . 80.1(4) ?
    C15 C16 C20 C21 . . . . 4.5(10) ?
    C17 C16 C20 C21 . . . . -171.9(5) ?
    C16 C20 C21 N26 . . . . -3.6(9) ?
    C16 C20 C21 C22 . . . . 175.7(6) ?
    N26 C21 C22 C23 . . . . 3.5(9) ?
    C20 C21 C22 C23 . . . . -175.8(6) ?
    C21 C22 C23 C24 . . . . -1.0(11) ?
    C22 C23 C24 C25 . . . . -0.8(12) ?
    C23 C24 C25 N26 . . . . 0.2(13) ?
    C24 C25 N26 C21 . . . . 2.2(11) ?
    C22 C21 N26 C25 . . . . -3.9(9) ?
    C20 C21 N26 C25 . . . . 175.3(6) ?
    C2 C3 N28 C32 . . . . -64.9(5) ?
    C4 C3 N28 C32 . . . . 58.6(5) ?
    C2 C3 N28 C29 . . . . 53.4(6) ?
    C4 C3 N28 C29 . . . . 176.9(4) ?
    C2 C3 N28 C33 . . . . 174.3(4) ?
    C4 C3 N28 C33 . . . . -62.1(5) ?
    C32 N28 C29 C30 . . . . 6.4(5) ?
    C33 N28 C29 C30 . . . . 122.7(4) ?
    C3 N28 C29 C30 . . . . -116.1(4) ?
    N28 C29 C30 C31 . . . . -30.1(6) ?
    C29 C30 C31 C32 . . . . 42.3(7) ?
    C30 C31 C32 N28 . . . . -37.8(6) ?
    C29 N28 C32 C31 . . . . 19.1(5) ?
    C33 N28 C32 C31 . . . . -98.1(5) ?
    C3 N28 C32 C31 . . . . 140.1(4) ?
    C32 N28 C33 C34 . . . . 179.3(4) ?
    C29 N28 C33 C34 . . . . 64.5(5) ?
    C3 N28 C33 C34 . . . . -57.2(5) ?
    N28 C33 C34 C35 . . . . 120.3(5) ?
    C13 C17 O27 H27 . . . . -113(4) ?
    C16 C17 O27 H27 . . . . 126(4) ?
    C15 C16 C17 H17 . . . . -95.0 ?
    C20 C16 C17 H17 . . . . 82.1 ?
    C17 C16 C20 H20 . . . . 8.1 ?
    C22 C21 C20 H20 . . . . -4.3 ?
    C15 C16 C20 H20 . . . . -175.5 ?
    N26 C21 C20 H20 . . . . 176.4 ?
    C18 C13 C14 H14 . . . . 178.0 ?
    H9 C9 C8 H8 . . . . -172.9 ?
    C19 C10 C13 C18 . . . . 7.5(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
    O27 H27 Br . 0.81(3) 2.38(3) 3.194(4) 178(6) yes
    O1W H1W Br 3_555 0.88(4) 2.53(4) 3.405(5) 172(3) yes
data_global
_journal_date_recd_electronic     2002-05-07
_journal_date_accepted     2002-07-24
_journal_name_full     'Acta Crystallographica, Section C'
_journal_year     2002
_journal_volume     58
_journal_issue     10
_journal_page_first     o598
_journal_page_last     o599
_journal_paper_category     FO
_publ_contact_author_name     'Dr V. Parthasarathi'
_publ_contact_author_address
;
Department of Physics
Bharathidasan University
Tiruchirappalli 620 024
India
;
_publ_contact_author_email     sarati@yahoo.com
_publ_contact_author_fax     '+91 0431 660245'
_publ_contact_author_phone     '(0091) 431 660357'
_publ_section_title
;
3β-(1-Allyl-1-pyrrolidinio)-16-(2-pyridylmethylene)androst-5-ene-17β-ol
bromide hemihydrate
;
loop_
    _publ_author_name
    _publ_author_address
    'Vasuki, G.'
;
Department of Physics
Bharathidasan University
Tiruchirappalli 620 024
India
;
    'Thamotharan, S.'
;
Department of Physics
Bharathidasan University
Tiruchirappalli 620 024
India
;
    'Parthasarathi, V.'
;
Department of Physics
Bharathidasan University
Tiruchirappalli 620 024
India
;
    'Ramamurthi, K.'
;
Department of Physics
Bharathidasan University
Tiruchirappalli 620 024
India
;
    'Dubey, S.'
;
University Institute of Pharmaceutical Sciences
Panjab University
Chandigarh 160 014
India
;
    'Jindal, D. P.'
;
University Institute of Pharmaceutical Sciences
Panjab University
Chandigarh 160 014
India
;
