##############################################################################
###                                                                        ###
###        Electronic paper (Acta Crystallographica Section E)             ###
###                                                                        ###
##############################################################################
#                                                                            #
# 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 2.1.    #
#                                                                            #
# 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     SHELXL-97
_chemical_name_systematic
;
5α-androst-3-en-one
;
_chemical_name_common     ?
_chemical_formula_moiety     'C19 H28 O'
_chemical_formula_sum     'C19 H28 O'
_chemical_formula_weight     272.41
_chemical_melting_point     399
_symmetry_cell_setting     orthorhombic
_symmetry_space_group_name_H-M     'P 21 21 21'
loop_
    _symmetry_equiv_pos_as_xyz
    'x, y, z'
    '-x+1/2, -y, z+1/2'
    'x+1/2, -y+1/2, -z'
    '-x, y+1/2, -z+1/2'
_cell_length_a     6.451(3)
_cell_length_b     9.2109(9)
_cell_length_c     26.558(8)
_cell_angle_alpha     90.00
_cell_angle_beta     90.00
_cell_angle_gamma     90.00
_cell_volume     1578.0(10)
_cell_formula_units_Z     4
_cell_measurement_reflns_used     25
_cell_measurement_theta_min     5.89
_cell_measurement_theta_max     10.28
_cell_measurement_temperature     293(2)
_exptl_crystal_description     block
_exptl_crystal_colour     'colourless'
_exptl_crystal_size_max      .50
_exptl_crystal_size_mid      .45
_exptl_crystal_size_min      .30
_exptl_crystal_density_diffrn     1.147
_exptl_crystal_density_meas     ?
_exptl_crystal_density_method     'not measured'
_exptl_crystal_F_000     600
_exptl_absorpt_coefficient_mu      .068
_exptl_absorpt_correction_type     none
_exptl_absorpt_process_details     ?
_exptl_absorpt_correction_T_min     ?
_exptl_absorpt_correction_T_max     ?
_exptl_special_details
;
νₘₐₓ (KBr)/cm⁻¹
3014 (C--H), 1737 (C=O); ¹H NMR (500 MHz, CDCl₃) δ: 0.80 (3H,s,
19-H₃), 0.88 (3H, s, 18-H₃),
5.29 (1H, ddd, J~4,3~ 9.5, J~4,5~ 3.8, J~\{4,2\\alpha\}~ 2.0, \{4-H\}),
5.57 (1H, ddd, J~3,4~ 9.5, J~\{3,2\\beta\}~ 6.8,
J~\{3,2\\alpha\}~ 3.2,
\{3-H\});
¹³C NMR (75.6 MHz, CDCl₃) δ: 11.9 (C-19), 14.0 (C-18), 46.1 (C-5),
125.6 (C-3), 131.0 (C-4), 220.3 (C-17).
;
_diffrn_ambient_temperature     293(2)
_diffrn_radiation_type     MoK\a
_diffrn_radiation_wavelength      .71073
_diffrn_radiation_source     'fine-focus sealed tube'
_diffrn_radiation_monochromator     graphite
_diffrn_measurement_device_type     'Enraf-Nonius CAD-4'
_diffrn_measurement_method     'profile data from ω-2θ'
_diffrn_reflns_number     3713
_diffrn_reflns_av_R_equivalents      .0475
_diffrn_reflns_av_sigmaI/netI      .0271
_diffrn_reflns_theta_min     3.07
_diffrn_reflns_theta_max     27.47
_diffrn_reflns_theta_full     27.47
_diffrn_measured_fraction_theta_max      .988
_diffrn_measured_fraction_theta_full      .988
_diffrn_reflns_limit_h_min     0
_diffrn_reflns_limit_h_max     8
_diffrn_reflns_limit_k_min     0
_diffrn_reflns_limit_k_max     11
_diffrn_reflns_limit_l_min     -34
_diffrn_reflns_limit_l_max     34
_diffrn_standards_number     3
_diffrn_standards_interval_count     ?
_diffrn_standards_interval_time     180
_diffrn_standards_decay_%     1.4
_refine_special_details
;
Due to the absence of a strong enough anomalous
scatterer at the Mo wavelength the absolute configuration could not
be confirmed from the X-ray data.
 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.
Examination of the crystal structure with PLATON (Spek, 1995) showed that
there are no solvent-accessible voids in the crystal lattice. All
calculations were performed on a Pentium 350 MHz PC running LINUX.
;
_reflns_number_total     2091
_reflns_number_gt     1607
_reflns_threshold_expression     I>2σ(I)
_refine_ls_structure_factor_coef     Fsqd
_refine_ls_matrix_type     full
_refine_ls_R_factor_all      .0675
_refine_ls_R_factor_gt      .0402
_refine_ls_wR_factor_ref      .1094
_refine_ls_goodness_of_fit_ref     1.068
_refine_ls_restrained_S_all     1.068
_refine_ls_number_reflns     2091
_refine_ls_number_parameters     184
_refine_ls_number_restraints     0
_refine_ls_hydrogen_treatment     constr
_refine_ls_weighting_scheme     calc
_refine_ls_weighting_details
     'calc w = 1/[σ²(Fo²)+(0.0409P)²+0.3113P] where P = (Fo²+2Fc²)/3'
_refine_ls_shift/su_max      .000
_refine_ls_shift/su_mean      .000
_refine_diff_density_max      .186
_refine_diff_density_min      -.137
_refine_ls_extinction_method     SHELXL97
_refine_ls_extinction_coef      .0101(18)
loop_
    _atom_type_symbol
    _atom_type_description
    _atom_type_scat_dispersion_real
    _atom_type_scat_dispersion_imag
    _atom_type_scat_source
    'C' 'C'  .0033  .0016
                         'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
    'O' 'O'  .0106  .0060
                         'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
    'H' 'H'  .0000  .0000
                         'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
_computing_data_collection     'CAD-4 Software (Enraf-Nonius, 1989)'
_computing_cell_refinement     'CAD-4 Software'
_computing_data_reduction     'PLATON (Spek, 1995)'
_computing_structure_solution     'SHELXS97 (Sheldrick, 1997)'
_computing_structure_refinement     'SHELXL97 (Sheldrick, 1997)'
_computing_molecular_graphics     'ORTEPII (Johnson, 1976)'
_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
    C10  .6580(3)  .2096(2)  .14778(8)  .0427(5) Uani d . 1 . . C
    C9  .6231(3)  .3395(2)  .11206(7)  .0385(5) Uani d . 1 . . C
    H9  .7608  .3811  .1060  .046 Uiso calc R 1 . . H
    C8  .4948(3)  .4618(2)  .13743(7)  .0393(5) Uani d . 1 . . C
    H8  .3571  .4232  .1454  .047 Uiso calc R 1 . . H
    C14  .4689(3)  .5861(2)  .10079(8)  .0409(5) Uani d . 1 . . C
    H14  .6093  .6185  .0924  .049 Uiso calc R 1 . . H
    O17  .3318(3)  .7081(2)  -.01963(7)  .0666(5) Uani d . 1 . . O
    C11  .5378(4)  .2990(3)  .05997(8)  .0529(6) Uani d . 1 . . C
    H11A  .6332  .2321  .0439  .063 Uiso calc R 1 . . H
    H11B  .4065  .2491  .0642  .063 Uiso calc R 1 . . H
    C12  .5052(4)  .4294(3)  .02541(8)  .0529(6) Uani d . 1 . . C
    H12A  .6381  .4728  .0173  .063 Uiso calc R 1 . . H
    H12B  .4411  .3978  -.0058  .063 Uiso calc R 1 . . H
    C13  .3683(3)  .5408(2)  .05079(9)  .0425(5) Uani d . 1 . . C
    C1  .8088(4)  .0984(3)  .12457(10)  .0603(7) Uani d . 1 . . C
    H1A  .7487  .0600  .0938  .072 Uiso calc R 1 . . H
    H1B  .9370  .1472  .1157  .072 Uiso calc R 1 . . H
    C7  .5983(4)  .5102(3)  .18674(8)  .0545(6) Uani d . 1 . . C
    H7A  .7290  .5573  .1791  .065 Uiso calc R 1 . . H
    H7B  .5101  .5805  .2035  .065 Uiso calc R 1 . . H
    C5  .7657(4)  .2681(3)  .19566(9)  .0517(6) Uani d . 1 . . C
    H5  .8918  .3172  .1841  .062 Uiso calc R 1 . . H
    C6  .6376(4)  .3829(3)  .22207(9)  .0593(7) Uani d . 1 . . C
    H6A  .7104  .4166  .2518  .071 Uiso calc R 1 . . H
    H6B  .5064  .3415  .2327  .071 Uiso calc R 1 . . H
    C15  .3490(4)  .7228(2)  .11589(9)  .0545(6) Uani d . 1 . . C
    H15A  .4267  .7807  .1399  .065 Uiso calc R 1 . . H
    H15B  .2151  .6985  .1302  .065 Uiso calc R 1 . . H
    C17  .3420(4)  .6876(3)  .02537(9)  .0510(6) Uani d . 1 . . C
    C16  .3250(4)  .8025(3)  .06524(10)  .0602(7) Uani d . 1 . . C
    H16A  .1914  .8506  .0634  .072 Uiso calc R 1 . . H
    H16B  .4333  .8746  .0612  .072 Uiso calc R 1 . . H
    C19  .4529(4)  .1326(3)  .16007(10)  .0581(7) Uani d . 1 . . C
    H19A  .4771  .0587  .1849  .087 Uiso calc R 1 . . H
    H19B  .3982  .0890  .1300  .087 Uiso calc R 1 . . H
    H19C  .3553  .2019  .1730  .087 Uiso calc R 1 . . H
    C2  .8573(5)  -.0278(3)  .16035(12)  .0771(9) Uani d . 1 . . C
    H2A  .7473  -.0993  .1579  .093 Uiso calc R 1 . . H
    H2B  .9850  -.0739  .1496  .093 Uiso calc R 1 . . H
    C4  .8364(4)  .1486(3)  .22969(10)  .0643(7) Uani d . 1 . . C
    H4  .8508  .1685  .2638  .077 Uiso calc R 1 . . H
    C3  .8790(5)  .0169(3)  .21371(13)  .0763(9) Uani d . 1 . . C
    H3  .9249  -.0515  .2370  .092 Uiso calc R 1 . . H
    C18  .1442(4)  .4843(3)  .05704(10)  .0573(6) Uani d . 1 . . C
    H18A  .1442  .4015  .0789  .086 Uiso calc R 1 . . H
    H18B  .0900  .4571  .0247  .086 Uiso calc R 1 . . H
    H18C  .0593  .5594  .0713  .086 Uiso calc R 1 . . H
loop_
    _atom_site_aniso_label
    _atom_site_aniso_U_11
    _atom_site_aniso_U_22
    _atom_site_aniso_U_33
    _atom_site_aniso_U_12
    _atom_site_aniso_U_13
    _atom_site_aniso_U_23
    C10  .0427(11)  .0411(10)  .0445(11)  .0074(11)  .0047(10)  .0025(10)
    C9  .0371(10)  .0419(10)  .0366(11)  -.0005(9)  .0036(8)  -.0015(9)
    C8  .0393(11)  .0419(11)  .0368(10)  .0019(10)  .0022(9)  -.0021(9)
    C14  .0398(10)  .0392(11)  .0438(11)  -.0015(9)  -.0001(9)  -.0023(9)
    O17  .0621(11)  .0817(12)  .0559(10)  -.0006(12)  -.0048(9)  .0239(10)
    C11  .0679(15)  .0473(12)  .0434(12)  .0098(12)  -.0031(11)  -.0102(11)
    C12  .0597(14)  .0639(15)  .0350(11)  .0082(13)  -.0017(11)  -.0041(11)
    C13  .0380(10)  .0476(12)  .0419(11)  -.0019(10)  -.0023(9)  .0027(10)
    C1  .0600(15)  .0533(14)  .0675(17)  .0163(13)  .0070(13)  -.0002(13)
    C7  .0661(15)  .0548(13)  .0428(12)  .0099(13)  -.0057(11)  -.0125(11)
    C5  .0470(12)  .0619(15)  .0461(13)  .0080(12)  -.0024(10)  .0029(12)
    C6  .0651(15)  .0713(16)  .0414(12)  .0161(15)  -.0062(11)  -.0055(12)
    C15  .0635(14)  .0432(11)  .0567(14)  .0080(13)  -.0057(13)  -.0031(11)
    C17  .0383(11)  .0587(14)  .0560(14)  -.0028(12)  -.0028(10)  .0145(12)
    C16  .0617(15)  .0475(12)  .0713(17)  .0028(13)  -.0037(13)  .0102(12)
    C19  .0553(14)  .0516(13)  .0675(16)  -.0047(12)  .0032(12)  .0098(13)
    C2  .0759(18)  .0558(16)  .100(2)  .0239(16)  .0069(18)  .0109(16)
    C4  .0510(14)  .0833(19)  .0585(15)  .0116(15)  -.0061(12)  .0173(15)
    C3  .0649(18)  .0768(19)  .087(2)  .0214(17)  -.0020(16)  .0279(18)
    C18  .0432(12)  .0585(14)  .0703(16)  -.0097(12)  -.0073(12)  .0062(13)
_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
    C10 C19 . 1.536(3) ?
    C10 C1 . 1.542(3) ?
    C10 C9 . 1.544(3) ?
    C10 C5 . 1.546(3) ?
    C9 C11 . 1.535(3) ?
    C9 C8 . 1.552(3) ?
    C8 C14 . 1.511(3) ?
    C8 C7 . 1.536(3) ?
    C14 C15 . 1.531(3) ?
    C14 C13 . 1.536(3) ?
    O17 C17 . 1.212(3) yes
    C11 C12 . 1.526(3) ?
    C12 C13 . 1.512(3) ?
    C13 C17 . 1.520(3) ?
    C13 C18 . 1.545(3) ?
    C1 C2 . 1.533(4) ?
    C7 C6 . 1.523(3) ?
    C5 C4 . 1.496(3) yes
    C5 C6 . 1.514(3) ?
    C15 C16 . 1.540(3) ?
    C17 C16 . 1.501(4) ?
    C2 C3 . 1.482(4) yes
    C4 C3 . 1.315(4) yes
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
    C19 C10 C1 . . 108.74(19) ?
    C19 C10 C9 . . 111.30(18) ?
    C1 C10 C9 . . 111.19(18) ?
    C19 C10 C5 . . 111.9(2) ?
    C1 C10 C5 . . 106.08(19) ?
    C9 C10 C5 . . 107.50(18) ?
    C11 C9 C10 . . 114.68(17) ?
    C11 C9 C8 . . 112.11(17) ?
    C10 C9 C8 . . 111.93(16) ?
    C14 C8 C7 . . 112.17(18) ?
    C14 C8 C9 . . 109.21(16) ?
    C7 C8 C9 . . 110.41(18) ?
    C8 C14 C15 . . 120.66(18) ?
    C8 C14 C13 . . 113.46(17) ?
    C15 C14 C13 . . 103.65(18) ?
    C12 C11 C9 . . 113.58(18) ?
    C13 C12 C11 . . 110.26(18) ?
    C12 C13 C17 . . 118.1(2) ?
    C12 C13 C14 . . 108.83(18) ?
    C17 C13 C14 . . 100.96(18) ?
    C12 C13 C18 . . 111.4(2) ?
    C17 C13 C18 . . 104.05(18) ?
    C14 C13 C18 . . 113.20(19) ?
    C2 C1 C10 . . 112.6(2) ?
    C6 C7 C8 . . 112.0(2) ?
    C4 C5 C6 . . 113.6(2) ?
    C4 C5 C10 . . 112.2(2) ?
    C6 C5 C10 . . 112.28(19) ?
    C5 C6 C7 . . 110.0(2) ?
    C14 C15 C16 . . 102.37(19) ?
    O17 C17 C16 . . 125.6(2) ?
    O17 C17 C13 . . 125.7(2) ?
    C16 C17 C13 . . 108.75(19) ?
    C17 C16 C15 . . 105.82(19) ?
    C3 C2 C1 . . 113.7(2) ?
    C3 C4 C5 . . 123.2(3) ?
    C4 C3 C2 . . 123.0(3) ?
data_global
_journal_date_recd_electronic     2001-01-18
_journal_date_accepted     2001-01-24
_journal_name_full     'Acta Crystallographica, Section E'
_journal_year     2001
_journal_volume     57
_journal_issue      2
_journal_page_first     o189
_journal_page_last     o191
_publ_contact_author_name     'J. A. Paixao'
_publ_contact_author_address
;
Fac. Ciencias e Tecnologia
Departamento de Fisica
Universidade de Coimbra
P-3000 Coimbra
Portugal
;
_publ_contact_author_email     jap@pollux.fis.uc.pt
_publ_contact_author_fax     351-39-29158
_publ_contact_author_phone     351-39-23671
_publ_section_title
;
5α-Androst-3-en-17-one
;
loop_
    _publ_author_name
    _publ_author_address
    'Paixão, J. A.'
;
     CEMDRX, Departamento de Física
     Fac. Ciências e Tecnologia
     Universidade de Coimbra
     P-3004-516 Coimbra
     Portugal
;
    'Andrade, L. C. R.'
;
     CEMDRX, Departamento de Física
     Fac. Ciências e Tecnologia
     Universidade de Coimbra
     P-3004-516 Coimbra
     Portugal
;
    'de Almeida, M. J.'
;
     CEMDRX, Departamento de Física
     Fac. Ciências e Tecnologia
     Universidade de Coimbra
     P-3004-516 Coimbra
     Portugal
;
    'Tavares da Silva, E. J.'
;
      Centro de Estudos Farmacêuticos
      Laboratório de Química Farmaceutica
      Faculdade de Farmácia
      Universidade de Coimbra
      P-3000-295 Coimbra
      Portugal
;
    'Fernandes Roleira, F. M.'
;
      Centro de Estudos Farmacêuticos
      Laboratório de Química Farmaceutica
      Faculdade de Farmácia
      Universidade de Coimbra
      P-3000-295 Coimbra
      Portugal
;
    "Sá e Melo, M. L."
;
      Centro de Estudos Farmacêuticos
      Laboratório de Química Farmaceutica
      Faculdade de Farmácia
      Universidade de Coimbra
      P-3000-295 Coimbra
      Portugal
;
    'Campos Neves, A. S.'
;
      Centro de Estudos Farmacêuticos
      Laboratório de Química Farmaceutica
      Faculdade de Farmácia
      Universidade de Coimbra
      P-3000-295 Coimbra
      Portugal
;
