#------------------------------------------------------------------------------
#$Date: 2017-10-13 03:48:21 +0300 (Fri, 13 Oct 2017) $
#$Revision: 201957 $
#$URL: file:///home/coder/svn-repositories/cod/cif/2/01/22/2012232.cif $
#------------------------------------------------------------------------------
#
# This file is available in the Crystallography Open Database (COD),
# http://www.crystallography.net/. The original data for this entry
# were provided by IUCr Journals, http://journals.iucr.org/.
#
# The file may be used within the scientific community so long as
# proper attribution is given to the journal article from which the
# data were obtained.
#
data_2012232
loop_
_publ_author_name
'Vasuki, G.'
'Parthasarathi, V.'
'Ramamurthi, K.'
'Jindal, D. P.'
'Dubey, S.'
_publ_section_title
;
 17-Oxo-16-(2-pyridylmethylene)androst-5-en-3β-ol monohydrate
;
_journal_issue                   9
_journal_name_full               'Acta Crystallographica Section C'
_journal_page_first              1062
_journal_page_last               1063
_journal_paper_doi               10.1107/S010827010100912X
_journal_volume                  57
_journal_year                    2001
_chemical_formula_iupac          'C25 H31 N O2, H2 O'
_chemical_formula_moiety         'C25 H31 N O2, H2 O'
_chemical_formula_sum            'C25 H33 N O3'
_chemical_formula_weight         395.52
_chemical_name_systematic
;
17-Oxo-16-(2-pyridylmethylene)-androst-5-en-3β-ol monohydrate
;
_space_group_IT_number           4
_symmetry_cell_setting           monoclinic
_symmetry_space_group_name_Hall  'P 2yb'
_symmetry_space_group_name_H-M   'P 1 21 1'
_audit_creation_method           SHELXL-97
_cell_angle_alpha                90.00
_cell_angle_beta                 91.197(12)
_cell_angle_gamma                90.00
_cell_formula_units_Z            2
_cell_length_a                   6.5376(3)
_cell_length_b                   11.8766(10)
_cell_length_c                   13.5312(15)
_cell_measurement_reflns_used    25
_cell_measurement_temperature    293(2)
_cell_measurement_theta_max      30
_cell_measurement_theta_min      20
_cell_volume                     1050.39(15)
_computing_cell_refinement       'CAD-4 EXPRESS'
_computing_data_collection       'CAD-4 EXPRESS (Enraf-Nonius, 1994)'
_computing_data_reduction        'MolEN (Fair, 1990)'
_computing_molecular_graphics    'ZORTEP (Zsolnai, 1997)'
_computing_publication_material  'SHELXL97 '
_computing_structure_refinement  'SHELXL97 (Sheldrick, 1997)'
_computing_structure_solution    'SHELXS97 (Sheldrick, 1997)'
_diffrn_ambient_temperature      293(2)
_diffrn_measured_fraction_theta_full .995
_diffrn_measured_fraction_theta_max .995
_diffrn_measurement_device_type  'Enraf-Nonius CAD-4'
_diffrn_measurement_method       ω--2θ
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_source         'fine-focus sealed tube'
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.5418
_diffrn_reflns_av_R_equivalents  .0229
_diffrn_reflns_av_sigmaI/netI    .0160
_diffrn_reflns_limit_h_max       7
_diffrn_reflns_limit_h_min       0
_diffrn_reflns_limit_k_max       14
_diffrn_reflns_limit_k_min       0
_diffrn_reflns_limit_l_max       16
_diffrn_reflns_limit_l_min       -16
_diffrn_reflns_number            2187
_diffrn_reflns_theta_full        67.92
_diffrn_reflns_theta_max         67.92
_diffrn_reflns_theta_min         3.27
_diffrn_standards_decay_%        0
_diffrn_standards_interval_time  120
_diffrn_standards_number         2
_exptl_absorpt_coefficient_mu    .639
_exptl_absorpt_correction_T_max  .9880
_exptl_absorpt_correction_T_min  .7999
_exptl_absorpt_correction_type   psi-scan
_exptl_absorpt_process_details   '(North et al., 1968)'
_exptl_crystal_colour            colourless
_exptl_crystal_density_diffrn    1.251
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       rectangular
_exptl_crystal_F_000             428
_exptl_crystal_size_max          .3
_exptl_crystal_size_mid          .2
_exptl_crystal_size_min          .1
_refine_diff_density_max         .272
_refine_diff_density_min         -.220
_refine_ls_extinction_coef       .0044(10)
_refine_ls_extinction_method     SHELXL97
_refine_ls_goodness_of_fit_ref   1.143
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     267
_refine_ls_number_reflns         2003
_refine_ls_number_restraints     3
_refine_ls_restrained_S_all      1.142
_refine_ls_R_factor_all          .0422
_refine_ls_R_factor_gt           .0389
_refine_ls_shift/su_max          <0.001
_refine_ls_shift/su_mean         .000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'w = 1/[σ²(Fo²)+(0.0724P)²+0.1862P] where P = (Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_ref         .1165
_reflns_number_gt                1888
_reflns_number_total             2003
_reflns_threshold_expression     I>2s(I)
_cod_data_source_file            vj1136.cif
_cod_data_source_block           I
_cod_original_sg_symbol_H-M      'P 21'
_cod_database_code               2012232
_cod_database_fobs_code          2012232
loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'-x, y+1/2, -z'
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
O3 -.2397(4) .7248(3) -.28994(15) .0603(7) Uani d . 1 . . O
H3 -.1564 .7538 -.3265 .090 Uiso calc R 1 . . H
O17 .3275(3) .6155(2) .46889(15) .0523(6) Uani d . 1 . . O
N26 .9804(4) .8130(2) .54939(17) .0432(6) Uani d . 1 . . N
C1 -.1706(4) .6331(3) -.02775(19) .0351(6) Uani d . 1 . . C
H1A -.2176 .5653 .0047 .042 Uiso calc R 1 . . H
H1B -.2349 .6968 .0040 .042 Uiso calc R 1 . . H
C2 -.2407(4) .6297(3) -.1358(2) .0411(7) Uani d . 1 . . C
H2A -.1876 .5624 -.1668 .049 Uiso calc R 1 . . H
H2B -.3889 .6265 -.1397 .049 Uiso calc R 1 . . H
C3 -.1671(4) .7322(3) -.19021(19) .0387(6) Uani d . 1 . . C
H3A -.2273 .7991 -.1600 .046 Uiso calc R 1 . . H
C4 .0656(4) .7417(3) -.18152(19) .0380(6) Uani d . 1 . . C
H4A .1272 .6805 -.2178 .046 Uiso calc R 1 . . H
H4B .1086 .8119 -.2113 .046 Uiso calc R 1 . . H
C5 .1415(4) .7380(2) -.07507(18) .0299(5) Uani d . 1 . . C
C6 .2728(4) .8155(2) -.04007(19) .0331(6) Uani d . 1 . . C
H6 .3135 .8718 -.0832 .040 Uiso calc R 1 . . H
C7 .3592(4) .8183(2) .06345(19) .0349(6) Uani d . 1 . . C
H7A .2949 .8790 .0993 .042 Uiso calc R 1 . . H
H7B .5045 .8342 .0612 .042 Uiso calc R 1 . . H
C8 .3279(4) .7087(2) .11905(18) .0276(5) Uani d . 1 . . C
H8 .4249 .6524 .0953 .033 Uiso calc R 1 . . H
C9 .1071(4) .6658(2) .09947(18) .0279(5) Uani d . 1 . . C
H9 .0165 .7280 .1173 .033 Uiso calc R 1 . . H
C10 .0638(4) .6425(2) -.01221(18) .0286(5) Uani d . 1 . . C
C11 .0480(4) .5661(3) .16598(19) .0357(6) Uani d . 1 . . C
H11A -.0978 .5526 .1580 .043 Uiso calc R 1 . . H
H11B .1184 .4992 .1434 .043 Uiso calc R 1 . . H
C12 .0980(4) .5828(3) .27624(19) .0367(6) Uani d . 1 . . C
H12A .0116 .6413 .3028 .044 Uiso calc R 1 . . H
H12B .0723 .5136 .3120 .044 Uiso calc R 1 . . H
C13 .3226(4) .6160(2) .28874(18) .0309(6) Uani d . 1 . . C
C14 .3600(4) .7239(2) .23019(18) .0289(5) Uani d . 1 . . C
H14 .2547 .7772 .2508 .035 Uiso calc R 1 . . H
C15 .5654(4) .7707(3) .27197(18) .0346(6) Uani d . 1 . . C
H15A .6808 .7380 .2384 .042 Uiso calc R 1 . . H
H15B .5712 .8521 .2660 .042 Uiso calc R 1 . . H
C16 .5625(4) .7348(3) .37945(19) .0354(6) Uani d . 1 . . C
C17 .3912(4) .6510(3) .39193(19) .0363(6) Uani d . 1 . . C
C18 .4657(4) .5173(3) .2622(2) .0411(7) Uani d . 1 . . C
H18A .6052 .5385 .2758 .062 Uiso calc R 1 . . H
H18B .4489 .4996 .1933 .062 Uiso calc R 1 . . H
H18C .4320 .4525 .3010 .062 Uiso calc R 1 . . H
C19 .1667(5) .5319(3) -.0459(2) .0409(7) Uani d . 1 . . C
H19A .1563 .5259 -.1166 .061 Uiso calc R 1 . . H
H19B .0994 .4688 -.0164 .061 Uiso calc R 1 . . H
H19C .3083 .5323 -.0256 .061 Uiso calc R 1 . . H
C20 .6861(4) .7582(3) .4573(2) .0370(6) Uani d . 1 . . C
H20 .6468 .7262 .5167 .044 Uiso calc R 1 . . H
C21 .8725(4) .8259(3) .46345(19) .0361(6) Uani d . 1 . . C
C22 .9409(5) .8958(3) .3895(2) .0481(8) Uani d . 1 . . C
H22 .8645 .9042 .3312 .058 Uiso calc R 1 . . H
C23 1.1231(5) .9531(3) .4025(3) .0550(9) Uani d . 1 . . C
H23 1.1685 1.0024 .3543 .066 Uiso calc R 1 . . H
C24 1.2368(5) .9358(3) .4881(3) .0520(8) Uani d . 1 . . C
H24 1.3632 .9704 .4977 .062 Uiso calc R 1 . . H
C25 1.1584(5) .8666(3) .5585(2) .0514(9) Uani d . 1 . . C
H25 1.2345 .8562 .6166 .062 Uiso calc R 1 . . H
O27 -.5891(4) .5797(3) -.32162(17) .0683(8) Uani d D 1 . . O
H27A -.5206 .6560 -.3215 .097 Uiso d D 1 . . H
H27B -.6254 .5933 -.3937 .097 Uiso d D 1 . . H
loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C .0181 .0091 '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'
N N .0311 .0180 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O .0492 .0322 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_publ_flag
C3 O3 H3 109.5 ?
C25 N26 C21 117.6(3) ?
C2 C1 C10 114.2(2) yes
C2 C1 H1A 108.7 ?
C10 C1 H1A 108.7 ?
C2 C1 H1B 108.7 ?
C10 C1 H1B 108.7 ?
H1A C1 H1B 107.6 ?
C3 C2 C1 110.8(2) ?
C3 C2 H2A 109.5 ?
C1 C2 H2A 109.5 ?
C3 C2 H2B 109.5 ?
C1 C2 H2B 109.5 ?
H2A C2 H2B 108.1 ?
O3 C3 C2 108.1(2) yes
O3 C3 C4 112.9(2) ?
C2 C3 C4 110.5(2) ?
O3 C3 H3A 108.4 ?
C2 C3 H3A 108.4 ?
C4 C3 H3A 108.4 ?
C5 C4 C3 112.1(2) ?
C5 C4 H4A 109.2 ?
C3 C4 H4A 109.2 ?
C5 C4 H4B 109.2 ?
C3 C4 H4B 109.2 ?
H4A C4 H4B 107.9 ?
C6 C5 C10 122.5(2) ?
C6 C5 C4 120.8(2) ?
C10 C5 C4 116.7(2) ?
C5 C6 C7 124.9(2) ?
C5 C6 H6 117.6 ?
C7 C6 H6 117.6 ?
C6 C7 C8 113.1(2) ?
C6 C7 H7A 109.0 ?
C8 C7 H7A 109.0 ?
C6 C7 H7B 109.0 ?
C8 C7 H7B 109.0 ?
H7A C7 H7B 107.8 ?
C7 C8 C14 111.7(2) ?
C7 C8 C9 109.4(2) ?
C14 C8 C9 108.44(18) ?
C7 C8 H8 109.1 ?
C14 C8 H8 109.1 ?
C9 C8 H8 109.1 ?
C11 C9 C8 113.38(19) ?
C11 C9 C10 112.8(2) ?
C8 C9 C10 111.99(19) ?
C11 C9 H9 106.0 ?
C8 C9 H9 106.0 ?
C10 C9 H9 106.0 ?
C5 C10 C1 108.8(2) ?
C5 C10 C19 108.5(2) yes
C1 C10 C19 109.5(2) ?
C5 C10 C9 110.9(2) ?
C1 C10 C9 107.72(18) ?
C19 C10 C9 111.4(2) ?
C12 C11 C9 114.7(2) ?
C12 C11 H11A 108.6 ?
C9 C11 H11A 108.6 ?
C12 C11 H11B 108.6 ?
C9 C11 H11B 108.6 ?
H11A C11 H11B 107.6 ?
C13 C12 C11 109.0(2) ?
C13 C12 H12A 109.9 ?
C11 C12 H12A 109.9 ?
C13 C12 H12B 109.9 ?
C11 C12 H12B 109.9 ?
H12A C12 H12B 108.3 ?
C17 C13 C12 116.0(2) ?
C17 C13 C14 101.5(2) ?
C12 C13 C14 108.9(2) ?
C17 C13 C18 104.7(2) yes
C12 C13 C18 111.3(2) ?
C14 C13 C18 114.2(2) ?
C8 C14 C13 113.1(2) ?
C8 C14 C15 120.2(2) ?
C13 C14 C15 105.0(2) ?
C8 C14 H14 105.9 ?
C13 C14 H14 105.9 ?
C15 C14 H14 105.9 ?
C16 C15 C14 102.7(2) ?
C16 C15 H15A 111.2 ?
C14 C15 H15A 111.2 ?
C16 C15 H15B 111.2 ?
C14 C15 H15B 111.2 ?
H15A C15 H15B 109.1 ?
C20 C16 C17 118.9(2) ?
C20 C16 C15 132.4(3) ?
C17 C16 C15 108.5(2) ?
O17 C17 C16 126.7(2) ?
O17 C17 C13 126.8(3) yes
C16 C17 C13 106.5(2) ?
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 130.2(3) ?
C16 C20 H20 114.9 ?
C21 C20 H20 114.9 ?
N26 C21 C22 121.3(3) ?
N26 C21 C20 113.9(3) ?
C22 C21 C20 124.9(2) ?
C23 C22 C21 119.7(3) ?
C23 C22 H22 120.1 ?
C21 C22 H22 120.1 ?
C24 C23 C22 118.8(3) ?
C24 C23 H23 120.6 ?
C22 C23 H23 120.6 ?
C25 C24 C23 118.1(3) ?
C25 C24 H24 120.9 ?
C23 C24 H24 120.9 ?
N26 C25 C24 124.3(3) ?
N26 C25 H25 117.8 ?
C24 C25 H25 117.8 ?
H27A O27 H27B 87.3 ?
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
O3 C3 . 1.424(3) ?
O3 H3 . .82 ?
O17 C17 . 1.206(3) yes
N26 C25 . 1.330(4) ?
N26 C21 . 1.356(3) ?
C1 C2 . 1.523(3) yes
C1 C10 . 1.546(3) ?
C1 H1A . .97 ?
C1 H1B . .97 ?
C2 C3 . 1.507(4) ?
C2 H2A . .97 ?
C2 H2B . .97 ?
C3 C4 . 1.528(4) ?
C3 H3A . .98 ?
C4 C5 . 1.514(3) ?
C4 H4A . .97 ?
C4 H4B . .97 ?
C5 C6 . 1.338(4) ?
C5 C10 . 1.512(4) ?
C6 C7 . 1.500(3) ?
C6 H6 . .93 ?
C7 C8 . 1.519(4) ?
C7 H7A . .97 ?
C7 H7B . .97 ?
C8 C14 . 1.525(3) ?
C8 C9 . 1.549(3) ?
C8 H8 . .98 ?
C9 C11 . 1.542(4) ?
C9 C10 . 1.556(3) ?
C9 H9 . .98 ?
C10 C19 . 1.549(4) yes
C11 C12 . 1.534(3) ?
C11 H11A . .97 ?
C11 H11B . .97 ?
C12 C13 . 1.526(3) ?
C12 H12A . .97 ?
C12 H12B . .97 ?
C13 C17 . 1.516(3) ?
C13 C14 . 1.529(4) ?
C13 C18 . 1.547(4) yes
C14 C15 . 1.550(3) ?
C14 H14 . .98 ?
C15 C16 . 1.516(4) ?
C15 H15A . .97 ?
C15 H15B . .97 ?
C16 C20 . 1.343(4) ?
C16 C17 . 1.510(4) ?
C18 H18A . .96 ?
C18 H18B . .96 ?
C18 H18C . .96 ?
C19 H19A . .96 ?
C19 H19B . .96 ?
C19 H19C . .96 ?
C20 C21 . 1.461(4) ?
C20 H20 . .93 ?
C21 C22 . 1.382(4) ?
C22 C23 . 1.379(5) ?
C22 H22 . .93 ?
C23 C24 . 1.379(5) ?
C23 H23 . .93 ?
C24 C25 . 1.366(5) ?
C24 H24 . .93 ?
C25 H25 . .93 ?
O27 H27A . 1.01 ?
O27 H27B . 1.01 ?
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
O3 H3 N26 1_454 .82 2.04 2.833(3) 162 yes
O27 H27A O3 . 1.01 2.05 2.886(3) 139 yes
O27 H27B O17 1_454 1.01 1.90 2.907(3) 176 yes
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
_geom_torsion_publ_flag
C10 C1 C2 C3 -57.1(3) yes
C1 C2 C3 O3 -179.2(2) ?
C1 C2 C3 C4 56.8(3) ?
O3 C3 C4 C5 -174.4(3) ?
C2 C3 C4 C5 -53.3(3) ?
C3 C4 C5 C6 -130.4(3) ?
C3 C4 C5 C10 50.4(3) ?
C10 C5 C6 C7 .1(4) yes
C4 C5 C6 C7 -179.1(3) ?
C5 C6 C7 C8 14.8(4) yes
C6 C7 C8 C14 -163.7(2) ?
C6 C7 C8 C9 -43.6(3) yes
C7 C8 C9 C11 -170.3(2) ?
C14 C8 C9 C11 -48.3(3) ?
C7 C8 C9 C10 60.6(3) yes
C14 C8 C9 C10 -177.3(2) ?
C6 C5 C10 C1 133.7(3) ?
C4 C5 C10 C1 -47.1(3) ?
C6 C5 C10 C19 -107.3(3) ?
C4 C5 C10 C19 72.0(3) ?
C6 C5 C10 C9 15.4(3) yes
C4 C5 C10 C9 -165.4(2) ?
C2 C1 C10 C5 50.1(3) ?
C2 C1 C10 C19 -68.3(3) ?
C2 C1 C10 C9 170.4(2) ?
C11 C9 C10 C5 -174.9(2) ?
C8 C9 C10 C5 -45.5(3) yes
C11 C9 C10 C1 66.2(3) ?
C8 C9 C10 C1 -164.4(2) ?
C11 C9 C10 C19 -53.9(3) ?
C8 C9 C10 C19 75.5(3) ?
C8 C9 C11 C12 48.4(3) ?
C10 C9 C11 C12 177.0(2) ?
C9 C11 C12 C13 -52.6(3) ?
C11 C12 C13 C17 172.1(2) ?
C11 C12 C13 C14 58.5(3) ?
C11 C12 C13 C18 -68.3(3) ?
C7 C8 C14 C13 178.1(2) ?
C9 C8 C14 C13 57.4(3) ?
C7 C8 C14 C15 -57.0(3) ?
C9 C8 C14 C15 -177.6(2) ?
C17 C13 C14 C8 172.93(19) ?
C12 C13 C14 C8 -64.2(3) ?
C18 C13 C14 C8 60.9(3) ?
C17 C13 C14 C15 40.1(3) ?
C12 C13 C14 C15 163.0(2) ?
C18 C13 C14 C15 -71.9(3) ?
C8 C14 C15 C16 -161.1(2) ?
C13 C14 C15 C16 -32.4(3) ?
C14 C15 C16 C20 -172.7(3) ?
C14 C15 C16 C17 12.0(3) ?
C20 C16 C17 O17 13.9(5) ?
C15 C16 C17 O17 -170.0(3) ?
C20 C16 C17 C13 -163.2(3) ?
C15 C16 C17 C13 12.8(3) ?
C12 C13 C17 O17 32.7(4) ?
C14 C13 C17 O17 150.5(3) ?
C18 C13 C17 O17 -90.4(3) ?
C12 C13 C17 C16 -150.1(2) ?
C14 C13 C17 C16 -32.3(3) ?
C18 C13 C17 C16 86.8(3) ?
C17 C16 C20 C21 173.2(3) ?
C15 C16 C20 C21 -1.7(6) ?
C25 N26 C21 C22 -2.5(5) ?
C25 N26 C21 C20 176.1(3) ?
C16 C20 C21 N26 -167.4(3) ?
C16 C20 C21 C22 11.2(5) ?
N26 C21 C22 C23 .5(5) ?
C20 C21 C22 C23 -177.9(3) ?
C21 C22 C23 C24 2.3(6) ?
C22 C23 C24 C25 -3.0(6) ?
C21 N26 C25 C24 1.7(5) ?
C23 C24 C25 N26 1.0(6) ?
loop_
_cod_related_entry_id
_cod_related_entry_database
_cod_related_entry_code
1 ChemSpider 21182035
