#------------------------------------------------------------------------------
#$Date: 2016-02-19 16:29:56 +0200 (Fri, 19 Feb 2016) $
#$Revision: 176759 $
#$URL: svn://www.crystallography.net/cod/cif/2/00/65/2006565.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_2006565
loop_
_publ_author_name
'Díaz, Eduardo'
'Barrios, Héctor'
'Toscano, Rubén A.'
_publ_section_title
;
 Three trans-2,6-Diaryl Derivatives of Oximes of
 N-Hydroxy-4-piperidone
;
_journal_issue                   10
_journal_name_full               'Acta Crystallographica Section C'
_journal_page_first              1468
_journal_page_last               1471
_journal_paper_doi               10.1107/S0108270197002953
_journal_volume                  53
_journal_year                    1997
_chemical_formula_moiety         'C13 H14 N2 O2 S2'
_chemical_formula_sum            'C13 H14 N2 O2 S2'
_chemical_formula_weight         294.38
_chemical_name_systematic
;
trans 1-hydroxy-2,6-bis(2-thiophenyl)-4-piperidone oxime
;
_space_group_IT_number           2
_symmetry_cell_setting           triclinic
_symmetry_space_group_name_Hall  '-P 1'
_symmetry_space_group_name_H-M   'P -1'
_cell_angle_alpha                108.98(2)
_cell_angle_beta                 112.91(2)
_cell_angle_gamma                91.69(2)
_cell_formula_units_Z            2
_cell_length_a                   9.479(3)
_cell_length_b                   10.229(3)
_cell_length_c                   8.625(2)
_cell_measurement_reflns_used    25
_cell_measurement_temperature    293(2)
_cell_measurement_theta_max      16.65
_cell_measurement_theta_min      4.15
_cell_volume                     716.6(4)
_computing_cell_refinement       'Nicolet P3 software'
_computing_data_collection
'Nicolet P3 software (Nicolet XRD Corporation, 1980)'
_computing_data_reduction        'Nicolet P3 software'
_computing_molecular_graphics    SHELXTL-PC
_computing_publication_material  SHELXTL-PC
_computing_structure_refinement  'SHELXL-93 (Sheldrick, 1993)'
_computing_structure_solution    'SHELXTL-PC (Sheldrick, 1990)'
_diffrn_ambient_temperature      293(2)
_diffrn_measurement_device       'Nicolet P3/F diffractometer'
_diffrn_measurement_method       θ/2θ
_diffrn_radiation_monochromator  'Ni filter'
_diffrn_radiation_source         'fine-focus sealed tube'
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54178
_diffrn_reflns_av_R_equivalents  0.0438
_diffrn_reflns_av_sigmaI/netI    0.0186
_diffrn_reflns_limit_h_max       9
_diffrn_reflns_limit_h_min       0
_diffrn_reflns_limit_k_max       10
_diffrn_reflns_limit_k_min       -10
_diffrn_reflns_limit_l_max       7
_diffrn_reflns_limit_l_min       -8
_diffrn_reflns_number            1592
_diffrn_reflns_theta_max         50.05
_diffrn_reflns_theta_min         1.50
_diffrn_standards_decay_%        3
_diffrn_standards_interval_count 98
_diffrn_standards_number         2
_exptl_absorpt_coefficient_mu    3.369
_exptl_absorpt_correction_T_max  0.67
_exptl_absorpt_correction_T_min  0.38
_exptl_absorpt_correction_type   'refDF (DIFABS; Walker & Stuart, 1983)'
_exptl_crystal_colour            colourless
_exptl_crystal_density_diffrn    1.364
_exptl_crystal_description       'truncated square pyramid'
_exptl_crystal_F_000             308
_exptl_crystal_size_max          0.40
_exptl_crystal_size_mid          0.32
_exptl_crystal_size_min          0.12
_refine_diff_density_max         0.380
_refine_diff_density_min         -0.390
_refine_ls_extinction_coef       0.011(3)
_refine_ls_extinction_method     'SHELXL93 (Sheldrick, 1993)'
_refine_ls_goodness_of_fit_all   1.064
_refine_ls_goodness_of_fit_obs   1.100
_refine_ls_hydrogen_treatment    'H atoms riding'
_refine_ls_matrix_type           full
_refine_ls_number_parameters     226
_refine_ls_number_reflns         1475
_refine_ls_restrained_S_all      1.025
_refine_ls_restrained_S_obs      1.055
_refine_ls_R_factor_all          0.0717
_refine_ls_R_factor_obs          .0696
_refine_ls_shift/esd_max         0.091
_refine_ls_shift/esd_mean        0.020
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'w = 1/[σ²(Fo²)+(0.1454P)²+0.5240P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_all         0.1938
_refine_ls_wR_factor_obs         .1909
_reflns_number_observed          1357
_reflns_number_total             1475
_reflns_observed_criterion       >2sigma(I)
_cod_data_source_file            cf1113.cif
_cod_data_source_block           3
_cod_depositor_comments
;
The following automatic conversions were performed:

'_refine_ls_weighting_scheme' value 'calc w =
1/[\s^2^(Fo^2^)+(0.1454P)^2^+0.5240P] where P=(Fo^2^+2Fc^2^)/3' was
changed to 'calc'. New tag '_refine_ls_weighting_details' was
created. The value of the new tag was set to 'w =
1/[\s^2^(Fo^2^)+(0.1454P)^2^+0.5240P] where P=(Fo^2^+2Fc^2^)/3'.

Automatic conversion script
Id: cif_fix_values 3143 2015-03-26 13:38:13Z robertas 
;
_cod_database_code               2006565
loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'-x, -y, -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_thermal_displace_type
_atom_site_calc_flag
_atom_site_refinement_flags
_atom_site_occupancy
_atom_site_disorder_group
_atom_site_type_symbol
N1 .1087(3) .3905(3) .4676(4) .0392(9) Uani d . 1 . N
C2 .0551(4) .2432(4) .3405(5) .0453(11) Uani d . 1 . C
C3 .1240(5) .1386(4) .4301(6) .0553(12) Uani d . 1 . C
C4 .2964(5) .1829(5) .5382(6) .0547(12) Uani d . 1 . C
C5 .3557(5) .3309(5) .6584(6) .0574(12) Uani d . 1 . C
C6 .2817(4) .4278(4) .5557(5) .0460(11) Uani d . 1 . C
O7 .0604(3) .3996(3) .6102(4) .0481(8) Uani d D 1 . O
N8 .3900(4) .0965(4) .5264(5) .0644(11) Uani d . 1 . N
O9A .3132(6) -.0454(5) .3978(8) .084(2) Uani d PD .646(10) . O
O9B .5585(10) .1561(10) .6611(12) .073(4) Uani d P .354(10) . O
S10 .0178(2) .3371(2) .0622(2) .0951(8) Uani d D 1 . S
C11 .0986(7) .2666(6) -.0840(7) .085(2) Uani d D 1 . C
C12 .1736(6) .1662(6) -.0459(7) .081(2) Uani d D 1 . C
C13 .1731(5) .1427(5) .1067(6) .0634(13) Uani d D 1 . C
C14 .0878(5) .2301(4) .1789(5) .0481(11) Uani d D 1 . C
S15 .3540(9) .6967(5) .5731(7) .0771(15) Uani d PDU .574(7) 1 S
C16 .399(4) .8378(15) .776(3) .093(5) Uani d PDU .574(7) 1 C
C17 .398(4) .7917(16) .903(2) .097(6) Uani d PDU .574(7) 1 C
C18 .358(4) .643(2) .842(3) .086(6) Uani d PDU .574(7) 1 C
C19 .3304(4) .5807(4) .6676(6) .0531(11) Uani d DU 1 . C
S15X .3486(14) .6509(8) .8846(7) .075(2) Uani d PDU .426(7) 2 S
C16X .377(4) .8199(17) .888(3) .068(5) Uani d PDU .426(7) 2 C
C17X .377(5) .8183(18) .732(3) .075(5) Uani d PDU .426(7) 2 C
C18X .361(5) .682(2) .612(3) .075(6) Uani d PDU .426(7) 2 C
H2 -.0581 .2224 .2976 .054 Uiso calc R 1 . H
H3A .0756 .1325 .5086 .066 Uiso calc R 1 . H
H3B .1015 .0461 .3376 .066 Uiso calc R 1 . H
H5A .4680 .3506 .7024 .069 Uiso calc R 1 . H
H5B .3312 .3490 .7618 .069 Uiso calc R 1 . H
H6 .3162 .4115 .4587 .055 Uiso calc R 1 . H
H7 .003(4) .461(3) .614(6) .058 Uiso d D 1 . H
H9 .384(5) -.091(6) .382(9) .101 Uiso d D 1 . H
H11 .0911 .2950 -.1786 .102 Uiso calc R 1 . H
H12 .2229 .1150 -.1141 .098 Uiso calc R 1 . H
H13 .2231 .0776 .1521 .076 Uiso calc R 1 . H
H16 .4212 .9319 .7922 .111 Uiso calc PR .574(7) 1 H
H17 .4210 .8511 1.0201 .117 Uiso calc PR .574(7) 1 H
H18 .3525 .5943 .9141 .103 Uiso calc PR .574(7) 1 H
H16X .3904 .9010 .9854 .082 Uiso calc PR .426(7) 2 H
H17X .3863 .8987 .7063 .090 Uiso calc PR .426(7) 2 H
H18X .3702 .6629 .5035 .090 Uiso calc PR .426(7) 2 H
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'
S S 0.3331 0.5567 '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_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle
_geom_angle_publ_flag
O7 H7 N1 . 2_566 154(4) no
O9A H9 N8 . 2_656 146(6) no
O9A H9 O9B . 2_656 166(9) no
O7 N1 C2 . . 106.1(2) ?
O7 N1 C6 . . 106.3(3) ?
C2 N1 C6 . . 111.4(3) ?
N1 C2 C14 . . 108.6(3) ?
N1 C2 C3 . . 112.7(3) ?
C14 C2 C3 . . 113.2(3) ?
N1 C2 H2 . . 107.3(2) ?
C14 C2 H2 . . 107.3(2) ?
C3 C2 H2 . . 107.3(2) ?
C4 C3 C2 . . 111.1(3) ?
C4 C3 H3A . . 109.4(2) ?
C2 C3 H3A . . 109.4(2) ?
C4 C3 H3B . . 109.4(2) ?
C2 C3 H3B . . 109.4(2) ?
H3A C3 H3B . . 108.0 ?
N8 C4 C5 . . 120.6(4) ?
N8 C4 C3 . . 121.9(4) ?
C5 C4 C3 . . 117.5(3) ?
C4 C5 C6 . . 110.2(3) ?
C4 C5 H5A . . 109.6(2) ?
C6 C5 H5A . . 109.6(2) ?
C4 C5 H5B . . 109.6(2) ?
C6 C5 H5B . . 109.6(2) ?
H5A C5 H5B . . 108.1 ?
N1 C6 C19 . . 109.7(3) ?
N1 C6 C5 . . 111.6(3) ?
C19 C6 C5 . . 114.5(3) ?
N1 C6 H6 . . 106.9(2) ?
C19 C6 H6 . . 106.9(2) ?
C5 C6 H6 . . 106.9(2) ?
N1 O7 H7 . . 108.(3) ?
C4 N8 O9A . . 113.9(4) ?
C4 N8 O9B . . 114.4(4) ?
O9A N8 O9B . . 131.4(4) ?
N8 O9A O9B . 2_656 114.5(5) ?
N8 O9A H9 . . 108.(5) ?
O9B O9A H9 2_656 . 7.(5) ?
N8 O9B O9A . 2_656 111.3(6) ?
C14 S10 C11 . . 92.4(2) ?
C12 C11 S10 . . 111.3(4) ?
C12 C11 H11 . . 124.4(3) ?
S10 C11 H11 . . 124.4(2) ?
C11 C12 C13 . . 114.7(5) ?
C11 C12 H12 . . 122.6(3) ?
C13 C12 H12 . . 122.6(3) ?
C14 C13 C12 . . 110.4(4) ?
C14 C13 H13 . . 124.8(2) ?
C12 C13 H13 . . 124.8(3) ?
C13 C14 C2 . . 129.6(4) ?
C13 C14 S10 . . 111.1(3) ?
C2 C14 S10 . . 119.3(3) ?
C19 S15 C16 . . 91.1(7) ?
C17 C16 S15 . . 110.4(12) ?
C17 C16 H16 . . 124.8(9) ?
S15 C16 H16 . . 124.8(6) ?
C16 C17 C18 . . 113.8(14) ?
C16 C17 H17 . . 123.1(9) ?
C18 C17 H17 . . 123.1(10) ?
C19 C18 C17 . . 111.8(14) ?
C19 C18 H18 . . 124.1(9) ?
C17 C18 H18 . . 124.1(10) ?
C18 C19 C6 . . 127.4(10) ?
C18X C19 C6 . . 125.3(10) ?
C18 C19 S15 . . 112.9(9) ?
C6 C19 S15 . . 119.7(3) ?
C18X C19 S15X . . 110.9(9) ?
C6 C19 S15X . . 123.7(4) ?
C19 S15X C16X . . 91.4(7) ?
C17X C16X S15X . . 110.9(13) ?
C17X C16X H16X . . 124.5(11) ?
S15X C16X H16X . . 124.6(7) ?
C16X C17X C18X . . 112.6(15) ?
C16X C17X H17X . . 123.7(11) ?
C18X C17X H17X . . 123.7(10) ?
C19 C18X C17X . . 113.5(15) ?
C19 C18X H18X . . 123.2(9) ?
C17X C18X H18X . . 123.3(11) ?
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
N1 O7 . 1.449(4) ?
N1 C2 . 1.476(5) ?
N1 C6 . 1.489(5) ?
C2 C14 . 1.508(5) ?
C2 C3 . 1.534(5) ?
C2 H2 . .98 ?
C3 C4 . 1.497(6) ?
C3 H3A . .97 ?
C3 H3B . .97 ?
C4 N8 . 1.279(5) ?
C4 C5 . 1.469(6) ?
C5 C6 . 1.545(6) ?
C5 H5A . .97 ?
C5 H5B . .97 ?
C6 C19 . 1.489(6) ?
C6 H6 . .98 ?
O7 H7 . .848(10) ?
N8 O9A . 1.459(7) ?
N8 O9B . 1.520(10) ?
O9A O9B 2_656 1.791(9) ?
O9A H9 . .851(10) ?
O9B O9A 2_656 1.791(9) ?
S10 C14 . 1.700(4) ?
S10 C11 . 1.700(5) ?
C11 C12 . 1.323(7) ?
C11 H11 . .93 ?
C12 C13 . 1.415(7) ?
C12 H12 . .93 ?
C13 C14 . 1.384(6) ?
C13 H13 . .93 ?
S15 C19 . 1.696(6) ?
S15 C16 . 1.749(15) ?
C16 C17 . 1.33(2) ?
C16 H16 . .93 ?
C17 C18 . 1.43(2) ?
C17 H17 . .93 ?
C18 C19 . 1.34(2) ?
C18 H18 . .93 ?
C19 C18X . 1.34(2) ?
C19 S15X . 1.708(7) ?
S15X C16X . 1.73(2) ?
C16X C17X . 1.34(2) ?
C16X H16X . .93 ?
C17X C18X . 1.41(2) ?
C17X H17X . .93 ?
C18X H18X . .93 ?
loop_
_geom_contact_atom_site_label_1
_geom_contact_atom_site_label_2
_geom_contact_distance
_geom_contact_site_symmetry_2
_geom_contact_publ_flag
H7 N1 2.03(2) 2_566 no
O7 N1 2.817(4) 2_566 no
H9 N8 1.99(4) 2_656 no
O9A N8 2.738(6) 2_656 no
H9 O9B 0.95(2) 2_656 no
O9A O9B 1.791(9) 2_656 no
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_4
_geom_torsion
O7 N1 C2 C14 . 174.4(3)
C6 N1 C2 C14 . -70.3(4)
O7 N1 C2 C3 . -59.3(4)
C6 N1 C2 C3 . 56.0(4)
N1 C2 C3 C4 . -48.4(4)
C14 C2 C3 C4 . 75.4(4)
C2 C3 C4 N8 . -133.1(4)
C2 C3 C4 C5 . 46.2(5)
N8 C4 C5 C6 . 131.0(4)
C3 C4 C5 C6 . -48.3(5)
O7 N1 C6 C19 . -70.8(4)
C2 N1 C6 C19 . 174.0(3)
O7 N1 C6 C5 . 57.1(4)
C2 N1 C6 C5 . -58.0(4)
C4 C5 C6 N1 . 52.8(4)
C4 C5 C6 C19 . 178.1(3)
C5 C4 N8 O9A . -178.4(4)
C3 C4 N8 O9A . 0.8(6)
C5 C4 N8 O9B . 7.2(7)
C3 C4 N8 O9B . -173.5(5)
C4 N8 O9A O9B 2_656 165.9(5)
O9B N8 O9A O9B 2_656 -21.0(10)
C4 N8 O9B O9A 2_656 -166.4(5)
O9A N8 O9B O9A 2_656 20.5(10)
C14 S10 C11 C12 . 0.5(5)
S10 C11 C12 C13 . -1.4(7)
C11 C12 C13 C14 . 1.8(7)
C12 C13 C14 C2 . -179.8(4)
C12 C13 C14 S10 . -1.4(5)
N1 C2 C14 C13 . 123.6(4)
C3 C2 C14 C13 . -2.4(6)
N1 C2 C14 S10 . -54.7(4)
C3 C2 C14 S10 . 179.3(3)
C11 S10 C14 C13 . 0.5(4)
C11 S10 C14 C2 . 179.2(4)
C19 S15 C16 C17 . 1.(3)
S15 C16 C17 C18 . -1.(4)
C16 C17 C18 C19 . 0.(4)
C17 C18 C19 C18X . 4.(4)
C17 C18 C19 C6 . -178.2(17)
C17 C18 C19 S15 . 1.(3)
C17 C18 C19 S15X . -127.(17)
N1 C6 C19 C18 . 90.(2)
C5 C6 C19 C18 . -37.(2)
N1 C6 C19 C18X . -93.(2)
C5 C6 C19 C18X . 141.(2)
N1 C6 C19 S15 . -89.5(5)
C5 C6 C19 S15 . 144.2(4)
N1 C6 C19 S15X . 84.6(6)
C5 C6 C19 S15X . -41.8(7)
C16 S15 C19 C18 . -2.(2)
C16 S15 C19 C18X . -30.(17)
C16 S15 C19 C6 . 177.9(13)
C16 S15 C19 S15X . 3.5(14)
C18 C19 S15X C16X . 56.(14)
C18X C19 S15X C16X . 6.(3)
C6 C19 S15X C16X . -171.9(13)
S15 C19 S15X C16X . 2.3(14)
C19 S15X C16X C17X . -2.(3)
S15X C16X C17X C18X . -3.(5)
C18 C19 C18X C17X . -13.(4)
C6 C19 C18X C17X . 169.(3)
S15 C19 C18X C17X . 139.(19)
S15X C19 C18X C17X . -9.(4)
C16X C17X C18X C19 . 8.(5)
