#------------------------------------------------------------------------------
#$Date: 2011-09-10 04:16:28 +0100 (Sat, 10 Sep 2011) $
#$Revision: 25271 $
#$URL: svn://www.crystallography.net/cod/cif/2/2006563.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_2006563
loop_
_publ_author_name
'D\'iaz, E.'
'Barrios, H.'
'Toscano, R. A.'
_publ_section_title
;
 Three <i>trans</i>-2,6-Diaryl Derivatives of Oximes of
 <i>N</i>-Hydroxy-4-piperidone
;
_journal_issue                   10
_journal_name_full               'Acta Crystallographica Section C'
_journal_page_first              1468
_journal_page_last               1471
_journal_volume                  53
_journal_year                    1997
_chemical_formula_moiety         'C17 H18 N2 O2'
_chemical_formula_sum            'C17 H18 N2 O2'
_chemical_formula_weight         282.33
_chemical_name_systematic
;
trans 1-hydroxy-2,6-diphenyl-4-piperidone oxime ?
;
_space_group_IT_number           14
_symmetry_cell_setting           monoclinic
_symmetry_space_group_name_Hall  '-P 2yn'
_symmetry_space_group_name_H-M   'P 1 21/n 1'
_cell_angle_alpha                90.00
_cell_angle_beta                 97.75(2)
_cell_angle_gamma                90.00
_cell_formula_units_Z            4
_cell_length_a                   9.890(3)
_cell_length_b                   10.437(3)
_cell_length_c                   14.790(4)
_cell_measurement_reflns_used    25
_cell_measurement_temperature    273(2)
_cell_measurement_theta_max      13.3
_cell_measurement_theta_min      5.1
_cell_volume                     1512.7(8)
_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      273(2)
_diffrn_measurement_device       'Nicolet P3/F diffractometer'
_diffrn_measurement_method       \q/2\q
_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  0.0350
_diffrn_reflns_av_sigmaI/netI    0.0313
_diffrn_reflns_limit_h_max       10
_diffrn_reflns_limit_h_min       0
_diffrn_reflns_limit_k_max       11
_diffrn_reflns_limit_k_min       0
_diffrn_reflns_limit_l_max       15
_diffrn_reflns_limit_l_min       -15
_diffrn_reflns_number            2033
_diffrn_reflns_theta_max         55.06
_diffrn_reflns_theta_min         5.08
_diffrn_standards_decay_%        3
_diffrn_standards_interval_count 98
_diffrn_standards_number         2
_exptl_absorpt_coefficient_mu    0.660
_exptl_absorpt_correction_type   none
_exptl_crystal_colour            colourless
_exptl_crystal_density_diffrn    1.240
_exptl_crystal_description       irregular
_exptl_crystal_F_000             600
_exptl_crystal_size_max          0.30
_exptl_crystal_size_mid          0.18
_exptl_crystal_size_min          0.14
_refine_diff_density_max         0.140
_refine_diff_density_min         -0.194
_refine_ls_extinction_coef       0.0032(6)
_refine_ls_extinction_method     'SHELXL93 (Sheldrick, 1993)'
_refine_ls_goodness_of_fit_all   1.058
_refine_ls_goodness_of_fit_obs   1.188
_refine_ls_hydrogen_treatment    'H atoms riding'
_refine_ls_matrix_type           full
_refine_ls_number_parameters     207
_refine_ls_number_reflns         1902
_refine_ls_number_restraints     1
_refine_ls_restrained_S_all      1.058
_refine_ls_restrained_S_obs      1.187
_refine_ls_R_factor_all          0.0712
_refine_ls_R_factor_obs          0.0501
_refine_ls_shift/esd_max         0.000
_refine_ls_shift/esd_mean        0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_scheme
'calc w = 1/[\s^2^(Fo^2^)+(0.0737P)^2^+0.2342P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_wR_factor_all         0.1383
_refine_ls_wR_factor_obs         0.1280
_reflns_number_observed          1353
_reflns_number_total             1902
_reflns_observed_criterion       >2sigma(I)
_[local]_cod_data_source_file    cf1113.cif
_[local]_cod_data_source_block   1
_[local]_cod_cif_authors_sg_H-M  'P 21/n'
_cod_database_code               2006563
loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'-x+1/2, y+1/2, -z+1/2'
'-x, -y, -z'
'x-1/2, -y-1/2, z-1/2'
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
N1 0.0541(14) 0.0483(13) 0.0557(13) -0.0080(10) 0.0021(11) 0.0057(11)
C2 0.059(2) 0.053(2) 0.062(2) -0.0110(14) 0.0051(14) -0.0030(14)
C3 0.074(2) 0.055(2) 0.069(2) -0.016(2) -0.005(2) 0.0005(15)
C4 0.063(2) 0.059(2) 0.075(2) -0.021(2) -0.009(2) 0.005(2)
C5 0.054(2) 0.064(2) 0.082(2) -0.0123(15) 0.0054(15) 0.009(2)
C6 0.048(2) 0.052(2) 0.066(2) -0.0095(13) 0.0063(13) 0.0077(14)
O7 0.0625(13) 0.0604(13) 0.0632(12) -0.0175(10) -0.0007(10) 0.0104(10)
N8 0.065(2) 0.062(2) 0.096(2) -0.0211(14) 0.0065(15) -0.0037(15)
O9A 0.085(3) 0.058(3) 0.130(4) -0.034(2) 0.024(3) -0.021(3)
O9B 0.077(4) 0.089(4) 0.111(4) -0.040(3) 0.011(3) -0.006(3)
C10 0.063(2) 0.051(2) 0.073(2) -0.0014(15) 0.004(2) -0.001(2)
C11 0.075(2) 0.077(2) 0.090(2) -0.014(2) -0.007(2) 0.008(2)
C12 0.077(2) 0.100(3) 0.105(3) -0.006(2) -0.024(2) -0.003(3)
C13 0.114(3) 0.091(3) 0.082(2) 0.012(2) -0.020(2) 0.012(2)
C14 0.105(3) 0.082(3) 0.090(3) -0.005(2) -0.002(2) 0.026(2)
C15 0.074(2) 0.064(2) 0.090(2) -0.009(2) -0.003(2) 0.013(2)
C16 0.058(2) 0.053(2) 0.070(2) -0.0062(15) 0.0156(15) 0.004(2)
C17 0.079(2) 0.062(2) 0.101(2) 0.003(2) 0.005(2) 0.003(2)
C18 0.101(3) 0.069(3) 0.140(4) 0.020(2) 0.030(3) 0.012(3)
C19 0.112(3) 0.062(2) 0.139(4) -0.001(2) 0.062(3) -0.017(3)
C20 0.105(3) 0.088(3) 0.092(3) -0.018(2) 0.023(2) -0.032(2)
C21 0.075(2) 0.066(2) 0.083(2) -0.002(2) 0.015(2) -0.006(2)
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_type_symbol
N1 0.0840(2) 0.6226(2) 0.47643(14) 0.0532(6) Uani d . 1 N
C2 0.0559(3) 0.7566(3) 0.5026(2) 0.0583(8) Uani d . 1 C
C3 0.1833(3) 0.8241(3) 0.5515(2) 0.0673(8) Uani d . 1 C
C4 0.3074(3) 0.8050(3) 0.5056(2) 0.0673(9) Uani d . 1 C
C5 0.3289(3) 0.6742(3) 0.4708(2) 0.0673(8) Uani d . 1 C
C6 0.1963(3) 0.6195(3) 0.4198(2) 0.0556(7) Uani d . 1 C
O7 0.1330(2) 0.5549(2) 0.56002(13) 0.0629(6) Uani d . 1 O
N8 0.3934(3) 0.8942(2) 0.5001(2) 0.0750(8) Uani d . 1 N
O9A 0.3606(4) 1.0109(4) 0.5454(3) 0.090(2) Uani d PD 0.526(5) O
O9B 0.5083(5) 0.8620(5) 0.4496(3) 0.093(2) Uani d P 0.474(5) O
C10 -0.0152(3) 0.8233(3) 0.4182(2) 0.0629(8) Uani d . 1 C
C11 -0.1451(3) 0.7843(3) 0.3829(2) 0.0824(10) Uani d . 1 C
C12 -0.2113(4) 0.8360(4) 0.3037(3) 0.0974(12) Uani d . 1 C
C13 -0.1504(4) 0.9281(4) 0.2578(3) 0.0986(12) Uani d . 1 C
C14 -0.0233(4) 0.9688(4) 0.2916(2) 0.0939(11) Uani d . 1 C
C15 0.0439(3) 0.9175(3) 0.3707(2) 0.0774(9) Uani d . 1 C
C16 0.2083(3) 0.4875(3) 0.3797(2) 0.0598(8) Uani d . 1 C
C17 0.3009(3) 0.3976(3) 0.4173(3) 0.0814(10) Uani d . 1 C
C18 0.3070(4) 0.2791(4) 0.3790(3) 0.1022(13) Uani d . 1 C
C19 0.2225(5) 0.2469(4) 0.3027(3) 0.1000(13) Uani d . 1 C
C20 0.1281(4) 0.3344(4) 0.2639(3) 0.0938(11) Uani d . 1 C
C21 0.1224(3) 0.4542(3) 0.3024(2) 0.0742(9) Uani d . 1 C
H2 -0.0102 0.7520 0.5463 0.060 Uiso calc R 1 H
H3A 0.1648 0.9151 0.5547 0.060 Uiso calc R 1 H
H3B 0.2016 0.7920 0.6135 0.060 Uiso calc R 1 H
H5A 0.3618 0.6185 0.5216 0.060 Uiso calc R 1 H
H5B 0.3979 0.6771 0.4301 0.060 Uiso calc R 1 H
H6 0.1693 0.6771 0.3682 0.060 Uiso calc R 1 H
H7 0.074(3) 0.496(3) 0.5633(18) 0.060 Uiso d . 1 H
H9 0.427(2) 1.060(2) 0.5379(19) 0.060 Uiso d D 1 H
H11 -0.1885 0.7217 0.4133 0.060 Uiso calc R 1 H
H12 -0.2986 0.8080 0.2812 0.060 Uiso calc R 1 H
H13 -0.1954 0.9626 0.2041 0.060 Uiso calc R 1 H
H14 0.0188 1.0320 0.2609 0.060 Uiso calc R 1 H
H15 0.1309 0.9467 0.3927 0.060 Uiso calc R 1 H
H17 0.3603 0.4178 0.4695 0.060 Uiso calc R 1 H
H18 0.3701 0.2196 0.4057 0.060 Uiso calc R 1 H
H19 0.2282 0.1663 0.2766 0.060 Uiso calc R 1 H
H20 0.0684 0.3129 0.2120 0.060 Uiso calc R 1 H
H21 0.0593 0.5136 0.2755 0.060 Uiso calc R 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 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'
loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle_site_symmetry_3
_geom_angle
_geom_angle_publ_flag
O7 H7 N1 3_566 159(3) no
O9A H9 N8 3_676 156(3) no
O9A H9 O9B 3_676 157(4) no
O7 N1 C6 . 106.4(2) ?
O7 N1 C2 . 106.8(2) ?
C6 N1 C2 . 110.4(2) ?
N1 C2 C10 . 107.4(2) ?
N1 C2 C3 . 112.5(2) ?
C10 C2 C3 . 115.9(2) ?
N1 C2 H2 . 106.82(13) ?
C10 C2 H2 . 106.8(2) ?
C3 C2 H2 . 106.8(2) ?
C4 C3 C2 . 113.4(2) ?
C4 C3 H3A . 108.9(2) ?
C2 C3 H3A . 108.9(2) ?
C4 C3 H3B . 108.9(2) ?
C2 C3 H3B . 108.9(2) ?
H3A C3 H3B . 107.7 ?
N8 C4 C5 . 121.5(3) ?
N8 C4 C3 . 122.0(3) ?
C5 C4 C3 . 116.4(2) ?
C4 C5 C6 . 111.1(2) ?
C4 C5 H5A . 109.4(2) ?
C6 C5 H5A . 109.42(15) ?
C4 C5 H5B . 109.4(2) ?
C6 C5 H5B . 109.4(2) ?
H5A C5 H5B . 108.0 ?
N1 C6 C16 . 110.3(2) ?
N1 C6 C5 . 111.8(2) ?
C16 C6 C5 . 115.2(2) ?
N1 C6 H6 . 106.29(13) ?
C16 C6 H6 . 106.3(2) ?
C5 C6 H6 . 106.29(15) ?
N1 O7 H7 . 104.3(18) ?
C4 N8 O9A . 113.1(3) ?
C4 N8 O9B . 115.6(3) ?
O9A N8 O9B . 131.3(3) ?
N8 O9A H9 . 103.(2) ?
C11 C10 C15 . 116.9(3) ?
C11 C10 C2 . 118.7(3) ?
C15 C10 C2 . 124.3(3) ?
C12 C11 C10 . 121.3(3) ?
C12 C11 H11 . 119.4(2) ?
C10 C11 H11 . 119.4(2) ?
C13 C12 C11 . 120.7(3) ?
C13 C12 H12 . 119.7(2) ?
C11 C12 H12 . 119.7(2) ?
C14 C13 C12 . 119.2(3) ?
C14 C13 H13 . 120.4(2) ?
C12 C13 H13 . 120.4(2) ?
C13 C14 C15 . 120.6(4) ?
C13 C14 H14 . 119.7(2) ?
C15 C14 H14 . 119.7(2) ?
C14 C15 C10 . 121.4(3) ?
C14 C15 H15 . 119.3(2) ?
C10 C15 H15 . 119.3(2) ?
C21 C16 C17 . 117.8(3) ?
C21 C16 C6 . 119.0(3) ?
C17 C16 C6 . 123.1(3) ?
C18 C17 C16 . 121.0(4) ?
C18 C17 H17 . 119.5(3) ?
C16 C17 H17 . 119.5(2) ?
C19 C18 C17 . 120.9(4) ?
C19 C18 H18 . 119.5(3) ?
C17 C18 H18 . 119.5(3) ?
C18 C19 C20 . 119.4(4) ?
C18 C19 H19 . 120.3(3) ?
C20 C19 H19 . 120.3(2) ?
C19 C20 C21 . 119.6(4) ?
C19 C20 H20 . 120.2(2) ?
C21 C20 H20 . 120.2(2) ?
C16 C21 C20 . 121.2(3) ?
C16 C21 H21 . 119.4(2) ?
C20 C21 H21 . 119.4(2) ?
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
N1 O7 1.450(3)
N1 C6 1.479(3)
N1 C2 1.488(3)
C2 C10 1.516(4)
C2 C3 1.536(4)
C2 H2 0.98
C3 C4 1.494(4)
C3 H3A 0.97
C3 H3B 0.97
C4 N8 1.271(3)
C4 C5 1.485(4)
C5 C6 1.532(4)
C5 H5A 0.97
C5 H5B 0.97
C6 C16 1.511(4)
C6 H6 0.98
O7 H7 0.85(3)
N8 O9A 1.448(5)
N8 O9B 1.481(6)
O9A H9 0.848(11)
C10 C11 1.381(4)
C10 C15 1.383(4)
C11 C12 1.373(5)
C11 H11 0.93
C12 C13 1.363(5)
C12 H12 0.93
C13 C14 1.357(5)
C13 H13 0.93
C14 C15 1.373(4)
C14 H14 0.93
C15 H15 0.93
C16 C21 1.374(4)
C16 C17 1.376(4)
C17 C18 1.365(5)
C17 H17 0.93
C18 C19 1.353(5)
C18 H18 0.93
C19 C20 1.375(5)
C19 H19 0.93
C20 C21 1.378(5)
C20 H20 0.93
C21 H21 0.93
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 2.02(3) 3_566 no
O7 N1 2.831(3) 3_566 no
H9 N8 2.00(2) 3_676 no
O9A N8 2.792(5) 3_676 no
H9 O9B 1.04(2) 3_676 no
O9A O9B 1.850(6) 3_676 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
O7 N1 C2 C10 -171.7(2)
C6 N1 C2 C10 73.1(3)
O7 N1 C2 C3 59.6(3)
C6 N1 C2 C3 -55.7(3)
N1 C2 C3 C4 46.0(3)
C10 C2 C3 C4 -78.2(3)
C2 C3 C4 N8 141.4(3)
C2 C3 C4 C5 -41.7(4)
N8 C4 C5 C6 -137.8(3)
C3 C4 C5 C6 45.3(3)
O7 N1 C6 C16 74.4(2)
C2 N1 C6 C16 -170.0(2)
O7 N1 C6 C5 -55.2(3)
C2 N1 C6 C5 60.4(3)
C4 C5 C6 N1 -54.5(3)
C4 C5 C6 C16 178.6(2)
C5 C4 N8 O9A -174.5(3)
C3 C4 N8 O9A 2.3(4)
C5 C4 N8 O9B 5.5(4)
C3 C4 N8 O9B -177.8(3)
N1 C2 C10 C11 67.3(3)
C3 C2 C10 C11 -165.9(3)
N1 C2 C10 C15 -109.3(3)
C3 C2 C10 C15 17.4(4)
C15 C10 C11 C12 0.7(5)
C2 C10 C11 C12 -176.3(3)
C10 C11 C12 C13 -0.2(6)
C11 C12 C13 C14 -0.4(6)
C12 C13 C14 C15 0.4(6)
C13 C14 C15 C10 0.1(6)
C11 C10 C15 C14 -0.6(5)
C2 C10 C15 C14 176.1(3)
N1 C6 C16 C21 81.7(3)
C5 C6 C16 C21 -150.6(3)
N1 C6 C16 C17 -97.9(3)
C5 C6 C16 C17 29.9(4)
C21 C16 C17 C18 -0.2(5)
C6 C16 C17 C18 179.4(3)
C16 C17 C18 C19 0.4(6)
C17 C18 C19 C20 -0.9(6)
C18 C19 C20 C21 1.1(6)
C17 C16 C21 C20 0.4(5)
C6 C16 C21 C20 -179.1(3)
C19 C20 C21 C16 -0.9(5)