#------------------------------------------------------------------------------
#$Date: 2016-02-20 02:53:41 +0200 (Sat, 20 Feb 2016) $
#$Revision: 176768 $
#$URL: svn://www.crystallography.net/cod/cif/2/10/18/2101875.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_2101875
loop_
_publ_author_name
'Maurin, Jan K.'
'Czarnocki, Zbigniew'
'Paluchowska, Beata'
'Winnicka-Maurin, Małgorzata'
_publ_section_title
;
 Conformation-Related Reaction Efficiency of Glutarimides with
 Phenyllithium. Structures of 3,3,5,5-Tetramethylglutarimide and
 2-Hydroxy-2-phenyl-3,3,5,5-tetramethyl-6-piperidone. X-ray and
 Theoretical Study
;
_journal_issue                   4
_journal_name_full               'Acta Crystallographica Section B'
_journal_page_first              719
_journal_page_last               725
_journal_paper_doi               10.1107/S0108768197004874
_journal_volume                  53
_journal_year                    1997
_chemical_formula_sum            'C15 H21 N O2'
_chemical_formula_weight         247.33
_chemical_melting_point          375.0(10)
_chemical_name_systematic
2-hydroxy-2-phenyl-3,3,5,5-tetramethyl-6-piperidone
_space_group_IT_number           2
_symmetry_cell_setting           triclinic
_symmetry_space_group_name_Hall  '-P 1'
_symmetry_space_group_name_H-M   'P -1'
_audit_creation_method           SHELXL
_cell_angle_alpha                117.100(10)
_cell_angle_beta                 103.390(10)
_cell_angle_gamma                91.288(7)
_cell_formula_units_Z            2
_cell_length_a                   6.1685(6)
_cell_length_b                   11.1475(10)
_cell_length_c                   11.526(2)
_cell_measurement_reflns_used    25
_cell_measurement_temperature    293(2)
_cell_measurement_theta_max      29
_cell_measurement_theta_min      18
_cell_volume                     678.84(17)
_computing_cell_refinement       'Kuma software, 1991'
_computing_data_collection       'Kuma software, 1991'
_computing_data_reduction        'Kuma software, 1991'
_computing_molecular_graphics    'ORTEP II, Johnson, 1976'
_computing_publication_material  'SHELXL-93 (Sheldrick, 1993)'
_computing_structure_refinement  'SHELXL-93 (Sheldrick, 1993)'
_computing_structure_solution    'SHELXS-86 (Sheldrick, 1990)'
_diffrn_ambient_temperature      293(2)
_diffrn_measurement_device       'Kuma KM-4 κ axis diffractometer'
_diffrn_measurement_method       'profile data from ω-2θ'
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_source         'fine-focus sealed tube'
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54178
_diffrn_reflns_av_R_equivalents  0.0463
_diffrn_reflns_av_sigmaI/netI    0.0251
_diffrn_reflns_limit_h_max       0
_diffrn_reflns_limit_h_min       -7
_diffrn_reflns_limit_k_max       13
_diffrn_reflns_limit_k_min       -13
_diffrn_reflns_limit_l_max       13
_diffrn_reflns_limit_l_min       -13
_diffrn_reflns_number            2449
_diffrn_reflns_theta_max         64.94
_diffrn_reflns_theta_min         4.48
_diffrn_standards_decay_%        'not observed'
_diffrn_standards_interval_count 200
_diffrn_standards_number         3
_exptl_absorpt_coefficient_mu    0.631
_exptl_absorpt_correction_type   none
_exptl_crystal_colour            'colorless, transparent'
_exptl_crystal_density_diffrn    1.210
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    .
_exptl_crystal_description       platy
_exptl_crystal_F_000             268
_exptl_crystal_size_max          0.4
_exptl_crystal_size_mid          0.2
_exptl_crystal_size_min          0.2
_refine_diff_density_max         0.239
_refine_diff_density_min         -0.202
_refine_ls_extinction_coef       0.028(3)
_refine_ls_extinction_method     'SHELXL93 (Sheldrick, 1993)'
_refine_ls_goodness_of_fit_all   1.005
_refine_ls_goodness_of_fit_obs   1.057
_refine_ls_hydrogen_treatment    refall
_refine_ls_matrix_type           full
_refine_ls_number_parameters     248
_refine_ls_number_reflns         2225
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.016
_refine_ls_restrained_S_obs      1.057
_refine_ls_R_factor_all          0.0547
_refine_ls_R_factor_obs          0.0410
_refine_ls_shift/esd_max         0.000
_refine_ls_shift/esd_mean        0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'w=1/[σ²(Fo²)+(0.0711P)²+0.1785P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_all         0.1250
_refine_ls_wR_factor_obs         0.1154
_reflns_number_observed          1800
_reflns_number_total             2226
_reflns_observed_criterion       >2sigma(I)
_cod_data_source_file            ab0372.cif
_cod_data_source_block           9
_cod_depositor_comments
;
The following automatic conversions were performed:

'_chemical_melting_point' value '374-376 K' was changed to
'375.0(10)' - the average value was taken and precision was
estimated.

Automatic conversion script
Id: cif_fix_values 1646 2011-03-28 12:23:43Z adriana 

The following automatic conversions were performed:

'_chemical_melting_point' value '374-376 K' was changed to
'375.0(10)' - the average value was taken and precision was
estimated.

Automatic conversion script
Id: cif_fix_values 1715 2011-07-08 13:25:40Z adriana 

The following automatic conversions were performed:

'_refine_ls_weighting_scheme' value 'calc
w=1/[\s^2^(Fo^2^)+(0.0711P)^2^+0.1785P] 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^)+(0.0711P)^2^+0.1785P] where P=(Fo^2^+2Fc^2^)/3'.

Automatic conversion script
Id: cif_fix_values 3143 2015-03-26 13:38:13Z robertas 
;
_cod_original_cell_volume        678.84(15)
_cod_database_code               2101875
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_occupancy
_atom_site_type_symbol
O2 0.7400(2) 0.71197(12) 0.14133(13) 0.0471(4) Uani d 1 O
O1 0.0976(2) 0.52412(12) -0.11829(13) 0.0546(4) Uani d 1 O
N 0.3560(2) 0.62561(14) 0.08216(15) 0.0420(4) Uani d 1 N
C2 0.5429(3) 0.7290(2) 0.1879(2) 0.0388(4) Uani d 1 C
C3 0.4847(3) 0.8709(2) 0.2079(2) 0.0416(4) Uani d 1 C
C4 0.4437(3) 0.8666(2) 0.0694(2) 0.0477(5) Uani d 1 C
H4A 0.593(4) 0.865(2) 0.053(2) 0.063(6) Uiso d 1 H
H4B 0.401(3) 0.957(2) 0.0805(18) 0.049(5) Uiso d 1 H
C5 0.2691(3) 0.7492(2) -0.0507(2) 0.0468(4) Uani d 1 C
C6 0.2349(3) 0.6254(2) -0.0307(2) 0.0414(4) Uani d 1 C
C11 0.5779(3) 0.7112(2) 0.3139(2) 0.0404(4) Uani d 1 C
C12 0.3995(3) 0.6634(2) 0.3449(2) 0.0479(4) Uani d 1 C
H12 0.251(3) 0.6421(19) 0.285(2) 0.049(5) Uiso d 1 H
C13 0.4361(4) 0.6476(2) 0.4599(2) 0.0590(5) Uani d 1 C
H13 0.313(4) 0.612(3) 0.476(3) 0.082(7) Uiso d 1 H
C14 0.6488(4) 0.6786(2) 0.5457(2) 0.0629(6) Uani d 1 C
H14 0.670(4) 0.667(3) 0.625(3) 0.087(8) Uiso d 1 H
C15 0.8264(4) 0.7267(2) 0.5167(2) 0.0600(5) Uani d 1 C
H15 0.983(4) 0.751(2) 0.579(3) 0.076(7) Uiso d 1 H
C16 0.7921(3) 0.7428(2) 0.4022(2) 0.0504(5) Uani d 1 C
H16 0.910(4) 0.773(2) 0.378(2) 0.058(6) Uiso d 1 H
C31 0.6830(3) 0.9825(2) 0.3077(2) 0.0551(5) Uani d 1 C
H31A 0.818(4) 0.970(2) 0.276(2) 0.074(7) Uiso d 1 H
H31B 0.719(4) 0.991(2) 0.403(3) 0.070(7) Uiso d 1 H
H31C 0.643(4) 1.071(3) 0.321(2) 0.071(6) Uiso d 1 H
C32 0.2785(3) 0.9040(2) 0.2632(2) 0.0521(5) Uani d 1 C
H32A 0.143(4) 0.832(2) 0.210(2) 0.065(6) Uiso d 1 H
H32B 0.238(4) 0.994(3) 0.272(2) 0.070(6) Uiso d 1 H
H32C 0.305(4) 0.914(2) 0.355(3) 0.069(7) Uiso d 1 H
C51 0.0371(4) 0.7944(3) -0.0777(3) 0.0737(7) Uani d 1 C
H51A 0.054(4) 0.871(3) -0.104(3) 0.086(8) Uiso d 1 H
H51B -0.021(5) 0.832(3) 0.007(3) 0.106(10) Uiso d 1 H
H51C -0.075(5) 0.716(3) -0.152(3) 0.088(8) Uiso d 1 H
C52 0.3520(6) 0.6993(3) -0.1788(3) 0.0760(7) Uani d 1 C
H52A 0.378(4) 0.780(3) -0.195(3) 0.088(8) Uiso d 1 H
H52B 0.239(4) 0.623(3) -0.259(3) 0.083(8) Uiso d 1 H
H52C 0.502(5) 0.663(3) -0.168(3) 0.082(8) Uiso d 1 H
H1 0.330(3) 0.552(2) 0.088(2) 0.051(5) Uiso d 1 H
H2 0.790(4) 0.634(2) 0.143(2) 0.066(6) Uiso 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 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
_geom_angle_publ_flag
C2 O2 H2 106.6(13) no
C6 N C2 127.14(14) yes
C6 N H1 115.4(13) no
C2 N H1 117.0(13) no
O2 C2 N 109.28(13) yes
O2 C2 C11 111.08(13) yes
N C2 C11 107.96(12) yes
O2 C2 C3 105.97(12) yes
N C2 C3 107.82(13) yes
C11 C2 C3 114.60(13) yes
C31 C3 C32 108.3(2) yes
C31 C3 C4 108.56(15) yes
C32 C3 C4 111.6(2) yes
C31 C3 C2 110.41(14) yes
C32 C3 C2 111.11(13) yes
C4 C3 C2 106.86(13) yes
C3 C4 C5 117.01(13) yes
C3 C4 H4A 104.9(13) no
C5 C4 H4A 111.5(12) no
C3 C4 H4B 107.6(11) no
C5 C4 H4B 110.2(10) no
H4A C4 H4B 104.9(16) no
C6 C5 C52 105.8(2) yes
C6 C5 C51 107.3(2) yes
C52 C5 C51 109.0(2) yes
C6 C5 C4 113.38(15) yes
C52 C5 C4 109.4(2) yes
C51 C5 C4 111.7(2) yes
O1 C6 N 119.99(15) yes
O1 C6 C5 120.4(2) yes
N C6 C5 119.57(15) yes
C16 C11 C12 118.0(2) yes
C16 C11 C2 120.13(15) yes
C12 C11 C2 121.89(15) yes
C13 C12 C11 120.7(2) yes
C13 C12 H12 120.9(12) no
C11 C12 H12 118.4(12) no
C14 C13 C12 120.6(2) yes
C14 C13 H13 120.9(16) no
C12 C13 H13 118.5(16) no
C13 C14 C15 119.4(2) yes
C13 C14 H14 119.1(15) no
C15 C14 H14 121.5(15) no
C14 C15 C16 120.6(2) yes
C14 C15 H15 120.7(14) no
C16 C15 H15 118.7(14) no
C15 C16 C11 120.7(2) yes
C15 C16 H16 122.7(13) no
C11 C16 H16 116.5(13) no
C3 C31 H31A 112.4(14) no
C3 C31 H31B 112.4(13) no
H31A C31 H31B 109.5(19) no
C3 C31 H31C 109.6(14) no
H31A C31 H31C 108.5(19) no
H31B C31 H31C 104.0(18) no
C3 C32 H32A 114.8(13) no
C3 C32 H32B 110.4(13) no
H32A C32 H32B 109.9(18) no
C3 C32 H32C 113.0(13) no
H32A C32 H32C 103.0(18) no
H32B C32 H32C 105.0(18) no
C5 C51 H51A 108.3(14) no
C5 C51 H51B 111.2(17) no
H51A C51 H51B 109.(2) no
C5 C51 H51C 110.7(15) no
H51A C51 H51C 110.(2) no
H51B C51 H51C 108.(2) no
C5 C52 H52A 107.8(15) no
C5 C52 H52B 110.6(15) no
H52A C52 H52B 112.(2) no
C5 C52 H52C 112.5(15) no
H52A C52 H52C 107.(2) no
H52B C52 H52C 107.(2) no
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_publ_flag
O2 C2 1.422(2) yes
O2 H2 0.94(2) no
O1 C6 1.238(2) yes
N C6 1.341(2) yes
N C2 1.468(2) yes
N H1 0.87(2) no
C2 C11 1.521(2) yes
C2 C3 1.555(2) yes
C3 C31 1.531(2) yes
C3 C32 1.531(2) yes
C3 C4 1.534(3) yes
C4 C5 1.545(3) yes
C4 H4A 0.98(2) no
C4 H4B 1.01(2) no
C5 C6 1.518(2) yes
C5 C52 1.538(3) yes
C5 C51 1.538(3) yes
C11 C16 1.391(2) yes
C11 C12 1.398(2) yes
C12 C13 1.382(3) yes
C12 H12 0.96(2) no
C13 C14 1.373(3) yes
C13 H13 0.94(3) no
C14 C15 1.380(3) yes
C14 H14 0.96(3) no
C15 C16 1.381(3) yes
C15 H15 1.00(2) no
C16 H16 0.94(2) no
C31 H31A 0.97(2) no
C31 H31B 1.02(2) no
C31 H31C 0.97(2) no
C32 H32A 1.00(2) no
C32 H32B 1.01(2) no
C32 H32C 0.98(2) no
C51 H51A 1.03(3) no
C51 H51B 1.03(3) no
C51 H51C 0.99(3) no
C52 H52A 1.02(3) no
C52 H52B 1.01(3) no
C52 H52C 1.02(3) 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
_geom_torsion_publ_flag
C6 N C2 O2 -76.7(2) no
C6 N C2 C11 162.3(2) no
C6 N C2 C3 38.0(2) no
O2 C2 C3 C31 -57.8(2) no
N C2 C3 C31 -174.73(14) no
C11 C2 C3 C31 65.0(2) no
O2 C2 C3 C32 -177.97(15) no
N C2 C3 C32 65.1(2) no
C11 C2 C3 C32 -55.1(2) no
O2 C2 C3 C4 60.1(2) no
N C2 C3 C4 -56.8(2) no
C11 C2 C3 C4 -177.07(13) no
C31 C3 C4 C5 172.80(15) no
C32 C3 C4 C5 -67.9(2) no
C2 C3 C4 C5 53.7(2) no
C3 C4 C5 C6 -24.1(2) no
C3 C4 C5 C52 -141.9(2) no
C3 C4 C5 C51 97.4(2) no
C2 N C6 O1 172.29(15) no
C2 N C6 C5 -7.2(2) no
C52 C5 C6 O1 -61.1(2) no
C51 C5 C6 O1 55.2(2) no
C4 C5 C6 O1 179.1(2) no
C52 C5 C6 N 118.4(2) no
C51 C5 C6 N -125.3(2) no
C4 C5 C6 N -1.5(2) no
O2 C2 C11 C16 29.0(2) no
N C2 C11 C16 148.8(2) no
C3 C2 C11 C16 -91.1(2) no
O2 C2 C11 C12 -151.1(2) no
N C2 C11 C12 -31.3(2) no
C3 C2 C11 C12 88.9(2) no
C16 C11 C12 C13 -0.3(3) no
C2 C11 C12 C13 179.8(2) no
C11 C12 C13 C14 -0.1(3) no
C12 C13 C14 C15 0.4(3) no
C13 C14 C15 C16 -0.4(3) no
C14 C15 C16 C11 0.1(3) no
C12 C11 C16 C15 0.2(3) no
C2 C11 C16 C15 -179.8(2) no
