#------------------------------------------------------------------------------
#$Date: 2016-02-20 22:30:07 +0200 (Sat, 20 Feb 2016) $
#$Revision: 176789 $
#$URL: svn://www.crystallography.net/cod/cif/2/22/36/2223620.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_2223620
loop_
_publ_author_name
'Thenmozhi, M.'
'Ponnuswamy, S.'
'Umamaheshwari, J.'
'Jamesh, M.'
'Ponnuswamy, M. N.'
_publ_section_title
;
 c-3,t-3-Dimethyl-r-2,c-6-diphenylpiperidin-4-one
;
_journal_coeditor_code           BT5058
_journal_issue                   11
_journal_name_full               'Acta Crystallographica Section E'
_journal_page_first              o2794
_journal_paper_doi               10.1107/S1600536809041580
_journal_volume                  65
_journal_year                    2009
_chemical_formula_iupac          'C19 H21 N O'
_chemical_formula_moiety         'C19 H21 N O'
_chemical_formula_sum            'C19 H21 N O'
_chemical_formula_weight         279.37
_chemical_name_systematic
;
c-3,t-3-Dimethyl-r-2,c-6-diphenylpiperidin-4-one
;
_space_group_IT_number           2
_symmetry_cell_setting           triclinic
_symmetry_space_group_name_Hall  '-P 1'
_symmetry_space_group_name_H-M   'P -1'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_audit_creation_method           SHELXL-97
_cell_angle_alpha                98.559(2)
_cell_angle_beta                 92.836(3)
_cell_angle_gamma                96.677(3)
_cell_formula_units_Z            2
_cell_length_a                   6.0293(4)
_cell_length_b                   10.8198(6)
_cell_length_c                   12.1649(6)
_cell_measurement_reflns_used    3556
_cell_measurement_temperature    293(2)
_cell_measurement_theta_max      28.2
_cell_measurement_theta_min      1.7
_cell_volume                     777.62(8)
_computing_cell_refinement       'SAINT (Bruker, 2004)'
_computing_data_collection       'APEX2 (Bruker, 2004)'
_computing_data_reduction        'SAINT (Bruker, 2004)'
_computing_molecular_graphics    'ORTEP-3 (Farrugia, 1997)'
_computing_publication_material
'SHELXL97 (Sheldrick, 2008) and PLATON (Spek, 2009)'
_computing_structure_refinement  'SHELXL97 (Sheldrick, 2008)'
_computing_structure_solution    'SHELXS97 (Sheldrick, 2008)'
_diffrn_ambient_temperature      293(2)
_diffrn_measured_fraction_theta_full 0.985
_diffrn_measured_fraction_theta_max 0.926
_diffrn_measurement_device_type  'Bruker Kappa APEXII area-detector'
_diffrn_measurement_method       'ω and φ'
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_source         'fine-focus sealed tube'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0363
_diffrn_reflns_av_sigmaI/netI    0.0440
_diffrn_reflns_limit_h_max       7
_diffrn_reflns_limit_h_min       -8
_diffrn_reflns_limit_k_max       13
_diffrn_reflns_limit_k_min       -14
_diffrn_reflns_limit_l_max       15
_diffrn_reflns_limit_l_min       -15
_diffrn_reflns_number            15310
_diffrn_reflns_theta_full        25.00
_diffrn_reflns_theta_max         28.24
_diffrn_reflns_theta_min         1.70
_diffrn_standards_decay_%        0
_diffrn_standards_interval_count 0
_diffrn_standards_interval_time  0
_diffrn_standards_number         0
_exptl_absorpt_coefficient_mu    0.073
_exptl_absorpt_correction_T_max  0.9870
_exptl_absorpt_correction_T_min  0.9856
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   '(SADABS; Sheldrick, 2001)'
_exptl_crystal_colour            Colourless
_exptl_crystal_density_diffrn    1.193
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       Block
_exptl_crystal_F_000             300
_exptl_crystal_size_max          0.20
_exptl_crystal_size_mid          0.20
_exptl_crystal_size_min          0.18
_refine_diff_density_max         0.179
_refine_diff_density_min         -0.190
_refine_ls_extinction_coef       0.020(5)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc²λ³/sin(2θ)]^-1/4^
_refine_ls_extinction_method     'SHELXL97 (Sheldrick, 2008)'
_refine_ls_goodness_of_fit_ref   1.063
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     197
_refine_ls_number_reflns         3556
_refine_ls_number_restraints     1
_refine_ls_restrained_S_all      1.063
_refine_ls_R_factor_all          0.1126
_refine_ls_R_factor_gt           0.0504
_refine_ls_shift/su_max          0.014
_refine_ls_shift/su_mean         0.001
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'calc w=1/[σ²(Fo²)+(0.0729P)²+0.1205P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1224
_refine_ls_wR_factor_ref         0.1682
_reflns_number_gt                1930
_reflns_number_total             3556
_reflns_threshold_expression     I>2σ(I)
_cod_data_source_file            bt5058.cif
_cod_data_source_block           I
_cod_depositor_comments
;
The following automatic conversions were performed:
'_symmetry_cell_setting' value 'Triclinic' changed to 'triclinic'
according to '/home/saulius/struct/CIF-dictionaries/cif_core.dic'
dictionary named 'cif_core.dic' version 2.4.1 from 2010-06-29.

Automatic conversion script
Id: cif_fix_enum 1527 2010-12-29 10:47:43Z saulius 

The following automatic conversions were performed:

'_symmetry_cell_setting' value 'Triclinic' changed to 'triclinic'
according to /home/saulius/struct/CIF-dictionaries/cif_core.dic
dictionary named 'cif_core.dic' version 2.4.1 from 2010-06-29.

Automatic conversion script
Id: cif_fix_values 1715 2011-07-08 13:25:40Z adriana 
;
_cod_database_code               2223620
_cod_database_fobs_code          2223620
loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'-x, -y, -z'
loop_
_atom_site_type_symbol
_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
C C2 0.1988(3) 0.24655(18) 0.32290(15) 0.0425(5) Uani d . 1 . .
H H2 0.0400 0.2403 0.3379 0.051 Uiso calc R 1 . .
C C3 0.3320(3) 0.22876(19) 0.43103(15) 0.0468(5) Uani d . 1 . .
C C4 0.2694(3) 0.0952(2) 0.45372(16) 0.0493(5) Uani d . 1 . .
C C5 0.2448(4) -0.00903(19) 0.35615(16) 0.0524(6) Uani d . 1 . .
H H5A 0.1674 -0.0845 0.3778 0.063 Uiso calc R 1 . .
H H5B 0.3923 -0.0271 0.3353 0.063 Uiso calc R 1 . .
C C6 0.1161(3) 0.02397(18) 0.25591(15) 0.0442(5) Uani d . 1 . .
H H6 -0.0376 0.0336 0.2750 0.053 Uiso calc R 1 . .
C C7 0.2596(3) 0.37123(18) 0.28453(15) 0.0455(5) Uani d . 1 . .
C C8 0.1269(4) 0.4668(2) 0.30562(18) 0.0588(6) Uani d . 1 . .
H H8 0.0030 0.4548 0.3472 0.071 Uiso calc R 1 . .
C C9 0.1733(5) 0.5791(2) 0.2668(2) 0.0723(7) Uani d . 1 . .
H H9 0.0818 0.6421 0.2825 0.087 Uiso calc R 1 . .
C C10 0.3532(5) 0.5982(2) 0.2053(2) 0.0750(8) Uani d . 1 . .
H H10 0.3836 0.6738 0.1781 0.090 Uiso calc R 1 . .
C C11 0.4897(5) 0.5055(2) 0.18330(19) 0.0704(7) Uani d . 1 . .
H H11 0.6138 0.5187 0.1421 0.084 Uiso calc R 1 . .
C C12 0.4420(4) 0.3928(2) 0.22252(17) 0.0551(6) Uani d . 1 . .
H H12 0.5344 0.3301 0.2069 0.066 Uiso calc R 1 . .
C C13 0.2732(5) 0.3230(2) 0.52803(18) 0.0740(8) Uani d . 1 . .
H H13A 0.1152 0.3097 0.5367 0.111 Uiso calc R 1 . .
H H13B 0.3139 0.4072 0.5133 0.111 Uiso calc R 1 . .
H H13C 0.3535 0.3117 0.5952 0.111 Uiso calc R 1 . .
C C14 0.5846(4) 0.2435(2) 0.41959(19) 0.0644(7) Uani d . 1 . .
H H14A 0.6588 0.2207 0.4839 0.097 Uiso calc R 1 . .
H H14B 0.6361 0.3294 0.4137 0.097 Uiso calc R 1 . .
H H14C 0.6176 0.1895 0.3540 0.097 Uiso calc R 1 . .
C C15 0.1096(4) -0.07639(18) 0.15558(16) 0.0460(5) Uani d . 1 . .
C C16 0.2873(4) -0.0837(2) 0.08964(18) 0.0605(6) Uani d . 1 . .
H H16 0.4134 -0.0243 0.1061 0.073 Uiso calc R 1 . .
C C17 0.2818(5) -0.1775(2) -0.0003(2) 0.0728(7) Uani d . 1 . .
H H17 0.4041 -0.1810 -0.0438 0.087 Uiso calc R 1 . .
C C18 0.0987(5) -0.2653(2) -0.0261(2) 0.0726(7) Uani d U 1 . .
H H18 0.0952 -0.3285 -0.0872 0.087 Uiso calc R 1 . .
C C19 -0.0791(5) -0.2598(2) 0.0383(2) 0.0732(7) Uani d U 1 . .
H H19 -0.2041 -0.3199 0.0214 0.088 Uiso calc R 1 . .
C C20 -0.0753(4) -0.1654(2) 0.12890(19) 0.0620(6) Uani d . 1 . .
H H20 -0.1982 -0.1621 0.1720 0.074 Uiso calc R 1 . .
N N1 0.2245(3) 0.14438(15) 0.23353(13) 0.0435(4) Uani d . 1 . .
O O1 0.2492(3) 0.07213(16) 0.54724(12) 0.0687(5) Uani d . 1 . .
H H1 0.168(4) 0.1575(19) 0.1717(19) 0.058(7) Uiso d . 1 . .
loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0033 0.0016 '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 0.0061 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0106 0.0060 '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
N1 C2 C7 . . 109.70(15) ?
N1 C2 C3 . . 109.78(16) ?
C7 C2 C3 . . 114.76(15) ?
N1 C2 H2 . . 107.4 ?
C7 C2 H2 . . 107.4 ?
C3 C2 H2 . . 107.4 ?
C4 C3 C13 . . 109.95(17) ?
C4 C3 C14 . . 106.01(17) ?
C13 C3 C14 . . 110.43(18) ?
C4 C3 C2 . . 108.99(15) ?
C13 C3 C2 . . 109.16(18) ?
C14 C3 C2 . . 112.25(16) ?
O1 C4 C5 . . 120.6(2) ?
O1 C4 C3 . . 121.75(19) ?
C5 C4 C3 . . 117.57(16) ?
C4 C5 C6 . . 112.35(17) ?
C4 C5 H5A . . 109.1 ?
C6 C5 H5A . . 109.1 ?
C4 C5 H5B . . 109.1 ?
C6 C5 H5B . . 109.1 ?
H5A C5 H5B . . 107.9 ?
N1 C6 C15 . . 111.07(15) ?
N1 C6 C5 . . 107.32(16) ?
C15 C6 C5 . . 111.89(17) ?
N1 C6 H6 . . 108.8 ?
C15 C6 H6 . . 108.8 ?
C5 C6 H6 . . 108.8 ?
C12 C7 C8 . . 117.4(2) ?
C12 C7 C2 . . 121.77(19) ?
C8 C7 C2 . . 120.70(19) ?
C9 C8 C7 . . 121.6(2) ?
C9 C8 H8 . . 119.2 ?
C7 C8 H8 . . 119.2 ?
C10 C9 C8 . . 120.0(3) ?
C10 C9 H9 . . 120.0 ?
C8 C9 H9 . . 120.0 ?
C9 C10 C11 . . 119.9(2) ?
C9 C10 H10 . . 120.0 ?
C11 C10 H10 . . 120.0 ?
C10 C11 C12 . . 119.8(2) ?
C10 C11 H11 . . 120.1 ?
C12 C11 H11 . . 120.1 ?
C11 C12 C7 . . 121.2(2) ?
C11 C12 H12 . . 119.4 ?
C7 C12 H12 . . 119.4 ?
C3 C13 H13A . . 109.5 ?
C3 C13 H13B . . 109.5 ?
H13A C13 H13B . . 109.5 ?
C3 C13 H13C . . 109.5 ?
H13A C13 H13C . . 109.5 ?
H13B C13 H13C . . 109.5 ?
C3 C14 H14A . . 109.5 ?
C3 C14 H14B . . 109.5 ?
H14A C14 H14B . . 109.5 ?
C3 C14 H14C . . 109.5 ?
H14A C14 H14C . . 109.5 ?
H14B C14 H14C . . 109.5 ?
C16 C15 C20 . . 118.2(2) ?
C16 C15 C6 . . 121.47(18) ?
C20 C15 C6 . . 120.3(2) ?
C17 C16 C15 . . 121.0(2) ?
C17 C16 H16 . . 119.5 ?
C15 C16 H16 . . 119.5 ?
C18 C17 C16 . . 120.4(2) ?
C18 C17 H17 . . 119.8 ?
C16 C17 H17 . . 119.8 ?
C17 C18 C19 . . 119.4(2) ?
C17 C18 H18 . . 120.3 ?
C19 C18 H18 . . 120.3 ?
C18 C19 C20 . . 120.5(2) ?
C18 C19 H19 . . 119.8 ?
C20 C19 H19 . . 119.8 ?
C15 C20 C19 . . 120.4(2) ?
C15 C20 H20 . . 119.8 ?
C19 C20 H20 . . 119.8 ?
C6 N1 C2 . . 111.51(15) ?
C6 N1 H1 . . 107.9(14) ?
C2 N1 H1 . . 111.3(15) ?
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
C2 N1 . 1.458(2) ?
C2 C7 . 1.504(3) ?
C2 C3 . 1.555(3) ?
C2 H2 . 0.9800 ?
C3 C4 . 1.520(3) ?
C3 C13 . 1.525(3) ?
C3 C14 . 1.528(3) ?
C4 O1 . 1.209(2) ?
C4 C5 . 1.499(3) ?
C5 C6 . 1.522(3) ?
C5 H5A . 0.9700 ?
C5 H5B . 0.9700 ?
C6 N1 . 1.457(2) ?
C6 C15 . 1.504(3) ?
C6 H6 . 0.9800 ?
C7 C12 . 1.381(3) ?
C7 C8 . 1.382(3) ?
C8 C9 . 1.371(3) ?
C8 H8 . 0.9300 ?
C9 C10 . 1.361(4) ?
C9 H9 . 0.9300 ?
C10 C11 . 1.374(4) ?
C10 H10 . 0.9300 ?
C11 C12 . 1.380(3) ?
C11 H11 . 0.9300 ?
C12 H12 . 0.9300 ?
C13 H13A . 0.9600 ?
C13 H13B . 0.9600 ?
C13 H13C . 0.9600 ?
C14 H14A . 0.9600 ?
C14 H14B . 0.9600 ?
C14 H14C . 0.9600 ?
C15 C16 . 1.372(3) ?
C15 C20 . 1.377(3) ?
C16 C17 . 1.372(3) ?
C16 H16 . 0.9300 ?
C17 C18 . 1.362(4) ?
C17 H17 . 0.9300 ?
C18 C19 . 1.360(4) ?
C18 H18 . 0.9300 ?
C19 C20 . 1.383(3) ?
C19 H19 . 0.9300 ?
C20 H20 . 0.9300 ?
N1 H1 . 0.85(2) ?
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
C10 H10 Cg3 1_565 0.93 2.9466 3.648 133.31
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_1
_geom_torsion_site_symmetry_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
_geom_torsion
_geom_torsion_publ_flag
N1 C2 C3 C4 . . . . -50.7(2) ?
C7 C2 C3 C4 . . . . -174.77(16) ?
N1 C2 C3 C13 . . . . -170.78(17) ?
C7 C2 C3 C13 . . . . 65.1(2) ?
N1 C2 C3 C14 . . . . 66.4(2) ?
C7 C2 C3 C14 . . . . -57.6(2) ?
C13 C3 C4 O1 . . . . -22.3(3) ?
C14 C3 C4 O1 . . . . 97.1(2) ?
C2 C3 C4 O1 . . . . -141.9(2) ?
C13 C3 C4 C5 . . . . 160.91(19) ?
C14 C3 C4 C5 . . . . -79.7(2) ?
C2 C3 C4 C5 . . . . 41.3(2) ?
O1 C4 C5 C6 . . . . 139.4(2) ?
C3 C4 C5 C6 . . . . -43.7(2) ?
C4 C5 C6 N1 . . . . 53.0(2) ?
C4 C5 C6 C15 . . . . 175.09(16) ?
N1 C2 C7 C12 . . . . -41.6(2) ?
C3 C2 C7 C12 . . . . 82.6(2) ?
N1 C2 C7 C8 . . . . 135.14(19) ?
C3 C2 C7 C8 . . . . -100.7(2) ?
C12 C7 C8 C9 . . . . 0.0(3) ?
C2 C7 C8 C9 . . . . -176.82(19) ?
C7 C8 C9 C10 . . . . 0.4(4) ?
C8 C9 C10 C11 . . . . -0.8(4) ?
C9 C10 C11 C12 . . . . 0.8(4) ?
C10 C11 C12 C7 . . . . -0.5(3) ?
C8 C7 C12 C11 . . . . 0.0(3) ?
C2 C7 C12 C11 . . . . 176.84(19) ?
N1 C6 C15 C16 . . . . 39.6(3) ?
C5 C6 C15 C16 . . . . -80.3(2) ?
N1 C6 C15 C20 . . . . -141.7(2) ?
C5 C6 C15 C20 . . . . 98.4(2) ?
C20 C15 C16 C17 . . . . -0.3(3) ?
C6 C15 C16 C17 . . . . 178.5(2) ?
C15 C16 C17 C18 . . . . 0.2(4) ?
C16 C17 C18 C19 . . . . -0.3(4) ?
C17 C18 C19 C20 . . . . 0.5(4) ?
C16 C15 C20 C19 . . . . 0.5(3) ?
C6 C15 C20 C19 . . . . -178.3(2) ?
C18 C19 C20 C15 . . . . -0.6(4) ?
C15 C6 N1 C2 . . . . 170.45(16) ?
C5 C6 N1 C2 . . . . -67.0(2) ?
C7 C2 N1 C6 . . . . -165.75(16) ?
C3 C2 N1 C6 . . . . 67.3(2) ?
