#------------------------------------------------------------------------------
#$Date: 2017-10-13 11:42:48 +0300 (Fri, 13 Oct 2017) $
#$Revision: 201978 $
#$URL: file:///home/coder/svn-repositories/cod/cif/2/22/25/2222584.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_2222584
loop_
_publ_author_name
'Aravindhan, S.'
'Ponnuswamy, S.'
'Jamesh, M.'
'Ramesh, P.'
'Ponnuswamy, M. N.'
_publ_section_title
1-Acetyl-c-3,t-3-dimethyl-r-2,c-6-diphenylpiperidin-4-one
_journal_coeditor_code           BT2989
_journal_issue                   8
_journal_name_full               'Acta Crystallographica Section E'
_journal_page_first              o1974
_journal_paper_doi               10.1107/S1600536809028049
_journal_volume                  65
_journal_year                    2009
_chemical_formula_iupac          'C21 H23 N O2'
_chemical_formula_moiety         'C21 H23 N O2'
_chemical_formula_sum            'C21 H23 N O2'
_chemical_formula_weight         321.40
_chemical_name_systematic
1-Acetyl-c-3,t-3-dimethyl-r-2,c-6-diphenylpiperidin-4-one
_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'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_audit_creation_method           SHELXL-97
_cell_angle_alpha                90.00
_cell_angle_beta                 100.373(3)
_cell_angle_gamma                90.00
_cell_formula_units_Z            2
_cell_length_a                   7.5622(4)
_cell_length_b                   10.6369(5)
_cell_length_c                   11.1497(7)
_cell_measurement_reflns_used    3546
_cell_measurement_temperature    293(2)
_cell_measurement_theta_max      34.78
_cell_measurement_theta_min      1.86
_cell_volume                     882.21(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 1.000
_diffrn_measured_fraction_theta_max 0.867
_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  0.0420
_diffrn_reflns_av_sigmaI/netI    0.0358
_diffrn_reflns_limit_h_max       11
_diffrn_reflns_limit_h_min       -11
_diffrn_reflns_limit_k_max       11
_diffrn_reflns_limit_k_min       -17
_diffrn_reflns_limit_l_max       16
_diffrn_reflns_limit_l_min       -16
_diffrn_reflns_number            12819
_diffrn_reflns_theta_full        25.00
_diffrn_reflns_theta_max         34.78
_diffrn_reflns_theta_min         1.86
_diffrn_standards_decay_%        0
_diffrn_standards_interval_time  0
_diffrn_standards_number         0
_exptl_absorpt_coefficient_mu    0.077
_exptl_absorpt_correction_T_max  0.985
_exptl_absorpt_correction_T_min  0.977
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   '(SADABS; Sheldrick, 2001)'
_exptl_crystal_colour            Colorless
_exptl_crystal_density_diffrn    1.210
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       Block
_exptl_crystal_F_000             344
_exptl_crystal_size_max          0.30
_exptl_crystal_size_mid          0.25
_exptl_crystal_size_min          0.20
_refine_diff_density_max         0.226
_refine_diff_density_min         -0.172
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.023
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     220
_refine_ls_number_reflns         3457
_refine_ls_number_restraints     1
_refine_ls_restrained_S_all      1.023
_refine_ls_R_factor_all          0.0722
_refine_ls_R_factor_gt           0.0458
_refine_ls_shift/su_max          0.012
_refine_ls_shift/su_mean         0.001
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'calc w=1/[σ²(Fo²)+(0.0853P)²] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1220
_refine_ls_wR_factor_ref         0.1453
_reflns_number_gt                2400
_reflns_number_total             3457
_reflns_threshold_expression     I>2σ(I)
_cod_data_source_file            bt2989.cif
_cod_data_source_block           I
_cod_depositor_comments
;
The following automatic conversions were performed:
'_symmetry_cell_setting' value 'Monoclinic' changed to 'monoclinic'
according to '/home/saulius/struct/CIF-dictionaries/cif_core.dic'
dictionary named 'cif_core.dic' version 2.4.1 from
2010-06-29.

'_exptl_absorpt_correction_type' value 'Multi-scan' changed
to 'multi-scan' 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 'Monoclinic' changed to 'monoclinic'
according to /home/saulius/struct/CIF-dictionaries/cif_core.dic
dictionary named 'cif_core.dic' version 2.4.1 from
2010-06-29.

'_exptl_absorpt_correction_type' value 'Multi-scan'
changed to 'multi-scan' 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_original_sg_symbol_H-M      'P 21'
_cod_database_code               2222584
_cod_database_fobs_code          2222584
loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'-x, y+1/2, -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
O O1 1.0626(2) 0.57532(19) 0.23859(18) 0.0680(5) Uani d . 1 . .
O O2 0.4399(3) 0.3113(2) -0.07440(15) 0.0763(5) Uani d . 1 . .
N N1 0.7953(2) 0.47573(14) 0.20329(14) 0.0393(3) Uani d . 1 . .
C C2 0.6053(2) 0.47297(17) 0.21592(15) 0.0392(3) Uani d . 1 . .
H H2 0.5538 0.5559 0.1928 0.047 Uiso calc R 1 . .
C C3 0.4980(3) 0.3754(2) 0.13125(18) 0.0493(4) Uani d . 1 . .
H H3A 0.5087 0.2952 0.1735 0.059 Uiso calc R 1 . .
H H3B 0.3722 0.3993 0.1187 0.059 Uiso calc R 1 . .
C C4 0.5484(3) 0.3556(2) 0.00799(18) 0.0507(5) Uani d . 1 . .
C C5 0.7355(3) 0.3903(2) -0.00532(17) 0.0492(4) Uani d . 1 . .
C C6 0.8617(3) 0.38858(19) 0.11952(16) 0.0414(4) Uani d . 1 . .
H H6 0.9759 0.4240 0.1055 0.050 Uiso calc R 1 . .
C C7 0.9060(3) 0.57188(19) 0.25158(18) 0.0464(4) Uani d . 1 . .
C C8 0.8306(4) 0.6735(2) 0.3207(2) 0.0600(5) Uani d . 1 . .
H H8A 0.7347 0.7155 0.2675 0.090 Uiso calc R 1 . .
H H8B 0.9234 0.7330 0.3509 0.090 Uiso calc R 1 . .
H H8C 0.7852 0.6371 0.3879 0.090 Uiso calc R 1 . .
C C9 0.5778(2) 0.44554(17) 0.34515(16) 0.0406(4) Uani d . 1 . .
C C10 0.6819(3) 0.3583(2) 0.41885(18) 0.0508(4) Uani d . 1 . .
H H10 0.7759 0.3178 0.3912 0.061 Uiso calc R 1 . .
C C11 0.6462(4) 0.3315(2) 0.5329(2) 0.0606(6) Uani d . 1 . .
H H11 0.7158 0.2726 0.5819 0.073 Uiso calc R 1 . .
C C12 0.5085(4) 0.3913(3) 0.5744(2) 0.0670(7) Uani d . 1 . .
H H12 0.4851 0.3732 0.6517 0.080 Uiso calc R 1 . .
C C13 0.4058(4) 0.4773(3) 0.5026(3) 0.0726(7) Uani d . 1 . .
H H13 0.3123 0.5175 0.5310 0.087 Uiso calc R 1 . .
C C14 0.4399(3) 0.5051(2) 0.3878(2) 0.0571(5) Uani d . 1 . .
H H14 0.3696 0.5641 0.3393 0.069 Uiso calc R 1 . .
C C15 0.7232(4) 0.5268(2) -0.0542(2) 0.0616(6) Uani d . 1 . .
H H15A 0.6699 0.5795 -0.0005 0.092 Uiso calc R 1 . .
H H15B 0.6505 0.5286 -0.1341 0.092 Uiso calc R 1 . .
H H15C 0.8416 0.5571 -0.0581 0.092 Uiso calc R 1 . .
C C16 0.8096(4) 0.3069(3) -0.0963(2) 0.0699(7) Uani d . 1 . .
H H16A 0.7373 0.3168 -0.1758 0.105 Uiso calc R 1 . .
H H16B 0.8067 0.2206 -0.0714 0.105 Uiso calc R 1 . .
H H16C 0.9313 0.3308 -0.0988 0.105 Uiso calc R 1 . .
C C17 0.9083(2) 0.26144(18) 0.17969(16) 0.0417(4) Uani d . 1 . .
C C18 0.8065(3) 0.1533(2) 0.1580(2) 0.0525(5) Uani d . 1 . .
H H18 0.7036 0.1538 0.0981 0.063 Uiso calc R 1 . .
C C19 0.8543(4) 0.0441(2) 0.2235(2) 0.0634(6) Uani d . 1 . .
H H19 0.7835 -0.0276 0.2077 0.076 Uiso calc R 1 . .
C C20 1.0062(4) 0.0418(2) 0.3117(2) 0.0654(6) Uani d . 1 . .
H H20 1.0375 -0.0309 0.3570 0.079 Uiso calc R 1 . .
C C21 1.1104(3) 0.1459(3) 0.3327(2) 0.0600(6) Uani d . 1 . .
H H21 1.2149 0.1434 0.3912 0.072 Uiso calc R 1 . .
C C22 1.0634(3) 0.2562(2) 0.26817(18) 0.0500(4) Uani d . 1 . .
H H22 1.1360 0.3270 0.2842 0.060 Uiso calc R 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
C7 N1 C6 . . 117.82(15) ?
C7 N1 C2 . . 121.12(15) ?
C6 N1 C2 . . 120.09(15) ?
N1 C2 C9 . . 113.43(14) ?
N1 C2 C3 . . 111.90(14) ?
C9 C2 C3 . . 107.80(15) ?
N1 C2 H2 . . 107.8 ?
C9 C2 H2 . . 107.8 ?
C3 C2 H2 . . 107.8 ?
C4 C3 C2 . . 117.60(17) ?
C4 C3 H3A . . 107.9 ?
C2 C3 H3A . . 107.9 ?
C4 C3 H3B . . 107.9 ?
C2 C3 H3B . . 107.9 ?
H3A C3 H3B . . 107.2 ?
O2 C4 C5 . . 123.0(2) ?
O2 C4 C3 . . 119.9(2) ?
C5 C4 C3 . . 117.11(17) ?
C4 C5 C16 . . 112.9(2) ?
C4 C5 C6 . . 110.54(15) ?
C16 C5 C6 . . 110.58(18) ?
C4 C5 C15 . . 105.60(19) ?
C16 C5 C15 . . 108.50(18) ?
C6 C5 C15 . . 108.51(18) ?
N1 C6 C17 . . 111.05(14) ?
N1 C6 C5 . . 109.90(15) ?
C17 C6 C5 . . 117.75(17) ?
N1 C6 H6 . . 105.7 ?
C17 C6 H6 . . 105.7 ?
C5 C6 H6 . . 105.7 ?
O1 C7 N1 . . 120.9(2) ?
O1 C7 C8 . . 120.5(2) ?
N1 C7 C8 . . 118.58(18) ?
C7 C8 H8A . . 109.5 ?
C7 C8 H8B . . 109.5 ?
H8A C8 H8B . . 109.5 ?
C7 C8 H8C . . 109.5 ?
H8A C8 H8C . . 109.5 ?
H8B C8 H8C . . 109.5 ?
C14 C9 C10 . . 119.22(17) ?
C14 C9 C2 . . 118.71(18) ?
C10 C9 C2 . . 122.00(16) ?
C11 C10 C9 . . 120.1(2) ?
C11 C10 H10 . . 120.0 ?
C9 C10 H10 . . 120.0 ?
C12 C11 C10 . . 120.3(2) ?
C12 C11 H11 . . 119.9 ?
C10 C11 H11 . . 119.9 ?
C13 C12 C11 . . 120.0(2) ?
C13 C12 H12 . . 120.0 ?
C11 C12 H12 . . 120.0 ?
C12 C13 C14 . . 120.4(2) ?
C12 C13 H13 . . 119.8 ?
C14 C13 H13 . . 119.8 ?
C9 C14 C13 . . 120.0(2) ?
C9 C14 H14 . . 120.0 ?
C13 C14 H14 . . 120.0 ?
C5 C15 H15A . . 109.5 ?
C5 C15 H15B . . 109.5 ?
H15A C15 H15B . . 109.5 ?
C5 C15 H15C . . 109.5 ?
H15A C15 H15C . . 109.5 ?
H15B C15 H15C . . 109.5 ?
C5 C16 H16A . . 109.5 ?
C5 C16 H16B . . 109.5 ?
H16A C16 H16B . . 109.5 ?
C5 C16 H16C . . 109.5 ?
H16A C16 H16C . . 109.5 ?
H16B C16 H16C . . 109.5 ?
C18 C17 C22 . . 117.57(18) ?
C18 C17 C6 . . 125.84(17) ?
C22 C17 C6 . . 116.52(18) ?
C17 C18 C19 . . 121.5(2) ?
C17 C18 H18 . . 119.3 ?
C19 C18 H18 . . 119.3 ?
C20 C19 C18 . . 119.9(2) ?
C20 C19 H19 . . 120.1 ?
C18 C19 H19 . . 120.1 ?
C21 C20 C19 . . 119.7(2) ?
C21 C20 H20 . . 120.1 ?
C19 C20 H20 . . 120.1 ?
C20 C21 C22 . . 121.0(2) ?
C20 C21 H21 . . 119.5 ?
C22 C21 H21 . . 119.5 ?
C21 C22 C17 . . 120.4(2) ?
C21 C22 H22 . . 119.8 ?
C17 C22 H22 . . 119.8 ?
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
O1 C7 . 1.219(3) ?
O2 C4 . 1.211(3) ?
N1 C7 . 1.369(2) ?
N1 C6 . 1.467(2) ?
N1 C2 . 1.469(2) ?
C2 C9 . 1.521(2) ?
C2 C3 . 1.534(3) ?
C2 H2 . 0.9800 ?
C3 C4 . 1.506(3) ?
C3 H3A . 0.9700 ?
C3 H3B . 0.9700 ?
C4 C5 . 1.495(3) ?
C5 C16 . 1.528(3) ?
C5 C6 . 1.540(3) ?
C5 C15 . 1.548(3) ?
C6 C17 . 1.523(3) ?
C6 H6 . 0.9800 ?
C7 C8 . 1.499(3) ?
C8 H8A . 0.9600 ?
C8 H8B . 0.9600 ?
C8 H8C . 0.9600 ?
C9 C14 . 1.376(3) ?
C9 C10 . 1.387(3) ?
C10 C11 . 1.376(3) ?
C10 H10 . 0.9300 ?
C11 C12 . 1.370(4) ?
C11 H11 . 0.9300 ?
C12 C13 . 1.362(4) ?
C12 H12 . 0.9300 ?
C13 C14 . 1.383(4) ?
C13 H13 . 0.9300 ?
C14 H14 . 0.9300 ?
C15 H15A . 0.9600 ?
C15 H15B . 0.9600 ?
C15 H15C . 0.9600 ?
C16 H16A . 0.9600 ?
C16 H16B . 0.9600 ?
C16 H16C . 0.9600 ?
C17 C18 . 1.381(3) ?
C17 C22 . 1.391(3) ?
C18 C19 . 1.385(3) ?
C18 H18 . 0.9300 ?
C19 C20 . 1.371(4) ?
C19 H19 . 0.9300 ?
C20 C21 . 1.355(4) ?
C20 H20 . 0.9300 ?
C21 C22 . 1.389(3) ?
C21 H21 . 0.9300 ?
C22 H22 . 0.9300 ?
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
C6 H6 O1 1 0.98 2.21 2.700(3) 109.7
C8 H8A O2 2_655 0.96 2.53 3.442(3) 159.0
C14 H14 O1 1_455 0.93 2.39 3.124(3) 135.3
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
C7 N1 C2 C9 . . . . -70.9(2) ?
C6 N1 C2 C9 . . . . 120.55(17) ?
C7 N1 C2 C3 . . . . 166.82(16) ?
C6 N1 C2 C3 . . . . -1.7(2) ?
N1 C2 C3 C4 . . . . -35.4(2) ?
C9 C2 C3 C4 . . . . -160.78(17) ?
C2 C3 C4 O2 . . . . -157.6(2) ?
C2 C3 C4 C5 . . . . 23.6(3) ?
O2 C4 C5 C16 . . . . -31.1(3) ?
C3 C4 C5 C16 . . . . 147.7(2) ?
O2 C4 C5 C6 . . . . -155.5(2) ?
C3 C4 C5 C6 . . . . 23.3(3) ?
O2 C4 C5 C15 . . . . 87.3(3) ?
C3 C4 C5 C15 . . . . -93.9(2) ?
C7 N1 C6 C17 . . . . 107.34(18) ?
C2 N1 C6 C17 . . . . -83.8(2) ?
C7 N1 C6 C5 . . . . -120.60(18) ?
C2 N1 C6 C5 . . . . 48.3(2) ?
C4 C5 C6 N1 . . . . -58.1(2) ?
C16 C5 C6 N1 . . . . 176.13(18) ?
C15 C5 C6 N1 . . . . 57.2(2) ?
C4 C5 C6 C17 . . . . 70.3(2) ?
C16 C5 C6 C17 . . . . -55.4(2) ?
C15 C5 C6 C17 . . . . -174.30(17) ?
C6 N1 C7 O1 . . . . -9.6(3) ?
C2 N1 C7 O1 . . . . -178.35(18) ?
C6 N1 C7 C8 . . . . 170.20(17) ?
C2 N1 C7 C8 . . . . 1.4(3) ?
N1 C2 C9 C14 . . . . 143.64(19) ?
C3 C2 C9 C14 . . . . -91.9(2) ?
N1 C2 C9 C10 . . . . -39.4(2) ?
C3 C2 C9 C10 . . . . 85.1(2) ?
C14 C9 C10 C11 . . . . 0.4(3) ?
C2 C9 C10 C11 . . . . -176.5(2) ?
C9 C10 C11 C12 . . . . -0.4(4) ?
C10 C11 C12 C13 . . . . 0.3(4) ?
C11 C12 C13 C14 . . . . -0.2(4) ?
C10 C9 C14 C13 . . . . -0.3(3) ?
C2 C9 C14 C13 . . . . 176.7(2) ?
C12 C13 C14 C9 . . . . 0.2(4) ?
N1 C6 C17 C18 . . . . 104.0(2) ?
C5 C6 C17 C18 . . . . -23.9(3) ?
N1 C6 C17 C22 . . . . -73.0(2) ?
C5 C6 C17 C22 . . . . 159.13(16) ?
C22 C17 C18 C19 . . . . 1.4(3) ?
C6 C17 C18 C19 . . . . -175.6(2) ?
C17 C18 C19 C20 . . . . -0.3(4) ?
C18 C19 C20 C21 . . . . -1.2(4) ?
C19 C20 C21 C22 . . . . 1.6(4) ?
C20 C21 C22 C17 . . . . -0.5(3) ?
C18 C17 C22 C21 . . . . -1.0(3) ?
C6 C17 C22 C21 . . . . 176.26(18) ?
loop_
_cod_related_entry_id
_cod_related_entry_database
_cod_related_entry_code
1 ChemSpider 24742893
