#------------------------------------------------------------------------------
#$Date: 2016-02-20 22:30:07 +0200 (Sat, 20 Feb 2016) $
#$Revision: 176789 $
#$URL: svn://www.crystallography.net/cod/cif/2/22/60/2226078.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_2226078
loop_
_publ_author_name
'Ravichandran, K.'
'Ramesh, P.'
'Sakthivel, P.'
'Ponnuswamy, S.'
'Ponnuswamy, M. N.'
_publ_section_title
;
 1-Formyl-t-3,t-5-dimethyl-r-2,c-6-diphenylpiperidin-4-one
;
_journal_coeditor_code           CI5087
_journal_issue                   6
_journal_name_full               'Acta Crystallographica Section E'
_journal_page_first              o1505
_journal_paper_doi               10.1107/S1600536810018490
_journal_volume                  66
_journal_year                    2010
_chemical_formula_iupac          'C20 H21 N O2'
_chemical_formula_moiety         'C20 H21 N O2'
_chemical_formula_sum            'C20 H21 N O2'
_chemical_formula_weight         307.38
_chemical_name_systematic
1-Formyl-t-3,t-5-dimethyl-r-2,c-6-diphenylpiperidin-4-one
_space_group_IT_number           61
_symmetry_cell_setting           orthorhombic
_symmetry_space_group_name_Hall  '-P 2ac 2ab'
_symmetry_space_group_name_H-M   'P b c a'
_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                 90.00
_cell_angle_gamma                90.00
_cell_formula_units_Z            8
_cell_length_a                   7.4303(4)
_cell_length_b                   15.3567(6)
_cell_length_c                   29.6732(13)
_cell_measurement_reflns_used    1246
_cell_measurement_temperature    292(2)
_cell_measurement_theta_max      28.44
_cell_measurement_theta_min      1.37
_cell_volume                     3385.9(3)
_computing_cell_refinement       'SAINT (Bruker, 2008)'
_computing_data_collection       'APEX2 (Bruker, 2008)'
_computing_data_reduction        'SAINT (Bruker, 2008)'
_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      292(2)
_diffrn_measured_fraction_theta_full 0.986
_diffrn_measured_fraction_theta_max 0.986
_diffrn_measurement_device_type
'Bruker SMART APEXII area-detector diffractometer'
_diffrn_measurement_method       'ω and φ scans'
_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  0.0296
_diffrn_reflns_av_sigmaI/netI    0.0323
_diffrn_reflns_limit_h_max       6
_diffrn_reflns_limit_h_min       -9
_diffrn_reflns_limit_k_max       18
_diffrn_reflns_limit_k_min       -20
_diffrn_reflns_limit_l_max       38
_diffrn_reflns_limit_l_min       -39
_diffrn_reflns_number            16882
_diffrn_reflns_theta_full        28.44
_diffrn_reflns_theta_max         28.44
_diffrn_reflns_theta_min         1.37
_diffrn_standards_number         0
_exptl_absorpt_coefficient_mu    0.077
_exptl_absorpt_correction_T_max  0.988
_exptl_absorpt_correction_T_min  0.983
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   '(SADABS; Bruker, 2008)'
_exptl_crystal_colour            Colourless
_exptl_crystal_density_diffrn    1.206
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       Block
_exptl_crystal_F_000             1312
_exptl_crystal_size_max          0.22
_exptl_crystal_size_mid          0.19
_exptl_crystal_size_min          0.16
_refine_diff_density_max         0.371
_refine_diff_density_min         -0.225
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.015
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     213
_refine_ls_number_reflns         4198
_refine_ls_number_restraints     25
_refine_ls_restrained_S_all      1.104
_refine_ls_R_factor_all          0.1239
_refine_ls_R_factor_gt           0.0585
_refine_ls_shift/su_max          0.001
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'calc w=1/[σ²(Fo²)+(0.0741P)²+1.1948P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1541
_refine_ls_wR_factor_ref         0.1937
_reflns_number_gt                2097
_reflns_number_total             4198
_reflns_threshold_expression     I>2σ(I)
_cod_data_source_file            ci5087.cif
_cod_data_source_block           I
_cod_depositor_comments
;
The following automatic conversions were performed:
'_symmetry_cell_setting' value 'Orthorhombic' changed to 'orthorhombic'
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 
;
_cod_database_code               2226078
_cod_database_fobs_code          2226078
loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'-x+1/2, -y, z+1/2'
'x+1/2, -y+1/2, -z'
'-x, y+1/2, -z+1/2'
'-x, -y, -z'
'x-1/2, y, -z-1/2'
'-x-1/2, y-1/2, z'
'x, -y-1/2, z-1/2'
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 0.0192(4) 0.2060(2) 0.13459(14) 0.1697(16) Uani d U 1 . .
O O2 0.6395(3) 0.38855(13) 0.21978(6) 0.0841(6) Uani d . 1 . .
N N1 0.2046(3) 0.31856(13) 0.14813(8) 0.0690(6) Uani d . 1 . .
C C2 0.3721(3) 0.27494(15) 0.13546(9) 0.0645(7) Uani d . 1 . .
H H2 0.3426 0.2132 0.1317 0.077 Uiso calc R 1 . .
C C3 0.5024(3) 0.28034(15) 0.17521(8) 0.0565(6) Uani d . 1 . .
H H3 0.6204 0.2596 0.1651 0.068 Uiso calc R 1 . .
C C4 0.5235(3) 0.37170(15) 0.19238(8) 0.0563(6) Uani d . 1 . .
C C5 0.3986(3) 0.44063(14) 0.17429(8) 0.0535(6) Uani d . 1 . .
H H5 0.4444 0.4570 0.1445 0.064 Uiso calc R 1 . .
C C6 0.2059(3) 0.40703(16) 0.16730(8) 0.0586(6) Uani d . 1 . .
H H6 0.1498 0.4034 0.1971 0.070 Uiso calc R 1 . .
C C7 0.0458(5) 0.2769(3) 0.14840(17) 0.1186(15) Uani d U 1 . .
C C8 0.4415(4) 0.30662(16) 0.09006(9) 0.0715(8) Uani d . 1 . .
C C9 0.3332(6) 0.2922(2) 0.05318(12) 0.1179(14) Uani d . 1 . .
H H9 0.2243 0.2632 0.0569 0.141 Uiso calc R 1 . .
C C10 0.3834(9) 0.3199(3) 0.01118(15) 0.1455(18) Uani d U 1 . .
H H10 0.3106 0.3078 -0.0135 0.175 Uiso calc R 1 . .
C C11 0.5382(9) 0.3649(3) 0.00538(13) 0.1369(17) Uani d U 1 . .
H H11 0.5679 0.3869 -0.0229 0.164 Uiso calc R 1 . .
C C12 0.6510(6) 0.3778(3) 0.04115(13) 0.1199(14) Uani d . 1 . .
H H12 0.7601 0.4065 0.0371 0.144 Uiso calc R 1 . .
C C13 0.6019(5) 0.3479(2) 0.08344(10) 0.0854(9) Uani d . 1 . .
H H13 0.6794 0.3560 0.1077 0.103 Uiso calc R 1 . .
C C14 0.4401(4) 0.22289(18) 0.21443(10) 0.0781(8) Uani d . 1 . .
H H14A 0.5236 0.2281 0.2390 0.117 Uiso calc R 1 . .
H H14B 0.4348 0.1633 0.2047 0.117 Uiso calc R 1 . .
H H14C 0.3229 0.2413 0.2242 0.117 Uiso calc R 1 . .
C C15 0.3989(4) 0.52323(17) 0.20290(10) 0.0779(8) Uani d . 1 . .
H H15A 0.3343 0.5128 0.2304 0.117 Uiso calc R 1 . .
H H15B 0.3418 0.5695 0.1865 0.117 Uiso calc R 1 . .
H H15C 0.5207 0.5393 0.2098 0.117 Uiso calc R 1 . .
C C16 0.0934(3) 0.46917(17) 0.13948(9) 0.0627(6) Uani d . 1 . .
C C17 -0.0611(4) 0.50498(19) 0.15754(11) 0.0781(8) Uani d . 1 . .
H H17 -0.0950 0.4895 0.1866 0.094 Uiso calc R 1 . .
C C18 -0.1656(4) 0.5623(2) 0.13407(17) 0.1041(12) Uani d . 1 . .
H H18 -0.2686 0.5855 0.1472 0.125 Uiso calc R 1 . .
C C19 -0.1192(6) 0.5849(2) 0.09201(18) 0.1146(14) Uani d . 1 . .
H H19 -0.1902 0.6241 0.0760 0.138 Uiso calc R 1 . .
C C20 0.0328(6) 0.5506(2) 0.07227(12) 0.1109(12) Uani d . 1 . .
H H20 0.0638 0.5662 0.0430 0.133 Uiso calc R 1 . .
C C21 0.1400(5) 0.4924(2) 0.09632(10) 0.0881(9) Uani d . 1 . .
H H21 0.2432 0.4694 0.0832 0.106 Uiso calc R 1 . .
H H7 -0.076(5) 0.287(2) 0.1562(11) 0.106 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
C7 N1 C2 . . 122.1(3) ?
C7 N1 C6 . . 116.3(3) ?
C2 N1 C6 . . 121.11(17) ?
N1 C2 C8 . . 111.7(2) ?
N1 C2 C3 . . 108.4(2) ?
C8 C2 C3 . . 116.8(2) ?
N1 C2 H2 . . 106.4 ?
C8 C2 H2 . . 106.4 ?
C3 C2 H2 . . 106.4 ?
C4 C3 C2 . . 112.28(19) ?
C4 C3 C14 . . 108.2(2) ?
C2 C3 C14 . . 111.3(2) ?
C4 C3 H3 . . 108.3 ?
C2 C3 H3 . . 108.3 ?
C14 C3 H3 . . 108.3 ?
O2 C4 C3 . . 120.1(2) ?
O2 C4 C5 . . 121.8(2) ?
C3 C4 C5 . . 118.12(19) ?
C4 C5 C15 . . 112.6(2) ?
C4 C5 C6 . . 112.73(18) ?
C15 C5 C6 . . 110.8(2) ?
C4 C5 H5 . . 106.7 ?
C15 C5 H5 . . 106.7 ?
C6 C5 H5 . . 106.7 ?
N1 C6 C16 . . 111.6(2) ?
N1 C6 C5 . . 111.58(19) ?
C16 C6 C5 . . 112.11(19) ?
N1 C6 H6 . . 107.1 ?
C16 C6 H6 . . 107.1 ?
C5 C6 H6 . . 107.1 ?
O1 C7 N1 . . 125.8(5) ?
O1 C7 H7 . . 94(2) ?
N1 C7 H7 . . 140(2) ?
C13 C8 C9 . . 118.1(3) ?
C13 C8 C2 . . 124.9(2) ?
C9 C8 C2 . . 117.0(3) ?
C10 C9 C8 . . 121.0(4) ?
C10 C9 H9 . . 119.5 ?
C8 C9 H9 . . 119.5 ?
C11 C10 C9 . . 120.4(4) ?
C11 C10 H10 . . 119.8 ?
C9 C10 H10 . . 119.8 ?
C10 C11 C12 . . 119.8(4) ?
C10 C11 H11 . . 120.1 ?
C12 C11 H11 . . 120.1 ?
C11 C12 C13 . . 119.6(4) ?
C11 C12 H12 . . 120.2 ?
C13 C12 H12 . . 120.2 ?
C8 C13 C12 . . 121.0(3) ?
C8 C13 H13 . . 119.5 ?
C12 C13 H13 . . 119.5 ?
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 ?
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 ?
C21 C16 C17 . . 117.9(3) ?
C21 C16 C6 . . 122.2(2) ?
C17 C16 C6 . . 119.9(2) ?
C18 C17 C16 . . 122.1(3) ?
C18 C17 H17 . . 118.9 ?
C16 C17 H17 . . 118.9 ?
C19 C18 C17 . . 119.7(3) ?
C19 C18 H18 . . 120.1 ?
C17 C18 H18 . . 120.1 ?
C18 C19 C20 . . 120.5(3) ?
C18 C19 H19 . . 119.8 ?
C20 C19 H19 . . 119.8 ?
C19 C20 C21 . . 119.8(3) ?
C19 C20 H20 . . 120.1 ?
C21 C20 H20 . . 120.1 ?
C16 C21 C20 . . 120.0(3) ?
C16 C21 H21 . . 120.0 ?
C20 C21 H21 . . 120.0 ?
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 . 1.180(5) ?
O2 C4 . 1.213(3) ?
N1 C7 . 1.342(4) ?
N1 C2 . 1.462(3) ?
N1 C6 . 1.473(3) ?
C2 C8 . 1.522(4) ?
C2 C3 . 1.528(3) ?
C2 H2 . 0.98 ?
C3 C4 . 1.501(3) ?
C3 C14 . 1.532(3) ?
C3 H3 . 0.98 ?
C4 C5 . 1.507(3) ?
C5 C15 . 1.526(3) ?
C5 C6 . 1.536(3) ?
C5 H5 . 0.98 ?
C6 C16 . 1.513(3) ?
C6 H6 . 0.98 ?
C7 H7 . 0.95(4) ?
C8 C13 . 1.363(4) ?
C8 C9 . 1.376(4) ?
C9 C10 . 1.369(6) ?
C9 H9 . 0.93 ?
C10 C11 . 1.353(7) ?
C10 H10 . 0.93 ?
C11 C12 . 1.367(6) ?
C11 H11 . 0.93 ?
C12 C13 . 1.385(4) ?
C12 H12 . 0.93 ?
C13 H13 . 0.93 ?
C14 H14A . 0.96 ?
C14 H14B . 0.96 ?
C14 H14C . 0.96 ?
C15 H15A . 0.96 ?
C15 H15B . 0.96 ?
C15 H15C . 0.96 ?
C16 C21 . 1.374(4) ?
C16 C17 . 1.381(4) ?
C17 C18 . 1.365(4) ?
C17 H17 . 0.93 ?
C18 C19 . 1.341(5) ?
C18 H18 . 0.93 ?
C19 C20 . 1.378(5) ?
C19 H19 . 0.93 ?
C20 C21 . 1.393(4) ?
C20 H20 . 0.93 ?
C21 H21 . 0.93 ?
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 O2 6_556 0.98 2.48 3.398(3) 156
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 C8 . . . . 109.2(3) ?
C6 N1 C2 C8 . . . . -79.4(3) ?
C7 N1 C2 C3 . . . . -120.7(3) ?
C6 N1 C2 C3 . . . . 50.6(3) ?
N1 C2 C3 C4 . . . . -51.5(3) ?
C8 C2 C3 C4 . . . . 75.6(3) ?
N1 C2 C3 C14 . . . . 69.9(2) ?
C8 C2 C3 C14 . . . . -162.9(2) ?
C2 C3 C4 O2 . . . . -170.3(2) ?
C14 C3 C4 O2 . . . . 66.4(3) ?
C2 C3 C4 C5 . . . . 9.2(3) ?
C14 C3 C4 C5 . . . . -114.1(2) ?
O2 C4 C5 C15 . . . . -16.0(3) ?
C3 C4 C5 C15 . . . . 164.5(2) ?
O2 C4 C5 C6 . . . . -142.4(2) ?
C3 C4 C5 C6 . . . . 38.2(3) ?
C7 N1 C6 C16 . . . . -65.6(3) ?
C2 N1 C6 C16 . . . . 122.6(2) ?
C7 N1 C6 C5 . . . . 168.1(3) ?
C2 N1 C6 C5 . . . . -3.7(3) ?
C4 C5 C6 N1 . . . . -40.9(3) ?
C15 C5 C6 N1 . . . . -168.1(2) ?
C4 C5 C6 C16 . . . . -166.8(2) ?
C15 C5 C6 C16 . . . . 65.9(3) ?
C2 N1 C7 O1 . . . . -8.2(6) ?
C6 N1 C7 O1 . . . . -179.9(4) ?
N1 C2 C8 C13 . . . . 117.9(3) ?
C3 C2 C8 C13 . . . . -7.7(4) ?
N1 C2 C8 C9 . . . . -62.1(3) ?
C3 C2 C8 C9 . . . . 172.3(3) ?
C13 C8 C9 C10 . . . . -1.2(5) ?
C2 C8 C9 C10 . . . . 178.8(4) ?
C8 C9 C10 C11 . . . . -2.3(7) ?
C9 C10 C11 C12 . . . . 4.3(8) ?
C10 C11 C12 C13 . . . . -2.7(7) ?
C9 C8 C13 C12 . . . . 2.7(5) ?
C2 C8 C13 C12 . . . . -177.3(3) ?
C11 C12 C13 C8 . . . . -0.8(6) ?
N1 C6 C16 C21 . . . . -66.4(3) ?
C5 C6 C16 C21 . . . . 59.5(3) ?
N1 C6 C16 C17 . . . . 114.1(3) ?
C5 C6 C16 C17 . . . . -120.0(3) ?
C21 C16 C17 C18 . . . . -0.5(4) ?
C6 C16 C17 C18 . . . . 179.0(3) ?
C16 C17 C18 C19 . . . . 0.3(5) ?
C17 C18 C19 C20 . . . . 0.2(6) ?
C18 C19 C20 C21 . . . . -0.5(6) ?
C17 C16 C21 C20 . . . . 0.1(5) ?
C6 C16 C21 C20 . . . . -179.4(3) ?
C19 C20 C21 C16 . . . . 0.4(5) ?
