#------------------------------------------------------------------------------
#$Date: 2017-10-13 12:31:46 +0300 (Fri, 13 Oct 2017) $
#$Revision: 201979 $
#$URL: file:///home/coder/svn-repositories/cod/cif/2/23/08/2230873.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_2230873
loop_
_publ_author_name
'Siddegowda, M. S.'
'Jasinski, Jerry P.'
'Golen, James A.'
'Yathirajan, H. S.'
'Swamy, M. T.'
_publ_section_title
;
 2,2-Diphenyl-4-(piperidin-1-yl)butanamide
;
_journal_coeditor_code           SJ5167
_journal_issue                   7
_journal_name_full               'Acta Crystallographica Section E'
_journal_page_first              o1827
_journal_paper_doi               10.1107/S1600536811024585
_journal_volume                  67
_journal_year                    2011
_chemical_formula_iupac          'C21 H26 N2 O'
_chemical_formula_moiety         'C21 H26 N2 O'
_chemical_formula_sum            'C21 H26 N2 O'
_chemical_formula_weight         322.44
_chemical_name_systematic
;
2,2-Diphenyl-4-(piperidin-1-yl)butanamide
;
_space_group_IT_number           29
_symmetry_cell_setting           orthorhombic
_symmetry_space_group_name_Hall  'P 2c -2ac'
_symmetry_space_group_name_H-M   'P c a 21'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_cell_angle_alpha                90.00
_cell_angle_beta                 90.00
_cell_angle_gamma                90.00
_cell_formula_units_Z            4
_cell_length_a                   18.1070(12)
_cell_length_b                   10.3025(9)
_cell_length_c                   9.6150(6)
_cell_measurement_reflns_used    9220
_cell_measurement_temperature    173(2)
_cell_measurement_theta_max      32.51
_cell_measurement_theta_min      3.37
_cell_volume                     1793.7(2)
_computing_cell_refinement
'CrysAlis PRO (Oxford Diffraction, 2010)'
_computing_data_collection
'CrysAlis PRO (Oxford Diffraction, 2010)'
_computing_data_reduction
'CrysAlis RED (Oxford Diffraction, 2010)'
_computing_molecular_graphics    'SHELXTL (Sheldrick, 2008)'
_computing_publication_material  'SHELXTL (Sheldrick, 2008)'
_computing_structure_refinement  'SHELXL97 (Sheldrick, 2008)'
_computing_structure_solution    'SHELXS97 (Sheldrick, 2008)'
_diffrn_ambient_temperature      173(2)
_diffrn_detector_area_resol_mean 16.1500
_diffrn_measured_fraction_theta_full 0.998
_diffrn_measured_fraction_theta_max 0.998
_diffrn_measurement_device_type  'Oxford Diffraction Xcalibur Eos Gemini'
_diffrn_measurement_method       ω
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_source         'Enhance (Mo) X-ray Source'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0197
_diffrn_reflns_av_sigmaI/netI    0.0154
_diffrn_reflns_limit_h_max       24
_diffrn_reflns_limit_h_min       -24
_diffrn_reflns_limit_k_max       14
_diffrn_reflns_limit_k_min       -13
_diffrn_reflns_limit_l_max       13
_diffrn_reflns_limit_l_min       -13
_diffrn_reflns_number            19279
_diffrn_reflns_theta_full        25.24
_diffrn_reflns_theta_max         29.12
_diffrn_reflns_theta_min         3.67
_diffrn_standards_number         0
_exptl_absorpt_coefficient_mu    0.073
_exptl_absorpt_correction_T_max  0.9855
_exptl_absorpt_correction_T_min  0.9712
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
(CrysAlis RED; Oxford Diffraction, 2010)
;
_exptl_crystal_colour            colorless
_exptl_crystal_density_diffrn    1.194
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       block
_exptl_crystal_F_000             696
_exptl_crystal_size_max          0.40
_exptl_crystal_size_mid          0.32
_exptl_crystal_size_min          0.20
_refine_diff_density_max         0.216
_refine_diff_density_min         -0.156
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.019
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     224
_refine_ls_number_reflns         4817
_refine_ls_number_restraints     4
_refine_ls_restrained_S_all      1.020
_refine_ls_R_factor_all          0.0385
_refine_ls_R_factor_gt           0.0355
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'calc w=1/[σ²(Fo²)+(0.0674P)²+0.1453P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0987
_refine_ls_wR_factor_ref         0.1022
_reflns_number_gt                4547
_reflns_number_total             4817
_reflns_threshold_expression     I>2σ(I)
_cod_data_source_file            sj5167.cif
_cod_data_source_block           I
_cod_original_sg_symbol_Hall     'P 2c -2ac '
_cod_database_code               2230873
_cod_database_fobs_code          2230873
loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'-x, -y, z+1/2'
'x+1/2, -y, z'
'-x+1/2, y, 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_symmetry_multiplicity
_atom_site_disorder_assembly
_atom_site_disorder_group
O O1 0.68400(5) 0.34583(11) 0.96707(9) 0.0432(2) Uani d . 1 1 . .
N N1 0.75885(6) 0.33139(12) 0.78130(11) 0.0375(2) Uani d D 1 1 . .
H H1NB 0.7944(8) 0.2941(16) 0.8267(16) 0.045 Uiso d D 1 1 . .
H H1NA 0.7651(9) 0.3416(16) 0.6956(14) 0.045 Uiso d D 1 1 . .
N N2 0.62349(5) 0.19366(9) 0.43291(9) 0.02659(18) Uani d . 1 1 . .
C C1 0.69459(6) 0.36080(11) 0.84208(11) 0.0287(2) Uani d . 1 1 . .
C C2 0.63630(5) 0.42567(10) 0.74607(9) 0.02408(18) Uani d . 1 1 . .
C C3 0.64319(6) 0.37719(10) 0.59391(10) 0.02621(19) Uani d . 1 1 . .
H H3A 0.6058 0.4219 0.5361 0.031 Uiso calc R 1 1 . .
H H3B 0.6925 0.4011 0.5577 0.031 Uiso calc R 1 1 . .
C C4 0.63287(7) 0.23102(11) 0.57931(11) 0.0318(2) Uani d . 1 1 . .
H H4A 0.6764 0.1858 0.6183 0.038 Uiso calc R 1 1 . .
H H4B 0.5889 0.2036 0.6330 0.038 Uiso calc R 1 1 . .
C C5 0.54694(6) 0.21203(12) 0.38868(13) 0.0356(2) Uani d . 1 1 . .
H H5A 0.5320 0.3030 0.4065 0.043 Uiso calc R 1 1 . .
H H5B 0.5144 0.1547 0.4440 0.043 Uiso calc R 1 1 . .
C C6 0.53738(9) 0.18176(15) 0.23557(15) 0.0470(3) Uani d . 1 1 . .
H H6A 0.5671 0.2433 0.1797 0.056 Uiso calc R 1 1 . .
H H6B 0.4849 0.1928 0.2094 0.056 Uiso calc R 1 1 . .
C C7 0.56157(11) 0.04385(16) 0.20378(18) 0.0579(4) Uani d . 1 1 . .
H H7A 0.5270 -0.0182 0.2477 0.070 Uiso calc R 1 1 . .
H H7B 0.5606 0.0292 0.1020 0.070 Uiso calc R 1 1 . .
C C8 0.63853(10) 0.02107(16) 0.25826(18) 0.0578(4) Uani d . 1 1 . .
H H8A 0.6740 0.0726 0.2028 0.069 Uiso calc R 1 1 . .
H H8B 0.6513 -0.0718 0.2471 0.069 Uiso calc R 1 1 . .
C C9 0.64546(8) 0.05852(13) 0.41083(16) 0.0438(3) Uani d . 1 1 . .
H H9A 0.6138 0.0009 0.4677 0.053 Uiso calc R 1 1 . .
H H9B 0.6972 0.0465 0.4414 0.053 Uiso calc R 1 1 . .
C C10 0.55575(5) 0.40102(11) 0.78870(11) 0.0274(2) Uani d . 1 1 . .
C C11 0.53249(7) 0.30304(12) 0.87673(13) 0.0371(2) Uani d . 1 1 . .
H H11A 0.5678 0.2506 0.9235 0.044 Uiso calc R 1 1 . .
C C12 0.45683(8) 0.28120(16) 0.89694(16) 0.0494(3) Uani d . 1 1 . .
H H12A 0.4414 0.2148 0.9589 0.059 Uiso calc R 1 1 . .
C C13 0.40475(7) 0.35405(17) 0.82879(16) 0.0498(4) Uani d . 1 1 . .
H H13A 0.3537 0.3367 0.8417 0.060 Uiso calc R 1 1 . .
C C14 0.42691(7) 0.45219(15) 0.74177(16) 0.0455(3) Uani d . 1 1 . .
H H14A 0.3912 0.5038 0.6951 0.055 Uiso calc R 1 1 . .
C C15 0.50184(6) 0.47598(12) 0.72201(13) 0.0361(2) Uani d . 1 1 . .
H H15A 0.5167 0.5445 0.6621 0.043 Uiso calc R 1 1 . .
C C16 0.65362(5) 0.57150(11) 0.76043(11) 0.0287(2) Uani d . 1 1 . .
C C17 0.63429(7) 0.63353(13) 0.88404(14) 0.0404(3) Uani d . 1 1 . .
H H17A 0.6108 0.5856 0.9559 0.048 Uiso calc R 1 1 . .
C C18 0.64896(8) 0.76405(15) 0.90339(19) 0.0528(4) Uani d . 1 1 . .
H H18A 0.6355 0.8050 0.9882 0.063 Uiso calc R 1 1 . .
C C19 0.68294(9) 0.83480(15) 0.8005(2) 0.0565(4) Uani d . 1 1 . .
H H19A 0.6922 0.9248 0.8133 0.068 Uiso calc R 1 1 . .
C C20 0.70346(9) 0.77430(15) 0.6784(2) 0.0544(4) Uani d . 1 1 . .
H H20A 0.7272 0.8228 0.6073 0.065 Uiso calc R 1 1 . .
C C21 0.68962(7) 0.64287(13) 0.65859(15) 0.0400(3) Uani d . 1 1 . .
H H21A 0.7049 0.6018 0.5749 0.048 Uiso calc R 1 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
C1 N1 H1NB . . 121.7(11) ?
C1 N1 H1NA . . 121.3(11) ?
H1NB N1 H1NA . . 116.7(15) ?
C5 N2 C9 . . 109.79(9) ?
C5 N2 C4 . . 110.75(9) ?
C9 N2 C4 . . 110.90(10) ?
O1 C1 N1 . . 122.40(10) ?
O1 C1 C2 . . 122.01(10) ?
N1 C1 C2 . . 115.41(9) ?
C10 C2 C16 . . 109.30(8) ?
C10 C2 C3 . . 105.96(8) ?
C16 C2 C3 . . 112.46(8) ?
C10 C2 C1 . . 114.55(8) ?
C16 C2 C1 . . 103.17(8) ?
C3 C2 C1 . . 111.55(8) ?
C4 C3 C2 . . 113.28(8) ?
C4 C3 H3A . . 108.9 ?
C2 C3 H3A . . 108.9 ?
C4 C3 H3B . . 108.9 ?
C2 C3 H3B . . 108.9 ?
H3A C3 H3B . . 107.7 ?
N2 C4 C3 . . 111.18(8) ?
N2 C4 H4A . . 109.4 ?
C3 C4 H4A . . 109.4 ?
N2 C4 H4B . . 109.4 ?
C3 C4 H4B . . 109.4 ?
H4A C4 H4B . . 108.0 ?
N2 C5 C6 . . 111.37(11) ?
N2 C5 H5A . . 109.4 ?
C6 C5 H5A . . 109.4 ?
N2 C5 H5B . . 109.4 ?
C6 C5 H5B . . 109.4 ?
H5A C5 H5B . . 108.0 ?
C5 C6 C7 . . 110.82(12) ?
C5 C6 H6A . . 109.5 ?
C7 C6 H6A . . 109.5 ?
C5 C6 H6B . . 109.5 ?
C7 C6 H6B . . 109.5 ?
H6A C6 H6B . . 108.1 ?
C8 C7 C6 . . 110.04(12) ?
C8 C7 H7A . . 109.7 ?
C6 C7 H7A . . 109.7 ?
C8 C7 H7B . . 109.7 ?
C6 C7 H7B . . 109.7 ?
H7A C7 H7B . . 108.2 ?
C7 C8 C9 . . 111.82(13) ?
C7 C8 H8A . . 109.3 ?
C9 C8 H8A . . 109.3 ?
C7 C8 H8B . . 109.3 ?
C9 C8 H8B . . 109.3 ?
H8A C8 H8B . . 107.9 ?
N2 C9 C8 . . 111.01(12) ?
N2 C9 H9A . . 109.4 ?
C8 C9 H9A . . 109.4 ?
N2 C9 H9B . . 109.4 ?
C8 C9 H9B . . 109.4 ?
H9A C9 H9B . . 108.0 ?
C11 C10 C15 . . 118.07(10) ?
C11 C10 C2 . . 124.97(10) ?
C15 C10 C2 . . 116.65(10) ?
C10 C11 C12 . . 119.97(12) ?
C10 C11 H11A . . 120.0 ?
C12 C11 H11A . . 120.0 ?
C13 C12 C11 . . 121.18(14) ?
C13 C12 H12A . . 119.4 ?
C11 C12 H12A . . 119.4 ?
C12 C13 C14 . . 119.56(12) ?
C12 C13 H13A . . 120.2 ?
C14 C13 H13A . . 120.2 ?
C13 C14 C15 . . 119.87(13) ?
C13 C14 H14A . . 120.1 ?
C15 C14 H14A . . 120.1 ?
C14 C15 C10 . . 121.33(12) ?
C14 C15 H15A . . 119.3 ?
C10 C15 H15A . . 119.3 ?
C21 C16 C17 . . 118.48(11) ?
C21 C16 C2 . . 123.31(10) ?
C17 C16 C2 . . 118.18(10) ?
C18 C17 C16 . . 120.80(14) ?
C18 C17 H17A . . 119.6 ?
C16 C17 H17A . . 119.6 ?
C19 C18 C17 . . 120.31(15) ?
C19 C18 H18A . . 119.8 ?
C17 C18 H18A . . 119.8 ?
C18 C19 C20 . . 119.56(14) ?
C18 C19 H19A . . 120.2 ?
C20 C19 H19A . . 120.2 ?
C19 C20 C21 . . 120.52(16) ?
C19 C20 H20A . . 119.7 ?
C21 C20 H20A . . 119.7 ?
C16 C21 C20 . . 120.29(13) ?
C16 C21 H21A . . 119.9 ?
C20 C21 H21A . . 119.9 ?
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 C1 . 1.2267(14) ?
N1 C1 . 1.3368(14) ?
N1 H1NB . 0.867(12) ?
N1 H1NA . 0.838(13) ?
N2 C5 . 1.4621(14) ?
N2 C9 . 1.4635(14) ?
N2 C4 . 1.4692(13) ?
C1 C2 . 1.5534(13) ?
C2 C10 . 1.5362(13) ?
C2 C16 . 1.5411(14) ?
C2 C3 . 1.5509(13) ?
C3 C4 . 1.5239(15) ?
C3 H3A . 0.9900 ?
C3 H3B . 0.9900 ?
C4 H4A . 0.9900 ?
C4 H4B . 0.9900 ?
C5 C6 . 1.5147(18) ?
C5 H5A . 0.9900 ?
C5 H5B . 0.9900 ?
C6 C7 . 1.518(2) ?
C6 H6A . 0.9900 ?
C6 H6B . 0.9900 ?
C7 C8 . 1.507(2) ?
C7 H7A . 0.9900 ?
C7 H7B . 0.9900 ?
C8 C9 . 1.522(2) ?
C8 H8A . 0.9900 ?
C8 H8B . 0.9900 ?
C9 H9A . 0.9900 ?
C9 H9B . 0.9900 ?
C10 C11 . 1.3830(16) ?
C10 C15 . 1.4002(16) ?
C11 C12 . 1.4017(18) ?
C11 H11A . 0.9500 ?
C12 C13 . 1.372(2) ?
C12 H12A . 0.9500 ?
C13 C14 . 1.372(2) ?
C13 H13A . 0.9500 ?
C14 C15 . 1.3918(17) ?
C14 H14A . 0.9500 ?
C15 H15A . 0.9500 ?
C16 C21 . 1.3871(17) ?
C16 C17 . 1.3941(16) ?
C17 C18 . 1.3832(19) ?
C17 H17A . 0.9500 ?
C18 C19 . 1.375(3) ?
C18 H18A . 0.9500 ?
C19 C20 . 1.380(3) ?
C19 H19A . 0.9500 ?
C20 C21 . 1.390(2) ?
C20 H20A . 0.9500 ?
C21 H21A . 0.9500 ?
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
N1 H1NB N2 4_655 0.867(12) 2.080(13) 2.9457(13) 176.5(16)
N1 H1NA O1 4_654 0.838(13) 2.383(14) 3.1971(14) 164.0(15)
C3 H3B O1 4_654 0.99 2.47 3.3738(14) 152
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
O1 C1 C2 C10 . . . . -32.45(15) ?
N1 C1 C2 C10 . . . . 152.28(10) ?
O1 C1 C2 C16 . . . . 86.24(13) ?
N1 C1 C2 C16 . . . . -89.03(11) ?
O1 C1 C2 C3 . . . . -152.81(11) ?
N1 C1 C2 C3 . . . . 31.92(13) ?
C10 C2 C3 C4 . . . . -65.67(11) ?
C16 C2 C3 C4 . . . . 174.97(8) ?
C1 C2 C3 C4 . . . . 59.61(12) ?
C5 N2 C4 C3 . . . . -82.56(11) ?
C9 N2 C4 C3 . . . . 155.28(10) ?
C2 C3 C4 N2 . . . . 167.45(9) ?
C9 N2 C5 C6 . . . . -60.68(14) ?
C4 N2 C5 C6 . . . . 176.51(10) ?
N2 C5 C6 C7 . . . . 57.66(16) ?
C5 C6 C7 C8 . . . . -52.61(19) ?
C6 C7 C8 C9 . . . . 52.17(19) ?
C5 N2 C9 C8 . . . . 59.41(15) ?
C4 N2 C9 C8 . . . . -177.87(12) ?
C7 C8 C9 N2 . . . . -56.18(18) ?
C16 C2 C10 C11 . . . . -133.19(11) ?
C3 C2 C10 C11 . . . . 105.40(11) ?
C1 C2 C10 C11 . . . . -18.01(15) ?
C16 C2 C10 C15 . . . . 53.39(12) ?
C3 C2 C10 C15 . . . . -68.02(12) ?
C1 C2 C10 C15 . . . . 168.56(10) ?
C15 C10 C11 C12 . . . . 0.03(17) ?
C2 C10 C11 C12 . . . . -173.31(11) ?
C10 C11 C12 C13 . . . . 1.2(2) ?
C11 C12 C13 C14 . . . . -1.6(2) ?
C12 C13 C14 C15 . . . . 0.8(2) ?
C13 C14 C15 C10 . . . . 0.40(19) ?
C11 C10 C15 C14 . . . . -0.80(17) ?
C2 C10 C15 C14 . . . . 173.09(11) ?
C10 C2 C16 C21 . . . . -133.26(11) ?
C3 C2 C16 C21 . . . . -15.87(14) ?
C1 C2 C16 C21 . . . . 104.46(12) ?
C10 C2 C16 C17 . . . . 48.96(12) ?
C3 C2 C16 C17 . . . . 166.35(10) ?
C1 C2 C16 C17 . . . . -73.32(11) ?
C21 C16 C17 C18 . . . . 1.61(19) ?
C2 C16 C17 C18 . . . . 179.50(11) ?
C16 C17 C18 C19 . . . . 0.0(2) ?
C17 C18 C19 C20 . . . . -1.1(2) ?
C18 C19 C20 C21 . . . . 0.4(3) ?
C17 C16 C21 C20 . . . . -2.26(19) ?
C2 C16 C21 C20 . . . . 179.98(12) ?
C19 C20 C21 C16 . . . . 1.3(2) ?
loop_
_cod_related_entry_id
_cod_related_entry_database
_cod_related_entry_code
1 ChemSpider 59016
