##############################################################################
#                                                                            #
# This CIF contains the data for a data article accepted for                 #
# publication in IUCrData. It conforms to the requirements of                #
# Notes for Authors for IUCrData, and has been                               #
# peer reviewed under the auspices of IUCrData.                              #
#                                                                            #
# Full details of the Crystallographic Information File format               #
# are given in the paper "The Crystallographic Information File (CIF):       #
# a New Standard Archive File for Crystallography" by S. R. Hall, F. H.      #
# Allen and I. D. Brown [Acta Cryst. (1991), A47, 655-685].                  #
#                                                                            #
# The current version of the core CIF dictionary is obtainable from          #
# ftp://ftp.iucr.org/pub/cif_core.dic.                                       #
#                                                                            #
# Software is freely available for graphical display of the structure(s)     #
# in this CIF. For information consult the CIF software page                 #
# http://www.iucr.org/resources/cif/software.                                #
#                                                                            #
# This file may be used for bona fide research purposes within the           #
# scientific community so long as proper attribution is given to the data    # 
# article from which it was obtained.                                        #
#                                                                            #
##############################################################################
data_I
_database_code_depnum_ccdc_archive 'CCDC 1996936'
_audit_creation_method     'SHELXL-2018/3'
_chemical_name_systematic
;
2,6-Diphenyl-3-(prop-2-en-1-yl)piperidin-4-one
;
_chemical_name_common     ?
_chemical_formula_moiety     'C20 H21 N O'
_chemical_formula_sum     'C20 H21 N O'
_chemical_formula_iupac     'C20 H21 N O'
_chemical_formula_weight     291.38
_chemical_melting_point     ?
_space_group_crystal_system     monoclinic
_space_group_name_H-M_alt     'C 2/c'
_space_group_name_Hall     '-C 2yc'
loop_
    _space_group_symop_operation_xyz
    'x, y, z'
    '-x, y, -z+1/2'
    'x+1/2, y+1/2, z'
    '-x+1/2, y+1/2, -z+1/2'
    '-x, -y, -z'
    'x, -y, z-1/2'
    '-x+1/2, -y+1/2, -z'
    'x+1/2, -y+1/2, z-1/2'
_cell_length_a     16.7588(4)
_cell_length_b     23.4597(5)
_cell_length_c     8.7769(2)
_cell_angle_alpha     90
_cell_angle_beta     98.7710(10)
_cell_angle_gamma     90
_cell_volume     3410.34(13)
_cell_formula_units_Z     8
_cell_measurement_reflns_used     12118
_cell_measurement_theta_min     2.6
_cell_measurement_theta_max     25.8
_cell_measurement_temperature     296(2)
_exptl_crystal_description     Block
_exptl_crystal_colour     Colourless
_exptl_crystal_size_max     0.24
_exptl_crystal_size_mid     0.21
_exptl_crystal_size_min     0.19
_exptl_crystal_density_diffrn     1.135
_exptl_crystal_density_meas     ?
_exptl_crystal_density_method     'not measured'
_exptl_crystal_F_000     1248
_exptl_absorpt_coefficient_mu     0.069
_exptl_absorpt_correction_type     none
_exptl_absorpt_process_details     ?
_exptl_absorpt_correction_T_min     ?
_exptl_absorpt_correction_T_max     ?
_diffrn_ambient_temperature     296(2)
_diffrn_radiation_type     MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_source     'fine-focus sealed tube'
_diffrn_measurement_device_type     'Bruker SMART APEX CCD'
_diffrn_measurement_method     'ω and φ scans'
_diffrn_detector_area_resol_mean     ?
_diffrn_reflns_number     28337
_diffrn_reflns_av_R_equivalents     0.0711
_diffrn_reflns_av_unetI/netI     0.0701
_diffrn_reflns_theta_min     2.459
_diffrn_reflns_theta_max     30.497
_diffrn_reflns_theta_full     25.242
_diffrn_measured_fraction_theta_max     0.998
_diffrn_measured_fraction_theta_full     0.999
_diffrn_reflns_limit_h_min     -23
_diffrn_reflns_limit_h_max     23
_diffrn_reflns_limit_k_min     -24
_diffrn_reflns_limit_k_max     33
_diffrn_reflns_limit_l_min     -12
_diffrn_reflns_limit_l_max     12
_refine_special_details
;
The C-bound H atoms were placed in idealized locations and refined as
riding atoms. The N-bound H atom was located in a difference map and refined
with a restraint.
;
_reflns_number_total     5208
_reflns_number_gt     2586
_reflns_threshold_expression     'I > 2σ(I)'
_refine_ls_structure_factor_coef     Fsqd
_refine_ls_matrix_type     full
_refine_ls_R_factor_all     0.1723
_refine_ls_R_factor_gt     0.0797
_refine_ls_wR_factor_gt     0.1648
_refine_ls_wR_factor_ref     0.2005
_refine_ls_goodness_of_fit_ref     1.030
_refine_ls_restrained_S_all     1.030
_refine_ls_number_reflns     5208
_refine_ls_number_parameters     203
_refine_ls_number_restraints     1
_refine_ls_hydrogen_treatment     mixed
_refine_ls_weighting_scheme     calc
_refine_ls_weighting_details
              'w=1/[σ²(Fo²)+(0.0736P)²+2.1792P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_hydrogens     mixed
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary     ?
_refine_ls_shift/su_max     0.000
_refine_ls_shift/su_mean     0.000
_refine_diff_density_max     0.224
_refine_diff_density_min     -0.194
_refine_ls_extinction_method     none
_refine_ls_extinction_coef     .
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'
_computing_data_collection
;
SMART (Bruker, 2002)
;
_computing_cell_refinement
;
SAINT (Bruker, 2002)
;
_computing_data_reduction
;
SAINT (Bruker, 2002)
;
_computing_structure_solution
;
SHELXS97 (Sheldrick, 2008)
;
_computing_structure_refinement
;
SHELXL2018/3 (Sheldrick, 2015)
;
_computing_molecular_graphics
;
ORTEP-3 for Windows (Farrugia, 2012) and PLATON (Spek, 2020)
;
_computing_publication_material
;
SHELXL2018/3 (Sheldrick, 2015) and PLATON (Spek, 2020)
;
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_occupancy
    _atom_site_disorder_assembly
    _atom_site_disorder_group
    H H1N 0.1365(10) 0.3964(7) 0.4008(13) 0.034(5) Uiso d 1 . .
    O O1 0.20727(10) 0.25243(7) 0.7596(2) 0.0756(5) Uani d 1 . .
    N N1 0.14621(9) 0.38387(7) 0.4932(2) 0.0440(4) Uani d 1 . .
    C C1 0.08589(11) 0.34078(9) 0.5144(2) 0.0454(5) Uani d 1 . .
    H H1 0.091163 0.308720 0.445077 0.054 Uiso calc 1 . .
    C C2 0.10339(12) 0.31960(10) 0.6811(3) 0.0537(5) Uani d 1 . .
    H H2A 0.093153 0.349981 0.750586 0.064 Uiso calc 1 . .
    H H2B 0.067787 0.288036 0.694966 0.064 Uiso calc 1 . .
    C C3 0.18939(13) 0.30065(10) 0.7189(2) 0.0520(5) Uani d 1 . .
    C C4 0.25116(12) 0.34443(9) 0.6888(2) 0.0475(5) Uani d 1 . .
    H H4 0.244557 0.378105 0.751803 0.057 Uiso calc 1 . .
    C C5 0.22884(11) 0.36147(9) 0.5167(2) 0.0437(5) Uani d 1 . .
    H H5 0.230394 0.327262 0.453108 0.052 Uiso calc 1 . .
    C C6 0.00096(11) 0.36388(9) 0.4799(2) 0.0457(5) Uani d 1 . .
    C C7 -0.01719(13) 0.41865(10) 0.5187(3) 0.0700(7) Uani d 1 . .
    H H7 0.023993 0.443022 0.561372 0.084 Uiso calc 1 . .
    C C8 -0.09651(15) 0.43787(11) 0.4947(4) 0.0828(9) Uani d 1 . .
    H H8 -0.108226 0.474984 0.521265 0.099 Uiso calc 1 . .
    C C9 -0.15798(13) 0.40190(12) 0.4315(3) 0.0697(7) Uani d 1 . .
    H H9 -0.210973 0.414956 0.413381 0.084 Uiso calc 1 . .
    C C10 -0.14082(13) 0.34762(12) 0.3960(3) 0.0604(6) Uani d 1 . .
    H H10 -0.182316 0.323007 0.356199 0.072 Uiso calc 1 . .
    C C11 -0.06178(12) 0.32856(10) 0.4187(2) 0.0516(5) Uani d 1 . .
    H H11 -0.050688 0.291315 0.392277 0.062 Uiso calc 1 . .
    C C12 0.33802(13) 0.32300(11) 0.7319(3) 0.0639(6) Uani d 1 . .
    H H12A 0.342670 0.286037 0.684469 0.077 Uiso calc 1 . .
    H H12B 0.374059 0.349014 0.689870 0.077 Uiso calc 1 . .
    C C13 0.36444(17) 0.31778(12) 0.9013(3) 0.0778(8) Uani d 1 . .
    H H13 0.330510 0.298403 0.958095 0.093 Uiso calc 1 . .
    C C14 0.4310(2) 0.33817(16) 0.9754(5) 0.1174(13) Uani d 1 . .
    H H14A 0.466503 0.357808 0.922576 0.141 Uiso calc 1 . .
    H H14B 0.443395 0.333178 1.081520 0.141 Uiso calc 1 . .
    C C15 0.28595(11) 0.40515(9) 0.4675(2) 0.0456(5) Uani d 1 . .
    C C16 0.34151(12) 0.38922(11) 0.3724(3) 0.0612(6) Uani d 1 . .
    H H16 0.342811 0.351815 0.337808 0.073 Uiso calc 1 . .
    C C17 0.39434(14) 0.42874(14) 0.3297(3) 0.0784(8) Uani d 1 . .
    H H17 0.431583 0.417627 0.267007 0.094 Uiso calc 1 . .
    C C18 0.39317(15) 0.48407(15) 0.3776(3) 0.0789(8) Uani d 1 . .
    H H18 0.429663 0.510311 0.348618 0.095 Uiso calc 1 . .
    C C19 0.33762(16) 0.50067(12) 0.4689(3) 0.0748(7) Uani d 1 . .
    H H19 0.335531 0.538466 0.500032 0.090 Uiso calc 1 . .
    C C20 0.28487(13) 0.46112(10) 0.5145(3) 0.0609(6) Uani d 1 . .
    H H20 0.248064 0.472486 0.577783 0.073 Uiso calc 1 . .
_geom_special_details
;
 All esds (except the esd in the dihedral angle between two l.s. planes)
 are estimated using the full covariance matrix.  The cell esds are taken
 into account individually in the estimation of esds in distances, angles
 and torsion angles; correlations between esds in cell parameters are only
 used when they are defined by crystal symmetry.  An approximate (isotropic)
 treatment of cell esds is used for estimating esds involving l.s. planes.
;
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 C3 . 1.210(3) ?
    N1 C1 . 1.461(2) ?
    N1 C5 . 1.466(2) ?
    N1 H1N . 0.854(9) ?
    C1 C6 . 1.510(3) ?
    C1 C2 . 1.531(3) ?
    C1 H1 . 0.9800 ?
    C2 C3 . 1.496(3) ?
    C2 H2A . 0.9700 ?
    C2 H2B . 0.9700 ?
    C3 C4 . 1.510(3) ?
    C4 C12 . 1.532(3) ?
    C4 C5 . 1.552(3) ?
    C4 H4 . 0.9800 ?
    C5 C15 . 1.509(3) ?
    C5 H5 . 0.9800 ?
    C6 C7 . 1.375(3) ?
    C6 C11 . 1.381(3) ?
    C7 C8 . 1.389(3) ?
    C7 H7 . 0.9300 ?
    C8 C9 . 1.381(4) ?
    C8 H8 . 0.9300 ?
    C9 C10 . 1.352(3) ?
    C9 H9 . 0.9300 ?
    C10 C11 . 1.383(3) ?
    C10 H10 . 0.9300 ?
    C11 H11 . 0.9300 ?
    C12 C13 . 1.491(4) ?
    C12 H12A . 0.9700 ?
    C12 H12B . 0.9700 ?
    C13 C14 . 1.295(4) ?
    C13 H13 . 0.9300 ?
    C14 H14A . 0.9300 ?
    C14 H14B . 0.9300 ?
    C15 C20 . 1.377(3) ?
    C15 C16 . 1.393(3) ?
    C16 C17 . 1.373(4) ?
    C16 H16 . 0.9300 ?
    C17 C18 . 1.365(4) ?
    C17 H17 . 0.9300 ?
    C18 C19 . 1.374(4) ?
    C18 H18 . 0.9300 ?
    C19 C20 . 1.382(3) ?
    C19 H19 . 0.9300 ?
    C20 H20 . 0.9300 ?
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 C5 . . 113.02(16) ?
    C1 N1 H1N . . 108.8(12) ?
    C5 N1 H1N . . 107.2(12) ?
    N1 C1 C6 . . 112.05(16) ?
    N1 C1 C2 . . 108.11(16) ?
    C6 C1 C2 . . 110.23(16) ?
    N1 C1 H1 . . 108.8 ?
    C6 C1 H1 . . 108.8 ?
    C2 C1 H1 . . 108.8 ?
    C3 C2 C1 . . 110.24(16) ?
    C3 C2 H2A . . 109.6 ?
    C1 C2 H2A . . 109.6 ?
    C3 C2 H2B . . 109.6 ?
    C1 C2 H2B . . 109.6 ?
    H2A C2 H2B . . 108.1 ?
    O1 C3 C2 . . 122.0(2) ?
    O1 C3 C4 . . 122.82(19) ?
    C2 C3 C4 . . 114.97(18) ?
    C3 C4 C12 . . 112.63(19) ?
    C3 C4 C5 . . 105.99(17) ?
    C12 C4 C5 . . 113.78(16) ?
    C3 C4 H4 . . 108.1 ?
    C12 C4 H4 . . 108.1 ?
    C5 C4 H4 . . 108.1 ?
    N1 C5 C15 . . 110.06(16) ?
    N1 C5 C4 . . 108.14(14) ?
    C15 C5 C4 . . 112.57(16) ?
    N1 C5 H5 . . 108.7 ?
    C15 C5 H5 . . 108.7 ?
    C4 C5 H5 . . 108.7 ?
    C7 C6 C11 . . 118.21(19) ?
    C7 C6 C1 . . 121.52(18) ?
    C11 C6 C1 . . 120.08(19) ?
    C6 C7 C8 . . 120.6(2) ?
    C6 C7 H7 . . 119.7 ?
    C8 C7 H7 . . 119.7 ?
    C9 C8 C7 . . 120.0(2) ?
    C9 C8 H8 . . 120.0 ?
    C7 C8 H8 . . 120.0 ?
    C10 C9 C8 . . 119.8(2) ?
    C10 C9 H9 . . 120.1 ?
    C8 C9 H9 . . 120.1 ?
    C9 C10 C11 . . 120.2(2) ?
    C9 C10 H10 . . 119.9 ?
    C11 C10 H10 . . 119.9 ?
    C6 C11 C10 . . 121.2(2) ?
    C6 C11 H11 . . 119.4 ?
    C10 C11 H11 . . 119.4 ?
    C13 C12 C4 . . 113.5(2) ?
    C13 C12 H12A . . 108.9 ?
    C4 C12 H12A . . 108.9 ?
    C13 C12 H12B . . 108.9 ?
    C4 C12 H12B . . 108.9 ?
    H12A C12 H12B . . 107.7 ?
    C14 C13 C12 . . 125.0(3) ?
    C14 C13 H13 . . 117.5 ?
    C12 C13 H13 . . 117.5 ?
    C13 C14 H14A . . 120.0 ?
    C13 C14 H14B . . 120.0 ?
    H14A C14 H14B . . 120.0 ?
    C20 C15 C16 . . 118.4(2) ?
    C20 C15 C5 . . 121.60(18) ?
    C16 C15 C5 . . 120.0(2) ?
    C17 C16 C15 . . 120.0(2) ?
    C17 C16 H16 . . 120.0 ?
    C15 C16 H16 . . 120.0 ?
    C18 C17 C16 . . 121.2(2) ?
    C18 C17 H17 . . 119.4 ?
    C16 C17 H17 . . 119.4 ?
    C17 C18 C19 . . 119.5(2) ?
    C17 C18 H18 . . 120.3 ?
    C19 C18 H18 . . 120.3 ?
    C18 C19 C20 . . 119.9(3) ?
    C18 C19 H19 . . 120.0 ?
    C20 C19 H19 . . 120.0 ?
    C15 C20 C19 . . 121.0(2) ?
    C15 C20 H20 . . 119.5 ?
    C19 C20 H20 . . 119.5 ?
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
    C5 N1 C1 C6 . . . . -176.38(16) ?
    C5 N1 C1 C2 . . . . 61.9(2) ?
    N1 C1 C2 C3 . . . . -53.1(2) ?
    C6 C1 C2 C3 . . . . -175.88(17) ?
    C1 C2 C3 O1 . . . . -120.6(2) ?
    C1 C2 C3 C4 . . . . 54.2(2) ?
    O1 C3 C4 C12 . . . . -6.1(3) ?
    C2 C3 C4 C12 . . . . 179.14(18) ?
    O1 C3 C4 C5 . . . . 118.9(2) ?
    C2 C3 C4 C5 . . . . -55.8(2) ?
    C1 N1 C5 C15 . . . . 170.62(16) ?
    C1 N1 C5 C4 . . . . -66.1(2) ?
    C3 C4 C5 N1 . . . . 58.6(2) ?
    C12 C4 C5 N1 . . . . -177.06(18) ?
    C3 C4 C5 C15 . . . . -179.56(16) ?
    C12 C4 C5 C15 . . . . -55.3(2) ?
    N1 C1 C6 C7 . . . . -37.4(3) ?
    C2 C1 C6 C7 . . . . 83.0(3) ?
    N1 C1 C6 C11 . . . . 147.64(19) ?
    C2 C1 C6 C11 . . . . -91.9(2) ?
    C11 C6 C7 C8 . . . . -0.9(4) ?
    C1 C6 C7 C8 . . . . -175.9(2) ?
    C6 C7 C8 C9 . . . . 0.0(5) ?
    C7 C8 C9 C10 . . . . 1.3(4) ?
    C8 C9 C10 C11 . . . . -1.9(4) ?
    C7 C6 C11 C10 . . . . 0.4(3) ?
    C1 C6 C11 C10 . . . . 175.5(2) ?
    C9 C10 C11 C6 . . . . 1.0(3) ?
    C3 C4 C12 C13 . . . . -70.9(3) ?
    C5 C4 C12 C13 . . . . 168.4(2) ?
    C4 C12 C13 C14 . . . . -130.5(3) ?
    N1 C5 C15 C20 . . . . 48.1(2) ?
    C4 C5 C15 C20 . . . . -72.7(2) ?
    N1 C5 C15 C16 . . . . -131.9(2) ?
    C4 C5 C15 C16 . . . . 107.4(2) ?
    C20 C15 C16 C17 . . . . 1.1(3) ?
    C5 C15 C16 C17 . . . . -179.0(2) ?
    C15 C16 C17 C18 . . . . -0.7(4) ?
    C16 C17 C18 C19 . . . . -0.6(4) ?
    C17 C18 C19 C20 . . . . 1.5(4) ?
    C16 C15 C20 C19 . . . . -0.2(3) ?
    C5 C15 C20 C19 . . . . 179.8(2) ?
    C18 C19 C20 C15 . . . . -1.1(4) ?
_shelx_space_group_comment
;
The symmetry employed for this shelxl refinement is uniquely defined
by the following loop, which should always be used as a source of
symmetry information in preference to the above space-group names.
They are only intended as comments.
;
_shelx_estimated_absorpt_T_min     ?
_shelx_estimated_absorpt_T_max     ?
data_global
_journal_date_recd_electronic     2020-03-26
_journal_date_accepted     2020-04-15
_journal_name_full     'IUCrData'
_journal_year     2020
_journal_volume     5
_journal_issue      4
_journal_page_first     0
_journal_page_last     0
_journal_paper_category     HO
_journal_paper_doi     10.1107/S241431462000526X
_journal_coeditor_code     HB4345
_publ_contact_author_name     'Dr. J. Dharmaraja'
_publ_contact_author_address
;
Department of Chemistry
Anna Government Arts College
Vadachennimalai
Attur 636 121
India
;
_publ_contact_author_email     jagandharma77@gmail.com
_publ_contact_author_fax     '91-9976240753'
_publ_contact_author_phone     '91-9976240753'
_publ_section_title
;
2,6-Diphenyl-3-(prop-2-en-1-yl)piperidin-4-one
;
loop_
    _publ_author_name
    _publ_author_footnote
    _publ_author_address
    'V. Manjula' .
;     Department of Chemistry
      Periyar University
      Salem 636 011
      India
;
    'R. Venkateswaramoorthi' .
;     Department of Chemistry
      PGP College of Arts and Science
      Namakkal 637 207
      India
;
    'J. Dharmaraja' .
;     Department of Chemistry
      Anna Government Arts College
      Vadachennimalai
      Attur 636 121
      India
;
    'S. Selvanayagam' .
;     PG & Research Department of Physics
      Government Arts College
      Melur 625 106
      India
;
_publ_section_synopsis
;
In the title piperidine derivative, the molecules are linked by C---H...π
interactions into dimers related by twofold symmetry.
;
