#------------------------------------------------------------------------------
#$Date: 2020-04-22 06:38:44 +0300 (Wed, 22 Apr 2020) $
#$Revision: 251012 $
#$URL: file:///home/coder/svn-repositories/cod/cif/1/55/78/1557847.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_1557847
loop_
_publ_author_name
'Manjula, V.'
'Venkateswaramoorthi, R.'
'Dharmaraja, J.'
'Selvanayagam, S.'
_publ_section_title
;
 2,6-Diphenyl-3-(prop-2-en-1-yl)piperidin-4-one
;
_journal_coeditor_code           HB4345
_journal_issue                   4
_journal_name_full               IUCrData
_journal_page_first              x200526
_journal_paper_doi               10.1107/S241431462000526X
_journal_volume                  5
_journal_year                    2020
_chemical_formula_iupac          'C20 H21 N O'
_chemical_formula_moiety         'C20 H21 N O'
_chemical_formula_sum            'C20 H21 N O'
_chemical_formula_weight         291.38
_chemical_name_systematic
;
2,6-Diphenyl-3-(prop-2-en-1-yl)piperidin-4-one
;
_space_group_crystal_system      monoclinic
_space_group_IT_number           15
_space_group_name_Hall           '-C 2yc'
_space_group_name_H-M_alt        'C 1 2/c 1'
_atom_sites_solution_hydrogens   mixed
_atom_sites_solution_primary     direct
_audit_creation_method           SHELXL-2018/3
_cell_angle_alpha                90
_cell_angle_beta                 98.7710(10)
_cell_angle_gamma                90
_cell_formula_units_Z            8
_cell_length_a                   16.7588(4)
_cell_length_b                   23.4597(5)
_cell_length_c                   8.7769(2)
_cell_measurement_reflns_used    12118
_cell_measurement_temperature    296(2)
_cell_measurement_theta_max      25.8
_cell_measurement_theta_min      2.6
_cell_volume                     3410.34(13)
_computing_cell_refinement
;
SAINT (Bruker, 2002)
;
_computing_data_collection
;
SMART (Bruker, 2002)
;
_computing_data_reduction
;
SAINT (Bruker, 2002)
;
_computing_molecular_graphics
;
ORTEP-3 for Windows (Farrugia, 2012) and PLATON (Spek, 2020)
;
_computing_publication_material
;
SHELXL2018/3 (Sheldrick, 2015) and PLATON (Spek, 2020)
;
_computing_structure_refinement
;
SHELXL2018/3 (Sheldrick, 2015)
;
_computing_structure_solution
;
SHELXS97 (Sheldrick, 2008)
;
_diffrn_ambient_temperature      296(2)
_diffrn_measured_fraction_theta_full 0.999
_diffrn_measured_fraction_theta_max 0.998
_diffrn_measurement_device_type  'Bruker SMART APEX CCD'
_diffrn_measurement_method       'ω and φ scans'
_diffrn_radiation_source         'fine-focus sealed tube'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0711
_diffrn_reflns_av_unetI/netI     0.0701
_diffrn_reflns_limit_h_max       23
_diffrn_reflns_limit_h_min       -23
_diffrn_reflns_limit_k_max       33
_diffrn_reflns_limit_k_min       -24
_diffrn_reflns_limit_l_max       12
_diffrn_reflns_limit_l_min       -12
_diffrn_reflns_number            28337
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         30.497
_diffrn_reflns_theta_min         2.459
_exptl_absorpt_coefficient_mu    0.069
_exptl_absorpt_correction_type   none
_exptl_crystal_colour            Colourless
_exptl_crystal_density_diffrn    1.135
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       Block
_exptl_crystal_F_000             1248
_exptl_crystal_size_max          0.24
_exptl_crystal_size_mid          0.21
_exptl_crystal_size_min          0.19
_refine_diff_density_max         0.224
_refine_diff_density_min         -0.194
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.030
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     203
_refine_ls_number_reflns         5208
_refine_ls_number_restraints     1
_refine_ls_restrained_S_all      1.030
_refine_ls_R_factor_all          0.1723
_refine_ls_R_factor_gt           0.0797
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'w=1/[σ²(Fo²)+(0.0736P)²+2.1792P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1648
_refine_ls_wR_factor_ref         0.2005
_reflns_number_gt                2586
_reflns_number_total             5208
_reflns_threshold_expression     'I > 2σ(I)'
_cod_data_source_file            hb4345sup1.cif
_cod_data_source_block           I
_cod_original_sg_symbol_H-M      'C 2/c'
_cod_database_code               1557847
_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.
;
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'
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 . .
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 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_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_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) ?

_cod_database_fobs_code 1557847
