#------------------------------------------------------------------------------
#$Date: 2016-02-20 21:30:07 +0100 (Sat 20 de Feb de 2016) $
#$Revision: 176789 $
#$URL: svn://www.crystallography.net/cod/cif/2/22/60/2226070.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_2226070
loop_
_publ_author_name
'Aridoss, G.'
'Sundaramoorthy, S.'
'Velmurugan, D.'
'Park, K. S.'
'Jeong, Y. T.'
_publ_section_title
;
 1-(2-Bromoacetyl)-3-methyl-2,6-diphenylpiperidin-4-one
;
_journal_coeditor_code           BT5275
_journal_issue                   6
_journal_name_full               'Acta Crystallographica Section E'
_journal_page_first              o1479
_journal_paper_doi               10.1107/S160053681001901X
_journal_volume                  66
_journal_year                    2010
_chemical_formula_iupac          'C20 H20 Br N O2'
_chemical_formula_moiety         'C20 H20 Br N O2'
_chemical_formula_sum            'C20 H20 Br N O2'
_chemical_formula_weight         386.28
_chemical_name_systematic
;
1-(2-Bromoacetyl)-3-methyl-2,6-diphenylpiperidin-4-one
;
_space_group_IT_number           15
_symmetry_cell_setting           monoclinic
_symmetry_space_group_name_Hall  '-C 2yc'
_symmetry_space_group_name_H-M   'C 1 2/c 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                 125.368(2)
_cell_angle_gamma                90.00
_cell_formula_units_Z            8
_cell_length_a                   21.4006(8)
_cell_length_b                   14.5873(6)
_cell_length_c                   13.8107(5)
_cell_measurement_reflns_used    2025
_cell_measurement_temperature    292(2)
_cell_measurement_theta_max      0.596
_cell_measurement_theta_min      0.499
_cell_volume                     3515.7(2)
_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 0.996
_diffrn_measured_fraction_theta_max 0.987
_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  0.0354
_diffrn_reflns_av_sigmaI/netI    0.0368
_diffrn_reflns_limit_h_max       28
_diffrn_reflns_limit_h_min       -27
_diffrn_reflns_limit_k_max       19
_diffrn_reflns_limit_k_min       -19
_diffrn_reflns_limit_l_max       18
_diffrn_reflns_limit_l_min       -18
_diffrn_reflns_number            17094
_diffrn_reflns_theta_full        25.00
_diffrn_reflns_theta_max         28.47
_diffrn_reflns_theta_min         1.82
_diffrn_standards_number         0
_exptl_absorpt_coefficient_mu    2.350
_exptl_absorpt_correction_T_max  0.596
_exptl_absorpt_correction_T_min  0.499
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   '(SADABS; Bruker, 2008)'
_exptl_crystal_colour            colorless
_exptl_crystal_density_diffrn    1.460
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       Block
_exptl_crystal_F_000             1584
_exptl_crystal_size_max          0.3
_exptl_crystal_size_mid          0.26
_exptl_crystal_size_min          0.22
_refine_diff_density_max         0.533
_refine_diff_density_min         -0.773
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.021
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     218
_refine_ls_number_reflns         4398
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.021
_refine_ls_R_factor_all          0.0984
_refine_ls_R_factor_gt           0.0590
_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)+(0.1259P)²+4.1414P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1835
_refine_ls_wR_factor_ref         0.2130
_reflns_number_gt                2725
_reflns_number_total             4398
_reflns_threshold_expression     I>2σ(I)
_cod_data_source_file            bt5275.cif
_cod_data_source_block           I
_cod_original_sg_symbol_H-M      'C 2/c'
_cod_database_code               2226070
_cod_database_fobs_code          2226070
loop_
_symmetry_equiv_pos_as_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_refinement_flags
_atom_site_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
C C1 0.00908(18) 0.2545(2) 0.0494(3) 0.0355(7) Uani d . 1 . .
H H1 0.0555 0.2317 0.1229 0.043 Uiso calc R 1 . .
C C2 0.0317(2) 0.3418(3) 0.0168(4) 0.0517(10) Uani d . 1 . .
H H2A 0.0432 0.3889 0.0745 0.062 Uiso calc R 1 . .
H H2B 0.0780 0.3303 0.0214 0.062 Uiso calc R 1 . .
C C3 -0.0287(3) 0.3764(3) -0.1039(4) 0.0581(11) Uani d . 1 . .
C C4 -0.0933(2) 0.3111(3) -0.1867(3) 0.0463(8) Uani d . 1 . .
H H4 -0.1307 0.3148 -0.1674 0.056 Uiso calc R 1 . .
C C5 -0.06703(18) 0.2104(2) -0.1692(3) 0.0359(7) Uani d . 1 . .
H H5 -0.0393 0.2039 -0.2056 0.043 Uiso calc R 1 . .
C C6 -0.13640(19) 0.1469(2) -0.2373(3) 0.0355(7) Uani d . 1 . .
C C7 -0.1502(2) 0.0969(3) -0.3328(3) 0.0502(9) Uani d . 1 . .
H H7 -0.1150 0.0987 -0.3518 0.060 Uiso calc R 1 . .
C C8 -0.2159(3) 0.0440(3) -0.4008(3) 0.0605(11) Uani d . 1 . .
H H8 -0.2249 0.0115 -0.4657 0.073 Uiso calc R 1 . .
C C9 -0.2672(2) 0.0396(3) -0.3726(4) 0.0622(12) Uani d . 1 . .
H H9 -0.3110 0.0038 -0.4179 0.075 Uiso calc R 1 . .
C C10 -0.2541(2) 0.0881(3) -0.2772(4) 0.0526(10) Uani d . 1 . .
H H10 -0.2891 0.0848 -0.2577 0.063 Uiso calc R 1 . .
C C11 -0.1889(2) 0.1421(2) -0.2096(3) 0.0408(8) Uani d . 1 . .
H H11 -0.1805 0.1752 -0.1455 0.049 Uiso calc R 1 . .
C C12 -0.05143(17) 0.2656(2) 0.0741(3) 0.0334(7) Uani d . 1 . .
C C13 -0.0720(2) 0.3505(2) 0.0908(4) 0.0470(9) Uani d . 1 . .
H H13 -0.0510 0.4034 0.0831 0.056 Uiso calc R 1 . .
C C14 -0.1253(3) 0.3567(3) 0.1196(4) 0.0584(11) Uani d . 1 . .
H H14 -0.1388 0.4140 0.1315 0.070 Uiso calc R 1 . .
C C15 -0.1573(2) 0.2800(3) 0.1301(4) 0.0566(11) Uani d . 1 . .
H H15 -0.1934 0.2850 0.1469 0.068 Uiso calc R 1 . .
C C16 -0.1354(2) 0.1944(3) 0.1156(3) 0.0508(9) Uani d . 1 . .
H H16 -0.1566 0.1417 0.1233 0.061 Uiso calc R 1 . .
C C17 -0.0820(2) 0.1873(3) 0.0896(3) 0.0408(8) Uani d . 1 . .
H H17 -0.0665 0.1297 0.0825 0.049 Uiso calc R 1 . .
C C18 -0.1349(3) 0.3390(3) -0.3166(5) 0.0706(14) Uani d . 1 . .
H H18A -0.1495 0.4023 -0.3255 0.106 Uiso calc R 1 . .
H H18B -0.1800 0.3019 -0.3648 0.106 Uiso calc R 1 . .
H H18C -0.1016 0.3302 -0.3412 0.106 Uiso calc R 1 . .
C C19 0.02886(17) 0.1079(2) -0.0205(3) 0.0353(7) Uani d . 1 . .
C C20 0.09463(19) 0.0844(3) 0.1063(3) 0.0432(8) Uani d . 1 . .
H H20A 0.1063 0.0195 0.1125 0.052 Uiso calc R 1 . .
H H20B 0.0803 0.0982 0.1598 0.052 Uiso calc R 1 . .
N N1 -0.01254(14) 0.18526(19) -0.0422(2) 0.0328(6) Uani d . 1 . .
O O1 -0.0265(3) 0.4523(2) -0.1361(4) 0.1037(15) Uani d . 1 . .
O O2 0.01584(14) 0.05669(18) -0.1000(2) 0.0472(6) Uani d . 1 . .
Br Br1 0.18249(2) 0.15486(4) 0.14906(5) 0.0736(3) Uani 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'
Br Br -0.2901 2.4595 '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
N1 C1 C2 . . 108.5(3) ?
N1 C1 C12 . . 112.4(2) ?
C2 C1 C12 . . 115.7(3) ?
N1 C1 H1 . . 106.6 ?
C2 C1 H1 . . 106.6 ?
C12 C1 H1 . . 106.6 ?
C3 C2 C1 . . 113.4(3) ?
C3 C2 H2A . . 108.9 ?
C1 C2 H2A . . 108.9 ?
C3 C2 H2B . . 108.9 ?
C1 C2 H2B . . 108.9 ?
H2A C2 H2B . . 107.7 ?
O1 C3 C2 . . 122.2(5) ?
O1 C3 C4 . . 120.8(5) ?
C2 C3 C4 . . 117.0(3) ?
C3 C4 C18 . . 112.1(3) ?
C3 C4 C5 . . 112.9(3) ?
C18 C4 C5 . . 110.5(3) ?
C3 C4 H4 . . 107.0 ?
C18 C4 H4 . . 107.0 ?
C5 C4 H4 . . 107.0 ?
N1 C5 C6 . . 113.4(3) ?
N1 C5 C4 . . 112.7(3) ?
C6 C5 C4 . . 110.2(3) ?
N1 C5 H5 . . 106.7 ?
C6 C5 H5 . . 106.7 ?
C4 C5 H5 . . 106.7 ?
C7 C6 C11 . . 118.6(3) ?
C7 C6 C5 . . 120.2(3) ?
C11 C6 C5 . . 121.1(3) ?
C6 C7 C8 . . 120.8(4) ?
C6 C7 H7 . . 119.6 ?
C8 C7 H7 . . 119.6 ?
C9 C8 C7 . . 120.1(4) ?
C9 C8 H8 . . 120.0 ?
C7 C8 H8 . . 120.0 ?
C8 C9 C10 . . 120.0(4) ?
C8 C9 H9 . . 120.0 ?
C10 C9 H9 . . 120.0 ?
C9 C10 C11 . . 120.1(4) ?
C9 C10 H10 . . 119.9 ?
C11 C10 H10 . . 119.9 ?
C6 C11 C10 . . 120.3(3) ?
C6 C11 H11 . . 119.8 ?
C10 C11 H11 . . 119.8 ?
C13 C12 C17 . . 119.2(3) ?
C13 C12 C1 . . 121.9(3) ?
C17 C12 C1 . . 118.8(3) ?
C12 C13 C14 . . 119.5(4) ?
C12 C13 H13 . . 120.2 ?
C14 C13 H13 . . 120.2 ?
C15 C14 C13 . . 121.0(4) ?
C15 C14 H14 . . 119.5 ?
C13 C14 H14 . . 119.5 ?
C14 C15 C16 . . 119.4(4) ?
C14 C15 H15 . . 120.3 ?
C16 C15 H15 . . 120.3 ?
C17 C16 C15 . . 120.2(4) ?
C17 C16 H16 . . 119.9 ?
C15 C16 H16 . . 119.9 ?
C16 C17 C12 . . 120.6(4) ?
C16 C17 H17 . . 119.7 ?
C12 C17 H17 . . 119.7 ?
C4 C18 H18A . . 109.5 ?
C4 C18 H18B . . 109.5 ?
H18A C18 H18B . . 109.5 ?
C4 C18 H18C . . 109.5 ?
H18A C18 H18C . . 109.5 ?
H18B C18 H18C . . 109.5 ?
O2 C19 N1 . . 122.1(3) ?
O2 C19 C20 . . 118.4(3) ?
N1 C19 C20 . . 119.5(3) ?
C19 C20 Br1 . . 108.9(2) ?
C19 C20 H20A . . 109.9 ?
Br1 C20 H20A . . 109.9 ?
C19 C20 H20B . . 109.9 ?
Br1 C20 H20B . . 109.9 ?
H20A C20 H20B . . 108.3 ?
C19 N1 C1 . . 122.8(3) ?
C19 N1 C5 . . 115.6(3) ?
C1 N1 C5 . . 119.2(3) ?
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
C1 N1 . 1.468(4) ?
C1 C2 . 1.521(5) ?
C1 C12 . 1.527(4) ?
C1 H1 . 0.9800 ?
C2 C3 . 1.486(7) ?
C2 H2A . 0.9700 ?
C2 H2B . 0.9700 ?
C3 O1 . 1.204(5) ?
C3 C4 . 1.516(6) ?
C4 C18 . 1.525(6) ?
C4 C5 . 1.541(5) ?
C4 H4 . 0.9800 ?
C5 N1 . 1.485(4) ?
C5 C6 . 1.527(5) ?
C5 H5 . 0.9800 ?
C6 C7 . 1.382(5) ?
C6 C11 . 1.381(5) ?
C7 C8 . 1.387(6) ?
C7 H7 . 0.9300 ?
C8 C9 . 1.362(7) ?
C8 H8 . 0.9300 ?
C9 C10 . 1.375(6) ?
C9 H9 . 0.9300 ?
C10 C11 . 1.391(5) ?
C10 H10 . 0.9300 ?
C11 H11 . 0.9300 ?
C12 C13 . 1.378(5) ?
C12 C17 . 1.394(5) ?
C13 C14 . 1.411(6) ?
C13 H13 . 0.9300 ?
C14 C15 . 1.362(7) ?
C14 H14 . 0.9300 ?
C15 C16 . 1.389(6) ?
C15 H15 . 0.9300 ?
C16 C17 . 1.384(5) ?
C16 H16 . 0.9300 ?
C17 H17 . 0.9300 ?
C18 H18A . 0.9600 ?
C18 H18B . 0.9600 ?
C18 H18C . 0.9600 ?
C19 O2 . 1.219(4) ?
C19 N1 . 1.357(4) ?
C19 C20 . 1.520(5) ?
C20 Br1 . 1.912(4) ?
C20 H20A . 0.9700 ?
C20 H20B . 0.9700 ?
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
C2 H2A O1 5_565 0.97 2.56 3.458(6) 153.5
C13 H13 O1 5_565 0.93 2.51 3.404(5) 160.7
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
N1 C1 C2 C3 . . . . 55.3(4) ?
C12 C1 C2 C3 . . . . -72.0(4) ?
C1 C2 C3 O1 . . . . 166.4(5) ?
C1 C2 C3 C4 . . . . -14.4(5) ?
O1 C3 C4 C18 . . . . 19.2(6) ?
C2 C3 C4 C18 . . . . -159.9(4) ?
O1 C3 C4 C5 . . . . 144.8(5) ?
C2 C3 C4 C5 . . . . -34.4(5) ?
C3 C4 C5 N1 . . . . 41.5(4) ?
C18 C4 C5 N1 . . . . 167.9(3) ?
C3 C4 C5 C6 . . . . 169.2(3) ?
C18 C4 C5 C6 . . . . -64.3(4) ?
N1 C5 C6 C7 . . . . -119.1(3) ?
C4 C5 C6 C7 . . . . 113.5(3) ?
N1 C5 C6 C11 . . . . 64.7(4) ?
C4 C5 C6 C11 . . . . -62.7(4) ?
C11 C6 C7 C8 . . . . 0.9(5) ?
C5 C6 C7 C8 . . . . -175.3(3) ?
C6 C7 C8 C9 . . . . -1.1(6) ?
C7 C8 C9 C10 . . . . 0.4(7) ?
C8 C9 C10 C11 . . . . 0.4(6) ?
C7 C6 C11 C10 . . . . -0.1(5) ?
C5 C6 C11 C10 . . . . 176.1(3) ?
C9 C10 C11 C6 . . . . -0.5(6) ?
N1 C1 C12 C13 . . . . -138.6(3) ?
C2 C1 C12 C13 . . . . -13.3(5) ?
N1 C1 C12 C17 . . . . 46.6(4) ?
C2 C1 C12 C17 . . . . 172.0(3) ?
C17 C12 C13 C14 . . . . -1.9(5) ?
C1 C12 C13 C14 . . . . -176.7(3) ?
C12 C13 C14 C15 . . . . -0.6(7) ?
C13 C14 C15 C16 . . . . 1.8(7) ?
C14 C15 C16 C17 . . . . -0.5(6) ?
C15 C16 C17 C12 . . . . -2.0(5) ?
C13 C12 C17 C16 . . . . 3.2(5) ?
C1 C12 C17 C16 . . . . 178.1(3) ?
O2 C19 C20 Br1 . . . . 98.6(3) ?
N1 C19 C20 Br1 . . . . -80.3(3) ?
O2 C19 N1 C1 . . . . -170.7(3) ?
C20 C19 N1 C1 . . . . 8.1(5) ?
O2 C19 N1 C5 . . . . -8.3(5) ?
C20 C19 N1 C5 . . . . 170.5(3) ?
C2 C1 N1 C19 . . . . 113.0(3) ?
C12 C1 N1 C19 . . . . -117.8(3) ?
C2 C1 N1 C5 . . . . -48.8(4) ?
C12 C1 N1 C5 . . . . 80.3(3) ?
C6 C5 N1 C19 . . . . 71.5(3) ?
C4 C5 N1 C19 . . . . -162.4(3) ?
C6 C5 N1 C1 . . . . -125.4(3) ?
C4 C5 N1 C1 . . . . 0.7(4) ?
