#------------------------------------------------------------------------------
#$Date: 2016-02-20 22:30:07 +0200 (Sat, 20 Feb 2016) $
#$Revision: 176789 $
#$URL: svn://www.crystallography.net/cod/cif/2/22/60/2226051.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_2226051
loop_
_publ_author_name
'Ravichandran, K.'
'Ramesh, P.'
'Rani, M.'
'Kabilan, S.'
'Ponnuswamy, M. N.'
_publ_section_title
;
 1-Chloroacetyl-2,6-bis(2-chlorophenyl)-3,5-dimethylpiperidin-4-one
 oxime
;
_journal_coeditor_code           BT5245
_journal_issue                   6
_journal_name_full               'Acta Crystallographica Section E'
_journal_page_first              o1506
_journal_paper_doi               10.1107/S1600536810018489
_journal_volume                  66
_journal_year                    2010
_chemical_formula_iupac          'C21 H21 Cl3 N2 O2'
_chemical_formula_moiety         'C21 H21 Cl3 N2 O2'
_chemical_formula_sum            'C21 H21 Cl3 N2 O2'
_chemical_formula_weight         439.75
_chemical_name_systematic
;
1-chloroacetyl-2,6-bis(2-chlorophenyl)-3,5-dimethyl-piperidin-4-one oxime
;
_space_group_IT_number           9
_symmetry_cell_setting           monoclinic
_symmetry_space_group_name_Hall  'C -2yc'
_symmetry_space_group_name_H-M   'C 1 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                 93.529(4)
_cell_angle_gamma                90.00
_cell_formula_units_Z            4
_cell_length_a                   9.8147(6)
_cell_length_b                   15.5929(11)
_cell_length_c                   13.9498(9)
_cell_measurement_reflns_used    1231
_cell_measurement_temperature    293(2)
_cell_measurement_theta_max      28.34
_cell_measurement_theta_min      2.46
_cell_volume                     2130.8(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      293(2)
_diffrn_measured_fraction_theta_full 1.000
_diffrn_measured_fraction_theta_max 0.990
_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  0.0194
_diffrn_reflns_av_sigmaI/netI    0.0272
_diffrn_reflns_limit_h_max       13
_diffrn_reflns_limit_h_min       -13
_diffrn_reflns_limit_k_max       20
_diffrn_reflns_limit_k_min       -20
_diffrn_reflns_limit_l_max       18
_diffrn_reflns_limit_l_min       -18
_diffrn_reflns_number            10047
_diffrn_reflns_theta_full        25.00
_diffrn_reflns_theta_max         28.34
_diffrn_reflns_theta_min         2.46
_diffrn_standards_decay_%        0
_diffrn_standards_number         0
_exptl_absorpt_coefficient_mu    0.449
_exptl_absorpt_correction_T_max  0.927
_exptl_absorpt_correction_T_min  0.903
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   '(SADABS; Bruker, 2008)'
_exptl_crystal_colour            Colorless
_exptl_crystal_density_diffrn    1.371
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       Block
_exptl_crystal_F_000             912
_exptl_crystal_size_max          0.23
_exptl_crystal_size_mid          0.19
_exptl_crystal_size_min          0.17
_refine_diff_density_max         0.202
_refine_diff_density_min         -0.182
_refine_ls_abs_structure_details 'Flack (1983), 2045 Friedel pairs'
_refine_ls_abs_structure_Flack   0.04(4)
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.027
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     255
_refine_ls_number_reflns         4689
_refine_ls_number_restraints     2
_refine_ls_restrained_S_all      1.027
_refine_ls_R_factor_all          0.0368
_refine_ls_R_factor_gt           0.0306
_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)+(0.0346P)²+0.6047P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0728
_refine_ls_wR_factor_ref         0.0764
_reflns_number_gt                4181
_reflns_number_total             4689
_reflns_threshold_expression     I>2σ(I)
_cod_data_source_file            bt5245.cif
_cod_data_source_block           I
_cod_original_sg_symbol_H-M      'C c'
_cod_database_code               2226051
_cod_database_fobs_code          2226051
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'
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
Cl Cl1 0.88541(8) 0.18026(6) 0.71303(5) 0.0929(3) Uani d . 1 . .
Cl Cl2 0.40087(5) 0.06564(4) 0.47110(4) 0.05560(15) Uani d . 1 . .
Cl Cl3 1.07034(7) -0.00744(6) 0.60948(5) 0.0826(2) Uani d . 1 . .
O O1 0.57421(15) 0.18007(9) 0.60868(9) 0.0470(3) Uani d . 1 . .
O O2 0.91903(18) 0.31451(10) 0.26625(12) 0.0605(4) Uani d . 1 . .
H H2A 0.9746 0.3323 0.2295 0.091 Uiso calc R 1 . .
N N1 0.71338(13) 0.12798(9) 0.49843(9) 0.0296(3) Uani d . 1 . .
C C2 0.64401(17) 0.18068(11) 0.42143(12) 0.0328(3) Uani d . 1 . .
H H2 0.5740 0.2141 0.4519 0.039 Uiso calc R 1 . .
C C3 0.74830(19) 0.24562(13) 0.38710(13) 0.0400(4) Uani d . 1 . .
H H3 0.7049 0.2779 0.3332 0.048 Uiso calc R 1 . .
C C4 0.87049(17) 0.19941(13) 0.35168(12) 0.0372(4) Uani d . 1 . .
C C5 0.89159(17) 0.10640(13) 0.37891(12) 0.0365(4) Uani d . 1 . .
H H5 0.8338 0.0725 0.3334 0.044 Uiso calc R 1 . .
C C6 0.84595(16) 0.08546(12) 0.48021(11) 0.0326(4) Uani d . 1 . .
H H6 0.9157 0.1072 0.5274 0.039 Uiso calc R 1 . .
C C7 0.67616(17) 0.13972(11) 0.58982(12) 0.0334(4) Uani d . 1 . .
C C8 0.7634(2) 0.10242(15) 0.67283(13) 0.0480(5) Uani d . 1 . .
H H8A 0.8093 0.0511 0.6523 0.058 Uiso calc R 1 . .
H H8B 0.7066 0.0870 0.7247 0.058 Uiso calc R 1 . .
C C9 0.56989(17) 0.12926(12) 0.34100(11) 0.0343(4) Uani d . 1 . .
C C10 0.45857(18) 0.07723(13) 0.35647(13) 0.0403(4) Uani d . 1 . .
C C11 0.3877(2) 0.03212(19) 0.28473(16) 0.0584(6) Uani d . 1 . .
H H11 0.3146 -0.0027 0.2987 0.070 Uiso calc R 1 . .
C C12 0.4266(2) 0.0394(2) 0.19198(18) 0.0749(8) Uani d . 1 . .
H H12 0.3798 0.0094 0.1427 0.090 Uiso calc R 1 . .
C C13 0.5331(2) 0.0905(2) 0.17247(14) 0.0668(7) Uani d . 1 . .
H H13 0.5585 0.0956 0.1096 0.080 Uiso calc R 1 . .
C C14 0.6050(2) 0.13518(15) 0.24530(13) 0.0467(5) Uani d . 1 . .
H H14 0.6779 0.1698 0.2303 0.056 Uiso calc R 1 . .
C C15 0.7918(3) 0.30940(15) 0.46641(19) 0.0625(6) Uani d . 1 . .
H H15A 0.8360 0.2792 0.5196 0.094 Uiso calc R 1 . .
H H15B 0.7127 0.3386 0.4873 0.094 Uiso calc R 1 . .
H H15C 0.8539 0.3504 0.4421 0.094 Uiso calc R 1 . .
N N16 0.95359(17) 0.23024(11) 0.29455(11) 0.0465(4) Uani d . 1 . .
C C17 1.0382(2) 0.07602(18) 0.36986(17) 0.0626(7) Uani d . 1 . .
H H17A 1.0663 0.0894 0.3069 0.094 Uiso calc R 1 . .
H H17B 1.0430 0.0152 0.3799 0.094 Uiso calc R 1 . .
H H17C 1.0974 0.1044 0.4172 0.094 Uiso calc R 1 . .
C C18 0.83630(18) -0.01119(13) 0.49265(12) 0.0383(4) Uani d . 1 . .
C C19 0.9322(2) -0.05775(16) 0.54924(15) 0.0545(6) Uani d . 1 . .
C C20 0.9212(3) -0.14576(19) 0.5596(2) 0.0722(8) Uani d . 1 . .
H H20 0.9846 -0.1754 0.5993 0.087 Uiso calc R 1 . .
C C21 0.8168(3) -0.18886(17) 0.5115(2) 0.0773(9) Uani d . 1 . .
H H21 0.8093 -0.2479 0.5186 0.093 Uiso calc R 1 . .
C C22 0.7226(3) -0.14545(15) 0.4525(2) 0.0633(6) Uani d . 1 . .
H H22 0.6528 -0.1751 0.4187 0.076 Uiso calc R 1 . .
C C23 0.7326(2) -0.05725(13) 0.44401(14) 0.0442(4) Uani d . 1 . .
H H23 0.6682 -0.0281 0.4047 0.053 Uiso calc R 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'
Cl Cl 0.1484 0.1585 '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
N16 O2 H2A . . 109.5 ?
C7 N1 C2 . . 117.79(13) ?
C7 N1 C6 . . 120.37(13) ?
C2 N1 C6 . . 119.18(12) ?
N1 C2 C9 . . 114.70(14) ?
N1 C2 C3 . . 107.79(14) ?
C9 C2 C3 . . 114.42(14) ?
N1 C2 H2 . . 106.4 ?
C9 C2 H2 . . 106.4 ?
C3 C2 H2 . . 106.4 ?
C4 C3 C15 . . 110.84(17) ?
C4 C3 C2 . . 110.21(15) ?
C15 C3 C2 . . 111.38(15) ?
C4 C3 H3 . . 108.1 ?
C15 C3 H3 . . 108.1 ?
C2 C3 H3 . . 108.1 ?
N16 C4 C3 . . 125.40(18) ?
N16 C4 C5 . . 115.98(16) ?
C3 C4 C5 . . 118.42(14) ?
C4 C5 C17 . . 113.10(16) ?
C4 C5 C6 . . 112.98(14) ?
C17 C5 C6 . . 109.75(15) ?
C4 C5 H5 . . 106.9 ?
C17 C5 H5 . . 106.9 ?
C6 C5 H5 . . 106.9 ?
N1 C6 C18 . . 111.03(13) ?
N1 C6 C5 . . 111.49(13) ?
C18 C6 C5 . . 109.74(14) ?
N1 C6 H6 . . 108.2 ?
C18 C6 H6 . . 108.2 ?
C5 C6 H6 . . 108.2 ?
O1 C7 N1 . . 122.74(16) ?
O1 C7 C8 . . 117.68(15) ?
N1 C7 C8 . . 119.57(15) ?
C7 C8 Cl1 . . 108.57(15) ?
C7 C8 H8A . . 110.0 ?
Cl1 C8 H8A . . 110.0 ?
C7 C8 H8B . . 110.0 ?
Cl1 C8 H8B . . 110.0 ?
H8A C8 H8B . . 108.4 ?
C10 C9 C14 . . 115.36(17) ?
C10 C9 C2 . . 122.45(14) ?
C14 C9 C2 . . 122.10(17) ?
C11 C10 C9 . . 123.57(17) ?
C11 C10 Cl2 . . 115.90(15) ?
C9 C10 Cl2 . . 120.52(14) ?
C12 C11 C10 . . 118.9(2) ?
C12 C11 H11 . . 120.5 ?
C10 C11 H11 . . 120.5 ?
C13 C12 C11 . . 120.0(2) ?
C13 C12 H12 . . 120.0 ?
C11 C12 H12 . . 120.0 ?
C12 C13 C14 . . 120.8(2) ?
C12 C13 H13 . . 119.6 ?
C14 C13 H13 . . 119.6 ?
C13 C14 C9 . . 121.3(2) ?
C13 C14 H14 . . 119.3 ?
C9 C14 H14 . . 119.3 ?
C3 C15 H15A . . 109.5 ?
C3 C15 H15B . . 109.5 ?
H15A C15 H15B . . 109.5 ?
C3 C15 H15C . . 109.5 ?
H15A C15 H15C . . 109.5 ?
H15B C15 H15C . . 109.5 ?
C4 N16 O2 . . 112.12(16) ?
C5 C17 H17A . . 109.5 ?
C5 C17 H17B . . 109.5 ?
H17A C17 H17B . . 109.5 ?
C5 C17 H17C . . 109.5 ?
H17A C17 H17C . . 109.5 ?
H17B C17 H17C . . 109.5 ?
C23 C18 C19 . . 117.14(19) ?
C23 C18 C6 . . 120.39(16) ?
C19 C18 C6 . . 122.42(19) ?
C20 C19 C18 . . 121.4(2) ?
C20 C19 Cl3 . . 117.39(19) ?
C18 C19 Cl3 . . 121.19(18) ?
C21 C20 C19 . . 119.8(2) ?
C21 C20 H20 . . 120.1 ?
C19 C20 H20 . . 120.1 ?
C20 C21 C22 . . 120.5(2) ?
C20 C21 H21 . . 119.8 ?
C22 C21 H21 . . 119.8 ?
C21 C22 C23 . . 119.4(3) ?
C21 C22 H22 . . 120.3 ?
C23 C22 H22 . . 120.3 ?
C22 C23 C18 . . 121.7(2) ?
C22 C23 H23 . . 119.1 ?
C18 C23 H23 . . 119.1 ?
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
Cl1 C8 . 1.772(2) ?
Cl2 C10 . 1.7383(18) ?
Cl3 C19 . 1.738(3) ?
O1 C7 . 1.224(2) ?
O2 N16 . 1.408(2) ?
O2 H2A . 0.8200 ?
N1 C7 . 1.360(2) ?
N1 C2 . 1.484(2) ?
N1 C6 . 1.496(2) ?
C2 C9 . 1.527(3) ?
C2 C3 . 1.537(2) ?
C2 H2 . 0.9800 ?
C3 C4 . 1.508(2) ?
C3 C15 . 1.529(3) ?
C3 H3 . 0.9800 ?
C4 N16 . 1.269(2) ?
C4 C5 . 1.510(3) ?
C5 C17 . 1.527(3) ?
C5 C6 . 1.543(2) ?
C5 H5 . 0.9800 ?
C6 C18 . 1.521(3) ?
C6 H6 . 0.9800 ?
C7 C8 . 1.513(3) ?
C8 H8A . 0.9700 ?
C8 H8B . 0.9700 ?
C9 C10 . 1.388(3) ?
C9 C14 . 1.402(2) ?
C10 C11 . 1.377(3) ?
C11 C12 . 1.376(3) ?
C11 H11 . 0.9300 ?
C12 C13 . 1.355(4) ?
C12 H12 . 0.9300 ?
C13 C14 . 1.388(3) ?
C13 H13 . 0.9300 ?
C14 H14 . 0.9300 ?
C15 H15A . 0.9600 ?
C15 H15B . 0.9600 ?
C15 H15C . 0.9600 ?
C17 H17A . 0.9600 ?
C17 H17B . 0.9600 ?
C17 H17C . 0.9600 ?
C18 C23 . 1.388(3) ?
C18 C19 . 1.394(3) ?
C19 C20 . 1.385(4) ?
C20 C21 . 1.367(4) ?
C20 H20 . 0.9300 ?
C21 C22 . 1.377(4) ?
C21 H21 . 0.9300 ?
C22 C23 . 1.384(3) ?
C22 H22 . 0.9300 ?
C23 H23 . 0.9300 ?
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
O2 H2A O1 4_554 0.82 2.01 2.7515(18) 150.3
C12 H12 Cl2 2_554 0.93 2.68 3.485(3) 144.8
C20 H20 O1 3_545 0.93 2.42 3.158(3) 136.3
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 C9 . . . . -121.63(16) ?
C6 N1 C2 C9 . . . . 76.79(18) ?
C7 N1 C2 C3 . . . . 109.65(16) ?
C6 N1 C2 C3 . . . . -51.92(19) ?
N1 C2 C3 C4 . . . . 58.14(18) ?
C9 C2 C3 C4 . . . . -70.73(19) ?
N1 C2 C3 C15 . . . . -65.3(2) ?
C9 C2 C3 C15 . . . . 165.81(17) ?
C15 C3 C4 N16 . . . . -77.9(2) ?
C2 C3 C4 N16 . . . . 158.32(18) ?
C15 C3 C4 C5 . . . . 107.4(2) ?
C2 C3 C4 C5 . . . . -16.4(2) ?
N16 C4 C5 C17 . . . . 24.7(2) ?
C3 C4 C5 C17 . . . . -160.10(18) ?
N16 C4 C5 C6 . . . . 150.15(16) ?
C3 C4 C5 C6 . . . . -34.6(2) ?
C7 N1 C6 C18 . . . . 77.29(19) ?
C2 N1 C6 C18 . . . . -121.62(16) ?
C7 N1 C6 C5 . . . . -160.01(15) ?
C2 N1 C6 C5 . . . . 1.1(2) ?
C4 C5 C6 N1 . . . . 42.4(2) ?
C17 C5 C6 N1 . . . . 169.59(18) ?
C4 C5 C6 C18 . . . . 165.79(15) ?
C17 C5 C6 C18 . . . . -67.0(2) ?
C2 N1 C7 O1 . . . . 12.7(2) ?
C6 N1 C7 O1 . . . . 174.07(17) ?
C2 N1 C7 C8 . . . . -166.86(16) ?
C6 N1 C7 C8 . . . . -5.5(2) ?
O1 C7 C8 Cl1 . . . . -88.46(18) ?
N1 C7 C8 Cl1 . . . . 91.14(18) ?
N1 C2 C9 C10 . . . . 64.5(2) ?
C3 C2 C9 C10 . . . . -170.16(16) ?
N1 C2 C9 C14 . . . . -119.16(18) ?
C3 C2 C9 C14 . . . . 6.2(2) ?
C14 C9 C10 C11 . . . . 1.6(3) ?
C2 C9 C10 C11 . . . . 178.1(2) ?
C14 C9 C10 Cl2 . . . . -178.56(15) ?
C2 C9 C10 Cl2 . . . . -2.0(2) ?
C9 C10 C11 C12 . . . . -1.1(4) ?
Cl2 C10 C11 C12 . . . . 179.0(2) ?
C10 C11 C12 C13 . . . . 0.0(4) ?
C11 C12 C13 C14 . . . . 0.6(4) ?
C12 C13 C14 C9 . . . . -0.1(4) ?
C10 C9 C14 C13 . . . . -1.0(3) ?
C2 C9 C14 C13 . . . . -177.52(19) ?
C3 C4 N16 O2 . . . . -0.2(3) ?
C5 C4 N16 O2 . . . . 174.59(16) ?
N1 C6 C18 C23 . . . . 52.7(2) ?
C5 C6 C18 C23 . . . . -71.05(19) ?
N1 C6 C18 C19 . . . . -129.93(16) ?
C5 C6 C18 C19 . . . . 106.36(18) ?
C23 C18 C19 C20 . . . . -2.6(3) ?
C6 C18 C19 C20 . . . . 179.90(18) ?
C23 C18 C19 Cl3 . . . . 177.34(14) ?
C6 C18 C19 Cl3 . . . . -0.2(2) ?
C18 C19 C20 C21 . . . . 1.9(3) ?
Cl3 C19 C20 C21 . . . . -178.02(19) ?
C19 C20 C21 C22 . . . . 0.2(4) ?
C20 C21 C22 C23 . . . . -1.5(4) ?
C21 C22 C23 C18 . . . . 0.7(3) ?
C19 C18 C23 C22 . . . . 1.3(3) ?
C6 C18 C23 C22 . . . . 178.83(17) ?
