#------------------------------------------------------------------------------
#$Date: 2016-02-20 22:30:07 +0200 (Sat, 20 Feb 2016) $
#$Revision: 176789 $
#$URL: svn://www.crystallography.net/cod/cif/2/22/85/2228518.cif $
#------------------------------------------------------------------------------
#
# This file is available in the Crystallography Open Database (COD),
# http://www.crystallography.net/
#
# All data on this site have been placed in the public domain by the
# contributors.
#
data_2228518
loop_
_publ_author_name
'Vimalraj, V.'
'Pandiarajan, K.'
_publ_section_title
;
 1-Acetyl-2-r,6-c-bis(4-chlorophenyl)-3-methyl-1,2,5,6-tetrahydropyridin-4-yl
 acetate
;
_journal_coeditor_code           PV2343
_journal_issue                   12
_journal_name_full               'Acta Crystallographica Section E'
_journal_page_first              o3259
_journal_paper_doi               10.1107/S1600536810047586
_journal_volume                  66
_journal_year                    2010
_chemical_formula_iupac          'C22 H21 Cl2 N O3'
_chemical_formula_moiety         'C22 H21 Cl2 N O3'
_chemical_formula_sum            'C22 H21 Cl2 N O3'
_chemical_formula_weight         418.30
_chemical_melting_point          411
_chemical_name_systematic
;
1-Acetyl-2-r,6-c-bis(4-chlorophenyl)-3-methyl-1,2,5,6-tetrahydropyridin-4-yl
acetate
;
_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                 124.27(3)
_cell_angle_gamma                90.00
_cell_formula_units_Z            4
_cell_length_a                   16.560(3)
_cell_length_b                   14.809(3)
_cell_length_c                   10.241(2)
_cell_measurement_reflns_used    6663
_cell_measurement_temperature    293(2)
_cell_measurement_theta_max      59.23
_cell_measurement_theta_min      2.75
_cell_volume                     2075.5(10)
_computing_cell_refinement       'APEX2 and SAINT (Bruker, 2004)'
_computing_data_collection       'APEX2 (Bruker, 2004)'
_computing_data_reduction        'SAINT (Bruker, 2004)'
_computing_molecular_graphics
'ORTEP-3 (Farrugia, 1997) and Mercury (Bruno et al., 2002)'
_computing_publication_material  'PLATON (Spek, 2009)'
_computing_structure_refinement  'SHELXL97 (Sheldrick, 2008)'
_computing_structure_solution    'SIR92 (Altomare et al., 1993)'
_diffrn_ambient_temperature      293(2)
_diffrn_measured_fraction_theta_full 0.990
_diffrn_measured_fraction_theta_max 0.990
_diffrn_measurement_device_type  'Bruker Kappa APEXII CCD'
_diffrn_measurement_method       'ω and φ'
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0197
_diffrn_reflns_av_sigmaI/netI    0.0259
_diffrn_reflns_limit_h_max       22
_diffrn_reflns_limit_h_min       -22
_diffrn_reflns_limit_k_max       20
_diffrn_reflns_limit_k_min       -20
_diffrn_reflns_limit_l_max       14
_diffrn_reflns_limit_l_min       -14
_diffrn_reflns_number            13520
_diffrn_reflns_theta_full        29.64
_diffrn_reflns_theta_max         29.64
_diffrn_reflns_theta_min         2.03
_diffrn_standards_decay_%        0
_diffrn_standards_number         0
_exptl_absorpt_coefficient_mu    0.335
_exptl_absorpt_correction_T_max  0.9360
_exptl_absorpt_correction_T_min  0.8661
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   '(SADABS; Bruker, 1999)'
_exptl_crystal_colour            colourless
_exptl_crystal_density_diffrn    1.339
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       block
_exptl_crystal_F_000             872
_exptl_crystal_size_max          0.30
_exptl_crystal_size_mid          0.25
_exptl_crystal_size_min          0.20
_refine_diff_density_max         0.268
_refine_diff_density_min         -0.167
_refine_ls_abs_structure_details 'Flack (1983), 2649 Friedel pairs'
_refine_ls_abs_structure_Flack   0.02(5)
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.039
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     256
_refine_ls_number_reflns         5546
_refine_ls_number_restraints     2
_refine_ls_restrained_S_all      1.039
_refine_ls_R_factor_all          0.0485
_refine_ls_R_factor_gt           0.0370
_refine_ls_shift/su_max          0.011
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'calc w=1/[σ²(Fo²)+(0.0528P)²+0.2729P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0931
_refine_ls_wR_factor_ref         0.1002
_reflns_number_gt                4578
_reflns_number_total             5546
_reflns_threshold_expression     I>2σ(I)
_cod_data_source_file            pv2343.cif
_cod_data_source_block           I
_cod_original_sg_symbol_H-M      'C c'
_cod_database_code               2228518
_cod_database_fobs_code          2228518
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 Cl2 0.12844(5) 0.18128(4) -0.47636(7) 0.07210(17) Uani d . 1 . .
Cl Cl1 0.25477(6) -0.00598(5) -0.08332(9) 0.0858(2) Uani d . 1 . .
O O2 0.03552(10) 0.37134(10) 0.21164(17) 0.0576(4) Uani d . 1 . .
N N1 0.26481(10) 0.40891(9) 0.16833(17) 0.0389(3) Uani d . 1 . .
C C2 0.33771(12) 0.46887(12) 0.2128(2) 0.0478(4) Uani d . 1 . .
O O1 0.32636(10) 0.53254(10) 0.1281(2) 0.0664(4) Uani d . 1 . .
C C20 0.13277(14) 0.25613(13) -0.3423(2) 0.0488(4) Uani d . 1 . .
C C17 0.14951(12) 0.36840(12) -0.1132(2) 0.0395(3) Uani d . 1 . .
O O3 -0.01433(13) 0.24011(13) 0.0838(2) 0.0784(5) Uani d . 1 . .
C C19 0.08085(13) 0.23746(14) -0.2795(2) 0.0496(4) Uani d . 1 . .
H H19 0.0403 0.1871 -0.3131 0.059 Uiso calc R 1 . .
C C3 0.27461(12) 0.33000(11) 0.2627(2) 0.0398(3) Uani d . 1 . .
H H3 0.3404 0.3321 0.3604 0.048 Uiso calc R 1 . .
C C7 0.16844(11) 0.42629(12) 0.0235(2) 0.0398(3) Uani d . 1 . .
H H7 0.1680 0.4894 -0.0058 0.048 Uiso calc R 1 . .
C C4 0.20259(13) 0.33908(12) 0.3092(2) 0.0457(4) Uani d . 1 . .
H H4A 0.1924 0.2803 0.3393 0.055 Uiso calc R 1 . .
H H4B 0.2301 0.3785 0.4003 0.055 Uiso calc R 1 . .
C C11 0.26760(11) 0.24311(10) 0.17759(19) 0.0391(3) Uani d . 1 . .
C C18 0.08892(12) 0.29388(13) -0.1653(2) 0.0442(4) Uani d . 1 . .
H H18 0.0531 0.2815 -0.1229 0.053 Uiso calc R 1 . .
C C21 0.19096(16) 0.33134(13) -0.2975(3) 0.0539(5) Uani d . 1 . .
H H21 0.2246 0.3444 -0.3435 0.065 Uiso calc R 1 . .
C C16 0.32496(13) 0.23387(13) 0.1197(2) 0.0492(4) Uani d . 1 . .
H H16 0.3668 0.2807 0.1349 0.059 Uiso calc R 1 . .
C C15 0.32233(15) 0.15862(14) 0.0411(3) 0.0557(5) Uani d . 1 . .
H H15 0.3611 0.1545 0.0022 0.067 Uiso calc R 1 . .
C C5 0.10804(13) 0.37564(13) 0.1803(2) 0.0446(4) Uani d . 1 . .
C C12 0.20837(14) 0.17175(12) 0.1571(2) 0.0462(4) Uani d . 1 . .
H H12 0.1699 0.1757 0.1966 0.055 Uiso calc R 1 . .
C C22 0.19884(14) 0.38696(13) -0.1840(2) 0.0497(4) Uani d . 1 . .
H H22 0.2380 0.4382 -0.1537 0.060 Uiso calc R 1 . .
C C6 0.08920(12) 0.41668(12) 0.0530(2) 0.0437(4) Uani d . 1 . .
C C14 0.26133(15) 0.08872(13) 0.0203(2) 0.0518(4) Uani d . 1 . .
C C13 0.20498(15) 0.09451(14) 0.0792(2) 0.0536(4) Uani d . 1 . .
H H13 0.1648 0.0467 0.0666 0.064 Uiso calc R 1 . .
C C9 -0.02127(14) 0.29704(16) 0.1591(3) 0.0569(5) Uani d . 1 . .
C C8 -0.00692(15) 0.45758(17) -0.0687(3) 0.0646(5) Uani d . 1 . .
H H8A -0.0584 0.4164 -0.0930 0.097 Uiso calc R 1 . .
H H8B -0.0091 0.4697 -0.1627 0.097 Uiso calc R 1 . .
H H8C -0.0152 0.5130 -0.0289 0.097 Uiso calc R 1 . .
C C1 0.43369(16) 0.45659(18) 0.3692(3) 0.0773(7) Uani d . 1 . .
H H1A 0.4787 0.5024 0.3819 0.116 Uiso calc R 1 . .
H H1B 0.4598 0.3981 0.3727 0.116 Uiso calc R 1 . .
H H1C 0.4239 0.4615 0.4528 0.116 Uiso calc R 1 . .
C C10 -0.0915(2) 0.2967(2) 0.2046(4) 0.0833(8) Uani d . 1 . .
H H10A -0.1459 0.3350 0.1341 0.125 Uiso calc R 1 . .
H H10B -0.0599 0.3187 0.3108 0.125 Uiso calc R 1 . .
H H10C -0.1143 0.2363 0.1985 0.125 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
C9 O2 C5 . . 116.06(15) ?
C2 N1 C7 . . 118.79(14) ?
C2 N1 C3 . . 123.66(14) ?
C7 N1 C3 . . 117.42(13) ?
O1 C2 N1 . . 121.05(17) ?
O1 C2 C1 . . 119.84(18) ?
N1 C2 C1 . . 119.11(17) ?
C19 C20 C21 . . 121.22(17) ?
C19 C20 Cl2 . . 119.27(15) ?
C21 C20 Cl2 . . 119.48(14) ?
C18 C17 C22 . . 117.96(17) ?
C18 C17 C7 . . 122.41(14) ?
C22 C17 C7 . . 119.52(16) ?
C20 C19 C18 . . 119.45(17) ?
C20 C19 H19 . . 120.3 ?
C18 C19 H19 . . 120.3 ?
N1 C3 C4 . . 108.74(14) ?
N1 C3 C11 . . 110.61(13) ?
C4 C3 C11 . . 115.75(14) ?
N1 C3 H3 . . 107.1 ?
C4 C3 H3 . . 107.1 ?
C11 C3 H3 . . 107.1 ?
N1 C7 C6 . . 110.78(13) ?
N1 C7 C17 . . 112.11(14) ?
C6 C7 C17 . . 112.35(14) ?
N1 C7 H7 . . 107.1 ?
C6 C7 H7 . . 107.1 ?
C17 C7 H7 . . 107.1 ?
C5 C4 C3 . . 112.22(14) ?
C5 C4 H4A . . 109.2 ?
C3 C4 H4A . . 109.2 ?
C5 C4 H4B . . 109.2 ?
C3 C4 H4B . . 109.2 ?
H4A C4 H4B . . 107.9 ?
C12 C11 C16 . . 117.53(16) ?
C12 C11 C3 . . 123.71(15) ?
C16 C11 C3 . . 118.74(15) ?
C17 C18 C19 . . 120.89(15) ?
C17 C18 H18 . . 119.6 ?
C19 C18 H18 . . 119.6 ?
C22 C21 C20 . . 119.07(16) ?
C22 C21 H21 . . 120.5 ?
C20 C21 H21 . . 120.5 ?
C15 C16 C11 . . 122.30(17) ?
C15 C16 H16 . . 118.9 ?
C11 C16 H16 . . 118.9 ?
C16 C15 C14 . . 118.94(18) ?
C16 C15 H15 . . 120.5 ?
C14 C15 H15 . . 120.5 ?
C6 C5 O2 . . 119.56(17) ?
C6 C5 C4 . . 127.06(15) ?
O2 C5 C4 . . 113.09(16) ?
C11 C12 C13 . . 121.28(17) ?
C11 C12 H12 . . 119.4 ?
C13 C12 H12 . . 119.4 ?
C21 C22 C17 . . 121.33(18) ?
C21 C22 H22 . . 119.3 ?
C17 C22 H22 . . 119.3 ?
C5 C6 C8 . . 124.46(16) ?
C5 C6 C7 . . 119.81(15) ?
C8 C6 C7 . . 115.73(16) ?
C13 C14 C15 . . 120.48(18) ?
C13 C14 Cl1 . . 119.96(17) ?
C15 C14 Cl1 . . 119.55(15) ?
C14 C13 C12 . . 119.44(18) ?
C14 C13 H13 . . 120.3 ?
C12 C13 H13 . . 120.3 ?
O3 C9 O2 . . 122.43(18) ?
O3 C9 C10 . . 125.6(2) ?
O2 C9 C10 . . 111.9(2) ?
C6 C8 H8A . . 109.5 ?
C6 C8 H8B . . 109.5 ?
H8A C8 H8B . . 109.5 ?
C6 C8 H8C . . 109.5 ?
H8A C8 H8C . . 109.5 ?
H8B C8 H8C . . 109.5 ?
C2 C1 H1A . . 109.5 ?
C2 C1 H1B . . 109.5 ?
H1A C1 H1B . . 109.5 ?
C2 C1 H1C . . 109.5 ?
H1A C1 H1C . . 109.5 ?
H1B C1 H1C . . 109.5 ?
C9 C10 H10A . . 109.5 ?
C9 C10 H10B . . 109.5 ?
H10A C10 H10B . . 109.5 ?
C9 C10 H10C . . 109.5 ?
H10A C10 H10C . . 109.5 ?
H10B C10 H10C . . 109.5 ?
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
Cl2 C20 . 1.7343(19) ?
Cl1 C14 . 1.725(2) ?
O2 C9 . 1.347(3) ?
O2 C5 . 1.409(2) ?
N1 C2 . 1.354(2) ?
N1 C7 . 1.465(2) ?
N1 C3 . 1.466(2) ?
C2 O1 . 1.222(2) ?
C2 C1 . 1.503(3) ?
C20 C19 . 1.361(2) ?
C20 C21 . 1.372(3) ?
C17 C18 . 1.381(3) ?
C17 C22 . 1.391(2) ?
C17 C7 . 1.516(2) ?
O3 C9 . 1.191(3) ?
C19 C18 . 1.381(3) ?
C19 H19 . 0.9300 ?
C3 C4 . 1.519(2) ?
C3 C11 . 1.521(2) ?
C3 H3 . 0.9800 ?
C7 C6 . 1.510(2) ?
C7 H7 . 0.9800 ?
C4 C5 . 1.470(3) ?
C4 H4A . 0.9700 ?
C4 H4B . 0.9700 ?
C11 C12 . 1.375(2) ?
C11 C16 . 1.381(2) ?
C18 H18 . 0.9300 ?
C21 C22 . 1.369(3) ?
C21 H21 . 0.9300 ?
C16 C15 . 1.361(3) ?
C16 H16 . 0.9300 ?
C15 C14 . 1.377(3) ?
C15 H15 . 0.9300 ?
C5 C6 . 1.307(3) ?
C12 C13 . 1.378(3) ?
C12 H12 . 0.9300 ?
C22 H22 . 0.9300 ?
C6 C8 . 1.490(3) ?
C14 C13 . 1.369(3) ?
C13 H13 . 0.9300 ?
C9 C10 . 1.475(3) ?
C8 H8A . 0.9600 ?
C8 H8B . 0.9600 ?
C8 H8C . 0.9600 ?
C1 H1A . 0.9600 ?
C1 H1B . 0.9600 ?
C1 H1C . 0.9600 ?
C10 H10A . 0.9600 ?
C10 H10B . 0.9600 ?
C10 H10C . 0.9600 ?
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
C3 H3 O3 4 0.98 2.44 3.341(3) 152
C4 H4B O1 2_565 0.97 2.35 3.308(3) 169
C7 H7 O1 . 0.98 2.26 2.701(2) 106
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 O1 . . . . -5.9(3) ?
C3 N1 C2 O1 . . . . 178.46(18) ?
C7 N1 C2 C1 . . . . 173.89(19) ?
C3 N1 C2 C1 . . . . -1.8(3) ?
C21 C20 C19 C18 . . . . -1.8(3) ?
Cl2 C20 C19 C18 . . . . 175.93(15) ?
C2 N1 C3 C4 . . . . 117.77(18) ?
C7 N1 C3 C4 . . . . -57.97(18) ?
C2 N1 C3 C11 . . . . -114.08(18) ?
C7 N1 C3 C11 . . . . 70.18(18) ?
C2 N1 C7 C6 . . . . -130.70(16) ?
C3 N1 C7 C6 . . . . 45.2(2) ?
C2 N1 C7 C17 . . . . 102.91(18) ?
C3 N1 C7 C17 . . . . -81.14(17) ?
C18 C17 C7 N1 . . . . 103.99(18) ?
C22 C17 C7 N1 . . . . -72.1(2) ?
C18 C17 C7 C6 . . . . -21.5(2) ?
C22 C17 C7 C6 . . . . 162.36(16) ?
N1 C3 C4 C5 . . . . 39.76(19) ?
C11 C3 C4 C5 . . . . -85.43(19) ?
N1 C3 C11 C12 . . . . -131.11(17) ?
C4 C3 C11 C12 . . . . -6.9(2) ?
N1 C3 C11 C16 . . . . 50.2(2) ?
C4 C3 C11 C16 . . . . 174.38(15) ?
C22 C17 C18 C19 . . . . 2.7(3) ?
C7 C17 C18 C19 . . . . -173.48(16) ?
C20 C19 C18 C17 . . . . -0.6(3) ?
C19 C20 C21 C22 . . . . 1.9(3) ?
Cl2 C20 C21 C22 . . . . -175.81(16) ?
C12 C11 C16 C15 . . . . 1.7(3) ?
C3 C11 C16 C15 . . . . -179.45(18) ?
C11 C16 C15 C14 . . . . -0.8(3) ?
C9 O2 C5 C6 . . . . 93.2(2) ?
C9 O2 C5 C4 . . . . -92.5(2) ?
C3 C4 C5 C6 . . . . -15.7(3) ?
C3 C4 C5 O2 . . . . 170.56(14) ?
C16 C11 C12 C13 . . . . -1.2(3) ?
C3 C11 C12 C13 . . . . -179.91(18) ?
C20 C21 C22 C17 . . . . 0.3(3) ?
C18 C17 C22 C21 . . . . -2.6(3) ?
C7 C17 C22 C21 . . . . 173.71(17) ?
O2 C5 C6 C8 . . . . -2.5(3) ?
C4 C5 C6 C8 . . . . -175.8(2) ?
O2 C5 C6 C7 . . . . 176.44(15) ?
C4 C5 C6 C7 . . . . 3.1(3) ?
N1 C7 C6 C5 . . . . -16.0(2) ?
C17 C7 C6 C5 . . . . 110.29(17) ?
N1 C7 C6 C8 . . . . 163.06(16) ?
C17 C7 C6 C8 . . . . -70.7(2) ?
C16 C15 C14 C13 . . . . -0.7(3) ?
C16 C15 C14 Cl1 . . . . 178.36(16) ?
C15 C14 C13 C12 . . . . 1.2(3) ?
Cl1 C14 C13 C12 . . . . -177.82(16) ?
C11 C12 C13 C14 . . . . -0.3(3) ?
C5 O2 C9 O3 . . . . -3.6(3) ?
C5 O2 C9 C10 . . . . 177.1(2) ?
