#------------------------------------------------------------------------------
#$Date: 2017-10-13 11:42:48 +0300 (Fri, 13 Oct 2017) $
#$Revision: 201978 $
#$URL: file:///home/coder/svn-repositories/cod/cif/2/22/98/2229847.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_2229847
loop_
_publ_author_name
'Nesterov, Volodymyr V.'
'Sarkisov, Sergey S.'
'Shulaev, Vladimir'
'Nesterov, Vladimir N.'
_publ_section_title
;
 3,5-Bis(4-chlorobenzylidene)-1-methylpiperidin-4-one
;
_journal_coeditor_code           SU2255
_journal_issue                   4
_journal_name_full               'Acta Crystallographica Section E'
_journal_page_first              o760
_journal_page_last               o761
_journal_paper_doi               10.1107/S1600536811006994
_journal_volume                  67
_journal_year                    2011
_chemical_formula_iupac          'C20 H17 Cl2 N O'
_chemical_formula_moiety         'C20 H17 Cl2 N O'
_chemical_formula_sum            'C20 H17 Cl2 N O'
_chemical_formula_weight         358.25
_chemical_name_systematic
;
3,5-Bis(4-chlorobenzylidene)-1-methylpiperidin-4-one
;
_space_group_IT_number           14
_symmetry_cell_setting           monoclinic
_symmetry_space_group_name_Hall  '-P 2yn'
_symmetry_space_group_name_H-M   'P 1 21/n 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                 90.847(3)
_cell_angle_gamma                90.00
_cell_formula_units_Z            4
_cell_length_a                   5.4568(11)
_cell_length_b                   13.916(3)
_cell_length_c                   22.289(4)
_cell_measurement_reflns_used    2327
_cell_measurement_temperature    100(2)
_cell_measurement_theta_max      25.21
_cell_measurement_theta_min      2.43
_cell_volume                     1692.4(6)
_computing_cell_refinement       'SAINT (Bruker, 2007)'
_computing_data_collection       'APEX2 (Bruker, 2007)'
_computing_data_reduction        'SAINT (Bruker, 2007)'
_computing_molecular_graphics    'SHELXTL (Sheldrick, 2008)'
_computing_publication_material  'SHELXTL (Sheldrick, 2008)'
_computing_structure_refinement  'SHELXL97 (Sheldrick, 2008)'
_computing_structure_solution    'SHELXS97 (Sheldrick, 2008)'
_diffrn_ambient_temperature      100(2)
_diffrn_measured_fraction_theta_full 1.000
_diffrn_measured_fraction_theta_max 1.000
_diffrn_measurement_device_type  'Bruker SMART APEX II CCD'
_diffrn_measurement_method       ω
_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  0.0421
_diffrn_reflns_av_sigmaI/netI    0.0343
_diffrn_reflns_limit_h_max       6
_diffrn_reflns_limit_h_min       -6
_diffrn_reflns_limit_k_max       17
_diffrn_reflns_limit_k_min       -17
_diffrn_reflns_limit_l_max       27
_diffrn_reflns_limit_l_min       -27
_diffrn_reflns_number            14890
_diffrn_reflns_theta_full        26.37
_diffrn_reflns_theta_max         26.37
_diffrn_reflns_theta_min         1.83
_exptl_absorpt_coefficient_mu    0.390
_exptl_absorpt_correction_T_max  0.9695
_exptl_absorpt_correction_T_min  0.9157
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   '(SADABS; Bruker, 2001)'
_exptl_crystal_colour            yellow
_exptl_crystal_density_diffrn    1.406
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       plate
_exptl_crystal_F_000             744
_exptl_crystal_size_max          0.23
_exptl_crystal_size_mid          0.18
_exptl_crystal_size_min          0.08
_refine_diff_density_max         0.272
_refine_diff_density_min         -0.276
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.029
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     218
_refine_ls_number_reflns         3461
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.029
_refine_ls_R_factor_all          0.0459
_refine_ls_R_factor_gt           0.0343
_refine_ls_shift/su_max          0.001
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'calc w=1/[σ²(Fo²)+(0.0300P)²+0.8500P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0748
_refine_ls_wR_factor_ref         0.0802
_reflns_number_gt                2830
_reflns_number_total             3461
_reflns_threshold_expression     I>2σ(I)
_cod_data_source_file            su2255.cif
_cod_data_source_block           I
_cod_original_sg_symbol_H-M      'P 21/n'
_cod_database_code               2229847
_cod_database_fobs_code          2229847
loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'-x+1/2, y+1/2, -z+1/2'
'-x, -y, -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 0.64148(8) 0.85150(3) 0.742372(19) 0.02375(12) Uani d . 1 . .
Cl Cl2 0.64623(9) 0.87411(3) 0.01133(2) 0.02727(13) Uani d . 1 . .
O O1 0.1157(2) 0.92396(9) 0.37523(5) 0.0245(3) Uani d . 1 . .
N N1 0.5768(3) 0.71047(10) 0.37453(6) 0.0191(3) Uani d . 1 . .
C C1 0.7423(4) 0.62787(13) 0.37437(8) 0.0245(4) Uani d . 1 . .
H H1A 0.7070 0.5863 0.4087 0.037 Uiso calc R 1 . .
H H1B 0.9123 0.6503 0.3773 0.037 Uiso calc R 1 . .
H H1C 0.7187 0.5916 0.3370 0.037 Uiso calc R 1 . .
C C2 0.6145(3) 0.76651(12) 0.42936(8) 0.0187(4) Uani d . 1 . .
H H2A 0.7803 0.7953 0.4295 0.022 Uiso calc R 1 . .
H H2B 0.6023 0.7239 0.4648 0.022 Uiso calc R 1 . .
C C3 0.4243(3) 0.84484(12) 0.43294(8) 0.0172(4) Uani d . 1 . .
C C4 0.3040(3) 0.87585(12) 0.37573(8) 0.0188(4) Uani d . 1 . .
C C5 0.4283(3) 0.84936(12) 0.31884(8) 0.0170(4) Uani d . 1 . .
C C6 0.6202(3) 0.77144(12) 0.32221(8) 0.0183(4) Uani d . 1 . .
H H6A 0.6132 0.7321 0.2852 0.022 Uiso calc R 1 . .
H H6B 0.7852 0.8007 0.3255 0.022 Uiso calc R 1 . .
C C7 0.3539(3) 0.89000(12) 0.48316(8) 0.0181(4) Uani d . 1 . .
H H7A 0.2281 0.9364 0.4772 0.022 Uiso calc R 1 . .
C C8 0.4384(3) 0.87971(12) 0.54539(8) 0.0176(4) Uani d . 1 . .
C C9 0.2897(3) 0.91907(12) 0.59029(8) 0.0190(4) Uani d . 1 . .
H H9A 0.1438 0.9519 0.5788 0.023 Uiso calc R 1 . .
C C10 0.3496(3) 0.91133(13) 0.65039(8) 0.0201(4) Uani d . 1 . .
H H10A 0.2454 0.9374 0.6800 0.024 Uiso calc R 1 . .
C C11 0.5648(3) 0.86468(12) 0.66671(8) 0.0187(4) Uani d . 1 . .
C C12 0.7215(3) 0.82827(12) 0.62392(8) 0.0194(4) Uani d . 1 . .
H H12A 0.8710 0.7983 0.6358 0.023 Uiso calc R 1 . .
C C13 0.6586(3) 0.83584(12) 0.56397(8) 0.0191(4) Uani d . 1 . .
H H13A 0.7662 0.8109 0.5347 0.023 Uiso calc R 1 . .
C C14 0.3592(3) 0.89801(12) 0.26932(8) 0.0176(4) Uani d . 1 . .
H H14A 0.2328 0.9438 0.2755 0.021 Uiso calc R 1 . .
C C15 0.4450(3) 0.89257(12) 0.20763(8) 0.0174(4) Uani d . 1 . .
C C16 0.2956(3) 0.93346(13) 0.16272(8) 0.0204(4) Uani d . 1 . .
H H16A 0.1495 0.9655 0.1739 0.024 Uiso calc R 1 . .
C C17 0.3543(3) 0.92871(13) 0.10259(8) 0.0206(4) Uani d . 1 . .
H H17A 0.2491 0.9560 0.0728 0.025 Uiso calc R 1 . .
C C18 0.5693(3) 0.88342(12) 0.08676(8) 0.0192(4) Uani d . 1 . .
C C19 0.7270(3) 0.84500(12) 0.12966(8) 0.0199(4) Uani d . 1 . .
H H19A 0.8760 0.8155 0.1181 0.024 Uiso calc R 1 . .
C C20 0.6655(3) 0.84995(12) 0.18978(8) 0.0191(4) Uani d . 1 . .
H H20A 0.7742 0.8241 0.2193 0.023 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
C2 N1 C1 . . 110.01(14) ?
C2 N1 C6 . . 109.53(14) ?
C1 N1 C6 . . 110.27(13) ?
N1 C1 H1A . . 109.5 ?
N1 C1 H1B . . 109.5 ?
H1A C1 H1B . . 109.5 ?
N1 C1 H1C . . 109.5 ?
H1A C1 H1C . . 109.5 ?
H1B C1 H1C . . 109.5 ?
N1 C2 C3 . . 109.96(14) ?
N1 C2 H2A . . 109.7 ?
C3 C2 H2A . . 109.7 ?
N1 C2 H2B . . 109.7 ?
C3 C2 H2B . . 109.7 ?
H2A C2 H2B . . 108.2 ?
C7 C3 C4 . . 116.71(16) ?
C7 C3 C2 . . 125.96(16) ?
C4 C3 C2 . . 117.33(15) ?
O1 C4 C3 . . 121.64(16) ?
O1 C4 C5 . . 121.21(16) ?
C3 C4 C5 . . 117.10(15) ?
C14 C5 C4 . . 116.58(15) ?
C14 C5 C6 . . 126.10(16) ?
C4 C5 C6 . . 117.31(15) ?
N1 C6 C5 . . 109.62(14) ?
N1 C6 H6A . . 109.7 ?
C5 C6 H6A . . 109.7 ?
N1 C6 H6B . . 109.7 ?
C5 C6 H6B . . 109.7 ?
H6A C6 H6B . . 108.2 ?
C3 C7 C8 . . 130.82(17) ?
C3 C7 H7A . . 114.6 ?
C8 C7 H7A . . 114.6 ?
C13 C8 C9 . . 117.31(16) ?
C13 C8 C7 . . 125.35(16) ?
C9 C8 C7 . . 117.31(16) ?
C10 C9 C8 . . 121.96(16) ?
C10 C9 H9A . . 119.0 ?
C8 C9 H9A . . 119.0 ?
C9 C10 C11 . . 118.66(16) ?
C9 C10 H10A . . 120.7 ?
C11 C10 H10A . . 120.7 ?
C10 C11 C12 . . 121.30(16) ?
C10 C11 Cl1 . . 119.61(13) ?
C12 C11 Cl1 . . 119.09(14) ?
C13 C12 C11 . . 119.45(16) ?
C13 C12 H12A . . 120.3 ?
C11 C12 H12A . . 120.3 ?
C12 C13 C8 . . 121.23(16) ?
C12 C13 H13A . . 119.4 ?
C8 C13 H13A . . 119.4 ?
C5 C14 C15 . . 131.05(16) ?
C5 C14 H14A . . 114.5 ?
C15 C14 H14A . . 114.5 ?
C16 C15 C20 . . 117.43(16) ?
C16 C15 C14 . . 117.37(15) ?
C20 C15 C14 . . 125.19(16) ?
C17 C16 C15 . . 122.11(17) ?
C17 C16 H16A . . 118.9 ?
C15 C16 H16A . . 118.9 ?
C18 C17 C16 . . 118.58(16) ?
C18 C17 H17A . . 120.7 ?
C16 C17 H17A . . 120.7 ?
C17 C18 C19 . . 121.41(16) ?
C17 C18 Cl2 . . 119.84(14) ?
C19 C18 Cl2 . . 118.75(14) ?
C18 C19 C20 . . 119.40(16) ?
C18 C19 H19A . . 120.3 ?
C20 C19 H19A . . 120.3 ?
C19 C20 C15 . . 120.99(16) ?
C19 C20 H20A . . 119.5 ?
C15 C20 H20A . . 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
Cl1 C11 . 1.7412(18) ?
Cl2 C18 . 1.7437(18) ?
O1 C4 . 1.226(2) ?
N1 C2 . 1.462(2) ?
N1 C1 . 1.462(2) ?
N1 C6 . 1.464(2) ?
C1 H1A . 0.9800 ?
C1 H1B . 0.9800 ?
C1 H1C . 0.9800 ?
C2 C3 . 1.508(2) ?
C2 H2A . 0.9900 ?
C2 H2B . 0.9900 ?
C3 C7 . 1.345(2) ?
C3 C4 . 1.489(2) ?
C4 C5 . 1.493(2) ?
C5 C14 . 1.344(2) ?
C5 C6 . 1.509(2) ?
C6 H6A . 0.9900 ?
C6 H6B . 0.9900 ?
C7 C8 . 1.462(2) ?
C7 H7A . 0.9500 ?
C8 C13 . 1.405(2) ?
C8 C9 . 1.408(2) ?
C9 C10 . 1.378(2) ?
C9 H9A . 0.9500 ?
C10 C11 . 1.386(2) ?
C10 H10A . 0.9500 ?
C11 C12 . 1.386(2) ?
C12 C13 . 1.379(2) ?
C12 H12A . 0.9500 ?
C13 H13A . 0.9500 ?
C14 C15 . 1.461(2) ?
C14 H14A . 0.9500 ?
C15 C16 . 1.402(2) ?
C15 C20 . 1.404(2) ?
C16 C17 . 1.384(2) ?
C16 H16A . 0.9500 ?
C17 C18 . 1.382(2) ?
C17 H17A . 0.9500 ?
C18 C19 . 1.385(2) ?
C19 C20 . 1.388(2) ?
C19 H19A . 0.9500 ?
C20 H20A . 0.9500 ?
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
C9 H9A O1 3_576 0.95 2.47 3.210(2) 135
C12 H12A Cg1 4_676 0.95 2.72 3.439(2) 133
C19 H19A Cg2 4_675 0.95 2.73 3.432(2) 131
loop_
_cod_related_entry_id
_cod_related_entry_database
_cod_related_entry_code
1 ChemSpider 1458771
