#------------------------------------------------------------------------------
#$Date: 2017-10-13 11:42:48 +0300 (Fri, 13 Oct 2017) $
#$Revision: 201978 $
#$URL: file:///home/coder/svn-repositories/cod/cif/2/22/09/2220932.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_2220932
loop_
_publ_author_name
'Ahmad, Kartini'
'Awang, Khalijah'
'Thomas, Noel F.'
'Weber, Jean-Frederic Faizal'
'Ng, Seik Weng'
_publ_section_title
;
 N-{2-[2-(2,6-Dichloro-3,5-dimethoxyphenyl)ethenyl]phenyl}acetamide
;
_journal_coeditor_code           TK2361
_journal_issue                   2
_journal_name_full               'Acta Crystallographica Section E'
_journal_page_first              o438
_journal_paper_doi               10.1107/S1600536809003250
_journal_volume                  65
_journal_year                    2009
_chemical_formula_iupac          'C18 H17 Cl2 N O3'
_chemical_formula_moiety         'C18 H17 Cl2 N O3'
_chemical_formula_sum            'C18 H17 Cl2 N O3'
_chemical_formula_weight         366.23
_chemical_name_systematic
;
N-{2-[2-(2,6-Dichloro-3,5-dimethoxyphenyl)ethenyl]phenyl}acetamide
;
_space_group_IT_number           2
_symmetry_cell_setting           triclinic
_symmetry_space_group_name_Hall  '-P 1'
_symmetry_space_group_name_H-M   'P -1'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_audit_creation_method           SHELXL97
_cell_angle_alpha                78.561(2)
_cell_angle_beta                 77.716(2)
_cell_angle_gamma                85.969(3)
_cell_formula_units_Z            2
_cell_length_a                   7.5646(3)
_cell_length_b                   9.1485(3)
_cell_length_c                   12.2969(5)
_cell_measurement_reflns_used    1123
_cell_measurement_temperature    100(2)
_cell_measurement_theta_max      26.5
_cell_measurement_theta_min      2.6
_cell_volume                     814.65(5)
_computing_cell_refinement       'SAINT (Bruker, 2007)'
_computing_data_collection       'APEX2 (Bruker, 2007)'
_computing_data_reduction        'SAINT (Bruker, 2007)'
_computing_molecular_graphics    'X-SEED (Barbour, 2001)'
_computing_publication_material  'publCIF (Westrip, 2009)'
_computing_structure_refinement  'SHELXL97 (Sheldrick, 2008)'
_computing_structure_solution    'SHELXS97 (Sheldrick, 2008)'
_diffrn_ambient_temperature      100(2)
_diffrn_measured_fraction_theta_full 0.979
_diffrn_measured_fraction_theta_max 0.979
_diffrn_measurement_device_type  'Bruker SMART APEX'
_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  0.048
_diffrn_reflns_av_sigmaI/netI    0.085
_diffrn_reflns_limit_h_max       9
_diffrn_reflns_limit_h_min       -9
_diffrn_reflns_limit_k_max       11
_diffrn_reflns_limit_k_min       -11
_diffrn_reflns_limit_l_max       15
_diffrn_reflns_limit_l_min       -15
_diffrn_reflns_number            6677
_diffrn_reflns_theta_full        27.5
_diffrn_reflns_theta_max         27.5
_diffrn_reflns_theta_min         2.3
_diffrn_standards_decay_%        0
_diffrn_standards_interval_count 0
_diffrn_standards_interval_time  0
_diffrn_standards_number         0
_exptl_absorpt_coefficient_mu    0.415
_exptl_absorpt_correction_T_max  0.988
_exptl_absorpt_correction_T_min  0.886
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   '(SADABS; Sheldrick, 1996)'
_exptl_crystal_colour            colourless
_exptl_crystal_density_diffrn    1.493
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       prism
_exptl_crystal_F_000             380
_exptl_crystal_size_max          0.30
_exptl_crystal_size_mid          0.03
_exptl_crystal_size_min          0.03
_refine_diff_density_max         0.40
_refine_diff_density_min         -0.37
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   0.99
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     220
_refine_ls_number_reflns         3657
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      0.99
_refine_ls_R_factor_all          0.075
_refine_ls_R_factor_gt           0.048
_refine_ls_shift/su_max          0.001
_refine_ls_shift/su_mean         0.001
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'calc w = 1/[σ²(Fo²)+(0.046P)²] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.105
_refine_ls_wR_factor_ref         0.117
_reflns_number_gt                2490
_reflns_number_total             3657
_reflns_threshold_expression     I>2σ(I)
_cod_data_source_file            tk2361.cif
_cod_data_source_block           I
_cod_database_code               2220932
_cod_database_fobs_code          2220932
loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'-x, -y, -z'
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 0.21992(9) 0.40664(7) 0.21221(5) 0.02175(18) Uani d . 1 . .
Cl Cl2 0.28411(9) 0.66314(7) 0.56854(5) 0.01944(18) Uani d . 1 . .
O O1 0.3311(3) 0.68767(19) 0.08280(14) 0.0248(5) Uani d . 1 . .
O O2 0.4014(2) 0.90427(18) 0.39962(15) 0.0203(4) Uani d . 1 . .
O O3 0.1911(3) 0.2547(2) 0.96831(17) 0.0353(5) Uani d . 1 . .
N N1 0.1666(3) 0.3365(2) 0.78526(18) 0.0198(5) Uani d . 1 . .
H H1 0.1734 0.4173 0.7322 0.024 Uiso calc R 1 . .
C C1 0.2581(3) 0.5380(3) 0.3861(2) 0.0141(5) Uani d . 1 . .
C C2 0.2725(3) 0.5540(3) 0.2691(2) 0.0162(6) Uani d . 1 . .
C C3 0.3281(4) 0.6856(3) 0.1940(2) 0.0171(6) Uani d . 1 . .
C C4 0.3763(4) 0.8042(3) 0.2354(2) 0.0183(6) Uani d . 1 . .
H H4 0.4190 0.8928 0.1845 0.022 Uiso calc R 1 . .
C C5 0.3624(3) 0.7936(3) 0.3506(2) 0.0158(6) Uani d . 1 . .
C C6 0.3045(3) 0.6611(3) 0.4245(2) 0.0149(5) Uani d . 1 . .
C C7 0.3852(4) 0.8217(3) 0.0026(2) 0.0285(7) Uani d . 1 . .
H H7A 0.3723 0.8102 -0.0729 0.043 Uiso calc R 1 . .
H H7B 0.5119 0.8405 0.0009 0.043 Uiso calc R 1 . .
H H7C 0.3085 0.9060 0.0250 0.043 Uiso calc R 1 . .
C C8 0.4638(4) 1.0415(3) 0.3273(2) 0.0232(6) Uani d . 1 . .
H H8A 0.4852 1.1118 0.3735 0.035 Uiso calc R 1 . .
H H8B 0.3721 1.0843 0.2836 0.035 Uiso calc R 1 . .
H H8C 0.5768 1.0225 0.2753 0.035 Uiso calc R 1 . .
C C9 0.1833(3) 0.4005(3) 0.4615(2) 0.0154(6) Uani d . 1 . .
H H9 0.0883 0.3559 0.4413 0.019 Uiso calc R 1 . .
C C10 0.2381(3) 0.3337(3) 0.5558(2) 0.0144(5) Uani d . 1 . .
H H10 0.3401 0.3734 0.5723 0.017 Uiso calc R 1 . .
C C11 0.1548(3) 0.2039(3) 0.6366(2) 0.0159(6) Uani d . 1 . .
C C12 0.1058(4) 0.0794(3) 0.6023(2) 0.0193(6) Uani d . 1 . .
H H12 0.1223 0.0778 0.5238 0.023 Uiso calc R 1 . .
C C13 0.0330(4) -0.0426(3) 0.6812(2) 0.0207(6) Uani d . 1 . .
H H13 -0.0016 -0.1264 0.6565 0.025 Uiso calc R 1 . .
C C14 0.0106(4) -0.0427(3) 0.7955(2) 0.0222(6) Uani d . 1 . .
H H14 -0.0367 -0.1275 0.8492 0.027 Uiso calc R 1 . .
C C15 0.0568(4) 0.0805(3) 0.8323(2) 0.0203(6) Uani d . 1 . .
H H15 0.0404 0.0803 0.9111 0.024 Uiso calc R 1 . .
C C16 0.1273(4) 0.2042(3) 0.7536(2) 0.0178(6) Uani d . 1 . .
C C17 0.1954(4) 0.3555(3) 0.8874(2) 0.0234(6) Uani d . 1 . .
C C18 0.2350(4) 0.5142(3) 0.8907(2) 0.0289(7) Uani d . 1 . .
H H18A 0.2924 0.5147 0.9549 0.043 Uiso calc R 1 . .
H H18B 0.1216 0.5736 0.8993 0.043 Uiso calc R 1 . .
H H18C 0.3165 0.5572 0.8201 0.043 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
C3 O1 C7 . . 118.2(2) ?
C5 O2 C8 . . 118.00(19) ?
C17 N1 C16 . . 128.5(2) ?
C17 N1 H1 . . 115.7 ?
C16 N1 H1 . . 115.7 ?
C6 C1 C2 . . 116.4(2) ?
C6 C1 C9 . . 124.0(2) ?
C2 C1 C9 . . 119.5(2) ?
C3 C2 C1 . . 122.4(2) ?
C3 C2 Cl1 . . 117.50(19) ?
C1 C2 Cl1 . . 120.11(19) ?
O1 C3 C4 . . 124.3(2) ?
O1 C3 C2 . . 116.4(2) ?
C4 C3 C2 . . 119.4(2) ?
C5 C4 C3 . . 120.1(2) ?
C5 C4 H4 . . 120.0 ?
C3 C4 H4 . . 120.0 ?
O2 C5 C4 . . 124.6(2) ?
O2 C5 C6 . . 115.8(2) ?
C4 C5 C6 . . 119.6(2) ?
C5 C6 C1 . . 122.2(2) ?
C5 C6 Cl2 . . 115.48(18) ?
C1 C6 Cl2 . . 122.29(19) ?
O1 C7 H7A . . 109.5 ?
O1 C7 H7B . . 109.5 ?
H7A C7 H7B . . 109.5 ?
O1 C7 H7C . . 109.5 ?
H7A C7 H7C . . 109.5 ?
H7B C7 H7C . . 109.5 ?
O2 C8 H8A . . 109.5 ?
O2 C8 H8B . . 109.5 ?
H8A C8 H8B . . 109.5 ?
O2 C8 H8C . . 109.5 ?
H8A C8 H8C . . 109.5 ?
H8B C8 H8C . . 109.5 ?
C10 C9 C1 . . 125.3(2) ?
C10 C9 H9 . . 117.3 ?
C1 C9 H9 . . 117.3 ?
C9 C10 C11 . . 125.8(2) ?
C9 C10 H10 . . 117.1 ?
C11 C10 H10 . . 117.1 ?
C12 C11 C16 . . 118.6(2) ?
C12 C11 C10 . . 122.6(2) ?
C16 C11 C10 . . 118.8(2) ?
C13 C12 C11 . . 120.9(2) ?
C13 C12 H12 . . 119.6 ?
C11 C12 H12 . . 119.6 ?
C14 C13 C12 . . 120.1(2) ?
C14 C13 H13 . . 119.9 ?
C12 C13 H13 . . 119.9 ?
C13 C14 C15 . . 120.3(2) ?
C13 C14 H14 . . 119.8 ?
C15 C14 H14 . . 119.8 ?
C14 C15 C16 . . 119.8(2) ?
C14 C15 H15 . . 120.1 ?
C16 C15 H15 . . 120.1 ?
C15 C16 N1 . . 122.6(2) ?
C15 C16 C11 . . 120.3(2) ?
N1 C16 C11 . . 117.0(2) ?
O3 C17 N1 . . 123.4(3) ?
O3 C17 C18 . . 122.7(3) ?
N1 C17 C18 . . 114.0(2) ?
C17 C18 H18A . . 109.5 ?
C17 C18 H18B . . 109.5 ?
H18A C18 H18B . . 109.5 ?
C17 C18 H18C . . 109.5 ?
H18A C18 H18C . . 109.5 ?
H18B C18 H18C . . 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
Cl1 C2 . 1.742(2) ?
Cl2 C6 . 1.748(2) ?
O1 C3 . 1.359(3) ?
O1 C7 . 1.437(3) ?
O2 C5 . 1.355(3) ?
O2 C8 . 1.433(3) ?
O3 C17 . 1.211(3) ?
N1 C17 . 1.365(3) ?
N1 C16 . 1.411(3) ?
N1 H1 . 0.8800 ?
C1 C6 . 1.397(3) ?
C1 C2 . 1.399(3) ?
C1 C9 . 1.476(3) ?
C2 C3 . 1.395(3) ?
C3 C4 . 1.387(3) ?
C4 C5 . 1.382(3) ?
C4 H4 . 0.9500 ?
C5 C6 . 1.398(3) ?
C7 H7A . 0.9800 ?
C7 H7B . 0.9800 ?
C7 H7C . 0.9800 ?
C8 H8A . 0.9800 ?
C8 H8B . 0.9800 ?
C8 H8C . 0.9800 ?
C9 C10 . 1.333(4) ?
C9 H9 . 0.9500 ?
C10 C11 . 1.471(3) ?
C10 H10 . 0.9500 ?
C11 C12 . 1.389(3) ?
C11 C16 . 1.410(3) ?
C12 C13 . 1.386(4) ?
C12 H12 . 0.9500 ?
C13 C14 . 1.379(4) ?
C13 H13 . 0.9500 ?
C14 C15 . 1.386(4) ?
C14 H14 . 0.9500 ?
C15 C16 . 1.391(4) ?
C15 H15 . 0.9500 ?
C17 C18 . 1.513(4) ?
C18 H18A . 0.9800 ?
C18 H18B . 0.9800 ?
C18 H18C . 0.9800 ?
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
C6 C1 C2 C3 . . . . -0.7(4) ?
C9 C1 C2 C3 . . . . 174.7(2) ?
C6 C1 C2 Cl1 . . . . 179.43(19) ?
C9 C1 C2 Cl1 . . . . -5.2(3) ?
C7 O1 C3 C4 . . . . -0.9(4) ?
C7 O1 C3 C2 . . . . 179.2(2) ?
C1 C2 C3 O1 . . . . -178.1(2) ?
Cl1 C2 C3 O1 . . . . 1.8(3) ?
C1 C2 C3 C4 . . . . 2.0(4) ?
Cl1 C2 C3 C4 . . . . -178.1(2) ?
O1 C3 C4 C5 . . . . 177.6(2) ?
C2 C3 C4 C5 . . . . -2.5(4) ?
C8 O2 C5 C4 . . . . -0.8(4) ?
C8 O2 C5 C6 . . . . 179.1(2) ?
C3 C4 C5 O2 . . . . -178.2(2) ?
C3 C4 C5 C6 . . . . 1.9(4) ?
O2 C5 C6 C1 . . . . 179.5(2) ?
C4 C5 C6 C1 . . . . -0.6(4) ?
O2 C5 C6 Cl2 . . . . 2.3(3) ?
C4 C5 C6 Cl2 . . . . -177.7(2) ?
C2 C1 C6 C5 . . . . 0.0(4) ?
C9 C1 C6 C5 . . . . -175.1(2) ?
C2 C1 C6 Cl2 . . . . 176.94(19) ?
C9 C1 C6 Cl2 . . . . 1.8(4) ?
C6 C1 C9 C10 . . . . -40.8(4) ?
C2 C1 C9 C10 . . . . 144.2(3) ?
C1 C9 C10 C11 . . . . 174.6(2) ?
C9 C10 C11 C12 . . . . 45.5(4) ?
C9 C10 C11 C16 . . . . -136.0(3) ?
C16 C11 C12 C13 . . . . -0.6(4) ?
C10 C11 C12 C13 . . . . 177.9(2) ?
C11 C12 C13 C14 . . . . -0.9(4) ?
C12 C13 C14 C15 . . . . 1.5(4) ?
C13 C14 C15 C16 . . . . -0.5(4) ?
C14 C15 C16 N1 . . . . 176.0(2) ?
C14 C15 C16 C11 . . . . -1.1(4) ?
C17 N1 C16 C15 . . . . 20.7(4) ?
C17 N1 C16 C11 . . . . -162.1(3) ?
C12 C11 C16 C15 . . . . 1.6(4) ?
C10 C11 C16 C15 . . . . -177.0(2) ?
C12 C11 C16 N1 . . . . -175.6(2) ?
C10 C11 C16 N1 . . . . 5.8(4) ?
C16 N1 C17 O3 . . . . 0.3(5) ?
C16 N1 C17 C18 . . . . 179.8(2) ?
loop_
_cod_related_entry_id
_cod_related_entry_database
_cod_related_entry_code
1 ChemSpider 24741666
