#------------------------------------------------------------------------------
#$Date: 2017-10-13 11:03:29 +0300 (Fri, 13 Oct 2017) $
#$Revision: 201974 $
#$URL: file:///home/coder/svn-repositories/cod/cif/2/21/08/2210864.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_2210864
loop_
_publ_author_name
'Yang, Shu-Ping'
'Han, Li-Jun'
'Wang, Da-Qi'
'Ding, Tie-Zhu'
_publ_section_title
;
 (E,E)-4-(Dimethylamino)benzaldehyde
 O-[3-(3-chlorophenyl)propenoyl]oxime
;
_journal_coeditor_code           AT2137
_journal_issue                   11
_journal_name_full               'Acta Crystallographica Section E'
_journal_page_first              o5199
_journal_page_last               o5201
_journal_paper_doi               10.1107/S1600536806043741
_journal_volume                  62
_journal_year                    2006
_chemical_formula_iupac          'C18 H17 Cl N2 O2'
_chemical_formula_moiety         'C18 H17 Cl N2 O2'
_chemical_formula_sum            'C18 H17 Cl N2 O2'
_chemical_formula_weight         328.79
_chemical_melting_point          436
_chemical_name_systematic
;
(E,E)-4-(Dimethylamino)benzaldehyde O-[3-(3-chlorophenyl)propenoyl]oxime
;
_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                108.706(5)
_cell_angle_beta                 104.242(5)
_cell_angle_gamma                94.628(5)
_cell_formula_units_Z            2
_cell_length_a                   8.161(3)
_cell_length_b                   9.792(3)
_cell_length_c                   11.228(4)
_cell_measurement_reflns_used    1077
_cell_measurement_temperature    298(2)
_cell_measurement_theta_max      22.57
_cell_measurement_theta_min      2.414
_cell_volume                     811.2(5)
_computing_cell_refinement       SMART
_computing_data_collection       'SMART (Siemens, 1996)'
_computing_data_reduction        'SAINT (Siemens, 1996)'
_computing_molecular_graphics    'SHELXTL (Sheldrick, 1997b)'
_computing_publication_material  SHELXTL
_computing_structure_refinement  'SHELXL97 (Sheldrick, 1997a)'
_computing_structure_solution    'SHELXS97 (Sheldrick, 1997a)'
_diffrn_ambient_temperature      298(2)
_diffrn_measured_fraction_theta_full 0.987
_diffrn_measured_fraction_theta_max 0.987
_diffrn_measurement_device_type  'Siemens SMART 1000 CCD area-detector'
_diffrn_measurement_method       'φ and 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  0.0214
_diffrn_reflns_av_sigmaI/netI    0.0518
_diffrn_reflns_limit_h_max       9
_diffrn_reflns_limit_h_min       -9
_diffrn_reflns_limit_k_max       9
_diffrn_reflns_limit_k_min       -11
_diffrn_reflns_limit_l_max       13
_diffrn_reflns_limit_l_min       -8
_diffrn_reflns_number            4304
_diffrn_reflns_theta_full        25.01
_diffrn_reflns_theta_max         25.01
_diffrn_reflns_theta_min         2.00
_diffrn_standards_number         0
_exptl_absorpt_coefficient_mu    0.247
_exptl_absorpt_correction_T_max  0.9640
_exptl_absorpt_correction_T_min  0.8972
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   '(SADABS; Sheldrick, 1996)'
_exptl_crystal_colour            yellow
_exptl_crystal_density_diffrn    1.346
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       columnar
_exptl_crystal_F_000             344
_exptl_crystal_size_max          0.45
_exptl_crystal_size_mid          0.28
_exptl_crystal_size_min          0.15
_refine_diff_density_max         0.215
_refine_diff_density_min         -0.202
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc²λ³/sin(2θ)]^-1/4^
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.022
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     211
_refine_ls_number_reflns         2840
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.022
_refine_ls_R_factor_all          0.0967
_refine_ls_R_factor_gt           0.0497
_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)+(0.0554P)²+0.0567P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1066
_refine_ls_wR_factor_ref         0.1308
_reflns_number_gt                1623
_reflns_number_total             2840
_reflns_threshold_expression     I>2σ(I)
_cod_data_source_file            at2137.cif
_cod_data_source_block           I
_cod_original_cell_volume        811.1(5)
_cod_database_code               2210864
_cod_database_fobs_code          2210864
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
Cl Cl1 0.47606(11) -0.31483(8) -0.53841(8) 0.0756(3) Uani d . 1
N N1 0.2248(3) 0.6025(2) 0.0179(2) 0.0597(7) Uani d . 1
N N2 0.0979(3) 1.2383(2) 0.3388(2) 0.0622(7) Uani d . 1
O O1 0.2443(3) 0.45227(18) -0.00377(18) 0.0638(6) Uani d . 1
O O2 0.3118(4) 0.4463(2) -0.1870(2) 0.1073(10) Uani d . 1
C C1 0.2900(4) 0.3877(3) -0.1135(3) 0.0597(8) Uani d . 1
C C2 0.3081(4) 0.2377(3) -0.1265(3) 0.0568(8) Uani d . 1
H H2 0.2849 0.2020 -0.0638 0.068 Uiso calc R 1
C C3 0.3556(4) 0.1507(3) -0.2226(3) 0.0544(8) Uani d . 1
H H3 0.3803 0.1919 -0.2816 0.065 Uiso calc R 1
C C4 0.3750(3) -0.0024(3) -0.2499(3) 0.0466(7) Uani d . 1
C C5 0.4150(3) -0.0782(3) -0.3637(2) 0.0512(7) Uani d . 1
H H5 0.4311 -0.0305 -0.4206 0.061 Uiso calc R 1
C C6 0.4310(3) -0.2230(3) -0.3930(3) 0.0499(7) Uani d . 1
C C7 0.4089(4) -0.2952(3) -0.3105(3) 0.0601(8) Uani d . 1
H H7 0.4188 -0.3935 -0.3315 0.072 Uiso calc R 1
C C8 0.3718(4) -0.2211(3) -0.1962(3) 0.0633(8) Uani d . 1
H H8 0.3589 -0.2689 -0.1388 0.076 Uiso calc R 1
C C9 0.3537(4) -0.0766(3) -0.1666(3) 0.0580(8) Uani d . 1
H H9 0.3270 -0.0279 -0.0898 0.070 Uiso calc R 1
C C10 0.1916(4) 0.6533(3) 0.1263(3) 0.0555(8) Uani d . 1
H H10 0.1837 0.5927 0.1744 0.067 Uiso calc R 1
C C11 0.1652(3) 0.8034(3) 0.1780(2) 0.0478(7) Uani d . 1
C C12 0.1688(4) 0.8991(3) 0.1108(3) 0.0545(8) Uani d . 1
H H12 0.1867 0.8667 0.0284 0.065 Uiso calc R 1
C C13 0.1465(4) 1.0404(3) 0.1632(3) 0.0559(8) Uani d . 1
H H13 0.1497 1.1018 0.1152 0.067 Uiso calc R 1
C C14 0.1190(3) 1.0959(3) 0.2866(3) 0.0486(7) Uani d . 1
C C15 0.1155(4) 0.9988(3) 0.3538(3) 0.0575(8) Uani d . 1
H H15 0.0981 1.0306 0.4364 0.069 Uiso calc R 1
C C16 0.1375(4) 0.8571(3) 0.2998(3) 0.0572(8) Uani d . 1
H H16 0.1337 0.7949 0.3469 0.069 Uiso calc R 1
C C17 0.1051(5) 1.3400(3) 0.2704(3) 0.0812(10) Uani d . 1
H H17A 0.1063 1.4369 0.3280 0.122 Uiso calc R 1
H H17B 0.0064 1.3123 0.1949 0.122 Uiso calc R 1
H H17C 0.2075 1.3384 0.2427 0.122 Uiso calc R 1
C C18 0.0621(4) 1.2906(3) 0.4644(3) 0.0805(10) Uani d . 1
H H18A 0.0456 1.3905 0.4841 0.121 Uiso calc R 1
H H18B 0.1570 1.2845 0.5317 0.121 Uiso calc R 1
H H18C -0.0400 1.2313 0.4608 0.121 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
_geom_angle_publ_flag
C10 N1 O1 107.9(2) y
C14 N2 C17 122.0(2) ?
C14 N2 C18 120.4(2) ?
C17 N2 C18 117.6(2) ?
C1 O1 N1 113.7(2) ?
O2 C1 O1 124.3(3) ?
O2 C1 C2 125.9(3) ?
O1 C1 C2 109.8(3) ?
C3 C2 C1 122.7(3) y
C3 C2 H2 118.7 ?
C1 C2 H2 118.7 ?
C2 C3 C4 128.7(3) y
C2 C3 H3 115.7 ?
C4 C3 H3 115.7 ?
C5 C4 C9 118.2(2) ?
C5 C4 C3 119.2(2) ?
C9 C4 C3 122.6(2) ?
C6 C5 C4 120.5(3) ?
C6 C5 H5 119.8 ?
C4 C5 H5 119.8 ?
C7 C6 C5 120.8(3) ?
C7 C6 Cl1 120.2(2) ?
C5 C6 Cl1 119.0(2) ?
C6 C7 C8 119.4(2) ?
C6 C7 H7 120.3 ?
C8 C7 H7 120.3 ?
C9 C8 C7 120.2(3) ?
C9 C8 H8 119.9 ?
C7 C8 H8 119.9 ?
C8 C9 C4 120.9(3) ?
C8 C9 H9 119.6 ?
C4 C9 H9 119.6 ?
N1 C10 C11 122.0(3) ?
N1 C10 H10 119.0 ?
C11 C10 H10 119.0 ?
C12 C11 C16 117.0(2) ?
C12 C11 C10 122.7(2) ?
C16 C11 C10 120.3(3) y
C13 C12 C11 121.2(3) ?
C13 C12 H12 119.4 ?
C11 C12 H12 119.4 ?
C12 C13 C14 122.2(3) ?
C12 C13 H13 118.9 ?
C14 C13 H13 118.9 ?
N2 C14 C15 121.9(2) ?
N2 C14 C13 121.8(3) ?
C15 C14 C13 116.2(2) ?
C16 C15 C14 120.9(3) ?
C16 C15 H15 119.5 ?
C14 C15 H15 119.5 ?
C15 C16 C11 122.4(3) ?
C15 C16 H16 118.8 ?
C11 C16 H16 118.8 ?
N2 C17 H17A 109.5 ?
N2 C17 H17B 109.5 ?
H17A C17 H17B 109.5 ?
N2 C17 H17C 109.5 ?
H17A C17 H17C 109.5 ?
H17B C17 H17C 109.5 ?
N2 C18 H18A 109.5 ?
N2 C18 H18B 109.5 ?
H18A C18 H18B 109.5 ?
N2 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_distance
_geom_bond_publ_flag
Cl1 C6 1.737(3) ?
N1 C10 1.263(3) y
N1 O1 1.441(3) y
N2 C14 1.371(3) ?
N2 C17 1.446(3) ?
N2 C18 1.450(3) ?
O1 C1 1.350(3) ?
O2 C1 1.184(3) ?
C1 C2 1.452(4) ?
C2 C3 1.308(3) ?
C2 H2 0.9300 ?
C3 C4 1.461(3) ?
C3 H3 0.9300 ?
C4 C5 1.388(3) ?
C4 C9 1.388(4) ?
C5 C6 1.374(3) ?
C5 H5 0.9300 ?
C6 C7 1.368(4) ?
C7 C8 1.376(4) ?
C7 H7 0.9300 ?
C8 C9 1.375(3) ?
C8 H8 0.9300 ?
C9 H9 0.9300 ?
C10 C11 1.453(3) ?
C10 H10 0.9300 ?
C11 C12 1.381(3) ?
C11 C16 1.381(3) ?
C12 C13 1.366(3) ?
C12 H12 0.9300 ?
C13 C14 1.398(3) ?
C13 H13 0.9300 ?
C14 C15 1.393(4) ?
C15 C16 1.371(4) ?
C15 H15 0.9300 ?
C16 H16 0.9300 ?
C17 H17A 0.9600 ?
C17 H17B 0.9600 ?
C17 H17C 0.9600 ?
C18 H18A 0.9600 ?
C18 H18B 0.9600 ?
C18 H18C 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
C8 H8 O2 1_545 0.93 2.64 3.292(3) 127.7
C8 H8 N1 1_545 0.93 2.83 3.735(4) 163.9
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
_geom_torsion_publ_flag
C10 N1 O1 C1 -176.4(2) ?
N1 O1 C1 O2 -0.4(4) ?
N1 O1 C1 C2 179.5(2) y
O2 C1 C2 C3 1.6(5) ?
O1 C1 C2 C3 -178.3(3) ?
C1 C2 C3 C4 -178.4(3) y
C2 C3 C4 C5 175.2(3) ?
C2 C3 C4 C9 -4.2(5) ?
C9 C4 C5 C6 0.7(4) ?
C3 C4 C5 C6 -178.8(2) ?
C4 C5 C6 C7 -0.4(4) ?
C4 C5 C6 Cl1 178.5(2) ?
C5 C6 C7 C8 -0.6(4) ?
Cl1 C6 C7 C8 -179.5(2) ?
C6 C7 C8 C9 1.3(5) ?
C7 C8 C9 C4 -1.0(5) ?
C5 C4 C9 C8 0.0(4) ?
C3 C4 C9 C8 179.5(3) ?
O1 N1 C10 C11 179.6(2) y
N1 C10 C11 C12 2.3(4) ?
N1 C10 C11 C16 -176.8(3) ?
C16 C11 C12 C13 0.2(4) ?
C10 C11 C12 C13 -178.8(3) ?
C11 C12 C13 C14 0.0(5) ?
C17 N2 C14 C15 178.6(3) ?
C18 N2 C14 C15 -3.2(4) ?
C17 N2 C14 C13 -0.9(4) ?
C18 N2 C14 C13 177.3(3) ?
C12 C13 C14 N2 179.6(3) ?
C12 C13 C14 C15 0.0(4) ?
N2 C14 C15 C16 -179.8(3) ?
C13 C14 C15 C16 -0.2(4) ?
C14 C15 C16 C11 0.5(5) ?
C12 C11 C16 C15 -0.5(4) ?
C10 C11 C16 C15 178.6(3) ?
loop_
_cod_related_entry_id
_cod_related_entry_database
_cod_related_entry_code
1 ChemSpider 30655081
