#------------------------------------------------------------------------------
#$Date: 2017-10-13 11:03:29 +0300 (Fri, 13 Oct 2017) $
#$Revision: 201974 $
#$URL: file:///home/coder/svn-repositories/cod/cif/2/21/00/2210067.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_2210067
loop_
_publ_author_name
'Yang, Shu-Ping'
'Han, Li-Jun'
'Wang, Da-Qi'
'Xia, Hai-Tao'
_publ_section_title
;
 (E,E)-4-(Dimethylamino)benzaldehyde
 O-(3-phenylpropenoyl)oxime
;
_journal_coeditor_code           AT2086
_journal_issue                   9
_journal_name_full               'Acta Crystallographica Section E'
_journal_page_first              o3923
_journal_page_last               o3925
_journal_paper_doi               10.1107/S1600536806032132
_journal_volume                  62
_journal_year                    2006
_chemical_formula_iupac          'C18 H18 N2 O2'
_chemical_formula_moiety         'C18 H18 N2 O2'
_chemical_formula_sum            'C18 H18 N2 O2'
_chemical_formula_weight         294.34
_chemical_melting_point          416
_chemical_name_systematic
;
(E,E)-4-Dimethylaminobenzaldehyde O-(3-phenylpropenoyl)oxime
;
_space_group_IT_number           15
_symmetry_cell_setting           monoclinic
_symmetry_space_group_name_Hall  '-C 2yc'
_symmetry_space_group_name_H-M   'C 1 2/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                 106.092(14)
_cell_angle_gamma                90.00
_cell_formula_units_Z            8
_cell_length_a                   23.88(2)
_cell_length_b                   6.406(6)
_cell_length_c                   21.41(2)
_cell_measurement_reflns_used    972
_cell_measurement_temperature    298(2)
_cell_measurement_theta_max      20.79
_cell_measurement_theta_min      3.004
_cell_volume                     3147(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 0.998
_diffrn_measured_fraction_theta_max 0.998
_diffrn_measurement_device_type  'Bruker SMART 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  0.0697
_diffrn_reflns_av_sigmaI/netI    0.0942
_diffrn_reflns_limit_h_max       28
_diffrn_reflns_limit_h_min       -25
_diffrn_reflns_limit_k_max       7
_diffrn_reflns_limit_k_min       -7
_diffrn_reflns_limit_l_max       25
_diffrn_reflns_limit_l_min       -22
_diffrn_reflns_number            7760
_diffrn_reflns_theta_full        25.01
_diffrn_reflns_theta_max         25.01
_diffrn_reflns_theta_min         1.77
_diffrn_standards_number         0
_exptl_absorpt_coefficient_mu    0.082
_exptl_absorpt_correction_T_max  0.9927
_exptl_absorpt_correction_T_min  0.9540
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   '(SADABS; Sheldrick, 1996)'
_exptl_crystal_colour            yellow
_exptl_crystal_density_diffrn    1.242
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       column
_exptl_crystal_F_000             1248
_exptl_crystal_size_max          0.58
_exptl_crystal_size_mid          0.31
_exptl_crystal_size_min          0.09
_refine_diff_density_max         0.171
_refine_diff_density_min         -0.216
_refine_ls_abs_structure_details
;
?
;
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.003
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     199
_refine_ls_number_reflns         2781
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.003
_refine_ls_R_factor_all          0.1502
_refine_ls_R_factor_gt           0.0552
_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)+(0.0457P)²] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1090
_refine_ls_wR_factor_ref         0.1430
_reflns_number_gt                1160
_reflns_number_total             2781
_reflns_threshold_expression     I>2σ(I)
_cod_data_source_file            at2086.cif
_cod_data_source_block           I
_cod_original_sg_symbol_H-M      'C 2/c'
_cod_database_code               2210067
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'
'-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
N N1 0.16599(11) 0.9931(5) 0.46307(12) 0.0606(8) Uani d . 1
N N2 0.00803(12) 0.5521(5) 0.62357(14) 0.0679(9) Uani d . 1
O O1 0.20919(9) 1.0075(4) 0.42703(10) 0.0611(7) Uani d . 1
O O2 0.19554(11) 1.3565(4) 0.42541(13) 0.0862(9) Uani d . 1
C C1 0.21741(14) 1.2060(6) 0.40815(16) 0.0551(9) Uani d . 1
C C2 0.25569(13) 1.2028(5) 0.36569(15) 0.0565(10) Uani d . 1
H H2 0.2643 1.0756 0.3496 0.068 Uiso calc R 1
C C3 0.27849(13) 1.3755(5) 0.34941(15) 0.0564(9) Uani d . 1
H H3 0.2708 1.4984 0.3686 0.068 Uiso calc R 1
C C4 0.31449(13) 1.3945(5) 0.30453(14) 0.0489(9) Uani d . 1
C C5 0.34239(13) 1.5817(6) 0.30048(15) 0.0617(10) Uani d . 1
H H5 0.3385 1.6927 0.3270 0.074 Uiso calc R 1
C C6 0.37603(15) 1.6061(6) 0.25757(18) 0.0742(11) Uani d . 1
H H6 0.3948 1.7323 0.2560 0.089 Uiso calc R 1
C C7 0.38177(15) 1.4459(7) 0.21752(18) 0.0738(12) Uani d . 1
H H7 0.4043 1.4631 0.1887 0.089 Uiso calc R 1
C C8 0.35392(15) 1.2585(6) 0.22009(17) 0.0716(11) Uani d . 1
H H8 0.3573 1.1494 0.1927 0.086 Uiso calc R 1
C C9 0.32088(13) 1.2331(6) 0.26342(16) 0.0590(10) Uani d . 1
H H9 0.3026 1.1059 0.2651 0.071 Uiso calc R 1
C C10 0.16263(13) 0.8050(5) 0.47986(15) 0.0541(9) Uani d . 1
H H10 0.1871 0.7060 0.4694 0.065 Uiso calc R 1
C C11 0.12193(13) 0.7405(5) 0.51476(14) 0.0460(8) Uani d . 1
C C12 0.08296(13) 0.8785(5) 0.53060(15) 0.0559(9) Uani d . 1
H H12 0.0829 1.0174 0.5179 0.067 Uiso calc R 1
C C13 0.04462(13) 0.8169(5) 0.56431(16) 0.0609(10) Uani d . 1
H H13 0.0183 0.9132 0.5724 0.073 Uiso calc R 1
C C14 0.04433(13) 0.6109(5) 0.58692(15) 0.0494(9) Uani d . 1
C C15 0.08271(13) 0.4715(5) 0.57031(15) 0.0538(9) Uani d . 1
H H15 0.0831 0.3326 0.5831 0.065 Uiso calc R 1
C C16 0.12001(12) 0.5361(5) 0.53532(15) 0.0550(9) Uani d . 1
H H16 0.1449 0.4387 0.5251 0.066 Uiso calc R 1
C C17 -0.03535(16) 0.6932(6) 0.6353(2) 0.0969(14) Uani d . 1
H H17A -0.0165 0.8159 0.6571 0.145 Uiso calc R 1
H H17B -0.0562 0.6252 0.6619 0.145 Uiso calc R 1
H H17C -0.0621 0.7322 0.5946 0.145 Uiso calc R 1
C C18 0.00342(15) 0.3390(6) 0.64213(19) 0.0848(13) Uani d . 1
H H18A -0.0176 0.2601 0.6049 0.127 Uiso calc R 1
H H18B -0.0169 0.3331 0.6750 0.127 Uiso calc R 1
H H18C 0.0417 0.2810 0.6589 0.127 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'
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 108.7(3) y
C14 N2 C18 121.9(3) ?
C14 N2 C17 121.5(3) ?
C18 N2 C17 115.6(3) ?
C1 O1 N1 113.5(2) y
O2 C1 O1 123.0(3) ?
O2 C1 C2 127.2(3) ?
O1 C1 C2 109.8(3) ?
C3 C2 C1 121.9(3) ?
C3 C2 H2 119.1 ?
C1 C2 H2 119.1 ?
C2 C3 C4 127.1(3) ?
C2 C3 H3 116.4 ?
C4 C3 H3 116.4 ?
C5 C4 C9 117.6(3) ?
C5 C4 C3 119.6(3) ?
C9 C4 C3 122.8(3) ?
C4 C5 C6 121.1(3) ?
C4 C5 H5 119.5 ?
C6 C5 H5 119.5 ?
C7 C6 C5 120.5(4) ?
C7 C6 H6 119.7 ?
C5 C6 H6 119.7 ?
C6 C7 C8 119.6(3) ?
C6 C7 H7 120.2 ?
C8 C7 H7 120.2 ?
C7 C8 C9 120.0(4) ?
C7 C8 H8 120.0 ?
C9 C8 H8 120.0 ?
C8 C9 C4 121.3(3) ?
C8 C9 H9 119.4 ?
C4 C9 H9 119.4 ?
N1 C10 C11 121.7(3) ?
N1 C10 H10 119.2 ?
C11 C10 H10 119.2 ?
C16 C11 C12 116.1(3) ?
C16 C11 C10 121.5(3) ?
C12 C11 C10 122.4(3) ?
C13 C12 C11 122.3(3) ?
C13 C12 H12 118.9 ?
C11 C12 H12 118.9 ?
C12 C13 C14 121.3(3) ?
C12 C13 H13 119.4 ?
C14 C13 H13 119.4 ?
N2 C14 C15 122.2(3) ?
N2 C14 C13 121.2(3) ?
C15 C14 C13 116.5(3) ?
C16 C15 C14 121.1(3) ?
C16 C15 H15 119.5 ?
C14 C15 H15 119.5 ?
C15 C16 C11 122.7(3) ?
C15 C16 H16 118.6 ?
C11 C16 H16 118.6 ?
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
N1 C10 1.266(4) y
N1 O1 1.453(3) y
N2 C14 1.373(4) ?
N2 C18 1.435(4) ?
N2 C17 1.448(4) ?
O1 C1 1.365(4) ?
O2 C1 1.202(4) ?
C1 C2 1.457(4) ?
C2 C3 1.322(4) ?
C2 H2 0.9300 ?
C3 C4 1.461(4) ?
C3 H3 0.9300 ?
C4 C5 1.386(4) ?
C4 C9 1.393(4) ?
C5 C6 1.387(4) ?
C5 H5 0.9300 ?
C6 C7 1.369(5) ?
C6 H6 0.9300 ?
C7 C8 1.381(5) ?
C7 H7 0.9300 ?
C8 C9 1.384(4) ?
C8 H8 0.9300 ?
C9 H9 0.9300 ?
C10 C11 1.441(4) ?
C10 H10 0.9300 ?
C11 C16 1.386(4) ?
C11 C12 1.392(4) ?
C12 C13 1.372(4) ?
C12 H12 0.9300 ?
C13 C14 1.406(4) ?
C13 H13 0.9300 ?
C14 C15 1.395(4) ?
C15 C16 1.377(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 4_545 0.93 3.12 3.961(5) 151.1
C10 H10 O1 7_566 0.93 3.14 3.737(5) 123.3
C10 H10 O2 1_545 0.93 2.46 3.275(5) 146.9
C16 H16 O2 1_545 0.93 2.78 3.530(4) 138.7
C17 H17C N1 5_576 0.96 3.01 3.817(5) 142.0
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 -178.2(3) y
N1 O1 C1 O2 7.3(5) y
N1 O1 C1 C2 -172.9(2) y
O2 C1 C2 C3 11.4(6) ?
O1 C1 C2 C3 -168.4(3) ?
C1 C2 C3 C4 -176.1(3) ?
C2 C3 C4 C5 -170.0(3) ?
C2 C3 C4 C9 12.0(5) ?
C9 C4 C5 C6 -0.8(5) ?
C3 C4 C5 C6 -178.8(3) ?
C4 C5 C6 C7 0.9(5) ?
C5 C6 C7 C8 -0.2(6) ?
C6 C7 C8 C9 -0.6(5) ?
C7 C8 C9 C4 0.7(5) ?
C5 C4 C9 C8 0.0(5) ?
C3 C4 C9 C8 178.0(3) ?
O1 N1 C10 C11 -178.0(3) ?
N1 C10 C11 C16 -177.4(3) ?
N1 C10 C11 C12 1.7(5) ?
C16 C11 C12 C13 -0.3(5) ?
C10 C11 C12 C13 -179.4(3) ?
C11 C12 C13 C14 2.5(5) ?
C18 N2 C14 C15 -5.8(5) ?
C17 N2 C14 C15 -174.1(3) ?
C18 N2 C14 C13 174.4(3) ?
C17 N2 C14 C13 6.0(5) ?
C12 C13 C14 N2 176.6(3) ?
C12 C13 C14 C15 -3.3(5) ?
N2 C14 C15 C16 -177.8(3) ?
C13 C14 C15 C16 2.0(5) ?
C14 C15 C16 C11 0.1(5) ?
C12 C11 C16 C15 -1.0(5) ?
C10 C11 C16 C15 178.1(3) ?
loop_
_cod_related_entry_id
_cod_related_entry_database
_cod_related_entry_code
1 ChemSpider 30655026
