#------------------------------------------------------------------------------
#$Date: 2011-09-10 05:16:28 +0200 (Sat, 10 Sep 2011) $
#$Revision: 25271 $
#$URL: svn://www.crystallography.net/cod/cif/2/2009024.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_2009024
loop_
_publ_author_name
'Ayg\"un, M.'
'I\,sik, \,S.'
'Turgut, Z.'
'\"Ozbey, S.'
'Kendi, E.'
_publ_section_title
;
 4-Ethoxy-<i>N</i>-(6-methylquinolin-2-ylmethylene)aniline
;
_journal_issue                   10
_journal_name_full               'Acta Crystallographica Section C'
_journal_page_first              1689
_journal_page_last               1690
_journal_volume                  55
_journal_year                    1999
_chemical_formula_sum            'C19 H18 N2 O'
_chemical_formula_weight         290.35
_chemical_name_systematic
;
 ?
;
_space_group_IT_number           2
_symmetry_cell_setting           triclinic
_symmetry_space_group_name_Hall  '-P 1'
_symmetry_space_group_name_H-M   'P -1'
_audit_creation_method           SHELXL
_cell_angle_alpha                85.969(11)
_cell_angle_beta                 74.899(8)
_cell_angle_gamma                78.473(12)
_cell_formula_units_Z            2
_cell_length_a                   7.4127(8)
_cell_length_b                   10.1982(17)
_cell_length_c                   10.8971(11)
_cell_measurement_reflns_used    25
_cell_measurement_temperature    293(2)
_cell_measurement_theta_max      18.64
_cell_measurement_theta_min      11.12
_cell_volume                     779.15(18)
_computing_cell_refinement       'CAD-4 Express'
_computing_data_collection       'CAD-4 Express (Enraf-Nonius, 1993)'
_computing_data_reduction        'MolEN (Fair, 1990)'
_computing_molecular_graphics
'ORTEPIII (Burnett & Johnson, 1996) and PLUTON (Spek, 1997)'
_computing_publication_material  SHELXL97
_computing_structure_refinement  'SHELXL97 (Sheldrick, 1997a)'
_computing_structure_solution    'SHELXS97 (Sheldrick, 1997b)'
_diffrn_ambient_temperature      293(2)
_diffrn_measured_fraction_theta_full 0.875
_diffrn_measured_fraction_theta_max 0.875
_diffrn_measurement_device_type  'Enraf-Nonius CAD-4'
_diffrn_measurement_method       '\w/2\q scans'
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_source         'fine-focus sealed tube'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71070
_diffrn_reflns_av_R_equivalents  0.0000
_diffrn_reflns_av_sigmaI/netI    0.0245
_diffrn_reflns_limit_h_max       9
_diffrn_reflns_limit_h_min       0
_diffrn_reflns_limit_k_max       12
_diffrn_reflns_limit_k_min       -12
_diffrn_reflns_limit_l_max       13
_diffrn_reflns_limit_l_min       -12
_diffrn_reflns_number            2769
_diffrn_reflns_theta_full        26.29
_diffrn_reflns_theta_max         26.29
_diffrn_reflns_theta_min         2.84
_diffrn_standards_decay_%        0.3
_diffrn_standards_interval_time  120
_diffrn_standards_number         3
_exptl_absorpt_coefficient_mu    0.077
_exptl_absorpt_correction_type   none
_exptl_crystal_colour            'pale yellow'
_exptl_crystal_density_diffrn    1.238
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       prismatic
_exptl_crystal_F_000             308
_exptl_crystal_size_max          0.48
_exptl_crystal_size_mid          0.48
_exptl_crystal_size_min          0.30
_refine_diff_density_max         0.188
_refine_diff_density_min         -0.172
_refine_ls_extinction_coef       0.010(2)
_refine_ls_extinction_method     'SHELXL97 (Sheldrick, 1997a)'
_refine_ls_goodness_of_fit_ref   0.933
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     272
_refine_ls_number_reflns         2769
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      0.933
_refine_ls_R_factor_all          0.0717
_refine_ls_R_factor_gt           0.0455
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_scheme
'calc w = 1/[\s^2^(Fo^2^)+(0.0436P)^2^+0.3468P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_wR_factor_ref         0.1158
_reflns_number_gt                1919
_reflns_number_total             2769
_reflns_threshold_expression     I>2\s(I)
_[local]_cod_data_source_file    fr1194.cif
_[local]_cod_data_source_block   mav
_[local]_cod_cif_authors_sg_H-M  P-1
_cod_original_cell_volume        779.15(17)
_cod_database_code               2009024
loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'-x, -y, -z'
loop_
_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_occupancy
_atom_site_type_symbol
N1 0.5617(2) 0.19430(16) 0.10009(15) 0.0494(4) Uani d 1 N
N2 1.0285(2) 0.23764(15) -0.05529(14) 0.0440(4) Uani d 1 N
O1 0.15643(19) -0.15383(14) 0.42265(13) 0.0569(4) Uani d 1 O
C1 -0.0782(5) -0.2880(4) 0.4895(3) 0.0853(9) Uani d 1 C
C2 -0.0088(4) -0.1856(3) 0.3958(2) 0.0643(6) Uani d 1 C
C3 0.2494(3) -0.06744(19) 0.34022(18) 0.0464(5) Uani d 1 C
C4 0.1900(3) -0.0024(2) 0.2387(2) 0.0547(6) Uani d 1 C
C5 0.2945(3) 0.0834(2) 0.1613(2) 0.0543(5) Uani d 1 C
C6 0.4643(3) 0.10284(19) 0.18183(18) 0.0450(5) Uani d 1 C
C7 0.5232(3) 0.0374(2) 0.28462(19) 0.0482(5) Uani d 1 C
C8 0.4172(3) -0.0459(2) 0.36380(19) 0.0488(5) Uani d 1 C
C9 0.7416(3) 0.1705(2) 0.06105(18) 0.0474(5) Uani d 1 C
C10 0.8404(2) 0.26968(19) -0.01819(17) 0.0432(4) Uani d 1 C
C11 0.7361(3) 0.3921(2) -0.0506(2) 0.0534(5) Uani d 1 C
C12 0.8271(3) 0.4846(2) -0.1203(2) 0.0553(5) Uani d 1 C
C13 1.0280(3) 0.45639(19) -0.16249(17) 0.0458(5) Uani d 1 C
C14 1.1355(3) 0.5467(2) -0.2371(2) 0.0551(5) Uani d 1 C
C15 1.3291(3) 0.5137(2) -0.27881(19) 0.0573(6) Uani d 1 C
C16 1.4202(3) 0.3880(2) -0.2441(2) 0.0604(6) Uani d 1 C
C17 1.3233(3) 0.2986(2) -0.1698(2) 0.0527(5) Uani d 1 C
C18 1.1224(2) 0.33057(18) -0.12776(17) 0.0426(4) Uani d 1 C
C19 1.4439(6) 0.6101(4) -0.3588(3) 0.0835(9) Uani d 1 C
H1A 0.021(4) -0.366(3) 0.484(3) 0.101(11) Uiso d 1 H
H1B -0.108(4) -0.259(3) 0.577(3) 0.112(11) Uiso d 1 H
H1C -0.183(5) -0.315(3) 0.475(3) 0.133(12) Uiso d 1 H
H2A -0.109(4) -0.097(3) 0.398(2) 0.084(8) Uiso d 1 H
H2B 0.031(3) -0.216(3) 0.305(3) 0.095(9) Uiso d 1 H
H4 0.081(3) -0.019(2) 0.220(2) 0.067(6) Uiso d 1 H
H5 0.249(3) 0.131(2) 0.088(2) 0.064(6) Uiso d 1 H
H7 0.635(3) 0.057(2) 0.305(2) 0.071(7) Uiso d 1 H
H8 0.454(3) -0.0922(19) 0.4375(18) 0.051(5) Uiso d 1 H
H9 0.818(3) 0.083(2) 0.0807(19) 0.060(6) Uiso d 1 H
H11 0.602(4) 0.402(2) -0.017(2) 0.085(8) Uiso d 1 H
H12 0.759(3) 0.572(2) -0.1419(19) 0.062(6) Uiso d 1 H
H14 1.066(3) 0.637(2) -0.2612(19) 0.063(6) Uiso d 1 H
H16 1.552(4) 0.362(2) -0.276(2) 0.083(8) Uiso d 1 H
H17 1.386(3) 0.207(2) -0.1437(19) 0.064(6) Uiso d 1 H
H19A 1.531(4) 0.572(3) -0.426(3) 0.116(11) Uiso d 1 H
H19B 1.497(4) 0.649(3) -0.308(3) 0.112(11) Uiso d 1 H
H19C 1.363(6) 0.688(4) -0.392(4) 0.175(19) Uiso d 1 H
loop_
_atom_site_aniso_label
_atom_site_aniso_U_11
_atom_site_aniso_U_22
_atom_site_aniso_U_33
_atom_site_aniso_U_12
_atom_site_aniso_U_13
_atom_site_aniso_U_23
N1 0.0396(9) 0.0546(10) 0.0541(10) -0.0119(8) -0.0107(7) 0.0026(8)
N2 0.0367(8) 0.0497(10) 0.0453(9) -0.0062(7) -0.0104(7) -0.0029(7)
O1 0.0528(8) 0.0666(9) 0.0586(9) -0.0266(7) -0.0182(7) 0.0103(7)
C1 0.085(2) 0.095(2) 0.086(2) -0.051(2) -0.0200(17) 0.0199(18)
C2 0.0561(14) 0.0833(18) 0.0628(15) -0.0348(13) -0.0159(11) 0.0034(13)
C3 0.0435(10) 0.0489(11) 0.0473(11) -0.0138(9) -0.0085(8) -0.0014(9)
C4 0.0419(11) 0.0736(15) 0.0557(12) -0.0219(11) -0.0184(10) 0.0068(11)
C5 0.0455(11) 0.0689(14) 0.0522(12) -0.0160(10) -0.0184(9) 0.0112(11)
C6 0.0392(10) 0.0472(11) 0.0480(11) -0.0099(8) -0.0093(8) 0.0005(9)
C7 0.0402(10) 0.0532(12) 0.0565(12) -0.0139(9) -0.0175(9) -0.0008(10)
C8 0.0494(11) 0.0532(12) 0.0495(11) -0.0151(9) -0.0197(9) 0.0037(10)
C9 0.0435(11) 0.0498(12) 0.0484(11) -0.0079(9) -0.0118(9) -0.0001(9)
C10 0.0384(10) 0.0479(11) 0.0442(10) -0.0083(8) -0.0119(8) -0.0015(9)
C11 0.0377(11) 0.0536(13) 0.0683(13) -0.0071(10) -0.0144(10) 0.0026(11)
C12 0.0482(12) 0.0495(13) 0.0689(14) -0.0041(10) -0.0218(10) 0.0059(11)
C13 0.0479(11) 0.0496(12) 0.0448(10) -0.0132(9) -0.0169(8) -0.0020(9)
C14 0.0665(14) 0.0503(13) 0.0540(12) -0.0204(11) -0.0189(10) 0.0015(10)
C15 0.0629(14) 0.0655(15) 0.0494(12) -0.0319(12) -0.0072(10) -0.0104(10)
C16 0.0455(12) 0.0729(16) 0.0621(14) -0.0203(12) -0.0023(10) -0.0129(12)
C17 0.0404(11) 0.0585(13) 0.0568(12) -0.0086(10) -0.0070(9) -0.0061(10)
C18 0.0414(10) 0.0467(11) 0.0415(10) -0.0110(9) -0.0109(8) -0.0045(8)
C19 0.102(2) 0.087(2) 0.0672(18) -0.059(2) 0.0006(17) -0.0087(16)
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'
O O 0.0106 0.0060 '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'
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
C9 N1 C6 121.10(17) yes
C10 N2 C18 117.19(16) yes
C3 O1 C2 117.10(16) yes
O1 C2 C1 108.5(2) yes
O1 C3 C4 125.14(17) yes
O1 C3 C8 115.71(17) ?
C4 C3 C8 119.15(18) ?
C3 C4 C5 120.49(19) ?
C4 C5 C6 120.83(19) ?
C7 C6 C5 118.40(17) ?
C7 C6 N1 123.90(17) yes
C5 C6 N1 117.60(17) ?
C8 C7 C6 120.98(18) ?
C7 C8 C3 120.11(19) ?
N1 C9 C10 120.21(19) yes
N2 C10 C11 123.15(17) ?
N2 C10 C9 116.73(17) ?
C11 C10 C9 120.12(17) ?
C12 C11 C10 120.10(19) ?
C11 C12 C13 119.4(2) ?
C18 C13 C14 119.42(19) ?
C18 C13 C12 117.19(17) ?
C14 C13 C12 123.39(19) yes
C15 C14 C13 121.4(2) ?
C14 C15 C16 118.3(2) ?
C14 C15 C19 121.4(3) ?
C16 C15 C19 120.3(3) ?
C17 C16 C15 122.5(2) ?
C16 C17 C18 119.7(2) ?
N2 C18 C13 122.97(16) ?
N2 C18 C17 118.45(18) yes
C13 C18 C17 118.57(17) ?
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_publ_flag
N1 C9 1.268(2) yes
N1 C6 1.415(2) yes
N2 C10 1.326(2) yes
N2 C18 1.371(2) yes
O1 C3 1.366(2) yes
O1 C2 1.431(2) yes
C1 C2 1.479(4) yes
C3 C4 1.376(3) ?
C3 C8 1.395(3) ?
C4 C5 1.380(3) ?
C5 C6 1.387(3) ?
C6 C7 1.387(3) ?
C7 C8 1.376(3) ?
C9 C10 1.466(3) yes
C10 C11 1.405(3) ?
C11 C12 1.345(3) ?
C12 C13 1.415(3) ?
C13 C18 1.411(3) ?
C13 C14 1.412(3) ?
C14 C15 1.367(3) ?
C15 C16 1.400(3) ?
C15 C19 1.509(3) ?
C16 C17 1.363(3) ?
C17 C18 1.416(3) ?