#------------------------------------------------------------------------------
#$Date: 2011-09-10 06:16:28 +0300 (Sat, 10 Sep 2011) $
#$Revision: 25271 $
#$URL: file:///home/coder/svn-repositories/cod/cif/2/2300127.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_2300127
loop_
_publ_author_name
'Zeng, He-Ping'
'Wang, Ting-Ting'
'Xu, Dan-Feng'
'Cai, Yue-Peng'
'Chen, Dong-Feng'
_publ_section_title
;
 Synthesis, crystal structure and biological activity of
 2-[2-(quinolin-2-yl)vinyl]-8-hydroxyquinoline and
 2-[2-(quinolin-4-yl)vinyl]-8-hydroxyquinoline
;
_journal_coeditor_code           KK5009
_journal_issue                   3
_journal_name_full               'Journal of Applied Crystallography'
_journal_page_first              471
_journal_page_last               475
_journal_volume                  40
_journal_year                    2007
_chemical_formula_moiety         'C20 H14 N2 O'
_chemical_formula_sum            'C20 H14 N2 O'
_chemical_formula_weight         298.33
_chemical_name_systematic
;
 ?
;
_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                 102.039(4)
_cell_angle_gamma                90.00
_cell_formula_units_Z            4
_cell_length_a                   10.7240(6)
_cell_length_b                   8.9019(5)
_cell_length_c                   16.1894(8)
_cell_measurement_reflns_used    2512
_cell_measurement_temperature    298(2)
_cell_measurement_theta_max      25.13
_cell_measurement_theta_min      2.54
_cell_volume                     1511.51(14)
_computing_cell_refinement       'Bruker SMART'
_computing_data_collection       'Bruker SMART'
_computing_data_reduction        'Bruker SAINT'
_computing_molecular_graphics    'Bruker SHELXTL'
_computing_publication_material  'Bruker SHELXTL'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 1990)'
_diffrn_ambient_temperature      298(2)
_diffrn_measured_fraction_theta_full 0.990
_diffrn_measured_fraction_theta_max 0.990
_diffrn_measurement_device_type  'CCD area detector'
_diffrn_measurement_method       'phi and omega scans'
_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  0.0332
_diffrn_reflns_av_sigmaI/netI    0.0295
_diffrn_reflns_limit_h_max       13
_diffrn_reflns_limit_h_min       -10
_diffrn_reflns_limit_k_max       10
_diffrn_reflns_limit_k_min       -11
_diffrn_reflns_limit_l_max       20
_diffrn_reflns_limit_l_min       -21
_diffrn_reflns_number            13247
_diffrn_reflns_theta_full        27.56
_diffrn_reflns_theta_max         27.56
_diffrn_reflns_theta_min         2.09
_exptl_absorpt_coefficient_mu    0.082
_exptl_absorpt_correction_T_max  0.9798
_exptl_absorpt_correction_T_min  0.9774
_exptl_absorpt_correction_type   none
_exptl_crystal_colour            yellow
_exptl_crystal_density_diffrn    1.311
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       block
_exptl_crystal_F_000             624
_exptl_crystal_size_max          0.32
_exptl_crystal_size_mid          0.29
_exptl_crystal_size_min          0.28
_refine_diff_density_max         0.118
_refine_diff_density_min         -0.188
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.050
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     209
_refine_ls_number_reflns         3460
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.050
_refine_ls_R_factor_all          0.0688
_refine_ls_R_factor_gt           0.0430
_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/[\s^2^(Fo^2^)+(0.0526P)^2^+0.1209P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1012
_refine_ls_wR_factor_ref         0.1163
_reflns_number_gt                2376
_reflns_number_total             3460
_reflns_threshold_expression     >2sigma(I)
_[local]_cod_data_source_file    kk5009.cif
_[local]_cod_data_source_block   3b
_[local]_cod_cif_authors_sg_H-M  P2(1)/n
_[local]_cod_cif_authors_sg_Hall -P2yn
_cod_depositor_comments
;
The following automatic conversions were performed:

'_symmetry_cell_setting' value 'Monoclinic' changed to 'monoclinic'
according to /home/saulius/struct/CIF-dictionaries/cif_core.dic
dictionary named 'cif_core.dic' version 2.4.1 from 2010-06-29.

Automatic conversion script
Id: cif_fix_values 1715 2011-07-08 13:25:40Z adriana 
;
_cod_database_code               2300127
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
O O1 0.28263(10) 0.49707(12) 0.16643(7) 0.0578(3) Uani d . 1
H H1 0.3032 0.5676 0.1396 0.087 Uiso calc R 1
N N1 0.50709(11) 0.55344(13) 0.11577(7) 0.0430(3) Uani d . 1
N N2 0.74000(12) 1.22073(14) -0.08230(7) 0.0502(3) Uani d . 1
C C1 0.49795(13) 0.42565(15) 0.16041(8) 0.0417(3) Uani d . 1
C C2 0.38159(14) 0.40009(16) 0.18676(9) 0.0464(3) Uani d . 1
C C3 0.36949(16) 0.27616(18) 0.23504(9) 0.0558(4) Uani d . 1
H H3 0.2938 0.2600 0.2531 0.067 Uiso calc R 1
C C4 0.46986(18) 0.17414(18) 0.25717(10) 0.0608(4) Uani d . 1
H H4 0.4600 0.0912 0.2901 0.073 Uiso calc R 1
C C5 0.58216(17) 0.19378(17) 0.23135(9) 0.0568(4) Uani d . 1
H H5 0.6474 0.1238 0.2459 0.068 Uiso calc R 1
C C6 0.59899(14) 0.32088(15) 0.18237(9) 0.0464(3) Uani d . 1
C C7 0.71088(15) 0.35195(17) 0.15318(10) 0.0538(4) Uani d . 1
H H7 0.7789 0.2850 0.1642 0.065 Uiso calc R 1
C C8 0.71976(14) 0.47981(16) 0.10877(10) 0.0513(4) Uani d . 1
H H8 0.7937 0.5004 0.0894 0.062 Uiso calc R 1
C C9 0.61637(13) 0.58097(15) 0.09222(9) 0.0431(3) Uani d . 1
C C10 0.62348(14) 0.72455(16) 0.04910(9) 0.0465(3) Uani d . 1
H H10 0.5472 0.7652 0.0196 0.056 Uiso calc R 1
C C11 0.72883(14) 0.80146(15) 0.04840(9) 0.0463(3) Uani d . 1
H H11 0.8056 0.7607 0.0771 0.056 Uiso calc R 1
C C12 0.73372(13) 0.94639(15) 0.00569(8) 0.0421(3) Uani d . 1
C C13 0.64171(15) 0.98503(17) -0.06289(10) 0.0510(4) Uani d . 1
H H13 0.5743 0.9198 -0.0823 0.061 Uiso calc R 1
C C14 0.64829(15) 1.12191(18) -0.10403(10) 0.0541(4) Uani d . 1
H H14 0.5832 1.1445 -0.1500 0.065 Uiso calc R 1
C C15 0.83499(13) 1.18596(15) -0.01465(9) 0.0431(3) Uani d . 1
C C16 0.93575(15) 1.28937(16) 0.00899(10) 0.0519(4) Uani d . 1
H H16 0.9369 1.3767 -0.0224 0.062 Uiso calc R 1
C C17 1.03098(15) 1.26297(18) 0.07688(11) 0.0589(4) Uani d . 1
H H17 1.0966 1.3323 0.0919 0.071 Uiso calc R 1
C C18 1.03080(15) 1.13168(19) 0.12437(11) 0.0598(4) Uani d . 1
H H18 1.0961 1.1149 0.1712 0.072 Uiso calc R 1
C C19 0.93615(14) 1.02835(17) 0.10280(10) 0.0511(4) Uani d . 1
H H19 0.9378 0.9416 0.1350 0.061 Uiso calc R 1
C C20 0.83558(12) 1.05068(14) 0.03233(8) 0.0405(3) Uani d . 1
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
O1 0.0494(6) 0.0559(6) 0.0713(7) -0.0055(5) 0.0198(5) 0.0106(5)
N1 0.0423(6) 0.0407(6) 0.0451(6) -0.0055(5) 0.0074(5) 0.0011(5)
N2 0.0531(7) 0.0470(7) 0.0514(7) -0.0005(6) 0.0127(6) 0.0067(6)
C1 0.0478(8) 0.0376(7) 0.0379(7) -0.0084(6) 0.0049(6) -0.0026(6)
C2 0.0509(9) 0.0445(8) 0.0429(7) -0.0106(7) 0.0080(6) -0.0026(6)
C3 0.0658(10) 0.0547(9) 0.0477(8) -0.0169(8) 0.0140(8) 0.0011(7)
C4 0.0851(12) 0.0464(9) 0.0479(9) -0.0158(9) 0.0070(9) 0.0066(7)
C5 0.0707(11) 0.0432(8) 0.0503(9) -0.0018(8) -0.0016(8) 0.0044(7)
C6 0.0539(9) 0.0393(7) 0.0428(7) -0.0044(7) 0.0025(6) -0.0031(6)
C7 0.0527(9) 0.0419(8) 0.0645(10) 0.0047(7) 0.0066(8) -0.0041(7)
C8 0.0459(8) 0.0449(8) 0.0652(10) -0.0020(7) 0.0167(7) -0.0059(7)
C9 0.0453(8) 0.0391(7) 0.0446(7) -0.0062(6) 0.0086(6) -0.0029(6)
C10 0.0457(8) 0.0433(8) 0.0513(8) -0.0005(6) 0.0119(7) 0.0021(6)
C11 0.0458(8) 0.0424(8) 0.0508(8) -0.0035(6) 0.0102(7) 0.0018(6)
C12 0.0430(8) 0.0403(7) 0.0451(7) -0.0019(6) 0.0143(6) -0.0015(6)
C13 0.0503(8) 0.0510(9) 0.0503(8) -0.0096(7) 0.0074(7) 0.0016(7)
C14 0.0542(9) 0.0564(9) 0.0488(8) -0.0016(8) 0.0041(7) 0.0064(7)
C15 0.0428(8) 0.0397(7) 0.0496(8) 0.0015(6) 0.0157(6) -0.0001(6)
C16 0.0529(9) 0.0399(8) 0.0664(10) -0.0045(7) 0.0202(8) 0.0030(7)
C17 0.0494(9) 0.0481(9) 0.0788(11) -0.0121(7) 0.0124(8) -0.0031(8)
C18 0.0493(9) 0.0572(10) 0.0674(10) -0.0059(8) -0.0004(8) 0.0012(8)
C19 0.0476(8) 0.0465(8) 0.0577(9) -0.0020(7) 0.0075(7) 0.0052(7)
C20 0.0400(7) 0.0373(7) 0.0462(8) -0.0004(6) 0.0133(6) -0.0015(6)
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 0.0000 '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 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0106 0.0000 '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
C2 O1 H1 109.5
C9 N1 C1 118.14(12)
C14 N2 C15 117.06(12)
N1 C1 C6 123.14(13)
N1 C1 C2 117.29(13)
C6 C1 C2 119.55(13)
O1 C2 C3 119.20(14)
O1 C2 C1 121.23(12)
C3 C2 C1 119.56(14)
C2 C3 C4 120.59(15)
C2 C3 H3 119.7
C4 C3 H3 119.7
C5 C4 C3 121.31(15)
C5 C4 H4 119.3
C3 C4 H4 119.3
C4 C5 C6 119.84(15)
C4 C5 H5 120.1
C6 C5 H5 120.1
C7 C6 C5 124.30(15)
C7 C6 C1 116.59(13)
C5 C6 C1 119.12(14)
C8 C7 C6 120.08(14)
C8 C7 H7 120.0
C6 C7 H7 120.0
C7 C8 C9 119.73(14)
C7 C8 H8 120.1
C9 C8 H8 120.1
N1 C9 C8 122.23(13)
N1 C9 C10 115.73(12)
C8 C9 C10 122.03(13)
C11 C10 C9 125.77(14)
C11 C10 H10 117.1
C9 C10 H10 117.1
C10 C11 C12 124.92(14)
C10 C11 H11 117.5
C12 C11 H11 117.5
C13 C12 C20 117.28(12)
C13 C12 C11 120.83(13)
C20 C12 C11 121.87(12)
C12 C13 C14 120.47(14)
C12 C13 H13 119.8
C14 C13 H13 119.8
N2 C14 C13 124.50(14)
N2 C14 H14 117.7
C13 C14 H14 117.7
N2 C15 C16 118.06(13)
N2 C15 C20 122.63(12)
C16 C15 C20 119.30(13)
C17 C16 C15 120.78(14)
C17 C16 H16 119.6
C15 C16 H16 119.6
C16 C17 C18 120.21(14)
C16 C17 H17 119.9
C18 C17 H17 119.9
C19 C18 C17 120.68(15)
C19 C18 H18 119.7
C17 C18 H18 119.7
C18 C19 C20 121.05(14)
C18 C19 H19 119.5
C20 C19 H19 119.5
C19 C20 C15 117.94(12)
C19 C20 C12 124.01(12)
C15 C20 C12 118.04(12)
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
O1 C2 1.3543(18)
O1 H1 0.8200
N1 C9 1.3286(18)
N1 C1 1.3621(17)
N2 C14 1.3117(19)
N2 C15 1.3667(18)
C1 C6 1.418(2)
C1 C2 1.419(2)
C2 C3 1.374(2)
C3 C4 1.397(2)
C3 H3 0.9300
C4 C5 1.366(2)
C4 H4 0.9300
C5 C6 1.415(2)
C5 H5 0.9300
C6 C7 1.406(2)
C7 C8 1.360(2)
C7 H7 0.9300
C8 C9 1.410(2)
C8 H8 0.9300
C9 C10 1.4660(19)
C10 C11 1.323(2)
C10 H10 0.9300
C11 C12 1.4699(19)
C11 H11 0.9300
C12 C13 1.367(2)
C12 C20 1.4299(19)
C13 C14 1.397(2)
C13 H13 0.9300
C14 H14 0.9300
C15 C16 1.410(2)
C15 C20 1.4236(19)
C16 C17 1.356(2)
C16 H16 0.9300
C17 C18 1.399(2)
C17 H17 0.9300
C18 C19 1.360(2)
C18 H18 0.9300
C19 C20 1.411(2)
C19 H19 0.9300
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
O1 H1 N2 3_675 0.82 2.11 2.8438(15) 149.2
O1 H1 N1 1_555 0.82 2.301 2.7463(16) 114.63
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
C9 N1 C1 C6 -0.34(19)
C9 N1 C1 C2 178.49(12)
N1 C1 C2 O1 1.63(19)
C6 C1 C2 O1 -179.49(12)
N1 C1 C2 C3 -177.22(12)
C6 C1 C2 C3 1.7(2)
O1 C2 C3 C4 -179.91(13)
C1 C2 C3 C4 -1.0(2)
C2 C3 C4 C5 -0.3(2)
C3 C4 C5 C6 1.1(2)
C4 C5 C6 C7 179.56(14)
C4 C5 C6 C1 -0.4(2)
N1 C1 C6 C7 -2.10(19)
C2 C1 C6 C7 179.09(13)
N1 C1 C6 C5 177.87(12)
C2 C1 C6 C5 -0.93(19)
C5 C6 C7 C8 -177.81(14)
C1 C6 C7 C8 2.2(2)
C6 C7 C8 C9 0.0(2)
C1 N1 C9 C8 2.76(19)
C1 N1 C9 C10 -176.27(12)
C7 C8 C9 N1 -2.7(2)
C7 C8 C9 C10 176.30(14)
N1 C9 C10 C11 152.78(15)
C8 C9 C10 C11 -26.2(2)
C9 C10 C11 C12 -179.12(13)
C10 C11 C12 C13 -26.6(2)
C10 C11 C12 C20 155.01(14)
C20 C12 C13 C14 -0.4(2)
C11 C12 C13 C14 -178.87(13)
C15 N2 C14 C13 0.0(2)
C12 C13 C14 N2 0.9(2)
C14 N2 C15 C16 178.94(14)
C14 N2 C15 C20 -1.2(2)
N2 C15 C16 C17 178.27(14)
C20 C15 C16 C17 -1.6(2)
C15 C16 C17 C18 0.3(2)
C16 C17 C18 C19 0.6(3)
C17 C18 C19 C20 -0.2(3)
C18 C19 C20 C15 -1.1(2)
C18 C19 C20 C12 179.48(14)
N2 C15 C20 C19 -177.91(13)
C16 C15 C20 C19 1.95(19)
N2 C15 C20 C12 1.56(19)
C16 C15 C20 C12 -178.57(13)
C13 C12 C20 C19 178.75(13)
C11 C12 C20 C19 -2.8(2)
C13 C12 C20 C15 -0.69(19)
C11 C12 C20 C15 177.74(12)