#------------------------------------------------------------------------------
#$Date: 2011-09-10 04:16:28 +0100 (Sat, 10 Sep 2011) $
#$Revision: 25271 $
#$URL: svn://www.crystallography.net/cod/cif/2/2012946.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_2012946
loop_
_publ_author_name
'Okabe, Nobuo'
'Muranishi, Yasunori'
_publ_section_title
;
 8-Hydroxyquinaldinic acid and its nickel(II) complex
;
_journal_issue                   9
_journal_name_full               'Acta Crystallographica Section C'
_journal_page_first              m475
_journal_page_last               m477
_journal_volume                  58
_journal_year                    2002
_chemical_formula_moiety         'C10 H7 N O3'
_chemical_formula_sum            'C10 H7 N O3'
_chemical_formula_weight         189.17
_chemical_name_common            '8-Hydroxyquinaldinic acid'
_chemical_name_systematic
;
8-hydroxyquinolinium-2-carboxylate
;
_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'
_cell_angle_alpha                90
_cell_angle_beta                 90.680(10)
_cell_angle_gamma                90
_cell_formula_units_Z            8
_cell_length_a                   12.748(2)
_cell_length_b                   7.476(3)
_cell_length_c                   16.657(2)
_cell_measurement_reflns_used    16
_cell_measurement_temperature    296.2
_cell_measurement_theta_max      12.9
_cell_measurement_theta_min      10.2
_cell_volume                     1587.4(7)
_computing_cell_refinement       'MSC/AFC Diffractometer Control Software'
_computing_data_collection
;
MSC/AFC Diffractometer Control Software (Molecular Structure Corporation &
Rigaku Corporation, 1999)
;
_computing_data_reduction
'TEXSAN (Molecular Structure Corporation & Rigaku Corporation, 1999)'
_computing_molecular_graphics    'ORTEPII (Johnson, 1976)'
_computing_publication_material  TEXSAN
_computing_structure_refinement  'SHELXL97 (Sheldrick, 1997)'
_computing_structure_solution
'SIR97 (Altomare et al., 1999) and DIRDIF94 (Beurskens et al., 1994)'
_diffrn_measured_fraction_theta_full 1.000
_diffrn_measured_fraction_theta_max 1.000
_diffrn_measurement_device_type  'Rigaku AFC-5R'
_diffrn_measurement_method       \w/2\q
_diffrn_radiation_type           'Mo K\a'
_diffrn_radiation_wavelength     0.7107
_diffrn_reflns_av_R_equivalents  0.066
_diffrn_reflns_limit_h_max       16
_diffrn_reflns_limit_h_min       12
_diffrn_reflns_limit_k_max       9
_diffrn_reflns_limit_k_min       0
_diffrn_reflns_limit_l_max       21
_diffrn_reflns_limit_l_min       -21
_diffrn_reflns_number            2068
_diffrn_reflns_theta_full        27.5
_diffrn_reflns_theta_max         27.50
_diffrn_standards_decay_%        0.79
_diffrn_standards_interval_count 150
_diffrn_standards_number         3
_exptl_absorpt_coefficient_mu    0.119
_exptl_absorpt_correction_type   none
_exptl_crystal_colour            yellow
_exptl_crystal_density_diffrn    1.583
_exptl_crystal_density_meas      'not measured'
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       plate
_exptl_crystal_F_000             784.0
_exptl_crystal_size_max          0.20
_exptl_crystal_size_mid          0.10
_exptl_crystal_size_min          0.05
_refine_diff_density_max         0.28
_refine_diff_density_min         -0.27
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc^2^\l^3^/sin(2\q)]^-1/4^
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   0.870
_refine_ls_hydrogen_treatment    constr
_refine_ls_number_parameters     128
_refine_ls_number_reflns         1838
_refine_ls_R_factor_gt           0.053
_refine_ls_shift/su_max          <0.001
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'w = 1/[\s^2^(Fo^2^) + (0.1P)^2^] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_ref         0.197
_reflns_number_gt                691
_reflns_number_total             1838
_reflns_threshold_expression     I>2\s(I)
_[local]_cod_data_source_file    ob1077.cif
_[local]_cod_data_source_block   I
_[local]_cod_cif_authors_sg_H-M  'C 2/c'
_cod_original_cell_volume        1587.3(7)
_cod_database_code               2012946
loop_
_symmetry_equiv_pos_as_xyz
x,y,z
-x,y,1/2-z
-x,-y,-z
x,-y,1/2+z
1/2+x,1/2+y,z
1/2-x,1/2+y,1/2-z
1/2-x,1/2-y,-z
1/2+x,1/2-y,1/2+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
O1 0.3802(2) 0.1005(4) 0.7905(2) 0.0381(8) Uani d 1.00 O
O2 0.3821(3) -0.1027(4) 0.6906(2) 0.0443(9) Uani d 1.00 O
O3E 0.4069(3) 0.0399(4) 0.4296(2) 0.0347(8) Uani d 1.00 O
N1 0.3840(3) 0.1568(4) 0.5812(2) 0.0248(8) Uani d 1.00 N
C1 0.3718(3) 0.2025(5) 0.6578(2) 0.0268(9) Uani d 1.00 C
C2 0.3518(4) 0.3799(5) 0.6771(2) 0.0330(10) Uani d 1.00 C
C3 0.3478(4) 0.5061(5) 0.6176(2) 0.0350(10) Uani d 1.00 C
C4 0.3621(3) 0.4587(5) 0.5368(2) 0.0263(9) Uani d 1.00 C
C5 0.3606(3) 0.5821(6) 0.4732(2) 0.0340(10) Uani d 1.00 C
C6 0.3749(4) 0.5240(6) 0.3965(3) 0.0380(10) Uani d 1.00 C
C7 0.3908(4) 0.3418(6) 0.3786(2) 0.0350(10) Uani d 1.00 C
C8 0.3927(3) 0.2162(5) 0.4383(2) 0.0257(9) Uani d 1.00 C
C9 0.3799(3) 0.2773(5) 0.5195(2) 0.0230(9) Uani d 1.00 C
C10 0.3792(3) 0.0492(6) 0.7188(2) 0.0288(10) Uani d 1.00 C
H1 0.3950 0.0461 0.5700 0.0297 Uiso calc 1.00 H
H2 0.3412 0.4128 0.7302 0.0396 Uiso calc 1.00 H
H3 0.3355 0.6250 0.6308 0.0419 Uiso calc 1.00 H
H3E 0.4021 0.0136 0.3819 0.0521 Uiso calc 1.00 H
H5 0.3499 0.7030 0.4833 0.0409 Uiso calc 1.00 H
H6 0.3742 0.6069 0.3548 0.0454 Uiso calc 1.00 H
H7 0.4002 0.3066 0.3256 0.0416 Uiso calc 1.00 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
O1 0.061(2) 0.035(2) 0.0180(10) 0.006(2) 0.0020(10) 0.0040(10)
O2 0.075(3) 0.027(2) 0.031(2) -0.002(2) -0.003(2) -0.0010(10)
O3E 0.056(2) 0.030(2) 0.0180(10) 0.012(2) -0.0020(10) -0.0030(10)
N1 0.034(2) 0.020(2) 0.0200(10) 0.0000(10) -0.0020(10) -0.0050(10)
C1 0.032(2) 0.027(2) 0.022(2) 0.000(2) -0.002(2) 0.001(2)
C2 0.056(3) 0.024(2) 0.020(2) 0.002(2) -0.001(2) -0.002(2)
C3 0.050(3) 0.025(2) 0.030(2) 0.003(2) -0.002(2) -0.006(2)
C4 0.030(2) 0.025(2) 0.025(2) -0.001(2) -0.002(2) -0.004(2)
C5 0.046(3) 0.026(2) 0.030(2) 0.002(2) -0.003(2) 0.003(2)
C6 0.061(3) 0.032(3) 0.020(2) -0.002(2) -0.007(2) 0.006(2)
C7 0.050(3) 0.038(3) 0.016(2) 0.001(2) -0.002(2) -0.001(2)
C8 0.030(2) 0.026(2) 0.021(2) 0.004(2) -0.002(2) 0.000(2)
C9 0.026(2) 0.026(2) 0.016(2) -0.003(2) -0.003(2) 0.000(2)
C10 0.032(2) 0.033(3) 0.021(2) -0.002(2) 0.003(2) 0.004(2)
loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.003 0.002
;International Tables for Crystallography
(1992, Vol. C, Tables 4.2.6.8 and 6.1.1.4)
;
H H 0.000 0.000
;International Tables for Crystallography
(1992, Vol. C, Table 6.1.1.4)
;
O O 0.011 0.006
;International Tables for Crystallography
(1992, Vol. C, Tables 4.2.6.8 and 6.1.1.4)
;
N N 0.006 0.003
;International Tables for Crystallography
(1992, 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
C8 O3E H3E 109.5 no
C1 N1 C9 123.2(3) no
C1 N1 H1 118.4 no
C9 N1 H1 118.4 no
N1 C1 C2 119.3(3) no
N1 C1 C10 115.8(3) yes
C2 C1 C10 124.8(3) yes
C1 C2 C3 119.8(4) no
C1 C2 H2 120.1 no
C3 C2 H2 120.1 no
C2 C3 C4 121.0(4) no
C2 C3 H3 119.5 no
C4 C3 H3 119.5 no
C3 C4 C5 123.8(4) no
C3 C4 C9 117.6(3) no
C5 C4 C9 118.6(3) no
C4 C5 C6 119.8(4) no
C4 C5 H5 120.1 no
C6 C5 H5 120.1 no
C5 C6 C7 121.8(4) no
C5 C6 H6 119.1 no
C7 C6 H6 119.1 no
C6 C7 C8 120.8(4) no
C6 C7 H7 119.6 no
C8 C7 H7 119.6 no
O3E C8 C7 126.7(3) yes
O3E C8 C9 115.6(3) yes
C7 C8 C9 117.7(4) no
N1 C9 C4 119.1(3) no
N1 C9 C8 119.6(3) no
C4 C9 C8 121.3(3) no
O1 C10 O2 130.2(4) yes
O1 C10 C1 113.7(3) yes
O2 C10 C1 116.0(3) yes
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_publ_flag
O1 C10 1.255(4) yes
O2 C10 1.230(5) yes
O3E C8 1.338(5) yes
O3E H3E 0.820 no
N1 C1 1.332(4) yes
N1 C9 1.367(5) yes
N1 H1 0.860 no
C1 C2 1.388(6) yes
C1 C10 1.533(5) yes
C2 C3 1.369(6) yes
C2 H2 0.930 no
C3 C4 1.405(6) yes
C3 H3 0.930 no
C4 C5 1.405(6) yes
C4 C9 1.406(6) yes
C5 C6 1.364(6) yes
C5 H5 0.930 no
C6 C7 1.409(6) yes
C6 H6 0.930 no
C7 C8 1.368(6) yes
C7 H7 0.930 no
C8 C9 1.438(5) yes
loop_
_geom_contact_atom_site_label_1
_geom_contact_atom_site_label_2
_geom_contact_distance
_geom_contact_site_symmetry_2
O1 O3E 2.562(4) 4_555
O1 C10 3.098(5) 2_656
O1 C6 3.317(5) 4_565
O1 O1 3.354(6) 2_656
O1 C1 3.355(5) 2_656
O1 C3 3.375(5) 6_546
O1 O2 3.401(5) 2_656
O1 C8 3.418(5) 4_555
O1 C2 3.435(5) 6_546
O2 C3 3.195(5) 1_545
O2 O3E 3.404(4) 3_656
O2 C10 3.567(5) 2_656
O2 O2 3.580(7) 2_656
O3E N1 3.052(4) 3_656
O3E C3 3.349(5) 7_556
O3E O3E 3.371(6) 3_656
O3E C4 3.480(5) 7_556
O3E C5 3.549(5) 1_545
O3E C10 3.587(4) 4_554
N1 C7 3.574(6) 7_556
N1 C6 3.590(6) 7_556
C1 C7 3.411(6) 7_556
C3 C7 3.520(6) 3_666
C3 C6 3.552(7) 3_666
C4 C6 3.522(6) 3_666
C4 C8 3.530(6) 7_556
C4 C5 3.554(6) 3_666
C5 C9 3.472(6) 3_666
C8 C9 3.553(5) 7_556
C9 C9 3.391(7) 7_556
C10 C10 3.240(8) 2_656
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
N1 H1 O2 . 0.86 2.30 2.662(4) 105
N1 H1 O3E . 0.86 2.35 2.692(4) 104
O3E H3E O1 4_554 0.82 1.76 2.562(4) 164
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
O1 C10 C1 N1 171.7(4) no
O1 C10 C1 C2 -9.5(6) no
O2 C10 C1 N1 -9.0(5) no
O2 C10 C1 C2 169.8(4) no
O3E C8 C7 C6 179.9(4) no
O3E C8 C9 N1 0.8(5) no
O3E C8 C9 C4 -178.6(3) no
N1 C1 C2 C3 -1.8(6) no
N1 C9 C4 C3 -0.9(5) no
N1 C9 C4 C5 178.4(4) no
N1 C9 C8 C7 -178.3(4) no
C1 N1 C9 C4 0.1(5) no
C1 N1 C9 C8 -179.3(4) no
C1 C2 C3 C4 1.0(7) no
C2 C1 N1 C9 1.3(6) no
C2 C3 C4 C5 -178.9(4) no
C2 C3 C4 C9 0.4(6) no
C3 C2 C1 C10 179.5(4) no
C3 C4 C5 C6 -179.9(4) no
C3 C4 C9 C8 178.4(4) no
C4 C5 C6 C7 0.4(7) no
C4 C9 C8 C7 2.4(6) no
C5 C4 C9 C8 -2.2(6) no
C5 C6 C7 C8 -0.2(7) no
C6 C5 C4 C9 0.9(6) no
C6 C7 C8 C9 -1.1(6) no
C9 N1 C1 C10 -179.8(3) no
C9 N1 C1 C10 -179.8(3) no