#------------------------------------------------------------------------------
#$Date: 2013-01-18 12:43:08 +0200 (Fri, 18 Jan 2013) $
#$Revision: 71116 $
#$URL: file:///home/coder/svn-repositories/cod/cif/2/01/87/2018706.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_2018706
loop_
_publ_author_name
'Vranec, Peter'
'Poto\<c\<n\'ak, Ivan'
'Repovsk\'y, Peter'
_publ_section_title
;
 Low-dimensional compounds containing bioactive ligands. IV. Unusual ionic
 forms of 5-chloroquinolin-8-ol
;
_journal_coeditor_code           FG3281
_journal_issue                   12
_journal_name_full               'Acta Crystallographica Section C'
_journal_page_first              m370
_journal_page_last               m376
_journal_volume                  68
_journal_year                    2012
_chemical_formula_moiety         'C9 H7 Cl N O, Cl'
_chemical_formula_sum            'C9 H7 Cl2 N O'
_chemical_formula_weight         216.06
_chemical_name_systematic
;
5-chloro-8-hydroxyquinolinium chloride
;
_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           SHELXL-97
_cell_angle_alpha                72.400(5)
_cell_angle_beta                 76.797(5)
_cell_angle_gamma                84.615(5)
_cell_formula_units_Z            2
_cell_length_a                   7.3980(4)
_cell_length_b                   7.6612(5)
_cell_length_c                   8.4536(4)
_cell_measurement_reflns_used    2895
_cell_measurement_temperature    183(2)
_cell_measurement_theta_max      29.1715
_cell_measurement_theta_min      3.2017
_cell_volume                     444.47(5)
_computing_cell_refinement       'CrysAlis RED (Oxford Diffraction, 2007)'
_computing_data_collection       'CrysAlis CCD (Oxford Diffraction, 2007)'
_computing_data_reduction        'CrysAlis RED (Oxford Diffraction, 2007)'
_computing_molecular_graphics    'DIAMOND (Brandenburg, 2001)'
_computing_publication_material  'SHELXL97 (Sheldrick, 2008)'
_computing_structure_refinement  'SHELXL97 (Sheldrick, 2008)'
_computing_structure_solution    'SHELXS97 (Sheldrick, 2008)'
_diffrn_ambient_temperature      183(2)
_diffrn_detector_area_resol_mean 8.3438
_diffrn_measured_fraction_theta_full 0.996
_diffrn_measured_fraction_theta_max 0.996
_diffrn_measurement_device_type
'Oxford Diffraction Xcalibur (Sapphire2, large Be window)'
_diffrn_measurement_method       '\w 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  0.0232
_diffrn_reflns_av_sigmaI/netI    0.0293
_diffrn_reflns_limit_h_max       9
_diffrn_reflns_limit_h_min       -9
_diffrn_reflns_limit_k_max       9
_diffrn_reflns_limit_k_min       -9
_diffrn_reflns_limit_l_max       10
_diffrn_reflns_limit_l_min       -10
_diffrn_reflns_number            5950
_diffrn_reflns_theta_full        26.49
_diffrn_reflns_theta_max         26.49
_diffrn_reflns_theta_min         3.21
_exptl_absorpt_coefficient_mu    0.682
_exptl_absorpt_correction_T_max  0.935
_exptl_absorpt_correction_T_min  0.775
_exptl_absorpt_correction_type   analytical
_exptl_absorpt_process_details
;
[CrysAlis PRO (Oxford Diffraction, 2007), based on expressions derived
by
Clark & Reid (1995)]
;
_exptl_crystal_colour            'light yellow'
_exptl_crystal_density_diffrn    1.614
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       plate
_exptl_crystal_F_000             220
_exptl_crystal_size_max          0.6388
_exptl_crystal_size_mid          0.4170
_exptl_crystal_size_min          0.1161
_refine_diff_density_max         0.281
_refine_diff_density_min         -0.197
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   0.943
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     126
_refine_ls_number_reflns         1836
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      0.943
_refine_ls_R_factor_all          0.0406
_refine_ls_R_factor_gt           0.0288
_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^)+(0.0338P)^2^+0.2637P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0674
_refine_ls_wR_factor_ref         0.0734
_reflns_number_gt                1508
_reflns_number_total             1836
_reflns_threshold_expression     I>2sigma(I)
_iucr_refine_instructions_details
;
TITL IV
CELL  0.71073   7.3980   7.6612   8.4536   72.400   76.797   84.615
ZERR     2.00   0.0004   0.0005   0.0004    0.005    0.005    0.005
LATT   1
SFAC  C    H    N    O    CL
UNIT  18   14   2    2    4
MERG   2
OMIT    -2.00  53.00
FMAP   2
PLAN   10
ACTA
BOND   $H
EQIV $1 -x+3, -y, -z+1
HTAB O1 Cl2
HTAB N1 Cl2_$1
L.S.  10
TEMP   -90.00
WGHT    0.033800    0.263700
FVAR       7.73567
CL1   5   -0.271681    1.088495    0.230238    11.00000    0.02744    0.03552 =
         0.03125   -0.01266   -0.01045    0.01028
CL2   5    0.685200    0.637694    0.146471    11.00000    0.02405    0.02853 =
         0.02069   -0.00325    0.00148    0.00215
C1    1   -0.110944    0.563758    0.761537    11.00000    0.02672    0.02400 =
         0.02113   -0.00836    0.00125   -0.00510
AFIX  43
H1    2   -0.113355    0.475532    0.868705    11.00000   -1.20000
AFIX   0
C2    1   -0.275958    0.648982    0.720765    11.00000    0.02064    0.03250 =
         0.02628   -0.01293    0.00311   -0.00635
AFIX  43
H2    2   -0.391035    0.617281    0.798526    11.00000   -1.20000
AFIX   0
C3    1   -0.270565    0.778670    0.567733    11.00000    0.01775    0.02972 =
         0.02683   -0.01507   -0.00255   -0.00161
AFIX  43
H3    2   -0.382737    0.837260    0.539575    11.00000   -1.20000
AFIX   0
C4    1   -0.100265    0.826688    0.450895    11.00000    0.01861    0.02280 =
         0.02089   -0.01314   -0.00351   -0.00012
C5    1   -0.079029    0.959518    0.290145    11.00000    0.02132    0.02368 =
         0.02421   -0.01213   -0.00713    0.00304
C6    1    0.090423    0.991421    0.182690    11.00000    0.02744    0.02346 =
         0.01931   -0.00681   -0.00487   -0.00224
AFIX  43
H6    2    0.100983    1.081341    0.075459    11.00000   -1.20000
AFIX   0
C7    1    0.249980    0.892508    0.228944    11.00000    0.01939    0.02867 =
         0.02129   -0.00929    0.00153   -0.00480
AFIX  43
H7    2    0.366471    0.914890    0.151548    11.00000   -1.20000
AFIX   0
C8    1    0.239450    0.764328    0.384190    11.00000    0.01696    0.02433 =
         0.02067   -0.01096   -0.00251    0.00036
C9    1    0.062641    0.732361    0.496693    11.00000    0.01959    0.01799 =
         0.01871   -0.00944   -0.00235   -0.00151
O1    4    0.382140    0.663383    0.443088    11.00000    0.01640    0.03642 =
         0.02220   -0.00843   -0.00059    0.00415
N1    3    0.049580    0.605002    0.651671    11.00000    0.02036    0.02090 =
         0.01990   -0.00847   -0.00262    0.00070
H1O1  2    0.466326    0.661374    0.366488    11.00000    0.04264
H1N1  2    0.154504    0.538002    0.689168    11.00000    0.04798
HKLF 4
REM  exp_336t
REM R1 =  0.0288 for   1508 Fo > 4sig(Fo)  and  0.0406 for all   1836 data
REM    126 parameters refined using      0 restraints
END
WGHT      0.0327      0.1208
REM Highest difference peak  0.281,  deepest hole -0.197,  1-sigma level  0.049
Q1    1   0.1434  0.7349  0.4387  11.00000  0.05    0.28
Q2    1  -0.0216  0.7705  0.4596  11.00000  0.05    0.25
Q3    1  -0.0014  0.9318  0.2072  11.00000  0.05    0.24
Q4    1   0.0535  0.6822  0.5659  11.00000  0.05    0.24
Q5    1   0.2405  0.8680  0.3224  11.00000  0.05    0.22
Q6    1  -0.1824  0.8012  0.4927  11.00000  0.05    0.22
Q7    1  -0.0960  0.8688  0.3548  11.00000  0.05    0.21
Q8    1   0.0035  1.0050  0.2603  11.00000  0.05    0.21
Q9    1  -0.1531  0.9999  0.2608  11.00000  0.05    0.21
Q10   1   0.1569  0.9226  0.2242  11.00000  0.05    0.20
;
_[local]_cod_data_source_file    fg3281.cif
_[local]_cod_data_source_block   IV
_cod_original_cell_volume        444.47(4)
_cod_database_code               2018706
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
_atom_site_symmetry_multiplicity
Cl Cl1 -0.27168(7) 1.08850(7) 0.23024(6) 0.03076(15) Uani d . 1 1
Cl Cl2 0.68520(6) 0.63769(6) 0.14647(5) 0.02654(14) Uani d . 1 1
C C1 -0.1109(3) 0.5638(3) 0.7615(2) 0.0243(4) Uani d . 1 1
H H1 -0.1134 0.4755 0.8687 0.029 Uiso calc R 1 1
C C2 -0.2760(3) 0.6490(3) 0.7208(2) 0.0264(4) Uani d . 1 1
H H2 -0.3910 0.6173 0.7985 0.032 Uiso calc R 1 1
C C3 -0.2706(3) 0.7787(3) 0.5677(2) 0.0235(4) Uani d . 1 1
H H3 -0.3827 0.8373 0.5396 0.028 Uiso calc R 1 1
C C4 -0.1003(2) 0.8267(2) 0.4509(2) 0.0194(4) Uani d . 1 1
C C5 -0.0790(3) 0.9595(2) 0.2901(2) 0.0217(4) Uani d . 1 1
C C6 0.0904(3) 0.9914(3) 0.1827(2) 0.0232(4) Uani d . 1 1
H H6 0.1010 1.0813 0.0755 0.028 Uiso calc R 1 1
C C7 0.2500(3) 0.8925(3) 0.2289(2) 0.0233(4) Uani d . 1 1
H H7 0.3665 0.9149 0.1515 0.028 Uiso calc R 1 1
C C8 0.2395(2) 0.7643(2) 0.3842(2) 0.0200(4) Uani d . 1 1
C C9 0.0626(2) 0.7324(2) 0.4967(2) 0.0180(4) Uani d . 1 1
O O1 0.38214(19) 0.66338(19) 0.44309(17) 0.0259(3) Uani d . 1 1
N N1 0.0496(2) 0.6050(2) 0.65167(18) 0.0202(3) Uani d . 1 1
H H1O1 0.466(3) 0.661(3) 0.366(3) 0.043(7) Uiso d . 1 1
H H1N1 0.155(3) 0.538(3) 0.689(3) 0.048(7) Uiso d . 1 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
Cl1 0.0274(3) 0.0355(3) 0.0313(3) 0.0103(2) -0.0104(2) -0.0127(2)
Cl2 0.0241(3) 0.0285(3) 0.0207(2) 0.00215(19) 0.00148(17) -0.00325(18)
C1 0.0267(10) 0.0240(9) 0.0211(9) -0.0051(8) 0.0013(7) -0.0084(8)
C2 0.0206(10) 0.0325(11) 0.0263(10) -0.0063(8) 0.0031(8) -0.0129(8)
C3 0.0178(9) 0.0297(10) 0.0268(10) -0.0016(8) -0.0025(7) -0.0151(8)
C4 0.0186(9) 0.0228(9) 0.0209(9) -0.0001(7) -0.0035(7) -0.0131(7)
C5 0.0213(9) 0.0237(9) 0.0242(9) 0.0030(8) -0.0071(7) -0.0121(8)
C6 0.0274(10) 0.0235(9) 0.0193(9) -0.0022(8) -0.0049(7) -0.0068(7)
C7 0.0194(9) 0.0287(10) 0.0213(9) -0.0048(8) 0.0015(7) -0.0093(8)
C8 0.0170(9) 0.0243(9) 0.0207(9) 0.0004(7) -0.0025(7) -0.0110(7)
C9 0.0196(9) 0.0180(9) 0.0187(8) -0.0015(7) -0.0023(7) -0.0094(7)
O1 0.0164(7) 0.0364(8) 0.0222(7) 0.0041(6) -0.0006(6) -0.0084(6)
N1 0.0204(8) 0.0209(8) 0.0199(8) 0.0007(6) -0.0026(6) -0.0085(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 0.0016 '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
N1 C1 C2 120.46(17)
N1 C1 H1 119.8
C2 C1 H1 119.8
C3 C2 C1 119.33(17)
C3 C2 H2 120.3
C1 C2 H2 120.3
C2 C3 C4 120.84(18)
C2 C3 H3 119.6
C4 C3 H3 119.6
C3 C4 C9 117.52(16)
C3 C4 C5 125.40(17)
C9 C4 C5 117.06(16)
C6 C5 C4 121.27(17)
C6 C5 Cl1 119.26(14)
C4 C5 Cl1 119.45(14)
C5 C6 C7 120.72(17)
C5 C6 H6 119.6
C7 C6 H6 119.6
C8 C7 C6 120.90(17)
C8 C7 H7 119.5
C6 C7 H7 119.5
O1 C8 C7 126.23(16)
O1 C8 C9 115.51(16)
C7 C8 C9 118.26(16)
N1 C9 C4 119.21(16)
N1 C9 C8 119.03(16)
C4 C9 C8 121.75(16)
C8 O1 H1O1 109.9(18)
C1 N1 C9 122.60(16)
C1 N1 H1N1 114.6(15)
C9 N1 H1N1 122.8(15)
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_publ_flag
Cl1 C5 1.7398(18) yes
C1 N1 1.327(2) yes
C1 C2 1.394(3) ?
C1 H1 0.9500 ?
C2 C3 1.367(3) ?
C2 H2 0.9500 ?
C3 C4 1.413(2) ?
C3 H3 0.9500 ?
C4 C9 1.416(2) ?
C4 C5 1.415(3) ?
C5 C6 1.364(3) ?
C6 C7 1.409(3) ?
C6 H6 0.9500 ?
C7 C8 1.372(3) ?
C7 H7 0.9500 ?
C8 O1 1.347(2) yes
C8 C9 1.424(2) ?
C9 N1 1.366(2) yes
O1 H1O1 0.79(2) ?
N1 H1N1 0.95(3) ?
loop_
_geom_hbond_atom_site_label_D
_geom_hbond_atom_site_label_H
_geom_hbond_atom_site_label_A
_geom_hbond_distance_DH
_geom_hbond_distance_HA
_geom_hbond_distance_DA
_geom_hbond_angle_DHA
O1 H1O1 Cl2 0.79(2) 2.21(3) 3.0001(14) 174(2)