#------------------------------------------------------------------------------
#$Date: 2017-10-13 11:42:48 +0300 (Fri, 13 Oct 2017) $
#$Revision: 201978 $
#$URL: file:///home/coder/svn-repositories/cod/cif/2/22/72/2227201.cif $
#------------------------------------------------------------------------------
#
# This file is available in the Crystallography Open Database (COD),
# http://www.crystallography.net/
#
# All data on this site have been placed in the public domain by the
# contributors.
#
data_2227201
loop_
_publ_author_name
'Quah, Ching Kheng'
'Loh, Wan-Sin'
'Hemamalini, Madhukar'
'Fun, Hoong-Kun'
_publ_section_title
;
 8-Hydroxyquinolinium 2-carboxyacetate
;
_journal_coeditor_code           BT5313
_journal_issue                   9
_journal_name_full               'Acta Crystallographica Section E'
_journal_page_first              o2254
_journal_paper_doi               10.1107/S1600536810030990
_journal_volume                  66
_journal_year                    2010
_chemical_formula_iupac          'C9 H8 N O +, C3 H3 O4 -'
_chemical_formula_moiety         'C9 H8 N O +, C3 H3 O4 -'
_chemical_formula_sum            'C12 H11 N O5'
_chemical_formula_weight         249.22
_chemical_name_systematic
;
8-Hydroxyquinolinium 2-carboxyacetate
;
_space_group_IT_number           14
_symmetry_cell_setting           monoclinic
_symmetry_space_group_name_Hall  '-P 2ybc'
_symmetry_space_group_name_H-M   'P 1 21/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                 90.999(3)
_cell_angle_gamma                90.00
_cell_formula_units_Z            4
_cell_length_a                   8.7089(4)
_cell_length_b                   5.2930(2)
_cell_length_c                   23.4672(9)
_cell_measurement_reflns_used    3422
_cell_measurement_temperature    100.00(10)
_cell_measurement_theta_max      30.00
_cell_measurement_theta_min      3.47
_cell_volume                     1081.58(8)
_computing_cell_refinement       'SAINT (Bruker, 2009)'
_computing_data_collection       'APEX2 (Bruker, 2009)'
_computing_data_reduction        'SAINT (Bruker, 2009)'
_computing_molecular_graphics    'SHELXTL (Sheldrick, 2008)'
_computing_publication_material
;
SHELXTL (Sheldrick, 2008) and PLATON (Spek, 2009)
;
_computing_structure_refinement  'SHELXTL (Sheldrick, 2008)'
_computing_structure_solution    'SHELXTL (Sheldrick, 2008)'
_diffrn_ambient_temperature      100
_diffrn_measured_fraction_theta_full 0.993
_diffrn_measured_fraction_theta_max 0.993
_diffrn_measurement_device_type
;
Bruker SMART APEXII CCD area-detector diffractometer
;
_diffrn_measurement_method       'φ and ω 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  0.0408
_diffrn_reflns_av_sigmaI/netI    0.0374
_diffrn_reflns_limit_h_max       12
_diffrn_reflns_limit_h_min       -11
_diffrn_reflns_limit_k_max       7
_diffrn_reflns_limit_k_min       -7
_diffrn_reflns_limit_l_max       32
_diffrn_reflns_limit_l_min       -33
_diffrn_reflns_number            12061
_diffrn_reflns_theta_full        30.06
_diffrn_reflns_theta_max         30.06
_diffrn_reflns_theta_min         2.34
_diffrn_standards_number         0
_exptl_absorpt_coefficient_mu    0.121
_exptl_absorpt_correction_T_max  0.9918
_exptl_absorpt_correction_T_min  0.9289
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   '(SADABS; Bruker, 2009)'
_exptl_crystal_colour            yellow
_exptl_crystal_density_diffrn    1.530
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       plate
_exptl_crystal_F_000             520
_exptl_crystal_size_max          0.519
_exptl_crystal_size_mid          0.169
_exptl_crystal_size_min          0.068
_refine_diff_density_max         0.330
_refine_diff_density_min         -0.292
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.044
_refine_ls_hydrogen_treatment    refall
_refine_ls_matrix_type           full
_refine_ls_number_parameters     207
_refine_ls_number_reflns         3170
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.044
_refine_ls_R_factor_all          0.0559
_refine_ls_R_factor_gt           0.0426
_refine_ls_shift/su_max_lt       0.001
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'calc w=1/[σ²(Fo²)+(0.0618P)²+0.2285P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1094
_refine_ls_wR_factor_ref         0.1182
_reflns_number_gt                2552
_reflns_number_total             3170
_reflns_threshold_expression     I>2σ(I)
_cod_data_source_file            bt5313.cif
_cod_data_source_block           I
_cod_original_sg_symbol_H-M      'P 21/c'
_cod_database_code               2227201
_cod_database_fobs_code          2227201
loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'-x, y+1/2, -z+1/2'
'-x, -y, -z'
'x, -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
_atom_site_disorder_assembly
_atom_site_disorder_group
O O1 0.09573(11) 0.85826(16) 0.23539(4) 0.0178(2) Uani d . 1 . .
N N1 0.16598(13) 0.89411(19) 0.12400(4) 0.0152(2) Uani d . 1 . .
C C1 0.23458(14) 0.7104(2) 0.15690(5) 0.0142(2) Uani d . 1 . .
C C2 0.19403(16) 0.9186(2) 0.06877(5) 0.0183(3) Uani d . 1 . .
C C3 0.29489(16) 0.7560(3) 0.04150(5) 0.0204(3) Uani d . 1 . .
C C4 0.36509(16) 0.5673(2) 0.07247(5) 0.0201(3) Uani d . 1 . .
C C5 0.33690(14) 0.5386(2) 0.13142(5) 0.0165(2) Uani d . 1 . .
C C6 0.40592(15) 0.3468(2) 0.16573(6) 0.0193(3) Uani d . 1 . .
C C7 0.37370(15) 0.3379(2) 0.22279(6) 0.0193(3) Uani d . 1 . .
C C8 0.27372(15) 0.5121(2) 0.24808(5) 0.0172(2) Uani d . 1 . .
C C9 0.19971(14) 0.6941(2) 0.21562(5) 0.0144(2) Uani d . 1 . .
O O2 0.79886(13) 0.74847(19) 0.03808(4) 0.0268(2) Uani d . 1 . .
O O3 0.66717(12) 0.95987(18) 0.10240(4) 0.0237(2) Uani d . 1 . .
O O4 0.96190(11) 0.38081(17) 0.06705(4) 0.0208(2) Uani d . 1 . .
O O5 0.97057(11) 0.25359(16) 0.15766(3) 0.0177(2) Uani d . 1 . .
C C10 0.75145(15) 0.7864(2) 0.09062(5) 0.0176(2) Uani d . 1 . .
C C11 0.80638(16) 0.5972(2) 0.13524(5) 0.0195(3) Uani d . 1 . .
C C12 0.92134(14) 0.3958(2) 0.11786(5) 0.0155(2) Uani d . 1 . .
H H1O1 0.073(2) 0.817(4) 0.2748(9) 0.042(5) Uiso d . 1 . .
H H1O2 0.866(3) 0.602(4) 0.0417(9) 0.057(6) Uiso d . 1 . .
H H1N1 0.098(2) 1.015(4) 0.1398(8) 0.037(5) Uiso d . 1 . .
H H2A 0.141(2) 1.051(3) 0.0516(7) 0.022(4) Uiso d . 1 . .
H H3A 0.3100(19) 0.781(3) 0.0005(7) 0.023(4) Uiso d . 1 . .
H H4A 0.437(2) 0.447(3) 0.0560(7) 0.027(4) Uiso d . 1 . .
H H6A 0.4720(18) 0.226(3) 0.1476(7) 0.019(4) Uiso d . 1 . .
H H7A 0.4224(19) 0.207(3) 0.2466(7) 0.024(4) Uiso d . 1 . .
H H8A 0.2547(19) 0.505(3) 0.2888(7) 0.020(4) Uiso d . 1 . .
H H11A 0.716(2) 0.510(4) 0.1503(8) 0.039(5) Uiso d . 1 . .
H H11B 0.852(2) 0.689(4) 0.1680(8) 0.035(5) Uiso d . 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_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle
_geom_angle_publ_flag
C9 O1 H1O1 . . 109.3(12) ?
C2 N1 C1 . . 122.14(11) ?
C2 N1 H1N1 . . 116.1(11) ?
C1 N1 H1N1 . . 121.7(11) ?
N1 C1 C5 . . 119.31(10) ?
N1 C1 C9 . . 119.40(10) ?
C5 C1 C9 . . 121.28(11) ?
N1 C2 C3 . . 121.04(12) ?
N1 C2 H2A . . 113.5(10) ?
C3 C2 H2A . . 125.5(10) ?
C4 C3 C2 . . 119.00(11) ?
C4 C3 H3A . . 123.3(10) ?
C2 C3 H3A . . 117.6(10) ?
C3 C4 C5 . . 120.77(12) ?
C3 C4 H4A . . 123.2(10) ?
C5 C4 H4A . . 116.1(10) ?
C1 C5 C4 . . 117.72(11) ?
C1 C5 C6 . . 118.88(11) ?
C4 C5 C6 . . 123.40(12) ?
C7 C6 C5 . . 119.01(12) ?
C7 C6 H6A . . 122.8(9) ?
C5 C6 H6A . . 118.2(9) ?
C6 C7 C8 . . 121.81(12) ?
C6 C7 H7A . . 119.1(10) ?
C8 C7 H7A . . 119.1(10) ?
C9 C8 C7 . . 120.74(11) ?
C9 C8 H8A . . 118.7(10) ?
C7 C8 H8A . . 120.5(10) ?
O1 C9 C8 . . 124.86(11) ?
O1 C9 C1 . . 116.96(10) ?
C8 C9 C1 . . 118.17(11) ?
C10 O2 H1O2 . . 103.7(13) ?
O3 C10 O2 . . 121.90(12) ?
O3 C10 C11 . . 121.81(11) ?
O2 C10 C11 . . 116.29(11) ?
C10 C11 C12 . . 118.50(10) ?
C10 C11 H11A . . 108.4(12) ?
C12 C11 H11A . . 107.4(12) ?
C10 C11 H11B . . 109.3(11) ?
C12 C11 H11B . . 107.1(11) ?
H11A C11 H11B . . 105.5(16) ?
O4 C12 O5 . . 124.50(11) ?
O4 C12 C11 . . 119.80(11) ?
O5 C12 C11 . . 115.70(10) ?
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_site_symmetry_2
_geom_bond_distance
_geom_bond_publ_flag
O1 C9 . 1.3434(15) ?
O1 H1O1 . 0.97(2) ?
N1 C2 . 1.3295(15) ?
N1 C1 . 1.3722(15) ?
N1 H1N1 . 0.95(2) ?
C1 C5 . 1.4132(17) ?
C1 C9 . 1.4187(16) ?
C2 C3 . 1.3933(18) ?
C2 H2A . 0.928(17) ?
C3 C4 . 1.3727(19) ?
C3 H3A . 0.982(16) ?
C4 C5 . 1.4174(17) ?
C4 H4A . 0.977(18) ?
C5 C6 . 1.4222(17) ?
C6 C7 . 1.3736(18) ?
C6 H6A . 0.963(17) ?
C7 C8 . 1.4066(18) ?
C7 H7A . 0.981(17) ?
C8 C9 . 1.3811(17) ?
C8 H8A . 0.973(16) ?
O2 C10 . 1.3223(15) ?
O2 H1O2 . 0.97(2) ?
O3 C10 . 1.2107(16) ?
O4 C12 . 1.2521(14) ?
O5 C12 . 1.2683(14) ?
C10 C11 . 1.5198(17) ?
C11 C12 . 1.5231(17) ?
C11 H11A . 0.98(2) ?
C11 H11B . 0.990(19) ?
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
_geom_hbond_publ_flag
O1 H1O1 O5 2_655 0.97(2) 1.67(2) 2.6439(12) 178.1(14) yes
O2 H1O2 O4 . 0.97(2) 1.55(2) 2.4963(14) 162(2) yes
N1 H1N1 O5 1_465 0.95(2) 1.74(2) 2.6809(14) 170.9(17) yes
C2 H2A O4 1_465 0.928(16) 2.373(17) 3.1735(15) 144.4(14) yes
C2 H2A O2 3_675 0.928(16) 2.423(16) 3.0663(15) 126.5(13) yes
C6 H6A O3 1_545 0.964(16) 2.462(16) 3.4202(16) 172.5(13) yes
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_site_symmetry_1
_geom_torsion_site_symmetry_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
_geom_torsion
_geom_torsion_publ_flag
C2 N1 C1 C5 . . . . -0.90(18) ?
C2 N1 C1 C9 . . . . -179.97(11) ?
C1 N1 C2 C3 . . . . 0.34(19) ?
N1 C2 C3 C4 . . . . 0.4(2) ?
C2 C3 C4 C5 . . . . -0.5(2) ?
N1 C1 C5 C4 . . . . 0.71(17) ?
C9 C1 C5 C4 . . . . 179.77(11) ?
N1 C1 C5 C6 . . . . -179.22(11) ?
C9 C1 C5 C6 . . . . -0.16(18) ?
C3 C4 C5 C1 . . . . -0.01(19) ?
C3 C4 C5 C6 . . . . 179.92(13) ?
C1 C5 C6 C7 . . . . -1.42(18) ?
C4 C5 C6 C7 . . . . 178.66(12) ?
C5 C6 C7 C8 . . . . 0.37(19) ?
C6 C7 C8 C9 . . . . 2.3(2) ?
C7 C8 C9 O1 . . . . 175.89(11) ?
C7 C8 C9 C1 . . . . -3.83(18) ?
N1 C1 C9 O1 . . . . 2.09(16) ?
C5 C1 C9 O1 . . . . -176.97(11) ?
N1 C1 C9 C8 . . . . -178.17(11) ?
C5 C1 C9 C8 . . . . 2.77(18) ?
O3 C10 C11 C12 . . . . -175.64(12) ?
O2 C10 C11 C12 . . . . 5.39(18) ?
C10 C11 C12 O4 . . . . -3.81(18) ?
C10 C11 C12 O5 . . . . 175.62(11) ?
loop_
_cod_related_entry_id
_cod_related_entry_database
_cod_related_entry_code
1 ChemSpider 30656182
