#------------------------------------------------------------------------------
#$Date: 2017-10-13 03:48:21 +0300 (Fri, 13 Oct 2017) $
#$Revision: 201957 $
#$URL: file:///home/coder/svn-repositories/cod/cif/2/01/46/2014636.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_2014636
loop_
_publ_author_name
'Firley, Delphine'
'Fraisse, Bernard'
'Zouhiri, Fatima'
'Spasojević-de Biré, Anne'
'Desmaële, Didier'
'd'Angelo, Jean'
'Ghermani, Nour Eddine'
_publ_section_title
;
 7-Carboxylato-8-hydroxy-2-methylquinolinium monohydrate and
 7-carboxy-8-hydroxy-2-methylquinolinium chloride monohydrate at 100K
;
_journal_issue                   3
_journal_name_full               'Acta Crystallographica Section C'
_journal_page_first              o154
_journal_page_last               o157
_journal_paper_doi               10.1107/S0108270104031403
_journal_volume                  61
_journal_year                    2005
_chemical_formula_iupac          'C11 H9 N O3 , H2 O'
_chemical_formula_moiety         'C11 H9 N O3 , H2 O'
_chemical_formula_sum            'C11 H11 N O4'
_chemical_formula_weight         221.21
_chemical_name_systematic
;
8-Hydroxy-2-methylquinoline-7-carboxylic acid monohydrate
;
_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   difmap
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_audit_creation_method           SHELXL97
_cell_angle_alpha                75.043(2)
_cell_angle_beta                 86.534(2)
_cell_angle_gamma                79.042(2)
_cell_formula_units_Z            2
_cell_length_a                   6.6556(7)
_cell_length_b                   7.8062(8)
_cell_length_c                   9.6690(10)
_cell_measurement_reflns_used    2110
_cell_measurement_temperature    100(2)
_cell_measurement_theta_max      30.08
_cell_measurement_theta_min      2.18
_cell_volume                     476.45(9)
_computing_cell_refinement       'SAINT-Plus (Bruker, 1998)'
_computing_data_collection       'SMART (Bruker, 1998)'
_computing_data_reduction        SAINT-Plus
_computing_molecular_graphics    'ORTEPIII (Farrugia, 1999)'
_computing_publication_material  SHELXL97
_computing_structure_refinement  'SHELXL97 (Sheldrick, 1997)'
_computing_structure_solution    'SIR97 (Altomare et al., 1999)'
_diffrn_ambient_temperature      100(2)
_diffrn_measured_fraction_theta_full 84.7
_diffrn_measured_fraction_theta_max 0.847
_diffrn_measurement_device_type  'Bruker SMART CCD area-detector'
_diffrn_measurement_method       ω
_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  0.0083
_diffrn_reflns_av_sigmaI/netI    0.0174
_diffrn_reflns_limit_h_max       9
_diffrn_reflns_limit_h_min       -9
_diffrn_reflns_limit_k_max       10
_diffrn_reflns_limit_k_min       -10
_diffrn_reflns_limit_l_max       13
_diffrn_reflns_limit_l_min       0
_diffrn_reflns_number            3364
_diffrn_reflns_theta_full        30.09
_diffrn_reflns_theta_max         30.09
_diffrn_reflns_theta_min         2.18
_diffrn_standards_number         0
_exptl_absorpt_coefficient_mu    0.119
_exptl_absorpt_correction_type   none
_exptl_crystal_colour            yellow
_exptl_crystal_density_diffrn    1.542
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       prism
_exptl_crystal_F_000             232
_exptl_crystal_size_max          0.40
_exptl_crystal_size_mid          0.30
_exptl_crystal_size_min          0.20
_refine_diff_density_max         0.440
_refine_diff_density_min         -0.238
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.049
_refine_ls_hydrogen_treatment    refall
_refine_ls_matrix_type           full
_refine_ls_number_parameters     189
_refine_ls_number_reflns         2364
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.049
_refine_ls_R_factor_all          0.0430
_refine_ls_R_factor_gt           0.0371
_refine_ls_shift/su_max          0.001
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'calc w = 1/[σ²(Fo²)+(0.0746P)²+0.0491P] where P = (Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1052
_refine_ls_wR_factor_ref         0.1089
_reflns_number_gt                2052
_reflns_number_total             2364
_reflns_threshold_expression     I>2σ(I)
_cod_data_source_file            dn1072.cif
_cod_data_source_block           I
_cod_database_code               2014636
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_refinement_flags
_atom_site_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
_atom_site_type_symbol
C2 0.78729(14) -0.19129(13) 0.81555(11) 0.0125(2) Uani d . 1 . . C
C3 0.81738(15) -0.35224(13) 0.77026(11) 0.0144(2) Uani d . 1 . . C
C4 0.81565(15) -0.34664(13) 0.62766(11) 0.0139(2) Uani d . 1 . . C
C5 0.78612(15) -0.16421(13) 0.37397(11) 0.0135(2) Uani d . 1 . . C
C6 0.75746(15) 0.00336(13) 0.28072(11) 0.0128(2) Uani d . 1 . . C
C7 0.72336(14) 0.16290(12) 0.32882(10) 0.0109(2) Uani d . 1 . . C
C8 0.71830(14) 0.15343(13) 0.47521(10) 0.0104(2) Uani d . 1 . . C
C9 0.75309(14) -0.02043(12) 0.57276(10) 0.0105(2) Uani d . 1 . . C
C10 0.78608(14) -0.17894(12) 0.52316(11) 0.0118(2) Uani d . 1 . . C
C11 0.79301(17) -0.19091(14) 0.96917(11) 0.0177(2) Uani d . 1 . . C
C12 0.69288(14) 0.34441(13) 0.22357(10) 0.0122(2) Uani d . 1 . . C
H1 0.730(2) 0.066(2) 0.7513(18) 0.032(4) Uiso d . 1 . . H
H3 0.837(2) -0.467(2) 0.8448(18) 0.030(4) Uiso d . 1 . . H
H4 0.836(2) -0.455(2) 0.5954(16) 0.026(4) Uiso d . 1 . . H
H5 0.804(2) -0.2729(19) 0.3385(16) 0.022(3) Uiso d . 1 . . H
H6 0.760(2) 0.0218(19) 0.1796(16) 0.021(3) Uiso d . 1 . . H
H31 0.658(3) 0.404(3) 0.429(2) 0.060(6) Uiso d . 1 . . H
H111 0.926(3) -0.169(2) 0.988(2) 0.046(5) Uiso d . 1 . . H
H112 0.689(3) -0.095(2) 0.9918(19) 0.041(5) Uiso d . 1 . . H
H113 0.772(3) -0.305(3) 1.029(2) 0.054(5) Uiso d . 1 . . H
HW1 0.669(2) 0.266(2) 0.9328(19) 0.028(4) Uiso d . 1 . . H
HW2 0.563(3) 0.326(3) 0.808(2) 0.046(5) Uiso d . 1 . . H
N 0.75478(12) -0.03384(11) 0.71716(9) 0.01095(18) Uani d . 1 . . N
O1 0.70883(13) 0.35645(10) 0.09333(8) 0.01858(19) Uani d . 1 . . O
O2 0.65155(11) 0.48123(9) 0.27950(8) 0.01463(18) Uani d . 1 . . O
O3 0.68211(11) 0.29915(9) 0.52690(8) 0.01316(17) Uani d . 1 . . O
OW 0.66319(13) 0.24405(10) 0.84906(9) 0.0198(2) Uani d . 1 . . O
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
_geom_angle_publ_flag
N C2 C3 118.86(9) ?
N C2 C11 118.88(9) yes
C3 C2 C11 122.26(9) ?
C4 C3 C2 120.40(9) ?
C4 C3 H3 122.2(9) ?
C2 C3 H3 117.4(9) ?
C3 C4 C10 120.55(9) ?
C3 C4 H4 121.3(9) ?
C10 C4 H4 118.2(9) ?
C6 C5 C10 119.28(9) ?
C6 C5 H5 120.7(8) ?
C10 C5 H5 120.1(9) ?
C5 C6 C7 121.98(9) ?
C5 C6 H6 123.2(9) ?
C7 C6 H6 114.9(9) ?
C8 C7 C6 120.26(9) ?
C8 C7 C12 119.18(8) yes
C6 C7 C12 120.57(9) ?
O3 C8 C7 122.93(9) yes
O3 C8 C9 119.00(9) ?
C7 C8 C9 118.08(9) ?
N C9 C10 119.60(8) ?
N C9 C8 119.36(8) ?
C10 C9 C8 121.04(9) ?
C9 C10 C5 119.33(9) ?
C9 C10 C4 117.41(9) ?
C5 C10 C4 123.25(9) ?
C2 C11 H111 108.2(11) ?
C2 C11 H112 111.4(10) ?
H111 C11 H112 107.9(15) ?
C2 C11 H113 110.1(11) ?
H111 C11 H113 109.9(15) ?
H112 C11 H113 109.2(16) ?
O1 C12 O2 124.27(9) yes
O1 C12 C7 120.44(9) ?
O2 C12 C7 115.29(8) yes
C2 N C9 123.14(8) yes
C2 N H1 115.9(10) ?
C9 N H1 121.0(10) ?
C12 O2 H31 104.6(8) ?
C8 O3 H31 100.7(11) ?
HW1 OW HW2 103.3(15) ?
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
C2 N . 1.3352(12) yes
C2 C3 . 1.4100(14) ?
C2 C11 . 1.4889(14) yes
C3 C4 . 1.3688(15) ?
C3 H3 . 0.984(16) ?
C4 C10 . 1.4201(13) ?
C4 H4 . 0.956(16) ?
C5 C6 . 1.3702(14) ?
C5 C10 . 1.4172(14) ?
C5 H5 . 0.979(15) ?
C6 C7 . 1.4133(13) ?
C6 H6 . 0.950(15) ?
C7 C8 . 1.3969(13) yes
C7 C12 . 1.5019(13) yes
C8 O3 . 1.3328(11) yes
C8 C9 . 1.4253(13) yes
C9 N . 1.3735(12) yes
C9 C10 . 1.4141(13) ?
C11 H111 . 0.971(18) ?
C11 H112 . 0.978(18) ?
C11 H113 . 0.96(2) ?
C12 O1 . 1.2379(12) yes
C12 O2 . 1.2951(12) yes
N H1 . 0.907(17) ?
O3 H31 . 1.08(2) ?
OW HW1 . 0.876(18) ?
OW HW2 . 0.87(2) ?
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
O3 H31 O2 . 1.08(2) 1.42(2) 2.4449(11) 157(2) yes
N H1 Ow . 0.91(2) 1.85(2) 2.7450(12) 170(2) yes
Ow Hw1 O1 1_556 0.87(2) 1.91(2) 2.7746(12) 168(2) yes
Ow Hw2 O2 2_666 0.87(2) 1.92(2) 2.7863(12) 176(2) yes
loop_
_cod_related_entry_id
_cod_related_entry_database
_cod_related_entry_code
1 ChemSpider 21133939
