#------------------------------------------------------------------------------
#$Date: 2017-10-13 03:48:21 +0300 (Fri, 13 Oct 2017) $
#$Revision: 201957 $
#$URL: file:///home/coder/svn-repositories/cod/cif/2/01/46/2014637.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_2014637
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 H10 N O3 + , Cl - , H2 O'
_chemical_formula_moiety         'C11 H10 N O3 + , Cl - , H2 O'
_chemical_formula_sum            'C11 H12 Cl N O4'
_chemical_formula_weight         257.67
_chemical_name_systematic
;
7-carboxy-8-hydroxy-2-methylquinolinium chloride 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           SHELXL-97
_cell_angle_alpha                96.7190(10)
_cell_angle_beta                 110.1840(10)
_cell_angle_gamma                107.9410(10)
_cell_formula_units_Z            2
_cell_length_a                   7.1089(4)
_cell_length_b                   9.4102(5)
_cell_length_c                   9.6230(5)
_cell_measurement_reflns_used    2975
_cell_measurement_temperature    100(2)
_cell_measurement_theta_max      30.21
_cell_measurement_theta_min      2.33
_cell_volume                     556.57(5)
_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 87.3
_diffrn_measured_fraction_theta_max 0.873
_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  0.0096
_diffrn_reflns_av_sigmaI/netI    0.0183
_diffrn_reflns_limit_h_max       9
_diffrn_reflns_limit_h_min       -9
_diffrn_reflns_limit_k_max       8
_diffrn_reflns_limit_k_min       -12
_diffrn_reflns_limit_l_max       12
_diffrn_reflns_limit_l_min       -13
_diffrn_reflns_number            3978
_diffrn_reflns_theta_full        30.29
_diffrn_reflns_theta_max         30.29
_diffrn_reflns_theta_min         2.33
_diffrn_standards_number         0
_exptl_absorpt_coefficient_mu    0.346
_exptl_absorpt_correction_type   none
_exptl_crystal_colour            white
_exptl_crystal_density_diffrn    1.538
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       prism
_exptl_crystal_F_000             268
_exptl_crystal_size_max          0.60
_exptl_crystal_size_mid          0.30
_exptl_crystal_size_min          0.20
_refine_diff_density_max         0.429
_refine_diff_density_min         -0.228
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.080
_refine_ls_hydrogen_treatment    refall
_refine_ls_matrix_type           full
_refine_ls_number_parameters     202
_refine_ls_number_reflns         2904
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.080
_refine_ls_R_factor_all          0.0344
_refine_ls_R_factor_gt           0.0301
_refine_ls_shift/su_max          0.002
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'calc w = 1/[σ²(Fo²)+(0.0528P)²+0.1462P] where P = (Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0837
_refine_ls_wR_factor_ref         0.0862
_reflns_number_gt                2627
_reflns_number_total             2904
_reflns_threshold_expression     I>2σ(I)
_cod_data_source_file            dn1072.cif
_cod_data_source_block           II
_cod_database_code               2014637
_cod_database_fobs_code          2014637
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 0.51807(18) 0.69963(13) 0.26054(12) 0.0130(2) Uani d . 1 . . C
C3 0.59355(18) 0.81641(13) 0.19077(12) 0.0140(2) Uani d . 1 . . C
C4 0.70536(18) 0.96635(13) 0.27376(13) 0.0133(2) Uani d . 1 . . C
C5 0.86469(18) 1.15942(13) 0.52474(13) 0.0132(2) Uani d . 1 . . C
C6 0.89649(18) 1.19039(13) 0.67549(13) 0.0132(2) Uani d . 1 . . C
C7 0.81901(17) 1.07035(13) 0.74203(12) 0.0119(2) Uani d . 1 . . C
C8 0.71063(17) 0.91830(12) 0.65502(12) 0.0117(2) Uani d . 1 . . C
C9 0.67491(17) 0.88688(12) 0.49811(12) 0.0111(2) Uani d . 1 . . C
C10 0.75085(17) 1.00612(13) 0.43216(12) 0.0117(2) Uani d . 1 . . C
C11 0.3932(2) 0.53534(14) 0.17359(14) 0.0177(2) Uani d . 1 . . C
C12 0.83898(17) 1.10360(13) 0.90190(12) 0.0132(2) Uani d . 1 . . C
Cl 0.17327(4) 0.63087(3) 0.77817(3) 0.01637(9) Uani d . 1 . . Cl
H1 0.499(3) 0.669(2) 0.446(2) 0.045(6) Uiso d . 1 . . H
H3 0.564(3) 0.7853(18) 0.0829(18) 0.016(4) Uiso d . 1 . . H
H4 0.752(3) 1.047(2) 0.228(2) 0.026(4) Uiso d . 1 . . H
H5 0.914(3) 1.239(2) 0.480(2) 0.027(4) Uiso d . 1 . . H
H6 0.973(2) 1.2911(18) 0.7394(18) 0.015(4) Uiso d . 1 . . H
H11 0.920(3) 1.267(2) 1.061(2) 0.041(5) Uiso d . 1 . . H
H111 0.503(3) 0.494(2) 0.159(2) 0.043(5) Uiso d . 1 . . H
H112 0.322(3) 0.478(2) 0.228(2) 0.043(5) Uiso d . 1 . . H
H113 0.293(3) 0.528(2) 0.077(2) 0.036(5) Uiso d . 1 . . H
H31 0.651(3) 0.838(2) 0.801(2) 0.042(5) Uiso d . 1 . . H
HW1 0.276(3) 0.552(2) 0.570(2) 0.039(5) Uiso d . 1 . . H
HW2 0.168(4) 0.475(2) 0.426(2) 0.037(5) Uiso d . 1 . . H
N 0.55970(15) 0.73849(11) 0.40861(10) 0.01174(18) Uani d . 1 . . N
O1 0.93675(15) 1.25173(10) 0.97271(10) 0.01852(19) Uani d . 1 . . O
O2 0.76556(14) 1.00293(10) 0.96030(9) 0.01691(18) Uani d . 1 . . O
O3 0.63225(14) 0.79801(10) 0.70810(10) 0.01678(18) Uani d . 1 . . O
OW 0.28687(14) 0.51444(10) 0.49358(10) 0.01639(18) 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'
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
_geom_angle_publ_flag
N C2 C3 118.74(10) ?
N C2 C11 119.09(10) yes
C3 C2 C11 122.16(10) ?
C4 C3 C2 120.53(10) ?
C4 C3 H3 122.0(9) ?
C2 C3 H3 117.4(9) ?
C3 C4 C10 120.18(10) ?
C3 C4 H4 121.8(11) ?
C10 C4 H4 118.0(11) ?
C6 C5 C10 120.06(10) ?
C6 C5 H5 121.0(11) ?
C10 C5 H5 118.9(10) ?
C5 C6 C7 120.90(10) ?
C5 C6 H6 121.5(9) ?
C7 C6 H6 117.6(9) ?
C8 C7 C6 120.42(10) ?
C8 C7 C12 118.07(10) yes
C6 C7 C12 121.41(10) ?
O3 C8 C7 124.50(10) yes
O3 C8 C9 116.94(10) ?
C7 C8 C9 118.54(10) ?
N C9 C10 119.61(10) ?
N C9 C8 119.42(10) ?
C10 C9 C8 120.95(10) ?
C9 C10 C5 119.11(10) ?
C9 C10 C4 117.76(10) ?
C5 C10 C4 123.11(10) ?
C2 C11 H111 105.8(12) ?
C2 C11 H112 111.3(12) ?
H111 C11 H112 110.2(16) ?
C2 C11 H113 111.0(12) ?
H111 C11 H113 108.2(16) ?
H112 C11 H113 110.2(17) ?
O2 C12 O1 123.77(10) yes
O2 C12 C7 122.80(10) yes
O1 C12 C7 113.40(10) ?
C2 N C9 123.14(10) yes
C2 N H1 117.5(14) ?
C9 N H1 119.0(14) ?
C12 O1 H11 109.2(13) ?
C8 O3 H31 105.4(14) ?
HW1 OW HW2 108(2) ?
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 . 1.3312(14) yes
C2 C3 . 1.4158(15) ?
C2 C11 . 1.4892(16) yes
C3 C4 . 1.3666(16) ?
C3 H3 . 0.973(16) ?
C4 C10 . 1.4212(15) ?
C4 H4 . 0.955(18) ?
C5 C6 . 1.3692(15) ?
C5 C10 . 1.4185(15) ?
C5 H5 . 0.945(18) ?
C6 C7 . 1.4208(15) ?
C6 H6 . 0.942(16) ?
C7 C8 . 1.3919(15) yes
C7 C12 . 1.4812(15) yes
C8 O3 . 1.3401(13) yes
C8 C9 . 1.4200(14) yes
C9 N . 1.3746(14) yes
C9 C10 . 1.4082(15) ?
C11 H111 . 1.02(2) ?
C11 H112 . 0.95(2) ?
C11 H113 . 0.93(2) ?
C12 O2 . 1.2280(14) yes
C12 O1 . 1.3209(14) yes
N H1 . 0.86(2) ?
O1 H11 . 0.90(2) ?
O3 H31 . 0.88(2) ?
OW HW1 . 0.82(2) ?
OW HW2 . 0.81(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
N H1 Ow . 0.86(2) 1.97(2) 2.8025(14) 164(2) yes
O1 H11 Cl 2_677 0.90(2) 2.12(2) 2.9641(11) 155(2) yes
O3 H31 O2 . 0.88(2) 1.80(2) 2.5881(12) 149(2) yes
Ow Hw1 Cl . 0.82(2) 2.47(2) 3.2744(10) 169(2) yes
Ow Hw2 Cl 2_566 0.80(2) 2.35(2) 3.1485(10) 177(2) yes
loop_
_cod_related_entry_id
_cod_related_entry_database
_cod_related_entry_code
1 ChemSpider 21133938
