#------------------------------------------------------------------------------
#$Date: 2016-06-26 05:08:59 +0300 (Sun, 26 Jun 2016) $
#$Revision: 183948 $
#$URL: file:///home/coder/svn-repositories/cod/cif/1/54/35/1543531.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_1543531
loop_
_publ_author_name
'Filali Baba, Yassir'
'Mague, Joel T.'
'Kandri Rodi, Youssef'
'Ouzidan, Younes'
'Essassi, El Mokhtar'
'Zouihri, Hafid'
_publ_section_title
;
 2-Oxo-1,2-dihydroquinoline-4-carboxylic acid monohydrate
;
_journal_coeditor_code           BH4007
_journal_issue                   6
_journal_name_full               IUCrData
_journal_page_first              x160997
_journal_paper_doi               10.1107/S2414314616009974
_journal_volume                  1
_journal_year                    2016
_chemical_formula_iupac          'C10 H7 N O3, H2 O'
_chemical_formula_moiety         'C10 H7 N O3, H2 O'
_chemical_formula_sum            'C10 H9 N O4'
_chemical_formula_weight         207.18
_chemical_name_systematic
;
2-Oxo-1,2-dihydroquinoline-4-carboxylic acid monohydrate
;
_space_group_crystal_system      monoclinic
_space_group_IT_number           13
_space_group_name_Hall           '-P 2yac'
_space_group_name_H-M_alt        'P 1 2/n 1'
_symmetry_space_group_name_Hall  '-P 2yac'
_symmetry_space_group_name_H-M   'P 1 2/n 1'
_atom_sites_solution_hydrogens   mixed
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_audit_creation_method           SHELXL-2014/7
_cell_angle_alpha                90
_cell_angle_beta                 98.582(2)
_cell_angle_gamma                90
_cell_formula_units_Z            8
_cell_length_a                   20.7884(8)
_cell_length_b                   3.72150(10)
_cell_length_c                   23.8849(9)
_cell_measurement_reflns_used    8389
_cell_measurement_temperature    150(2)
_cell_measurement_theta_max      72.2342
_cell_measurement_theta_min      2.6307
_cell_volume                     1827.14(11)
_computing_cell_refinement
;
SAINT (Bruker, 2016)
;
_computing_data_collection
;
APEX3 (Bruker, 2016)
;
_computing_data_reduction
;
SAINT (Bruker, 2016)
;
_computing_molecular_graphics
;
PLATON (Spek, 2009)
;
_computing_publication_material
;
publCIF (Westrip, 2010)
;
_computing_structure_refinement
;
SHELXL2014 (Sheldrick, 2015b)
;
_computing_structure_solution
;
SHELXT (Sheldrick, 2015a)
;
_diffrn_ambient_temperature      150(2)
_diffrn_detector_area_resol_mean 10.4167
_diffrn_measured_fraction_theta_full 0.987
_diffrn_measured_fraction_theta_max 0.976
_diffrn_measurement_device_type  'Bruker D8 VENTURE PHOTON 100 CMOS'
_diffrn_measurement_method       'ω scans'
_diffrn_radiation_monochromator  mirror
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54178
_diffrn_reflns_av_R_equivalents  0.0352
_diffrn_reflns_limit_h_max       20
_diffrn_reflns_limit_h_min       -24
_diffrn_reflns_limit_k_max       4
_diffrn_reflns_limit_k_min       -4
_diffrn_reflns_limit_l_max       28
_diffrn_reflns_limit_l_min       -29
_diffrn_reflns_number            12922
_diffrn_reflns_theta_full        67.500
_diffrn_reflns_theta_max         72.230
_diffrn_reflns_theta_min         3.053
_exptl_absorpt_coefficient_mu    1.004
_exptl_absorpt_correction_T_max  0.96
_exptl_absorpt_correction_T_min  0.85
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
(SADABS; Bruker, 2016)
;
_exptl_crystal_colour            colourless
_exptl_crystal_density_diffrn    1.506
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       plate
_exptl_crystal_F_000             864
_exptl_crystal_size_max          0.182
_exptl_crystal_size_mid          0.145
_exptl_crystal_size_min          0.044
_refine_diff_density_max         0.381
_refine_diff_density_min         -0.250
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.040
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_constraints    0
_refine_ls_number_parameters     281
_refine_ls_number_reflns         3541
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.040
_refine_ls_R_factor_all          0.0498
_refine_ls_R_factor_gt           0.0408
_refine_ls_shift/su_max          0.001
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'w=1/[σ²(Fo²)+(0.0589P)²+0.7256P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1028
_refine_ls_wR_factor_ref         0.1099
_reflns_number_gt                2964
_reflns_number_total             3541
_reflns_threshold_expression     'I > 2σ(I)'
_cod_data_source_file            bh4007sup1.cif
_cod_data_source_block           I
_cod_database_code               1543531
_shelx_estimated_absorpt_t_min   0.838
_shelx_estimated_absorpt_t_max   0.957
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x+1/2, y, -z+1/2'
'-x, -y, -z'
'x-1/2, -y, 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_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
O O1 0.05828(5) 0.4566(3) 0.55972(4) 0.0263(3) Uani d 1 . .
O O2 0.30022(5) 0.0876(3) 0.48988(4) 0.0271(3) Uani d 1 . .
H H2 0.3400 0.0624 0.5069 0.032 Uiso d 1 . .
O O3 0.28157(6) -0.1782(4) 0.57018(5) 0.0341(3) Uani d 1 . .
N N1 0.06261(6) 0.2096(4) 0.47364(5) 0.0203(3) Uani d 1 . .
H H1 0.0213 0.2875 0.4620 0.024 Uiso d 1 . .
C C1 0.09018(7) 0.2917(4) 0.52711(6) 0.0208(3) Uani d 1 . .
C C2 0.15720(7) 0.1848(4) 0.54320(6) 0.0216(3) Uani d 1 . .
H H2A 0.1777 0.2205 0.5811 0.026 Uiso calc 1 . .
C C3 0.19130(7) 0.0348(4) 0.50521(6) 0.0199(3) Uani d 1 . .
C C4 0.16090(7) -0.0446(4) 0.44812(6) 0.0195(3) Uani d 1 . .
C C5 0.19256(8) -0.2098(4) 0.40645(6) 0.0226(3) Uani d 1 . .
H H5 0.2373 -0.2721 0.4150 0.027 Uiso calc 1 . .
C C6 0.15898(8) -0.2811(4) 0.35347(6) 0.0244(3) Uani d 1 . .
H H6 0.1809 -0.3876 0.3255 0.029 Uiso calc 1 . .
C C7 0.09275(8) -0.1973(4) 0.34063(6) 0.0241(3) Uani d 1 . .
H H7 0.0699 -0.2517 0.3041 0.029 Uiso calc 1 . .
C C8 0.06040(8) -0.0374(4) 0.38018(6) 0.0221(3) Uani d 1 . .
H H8 0.0154 0.0180 0.3713 0.027 Uiso calc 1 . .
C C9 0.09468(7) 0.0431(4) 0.43393(6) 0.0197(3) Uani d 1 . .
C C10 0.26237(7) -0.0371(4) 0.52540(6) 0.0217(3) Uani d 1 . .
O O4 0.42412(5) 0.0548(3) 0.52056(4) 0.0251(3) Uani d 1 . .
O O5 0.37123(6) 0.7177(4) 0.69734(5) 0.0375(3) Uani d 1 . .
O O6 0.45531(6) 0.4850(4) 0.75528(5) 0.0347(3) Uani d 1 . .
H H6A 0.4327 0.5472 0.7816 0.042 Uiso d 1 . .
N N2 0.51852(6) 0.2797(4) 0.56588(5) 0.0197(3) Uani d 1 . .
H H2B 0.5374 0.1958 0.5365 0.024 Uiso d 1 . .
C C11 0.45441(7) 0.2135(4) 0.56345(6) 0.0203(3) Uani d 1 . .
C C12 0.42424(7) 0.3275(4) 0.61097(6) 0.0221(3) Uani d 1 . .
H H12 0.3787 0.2959 0.6100 0.026 Uiso calc 1 . .
C C13 0.46007(8) 0.4797(4) 0.65710(6) 0.0209(3) Uani d 1 . .
C C14 0.52881(7) 0.5455(4) 0.65896(6) 0.0197(3) Uani d 1 . .
C C15 0.56950(8) 0.7117(4) 0.70415(6) 0.0231(3) Uani d 1 . .
H H15 0.5519 0.7850 0.7368 0.028 Uiso calc 1 . .
C C16 0.63443(8) 0.7692(4) 0.70153(7) 0.0260(4) Uani d 1 . .
H H16 0.6613 0.8780 0.7326 0.031 Uiso calc 1 . .
C C17 0.66096(8) 0.6681(5) 0.65332(7) 0.0254(3) Uani d 1 . .
H H17 0.7057 0.7105 0.6518 0.030 Uiso calc 1 . .
C C18 0.62274(8) 0.5076(4) 0.60813(6) 0.0226(3) Uani d 1 . .
H H18 0.6408 0.4413 0.5753 0.027 Uiso calc 1 . .
C C19 0.55683(7) 0.4432(4) 0.61111(6) 0.0196(3) Uani d 1 . .
C C20 0.42396(8) 0.5753(5) 0.70562(6) 0.0245(3) Uani d 1 . .
O O7 0.39711(6) 0.7156(4) 0.83450(5) 0.0389(3) Uani d 1 . .
H H7A 0.4043 0.6144 0.8677 0.058 Uiso d 1 . .
H H7B 0.3549 0.7252 0.8268 0.058 Uiso d 1 . .
O O8 0.26582(17) 0.934(2) 0.80246(18) 0.0619(19) Uani d 0.494(12) A 1
H H8A 0.2609 1.1497 0.8152 0.093 Uiso d 0.494(12) A 1
H H8B 0.2407 0.7859 0.8173 0.093 Uiso d 0.494(12) A 1
O O8A 0.26537(17) 0.681(3) 0.8129(2) 0.071(2) Uani d 0.506(12) A 2
H H8AA 0.2488 0.7914 0.7819 0.107 Uiso d 0.506(12) A 2
H H8AB 0.2466 0.7575 0.8408 0.107 Uiso d 0.506(12) A 2
loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0181 0.0091 '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 0.0311 0.0180 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0492 0.0322 '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
C10 O2 H2 106.1
C1 N1 C9 124.59(13)
C1 N1 H1 117.5
C9 N1 H1 117.6
O1 C1 N1 120.45(13)
O1 C1 C2 123.16(13)
N1 C1 C2 116.37(13)
C3 C2 C1 121.09(13)
C3 C2 H2A 119.5
C1 C2 H2A 119.5
C2 C3 C4 121.21(14)
C2 C3 C10 116.44(13)
C4 C3 C10 122.35(14)
C9 C4 C5 118.25(13)
C9 C4 C3 117.03(14)
C5 C4 C3 124.70(14)
C6 C5 C4 120.36(15)
C6 C5 H5 119.8
C4 C5 H5 119.8
C5 C6 C7 120.38(15)
C5 C6 H6 119.8
C7 C6 H6 119.8
C8 C7 C6 120.79(14)
C8 C7 H7 119.6
C6 C7 H7 119.6
C7 C8 C9 119.15(14)
C7 C8 H8 120.4
C9 C8 H8 120.4
N1 C9 C8 119.41(14)
N1 C9 C4 119.54(13)
C8 C9 C4 121.05(14)
O3 C10 O2 124.87(14)
O3 C10 C3 122.70(14)
O2 C10 C3 112.36(12)
C20 O6 H6A 109.7
C11 N2 C19 124.34(13)
C11 N2 H2B 116.2
C19 N2 H2B 119.3
O4 C11 N2 119.30(14)
O4 C11 C12 123.55(14)
N2 C11 C12 117.15(13)
C13 C12 C11 120.77(14)
C13 C12 H12 119.6
C11 C12 H12 119.6
C12 C13 C14 121.06(14)
C12 C13 C20 116.39(14)
C14 C13 C20 122.55(13)
C19 C14 C15 117.74(14)
C19 C14 C13 117.11(13)
C15 C14 C13 125.13(14)
C16 C15 C14 120.87(15)
C16 C15 H15 119.6
C14 C15 H15 119.6
C15 C16 C17 120.29(14)
C15 C16 H16 119.9
C17 C16 H16 119.9
C18 C17 C16 120.60(15)
C18 C17 H17 119.7
C16 C17 H17 119.7
C17 C18 C19 119.20(15)
C17 C18 H18 120.4
C19 C18 H18 120.4
N2 C19 C18 119.21(13)
N2 C19 C14 119.49(14)
C18 C19 C14 121.29(14)
O5 C20 O6 125.33(15)
O5 C20 C13 121.30(14)
O6 C20 C13 113.37(14)
H7A O7 H7B 104.1
H8A O8 H8B 109.5
H8AA O8A H8AB 109.5
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
O1 C1 1.2558(19)
O2 C10 1.3242(19)
O2 H2 0.8700
O3 C10 1.2047(19)
N1 C1 1.3545(19)
N1 C9 1.3844(19)
N1 H1 0.9101
C1 C2 1.445(2)
C2 C3 1.353(2)
C2 H2A 0.9500
C3 C4 1.445(2)
C3 C10 1.508(2)
C4 C9 1.406(2)
C4 C5 1.413(2)
C5 C6 1.377(2)
C5 H5 0.9500
C6 C7 1.400(2)
C6 H6 0.9500
C7 C8 1.374(2)
C7 H7 0.9500
C8 C9 1.405(2)
C8 H8 0.9500
O4 C11 1.2661(18)
O5 C20 1.207(2)
O6 C20 1.3091(19)
O6 H6A 0.8703
N2 C11 1.348(2)
N2 C19 1.3836(19)
N2 H2B 0.9098
C11 C12 1.440(2)
C12 C13 1.358(2)
C12 H12 0.9500
C13 C14 1.444(2)
C13 C20 1.514(2)
C14 C19 1.410(2)
C14 C15 1.411(2)
C15 C16 1.377(2)
C15 H15 0.9500
C16 C17 1.400(2)
C16 H16 0.9500
C17 C18 1.377(2)
C17 H17 0.9500
C18 C19 1.403(2)
C18 H18 0.9500
O7 H7A 0.8700
O7 H7B 0.8701
O8 H8A 0.8700
O8 H8B 0.8702
O8A H8AA 0.8699
O8A H8AB 0.8700
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
O2 H2 O4 . 0.87 1.73 2.5734(15) 162 yes
N1 H1 O1 3_566 0.91 1.91 2.8100(17) 169 yes
O6 H6A O7 . 0.87 1.68 2.5423(17) 172 yes
N2 H2B O4 3_656 0.91 1.92 2.8229(16) 171 yes
O7 H7A O1 2_556 0.87 1.88 2.7336(16) 165 yes
O7 H7B O8 . 0.87 2.01 2.841(5) 159 yes
O7 H7B O8A . 0.87 1.85 2.713(4) 172 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
C9 N1 C1 O1 177.00(14)
C9 N1 C1 C2 -2.0(2)
O1 C1 C2 C3 -174.35(15)
N1 C1 C2 C3 4.6(2)
C1 C2 C3 C4 -3.9(2)
C1 C2 C3 C10 174.98(14)
C2 C3 C4 C9 0.4(2)
C10 C3 C4 C9 -178.41(14)
C2 C3 C4 C5 -178.18(15)
C10 C3 C4 C5 3.0(2)
C9 C4 C5 C6 0.1(2)
C3 C4 C5 C6 178.66(15)
C4 C5 C6 C7 -1.3(2)
C5 C6 C7 C8 1.1(2)
C6 C7 C8 C9 0.2(2)
C1 N1 C9 C8 178.27(15)
C1 N1 C9 C4 -1.4(2)
C7 C8 C9 N1 178.94(14)
C7 C8 C9 C4 -1.4(2)
C5 C4 C9 N1 -179.12(14)
C3 C4 C9 N1 2.2(2)
C5 C4 C9 C8 1.2(2)
C3 C4 C9 C8 -177.40(14)
C2 C3 C10 O3 46.5(2)
C4 C3 C10 O3 -134.67(17)
C2 C3 C10 O2 -130.40(15)
C4 C3 C10 O2 48.4(2)
C19 N2 C11 O4 -178.38(14)
C19 N2 C11 C12 1.1(2)
O4 C11 C12 C13 176.50(15)
N2 C11 C12 C13 -3.0(2)
C11 C12 C13 C14 2.6(2)
C11 C12 C13 C20 -177.53(14)
C12 C13 C14 C19 -0.4(2)
C20 C13 C14 C19 179.79(14)
C12 C13 C14 C15 177.96(15)
C20 C13 C14 C15 -1.9(2)
C19 C14 C15 C16 -0.4(2)
C13 C14 C15 C16 -178.72(15)
C14 C15 C16 C17 1.0(2)
C15 C16 C17 C18 -0.5(2)
C16 C17 C18 C19 -0.6(2)
C11 N2 C19 C18 -178.15(14)
C11 N2 C19 C14 1.1(2)
C17 C18 C19 N2 -179.57(14)
C17 C18 C19 C14 1.2(2)
C15 C14 C19 N2 -179.93(13)
C13 C14 C19 N2 -1.5(2)
C15 C14 C19 C18 -0.7(2)
C13 C14 C19 C18 177.75(14)
C12 C13 C20 O5 -43.5(2)
C14 C13 C20 O5 136.39(18)
C12 C13 C20 O6 135.88(16)
C14 C13 C20 O6 -44.3(2)

_cod_database_fobs_code 1543531
