#------------------------------------------------------------------------------
#$Date: 2016-02-21 02:03:34 +0200 (Sun, 21 Feb 2016) $
#$Revision: 176798 $
#$URL: svn://www.crystallography.net/cod/cif/2/23/66/2236677.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_2236677
loop_
_publ_author_name
'Kafka, Stanislav'
'Pevec, Andrej'
'Proisl, Karel'
'Kimmel, Roman'
'Košmrlj, Janez'
_publ_section_title
;
 3-Ethyl-3-hydroxy-8-methoxyquinoline-2,4(1H,3H)-dione
 monohydrate
;
_journal_coeditor_code           TK5162
_journal_issue                   11
_journal_name_full               'Acta Crystallographica Section E'
_journal_page_first              o3199
_journal_page_last               o3200
_journal_paper_doi               10.1107/S1600536812043280
_journal_volume                  68
_journal_year                    2012
_chemical_formula_iupac          'C12 H13 N O4, H2 O'
_chemical_formula_moiety         'C12 H13 N O4, H2 O'
_chemical_formula_sum            'C12 H15 N O5'
_chemical_formula_weight         253.25
_chemical_melting_point_gt       371
_chemical_melting_point_lt       372
_chemical_name_systematic
;
3-Ethyl-3-hydroxy-8-methoxyquinoline-2,4(1H,3H)-dione
monohydrate
;
_space_group_IT_number           61
_symmetry_cell_setting           orthorhombic
_symmetry_space_group_name_Hall  '-P 2ac 2ab'
_symmetry_space_group_name_H-M   'P b c a'
_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                 90.00
_cell_angle_gamma                90.00
_cell_formula_units_Z            8
_cell_length_a                   16.5055(4)
_cell_length_b                   8.8068(2)
_cell_length_c                   16.6690(4)
_cell_measurement_reflns_used    3161
_cell_measurement_temperature    293(2)
_cell_measurement_theta_max      27.48
_cell_measurement_theta_min      1.00
_cell_volume                     2423.02(10)
_computing_cell_refinement
;
DENZO and SCALEPACK (Otwinowski & Minor, 1997)
;
_computing_data_collection       'COLLECT (Nonius, 1998)'
_computing_data_reduction
;
DENZO and SCALEPACK (Otwinowski & Minor, 1997)
;
_computing_molecular_graphics
'PLATON (Spek, 2009) and DIAMOND (Brandenburg, 1999)'
_computing_publication_material  'WinGX (Farrugia, 1999)'
_computing_structure_refinement  'SHELXL97 (Sheldrick, 2008)'
_computing_structure_solution    'SIR92 (Altomare et al., 1994)'
_diffrn_ambient_temperature      293(2)
_diffrn_measured_fraction_theta_full 0.998
_diffrn_measured_fraction_theta_max 0.998
_diffrn_measurement_device_type
;
Nonius KappaCCD area-detector
;
_diffrn_measurement_method       'φ scans + 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  0.0189
_diffrn_reflns_av_sigmaI/netI    0.0249
_diffrn_reflns_limit_h_max       21
_diffrn_reflns_limit_h_min       -21
_diffrn_reflns_limit_k_max       11
_diffrn_reflns_limit_k_min       -11
_diffrn_reflns_limit_l_max       21
_diffrn_reflns_limit_l_min       -21
_diffrn_reflns_number            5200
_diffrn_reflns_theta_full        27.49
_diffrn_reflns_theta_max         27.49
_diffrn_reflns_theta_min         3.38
_diffrn_standards_number         0
_exptl_absorpt_coefficient_mu    0.109
_exptl_absorpt_correction_T_max  0.9786
_exptl_absorpt_correction_T_min  0.9476
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   '(SCALEPACK; Otwinowski & Minor, 1997)'
_exptl_crystal_colour            yellow
_exptl_crystal_density_diffrn    1.388
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       prism
_exptl_crystal_F_000             1072
_exptl_crystal_size_max          0.50
_exptl_crystal_size_mid          0.25
_exptl_crystal_size_min          0.20
_refine_diff_density_max         0.262
_refine_diff_density_min         -0.225
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.033
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     175
_refine_ls_number_reflns         2779
_refine_ls_number_restraints     3
_refine_ls_restrained_S_all      1.034
_refine_ls_R_factor_all          0.0685
_refine_ls_R_factor_gt           0.0442
_refine_ls_shift/su_max          0.0001
_refine_ls_shift/su_mean         0.0001
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'calc w=1/[σ²(Fo²)+(0.0662P)²+0.4669P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1147
_refine_ls_wR_factor_ref         0.1274
_reflns_number_gt                1963
_reflns_number_total             2779
_reflns_threshold_expression     I>2σ(I)
_cod_data_source_file            tk5162.cif
_cod_data_source_block           I
_cod_database_code               2236677
_cod_database_fobs_code          2236677
loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'-x+1/2, -y, z+1/2'
'x+1/2, -y+1/2, -z'
'-x, y+1/2, -z+1/2'
'-x, -y, -z'
'x-1/2, y, -z-1/2'
'-x-1/2, y-1/2, 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_symmetry_multiplicity
O O1 0.08014(8) 0.56475(12) 0.75104(6) 0.0505(3) Uani d . 1 1
O O2 0.04557(8) 0.18242(13) 0.56925(8) 0.0576(4) Uani d . 1 1
O O3 0.05871(8) 0.26982(13) 0.72594(7) 0.0527(3) Uani d . 1 1
H H3 0.0359 0.1965 0.7058 0.079 Uiso calc R 1 1
O O4 0.14902(8) 0.81485(13) 0.51080(7) 0.0542(3) Uani d . 1 1
N N1 0.11348(8) 0.61105(15) 0.62211(7) 0.0395(3) Uani d D 1 1
H H1N 0.1065(10) 0.7068(16) 0.6299(11) 0.047 Uiso d D 1 1
C C1 0.09586(9) 0.51728(17) 0.68405(8) 0.0374(3) Uani d . 1 1
C C2 0.10269(9) 0.34757(17) 0.66669(9) 0.0392(4) Uani d . 1 1
C C3 0.07607(9) 0.30617(16) 0.58203(10) 0.0408(4) Uani d . 1 1
C C4 0.09477(9) 0.41692(17) 0.51912(9) 0.0381(3) Uani d . 1 1
C C5 0.09051(10) 0.3782(2) 0.43780(10) 0.0481(4) Uani d . 1 1
H H5 0.0777 0.2795 0.4227 0.058 Uiso calc R 1 1
C C6 0.10534(11) 0.4863(2) 0.38047(10) 0.0527(4) Uani d . 1 1
H H6 0.1023 0.4608 0.3264 0.063 Uiso calc R 1 1
C C7 0.12485(10) 0.6336(2) 0.40285(9) 0.0492(4) Uani d . 1 1
H H7 0.1344 0.7062 0.3634 0.059 Uiso calc R 1 1
C C8 0.13022(9) 0.67423(18) 0.48253(9) 0.0410(4) Uani d . 1 1
C C9 0.11398(9) 0.56549(17) 0.54186(8) 0.0358(3) Uani d . 1 1
C C10 0.19372(10) 0.3023(2) 0.67026(10) 0.0523(4) Uani d . 1 1
H H10A 0.1986 0.1950 0.6581 0.063 Uiso calc R 1 1
H H10B 0.2228 0.3579 0.6291 0.063 Uiso calc R 1 1
C C11 0.23315(12) 0.3326(3) 0.74990(11) 0.0683(6) Uani d . 1 1
H H11A 0.2035 0.2817 0.7915 0.102 Uiso calc R 1 1
H H11B 0.2333 0.4399 0.7602 0.102 Uiso calc R 1 1
H H11C 0.2879 0.2957 0.7490 0.102 Uiso calc R 1 1
C C12 0.16490(14) 0.9320(2) 0.45424(12) 0.0670(6) Uani d . 1 1
H H12A 0.1179 0.9477 0.4214 0.101 Uiso calc R 1 1
H H12B 0.2099 0.9033 0.4210 0.101 Uiso calc R 1 1
H H12C 0.1777 1.0243 0.4822 0.101 Uiso calc R 1 1
O O1W 0.06321(11) 0.90745(16) 0.66799(10) 0.0752(5) Uani d D 1 1
H H1W 0.0478(14) 0.978(3) 0.6301(13) 0.090 Uiso d D 1 1
H H2W 0.0132(11) 0.900(3) 0.6914(14) 0.090 Uiso d D 1 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
C2 O3 H3 109.5
C8 O4 C12 118.23(14)
C1 N1 C9 123.82(13)
C1 N1 H1N 117.0(12)
C9 N1 H1N 115.2(12)
O1 C1 N1 122.32(14)
O1 C1 C2 121.64(13)
N1 C1 C2 115.90(12)
O3 C2 C3 112.71(13)
O3 C2 C1 107.81(12)
C3 C2 C1 112.89(12)
O3 C2 C10 110.35(13)
C3 C2 C10 104.65(12)
C1 C2 C10 108.35(13)
O2 C3 C4 123.84(15)
O2 C3 C2 119.69(14)
C4 C3 C2 116.32(13)
C9 C4 C5 120.10(14)
C9 C4 C3 118.46(13)
C5 C4 C3 121.38(14)
C6 C5 C4 119.83(16)
C6 C5 H5 120.1
C4 C5 H5 120.1
C5 C6 C7 120.20(15)
C5 C6 H6 119.9
C7 C6 H6 119.9
C8 C7 C6 121.09(16)
C8 C7 H7 119.5
C6 C7 H7 119.5
O4 C8 C7 125.75(15)
O4 C8 C9 114.89(13)
C7 C8 C9 119.34(15)
N1 C9 C4 121.80(13)
N1 C9 C8 118.71(13)
C4 C9 C8 119.41(13)
C11 C10 C2 114.01(15)
C11 C10 H10A 108.8
C2 C10 H10A 108.8
C11 C10 H10B 108.8
C2 C10 H10B 108.8
H10A C10 H10B 107.6
C10 C11 H11A 109.5
C10 C11 H11B 109.5
H11A C11 H11B 109.5
C10 C11 H11C 109.5
H11A C11 H11C 109.5
H11B C11 H11C 109.5
O4 C12 H12A 109.5
O4 C12 H12B 109.5
H12A C12 H12B 109.5
O4 C12 H12C 109.5
H12A C12 H12C 109.5
H12B C12 H12C 109.5
H1W O1W H2W 95(2)
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
O1 C1 1.2202(17)
O2 C3 1.2193(19)
O3 C2 1.4040(18)
O3 H3 0.8200
O4 C8 1.361(2)
O4 C12 1.422(2)
N1 C1 1.3537(19)
N1 C9 1.3966(18)
N1 H1N 0.861(14)
C1 C2 1.527(2)
C2 C3 1.522(2)
C2 C10 1.555(2)
C3 C4 1.465(2)
C4 C9 1.399(2)
C4 C5 1.399(2)
C5 C6 1.371(3)
C5 H5 0.9300
C6 C7 1.388(3)
C6 H6 0.9300
C7 C8 1.378(2)
C7 H7 0.9300
C8 C9 1.402(2)
C10 C11 1.502(2)
C10 H10A 0.9700
C10 H10B 0.9700
C11 H11A 0.9600
C11 H11B 0.9600
C11 H11C 0.9600
C12 H12A 0.9600
C12 H12B 0.9600
C12 H12C 0.9600
O1W H1W 0.923(16)
O1W H2W 0.916(16)
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
O3 H3 O1 4_546 0.82 2.35 2.9430(17) 130
N1 H1N O1W . 0.861(14) 2.009(15) 2.8438(19) 163.1(17)
O1W H1W O2 1_565 0.923(16) 2.065(19) 2.9425(19) 158(2)
O1W H2W O3 4_556 0.916(16) 2.15(2) 2.9401(19) 144(2)
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 -165.15(15)
C9 N1 C1 C2 19.1(2)
O1 C1 C2 O3 22.8(2)
N1 C1 C2 O3 -161.35(13)
O1 C1 C2 C3 147.98(15)
N1 C1 C2 C3 -36.19(18)
O1 C1 C2 C10 -96.60(17)
N1 C1 C2 C10 79.22(16)
O3 C2 C3 O2 -26.4(2)
C1 C2 C3 O2 -148.87(14)
C10 C2 C3 O2 93.51(17)
O3 C2 C3 C4 157.87(13)
C1 C2 C3 C4 35.42(18)
C10 C2 C3 C4 -82.20(16)
O2 C3 C4 C9 167.10(15)
C2 C3 C4 C9 -17.4(2)
O2 C3 C4 C5 -10.3(2)
C2 C3 C4 C5 165.20(14)
C9 C4 C5 C6 0.1(2)
C3 C4 C5 C6 177.47(15)
C4 C5 C6 C7 0.2(2)
C5 C6 C7 C8 0.4(3)
C12 O4 C8 C7 -0.1(3)
C12 O4 C8 C9 -178.93(16)
C6 C7 C8 O4 179.85(16)
C6 C7 C8 C9 -1.4(2)
C1 N1 C9 C4 0.9(2)
C1 N1 C9 C8 177.65(14)
C5 C4 C9 N1 175.61(14)
C3 C4 C9 N1 -1.8(2)
C5 C4 C9 C8 -1.1(2)
C3 C4 C9 C8 -178.52(14)
O4 C8 C9 N1 3.8(2)
C7 C8 C9 N1 -175.08(14)
O4 C8 C9 C4 -179.40(14)
C7 C8 C9 C4 1.7(2)
O3 C2 C10 C11 -58.1(2)
C3 C2 C10 C11 -179.62(16)
C1 C2 C10 C11 59.70(19)
