#------------------------------------------------------------------------------
#$Date: 2017-10-13 09:09:21 +0300 (Fri, 13 Oct 2017) $
#$Revision: 201973 $
#$URL: file:///home/coder/svn-repositories/cod/cif/2/20/23/2202335.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_2202335
loop_
_publ_author_name
'Pozzi, C. Gustavo'
'Goeta, Andrés E.'
'Autino, Juan C.'
'Punte, Graciela'
_publ_section_title
;
 3-Ethoxycarbonyl-4-hydroxy-6-(methoxymethoxy)-1-methyl-2-quinolone
;
_journal_issue                   8
_journal_name_full               'Acta Crystallographica Section E'
_journal_page_first              o1196
_journal_page_last               o1198
_journal_paper_doi               10.1107/S1600536803016192
_journal_volume                  59
_journal_year                    2003
_chemical_formula_iupac          'C15 H17 N O6'
_chemical_formula_moiety         'C15 H17 N O6'
_chemical_formula_sum            'C15 H17 N O6'
_chemical_formula_weight         307.30
_chemical_name_systematic
;
3-ethoxycarbonyl-4-hydroxy-6-methoxymethyleneoxy-1-methyl-2-quinolone
;
_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   difmap
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_audit_creation_method           SHELXL97
_cell_angle_alpha                90.00
_cell_angle_beta                 98.823(3)
_cell_angle_gamma                90.00
_cell_formula_units_Z            4
_cell_length_a                   11.558(3)
_cell_length_b                   10.476(2)
_cell_length_c                   11.750(2)
_cell_measurement_reflns_used    755
_cell_measurement_temperature    100(2)
_cell_measurement_theta_max      24.33
_cell_measurement_theta_min      13.71
_cell_volume                     1405.9(5)
_computing_cell_refinement       SMART-NT
_computing_data_collection       'SMART-NT (Bruker, 1998)'
_computing_data_reduction        'SAINT-NT (Bruker, 1998)'
_computing_molecular_graphics    'ORTEP-3 for Windows (Farrugia, 1997)'
_computing_publication_material  'SHELXTL-NT (Bruker, 1998)'
_computing_structure_refinement  'SHELXL97 (Sheldrick, 1997)'
_computing_structure_solution    'SHELXS97 (Sheldrick, 1990)'
_diffrn_ambient_temperature      100(2)
_diffrn_measured_fraction_theta_full 0.931
_diffrn_measured_fraction_theta_max 0.931
_diffrn_measurement_device_type  'Bruker SMART 1K CCD'
_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  0.0369
_diffrn_reflns_av_sigmaI/netI    0.0290
_diffrn_reflns_limit_h_max       15
_diffrn_reflns_limit_h_min       -16
_diffrn_reflns_limit_k_max       14
_diffrn_reflns_limit_k_min       -14
_diffrn_reflns_limit_l_max       16
_diffrn_reflns_limit_l_min       -16
_diffrn_reflns_number            16953
_diffrn_reflns_theta_full        30.39
_diffrn_reflns_theta_max         30.39
_diffrn_reflns_theta_min         1.78
_diffrn_standards_decay_%        0
_diffrn_standards_number         0
_exptl_absorpt_coefficient_mu    0.113
_exptl_absorpt_correction_type   none
_exptl_crystal_colour            colourless
_exptl_crystal_density_diffrn    1.445
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       'irregular shape'
_exptl_crystal_F_000             648
_exptl_crystal_size_max          0.36
_exptl_crystal_size_mid          0.26
_exptl_crystal_size_min          0.18
_refine_diff_density_max         0.358
_refine_diff_density_min         -0.286
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.011
_refine_ls_hydrogen_treatment    refall
_refine_ls_matrix_type           full
_refine_ls_number_parameters     267
_refine_ls_number_reflns         3978
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.011
_refine_ls_R_factor_all          0.0660
_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
'calc w = 1/[σ²(Fo²)+(0.0632P)²+0.3584P] where P = (Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1025
_refine_ls_wR_factor_ref         0.1159
_reflns_number_gt                2908
_reflns_number_total             3978
_reflns_threshold_expression     I>2σ(I)
_cod_data_source_file            bt6304.cif
_cod_data_source_block           I
_cod_original_sg_symbol_H-M      'P 21/c'
_cod_database_code               2202335
_cod_database_fobs_code          2202335
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_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
N1 -0.10217(9) 0.49877(10) 0.31837(9) 0.0167(2) Uani d . 1 . . N
C2 -0.17015(11) 0.41122(12) 0.36837(10) 0.0170(2) Uani d . 1 . . C
C3 -0.10626(11) 0.31269(12) 0.44051(10) 0.0162(2) Uani d . 1 . . C
C4A 0.08094(10) 0.39480(12) 0.39502(10) 0.0159(2) Uani d . 1 . . C
C4 0.01511(11) 0.30558(12) 0.45308(10) 0.0156(2) Uani d . 1 . . C
C5 0.20385(11) 0.38476(12) 0.40468(10) 0.0172(2) Uani d . 1 . . C
H5 0.2407(14) 0.3171(16) 0.4490(13) 0.020(4) Uiso d . 1 . . H
C6 0.26489(11) 0.47201(13) 0.34883(11) 0.0185(3) Uani d . 1 . . C
C7 0.20362(12) 0.56976(13) 0.28376(11) 0.0204(3) Uani d . 1 . . C
H7 0.2476(16) 0.6305(16) 0.2434(15) 0.030(4) Uiso d . 1 . . H
C8A 0.01903(10) 0.49094(12) 0.32839(10) 0.0162(2) Uani d . 1 . . C
C8 0.08353(11) 0.57944(13) 0.27316(11) 0.0192(3) Uani d . 1 . . C
H8 0.0435(14) 0.6471(16) 0.2291(14) 0.024(4) Uiso d . 1 . . H
C9 -0.16595(11) 0.21633(12) 0.50186(10) 0.0172(2) Uani d . 1 . . C
O10 -0.28169(8) 0.22102(9) 0.48625(8) 0.0201(2) Uani d . 1 . . O
C11 -0.34014(12) 0.12130(14) 0.54398(12) 0.0219(3) Uani d . 1 . . C
H11B -0.2986(14) 0.1111(15) 0.6211(14) 0.021(4) Uiso d . 1 . . H
H11A -0.4156(15) 0.1570(16) 0.5453(13) 0.023(4) Uiso d . 1 . . H
C12 -0.34791(13) -0.00083(14) 0.47535(13) 0.0259(3) Uani d . 1 . . C
H12C -0.3935(16) 0.0134(17) 0.3985(16) 0.031(4) Uiso d . 1 . . H
H12B -0.3837(16) -0.0683(18) 0.5173(15) 0.034(5) Uiso d . 1 . . H
H12A -0.2683(17) -0.0352(18) 0.4637(15) 0.035(5) Uiso d . 1 . . H
O13 -0.11068(8) 0.13483(9) 0.56458(8) 0.0225(2) Uani d . 1 . . O
O14 0.07756(8) 0.21692(9) 0.51637(8) 0.0200(2) Uani d . 1 . . O
H14 0.025(2) 0.172(2) 0.5492(18) 0.051(6) Uiso d . 1 . . H
O15 -0.27786(8) 0.42042(10) 0.35004(8) 0.0245(2) Uani d . 1 . . O
C16 -0.16336(12) 0.60044(13) 0.24695(12) 0.0202(3) Uani d . 1 . . C
H16C -0.1358(15) 0.6839(17) 0.2792(14) 0.025(4) Uiso d . 1 . . H
H16B -0.2440(17) 0.5932(17) 0.2538(15) 0.032(5) Uiso d . 1 . . H
H16A -0.1508(14) 0.5914(16) 0.1674(14) 0.023(4) Uiso d . 1 . . H
O17 0.38414(8) 0.47260(9) 0.35095(8) 0.0215(2) Uani d . 1 . . O
C18 0.45109(12) 0.37448(13) 0.41508(12) 0.0218(3) Uani d . 1 . . C
H18B 0.4336(14) 0.3724(15) 0.4930(14) 0.019(4) Uiso d . 1 . . H
H18A 0.5313(15) 0.4014(16) 0.4119(14) 0.026(4) Uiso d . 1 . . H
O19 0.42767(8) 0.25349(9) 0.36709(8) 0.0225(2) Uani d . 1 . . O
C20 0.46905(14) 0.23784(16) 0.25916(13) 0.0278(3) Uani d . 1 . . C
H20C 0.4628(15) 0.1462(18) 0.2392(15) 0.028(4) Uiso d . 1 . . H
H20B 0.4212(17) 0.2879(18) 0.2002(16) 0.034(5) Uiso d . 1 . . H
H20A 0.552(2) 0.2680(19) 0.2675(17) 0.045(6) Uiso d . 1 . . H
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
C8A N1 C2 123.44(10)
C8A N1 C16 118.81(10)
C2 N1 C16 117.68(10)
O15 C2 N1 119.57(11)
O15 C2 C3 124.23(11)
N1 C2 C3 116.19(10)
C4 C3 C2 120.75(11)
C4 C3 C9 116.90(11)
C2 C3 C9 122.35(11)
C8A C4A C5 121.29(11)
C8A C4A C4 117.95(11)
C5 C4A C4 120.76(11)
O14 C4 C3 123.28(11)
O14 C4 C4A 115.88(11)
C3 C4 C4A 120.83(11)
C6 C5 C4A 119.59(12)
C6 C5 H5 122.7(10)
C4A C5 H5 117.7(10)
O17 C6 C5 125.34(12)
O17 C6 C7 115.31(11)
C5 C6 C7 119.36(12)
C8 C7 C6 121.34(12)
C8 C7 H7 119.9(11)
C6 C7 H7 118.7(11)
N1 C8A C4A 120.72(11)
N1 C8A C8 121.31(11)
C4A C8A C8 117.97(11)
C7 C8 C8A 120.44(12)
C7 C8 H8 120.1(10)
C8A C8 H8 119.5(10)
O13 C9 O10 121.74(11)
O13 C9 C3 121.75(11)
O10 C9 C3 116.51(11)
C9 O10 C11 115.93(10)
O10 C11 C12 110.57(11)
O10 C11 H11B 108.4(9)
C12 C11 H11B 112.9(10)
O10 C11 H11A 102.5(10)
C12 C11 H11A 111.3(10)
H11B C11 H11A 110.7(13)
C11 C12 H12C 110.0(10)
C11 C12 H12B 109.6(10)
H12C C12 H12B 111.0(15)
C11 C12 H12A 113.1(11)
H12C C12 H12A 107.3(14)
H12B C12 H12A 105.7(15)
C4 O14 H14 104.7(14)
N1 C16 H16C 108.9(10)
N1 C16 H16B 106.7(11)
H16C C16 H16B 107.5(14)
N1 C16 H16A 110.4(10)
H16C C16 H16A 111.7(14)
H16B C16 H16A 111.5(14)
C6 O17 C18 117.80(10)
O19 C18 O17 112.57(11)
O19 C18 H18B 107.8(9)
O17 C18 H18B 109.8(9)
O19 C18 H18A 111.9(10)
O17 C18 H18A 102.3(10)
H18B C18 H18A 112.4(13)
C18 O19 C20 113.02(11)
O19 C20 H20C 107.4(10)
O19 C20 H20B 109.8(11)
H20C C20 H20B 110.1(14)
O19 C20 H20A 108.9(12)
H20C C20 H20A 111.3(15)
H20B C20 H20A 109.4(16)
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
O13 C9 . 1.2392(16) ?
C9 C3 . 1.4721(17) ?
C3 C4 . 1.3899(17) ?
C4 O14 . 1.3312(15) ?
N1 C8A . 1.3901(16) ?
N1 C2 . 1.3948(16) ?
N1 C16 . 1.4686(16) ?
C2 O15 . 1.2342(15) ?
C2 C3 . 1.4619(17) ?
C4A C8A . 1.4027(17) ?
C4A C5 . 1.4116(17) ?
C4A C4 . 1.4412(17) ?
C5 C6 . 1.3805(18) ?
C5 H5 . 0.941(17) ?
C6 O17 . 1.3747(15) ?
C6 C7 . 1.4030(19) ?
C7 C8 . 1.3782(19) ?
C7 H7 . 0.981(18) ?
C8A C8 . 1.4088(17) ?
C8 H8 . 0.955(17) ?
C9 O10 . 1.3230(15) ?
O10 C11 . 1.4657(15) ?
C11 C12 . 1.508(2) ?
C11 H11B . 0.964(16) ?
C11 H11A . 0.951(17) ?
C12 H12C . 0.984(18) ?
C12 H12B . 0.988(19) ?
C12 H12A . 1.016(19) ?
O14 H14 . 0.90(2) ?
C16 H16C . 0.986(18) ?
C16 H16B . 0.95(2) ?
C16 H16A . 0.972(16) ?
O17 C18 . 1.4298(16) ?
C18 O19 . 1.3968(17) ?
C18 H18B . 0.967(16) ?
C18 H18A . 0.975(17) ?
O19 C20 . 1.4318(17) ?
C20 H20C . 0.988(18) ?
C20 H20B . 0.971(19) ?
C20 H20A . 1.00(2) ?
loop_
_geom_hbond_atom_site_label_D
_geom_hbond_atom_site_label_H
_geom_hbond_atom_site_label_A
_geom_hbond_distance_DH
_geom_hbond_distance_HA
_geom_hbond_distance_DA
_geom_hbond_angle_DHA
O14 H14 O13 0.90(2) 1.65(2) 2.4844(14) 153(2)
loop_
_cod_related_entry_id
_cod_related_entry_database
_cod_related_entry_code
1 ChemSpider 21131597
