#------------------------------------------------------------------------------
#$Date: 2025-08-19 09:12:48 +0300 (Tue, 19 Aug 2025) $
#$Revision: 301798 $
#$URL: file:///home/coder/svn-repositories/cod/cif/2/01/19/2011925.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_2011925
loop_
_publ_author_name
'Kettmann, Viktor'
'Světlík, Jan'
'Kratky, Christoph'
_publ_section_title
4-Hydroxy-7-methoxy-2-methyl-5H-1-benzopyrano[4,3-b]pyridin-5-one
_journal_issue                   5
_journal_name_full               'Acta Crystallographica Section C'
_journal_page_first              590
_journal_page_last               592
_journal_paper_doi               10.1107/S0108270101002360
_journal_volume                  57
_journal_year                    2001
_chemical_formula_moiety         'C14 H11 N O4'
_chemical_formula_sum            'C14 H11 N O4'
_chemical_formula_weight         257.24
_chemical_melting_point          480
_chemical_name_systematic
;
4-hydroxy-7-methoxy-2-methyl-5H-1-benzopyrano[4,3-b]pyridin-5-one
;
_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'
_cell_angle_alpha                90
_cell_angle_beta                 95.05(4)
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   7.333(3)
_cell_length_b                   9.389(4)
_cell_length_c                   17.161(7)
_cell_measurement_reflns_used    25
_cell_measurement_temperature    293(2)
_cell_measurement_theta_max      21
_cell_measurement_theta_min      7
_cell_volume                     1176.9(8)
_computing_cell_refinement       XSCANS
_computing_data_collection       'XSCANS (Siemens, 1991)'
_computing_data_reduction        XSCANS
_computing_molecular_graphics    'ORTEPII (Johnson, 1976)'
_computing_publication_material  SHELXL97
_computing_structure_refinement  'SHELXL97 (Sheldrick, 1997)'
_computing_structure_solution    'SHELXS97 (Sheldrick, 1990)'
_diffrn_ambient_temperature      293(2)
_diffrn_measurement_device       'Siemens P4'
_diffrn_measurement_method       ω/2θ
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_source         'fine-focus sealed tube'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     .71073
_diffrn_reflns_av_R_equivalents  .045
_diffrn_reflns_limit_h_max       1
_diffrn_reflns_limit_h_min       -9
_diffrn_reflns_limit_k_max       12
_diffrn_reflns_limit_k_min       -1
_diffrn_reflns_limit_l_max       22
_diffrn_reflns_limit_l_min       -22
_diffrn_reflns_number            3692
_diffrn_reflns_theta_max         27.51
_diffrn_reflns_theta_min         2.38
_diffrn_standards_decay_%        2
_diffrn_standards_interval_count 97
_diffrn_standards_number         3
_exptl_absorpt_coefficient_mu    .108
_exptl_absorpt_correction_type   none
_exptl_crystal_colour            colourless
_exptl_crystal_density_diffrn    1.452
_exptl_crystal_density_meas      1.450(10)
_exptl_crystal_density_method    'flotation in bromoform/c-hexane'
_exptl_crystal_description       plate
_exptl_crystal_F_000             536
_exptl_crystal_size_max          .35
_exptl_crystal_size_mid          .30
_exptl_crystal_size_min          .10
_refine_diff_density_max         .25
_refine_diff_density_min         -.32
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.022
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     172
_refine_ls_number_reflns         2698
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.022
_refine_ls_R_factor_all          .101
_refine_ls_R_factor_gt           .054
_refine_ls_shift/su_max          .001
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'calc w = 1/[σ²(Fo²)+(0.1035P)²+0.1985P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_all         .185
_refine_ls_wR_factor_ref         .150
_reflns_number_gt                1543
_reflns_number_total             2698
_reflns_threshold_expression     I>2σ(I)
_cod_data_source_file            av1068.cif
_cod_data_source_block           2e
_cod_original_sg_symbol_H-M      'P 21/c'
_cod_database_code               2011925
_cod_database_fobs_code          2011925
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 .8137(3) -.0282(2) -.10363(10) .0390(5) Uani d . 1 . . N
C2 .8672(3) .0677(3) -.15599(13) .0426(6) Uani d . 1 . . C
C3 .8833(3) .2119(3) -.14082(14) .0460(6) Uani d . 1 . . C
C4 .8497(3) .2642(2) -.06828(14) .0423(6) Uani d . 1 . . C
O4 .8688(3) .40450(18) -.05292(11) .0609(6) Uani d . 1 . . O
C4a .7956(3) .1664(2) -.01198(12) .0358(5) Uani d . 1 . . C
C5 .7589(3) .2162(2) .06476(13) .0413(6) Uani d . 1 . . C
O5 .7743(3) .33918(18) .08727(11) .0618(6) Uani d . 1 . . O
O6 .7034(2) .11987(17) .11734(9) .0439(5) Uani d . 1 . . O
C6a .6821(3) -.0229(2) .09770(13) .0362(5) Uani d . 1 . . C
C7 .6264(3) -.1114(3) .15770(13) .0414(6) Uani d . 1 . . C
O7 .6004(3) -.0459(2) .22669(9) .0536(5) Uani d . 1 . . O
C8 .6026(4) -.2551(3) .14168(15) .0483(6) Uani d . 1 . . C
C9 .6362(4) -.3100(3) .06881(16) .0488(6) Uani d . 1 . . C
C10 .6929(3) -.2227(2) .01079(14) .0425(6) Uani d . 1 . . C
C10a .7169(3) -.0762(2) .02503(12) .0347(5) Uani d . 1 . . C
C10b .7776(3) .0230(2) -.03319(12) .0334(5) Uani d . 1 . . C
C11 .9114(4) .0071(3) -.23303(14) .0565(7) Uani d . 1 . . C
C12 .5763(5) -.1362(4) .29246(17) .0751(10) Uani d . 1 . . C
HO4 .8531 .4149 .0033 .073 Uiso d . 1 . . H
H3 .9156 .2809 -.1806 .055 Uiso d . 1 . . H
H8 .5627 -.3146 .1804 .058 Uiso d . 1 . . H
H9 .6170 -.4115 .0617 .058 Uiso d . 1 . . H
H10 .7207 -.2607 -.0387 .051 Uiso d . 1 . . H
H11A .9587 .0812 -.2672 .086 Uiso d . 1 . . H
H11B 1.0184 -.0540 -.2292 .086 Uiso d . 1 . . H
H11C .8032 -.0087 -.2631 .086 Uiso d . 1 . . H
H12A .4485 -.2038 .2789 .112 Uiso d . 1 . . H
H12B .5579 -.0763 .3356 .112 Uiso d . 1 . . H
H12C .6832 -.2008 .3031 .112 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 .0033 .0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
H H .0000 .0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
N N .0061 .0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O .0106 .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
C10b N1 C2 116.7(2) yes
N1 C2 C3 123.5(2) yes
N1 C2 C11 115.5(2) ?
C3 C2 C11 121.1(2) ?
C4 C3 C2 119.9(2) yes
O4 C4 C3 120.0(2) ?
O4 C4 C4a 122.1(2) ?
C3 C4 C4a 117.9(2) yes
C10b C4a C4 118.2(2) yes
C10b C4a C5 121.88(19) ?
C4 C4a C5 119.9(2) ?
O5 C5 O6 116.3(2) ?
O5 C5 C4a 125.1(2) ?
O6 C5 C4a 118.6(2) yes
C5 O6 C6a 120.87(17) yes
O6 C6a C10a 122.77(19) ?
O6 C6a C7 115.18(19) ?
C10a C6a C7 122.0(2) ?
O7 C7 C8 126.0(2) ?
O7 C7 C6a 116.0(2) ?
C8 C7 C6a 118.0(2) ?
C7 O7 C12 116.9(2) ?
C7 C8 C9 120.6(2) ?
C10 C9 C8 121.0(2) ?
C9 C10 C10a 119.8(2) ?
C6a C10a C10 118.6(2) ?
C6a C10a C10b 118.3(2) ?
C10 C10a C10b 123.0(2) ?
N1 C10b C4a 123.70(19) yes
N1 C10b C10a 118.75(19) ?
C4a C10b C10a 117.55(19) ?
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
N1 C10b . 1.349(3) yes
N1 C2 . 1.354(3) yes
C2 C3 . 1.382(4) yes
C2 C11 . 1.501(3) ?
C3 C4 . 1.380(3) yes
C4 O4 . 1.348(3) yes
C4 C4a . 1.415(3) yes
C4a C10b . 1.398(3) yes
C4a C5 . 1.445(3) yes
C5 O5 . 1.220(3) yes
C5 O6 . 1.365(3) yes
O6 C6a . 1.387(3) yes
C6a C10a . 1.388(3) yes
C6a C7 . 1.411(3) ?
C7 O7 . 1.363(3) ?
C7 C8 . 1.385(4) ?
O7 C12 . 1.435(3) ?
C8 C9 . 1.395(4) ?
C9 C10 . 1.382(3) ?
C10 C10a . 1.405(3) ?
C10a C10b . 1.463(3) yes
C3 H3 . .985 ?
O4 HO4 . .987 ?
C8 H8 . .934 ?
C9 H9 . .969 ?
C10 H10 . .960 ?
C11 H11A . .992 ?
C11 H11B . .970 ?
C11 H11C . .920 ?
C12 H12A . 1.138 ?
C12 H12B . .948 ?
C12 H12C . .995 ?
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
_geom_torsion_publ_flag
C10b N1 C2 C3 -.8(3) ?
C10b N1 C2 C11 178.4(2) ?
N1 C2 C3 C4 2.1(4) ?
C11 C2 C3 C4 -177.1(2) ?
C2 C3 C4 O4 178.7(2) ?
C2 C3 C4 C4a -1.3(4) ?
O4 C4 C4a C10b 179.4(2) ?
C3 C4 C4a C10b -.6(3) ?
O4 C4 C4a C5 .0(4) ?
C3 C4 C4a C5 -180.0(2) ?
C10b C4a C5 O5 179.0(2) ?
C4 C4a C5 O5 -1.7(4) ?
C10b C4a C5 O6 -.7(4) ?
C4 C4a C5 O6 178.7(2) ?
O5 C5 O6 C6a -179.8(2) ?
C4a C5 O6 C6a -.1(3) ?
C5 O6 C6a C10a .6(3) ?
C5 O6 C6a C7 179.2(2) ?
O6 C6a C7 O7 .2(3) ?
C10a C6a C7 O7 178.7(2) ?
O6 C6a C7 C8 179.9(2) ?
C10a C6a C7 C8 -1.5(4) ?
C8 C7 O7 C12 11.1(4) yes
C6a C7 O7 C12 -169.1(2) ?
O7 C7 C8 C9 -179.1(2) ?
C6a C7 C8 C9 1.2(4) ?
C7 C8 C9 C10 -.4(4) ?
C8 C9 C10 C10a -.1(4) ?
O6 C6a C10a C10 179.5(2) ?
C7 C6a C10a C10 1.0(3) ?
O6 C6a C10a C10b -.3(3) ?
C7 C6a C10a C10b -178.8(2) ?
C9 C10 C10a C6a -.2(4) ?
C9 C10 C10a C10b 179.6(2) ?
C2 N1 C10b C4a -1.2(3) ?
C2 N1 C10b C10a 179.2(2) ?
C4 C4a C10b N1 1.9(3) ?
C5 C4a C10b N1 -178.7(2) ?
C4 C4a C10b C10a -178.4(2) ?
C5 C4a C10b C10a .9(3) ?
C6a C10a C10b N1 179.24(19) ?
C10 C10a C10b N1 -.5(3) ?
C6a C10a C10b C4a -.4(3) ?
C10 C10a C10b C4a 179.8(2) ?
loop_
_cod_related_entry_id
_cod_related_entry_database
_cod_related_entry_code
1 ChemSpider 8810242
2 PubChem 10634880
