data_2011925
_journal_name_full  'Acta Crystallographica, Section C'
_journal_year  2001
_journal_volume  57
_journal_page_first  590
_journal_page_last  592
_publ_section_title
;
4-Hydroxy-7-methoxy-2-methyl-5H-1-benzopyrano[4,3-b]pyridin-5-one
;
loop_
_publ_author_name
  'Kettmann, Viktor'
  "Sv\<etl\'ik, Jan"
  'Kratky, Christoph'
_chemical_formula_moiety  'C14 H11 N O4'
_chemical_formula_sum  'C14 H11 N O4'
_chemical_formula_weight  257.24
_chemical_melting_point  480
_symmetry_cell_setting  'monoclinic'
_symmetry_space_group_name_H-M  'P 21/c'
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'
_cell_length_a  7.333(3)
_cell_length_b  9.389(4)
_cell_length_c  17.161(7)
_cell_angle_alpha  90
_cell_angle_beta  95.05(4)
_cell_angle_gamma  90
_cell_volume  1176.9(8)
_cell_formula_units_Z  4
_cell_measurement_temperature  293(2)
_exptl_crystal_density_diffrn  1.452
_exptl_crystal_density_meas  1.450(10)
_diffrn_ambient_temperature  293(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_site_aniso_label
_atom_site_aniso_U_11
_atom_site_aniso_U_22
_atom_site_aniso_U_33
_atom_site_aniso_U_12
_atom_site_aniso_U_13
_atom_site_aniso_U_23
  N1  .0399(11)  .0431(11)  .0349(10)  .0021(9)  .0078(8)  -.0028(8)
  C2  .0389(12)  .0552(14)  .0346(11)  -.0015(11)  .0080(9)  .0007(10)
  C3  .0474(14)  .0499(14)  .0423(13)  -.0047(11)  .0134(11)  .0094(10)
  C4  .0432(13)  .0365(12)  .0483(13)  -.0016(10)  .0097(10)  .0049(10)
  O4  .0872(15)  .0371(10)  .0618(12)  -.0078(9)  .0255(11)  .0041(8)
  C4a  .0387(12)  .0352(11)  .0343(10)  .0037(9)  .0076(9)  .0024(9)
  C5  .0506(14)  .0353(12)  .0394(12)  .0029(10)  .0119(10)  -.0012(9)
  O5  .0978(16)  .0371(10)  .0542(11)  -.0059(10)  .0278(11)  -.0089(8)
  O6  .0625(11)  .0360(8)  .0356(8)  .0014(8)  .0167(8)  -.0006(6)
  C6a  .0390(12)  .0328(11)  .0379(11)  .0038(9)  .0086(9)  .0021(9)
  C7  .0413(13)  .0465(13)  .0378(11)  .0061(10)  .0114(10)  .0086(10)
  O7  .0705(12)  .0568(11)  .0361(9)  .0061(9)  .0191(8)  .0079(8)
  C8  .0485(14)  .0472(14)  .0501(14)  .0007(11)  .0104(11)  .0154(11)
  C9  .0502(15)  .0355(12)  .0615(16)  .0018(11)  .0101(12)  .0051(11)
  C10  .0468(14)  .0364(12)  .0447(12)  .0013(10)  .0064(10)  -.0013(10)
  C10a  .0347(11)  .0353(11)  .0344(11)  .0030(9)  .0050(9)  .0016(9)
  C10b  .0317(11)  .0359(11)  .0330(11)  .0037(9)  .0051(8)  .0002(8)
  C11  .0560(16)  .079(2)  .0363(12)  .0015(14)  .0120(11)  -.0047(12)
  C12  .108(3)  .074(2)  .0482(15)  .0243(19)  .0347(17)  .0258(14)
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 ?