#------------------------------------------------------------------------------
#$Date: 2008-11-20 19:58:43 +0000 (Thu, 20 Nov 2008) $
#$Revision: 481 $
#$URL: svn://www.crystallography.net/cod/cif/2/2008803.cif $
#------------------------------------------------------------------------------
#
# This file is available in the Crystallography Open Database (COD),
# http://www.crystallography.net/
#
# All data on this site have been placed in the public domain by the
# contributors.
#
data_2008803
_journal_name_full 'Acta Crystallographica Section C'
_journal_year  1999
_journal_volume 55
_journal_page_first  1313
_journal_page_last  1315
_publ_section_title
;
X-ray investigations of benzopyran derivatives substituted in position 3.
;
loop_
_publ_author_name
  'Rybarczyk, Agnieszka J.'
  'Olszak, Tomasz A.'
  'Ma\/lecka, Magdalena'
  'Nawrot-Modranka, Jolanta'
_chemical_formula_moiety  'C13 H15 N2 O5 P S'
_chemical_formula_sum  'C13 H15 N2 O5 P S'
_chemical_formula_analytical  'C13 H15 N2 O5 P S'
_chemical_formula_weight  342.30
_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  10.866(2)
_cell_length_b  12.3900(10)
_cell_length_c  11.8450(10)
_cell_angle_alpha  90.00
_cell_angle_beta  101.200(10)
_cell_angle_gamma  90.00
_cell_volume  1564.3(4)
_cell_formula_units_Z  4
_cell_measurement_temperature  293(2)
_exptl_crystal_density_diffrn  1.453
_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
  P1 0.42727(5) 0.55808(5) 0.21463(5) 0.05111(18) Uani d . 1 . . P
  S2 0.47107(7) 0.41447(5) 0.26432(6) 0.0775(2) Uani d . 1 . . S
  O641 0.2213(2) 0.84030(10)
  -0.00540(10)
  0.0623(4) Uani d . 1 . . O
  O61 0.10536(15) 1.03811(13) 0.23040(14) 0.0661(5) Uani d . 1 . . O
  O11 0.46725(14) 0.59724(13) 0.10030(13) 0.0630(4) Uani d . 1 . . O
  N3 0.27266(16) 0.57979(14) 0.18674(15) 0.0523(4) Uani d . 1 . . N
  C69 0.1208(2) 1.07835(19) 0.1254(2) 0.0573(6) Uani d . 1 . . C
  N4 0.23898(17) 0.68403(16) 0.14672(17) 0.0551(5) Uani d . 1 . . N
  C70 0.16339(19) 1.01544(18) 0.04389(19) 0.0509(5) Uani d . 1 . . C
  O13 0.48145(15) 0.65215(13) 0.29665(14) 0.0678(5) Uani d . 1 . . O
  C64 0.18930(18) 0.90042(18) 0.06799(18) 0.0499(5) Uani d . 1 . . C
  O621 0.11731(18) 0.90721(16) 0.35652(15) 0.0814(6) Uani d . 1 . . O
  C5 0.20463(18) 0.75747(19) 0.2136(2) 0.0503(5) Uani d . 1 . . C
  C62 0.1329(2) 0.9321(2) 0.2620(2) 0.0577(6) Uani d . 1 . . C
  C65 0.1779(2) 1.0628(2) -0.0589(2) 0.0630(6) Uani d . 1 . . C
  C68 0.0900(3) 1.1862(2) 0.1027(3) 0.0760(8) Uani d . 1 . . C
  C66 0.1506(3) 1.1695(2) -0.0799(3) 0.0755(8) Uani d . 1 . . C
  C63 0.17616(18) 0.86278(18) 0.17979(17) 0.0484(5) Uani d . 1 . . C
  C67 0.1054(3) 1.2305(2) 0.0007(3) 0.0832(9) Uani d . 1 . . C
  C31 0.1845(3) 0.4984(2) 0.1297(2) 0.0697(7) Uani d D 1 . . C
  H311 0.1081(17) 0.5162(19) 0.151(2) 0.081(9) Uiso d D 1 . . H
  H313 0.211(2) 0.4323(14) 0.163(2) 0.092(9) Uiso d D 1 . . H
  H312 0.174(2) 0.5024(19) 0.0494(11) 0.072(8) Uiso d D 1 . . H
  C12 0.5989(3) 0.6027(4) 0.0947(4) 0.0907(10) Uani d . 1 . . C
  H121 0.636(3) 0.535(3) 0.113(3) 0.117(13) Uiso d . 1 . . H
  H122 0.631(3) 0.653(3) 0.151(3) 0.116(14) Uiso d . 1 . . H
  H123 0.605(3) 0.624(3) 0.022(3) 0.119(13) Uiso d . 1 . . H
  C14 0.4979(3) 0.6458(3) 0.4193(3) 0.0874(9) Uani d D 1 . . C
  H143 0.548(2) 0.5842(16) 0.441(3) 0.114 Uiso d D 1 . . H
  H142 0.4213(17) 0.640(2) 0.441(2) 0.114 Uiso d D 1 . . H
  H141 0.549(2) 0.7033(17) 0.448(3) 0.114 Uiso d D 1 . . H
  H41 0.247(2) 0.705(2) 0.084(2) 0.067(8) Uiso d . 1 . . H
  H51 0.200(2) 0.7294(17) 0.2866(19) 0.062(7) Uiso d . 1 . . H
  H651 0.209(2) 1.022(2) -0.111(2) 0.075(8) Uiso d . 1 . . H
  H671 0.080(2) 1.296(2) -0.015(2) 0.082(9) Uiso d . 1 . . H
  H681 0.061(2) 1.220(2) 0.152(2) 0.073(9) Uiso d . 1 . . H
  H661 0.162(2) 1.202(2) -0.150(2) 0.072(8) 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
  P1 0.0535(3) 0.0494(3) 0.0504(3) 0.0021(3) 0.0098(2) 0.0024(3)
  S2 0.0939(5) 0.0564(4) 0.0824(5) 0.0184(3) 0.0179(4) 0.0148(3)
  O641 0.0735(10) 0.0659(10) 0.0523(9) 0.0130(8) 0.0241(8) -0.0029(8)
  O61 0.0667(10) 0.0683(11) 0.0647(11) 0.0024(8) 0.0166(8) -0.0213(9)
  O11 0.0590(9) 0.0724(10) 0.0615(9) 0.0046(8) 0.0216(7) 0.0099(8)
  N3 0.0538(10) 0.0509(10) 0.0527(10) 0.0017(8) 0.0117(8) 0.0017(8)
  C69 0.0419(11) 0.0612(14) 0.0636(14) -0.0035(10) -0.0029(10) -0.0143(12)
  N4 0.0590(12) 0.0599(12) 0.0502(11) 0.0116(9) 0.0197(9) 0.0065(10)
  C70 0.0378(11) 0.0576(12) 0.0544(12) -0.0042(9) 0.0018(9) -0.0082(11)
  O13 0.0750(11) 0.0620(10) 0.0627(10) -0.0124(8) 0.0045(8) -0.0053(8)
  C64 0.0374(11) 0.0590(13) 0.0533(12) 0.0030(9) 0.0092(9) -0.0072(11)
  O621 0.0994(14) 0.0943(14) 0.0596(11) 0.0066(11) 0.0382(10) -0.0118(10)
  C5 0.0366(10) 0.0667(14) 0.0494(12) -0.0001(10) 0.0129(9) -0.0021(11)
  C62 0.0490(12) 0.0664(15) 0.0576(14) 0.0002(11) 0.0103(10) -0.0143(12)
  C65 0.0533(14) 0.0697(16) 0.0615(15) -0.0024(12) -0.0002(11) 0.0001(13)
  C68 0.0687(18) 0.0633(17) 0.088(2) 0.0047(13) -0.0057(15) -0.0253(17)
  C66 0.0727(17) 0.0689(17) 0.0747(19) -0.0063(14) -0.0105(14) 0.0076(16)
  C63 0.0379(10) 0.0600(13) 0.0481(11) -0.0003(9) 0.0101(9) -0.0069(10)
  C67 0.0808(19) 0.0528(16) 0.099(2) -0.0028(15) -0.0250(17) -0.0022(17)
  C31 0.0667(18) 0.0784(19) 0.0622(17) -0.0211(15) 0.0079(13) 0.0062(15)
  C12 0.0641(19) 0.117(3) 0.099(3) 0.003(2) 0.0350(18) 0.012(3)
  C14 0.083(2) 0.107(3) 0.0660(18) -0.0056(18) 0.0008(16) -0.0208(18)
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
  P1 O13 . 1.558(2) yes
  P1 O11 . 1.577(2) yes
  P1 N3 . 1.670(2) yes
  P1 S2 . 1.9050(10)
  yes
  O641 C64 . 1.244(2) no
  O61 C69 . 1.380(3) no
  O61 C62 . 1.382(3) no
  O11 C12 . 1.446(3) yes
  N3 N4 . 1.400(2) yes
  N3 C31 . 1.463(3) yes
  C69 C70 . 1.388(3) no
  C69 C68 . 1.390(4) no
  N4 C5 . 1.308(3) no
  N4 H41 . 0.81(2) no
  C70 C65 . 1.388(3) no
  C70 C64 . 1.470(3) no
  O13 C14 . 1.431(3) yes
  C64 C63 . 1.437(3) no
  O621 C62 . 1.204(3) no
  C5 C63 . 1.382(3) yes
  C5 H51 . 0.94(2) no
  C62 C63 . 1.444(3) no
  C65 C66 . 1.367(4) no
  C65 H651 . 0.91(3) no
  C68 C67 . 1.367(4) no
  C68 H681 . 0.83(2) no
  C66 C67 . 1.381(4) no
  C66 H661 . 0.95(2) no
  C67 H671 . 0.87(3) no
  C31 H311 . 0.940(10)
  no
  C31 H313 . 0.930(10)
  no
  C31 H312 . 0.940(10)
  no
  C12 H121 . 0.94(3) no
  C12 H122 . 0.93(3) no
  C12 H123 . 0.91(3) no
  C14 H143 . 0.940(10)
  no
  C14 H142 . 0.920(10)
  no
  C14 H141 . 0.930(10)
  no