#------------------------------------------------------------------------------
#$Date: 2008-01-13 22:15:36 +0000 (Sun, 13 Jan 2008) $
#$Revision: 14 $
#$URL: svn://www.crystallography.net/cod/cif/2/2008804.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_2008804
_journal_name_full  'Acta Crystallographica'
_journal_year  1999
_journal_volume  C55
_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  'triclinic'
_symmetry_space_group_name_H-M  'P -1'
loop_
_symmetry_equiv_pos_as_xyz
  'x, y, z'
  '-x, -y, -z'
_cell_length_a  7.666(3)
_cell_length_b  15.521(2)
_cell_length_c  7.470(2)
_cell_angle_alpha  101.53(2)
_cell_angle_beta  115.50(3)
_cell_angle_gamma  91.91(3)
_cell_volume  778.8(4)
_cell_formula_units_Z  2
_cell_measurement_temperature  293(2)
_exptl_crystal_density_diffrn  1.460
_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 0.52996(4) 0.650631(18) 0.29385(4) 0.03468(9) Uani d . 1 . . P
  S2 0.54863(7) 0.71081(3) 0.55231(6) 0.06044(12) Uani d . 1 . . S
  O61 -0.26871(12) 0.87616(6) 0.14186(16) 0.0449(2) Uani d . 1 . . O
  O11 0.45593(14) 0.54774(6) 0.22307(17) 0.0502(2) Uani d . 1 . . O
  O13 0.72601(13) 0.64877(7) 0.27349(16) 0.0484(2) Uani d . 1 . . O
  C64 0.12146(15) 0.92034(7) 0.20488(17) 0.03426(19) Uani d . 1 . . C
  O641 0.28867(13) 0.94019(6) 0.23019(18) 0.0506(2) Uani d . 1 . . O
  C70 0.00297(15) 0.98795(7) 0.23918(16) 0.03366(19) Uani d . 1 . . C
  C63 0.02445(15) 0.82918(7) 0.14034(17) 0.03392(19) Uani d . 1 . . C
  C69 -0.18566(15) 0.96386(7) 0.20880(17) 0.0360(2) Uani d . 1 . . C
  N3 0.40411(16) 0.69622(7) 0.10391(16) 0.0426(2) Uani d . 1 . . N
  O51 0.03115(16) 0.67352(6) 0.0554(2) 0.0619(3) Uani d . 1 . . O
  C5 0.11637(17) 0.74855(7) 0.10441(19) 0.0389(2) Uani d . 1 . . C
  N4 0.30115(15) 0.76523(7) 0.13184(18) 0.0420(2) Uani d . 1 . . N
  C65 0.07708(19) 1.07850(8) 0.3071(2) 0.0428(2) Uani d . 1 . . C
  C68 -0.30100(19) 1.02584(9) 0.2444(2) 0.0448(3) Uani d . 1 . . C
  C67 -0.2231(2) 1.11439(9) 0.3118(2) 0.0502(3) Uani d . 1 . . C
  C66 -0.0354(2) 1.14052(9) 0.3416(2) 0.0506(3) Uani d . 1 . . C
  C62 -0.16041(16) 0.81414(8) 0.1132(2) 0.0406(2) Uani d . 1 . . C
  H621 -0.229(2) 0.7562(11) 0.073(3) 0.047(4) Uiso d . 1 . . H
  C12 0.2866(3) 0.51252(12) 0.2354(4) 0.0705(5) Uani d D 1 . . C
  H121 0.276(4) 0.4525(8) 0.185(4) 0.106(8) Uiso d D 1 . . H
  H122 0.175(3) 0.5385(15) 0.173(3) 0.105(8) Uiso d D 1 . . H
  H123 0.314(4) 0.5244(18) 0.375(2) 0.122(11) Uiso d D 1 . . H
  C31 0.3551(3) 0.65412(14) -0.1059(2) 0.0632(4) Uani d D 1 . . C
  H311 0.424(3) 0.6059(10) -0.113(3) 0.075(6) Uiso d D 1 . . H
  H312 0.347(3) 0.6929(13) -0.189(3) 0.094(7) Uiso d D 1 . . H
  H313 0.227(2) 0.6233(13) -0.172(3) 0.093(8) Uiso d D 1 . . H
  C14 0.8779(2) 0.60347(14) 0.3914(4) 0.0724(5) Uani d D 1 . . C
  H141 0.846(3) 0.5431(8) 0.332(3) 0.096(8) Uiso d D 1 . . H
  H142 0.891(4) 0.607(2) 0.524(2) 0.146(13) Uiso d D 1 . . H
  H143 0.996(2) 0.6266(12) 0.403(3) 0.077(6) Uiso d D 1 . . H
  H41 0.358(3) 0.8171(13) 0.166(3) 0.062(5) Uiso d . 1 . . H
  H671 -0.293(3) 1.1576(14) 0.349(3) 0.073(6) Uiso d . 1 . . H
  H651 0.199(3) 1.0929(13) 0.322(3) 0.069(6) Uiso d . 1 . . H
  H681 -0.426(2) 1.0041(11) 0.225(3) 0.049(4) Uiso d . 1 . . H
  H661 0.020(3) 1.2011(14) 0.383(3) 0.069(5) 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 0.03483(14) 0.03304(14) 0.04313(16) 0.00673(9) 0.02218(11) 0.01236(10)
  S2 0.0770(3) 0.0649(2) 0.04538(19) 0.01395(19) 0.03348(18) 0.01061(16)
  O61 0.0321(4) 0.0391(4) 0.0670(6) 0.0026(3) 0.0253(4) 0.0125(4)
  O11 0.0519(5) 0.0337(4) 0.0738(6) 0.0057(3) 0.0356(5) 0.0139(4)
  O13 0.0375(4) 0.0534(5) 0.0677(6) 0.0143(4) 0.0302(4) 0.0260(4)
  C64 0.0308(4) 0.0336(4) 0.0413(5) 0.0025(3) 0.0185(4) 0.0097(4)
  O641 0.0365(4) 0.0396(4) 0.0806(7) -0.0009(3) 0.0339(4) 0.0076(4)
  C70 0.0336(4) 0.0325(4) 0.0376(5) 0.0037(3) 0.0177(4) 0.0099(4)
  C63 0.0315(4) 0.0316(4) 0.0415(5) 0.0035(3) 0.0181(4) 0.0108(4)
  C69 0.0334(5) 0.0372(5) 0.0412(5) 0.0058(4) 0.0185(4) 0.0125(4)
  N3 0.0468(5) 0.0432(5) 0.0445(5) 0.0189(4) 0.0239(4) 0.0142(4)
  O51 0.0533(5) 0.0331(4) 0.1017(9) 0.0028(4) 0.0395(6) 0.0105(5)
  C5 0.0380(5) 0.0334(5) 0.0478(6) 0.0066(4) 0.0205(4) 0.0118(4)
  N4 0.0382(5) 0.0339(4) 0.0605(6) 0.0108(4) 0.0259(4) 0.0155(4)
  C65 0.0438(6) 0.0343(5) 0.0511(6) 0.0016(4) 0.0229(5) 0.0086(4)
  C68 0.0402(6) 0.0493(6) 0.0530(7) 0.0145(5) 0.0258(5) 0.0166(5)
  C67 0.0583(7) 0.0453(6) 0.0553(7) 0.0207(6) 0.0309(6) 0.0147(5)
  C66 0.0614(8) 0.0342(5) 0.0578(7) 0.0084(5) 0.0289(6) 0.0089(5)
  C62 0.0341(5) 0.0343(5) 0.0551(6) 0.0015(4) 0.0213(5) 0.0113(4)
  C12 0.0524(8) 0.0482(8) 0.1200(17) 0.0023(6) 0.0410(10) 0.0345(9)
  C31 0.0717(10) 0.0805(11) 0.0446(7) 0.0309(9) 0.0299(7) 0.0174(7)
  C14 0.0431(7) 0.0734(11) 0.1066(15) 0.0254(7) 0.0293(9) 0.0403(11)
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 . 1.5750(10)
  yes
  P1 O11 . 1.5700(10)
  yes
  P1 N3 . 1.6470(10)
  yes
  P1 S2 . 1.9110(10)
  yes
  O61 C62 . 1.336(2) no
  O61 C69 . 1.3800(10)
  no
  O11 C12 . 1.438(2) yes
  O13 C14 . 1.430(2) no
  C64 O641 . 1.2310(10)
  no
  C64 C63 . 1.462(2) no
  C64 C70 . 1.466(2) no
  C70 C69 . 1.390(2) no
  C70 C65 . 1.403(2) no
  C63 C62 . 1.348(2) no
  C63 C5 . 1.491(2) yes
  C69 C68 . 1.391(2) no
  N3 N4 . 1.3860(10)
  yes
  N3 C31 . 1.446(2) yes
  O51 C5 . 1.221(2) yes
  C5 N4 . 1.350(2) yes
  N4 H41 . 0.84(2) no
  C65 C66 . 1.373(2) no
  C65 H651 . 0.91(2) no
  C68 C67 . 1.382(2) no
  C68 H681 . 0.95(2) no
  C67 C66 . 1.391(2) no
  C67 H671 . 0.94(2) no
  C66 H661 . 0.95(2) no
  C62 H621 . 0.95(2) no
  C12 H121 . 0.920(10)
  no
  C12 H122 . 0.930(10)
  no
  C12 H123 . 0.950(10)
  no
  C31 H311 . 0.940(10)
  no
  C31 H312 . 0.930(10)
  no
  C31 H313 . 0.950(10)
  no
  C14 H141 . 0.930(10)
  no
  C14 H142 . 0.940(10)
  no
  C14 H143 . 0.920(10)
  no