#------------------------------------------------------------------------------
#$Date: 2008-01-13 22:15:36 +0000 (Sun, 13 Jan 2008) $
#$Revision: 14 $
#$URL: svn://www.crystallography.net/cod/cif/2/2012824.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_2012824
_journal_name_full  'Acta Crystallographica, Section C'
_journal_year  2002
_journal_volume  58
_journal_page_first  o405
_journal_page_last  o406
_publ_section_title
;
Benzopyran derivatives substituted in position 3
;
loop_
_publ_author_name
  'Rybarczyk-Pirek, Agnieszka J.'
  "Ma\/lecka, Magdalena"
  "Grabowski, S\/lawomir J."
  "Nawrot-Modranka, Jolanta"
_chemical_formula_moiety  'C23 H19 N2 O5 P'
_chemical_formula_sum  'C23 H19 N2 O5 P'
_chemical_formula_weight  434.37
_symmetry_cell_setting  'monoclinic'
_symmetry_space_group_name_H-M  'P 21/n'
_symmetry_space_group_name_Hall  '-P 2yn'
loop_
_symmetry_equiv_pos_as_xyz
  'x, y, z'
  '-x+1/2, y+1/2, -z+1/2'
  '-x, -y, -z'
  'x-1/2,-y-1/2, z-1/2'
_cell_length_a  8.312(2)
_cell_length_b  10.6110(10)
_cell_length_c  23.595(2)
_cell_angle_alpha  90
_cell_angle_beta  90.760(10)
_cell_angle_gamma  90
_cell_volume  2082.8(5)
_cell_formula_units_Z  4
_cell_measurement_temperature  293(2)
_exptl_crystal_density_diffrn  1.385
_exptl_crystal_density_meas  1.378
_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 0.22022(6) 0.36544(5) 0.18452(2) 0.0514(2) Uani d . 1 . . P
  O2 0.25073(18) 0.42753(14) 0.23831(6) 0.0654(4) Uani d . 1 . . O
  N3 0.33831(19) 0.24397(15) 0.17406(7) 0.0543(4) Uani d . 1 . . N
  C31 0.4785(3) 0.2169(3) 0.20950(11) 0.0658(6) Uani d . 1 . . C
  N4 0.29932(18) 0.16982(15) 0.12761(7) 0.0525(4) Uani d . 1 . . N
  C5 0.3904(2) 0.07810(18) 0.11550(8) 0.0503(5) Uani d . 1 . . C
  O61 0.17005(17) -0.06544(14) -0.00660(6) 0.0646(4) Uani d . 1 . . O
  C62 0.2186(2) 0.0101(2) 0.03608(9) 0.0561(5) Uani d . 1 . . C
  H62 0.145(3) 0.077(2) 0.0397(9) 0.072(7) Uiso d . 1 . . H
  C63 0.3510(2) -0.00580(17) 0.06826(8) 0.0472(4) Uani d . 1 . . C
  C64 0.4587(2) -0.11072(18) 0.05635(9) 0.0543(5) Uani d . 1 . . C
  O641 0.58513(19) -0.12694(15) 0.08232(8) 0.0838(5) Uani d . 1 . . O
  C65 0.4924(3) -0.2997(2) -0.00597(12) 0.0748(7) Uani d . 1 . . C
  H65 0.5881 -0.3194 0.0128 0.090 Uiso calc R 1 . . H
  C66 0.4379(4) -0.3747(2) -0.04955(12) 0.0866(8) Uani d . 1 . . C
  H66 0.4982 -0.4439 -0.0607 0.104 Uiso calc R 1 . . H
  C67 0.2949(4) -0.3482(3) -0.07680(12) 0.0878(8) Uani d . 1 . . C
  H67 0.2583 -0.4004 -0.1059 0.105 Uiso calc R 1 . . H
  C68 0.2065(3) -0.2459(2) -0.06157(10) 0.0785(7) Uani d . 1 . . C
  H68 0.1093 -0.2284 -0.0798 0.094 Uiso calc R 1 . . H
  C69 0.2629(3) -0.16894(19) -0.01875(9) 0.0565(5) Uani d . 1 . . C
  C70 0.4040(2) -0.19352(18) 0.01031(9) 0.0548(5) Uani d . 1 . . C
  O11 0.04154(15) 0.31704(12) 0.17435(5) 0.0530(4) Uani d . 1 . . O
  C12 -0.0294(2) 0.2327(2) 0.21271(8) 0.0544(5) Uani d . 1 . . C
  C13 -0.0638(3) 0.1127(2) 0.19307(11) 0.0744(7) Uani d . 1 . . C
  H13 -0.0312 0.0883 0.1572 0.089 Uiso calc R 1 . . H
  C14 -0.1455(3) 0.0301(3) 0.22641(15) 0.0970(9) Uani d . 1 . . C
  H14 -0.1707 -0.0500 0.2129 0.116 Uiso calc R 1 . . H
  C15 -0.1903(3) 0.0649(3) 0.27954(14) 0.0972(9) Uani d . 1 . . C
  H15 -0.2471 0.0088 0.3020 0.117 Uiso calc R 1 . . H
  C16 -0.1528(3) 0.1795(4) 0.29954(11) 0.0979(10) Uani d . 1 . . C
  H16 -0.1808 0.2009 0.3363 0.118 Uiso calc R 1 . . H
  C17 -0.0707(3) 0.2690(3) 0.26554(10) 0.0747(7) Uani d . 1 . . C
  H17 -0.0465 0.3492 0.2791 0.090 Uiso calc R 1 . . H
  O21 0.24129(17) 0.44753(12) 0.12929(6) 0.0603(4) Uani d . 1 . . O
  C22 0.1556(2) 0.56025(17) 0.12009(8) 0.0513(5) Uani d . 1 . . C
  C23 0.1895(3) 0.66578(19) 0.15090(9) 0.0625(5) Uani d . 1 . . C
  H23 0.2681 0.6638 0.1793 0.075 Uiso calc R 1 . . H
  C24 0.1064(3) 0.7754(2) 0.13971(10) 0.0710(6) Uani d . 1 . . C
  H24 0.1296 0.8479 0.1604 0.085 Uiso calc R 1 . . H
  C25 -0.0089(3) 0.7778(3) 0.09874(12) 0.0806(7) Uani d . 1 . . C
  H25 -0.0669 0.8514 0.0920 0.097 Uiso calc R 1 . . H
  C26 -0.0401(3) 0.6730(3) 0.06736(12) 0.0868(8) Uani d . 1 . . C
  H26 -0.1176 0.6759 0.0386 0.104 Uiso calc R 1 . . H
  C27 0.0425(3) 0.5617(2) 0.07787(10) 0.0716(6) Uani d . 1 . . C
  H27 0.0211 0.4897 0.0566 0.086 Uiso calc R 1 . . H
  H51 0.488(3) 0.0604(19) 0.1351(9) 0.063(6) Uiso d . 1 . . H
  H311 0.578(3) 0.227(2) 0.1883(10) 0.076(7) Uiso d . 1 . . H
  H312 0.482(3) 0.277(3) 0.2376(12) 0.090(8) Uiso d . 1 . . H
  H313 0.467(3) 0.136(2) 0.2267(10) 0.078(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 0.0536(3) 0.0488(3) 0.0518(3) 0.0030(2) -0.0007(2) -0.0055(2)
  O2 0.0721(9) 0.0631(9) 0.0608(9) 0.0006(7) -0.0044(7) -0.0154(7)
  N3 0.0539(9) 0.0540(9) 0.0548(9) 0.0062(7) -0.0092(7) -0.0089(8)
  C31 0.0571(13) 0.0751(16) 0.0649(14) 0.0098(12) -0.0147(11) -0.0099(13)
  N4 0.0536(9) 0.0488(9) 0.0549(9) 0.0051(7) -0.0055(7) -0.0049(8)
  C5 0.0459(10) 0.0491(11) 0.0557(11) 0.0029(9) -0.0030(9) 0.0013(9)
  O61 0.0632(8) 0.0660(9) 0.0641(9) 0.0094(7) -0.0145(7) -0.0117(7)
  C62 0.0543(11) 0.0528(11) 0.0609(12) 0.0105(9) -0.0054(9) -0.0050(10)
  C63 0.0460(10) 0.0436(10) 0.0522(11) 0.0039(8) 0.0023(8) 0.0025(8)
  C64 0.0503(11) 0.0506(11) 0.0620(12) 0.0052(9) 0.0020(9) 0.0023(9)
  O641 0.0642(10) 0.0849(11) 0.1015(13) 0.0287(8) -0.0251(9) -0.0147(10)
  C65 0.0747(14) 0.0566(13) 0.0934(17) 0.0078(11) 0.0187(13) -0.0068(13)
  C66 0.110(2) 0.0545(14) 0.096(2) -0.0043(14) 0.0463(17) -0.0201(14)
  C67 0.114(2) 0.0811(18) 0.0693(16) -0.0205(16) 0.0199(15) -0.0220(14)
  C68 0.0929(17) 0.0759(16) 0.0665(15) -0.0072(14) -0.0016(13) -0.0167(13)
  C69 0.0612(12) 0.0538(11) 0.0546(12) -0.0031(9) 0.0050(9) -0.0012(9)
  C70 0.0567(11) 0.0456(11) 0.0625(12) 0.0000(9) 0.0131(9) -0.0008(9)
  O11 0.0514(7) 0.0550(8) 0.0524(8) 0.0046(6) -0.0027(6) 0.0034(6)
  C12 0.0425(10) 0.0618(12) 0.0587(12) 0.0117(9) -0.0003(8) 0.0089(10)
  C13 0.0775(15) 0.0535(13) 0.0929(17) 0.0108(11) 0.0190(13) 0.0082(12)
  C14 0.092(2) 0.0692(17) 0.131(3) 0.0103(14) 0.0194(18) 0.0289(18)
  C15 0.0747(17) 0.115(2) 0.101(2) 0.0013(17) -0.0004(16) 0.046(2)
  C16 0.0648(15) 0.176(3) 0.0533(14) 0.0050(19) 0.0032(11) 0.0157(18)
  C17 0.0550(12) 0.1051(18) 0.0640(14) -0.0002(12) 0.0025(10) -0.0077(14)
  O21 0.0662(9) 0.0526(8) 0.0625(9) 0.0077(7) 0.0114(7) 0.0014(7)
  C22 0.0497(10) 0.0489(11) 0.0553(11) -0.0026(8) 0.0091(9) 0.0040(9)
  C23 0.0682(13) 0.0574(12) 0.0617(13) -0.0049(10) -0.0036(10) 0.0015(10)
  C24 0.0941(17) 0.0520(12) 0.0671(15) 0.0053(12) 0.0093(13) 0.0029(11)
  C25 0.0832(17) 0.0718(16) 0.0872(18) 0.0183(13) 0.0203(14) 0.0220(15)
  C26 0.0695(15) 0.106(2) 0.0840(18) 0.0013(15) -0.0188(13) 0.0220(17)
  C27 0.0764(15) 0.0703(14) 0.0678(14) -0.0122(12) -0.0118(12) -0.0022(12)
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 O2 . 1.4500(10)
  y
  P1 O21 . 1.5790(10)
  y
  P1 O11 . 1.5880(10)
  y
  P1 N3 . 1.641(2) y
  N3 N4 . 1.384(2) y
  N3 C31 . 1.455(3) y
  C31 H311 . 0.98(2) ?
  C31 H312 . 0.92(3) ?
  C31 H313 . 0.95(2) ?
  N4 C5 . 1.269(2) y
  C5 C63 . 1.460(3) y
  C5 H51 . 0.95(2) ?
  O61 C62 . 1.345(2) y
  O61 C69 . 1.375(2) y
  C62 C63 . 1.340(3) y
  C62 H62 . 0.94(2) .
  C63 C64 . 1.459(2) y
  C64 O641 . 1.222(2) y
  C64 C70 . 1.465(3) y
  C65 C66 . 1.372(4) ?
  C65 C70 . 1.402(3) ?
  C65 H65 . 0.9300 ?
  C66 C67 . 1.374(4) ?
  C66 H66 . 0.9300 ?
  C67 C68 . 1.361(4) ?
  C67 H67 . 0.9300 ?
  C68 C69 . 1.377(3) ?
  C68 H68 . 0.9300 ?
  C69 C70 . 1.376(3) y
  O11 C12 . 1.408(2) ?
  C12 C17 . 1.354(3) ?
  C12 C13 . 1.384(3) ?
  C13 C14 . 1.365(3) ?
  C13 H13 . 0.9300 ?
  C14 C15 . 1.364(4) ?
  C14 H14 . 0.9300 ?
  C15 C16 . 1.340(4) ?
  C15 H15 . 0.9300 ?
  C16 C17 . 1.424(4) ?
  C16 H16 . 0.9300 ?
  C17 H17 . 0.9300 ?
  O21 C22 . 1.408(2) ?
  C22 C27 . 1.361(3) ?
  C22 C23 . 1.363(3) ?
  C23 C24 . 1.377(3) ?
  C23 H23 . 0.9300 ?
  C24 C25 . 1.353(4) ?
  C24 H24 . 0.9300 ?
  C25 C26 . 1.360(4) ?
  C25 H25 . 0.9300 ?
  C26 C27 . 1.387(4) ?
  C26 H26 . 0.9300 ?
  C27 H27 . 0.9300 ?