data_2202636
_journal_name_full  'Acta Crystallographica, Section E'
_journal_year  2003
_journal_volume  59
_journal_page_first  o1395
_journal_page_last  o1397
_publ_section_title
;
6a,14a-cis-6,6a,7,14a-Tetrahydrochromeno[4',3':3,4]pyrano[3,2-c]coumarin
;
loop_
_publ_author_name
  'R. Krishna'
  'P. G. Aravindan'
  'M. Yogavel'
  'D. Velmurugan'
  'S. Shanmuga Sundara Raj'
  'H.-K. Fun'
  'M. Shanmuga Sundaram'
  'R. Raghunathan'
_chemical_formula_moiety  'C19 H14 O4'
_chemical_formula_sum  'C19 H14 O4'
_chemical_formula_iupac  'C19 H14 O4'
_chemical_formula_weight  306.30
_symmetry_cell_setting  monoclinic
_symmetry_space_group_name_H-M  'P 21/c'
_symmetry_space_group_name_Hall  '-P 2ybc'
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  12.22520(10)
_cell_length_b  16.3351(3)
_cell_length_c  15.3425(3)
_cell_angle_alpha  90.00
_cell_angle_beta  109.2070(10)
_cell_angle_gamma  90.00
_cell_volume  2893.35(8)
_cell_formula_units_Z  8
_cell_measurement_temperature  293(2)
_exptl_crystal_density_diffrn  1.406
_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
  O1A 0.81696(10) 0.52353(7) 0.40126(9) 0.0460(3) Uani d . 1 . . O
  O2A 0.68208(11) 0.60333(8) 0.42118(10) 0.0561(3) Uani d . 1 . . O
  O3A 0.59638(10) 0.32610(7) 0.33785(9) 0.0455(3) Uani d . 1 . . O
  O4A 0.25966(10) 0.43271(8) 0.26001(9) 0.0529(3) Uani d . 1 . . O
  C2A 0.70422(14) 0.53606(10) 0.39770(11) 0.0411(4) Uani d . 1 . . C
  C3A 0.62236(13) 0.46990(9) 0.36671(10) 0.0352(3) Uani d . 1 . . C
  C4A 0.66200(13) 0.39405(9) 0.35680(11) 0.0362(3) Uani d . 1 . . C
  C5A 0.78270(13) 0.37947(10) 0.36883(10) 0.0372(3) Uani d . 1 . . C
  C6A 0.85639(14) 0.44687(10) 0.38954(11) 0.0395(3) Uani d . 1 . . C
  C7A 0.97387(15) 0.43920(12) 0.40214(12) 0.0475(4) Uani d . 1 . . C
  H7A 1.0218 0.4849 0.4142 0.057 Uiso calc R 1 . . H
  C8A 1.01744(16) 0.36306(13) 0.39639(12) 0.0514(4) Uani d . 1 . . C
  H8A 1.0963 0.3570 0.4064 0.062 Uiso calc R 1 . . H
  C9A 0.94611(16) 0.29448(13) 0.37584(12) 0.0494(4) Uani d . 1 . . C
  H9A 0.9773 0.2432 0.3718 0.059 Uiso calc R 1 . . H
  C10A 0.82897(15) 0.30248(11) 0.36138(11) 0.0432(4) Uani d . 1 . . C
  H10A 0.7810 0.2568 0.3467 0.052 Uiso calc R 1 . . H
  C11A 0.47372(14) 0.33633(10) 0.31907(13) 0.0438(4) Uani d . 1 . . C
  H11A 0.4412 0.2851 0.3310 0.053 Uiso calc R 1 . . H
  H11B 0.4374 0.3494 0.2543 0.053 Uiso calc R 1 . . H
  C12A 0.44571(14) 0.40321(10) 0.37689(11) 0.0386(3) Uani d . 1 . . C
  H12A 0.4804 0.3887 0.4422 0.046 Uiso calc R 1 . . H
  C13A 0.49776(13) 0.48470(9) 0.35993(11) 0.0356(3) Uani d . 1 . . C
  H13A 0.4973 0.5227 0.4093 0.043 Uiso calc R 1 . . H
  C14A 0.42310(13) 0.52157(9) 0.26797(11) 0.0358(3) Uani d . 1 . . C
  C15A 0.31038(14) 0.49340(10) 0.22483(12) 0.0413(4) Uani d . 1 . . C
  C16A 0.31652(15) 0.41106(11) 0.35480(12) 0.0458(4) Uani d . 1 . . C
  H16A 0.2856 0.3595 0.3677 0.055 Uiso calc R 1 . . H
  H16B 0.3006 0.4526 0.3942 0.055 Uiso calc R 1 . . H
  C17A 0.24301(16) 0.52449(13) 0.13971(13) 0.0543(5) Uani d . 1 . . C
  H17A 0.1684 0.5046 0.1115 0.065 Uiso calc R 1 . . H
  C18A 0.28592(18) 0.58455(13) 0.09692(14) 0.0582(5) Uani d . 1 . . C
  H18A 0.2406 0.6050 0.0399 0.070 Uiso calc R 1 . . H
  C19A 0.39635(18) 0.61423(12) 0.13889(14) 0.0549(5) Uani d . 1 . . C
  H19A 0.4255 0.6551 0.1105 0.066 Uiso calc R 1 . . H
  C20A 0.46349(16) 0.58301(10) 0.22317(13) 0.0461(4) Uani d . 1 . . C
  H20A 0.5378 0.6036 0.2509 0.055 Uiso calc R 1 . . H
  O1B 0.66184(10) 0.16108(8) 0.08697(9) 0.0489(3) Uani d . 1 . . O
  O2B 0.79637(11) 0.07284(7) 0.08321(9) 0.0528(3) Uani d . 1 . . O
  O3B 0.89363(10) 0.35224(7) 0.14674(8) 0.0434(3) Uani d . 1 . . O
  O4B 1.22624(11) 0.23412(9) 0.22756(10) 0.0600(4) Uani d . 1 . . O
  C2B 0.77600(14) 0.14314(10) 0.09760(11) 0.0402(3) Uani d . 1 . . C
  C3B 0.86045(13) 0.20829(9) 0.12349(10) 0.0353(3) Uani d . 1 . . C
  C4B 0.82432(13) 0.28612(9) 0.12986(10) 0.0358(3) Uani d . 1 . . C
  C5B 0.70387(14) 0.30489(10) 0.11545(10) 0.0386(3) Uani d . 1 . . C
  C6B 0.62643(15) 0.23977(11) 0.09467(11) 0.0434(4) Uani d . 1 . . C
  C7B 0.50879(16) 0.25140(14) 0.07992(13) 0.0537(5) Uani d . 1 . . C
  H7B 0.4579 0.2073 0.0674 0.064 Uiso calc R 1 . . H
  C8B 0.46998(17) 0.32957(15) 0.08439(14) 0.0607(5) Uani d . 1 . . C
  H8B 0.3915 0.3383 0.0737 0.073 Uiso calc R 1 . . H
  C9B 0.54525(18) 0.39608(14) 0.10454(14) 0.0581(5) Uani d . 1 . . C
  H9B 0.5170 0.4486 0.1069 0.070 Uiso calc R 1 . . H
  C10B 0.66212(16) 0.38382(12) 0.12105(12) 0.0483(4) Uani d . 1 . . C
  H10B 0.7130 0.4279 0.1359 0.058 Uiso calc R 1 . . H
  C11B 1.01600(14) 0.33738(10) 0.16789(12) 0.0413(4) Uani d . 1 . . C
  H11C 1.0499 0.3248 0.2331 0.050 Uiso calc R 1 . . H
  H11D 1.0526 0.3867 0.1557 0.050 Uiso calc R 1 . . H
  C12B 1.04043(14) 0.26762(10) 0.11211(11) 0.0404(3) Uani d . 1 . . C
  H12B 1.0057 0.2808 0.0464 0.048 Uiso calc R 1 . . H
  C13B 0.98440(14) 0.18897(9) 0.13188(11) 0.0371(3) Uani d . 1 . . C
  H13B 0.9834 0.1488 0.0842 0.045 Uiso calc R 1 . . H
  C14B 1.05716(14) 0.15392(9) 0.22548(11) 0.0395(3) Uani d . 1 . . C
  C15B 1.17234(15) 0.17816(11) 0.26614(13) 0.0481(4) Uani d . 1 . . C
  C16B 1.16889(16) 0.25488(12) 0.13290(14) 0.0512(4) Uani d . 1 . . C
  H16C 1.1809 0.2114 0.0940 0.061 Uiso calc R 1 . . H
  H16D 1.2027 0.3046 0.1183 0.061 Uiso calc R 1 . . H
  C17B 1.23934(19) 0.14793(14) 0.35180(16) 0.0666(6) Uani d . 1 . . C
  H17B 1.3156 0.1653 0.3782 0.080 Uiso calc R 1 . . H
  C18B 1.1934(2) 0.09256(14) 0.39755(16) 0.0705(6) Uani d . 1 . . C
  H18B 1.2386 0.0723 0.4547 0.085 Uiso calc R 1 . . H
  C19B 1.0802(2) 0.06711(12) 0.35862(15) 0.0639(6) Uani d . 1 . . C
  H19B 1.0488 0.0297 0.3895 0.077 Uiso calc R 1 . . H
  C20B 1.01356(16) 0.09726(10) 0.27363(13) 0.0492(4) Uani d . 1 . . C
  H20B 0.9375 0.0793 0.2478 0.059 Uiso calc R 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
  O1A 0.0354(6) 0.0408(6) 0.0576(7) -0.0078(5) 0.0096(5) -0.0025(5)
  O2A 0.0495(7) 0.0369(6) 0.0764(9) -0.0064(5) 0.0132(6) -0.0111(6)
  O3A 0.0346(6) 0.0327(6) 0.0684(8) -0.0039(4) 0.0155(5) -0.0058(5)
  O4A 0.0353(6) 0.0609(8) 0.0576(8) -0.0098(6) 0.0086(5) 0.0119(6)
  C2A 0.0378(8) 0.0376(8) 0.0420(8) -0.0051(7) 0.0053(7) -0.0001(7)
  C3A 0.0319(7) 0.0336(7) 0.0365(7) -0.0032(6) 0.0065(6) -0.0005(6)
  C4A 0.0332(7) 0.0353(7) 0.0372(8) -0.0047(6) 0.0074(6) -0.0012(6)
  C5A 0.0338(8) 0.0415(8) 0.0343(7) -0.0003(6) 0.0087(6) 0.0008(6)
  C6A 0.0355(8) 0.0447(9) 0.0357(8) -0.0032(6) 0.0082(6) 0.0004(7)
  C7A 0.0354(8) 0.0620(11) 0.0443(9) -0.0084(8) 0.0122(7) -0.0009(8)
  C8A 0.0359(9) 0.0762(13) 0.0444(9) 0.0032(9) 0.0164(7) -0.0022(9)
  C9A 0.0473(10) 0.0594(11) 0.0443(9) 0.0119(9) 0.0186(8) 0.0011(8)
  C10A 0.0423(9) 0.0453(9) 0.0421(9) 0.0031(7) 0.0140(7) -0.0008(7)
  C11A 0.0340(8) 0.0352(8) 0.0602(11) -0.0050(6) 0.0129(7) -0.0031(7)
  C12A 0.0364(8) 0.0393(8) 0.0400(8) -0.0012(6) 0.0126(6) 0.0047(7)
  C13A 0.0349(8) 0.0334(7) 0.0365(7) -0.0005(6) 0.0093(6) -0.0017(6)
  C14A 0.0351(7) 0.0320(7) 0.0391(8) 0.0028(6) 0.0106(6) -0.0010(6)
  C15A 0.0367(8) 0.0412(8) 0.0453(9) 0.0016(7) 0.0124(7) 0.0029(7)
  C16A 0.0416(9) 0.0467(9) 0.0533(10) 0.0004(7) 0.0211(8) 0.0068(8)
  C17A 0.0394(9) 0.0625(12) 0.0520(10) -0.0003(8) 0.0029(8) 0.0077(9)
  C18A 0.0582(12) 0.0599(12) 0.0482(10) 0.0086(10) 0.0063(9) 0.0134(9)
  C19A 0.0637(12) 0.0437(10) 0.0545(11) -0.0001(9) 0.0156(9) 0.0147(8)
  C20A 0.0459(9) 0.0356(8) 0.0532(10) -0.0031(7) 0.0115(8) 0.0044(7)
  O1B 0.0391(6) 0.0468(7) 0.0569(7) -0.0125(5) 0.0107(5) -0.0048(6)
  O2B 0.0552(8) 0.0368(6) 0.0607(8) -0.0105(6) 0.0114(6) -0.0073(6)
  O3B 0.0372(6) 0.0325(5) 0.0589(7) -0.0049(5) 0.0137(5) -0.0036(5)
  O4B 0.0394(7) 0.0660(9) 0.0691(9) -0.0106(6) 0.0103(6) 0.0082(7)
  C2B 0.0403(8) 0.0395(8) 0.0367(8) -0.0087(7) 0.0072(6) -0.0008(6)
  C3B 0.0355(8) 0.0334(7) 0.0336(7) -0.0059(6) 0.0068(6) -0.0023(6)
  C4B 0.0354(8) 0.0359(7) 0.0340(7) -0.0058(6) 0.0085(6) -0.0006(6)
  C5B 0.0369(8) 0.0432(8) 0.0340(7) -0.0010(7) 0.0094(6) 0.0008(6)
  C6B 0.0385(8) 0.0522(10) 0.0370(8) -0.0050(7) 0.0090(7) -0.0009(7)
  C7B 0.0362(9) 0.0730(13) 0.0507(10) -0.0081(9) 0.0126(8) -0.0057(9)
  C8B 0.0398(10) 0.0899(16) 0.0527(11) 0.0065(10) 0.0158(8) -0.0026(11)
  C9B 0.0548(12) 0.0646(13) 0.0566(11) 0.0160(10) 0.0206(9) 0.0000(10)
  C10B 0.0480(10) 0.0485(10) 0.0494(10) 0.0036(8) 0.0172(8) -0.0003(8)
  C11B 0.0367(8) 0.0353(8) 0.0511(9) -0.0073(6) 0.0132(7) -0.0030(7)
  C12B 0.0415(9) 0.0416(8) 0.0395(8) -0.0054(7) 0.0152(7) -0.0019(7)
  C13B 0.0378(8) 0.0338(7) 0.0387(8) -0.0032(6) 0.0111(6) -0.0060(6)
  C14B 0.0402(8) 0.0318(7) 0.0435(8) 0.0006(6) 0.0096(7) -0.0040(6)
  C15B 0.0406(9) 0.0423(9) 0.0563(10) -0.0020(7) 0.0089(8) -0.0009(8)
  C16B 0.0448(10) 0.0538(11) 0.0605(11) -0.0033(8) 0.0248(9) -0.0009(9)
  C17B 0.0482(11) 0.0616(13) 0.0713(14) -0.0057(9) -0.0055(10) 0.0083(11)
  C18B 0.0684(14) 0.0557(12) 0.0651(13) -0.0010(10) -0.0081(11) 0.0141(10)
  C19B 0.0715(14) 0.0451(11) 0.0628(13) -0.0082(10) 0.0055(10) 0.0134(9)
  C20B 0.0488(10) 0.0372(8) 0.0548(10) -0.0063(7) 0.0078(8) 0.0034(8)
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
  O1A C6A . 1.375(2) y
  O1A C2A . 1.377(2) y
  O2A C2A . 1.214(2) y
  O3A C4A . 1.344(2) y
  O3A C11A . 1.441(2) y
  O4A C15A . 1.371(2) y
  O4A C16A . 1.435(2) y
  C2A C3A . 1.443(2) y
  C3A C4A . 1.357(2) y
  C3A C13A . 1.512(2) y
  C4A C5A . 1.445(2) y
  C5A C6A . 1.392(2) y
  C5A C10A . 1.399(2) ?
  C6A C7A . 1.390(2) ?
  C7A C8A . 1.367(3) ?
  C7A H7A . 0.9300 ?
  C8A C9A . 1.391(3) ?
  C8A H8A . 0.9300 ?
  C9A C10A . 1.381(2) ?
  C9A H9A . 0.9300 ?
  C10A H10A . 0.9300 ?
  C11A C12A . 1.516(2) y
  C11A H11A . 0.9700 ?
  C11A H11B . 0.9700 ?
  C12A C16A . 1.508(2) y
  C12A C13A . 1.534(2) y
  C12A H12A . 0.9800 ?
  C13A C14A . 1.529(2) y
  C13A H13A . 0.9800 ?
  C14A C20A . 1.395(2) ?
  C14A C15A . 1.396(2) ?
  C15A C17A . 1.391(2) ?
  C16A H16A . 0.9700 ?
  C16A H16B . 0.9700 ?
  C17A C18A . 1.377(3) ?
  C17A H17A . 0.9300 ?
  C18A C19A . 1.379(3) ?
  C18A H18A . 0.9300 ?
  C19A C20A . 1.381(3) ?
  C19A H19A . 0.9300 ?
  C20A H20A . 0.9300 ?
  O1B C6B . 1.374(2) y
  O1B C2B . 1.382(2) y
  O2B C2B . 1.211(2) y
  O3B C4B . 1.344(2) y
  O3B C11B . 1.443(2) y
  O4B C15B . 1.370(2) y
  O4B C16B . 1.430(2) y
  C2B C3B . 1.444(2) y
  C3B C4B . 1.360(2) y
  C3B C13B . 1.511(2) y
  C4B C5B . 1.448(2) y
  C5B C6B . 1.390(2) y
  C5B C10B . 1.400(2) ?
  C6B C7B . 1.393(2) ?
  C7B C8B . 1.372(3) ?
  C7B H7B . 0.9300 ?
  C8B C9B . 1.391(3) ?
  C8B H8B . 0.9300 ?
  C9B C10B . 1.381(3) ?
  C9B H9B . 0.9300 ?
  C10B H10B . 0.9300 ?
  C11B C12B . 1.513(2) y
  C11B H11C . 0.9700 ?
  C11B H11D . 0.9700 ?
  C12B C16B . 1.510(2) y
  C12B C13B . 1.532(2) y
  C12B H12B . 0.9800 ?
  C13B C14B . 1.530(2) y
  C13B H13B . 0.9800 ?
  C14B C20B . 1.395(2) ?
  C14B C15B . 1.397(2) ?
  C15B C17B . 1.391(3) ?
  C16B H16C . 0.9700 ?
  C16B H16D . 0.9700 ?
  C17B C18B . 1.373(3) ?
  C17B H17B . 0.9300 ?
  C18B C19B . 1.379(3) ?
  C18B H18B . 0.9300 ?
  C19B C20B . 1.381(3) ?
  C19B H19B . 0.9300 ?
  C20B H20B . 0.9300 ?