data_2202204
_journal_name_full  'Acta Crystallographica, Section E'
_journal_year  2003
_journal_volume  59
_journal_page_first  o290
_journal_page_last  o292
_publ_section_title
;
7,14-Dioxatetracyclo(14.2^4,5^.2^19,20^.2^21,22^.2^23,24^)tetracosa-
1,3,5,9,11,15,17,19,21,23-decaene
;
loop_
_publ_author_name
  'T. Ravishankar'
  'K. Chinnakali'
  'P. Rajakumar'
  'V. Murali'
  'Anwar Usman'
  'Hoong-Kun Fun'
_chemical_formula_moiety  'C22 H18 O2'
_chemical_formula_sum  'C22 H18 O2'
_chemical_formula_iupac  'C22 H18 O2'
_chemical_formula_weight  314.36
_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  9.5687(2)
_cell_length_b  10.5926(2)
_cell_length_c  16.6960(2)
_cell_angle_alpha  90.00
_cell_angle_beta  95.4230(10)
_cell_angle_gamma  90.00
_cell_volume  1684.69(5)
_cell_formula_units_Z  4
_cell_measurement_temperature  293(2)
_exptl_crystal_density_diffrn  1.239
_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
  O1 0.17399(15) 0.16090(14) 0.21384(10) 0.0543(4) Uani d . 1 . . O
  O2 0.80714(18) 0.38732(14) 0.37132(11) 0.0647(5) Uani d . 1 . . O
  C1 0.2258(3) 0.1027(3) 0.28874(16) 0.0537(6) Uani d . 1 . . C
  H1A 0.2555(19) 0.0175(19) 0.2779(11) 0.036(5) Uiso d . 1 . . H
  H1B 0.137(3) 0.0979(19) 0.3181(14) 0.064(7) Uiso d . 1 . . H
  C2 0.3422(2) 0.17881(19) 0.33218(13) 0.0443(5) Uani d . 1 . . C
  C3 0.3216(3) 0.3042(2) 0.35151(15) 0.0510(6) Uani d . 1 . . C
  H3 0.226(3) 0.335(2) 0.3418(15) 0.071(7) Uiso d . 1 . . H
  C4 0.4317(3) 0.3787(2) 0.38139(14) 0.0522(6) Uani d . 1 . . C
  H4 0.418(2) 0.466(2) 0.3889(13) 0.064(7) Uiso d . 1 . . H
  C5 0.5662(2) 0.33057(19) 0.39436(13) 0.0481(6) Uani d . 1 . . C
  C6 0.5864(3) 0.2031(2) 0.38035(15) 0.0528(6) Uani d . 1 . . C
  H6 0.686(3) 0.169(2) 0.3871(14) 0.067(7) Uiso d . 1 . . H
  C7 0.4755(3) 0.1291(2) 0.34972(14) 0.0514(6) Uani d . 1 . . C
  H7 0.497(2) 0.038(2) 0.3364(13) 0.060(6) Uiso d . 1 . . H
  C8 0.6909(3) 0.4158(3) 0.41730(18) 0.0629(7) Uani d . 1 . . C
  H8A 0.665(2) 0.511(2) 0.4074(13) 0.061(6) Uiso d . 1 . . H
  H8B 0.728(2) 0.402(2) 0.4764(16) 0.067(7) Uiso d . 1 . . H
  C9 0.7814(2) 0.3878(2) 0.28907(15) 0.0508(6) Uani d . 1 . . C
  C10 0.8710(3) 0.3156(2) 0.2472(2) 0.0606(7) Uani d . 1 . . C
  H10 0.946(3) 0.272(2) 0.2781(18) 0.102(10) Uiso d . 1 . . H
  C11 0.8490(3) 0.3053(2) 0.16485(19) 0.0598(7) Uani d . 1 . . C
  H11 0.905(3) 0.244(2) 0.1363(15) 0.074(8) Uiso d . 1 . . H
  C12 0.7360(2) 0.3630(2) 0.12129(15) 0.0514(6) Uani d . 1 . . C
  C13 0.6519(3) 0.4409(2) 0.16426(16) 0.0534(6) Uani d . 1 . . C
  H13 0.568(2) 0.4857(19) 0.1338(13) 0.062(7) Uiso d . 1 . . H
  C14 0.6737(3) 0.4543(2) 0.24637(16) 0.0525(6) Uani d . 1 . . C
  H14 0.616(3) 0.515(2) 0.2741(14) 0.068(7) Uiso d . 1 . . H
  C15 0.7008(3) 0.3405(2) 0.03448(17) 0.0645(7) Uani d . 1 . . C
  H15 0.783(3) 0.359(2) 0.0036(17) 0.089(9) Uiso d . 1 . . H
  C16 0.5776(3) 0.2994(2) 0.00325(17) 0.0641(7) Uani d . 1 . . C
  H16 0.558(3) 0.283(2) -0.0587(18) 0.098(9) Uiso d . 1 . . H
  C17 0.4655(2) 0.2574(2) 0.05302(13) 0.0468(6) Uani d . 1 . . C
  C18 0.3399(3) 0.3232(2) 0.05660(14) 0.0513(6) Uani d . 1 . . C
  H18 0.323(2) 0.399(2) 0.0204(14) 0.063(7) Uiso d . 1 . . H
  C19 0.2445(3) 0.2879(2) 0.10938(14) 0.0472(6) Uani d . 1 . . C
  H19 0.160(3) 0.334(2) 0.1158(14) 0.063(7) Uiso d . 1 . . H
  C20 0.2712(2) 0.18594(19) 0.16002(13) 0.0417(5) Uani d . 1 . . C
  C21 0.3915(2) 0.1157(2) 0.15415(14) 0.0472(6) Uani d . 1 . . C
  H21 0.408(2) 0.044(2) 0.1876(13) 0.060(7) Uiso d . 1 . . H
  C22 0.4860(3) 0.1520(2) 0.10124(14) 0.0512(6) Uani d . 1 . . C
  H22 0.573(2) 0.103(2) 0.0986(13) 0.066(7) 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
  O1 0.0300(8) 0.0734(10) 0.0605(11) -0.0045(7) 0.0095(8) 0.0060(8)
  O2 0.0495(11) 0.0689(11) 0.0717(13) -0.0048(8) -0.0150(10) -0.0063(9)
  C1 0.0426(15) 0.0593(16) 0.0619(17) -0.0060(12) 0.0186(13) 0.0076(13)
  C2 0.0445(13) 0.0484(13) 0.0415(13) -0.0009(10) 0.0132(10) 0.0098(10)
  C3 0.0464(15) 0.0545(14) 0.0537(15) 0.0069(12) 0.0126(12) 0.0052(11)
  C4 0.0664(18) 0.0437(14) 0.0470(14) 0.0095(12) 0.0079(12) 0.0008(11)
  C5 0.0567(15) 0.0454(13) 0.0406(13) 0.0030(11) -0.0035(11) 0.0012(10)
  C6 0.0520(16) 0.0486(14) 0.0555(15) 0.0076(11) -0.0075(13) -0.0029(11)
  C7 0.0562(15) 0.0440(14) 0.0537(15) 0.0034(11) 0.0038(12) 0.0026(11)
  C8 0.069(2) 0.0579(17) 0.0577(18) 0.0018(13) -0.0148(15) -0.0065(13)
  C9 0.0419(14) 0.0461(13) 0.0627(17) -0.0104(10) -0.0035(12) -0.0012(12)
  C10 0.0331(14) 0.0566(15) 0.091(2) -0.0039(11) 0.0022(14) -0.0034(15)
  C11 0.0384(15) 0.0521(15) 0.092(2) -0.0072(11) 0.0216(15) -0.0071(15)
  C12 0.0426(14) 0.0492(14) 0.0657(16) -0.0083(10) 0.0218(12) 0.0026(12)
  C13 0.0463(15) 0.0538(14) 0.0615(17) 0.0021(11) 0.0122(12) 0.0086(13)
  C14 0.0508(16) 0.0451(13) 0.0615(17) 0.0003(11) 0.0055(12) -0.0011(12)
  C15 0.066(2) 0.0650(16) 0.0685(19) -0.0051(14) 0.0372(16) 0.0065(14)
  C16 0.076(2) 0.0752(18) 0.0441(16) 0.0000(14) 0.0204(14) 0.0043(14)
  C17 0.0494(14) 0.0574(14) 0.0345(12) -0.0042(11) 0.0083(10) -0.0025(11)
  C18 0.0574(16) 0.0522(14) 0.0432(14) 0.0024(12) -0.0016(12) 0.0060(11)
  C19 0.0393(14) 0.0516(14) 0.0500(14) 0.0058(11) 0.0002(11) -0.0041(11)
  C20 0.0289(11) 0.0504(13) 0.0460(13) -0.0064(9) 0.0044(10) -0.0065(10)
  C21 0.0415(14) 0.0469(13) 0.0541(14) 0.0053(10) 0.0100(11) 0.0085(11)
  C22 0.0448(14) 0.0560(14) 0.0547(15) 0.0085(11) 0.0144(12) 0.0023(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
  O1 C20 . 1.379(3) yes
  O1 C1 . 1.440(3) yes
  O2 C9 . 1.372(3) yes
  O2 C8 . 1.441(3) yes
  C1 C2 . 1.504(3) yes
  C1 H1A . 0.97(2) ?
  C1 H1B . 1.02(3) ?
  C2 C3 . 1.386(3) ?
  C2 C7 . 1.386(3) ?
  C3 C4 . 1.372(3) ?
  C3 H3 . 0.97(2) ?
  C4 C5 . 1.382(3) ?
  C4 H4 . 0.95(2) ?
  C5 C6 . 1.387(3) ?
  C5 C8 . 1.517(3) yes
  C6 C7 . 1.378(3) ?
  C6 H6 . 1.02(2) ?
  C7 H7 . 1.02(2) ?
  C8 H8A . 1.05(2) ?
  C8 H8B . 1.03(2) ?
  C9 C10 . 1.386(4) ?
  C9 C14 . 1.388(3) ?
  C10 C11 . 1.376(4) ?
  C10 H10 . 0.96(3) ?
  C11 C12 . 1.387(3) ?
  C11 H11 . 0.99(3) ?
  C12 C13 . 1.397(3) ?
  C12 C15 . 1.476(4) yes
  C13 C14 . 1.374(3) ?
  C13 H13 . 1.02(2) ?
  C14 H14 . 0.99(2) ?
  C15 C16 . 1.317(4) yes
  C15 H15 . 1.00(3) ?
  C16 C17 . 1.486(3) yes
  C16 H16 . 1.05(3) ?
  C17 C22 . 1.380(3) ?
  C17 C18 . 1.395(3) ?
  C18 C19 . 1.379(3) ?
  C18 H18 . 1.01(2) ?
  C19 C20 . 1.381(3) ?
  C19 H19 . 0.96(2) ?
  C20 C21 . 1.382(3) ?
  C21 C22 . 1.377(3) ?
  C21 H21 . 0.95(2) ?
  C22 H22 . 0.99(2) ?