#------------------------------------------------------------------------------
#$Date: 2008-01-26 15:05:32 +0200 (Sat, 26 Jan 2008) $
#$Revision: 19 $
#$URL: file:///home/coder/svn-repositories/cod/cif/2/2013154.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_2013154
_journal_name_full  'Acta Crystallographica, Section C'
_journal_year  2003
_journal_volume  59
_journal_page_first  o85
_journal_page_last  o87
_publ_section_title
;
A semi-synthetic analog of the cembranoid sarcophine
;
loop_
_publ_author_name
  'Fahmy, Hesham'
  'Zjawiony, Jordan K.'
  'Khalifa, Sherief'
  'Fronczek, Frank R.'
_chemical_name_common  'sarcophine 13'
_chemical_formula_moiety  'C20 H32 O4'
_chemical_formula_sum  'C20 H32 O4'
_chemical_formula_weight  336.46
_symmetry_cell_setting  'Monoclinic'
_symmetry_space_group_name_H-M  'P 21'
_symmetry_space_group_name_Hall  'P 2yb'
loop_
_symmetry_equiv_pos_as_xyz
  'x, y, z'
  '-x, y+1/2, -z'
_cell_length_a  5.858(2)
_cell_length_b  8.232(2)
_cell_length_c  19.241(6)
_cell_angle_alpha  90
_cell_angle_beta  91.315(10)
_cell_angle_gamma  90
_cell_volume  927.6(5)
_cell_formula_units_Z  2
_cell_measurement_temperature  100
_exptl_crystal_density_diffrn  1.205
_diffrn_ambient_temperature  100
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 0.1484(2) 1.16959(16) 0.46428(7) 0.0216(3) Uani d . 1 . . O
  H10 0.107(4) 1.127(4) 0.5039(13) 0.032 Uiso d . 1 . . H
  O2 0.4888(2) 1.04091(18) 0.38159(7) 0.0277(3) Uani d . 1 . . O
  H20 0.501(4) 1.105(4) 0.4158(14) 0.042 Uiso d . 1 . . H
  O3 0.4902(2) 0.21273(16) 0.08076(7) 0.0222(3) Uani d . 1 . . O
  O4 0.0500(2) 0.49855(16) 0.42867(7) 0.0232(3) Uani d . 1 . . O
  H40 0.081(4) 0.409(4) 0.4366(14) 0.035 Uiso d . 1 . . H
  C1 0.2426(3) 0.8281(2) 0.33828(8) 0.0164(3) Uani d . 1 . . C
  C2 0.3698(3) 0.8305(2) 0.28077(9) 0.0178(3) Uani d . 1 . . C
  H2 0.5034 0.8960 0.2818 0.021 Uiso calc R 1 . . H
  C3 0.3179(3) 0.7407(2) 0.21742(9) 0.0178(3) Uani d . 1 . . C
  H3 0.1845 0.6751 0.2172 0.021 Uiso calc R 1 . . H
  C4 0.4400(3) 0.7410(2) 0.15896(9) 0.0179(3) Uani d . 1 . . C
  C5 0.3452(3) 0.6643(2) 0.09330(9) 0.0207(3) Uani d . 1 . . C
  H5A 0.3434 0.7474 0.0561 0.025 Uiso calc R 1 . . H
  H5B 0.1848 0.6328 0.1012 0.025 Uiso calc R 1 . . H
  C6 0.4730(3) 0.5147(2) 0.06692(9) 0.0225(4) Uani d . 1 . . C
  H6A 0.4165 0.4884 0.0194 0.027 Uiso calc R 1 . . H
  H6B 0.6376 0.5407 0.0643 0.027 Uiso calc R 1 . . H
  C7 0.4439(3) 0.3682(2) 0.11278(9) 0.0193(3) Uani d . 1 . . C
  H7 0.5050 0.3807 0.1614 0.023 Uiso calc R 1 . . H
  C8 0.2604(3) 0.2469(2) 0.10389(9) 0.0188(3) Uani d . 1 . . C
  C9 0.1944(3) 0.1413(2) 0.16450(9) 0.0202(3) Uani d . 1 . . C
  H9A 0.3331 0.1198 0.1934 0.024 Uiso calc R 1 . . H
  H9B 0.1397 0.0356 0.1460 0.024 Uiso calc R 1 . . H
  C10 0.0102(3) 0.2110(2) 0.21152(9) 0.0213(3) Uani d . 1 . . C
  H10A -0.1105 0.2623 0.1821 0.026 Uiso calc R 1 . . H
  H10B -0.0607 0.1209 0.2374 0.026 Uiso calc R 1 . . H
  C11 0.1021(3) 0.3347(2) 0.26265(8) 0.0176(3) Uani d . 1 . . C
  H11 0.2620 0.3538 0.2625 0.021 Uiso calc R 1 . . H
  C12 -0.0174(3) 0.4200(2) 0.30802(8) 0.0161(3) Uani d . 1 . . C
  C13 0.1040(3) 0.5352(2) 0.35744(8) 0.0159(3) Uani d . 1 . . C
  H13 0.2724 0.5229 0.3518 0.019 Uiso calc R 1 . . H
  C14 0.0387(3) 0.7159(2) 0.34457(8) 0.0166(3) Uani d . 1 . . C
  H14A -0.0557 0.7231 0.3013 0.020 Uiso calc R 1 . . H
  H14B -0.0557 0.7539 0.3834 0.020 Uiso calc R 1 . . H
  C15 0.2993(3) 0.9387(2) 0.39965(9) 0.0174(3) Uani d . 1 . . C
  C16 0.0945(3) 1.0506(2) 0.41186(9) 0.0196(3) Uani d . 1 . . C
  H16A 0.0511 1.1062 0.3679 0.023 Uiso calc R 1 . . H
  H16B -0.0374 0.9849 0.4265 0.023 Uiso calc R 1 . . H
  C17 0.3673(3) 0.8410(2) 0.46431(9) 0.0234(4) Uani d . 1 . . C
  H17A 0.5037 0.7764 0.4549 0.035 Uiso calc R 1 . . H
  H17B 0.2418 0.7685 0.4766 0.035 Uiso calc R 1 . . H
  H17C 0.4002 0.9154 0.5030 0.035 Uiso calc R 1 . . H
  C18 0.6652(3) 0.8263(3) 0.15228(10) 0.0242(4) Uani d . 1 . . C
  H18A 0.6443 0.9244 0.1239 0.036 Uiso calc R 1 . . H
  H18B 0.7740 0.7537 0.1300 0.036 Uiso calc R 1 . . H
  H18C 0.7243 0.8566 0.1986 0.036 Uiso calc R 1 . . H
  C19 0.0816(3) 0.2589(3) 0.04604(10) 0.0264(4) Uani d . 1 . . C
  H19A 0.1381 0.3289 0.0090 0.040 Uiso calc R 1 . . H
  H19B -0.0589 0.3053 0.0644 0.040 Uiso calc R 1 . . H
  H19C 0.0498 0.1503 0.0273 0.040 Uiso calc R 1 . . H
  C20 -0.2726(3) 0.4094(3) 0.31326(10) 0.0249(4) Uani d . 1 . . C
  H20A -0.3441 0.4950 0.2849 0.037 Uiso calc R 1 . . H
  H20B -0.3154 0.4232 0.3619 0.037 Uiso calc R 1 . . H
  H20C -0.3249 0.3030 0.2965 0.037 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
  O1 0.0304(6) 0.0163(6) 0.0183(6) -0.0022(5) 0.0031(5) -0.0026(5)
  O2 0.0275(6) 0.0277(7) 0.0281(7) -0.0116(6) 0.0086(5) -0.0081(6)
  O3 0.0232(6) 0.0194(6) 0.0243(6) 0.0033(5) 0.0056(5) -0.0034(5)
  O4 0.0397(7) 0.0151(6) 0.0148(6) 0.0024(6) 0.0044(5) 0.0008(5)
  C1 0.0190(7) 0.0134(7) 0.0168(7) 0.0014(6) 0.0015(6) 0.0006(6)
  C2 0.0198(7) 0.0143(7) 0.0194(8) -0.0003(6) 0.0020(6) 0.0011(6)
  C3 0.0216(7) 0.0133(7) 0.0185(7) -0.0006(6) 0.0030(6) 0.0020(6)
  C4 0.0222(7) 0.0134(7) 0.0182(8) 0.0025(6) 0.0027(6) 0.0016(6)
  C5 0.0263(8) 0.0198(8) 0.0163(7) 0.0013(7) 0.0025(6) 0.0009(6)
  C6 0.0298(9) 0.0195(8) 0.0186(8) -0.0001(7) 0.0078(6) -0.0016(6)
  C7 0.0227(7) 0.0179(8) 0.0175(8) 0.0025(7) 0.0025(6) -0.0011(6)
  C8 0.0209(7) 0.0184(8) 0.0173(7) 0.0019(6) 0.0024(6) -0.0030(6)
  C9 0.0271(8) 0.0152(7) 0.0183(8) -0.0003(7) 0.0021(6) -0.0017(6)
  C10 0.0232(7) 0.0220(8) 0.0189(8) -0.0055(7) 0.0039(6) -0.0049(7)
  C11 0.0186(7) 0.0168(7) 0.0176(7) -0.0019(6) 0.0018(6) -0.0001(6)
  C12 0.0169(7) 0.0152(7) 0.0163(7) -0.0005(6) 0.0019(5) 0.0017(6)
  C13 0.0188(7) 0.0149(7) 0.0142(7) 0.0002(6) 0.0028(5) 0.0009(6)
  C14 0.0183(7) 0.0140(7) 0.0175(7) 0.0005(6) 0.0030(6) 0.0006(6)
  C15 0.0179(7) 0.0168(8) 0.0177(7) -0.0018(6) 0.0023(6) -0.0007(6)
  C16 0.0262(8) 0.0149(7) 0.0175(7) 0.0014(7) -0.0004(6) -0.0014(6)
  C17 0.0243(8) 0.0246(9) 0.0210(8) 0.0030(7) -0.0027(6) 0.0002(7)
  C18 0.0253(8) 0.0261(9) 0.0215(8) -0.0014(8) 0.0080(6) -0.0003(7)
  C19 0.0267(8) 0.0326(10) 0.0198(8) -0.0014(8) -0.0014(7) -0.0008(8)
  C20 0.0194(8) 0.0263(9) 0.0291(9) -0.0020(7) 0.0043(7) -0.0047(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
  O1 C16 . 1.436(2) y
  O1 H10 . 0.88(3) ?
  O2 C15 . 1.442(2) y
  O2 H20 . 0.85(3) ?
  O3 C7 . 1.449(2) y
  O3 C8 . 1.455(2) y
  O4 C13 . 1.446(2) y
  O4 H40 . 0.77(3) ?
  C1 C2 . 1.348(2) y
  C1 C14 . 1.517(2) ?
  C1 C15 . 1.522(2) ?
  C2 C3 . 1.452(2) y
  C2 H2 . 0.9500 ?
  C3 C4 . 1.347(2) y
  C3 H3 . 0.9500 ?
  C4 C18 . 1.503(2) ?
  C4 C5 . 1.507(2) ?
  C5 C6 . 1.534(3) ?
  C5 H5A . 0.9900 ?
  C5 H5B . 0.9900 ?
  C6 C7 . 1.506(3) ?
  C6 H6A . 0.9900 ?
  C6 H6B . 0.9900 ?
  C7 C8 . 1.474(2) y
  C7 H7 . 1.0000 ?
  C8 C9 . 1.512(2) ?
  C8 C19 . 1.514(2) ?
  C9 C10 . 1.535(2) ?
  C9 H9A . 0.9900 ?
  C9 H9B . 0.9900 ?
  C10 C11 . 1.506(2) ?
  C10 H10A . 0.9900 ?
  C10 H10B . 0.9900 ?
  C11 C12 . 1.332(2) y
  C11 H11 . 0.9500 ?
  C12 C20 . 1.503(2) ?
  C12 C13 . 1.509(2) ?
  C13 C14 . 1.554(2) ?
  C13 H13 . 1.0000 ?
  C14 H14A . 0.9900 ?
  C14 H14B . 0.9900 ?
  C15 C17 . 1.527(2) ?
  C15 C16 . 1.535(2) ?
  C16 H16A . 0.9900 ?
  C16 H16B . 0.9900 ?
  C17 H17A . 0.9800 ?
  C17 H17B . 0.9800 ?
  C17 H17C . 0.9800 ?
  C18 H18A . 0.9800 ?
  C18 H18B . 0.9800 ?
  C18 H18C . 0.9800 ?
  C19 H19A . 0.9800 ?
  C19 H19B . 0.9800 ?
  C19 H19C . 0.9800 ?
  C20 H20A . 0.9800 ?
  C20 H20B . 0.9800 ?
  C20 H20C . 0.9800 ?