#------------------------------------------------------------------------------
#$Date: 2013-12-28 13:58:47 +0000 (Sat, 28 Dec 2013) $
#$Revision: 91933 $
#$URL: svn://www.crystallography.net/cod/cif/2/00/49/2004933.cif $
#------------------------------------------------------------------------------
#
# This file is available in the Crystallography Open Database (COD),
# http://www.crystallography.net/. The original data for this entry
# were provided by IUCr Journals, http://journals.iucr.org/.
#
# The file may be used within the scientific community so long as
# proper attribution is given to the journal article from which the
# data were obtained.
#
data_2004933
loop_
_publ_author_name
'Harmata, M.'
'Elomari, S.'
'Barnes, C. L.'
_publ_section_title
(+-)-(3a<i>R</i>*,6<i>S</i>*,7<i>S</i>*,14a<i>R</i>*)-2,3,3a,7,8,9,10,11,12,13,14,14a-Dodecahydro-1<i>H</i>,6<i>H</i>-3a,6-epoxy-7,14a-methanocyclopentacyclotridecen-15-one
_journal_issue                   5
_journal_name_full               'Acta Crystallographica Section C'
_journal_page_first              1209
_journal_page_last               1211
_journal_volume                  52
_journal_year                    1996
_chemical_formula_sum            'C17 H24 O2'
_chemical_formula_weight         260.37
_space_group_IT_number           15
_symmetry_cell_setting           monoclinic
_symmetry_space_group_name_Hall  '-C 2yc'
_symmetry_space_group_name_H-M   'C 1 2/c 1'
_atom_type_scat_source           IntTabIV
_cell_angle_alpha                90
_cell_angle_beta                 101.706(3)
_cell_angle_gamma                90
_cell_formula_units_Z            8
_cell_length_a                   31.208(2)
_cell_length_b                   8.7588(4)
_cell_length_c                   10.9435(11)
_cell_measurement_reflns_used    25
_cell_measurement_temperature    298
_cell_measurement_theta_max      25
_cell_measurement_theta_min      20
_cell_volume                     2929.1(4)
_computing_cell_refinement       'CAD-4 Software'
_computing_data_collection       'CAD-4 Software (Enraf-Nonius, 1989)'
_computing_data_reduction
'NRCVAX (Gabe, Le Page, Charland, Lee & White, 1989)'
_computing_molecular_graphics    'ORTEPII (Johnson, 1976)'
_computing_publication_material  NRCVAX
_computing_structure_refinement  NRCVAX
_computing_structure_solution    NRCVAX
_diffrn_measurement_device       'Enraf-Nonius CAD-4'
_diffrn_measurement_method       '\w/2\q scans'
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54184
_diffrn_reflns_av_R_equivalents  0.023
_diffrn_reflns_limit_h_max       34
_diffrn_reflns_limit_h_min       -34
_diffrn_reflns_limit_k_max       9
_diffrn_reflns_limit_k_min       0
_diffrn_reflns_limit_l_max       12
_diffrn_reflns_limit_l_min       0
_diffrn_reflns_number            2306
_diffrn_reflns_theta_max         60
_diffrn_standards_decay_%        none
_diffrn_standards_interval_time  60
_diffrn_standards_number         3
_exptl_absorpt_coefficient_mu    0.56
_exptl_absorpt_correction_type   none
_exptl_crystal_colour            colourless
_exptl_crystal_density_diffrn    1.181
_exptl_crystal_description       rod
_exptl_crystal_size_max          0.45
_exptl_crystal_size_mid          0.20
_exptl_crystal_size_min          0.20
_refine_diff_density_max         0.40
_refine_diff_density_min         -0.25
_refine_ls_extinction_coef       2.4(3)
_refine_ls_extinction_method     'Larson (1970)'
_refine_ls_goodness_of_fit_obs   3.18
_refine_ls_hydrogen_treatment    'H atoms riding'
_refine_ls_number_parameters     173
_refine_ls_number_reflns         1922
_refine_ls_R_factor_obs          0.054
_refine_ls_shift/esd_max         0.003
_refine_ls_structure_factor_coef F
_refine_ls_weighting_scheme      '                    1/[\s^2^(F)+0.0005F^2^]'
_refine_ls_wR_factor_obs         0.090
_reflns_number_observed          1922
_reflns_number_total             2169
_reflns_observed_criterion       I>2.5\s(I)
_[local]_cod_data_source_file    cf1040.cif
_[local]_cod_data_source_block   cf1040a
_[local]_cod_cif_authors_sg_H-M  'C 2/c'
_cod_database_code               2004933
loop_
_symmetry_equiv_pos_as_xyz
x,y,z
x,-y,1/2+z
-x,-y,-z
-x,y,1/2-z
1/2+x,1/2+y,z
1/2+x,1/2-y,1/2+z
1/2-x,1/2-y,-z
1/2-x,1/2+y,1/2-z
loop_
_atom_site_label
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_B_iso_or_equiv
O10 .13098(5) .0533(2) .27729(13) 4.85(8)
O11 .04541(4) .1017(3) .10242(13) 3.95(6)
C1 .11355(8) .2439(2) .1165(2) 4.36(9)
C2 .14303(8) .2806(3) .0230(3) 5.73(12)
C3 .19331(10) .2757(4) .0795(3) 7.5(2)
C4 .21278(8) .1218(4) .1277(3) 6.6(2)
C5 .20764(7) -.0076(4) .0329(3) 6.4(2)
C6 .20459(9) -0.1720(4) .0786(3) 7.4(2)
C7 .17361(9) -0.2134(3) .1609(3) 6.64(14)
C8 .12430(7) -0.1994(3) .1120(2) 4.70(10)
C9 .10892(6) -.0402(2) .0677(2) 3.51(8)
C10 .12085(6) .0820(2) .1666(2) 3.53(9)
C11 .05824(6) -.0153(2) .0236(2) 3.71(9)
C12 .04848(7) .0608(3) -0.1022(2) 4.59(11)
C13 .05123(7) .2091(3) -.0828(2) 5.12(11)
C14 .06193(7) .2394(2) .0555(2) 4.39(10)
C15 .04279(11) .3741(3) .1112(3) 7.1(2)
C16 .07088(13) .3852(4) .2433(4) 8.1(2)
C17 .11743(10) .3623(3) .2227(3) 6.64(14)
H2A .137 .196 -0.050 6.5
H2B .134 .392 -0.016 6.5
H3A .199 .355 .157 8.2
H3B .210 .314 .009 8.2
H4A .197 .086 .201 7.3
H4B .247 .137 .165 7.3
H5A .178 .015 -0.036 7.2
H5B .236 -0.002 -0.011 7.2
H6A .237 -0.203 .129 8.1
H6B .196 -0.242 -0.004 8.1
H7A .180 -0.330 .190 7.4
H7B .182 -0.139 .241 7.4
H8A .108 -0.230 .187 5.4
H8B .115 -0.278 .035 5.4
H9 .124 -0.012 -0.010 4.3
H11 .041 -0.121 .026 4.5
H12 .040 .004 -0.192 5.3
H13 .047 .296 -0.154 5.8
H15A .046 .477 .059 7.8
H15B .009 .355 .114 7.8
H16A .063 .295 .302 8.9
H16B .067 .494 .286 8.9
H17A .129 .469 .194 7.3
H17B .139 .322 .306 7.3
loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_publ_flag
C11 O11 C14 102.53(14) yes
C2 C1 C10 111.6(2) no
C2 C1 C14 114.3(2) no
C2 C1 C17 113.2(2) no
C10 C1 C14 100.9(2) no
C10 C1 C17 111.8(2) no
C14 C1 C17 104.3(2) no
C1 C2 C3 114.7(2) no
C2 C3 C4 117.2(2) no
C3 C4 C5 116.3(2) no
C4 C5 C6 118.8(3) no
C5 C6 C7 121.0(3) no
C6 C7 C8 119.9(3) no
C7 C8 C9 114.5(2) no
C8 C9 C10 113.8(2) no
C8 C9 C11 117.2(2) no
C10 C9 C11 102.0(2) no
O10 C10 C1 122.8(2) no
O10 C10 C9 122.9(2) no
C1 C10 C9 113.9(2) yes
O11 C11 C9 107.3(2) no
O11 C11 C12 101.7(2) no
C9 C11 C12 110.3(2) no
C11 C12 C13 107.2(2) no
C12 C13 C14 109.2(2) no
O11 C14 C1 105.8(2) no
O11 C14 C13 100.8(2) no
O11 C14 C15 108.1(2) no
C1 C14 C13 114.8(2) no
C1 C14 C15 105.0(2) no
C13 C14 C15 121.3(2) no
C14 C15 C16 103.5(2) no
C15 C16 C17 103.4(2) no
C1 C17 C16 105.5(2) no
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_publ_flag
O10 C10 1.215(2) no
O11 C11 1.447(2) no
O11 C14 1.446(3) no
C1 C2 1.542(3) no
C1 C10 1.521(3) no
C1 C14 1.614(3) no
C1 C17 1.544(4) no
C2 C3 1.566(4) no
C3 C4 1.528(5) no
C4 C5 1.523(5) no
C5 C6 1.533(5) no
C6 C7 1.493(5) no
C7 C8 1.528(4) no
C8 C9 1.522(3) no
C9 C10 1.514(3) no
C9 C11 1.572(3) no
C11 C12 1.503(3) no
C12 C13 1.316(4) no
C13 C14 1.506(3) no
C14 C15 1.506(4) no
C15 C16 1.534(5) no
C16 C17 1.527(5) no
loop_
_geom_torsion_atom_site_label_1
_geom_torsion_atom_site_label_2
_geom_torsion_atom_site_label_3
_geom_torsion_atom_site_label_4
_geom_torsion
_geom_torsion_publ_flag
C14 O11 C11 C9 74.5(3) yes
C11 O11 C14 C1 -79.7(3) yes
C14 C1 C10 C9 58.5(2) yes
C10 C1 C14 O11 13.4(2) yes
C11 C9 C10 C1 -64.0(3) yes
C10 C9 C11 O11 -4.6(2) yes
C14 O11 C11 C12 -41.3(2) yes
C11 O11 C14 C13 40.2(2) yes
O11 C11 C12 C13 26.4(2) yes
C11 C12 C13 C14 -1.2(2) yes
C12 C13 C14 O11 -24.5(2) yes
C10 C1 C2 C3 -62.8(3) yes
C2 C1 C10 C9 -63.3(3) yes
C1 C2 C3 C4 64.0(4) yes
C2 C3 C4 C5 59.1(4) yes
C3 C4 C5 C6 -150.1(6) yes
C4 C5 C6 C7 49.6(4) yes
C5 C6 C7 C8 64.4(4) yes
C6 C7 C8 C9 -57.7(3) yes
C7 C8 C9 C10 -57.6(3) yes
C8 C9 C10 C1 168.7(4) yes
C17 C1 C14 C15 11.5(3) yes
C14 C1 C17 C16 15.2(3) yes
C1 C14 C15 C16 -33.6(3) yes
C14 C15 C16 C17 43.8(3) yes
C15 C16 C17 C1 -36.2(3) yes
_journal_paper_doi 10.1107/S0108270195015782