#------------------------------------------------------------------------------
#$Date: 2016-02-19 16:29:56 +0200 (Fri, 19 Feb 2016) $
#$Revision: 176759 $
#$URL: svn://www.crystallography.net/cod/cif/2/00/79/2007908.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_2007908
loop_
_publ_author_name
'Santos, Marcelo H.'
'Speziali, Nivaldo L.'
'Nagem, Tanus J.'
'Oliveira, Tânia T.'
_publ_section_title
;
 Epiclusianone: a New Natural Product Derivative of
 Bicyclo[3.3.1]nonane-2,4,9-trione
;
_journal_issue                   12
_journal_name_full               'Acta Crystallographica Section C'
_journal_page_first              1990
_journal_page_last               1992
_journal_paper_doi               10.1107/S0108270198006477
_journal_volume                  54
_journal_year                    1998
_chemical_formula_structural     'C33 H42 O4'
_chemical_formula_sum            'C33 H42 O4'
_chemical_formula_weight         502.7
_chemical_name_systematic
;
 3-benzoyl-4-hydroxy-6-6-dimethyl-1,5,7-tri(3-methyl-2-butenyl)bicyclo[3.3.1]
non-3-ene-2,9-dione
;
_space_group_IT_number           19
_symmetry_cell_setting           orthorhombic
_symmetry_space_group_name_Hall  'P 2ac 2ab'
_symmetry_space_group_name_H-M   'P 21 21 21'
_cell_angle_alpha                90.000
_cell_angle_beta                 90.000
_cell_angle_gamma                90.000
_cell_formula_units_Z            4
_cell_length_a                   8.777(2)
_cell_length_b                   12.557(2)
_cell_length_c                   27.324(5)
_cell_measurement_reflns_used    27
_cell_measurement_temperature    298
_cell_measurement_theta_max      12.43
_cell_measurement_theta_min      10.93
_cell_volume                     3011.5(10)
_computing_cell_refinement       'XSCANS (Siemens,1991)'
_computing_data_collection       'XSCANS (Siemens,1991)'
_computing_data_reduction        'XSCANS (Siemens,1991)'
_computing_publication_material  'SHELXTL/PC (Sheldrick,1990)'
_computing_structure_refinement  'SHELXTL/PC (Sheldrick,1990)'
_computing_structure_solution    'SHELXTL/PC (Sheldrick,1990)'
_diffrn_ambient_temperature      298
_diffrn_measurement_device       'Siemens P4 diffractometer'
_diffrn_measurement_method       θ/2θ
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_source         'X-ray tube'
_diffrn_radiation_type           'Mo K\a'
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.06
_diffrn_reflns_limit_h_max       11
_diffrn_reflns_limit_h_min       -11
_diffrn_reflns_limit_k_max       16
_diffrn_reflns_limit_k_min       0
_diffrn_reflns_limit_l_max       35
_diffrn_reflns_limit_l_min       0
_diffrn_reflns_number            6375
_diffrn_reflns_theta_max         27.67
_diffrn_reflns_theta_min         3.50
_diffrn_standards_decay_%        none
_diffrn_standards_interval_count 247
_diffrn_standards_number         3
_exptl_absorpt_coefficient_mu    0.071
_exptl_absorpt_correction_type   none
_exptl_crystal_colour            'Light yellow'
_exptl_crystal_density_diffrn    1.109
_exptl_crystal_density_meas      ?
_exptl_crystal_description       'Prism '
_exptl_crystal_F_000             1088
_exptl_crystal_size_max          0.20
_exptl_crystal_size_mid          0.16
_exptl_crystal_size_min          0.16
_refine_diff_density_max         0.24
_refine_diff_density_min         -0.23
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_obs   1.54
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_constraints    0
_refine_ls_number_parameters     334
_refine_ls_number_reflns         2495
_refine_ls_number_restraints     0
_refine_ls_R_factor_obs          0.0648
_refine_ls_shift/esd_max         0.007
_refine_ls_shift/esd_mean        0.001
_refine_ls_structure_factor_coef F
_refine_ls_weighting_details     w=1/(σ(F))
_refine_ls_weighting_scheme      sigma
_refine_ls_wR_factor_obs         0.0585
_reflns_number_observed          2535
_reflns_number_total             6055
_reflns_observed_criterion       refl_observed_if_F_>=4.0_sigma(F)
_cod_data_source_file            da1009.cif
_cod_data_source_block           da1009
_cod_depositor_comments
;
The following automatic conversions were performed:
'_symmetry_cell_setting' value 'Orthorhombic' changed to 'orthorhombic'
according to '/home/saulius/struct/CIF-dictionaries/cif_core.dic'
dictionary named 'cif_core.dic' version 2.4.1 from 2010-06-29.

Automatic conversion script
Id: cif_fix_enum 1527 2010-12-29 10:47:43Z saulius 

The following automatic conversions were performed:

'_diffrn_ambient_temperature' value '298 (K)' was changed to '298' -
the value should be numeric and without a unit designator.

Automatic conversion script
Id: cif_fix_values 1646 2011-03-28 12:23:43Z adriana 

The following automatic conversions were performed:

'_diffrn_ambient_temperature' value '298 (K)' was changed to '298' -
the value should be numeric and without a unit
designator.

'_symmetry_cell_setting' value 'Orthorhombic' changed to
'orthorhombic' according to
/home/saulius/struct/CIF-dictionaries/cif_core.dic dictionary named
'cif_core.dic' version 2.4.1 from
2010-06-29.

'_refine_ls_matrix_type' value 'Full' changed to 'full'
according to /home/saulius/struct/CIF-dictionaries/cif_core.dic
dictionary named 'cif_core.dic' version 2.4.1 from 2010-06-29.

Automatic conversion script
Id: cif_fix_values 1715 2011-07-08 13:25:40Z adriana 

The following automatic conversions were performed:

'_exptl_crystal_density_meas' value 'not measured' was changed to '?'
- the value is perceived as not measured.

Automatic conversion script
Id: cif_fix_values 3008 2015-01-20 13:52:24Z robertas 
;
_cod_original_cell_volume        3011.6(11)
_cod_database_code               2007908
loop_
_symmetry_equiv_pos_as_xyz
x,y,z
'1/2-x, -y, 1/2+z'
'-x, 1/2+y, 1/2-z'
'1/2+x, 1/2-y, -z'
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
O2 0.6254(4) 0.9147(3) 0.06120(10) 0.0630(10) Uani
O4 0.8019(4) 1.1863(3) 0.15980(10) 0.0640(10) Uani
O9 0.4500(4) 0.9529(3) 0.21680(10) 0.0770(10) Uani
O10 0.9781(4) 1.1100(3) 0.10080(10) 0.0760(10) Uani
C1 0.4714(5) 0.9584(3) 0.1296(2) 0.046(2) Uani
C2 0.6198(5) 0.9621(4) 0.0996(2) 0.047(2) Uani
C3 0.7435(5) 1.0285(3) 0.1181(2) 0.042(2) Uani
C4 0.7093(5) 1.1078(4) 0.1514(2) 0.047(2) Uani
C5 0.5666(5) 1.1098(4) 0.1834(2) 0.051(2) Uani
C6 0.4403(5) 1.1892(4) 0.1612(2) 0.062(2) Uani
C7 0.3914(5) 1.1552(4) 0.1087(2) 0.060(2) Uani
C8 0.3533(5) 1.0356(4) 0.1057(2) 0.059(2) Uani
C9 0.4942(5) 0.9987(4) 0.1806(2) 0.053(2) Uani
C10 0.8920(5) 1.0300(4) 0.0949(2) 0.056(2) Uani
C11 0.9554(6) 0.9381(5) 0.0676(2) 0.061(2) Uani
C12 1.0504(7) 0.9576(6) 0.0282(2) 0.092(3) Uani
C13 1.1177(11) 0.8717(9) 0.0043(3) 0.139(5) Uani
C14 1.0906(13) 0.7705(10) 0.0200(4) 0.151(6) Uani
C15 1.0028(9) 0.7537(6) 0.0587(4) 0.127(4) Uani
C16 0.9330(6) 0.8360(5) 0.0837(3) 0.089(3) Uani
C17 0.4960(7) 1.3048(3) 0.1620(2) 0.075(2) Uani
C18 0.2980(6) 1.1849(5) 0.1944(2) 0.085(2) Uani
C19 0.6152(7) 1.1370(4) 0.2361(2) 0.072(2) Uani
C20 0.7348(8) 1.0640(5) 0.2554(2) 0.077(2) Uani
C21 0.8666(8) 1.0877(5) 0.2745(2) 0.087(3) Uani
C22 0.9235(7) 1.1977(5) 0.2801(3) 0.113(3) Uani
C23 0.9735(9) 1.0036(6) 0.2921(3) 0.129(3) Uani
C24 0.4894(6) 1.1948(4) 0.0656(2) 0.064(2) Uani
C25 0.4208(7) 1.1695(4) 0.0169(2) 0.073(2) Uani
C26 0.4850(9) 1.1279(4) -0.0216(2) 0.080(3) Uani
C27 0.6491(9) 1.0958(5) -0.0254(2) 0.106(3) Uani
C28 0.3968(10) 1.1053(5) -0.0681(2) 0.126(4) Uani
C29 0.4067(5) 0.8444(3) 0.1287(2) 0.064(2) Uani
C30 0.5189(5) 0.7624(4) 0.1453(2) 0.062(2) Uani
C31 0.5161(6) 0.6591(4) 0.1355(2) 0.063(2) Uani
C32 0.3883(7) 0.6076(4) 0.1080(2) 0.085(2) Uani
C33 0.6379(7) 0.5858(4) 0.1543(2) 0.087(2) Uani
H4A 0.8805 1.1777 0.1420 0.0800 Uiso
H7A 0.2957 1.1904 0.1035 0.0800 Uiso
H8A 0.2556 1.0237 0.1205 0.0800 Uiso
H8B 0.3447 1.0170 0.0718 0.0800 Uiso
H12A 1.0711 1.0289 0.0174 0.0800 Uiso
H13A 1.1835 0.8821 -0.0234 0.0800 Uiso
H14A 1.1333 0.7101 0.0034 0.0800 Uiso
H15A 0.9872 0.6827 0.0708 0.0800 Uiso
H16A 0.8692 0.8223 0.1116 0.0800 Uiso
H17A 0.4188 1.3509 0.1489 0.0800 Uiso
H17B 0.5182 1.3253 0.1951 0.0800 Uiso
H17C 0.5867 1.3106 0.1426 0.0800 Uiso
H18A 0.2219 1.2321 0.1815 0.0800 Uiso
H18B 0.2588 1.1135 0.1949 0.0800 Uiso
H18C 0.3241 1.2064 0.2270 0.0800 Uiso
H19A 0.5273 1.1334 0.2570 0.0800 Uiso
H19B 0.6529 1.2087 0.2370 0.0800 Uiso
H20A 0.7108 0.9895 0.2539 0.0800 Uiso
H22A 0.8486 1.2466 0.2678 0.0800 Uiso
H22B 0.9417 1.2122 0.3141 0.0800 Uiso
H22C 1.0166 1.2061 0.2621 0.0800 Uiso
H23A 0.9284 0.9348 0.2871 0.0800 Uiso
H23B 1.0677 1.0078 0.2744 0.0800 Uiso
H23C 0.9928 1.0138 0.3264 0.0800 Uiso
H24A 0.5884 1.1626 0.0676 0.0800 Uiso
H24B 0.5023 1.2705 0.0682 0.0800 Uiso
H25A 0.3143 1.1856 0.0138 0.0800 Uiso
H27A 0.6997 1.1121 0.0048 0.0800 Uiso
H27B 0.6566 1.0208 -0.0318 0.0800 Uiso
H27C 0.6964 1.1346 -0.0516 0.0800 Uiso
H28A 0.2925 1.1266 -0.0639 0.0800 Uiso
H28B 0.4409 1.1442 -0.0948 0.0800 Uiso
H28C 0.4011 1.0304 -0.0750 0.0800 Uiso
H29A 0.3761 0.8281 0.0958 0.0800 Uiso
H29B 0.3177 0.8408 0.1490 0.0800 Uiso
H30A 0.6013 0.7872 0.1654 0.0800 Uiso
H32A 0.3166 0.6606 0.0974 0.0800 Uiso
H32B 0.4279 0.5706 0.0800 0.0800 Uiso
H32C 0.3382 0.5579 0.1293 0.0800 Uiso
H33A 0.7141 0.6272 0.1709 0.0800 Uiso
H33B 0.5942 0.5356 0.1768 0.0800 Uiso
H33C 0.6838 0.5483 0.1275 0.0800 Uiso
loop_
_atom_type_symbol
_atom_type_scat_source
C International_Tables_Vol_IV_Table_2.2B
H International_Tables_Vol_IV_Table_2.2B
O International_Tables_Vol_IV_Table_2.2B
loop_
_diffrn_standard_refln_index_h
_diffrn_standard_refln_index_k
_diffrn_standard_refln_index_l
2 1 0
2 0 5
1 2 7
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
C2 C1 C8 108.6(4) yes
C2 C1 C9 111.9(4) yes
C8 C1 C9 105.6(4) yes
C2 C1 C29 109.3(4) yes
C8 C1 C29 109.0(4) no
C9 C1 C29 112.3(4) no
O2 C2 C1 118.9(4) no
O2 C2 C3 123.6(4) no
C1 C2 C3 117.4(4) yes
C2 C3 C4 118.6(4) yes
C2 C3 C10 121.6(4) no
C4 C3 C10 118.3(4) no
O4 C4 C3 121.9(4) no
O4 C4 C5 113.5(4) no
C3 C4 C5 124.6(4) yes
C4 C5 C6 111.0(4) no
C4 C5 C9 107.2(4) yes
C6 C5 C9 105.0(4) no
C4 C5 C19 108.2(4) no
C6 C5 C19 113.9(4) yes
C9 C5 C19 111.3(4) yes
C5 C6 C7 111.5(4) yes
C5 C6 C17 111.2(4) no
C7 C6 C17 111.2(4) no
C5 C6 C18 108.2(4) no
C7 C6 C18 107.9(4) no
C17 C6 C18 106.4(4) no
C6 C7 C8 112.1(4) yes
C6 C7 C24 117.4(4) yes
C8 C7 C24 113.3(4) no
C1 C8 C7 116.1(4) no
O9 C9 C1 124.0(4) no
O9 C9 C5 121.7(5) no
C1 C9 C5 114.2(4) yes
O10 C10 C3 119.4(4) no
O10 C10 C11 117.2(4) no
C3 C10 C11 123.2(4) yes
C10 C11 C12 118.7(6) no
C10 C11 C16 120.9(5) no
C12 C11 C16 120.2(6) no
C11 C12 C13 118.9(7) no
C12 C13 C14 120.0(9) no
C13 C14 C15 120.1(10) no
C14 C15 C16 122.2(9) no
C11 C16 C15 118.6(6) no
C5 C19 C20 113.0(4) no
C19 C20 C21 128.8(6) no
C20 C21 C22 123.8(6) no
C20 C21 C23 121.7(6) no
C22 C21 C23 114.5(6) no
C7 C24 C25 112.7(4) yes
C24 C25 C26 129.0(6) no
C25 C26 C27 125.5(6) yes
C25 C26 C28 122.1(7) no
C27 C26 C28 112.5(6) no
C1 C29 C30 113.1(4) no
C29 C30 C31 126.9(5) no
C30 C31 C32 122.6(5) no
C30 C31 C33 121.2(5) no
C32 C31 C33 116.2(4) no
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_site_symmetry_1
_geom_bond_site_symmetry_2
_geom_bond_distance
_geom_bond_publ_flag
O2 C2 . . 1.208(6) yes
O4 C4 . . 1.299(6) yes
O9 C9 . . 1.209(7) yes
O10 C10 . . 1.268(6) yes
C1 C2 . . 1.541(6) no
C1 C8 . . 1.562(6) yes
C1 C9 . . 1.496(7) yes
C2 C3 . . 1.460(6) yes
C3 C4 . . 1.380(6) yes
C3 C10 . . 1.449(6) yes
C4 C5 . . 1.528(6) no
C5 C6 . . 1.610(7) yes
C5 C9 . . 1.534(7) no
C6 C7 . . 1.557(8) yes
C7 C8 . . 1.541(7) no
C7 C24 . . 1.540(7) yes
C24 C25 . . 1.495(8) no
C25 C26 . . 1.302(9) yes
C26 C27 . . 1.499(10) yes
C26 C28 . . 1.516(10) no
