#------------------------------------------------------------------------------
#$Date: 2016-02-19 23:18:51 +0100 (vie 19 de feb de 2016) $
#$Revision: 176760 $
#$URL: svn://www.crystallography.net/cod/cif/2/01/01/2010178.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_2010178
loop_
_publ_author_name
'Toscano, R.A.'
'Sanchez, A.A.'
'Esquivel, B.'
'Esquivel, O.'
'Rodriguez-Hahn, L.'
_publ_section_title
;
 Salvireptanolide
;
_journal_issue                   11
_journal_name_full               'Acta Crystallographica Section C'
_journal_page_first              1794
_journal_page_last               1796
_journal_paper_doi               10.1107/S0108270194000181
_journal_volume                  50
_journal_year                    1994
_chemical_formula_sum            'C20 H18 O6'
_chemical_formula_weight         354.36
_chemical_name_systematic
;(7R,8S,9R)-5,6-seco-neo-clerodane-1,3,5(10),13(16),14-pentaene-12-oxo-15,
16-epoxy-18,19;20(7)-diolide
;
_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'
_atom_type_scat_source           IntTabIV
_cell_angle_alpha                90.
_cell_angle_beta                 90.
_cell_angle_gamma                90.
_cell_formula_units_Z            4
_cell_length_a                   9.439(3)
_cell_length_b                   12.979(4)
_cell_length_c                   13.773(5)
_cell_measurement_reflns_used    25
_cell_measurement_temperature    298
_cell_measurement_theta_max      16.6
_cell_measurement_theta_min      4.69
_cell_volume                     1687.3(10)
_diffrn_measurement_device       'Nicolet P3F'
_diffrn_measurement_method       2θ-θ
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54178
_diffrn_reflns_av_R_equivalents  0.035
_diffrn_reflns_limit_h_max       9
_diffrn_reflns_limit_h_min       0
_diffrn_reflns_limit_k_max       13
_diffrn_reflns_limit_k_min       0
_diffrn_reflns_limit_l_max       14
_diffrn_reflns_limit_l_min       0
_diffrn_reflns_number            1261
_diffrn_reflns_theta_max         52.4
_diffrn_standards_decay_%        +-3
_diffrn_standards_interval_count 50
_diffrn_standards_number         2
_exptl_absorpt_coefficient_mu    0.82
_exptl_absorpt_correction_type   none
_exptl_crystal_colour            colorless
_exptl_crystal_density_diffrn    1.395
_exptl_crystal_description       prismatic
_exptl_crystal_size_max          0.4
_exptl_crystal_size_mid          0.26
_exptl_crystal_size_min          0.22
_refine_diff_density_max         0.45
_refine_diff_density_min         -0.43
_refine_ls_extinction_coef       2.68(4)
_refine_ls_extinction_method     'Larson (1967)'
_refine_ls_goodness_of_fit_obs   1.08
_refine_ls_hydrogen_treatment    'H atoms refined using a riding model'
_refine_ls_number_parameters     237
_refine_ls_number_reflns         1115
_refine_ls_R_factor_obs          0.039
_refine_ls_shift/esd_max         0.002
_refine_ls_structure_factor_coef F
_refine_ls_weighting_scheme      'weighting scheme: counting statistics'
_refine_ls_wR_factor_obs         0.045
_reflns_number_observed          1115
_reflns_number_total             1136
_reflns_observed_criterion       I>2.5\s(I)
_cod_data_source_file            hh1055.cif
_cod_data_source_block           hh1055_structure_1_of_1
_cod_original_cell_volume        1687.2(5)
_cod_database_code               2010178
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
O(1) -.2724(3) .4931(2) .0559(2) .0510(10)
O(2) -.1753(3) .6353(2) .1145(2) .0560(10)
O(3) -.3505(3) .6576(2) -.0826(2) .0670(10)
O(4) -.2159(5) .8621(3) -.3342(3) .099(2)
O(5) .1348(3) .3710(2) .1994(2) .0620(10)
O(6) .3701(3) .3621(3) .2092(2) .0710(10)
C(1) .1810(4) .6065(3) -.0504(3) .0450(10)
C(2) .3234(4) .5938(3) -.0247(3) .0490(10)
C(3) .3624(4) .5279(3) .0482(3) .0510(10)
C(4) .2542(4) .4755(3) .0950(3) .0440(10)
C(5) .1139(4) .4884(2) .0720(2) .0400(10)
C(6) -.3081(6) .3268(3) -.0208(4) .083(2)
C(7) -.2765(4) .4397(3) -.0382(3) .0540(10)
C(8) -.1333(4) .4619(3) -.0849(3) .0460(10)
C(9) -.0841(3) .5637(2) -.0373(2) .0380(10)
C(10) .0731(3) .5546(2) -.0038(2) .0390(10)
C(11) -.0998(4) .6602(3) -.0996(3) .0440(10)
C(12) -.2511(4) .6891(2) -.1267(3) .0440(10)
C(13) -.2667(4) .7607(3) -.2091(2) .0440(10)
C(14) -.3919(5) .8088(3) -.2391(3) .0590(10)
C(15) -.3614(5) .8683(3) -.3124(3) .066(2)
C(16) -.1638(5) .7963(3) -.2692(3) .0640(10)
C(17) -.1416(5) .4602(4) -.1956(3) .0650(10)
C(18) .2663(4) .3999(3) .1725(3) .0530(10)
C(19) .0294(4) .4215(3) .1415(3) .0530(10)
C(20) -.1806(3) .5716(3) .0516(3) .0420(10)
H1 .158 .653 -.102 .050
H2 .395 .632 -.059 .059
H3 .460 .519 .066 .061
H6A -.311 .291 -.082 .099
H6B -.398 .320 .011 .099
H6C -.235 .297 .019 .099
H7 -.350 .463 -.081 .065
H8 -.063 .410 -.074 .055
H11A -.048 .649 -.159 .053
H11B -.059 .717 -.065 .053
H14 -.484 .800 -.211 .071
H15 -.429 .910 -.347 .079
H16 -.066 .777 -.265 .077
H17A -.050 .474 -.222 .078
H17B -.208 .512 -.217 .078
H17C -.173 .394 -.217 .078
H19A -.026 .372 .107 .052
H19B -.032 .463 .181 .052
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
C(7) O(1) C(20) 109.7(3) yes
C(18) O(5) C(19) 111.0(3) yes
C(1) C(2) C(3) 121.1(4) yes
C(3) C(4) C(5) 122.9(3) yes
C(5) C(4) C(18) 109.2(3) yes
(4) C(5) C(19) 106.9(3) yes
O(1) C(7) C(6) 108.8(3) yes
C(6) C(7) C(8) 115.1(3) yes
C(7) C(8) C(17) 111.9(3) yes
C(8) C(9) C(10) 110.3(3) yes
C(10) C(9) C(11) 108.7(3) yes
C(10) C(9) C(20) 109.5(3) yes
C(1) C(10) C(5) 116.3(3) yes
C(5) C(10) C(9) 121.7(3) yes
O(3) C(12) C(11) 121.9(3) yes
C(11) C(12) C(13) 116.0(3) yes
C(12) C(13) C(16) 127.9(3) yes
C(13) C(14) C(15) 107.9(4) yes
O(4) C(16) C(13) 111.4(4) yes
O(5) C(18) C(4) 108.5(3) yes
O(5) C(19) C(5) 104.4(3) yes
O(1) C(20) C(9) 111.7(3) yes
C(15) O(4) C(16) 104.7(4) yes
C(2) C(1) C(10) 122.3(3) yes
C(2) C(3) C(4) 116.7(3) yes
C(3) C(4) C(18) 127.9(3) yes
C(4) C(5) C(10) 120.7(3) yes
C(10) C(5) C(19) 132.4(3) yes
O(1) C(7) C(8) 105.1(3) yes
C(7) C(8) C(9) 104.3(3) yes
C(9) C(8) C(17) 116.9(3) yes
C(8) C(9) C(11) 115.6(3) yes
C(8) C(9) C(20) 102.6(3) yes
C(11) C(9) C(20) 109.8(3) yes
C(1) C(10) C(9) 121.9(3) yes
C(9) C(11) C(12) 115.6(3) yes
O(3) C(12) C(13) 122.1(3) yes
C(12) C(13) C(14) 126.4(3) yes
C(14) C(13) C(16) 105.7(3) yes
O(4) C(15) C(14) 110.3(4) yes
O(5) C(18) O(6) 121.2(4) yes
O(6) C(18) C(4) 130.3(4) yes
O(1) C(20) O(2) 121.3(3) yes
O(2) C(20) C(9) 126.9(3) yes
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
O(1) C(7) . . 1.472(5) yes
O(2) C(20) . . 1.201(4) yes
O(4) C(15) . . 1.408(7) yes
O(5) C(18) . . 1.348(5) yes
O(6) C(18) . . 1.207(5) yes
C(1) C(10) . . 1.379(5) yes
C(3) C(4) . . 1.387(5) yes
C(4) C(18) . . 1.457(5) yes
C(5) C(19) . . 1.520(5) yes
C(7) C(8) . . 1.525(5) yes
C(8) C(17) . . 1.529(5) yes
C(9) C(11) . . 1.527(5) yes
C(11) C(12) . . 1.522(5) yes
C(13) C(14) . . 1.399(6) yes
C(14) C(15) . . 1.305(6) yes
O(1) C(20) . . 1.338(4) yes
O(3) C(12) . . 1.190(5) yes
O(4) C(16) . . 1.333(6) yes
O(5) C(19) . . 1.434(5) yes
C(1) C(2) . . 1.398(5) yes
C(2) C(3) . . 1.371(5) yes
C(4) C(5) . . 1.371(5) yes
C(5) C(10) . . 1.408(5) yes
C(6) C(7) . . 1.515(6) yes
C(8) C(9) . . 1.547(5) yes
C(9) C(10) . . 1.557(5) yes
C(9) C(20) . . 1.530(5) yes
C(12) C(13) . . 1.475(5) yes
C(13) C(16) . . 1.358(6) yes
