#------------------------------------------------------------------------------
#$Date: 2017-10-13 09:09:21 +0300 (Fri, 13 Oct 2017) $
#$Revision: 201973 $
#$URL: file:///home/coder/svn-repositories/cod/cif/2/20/54/2205463.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_2205463
loop_
_publ_author_name
'Said, Ikram M. '
'Noor, Ainal F. A.'
'Syah, Yana M.'
'Latif, Jalifah'
'Ngah, Nurziana'
'Yamin, Bohari M.'
_publ_section_title
;ent-(8S,10R)-15,16-Epoxy-19-norcleroda-4,11,13(16),14-tetraene-18,6(R):20,12-diolactone
 (isocrotocaudin)
;
_journal_issue                   4
_journal_name_full               'Acta Crystallographica Section E'
_journal_page_first              o1035
_journal_page_last               o1037
_journal_paper_doi               10.1107/S1600536805007725
_journal_volume                  61
_journal_year                    2005
_chemical_formula_iupac          'C19 H18 O5'
_chemical_formula_moiety         'C19 H18 O5'
_chemical_formula_sum            'C19 H18 O5'
_chemical_formula_weight         326.33
_chemical_melting_point          486.1(7)
_chemical_name_common            Isocrotocaudin
_chemical_name_systematic
;
ent-(8S,10R)-15,16-epoxy-19-norcleroda-4,11,13(16),14-tetraene-
18,6(R):20,12-diolactone
;
_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_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_audit_creation_method           SHELXL-97
_cell_angle_alpha                90.00
_cell_angle_beta                 90.00
_cell_angle_gamma                90.00
_cell_formula_units_Z            4
_cell_length_a                   6.677(2)
_cell_length_b                   10.794(3)
_cell_length_c                   22.608(7)
_cell_measurement_reflns_used    743
_cell_measurement_temperature    298(2)
_cell_measurement_theta_max      26.0
_cell_measurement_theta_min      1.8
_cell_volume                     1629.4(8)
_computing_cell_refinement       'SAINT (Siemens, 1996)'
_computing_data_collection       'SMART (Siemens, 1996)'
_computing_data_reduction        SAINT
_computing_molecular_graphics    SHELXTL
_computing_publication_material
'SHELXTL, PARST (Nardelli, 1995) and PLATON (Spek, 2003)'
_computing_structure_refinement  SHELXTL
_computing_structure_solution    'SHELXTL (Sheldrick, 1997)'
_diffrn_ambient_temperature      298(2)
_diffrn_detector_area_resol_mean 83.66
_diffrn_measured_fraction_theta_full 0.99
_diffrn_measured_fraction_theta_max 0.99
_diffrn_measurement_device_type  'Bruker SMART APEX CCD area-detector'
_diffrn_measurement_method       ω
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_source         'fine-focus sealed tube'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0353
_diffrn_reflns_av_sigmaI/netI    0.0303
_diffrn_reflns_limit_h_max       8
_diffrn_reflns_limit_h_min       -8
_diffrn_reflns_limit_k_max       13
_diffrn_reflns_limit_k_min       -13
_diffrn_reflns_limit_l_max       27
_diffrn_reflns_limit_l_min       -18
_diffrn_reflns_number            8831
_diffrn_reflns_theta_full        26.0
_diffrn_reflns_theta_max         26.0
_diffrn_reflns_theta_min         1.8
_diffrn_standards_decay_%        0
_diffrn_standards_interval_time  0
_diffrn_standards_number         0
_exptl_absorpt_coefficient_mu    0.096
_exptl_absorpt_correction_T_max  0.991
_exptl_absorpt_correction_T_min  0.960
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   '(SADABS; Sheldrick, 1996)'
_exptl_crystal_colour            colourless
_exptl_crystal_density_diffrn    1.330
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       slab
_exptl_crystal_F_000             688
_exptl_crystal_size_max          0.42
_exptl_crystal_size_mid          0.10
_exptl_crystal_size_min          0.09
_refine_diff_density_max         0.16
_refine_diff_density_min         -0.13
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.18
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     217
_refine_ls_number_reflns         1866
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.18
_refine_ls_R_factor_all          0.068
_refine_ls_R_factor_gt           0.056
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'calc w = 1/[σ²(Fo²)+(0.0462P)²+0.3404P] where P = (Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.110
_refine_ls_wR_factor_ref         0.113
_reflns_number_gt                1583
_reflns_number_total             1866
_reflns_threshold_expression     I>2σ(I)
_cod_data_source_file            cv6464.cif
_cod_data_source_block           I
_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:

'_chemical_melting_point' value '485.5--486.8' was changed to
'486.1(7)' - the average value was taken and precision was estimated.

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

The following automatic conversions were performed:

'_chemical_melting_point' value '485.5--486.8' was changed to
'486.1(7)' - the average value was taken and precision was
estimated.

'_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_values 1715 2011-07-08 13:25:40Z adriana 
;
_cod_database_code               2205463
_cod_database_fobs_code          2205463
loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'-x+1/2, -y, z+1/2'
'-x, y+1/2, -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_U_iso_or_equiv
_atom_site_adp_type
_atom_site_calc_flag
_atom_site_refinement_flags
_atom_site_occupancy
_atom_site_type_symbol
O1 1.1679(6) 0.3232(3) 0.44225(11) 0.0774(9) Uani d . 1 O
O2 0.8829(4) 0.3716(2) 0.27849(9) 0.0481(6) Uani d . 1 O
O3 0.6987(4) 0.4292(2) 0.20096(10) 0.0521(6) Uani d . 1 O
O4 0.6785(4) 0.2900(3) 0.01985(10) 0.0605(7) Uani d . 1 O
O5 0.7258(5) 0.4628(3) -0.03299(12) 0.0869(10) Uani d . 1 O
C1 1.1822(5) 0.4127(3) 0.15144(14) 0.0475(9) Uani d . 1 C
H1A 1.0990 0.4719 0.1724 0.057 Uiso calc R 1 H
H1B 1.2949 0.3921 0.1767 0.057 Uiso calc R 1 H
C2 1.2589(6) 0.4714(4) 0.09482(16) 0.0605(11) Uani d . 1 C
H2A 1.3413 0.4120 0.0738 0.073 Uiso calc R 1 H
H2B 1.3421 0.5421 0.1046 0.073 Uiso calc R 1 H
C3 1.0880(6) 0.5137(3) 0.05458(16) 0.0573(10) Uani d . 1 C
H3A 1.0265 0.5879 0.0705 0.069 Uiso calc R 1 H
H3B 1.1393 0.5325 0.0155 0.069 Uiso calc R 1 H
C4 0.9381(5) 0.4130(3) 0.05087(13) 0.0418(8) Uani d . 1 C
C5 0.9356(5) 0.3159(3) 0.08600(13) 0.0352(7) Uani d . 1 C
C6 0.7800(5) 0.2275(3) 0.06742(14) 0.0457(8) Uani d . 1 C
H6A 0.8441 0.1524 0.0521 0.055 Uiso calc R 1 H
C7 0.6461(5) 0.1936(3) 0.11863(15) 0.0512(9) Uani d . 1 C
H7A 0.5567 0.1270 0.1070 0.061 Uiso calc R 1 H
H7B 0.5652 0.2645 0.1297 0.061 Uiso calc R 1 H
C8 0.7728(5) 0.1523(3) 0.17134(15) 0.0451(8) Uani d . 1 C
H8A 0.8488 0.0793 0.1587 0.054 Uiso calc R 1 H
C9 0.9281(5) 0.2511(3) 0.19197(12) 0.0351(7) Uani d . 1 C
C10 1.0609(5) 0.2958(3) 0.13902(12) 0.0343(7) Uani d . 1 C
H10A 1.1558 0.2292 0.1298 0.041 Uiso calc R 1 H
C11 1.0549(5) 0.2085(3) 0.24245(13) 0.0399(8) Uani d . 1 C
H11A 1.1413 0.1410 0.2411 0.048 Uiso calc R 1 H
C12 1.0280(5) 0.2792(3) 0.28895(13) 0.0406(8) Uani d . 1 C
C13 1.1131(6) 0.2818(3) 0.34758(14) 0.0461(9) Uani d . 1 C
C14 1.2892(7) 0.2164(4) 0.36677(16) 0.0648(11) Uani d . 1 C
H14A 1.3705 0.1651 0.3440 0.078 Uiso calc R 1 H
C15 1.3119(8) 0.2442(5) 0.42338(18) 0.0803(14) Uani d . 1 C
H15A 1.4139 0.2134 0.4472 0.096 Uiso calc R 1 H
C16 1.0483(7) 0.3431(3) 0.39508(15) 0.0578(10) Uani d . 1 C
H16A 0.9351 0.3933 0.3956 0.069 Uiso calc R 1 H
C17 0.6363(6) 0.1112(4) 0.22187(18) 0.0735(13) Uani d . 1 C
H17A 0.5439 0.0499 0.2077 0.110 Uiso calc R 1 H
H17B 0.5632 0.1814 0.2366 0.110 Uiso calc R 1 H
H17C 0.7158 0.0766 0.2531 0.110 Uiso calc R 1 H
C18 0.7761(6) 0.3981(4) 0.00767(15) 0.0551(10) Uani d . 1 C
C20 0.8209(5) 0.3598(3) 0.22091(14) 0.0396(8) Uani d . 1 C
loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0033 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0106 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
C16 O1 C15 105.8(3)
C20 O2 C12 107.5(2)
C18 O4 C6 109.1(3)
C2 C1 C10 111.7(3)
C2 C1 H1A 109.3
C10 C1 H1A 109.3
C2 C1 H1B 109.3
C10 C1 H1B 109.3
H1A C1 H1B 107.9
C1 C2 C3 112.0(3)
C1 C2 H2A 109.2
C3 C2 H2A 109.2
C1 C2 H2B 109.2
C3 C2 H2B 109.2
H2A C2 H2B 107.9
C4 C3 C2 108.6(3)
C4 C3 H3A 110.0
C2 C3 H3A 110.0
C4 C3 H3B 110.0
C2 C3 H3B 110.0
H3A C3 H3B 108.3
C5 C4 C18 107.8(3)
C5 C4 C3 124.0(3)
C18 C4 C3 128.1(3)
C4 C5 C6 110.7(3)
C4 C5 C10 126.8(3)
C6 C5 C10 122.4(3)
O4 C6 C5 104.0(3)
O4 C6 C7 114.1(3)
C5 C6 C7 110.9(3)
O4 C6 H6A 109.2
C5 C6 H6A 109.2
C7 C6 H6A 109.2
C6 C7 C8 110.0(3)
C6 C7 H7A 109.7
C8 C7 H7A 109.7
C6 C7 H7B 109.7
C8 C7 H7B 109.7
H7A C7 H7B 108.2
C17 C8 C7 109.7(3)
C17 C8 C9 111.8(3)
C7 C8 C9 113.7(3)
C17 C8 H8A 107.1
C7 C8 H8A 107.1
C9 C8 H8A 107.1
C11 C9 C20 100.1(2)
C11 C9 C8 113.3(2)
C20 C9 C8 110.1(3)
C11 C9 C10 111.0(3)
C20 C9 C10 110.9(2)
C8 C9 C10 111.0(2)
C5 C10 C1 109.2(2)
C5 C10 C9 110.1(3)
C1 C10 C9 114.5(2)
C5 C10 H10A 107.6
C1 C10 H10A 107.6
C9 C10 H10A 107.6
C12 C11 C9 110.8(3)
C12 C11 H11A 124.6
C9 C11 H11A 124.6
C11 C12 O2 111.8(3)
C11 C12 C13 134.0(3)
O2 C12 C13 114.3(3)
C16 C13 C14 105.4(3)
C16 C13 C12 128.5(4)
C14 C13 C12 126.1(3)
C15 C14 C13 105.9(4)
C15 C14 H14A 127.1
C13 C14 H14A 127.1
C14 C15 O1 111.5(4)
C14 C15 H15A 124.3
O1 C15 H15A 124.3
C13 C16 O1 111.4(4)
C13 C16 H16A 124.3
O1 C16 H16A 124.3
C8 C17 H17A 109.5
C8 C17 H17B 109.5
H17A C17 H17B 109.5
C8 C17 H17C 109.5
H17A C17 H17C 109.5
H17B C17 H17C 109.5
O5 C18 O4 121.2(4)
O5 C18 C4 130.7(4)
O4 C18 C4 108.2(3)
O3 C20 O2 120.4(3)
O3 C20 C9 129.9(3)
O2 C20 C9 109.7(3)
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_publ_flag
O1 C16 1.350(5) yes
O1 C15 1.354(5) yes
O2 C20 1.372(4) yes
O2 C12 1.411(4) yes
O3 C20 1.196(4) yes
O4 C18 1.365(5) yes
O4 C6 1.439(4) yes
O5 C18 1.202(4) yes
C1 C2 1.517(5) ?
C1 C10 1.526(4) ?
C1 H1A 0.9700 ?
C1 H1B 0.9700 ?
C2 C3 1.529(5) ?
C2 H2A 0.9700 ?
C2 H2B 0.9700 ?
C3 C4 1.480(5) ?
C3 H3A 0.9700 ?
C3 H3B 0.9700 ?
C4 C5 1.316(4) yes
C4 C18 1.466(5) ?
C5 C6 1.471(4) ?
C5 C10 1.478(4) ?
C6 C7 1.508(5) ?
C6 H6A 0.9800 ?
C7 C8 1.528(5) ?
C7 H7A 0.9700 ?
C7 H7B 0.9700 ?
C8 C17 1.527(5) ?
C8 C9 1.559(4) ?
C8 H8A 0.9800 ?
C9 C11 1.494(4) ?
C9 C20 1.522(4) ?
C9 C10 1.566(4) ?
C10 H10A 0.9800 ?
C11 C12 1.312(4) yes
C11 H11A 0.9300 ?
C12 C13 1.442(4) ?
C13 C16 1.334(5) yes
C13 C14 1.439(6) ?
C14 C15 1.323(5) yes
C14 H14A 0.9300 ?
C15 H15A 0.9300 ?
C16 H16A 0.9300 ?
C17 H17A 0.9600 ?
C17 H17B 0.9600 ?
C17 H17C 0.9600 ?
loop_
_geom_hbond_atom_site_label_D
_geom_hbond_atom_site_label_H
_geom_hbond_atom_site_label_A
_geom_hbond_site_symmetry_A
_geom_hbond_distance_DH
_geom_hbond_distance_HA
_geom_hbond_distance_DA
_geom_hbond_angle_DHA
_geom_hbond_publ_flag
C7 H7B O3 1_555 0.97 2.56 3.172(4) 121 yes
C16 H16A O5 2_665 0.93 2.49 3.223(4) 136 yes
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
C10 C1 C2 C3 62.5(4)
C1 C2 C3 C4 -46.3(4)
C2 C3 C4 C5 12.6(5)
C2 C3 C4 C18 -164.1(3)
C18 C4 C5 C6 2.6(4)
C3 C4 C5 C6 -174.7(3)
C18 C4 C5 C10 -174.7(3)
C3 C4 C5 C10 8.1(5)
C18 O4 C6 C5 5.5(3)
C18 O4 C6 C7 126.5(3)
C4 C5 C6 O4 -5.0(4)
C10 C5 C6 O4 172.4(3)
C4 C5 C6 C7 -128.1(3)
C10 C5 C6 C7 49.3(4)
O4 C6 C7 C8 -168.6(3)
C5 C6 C7 C8 -51.5(4)
C6 C7 C8 C17 -176.9(3)
C6 C7 C8 C9 57.0(4)
C17 C8 C9 C11 56.6(4)
C7 C8 C9 C11 -178.4(3)
C17 C8 C9 C20 -54.5(4)
C7 C8 C9 C20 70.4(3)
C17 C8 C9 C10 -177.8(3)
C7 C8 C9 C10 -52.8(3)
C4 C5 C10 C1 6.0(4)
C6 C5 C10 C1 -171.0(3)
C4 C5 C10 C9 132.5(3)
C6 C5 C10 C9 -44.4(4)
C2 C1 C10 C5 -39.7(4)
C2 C1 C10 C9 -163.7(3)
C11 C9 C10 C5 169.8(2)
C20 C9 C10 C5 -79.9(3)
C8 C9 C10 C5 42.9(3)
C11 C9 C10 C1 -66.8(3)
C20 C9 C10 C1 43.6(4)
C8 C9 C10 C1 166.3(3)
C20 C9 C11 C12 -1.1(4)
C8 C9 C11 C12 -118.3(3)
C10 C9 C11 C12 116.1(3)
C9 C11 C12 O2 2.1(4)
C9 C11 C12 C13 -178.4(4)
C20 O2 C12 C11 -2.2(3)
C20 O2 C12 C13 178.2(3)
C11 C12 C13 C16 -166.0(4)
O2 C12 C13 C16 13.5(5)
C11 C12 C13 C14 13.7(7)
O2 C12 C13 C14 -166.8(3)
C16 C13 C14 C15 0.3(5)
C12 C13 C14 C15 -179.5(4)
C13 C14 C15 O1 -0.9(5)
C16 O1 C15 C14 1.2(5)
C14 C13 C16 O1 0.4(4)
C12 C13 C16 O1 -179.8(4)
C15 O1 C16 C13 -1.0(5)
C6 O4 C18 O5 175.4(4)
C6 O4 C18 C4 -4.2(4)
C5 C4 C18 O5 -178.5(4)
C3 C4 C18 O5 -1.4(6)
C5 C4 C18 O4 1.0(4)
C3 C4 C18 O4 178.1(3)
C12 O2 C20 O3 -179.1(3)
C12 O2 C20 C9 1.4(3)
C11 C9 C20 O3 -179.7(3)
C8 C9 C20 O3 -60.2(4)
C10 C9 C20 O3 63.1(4)
C11 C9 C20 O2 -0.3(3)
C8 C9 C20 O2 119.3(3)
C10 C9 C20 O2 -117.5(3)
loop_
_cod_related_entry_id
_cod_related_entry_database
_cod_related_entry_code
1 ChemSpider 21173510
