#------------------------------------------------------------------------------
#$Date: 2017-10-13 09:09:21 +0300 (Fri, 13 Oct 2017) $
#$Revision: 201973 $
#$URL: file:///home/coder/svn-repositories/cod/cif/2/20/30/2203061.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_2203061
loop_
_publ_author_name
'K. Ravikumar'
'S. Selvanayagam'
'T. Venkateshwar Goud'
'P. Krishnaiah'
'Y. Venkateswarlu'
_publ_section_title
;
 A furodysinin lactone derivative from the marine sponge Dysidea
 fragilis
;
_journal_issue                   1
_journal_name_full               'Acta Crystallographica Section E'
_journal_page_first              o139
_journal_page_last               o141
_journal_paper_doi               10.1107/S1600536803029143
_journal_volume                  60
_journal_year                    2004
_chemical_formula_iupac          'C15 H20 O3'
_chemical_formula_moiety         'C15 H20 O3'
_chemical_formula_sum            'C15 H20 O3'
_chemical_formula_weight         248.31
_chemical_name_systematic
;
Furodysinin lactone
;
_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                   7.1736(7)
_cell_length_b                   8.7391(9)
_cell_length_c                   21.301(2)
_cell_measurement_reflns_used    4309
_cell_measurement_temperature    293(2)
_cell_measurement_theta_max      27.65
_cell_measurement_theta_min      2.52
_cell_volume                     1335.4(2)
_computing_cell_refinement       'SAINT (Bruker, 2001)'
_computing_data_collection       'SMART (Bruker, 2001)'
_computing_data_reduction        SAINT
_computing_molecular_graphics
'ORTEP-3 (Farrugia, 1997) and PLATON (Spek, 2003)'
_computing_publication_material  'SHELXL97 and PARST (Nardelli, 1995)'
_computing_structure_refinement  'SHELXL97 (Sheldrick, 1997)'
_computing_structure_solution    'SHELXS97 (Sheldrick, 1997)'
_diffrn_ambient_temperature      293(2)
_diffrn_measured_fraction_theta_full 0.978
_diffrn_measured_fraction_theta_max 0.978
_diffrn_measurement_device       'Bruker SMART APEX'
_diffrn_measurement_device_type  '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  0.0199
_diffrn_reflns_av_sigmaI/netI    0.0160
_diffrn_reflns_limit_h_max       9
_diffrn_reflns_limit_h_min       -8
_diffrn_reflns_limit_k_max       11
_diffrn_reflns_limit_k_min       -10
_diffrn_reflns_limit_l_max       28
_diffrn_reflns_limit_l_min       -27
_diffrn_reflns_number            8149
_diffrn_reflns_theta_full        28.02
_diffrn_reflns_theta_max         28.02
_diffrn_reflns_theta_min         1.91
_diffrn_standards_decay_%        0
_diffrn_standards_number         0
_exptl_absorpt_coefficient_mu    0.085
_exptl_absorpt_correction_T_max  0.9874
_exptl_absorpt_correction_T_min  0.9800
_exptl_absorpt_correction_type   multi-scan
_exptl_crystal_colour            Colourless
_exptl_crystal_density_diffrn    1.235
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       Needle
_exptl_crystal_F_000             536
_exptl_crystal_size_max          0.24
_exptl_crystal_size_mid          0.20
_exptl_crystal_size_min          0.15
_refine_diff_density_max         0.216
_refine_diff_density_min         -0.165
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.126
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     167
_refine_ls_number_reflns         1837
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.126
_refine_ls_R_factor_all          0.0424
_refine_ls_R_factor_gt           0.0397
_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)+(0.058P)²+0.1311P] where P = (Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1022
_refine_ls_wR_factor_ref         0.1041
_reflns_number_gt                1705
_reflns_number_total             1837
_reflns_threshold_expression     I>2σ(I)
_cod_data_source_file            cv6255.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:

'_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               2203061
_cod_database_fobs_code          2203061
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 0.4791(2) 0.66745(15) 0.08407(6) 0.0460(3) Uani d . 1 O
O2 0.3502(2) 0.58560(19) -0.00495(7) 0.0609(4) Uani d . 1 O
O3 0.69330(18) 0.84187(19) 0.12224(6) 0.0494(4) Uani d . 1 O
H3 0.7362 0.8698 0.0884 0.074 Uiso calc R 1 H
C1 0.3851(3) 0.6902(2) 0.03000(9) 0.0453(4) Uani d . 1 C
C2 0.3375(3) 0.8525(2) 0.02439(8) 0.0436(4) Uani d . 1 C
H2 0.2720 0.8965 -0.0087 0.052 Uiso calc R 1 H
C3 0.4028(2) 0.9266(2) 0.07401(7) 0.0361(4) Uani d . 1 C
C4 0.3771(3) 1.0888(2) 0.09503(8) 0.0393(4) Uani d . 1 C
C5 0.2900(2) 1.0833(2) 0.16244(7) 0.0357(4) Uani d . 1 C
H5 0.3029 1.1864 0.1801 0.043 Uiso calc R 1 H
C6 0.0830(3) 1.0446(3) 0.16444(9) 0.0474(5) Uani d . 1 C
H6A 0.0651 0.9393 0.1513 0.057 Uiso calc R 1 H
H6B 0.0163 1.1101 0.1353 0.057 Uiso calc R 1 H
C7 0.0042(3) 1.0660(3) 0.23023(10) 0.0614(6) Uani d . 1 C
H7A -0.0200 1.1739 0.2370 0.074 Uiso calc R 1 H
H7B -0.1139 1.0124 0.2330 0.074 Uiso calc R 1 H
C8 0.1301(3) 1.0093(2) 0.28139(9) 0.0477(5) Uani d . 1 C
C9 0.3038(3) 0.9689(2) 0.27027(8) 0.0431(4) Uani d . 1 C
H9 0.3744 0.9344 0.3040 0.052 Uiso calc R 1 H
C10 0.3968(3) 0.9745(2) 0.20673(7) 0.0367(4) Uani d . 1 C
H10 0.5226 1.0159 0.2125 0.044 Uiso calc R 1 H
C11 0.4157(3) 0.8116(2) 0.18021(8) 0.0406(4) Uani d . 1 C
H11A 0.4914 0.7501 0.2083 0.049 Uiso calc R 1 H
H11B 0.2934 0.7646 0.1773 0.049 Uiso calc R 1 H
C12 0.5046(3) 0.8157(2) 0.11599(8) 0.0374(4) Uani d . 1 C
C13 0.0467(4) 1.0048(3) 0.34651(10) 0.0698(7) Uani d . 1 C
H13A 0.1365 0.9643 0.3755 0.105 Uiso calc R 1 H
H13B -0.0621 0.9409 0.3463 0.105 Uiso calc R 1 H
H13C 0.0126 1.1065 0.3591 0.105 Uiso calc R 1 H
C14 0.2543(4) 1.1749(3) 0.04829(9) 0.0565(6) Uani d . 1 C
H14A 0.3174 1.1819 0.0086 0.085 Uiso calc R 1 H
H14B 0.2297 1.2759 0.0639 0.085 Uiso calc R 1 H
H14C 0.1388 1.1210 0.0429 0.085 Uiso calc R 1 H
C15 0.5670(3) 1.1716(3) 0.09819(10) 0.0526(5) Uani d . 1 C
H15A 0.6368 1.1338 0.1334 0.079 Uiso calc R 1 H
H15B 0.5470 1.2796 0.1029 0.079 Uiso calc R 1 H
H15C 0.6353 1.1527 0.0602 0.079 Uiso calc R 1 H
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 0.0016 '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 0.0060 '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
_geom_angle_publ_flag
C1 O1 C12 109.04(14) ?
C12 O3 H3 109.5 ?
O2 C1 O1 121.3(2) y
O2 C1 C2 129.5(2) y
O1 C1 C2 109.21(16) ?
C3 C2 C1 109.04(17) ?
C3 C2 H2 125.5 ?
C1 C2 H2 125.5 ?
C2 C3 C4 131.1(2) y
C2 C3 C12 109.3(2) y
C4 C3 C12 119.39(15) ?
C3 C4 C14 110.03(15) ?
C3 C4 C15 110.33(16) ?
C14 C4 C15 107.82(16) ?
C3 C4 C5 107.13(13) ?
C14 C4 C5 112.51(16) ?
C15 C4 C5 109.02(14) ?
C6 C5 C10 109.25(15) ?
C6 C5 C4 114.88(15) ?
C10 C5 C4 112.42(14) ?
C6 C5 H5 106.6 ?
C10 C5 H5 106.6 ?
C4 C5 H5 106.6 ?
C5 C6 C7 111.12(17) ?
C5 C6 H6A 109.4 ?
C7 C6 H6A 109.4 ?
C5 C6 H6B 109.4 ?
C7 C6 H6B 109.4 ?
H6A C6 H6B 108.0 ?
C8 C7 C6 113.87(18) ?
C8 C7 H7A 108.8 ?
C6 C7 H7A 108.8 ?
C8 C7 H7B 108.8 ?
C6 C7 H7B 108.8 ?
H7A C7 H7B 107.7 ?
C9 C8 C7 121.9(2) y
C9 C8 C13 122.2(2) ?
C7 C8 C13 115.9(2) ?
C8 C9 C10 124.8(2) y
C8 C9 H9 117.6 ?
C10 C9 H9 117.6 ?
C9 C10 C11 109.76(14) ?
C9 C10 C5 110.4(2) y
C11 C10 C5 112.93(14) ?
C9 C10 H10 107.9 ?
C11 C10 H10 107.9 ?
C5 C10 H10 107.9 ?
C12 C11 C10 110.36(14) ?
C12 C11 H11A 109.6 ?
C10 C11 H11A 109.6 ?
C12 C11 H11B 109.6 ?
C10 C11 H11B 109.6 ?
H11A C11 H11B 108.1 ?
O3 C12 O1 108.2(2) y
O3 C12 C11 109.40(10) y
O1 C12 C11 110.13(15) ?
O3 C12 C3 115.2(2) y
O1 C12 C3 103.36(13) ?
C11 C12 C3 110.37(14) ?
C8 C13 H13A 109.5 ?
C8 C13 H13B 109.5 ?
H13A C13 H13B 109.5 ?
C8 C13 H13C 109.5 ?
H13A C13 H13C 109.5 ?
H13B C13 H13C 109.5 ?
C4 C14 H14A 109.5 ?
C4 C14 H14B 109.5 ?
H14A C14 H14B 109.5 ?
C4 C14 H14C 109.5 ?
H14A C14 H14C 109.5 ?
H14B C14 H14C 109.5 ?
C4 C15 H15A 109.5 ?
C4 C15 H15B 109.5 ?
H15A C15 H15B 109.5 ?
C4 C15 H15C 109.5 ?
H15A C15 H15C 109.5 ?
H15B C15 H15C 109.5 ?
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_publ_flag
O1 C1 1.349(2) y
O1 C12 1.475(2) y
O2 C1 1.205(2) y
O3 C12 1.379(2) y
O3 H3 0.8200 ?
C1 C2 1.463(3) y
C2 C3 1.325(2) y
C2 H2 0.9300 ?
C3 C4 1.498(3) ?
C3 C12 1.508(2) y
C4 C14 1.527(3) ?
C4 C15 1.544(3) y
C4 C5 1.566(2) ?
C5 C6 1.524(3) ?
C5 C10 1.543(2) y
C5 H5 0.9800 ?
C6 C7 1.523(3) ?
C6 H6A 0.9700 ?
C6 H6B 0.9700 ?
C7 C8 1.500(3) ?
C7 H7A 0.9700 ?
C7 H7B 0.9700 ?
C8 C9 1.316(3) y
C8 C13 1.511(3) ?
C9 C10 1.510(2) ?
C9 H9 0.9300 ?
C10 C11 1.538(3) ?
C10 H10 0.9800 ?
C11 C12 1.510(2) y
C11 H11A 0.9700 ?
C11 H11B 0.9700 ?
C13 H13A 0.9600 ?
C13 H13B 0.9600 ?
C13 H13C 0.9600 ?
C14 H14A 0.9600 ?
C14 H14B 0.9600 ?
C14 H14C 0.9600 ?
C15 H15A 0.9600 ?
C15 H15B 0.9600 ?
C15 H15C 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
O3 H3 O2 4_565 0.82 2.00 2.812(2) 174
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
C12 O1 C1 O2 178.70(18) ?
C12 O1 C1 C2 -2.1(2) ?
O2 C1 C2 C3 179.5(2) ?
O1 C1 C2 C3 0.4(2) ?
C1 C2 C3 C4 -172.87(18) ?
C1 C2 C3 C12 1.4(2) ?
C2 C3 C4 C14 -0.6(3) ?
C12 C3 C4 C14 -174.40(17) ?
C2 C3 C4 C15 -119.4(2) ?
C12 C3 C4 C15 66.8(2) y
C2 C3 C4 C5 122.0(2) ?
C12 C3 C4 C5 -51.8(2) ?
C3 C4 C5 C6 -76.3(2) ?
C14 C4 C5 C6 44.8(2) ?
C15 C4 C5 C6 164.32(17) ?
C3 C4 C5 C10 49.5(2) y
C14 C4 C5 C10 170.5(2) y
C15 C4 C5 C10 -69.9(2) y
C10 C5 C6 C7 61.4(2) y
C4 C5 C6 C7 -171.21(16) ?
C5 C6 C7 C8 -41.5(3) y
C6 C7 C8 C9 10.6(3) y
C6 C7 C8 C13 -170.8(2) ?
C7 C8 C9 C10 0.2(3) y
C13 C8 C9 C10 -178.37(19) ?
C8 C9 C10 C11 -105.3(2) ?
C8 C9 C10 C5 19.8(3) y
C6 C5 C10 C9 -49.2(2) y
C4 C5 C10 C9 -177.98(15) ?
C6 C5 C10 C11 74.10(19) ?
C4 C5 C10 C11 -54.7(2) y
C9 C10 C11 C12 178.7(2) ?
C5 C10 C11 C12 55.1(2) y
C1 O1 C12 O3 -119.81(16) ?
C1 O1 C12 C11 120.71(16) ?
C1 O1 C12 C3 2.80(18) ?
C10 C11 C12 O3 75.7(2) y
C10 C11 C12 O1 -165.50(15) ?
C10 C11 C12 C3 -52.0(2) y
C2 C3 C12 O3 115.26(18) ?
C4 C3 C12 O3 -69.7(2) ?
C2 C3 C12 O1 -2.55(19) ?
C4 C3 C12 O1 172.50(15) ?
C2 C3 C12 C11 -120.30(17) ?
C4 C3 C12 C11 54.8(2) y
loop_
_cod_related_entry_id
_cod_related_entry_database
_cod_related_entry_code
1 ChemSpider 21174557
