#------------------------------------------------------------------------------
#$Date: 2025-08-19 01:52:38 +0300 (Tue, 19 Aug 2025) $
#$Revision: 301791 $
#$URL: file:///home/coder/svn-repositories/cod/cif/2/00/94/2009443.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_2009443
loop_
_publ_author_name
'Haltiwanger, R. Curtis'
'Eggleston, Drake S.'
'McKillop, Andrew'
'Taylor, R.J.K.'
'Watson, R.J.'
'Lewis, Norman'
_publ_section_title
;
 Structure of a model for the aranorosin nucleus
;
_journal_issue                   2
_journal_name_full               'Acta Crystallographica Section C'
_journal_page_first              274
_journal_page_last               276
_journal_paper_doi               10.1107/S0108270193009266
_journal_volume                  50
_journal_year                    1994
_chemical_formula_sum            'C9 H10 O5'
_chemical_formula_weight         198.18
_chemical_name_systematic
;
2-hydroxy-6,7:9,10-cis,cis-diepoxy-1-oxaspiro[4.5]decan-8-one
;
_space_group_IT_number           14
_space_group_name_Hall           '-P 2yn'
_space_group_name_H-M_alt        'P 1 21/n 1'
_symmetry_cell_setting           monoclinic
_symmetry_space_group_name_Hall  '-P 2yn'
_symmetry_space_group_name_H-M   'P 1 21/n 1'
_atom_type_scat_source           IntTabIV
_cell_angle_alpha                90.00
_cell_angle_beta                 107.86(2)
_cell_angle_gamma                90.00
_cell_formula_units_Z            8
_cell_length_a                   14.664(6)
_cell_length_b                   6.3190(10)
_cell_length_c                   19.440(7)
_cell_measurement_reflns_used    25
_cell_measurement_temperature    223
_cell_measurement_theta_max      12
_cell_measurement_theta_min      14
_cell_volume                     1714.5(10)
_computing_cell_refinement       SET4_(de_Boer_&_Duisenberg,_1984)
_computing_data_collection       CAD-4_(Enraf-Nonius,_1977)
_computing_data_reduction        PROCESS_MolEN_(Fair,_1990)
_computing_molecular_graphics    ORTEPII_(Johnson,_1976)
_computing_publication_material  BTABLE_PTABLE_CIF_IN_MolEN
_computing_structure_refinement  LSFM_MolEN
_computing_structure_solution    SHELXS86_(Sheldrick,_1985)
_diffrn_measurement_device       Enraf_Nonius_CAD4
_diffrn_measurement_method       θ/2θ
_diffrn_radiation_type           'Mo K\a'
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.141
_diffrn_reflns_limit_h_max       16
_diffrn_reflns_limit_h_min       0
_diffrn_reflns_limit_k_max       7
_diffrn_reflns_limit_k_min       -7
_diffrn_reflns_limit_l_max       21
_diffrn_reflns_limit_l_min       -21
_diffrn_reflns_number            5324
_diffrn_reflns_theta_max         22.98
_diffrn_standards_decay_%        1.17
_diffrn_standards_interval_time  180
_diffrn_standards_number         3
_exptl_absorpt_correction_type   none
_exptl_crystal_colour            colorless
_exptl_crystal_density_diffrn    1.536(gcm^-1^)
_exptl_crystal_description       'elongated flat plate'
_exptl_crystal_F_000             832
_exptl_crystal_size_max          0.65
_exptl_crystal_size_mid          0.20
_exptl_crystal_size_min          0.04
_refine_diff_density_max         0.3639
_refine_diff_density_min         -0.2917
_refine_ls_abs_structure_details
;
;
_refine_ls_extinction_coef       0.77E-06
_refine_ls_extinction_method     isotropic_(Zachariasen,_1963)
_refine_ls_goodness_of_fit_obs   1.095
_refine_ls_hydrogen_treatment    'H atoms refined with U = 1.3 x bonding atom'
_refine_ls_number_parameters     254
_refine_ls_number_reflns         1337
_refine_ls_R_factor_obs          0.060
_refine_ls_shift/esd_max         0.001
_refine_ls_structure_factor_coef F
_refine_ls_weighting_details     'w = 4Fo²/[σ²(Fo²) + 0.0121Fo⁴]'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_obs         0.074
_reflns_number_observed          1337
_reflns_number_total             2379
_reflns_observed_criterion       >3.0\s(I)
_cod_data_source_file            cr1079.cif
_cod_data_source_block           X819
_cod_depositor_comments
;
The following automatic conversions were performed:

'_refine_ls_weighting_scheme' value ' 4Fo^2^/[\s^2^(Fo^2^) +
0.0121Fo^4^]' was changed to 'calc'. New tag
'_refine_ls_weighting_details' was created. The value of the new tag
was set to 'w = 4Fo^2^/[\s^2^(Fo^2^) + 0.0121Fo^4^]'.

Automatic conversion script
Id: cif_fix_values 3143 2015-03-26 13:38:13Z robertas 
;
_cod_original_cell_volume        1714.0(10)
_cod_original_sg_symbol_H-M      'P 21/n'
_cod_database_code               2009443
loop_
_space_group_symop_id
_space_group_symop_operation_xyz
1 x,y,z
2 -x+1/2,y+1/2,-z+1/2
3 -x,-y,-z
4 x+1/2,-y+1/2,z+1/2
loop_
_atom_site_label
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_thermal_displace_type
_atom_site_calc_flag
O1 0.9411(2) -0.1286(5) 0.0839(2) 0.027(2) Uani ?
O2 1.1718(2) 0.0764(5) 0.1009(2) 0.036(2) Uani ?
O3 0.9339(2) 0.2599(5) 0.01950(10) 0.0280(10) Uani ?
O4 0.8296(2) 0.2229(5) 0.1386(2) 0.0310(10) Uani ?
O5 0.7939(2) 0.5436(6) 0.1825(2) 0.047(2) Uani ?
C1 0.9601(3) -0.0146(8) 0.1508(2) 0.028(2) Uani ?
C2 1.0385(3) -0.0767(7) 0.1229(2) 0.024(2) Uani ?
C3 1.0869(3) 0.0873(7) 0.0932(2) 0.024(2) Uani ?
C4 1.0323(3) 0.2861(8) 0.0627(2) 0.030(2) Uani ?
C5 0.9535(3) 0.3419(7) 0.0911(2) 0.025(2) Uani ?
C6 0.9313(3) 0.2167(7) 0.1484(2) 0.022(2) Uani ?
C7 0.9785(3) 0.3213(8) 0.2226(2) 0.032(2) Uani ?
C8 0.9040(4) 0.3060(10) 0.2591(3) 0.048(3) Uani ?
C9 0.8118(3) 0.3277(9) 0.1972(3) 0.039(2) Uani ?
O1' 0.6250(2) 0.3333(5) -0.0988(2) 0.034(2) Uani ?
O2' 0.7773(2) 0.5187(6) -0.1948(2) 0.056(2) Uani ?
O3' 0.5532(2) 0.6886(5) -0.1832(2) 0.030(2) Uani ?
O4' 0.5521(2) 0.6973(5) -0.03130(10) 0.0240(10) Uani ?
O5' 0.6062(2) 0.5664(5) 0.0865(2) 0.030(2) Uani ?
C1' 0.6794(3) 0.4804(8) -0.0478(2) 0.029(2) Uani ?
C2' 0.7162(3) 0.4002(8) -0.1040(3) 0.036(2) Uani ?
C3' 0.7179(3) 0.5387(8) -0.1647(2) 0.033(2) Uani ?
C4' 0.6518(3) 0.7253(8) -0.1804(2) 0.030(2) Uani ?
C5' 0.6149(3) 0.8038(7) -0.1237(2) 0.022(2) Uani ?
C6' 0.6399(3) 0.7030(7) -0.0504(2) 0.021(2) Uani ?
C7' 0.7090(3) 0.8429(8) 0.0086(2) 0.030(2) Uani ?
C8' 0.6522(3) 0.9112(8) 0.0568(2) 0.030(2) Uani ?
C9' 0.5729(3) 0.7470(7) 0.0435(2) 0.027(2) Uani ?
H1 0.9508 -0.0903 0.1915 0.0379 Uiso calc
H2 1.0822 -0.1861 0.1464 0.0362 Uiso calc
H3 0.7210 0.5562 0.1504 0.0671 Uiso calc
H4 1.0726 0.3719 0.0472 0.0428 Uiso calc
H5 0.9383 0.4601 0.0957 0.0362 Uiso calc
H7A 1.0290 0.2665 0.2401 0.0445 Uiso calc
H7B 0.9992 0.4732 0.2068 0.0445 Uiso calc
H8A 0.8943 0.4091 0.2881 0.0659 Uiso calc
H8B 0.8986 0.1673 0.2906 0.0659 Uiso calc
H9 0.7492 0.2829 0.2062 0.0494 Uiso calc
H1' 0.7031 0.4109 -0.0048 0.0412 Uiso calc
H2' 0.7585 0.3224 -0.0992 0.0477 Uiso calc
H3' 0.5465 0.5062 0.0746 0.0412 Uiso calc
H4' 0.6565 0.8123 -0.2110 0.0396 Uiso calc
H5' 0.6057 0.9457 -0.1222 0.0341 Uiso calc
H7'A 0.7628 0.7690 0.0319 0.0412 Uiso calc
H7'B 0.7279 0.9427 -0.0186 0.0412 Uiso calc
H8'A 0.6801 0.9027 0.1084 0.0412 Uiso calc
H8'B 0.6171 1.0724 0.0606 0.0412 Uiso calc
H9' 0.5110 0.7900 0.0540 0.0370 Uiso calc
loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
C1 O1 C2 61.5(3)
C4 O3 C5 61.7(3)
C6 O4 C9 110.3(3)
C9 O5 H3 106.5(3)
O1 C1 C2 59.1(3)
O1 C1 C6 118.6(3)
O1 C1 H1 117.2(4)
C2 C1 C6 119.2(4)
C2 C1 H1 119.6(4)
C6 C1 H1 113.1(4)
O1 C2 C1 59.3(3)
O1 C2 C3 118.5(3)
O1 C2 H2 120.0(4)
C1 C2 C3 119.1(4)
C1 C2 H2 120.2(4)
C3 C2 H2 111.1(4)
O2 C3 C2 121.1(4)
O2 C3 C4 119.9(4)
C2 C3 C4 118.4(4)
O3 C4 C3 116.8(4)
O3 C4 C5 58.8(3)
O3 C4 H4 120.5(4)
C3 C4 C5 115.9(4)
C3 C4 H4 107.5(4)
C5 C4 H4 130.1(5)
O3 C5 C4 59.5(3)
O3 C5 C6 121.0(4)
O3 C5 H5 118.2(4)
C4 C5 C6 122.4(4)
C4 C5 H5 123.3(5)
C6 C5 H5 106.4(5)
O4 C6 C1 107.3(3)
O4 C6 C5 110.1(3)
O4 C6 C7 105.0(4)
C1 C6 C5 114.4(4)
C1 C6 C7 110.0(3)
C5 C6 C7 109.7(4)
C6 C7 C8 103.7(4)
C6 C7 H7A 107.8(5)
C6 C7 H7B 101.5(4)
C8 C7 H7A 119.8(5)
C8 C7 H7B 120.6(5)
H7A C7 H7B 101.5(5)
C7 C8 C9 102.9(4)
C7 C8 H8A 122.5(6)
C7 C8 H8B 121.0(5)
C9 C8 H8A 99.1(5)
C9 C8 H8B 108.5(5)
H8A C8 H8B 100.2(5)
O4 C9 O5 111.1(4)
O4 C9 C8 105.0(4)
O4 C9 H9 114.0(4)
O5 C9 C8 108.4(4)
O5 C9 H9 100.4(4)
C8 C9 H9 117.8(5)
C1' O1' C2' 61.2(3)
C4' O3' C5' 60.8(3)
C6' O4' C9' 109.2(3)
C9' O5' H3' 93.2(3)
O1' C1' C2' 60.2(3)
O1' C1' C6' 117.3(3)
O1' C1' H1' 107.6(4)
C2' C1' C6' 121.7(4)
C2' C1' H1' 113.4(4)
C6' C1' H1' 120.6(5)
O1' C2' C1' 58.5(3)
O1' C2' C3' 118.4(3)
O1' C2' H2' 122.4(5)
C1' C2' C3' 119.9(4)
C1' C2' H2' 127.0(5)
C3' C2' H2' 105.1(5)
O2' C3' C2' 121.5(4)
O2' C3' C4' 120.5(5)
C2' C3' C4' 117.3(4)
O3' C4' C3' 117.4(4)
O3' C4' C5' 58.8(3)
O3' C4' H4' 112.4(4)
C3' C4' C5' 118.9(4)
C3' C4' H4' 118.4(5)
C5' C4' H4' 116.8(5)
O3' C5' C4' 60.4(3)
O3' C5' C6' 117.6(4)
O3' C5' H5' 117.7(3)
C4' C5' C6' 122.4(4)
C4' C5' H5' 117.0(5)
C6' C5' H5' 112.5(4)
O4' C6' C1' 109.3(4)
O4' C6' C5' 106.2(3)
O4' C6' C7' 104.8(3)
C1' C6' C5' 113.8(4)
C1' C6' C7' 110.3(3)
C5' C6' C7' 112.0(4)
C6' C7' C8' 105.2(3)
C6' C7' H7'A 110.2(4)
C6' C7' H7'B 102.0(4)
C8' C7' H7'A 113.8(4)
C8' C7' H7'B 119.3(5)
H7'A C7' H7'B 105.5(5)
C7' C8' C9' 104.1(4)
C7' C8' H8'A 119.8(4)
C7' C8' H8'B 129.8(4)
C9' C8' H8'A 101.3(4)
C9' C8' H8'B 106.1(4)
H8'A C8' H8'B 92.1(4)
O4' C9' O5' 110.7(4)
O4' C9' C8' 103.6(4)
O4' C9' H9' 109.6(3)
O5' C9' C8' 110.1(3)
O5' C9' H9' 105.2(4)
C8' C9' H9' 117.7(4)
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_publ_flag
O1 C1 1.438(5) ?
O1 C2 1.436(4) ?
O2 C3 1.211(5) ?
O3 C4 1.439(5) ?
O3 C5 1.430(5) ?
O4 C6 1.447(5) ?
O4 C9 1.410(6) ?
O5 C9 1.400(6) ?
O5 H3 1.064(3) ?
C1 C2 1.470(7) ?
C1 C6 1.516(7) ?
C1 H1 0.968(5) ?
C2 C3 1.470(7) ?
C2 H2 0.957(4) ?
C3 C4 1.509(6) ?
C4 C5 1.470(7) ?
C4 H4 0.919(5) ?
C5 C6 1.482(7) ?
C5 H5 0.792(5) ?
C6 C7 1.543(6) ?
C7 C8 1.481(8) ?
C7 H7A 0.793(4) ?
C7 H7B 1.078(5) ?
C8 C9 1.515(6) ?
C8 H8A 0.900(6) ?
C8 H8B 1.085(6) ?
C9 H9 1.027(5) ?
O1' C1' 1.413(5) ?
O1' C2' 1.437(6) ?
O2' C3' 1.197(7) ?
O3' C4' 1.451(5) ?
O3' C5' 1.429(5) ?
O4' C6' 1.449(5) ?
O4' C9' 1.426(5) ?
O5' C9' 1.408(5) ?
O5' H3' 0.917(3) ?
C1' C2' 1.451(7) ?
C1' C6' 1.515(7) ?
C1' H1' 0.913(4) ?
C2' C3' 1.476(7) ?
C2' H2' 0.774(5) ?
C3' C4' 1.496(7) ?
C4' C5' 1.457(7) ?
C4' H4' 0.828(5) ?
C5' C6' 1.500(6) ?
C5' H5' 0.907(4) ?
C6' C7' 1.552(6) ?
C7' C8' 1.497(7) ?
C7' H7'A 0.909(4) ?
C7' H7'B 0.919(5) ?
C8' C9' 1.519(6) ?
C8' H8'A 0.962(4) ?
C8' H8'B 1.153(5) ?
C9' H9' 1.028(5) ?
loop_
_cod_related_entry_id
_cod_related_entry_database
_cod_related_entry_code
1 PubChem 139057026
