#------------------------------------------------------------------------------
#$Date: 2025-08-19 17:49:58 +0300 (Tue, 19 Aug 2025) $
#$Revision: 301806 $
#$URL: file:///home/coder/svn-repositories/cod/cif/2/23/77/2237774.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_2237774
loop_
_publ_author_name
'Selaïmia-Ferdjani, Ouassila'
'Bidjou-Haiour, Chahra'
'Planchat, Aurelien'
'Pipelier, Muriel'
_publ_section_title
;
 (1R,2S,4S,4aS,8S,8aS)-4-Hydroxy-8,8a-dimethyl-10-oxo-2,3,4,7,8,8a-hexahydro-1H-4a,1-(epoxymethano)naphthalen-2-yl
 acetate
;
_journal_coeditor_code           BT6907
_journal_issue                   6
_journal_name_full               'Acta Crystallographica Section E'
_journal_page_first              o938
_journal_page_last               o939
_journal_paper_doi               10.1107/S1600536813013524
_journal_volume                  69
_journal_year                    2013
_chemical_formula_iupac          'C15 H20 O5'
_chemical_formula_moiety         'C15 H20 O5'
_chemical_formula_sum            'C15 H20 O5'
_chemical_formula_weight         280.3
_chemical_name_systematic
;(1R,2S,4S,4aS,8S,8aS)-4-Hydroxy-8,8a-dimethyl-10-oxo-2,3,4,7,8,8a-hexahydro-1H-
4a,1-(epoxymethano)naphthalen-2-yl acetate
;
_space_group_IT_number           4
_symmetry_cell_setting           monoclinic
_symmetry_space_group_name_Hall  'P 2yb'
_symmetry_space_group_name_H-M   'P 1 21 1'
_cell_angle_alpha                90
_cell_angle_beta                 115.958(5)
_cell_angle_gamma                90
_cell_formula_units_Z            2
_cell_length_a                   10.3312(10)
_cell_length_b                   7.1692(8)
_cell_length_c                   10.8502(6)
_cell_measurement_temperature    293
_cell_volume                     722.56(12)
_computing_cell_refinement       'EVALCCD (Duisenberg et al., 2003)'
_computing_data_collection       'COLLECT (Nonius, 1998)'
_computing_data_reduction        'COLLECT (Nonius, 1998)'
_computing_molecular_graphics    'Mercury (Macrae et al., 2006)'
_computing_publication_material
'JANA2006 (Petříček et al., 2006)'
_computing_structure_refinement
'JANA2006 (Petříček et al., 2006)'
_computing_structure_solution    'SIR2004 (Burla et al., 2005)'
_diffrn_ambient_temperature      293
_diffrn_measured_fraction_theta_full 0.98
_diffrn_measured_fraction_theta_max 0.98
_diffrn_measurement_device       'four-cycle diffractometer'
_diffrn_measurement_device_type  'Nonius KappaCCD'
_diffrn_measurement_method       'CCD, φ and ω frames'
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_source         'X-ray tube'
_diffrn_radiation_type           'Mo K\a'
_diffrn_radiation_wavelength     0.71069
_diffrn_reflns_av_R_equivalents  0.0493
_diffrn_reflns_av_sigmaI/netI    0.0243
_diffrn_reflns_limit_h_max       13
_diffrn_reflns_limit_h_min       -13
_diffrn_reflns_limit_k_max       9
_diffrn_reflns_limit_k_min       -9
_diffrn_reflns_limit_l_max       14
_diffrn_reflns_limit_l_min       -14
_diffrn_reflns_number            12282
_diffrn_reflns_theta_full        28.1
_diffrn_reflns_theta_max         28.1
_diffrn_reflns_theta_min         6.53
_exptl_absorpt_coefficient_mu    0.096
_exptl_absorpt_correction_T_max  0.9718
_exptl_absorpt_correction_T_min  0.9668
_exptl_absorpt_correction_type   gaussian
_exptl_absorpt_process_details
'(JANA2006; Petříček et al., 2006)'
_exptl_crystal_colour            colourless
_exptl_crystal_density_diffrn    1.288
_exptl_crystal_description       block
_exptl_crystal_F_000             300
_exptl_crystal_size_max          0.48
_exptl_crystal_size_mid          0.42
_exptl_crystal_size_min          0.30
_refine_diff_density_max         0.15
_refine_diff_density_min         -0.12
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.84
_refine_ls_hydrogen_treatment    mixed
_refine_ls_number_constraints    77
_refine_ls_number_parameters     185
_refine_ls_number_reflns         3328
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0705
_refine_ls_R_factor_gt           0.0502
_refine_ls_shift/su_max          0.0126
_refine_ls_shift/su_mean         0.0013
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details     w=1/(σ²(I)+0.0025000002I²)
_refine_ls_weighting_scheme      sigma
_refine_ls_wR_factor_gt          0.1229
_refine_ls_wR_factor_ref         0.1383
_reflns_number_gt                2774
_reflns_number_total             3328
_reflns_threshold_expression     I>2σ(I)
_cod_data_source_file            bt6907.cif
_cod_data_source_block           I
_cod_original_sg_symbol_H-M      'P 21'
_cod_database_code               2237774
_cod_database_fobs_code          2237774
loop_
_symmetry_equiv_pos_site_id
_symmetry_equiv_pos_as_xyz
1 x,y,z
2 -x,y+1/2,-z
loop_
_atom_site_type_symbol
_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_occupancy
_atom_site_symmetry_multiplicity
O O4a -0.24245(17) -0.3248(2) -0.96277(13) 0.0469(6) Uani d 1 2
O O2 0.13229(15) -0.5347(2) -0.74186(16) 0.0540(6) Uani d 1 2
O O9 -0.1870(2) -0.6248(2) -0.95660(17) 0.0580(7) Uani d 1 2
O O4 -0.0236(2) 0.0757(2) -0.7741(2) 0.0747(9) Uani d 1 2
O O12 0.3391(2) -0.4418(4) -0.5763(2) 0.0969(10) Uani d 1 2
C C1 -0.0910(2) -0.4390(3) -0.74640(18) 0.0373(6) Uani d 1 2
C C2 0.0592(2) -0.3717(3) -0.7223(2) 0.0452(8) Uani d 1 2
C C3 0.0495(3) -0.2237(3) -0.8268(3) 0.0614(11) Uani d 1 2
C C4 -0.0719(3) -0.0820(3) -0.8628(3) 0.0554(10) Uani d 1 2
C C5 -0.3316(3) -0.0382(3) -0.9057(3) 0.0649(10) Uani d 1 2
C C6 -0.4264(3) -0.0442(5) -0.8551(3) 0.0789(12) Uani d 1 2
C C7 -0.4257(3) -0.1856(5) -0.7544(3) 0.0787(13) Uani d 1 2
C C8 -0.3245(2) -0.3495(4) -0.7387(2) 0.0565(9) Uani d 1 2
C C9 -0.1760(2) -0.4802(3) -0.8969(2) 0.0409(7) Uani d 1 2
C C10 -0.0991(3) -0.1656(4) -0.5957(2) 0.0558(9) Uani d 1 2
C C11 -0.3100(3) -0.4779(6) -0.6212(3) 0.0855(15) Uani d 1 2
C C12 0.2732(2) -0.5534(3) -0.6613(2) 0.0504(8) Uani d 1 2
C C13 0.3297(3) -0.7288(4) -0.6924(3) 0.0661(11) Uani d 1 2
C C8a -0.1778(2) -0.2776(3) -0.72788(18) 0.0400(7) Uani d 1 2
C C4a -0.2064(2) -0.1689(3) -0.8603(2) 0.0446(7) Uani d 1 2
H H1c5 -0.343345 0.053419 -0.97428 0.0778 Uiso d 1 2
H H1c6 -0.500769 0.048719 -0.885126 0.0947 Uiso d 1 2
H H1c7 -0.521658 -0.231528 -0.781906 0.0945 Uiso d 1 2
H H2c7 -0.398331 -0.127184 -0.666953 0.0945 Uiso d 1 2
H H1c8 -0.365931 -0.42545 -0.819637 0.0678 Uiso d 1 2
H H1c11 -0.262203 -0.590901 -0.625442 0.1026 Uiso d 1 2
H H2c11 -0.254686 -0.416546 -0.535349 0.1026 Uiso d 1 2
H H3c11 -0.403884 -0.507108 -0.628833 0.1026 Uiso d 1 2
H H1c10 -0.162091 -0.070956 -0.590084 0.0669 Uiso d 1 2
H H2c10 -0.070651 -0.247485 -0.518177 0.0669 Uiso d 1 2
H H3c10 -0.015259 -0.108038 -0.595774 0.0669 Uiso d 1 2
H H1c1 -0.078238 -0.541924 -0.68555 0.0448 Uiso d 1 2
H H1c2 0.108852 -0.317946 -0.632628 0.0543 Uiso d 1 2
H H1c13 0.266544 -0.830237 -0.698342 0.0793 Uiso d 1 2
H H2c13 0.335007 -0.715916 -0.778133 0.0793 Uiso d 1 2
H H3c13 0.42399 -0.753581 -0.620827 0.0793 Uiso d 1 2
H H1c3 0.041767 -0.283227 -0.908981 0.0736 Uiso d 1 2
H H2c3 0.139807 -0.159392 -0.795406 0.0736 Uiso d 1 2
H H1c4 -0.099131 -0.040857 -0.955087 0.0665 Uiso d 1 2
H H1 -0.056(5) 0.173(7) -0.818(4) 0.107(13) Uiso d 1 2
loop_
_atom_type_symbol
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C 0.0033 0.0016 'International Tables Vol C tables 4.2.6.8 and 6.1.1.1'
H 0.0000 0.0000 'International Tables Vol C tables 4.2.6.8 and 6.1.1.1'
O 0.0106 0.0060 'International Tables Vol C tables 4.2.6.8 and 6.1.1.1'
loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
C9 O4a C4a 108.72(13)
C2 O2 C12 118.11(17)
C4 O4 H1 111(3)
C2 C1 C9 108.2(2)
C2 C1 C8a 110.30(16)
C2 C1 H1c1 107.44
C9 C1 C8a 101.19(14)
C9 C1 H1c1 115.73
C8a C1 H1c1 113.8
O2 C2 C1 105.87(16)
O2 C2 C3 108.7(2)
O2 C2 H1c2 112.88
C1 C2 C3 111.08(17)
C1 C2 H1c2 110.54
C3 C2 H1c2 107.84
C2 C3 C4 115.7(3)
C2 C3 H1c3 109.47
C2 C3 H2c3 109.47
C4 C3 H1c3 109.47
C4 C3 H2c3 109.47
H1c3 C3 H2c3 102.43
O4 C4 C3 110.43(19)
O4 C4 C4a 111.3(3)
O4 C4 H1c4 108.45
C3 C4 C4a 111.97(19)
C3 C4 H1c4 107.71
C4a C4 H1c4 106.8
C6 C5 C4a 122.5(3)
C6 C5 H1c5 118.76
C4a C5 H1c5 118.76
C5 C6 C7 124.3(3)
C5 C6 H1c6 117.87
C7 C6 H1c6 117.87
C6 C7 C8 112.8(3)
C6 C7 H1c7 109.47
C6 C7 H2c7 109.47
C8 C7 H1c7 109.47
C8 C7 H2c7 109.47
H1c7 C7 H2c7 105.88
C7 C8 C11 111.6(3)
C7 C8 C8a 110.4(2)
C7 C8 H1c8 108.87
C11 C8 C8a 113.63(18)
C11 C8 H1c8 105.3
C8a C8 H1c8 106.65
O4a C9 O9 121.67(17)
O4a C9 C1 109.53(16)
O9 C9 C1 128.80(17)
C8a C10 H1c10 109.47
C8a C10 H2c10 109.47
C8a C10 H3c10 109.47
H1c10 C10 H2c10 109.47
H1c10 C10 H3c10 109.47
H2c10 C10 H3c10 109.47
C8 C11 H1c11 109.47
C8 C11 H2c11 109.47
C8 C11 H3c11 109.47
H1c11 C11 H2c11 109.47
H1c11 C11 H3c11 109.47
H2c11 C11 H3c11 109.47
O2 C12 O12 122.1(2)
O2 C12 C13 111.11(19)
O12 C12 C13 126.8(2)
C12 C13 H1c13 109.47
C12 C13 H2c13 109.47
C12 C13 H3c13 109.47
H1c13 C13 H2c13 109.47
H1c13 C13 H3c13 109.47
H2c13 C13 H3c13 109.47
C1 C8a C8 110.28(18)
C1 C8a C10 114.76(15)
C1 C8a C4a 98.29(18)
C8 C8a C10 110.2(2)
C8 C8a C4a 108.26(15)
C10 C8a C4a 114.46(17)
O4a C4a C4 102.8(2)
O4a C4a C5 108.89(15)
O4a C4a C8a 101.37(14)
C4 C4a C5 113.57(19)
C4 C4a C8a 114.52(16)
C5 C4a C8a 114.1(2)
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
O4a C9 1.340(2)
O4a C4a 1.504(2)
O2 C2 1.456(3)
O2 C12 1.337(2)
O9 C9 1.201(3)
O4 C4 1.426(3)
O4 H1 0.83(5)
O12 C12 1.185(3)
C1 C2 1.535(3)
C1 C9 1.507(3)
C1 C8a 1.530(3)
C1 H1c1 0.96
C2 C3 1.524(4)
C2 H1c2 0.96
C3 C4 1.526(4)
C3 H1c3 0.96
C3 H2c3 0.96
C4 C4a 1.534(4)
C4 H1c4 0.96
C5 C6 1.316(5)
C5 C4a 1.495(3)
C5 H1c5 0.96
C6 C7 1.488(5)
C6 H1c6 0.96
C7 C8 1.532(4)
C7 H1c7 0.96
C7 H2c7 0.96
C8 C11 1.526(5)
C8 C8a 1.556(3)
C8 H1c8 0.96
C10 C8a 1.531(3)
C10 H1c10 0.96
C10 H2c10 0.96
C10 H3c10 0.96
C11 H1c11 0.96
C11 H2c11 0.96
C11 H3c11 0.96
C12 C13 1.486(4)
C13 H1c13 0.96
C13 H2c13 0.96
C13 H3c13 0.96
C8a C4a 1.545(3)
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
C8 H1c8 C9 . 0.96 2.48 2.913(4) 107.28 ?
C10 H3c10 O4 . 0.96 2.31 2.946(4) 122.91 y
C2 H1c2 O12 . 0.96 2.36 2.668(3) 98.20 ?
O4 H1 O9 1_565 0.83(5) 2.10(4) 2.907(2) 165(4) y
loop_
_cod_related_entry_id
_cod_related_entry_database
_cod_related_entry_code
1 PubChem 139085455
