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#$Date: 2025-08-22 13:33:34 +0300 (Fri, 22 Aug 2025) $
#$Revision: 301861 $
#$URL: file:///home/coder/svn-repositories/cod/cif/7/15/18/7151895.cif $
#------------------------------------------------------------------------------
#
# This file is available in the Crystallography Open Database (COD),
# http://www.crystallography.net/
#
# All data on this site have been placed in the public domain by the
# contributors.
#
data_7151895
loop_
_publ_author_name
'Merritt, Andrew T.'
'Pouwer, Rebecca H.'
'Williams, David J.'
'Williams, Craig M.'
'Ley, Steven V.'
_publ_section_title
;
 The clerodane ring system: investigating the viability of a direct
 Diels--Alder approach
;
_journal_issue                   13
_journal_name_full               'Organic & Biomolecular Chemistry'
_journal_page_first              4745
_journal_paper_doi               10.1039/c1ob05422h
_journal_volume                  9
_journal_year                    2011
_chemical_formula_moiety         'C17 H20 O4'
_chemical_formula_sum            'C17 H20 O4'
_chemical_formula_weight         288.33
_space_group_IT_number           2
_symmetry_cell_setting           triclinic
_symmetry_space_group_name_Hall  '-P 1'
_symmetry_space_group_name_H-M   'P -1'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_audit_creation_method           SHELXL-97
_cell_angle_alpha                110.08(3)
_cell_angle_beta                 93.86(3)
_cell_angle_gamma                95.48(3)
_cell_formula_units_Z            2
_cell_length_a                   6.246(2)
_cell_length_b                   10.219(3)
_cell_length_c                   12.572(5)
_cell_measurement_temperature    298(2)
_cell_volume                     745.9(5)
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 1990)'
_diffrn_ambient_temperature      298(2)
_diffrn_measured_fraction_theta_full 0.998
_diffrn_measured_fraction_theta_max 0.998
_diffrn_measurement_device_type  'Nicolet R3m'
_diffrn_measurement_method       'omega scans'
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_source         'fine-focus sealed tube'
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54178
_diffrn_reflns_av_R_equivalents  0.0000
_diffrn_reflns_av_sigmaI/netI    0.0535
_diffrn_reflns_limit_h_max       6
_diffrn_reflns_limit_h_min       -6
_diffrn_reflns_limit_k_max       9
_diffrn_reflns_limit_k_min       -10
_diffrn_reflns_limit_l_max       12
_diffrn_reflns_limit_l_min       0
_diffrn_reflns_number            1537
_diffrn_reflns_theta_full        50.00
_diffrn_reflns_theta_max         50.00
_diffrn_reflns_theta_min         3.76
_exptl_absorpt_coefficient_mu    0.739
_exptl_absorpt_correction_type   none
_exptl_crystal_colour            Colourless
_exptl_crystal_density_diffrn    1.284
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       prisms
_exptl_crystal_F_000             308
_refine_diff_density_max         0.174
_refine_diff_density_min         -0.202
_refine_diff_density_rms         0.042
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   0.972
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     190
_refine_ls_number_reflns         1537
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      0.972
_refine_ls_R_factor_all          0.0763
_refine_ls_R_factor_gt           0.0540
_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)+(0.0861P)²+0.0000P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1286
_refine_ls_wR_factor_ref         0.1370
_reflns_number_gt                1093
_reflns_number_total             1537
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            c1ob05422h.txt
_cod_data_source_block           18
_cod_depositor_comments
;
The following automatic conversions were performed:
'_symmetry_cell_setting' value 'Triclinic' changed to 'triclinic'
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 1555 2011-01-17 13:19:09Z saulius 
;
_cod_original_cell_volume        745.9(4)
_cod_original_sg_symbol_H-M      P-1
_cod_database_code               7151895
loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'-x, -y, -z'
loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_symmetry_multiplicity
_atom_site_calc_flag
_atom_site_refinement_flags
_atom_site_disorder_assembly
_atom_site_disorder_group
O1 O 0.9699(4) 0.3457(3) 0.5151(2) 0.0533(7) Uani 1 1 d . . .
C2 C 1.0553(7) 0.3050(4) 0.4160(3) 0.0509(10) Uani 1 1 d . . .
O2 O 1.2473(4) 0.3317(3) 0.4129(2) 0.0692(9) Uani 1 1 d . . .
C3 C 0.8878(5) 0.2202(4) 0.3165(3) 0.0442(9) Uani 1 1 d . . .
C4 C 0.7073(6) 0.1799(4) 0.3813(3) 0.0481(10) Uani 1 1 d . . .
H4A H 0.5659 0.1729 0.3414 0.058 Uiso 1 1 calc R . .
H4B H 0.7240 0.0910 0.3908 0.058 Uiso 1 1 calc R . .
C5 C 0.7359(5) 0.2989(4) 0.4954(3) 0.0462(10) Uani 1 1 d . . .
H5A H 0.6574 0.3754 0.4901 0.055 Uiso 1 1 calc R . .
C6 C 0.8132(5) 0.3173(4) 0.2529(3) 0.0470(10) Uani 1 1 d . . .
H6A H 0.7434 0.3905 0.3066 0.056 Uiso 1 1 calc R . .
C7 C 0.9991(6) 0.3914(4) 0.2126(3) 0.0581(11) Uani 1 1 d . . .
H7A H 1.1037 0.4447 0.2773 0.070 Uiso 1 1 calc R . .
H7B H 1.0716 0.3215 0.1590 0.070 Uiso 1 1 calc R . .
C8 C 0.9172(7) 0.4895(5) 0.1560(4) 0.0700(13) Uani 1 1 d . . .
H8A H 1.0378 0.5333 0.1302 0.084 Uiso 1 1 calc R . .
H8B H 0.8535 0.5631 0.2111 0.084 Uiso 1 1 calc R . .
C9 C 0.7491(7) 0.4103(5) 0.0549(4) 0.0775(14) Uani 1 1 d . . .
H9A H 0.8171 0.3439 -0.0039 0.093 Uiso 1 1 calc R . .
H9B H 0.6934 0.4763 0.0234 0.093 Uiso 1 1 calc R . .
C10 C 0.5621(7) 0.3317(5) 0.0896(4) 0.0685(12) Uani 1 1 d . . .
H10A H 0.4659 0.2752 0.0223 0.082 Uiso 1 1 calc R . .
H10B H 0.4804 0.3990 0.1396 0.082 Uiso 1 1 calc R . .
C11 C 0.6437(6) 0.2362(4) 0.1511(3) 0.0528(11) Uani 1 1 d . . .
H11A H 0.5187 0.2039 0.1828 0.063 Uiso 1 1 calc R . .
C12 C 0.7234(6) 0.1072(4) 0.0746(3) 0.0553(11) Uani 1 1 d . . .
O12 O 0.7136(5) 0.0748(3) -0.0289(2) 0.0774(9) Uani 1 1 d . . .
C13 C 0.8125(6) 0.0137(4) 0.1317(3) 0.0631(12) Uani 1 1 d . . .
H13A H 0.8818 -0.0572 0.0771 0.076 Uiso 1 1 calc R . .
H13B H 0.6942 -0.0341 0.1559 0.076 Uiso 1 1 calc R . .
C14 C 0.9761(6) 0.0947(4) 0.2349(3) 0.0573(11) Uani 1 1 d . . .
H14A H 1.0131 0.0324 0.2747 0.069 Uiso 1 1 calc R . .
H14B H 1.1071 0.1270 0.2091 0.069 Uiso 1 1 calc R . .
C15 C 0.6710(6) 0.2586(4) 0.5933(3) 0.0492(10) Uani 1 1 d . . .
C16 C 0.4946(8) 0.2851(5) 0.6437(4) 0.0820(15) Uani 1 1 d . . .
H16A H 0.3913 0.3354 0.6247 0.098 Uiso 1 1 calc R . .
O17 O 0.4821(6) 0.2290(4) 0.7283(3) 0.0895(11) Uani 1 1 d . . .
C18 C 0.6620(8) 0.1694(5) 0.7302(4) 0.0709(13) Uani 1 1 d . . .
H18A H 0.6999 0.1250 0.7808 0.085 Uiso 1 1 calc R . .
C19 C 0.7790(7) 0.1826(5) 0.6500(4) 0.0672(12) Uani 1 1 d . . .
H19A H 0.9099 0.1478 0.6338 0.081 Uiso 1 1 calc R . .
loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0181 0.0091 '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 0.0492 0.0322 '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_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
C2 O1 C5 109.6(3) . . ?
O2 C2 O1 120.5(4) . . ?
O2 C2 C3 127.1(4) . . ?
O1 C2 C3 112.3(3) . . ?
C14 C3 C2 111.7(3) . . ?
C14 C3 C4 113.7(3) . . ?
C2 C3 C4 100.1(3) . . ?
C14 C3 C6 110.4(3) . . ?
C2 C3 C6 109.2(3) . . ?
C4 C3 C6 111.3(3) . . ?
C5 C4 C3 104.1(3) . . ?
O1 C5 C15 108.3(3) . . ?
O1 C5 C4 104.0(3) . . ?
C15 C5 C4 115.1(3) . . ?
C7 C6 C11 109.5(3) . . ?
C7 C6 C3 113.9(3) . . ?
C11 C6 C3 111.2(3) . . ?
C8 C7 C6 111.3(3) . . ?
C7 C8 C9 111.2(3) . . ?
C8 C9 C10 111.5(3) . . ?
C9 C10 C11 111.5(3) . . ?
C12 C11 C6 111.0(3) . . ?
C12 C11 C10 114.2(3) . . ?
C6 C11 C10 112.0(3) . . ?
O12 C12 C11 123.5(4) . . ?
O12 C12 C13 120.5(4) . . ?
C11 C12 C13 116.0(3) . . ?
C12 C13 C14 112.6(3) . . ?
C3 C14 C13 111.8(3) . . ?
C16 C15 C19 104.8(4) . . ?
C16 C15 C5 126.5(4) . . ?
C19 C15 C5 128.6(4) . . ?
C15 C16 O17 111.3(4) . . ?
C18 O17 C16 105.6(3) . . ?
C19 C18 O17 110.2(4) . . ?
C18 C19 C15 108.1(4) . . ?
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
O1 C2 1.336(4) . ?
O1 C5 1.471(4) . ?
C2 O2 1.211(4) . ?
C2 C3 1.522(5) . ?
C3 C14 1.519(5) . ?
C3 C4 1.539(5) . ?
C3 C6 1.557(5) . ?
C4 C5 1.515(5) . ?
C5 C15 1.493(5) . ?
C6 C7 1.533(5) . ?
C6 C11 1.539(5) . ?
C7 C8 1.521(5) . ?
C8 C9 1.525(6) . ?
C9 C10 1.526(5) . ?
C10 C11 1.539(5) . ?
C11 C12 1.493(6) . ?
C12 O12 1.223(4) . ?
C12 C13 1.502(5) . ?
C13 C14 1.528(5) . ?
C15 C16 1.312(6) . ?
C15 C19 1.408(5) . ?
C16 O17 1.373(5) . ?
O17 C18 1.331(5) . ?
C18 C19 1.320(5) . ?
loop_
_cod_related_entry_id
_cod_related_entry_database
_cod_related_entry_code
1 PubChem 53474683
