#------------------------------------------------------------------------------
#$Date: 2025-08-22 12:33:34 +0200 (Fri 22 de Aug de 2025) $
#$Revision: 301861 $
#$URL: svn://www.crystallography.net/cod/cif/7/15/10/7151032.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_7151032
loop_
_publ_author_name
'Butters, Michael'
'Beetstra, Dirk J.'
'Elliott, Mark C.'
'Hill-Cousins, Joseph'
'Kariuki, Benson M.'
_publ_section_title
;
 Directed epoxidation of cyclohexa-1,4-dienes--stereoselective
 formation of up to six contiguous stereogenic centres
;
_journal_issue                   23
_journal_name_full               'Organic & Biomolecular Chemistry'
_journal_page_first              4426
_journal_page_last               4434
_journal_paper_doi               10.1039/b814131m
_journal_volume                  6
_journal_year                    2008
_chemical_formula_moiety         'C13 H22 O4'
_chemical_formula_sum            'C13 H22 O4'
_chemical_formula_weight         242.31
_space_group_IT_number           14
_symmetry_cell_setting           monoclinic
_symmetry_space_group_name_Hall  '-P 2yab'
_symmetry_space_group_name_H-M   'P 1 21/a 1'
_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                 102.4210(10)
_cell_angle_gamma                90.00
_cell_formula_units_Z            4
_cell_length_a                   11.8532(3)
_cell_length_b                   7.1565(2)
_cell_length_c                   16.0428(4)
_cell_measurement_reflns_used    2230
_cell_measurement_temperature    150(2)
_cell_measurement_theta_max      27.46
_cell_measurement_theta_min      3.13
_cell_volume                     1329.02(6)
_computing_cell_refinement       DENZO/SCALEPACK
_computing_data_collection       'cOLLECT,Nonius BV, 1997-2001'
_computing_data_reduction        DENZO/SCALEPACK
_computing_structure_refinement  SHELXL-97
_computing_structure_solution    SHELXs-97
_diffrn_ambient_temperature      150(2)
_diffrn_measured_fraction_theta_full 0.997
_diffrn_measured_fraction_theta_max 0.997
_diffrn_measurement_device_type  'Nonius KappaCCD'
_diffrn_measurement_method       'CCD scans'
_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  0.1095
_diffrn_reflns_av_sigmaI/netI    0.1352
_diffrn_reflns_limit_h_max       15
_diffrn_reflns_limit_h_min       -15
_diffrn_reflns_limit_k_max       9
_diffrn_reflns_limit_k_min       -9
_diffrn_reflns_limit_l_max       20
_diffrn_reflns_limit_l_min       -20
_diffrn_reflns_number            20521
_diffrn_reflns_theta_full        27.46
_diffrn_reflns_theta_max         27.46
_diffrn_reflns_theta_min         3.13
_exptl_absorpt_coefficient_mu    0.088
_exptl_absorpt_correction_T_max  0.9912
_exptl_absorpt_correction_T_min  0.9672
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   Denzo/scalepack
_exptl_crystal_colour            colourless
_exptl_crystal_density_diffrn    1.211
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       plate
_exptl_crystal_F_000             528
_exptl_crystal_size_max          0.38
_exptl_crystal_size_mid          0.25
_exptl_crystal_size_min          0.10
_refine_diff_density_max         0.391
_refine_diff_density_min         -0.336
_refine_diff_density_rms         0.076
_refine_ls_extinction_coef       0.056(10)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc²λ³/sin(2θ)]^-1/4^
_refine_ls_extinction_method     SHELXL
_refine_ls_goodness_of_fit_ref   1.044
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     160
_refine_ls_number_reflns         3023
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.044
_refine_ls_R_factor_all          0.1026
_refine_ls_R_factor_gt           0.0752
_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)+(0.0891P)²+0.3703P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1923
_refine_ls_wR_factor_ref         0.2130
_reflns_number_gt                2230
_reflns_number_total             3023
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            b814131m.txt
_cod_data_source_block           mce0801
_cod_depositor_comments
;
The following automatic conversions were performed:
'_symmetry_cell_setting' value 'Monoclinic' changed to 'monoclinic'
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 
;
_cod_original_sg_symbol_H-M      P21/a
_cod_database_code               7151032
loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'-x+1/2, y+1/2, -z'
'-x, -y, -z'
'x-1/2, -y-1/2, 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
C1 C 0.3519(2) 0.3753(3) 0.78183(13) 0.0247(5) Uani 1 1 d . . .
H1 H 0.2704 0.4052 0.7531 0.030 Uiso 1 1 calc R . .
C2 C 0.4054(2) 0.2612(3) 0.72058(13) 0.0224(5) Uani 1 1 d . . .
H2A H 0.3510 0.1652 0.6912 0.027 Uiso 1 1 calc R . .
H2B H 0.4775 0.1995 0.7506 0.027 Uiso 1 1 calc R . .
C3 C 0.43011(18) 0.4090(3) 0.65742(12) 0.0190(5) Uani 1 1 d . . .
C4 C 0.32068(18) 0.4399(3) 0.59007(12) 0.0206(5) Uani 1 1 d . . .
H4 H 0.2762 0.3244 0.5690 0.025 Uiso 1 1 calc R . .
C5 C 0.25188(19) 0.6114(3) 0.58573(13) 0.0240(5) Uani 1 1 d . . .
H5 H 0.1668 0.5985 0.5629 0.029 Uiso 1 1 calc R . .
C6 C 0.2898(2) 0.7692(3) 0.64714(14) 0.0261(5) Uani 1 1 d . . .
H6A H 0.2503 0.7583 0.6954 0.031 Uiso 1 1 calc R . .
H6B H 0.2663 0.8893 0.6179 0.031 Uiso 1 1 calc R . .
C7 C 0.4197(2) 0.7707(3) 0.68174(13) 0.0229(5) Uani 1 1 d . . .
H7 H 0.4347 0.8594 0.7311 0.027 Uiso 1 1 calc R . .
C8 C 0.46378(19) 0.5791(3) 0.71712(13) 0.0209(5) Uani 1 1 d . . .
H8 H 0.5499 0.5844 0.7349 0.025 Uiso 1 1 calc R . .
C9 C 0.52920(19) 0.3543(3) 0.61450(13) 0.0217(5) Uani 1 1 d . . .
H9A H 0.5502 0.4639 0.5834 0.026 Uiso 1 1 calc R . .
H9B H 0.5976 0.3201 0.6592 0.026 Uiso 1 1 calc R . .
C10 C 0.3516(2) 0.2931(3) 0.86995(13) 0.0295(6) Uani 1 1 d . . .
C11 C 0.2800(3) 0.1141(4) 0.85747(16) 0.0424(7) Uani 1 1 d . . .
H11A H 0.3158 0.0233 0.8255 0.064 Uiso 1 1 calc R . .
H11B H 0.2016 0.1424 0.8256 0.064 Uiso 1 1 calc R . .
H11C H 0.2764 0.0617 0.9133 0.064 Uiso 1 1 calc R . .
C12 C 0.4737(3) 0.2522(4) 0.91995(16) 0.0467(7) Uani 1 1 d . . .
H12A H 0.4711 0.2159 0.9784 0.070 Uiso 1 1 calc R . .
H12B H 0.5215 0.3642 0.9212 0.070 Uiso 1 1 calc R . .
H12C H 0.5069 0.1500 0.8923 0.070 Uiso 1 1 calc R . .
C13 C 0.2937(3) 0.4348(4) 0.91917(16) 0.0455(7) Uani 1 1 d . . .
H13A H 0.2155 0.4619 0.8867 0.068 Uiso 1 1 calc R . .
H13B H 0.3391 0.5504 0.9274 0.068 Uiso 1 1 calc R . .
H13C H 0.2895 0.3826 0.9749 0.068 Uiso 1 1 calc R . .
O1 O 0.41759(14) 0.5463(2) 0.79147(9) 0.0278(4) Uani 1 1 d . . .
O2 O 0.32600(13) 0.57927(19) 0.52545(9) 0.0236(4) Uani 1 1 d . . .
O3 O 0.48295(14) 0.8391(2) 0.62165(9) 0.0267(4) Uani 1 1 d . . .
H3 H 0.4593 0.7862 0.5744 0.040 Uiso 1 1 calc R . .
O4 O 0.50110(14) 0.2023(2) 0.55650(9) 0.0249(4) Uani 1 1 d . . .
H4A H 0.4926 0.1048 0.5836 0.037 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 0.0033 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_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
O1 C1 C2 103.60(16) . . ?
O1 C1 C10 109.61(17) . . ?
C2 C1 C10 118.39(19) . . ?
O1 C1 H1 108.3 . . ?
C2 C1 H1 108.3 . . ?
C10 C1 H1 108.3 . . ?
C1 C2 C3 102.86(16) . . ?
C1 C2 H2A 111.2 . . ?
C3 C2 H2A 111.2 . . ?
C1 C2 H2B 111.2 . . ?
C3 C2 H2B 111.2 . . ?
H2A C2 H2B 109.1 . . ?
C4 C3 C9 109.75(16) . . ?
C4 C3 C2 108.40(17) . . ?
C9 C3 C2 113.18(16) . . ?
C4 C3 C8 113.16(16) . . ?
C9 C3 C8 110.97(17) . . ?
C2 C3 C8 101.17(15) . . ?
O2 C4 C5 59.99(13) . . ?
O2 C4 C3 116.63(16) . . ?
C5 C4 C3 122.56(17) . . ?
O2 C4 H4 115.4 . . ?
C5 C4 H4 115.4 . . ?
C3 C4 H4 115.4 . . ?
O2 C5 C4 59.42(13) . . ?
O2 C5 C6 114.55(18) . . ?
C4 C5 C6 120.85(18) . . ?
O2 C5 H5 116.5 . . ?
C4 C5 H5 116.5 . . ?
C6 C5 H5 116.5 . . ?
C5 C6 C7 112.41(18) . . ?
C5 C6 H6A 109.1 . . ?
C7 C6 H6A 109.1 . . ?
C5 C6 H6B 109.1 . . ?
C7 C6 H6B 109.1 . . ?
H6A C6 H6B 107.9 . . ?
O3 C7 C6 113.13(17) . . ?
O3 C7 C8 111.73(18) . . ?
C6 C7 C8 111.54(18) . . ?
O3 C7 H7 106.7 . . ?
C6 C7 H7 106.7 . . ?
C8 C7 H7 106.7 . . ?
O1 C8 C7 107.08(16) . . ?
O1 C8 C3 106.98(15) . . ?
C7 C8 C3 116.93(16) . . ?
O1 C8 H8 108.5 . . ?
C7 C8 H8 108.5 . . ?
C3 C8 H8 108.5 . . ?
O4 C9 C3 113.20(17) . . ?
O4 C9 H9A 108.9 . . ?
C3 C9 H9A 108.9 . . ?
O4 C9 H9B 108.9 . . ?
C3 C9 H9B 108.9 . . ?
H9A C9 H9B 107.8 . . ?
C12 C10 C11 110.2(2) . . ?
C12 C10 C1 111.64(19) . . ?
C11 C10 C1 108.23(18) . . ?
C12 C10 C13 109.6(2) . . ?
C11 C10 C13 108.9(2) . . ?
C1 C10 C13 108.1(2) . . ?
C10 C11 H11A 109.5 . . ?
C10 C11 H11B 109.5 . . ?
H11A C11 H11B 109.5 . . ?
C10 C11 H11C 109.5 . . ?
H11A C11 H11C 109.5 . . ?
H11B C11 H11C 109.5 . . ?
C10 C12 H12A 109.5 . . ?
C10 C12 H12B 109.5 . . ?
H12A C12 H12B 109.5 . . ?
C10 C12 H12C 109.5 . . ?
H12A C12 H12C 109.5 . . ?
H12B C12 H12C 109.5 . . ?
C10 C13 H13A 109.5 . . ?
C10 C13 H13B 109.5 . . ?
H13A C13 H13B 109.5 . . ?
C10 C13 H13C 109.5 . . ?
H13A C13 H13C 109.5 . . ?
H13B C13 H13C 109.5 . . ?
C8 O1 C1 110.11(14) . . ?
C4 O2 C5 60.60(13) . . ?
C7 O3 H3 109.5 . . ?
C9 O4 H4A 109.5 . . ?
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
C1 O1 1.441(3) . ?
C1 C2 1.517(3) . ?
C1 C10 1.532(3) . ?
C1 H1 1.0000 . ?
C2 C3 1.536(3) . ?
C2 H2A 0.9900 . ?
C2 H2B 0.9900 . ?
C3 C4 1.515(3) . ?
C3 C9 1.534(3) . ?
C3 C8 1.548(3) . ?
C4 O2 1.450(2) . ?
C4 C5 1.467(3) . ?
C4 H4 1.0000 . ?
C5 O2 1.458(2) . ?
C5 C6 1.502(3) . ?
C5 H5 1.0000 . ?
C6 C7 1.520(3) . ?
C6 H6A 0.9900 . ?
C6 H6B 0.9900 . ?
C7 O3 1.429(3) . ?
C7 C8 1.532(3) . ?
C7 H7 1.0000 . ?
C8 O1 1.435(2) . ?
C8 H8 1.0000 . ?
C9 O4 1.424(2) . ?
C9 H9A 0.9900 . ?
C9 H9B 0.9900 . ?
C10 C12 1.525(4) . ?
C10 C11 1.526(4) . ?
C10 C13 1.535(4) . ?
C11 H11A 0.9800 . ?
C11 H11B 0.9800 . ?
C11 H11C 0.9800 . ?
C12 H12A 0.9800 . ?
C12 H12B 0.9800 . ?
C12 H12C 0.9800 . ?
C13 H13A 0.9800 . ?
C13 H13B 0.9800 . ?
C13 H13C 0.9800 . ?
O3 H3 0.8400 . ?
O4 H4A 0.8400 . ?
loop_
_cod_related_entry_id
_cod_related_entry_database
_cod_related_entry_code
1 PubChem 139190347
