#------------------------------------------------------------------------------
#$Date: 2017-10-14 22:27:35 +0300 (Sat, 14 Oct 2017) $
#$Revision: 202017 $
#$URL: file:///home/coder/svn-repositories/cod/cif/7/10/45/7104548.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_7104548
loop_
_publ_author_name
'Boyd, Derek R'
'Sharma, Narain D'
'Malone, John F'
'Allen, Christopher C R'
_publ_section_title
;
 New families of enantiopure cyclohexenone cis-diol, o-quinol dimer and
 hydrate metabolites from dioxygenase-catalysed dihydroxylation of
 phenols.
;
_journal_issue                   24
_journal_name_full
'Chemical communications (Cambridge, England)'
_journal_page_first              3633
_journal_page_last               3635
_journal_paper_doi               10.1039/b905940g
_journal_volume                  34
_journal_year                    2009
_chemical_absolute_configuration rm
_chemical_formula_moiety         'C18 H24 O6'
_chemical_formula_sum            'C18 H24 O6'
_chemical_formula_weight         336.37
_chemical_melting_point          158
_chemical_name_systematic
;
?
;
_space_group_IT_number           1
_symmetry_cell_setting           triclinic
_symmetry_space_group_name_Hall  'P 1'
_symmetry_space_group_name_H-M   'P 1'
_atom_sites_solution_hydrogens   difmap
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_audit_creation_method           SHELXL-97
_cell_angle_alpha                102.325(16)
_cell_angle_beta                 96.496(17)
_cell_angle_gamma                110.764(16)
_cell_formula_units_Z            1
_cell_length_a                   6.581(8)
_cell_length_b                   7.123(8)
_cell_length_c                   11.041(13)
_cell_measurement_reflns_used    1911
_cell_measurement_temperature    298(2)
_cell_measurement_theta_max      26.69
_cell_measurement_theta_min      3.18
_cell_volume                     462.6(9)
_computing_cell_refinement       'Bruker SMART'
_computing_data_collection       'Bruker SMART'
_computing_data_reduction        'Bruker SAINT'
_computing_molecular_graphics    'Bruker SHELXTL'
_computing_publication_material  'SHELXL-97 (Sheldrick, 1997)'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 1990)'
_diffrn_ambient_temperature      298(2)
_diffrn_measured_fraction_theta_full 0.832
_diffrn_measured_fraction_theta_max 0.832
_diffrn_measurement_device_type  'Bruker SMART CCD area detector'
_diffrn_measurement_method       'phi and omega scan'
_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  0.0121
_diffrn_reflns_av_sigmaI/netI    0.0403
_diffrn_reflns_limit_h_max       8
_diffrn_reflns_limit_h_min       -8
_diffrn_reflns_limit_k_max       8
_diffrn_reflns_limit_k_min       -8
_diffrn_reflns_limit_l_max       14
_diffrn_reflns_limit_l_min       -14
_diffrn_reflns_number            3590
_diffrn_reflns_theta_full        28.23
_diffrn_reflns_theta_max         28.23
_diffrn_reflns_theta_min         1.93
_exptl_absorpt_coefficient_mu    0.090
_exptl_absorpt_correction_T_max  0.969
_exptl_absorpt_correction_T_min  0.890
_exptl_absorpt_correction_type   empirical
_exptl_absorpt_process_details   'Bruker SADABS'
_exptl_crystal_colour            colourless
_exptl_crystal_density_diffrn    1.207
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       plates
_exptl_crystal_F_000             180
_exptl_crystal_size_max          1.0
_exptl_crystal_size_mid          0.75
_exptl_crystal_size_min          0.40
_refine_diff_density_max         0.180
_refine_diff_density_min         -0.157
_refine_diff_density_rms         0.031
_refine_ls_abs_structure_details 'Flack H D (1983), Acta Cryst. A39, 876-881'
_refine_ls_abs_structure_Flack   1.8(14)
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.045
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     223
_refine_ls_number_reflns         3246
_refine_ls_number_restraints     3
_refine_ls_restrained_S_all      1.045
_refine_ls_R_factor_all          0.0568
_refine_ls_R_factor_gt           0.0494
_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)+(0.0631P)²+0.1126P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1259
_refine_ls_wR_factor_ref         0.1329
_reflns_number_gt                2834
_reflns_number_total             3246
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            b905940g.txt
_cod_data_source_block           7d
_cod_original_sg_symbol_H-M      P1
_cod_database_code               7104548
loop_
_symmetry_equiv_pos_as_xyz
'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
C1 C 0.0060(5) 1.0185(4) -0.1099(3) 0.0510(6) Uani 1 1 d . . .
O1 O 0.0619(4) 1.2086(3) -0.0872(3) 0.0846(7) Uani 1 1 d . . .
C2 C -0.2248(5) 0.8732(4) -0.1658(3) 0.0509(6) Uani 1 1 d . . .
H2 H -0.3295 0.9276 -0.1857 0.061 Uiso 1 1 calc R . .
C3 C -0.2909(5) 0.6662(4) -0.1893(2) 0.0497(6) Uani 1 1 d . . .
C3' C -0.5277(6) 0.5169(6) -0.2518(4) 0.0830(11) Uani 1 1 d . . .
H3'1 H -0.5970 0.4504 -0.1918 0.124 Uiso 1 1 calc R . .
H3'2 H -0.5265 0.4130 -0.3229 0.124 Uiso 1 1 calc R . .
H3'3 H -0.6093 0.5930 -0.2803 0.124 Uiso 1 1 calc R . .
C4 C -0.1282(5) 0.5680(4) -0.1583(3) 0.0489(6) Uani 1 1 d . . .
H4 H -0.0744 0.5298 -0.2353 0.059 Uiso 1 1 calc R . .
O4 O -0.2433(4) 0.3810(3) -0.1260(3) 0.0793(7) Uani 1 1 d . . .
H4A H -0.1581 0.3236 -0.1128 0.119 Uiso 1 1 calc R . .
C5 C 0.0728(4) 0.7182(4) -0.0556(2) 0.0441(6) Uani 1 1 d . . .
H5 H 0.1827 0.6558 -0.0466 0.053 Uiso 1 1 calc R . .
O5 O -0.0044(3) 0.7560(3) 0.06392(16) 0.0485(4) Uani 1 1 d . . .
C6 C 0.1790(4) 0.9282(4) -0.0859(2) 0.0471(6) Uani 1 1 d . . .
H6 H 0.2267 0.8975 -0.1662 0.057 Uiso 1 1 calc R . .
C6' C 0.3879(5) 1.0835(6) 0.0118(3) 0.0698(9) Uani 1 1 d . . .
H6'1 H 0.4593 1.2009 -0.0195 0.105 Uiso 1 1 calc R . .
H6'2 H 0.4881 1.0163 0.0262 0.105 Uiso 1 1 calc R . .
H6'3 H 0.3470 1.1303 0.0900 0.105 Uiso 1 1 calc R . .
C7 C 0.0908(4) 0.7171(4) 0.1638(2) 0.0470(6) Uani 1 1 d . . .
O7 O 0.2440(5) 0.6621(5) 0.1660(2) 0.0907(9) Uani 1 1 d . . .
C8 C -0.0190(4) 0.7565(4) 0.2752(2) 0.0467(6) Uani 1 1 d . . .
O8 O 0.0962(4) 0.7123(4) 0.3823(2) 0.0715(7) Uani 1 1 d . . .
C9 C -0.2632(5) 0.6207(5) 0.2598(3) 0.0642(8) Uani 1 1 d . . .
H9A H -0.2847 0.4777 0.2568 0.077 Uiso 1 1 calc R . .
H9B H -0.3516 0.6224 0.1838 0.077 Uiso 1 1 calc R . .
C10 C -0.3219(5) 0.7278(6) 0.3816(3) 0.0719(9) Uani 1 1 d . . .
H10A H -0.3668 0.6339 0.4344 0.086 Uiso 1 1 calc R . .
H10B H -0.4402 0.7739 0.3604 0.086 Uiso 1 1 calc R . .
C11 C -0.0997(5) 0.9178(5) 0.4493(3) 0.0626(8) Uani 1 1 d . . .
C12 C 0.0489(6) 0.8122(7) 0.4898(3) 0.0782(11) Uani 1 1 d . . .
O12 O 0.1171(6) 0.7995(7) 0.5929(3) 0.1279(14) Uani 1 1 d . . .
C13 C -0.1183(7) 1.0872(8) 0.5547(3) 0.0950(13) Uani 1 1 d . . .
H13A H -0.2045 1.0229 0.6102 0.143 Uiso 1 1 calc R . .
H13B H -0.1895 1.1641 0.5176 0.143 Uiso 1 1 calc R . .
H13C H 0.0275 1.1803 0.6020 0.143 Uiso 1 1 calc R . .
C14 C -0.0004(5) 0.9828(4) 0.3349(3) 0.0532(6) Uani 1 1 d . . .
C15 C -0.1440(8) 1.0591(6) 0.2533(3) 0.0794(10) Uani 1 1 d . . .
H15A H -0.1503 1.1841 0.3033 0.119 Uiso 1 1 calc R . .
H15B H -0.2915 0.9531 0.2237 0.119 Uiso 1 1 calc R . .
H15C H -0.0796 1.0874 0.1820 0.119 Uiso 1 1 calc R . .
C16 C 0.2395(7) 1.1428(7) 0.3761(4) 0.0939(13) Uani 1 1 d . . .
H16A H 0.3020 1.1583 0.3025 0.141 Uiso 1 1 calc R . .
H16B H 0.3250 1.0959 0.4297 0.141 Uiso 1 1 calc R . .
H16C H 0.2421 1.2747 0.4217 0.141 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 121.6(3) . . ?
O1 C1 C6 120.0(3) . . ?
C2 C1 C6 118.3(2) . . ?
C3 C2 C1 122.9(3) . . ?
C2 C3 C4 121.1(3) . . ?
C2 C3 C3' 122.5(3) . . ?
C4 C3 C3' 116.4(3) . . ?
O4 C4 C3 108.8(2) . . ?
O4 C4 C5 112.4(2) . . ?
C3 C4 C5 112.4(2) . . ?
O5 C5 C4 107.7(2) . . ?
O5 C5 C6 108.4(2) . . ?
C4 C5 C6 111.4(2) . . ?
C7 O5 C5 118.5(2) . . ?
C1 C6 C6' 113.1(3) . . ?
C1 C6 C5 110.3(2) . . ?
C6' C6 C5 113.8(2) . . ?
O7 C7 O5 124.9(3) . . ?
O7 C7 C8 124.9(2) . . ?
O5 C7 C8 110.3(2) . . ?
O8 C8 C7 107.2(2) . . ?
O8 C8 C9 104.7(2) . . ?
C7 C8 C9 117.5(2) . . ?
O8 C8 C14 102.2(2) . . ?
C7 C8 C14 119.0(2) . . ?
C9 C8 C14 104.4(2) . . ?
C12 O8 C8 105.9(2) . . ?
C8 C9 C10 102.1(2) . . ?
C9 C10 C11 103.4(3) . . ?
C12 C11 C13 115.7(3) . . ?
C12 C11 C10 102.2(3) . . ?
C13 C11 C10 115.8(3) . . ?
C12 C11 C14 99.7(3) . . ?
C13 C11 C14 118.3(3) . . ?
C10 C11 C14 102.5(2) . . ?
O12 C12 O8 120.9(4) . . ?
O12 C12 C11 131.4(4) . . ?
O8 C12 C11 107.7(2) . . ?
C16 C14 C15 110.5(3) . . ?
C16 C14 C8 113.1(3) . . ?
C15 C14 C8 114.5(2) . . ?
C16 C14 C11 112.5(3) . . ?
C15 C14 C11 113.6(3) . . ?
C8 C14 C11 91.4(2) . . ?
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 1.230(4) . ?
C1 C2 1.470(4) . ?
C1 C6 1.517(4) . ?
C2 C3 1.337(4) . ?
C3 C4 1.517(4) . ?
C3 C3' 1.518(5) . ?
C4 O4 1.422(4) . ?
C4 C5 1.523(4) . ?
C5 O5 1.472(3) . ?
C5 C6 1.538(4) . ?
O5 C7 1.335(3) . ?
C6 C6' 1.535(4) . ?
C7 O7 1.204(4) . ?
C7 C8 1.520(4) . ?
C8 O8 1.482(3) . ?
C8 C9 1.521(4) . ?
C8 C14 1.561(4) . ?
O8 C12 1.376(5) . ?
C9 C10 1.559(5) . ?
C10 C11 1.564(5) . ?
C11 C12 1.513(5) . ?
C11 C13 1.537(5) . ?
C11 C14 1.568(4) . ?
C12 O12 1.209(4) . ?
C14 C16 1.529(5) . ?
C14 C15 1.543(5) . ?
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_site_symmetry_1
_geom_torsion_site_symmetry_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
_geom_torsion_publ_flag
O1 C1 C2 C3 -178.8(3) . . . . ?
C6 C1 C2 C3 4.1(4) . . . . ?
C1 C2 C3 C4 0.3(4) . . . . ?
C1 C2 C3 C3' -177.5(3) . . . . ?
C2 C3 C4 O4 148.6(3) . . . . ?
C3' C3 C4 O4 -33.3(4) . . . . ?
C2 C3 C4 C5 23.4(4) . . . . ?
C3' C3 C4 C5 -158.6(3) . . . . ?
O4 C4 C5 O5 -55.0(3) . . . . ?
C3 C4 C5 O5 68.2(3) . . . . ?
O4 C4 C5 C6 -173.7(2) . . . . ?
C3 C4 C5 C6 -50.5(3) . . . . ?
C4 C5 O5 C7 123.9(2) . . . . ?
C6 C5 O5 C7 -115.5(2) . . . . ?
O1 C1 C6 C6' 23.0(4) . . . . ?
C2 C1 C6 C6' -159.8(2) . . . . ?
O1 C1 C6 C5 151.6(3) . . . . ?
C2 C1 C6 C5 -31.2(3) . . . . ?
O5 C5 C6 C1 -64.4(3) . . . . ?
C4 C5 C6 C1 53.9(3) . . . . ?
O5 C5 C6 C6' 63.9(3) . . . . ?
C4 C5 C6 C6' -177.8(2) . . . . ?
C5 O5 C7 O7 3.8(4) . . . . ?
C5 O5 C7 C8 -177.4(2) . . . . ?
O7 C7 C8 O8 -0.6(4) . . . . ?
O5 C7 C8 O8 -179.4(2) . . . . ?
O7 C7 C8 C9 -118.0(4) . . . . ?
O5 C7 C8 C9 63.2(3) . . . . ?
O7 C7 C8 C14 114.5(3) . . . . ?
O5 C7 C8 C14 -64.3(3) . . . . ?
C7 C8 O8 C12 160.5(3) . . . . ?
C9 C8 O8 C12 -74.1(3) . . . . ?
C14 C8 O8 C12 34.6(3) . . . . ?
O8 C8 C9 C10 69.5(3) . . . . ?
C7 C8 C9 C10 -171.8(2) . . . . ?
C14 C8 C9 C10 -37.6(3) . . . . ?
C8 C9 C10 C11 1.5(3) . . . . ?
C9 C10 C11 C12 -68.5(3) . . . . ?
C9 C10 C11 C13 164.7(3) . . . . ?
C9 C10 C11 C14 34.5(3) . . . . ?
C8 O8 C12 O12 178.2(4) . . . . ?
C8 O8 C12 C11 0.7(4) . . . . ?
C13 C11 C12 O12 19.6(7) . . . . ?
C10 C11 C12 O12 -107.2(5) . . . . ?
C14 C11 C12 O12 147.6(5) . . . . ?
C13 C11 C12 O8 -163.3(3) . . . . ?
C10 C11 C12 O8 69.9(3) . . . . ?
C14 C11 C12 O8 -35.2(4) . . . . ?
O8 C8 C14 C16 63.0(3) . . . . ?
C7 C8 C14 C16 -54.8(3) . . . . ?
C9 C8 C14 C16 171.9(3) . . . . ?
O8 C8 C14 C15 -169.2(3) . . . . ?
C7 C8 C14 C15 73.1(3) . . . . ?
C9 C8 C14 C15 -60.3(3) . . . . ?
O8 C8 C14 C11 -52.3(2) . . . . ?
C7 C8 C14 C11 -170.0(2) . . . . ?
C9 C8 C14 C11 56.6(2) . . . . ?
C12 C11 C14 C16 -64.7(4) . . . . ?
C13 C11 C14 C16 61.6(4) . . . . ?
C10 C11 C14 C16 -169.7(3) . . . . ?
C12 C11 C14 C15 168.7(3) . . . . ?
C13 C11 C14 C15 -65.0(4) . . . . ?
C10 C11 C14 C15 63.7(4) . . . . ?
C12 C11 C14 C8 51.1(3) . . . . ?
C13 C11 C14 C8 177.4(3) . . . . ?
C10 C11 C14 C8 -53.9(3) . . . . ?
loop_
_cod_related_entry_id
_cod_related_entry_database
_cod_related_entry_code
1 ChemSpider 30653129
