#------------------------------------------------------------------------------
#$Date: 2017-10-13 14:42:48 +0300 (Fri, 13 Oct 2017) $
#$Revision: 201982 $
#$URL: file:///home/coder/svn-repositories/cod/cif/4/02/41/4024101.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_4024101
loop_
_publ_author_name
'Nathalie Lebrasseur'
'Julien Gagnepain'
'Aurélie Ozanne-Beaudenon'
'Jean-Michel Léger'
'Stéphane Quideau'
_publ_section_title
;
 Efficient Access to Orthoquinols and Their [4 + 2] Cyclodimers
 via SIBX-Mediated Hydroxylative Phenol Dearomatization
;
_journal_name_full               'Journal of Organic Chemistry'
_journal_page_first              6280
_journal_page_last               6283
_journal_paper_doi               10.1021/jo0708893
_journal_volume                  72
_journal_year                    2007
_chemical_formula_sum            'C18 H24 O4'
_chemical_formula_weight         304.37
_chemical_name_systematic
; 
 ? 
;
_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                94.330(4)
_cell_angle_beta                 92.990(5)
_cell_angle_gamma                111.162(5)
_cell_formula_units_Z            2
_cell_length_a                   6.7731(10)
_cell_length_b                   8.4962(13)
_cell_length_c                   15.1193(19)
_cell_measurement_temperature    133(2)
_cell_volume                     806.1(2)
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 1990)'
_diffrn_ambient_temperature      133(2)
_diffrn_measured_fraction_theta_full 0.906
_diffrn_measured_fraction_theta_max 0.906
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_source         'fine-focus sealed tube'
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54180
_diffrn_reflns_av_R_equivalents  0.0000
_diffrn_reflns_av_sigmaI/netI    0.0292
_diffrn_reflns_limit_h_max       8
_diffrn_reflns_limit_h_min       0
_diffrn_reflns_limit_k_max       9
_diffrn_reflns_limit_k_min       -10
_diffrn_reflns_limit_l_max       18
_diffrn_reflns_limit_l_min       -18
_diffrn_reflns_number            2868
_diffrn_reflns_theta_full        71.61
_diffrn_reflns_theta_max         71.61
_diffrn_reflns_theta_min         7.04
_exptl_absorpt_coefficient_mu    0.707
_exptl_absorpt_correction_T_max  0.9014
_exptl_absorpt_correction_T_min  0.8715
_exptl_crystal_density_diffrn    1.254
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             328
_exptl_crystal_size_max          0.20
_exptl_crystal_size_mid          0.20
_exptl_crystal_size_min          0.15
_refine_diff_density_max         0.343
_refine_diff_density_min         -0.239
_refine_diff_density_rms         0.056
_refine_ls_extinction_coef       0.042(3)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc²λ³/sin(2θ)]^-1/4^
_refine_ls_extinction_method     SHELXL
_refine_ls_goodness_of_fit_ref   1.057
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     208
_refine_ls_number_reflns         2868
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.057
_refine_ls_R_factor_all          0.0487
_refine_ls_R_factor_gt           0.0465
_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)+(0.0838P)²+0.3936P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1361
_refine_ls_wR_factor_ref         0.1430
_reflns_number_gt                2714
_reflns_number_total             2868
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            jo0708893si20070430_022225.cif
_cod_data_source_block           jgd47
_cod_database_code               4024101
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
C1 C 0.3404(2) 0.44471(19) 0.23962(11) 0.0211(4) Uani 1 1 d . . .
H1 H 0.3839 0.5582 0.2663 0.025 Uiso 1 1 calc R . .
C2 C 0.2319(2) 0.4095(2) 0.16028(11) 0.0233(4) Uani 1 1 d . . .
C3 C 0.1832(3) 0.2394(2) 0.11268(11) 0.0250(4) Uani 1 1 d . . .
C4 C 0.3410(3) 0.1536(2) 0.13330(11) 0.0241(4) Uani 1 1 d . . .
C5 C 0.3894(2) 0.15555(19) 0.23461(11) 0.0191(4) Uani 1 1 d . . .
H5 H 0.5328 0.1476 0.2432 0.023 Uiso 1 1 calc R . .
C6 C 0.4010(2) 0.32194(19) 0.29143(10) 0.0184(4) Uani 1 1 d . . .
C7 C 0.1572(3) 0.5320(2) 0.11486(13) 0.0329(4) Uani 1 1 d . . .
H7A H 0.2185 0.6444 0.1484 0.049 Uiso 1 1 calc R . .
H7B H 0.0018 0.4925 0.1123 0.049 Uiso 1 1 calc R . .
H7C H 0.2025 0.5389 0.0543 0.049 Uiso 1 1 calc R . .
O8 O 0.0375(2) 0.17717(17) 0.05462(9) 0.0381(4) Uani 1 1 d . . .
O9 O 0.2608(2) -0.01696(16) 0.09502(9) 0.0322(3) Uani 1 1 d . . .
H9 H 0.1725 -0.0280 0.0517 0.048 Uiso 1 1 calc R . .
C10 C 0.5442(3) 0.2510(3) 0.09001(13) 0.0364(5) Uani 1 1 d . . .
H10A H 0.6474 0.1958 0.0981 0.055 Uiso 1 1 calc R . .
H10B H 0.6050 0.3680 0.1180 0.055 Uiso 1 1 calc R . .
H10C H 0.5097 0.2513 0.0263 0.055 Uiso 1 1 calc R . .
C11 C 0.6275(2) 0.4155(2) 0.33677(11) 0.0235(4) Uani 1 1 d . . .
H11A H 0.7288 0.4457 0.2912 0.035 Uiso 1 1 calc R . .
H11B H 0.6643 0.3413 0.3757 0.035 Uiso 1 1 calc R . .
H11C H 0.6331 0.5188 0.3722 0.035 Uiso 1 1 calc R . .
C12 C 0.2300(2) -0.00215(19) 0.27126(11) 0.0203(4) Uani 1 1 d . . .
H12 H 0.2203 -0.1081 0.2345 0.024 Uiso 1 1 calc R . .
C13 C 0.3022(2) -0.00745(19) 0.36870(11) 0.0211(4) Uani 1 1 d . . .
C14 C 0.3042(2) 0.15530(19) 0.42150(11) 0.0190(4) Uani 1 1 d . . .
C15 C 0.2320(2) 0.26857(19) 0.36515(10) 0.0183(4) Uani 1 1 d . . .
O16 O 0.51378(17) -0.00565(15) 0.37244(8) 0.0280(3) Uani 1 1 d . . .
H16 H 0.5328 -0.0587 0.4147 0.042 Uiso 1 1 calc R . .
C17 C 0.1529(3) -0.1620(2) 0.40827(13) 0.0301(4) Uani 1 1 d . . .
H17A H 0.1445 -0.2655 0.3723 0.045 Uiso 1 1 calc R . .
H17B H 0.0111 -0.1561 0.4085 0.045 Uiso 1 1 calc R . .
H17C H 0.2072 -0.1637 0.4694 0.045 Uiso 1 1 calc R . .
O18 O 0.36011(18) 0.18857(15) 0.50054(8) 0.0261(3) Uani 1 1 d . . .
C19 C 0.2122(3) 0.4176(2) 0.42130(11) 0.0228(4) Uani 1 1 d . . .
H19A H 0.1395 0.4743 0.3849 0.034 Uiso 1 1 calc R . .
H19B H 0.3541 0.4981 0.4433 0.034 Uiso 1 1 calc R . .
H19C H 0.1301 0.3764 0.4719 0.034 Uiso 1 1 calc R . .
C20 C 0.0155(2) 0.0147(2) 0.26958(11) 0.0220(4) Uani 1 1 d . . .
C21 C 0.0194(2) 0.15283(19) 0.31808(11) 0.0203(4) Uani 1 1 d . . .
H21 H -0.1053 0.1783 0.3232 0.024 Uiso 1 1 calc R . .
C22 C -0.1757(3) -0.1166(2) 0.21762(14) 0.0321(4) Uani 1 1 d . . .
H22A H -0.3015 -0.0885 0.2275 0.048 Uiso 1 1 calc R . .
H22B H -0.1967 -0.2283 0.2374 0.048 Uiso 1 1 calc R . .
H22C H -0.1534 -0.1185 0.1541 0.048 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 C1 C6 126.23(15) . . ?
C1 C2 C3 118.06(14) . . ?
C1 C2 C7 124.30(16) . . ?
C3 C2 C7 117.64(15) . . ?
O8 C3 C2 122.40(15) . . ?
O8 C3 C4 121.38(16) . . ?
C2 C3 C4 115.90(14) . . ?
O9 C4 C3 110.44(14) . . ?
O9 C4 C10 108.73(14) . . ?
C3 C4 C10 106.46(14) . . ?
O9 C4 C5 108.45(13) . . ?
C3 C4 C5 112.09(13) . . ?
C10 C4 C5 110.63(14) . . ?
C4 C5 C12 111.25(13) . . ?
C4 C5 C6 114.58(12) . . ?
C12 C5 C6 110.18(12) . . ?
C1 C6 C11 108.23(12) . . ?
C1 C6 C5 114.63(13) . . ?
C11 C6 C5 110.02(12) . . ?
C1 C6 C15 105.55(12) . . ?
C11 C6 C15 110.34(13) . . ?
C5 C6 C15 107.97(11) . . ?
C20 C12 C13 107.73(13) . . ?
C20 C12 C5 108.65(12) . . ?
C13 C12 C5 109.33(13) . . ?
O16 C13 C17 111.21(12) . . ?
O16 C13 C12 108.37(12) . . ?
C17 C13 C12 111.83(14) . . ?
O16 C13 C14 108.51(13) . . ?
C17 C13 C14 109.47(13) . . ?
C12 C13 C14 107.32(12) . . ?
O18 C14 C15 124.07(14) . . ?
O18 C14 C13 122.37(13) . . ?
C15 C14 C13 113.56(13) . . ?
C14 C15 C21 104.97(12) . . ?
C14 C15 C19 112.00(13) . . ?
C21 C15 C19 111.68(12) . . ?
C14 C15 C6 105.21(11) . . ?
C21 C15 C6 108.05(12) . . ?
C19 C15 C6 114.30(12) . . ?
C21 C20 C22 126.23(14) . . ?
C21 C20 C12 112.77(14) . . ?
C22 C20 C12 121.00(14) . . ?
C20 C21 C15 117.14(13) . . ?
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 C2 1.328(2) . ?
C1 C6 1.506(2) . ?
C2 C3 1.479(2) . ?
C2 C7 1.505(2) . ?
C3 O8 1.219(2) . ?
C3 C4 1.528(2) . ?
C4 O9 1.415(2) . ?
C4 C10 1.536(2) . ?
C4 C5 1.547(2) . ?
C5 C12 1.549(2) . ?
C5 C6 1.572(2) . ?
C6 C11 1.544(2) . ?
C6 C15 1.610(2) . ?
C12 C20 1.510(2) . ?
C12 C13 1.537(2) . ?
C13 O16 1.4257(18) . ?
C13 C17 1.526(2) . ?
C13 C14 1.539(2) . ?
C14 O18 1.215(2) . ?
C14 C15 1.5200(19) . ?
C15 C21 1.521(2) . ?
C15 C19 1.521(2) . ?
C20 C21 1.327(2) . ?
C20 C22 1.502(2) . ?
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
C6 C1 C2 C3 -6.8(2) . . . . ?
C6 C1 C2 C7 173.96(15) . . . . ?
C1 C2 C3 O8 157.96(17) . . . . ?
C7 C2 C3 O8 -22.8(2) . . . . ?
C1 C2 C3 C4 -28.5(2) . . . . ?
C7 C2 C3 C4 150.82(15) . . . . ?
O8 C3 C4 O9 -15.5(2) . . . . ?
C2 C3 C4 O9 170.86(13) . . . . ?
O8 C3 C4 C10 102.38(19) . . . . ?
C2 C3 C4 C10 -71.27(18) . . . . ?
O8 C3 C4 C5 -136.53(17) . . . . ?
C2 C3 C4 C5 49.82(19) . . . . ?
O9 C4 C5 C12 -33.46(16) . . . . ?
C3 C4 C5 C12 88.73(16) . . . . ?
C10 C4 C5 C12 -152.62(14) . . . . ?
O9 C4 C5 C6 -159.25(12) . . . . ?
C3 C4 C5 C6 -37.06(18) . . . . ?
C10 C4 C5 C6 81.58(16) . . . . ?
C2 C1 C6 C11 141.10(16) . . . . ?
C2 C1 C6 C5 17.9(2) . . . . ?
C2 C1 C6 C15 -100.77(18) . . . . ?
C4 C5 C6 C1 6.18(18) . . . . ?
C12 C5 C6 C1 -120.17(13) . . . . ?
C4 C5 C6 C11 -116.04(14) . . . . ?
C12 C5 C6 C11 117.60(13) . . . . ?
C4 C5 C6 C15 123.49(13) . . . . ?
C12 C5 C6 C15 -2.86(16) . . . . ?
C4 C5 C12 C20 -70.41(16) . . . . ?
C6 C5 C12 C20 57.79(17) . . . . ?
C4 C5 C12 C13 172.28(12) . . . . ?
C6 C5 C12 C13 -59.52(15) . . . . ?
C20 C12 C13 O16 -174.07(12) . . . . ?
C5 C12 C13 O16 -56.17(15) . . . . ?
C20 C12 C13 C17 62.99(16) . . . . ?
C5 C12 C13 C17 -179.11(12) . . . . ?
C20 C12 C13 C14 -57.07(15) . . . . ?
C5 C12 C13 C14 60.82(15) . . . . ?
O16 C13 C14 O18 -61.21(18) . . . . ?
C17 C13 C14 O18 60.32(19) . . . . ?
C12 C13 C14 O18 -178.12(13) . . . . ?
O16 C13 C14 C15 118.25(13) . . . . ?
C17 C13 C14 C15 -120.21(14) . . . . ?
C12 C13 C14 C15 1.34(16) . . . . ?
O18 C14 C15 C21 -128.36(15) . . . . ?
C13 C14 C15 C21 52.19(15) . . . . ?
O18 C14 C15 C19 -7.0(2) . . . . ?
C13 C14 C15 C19 173.55(12) . . . . ?
O18 C14 C15 C6 117.74(16) . . . . ?
C13 C14 C15 C6 -61.71(15) . . . . ?
C1 C6 C15 C14 -175.86(12) . . . . ?
C11 C6 C15 C14 -59.15(15) . . . . ?
C5 C6 C15 C14 61.11(15) . . . . ?
C1 C6 C15 C21 72.42(14) . . . . ?
C11 C6 C15 C21 -170.87(11) . . . . ?
C5 C6 C15 C21 -50.61(14) . . . . ?
C1 C6 C15 C19 -52.57(17) . . . . ?
C11 C6 C15 C19 64.13(16) . . . . ?
C5 C6 C15 C19 -175.61(12) . . . . ?
C13 C12 C20 C21 58.89(17) . . . . ?
C5 C12 C20 C21 -59.44(18) . . . . ?
C13 C12 C20 C22 -120.66(16) . . . . ?
C5 C12 C20 C22 121.01(16) . . . . ?
C22 C20 C21 C15 -179.94(15) . . . . ?
C12 C20 C21 C15 0.5(2) . . . . ?
C14 C15 C21 C20 -56.03(17) . . . . ?
C19 C15 C21 C20 -177.61(13) . . . . ?
C6 C15 C21 C20 55.86(17) . . . . ?
loop_
_cod_related_entry_id
_cod_related_entry_database
_cod_related_entry_code
1 ChemSpider 211326
