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#$Date: 2019-03-05 10:52:05 +0200 (Tue, 05 Mar 2019) $
#$Revision: 213973 $
#$URL: file:///home/coder/svn-repositories/cod/cif/7/15/15/7151567.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_7151567
loop_
_publ_author_name
'Dang, Hai-Shan'
'Roberts, Brian P.'
'Tocher, Derek A.'
_publ_section_title
;
 Thiol-catalysed radical-chain redox rearrangement reactions of
 benzylidene acetals derived from terpenoid diols
;
_journal_issue                   22
_journal_name_full               'Organic &  Biomolecular Chemistry'
_journal_page_first              4073
_journal_paper_doi               10.1039/b309060b
_journal_volume                  1
_journal_year                    2003
_chemical_formula_sum            'C19 H28 O2'
_chemical_formula_weight         288.41
_space_group_IT_number           19
_symmetry_cell_setting           orthorhombic
_symmetry_space_group_name_Hall  'P 2ac 2ab'
_symmetry_space_group_name_H-M   'P 21 21 21'
_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                 90.00
_cell_angle_gamma                90.00
_cell_formula_units_Z            4
_cell_length_a                   8.804(3)
_cell_length_b                   10.274(3)
_cell_length_c                   18.428(5)
_cell_measurement_temperature    150(2)
_cell_volume                     1666.9(9)
_computing_cell_refinement       'Bruker SAINT'
_computing_data_collection       'Bruker SMART'
_computing_data_reduction        'Bruker SAINT'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 1990)'
_diffrn_ambient_temperature      150(2)
_diffrn_measured_fraction_theta_full 1.000
_diffrn_measured_fraction_theta_max 0.974
_diffrn_measurement_device_type  'Bruker SMART APEX diffractometer'
_diffrn_measurement_method       'ω rotation with narrow frames'
_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  0.0698
_diffrn_reflns_av_sigmaI/netI    0.0731
_diffrn_reflns_limit_h_max       11
_diffrn_reflns_limit_h_min       -11
_diffrn_reflns_limit_k_max       13
_diffrn_reflns_limit_k_min       -13
_diffrn_reflns_limit_l_max       23
_diffrn_reflns_limit_l_min       -23
_diffrn_reflns_number            14443
_diffrn_reflns_theta_full        26.00
_diffrn_reflns_theta_max         28.26
_diffrn_reflns_theta_min         2.21
_diffrn_standards_number         0
_exptl_absorpt_coefficient_mu    0.072
_exptl_absorpt_correction_T_max  0.9986
_exptl_absorpt_correction_T_min  0.9648
_exptl_absorpt_correction_type   multi-scan
_exptl_crystal_colour            colourless
_exptl_crystal_density_diffrn    1.149
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       needle
_exptl_crystal_F_000             632
_exptl_crystal_size_max          0.50
_exptl_crystal_size_mid          0.04
_exptl_crystal_size_min          0.02
_refine_diff_density_max         0.250
_refine_diff_density_min         -0.199
_refine_diff_density_rms         0.041
_refine_ls_abs_structure_details 'Flack H D (1983), Acta Cryst. A39, 876-881'
_refine_ls_abs_structure_Flack   2.1(15)
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   0.987
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     194
_refine_ls_number_reflns         3899
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      0.987
_refine_ls_R_factor_all          0.0817
_refine_ls_R_factor_gt           0.0579
_refine_ls_shift/su_max          0.001
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'calc w=1/[σ²(Fo²)+(0.0660P)²+0.0000P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1220
_refine_ls_wR_factor_ref         0.1329
_reflns_number_gt                2927
_reflns_number_total             3899
_reflns_threshold_expression     I>2σ(I)
_cod_data_source_file            b309060b.txt
_cod_data_source_block           str0165_Compound_56
_cod_original_cell_volume        1666.9(8)
_cod_original_sg_symbol_H-M      P2(1)2(1)2(1)
_cod_database_code               7151567
loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'-x+1/2, -y, z+1/2'
'-x, y+1/2, -z+1/2'
'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
O1 O 0.15357(17) 0.16319(12) 1.03009(7) 0.0232(3) Uani 1 1 d . . .
O2 O 0.11113(18) 0.36569(12) 0.98012(7) 0.0255(4) Uani 1 1 d . . .
C1 C 0.1945(2) 0.29512(18) 1.03172(11) 0.0231(5) Uani 1 1 d . . .
H1 H 0.3054 0.3037 1.0210 0.028 Uiso 1 1 calc R . .
C2 C 0.1615(2) 0.35216(19) 1.10605(11) 0.0240(5) Uani 1 1 d . . .
C3 C 0.1508(3) 0.4863(2) 1.11330(12) 0.0298(5) Uani 1 1 d . . .
H3 H 0.1586 0.5405 1.0717 0.036 Uiso 1 1 calc R . .
C4 C 0.1287(3) 0.5414(2) 1.18130(12) 0.0359(6) Uani 1 1 d . . .
H4 H 0.1227 0.6333 1.1861 0.043 Uiso 1 1 calc R . .
C5 C 0.1156(3) 0.4637(2) 1.24170(12) 0.0392(6) Uani 1 1 d . . .
H5 H 0.0993 0.5014 1.2881 0.047 Uiso 1 1 calc R . .
C6 C 0.1262(3) 0.3299(2) 1.23427(12) 0.0384(6) Uani 1 1 d . . .
H6 H 0.1180 0.2758 1.2759 0.046 Uiso 1 1 calc R . .
C7 C 0.1488(3) 0.2744(2) 1.16671(11) 0.0306(5) Uani 1 1 d . . .
H7 H 0.1556 0.1825 1.1621 0.037 Uiso 1 1 calc R . .
C8 C 0.0462(3) 0.4146(2) 0.86171(12) 0.0386(6) Uani 1 1 d . . .
H8A H -0.0604 0.3900 0.8686 0.058 Uiso 1 1 calc R . .
H8B H 0.0732 0.4060 0.8103 0.058 Uiso 1 1 calc R . .
H8C H 0.0610 0.5050 0.8772 0.058 Uiso 1 1 calc R . .
C9 C 0.1463(3) 0.32625(18) 0.90653(10) 0.0247(5) Uani 1 1 d . . .
H9 H 0.2550 0.3473 0.8961 0.030 Uiso 1 1 calc R . .
C10 C 0.1223(2) 0.17812(18) 0.89768(10) 0.0211(4) Uani 1 1 d . . .
H10 H 0.0108 0.1600 0.8996 0.025 Uiso 1 1 calc R . .
C11 C 0.1986(2) 0.10725(19) 0.96155(10) 0.0218(4) Uani 1 1 d . . .
H11 H 0.3107 0.1203 0.9566 0.026 Uiso 1 1 calc R . .
C12 C 0.1700(2) -0.03978(19) 0.96391(11) 0.0258(5) Uani 1 1 d . . .
H12 H 0.2343 -0.0756 1.0040 0.031 Uiso 1 1 calc R . .
C13 C 0.0040(3) -0.0787(2) 0.98074(12) 0.0306(5) Uani 1 1 d . . .
H13 H -0.0639 -0.0137 0.9567 0.037 Uiso 1 1 calc R . .
C14 C -0.0400(3) -0.2141(2) 0.95222(14) 0.0440(7) Uani 1 1 d . . .
H14A H 0.0285 -0.2795 0.9728 0.066 Uiso 1 1 calc R . .
H14B H -0.0319 -0.2152 0.8992 0.066 Uiso 1 1 calc R . .
H14C H -0.1448 -0.2338 0.9665 0.066 Uiso 1 1 calc R . .
C15 C -0.0298(3) -0.0756(2) 1.06161(13) 0.0468(7) Uani 1 1 d . . .
H15A H -0.1370 -0.0965 1.0697 0.070 Uiso 1 1 calc R . .
H15B H -0.0080 0.0115 1.0807 0.070 Uiso 1 1 calc R . .
H15C H 0.0340 -0.1397 1.0865 0.070 Uiso 1 1 calc R . .
C16 C 0.2340(3) -0.0935(2) 0.89292(12) 0.0323(5) Uani 1 1 d . . .
H16A H 0.3454 -0.0805 0.8921 0.039 Uiso 1 1 calc R . .
H16B H 0.2140 -0.1882 0.8904 0.039 Uiso 1 1 calc R . .
C17 C 0.1638(3) -0.0274(2) 0.82687(11) 0.0322(5) Uani 1 1 d . . .
H17A H 0.0538 -0.0470 0.8256 0.039 Uiso 1 1 calc R . .
H17B H 0.2100 -0.0642 0.7824 0.039 Uiso 1 1 calc R . .
C18 C 0.1857(3) 0.1206(2) 0.82657(11) 0.0287(5) Uani 1 1 d . . .
H18 H 0.2974 0.1381 0.8255 0.034 Uiso 1 1 calc R . .
C19 C 0.1178(3) 0.1748(2) 0.75641(11) 0.0425(7) Uani 1 1 d . . .
H19A H 0.1532 0.1229 0.7151 0.064 Uiso 1 1 calc R . .
H19B H 0.1499 0.2654 0.7501 0.064 Uiso 1 1 calc R . .
H19C H 0.0067 0.1708 0.7590 0.064 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
C1 O1 C11 109.45(15) . . ?
C1 O2 C9 112.21(15) . . ?
O1 C1 O2 110.50(16) . . ?
O1 C1 C2 110.07(17) . . ?
O2 C1 C2 108.17(16) . . ?
C7 C2 C3 119.5(2) . . ?
C7 C2 C1 121.58(18) . . ?
C3 C2 C1 118.89(19) . . ?
C2 C3 C4 120.1(2) . . ?
C5 C4 C3 120.4(2) . . ?
C4 C5 C6 119.4(2) . . ?
C5 C6 C7 120.5(2) . . ?
C2 C7 C6 120.2(2) . . ?
O2 C9 C8 102.66(17) . . ?
O2 C9 C10 110.19(15) . . ?
C8 C9 C10 117.04(18) . . ?
C11 C10 C18 108.10(16) . . ?
C11 C10 C9 109.02(16) . . ?
C18 C10 C9 114.72(16) . . ?
O1 C11 C12 108.82(16) . . ?
O1 C11 C10 111.16(15) . . ?
C12 C11 C10 114.63(16) . . ?
C16 C12 C11 105.74(17) . . ?
C16 C12 C13 115.24(18) . . ?
C11 C12 C13 114.59(17) . . ?
C15 C13 C14 107.78(18) . . ?
C15 C13 C12 112.1(2) . . ?
C14 C13 C12 113.8(2) . . ?
C17 C16 C12 111.96(17) . . ?
C16 C17 C18 113.19(18) . . ?
C19 C18 C17 108.37(18) . . ?
C19 C18 C10 115.93(19) . . ?
C17 C18 C10 109.39(17) . . ?
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 C1 1.403(2) . ?
O1 C11 1.443(2) . ?
O2 C1 1.403(2) . ?
O2 C9 1.449(2) . ?
C1 C2 1.518(3) . ?
C2 C7 1.378(3) . ?
C2 C3 1.388(3) . ?
C3 C4 1.389(3) . ?
C4 C5 1.375(3) . ?
C5 C6 1.385(3) . ?
C6 C7 1.384(3) . ?
C8 C9 1.511(3) . ?
C9 C10 1.545(3) . ?
C10 C11 1.538(3) . ?
C10 C18 1.542(3) . ?
C11 C12 1.532(3) . ?
C12 C16 1.527(3) . ?
C12 C13 1.547(3) . ?
C13 C15 1.520(3) . ?
C13 C14 1.536(3) . ?
C16 C17 1.524(3) . ?
C17 C18 1.532(3) . ?
C18 C19 1.530(3) . ?
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
C11 O1 C1 O2 65.9(2) . . . . ?
C11 O1 C1 C2 -174.65(15) . . . . ?
C9 O2 C1 O1 -64.9(2) . . . . ?
C9 O2 C1 C2 174.55(16) . . . . ?
O1 C1 C2 C7 21.8(3) . . . . ?
O2 C1 C2 C7 142.6(2) . . . . ?
O1 C1 C2 C3 -161.17(19) . . . . ?
O2 C1 C2 C3 -40.3(3) . . . . ?
C7 C2 C3 C4 0.5(4) . . . . ?
C1 C2 C3 C4 -176.6(2) . . . . ?
C2 C3 C4 C5 -0.7(4) . . . . ?
C3 C4 C5 C6 0.7(4) . . . . ?
C4 C5 C6 C7 -0.5(4) . . . . ?
C3 C2 C7 C6 -0.3(4) . . . . ?
C1 C2 C7 C6 176.7(2) . . . . ?
C5 C6 C7 C2 0.3(4) . . . . ?
C1 O2 C9 C8 -179.48(17) . . . . ?
C1 O2 C9 C10 55.1(2) . . . . ?
O2 C9 C10 C11 -47.2(2) . . . . ?
C8 C9 C10 C11 -163.93(19) . . . . ?
O2 C9 C10 C18 -168.56(17) . . . . ?
C8 C9 C10 C18 74.7(3) . . . . ?
C1 O1 C11 C12 173.54(16) . . . . ?
C1 O1 C11 C10 -59.3(2) . . . . ?
C18 C10 C11 O1 175.47(15) . . . . ?
C9 C10 C11 O1 50.2(2) . . . . ?
C18 C10 C11 C12 -60.6(2) . . . . ?
C9 C10 C11 C12 174.08(17) . . . . ?
O1 C11 C12 C16 -174.77(16) . . . . ?
C10 C11 C12 C16 60.1(2) . . . . ?
O1 C11 C12 C13 57.2(2) . . . . ?
C10 C11 C12 C13 -68.0(2) . . . . ?
C16 C12 C13 C15 154.94(19) . . . . ?
C11 C12 C13 C15 -82.0(2) . . . . ?
C16 C12 C13 C14 32.3(3) . . . . ?
C11 C12 C13 C14 155.35(19) . . . . ?
C11 C12 C16 C17 -56.2(2) . . . . ?
C13 C12 C16 C17 71.5(2) . . . . ?
C12 C16 C17 C18 57.6(3) . . . . ?
C16 C17 C18 C19 177.32(19) . . . . ?
C16 C17 C18 C10 -55.4(3) . . . . ?
C11 C10 C18 C19 177.37(18) . . . . ?
C9 C10 C18 C19 -60.8(3) . . . . ?
C11 C10 C18 C17 54.5(2) . . . . ?
C9 C10 C18 C17 176.36(19) . . . . ?
loop_
_cod_related_entry_id
_cod_related_entry_database
_cod_related_entry_code
1 ChemSpider 9464207
