#------------------------------------------------------------------------------
#$Date: 2016-02-18 17:37:37 +0200 (Thu, 18 Feb 2016) $
#$Revision: 176729 $
#$URL: svn://www.crystallography.net/cod/cif/1/51/72/1517229.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_1517229
loop_
_publ_author_name
'Clark, J. Stephen'
'Delion, Laetitia'
'Farrugia, Louis J.'
_publ_section_title
;
 Total synthesis of the purported structure of sclerophytin f.
;
_journal_issue                   16
_journal_name_full               'Organic letters'
_journal_page_first              4300
_journal_page_last               4303
_journal_paper_doi               10.1021/ol5020152
_journal_volume                  16
_journal_year                    2014
_chemical_absolute_configuration rm
_chemical_compound_source        'as described'
_chemical_formula_moiety         'C20 H32 O3'
_chemical_formula_sum            'C20 H32 O3'
_chemical_formula_weight         320.45
_chemical_name_systematic
;
 ?
;
_space_group_IT_number           154
_symmetry_cell_setting           trigonal
_symmetry_Int_Tables_number      154
_symmetry_space_group_name_Hall  'P 32 2"'
_symmetry_space_group_name_H-M   'P 32 2 1'
_atom_sites_solution_hydrogens   mixed
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   direct
_audit_conform_dict_location     ftp://ftp.iucr.org/pub/cif_core.dic
_audit_conform_dict_name         cif_core.dic
_audit_conform_dict_version      2.4.3
_audit_creation_date             2014-03-27T15:45:19-00:00
_audit_creation_method           'WinGX routine CIF_UPDATE'
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                120
_cell_formula_units_Z            6
_cell_length_a                   17.4587(6)
_cell_length_b                   17.4587(6)
_cell_length_c                   10.7319(4)
_cell_measurement_reflns_used    9901
_cell_measurement_temperature    298(2)
_cell_measurement_theta_max      26.44
_cell_measurement_theta_min      2.33
_cell_measurement_wavelength     0.71073
_cell_volume                     2832.90(17)
_computing_cell_refinement       'SAINT V8.27B integration software'
_computing_data_collection       'Bruker APEX2 software'
_computing_data_reduction        'SORTAV (Blessing, 1995)'
_computing_molecular_graphics    'ORTEP-3 for Windows (Farrugia, 2012)'
_computing_publication_material  'WinGX publication routines (Farrugia, 2012)'
_computing_structure_refinement  'SHELXL-2013 (Sheldrick, 2008)'
_computing_structure_solution    'SIR-92 (Altomare et al., 1994)'
_diffrn_ambient_temperature      298(2)
_diffrn_detector                 'APEX-II CCD'
_diffrn_measured_fraction_theta_full 1
_diffrn_measured_fraction_theta_max 1
_diffrn_measurement_device       'κ-geometry diffractometer'
_diffrn_measurement_device_type  'Bruker APEX-II'
_diffrn_measurement_method       'φ or ω oscillation scans'
_diffrn_orient_matrix_UB_11      -0.055962
_diffrn_orient_matrix_UB_12      0.001494
_diffrn_orient_matrix_UB_13      0.012935
_diffrn_orient_matrix_UB_21      0.033665
_diffrn_orient_matrix_UB_22      0.065944
_diffrn_orient_matrix_UB_23      -0.007066
_diffrn_orient_matrix_UB_31      -0.010453
_diffrn_orient_matrix_UB_32      -0.004855
_diffrn_orient_matrix_UB_33      -0.092007
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.091
_diffrn_reflns_Laue_measured_fraction_full 1
_diffrn_reflns_Laue_measured_fraction_max 1
_diffrn_reflns_limit_h_max       22
_diffrn_reflns_limit_h_min       -22
_diffrn_reflns_limit_k_max       22
_diffrn_reflns_limit_k_min       -22
_diffrn_reflns_limit_l_max       13
_diffrn_reflns_limit_l_min       -13
_diffrn_reflns_number            74902
_diffrn_reflns_point_group_measured_fraction_full 1
_diffrn_reflns_point_group_measured_fraction_max 1
_diffrn_reflns_reduction_process
;
        Scaled and merged with Sortav
        R.H. Blessing, (1987) Cryst. Rev. 1, 3-58
        R.H. Blessing, (1989) J. Appl. Cryst. 22, 396-397
;
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         25.958
_diffrn_reflns_theta_min         1.347
_diffrn_source                   'sealed x-ray tube'
_exptl_absorpt_coefficient_mu    0.074
_exptl_absorpt_correction_T_max  0.746
_exptl_absorpt_correction_T_min  0.638
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
SADABS-2012/1 - Bruker AXS area detector scaling and absorption correction
;
_exptl_crystal_colour            colourless
_exptl_crystal_density_diffrn    1.127
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       plate
_exptl_crystal_F_000             1056
_exptl_crystal_size_max          0.6
_exptl_crystal_size_mid          0.2
_exptl_crystal_size_min          0.1
_refine_diff_density_max         0.244
_refine_diff_density_min         -0.223
_refine_diff_density_rms         0.031
_refine_ls_abs_structure_details
;
 Flack x determined using 1090 quotients [(I+)-(I-)]/[(I+)+(I-)]
 (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259).
;
_refine_ls_abs_structure_Flack   -0.2(5)
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.055
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_constraints    0
_refine_ls_number_parameters     212
_refine_ls_number_reflns         3714
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.055
_refine_ls_R_factor_all          0.0764
_refine_ls_R_factor_gt           0.0509
_refine_ls_shift/su_max          0
_refine_ls_shift/su_mean         0
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'w=1/[σ²(Fo²)+(0.0383P)²+0.6609P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1122
_refine_ls_wR_factor_ref         0.1192
_reflns_number_gt                2784
_reflns_number_total             3714
_reflns_threshold_expression     'I > 2σ(I)'
_cod_data_source_file            ol5020152_si_003.cif
_cod_data_source_block           shelx
_cod_depositor_comments
'Adding full bibliography for 1517229--1517231.cif.'
_cod_original_cell_volume        2832.9(2)
_cod_database_code               1517229
#BEGIN Tags that were not found in dictionaries:
_shelx_estimated_absorpt_t_min   0.957
_shelx_estimated_absorpt_t_max   0.993
#END Tags that were not found in dictionaries
loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'-y, x-y, z+2/3'
'-x+y, -x, z+1/3'
'x-y, -y, -z+1/3'
'-x, -x+y, -z+2/3'
'y, x, -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_calc_flag
O1 O 0.64104(15) 0.70519(14) 0.1165(2) 0.0549(6) Uani 1 d
O2 O 0.71032(15) 0.57575(15) 0.1209(2) 0.0622(6) Uani 1 d
H2 H 0.7097 0.602 0.0579 0.093 Uiso 1 calc
O3 O 0.8998(3) 0.9134(2) 0.1289(5) 0.152(2) Uani 1 d
H3A H 0.9288 0.9712 0.1596 0.228 Uiso 0.5 d
H3B H 0.9046 0.9091 0.0438 0.228 Uiso 0.5 d
C1 C 0.5404(2) 0.6225(2) 0.2759(3) 0.0473(7) Uani 1 d
H1 H 0.5412 0.592 0.3522 0.057 Uiso 1 calc
C2 C 0.6067(2) 0.6222(2) 0.1818(3) 0.0444(7) Uani 1 d
H2A H 0.5719 0.5756 0.1211 0.053 Uiso 1 calc
C3 C 0.6821(2) 0.6066(2) 0.2260(3) 0.0502(7) Uani 1 d
C4 C 0.7625(2) 0.6897(2) 0.2805(4) 0.0657(10) Uani 1 d
H4A H 0.7411 0.7159 0.3411 0.079 Uiso 1 calc
H4B H 0.799 0.6713 0.3248 0.079 Uiso 1 calc
C5 C 0.8206(3) 0.7611(2) 0.1861(4) 0.0786(12) Uani 1 d
H5A H 0.8724 0.756 0.169 0.094 Uiso 1 calc
H5B H 0.788 0.7501 0.1088 0.094 Uiso 1 calc
C6 C 0.8509(3) 0.8551(3) 0.2277(6) 0.0965(15) Uani 1 d
H6 H 0.8918 0.8682 0.2975 0.116 Uiso 1 calc
C7 C 0.7786(3) 0.8730(2) 0.2719(5) 0.0871(14) Uani 1 d
C8 C 0.7043(3) 0.8581(2) 0.1855(4) 0.0779(11) Uani 1 d
H8A H 0.7285 0.8734 0.102 0.093 Uiso 1 calc
H8B H 0.6854 0.8998 0.2084 0.093 Uiso 1 calc
C9 C 0.6215(2) 0.7662(2) 0.1792(3) 0.0591(9) Uani 1 d
H9 H 0.5771 0.7712 0.1297 0.071 Uiso 1 calc
C10 C 0.5783(2) 0.7220(2) 0.3038(3) 0.0545(8) Uani 1 d
H10 H 0.6251 0.74 0.3663 0.065 Uiso 1 calc
C11 C 0.5116(3) 0.7463(2) 0.3516(3) 0.0654(10) Uani 1 d
C12 C 0.4216(3) 0.6990(3) 0.2916(4) 0.0784(12) Uani 1 d
H12A H 0.4257 0.7193 0.2065 0.094 Uiso 1 calc
H12B H 0.3814 0.7123 0.3367 0.094 Uiso 1 calc
C13 C 0.3856(3) 0.5992(3) 0.2924(4) 0.0714(11) Uani 1 d
H13A H 0.3801 0.5788 0.3777 0.086 Uiso 1 calc
H13B H 0.3272 0.5694 0.2549 0.086 Uiso 1 calc
C14 C 0.4466(2) 0.5757(2) 0.2205(3) 0.0565(8) Uani 1 d
H14 H 0.4516 0.5988 0.1359 0.068 Uiso 1 calc
C15 C 0.4082(2) 0.4744(3) 0.2077(4) 0.0711(10) Uani 1 d
H15 H 0.456 0.4657 0.1766 0.085 Uiso 1 calc
C16 C 0.3340(3) 0.4344(4) 0.1110(6) 0.133(2) Uani 1 d
H16A H 0.315 0.3729 0.1002 0.2 Uiso 1 calc
H16B H 0.3554 0.4647 0.033 0.2 Uiso 1 calc
H16C H 0.2852 0.4406 0.139 0.2 Uiso 1 calc
C17 C 0.3779(4) 0.4252(3) 0.3325(6) 0.125(2) Uani 1 d
H17A H 0.4227 0.4562 0.3944 0.188 Uiso 1 calc
H17B H 0.3683 0.3664 0.323 0.188 Uiso 1 calc
H17C H 0.3239 0.4223 0.3582 0.188 Uiso 1 calc
C18 C 0.6476(2) 0.5309(2) 0.3195(3) 0.0614(9) Uani 1 d
H18A H 0.5922 0.483 0.2906 0.092 Uiso 1 calc
H18B H 0.6391 0.551 0.3988 0.092 Uiso 1 calc
H18C H 0.6896 0.511 0.3279 0.092 Uiso 1 calc
C19 C 0.7872(4) 0.9099(3) 0.3825(6) 0.1202(19) Uani 1 d
H19A H 0.747 0.9271 0.4079 0.144 Uiso 1 calc
H19B H 0.8333 0.9188 0.4349 0.144 Uiso 1 calc
C20 C 0.5310(4) 0.8033(3) 0.4437(4) 0.0929(14) Uani 1 d
H20A H 0.4882 0.8155 0.4738 0.112 Uiso 1 calc
H20B H 0.5873 0.8313 0.4784 0.112 Uiso 1 calc
loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
O O 0.0106 0.006 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
C C 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
H H 0 0 '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
C9 O1 C2 112.5(2)
C3 O2 H2 109.5
C6 O3 H3A 108.5
C6 O3 H3B 136.5
H3A O3 H3B 114.6
C2 C1 C14 110.3(2)
C2 C1 C10 103.4(3)
C14 C1 C10 114.5(2)
C2 C1 H1 109.5
C14 C1 H1 109.5
C10 C1 H1 109.5
O1 C2 C1 104.6(2)
O1 C2 C3 111.2(2)
C1 C2 C3 120.5(2)
O1 C2 H2A 106.6
C1 C2 H2A 106.6
C3 C2 H2A 106.6
O2 C3 C18 104.6(3)
O2 C3 C4 109.2(3)
C18 C3 C4 110.2(3)
O2 C3 C2 107.8(2)
C18 C3 C2 110.6(3)
C4 C3 C2 113.9(3)
C5 C4 C3 115.8(3)
C5 C4 H4A 108.3
C3 C4 H4A 108.3
C5 C4 H4B 108.3
C3 C4 H4B 108.3
H4A C4 H4B 107.4
C6 C5 C4 114.6(4)
C6 C5 H5A 108.6
C4 C5 H5A 108.6
C6 C5 H5B 108.6
C4 C5 H5B 108.6
H5A C5 H5B 107.6
O3 C6 C5 108.4(4)
O3 C6 C7 110.3(4)
C5 C6 C7 116.0(3)
O3 C6 H6 107.3
C5 C6 H6 107.3
C7 C6 H6 107.3
C19 C7 C8 120.9(5)
C19 C7 C6 118.5(5)
C8 C7 C6 120.2(4)
C7 C8 C9 119.2(3)
C7 C8 H8A 107.5
C9 C8 H8A 107.5
C7 C8 H8B 107.5
C9 C8 H8B 107.5
H8A C8 H8B 107
O1 C9 C8 110.3(3)
O1 C9 C10 105.9(2)
C8 C9 C10 117.1(3)
O1 C9 H9 107.7
C8 C9 H9 107.7
C10 C9 H9 107.7
C11 C10 C9 114.0(2)
C11 C10 C1 115.1(3)
C9 C10 C1 102.8(2)
C11 C10 H10 108.2
C9 C10 H10 108.2
C1 C10 H10 108.2
C20 C11 C12 122.5(4)
C20 C11 C10 121.4(4)
C12 C11 C10 116.1(3)
C11 C12 C13 110.1(3)
C11 C12 H12A 109.6
C13 C12 H12A 109.6
C11 C12 H12B 109.6
C13 C12 H12B 109.6
H12A C12 H12B 108.1
C14 C13 C12 111.1(3)
C14 C13 H13A 109.4
C12 C13 H13A 109.4
C14 C13 H13B 109.4
C12 C13 H13B 109.4
H13A C13 H13B 108
C13 C14 C1 111.2(3)
C13 C14 C15 112.9(3)
C1 C14 C15 112.2(3)
C13 C14 H14 106.7
C1 C14 H14 106.7
C15 C14 H14 106.7
C16 C15 C17 111.2(4)
C16 C15 C14 111.4(4)
C17 C15 C14 113.1(3)
C16 C15 H15 106.9
C17 C15 H15 106.9
C14 C15 H15 106.9
C15 C16 H16A 109.5
C15 C16 H16B 109.5
H16A C16 H16B 109.5
C15 C16 H16C 109.5
H16A C16 H16C 109.5
H16B C16 H16C 109.5
C15 C17 H17A 109.5
C15 C17 H17B 109.5
H17A C17 H17B 109.5
C15 C17 H17C 109.5
H17A C17 H17C 109.5
H17B C17 H17C 109.5
C3 C18 H18A 109.5
C3 C18 H18B 109.5
H18A C18 H18B 109.5
C3 C18 H18C 109.5
H18A C18 H18C 109.5
H18B C18 H18C 109.5
C7 C19 H19A 120
C7 C19 H19B 120
H19A C19 H19B 120
C11 C20 H20A 120
C11 C20 H20B 120
H20A C20 H20B 120
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
O1 C9 1.437(4)
O1 C2 1.443(3)
O2 C3 1.439(4)
O2 H2 0.82
O3 C6 1.422(6)
O3 H3A 0.9334
O3 H3B 0.9237
C1 C2 1.537(4)
C1 C14 1.539(5)
C1 C10 1.548(4)
C1 H1 0.98
C2 C3 1.547(4)
C2 H2A 0.98
C3 C18 1.523(4)
C3 C4 1.542(5)
C4 C5 1.532(5)
C4 H4A 0.97
C4 H4B 0.97
C5 C6 1.517(5)
C5 H5A 0.97
C5 H5B 0.97
C6 C7 1.521(6)
C6 H6 0.98
C7 C19 1.323(7)
C7 C8 1.508(6)
C8 C9 1.533(5)
C8 H8A 0.97
C8 H8B 0.97
C9 C10 1.539(5)
C9 H9 0.98
C10 C11 1.514(5)
C10 H10 0.98
C11 C20 1.322(5)
C11 C12 1.506(6)
C12 C13 1.528(6)
C12 H12A 0.97
C12 H12B 0.97
C13 C14 1.528(5)
C13 H13A 0.97
C13 H13B 0.97
C14 C15 1.551(5)
C14 H14 0.98
C15 C16 1.528(6)
C15 C17 1.536(6)
C15 H15 0.98
C16 H16A 0.96
C16 H16B 0.96
C16 H16C 0.96
C17 H17A 0.96
C17 H17B 0.96
C17 H17C 0.96
C18 H18A 0.96
C18 H18B 0.96
C18 H18C 0.96
C19 H19A 0.93
C19 H19B 0.93
C20 H20A 0.93
C20 H20B 0.93
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
C9 O1 C2 C1 14.9(3)
C9 O1 C2 C3 -116.6(3)
C14 C1 C2 O1 93.5(3)
C10 C1 C2 O1 -29.3(3)
C14 C1 C2 C3 -140.5(3)
C10 C1 C2 C3 96.7(3)
O1 C2 C3 O2 -79.4(3)
C1 C2 C3 O2 157.8(3)
O1 C2 C3 C18 166.8(2)
C1 C2 C3 C18 44.0(4)
O1 C2 C3 C4 42.0(4)
C1 C2 C3 C4 -80.8(4)
O2 C3 C4 C5 48.0(4)
C18 C3 C4 C5 162.4(3)
C2 C3 C4 C5 -72.6(4)
C3 C4 C5 C6 138.0(4)
C4 C5 C6 O3 -176.8(4)
C4 C5 C6 C7 -52.1(6)
O3 C6 C7 C19 -109.4(5)
C5 C6 C7 C19 127.0(5)
O3 C6 C7 C8 64.1(5)
C5 C6 C7 C8 -59.5(6)
C19 C7 C8 C9 -98.9(5)
C6 C7 C8 C9 87.7(5)
C2 O1 C9 C8 133.7(3)
C2 O1 C9 C10 6.0(4)
C7 C8 C9 O1 -71.8(5)
C7 C8 C9 C10 49.4(5)
O1 C9 C10 C11 -149.3(3)
C8 C9 C10 C11 87.2(4)
O1 C9 C10 C1 -24.0(3)
C8 C9 C10 C1 -147.5(3)
C2 C1 C10 C11 156.9(3)
C14 C1 C10 C11 36.9(4)
C2 C1 C10 C9 32.3(3)
C14 C1 C10 C9 -87.7(3)
C9 C10 C11 C20 -103.6(4)
C1 C10 C11 C20 138.0(4)
C9 C10 C11 C12 78.8(4)
C1 C10 C11 C12 -39.6(4)
C20 C11 C12 C13 -126.8(4)
C10 C11 C12 C13 50.8(4)
C11 C12 C13 C14 -60.1(4)
C12 C13 C14 C1 58.5(4)
C12 C13 C14 C15 -174.4(3)
C2 C1 C14 C13 -162.4(3)
C10 C1 C14 C13 -46.3(4)
C2 C1 C14 C15 70.1(3)
C10 C1 C14 C15 -173.9(3)
C13 C14 C15 C16 75.1(4)
C1 C14 C15 C16 -158.3(3)
C13 C14 C15 C17 -51.0(5)
C1 C14 C15 C17 75.6(4)
