#------------------------------------------------------------------------------
#$Date: 2016-03-22 11:50:55 +0200 (Tue, 22 Mar 2016) $
#$Revision: 178919 $
#$URL: svn://www.crystallography.net/cod/cif/4/11/48/4114887.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_4114887
loop_
_publ_author_name
'Alois Fürstner'
'Karin Radkowski'
'Conny Wirtz'
'Richard Goddard'
'Christian W. Lehmann'
'Richard Mynott'
_publ_section_title
;
 Total Syntheses of the Phytotoxic Lactones Herbarumin I and II and a
 Synthesis-Based Solution of the Pinolidoxin Puzzle
;
_journal_name_full               'Journal of the American Chemical Society'
_journal_page_first              7061
_journal_page_last               7069
_journal_paper_doi               10.1021/ja020238i
_journal_volume                  124
_journal_year                    2002
_chemical_compound_source        'see paper'
_chemical_formula_sum            'C15 H24 O4'
_chemical_formula_weight         268.34
_chemical_name_systematic
; 
 ? 
;
_space_group_IT_number           4
_symmetry_cell_setting           monoclinic
_symmetry_Int_Tables_number      4
_symmetry_space_group_name_Hall  'P 2yb'
_symmetry_space_group_name_H-M   'P 1 21 1'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_cell_angle_alpha                90.00
_cell_angle_beta                 101.287(2)
_cell_angle_gamma                90.00
_cell_formula_units_Z            2
_cell_length_a                   6.7055(3)
_cell_length_b                   8.2104(3)
_cell_length_c                   13.4884(6)
_cell_measurement_reflns_used    9159
_cell_measurement_temperature    100
_cell_measurement_theta_max      27.48
_cell_measurement_theta_min      1.00
_cell_volume                     728.24(5)
_computing_cell_refinement       'Denzo / Scalepack (Otwinowski 1997)'
_computing_data_collection       'Collect software (Nonius, 1998)'
_computing_data_reduction        'Denzo / Scalepack (Otwinowski 1997)'
_computing_molecular_graphics    'ORTEP (Johnson, 1976)'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 1990)'
_diffrn_ambient_temperature      100
_diffrn_measured_fraction_theta_full 0.996
_diffrn_measured_fraction_theta_max 0.996
_diffrn_measurement_device_type  'Nonius KappaCCD'
_diffrn_measurement_method       'CCD ω-scan'
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_source         '0.3 mm rotating anode'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0775
_diffrn_reflns_av_sigmaI/netI    0.1030
_diffrn_reflns_limit_h_max       7
_diffrn_reflns_limit_h_min       -8
_diffrn_reflns_limit_k_max       10
_diffrn_reflns_limit_k_min       -9
_diffrn_reflns_limit_l_max       17
_diffrn_reflns_limit_l_min       -16
_diffrn_reflns_number            5091
_diffrn_reflns_theta_full        27.47
_diffrn_reflns_theta_max         27.47
_diffrn_reflns_theta_min         2.92
_diffrn_standards_decay_%        0.00
_diffrn_standards_interval_time  0
_diffrn_standards_number         0
_exptl_absorpt_coefficient_mu    0.087
_exptl_absorpt_correction_T_max  0.49
_exptl_absorpt_correction_T_min  0.22
_exptl_absorpt_correction_type   psi-scan
_exptl_absorpt_process_details   'XPREP, Siemens (1995)'
_exptl_crystal_colour            colorless
_exptl_crystal_density_diffrn    1.224
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    none
_exptl_crystal_description       plate
_exptl_crystal_F_000             292
_exptl_crystal_size_max          0.33
_exptl_crystal_size_mid          0.08
_exptl_crystal_size_min          0.03
_refine_diff_density_max         0.286
_refine_diff_density_min         -0.225
_refine_diff_density_rms         0.061
_refine_ls_abs_structure_details
'Flack, H. D. (1983). Acta Cryst. A39, 876-881'
_refine_ls_abs_structure_Flack   0(2)
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.024
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     172
_refine_ls_number_reflns         2910
_refine_ls_number_restraints     1
_refine_ls_restrained_S_all      1.024
_refine_ls_R_factor_all          0.1100
_refine_ls_R_factor_gt           0.0725
_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)+(0.0813P)²+0.5905P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1666
_refine_ls_wR_factor_ref         0.1901
_reflns_number_gt                2113
_reflns_number_total             2910
_reflns_threshold_expression     I>2σ(I)
_cod_data_source_file            ja020238i_1.cif
_cod_data_source_block           3727
_cod_depositor_comments
;
The following automatic conversions were performed:

'_exptl_crystal_density_meas' value 'none' was changed to '?' - the
value is perceived as not measured.

Automatic conversion script
Id: cif_fix_values 3008 2015-01-20 13:52:24Z robertas 
;
_cod_database_code               4114887
loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'-x, 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
C1 C 0.0123(6) 0.3208(5) 0.8673(3) 0.0214(8) Uani 1 1 d .
C2 C 0.1566(6) 0.2166(5) 0.9400(3) 0.0241(9) Uani 1 1 d .
H2A H 0.2819 0.1977 0.9131 0.029 Uiso 1 1 calc R
H2B H 0.0930 0.1096 0.9474 0.029 Uiso 1 1 calc R
C3 C 0.2106(6) 0.2997(5) 1.0428(3) 0.0263(9) Uani 1 1 d .
H3A H 0.2661 0.2175 1.0946 0.032 Uiso 1 1 calc R
H3B H 0.0853 0.3451 1.0605 0.032 Uiso 1 1 calc R
C4 C 0.3668(6) 0.4372(5) 1.0451(3) 0.0289(10) Uani 1 1 d .
H4A H 0.3833 0.4949 1.1106 0.035 Uiso 1 1 calc R
H4B H 0.4999 0.3891 1.0401 0.035 Uiso 1 1 calc R
C5 C 0.3064(6) 0.5577(5) 0.9610(3) 0.0243(9) Uani 1 1 d .
H5 H 0.2194 0.6454 0.9704 0.029 Uiso 1 1 calc R
C6 C 0.3688(6) 0.5468(5) 0.8754(3) 0.0231(9) Uani 1 1 d .
H6 H 0.4662 0.4643 0.8713 0.028 Uiso 1 1 calc R
C7 C 0.3045(6) 0.6492(5) 0.7834(3) 0.0239(9) Uani 1 1 d .
H7 H 0.4294 0.6896 0.7611 0.029 Uiso 1 1 calc R
C8 C 0.1632(6) 0.5722(5) 0.6918(3) 0.0238(9) Uani 1 1 d .
H8 H 0.2439 0.5036 0.6527 0.029 Uiso 1 1 calc R
C9 C -0.0157(6) 0.4749(5) 0.7154(3) 0.0234(8) Uani 1 1 d .
H9 H -0.0947 0.5443 0.7549 0.028 Uiso 1 1 calc R
C11 C 0.2349(7) 0.9792(5) 0.6720(3) 0.0318(10) Uani 1 1 d .
H11A H 0.2436 1.0730 0.7176 0.048 Uiso 1 1 calc R
H11B H 0.1772 1.0139 0.6028 0.048 Uiso 1 1 calc R
H11C H 0.3712 0.9344 0.6745 0.048 Uiso 1 1 calc R
C12 C 0.0996(6) 0.8497(5) 0.7048(3) 0.0260(9) Uani 1 1 d .
C13 C -0.1122(4) 0.9106(4) 0.7071(3) 0.0307(10) Uani 1 1 d .
H13A H -0.1948 0.8206 0.7246 0.046 Uiso 1 1 calc R
H13B H -0.1745 0.9536 0.6405 0.046 Uiso 1 1 calc R
H13C H -0.1045 0.9971 0.7578 0.046 Uiso 1 1 calc R
C91 C -0.1548(4) 0.4161(4) 0.6201(3) 0.0245(9) Uani 1 1 d R
H91A H -0.0804 0.3359 0.5862 0.029 Uiso 1 1 calc R
H91B H -0.1901 0.5096 0.5736 0.029 Uiso 1 1 calc R
C92 C -0.3501(6) 0.3380(5) 0.6381(3) 0.0274(9) Uani 1 1 d .
H92A H -0.4231 0.4161 0.6742 0.033 Uiso 1 1 calc R
H92B H -0.3162 0.2409 0.6817 0.033 Uiso 1 1 calc R
C93 C -0.4886(7) 0.2876(6) 0.5396(3) 0.0381(11) Uani 1 1 d .
H93A H -0.5236 0.3835 0.4965 0.057 Uiso 1 1 calc R
H93B H -0.6130 0.2388 0.5542 0.057 Uiso 1 1 calc R
H93C H -0.4182 0.2079 0.5046 0.057 Uiso 1 1 calc R
O1 O -0.1368(4) 0.3837(4) 0.8862(2) 0.0287(7) Uani 1 1 d .
O7 O 0.1869(4) 0.7856(3) 0.80110(19) 0.0245(6) Uani 1 1 d .
O8 O 0.0883(4) 0.7137(4) 0.6347(2) 0.0283(7) Uani 1 1 d .
O10 O 0.0695(4) 0.3373(3) 0.7764(2) 0.0224(6) Uani 1 1 d .
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_publ_flag
O1 C1 O10 122.9(3) ?
O1 C1 C2 124.4(4) ?
O10 C1 C2 112.7(3) ?
C1 C2 C3 110.3(3) ?
C1 C2 H2A 109.6 n
C3 C2 H2A 109.6 n
C1 C2 H2B 109.6 n
C3 C2 H2B 109.6 n
H2A C2 H2B 108.1 n
C2 C3 C4 112.7(3) ?
C2 C3 H3A 109.0 n
C4 C3 H3A 109.0 n
C2 C3 H3B 109.0 n
C4 C3 H3B 109.0 n
H3A C3 H3B 107.8 n
C5 C4 C3 112.8(3) ?
C5 C4 H4A 109.0 n
C3 C4 H4A 109.0 n
C5 C4 H4B 109.0 n
C3 C4 H4B 109.0 n
H4A C4 H4B 107.8 n
C6 C5 C4 122.5(4) ?
C6 C5 H5 118.8 n
C4 C5 H5 118.8 n
C5 C6 C7 127.3(4) ?
C5 C6 H6 116.3 n
C7 C6 H6 116.3 n
O7 C7 C6 112.7(3) ?
O7 C7 C8 100.6(3) ?
C6 C7 C8 118.0(3) ?
O7 C7 H7 108.4 n
C6 C7 H7 108.4 n
C8 C7 H7 108.4 n
O8 C8 C9 109.3(3) ?
O8 C8 C7 101.2(3) ?
C9 C8 C7 115.7(3) ?
O8 C8 H8 110.1 n
C9 C8 H8 110.1 n
C7 C8 H8 110.1 n
O10 C9 C91 110.1(3) ?
O10 C9 C8 106.8(3) ?
C91 C9 C8 111.7(3) ?
O10 C9 H9 109.4 n
C91 C9 H9 109.4 n
C8 C9 H9 109.4 n
C12 C11 H11A 109.5 n
C12 C11 H11B 109.5 n
H11A C11 H11B 109.5 n
C12 C11 H11C 109.5 n
H11A C11 H11C 109.5 n
H11B C11 H11C 109.5 n
O7 C12 O8 105.7(3) ?
O7 C12 C13 108.9(3) ?
O8 C12 C13 109.7(3) ?
O7 C12 C11 111.3(3) ?
O8 C12 C11 107.9(3) ?
C13 C12 C11 113.1(3) ?
C12 C13 H13A 109.5 n
C12 C13 H13B 109.5 n
H13A C13 H13B 109.5 n
C12 C13 H13C 109.5 n
H13A C13 H13C 109.5 n
H13B C13 H13C 109.5 n
C9 C91 C92 113.9(3) ?
C9 C91 H91A 108.8 n
C92 C91 H91A 108.8 n
C9 C91 H91B 108.8 n
C92 C91 H91B 108.8 n
H91A C91 H91B 107.7 n
C91 C92 C93 111.8(4) ?
C91 C92 H92A 109.2 n
C93 C92 H92A 109.2 n
C91 C92 H92B 109.2 n
C93 C92 H92B 109.2 n
H92A C92 H92B 107.9 n
C92 C93 H93A 109.5 n
C92 C93 H93B 109.5 n
H93A C93 H93B 109.5 n
C92 C93 H93C 109.5 n
H93A C93 H93C 109.5 n
H93B C93 H93C 109.5 n
C7 O7 C12 106.4(3) ?
C8 O8 C12 107.8(3) ?
C1 O10 C9 116.1(3) ?
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_publ_flag
C1 O1 1.196(5) ?
C1 O10 1.361(5) ?
C1 C2 1.503(6) ?
C2 C3 1.525(5) ?
C2 H2A 0.9900 n
C2 H2B 0.9900 n
C3 C4 1.536(6) ?
C3 H3A 0.9900 n
C3 H3B 0.9900 n
C4 C5 1.500(6) ?
C4 H4A 0.9900 n
C4 H4B 0.9900 n
C5 C6 1.306(6) ?
C5 H5 0.9500 n
C6 C7 1.491(6) ?
C6 H6 0.9500 n
C7 O7 1.417(5) ?
C7 C8 1.539(6) ?
C7 H7 1.0000 n
C8 O8 1.429(5) ?
C8 C9 1.526(6) ?
C8 H8 1.0000 n
C9 O10 1.448(5) ?
C9 C91 1.512(5) ?
C9 H9 1.0000 n
C11 C12 1.518(6) ?
C11 H11A 0.9800 n
C11 H11B 0.9800 n
C11 H11C 0.9800 n
C12 O7 1.418(5) ?
C12 O8 1.455(5) ?
C12 C13 1.512(5) ?
C13 H13A 0.9800 n
C13 H13B 0.9800 n
C13 H13C 0.9800 n
C91 C92 1.520(5) ?
C91 H91A 0.9900 n
C91 H91B 0.9900 n
C92 C93 1.522(5) ?
C92 H92A 0.9900 n
C92 H92B 0.9900 n
C93 H93A 0.9800 n
C93 H93B 0.9800 n
C93 H93C 0.9800 n
