#------------------------------------------------------------------------------
#$Date: 2016-02-18 17:37:37 +0200 (Thu, 18 Feb 2016) $
#$Revision: 176729 $
#$URL: svn://www.crystallography.net/cod/cif/1/51/23/1512385.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_1512385
loop_
_publ_author_name
'Liu, Ya-Ping'
'Lai, Ren'
'Yao, Yong-Gang'
'Zhang, Zhong-Kai'
'Pu, En-Tang'
'Cai, Xiang-Hai'
'Luo, Xiao-Dong'
_publ_section_title
;
 Induced Furoeudesmanes: A Defense Mechanism Against Stress in Laggera
 pterodonta , a Chinese Herbal Plant.
;
_journal_issue                   19
_journal_name_full               'Organic letters'
_journal_page_first              4940
_journal_page_last               4943
_journal_paper_doi               10.1021/ol4024826
_journal_volume                  15
_journal_year                    2013
_chemical_absolute_configuration rm
_chemical_formula_sum            'C20 H28 O5'
_chemical_formula_weight         348.42
_chemical_name_systematic
; 
 ? 
;
_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                   7.3794(10)
_cell_length_b                   12.1840(16)
_cell_length_c                   21.074(3)
_cell_measurement_reflns_used    1923
_cell_measurement_temperature    298(2)
_cell_measurement_theta_max      20.61
_cell_measurement_theta_min      2.56
_cell_volume                     1894.8(4)
_computing_cell_refinement       'Bruker apex-II'
_computing_data_collection       'Bruker apex-II'
_computing_data_reduction        'Bruker SAINT'
_computing_molecular_graphics    'Bruker SHELXTL'
_computing_publication_material  'Bruker SHELXTL'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 1990)'
_diffrn_ambient_temperature      298(2)
_diffrn_measured_fraction_theta_full 0.983
_diffrn_measured_fraction_theta_max 0.963
_diffrn_measurement_device_type  'CCD area detector'
_diffrn_measurement_method       'phi and omega scans'
_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  0.0494
_diffrn_reflns_av_sigmaI/netI    0.0623
_diffrn_reflns_limit_h_max       9
_diffrn_reflns_limit_h_min       -9
_diffrn_reflns_limit_k_max       14
_diffrn_reflns_limit_k_min       -15
_diffrn_reflns_limit_l_max       27
_diffrn_reflns_limit_l_min       -27
_diffrn_reflns_number            13034
_diffrn_reflns_theta_full        28.38
_diffrn_reflns_theta_max         28.38
_diffrn_reflns_theta_min         1.93
_exptl_absorpt_coefficient_mu    0.087
_exptl_absorpt_correction_T_max  0.9880
_exptl_absorpt_correction_T_min  0.9770
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   sadabs
_exptl_crystal_colour            colourless
_exptl_crystal_density_diffrn    1.221
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       block
_exptl_crystal_F_000             752
_exptl_crystal_size_max          0.27
_exptl_crystal_size_mid          0.19
_exptl_crystal_size_min          0.14
_refine_diff_density_max         0.135
_refine_diff_density_min         -0.133
_refine_diff_density_rms         0.032
_refine_ls_abs_structure_details 'None, Friedel Pairs merged'
_refine_ls_abs_structure_Flack   1.9(14)
_refine_ls_extinction_coef       0.0046(11)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc²λ³/sin(2θ)]^-1/4^
_refine_ls_extinction_method     SHELXL
_refine_ls_goodness_of_fit_ref   0.999
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     233
_refine_ls_number_reflns         4465
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      0.999
_refine_ls_R_factor_all          0.1189
_refine_ls_R_factor_gt           0.0510
_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)+(0.0509P)²+0.0000P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0998
_refine_ls_wR_factor_ref         0.1244
_reflns_number_gt                2338
_reflns_number_total             4465
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            ol4024826_si_002.cif
_cod_data_source_block           101027b
_cod_depositor_comments
;
The following automatic conversions were performed:

'_symmetry_cell_setting' value 'Orthorhombic' changed to
'orthorhombic' according to
/home/saulius/struct/CIF-dictionaries/cif_core.dic dictionary named
'cif_core.dic' version 2.4.2 from 2011-04-26.

Automatic conversion script
Id: cif_fix_values 1891 2012-01-12 08:04:46Z andrius 
;
_cod_original_sg_symbol_H-M      P2(1)2(1)2(1)
_cod_database_code               1512385
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
O1 O 0.8379(3) 0.74089(16) 1.00155(8) 0.0771(6) Uani 1 1 d .
O2 O 0.7475(4) 0.51113(17) 0.99481(10) 0.1140(9) Uani 1 1 d .
O3 O 0.9264(3) 0.72262(13) 0.90027(7) 0.0604(5) Uani 1 1 d .
O4 O 1.2617(3) 0.76433(15) 0.86088(7) 0.0674(6) Uani 1 1 d .
H4 H 1.2885 0.7722 0.8984 0.101 Uiso 1 1 calc R
O5 O 0.9082(3) 0.72150(16) 0.59533(8) 0.0777(6) Uani 1 1 d .
C1 C 0.7363(4) 0.8605(2) 0.80794(13) 0.0677(8) Uani 1 1 d .
H1A H 0.6358 0.9065 0.7948 0.081 Uiso 1 1 calc R
H1B H 0.6905 0.7864 0.8130 0.081 Uiso 1 1 calc R
C2 C 0.8045(4) 0.9008(2) 0.87157(12) 0.0645(8) Uani 1 1 d .
H2A H 0.7096 0.8919 0.9030 0.077 Uiso 1 1 calc R
H2B H 0.8323 0.9785 0.8685 0.077 Uiso 1 1 calc R
C3 C 0.9723(4) 0.83944(19) 0.89328(11) 0.0518(7) Uani 1 1 d .
H3 H 1.0153 0.8692 0.9338 0.062 Uiso 1 1 calc R
C4 C 1.1246(4) 0.84289(19) 0.84374(10) 0.0497(7) Uani 1 1 d .
C5 C 1.0534(3) 0.8025(2) 0.77910(9) 0.0437(6) Uani 1 1 d .
H5 H 1.0171 0.7262 0.7865 0.052 Uiso 1 1 calc R
C6 C 1.2039(4) 0.7958(2) 0.72862(10) 0.0543(7) Uani 1 1 d .
H6A H 1.2589 0.8675 0.7231 0.065 Uiso 1 1 calc R
H6B H 1.2972 0.7451 0.7425 0.065 Uiso 1 1 calc R
C7 C 1.1251(4) 0.75735(19) 0.66664(11) 0.0541(7) Uani 1 1 d .
C8 C 0.9470(5) 0.7597(2) 0.65550(11) 0.0605(8) Uani 1 1 d .
C9 C 0.8004(4) 0.7924(2) 0.69901(12) 0.0672(8) Uani 1 1 d .
H9A H 0.7401 0.7275 0.7153 0.081 Uiso 1 1 calc R
H9B H 0.7117 0.8360 0.6763 0.081 Uiso 1 1 calc R
C10 C 0.8791(4) 0.8604(2) 0.75525(11) 0.0540(7) Uani 1 1 d .
C11 C 1.2114(5) 0.7135(2) 0.61027(12) 0.0650(8) Uani 1 1 d .
C12 C 1.0734(6) 0.6940(2) 0.56975(14) 0.0821(10) Uani 1 1 d .
H12 H 1.0884 0.6652 0.5292 0.098 Uiso 1 1 calc R
C13 C 1.4091(5) 0.6933(3) 0.60010(14) 0.0894(11) Uani 1 1 d .
H13A H 1.4275 0.6617 0.5589 0.134 Uiso 1 1 calc R
H13B H 1.4531 0.6437 0.6320 0.134 Uiso 1 1 calc R
H13C H 1.4738 0.7614 0.6029 0.134 Uiso 1 1 calc R
C14 C 0.9124(5) 0.9786(2) 0.73093(13) 0.0734(9) Uani 1 1 d .
H14A H 0.8038 1.0061 0.7115 0.110 Uiso 1 1 calc R
H14B H 1.0086 0.9780 0.7003 0.110 Uiso 1 1 calc R
H14C H 0.9453 1.0249 0.7659 0.110 Uiso 1 1 calc R
C15 C 1.2108(4) 0.9568(2) 0.84509(12) 0.0653(8) Uani 1 1 d .
H15A H 1.3026 0.9613 0.8129 0.098 Uiso 1 1 calc R
H15B H 1.2644 0.9693 0.8860 0.098 Uiso 1 1 calc R
H15C H 1.1196 1.0113 0.8372 0.098 Uiso 1 1 calc R
C1' C 0.8750(4) 0.6852(2) 0.95624(11) 0.0578(7) Uani 1 1 d .
C2' C 0.8771(5) 0.5619(2) 0.95464(11) 0.0630(8) Uani 1 1 d .
C3' C 0.7235(5) 0.5039(3) 0.92613(16) 0.0857(10) Uani 1 1 d .
H3' H 0.7528 0.4323 0.9076 0.103 Uiso 1 1 calc R
C4' C 0.5640(5) 0.5588(3) 0.8986(3) 0.1335(18) Uani 1 1 d .
H4'1 H 0.5812 0.5676 0.8537 0.200 Uiso 1 1 calc R
H4'2 H 0.5490 0.6296 0.9180 0.200 Uiso 1 1 calc R
H4'3 H 0.4580 0.5151 0.9062 0.200 Uiso 1 1 calc R
C5' C 1.0642(5) 0.5146(3) 0.95467(14) 0.0867(11) Uani 1 1 d .
H5'1 H 1.0572 0.4362 0.9509 0.130 Uiso 1 1 calc R
H5'2 H 1.1241 0.5335 0.9936 0.130 Uiso 1 1 calc R
H5'3 H 1.1313 0.5439 0.9195 0.130 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
C2' O2 C3' 61.12(17)
C1' O3 C3 119.33(18)
C4 O4 H4 109.5
C12 O5 C8 105.0(2)
C2 C1 C10 114.5(2)
C2 C1 H1A 108.6
C10 C1 H1A 108.6
C2 C1 H1B 108.6
C10 C1 H1B 108.6
H1A C1 H1B 107.6
C1 C2 C3 112.2(2)
C1 C2 H2A 109.2
C3 C2 H2A 109.2
C1 C2 H2B 109.2
C3 C2 H2B 109.2
H2A C2 H2B 107.9
O3 C3 C2 108.7(2)
O3 C3 C4 105.25(18)
C2 C3 C4 112.27(19)
O3 C3 H3 110.2
C2 C3 H3 110.2
C4 C3 H3 110.2
O4 C4 C15 107.9(2)
O4 C4 C3 109.03(18)
C15 C4 C3 108.5(2)
O4 C4 C5 104.43(18)
C15 C4 C5 116.7(2)
C3 C4 C5 110.1(2)
C6 C5 C4 112.4(2)
C6 C5 C10 113.46(19)
C4 C5 C10 115.1(2)
C6 C5 H5 104.9
C4 C5 H5 104.9
C10 C5 H5 104.9
C7 C6 C5 109.7(2)
C7 C6 H6A 109.7
C5 C6 H6A 109.7
C7 C6 H6B 109.7
C5 C6 H6B 109.7
H6A C6 H6B 108.2
C8 C7 C11 107.2(2)
C8 C7 C6 121.8(2)
C11 C7 C6 131.0(3)
C7 C8 O5 111.0(3)
C7 C8 C9 128.2(2)
O5 C8 C9 120.7(3)
C8 C9 C10 110.1(2)
C8 C9 H9A 109.6
C10 C9 H9A 109.6
C8 C9 H9B 109.6
C10 C9 H9B 109.6
H9A C9 H9B 108.2
C1 C10 C14 110.4(2)
C1 C10 C5 109.6(2)
C14 C10 C5 113.5(2)
C1 C10 C9 107.2(2)
C14 C10 C9 107.6(2)
C5 C10 C9 108.3(2)
C12 C11 C7 104.6(3)
C12 C11 C13 128.0(3)
C7 C11 C13 127.3(3)
C11 C12 O5 112.2(3)
C11 C12 H12 123.9
O5 C12 H12 123.9
C11 C13 H13A 109.5
C11 C13 H13B 109.5
H13A C13 H13B 109.5
C11 C13 H13C 109.5
H13A C13 H13C 109.5
H13B C13 H13C 109.5
C10 C14 H14A 109.5
C10 C14 H14B 109.5
H14A C14 H14B 109.5
C10 C14 H14C 109.5
H14A C14 H14C 109.5
H14B C14 H14C 109.5
C4 C15 H15A 109.5
C4 C15 H15B 109.5
H15A C15 H15B 109.5
C4 C15 H15C 109.5
H15A C15 H15C 109.5
H15B C15 H15C 109.5
O1 C1' O3 125.5(2)
O1 C1' C2' 125.7(2)
O3 C1' C2' 108.8(2)
O2 C2' C3' 60.8(2)
O2 C2' C5' 117.0(3)
C3' C2' C5' 121.9(2)
O2 C2' C1' 114.5(2)
C3' C2' C1' 118.9(3)
C5' C2' C1' 113.2(3)
O2 C3' C2' 58.04(19)
O2 C3' C4' 117.3(3)
C2' C3' C4' 124.1(3)
O2 C3' H3' 115.0
C2' C3' H3' 115.0
C4' C3' H3' 115.0
C3' C4' H4'1 109.5
C3' C4' H4'2 109.5
H4'1 C4' H4'2 109.5
C3' C4' H4'3 109.5
H4'1 C4' H4'3 109.5
H4'2 C4' H4'3 109.5
C2' C5' H5'1 109.5
C2' C5' H5'2 109.5
H5'1 C5' H5'2 109.5
C2' C5' H5'3 109.5
H5'1 C5' H5'3 109.5
H5'2 C5' H5'3 109.5
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
O1 C1' 1.203(3)
O2 C2' 1.419(3)
O2 C3' 1.461(4)
O3 C1' 1.320(3)
O3 C3 1.470(3)
O4 C4 1.439(3)
O4 H4 0.8200
O5 C12 1.374(4)
O5 C8 1.381(3)
C1 C2 1.514(4)
C1 C10 1.531(4)
C1 H1A 0.9700
C1 H1B 0.9700
C2 C3 1.517(4)
C2 H2A 0.9700
C2 H2B 0.9700
C3 C4 1.535(3)
C3 H3 0.9800
C4 C15 1.527(3)
C4 C5 1.541(3)
C5 C6 1.540(3)
C5 C10 1.551(3)
C5 H5 0.9800
C6 C7 1.505(3)
C6 H6A 0.9700
C6 H6B 0.9700
C7 C8 1.335(4)
C7 C11 1.450(4)
C8 C9 1.473(4)
C9 C10 1.559(3)
C9 H9A 0.9700
C9 H9B 0.9700
C10 C14 1.547(4)
C11 C12 1.350(4)
C11 C13 1.496(5)
C12 H12 0.9300
C13 H13A 0.9600
C13 H13B 0.9600
C13 H13C 0.9600
C14 H14A 0.9600
C14 H14B 0.9600
C14 H14C 0.9600
C15 H15A 0.9600
C15 H15B 0.9600
C15 H15C 0.9600
C1' C2' 1.503(4)
C2' C3' 1.465(4)
C2' C5' 1.496(4)
C3' C4' 1.473(5)
C3' H3' 0.9800
C4' H4'1 0.9600
C4' H4'2 0.9600
C4' H4'3 0.9600
C5' H5'1 0.9600
C5' H5'2 0.9600
C5' H5'3 0.9600
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
C10 C1 C2 C3 -53.6(3)
C1' O3 C3 C2 -93.3(3)
C1' O3 C3 C4 146.2(2)
C1 C2 C3 O3 -61.2(3)
C1 C2 C3 C4 54.8(3)
O3 C3 C4 O4 -49.4(2)
C2 C3 C4 O4 -167.47(19)
O3 C3 C4 C15 -166.7(2)
C2 C3 C4 C15 75.3(3)
O3 C3 C4 C5 64.6(2)
C2 C3 C4 C5 -53.5(3)
O4 C4 C5 C6 -58.8(2)
C15 C4 C5 C6 60.2(3)
C3 C4 C5 C6 -175.68(19)
O4 C4 C5 C10 169.24(19)
C15 C4 C5 C10 -71.8(3)
C3 C4 C5 C10 52.3(3)
C4 C5 C6 C7 -179.3(2)
C10 C5 C6 C7 -46.5(3)
C5 C6 C7 C8 16.6(3)
C5 C6 C7 C11 -163.4(2)
C11 C7 C8 O5 -0.6(3)
C6 C7 C8 O5 179.3(2)
C11 C7 C8 C9 176.9(3)
C6 C7 C8 C9 -3.2(4)
C12 O5 C8 C7 0.6(3)
C12 O5 C8 C9 -177.1(2)
C7 C8 C9 C10 17.9(4)
O5 C8 C9 C10 -164.8(2)
C2 C1 C10 C14 -76.0(3)
C2 C1 C10 C5 49.7(3)
C2 C1 C10 C9 167.0(2)
C6 C5 C10 C1 178.6(2)
C4 C5 C10 C1 -49.9(3)
C6 C5 C10 C14 -57.4(3)
C4 C5 C10 C14 74.1(3)
C6 C5 C10 C9 62.0(3)
C4 C5 C10 C9 -166.5(2)
C8 C9 C10 C1 -162.5(2)
C8 C9 C10 C14 78.7(3)
C8 C9 C10 C5 -44.3(3)
C8 C7 C11 C12 0.4(3)
C6 C7 C11 C12 -179.6(3)
C8 C7 C11 C13 -178.9(3)
C6 C7 C11 C13 1.2(4)
C7 C11 C12 O5 0.0(3)
C13 C11 C12 O5 179.3(3)
C8 O5 C12 C11 -0.4(3)
C3 O3 C1' O1 10.6(4)
C3 O3 C1' C2' -167.3(2)
C3' O2 C2' C5' -113.3(3)
C3' O2 C2' C1' 110.7(3)
O1 C1' C2' O2 32.4(5)
O3 C1' C2' O2 -149.7(3)
O1 C1' C2' C3' 101.3(4)
O3 C1' C2' C3' -80.8(3)
O1 C1' C2' C5' -105.3(3)
O3 C1' C2' C5' 72.6(3)
C2' O2 C3' C4' -114.9(3)
C5' C2' C3' O2 105.4(3)
C1' C2' C3' O2 -103.6(3)
O2 C2' C3' C4' 103.4(4)
C5' C2' C3' C4' -151.2(3)
C1' C2' C3' C4' -0.2(4)
