#------------------------------------------------------------------------------
#$Date: 2016-03-21 17:29:04 +0200 (Mon, 21 Mar 2016) $
#$Revision: 178784 $
#$URL: svn://www.crystallography.net/cod/cif/4/10/38/4103870.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_4103870
loop_
_publ_author_name
'Scott A. Snyder'
'Ferenc Kontes'
_publ_section_title
;
 Explorations into Neolignan Biosynthesis: Concise Total Syntheses of
 Helicterin B, Helisorin, and Helisterculin A from a Common Intermediate
;
_journal_name_full               'Journal of the American Chemical Society'
_journal_page_first              1745
_journal_page_last               1752
_journal_paper_doi               10.1021/ja806865u
_journal_volume                  131
_journal_year                    2009
_chemical_formula_sum            'C22 H25 O8'
_chemical_formula_weight         417.42
_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                70.152(4)
_cell_angle_beta                 81.717(4)
_cell_angle_gamma                81.656(4)
_cell_formula_units_Z            2
_cell_length_a                   8.224(2)
_cell_length_b                   10.543(3)
_cell_length_c                   12.410(3)
_cell_measurement_reflns_used    2455
_cell_measurement_temperature    125(2)
_cell_measurement_theta_max      30.37
_cell_measurement_theta_min      2.52
_cell_volume                     996.2(4)
_computing_cell_refinement       'Bruker SMART'
_computing_data_collection       'Bruker SMART'
_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      125(2)
_diffrn_measured_fraction_theta_full 0.991
_diffrn_measured_fraction_theta_max 0.991
_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  0.0987
_diffrn_reflns_av_sigmaI/netI    0.1586
_diffrn_reflns_limit_h_max       11
_diffrn_reflns_limit_h_min       -11
_diffrn_reflns_limit_k_max       15
_diffrn_reflns_limit_k_min       -15
_diffrn_reflns_limit_l_max       17
_diffrn_reflns_limit_l_min       -17
_diffrn_reflns_number            15972
_diffrn_reflns_theta_full        30.58
_diffrn_reflns_theta_max         30.58
_diffrn_reflns_theta_min         1.75
_exptl_absorpt_coefficient_mu    0.106
_exptl_absorpt_correction_T_max  0.9947
_exptl_absorpt_correction_T_min  0.9843
_exptl_absorpt_correction_type   empirical
_exptl_absorpt_process_details   SADABS
_exptl_crystal_colour            colorless
_exptl_crystal_density_diffrn    1.392
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       plate
_exptl_crystal_F_000             442
_exptl_crystal_size_max          0.15
_exptl_crystal_size_mid          0.05
_exptl_crystal_size_min          0.05
_refine_diff_density_max         0.550
_refine_diff_density_min         -0.688
_refine_diff_density_rms         0.070
_refine_ls_extinction_coef       0.0042(16)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc²λ³/sin(2θ)]^-1/4^
_refine_ls_extinction_method     SHELXL
_refine_ls_goodness_of_fit_ref   1.010
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     272
_refine_ls_number_reflns         6069
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.010
_refine_ls_R_factor_all          0.1891
_refine_ls_R_factor_gt           0.0641
_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)+(0.0500P)²+0.0000P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1234
_refine_ls_wR_factor_ref         0.1585
_reflns_number_gt                2470
_reflns_number_total             6069
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            ja806865u_si_006.cif
_cod_data_source_block           ky80as10
_cod_depositor_comments
;
The following automatic conversions were performed:

'_refine_ls_hydrogen_treatment' value 'CONSTR' changed to 'constr'
according to the built-in table from CIF Core dictionary named
'cif_core.dic' version 2.4.1 from 2010-06-29.

Automatic conversion script
Id: cif_fix_values 1715 2011-07-08 13:25:40Z adriana 
;
_cod_database_code               4103870
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
O1 O 0.2388(2) 1.05288(18) 0.00898(15) 0.0257(5) Uani 1 1 d .
H1A H 0.3246 1.0732 -0.0361 0.038 Uiso 1 1 calc R
O2 O 0.4890(2) 0.88025(19) 0.15372(16) 0.0296(5) Uani 1 1 d .
O3 O -0.1257(3) 1.37614(19) 0.45397(17) 0.0377(6) Uani 1 1 d .
O4 O -0.2038(3) 1.49525(19) 0.27873(17) 0.0356(6) Uani 1 1 d .
O5 O -0.2176(2) 0.90727(19) 0.36324(17) 0.0352(5) Uani 1 1 d .
O6 O -0.2528(2) 1.08150(18) 0.20098(16) 0.0256(5) Uani 1 1 d .
O7 O 0.3419(2) 0.35242(17) 0.29556(15) 0.0250(5) Uani 1 1 d .
O8 O 0.3300(3) 0.39491(18) 0.07939(16) 0.0298(5) Uani 1 1 d .
C1 C 0.2618(3) 1.0564(3) 0.1187(2) 0.0208(6) Uani 1 1 d .
H1B H 0.3242 1.1348 0.1093 0.025 Uiso 1 1 calc R
C2 C 0.3556(3) 0.9253(3) 0.1889(2) 0.0207(6) Uani 1 1 d .
C3 C 0.2612(3) 0.8566(3) 0.3030(2) 0.0202(6) Uani 1 1 d .
H3A H 0.3282 0.7757 0.3510 0.024 Uiso 1 1 calc R
C4 C 0.1014(3) 0.8165(2) 0.2715(2) 0.0193(6) Uani 1 1 d .
H4A H 0.0334 0.7746 0.3455 0.023 Uiso 1 1 calc R
C5 C -0.0008(3) 0.9474(2) 0.2035(2) 0.0181(6) Uani 1 1 d .
H5A H -0.0167 0.9419 0.1269 0.022 Uiso 1 1 calc R
C6 C 0.0934(3) 1.0728(2) 0.1853(2) 0.0186(6) Uani 1 1 d .
H6A H 0.0279 1.1585 0.1430 0.022 Uiso 1 1 calc R
C7 C 0.1192(3) 1.0734(3) 0.3032(2) 0.0200(6) Uani 1 1 d .
C8 C 0.2083(3) 0.9601(3) 0.3633(2) 0.0219(6) Uani 1 1 d .
H8A H 0.1421 0.9170 0.4367 0.026 Uiso 1 1 calc R
H8B H 0.3083 0.9865 0.3826 0.026 Uiso 1 1 calc R
C9 C 0.0428(3) 1.1779(3) 0.3516(2) 0.0213(6) Uani 1 1 d .
H9A H 0.0613 1.1661 0.4284 0.026 Uiso 1 1 calc R
C10 C -0.0516(4) 1.2893(3) 0.2969(2) 0.0249(7) Uani 1 1 d .
H10A H -0.0697 1.3053 0.2192 0.030 Uiso 1 1 calc R
C11 C -0.1280(3) 1.3877(3) 0.3545(2) 0.0240(6) Uani 1 1 d .
C12 C -0.2784(4) 1.6029(3) 0.3223(3) 0.0436(9) Uani 1 1 d .
H12A H -0.3305 1.6762 0.2609 0.065 Uiso 1 1 calc R
H12B H -0.1933 1.6376 0.3492 0.065 Uiso 1 1 calc R
H12C H -0.3621 1.5680 0.3865 0.065 Uiso 1 1 calc R
C13 C -0.1678(3) 0.9707(3) 0.2675(2) 0.0212(6) Uani 1 1 d .
C14 C -0.4011(4) 1.1323(3) 0.2568(3) 0.0319(7) Uani 1 1 d .
H14A H -0.4550 1.2113 0.2008 0.048 Uiso 1 1 calc R
H14B H -0.3730 1.1588 0.3197 0.048 Uiso 1 1 calc R
H14C H -0.4764 1.0614 0.2878 0.048 Uiso 1 1 calc R
C15 C 0.1496(3) 0.7084(2) 0.2130(2) 0.0197(6) Uani 1 1 d .
C16 C 0.2133(3) 0.5796(3) 0.2819(2) 0.0202(6) Uani 1 1 d .
H16A H 0.2150 0.5621 0.3620 0.024 Uiso 1 1 calc R
C17 C 0.2729(3) 0.4787(3) 0.2351(2) 0.0211(6) Uani 1 1 d .
C18 C 0.2667(4) 0.5014(3) 0.1181(2) 0.0245(6) Uani 1 1 d .
C19 C 0.2040(4) 0.6272(3) 0.0500(2) 0.0290(7) Uani 1 1 d .
H19A H 0.1996 0.6436 -0.0297 0.035 Uiso 1 1 calc R
C20 C 0.1467(4) 0.7309(3) 0.0970(2) 0.0268(7) Uani 1 1 d .
H20A H 0.1055 0.8174 0.0487 0.032 Uiso 1 1 calc R
C21 C 0.3480(4) 0.3257(3) 0.4158(2) 0.0308(7) Uani 1 1 d .
H21A H 0.4000 0.2334 0.4500 0.046 Uiso 1 1 calc R
H21B H 0.2356 0.3345 0.4533 0.046 Uiso 1 1 calc R
H21C H 0.4127 0.3907 0.4266 0.046 Uiso 1 1 calc R
C22 C 0.3178(4) 0.4150(3) -0.0395(2) 0.0353(8) Uani 1 1 d .
H22A H 0.3658 0.3329 -0.0575 0.053 Uiso 1 1 calc R
H22B H 0.3778 0.4917 -0.0880 0.053 Uiso 1 1 calc R
H22C H 0.2013 0.4340 -0.0542 0.053 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
C11 O4 C12 115.7(2)
C13 O6 C14 115.9(2)
C17 O7 C21 116.4(2)
C18 O8 C22 116.4(2)
O1 C1 C6 109.1(2)
O1 C1 C2 111.5(2)
C6 C1 C2 107.7(2)
O2 C2 C3 124.4(2)
O2 C2 C1 122.8(2)
C3 C2 C1 112.7(2)
C8 C3 C2 107.9(2)
C8 C3 C4 108.0(2)
C2 C3 C4 105.3(2)
C15 C4 C5 116.3(2)
C15 C4 C3 109.7(2)
C5 C4 C3 108.8(2)
C13 C5 C4 112.3(2)
C13 C5 C6 106.78(19)
C4 C5 C6 109.5(2)
C7 C6 C1 108.7(2)
C7 C6 C5 107.1(2)
C1 C6 C5 109.2(2)
C8 C7 C9 123.1(3)
C8 C7 C6 112.8(2)
C9 C7 C6 123.8(2)
C7 C8 C3 115.3(2)
C10 C9 C7 125.3(3)
C9 C10 C11 121.4(3)
O3 C11 O4 123.8(2)
O3 C11 C10 126.6(3)
O4 C11 C10 109.7(2)
O5 C13 O6 123.6(3)
O5 C13 C5 127.3(2)
O6 C13 C5 109.0(2)
C20 C15 C16 118.4(2)
C20 C15 C4 124.8(2)
C16 C15 C4 116.7(2)
C17 C16 C15 121.2(2)
O7 C17 C16 124.7(2)
O7 C17 C18 115.1(2)
C16 C17 C18 120.2(2)
O8 C18 C19 125.1(2)
O8 C18 C17 115.9(2)
C19 C18 C17 119.0(2)
C18 C19 C20 120.9(3)
C15 C20 C19 120.4(2)
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
O1 C1 1.415(3)
O2 C2 1.213(3)
O3 C11 1.201(3)
O4 C11 1.341(3)
O4 C12 1.441(3)
O5 C13 1.195(3)
O6 C13 1.345(3)
O6 C14 1.440(3)
O7 C17 1.371(3)
O7 C21 1.428(3)
O8 C18 1.373(3)
O8 C22 1.434(3)
C1 C6 1.526(4)
C1 C2 1.527(4)
C2 C3 1.511(4)
C3 C8 1.504(4)
C3 C4 1.574(4)
C4 C15 1.528(3)
C4 C5 1.549(3)
C5 C13 1.516(4)
C5 C6 1.562(3)
C6 C7 1.510(4)
C7 C8 1.349(3)
C7 C9 1.452(4)
C9 C10 1.338(4)
C10 C11 1.472(4)
C15 C20 1.380(3)
C15 C16 1.408(3)
C16 C17 1.377(3)
C17 C18 1.397(4)
C18 C19 1.380(4)
C19 C20 1.401(4)
