#------------------------------------------------------------------------------
#$Date: 2016-03-21 17:29:04 +0200 (Mon, 21 Mar 2016) $
#$Revision: 178784 $
#$URL: svn://www.crystallography.net/cod/cif/4/10/38/4103869.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_4103869
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            'C24 H28 O9'
_chemical_formula_weight         460.46
_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                65.243(2)
_cell_angle_beta                 65.777(2)
_cell_angle_gamma                81.552(2)
_cell_formula_units_Z            2
_cell_length_a                   10.4583(12)
_cell_length_b                   10.8459(12)
_cell_length_c                   11.8553(13)
_cell_measurement_reflns_used    7330
_cell_measurement_temperature    125(2)
_cell_measurement_theta_max      0.00
_cell_measurement_theta_min      0.00
_cell_volume                     1113.1(2)
_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 0.929
_diffrn_measured_fraction_theta_max 0.929
_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  0.0213
_diffrn_reflns_av_sigmaI/netI    0.0266
_diffrn_reflns_limit_h_max       15
_diffrn_reflns_limit_h_min       -15
_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            18902
_diffrn_reflns_theta_full        32.40
_diffrn_reflns_theta_max         32.40
_diffrn_reflns_theta_min         2.05
_exptl_absorpt_coefficient_mu    0.105
_exptl_absorpt_correction_T_max  0.9844
_exptl_absorpt_correction_T_min  0.9621
_exptl_absorpt_correction_type   empirical
_exptl_absorpt_process_details   sadabs
_exptl_crystal_colour            colorless
_exptl_crystal_density_diffrn    1.374
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       block
_exptl_crystal_F_000             488
_exptl_crystal_size_max          0.37
_exptl_crystal_size_mid          0.17
_exptl_crystal_size_min          0.15
_refine_diff_density_max         0.531
_refine_diff_density_min         -0.377
_refine_diff_density_rms         0.064
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.051
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     298
_refine_ls_number_reflns         7424
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.051
_refine_ls_R_factor_all          0.0639
_refine_ls_R_factor_gt           0.0492
_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)+(0.1400P)²+0.0000P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1681
_refine_ls_wR_factor_ref         0.1897
_reflns_number_gt                5810
_reflns_number_total             7424
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            ja806865u_si_005.cif
_cod_data_source_block           syn2s10
_cod_database_code               4103869
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 0.58699(11) 0.64142(10) 0.33240(10) 0.0274(2) Uani 1 1 d .
O2 O 0.49626(9) 0.81577(9) 0.49228(9) 0.01975(19) Uani 1 1 d .
O3 O 0.67689(9) 0.90264(8) 0.28001(8) 0.01731(18) Uani 1 1 d .
O4 O 0.92249(11) 0.82340(16) 0.55691(12) 0.0443(3) Uani 1 1 d .
O5 O 1.10000(12) 0.74394(16) 0.42520(15) 0.0479(4) Uani 1 1 d .
O6 O 0.54881(12) 0.62451(10) 1.02248(9) 0.0289(2) Uani 1 1 d .
O7 O 0.50001(11) 0.84594(10) 0.95479(9) 0.0265(2) Uani 1 1 d .
O8 O 0.96814(10) 0.85596(9) -0.10738(9) 0.0235(2) Uani 1 1 d .
O9 O 1.15828(10) 0.68259(9) -0.16398(9) 0.0219(2) Uani 1 1 d .
C1 C 0.64895(13) 0.66488(12) 0.38776(12) 0.0180(2) Uani 1 1 d .
C2 C 0.63363(11) 0.79904(11) 0.41004(11) 0.0155(2) Uani 1 1 d .
C3 C 0.72510(11) 0.78882(11) 0.48752(11) 0.0145(2) Uani 1 1 d .
H3A H 0.7152 0.8706 0.5089 0.017 Uiso 1 1 calc R
C4 C 0.87932(12) 0.77380(11) 0.39997(11) 0.0153(2) Uani 1 1 d .
H4A H 0.9045 0.8517 0.3100 0.018 Uiso 1 1 calc R
C5 C 0.89643(12) 0.63956(12) 0.37694(11) 0.0172(2) Uani 1 1 d .
H5A H 0.9540 0.5786 0.4271 0.021 Uiso 1 1 calc R
C6 C 0.74723(13) 0.56843(12) 0.44621(12) 0.0181(2) Uani 1 1 d .
H6A H 0.7521 0.4807 0.4361 0.022 Uiso 1 1 calc R
C7 C 0.68967(13) 0.54721(12) 0.59218(12) 0.0193(2) Uani 1 1 d .
H7A H 0.6631 0.4597 0.6631 0.023 Uiso 1 1 calc R
C8 C 0.67828(12) 0.65990(11) 0.61598(11) 0.0162(2) Uani 1 1 d .
C9 C 0.62748(12) 0.65465(12) 0.75159(11) 0.0181(2) Uani 1 1 d .
H9A H 0.6060 0.5668 0.8226 0.022 Uiso 1 1 calc R
C10 C 0.60741(13) 0.75939(12) 0.78804(12) 0.0194(2) Uani 1 1 d .
H10A H 0.6292 0.8496 0.7216 0.023 Uiso 1 1 calc R
C11 C 0.55098(13) 0.73315(12) 0.93276(12) 0.0194(2) Uani 1 1 d .
C12 C 0.43253(18) 0.82414(16) 1.09626(14) 0.0330(3) Uani 1 1 d .
H12A H 0.3986 0.9106 1.1039 0.050 Uiso 1 1 calc R
H12B H 0.5002 0.7878 1.1391 0.050 Uiso 1 1 calc R
H12C H 0.3533 0.7593 1.1412 0.050 Uiso 1 1 calc R
C13 C 0.39136(13) 0.83245(15) 0.43862(14) 0.0261(3) Uani 1 1 d .
H13A H 0.2998 0.8434 0.5035 0.039 Uiso 1 1 calc R
H13B H 0.3875 0.7522 0.4219 0.039 Uiso 1 1 calc R
H13C H 0.4151 0.9132 0.3539 0.039 Uiso 1 1 calc R
C14 C 0.68387(14) 1.03725(12) 0.27341(13) 0.0211(2) Uani 1 1 d .
H14A H 0.7149 1.1024 0.1792 0.032 Uiso 1 1 calc R
H14B H 0.7506 1.0398 0.3112 0.032 Uiso 1 1 calc R
H14C H 0.5909 1.0611 0.3253 0.032 Uiso 1 1 calc R
C15 C 0.98096(13) 0.77782(13) 0.46026(12) 0.0197(2) Uani 1 1 d .
C16 C 1.00652(19) 0.8208(3) 0.6293(2) 0.0610(7) Uani 1 1 d .
H16A H 0.9525 0.8564 0.6984 0.092 Uiso 1 1 calc R
H16B H 1.0920 0.8770 0.5662 0.092 Uiso 1 1 calc R
H16C H 1.0318 0.7271 0.6724 0.092 Uiso 1 1 calc R
C17 C 0.97116(12) 0.65456(12) 0.23204(12) 0.0176(2) Uani 1 1 d .
C18 C 0.93505(12) 0.75426(12) 0.12873(12) 0.0177(2) Uani 1 1 d .
H18A H 0.8659 0.8177 0.1486 0.021 Uiso 1 1 calc R
C19 C 0.99879(12) 0.76161(12) -0.00202(12) 0.0171(2) Uani 1 1 d .
C20 C 1.10179(12) 0.66781(12) -0.03265(11) 0.0178(2) Uani 1 1 d .
C21 C 1.13890(14) 0.57048(13) 0.06882(13) 0.0223(2) Uani 1 1 d .
H21A H 1.2091 0.5077 0.0490 0.027 Uiso 1 1 calc R
C22 C 1.07347(13) 0.56401(13) 0.20062(12) 0.0218(2) Uani 1 1 d .
H22A H 1.0996 0.4965 0.2696 0.026 Uiso 1 1 calc R
C23 C 0.85437(15) 0.94199(15) -0.07595(14) 0.0291(3) Uani 1 1 d .
H23A H 0.8422 1.0046 -0.1588 0.044 Uiso 1 1 calc R
H23B H 0.8743 0.9941 -0.0342 0.044 Uiso 1 1 calc R
H23C H 0.7683 0.8865 -0.0132 0.044 Uiso 1 1 calc R
C24 C 1.25473(15) 0.58150(14) -0.19439(13) 0.0249(3) Uani 1 1 d .
H24A H 1.2886 0.6019 -0.2908 0.037 Uiso 1 1 calc R
H24B H 1.2072 0.4919 -0.1421 0.037 Uiso 1 1 calc R
H24C H 1.3343 0.5816 -0.1710 0.037 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 C13 116.01(9)
C2 O3 C14 115.28(9)
C15 O4 C16 116.72(13)
C11 O7 C12 114.39(10)
C19 O8 C23 116.87(10)
C20 O9 C24 116.35(9)
O1 C1 C6 124.77(11)
O1 C1 C2 123.14(11)
C6 C1 C2 112.07(9)
O2 C2 O3 112.15(9)
O2 C2 C3 105.66(9)
O3 C2 C3 114.23(9)
O2 C2 C1 112.43(9)
O3 C2 C1 104.85(9)
C3 C2 C1 107.58(9)
C8 C3 C2 107.38(9)
C8 C3 C4 108.35(9)
C2 C3 C4 108.18(9)
C15 C4 C3 112.59(9)
C15 C4 C5 109.75(9)
C3 C4 C5 110.68(9)
C17 C5 C4 115.66(9)
C17 C5 C6 112.40(9)
C4 C5 C6 107.90(9)
C7 C6 C1 105.61(10)
C7 C6 C5 107.45(9)
C1 C6 C5 109.25(9)
C8 C7 C6 115.77(10)
C7 C8 C9 121.88(10)
C7 C8 C3 113.05(10)
C9 C8 C3 125.07(10)
C10 C9 C8 127.37(11)
C9 C10 C11 119.23(11)
O6 C11 O7 122.89(11)
O6 C11 C10 125.25(11)
O7 C11 C10 111.86(10)
O5 C15 O4 123.44(12)
O5 C15 C4 124.49(12)
O4 C15 C4 112.08(10)
C22 C17 C18 118.65(11)
C22 C17 C5 119.65(10)
C18 C17 C5 121.64(10)
C19 C18 C17 120.92(10)
O8 C19 C18 123.90(10)
O8 C19 C20 116.13(10)
C18 C19 C20 119.97(10)
O9 C20 C21 125.01(11)
O9 C20 C19 115.80(10)
C21 C20 C19 119.19(10)
C20 C21 C22 120.26(11)
C17 C22 C21 121.01(11)
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
O1 C1 1.2052(15)
O2 C2 1.4034(14)
O2 C13 1.4349(15)
O3 C2 1.4036(13)
O3 C14 1.4401(14)
O4 C15 1.3198(16)
O4 C16 1.4495(19)
O5 C15 1.1944(16)
O6 C11 1.2077(15)
O7 C11 1.3456(15)
O7 C12 1.4534(16)
O8 C19 1.3681(14)
O8 C23 1.4235(16)
O9 C20 1.3649(14)
O9 C24 1.4343(15)
C1 C6 1.5141(17)
C1 C2 1.5592(16)
C2 C3 1.5414(15)
C3 C8 1.5231(15)
C3 C4 1.5480(16)
C4 C15 1.5185(16)
C4 C5 1.5629(16)
C5 C17 1.5132(16)
C5 C6 1.5736(17)
C6 C7 1.5041(16)
C7 C8 1.3439(16)
C8 C9 1.4496(16)
C9 C10 1.3372(17)
C10 C11 1.4773(16)
C17 C22 1.3852(16)
C17 C18 1.4009(16)
C18 C19 1.3848(16)
C19 C20 1.4119(16)
C20 C21 1.3825(17)
C21 C22 1.3999(17)
