#------------------------------------------------------------------------------
#$Date: 2016-03-21 18:12:35 +0200 (Mon, 21 Mar 2016) $
#$Revision: 178805 $
#$URL: svn://www.crystallography.net/cod/cif/4/10/59/4105952.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_4105952
loop_
_publ_author_name
'Ying L. Zhang'
'Jie Zhang'
'Nan Jiang'
'Yan H. Lu'
'Lu Wang'
'Su H. Xu'
'Wei Wang'
'Gao F. Zhang'
'Qiang Xu'
'Hui M. Ge'
'Jing Ma'
'Yong C. Song'
'Ren X. Tan'
_publ_section_title
;
 Immunosuppressive Polyketides from Mantis-Associated Daldinia
 eschscholzii
;
_journal_name_full               'Journal of the American Chemical Society'
_journal_page_first              5931
_journal_page_last               5940
_journal_paper_doi               10.1021/ja110932p
_journal_volume                  133
_journal_year                    2011
_chemical_formula_sum            'C12 H12 O5'
_chemical_formula_weight         236.07
_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                   4.9131(11)
_cell_length_b                   8.5738(19)
_cell_length_c                   24.007(5)
_cell_measurement_temperature    273(2)
_cell_volume                     1011.3(4)
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 1990)'
_diffrn_ambient_temperature      273(2)
_diffrn_measured_fraction_theta_full 0.946
_diffrn_measured_fraction_theta_max 0.946
_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  0.0362
_diffrn_reflns_av_sigmaI/netI    0.0325
_diffrn_reflns_limit_h_max       6
_diffrn_reflns_limit_h_min       -6
_diffrn_reflns_limit_k_max       10
_diffrn_reflns_limit_k_min       -10
_diffrn_reflns_limit_l_max       31
_diffrn_reflns_limit_l_min       -24
_diffrn_reflns_number            5852
_diffrn_reflns_theta_full        28.23
_diffrn_reflns_theta_max         28.23
_diffrn_reflns_theta_min         2.52
_exptl_absorpt_coefficient_mu    0.122
_exptl_crystal_density_diffrn    1.551
_exptl_crystal_F_000             496
_refine_diff_density_max         0.358
_refine_diff_density_min         -0.266
_refine_diff_density_rms         0.057
_refine_ls_abs_structure_details 'Flack H D (1983), Acta Cryst. A39, 876-881'
_refine_ls_abs_structure_Flack   0.9(13)
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.096
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     157
_refine_ls_number_reflns         2315
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.096
_refine_ls_R_factor_all          0.0502
_refine_ls_R_factor_gt           0.0471
_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)+(0.0706P)²+0.1196P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1205
_refine_ls_wR_factor_ref         0.1229
_reflns_number_gt                2174
_reflns_number_total             2315
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            ja110932p_si_004.cif
_cod_data_source_block           Compound27
_cod_database_code               4105952
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
C5 C 0.8007(4) 0.7865(2) 0.10853(7) 0.0247(4) Uani 1 1 d .
O4 O 0.7904(3) 0.50410(15) 0.10817(6) 0.0368(4) Uani 1 1 d .
H4 H 0.6739 0.5225 0.0846 0.055 Uiso 1 1 calc R
O3 O 0.4844(3) 0.67442(17) 0.04666(7) 0.0386(4) Uani 1 1 d .
C6 C 0.9120(4) 0.9245(2) 0.13113(7) 0.0259(4) Uani 1 1 d .
C7 C 1.1078(4) 0.9167(2) 0.17249(8) 0.0281(4) Uani 1 1 d .
H7 H 1.1811 1.0072 0.1877 0.034 Uiso 1 1 calc R
C8 C 1.1929(4) 0.7707(2) 0.19083(7) 0.0283(4) Uani 1 1 d .
C10 C 0.8910(4) 0.6402(2) 0.12815(8) 0.0265(4) Uani 1 1 d .
O2 O 0.6654(3) 1.21423(17) 0.02567(6) 0.0357(3) Uani 1 1 d .
H2 H 0.7924 1.2555 0.0091 0.054 Uiso 1 1 calc R
C9 C 1.0888(4) 0.6350(2) 0.16878(8) 0.0290(4) Uani 1 1 d .
C3 C 0.5274(4) 0.9486(2) 0.03946(8) 0.0298(4) Uani 1 1 d .
H3A H 0.3618 0.9872 0.0566 0.036 Uiso 1 1 calc R
H3B H 0.4928 0.9362 -0.0001 0.036 Uiso 1 1 calc R
C1 C 0.8158(4) 1.0809(2) 0.10956(8) 0.0286(4) Uani 1 1 d .
H1 H 0.6501 1.1112 0.1296 0.034 Uiso 1 1 calc R
C12 C 1.2195(5) 0.4969(2) 0.19560(9) 0.0382(5) Uani 1 1 d .
H12A H 1.0854 0.4339 0.2149 0.046 Uiso 1 1 calc R
H12B H 1.3109 0.4327 0.1681 0.046 Uiso 1 1 calc R
C4 C 0.5966(4) 0.7918(2) 0.06418(7) 0.0268(4) Uani 1 1 d .
O1 O 1.0204(4) 1.19355(16) 0.11958(7) 0.0467(4) Uani 1 1 d .
H1A H 0.9681 1.2791 0.1087 0.070 Uiso 1 1 calc R
C2 C 0.7514(4) 1.0674(2) 0.04750(7) 0.0264(4) Uani 1 1 d .
H2A H 0.9147 1.0328 0.0276 0.032 Uiso 1 1 calc R
O5 O 1.4107(4) 0.56182(19) 0.23397(9) 0.0631(6) Uani 1 1 d .
C11 C 1.3982(5) 0.7283(3) 0.23426(8) 0.0371(5) Uani 1 1 d .
H11A H 1.5744 0.7727 0.2253 0.045 Uiso 1 1 calc R
H11B H 1.3419 0.7663 0.2705 0.045 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
C6 C5 C10 119.65(16)
C6 C5 C4 121.29(16)
C10 C5 C4 119.05(16)
C7 C6 C5 120.32(17)
C7 C6 C1 120.32(16)
C5 C6 C1 119.36(16)
C6 C7 C8 118.61(17)
C9 C8 C7 121.84(16)
C9 C8 C11 108.22(17)
C7 C8 C11 129.95(18)
O4 C10 C9 118.66(16)
O4 C10 C5 122.19(16)
C9 C10 C5 119.15(16)
C8 C9 C10 120.42(16)
C8 C9 C12 110.16(17)
C10 C9 C12 129.42(17)
C4 C3 C2 112.71(15)
O1 C1 C6 108.97(16)
O1 C1 C2 111.39(16)
C6 C1 C2 109.34(15)
O5 C12 C9 104.63(16)
O3 C4 C5 122.29(17)
O3 C4 C3 119.79(16)
C5 C4 C3 117.91(16)
O2 C2 C3 109.37(15)
O2 C2 C1 110.64(15)
C3 C2 C1 109.05(15)
C11 O5 C12 111.33(16)
O5 C11 C8 105.59(17)
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
C5 C6 1.411(3)
C5 C10 1.411(3)
C5 C4 1.463(2)
O4 C10 1.355(2)
O3 C4 1.222(2)
C6 C7 1.384(3)
C6 C1 1.513(2)
C7 C8 1.391(3)
C8 C9 1.377(3)
C8 C11 1.496(3)
C10 C9 1.377(3)
O2 C2 1.428(2)
C9 C12 1.492(3)
C3 C4 1.509(3)
C3 C2 1.512(3)
C1 O1 1.415(2)
C1 C2 1.527(3)
C12 O5 1.429(3)
O5 C11 1.429(3)
