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#$Date: 2025-08-20 17:12:52 +0300 (Wed, 20 Aug 2025) $
#$Revision: 301832 $
#$URL: file:///home/coder/svn-repositories/cod/cif/4/10/48/4104861.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_4104861
loop_
_publ_author_name
'Zhang Wang'
'Sun-Joon Min'
'Samuel J. Danishefsky'
_publ_section_title
;
 Total Synthesis and Structural Revision of (\+-)-Tricholomalides A and B
;
_journal_name_full               'Journal of the American Chemical Society'
_journal_page_first              10848
_journal_page_last               10849
_journal_paper_doi               10.1021/ja9049433
_journal_volume                  131
_journal_year                    2009
_chemical_formula_sum            'C20 H28 O5'
_chemical_formula_weight         348.42
_space_group_IT_number           15
_symmetry_cell_setting           monoclinic
_symmetry_space_group_name_Hall  '-C 2yc'
_symmetry_space_group_name_H-M   'C 1 2/c 1'
_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                 124.8310(10)
_cell_angle_gamma                90.00
_cell_formula_units_Z            8
_cell_length_a                   33.206(3)
_cell_length_b                   6.6255(6)
_cell_length_c                   19.8029(19)
_cell_measurement_reflns_used    2893
_cell_measurement_temperature    125(2)
_cell_measurement_theta_max      22.88
_cell_measurement_theta_min      2.58
_cell_volume                     3576.2(6)
_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 1.000
_diffrn_measured_fraction_theta_max 1.000
_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  0.1400
_diffrn_reflns_av_sigmaI/netI    0.1021
_diffrn_reflns_limit_h_max       41
_diffrn_reflns_limit_h_min       -41
_diffrn_reflns_limit_k_max       8
_diffrn_reflns_limit_k_min       -8
_diffrn_reflns_limit_l_max       24
_diffrn_reflns_limit_l_min       -24
_diffrn_reflns_number            20786
_diffrn_reflns_theta_full        26.37
_diffrn_reflns_theta_max         26.37
_diffrn_reflns_theta_min         1.49
_exptl_absorpt_coefficient_mu    0.092
_exptl_absorpt_correction_T_max  0.9982
_exptl_absorpt_correction_T_min  0.9819
_exptl_absorpt_correction_type   empirical
_exptl_absorpt_process_details   sadabs
_exptl_crystal_colour            colorless
_exptl_crystal_density_diffrn    1.294
_exptl_crystal_description       plate
_exptl_crystal_F_000             1504
_exptl_crystal_size_max          0.20
_exptl_crystal_size_mid          0.10
_exptl_crystal_size_min          0.02
_refine_diff_density_max         0.266
_refine_diff_density_min         -0.276
_refine_diff_density_rms         0.059
_refine_ls_extinction_coef       0.00056(18)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc²λ³/sin(2θ)]^-1/4^
_refine_ls_extinction_method     SHELXL
_refine_ls_goodness_of_fit_ref   1.067
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     227
_refine_ls_number_reflns         3665
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.067
_refine_ls_R_factor_all          0.1364
_refine_ls_R_factor_gt           0.0528
_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)+(0.0400P)²+0.0000P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0939
_refine_ls_wR_factor_ref         0.1170
_reflns_number_gt                1941
_reflns_number_total             3665
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            ja9049433_si_005.cif
_cod_data_source_block           15s10
_cod_database_code               4104861
loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'-x, y, -z+1/2'
'x+1/2, y+1/2, z'
'-x+1/2, y+1/2, -z+1/2'
'-x, -y, -z'
'x, -y, z-1/2'
'-x+1/2, -y+1/2, -z'
'x+1/2, -y+1/2, z-1/2'
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 0.23106(6) 0.4036(3) 0.21519(10) 0.0264(5) Uani 1 1 d .
O2 O 0.02619(6) 0.2101(3) 0.01772(10) 0.0246(5) Uani 1 1 d .
O3 O 0.27361(7) 0.4735(3) 0.16262(11) 0.0310(5) Uani 1 1 d .
O4 O -0.00575(6) 0.3562(3) 0.12359(11) 0.0263(5) Uani 1 1 d .
O5 O 0.09460(6) 0.5473(2) 0.02179(10) 0.0233(5) Uani 1 1 d .
H5A H 0.0673 0.5678 -0.0227 0.035 Uiso 1 1 calc R
C1 C 0.23484(10) 0.4316(4) 0.15193(17) 0.0242(7) Uani 1 1 d .
C2 C 0.18572(9) 0.4004(4) 0.07202(16) 0.0254(7) Uani 1 1 d .
H2A H 0.1890 0.3198 0.0333 0.030 Uiso 1 1 calc R
H2B H 0.1703 0.5314 0.0460 0.030 Uiso 1 1 calc R
C3 C 0.15553(9) 0.2870(4) 0.09581(15) 0.0198(6) Uani 1 1 d .
C4 C 0.10027(9) 0.3365(4) 0.04049(15) 0.0184(6) Uani 1 1 d .
C5 C 0.07088(9) 0.2132(4) -0.03848(15) 0.0211(6) Uani 1 1 d .
C6 C 0.03349(10) 0.0957(4) -0.03582(16) 0.0267(7) Uani 1 1 d .
H6A H 0.0026 0.0842 -0.0914 0.032 Uiso 1 1 calc R
H6B H 0.0457 -0.0415 -0.0136 0.032 Uiso 1 1 calc R
C7 C 0.07418(9) 0.2768(4) 0.08290(15) 0.0183(6) Uani 1 1 d .
H7A H 0.0922 0.1610 0.1209 0.022 Uiso 1 1 calc R
C8 C 0.06843(9) 0.4422(4) 0.13005(15) 0.0184(6) Uani 1 1 d .
H8A H 0.0514 0.5616 0.0936 0.022 Uiso 1 1 calc R
C9 C 0.03890(10) 0.3593(4) 0.16095(16) 0.0216(6) Uani 1 1 d .
C10 C 0.07315(9) 0.2830(4) 0.24726(15) 0.0243(7) Uani 1 1 d .
H10A H 0.0701 0.1348 0.2491 0.029 Uiso 1 1 calc R
H10B H 0.0656 0.3465 0.2840 0.029 Uiso 1 1 calc R
C11 C 0.12571(9) 0.3406(4) 0.27438(15) 0.0193(6) Uani 1 1 d .
H11A H 0.1397 0.2208 0.2640 0.023 Uiso 1 1 calc R
C12 C 0.11702(9) 0.5094(4) 0.21160(15) 0.0192(6) Uani 1 1 d .
C13 C 0.16020(9) 0.5416(4) 0.20347(15) 0.0214(6) Uani 1 1 d .
H13A H 0.1496 0.6401 0.1586 0.026 Uiso 1 1 calc R
H13B H 0.1875 0.6044 0.2550 0.026 Uiso 1 1 calc R
C14 C 0.18036(9) 0.3570(4) 0.18641(15) 0.0199(6) Uani 1 1 d .
H14A H 0.1808 0.2410 0.2192 0.024 Uiso 1 1 calc R
C15 C 0.16467(10) 0.0591(4) 0.09700(17) 0.0295(7) Uani 1 1 d .
H15A H 0.1502 0.0116 0.0407 0.044 Uiso 1 1 calc R
H15B H 0.1496 -0.0127 0.1206 0.044 Uiso 1 1 calc R
H15C H 0.2001 0.0330 0.1305 0.044 Uiso 1 1 calc R
C16 C 0.07482(10) 0.2214(4) -0.10085(17) 0.0333(8) Uani 1 1 d .
H16A H 0.0526 0.1482 -0.1498 0.040 Uiso 1 1 calc R
H16B H 0.0999 0.3007 -0.0970 0.040 Uiso 1 1 calc R
C17 C 0.15891(9) 0.3850(4) 0.36724(15) 0.0237(7) Uani 1 1 d .
H17A H 0.1430 0.4942 0.3791 0.028 Uiso 1 1 calc R
C18 C 0.16183(10) 0.1960(4) 0.41450(16) 0.0311(7) Uani 1 1 d .
H18A H 0.1822 0.2244 0.4737 0.047 Uiso 1 1 calc R
H18B H 0.1764 0.0851 0.4026 0.047 Uiso 1 1 calc R
H18C H 0.1288 0.1577 0.3975 0.047 Uiso 1 1 calc R
C19 C 0.21087(9) 0.4540(4) 0.39996(16) 0.0298(7) Uani 1 1 d .
H19A H 0.2285 0.4858 0.4586 0.045 Uiso 1 1 calc R
H19B H 0.2094 0.5745 0.3699 0.045 Uiso 1 1 calc R
H19C H 0.2281 0.3460 0.3923 0.045 Uiso 1 1 calc R
C20 C 0.10682(10) 0.7134(4) 0.23606(16) 0.0250(7) Uani 1 1 d .
H20A H 0.1013 0.8167 0.1962 0.038 Uiso 1 1 calc R
H20B H 0.1351 0.7517 0.2909 0.038 Uiso 1 1 calc R
H20C H 0.0776 0.7018 0.2367 0.038 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
C1 O1 C14 111.39(19)
C7 O2 C6 104.99(18)
O3 C1 O1 121.7(2)
O3 C1 C2 128.4(3)
O1 C1 C2 109.9(2)
C1 C2 C3 104.6(2)
C2 C3 C15 109.2(2)
C2 C3 C4 113.6(2)
C15 C3 C4 111.4(2)
C2 C3 C14 101.5(2)
C15 C3 C14 107.8(2)
C4 C3 C14 112.8(2)
O5 C4 C5 110.2(2)
O5 C4 C3 108.6(2)
C5 C4 C3 114.8(2)
O5 C4 C7 110.8(2)
C5 C4 C7 100.9(2)
C3 C4 C7 111.3(2)
C16 C5 C6 125.9(2)
C16 C5 C4 126.3(2)
C6 C5 C4 107.6(2)
O2 C6 C5 104.3(2)
O2 C7 C8 108.07(19)
O2 C7 C4 105.48(19)
C8 C7 C4 116.7(2)
C7 C8 C9 108.8(2)
C7 C8 C12 115.0(2)
C9 C8 C12 102.1(2)
O4 C9 C10 123.5(2)
O4 C9 C8 126.8(2)
C10 C9 C8 109.6(2)
C9 C10 C11 106.4(2)
C17 C11 C10 110.9(2)
C17 C11 C12 119.5(2)
C10 C11 C12 103.84(19)
C20 C12 C13 107.2(2)
C20 C12 C8 107.1(2)
C13 C12 C8 113.8(2)
C20 C12 C11 110.5(2)
C13 C12 C11 114.7(2)
C8 C12 C11 103.28(19)
C14 C13 C12 117.6(2)
O1 C14 C13 107.3(2)
O1 C14 C3 104.2(2)
C13 C14 C3 119.0(2)
C19 C17 C18 108.9(2)
C19 C17 C11 115.4(2)
C18 C17 C11 109.0(2)
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
O1 C1 1.341(3)
O1 C14 1.469(3)
O2 C7 1.432(3)
O2 C6 1.432(3)
O3 C1 1.212(3)
O4 C9 1.222(3)
O5 C4 1.429(3)
C1 C2 1.503(4)
C2 C3 1.527(3)
C3 C15 1.538(4)
C3 C4 1.542(3)
C3 C14 1.557(3)
C4 C5 1.524(3)
C4 C7 1.563(3)
C5 C16 1.315(3)
C5 C6 1.492(3)
C7 C8 1.521(3)
C8 C9 1.524(3)
C8 C12 1.560(3)
C9 C10 1.500(4)
C10 C11 1.552(3)
C11 C17 1.539(3)
C11 C12 1.572(3)
C12 C20 1.537(3)
C12 C13 1.546(3)
C13 C14 1.522(3)
C17 C19 1.526(3)
C17 C18 1.533(4)
loop_
_cod_related_entry_id
_cod_related_entry_database
_cod_related_entry_code
1 PubChem 139115639
