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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/4/10/48/4104858.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_4104858
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_absolute_configuration unk
_chemical_formula_sum            'C17 H26 O4'
_chemical_formula_weight         294.38
_space_group_IT_number           4
_symmetry_cell_setting           monoclinic
_symmetry_space_group_name_Hall  'P 2yb'
_symmetry_space_group_name_H-M   'P 1 21 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                 97.035(3)
_cell_angle_gamma                90.00
_cell_formula_units_Z            2
_cell_length_a                   6.6601(14)
_cell_length_b                   11.827(3)
_cell_length_c                   9.660(2)
_cell_measurement_reflns_used    5960
_cell_measurement_temperature    125(2)
_cell_measurement_theta_max      30.48
_cell_measurement_theta_min      2.73
_cell_volume                     755.2(3)
_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 0.998
_diffrn_measured_fraction_theta_max 0.998
_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  0.0425
_diffrn_reflns_av_sigmaI/netI    0.0328
_diffrn_reflns_limit_h_max       9
_diffrn_reflns_limit_h_min       -9
_diffrn_reflns_limit_k_max       16
_diffrn_reflns_limit_k_min       -16
_diffrn_reflns_limit_l_max       13
_diffrn_reflns_limit_l_min       -13
_diffrn_reflns_number            12175
_diffrn_reflns_theta_full        30.54
_diffrn_reflns_theta_max         30.54
_diffrn_reflns_theta_min         2.12
_exptl_absorpt_coefficient_mu    0.090
_exptl_absorpt_correction_T_max  0.9973
_exptl_absorpt_correction_T_min  0.9786
_exptl_absorpt_correction_type   empirical
_exptl_absorpt_process_details   SADABS
_exptl_crystal_colour            COLORLESS
_exptl_crystal_density_diffrn    1.295
_exptl_crystal_description       PLATE
_exptl_crystal_F_000             320
_exptl_crystal_size_max          0.24
_exptl_crystal_size_mid          0.23
_exptl_crystal_size_min          0.03
_refine_diff_density_max         0.272
_refine_diff_density_min         -0.197
_refine_diff_density_rms         0.044
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.054
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     190
_refine_ls_number_reflns         2417
_refine_ls_number_restraints     1
_refine_ls_restrained_S_all      1.054
_refine_ls_R_factor_all          0.0432
_refine_ls_R_factor_gt           0.0351
_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)+(0.0548P)²+0.0147P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0868
_refine_ls_wR_factor_ref         0.0906
_reflns_number_gt                2140
_reflns_number_total             2417
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            ja9049433_si_002.cif
_cod_data_source_block           zws10
_cod_database_code               4104858
loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'-x, 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 1.5866(2) 0.55075(14) 0.76265(15) 0.0315(3) Uani 1 1 d .
O2 O 1.3512(2) 0.55313(11) 0.90787(13) 0.0219(3) Uani 1 1 d .
O3 O 0.85282(18) 0.40807(11) 1.08659(13) 0.0191(3) Uani 1 1 d .
O4 O 1.2594(2) 0.16182(10) 0.88981(14) 0.0209(3) Uani 1 1 d .
H4A H 1.2183 0.1023 0.9244 0.031 Uiso 1 1 calc R
C1 C 1.4701(3) 0.49938(16) 0.82505(18) 0.0210(4) Uani 1 1 d .
C2 C 1.4330(3) 0.37354(15) 0.82832(19) 0.0196(3) Uani 1 1 d .
H2A H 1.5464 0.3346 0.8849 0.023 Uiso 1 1 calc R
H2B H 1.4173 0.3417 0.7329 0.023 Uiso 1 1 calc R
C3 C 1.2368(2) 0.36088(14) 0.89481(16) 0.0143(3) Uani 1 1 d .
C4 C 1.0534(3) 0.35984(17) 0.78229(18) 0.0202(3) Uani 1 1 d .
H4B H 1.0537 0.2899 0.7279 0.030 Uiso 1 1 calc R
H4C H 1.0603 0.4250 0.7204 0.030 Uiso 1 1 calc R
H4D H 0.9289 0.3639 0.8266 0.030 Uiso 1 1 calc R
C5 C 1.2470(2) 0.25336(14) 0.98453(17) 0.0145(3) Uani 1 1 d .
H5A H 1.3750 0.2554 1.0504 0.017 Uiso 1 1 calc R
C6 C 1.0699(3) 0.23661(13) 1.06971(18) 0.0159(3) Uani 1 1 d .
H6A H 0.9479 0.2163 1.0055 0.019 Uiso 1 1 calc R
H6B H 1.1014 0.1724 1.1345 0.019 Uiso 1 1 calc R
C7 C 1.0233(2) 0.33944(13) 1.15289(17) 0.0148(3) Uani 1 1 d .
C8 C 0.8387(3) 0.35096(16) 1.21887(18) 0.0192(3) Uani 1 1 d .
H8A H 0.7459 0.2849 1.2229 0.023 Uiso 1 1 calc R
C9 C 0.8753(3) 0.43071(16) 1.34035(19) 0.0192(3) Uani 1 1 d .
H9A H 0.8955 0.3886 1.4295 0.023 Uiso 1 1 calc R
H9B H 0.7599 0.4833 1.3421 0.023 Uiso 1 1 calc R
C10 C 1.0697(3) 0.49577(15) 1.31585(18) 0.0162(3) Uani 1 1 d .
H10A H 1.0279 0.5606 1.2523 0.019 Uiso 1 1 calc R
C11 C 1.1793(3) 0.54535(16) 1.45183(17) 0.0190(3) Uani 1 1 d .
H11A H 1.2309 0.4810 1.5133 0.023 Uiso 1 1 calc R
C12 C 1.0311(3) 0.61396(17) 1.5285(2) 0.0261(4) Uani 1 1 d .
H12A H 1.1028 0.6450 1.6148 0.039 Uiso 1 1 calc R
H12B H 0.9214 0.5647 1.5510 0.039 Uiso 1 1 calc R
H12C H 0.9747 0.6760 1.4687 0.039 Uiso 1 1 calc R
C13 C 1.3594(3) 0.62068(17) 1.4291(2) 0.0251(4) Uani 1 1 d .
H13A H 1.4224 0.6495 1.5192 0.038 Uiso 1 1 calc R
H13B H 1.3124 0.6842 1.3686 0.038 Uiso 1 1 calc R
H13C H 1.4586 0.5765 1.3850 0.038 Uiso 1 1 calc R
C14 C 1.1911(2) 0.41091(13) 1.23299(16) 0.0136(3) Uani 1 1 d .
C15 C 1.3202(2) 0.33064(14) 1.33339(17) 0.0159(3) Uani 1 1 d .
H15A H 1.3946 0.2784 1.2795 0.024 Uiso 1 1 calc R
H15B H 1.2318 0.2875 1.3879 0.024 Uiso 1 1 calc R
H15C H 1.4162 0.3750 1.3965 0.024 Uiso 1 1 calc R
C16 C 1.3249(3) 0.47007(14) 1.13287(17) 0.0153(3) Uani 1 1 d .
H16A H 1.3512 0.5487 1.1651 0.018 Uiso 1 1 calc R
H16B H 1.4568 0.4306 1.1395 0.018 Uiso 1 1 calc R
C17 C 1.2335(3) 0.47281(13) 0.98038(18) 0.0156(3) Uani 1 1 d .
H17A H 1.0908 0.5004 0.9748 0.019 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 O2 C17 111.42(13)
C8 O3 C7 59.60(11)
O1 C1 O2 121.30(18)
O1 C1 C2 128.69(19)
O2 C1 C2 110.00(15)
C1 C2 C3 104.79(14)
C2 C3 C4 110.50(13)
C2 C3 C5 109.67(14)
C4 C3 C5 111.70(14)
C2 C3 C17 101.95(13)
C4 C3 C17 108.68(14)
C5 C3 C17 113.92(13)
O4 C5 C6 110.84(13)
O4 C5 C3 105.57(13)
C6 C5 C3 115.28(13)
C7 C6 C5 113.80(13)
C8 C7 O3 59.58(11)
C8 C7 C6 123.14(15)
O3 C7 C6 114.15(13)
C8 C7 C14 109.21(14)
O3 C7 C14 112.96(13)
C6 C7 C14 121.86(14)
O3 C8 C7 60.82(10)
O3 C8 C9 111.84(15)
C7 C8 C9 109.60(14)
C8 C9 C10 104.54(14)
C11 C10 C9 112.14(14)
C11 C10 C14 117.35(14)
C9 C10 C14 104.64(14)
C13 C11 C12 108.81(16)
C13 C11 C10 113.41(14)
C12 C11 C10 110.34(15)
C7 C14 C15 107.08(13)
C7 C14 C16 111.78(13)
C15 C14 C16 110.46(13)
C7 C14 C10 102.78(13)
C15 C14 C10 110.83(13)
C16 C14 C10 113.51(13)
C17 C16 C14 114.71(14)
O2 C17 C16 107.60(13)
O2 C17 C3 104.68(13)
C16 C17 C3 117.62(13)
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
O1 C1 1.204(2)
O2 C1 1.351(2)
O2 C17 1.464(2)
O3 C8 1.459(2)
O3 C7 1.477(2)
O4 C5 1.427(2)
C1 C2 1.510(3)
C2 C3 1.532(2)
C3 C4 1.533(2)
C3 C5 1.536(2)
C3 C17 1.562(2)
C5 C6 1.531(2)
C6 C7 1.511(2)
C7 C8 1.459(2)
C7 C14 1.533(2)
C8 C9 1.502(3)
C9 C10 1.549(2)
C10 C11 1.538(2)
C10 C14 1.568(2)
C11 C13 1.531(3)
C11 C12 1.536(3)
C14 C15 1.542(2)
C14 C16 1.559(2)
C16 C17 1.524(2)
loop_
_cod_related_entry_id
_cod_related_entry_database
_cod_related_entry_code
1 PubChem 44238208
