#------------------------------------------------------------------------------
#$Date: 2025-08-19 22:06:29 +0200 (Tue 19 de Aug de 2025) $
#$Revision: 301812 $
#$URL: svn://www.crystallography.net/cod/cif/4/02/51/4025125.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_4025125
loop_
_publ_author_name
'Erin M. O'Brien'
'Jingxian Li'
'Patrick J. Carroll'
'Marisa C. Kozlowski'
_publ_section_title
;
 Synthesis of the Cores of Hypocrellin and Shiraiachrome:
 Diastereoselective 1,8-Diketone Aldol Cyclization
;
_journal_name_full               'Journal of Organic Chemistry'
_journal_page_first              69
_journal_page_last               73
_journal_paper_doi               10.1021/jo9018914
_journal_volume                  75
_journal_year                    2010
_chemical_formula_sum            'C29 H34 O9 S'
_chemical_formula_weight         558.62
_space_group_IT_number           2
_symmetry_cell_setting           triclinic
_symmetry_Int_Tables_number      2
_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
_audit_creation_method           SHELXL-97
_cell_angle_alpha                106.311(2)
_cell_angle_beta                 109.262(2)
_cell_angle_gamma                94.8020(10)
_cell_formula_units_Z            2
_cell_length_a                   9.8442(11)
_cell_length_b                   10.9208(13)
_cell_length_c                   14.2899(18)
_cell_measurement_temperature    143(1)
_cell_volume                     1365.3(3)
_computing_data_collection       'CrystalClear (Rigaku, 1999)'
_computing_data_reduction        'CrystalClear (Rigaku, 1999)'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_computing_structure_solution    'SIR97 (Altomare, 1999)'
_diffrn_ambient_temperature      143(1)
_diffrn_measured_fraction_theta_full 0.991
_diffrn_measured_fraction_theta_max 0.991
_diffrn_measurement_device       'CCD Area Detector'
_diffrn_measurement_device_type  'Rigaku Mercury'
_diffrn_measurement_method       'phi and omega rotations'
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_source         'rotating anode'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71069
_diffrn_reflns_av_R_equivalents  0.0192
_diffrn_reflns_av_sigmaI/netI    0.0246
_diffrn_reflns_limit_h_max       10
_diffrn_reflns_limit_h_min       -11
_diffrn_reflns_limit_k_max       12
_diffrn_reflns_limit_k_min       -12
_diffrn_reflns_limit_l_max       16
_diffrn_reflns_limit_l_min       -16
_diffrn_reflns_number            12296
_diffrn_reflns_theta_full        25.01
_diffrn_reflns_theta_max         25.01
_diffrn_reflns_theta_min         2.68
_exptl_absorpt_coefficient_mu    0.173
_exptl_absorpt_correction_T_max  1.0000
_exptl_absorpt_correction_T_min  0.9240
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;  Shape and scale corrections using equivalent reflections.
   Shape function based on spherical harmonics.
   Highest even and odd order for spherical harmonics:  4  and  3
   Laue group:  mmm
   Friedel opposites are equivalent.
;
_exptl_crystal_density_diffrn    1.359
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             592
_exptl_crystal_size_max          0.30
_exptl_crystal_size_mid          0.30
_exptl_crystal_size_min          0.10
_refine_diff_density_max         1.864
_refine_diff_density_min         -0.835
_refine_diff_density_rms         0.083
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.043
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     363
_refine_ls_number_reflns         4760
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.043
_refine_ls_R_factor_all          0.0811
_refine_ls_R_factor_gt           0.0753
_refine_ls_shift/su_max          0.009
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'calc w=1/[σ²(Fo²)+(0.1211P)²+2.3309P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.2062
_refine_ls_wR_factor_ref         0.2127
_reflns_number_gt                4211
_reflns_number_total             4760
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            jo9018914_si_002.cif
_cod_data_source_block           shelxl
_cod_depositor_comments
;
The following automatic conversions were performed:

data name '_atom_site_symetry_multiplicity' was replaced with
'_atom_site_symmetry_multiplicity' as specified in the replacement
file 'data/replacement-values/replacement_tags.lst'.

Automatic conversion script
Id: cif_correct_tags 9268 2022-04-12 08:56:07Z antanas 
;
_cod_original_sg_symbol_H-M      'P -1 '
_cod_database_code               4025125
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
_atom_site_disorder_assembly
_atom_site_disorder_group
C1 C 0.6192(3) 0.8177(3) 0.8589(2) 0.0199(6) Uani 1 1 d . . .
C2 C 0.7390(3) 0.7370(3) 0.8736(2) 0.0218(6) Uani 1 1 d . . .
H2 H 0.7171 0.6714 0.8051 0.029 Uiso 1 1 calc R . .
C3 C 0.7354(3) 0.6609(3) 0.9502(2) 0.0220(6) Uani 1 1 d . . .
C4 C 0.5778(3) 0.5944(3) 0.9261(2) 0.0240(6) Uani 1 1 d . . .
H4A H 0.5823 0.5295 0.9609 0.032 Uiso 1 1 calc R . .
H4B H 0.5281 0.6590 0.9556 0.032 Uiso 1 1 calc R . .
C5 C 0.4877(3) 0.5296(3) 0.8105(2) 0.0231(6) Uani 1 1 d . . .
C6 C 0.4503(3) 0.3948(3) 0.7650(2) 0.0270(7) Uani 1 1 d . . .
H6 H 0.4806 0.3427 0.8065 0.036 Uiso 1 1 calc R . .
C7 C 0.3683(3) 0.3373(3) 0.6586(3) 0.0280(7) Uani 1 1 d . . .
C8 C 0.3273(3) 0.4143(3) 0.5945(2) 0.0251(6) Uani 1 1 d . . .
C9 C 0.3664(3) 0.5485(3) 0.6400(2) 0.0219(6) Uani 1 1 d . . .
C10 C 0.4416(3) 0.6079(3) 0.7482(2) 0.0209(6) Uani 1 1 d . . .
C11 C 0.4743(3) 0.7517(3) 0.7977(2) 0.0204(6) Uani 1 1 d . . .
C12 C 0.3608(3) 0.8221(3) 0.7908(2) 0.0200(6) Uani 1 1 d . . .
C13 C 0.3906(3) 0.9554(3) 0.8429(2) 0.0208(6) Uani 1 1 d . . .
C14 C 0.5361(3) 1.0212(3) 0.8966(2) 0.0208(6) Uani 1 1 d . . .
C15 C 0.6499(3) 0.9522(3) 0.9064(2) 0.0209(6) Uani 1 1 d . . .
H15 H 0.7464 0.9960 0.9448 0.028 Uiso 1 1 calc R . .
C16 C 0.8893(3) 0.8187(3) 0.9026(2) 0.0248(6) Uani 1 1 d . . .
C17 C 0.9171(4) 0.8567(3) 0.8171(3) 0.0342(7) Uani 1 1 d . . .
H17A H 1.0095 0.9160 0.8456 0.051 Uiso 1 1 calc R . .
H17B H 0.8401 0.8980 0.7862 0.051 Uiso 1 1 calc R . .
H17C H 0.9195 0.7805 0.7645 0.051 Uiso 1 1 calc R . .
C18 C 0.8341(3) 0.5608(3) 0.9443(3) 0.0275(7) Uani 1 1 d . . .
H18A H 0.9320 0.6039 0.9602 0.041 Uiso 1 1 calc R . .
H18B H 0.7975 0.4984 0.8749 0.041 Uiso 1 1 calc R . .
H18C H 0.8349 0.5172 0.9941 0.041 Uiso 1 1 calc R . .
C19 C 0.3355(6) 0.1258(4) 0.6726(4) 0.0676(15) Uani 1 1 d . . .
H19A H 0.4359 0.1381 0.7180 0.101 Uiso 1 1 calc R . .
H19B H 0.3010 0.0361 0.6295 0.101 Uiso 1 1 calc R . .
H19C H 0.2766 0.1497 0.7141 0.101 Uiso 1 1 calc R . .
C20 C 0.4489(4) 0.6822(4) 0.5582(3) 0.0430(9) Uani 1 1 d . . .
H20A H 0.5348 0.7046 0.6210 0.064 Uiso 1 1 calc R . .
H20B H 0.4275 0.7595 0.5417 0.064 Uiso 1 1 calc R . .
H20C H 0.4661 0.6229 0.5013 0.064 Uiso 1 1 calc R . .
C21 C 0.1301(3) 0.7918(3) 0.6531(2) 0.0282(7) Uani 1 1 d . . .
H21A H 0.1067 0.8751 0.6794 0.042 Uiso 1 1 calc R . .
H21B H 0.0411 0.7281 0.6133 0.042 Uiso 1 1 calc R . .
H21C H 0.1841 0.7970 0.6088 0.042 Uiso 1 1 calc R . .
C22 C 0.6994(3) 1.2257(3) 0.9905(3) 0.0295(7) Uani 1 1 d . . .
H22A H 0.7492 1.1996 1.0497 0.044 Uiso 1 1 calc R . .
H22B H 0.6977 1.3168 1.0141 0.044 Uiso 1 1 calc R . .
H22C H 0.7499 1.2095 0.9425 0.044 Uiso 1 1 calc R . .
O1 O 0.9830(2) 0.8505(2) 0.99089(18) 0.0317(5) Uani 1 1 d . . .
O2 O 0.7813(2) 0.7490(2) 1.05635(15) 0.0259(5) Uani 1 1 d . . .
H2A H 0.8631 0.7919 1.0733 0.039 Uiso 1 1 calc R . .
O3 O 0.3251(3) 0.2052(2) 0.6074(2) 0.0410(6) Uani 1 1 d . . .
O4 O 0.2512(2) 0.3541(2) 0.48962(17) 0.0307(5) Uani 1 1 d . . .
H4 H 0.2490 0.4073 0.4588 0.046 Uiso 1 1 calc R . .
O5 O 0.3270(2) 0.6219(2) 0.57397(16) 0.0258(5) Uani 1 1 d . . .
O6 O 0.2178(2) 0.7547(2) 0.73961(16) 0.0235(5) Uani 1 1 d . . .
O7 O 0.2751(2) 1.0177(2) 0.84028(17) 0.0254(5) Uani 1 1 d . . .
H7 H 0.3048 1.0909 0.8837 0.038 Uiso 1 1 calc R . .
O8 O 0.5524(2) 1.1530(2) 0.93886(17) 0.0256(5) Uani 1 1 d . . .
S1 S 0.04466(11) 0.55306(9) 0.35332(7) 0.0424(3) Uani 1 1 d . . .
O9 O 0.1575(3) 0.4746(3) 0.3367(2) 0.0462(7) Uani 1 1 d . . .
C23 C 0.1112(5) 0.7147(4) 0.3604(3) 0.0502(10) Uani 1 1 d . . .
C24 C 0.0414(6) 0.8125(5) 0.3970(4) 0.0678(14) Uani 1 1 d . . .
H24 H -0.0383 0.7923 0.4149 0.090 Uiso 1 1 calc R . .
C25 C 0.0893(10) 0.9367(5) 0.4067(5) 0.107(3) Uani 1 1 d . . .
H25 H 0.0421 1.0019 0.4309 0.142 Uiso 1 1 calc R . .
C26 C 0.2113(13) 0.9677(7) 0.3800(6) 0.121(4) Uani 1 1 d . . .
H26 H 0.2437 1.0526 0.3850 0.160 Uiso 1 1 calc R . .
C27 C 0.2791(9) 0.8724(8) 0.3474(5) 0.104(3) Uani 1 1 d . . .
H27 H 0.3605 0.8939 0.3316 0.138 Uiso 1 1 calc R . .
C28 C 0.2335(6) 0.7402(5) 0.3358(4) 0.0676(14) Uani 1 1 d . . .
H28 H 0.2820 0.6754 0.3132 0.090 Uiso 1 1 calc R . .
C29 C -0.0949(4) 0.5095(4) 0.2259(3) 0.0465(9) Uani 1 1 d . . .
H29A H -0.0503 0.5006 0.1744 0.070 Uiso 1 1 calc R . .
H29B H -0.1525 0.5761 0.2233 0.070 Uiso 1 1 calc R . .
H29C H -0.1569 0.4285 0.2113 0.070 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'
S S 0.1246 0.1234 '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
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
C15 C1 C11 120.3(3) . . ?
C15 C1 C2 121.9(2) . . ?
C11 C1 C2 117.8(2) . . ?
C16 C2 C1 111.5(2) . . ?
C16 C2 C3 113.4(2) . . ?
C1 C2 C3 112.3(2) . . ?
O2 C3 C18 110.2(2) . . ?
O2 C3 C4 104.0(2) . . ?
C18 C3 C4 110.5(2) . . ?
O2 C3 C2 110.7(2) . . ?
C18 C3 C2 110.0(2) . . ?
C4 C3 C2 111.3(2) . . ?
C5 C4 C3 114.4(2) . . ?
C6 C5 C10 119.6(3) . . ?
C6 C5 C4 121.7(3) . . ?
C10 C5 C4 118.7(3) . . ?
C7 C6 C5 120.8(3) . . ?
O3 C7 C6 124.7(3) . . ?
O3 C7 C8 115.1(3) . . ?
C6 C7 C8 120.2(3) . . ?
O4 C8 C9 122.8(3) . . ?
O4 C8 C7 118.5(3) . . ?
C9 C8 C7 118.7(3) . . ?
O5 C9 C8 117.2(3) . . ?
O5 C9 C10 121.1(3) . . ?
C8 C9 C10 121.7(3) . . ?
C5 C10 C9 118.9(3) . . ?
C5 C10 C11 119.5(3) . . ?
C9 C10 C11 121.6(3) . . ?
C12 C11 C1 118.9(3) . . ?
C12 C11 C10 120.8(2) . . ?
C1 C11 C10 120.2(2) . . ?
O6 C12 C13 120.4(2) . . ?
O6 C12 C11 118.5(2) . . ?
C13 C12 C11 120.8(3) . . ?
O7 C13 C12 118.4(2) . . ?
O7 C13 C14 122.1(3) . . ?
C12 C13 C14 119.5(3) . . ?
O8 C14 C15 125.4(2) . . ?
O8 C14 C13 114.3(2) . . ?
C15 C14 C13 120.2(3) . . ?
C14 C15 C1 120.0(3) . . ?
O1 C16 C17 121.6(3) . . ?
O1 C16 C2 121.9(3) . . ?
C17 C16 C2 116.5(3) . . ?
C7 O3 C19 116.0(3) . . ?
C9 O5 C20 113.3(2) . . ?
C12 O6 C21 115.7(2) . . ?
C14 O8 C22 116.6(2) . . ?
O9 S1 C29 104.07(18) . . ?
O9 S1 C23 106.6(2) . . ?
C29 S1 C23 96.08(19) . . ?
C28 C23 C24 122.2(5) . . ?
C28 C23 S1 120.2(4) . . ?
C24 C23 S1 117.4(4) . . ?
C25 C24 C23 120.1(7) . . ?
C24 C25 C26 120.0(7) . . ?
C27 C26 C25 118.8(6) . . ?
C26 C27 C28 123.5(7) . . ?
C23 C28 C27 115.3(6) . . ?
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
C1 C15 1.393(4) . ?
C1 C11 1.404(4) . ?
C1 C2 1.526(4) . ?
C2 C16 1.525(4) . ?
C2 C3 1.555(4) . ?
C3 O2 1.444(3) . ?
C3 C18 1.525(4) . ?
C3 C4 1.540(4) . ?
C4 C5 1.513(4) . ?
C5 C6 1.392(4) . ?
C5 C10 1.399(4) . ?
C6 C7 1.389(5) . ?
C7 O3 1.377(4) . ?
C7 C8 1.398(4) . ?
C8 O4 1.365(4) . ?
C8 C9 1.387(4) . ?
C9 O5 1.385(4) . ?
C9 C10 1.400(4) . ?
C10 C11 1.486(4) . ?
C11 C12 1.401(4) . ?
C12 O6 1.380(3) . ?
C12 C13 1.390(4) . ?
C13 O7 1.369(3) . ?
C13 C14 1.396(4) . ?
C14 O8 1.368(3) . ?
C14 C15 1.392(4) . ?
C16 O1 1.223(4) . ?
C16 C17 1.492(5) . ?
C19 O3 1.427(5) . ?
C20 O5 1.434(4) . ?
C21 O6 1.440(4) . ?
C22 O8 1.429(3) . ?
S1 O9 1.498(3) . ?
S1 C29 1.784(4) . ?
S1 C23 1.794(4) . ?
C23 C28 1.388(7) . ?
C23 C24 1.390(7) . ?
C24 C25 1.352(9) . ?
C25 C26 1.418(13) . ?
C26 C27 1.340(13) . ?
C27 C28 1.421(9) . ?
loop_
_geom_hbond_atom_site_label_D
_geom_hbond_atom_site_label_H
_geom_hbond_atom_site_label_A
_geom_hbond_distance_DH
_geom_hbond_distance_HA
_geom_hbond_distance_DA
_geom_hbond_angle_DHA
_geom_hbond_site_symmetry_A
O2 H2A O1 0.82 2.10 2.736(3) 134.6 .
O4 H4 O9 0.82 2.05 2.801(4) 152.8 .
O4 H4 O5 0.82 2.34 2.761(3) 112.4 .
O7 H7 O2 0.82 2.10 2.765(3) 138.6 2_677
O7 H7 O8 0.82 2.28 2.691(3) 111.8 .
loop_
_cod_related_entry_id
_cod_related_entry_database
_cod_related_entry_code
1 PubChem 139091369
