#------------------------------------------------------------------------------
#$Date: 2025-08-18 15:30:32 +0200 (Mon 18 de Aug de 2025) $
#$Revision: 301775 $
#$URL: svn://www.crystallography.net/cod/cif/1/50/25/1502553.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_1502553
loop_
_publ_author_name
'Hong, Wan Pyo'
'Noshi, Mohammad N.'
'El-Awa, Ahmad'
'Fuchs, Philip L.'
_publ_section_title
;
 Synthesis of the C1-C20 and C15-C27 segments of aplyronine A.
;
_journal_issue                   24
_journal_name_full               'Organic letters'
_journal_page_first              6342
_journal_page_last               6345
_journal_paper_doi               10.1021/ol2024746
_journal_volume                  13
_journal_year                    2011
_chemical_absolute_configuration ad
_chemical_formula_moiety         'C22 H24 O4 S2'
_chemical_formula_sum            'C22 H24 O4 S2'
_chemical_formula_weight         416.56
_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_type_scat_source
'International Tables for Crystallography (Vol C)'
_cell_angle_alpha                90.00
_cell_angle_beta                 90.00
_cell_angle_gamma                90.00
_cell_formula_units_Z            4
_cell_length_a                   8.4312(2)
_cell_length_b                   8.9716(2)
_cell_length_c                   28.7625(10)
_cell_measurement_reflns_used    15044
_cell_measurement_temperature    150
_cell_measurement_theta_max      27
_cell_measurement_theta_min      2
_cell_volume                     2175.63(10)
_computing_cell_refinement       'DENZO/SCALEPACK (Otwinowski & Minor, 1996)'
_computing_data_collection       'Collect (Nonius, 1998)'
_computing_data_reduction        'DENZO/SCALEPACK (Otwinowski & Minor, 1996)'
_computing_molecular_graphics
;
    ORTEP (Johnson, 1976)
    PLATON (Spek, 1997)
;
_computing_publication_material  'SHELX97(Sheldrick, 2008) and local programs'
_computing_structure_refinement  'SHELX97 (Sheldrick, 2008)'
_computing_structure_solution
;
 Direct methods (SIR2004, Burla et al., 2005)
;
_diffrn_ambient_temperature      150
_diffrn_measured_fraction_theta_full 0.9834
_diffrn_measured_fraction_theta_max 0.8697
_diffrn_measurement_device_type  Nonius_KappaCCD
_diffrn_measurement_method       ω
_diffrn_radiation_monochromator  'graphite 002'
_diffrn_radiation_type           MO-K\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.064
_diffrn_reflns_limit_h_max       10
_diffrn_reflns_limit_h_min       -10
_diffrn_reflns_limit_k_max       11
_diffrn_reflns_limit_k_min       -11
_diffrn_reflns_limit_l_max       37
_diffrn_reflns_limit_l_min       -37
_diffrn_reflns_number            15044
_diffrn_reflns_theta_full        24.1
_diffrn_reflns_theta_max         27.49
_diffrn_reflns_theta_min         2.12
_diffrn_standards_number         0
_exptl_absorpt_coefficient_mu    0.257
_exptl_absorpt_correction_T_max  0.9499
_exptl_absorpt_correction_T_min  0.9105
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   'SCALEPACK (Otwinowski & Minor, 1997)'
_exptl_crystal_colour_primary    colourless
_exptl_crystal_density_diffrn    1.272
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       needle
_exptl_crystal_F_000             880
_exptl_crystal_size_max          0.60
_exptl_crystal_size_mid          0.30
_exptl_crystal_size_min          0.20
_refine_diff_density_max         0.24
_refine_diff_density_min         -0.41
_refine_ls_abs_structure_details 'Flack H. D. (1983), Acta Cryst. A39, 876-881'
_refine_ls_abs_structure_Flack   -0.03(8)
_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     255
_refine_ls_number_reflns         4776
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.069
_refine_ls_R_factor_gt           0.048
_refine_ls_shift/su_max          0.004
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'1/[σ²(Fo²)+(0.0549P)²+0.4843P] where P=(Fo²+2Fc²)/3  '
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.104
_refine_ls_wR_factor_ref         0.114
_reflns_Friedel_coverage         0.8195
_reflns_number_gt                3674
_reflns_number_total             4776
_reflns_threshold_expression     >2.0σ(I)
_cod_data_source_file            ol2024746_si_001.cif
_cod_data_source_block           MNBOAC
_cod_depositor_comments
;
The following automatic conversions were performed:

'_refine_ls_weighting_scheme' value 'calc ' changed to 'calc'
according to /home/saulius/struct/CIF-dictionaries/cif_core.dic
dictionary named 'cif_core.dic' version 2.4.1 from 2010-06-29.

Automatic conversion script
Id: cif_fix_values 1715 2011-07-08 13:25:40Z adriana 

The following automatic conversions were performed:

data name '_exptl_absorpt__process_details' was replaced with
'_exptl_absorpt_process_details' 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_database_code               1502553
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_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
S3 0.80707(7) 0.78946(8) 0.84606(3) 0.02934(18) Uani 1 1 d .
S5 0.25358(8) 0.97191(8) 0.92599(3) 0.03395(19) Uani 1 1 d .
O11 0.3577(2) 0.41111(19) 0.82638(7) 0.0321(5) Uani 1 1 d .
O12 0.5007(3) 0.3672(2) 0.76189(7) 0.0374(5) Uani 1 1 d .
O31 0.8685(2) 0.7544(2) 0.89133(7) 0.0393(5) Uani 1 1 d .
O32 0.8700(2) 0.7111(2) 0.80628(7) 0.0395(5) Uani 1 1 d .
C1 0.3957(3) 0.5701(3) 0.82481(10) 0.0267(6) Uani 1 1 d .
C2 0.5572(3) 0.5945(3) 0.84820(10) 0.0274(6) Uani 1 1 d .
C3 0.5966(3) 0.7633(3) 0.84585(10) 0.0244(6) Uani 1 1 d .
C4 0.5195(3) 0.8533(3) 0.88395(9) 0.0248(6) Uani 1 1 d .
C5 0.3635(3) 0.8777(3) 0.88292(9) 0.0257(6) Uani 1 1 d .
C6 0.2585(3) 0.8161(3) 0.84529(10) 0.0277(6) Uani 1 1 d .
C7 0.2530(3) 0.6446(3) 0.84601(10) 0.0291(6) Uani 1 1 d .
C12 0.4171(3) 0.3220(3) 0.79288(10) 0.0313(7) Uani 1 1 d .
C13 0.3644(4) 0.1649(3) 0.79943(11) 0.0434(8) Uani 1 1 d .
C21 0.5665(4) 0.5301(3) 0.89726(10) 0.0388(7) Uani 1 1 d .
C31 0.8344(3) 0.9832(3) 0.83684(10) 0.0296(6) Uani 1 1 d .
C32 0.8479(3) 1.0373(3) 0.79172(11) 0.0370(7) Uani 1 1 d .
C33 0.8732(4) 1.1881(4) 0.78495(13) 0.0461(8) Uani 1 1 d .
C34 0.8867(4) 1.2822(4) 0.82228(14) 0.0492(9) Uani 1 1 d .
C35 0.8750(4) 1.2276(4) 0.86722(14) 0.0505(9) Uani 1 1 d .
C36 0.8496(4) 1.0767(3) 0.87496(11) 0.0394(8) Uani 1 1 d .
C51 0.4023(3) 1.0227(3) 0.96661(10) 0.0304(6) Uani 1 1 d .
C52 0.4954(4) 1.1465(3) 0.95887(11) 0.0415(8) Uani 1 1 d .
C53 0.6102(4) 1.1878(4) 0.99088(11) 0.0512(9) Uani 1 1 d .
C54 0.6285(5) 1.1068(5) 1.03099(12) 0.0602(10) Uani 1 1 d .
C55 0.5344(5) 0.9847(5) 1.03903(13) 0.0638(11) Uani 1 1 d .
C56 0.4215(4) 0.9412(4) 1.00667(11) 0.0446(8) Uani 1 1 d .
H1 0.4039 0.6014 0.7915 0.032 Uiso 1 1 calc R
H2 0.6382 0.5413 0.8290 0.033 Uiso 1 1 calc R
H3 0.5556 0.8018 0.8155 0.029 Uiso 1 1 calc R
H4 0.5819 0.8924 0.9086 0.030 Uiso 1 1 calc R
H32 0.8399 0.9717 0.7659 0.044 Uiso 1 1 calc R
H33 0.8813 1.2266 0.7543 0.055 Uiso 1 1 calc R
H34 0.9041 1.3856 0.8173 0.059 Uiso 1 1 calc R
H35 0.8844 1.2938 0.8929 0.061 Uiso 1 1 calc R
H36 0.8427 1.0385 0.9057 0.047 Uiso 1 1 calc R
H52 0.4808 1.2038 0.9314 0.050 Uiso 1 1 calc R
H53 0.6759 1.2718 0.9851 0.061 Uiso 1 1 calc R
H54 0.7063 1.1353 1.0532 0.072 Uiso 1 1 calc R
H55 0.5467 0.9295 1.0670 0.077 Uiso 1 1 calc R
H56 0.3579 0.8556 1.0122 0.054 Uiso 1 1 calc R
H6A 0.2982 0.8499 0.8147 0.033 Uiso 1 1 calc R
H6B 0.1498 0.8556 0.8493 0.033 Uiso 1 1 calc R
H7A 0.2426 0.6111 0.8787 0.035 Uiso 1 1 calc R
H7B 0.1571 0.6113 0.8291 0.035 Uiso 1 1 calc R
H13A 0.3143 0.1289 0.7708 0.065 Uiso 1 1 calc R
H13B 0.2878 0.1600 0.8250 0.065 Uiso 1 1 calc R
H13C 0.4563 0.1023 0.8068 0.065 Uiso 1 1 calc R
H21A 0.4936 0.5844 0.9177 0.058 Uiso 1 1 calc R
H21B 0.6751 0.5401 0.9091 0.058 Uiso 1 1 calc R
H21C 0.5370 0.4245 0.8966 0.058 Uiso 1 1 calc R
loop_
_atom_type_symbol
_atom_type_radius_bond
S 1.02
O 0.73
C 0.77
H 0.32
loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
O31 S3 O32 118.63(13)
O31 S3 C31 107.67(13)
O32 S3 C31 108.13(13)
O31 S3 C3 109.37(13)
O32 S3 C3 107.33(13)
C31 S3 C3 104.88(12)
C5 S5 C51 102.39(13)
C12 O11 C1 118.4(2)
O11 C1 C7 104.2(2)
O11 C1 C2 108.6(2)
C7 C1 C2 117.9(2)
O11 C1 H1 108.60
C7 C1 H1 108.60
C2 C1 H1 108.60
C21 C2 C1 113.4(2)
C21 C2 C3 113.5(2)
C1 C2 C3 108.1(2)
C21 C2 H2 107.20
C1 C2 H2 107.20
C3 C2 H2 107.20
C4 C3 C2 113.5(2)
C4 C3 S3 110.78(19)
C2 C3 S3 109.88(17)
C4 C3 H3 107.50
C2 C3 H3 107.50
S3 C3 H3 107.50
C5 C4 C3 119.8(2)
C5 C4 H4 120.10
C3 C4 H4 120.10
C4 C5 C6 122.4(2)
C4 C5 S5 125.6(2)
C6 C5 S5 111.90(19)
C5 C6 C7 112.1(2)
C5 C6 H6A 109.20
C7 C6 H6A 109.20
C5 C6 H6B 109.20
C7 C6 H6B 109.20
H6A C6 H6B 107.90
C1 C7 C6 114.5(2)
C1 C7 H7A 108.60
C6 C7 H7A 108.60
C1 C7 H7B 108.60
C6 C7 H7B 108.60
H7A C7 H7B 107.60
O12 C12 O11 123.0(2)
O12 C12 C13 125.9(3)
O11 C12 C13 111.1(3)
C12 C13 H13A 109.50
C12 C13 H13B 109.50
H13A C13 H13B 109.50
C12 C13 H13C 109.50
H13A C13 H13C 109.50
H13B C13 H13C 109.50
C2 C21 H21A 109.50
C2 C21 H21B 109.50
H21A C21 H21B 109.50
C2 C21 H21C 109.50
H21A C21 H21C 109.50
H21B C21 H21C 109.50
C36 C31 C32 121.3(3)
C36 C31 S3 119.2(2)
C32 C31 S3 119.5(2)
C33 C32 C31 119.1(3)
C33 C32 H32 120.50
C31 C32 H32 120.50
C34 C33 C32 120.3(3)
C34 C33 H33 119.80
C32 C33 H33 119.80
C33 C34 C35 120.5(3)
C33 C34 H34 119.80
C35 C34 H34 119.80
C34 C35 C36 120.3(3)
C34 C35 H35 119.80
C36 C35 H35 119.80
C31 C36 C35 118.5(3)
C31 C36 H36 120.70
C35 C36 H36 120.70
C56 C51 C52 119.8(3)
C56 C51 S5 120.0(2)
C52 C51 S5 120.2(2)
C51 C52 C53 120.4(3)
C51 C52 H52 119.80
C53 C52 H52 119.80
C54 C53 C52 119.7(3)
C54 C53 H53 120.20
C52 C53 H53 120.20
C53 C54 C55 120.0(3)
C53 C54 H54 120.00
C55 C54 H54 120.00
C54 C55 C56 120.5(3)
C54 C55 H55 119.70
C56 C55 H55 119.70
C51 C56 C55 119.6(3)
C51 C56 H56 120.20
C55 C56 H56 120.20
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
S3 O31 1.436(2)
S3 O32 1.444(2)
S3 C31 1.773(3)
S3 C3 1.790(3)
S5 C5 1.763(3)
S5 C51 1.773(3)
O11 C12 1.349(3)
O11 C1 1.463(3)
O12 C12 1.207(3)
C1 C7 1.506(4)
C1 C2 1.534(4)
C1 H1 1.0000
C2 C21 1.527(4)
C2 C3 1.552(3)
C2 H2 1.0000
C3 C4 1.508(4)
C3 H3 1.0000
C4 C5 1.335(4)
C4 H4 0.9500
C5 C6 1.503(4)
C6 C7 1.539(3)
C6 H6A 0.9900
C6 H6B 0.9900
C7 H7A 0.9900
C7 H7B 0.9900
C12 C13 1.490(4)
C13 H13A 0.9800
C13 H13B 0.9800
C13 H13C 0.9800
C21 H21A 0.9800
C21 H21B 0.9800
C21 H21C 0.9800
C31 C36 1.387(4)
C31 C32 1.390(4)
C32 C33 1.383(4)
C32 H32 0.9500
C33 C34 1.371(5)
C33 H33 0.9500
C34 C35 1.386(5)
C34 H34 0.9500
C35 C36 1.389(5)
C35 H35 0.9500
C36 H36 0.9500
C51 C56 1.374(4)
C51 C52 1.378(4)
C52 C53 1.387(5)
C52 H52 0.9500
C53 C54 1.372(5)
C53 H53 0.9500
C54 C55 1.373(5)
C54 H54 0.9500
C55 C56 1.387(5)
C55 H55 0.9500
C56 H56 0.9500
loop_
_geom_torsion_atom_site_label_1
_geom_torsion_atom_site_label_2
_geom_torsion_atom_site_label_3
_geom_torsion_atom_site_label_4
_geom_torsion
C12 O11 C1 C7 149.2(2)
C12 O11 C1 C2 -84.3(3)
O11 C1 C2 C21 -53.8(3)
C7 C1 C2 C21 64.3(3)
O11 C1 C2 C3 179.5(2)
C7 C1 C2 C3 -62.4(3)
C21 C2 C3 C4 -44.0(3)
C1 C2 C3 C4 82.7(3)
C21 C2 C3 S3 80.7(3)
C1 C2 C3 S3 -152.68(19)
O31 S3 C3 C4 55.2(2)
O32 S3 C3 C4 -174.91(18)
C31 S3 C3 C4 -60.1(2)
O31 S3 C3 C2 -71.0(2)
O32 S3 C3 C2 58.9(2)
C31 S3 C3 C2 173.8(2)
C2 C3 C4 C5 -71.9(3)
S3 C3 C4 C5 164.0(2)
C3 C4 C5 C6 1.2(4)
C3 C4 C5 S5 176.60(19)
C51 S5 C5 C4 1.1(3)
C51 S5 C5 C6 176.93(19)
C4 C5 C6 C7 64.6(3)
S5 C5 C6 C7 -111.4(2)
O11 C1 C7 C6 -175.9(2)
C2 C1 C7 C6 63.6(3)
C5 C6 C7 C1 -78.3(3)
C1 O11 C12 O12 0.4(4)
C1 O11 C12 C13 -179.0(2)
O31 S3 C31 C36 -23.1(3)
O32 S3 C31 C36 -152.4(2)
C3 S3 C31 C36 93.3(2)
O31 S3 C31 C32 153.8(2)
O32 S3 C31 C32 24.5(2)
C3 S3 C31 C32 -89.8(2)
C36 C31 C32 C33 -1.5(4)
S3 C31 C32 C33 -178.4(2)
C31 C32 C33 C34 0.8(5)
C32 C33 C34 C35 -0.1(5)
C33 C34 C35 C36 0.0(5)
C32 C31 C36 C35 1.5(4)
S3 C31 C36 C35 178.4(2)
C34 C35 C36 C31 -0.8(5)
C5 S5 C51 C56 -101.2(3)
C5 S5 C51 C52 80.8(3)
C56 C51 C52 C53 1.1(5)
S5 C51 C52 C53 179.0(3)
C51 C52 C53 C54 -1.5(5)
C52 C53 C54 C55 0.6(6)
C53 C54 C55 C56 0.6(7)
C52 C51 C56 C55 0.2(5)
S5 C51 C56 C55 -177.8(3)
C54 C55 C56 C51 -1.1(6)
loop_
_cod_related_entry_id
_cod_related_entry_database
_cod_related_entry_code
1 PubChem 139037511
