#------------------------------------------------------------------------------
#$Date: 2025-08-19 01:52:38 +0300 (Tue, 19 Aug 2025) $
#$Revision: 301791 $
#$URL: file:///home/coder/svn-repositories/cod/cif/2/00/69/2006908.cif $
#------------------------------------------------------------------------------
#
# This file is available in the Crystallography Open Database (COD),
# http://www.crystallography.net/. The original data for this entry
# were provided by IUCr Journals, http://journals.iucr.org/.
#
# The file may be used within the scientific community so long as
# proper attribution is given to the journal article from which the
# data were obtained.
#
data_2006908
loop_
_publ_author_name
'Zukerman-Schpector, J.'
'Monteiro, Hugo J.'
_publ_section_title
;
 Intermediates in the Synthesis of (+)-Grandisol. II
;
_journal_issue                   1
_journal_name_full               'Acta Crystallographica Section C'
_journal_page_first              96
_journal_page_last               97
_journal_paper_doi               10.1107/S0108270197011426
_journal_volume                  54
_journal_year                    1998
_chemical_formula_moiety         'C14 H16 O3 S'
_chemical_formula_sum            'C14 H16 O3 S'
_chemical_formula_weight         264.33
_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'
_audit_creation_method           'manual editing of SHELXL93.CIF'
_cell_angle_alpha                90.00
_cell_angle_beta                 90.00
_cell_angle_gamma                90.00
_cell_formula_units_Z            4
_cell_length_a                   7.4828(8)
_cell_length_b                   12.1260(10)
_cell_length_c                   14.179(2)
_cell_measurement_reflns_used    25
_cell_measurement_temperature    293
_cell_measurement_theta_max      17.30
_cell_measurement_theta_min      10.87
_cell_volume                     1286.6(3)
_computing_cell_refinement       'CAD-4 Software'
_computing_data_collection       'CAD-4 Software (Enraf-Nonius, 1989)'
_computing_data_reduction        'MolEN (Fair, 1990)'
_computing_molecular_graphics    'ZORTEP (Zsolnai, 1995)'
_computing_publication_material  SHELXL93
_computing_structure_refinement  'SHELXL93 (Sheldrick, 1993)'
_computing_structure_solution    'SHELXS86 (Sheldrick, 1985)'
_diffrn_measurement_device_type  'Enraf-Nonius CAD-4'
_diffrn_measurement_method       ω/2θ
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_source         'fine-focus sealed tube'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_limit_h_max       9
_diffrn_reflns_limit_h_min       0
_diffrn_reflns_limit_k_max       0
_diffrn_reflns_limit_k_min       -16
_diffrn_reflns_limit_l_max       18
_diffrn_reflns_limit_l_min       0
_diffrn_reflns_number            1795
_diffrn_reflns_theta_max         28.0
_diffrn_standards_decay_%        0.9
_diffrn_standards_interval_time  30
_diffrn_standards_number         2
_exptl_absorpt_coefficient_mu    0.249
_exptl_absorpt_correction_type   none
_exptl_crystal_colour            colourless
_exptl_crystal_density_diffrn    1.365
_exptl_crystal_density_meas      ?
_exptl_crystal_description       prismatic
_exptl_crystal_F_000             560.0
_exptl_crystal_size_max          0.40
_exptl_crystal_size_mid          0.15
_exptl_crystal_size_min          0.15
_refine_diff_density_max         0.279
_refine_diff_density_min         -0.234
_refine_ls_abs_structure_details 'Flack (1983)'
_refine_ls_abs_structure_Flack   0.0(3)
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_all   1.130
_refine_ls_goodness_of_fit_ref   1.078
_refine_ls_hydrogen_treatment    'H atoms riding'
_refine_ls_matrix_type           full
_refine_ls_number_parameters     174
_refine_ls_number_reflns         1795
_refine_ls_number_restraints     6
_refine_ls_restrained_S_all      1.129
_refine_ls_restrained_S_obs      1.078
_refine_ls_R_factor_all          0.0988
_refine_ls_R_factor_gt           0.041
_refine_ls_shift/su_max          <0.001
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'w = 1/[σ²(Fo²)+(0.0337P)²+0.566P] where P = (Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_all         0.119
_refine_ls_wR_factor_ref         0.0857
_reflns_number_gt                1085
_reflns_number_total             1795
_reflns_threshold_expression     'F² > 2σ(F²)'
_cod_data_source_file            cf1177.cif
_cod_data_source_block           default
_cod_depositor_comments
;
The following automatic conversions were performed:

'_exptl_crystal_density_meas' value 'not measured' was changed to '?'
- the value is perceived as not measured.

Automatic conversion script
Id: cif_fix_values 3008 2015-01-20 13:52:24Z robertas 

The following automatic conversions were performed:

'_refine_ls_weighting_scheme' value 'calc w =
1/[\s^2^(Fo^2^)+(0.0337P)^2^+0.566P] where P = (Fo^2^+2Fc^2^)/3' was
changed to 'calc'. New tag '_refine_ls_weighting_details' was
created. The value of the new tag was set to 'w =
1/[\s^2^(Fo^2^)+(0.0337P)^2^+0.566P] where P = (Fo^2^+2Fc^2^)/3'.

Automatic conversion script
Id: cif_fix_values 3143 2015-03-26 13:38:13Z robertas 
;
_cod_database_code               2006908
loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'-x+1/2, -y, z+1/2'
'x+1/2, -y+1/2, -z'
'-x, y+1/2, -z+1/2'
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_calc_flag
_atom_site_refinement_flags
_atom_site_occupancy
_atom_site_disorder_group
_atom_site_type_symbol
S 1.0002(2) .35570(9) .80928(6) .0444(3) Uani d . 1 . S
O1 .9855(6) .2419(3) .8383(2) .0714(11) Uani d . 1 . O
O2 .9158(5) .4383(4) .8653(2) .0787(13) Uani d . 1 . O
O3A 1.320(4) .276(4) .6754(15) .089(8) Uani d PU .51(9) 1 O
O3B 1.287(6) .235(4) .691(3) .103(9) Uani d PU .49(9) 2 O
C1 1.2323(5) .3871(3) .8028(3) .0354(9) Uani d . 1 . C
C2 1.3346(7) .2916(4) .7574(3) .0529(12) Uani d . 1 . C
C3 1.4839(7) .2557(4) .8198(4) .0655(13) Uani d . 1 . C
H3A 1.5979(7) .2759(4) .7922(4) .079 Uiso calc R 1 . H
H3B 1.4812(7) .1764(4) .8280(4) .079 Uiso calc R 1 . H
C4 1.4596(6) .3125(4) .9130(3) .0576(14) Uani d . 1 . C
H4A 1.5744(6) .3356(4) .9380(3) .069 Uiso calc R 1 . H
H4B 1.4040(6) .2630(4) .9580(3) .069 Uiso calc R 1 . H
C5 1.3395(6) .4132(3) .8955(3) .0407(10) Uani d . 1 . C
C6 1.4269(7) .5095(4) .8402(3) .0551(13) Uani d . 1 . C
H6A 1.4223(7) .5795(4) .8734(3) .066 Uiso calc R 1 . H
H6B 1.5475(7) .4937(4) .8192(3) .066 Uiso calc R 1 . H
C7 1.2868(7) .4992(4) .7621(3) .0573(13) Uani d . 1 . C
H7A 1.3371(7) .4950(4) .6992(3) .069 Uiso calc R 1 . H
H7B 1.1933(7) .5545(4) .7653(3) .069 Uiso calc R 1 . H
C8 1.2444(7) .4490(4) .9839(3) .0601(14) Uani d . 1 . C
H8A 1.171(3) .5121(17) .9703(6) .090 Uiso calc R 1 . H
H8B 1.3307(7) .468(3) 1.0312(8) .090 Uiso calc R 1 . H
H8C 1.171(3) .3899(10) 1.0064(13) .090 Uiso calc R 1 . H
C9 .9123(5) .3693(3) .6940(3) .0400(9) Uani d . 1 . C
C10 .9085(7) .2792(4) .6350(3) .0510(12) Uani d . 1 . C
H10 .9568(7) .2121(4) .6542(3) .061 Uiso calc R 1 . H
C11 .8316(7) .2900(5) .5468(3) .0635(14) Uani d . 1 . C
H11 .8279(7) .2299(5) .5061(3) .076 Uiso calc R 1 . H
C12 .7606(7) .3892(4) .5192(3) .0573(13) Uani d . 1 . C
H12 .7074(7) .3955(4) .4602(3) .069 Uiso calc R 1 . H
C13 .7673(7) .4778(4) .5771(3) .0581(13) Uani d . 1 . C
H13 .7205(7) .5448(4) .5570(3) .070 Uiso calc R 1 . H
C14 .8434(6) .4697(4) .6662(3) .0505(12) Uani d . 1 . C
H14 .8477(6) .5304(4) .7061(3) .061 Uiso calc R 1 . H
loop_
_atom_site_aniso_label
_atom_site_aniso_U_11
_atom_site_aniso_U_22
_atom_site_aniso_U_33
_atom_site_aniso_U_12
_atom_site_aniso_U_13
_atom_site_aniso_U_23
S .0348(4) .0669(6) .0314(4) -.0032(6) .0021(6) -.0012(5)
O1 .083(3) .081(2) .051(2) -.035(2) -.013(2) .031(2)
O2 .048(2) .139(4) .049(2) .030(2) -.002(2) -.036(2)
O3A .088(9) .130(19) .050(7) .030(11) .009(8) -.047(9)
O3B .100(14) .105(17) .104(14) .059(12) -.056(11) -.069(11)
C1 .030(2) .043(2) .034(2) .002(2) .003(2) -.001(2)
C2 .043(3) .071(3) .045(2) .004(3) .006(2) -.016(3)
C3 .051(3) .066(3) .079(3) .021(3) -.008(3) -.008(3)
C4 .055(3) .061(3) .057(3) .008(2) -.013(2) -.001(2)
C5 .040(2) .044(2) .037(2) -.003(2) -.002(2) -.003(2)
C6 .056(3) .055(3) .054(3) -.011(2) -.002(2) .002(2)
C7 .063(3) .054(3) .055(3) -.012(3) -.008(3) .016(2)
C8 .057(3) .087(4) .037(2) .000(3) .000(2) -.017(2)
C9 .033(2) .053(3) .034(2) -.006(2) .003(2) .001(2)
C10 .063(3) .045(3) .044(2) -.005(2) -.006(2) .004(2)
C11 .075(4) .064(3) .051(3) -.004(3) -.012(3) -.012(3)
C12 .053(3) .073(4) .045(2) -.002(3) -.007(2) .012(2)
C13 .054(3) .061(3) .060(3) .010(3) -.006(3) .013(3)
C14 .041(2) .054(3) .057(3) .006(2) .000(2) -.007(2)
loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
S S 0.1246 0.1234 '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'
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'
loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_publ_flag
O2 S O1 118.6(3) yes
O2 S C9 106.5(2) yes
O1 S C9 108.9(2) yes
O2 S C1 108.1(2) yes
O1 S C1 107.1(2) yes
C9 S C1 107.2(2) yes
C2 C1 C7 112.3(3) yes
C2 C1 C5 104.4(3) yes
C7 C1 C5 90.0(3) yes
C2 C1 S 110.4(3) yes
C7 C1 S 118.0(3) yes
C5 C1 S 119.9(3) yes
O3A C2 C3 127.3(14) no
O3B C2 C3 120.7(14) no
O3A C2 C1 119.3(19) no
O3B C2 C1 127.4(13) no
C3 C2 C1 110.2(4) no
C2 C3 C4 107.3(4) no
C3 C4 C5 107.0(3) no
C8 C5 C4 111.8(4) yes
C8 C5 C6 113.7(4) yes
C4 C5 C6 115.7(4) yes
C8 C5 C1 120.8(3) yes
C4 C5 C1 105.9(3) yes
C6 C5 C1 86.8(3) yes
C7 C6 C5 90.9(3) yes
C6 C7 C1 89.0(3) yes
C10 C9 C14 121.3(4) no
C10 C9 S 119.7(3) no
C14 C9 S 119.0(3) no
C9 C10 C11 118.9(4) no
C12 C11 C10 120.1(5) no
C13 C12 C11 120.6(4) no
C12 C13 C14 120.7(4) no
C9 C14 C13 118.4(4) no
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_publ_flag
S O2 1.426(4) yes
S O1 1.444(3) yes
S C9 1.769(4) yes
S C1 1.780(4) yes
O3A C2 1.18(2) no
O3B C2 1.22(2) no
C1 C2 1.531(6) no
C1 C7 1.532(5) yes
C1 C5 1.572(5) yes
C2 C3 1.490(7) no
C3 C4 1.501(6) no
C4 C5 1.536(6) no
C5 C8 1.506(6) yes
C5 C6 1.551(6) yes
C6 C7 1.530(6) yes
C9 C10 1.376(6) no
C9 C14 1.380(6) no
C10 C11 1.384(6) no
C11 C12 1.371(7) no
C12 C13 1.353(7) no
C13 C14 1.390(6) no
loop_
_cod_related_entry_id
_cod_related_entry_database
_cod_related_entry_code
1 PubChem 101938664
