#------------------------------------------------------------------------------
#$Date: 2017-10-14 22:27:35 +0300 (Sat, 14 Oct 2017) $
#$Revision: 202017 $
#$URL: file:///home/coder/svn-repositories/cod/cif/7/15/09/7150930.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_7150930
loop_
_publ_author_name
'Hussain, Ibrar'
'Riahi, Abdolmajid'
'Yawer, Mirza Arfan'
'Villinger, Alexander'
'Fischer, Christine'
'Görls, Helmar'
'Langer, Peter'
_publ_section_title
;
 One-pot synthesis of 6-(thien-2-yl)- and 6-(fur-2-yl)salicylates based
 on regioselective [3 + 3] cyclocondensations of
 1,3-bis(trimethylsilyloxy)-1,3-butadienes
;
_journal_issue                   19
_journal_name_full               'Organic & Biomolecular Chemistry'
_journal_page_first              3542
_journal_page_last               3551
_journal_paper_doi               10.1039/b803472a
_journal_volume                  6
_journal_year                    2008
_chemical_formula_sum            'C14 H14 O3 S'
_chemical_formula_weight         262.31
_chemical_name_systematic
;
?
;
_space_group_IT_number           2
_symmetry_cell_setting           triclinic
_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
_atom_sites_solution_secondary   difmap
_audit_creation_method           SHELXL-97
_cell_angle_alpha                95.843(4)
_cell_angle_beta                 105.477(5)
_cell_angle_gamma                98.661(5)
_cell_formula_units_Z            2
_cell_length_a                   7.0866(5)
_cell_length_b                   9.2066(7)
_cell_length_c                   10.2121(9)
_cell_measurement_reflns_used    4319
_cell_measurement_temperature    183(2)
_cell_measurement_theta_max      27.42
_cell_measurement_theta_min      3.04
_cell_volume                     627.70(9)
_computing_cell_refinement       DENZO
_computing_data_collection       COLLECT
_computing_data_reduction        DENZO
_computing_molecular_graphics    SHELXTL/PC
_computing_publication_material  SHELXL-97
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 1990)'
_diffrn_ambient_temperature      183(2)
_diffrn_measured_fraction_theta_full 0.963
_diffrn_measured_fraction_theta_max 0.963
_diffrn_measurement_device_type  KappaCCD
_diffrn_measurement_method       'phi- + omega-scan'
_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  0.0407
_diffrn_reflns_av_sigmaI/netI    0.0914
_diffrn_reflns_limit_h_max       9
_diffrn_reflns_limit_h_min       -8
_diffrn_reflns_limit_k_max       11
_diffrn_reflns_limit_k_min       -11
_diffrn_reflns_limit_l_max       11
_diffrn_reflns_limit_l_min       -13
_diffrn_reflns_number            4319
_diffrn_reflns_theta_full        27.42
_diffrn_reflns_theta_max         27.42
_diffrn_reflns_theta_min         3.04
_exptl_absorpt_coefficient_mu    0.255
_exptl_absorpt_correction_type   none
_exptl_crystal_colour            colourless
_exptl_crystal_density_diffrn    1.388
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       prism
_exptl_crystal_F_000             276
_exptl_crystal_size_max          0.04
_exptl_crystal_size_mid          0.04
_exptl_crystal_size_min          0.03
_refine_diff_density_max         1.090
_refine_diff_density_min         -0.609
_refine_diff_density_rms         0.098
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.031
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     165
_refine_ls_number_reflns         2743
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.031
_refine_ls_R_factor_all          0.1367
_refine_ls_R_factor_gt           0.0757
_refine_ls_shift/su_max          0.003
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'calc w=1/[σ²(Fo²)+(0.1008P)²+1.4708P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1982
_refine_ls_wR_factor_ref         0.2341
_reflns_number_gt                1645
_reflns_number_total             2743
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            b803472a.txt
_cod_data_source_block           FO3241
_cod_depositor_comments
;
The following automatic conversions were performed:
'_exptl_absorpt_correction_type' value 'NONE' changed to 'none' 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_enum 1527 2010-12-29 10:47:43Z saulius 
;
_cod_original_sg_symbol_H-M      P-1
_cod_database_code               7150930
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
S S 0.7860(2) 0.35102(15) 0.04290(14) 0.0404(4) Uani 1 1 d . . .
O1 O 0.7992(5) 0.3946(4) 0.5998(4) 0.0301(8) Uani 1 1 d . . .
O2 O 0.5520(5) 0.4601(3) 0.3759(3) 0.0337(8) Uani 1 1 d . . .
O3 O 0.4672(4) 0.2722(3) 0.2018(3) 0.0265(7) Uani 1 1 d . . .
C1 C 0.7142(7) 0.2476(5) -0.1119(5) 0.0332(11) Uani 1 1 d . . .
H1A H 0.6875 0.2882 -0.1954 0.040 Uiso 1 1 calc R . .
C2 C 0.6977(7) 0.0994(5) -0.1068(5) 0.0349(11) Uani 1 1 d . . .
H2A H 0.6550 0.0279 -0.1876 0.042 Uiso 1 1 calc R . .
C3 C 0.7502(5) 0.0559(4) 0.0321(4) 0.0180(8) Uiso 1 1 d . . .
H3A H 0.7546 -0.0410 0.0556 0.022 Uiso 1 1 calc R . .
C4 C 0.7946(6) 0.1993(5) 0.1269(4) 0.0217(9) Uani 1 1 d . . .
C5 C 0.8645(6) 0.2158(4) 0.2791(4) 0.0201(9) Uani 1 1 d . . .
C6 C 0.7788(6) 0.2949(4) 0.3673(4) 0.0203(9) Uani 1 1 d . . .
C7 C 0.8705(6) 0.3167(4) 0.5094(4) 0.0211(9) Uani 1 1 d . . .
C8 C 1.0389(6) 0.2569(4) 0.5668(4) 0.0234(9) Uani 1 1 d . . .
C9 C 1.1193(6) 0.1762(5) 0.4779(5) 0.0241(9) Uani 1 1 d . . .
C10 C 1.0317(6) 0.1580(5) 0.3379(4) 0.0236(9) Uani 1 1 d . . .
H10A H 1.0884 0.1034 0.2791 0.028 Uiso 1 1 calc R . .
C12 C 0.2989(6) 0.3350(5) 0.1358(5) 0.0329(11) Uani 1 1 d . . .
H12A H 0.2023 0.2589 0.0660 0.049 Uiso 1 1 calc R . .
H12B H 0.3436 0.4182 0.0919 0.049 Uiso 1 1 calc R . .
H12C H 0.2360 0.3706 0.2044 0.049 Uiso 1 1 calc R . .
C11 C 0.5929(6) 0.3522(5) 0.3162(5) 0.0231(9) Uani 1 1 d . . .
C13 C 1.1291(7) 0.2810(5) 0.7201(5) 0.0333(11) Uani 1 1 d . . .
H13A H 1.2747 0.3024 0.7418 0.050 Uiso 1 1 calc R . .
H13B H 1.0878 0.1912 0.7571 0.050 Uiso 1 1 calc R . .
H13C H 1.0835 0.3649 0.7613 0.050 Uiso 1 1 calc R . .
C14 C 1.3057(6) 0.1127(5) 0.5326(5) 0.0338(11) Uani 1 1 d . . .
H14A H 1.3308 0.0512 0.4571 0.051 Uiso 1 1 calc R . .
H14B H 1.2871 0.0518 0.6030 0.051 Uiso 1 1 calc R . .
H14C H 1.4196 0.1942 0.5728 0.051 Uiso 1 1 calc R . .
H1O1 H 0.743(8) 0.435(6) 0.575(6) 0.027(17) Uiso 1 1 d . . .
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
C1 S C4 93.1(2) . . ?
C7 O1 H1O1 116(6) . . ?
C11 O3 C12 116.5(3) . . ?
C2 C1 S 113.3(4) . . ?
C2 C1 H1A 123.3 . . ?
S C1 H1A 123.3 . . ?
C1 C2 C3 116.1(4) . . ?
C1 C2 H2A 122.0 . . ?
C3 C2 H2A 122.0 . . ?
C2 C3 C4 104.2(3) . . ?
C2 C3 H3A 127.9 . . ?
C4 C3 H3A 127.9 . . ?
C5 C4 C3 125.1(3) . . ?
C5 C4 S 121.4(3) . . ?
C3 C4 S 113.1(3) . . ?
C10 C5 C6 118.3(4) . . ?
C10 C5 C4 117.7(4) . . ?
C6 C5 C4 123.9(3) . . ?
C7 C6 C5 118.8(3) . . ?
C7 C6 C11 118.4(4) . . ?
C5 C6 C11 122.7(4) . . ?
O1 C7 C8 116.0(4) . . ?
O1 C7 C6 122.0(4) . . ?
C8 C7 C6 122.0(4) . . ?
C7 C8 C9 118.3(4) . . ?
C7 C8 C13 119.8(4) . . ?
C9 C8 C13 121.9(4) . . ?
C10 C9 C8 119.6(4) . . ?
C10 C9 C14 119.2(4) . . ?
C8 C9 C14 121.2(4) . . ?
C9 C10 C5 122.9(4) . . ?
C9 C10 H10A 118.5 . . ?
C5 C10 H10A 118.5 . . ?
O3 C12 H12A 109.5 . . ?
O3 C12 H12B 109.5 . . ?
H12A C12 H12B 109.5 . . ?
O3 C12 H12C 109.5 . . ?
H12A C12 H12C 109.5 . . ?
H12B C12 H12C 109.5 . . ?
O2 C11 O3 122.1(4) . . ?
O2 C11 C6 123.6(4) . . ?
O3 C11 C6 114.2(3) . . ?
C8 C13 H13A 109.5 . . ?
C8 C13 H13B 109.5 . . ?
H13A C13 H13B 109.5 . . ?
C8 C13 H13C 109.5 . . ?
H13A C13 H13C 109.5 . . ?
H13B C13 H13C 109.5 . . ?
C9 C14 H14A 109.5 . . ?
C9 C14 H14B 109.5 . . ?
H14A C14 H14B 109.5 . . ?
C9 C14 H14C 109.5 . . ?
H14A C14 H14C 109.5 . . ?
H14B C14 H14C 109.5 . . ?
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
S C1 1.668(5) . ?
S C4 1.713(4) . ?
O1 C7 1.358(5) . ?
O1 H1O1 0.61(5) . ?
O2 C11 1.225(5) . ?
O3 C11 1.331(5) . ?
O3 C12 1.438(5) . ?
C1 C2 1.359(7) . ?
C1 H1A 0.9500 . ?
C2 C3 1.480(6) . ?
C2 H2A 0.9500 . ?
C3 C4 1.493(6) . ?
C3 H3A 0.9500 . ?
C4 C5 1.484(6) . ?
C5 C10 1.386(5) . ?
C5 C6 1.416(5) . ?
C6 C7 1.402(6) . ?
C6 C11 1.478(5) . ?
C7 C8 1.400(5) . ?
C8 C9 1.402(6) . ?
C8 C13 1.504(6) . ?
C9 C10 1.381(6) . ?
C9 C14 1.517(5) . ?
C10 H10A 0.9500 . ?
C12 H12A 0.9800 . ?
C12 H12B 0.9800 . ?
C12 H12C 0.9800 . ?
C13 H13A 0.9800 . ?
C13 H13B 0.9800 . ?
C13 H13C 0.9800 . ?
C14 H14A 0.9800 . ?
C14 H14B 0.9800 . ?
C14 H14C 0.9800 . ?
loop_
_cod_related_entry_id
_cod_related_entry_database
_cod_related_entry_code
1 ChemSpider 25938134
