#------------------------------------------------------------------------------
#$Date: 2017-10-14 22:27:35 +0300 (Sat, 14 Oct 2017) $
#$Revision: 202017 $
#$URL: file:///home/coder/svn-repositories/cod/cif/7/15/12/7151244.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_7151244
loop_
_publ_author_name
'Okuma, Kentaro'
'Koda, Masahiro'
'Maekawa, Shinobu'
'Shioji, Kosei'
'Inoue, Tohru'
'Kurisaki, Tsutomu'
'Wakita, Hisanobu'
'Yokomori, Yoshinobu'
_publ_section_title
;
 Reaction of thioketones with propiolic acids.
;
_journal_issue                   14
_journal_name_full               'Organic & biomolecular chemistry'
_journal_page_first              2745
_journal_page_last               2752
_journal_paper_doi               10.1039/b605068a
_journal_volume                  4
_journal_year                    2006
_chemical_compound_source        'K. Okuma'
_chemical_formula_moiety         'C13 H18 O2 S '
_chemical_formula_sum            'C13 H18 O2 S'
_chemical_formula_weight         238.349
_chemical_name_systematic
;
?
;
_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           maXus
_cell_angle_alpha                90.00
_cell_angle_beta                 90.00
_cell_angle_gamma                90.00
_cell_formula_units_Z            4
_cell_length_a                   7.69(5)
_cell_length_b                   9.26(5)
_cell_length_c                   17.15(5)
_cell_measurement_reflns_used    25
_cell_measurement_temperature    298
_cell_measurement_theta_max      15.0000
_cell_measurement_theta_min      11.5800
_cell_volume                     1221(11)
_computing_cell_refinement       'Enraf Nonius CAD4, 1989'
_computing_data_collection       'Enraf Nonius CAD4, 1989'
_computing_data_reduction        'maXus (Mackay et al., 1999)'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_diffrn_measured_fraction_theta_full 1.000
_diffrn_measured_fraction_theta_max 1.000
_diffrn_measurement_device       'Enraf Nonius CAD4, 1989'
_diffrn_measurement_method       'ω-2θ scan'
_diffrn_orient_matrix_type       X=UH
_diffrn_orient_matrix_UB_11      0.04499
_diffrn_orient_matrix_UB_12      0.09637
_diffrn_orient_matrix_UB_13      0.01684
_diffrn_orient_matrix_UB_21      0.11956
_diffrn_orient_matrix_UB_22      -0.04148
_diffrn_orient_matrix_UB_23      0.00504
_diffrn_orient_matrix_UB_31      0.02450
_diffrn_orient_matrix_UB_32      0.02544
_diffrn_orient_matrix_UB_33      -0.05557
_diffrn_radiation_source         'fine-focus sealed tube'
_diffrn_radiation_type           ' MoK\a'
_diffrn_radiation_wavelength_id  all
_diffrn_reflns_av_R_equivalents  0.033
_diffrn_reflns_limit_h_max       10
_diffrn_reflns_limit_h_min       0
_diffrn_reflns_limit_k_max       13
_diffrn_reflns_limit_k_min       0
_diffrn_reflns_limit_l_max       24
_diffrn_reflns_limit_l_min       -23
_diffrn_reflns_number            4013
_diffrn_reflns_theta_full        29.92
_diffrn_reflns_theta_max         29.91
_diffrn_standards_decay_%        4.091
_diffrn_standards_interval_time  5035
_diffrn_standards_number         3
_exptl_absorpt_coefficient_mu    0.248
_exptl_absorpt_correction_T_max  0.988
_exptl_absorpt_correction_T_min  0.904
_exptl_absorpt_correction_type   psi-scan
_exptl_crystal_colour            Colourless
_exptl_crystal_density_diffrn    1.296
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       Plate
_exptl_crystal_F_000             512.0
_exptl_crystal_size_max          0.40
_exptl_crystal_size_mid          0.30
_exptl_crystal_size_min          0.05
_refine_diff_density_max         0.275
_refine_diff_density_min         -0.235
_refine_diff_density_rms         0.051
_refine_ls_abs_structure_details 'Flack H D (1983), Acta Cryst. A39, 876-881'
_refine_ls_abs_structure_Flack   -0.10(18)
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   0.991
_refine_ls_hydrogen_treatment    refxyz
_refine_ls_matrix_type           full
_refine_ls_number_parameters     145
_refine_ls_number_reflns         2044
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      0.991
_refine_ls_R_factor_all          0.0781
_refine_ls_R_factor_gt           0.0485
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'w=1/[σ²(Fo²)+ (0.1000P)²+0.0000P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1291
_refine_ls_wR_factor_ref         0.1502
_reflns_number_gt                1458
_reflns_number_total             2044
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            b605068a.txt
_cod_data_source_block           compound_1
_cod_depositor_comments
;
The following automatic conversions were performed:
'_symmetry_cell_setting' value 'Orthorhombic' changed to 'orthorhombic'
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 

The following automatic conversions were performed:

'_refine_ls_weighting_scheme' value 'calc w=1/[\s^2^(Fo^2^)+
(0.1000P)^2^+0.0000P] 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^)+ (0.1000P)^2^+0.0000P]
where P=(Fo^2^+2Fc^2^)/3'.

Automatic conversion script
Id: cif_fix_values 3143 2015-03-26 13:38:13Z robertas 
;
_cod_original_cell_volume        1221.(11)
_cod_original_sg_symbol_H-M      'P 21 21 21 '
_cod_original_formula_sum        'C13 H18 O2 S '
_cod_database_code               7151244
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_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_calc_flag
_atom_site_refinement_flags
_atom_site_disorder_assembly
_atom_site_disorder_group
S1 S 0.29459(12) 0.00257(10) -0.00847(4) 0.0542(3) Uani 1 d . . .
O1 O 0.1971(3) -0.1293(2) 0.12183(12) 0.0414(5) Uani 1 d . . .
O2 O 0.2403(5) -0.3581(3) 0.14968(18) 0.0782(9) Uani 1 d . . .
C1 C 0.2830(3) 0.0015(3) 0.09834(13) 0.0361(5) Uani 1 d . . .
C2 C 0.1775(4) 0.1313(3) 0.12973(15) 0.0343(6) Uani 1 d . . .
C3 C 0.2475(5) 0.2670(3) 0.0892(2) 0.0489(8) Uani 1 d . . .
C4 C 0.4334(5) 0.2845(4) 0.1235(2) 0.0586(9) Uani 1 d . . .
C5 C 0.4443(4) 0.1615(4) 0.18250(19) 0.0479(7) Uani 1 d . . .
C6 C 0.4642(4) 0.0197(4) 0.13740(18) 0.0487(7) Uani 1 d . . .
C7 C 0.2561(4) 0.1511(3) 0.21316(15) 0.0372(6) Uani 1 d . . .
C8 C 0.2756(5) -0.2591(4) 0.1069(2) 0.0545(9) Uani 1 d . . .
C9 C 0.3767(6) -0.2696(5) 0.0362(2) 0.0717(12) Uani 1 d . . .
C10 C 0.3786(5) -0.1680(5) -0.0185(2) 0.0713(12) Uani 1 d . . .
C11 C -0.0192(4) 0.1144(3) 0.1231(2) 0.0451(7) Uani 1 d . . .
C12 C 0.2260(5) 0.0273(3) 0.27082(17) 0.0494(8) Uani 1 d . . .
C13 C 0.1926(6) 0.2888(4) 0.2541(2) 0.0559(8) Uani 1 d . . .
H3A H 0.1760 0.3504 0.1011 0.059 Uiso 1 calc R . .
H3B H 0.2515 0.2540 0.0331 0.059 Uiso 1 calc R . .
H4A H 0.5213 0.2743 0.0832 0.070 Uiso 1 calc R . .
H4B H 0.4472 0.3775 0.1487 0.070 Uiso 1 calc R . .
H5 H 0.5318 0.1760 0.2233 0.057 Uiso 1 calc R . .
H6A H 0.4893 -0.0601 0.1723 0.058 Uiso 1 calc R . .
H6B H 0.5557 0.0266 0.0986 0.058 Uiso 1 calc R . .
H9 H 0.4440 -0.3518 0.0286 0.086 Uiso 1 calc R . .
H10 H 0.4296 -0.1913 -0.0660 0.086 Uiso 1 calc R . .
H11A H -0.0509 0.1043 0.0693 0.054 Uiso 1 calc R . .
H11B H -0.0752 0.1981 0.1446 0.054 Uiso 1 calc R . .
H11C H -0.0554 0.0301 0.1514 0.054 Uiso 1 calc R . .
H12A H 0.2358 -0.0633 0.2440 0.059 Uiso 1 calc R . .
H12B H 0.1119 0.0357 0.2931 0.059 Uiso 1 calc R . .
H12C H 0.3115 0.0318 0.3115 0.059 Uiso 1 calc R . .
H13A H 0.2573 0.3028 0.3014 0.067 Uiso 1 calc R . .
H13B H 0.0712 0.2795 0.2662 0.067 Uiso 1 calc R . .
H13C H 0.2097 0.3702 0.2204 0.067 Uiso 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_
_diffrn_attenuator_code
_diffrn_attenuator_scale
1 19.200
loop_
_diffrn_orient_refln_index_h
_diffrn_orient_refln_index_k
_diffrn_orient_refln_index_l
_diffrn_orient_refln_angle_theta
_diffrn_orient_refln_angle_kappa
_diffrn_orient_refln_angle_omega
_diffrn_orient_refln_angle_phi
1 5 4 12.3300 -93.5900 15.1900 -8.9200
-1 5 4 12.3400 -116.3900 17.2000 -15.1900
1 -5 4 12.3300 61.1600 26.4800 -43.1400
1 5 -4 12.3300 -120.0300 -4.6300 50.5600
1 -5 -4 12.3300 54.3300 7.1500 14.7900
-1 5 -4 12.3300 -147.2600 -1.9200 42.8500
-1 -5 4 12.3200 93.9400 29.2800 -51.0900
-1 -5 -4 12.3200 80.7800 9.5000 8.5600
4 2 1 11.5900 -48.1200 7.6300 12.2300
-4 2 1 11.5900 -172.3700 16.0400 -14.0700
4 -2 1 11.5800 0.0500 11.9300 -1.2300
4 2 -1 11.5800 -51.3000 2.6400 27.5600
4 -2 -1 11.5800 -1.2700 7.2200 13.5100
-4 2 -1 11.5900 179.3900 11.2500 0.8100
-4 -2 1 11.5800 146.8200 20.6500 -28.1600
-4 -2 -1 11.5900 139.9400 15.6100 -12.7900
5 3 1 14.9800 -52.7000 10.2400 14.7500
-5 3 1 14.9800 -170.0400 18.3600 -10.7700
5 -3 1 14.9800 4.1000 15.2400 -0.9900
5 3 -1 14.9800 -55.3400 6.3400 26.6300
5 -3 -1 14.9700 3.1400 11.6200 10.4000
-5 3 -1 15.0000 -176.4400 14.7000 0.7000
-5 -3 1 14.9800 142.1400 23.7000 -27.1600
-5 -3 -1 14.9800 136.9300 19.7600 -15.1300
1 5 6 13.4600 -88.3800 20.3000 -21.1200
loop_
_diffrn_radiation_wavelength
0.71069
loop_
_diffrn_standard_refln_index_h
_diffrn_standard_refln_index_k
_diffrn_standard_refln_index_l
1 -4 5
5 -2 -3
4 -1 -1
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
C10 S1 C1 96.5(3) . . ?
C8 O1 C1 119.0(5) . . ?
O1 C1 C2 108.5(4) . . ?
O1 C1 C6 112.5(3) . . ?
C2 C1 C6 103.6(4) . . ?
O1 C1 S1 107.9(3) . . ?
C2 C1 S1 111.7(3) . . ?
C6 C1 S1 112.7(3) . . ?
C11 C2 C3 113.5(3) . . ?
C11 C2 C1 114.5(4) . . ?
C3 C2 C1 107.2(4) . . ?
C11 C2 C7 117.6(3) . . ?
C3 C2 C7 100.5(3) . . ?
C1 C2 C7 101.9(3) . . ?
C2 C3 C4 103.7(4) . . ?
C5 C4 C3 102.9(3) . . ?
C4 C5 C6 108.1(4) . . ?
C4 C5 C7 102.8(3) . . ?
C6 C5 C7 102.2(3) . . ?
C5 C6 C1 102.8(3) . . ?
C12 C7 C13 106.2(4) . . ?
C12 C7 C5 114.1(3) . . ?
C13 C7 C5 113.7(4) . . ?
C12 C7 C2 116.4(3) . . ?
C13 C7 C2 113.1(3) . . ?
C5 C7 C2 93.3(4) . . ?
O2 C8 O1 117.1(5) . . ?
O2 C8 C9 125.5(4) . . ?
O1 C8 C9 117.0(4) . . ?
C10 C9 C8 123.5(4) . . ?
C9 C10 S1 125.3(4) . . ?
C2 C3 H3A 111.0 . . ?
C4 C3 H3A 111.0 . . ?
C2 C3 H3B 111.0 . . ?
C4 C3 H3B 111.0 . . ?
H3A C3 H3B 109.0 . . ?
C5 C4 H4A 111.2 . . ?
C3 C4 H4A 111.2 . . ?
C5 C4 H4B 111.2 . . ?
C3 C4 H4B 111.2 . . ?
H4A C4 H4B 109.1 . . ?
C4 C5 H5 114.2 . . ?
C6 C5 H5 114.2 . . ?
C7 C5 H5 114.2 . . ?
C5 C6 H6A 111.2 . . ?
C1 C6 H6A 111.2 . . ?
C5 C6 H6B 111.2 . . ?
C1 C6 H6B 111.2 . . ?
H6A C6 H6B 109.1 . . ?
C10 C9 H9 118.3 . . ?
C8 C9 H9 118.3 . . ?
C9 C10 H10 117.4 . . ?
S1 C10 H10 117.4 . . ?
C2 C11 H11A 109.5 . . ?
C2 C11 H11B 109.5 . . ?
H11A C11 H11B 109.5 . . ?
C2 C11 H11C 109.5 . . ?
H11A C11 H11C 109.5 . . ?
H11B C11 H11C 109.5 . . ?
C7 C12 H12A 109.5 . . ?
C7 C12 H12B 109.5 . . ?
H12A C12 H12B 109.5 . . ?
C7 C12 H12C 109.5 . . ?
H12A C12 H12C 109.5 . . ?
H12B C12 H12C 109.5 . . ?
C7 C13 H13A 109.5 . . ?
C7 C13 H13B 109.5 . . ?
H13A C13 H13B 109.5 . . ?
C7 C13 H13C 109.5 . . ?
H13A C13 H13C 109.5 . . ?
H13B C13 H13C 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
S1 C10 1.716(9) . ?
S1 C1 1.834(6) . ?
O1 C8 1.370(7) . ?
O1 C1 1.438(7) . ?
O2 C8 1.205(7) . ?
C1 C2 1.546(8) . ?
C1 C6 1.555(9) . ?
C2 C11 1.525(11) . ?
C2 C3 1.534(7) . ?
C2 C7 1.564(6) . ?
C3 C4 1.554(10) . ?
C4 C5 1.526(7) . ?
C5 C6 1.533(8) . ?
C5 C7 1.542(10) . ?
C7 C12 1.532(7) . ?
C7 C13 1.536(8) . ?
C8 C9 1.443(7) . ?
C9 C10 1.329(8) . ?
C3 H3A 0.9700 . ?
C3 H3B 0.9700 . ?
C4 H4A 0.9700 . ?
C4 H4B 0.9700 . ?
C5 H5 0.9800 . ?
C6 H6A 0.9700 . ?
C6 H6B 0.9700 . ?
C9 H9 0.9300 . ?
C10 H10 0.9300 . ?
C11 H11A 0.9600 . ?
C11 H11B 0.9600 . ?
C11 H11C 0.9600 . ?
C12 H12A 0.9600 . ?
C12 H12B 0.9600 . ?
C12 H12C 0.9600 . ?
C13 H13A 0.9600 . ?
C13 H13B 0.9600 . ?
C13 H13C 0.9600 . ?
loop_
_cod_related_entry_id
_cod_related_entry_database
_cod_related_entry_code
1 ChemSpider 9732521
