#------------------------------------------------------------------------------
#$Date: 2016-03-26 16:53:33 +0200 (Sat, 26 Mar 2016) $
#$Revision: 180361 $
#$URL: svn://www.crystallography.net/cod/cif/7/20/30/7203061.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_7203061
loop_
_publ_author_name
'Lehane, K. Niamh'
'Moynihan, Edmond J. A.'
'Brondel, Nicolas'
'Lawrence, Simon E.'
'Maguire, Anita R.'
_publ_section_title
;
 Impact of sulfur substituents on the C--H⋯O interaction of
 terminal alkynes in crystal engineering
;
_journal_issue                   11
_journal_name_full               CrystEngComm
_journal_page_first              1041
_journal_paper_doi               10.1039/b709261j
_journal_volume                  9
_journal_year                    2007
_chemical_formula_moiety         'C10 H10 O2 S'
_chemical_formula_sum            'C10 H10 O2 S'
_chemical_formula_weight         194.24
_chemical_name_systematic
;
?
;
_space_group_IT_number           14
_symmetry_cell_setting           monoclinic
_symmetry_space_group_name_Hall  '-P 2yn'
_symmetry_space_group_name_H-M   'P 1 21/n 1'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_audit_creation_method           SHELXL-97
_cell_angle_alpha                90.00
_cell_angle_beta                 98.590(4)
_cell_angle_gamma                90.00
_cell_formula_units_Z            4
_cell_length_a                   10.5942(7)
_cell_length_b                   7.9196(3)
_cell_length_c                   11.5721(5)
_cell_measurement_reflns_used    25
_cell_measurement_temperature    293(2)
_cell_measurement_theta_max      13.92
_cell_measurement_theta_min      9.74
_cell_volume                     960.03(8)
_computing_cell_refinement       'Nonius MACH3'
_computing_data_collection       'Nonius MACH3'
_computing_data_reduction        'maXus (Gilmoreet al, 1998)'
_computing_molecular_graphics    'PLATON (Spek, 1999)'
_computing_publication_material  'SHELXL--97; PLATON'
_computing_structure_refinement  'SHELXL--97 (Sheldrick, 1997)'
_computing_structure_solution    'SHELXS--97 (Sheldrick, 1990)'
_diffrn_ambient_temperature      293(2)
_diffrn_measured_fraction_theta_full 1.000
_diffrn_measured_fraction_theta_max 1.000
_diffrn_measurement_device_type  'Nonius MACH3'
_diffrn_measurement_method       'ω-2θ scans'
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_source         'fine-focus sealed tube'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71069
_diffrn_reflns_av_R_equivalents  0.0275
_diffrn_reflns_av_sigmaI/netI    0.0156
_diffrn_reflns_limit_h_max       0
_diffrn_reflns_limit_h_min       -12
_diffrn_reflns_limit_k_max       0
_diffrn_reflns_limit_k_min       -9
_diffrn_reflns_limit_l_max       14
_diffrn_reflns_limit_l_min       -13
_diffrn_reflns_number            1875
_diffrn_reflns_theta_full        25.49
_diffrn_reflns_theta_max         25.49
_diffrn_reflns_theta_min         2.43
_diffrn_standards_decay_%        0
_diffrn_standards_interval_time  60
_diffrn_standards_number         3
_exptl_absorpt_coefficient_mu    0.299
_exptl_absorpt_correction_type   none
_exptl_crystal_colour            Colourless
_exptl_crystal_density_diffrn    1.344
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       needles
_exptl_crystal_F_000             408
_exptl_crystal_size_max          0.42
_exptl_crystal_size_mid          0.35
_exptl_crystal_size_min          0.27
_refine_diff_density_max         0.220
_refine_diff_density_min         -0.305
_refine_diff_density_rms         0.050
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.118
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     120
_refine_ls_number_reflns         1777
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.118
_refine_ls_R_factor_all          0.0503
_refine_ls_R_factor_gt           0.0388
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'calc w=1/[σ²(Fo²)+(0.0563P)²+0.2901P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1019
_refine_ls_wR_factor_ref         0.1151
_reflns_number_gt                1468
_reflns_number_total             1777
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            b709261j.txt
_cod_data_source_block           Compound5
_cod_depositor_comments
;
The following automatic conversions were performed:
'_symmetry_cell_setting' value 'Monoclinic' changed to 'monoclinic'
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 21/n'
_cod_database_code               7203061
loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'x+1/2, -y+1/2, z+1/2'
'-x, -y, -z'
'-x-1/2, 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_symmetry_multiplicity
_atom_site_calc_flag
_atom_site_refinement_flags
_atom_site_disorder_assembly
_atom_site_disorder_group
C1 C 0.4596(3) 0.2051(5) 0.4993(2) 0.0847(9) Uani 1 1 d . . .
H1 H 0.4266 0.1426 0.4336 0.102 Uiso 1 1 calc R . .
C2 C 0.5010(2) 0.2837(3) 0.58182(19) 0.0547(5) Uani 1 1 d . . .
C3 C 0.5496(2) 0.3767(3) 0.68617(19) 0.0526(5) Uani 1 1 d . . .
H3A H 0.4789 0.4321 0.7152 0.063 Uiso 1 1 calc R . .
H3B H 0.6070 0.4638 0.6663 0.063 Uiso 1 1 calc R . .
S4 S 0.63426(4) 0.24523(7) 0.80233(4) 0.0507(2) Uani 1 1 d . . .
O5 O 0.72740(15) 0.1428(2) 0.74783(16) 0.0725(5) Uani 1 1 d . . .
C6 C 0.50723(17) 0.1050(2) 0.82385(15) 0.0411(4) Uani 1 1 d . . .
C7 C 0.5174(2) -0.0648(3) 0.79934(17) 0.0506(5) Uani 1 1 d . . .
H7 H 0.5873 -0.1045 0.7675 0.061 Uiso 1 1 calc R . .
C8 C 0.4237(2) -0.1753(3) 0.8221(2) 0.0597(6) Uani 1 1 d . . .
H8 H 0.4299 -0.2895 0.8051 0.072 Uiso 1 1 calc R . .
C9 C 0.3208(2) -0.1163(3) 0.8701(2) 0.0591(6) Uani 1 1 d . . .
H9 H 0.2574 -0.1912 0.8844 0.071 Uiso 1 1 calc R . .
C10 C 0.31033(19) 0.0533(3) 0.89759(18) 0.0512(5) Uani 1 1 d . . .
H10 H 0.2405 0.0918 0.9302 0.061 Uiso 1 1 calc R . .
C11 C 0.40493(17) 0.1647(2) 0.87592(15) 0.0416(4) Uani 1 1 d . . .
O12 O 0.40788(14) 0.33269(18) 0.90080(13) 0.0539(4) Uani 1 1 d . . .
C13 C 0.3125(2) 0.3993(3) 0.9635(2) 0.0665(7) Uani 1 1 d . . .
H13A H 0.2304 0.3919 0.9158 0.100 Uiso 1 1 calc R . .
H13B H 0.3315 0.5154 0.9829 0.100 Uiso 1 1 calc R . .
H13C H 0.3117 0.3355 1.0339 0.100 Uiso 1 1 calc R . .
loop_
_atom_site_aniso_label
_atom_site_aniso_U_11
_atom_site_aniso_U_22
_atom_site_aniso_U_33
_atom_site_aniso_U_23
_atom_site_aniso_U_13
_atom_site_aniso_U_12
C1 0.0827(19) 0.117(2) 0.0526(14) -0.0114(16) 0.0058(14) 0.0170(18)
C2 0.0493(12) 0.0670(13) 0.0495(12) 0.0079(11) 0.0133(9) 0.0091(10)
C3 0.0465(11) 0.0472(11) 0.0655(13) 0.0039(10) 0.0134(9) -0.0022(9)
S4 0.0343(3) 0.0655(4) 0.0522(3) -0.0019(2) 0.0064(2) -0.0012(2)
O5 0.0457(9) 0.0925(13) 0.0846(11) 0.0169(10) 0.0274(8) 0.0222(8)
C6 0.0374(10) 0.0477(11) 0.0379(9) -0.0014(8) 0.0050(7) 0.0051(8)
C7 0.0530(12) 0.0534(12) 0.0447(11) -0.0075(9) 0.0050(9) 0.0122(10)
C8 0.0734(16) 0.0411(11) 0.0614(13) -0.0056(10) -0.0002(11) 0.0030(11)
C9 0.0586(13) 0.0522(13) 0.0645(13) 0.0060(11) 0.0018(11) -0.0097(10)
C10 0.0437(11) 0.0584(12) 0.0531(11) 0.0027(10) 0.0126(9) 0.0003(9)
C11 0.0422(10) 0.0433(11) 0.0394(9) -0.0032(8) 0.0066(8) 0.0029(8)
O12 0.0557(9) 0.0456(8) 0.0655(9) -0.0111(7) 0.0252(7) 0.0014(7)
C13 0.0699(15) 0.0639(14) 0.0707(15) -0.0141(12) 0.0273(12) 0.0144(12)
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
C2 C1 H1 180.0 . . ?
C1 C2 C3 177.9(3) . . ?
C2 C3 S4 113.56(15) . . ?
C2 C3 H3A 108.9 . . ?
S4 C3 H3A 108.9 . . ?
C2 C3 H3B 108.9 . . ?
S4 C3 H3B 108.9 . . ?
H3A C3 H3B 107.7 . . ?
O5 S4 C6 106.30(10) . . ?
O5 S4 C3 106.42(10) . . ?
C6 S4 C3 99.15(9) . . ?
C7 C6 C11 120.42(19) . . ?
C7 C6 S4 119.46(15) . . ?
C11 C6 S4 119.81(14) . . ?
C8 C7 C6 119.9(2) . . ?
C8 C7 H7 120.1 . . ?
C6 C7 H7 120.1 . . ?
C9 C8 C7 119.8(2) . . ?
C9 C8 H8 120.1 . . ?
C7 C8 H8 120.1 . . ?
C8 C9 C10 121.1(2) . . ?
C8 C9 H9 119.5 . . ?
C10 C9 H9 119.5 . . ?
C11 C10 C9 119.3(2) . . ?
C11 C10 H10 120.4 . . ?
C9 C10 H10 120.4 . . ?
O12 C11 C10 125.33(17) . . ?
O12 C11 C6 115.28(17) . . ?
C10 C11 C6 119.39(18) . . ?
C11 O12 C13 118.21(16) . . ?
O12 C13 H13A 109.5 . . ?
O12 C13 H13B 109.5 . . ?
H13A C13 H13B 109.5 . . ?
O12 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
C1 C2 1.169(4) . ?
C1 H1 0.9300 . ?
C2 C3 1.442(3) . ?
C3 S4 1.826(2) . ?
C3 H3A 0.9700 . ?
C3 H3B 0.9700 . ?
S4 O5 1.4884(16) . ?
S4 C6 1.791(2) . ?
C6 C7 1.382(3) . ?
C6 C11 1.399(2) . ?
C7 C8 1.378(3) . ?
C7 H7 0.9300 . ?
C8 C9 1.376(3) . ?
C8 H8 0.9300 . ?
C9 C10 1.389(3) . ?
C9 H9 0.9300 . ?
C10 C11 1.386(3) . ?
C10 H10 0.9300 . ?
C11 O12 1.360(2) . ?
O12 C13 1.430(2) . ?
C13 H13A 0.9600 . ?
C13 H13B 0.9600 . ?
C13 H13C 0.9600 . ?
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
_geom_torsion_site_symmetry_1
_geom_torsion_site_symmetry_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
_geom_torsion_publ_flag
C2 C3 S4 O5 49.61(18) . . . . ?
C2 C3 S4 C6 -60.50(16) . . . . ?
O5 S4 C6 C7 5.31(19) . . . . ?
C3 S4 C6 C7 115.51(17) . . . . ?
O5 S4 C6 C11 179.00(15) . . . . ?
C3 S4 C6 C11 -70.79(16) . . . . ?
C11 C6 C7 C8 2.5(3) . . . . ?
S4 C6 C7 C8 176.16(15) . . . . ?
C6 C7 C8 C9 -0.5(3) . . . . ?
C7 C8 C9 C10 -0.8(3) . . . . ?
C8 C9 C10 C11 0.2(3) . . . . ?
C9 C10 C11 O12 -178.51(19) . . . . ?
C9 C10 C11 C6 1.8(3) . . . . ?
C7 C6 C11 O12 177.14(17) . . . . ?
S4 C6 C11 O12 3.5(2) . . . . ?
C7 C6 C11 C10 -3.1(3) . . . . ?
S4 C6 C11 C10 -176.76(14) . . . . ?
C10 C11 O12 C13 5.8(3) . . . . ?
C6 C11 O12 C13 -174.49(18) . . . . ?
