#------------------------------------------------------------------------------
#$Date: 2017-10-14 22:27:35 +0300 (Sat, 14 Oct 2017) $
#$Revision: 202017 $
#$URL: file:///home/coder/svn-repositories/cod/cif/7/20/30/7203064.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_7203064
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_absolute_configuration unk
_chemical_formula_moiety         'C11 H12 O3 S'
_chemical_formula_sum            'C11 H12 O3 S'
_chemical_formula_weight         224.27
_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'
_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                 90.00
_cell_angle_gamma                90.00
_cell_formula_units_Z            4
_cell_length_a                   6.5860(2)
_cell_length_b                   10.1867(3)
_cell_length_c                   16.9358(6)
_cell_measurement_reflns_used    4794
_cell_measurement_temperature    240(2)
_cell_measurement_theta_max      27.48
_cell_measurement_theta_min      1.00
_cell_volume                     1136.22(6)
_computing_cell_refinement       'HKL Scalepack (Otwinowski & Minor 1997)'
_computing_data_collection       'Collect (Nonius B.V. 1998)'
_computing_data_reduction
;
HKL Denzo and Scalepack (Otwinowski & Minor 1997)
;
_computing_molecular_graphics    'PLATON (Spek, 2000)'
_computing_publication_material  'SHELXL-97; PLATON'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_computing_structure_solution    'SIR-92 (Altomare et al. 1994)'
_diffrn_ambient_temperature      240(2)
_diffrn_measured_fraction_theta_full 0.996
_diffrn_measured_fraction_theta_max 0.996
_diffrn_measurement_device_type  'Nonius Kappa CCD'
_diffrn_measurement_method       'Thin slice ω and φ scans'
_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    0.0413
_diffrn_reflns_limit_h_max       8
_diffrn_reflns_limit_h_min       -6
_diffrn_reflns_limit_k_max       13
_diffrn_reflns_limit_k_min       -9
_diffrn_reflns_limit_l_max       21
_diffrn_reflns_limit_l_min       -21
_diffrn_reflns_number            6747
_diffrn_reflns_theta_full        27.45
_diffrn_reflns_theta_max         27.45
_diffrn_reflns_theta_min         3.68
_exptl_absorpt_coefficient_mu    0.269
_exptl_absorpt_correction_T_max  0.975
_exptl_absorpt_correction_T_min  0.918
_exptl_absorpt_correction_type   multi-scan
_exptl_crystal_colour            colourless
_exptl_crystal_density_diffrn    1.311
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       blocks
_exptl_crystal_F_000             472
_exptl_crystal_size_max          0.28
_exptl_crystal_size_mid          0.12
_exptl_crystal_size_min          0.10
_refine_diff_density_max         0.165
_refine_diff_density_min         -0.324
_refine_diff_density_rms         0.055
_refine_ls_abs_structure_details 'Flack H D (1983), Acta Cryst. A39, 876-881'
_refine_ls_abs_structure_Flack   0.47(11)
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.037
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     138
_refine_ls_number_reflns         1514
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.037
_refine_ls_R_factor_all          0.0440
_refine_ls_R_factor_gt           0.0325
_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)+(0.0375P)²+0.2329P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0753
_refine_ls_wR_factor_ref         0.0800
_reflns_number_gt                1333
_reflns_number_total             1514
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            b709261j.txt
_cod_data_source_block           Compound8
_cod_database_code               7203064
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_symmetry_multiplicity
_atom_site_calc_flag
_atom_site_refinement_flags
_atom_site_disorder_assembly
_atom_site_disorder_group
C1 C 1.1446(5) 0.7755(3) 0.03797(17) 0.0555(7) Uani 1 1 d . . .
H1 H 1.1666 0.6884 0.0219 0.067 Uiso 1 1 calc R . .
C2 C 1.1171(4) 0.8840(2) 0.05792(15) 0.0410(6) Uani 1 1 d . . .
C3 C 1.0949(4) 1.0222(2) 0.07976(14) 0.0365(5) Uani 1 1 d . . .
H3 H 1.1737 1.0382 0.1286 0.044 Uiso 1 1 calc R . .
C4 C 1.1720(5) 1.1151(3) 0.01568(15) 0.0536(7) Uani 1 1 d . . .
H4A H 1.1037 1.0958 -0.0337 0.080 Uiso 1 1 calc R . .
H4B H 1.3172 1.1033 0.0091 0.080 Uiso 1 1 calc R . .
H4C H 1.1442 1.2051 0.0310 0.080 Uiso 1 1 calc R . .
S5 S 0.83153(9) 1.06115(5) 0.09878(3) 0.03469(16) Uani 1 1 d . . .
O6 O 0.7140(3) 1.02601(17) 0.03031(10) 0.0448(5) Uani 1 1 d . . .
O7 O 0.8267(3) 1.19572(15) 0.12411(10) 0.0459(4) Uani 1 1 d . . .
C8 C 0.7518(4) 0.9602(2) 0.17743(13) 0.0366(5) Uani 1 1 d . . .
C9 C 0.5789(4) 0.8833(3) 0.16656(17) 0.0471(6) Uani 1 1 d . . .
H9 H 0.5154 0.8803 0.1169 0.057 Uiso 1 1 calc R . .
C10 C 0.5010(5) 0.8116(3) 0.22882(18) 0.0610(8) Uani 1 1 d . . .
H10 H 0.3830 0.7609 0.2221 0.073 Uiso 1 1 calc R . .
C11 C 0.5977(5) 0.8151(3) 0.30067(19) 0.0636(9) Uani 1 1 d . . .
H11 H 0.5449 0.7658 0.3429 0.076 Uiso 1 1 calc R . .
C12 C 0.7698(5) 0.8890(3) 0.31240(16) 0.0578(8) Uani 1 1 d . . .
H12 H 0.8336 0.8892 0.3620 0.069 Uiso 1 1 calc R . .
C13 C 0.8496(4) 0.9634(2) 0.25094(14) 0.0429(6) Uani 1 1 d . . .
O14 O 1.0160(3) 1.03992(19) 0.25668(10) 0.0550(5) Uani 1 1 d . . .
C15 C 1.1284(6) 1.0381(3) 0.32946(15) 0.0659(9) Uani 1 1 d . . .
H15A H 1.1717 0.9490 0.3408 0.099 Uiso 1 1 calc R . .
H15B H 1.0427 1.0696 0.3720 0.099 Uiso 1 1 calc R . .
H15C H 1.2465 1.0944 0.3247 0.099 Uiso 1 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_
_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 176.1(3) . . ?
C2 C3 C4 112.5(2) . . ?
C2 C3 S5 110.61(18) . . ?
C4 C3 S5 108.04(18) . . ?
C2 C3 H3 108.5 . . ?
C4 C3 H3 108.5 . . ?
S5 C3 H3 108.5 . . ?
C3 C4 H4A 109.5 . . ?
C3 C4 H4B 109.5 . . ?
H4A C4 H4B 109.5 . . ?
C3 C4 H4C 109.5 . . ?
H4A C4 H4C 109.5 . . ?
H4B C4 H4C 109.5 . . ?
O7 S5 O6 117.77(11) . . ?
O7 S5 C8 108.94(11) . . ?
O6 S5 C8 107.68(11) . . ?
O7 S5 C3 106.49(12) . . ?
O6 S5 C3 108.52(11) . . ?
C8 S5 C3 106.98(11) . . ?
C9 C8 C13 120.4(2) . . ?
C9 C8 S5 118.10(19) . . ?
C13 C8 S5 121.36(19) . . ?
C10 C9 C8 120.0(3) . . ?
C10 C9 H9 120.0 . . ?
C8 C9 H9 120.0 . . ?
C11 C10 C9 119.3(3) . . ?
C11 C10 H10 120.3 . . ?
C9 C10 H10 120.3 . . ?
C10 C11 C12 121.6(3) . . ?
C10 C11 H11 119.2 . . ?
C12 C11 H11 119.2 . . ?
C11 C12 C13 120.1(3) . . ?
C11 C12 H12 119.9 . . ?
C13 C12 H12 119.9 . . ?
O14 C13 C12 124.6(3) . . ?
O14 C13 C8 116.8(2) . . ?
C12 C13 C8 118.6(3) . . ?
C13 O14 C15 118.2(2) . . ?
O14 C15 H15A 109.5 . . ?
O14 C15 H15B 109.5 . . ?
H15A C15 H15B 109.5 . . ?
O14 C15 H15C 109.5 . . ?
H15A C15 H15C 109.5 . . ?
H15B C15 H15C 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 1.170(3) . ?
C1 H1 0.9400 . ?
C2 C3 1.462(3) . ?
C3 C4 1.527(3) . ?
C3 S5 1.809(2) . ?
C3 H3 0.9900 . ?
C4 H4A 0.9700 . ?
C4 H4B 0.9700 . ?
C4 H4C 0.9700 . ?
S5 O7 1.4368(16) . ?
S5 O6 1.4393(17) . ?
S5 C8 1.763(2) . ?
C8 C9 1.394(3) . ?
C8 C13 1.402(3) . ?
C9 C10 1.382(4) . ?
C9 H9 0.9400 . ?
C10 C11 1.374(5) . ?
C10 H10 0.9400 . ?
C11 C12 1.375(5) . ?
C11 H11 0.9400 . ?
C12 C13 1.391(4) . ?
C12 H12 0.9400 . ?
C13 O14 1.348(3) . ?
O14 C15 1.438(3) . ?
C15 H15A 0.9700 . ?
C15 H15B 0.9700 . ?
C15 H15C 0.9700 . ?
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 S5 O7 176.68(17) . . . . ?
C4 C3 S5 O7 -59.72(18) . . . . ?
C2 C3 S5 O6 -55.6(2) . . . . ?
C4 C3 S5 O6 67.98(18) . . . . ?
C2 C3 S5 C8 60.3(2) . . . . ?
C4 C3 S5 C8 -176.10(17) . . . . ?
O7 S5 C8 C9 119.0(2) . . . . ?
O6 S5 C8 C9 -9.8(2) . . . . ?
C3 S5 C8 C9 -126.3(2) . . . . ?
O7 S5 C8 C13 -56.4(2) . . . . ?
O6 S5 C8 C13 174.8(2) . . . . ?
C3 S5 C8 C13 58.3(2) . . . . ?
C13 C8 C9 C10 1.1(4) . . . . ?
S5 C8 C9 C10 -174.4(2) . . . . ?
C8 C9 C10 C11 -1.2(4) . . . . ?
C9 C10 C11 C12 0.4(5) . . . . ?
C10 C11 C12 C13 0.5(5) . . . . ?
C11 C12 C13 O14 179.3(3) . . . . ?
C11 C12 C13 C8 -0.5(4) . . . . ?
C9 C8 C13 O14 179.9(2) . . . . ?
S5 C8 C13 O14 -4.8(3) . . . . ?
C9 C8 C13 C12 -0.3(4) . . . . ?
S5 C8 C13 C12 175.1(2) . . . . ?
C12 C13 O14 C15 4.6(4) . . . . ?
C8 C13 O14 C15 -175.5(2) . . . . ?
loop_
_cod_related_entry_id
_cod_related_entry_database
_cod_related_entry_code
1 ChemSpider 30653664
