#------------------------------------------------------------------------------
#$Date: 2017-10-14 21:27:35 +0200 (Sat 14 de Oct de 2017) $
#$Revision: 202017 $
#$URL: svn://www.crystallography.net/cod/cif/7/20/30/7203057.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_7203057
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 ad
_chemical_formula_moiety         'C9 H8 O S'
_chemical_formula_sum            'C9 H8 O S'
_chemical_formula_weight         164.21
_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                   5.9369(6)
_cell_length_b                   10.9023(10)
_cell_length_c                   13.2907(19)
_cell_measurement_reflns_used    22
_cell_measurement_temperature    293(2)
_cell_measurement_theta_max      17.79
_cell_measurement_theta_min      15.64
_cell_volume                     860.25(17)
_computing_cell_refinement       'Nonius MACH3'
_computing_data_collection       'Nonius MACH3'
_computing_data_reduction        'maXus (Gilmore et 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 0.999
_diffrn_measured_fraction_theta_max 0.999
_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     0.71073
_diffrn_reflns_av_R_equivalents  0.045
_diffrn_reflns_av_sigmaI/netI    0.0144
_diffrn_reflns_limit_h_max       7
_diffrn_reflns_limit_h_min       0
_diffrn_reflns_limit_k_max       13
_diffrn_reflns_limit_k_min       0
_diffrn_reflns_limit_l_max       16
_diffrn_reflns_limit_l_min       -15
_diffrn_reflns_number            1896
_diffrn_reflns_theta_full        25.46
_diffrn_reflns_theta_max         25.46
_diffrn_reflns_theta_min         2.42
_diffrn_standards_decay_%        0
_diffrn_standards_interval_time  60
_diffrn_standards_number         3
_exptl_absorpt_coefficient_mu    0.313
_exptl_absorpt_correction_type   none
_exptl_crystal_colour            colourless
_exptl_crystal_density_diffrn    1.268
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       blocks
_exptl_crystal_F_000             344
_exptl_crystal_size_max          0.35
_exptl_crystal_size_mid          0.32
_exptl_crystal_size_min          0.24
_refine_diff_density_max         0.155
_refine_diff_density_min         -0.156
_refine_diff_density_rms         0.031
_refine_ls_abs_structure_details 'Flack H D (1983), Acta Cryst. A39, 876-881'
_refine_ls_abs_structure_Flack   -0.04(11)
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.091
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     101
_refine_ls_number_reflns         1584
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.091
_refine_ls_R_factor_all          0.0345
_refine_ls_R_factor_gt           0.0290
_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)+(0.0474P)²+0.1106P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0770
_refine_ls_wR_factor_ref         0.0836
_reflns_number_gt                1467
_reflns_number_total             1584
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            b709261j.txt
_cod_data_source_block           Compound(S)1
_cod_database_code               7203057
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 0.1910(4) 0.53060(19) 0.32289(17) 0.0592(6) Uani 1 1 d . . .
H1 H 0.2006 0.6151 0.3141 0.071 Uiso 1 1 calc R . .
C2 C 0.1787(4) 0.42353(19) 0.33396(15) 0.0517(5) Uani 1 1 d . . .
C3 C 0.1613(3) 0.29321(17) 0.35051(14) 0.0454(4) Uani 1 1 d . . .
C4 C -0.0225(4) 0.24641(18) 0.40285(15) 0.0514(5) Uani 1 1 d . . .
H4 H -0.1344 0.2992 0.4259 0.062 Uiso 1 1 calc R . .
C5 C -0.0398(3) 0.12155(18) 0.42085(15) 0.0514(5) Uani 1 1 d . . .
H5 H -0.1636 0.0901 0.4551 0.062 Uiso 1 1 calc R . .
C6 C 0.1293(3) 0.04408(16) 0.38739(13) 0.0443(4) Uani 1 1 d . . .
C7 C 0.3113(4) 0.08866(18) 0.33459(16) 0.0504(5) Uani 1 1 d . . .
H7 H 0.4221 0.0354 0.3113 0.060 Uiso 1 1 calc R . .
C8 C 0.3282(4) 0.21355(19) 0.31637(15) 0.0515(5) Uani 1 1 d . . .
H8 H 0.4513 0.2443 0.2812 0.062 Uiso 1 1 calc R . .
C11 C 0.1885(5) -0.1197(2) 0.53553(18) 0.0732(7) Uani 1 1 d . . .
H11A H 0.1744 -0.2013 0.5619 0.110 Uiso 1 1 calc R . .
H11B H 0.0965 -0.0647 0.5743 0.110 Uiso 1 1 calc R . .
H11C H 0.3429 -0.0941 0.5394 0.110 Uiso 1 1 calc R . .
O10 O 0.2752(4) -0.18106(13) 0.34909(15) 0.0851(6) Uani 1 1 d . . .
S9 S 0.09836(10) -0.11764(4) 0.40750(4) 0.05619(18) Uani 1 1 d . . .
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 0.0746(15) 0.0376(11) 0.0655(13) 0.0035(10) 0.0028(11) 0.0001(10)
C2 0.0631(13) 0.0439(11) 0.0482(10) 0.0012(8) -0.0018(10) 0.0008(9)
C3 0.0584(12) 0.0354(9) 0.0425(9) -0.0001(7) -0.0033(9) -0.0009(8)
C4 0.0538(11) 0.0408(10) 0.0596(11) -0.0040(10) 0.0079(10) 0.0052(8)
C5 0.0531(11) 0.0416(10) 0.0594(11) 0.0012(10) 0.0117(9) -0.0032(9)
C6 0.0547(11) 0.0314(8) 0.0468(9) -0.0014(7) 0.0002(9) -0.0026(8)
C7 0.0556(11) 0.0384(10) 0.0571(11) -0.0047(8) 0.0111(10) 0.0028(8)
C8 0.0567(12) 0.0432(10) 0.0547(11) 0.0007(9) 0.0124(10) -0.0050(9)
C11 0.0904(17) 0.0554(13) 0.0739(15) 0.0147(12) -0.0036(13) 0.0115(13)
O10 0.1226(16) 0.0367(8) 0.0961(13) -0.0117(8) 0.0322(12) 0.0084(10)
S9 0.0673(3) 0.0322(2) 0.0690(3) -0.0007(2) 0.0022(3) -0.0064(2)
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 178.3(2) . . ?
C4 C3 C8 119.48(17) . . ?
C4 C3 C2 119.60(18) . . ?
C8 C3 C2 120.91(19) . . ?
C5 C4 C3 120.29(17) . . ?
C5 C4 H4 119.9 . . ?
C3 C4 H4 119.9 . . ?
C6 C5 C4 119.33(17) . . ?
C6 C5 H5 120.3 . . ?
C4 C5 H5 120.3 . . ?
C7 C6 C5 121.14(17) . . ?
C7 C6 S9 120.24(14) . . ?
C5 C6 S9 118.52(15) . . ?
C6 C7 C8 119.48(18) . . ?
C6 C7 H7 120.3 . . ?
C8 C7 H7 120.3 . . ?
C7 C8 C3 120.26(19) . . ?
C7 C8 H8 119.9 . . ?
C3 C8 H8 119.9 . . ?
S9 C11 H11A 109.5 . . ?
S9 C11 H11B 109.5 . . ?
H11A C11 H11B 109.5 . . ?
S9 C11 H11C 109.5 . . ?
H11A C11 H11C 109.5 . . ?
H11B C11 H11C 109.5 . . ?
O10 S9 C11 106.40(13) . . ?
O10 S9 C6 108.00(9) . . ?
C11 S9 C6 97.10(10) . . ?
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 1.179(3) . ?
C1 H1 0.9300 . ?
C2 C3 1.442(3) . ?
C3 C4 1.391(3) . ?
C3 C8 1.393(3) . ?
C4 C5 1.386(3) . ?
C4 H4 0.9300 . ?
C5 C6 1.385(3) . ?
C5 H5 0.9300 . ?
C6 C7 1.377(3) . ?
C6 S9 1.7928(18) . ?
C7 C8 1.387(3) . ?
C7 H7 0.9300 . ?
C8 H8 0.9300 . ?
C11 S9 1.784(2) . ?
C11 H11A 0.9600 . ?
C11 H11B 0.9600 . ?
C11 H11C 0.9600 . ?
O10 S9 1.4773(19) . ?
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
C8 C3 C4 C5 0.0(3) . . . . ?
C2 C3 C4 C5 -178.9(2) . . . . ?
C3 C4 C5 C6 0.9(3) . . . . ?
C4 C5 C6 C7 -1.5(3) . . . . ?
C4 C5 C6 S9 -177.76(16) . . . . ?
C5 C6 C7 C8 1.3(3) . . . . ?
S9 C6 C7 C8 177.52(17) . . . . ?
C6 C7 C8 C3 -0.5(3) . . . . ?
C4 C3 C8 C7 -0.1(3) . . . . ?
C2 C3 C8 C7 178.7(2) . . . . ?
C7 C6 S9 O10 -6.9(2) . . . . ?
C5 C6 S9 O10 169.41(16) . . . . ?
C7 C6 S9 C11 103.00(18) . . . . ?
C5 C6 S9 C11 -80.73(18) . . . . ?
loop_
_cod_related_entry_id
_cod_related_entry_database
_cod_related_entry_code
1 ChemSpider 28714706
