#------------------------------------------------------------------------------
#$Date: 2019-11-24 03:22:05 +0100 (dom 24 de nov de 2019) $
#$Revision: 236680 $
#$URL: svn://www.crystallography.net/cod/cif/4/51/65/4516591.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_4516591
loop_
_publ_author_name
'Partes, Christoph'
'Yildirim, Can'
'Schuster, Swen'
'Kind, Martin'
'Bats, Jan W.'
'Zharnikov, Michael'
'Terfort, Andreas'
_publ_section_title
;
 Self-Assembled Monolayers of Pseudo-C2v-Symmetric,
 Low-Band-Gap Areneoxazolethiolates on Gold Surfaces.
;
_journal_issue                   44
_journal_name_full
'Langmuir : the ACS journal of surfaces and colloids'
_journal_page_first              11474
_journal_page_last               11484
_journal_paper_doi               10.1021/acs.langmuir.6b03055
_journal_volume                  32
_journal_year                    2016
_chemical_formula_moiety         'C11 H7 N O S'
_chemical_formula_sum            'C11 H7 N O S'
_chemical_formula_weight         201.24
_space_group_IT_number           15
_space_group_name_Hall           '-C 2yc'
_space_group_name_H-M_alt        'C 1 2/c 1'
_symmetry_cell_setting           monoclinic
_symmetry_space_group_name_H-M   'C 1 2/c 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                 93.9420(10)
_cell_angle_gamma                90.00
_cell_formula_units_Z            8
_cell_length_a                   18.4892(18)
_cell_length_b                   13.1410(13)
_cell_length_c                   7.5192(7)
_cell_measurement_reflns_used    4969
_cell_measurement_temperature    191(2)
_cell_measurement_theta_max      25
_cell_measurement_theta_min      3
_cell_volume                     1822.6(3)
_computing_cell_refinement       'SAINT (Siemens, 1995)'
_computing_data_collection       'SMART (Siemens, 1995)'
_computing_data_reduction        'SAINT (Siemens, 1995)'
_computing_molecular_graphics    'SHELXTL (Sheldrick, 2008)'
_computing_publication_material  'SHELXL-97 (Sheldrick, 2008)'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 2008)'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 2008)'
_diffrn_ambient_temperature      191(2)
_diffrn_measured_fraction_theta_full 0.993
_diffrn_measured_fraction_theta_max 0.979
_diffrn_measurement_device_type  Siemens_SMART_1K_CCD
_diffrn_measurement_method       ω
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_source         'normal-focus sealed tube'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0604
_diffrn_reflns_av_unetI/netI     0.0475
_diffrn_reflns_limit_h_max       22
_diffrn_reflns_limit_h_min       -22
_diffrn_reflns_limit_k_max       16
_diffrn_reflns_limit_k_min       -16
_diffrn_reflns_limit_l_max       9
_diffrn_reflns_limit_l_min       -9
_diffrn_reflns_number            9598
_diffrn_reflns_theta_full        26.00
_diffrn_reflns_theta_max         26.49
_diffrn_reflns_theta_min         1.90
_diffrn_standards_decay_%        0.0
_diffrn_standards_interval_time  900
_diffrn_standards_number         178
_exptl_absorpt_coefficient_mu    0.314
_exptl_absorpt_correction_T_max  0.933
_exptl_absorpt_correction_T_min  0.801
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   'SADABS (Sheldrick, 2000)'
_exptl_crystal_colour            colorles
_exptl_crystal_density_diffrn    1.467
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       block
_exptl_crystal_F_000             832
_exptl_crystal_size_max          0.50
_exptl_crystal_size_mid          0.40
_exptl_crystal_size_min          0.22
_refine_diff_density_max         0.372
_refine_diff_density_min         -0.201
_refine_diff_density_rms         0.058
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.095
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     131
_refine_ls_number_reflns         1851
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.095
_refine_ls_R_factor_all          0.0665
_refine_ls_R_factor_gt           0.0463
_refine_ls_shift/su_max          0.001
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'calc w=1/[σ²(Fo²)+(0.049P)²+2.8P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1160
_refine_ls_wR_factor_ref         0.1247
_reflns_number_gt                1408
_reflns_number_total             1851
_reflns_threshold_expression     I>2sigma(I)
_cod_data_source_file            la6b03055_si_002.cif
_cod_data_source_block           partes1
_cod_original_sg_symbol_H-M      'C 2/c'
_cod_database_code               4516591
loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'-x, y, -z+1/2'
'x+1/2, y+1/2, z'
'-x+1/2, y+1/2, -z+1/2'
'-x, -y, -z'
'x, -y, z-1/2'
'-x+1/2, -y+1/2, -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
S1 S 0.04975(4) 0.63742(6) 1.03253(9) 0.0375(2) Uani 1 1 d .
O1 O 0.18417(9) 0.65275(13) 0.9382(2) 0.0315(4) Uani 1 1 d .
C1 C 0.22392(13) 0.64407(18) 0.7874(3) 0.0276(5) Uani 1 1 d .
C3 C 0.32337(13) 0.64168(18) 0.6069(3) 0.0304(6) Uani 1 1 d .
N1 N 0.10775(12) 0.61465(16) 0.7115(3) 0.0311(5) Uani 1 1 d .
C8 C 0.27519(14) 0.61595(17) 0.4562(3) 0.0283(6) Uani 1 1 d .
C5 C 0.42486(15) 0.6353(2) 0.4205(4) 0.0410(7) Uani 1 1 d .
H5A H 0.4754 0.6421 0.4073 0.049 Uiso 1 1 calc R
C11 C 0.11302(14) 0.63465(18) 0.8871(3) 0.0296(6) Uani 1 1 d .
C2 C 0.29592(14) 0.65636(19) 0.7773(3) 0.0313(6) Uani 1 1 d .
H2A H 0.3268 0.6740 0.8788 0.038 Uiso 1 1 calc R
C10 C 0.17553(13) 0.61979(17) 0.6411(3) 0.0267(5) Uani 1 1 d .
C6 C 0.37788(15) 0.6090(2) 0.2720(4) 0.0381(7) Uani 1 1 d .
H6A H 0.3969 0.5971 0.1596 0.046 Uiso 1 1 calc R
C9 C 0.19957(13) 0.60596(18) 0.4755(3) 0.0298(6) Uani 1 1 d .
H9A H 0.1669 0.5902 0.3763 0.036 Uiso 1 1 calc R
C7 C 0.30533(15) 0.60056(19) 0.2896(3) 0.0337(6) Uani 1 1 d .
H7A H 0.2741 0.5840 0.1881 0.040 Uiso 1 1 calc R
C4 C 0.39828(15) 0.6510(2) 0.5824(4) 0.0371(6) Uani 1 1 d .
H4A H 0.4307 0.6687 0.6811 0.044 Uiso 1 1 calc R
H1A H 0.0665(17) 0.613(2) 0.654(4) 0.038(8) Uiso 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
S1 0.0317(4) 0.0515(4) 0.0295(4) -0.0020(3) 0.0033(3) 0.0010(3)
O1 0.0296(10) 0.0377(10) 0.0268(9) -0.0039(7) -0.0008(7) 0.0003(7)
C1 0.0319(13) 0.0251(12) 0.0257(12) -0.0022(10) 0.0007(10) 0.0020(10)
C3 0.0291(13) 0.0249(13) 0.0368(14) 0.0006(11) -0.0009(11) -0.0002(10)
N1 0.0262(12) 0.0380(13) 0.0284(11) -0.0019(9) -0.0030(9) 0.0006(9)
C8 0.0305(13) 0.0233(12) 0.0307(13) 0.0022(10) -0.0002(10) 0.0011(10)
C5 0.0313(14) 0.0484(17) 0.0439(16) -0.0013(13) 0.0070(12) -0.0033(12)
C11 0.0311(13) 0.0275(13) 0.0295(13) -0.0008(10) -0.0031(10) 0.0020(11)
C2 0.0301(14) 0.0322(14) 0.0307(13) -0.0043(10) -0.0050(10) -0.0010(10)
C10 0.0270(12) 0.0255(13) 0.0272(12) -0.0003(9) -0.0010(10) -0.0007(10)
C6 0.0419(16) 0.0420(16) 0.0313(14) 0.0002(11) 0.0091(12) 0.0000(12)
C9 0.0320(14) 0.0300(13) 0.0263(13) -0.0001(10) -0.0049(10) -0.0012(10)
C7 0.0407(15) 0.0323(14) 0.0280(13) -0.0012(11) 0.0013(11) -0.0026(11)
C4 0.0321(14) 0.0428(16) 0.0359(14) -0.0042(12) -0.0010(11) -0.0048(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'
N N 0.0061 0.0033 '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
C11 O1 C1 107.93(18)
C2 C1 O1 127.8(2)
C2 C1 C10 124.1(2)
O1 C1 C10 108.1(2)
C4 C3 C2 121.2(2)
C4 C3 C8 118.6(2)
C2 C3 C8 120.2(2)
C11 N1 C10 110.9(2)
C11 N1 H1A 120.5(19)
C10 N1 H1A 127.1(19)
C7 C8 C9 121.7(2)
C7 C8 C3 118.1(2)
C9 C8 C3 120.2(2)
C4 C5 C6 120.4(3)
C4 C5 H5A 119.8
C6 C5 H5A 119.8
N1 C11 O1 108.3(2)
N1 C11 S1 130.3(2)
O1 C11 S1 121.39(18)
C1 C2 C3 116.7(2)
C1 C2 H2A 121.7
C3 C2 H2A 121.7
C9 C10 N1 134.3(2)
C9 C10 C1 121.0(2)
N1 C10 C1 104.7(2)
C7 C6 C5 120.1(2)
C7 C6 H6A 120.0
C5 C6 H6A 120.0
C10 C9 C8 117.8(2)
C10 C9 H9A 121.1
C8 C9 H9A 121.1
C6 C7 C8 121.5(2)
C6 C7 H7A 119.2
C8 C7 H7A 119.2
C5 C4 C3 121.4(3)
C5 C4 H4A 119.3
C3 C4 H4A 119.3
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
S1 C11 1.656(3)
O1 C11 1.366(3)
O1 C1 1.397(3)
C1 C2 1.348(3)
C1 C10 1.407(3)
C3 C4 1.415(4)
C3 C2 1.423(4)
C3 C8 1.433(4)
N1 C11 1.343(3)
N1 C10 1.395(3)
N1 H1A 0.85(3)
C8 C7 1.420(4)
C8 C9 1.422(3)
C5 C4 1.360(4)
C5 C6 1.409(4)
C5 H5A 0.9500
C2 H2A 0.9500
C10 C9 1.363(3)
C6 C7 1.361(4)
C6 H6A 0.9500
C9 H9A 0.9500
C7 H7A 0.9500
C4 H4A 0.9500
loop_
_geom_hbond_atom_site_label_D
_geom_hbond_atom_site_label_H
_geom_hbond_atom_site_label_A
_geom_hbond_distance_DH
_geom_hbond_distance_HA
_geom_hbond_distance_DA
_geom_hbond_angle_DHA
_geom_hbond_site_symmetry_A
N1 H1A S1 0.85(3) 2.50(3) 3.347(2) 171(3) 2_556
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
C11 O1 C1 C2 179.7(2)
C11 O1 C1 C10 -0.1(3)
C4 C3 C8 C7 0.4(3)
C2 C3 C8 C7 -179.0(2)
C4 C3 C8 C9 -179.9(2)
C2 C3 C8 C9 0.7(3)
C10 N1 C11 O1 -0.5(3)
C10 N1 C11 S1 -179.38(19)
C1 O1 C11 N1 0.4(3)
C1 O1 C11 S1 179.41(17)
O1 C1 C2 C3 179.1(2)
C10 C1 C2 C3 -1.1(4)
C4 C3 C2 C1 -178.9(2)
C8 C3 C2 C1 0.5(3)
C11 N1 C10 C9 179.7(3)
C11 N1 C10 C1 0.4(3)
C2 C1 C10 C9 0.6(4)
O1 C1 C10 C9 -179.6(2)
C2 C1 C10 N1 -180.0(2)
O1 C1 C10 N1 -0.1(3)
C4 C5 C6 C7 0.9(4)
N1 C10 C9 C8 -178.6(2)
C1 C10 C9 C8 0.6(3)
C7 C8 C9 C10 178.5(2)
C3 C8 C9 C10 -1.2(3)
C5 C6 C7 C8 -1.1(4)
C9 C8 C7 C6 -179.2(2)
C3 C8 C7 C6 0.5(4)
C6 C5 C4 C3 0.0(4)
C2 C3 C4 C5 178.8(2)
C8 C3 C4 C5 -0.6(4)
