#------------------------------------------------------------------------------
#$Date: 2016-03-26 22:19:53 +0200 (Sat, 26 Mar 2016) $
#$Revision: 180500 $
#$URL: svn://www.crystallography.net/cod/cif/7/21/69/7216952.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_7216952
loop_
_publ_author_name
'Otazo-Sánchez, Elena'
'Pérez-Marín, Leonel'
'Estévez-Hernández, Osvaldo'
'Rojas-Lima, Susana'
'Alonso-Chamarro, Julián'
_publ_section_title
;
 Aroylthioureas: new organic ionophores for heavy-metal ion selective
 electrodes
;
_journal_issue                   11
_journal_name_full
'Journal of the Chemical Society, Perkin Transactions 2'
_journal_page_first              2211
_journal_paper_doi               10.1039/b102029n
_journal_year                    2001
_chemical_formula_sum            'C12 H16 N2 O2 S'
_chemical_formula_weight         252.33
_chemical_name_systematic
; 
? 
;
_space_group_IT_number           61
_symmetry_space_group_name_Hall  '-P 2ac 2ab'
_symmetry_space_group_name_H-M   'P b c a'
_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            8
_cell_length_a                   7.3964(6)
_cell_length_b                   10.3444(9)
_cell_length_c                   34.536(3)
_cell_measurement_temperature    293(2)
_cell_volume                     2642.4(4)
_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_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  0.0471
_diffrn_reflns_av_sigmaI/netI    0.0278
_diffrn_reflns_limit_h_max       8
_diffrn_reflns_limit_h_min       -8
_diffrn_reflns_limit_k_max       11
_diffrn_reflns_limit_k_min       -11
_diffrn_reflns_limit_l_max       38
_diffrn_reflns_limit_l_min       -29
_diffrn_reflns_number            12221
_diffrn_reflns_theta_full        23.27
_diffrn_reflns_theta_max         23.27
_diffrn_reflns_theta_min         2.36
_exptl_absorpt_coefficient_mu    0.237
_exptl_crystal_density_diffrn    1.269
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             1072
_refine_diff_density_max         0.132
_refine_diff_density_min         -0.149
_refine_diff_density_rms         0.032
_refine_ls_extinction_coef       0.0114(10)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc²λ³/sin(2θ)]^-1/4^
_refine_ls_extinction_method     SHELXL
_refine_ls_goodness_of_fit_ref   0.996
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     163
_refine_ls_number_reflns         1897
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      0.996
_refine_ls_R_factor_all          0.0444
_refine_ls_R_factor_gt           0.0313
_refine_ls_shift/su_max          0.003
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'calc w=1/[σ²(Fo²)+(0.0516P)²+0.0044P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0770
_refine_ls_wR_factor_ref         0.0819
_reflns_number_gt                1490
_reflns_number_total             1897
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            b102029n.txt
_cod_data_source_block           otazo2m
_cod_database_code               7216952
loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'-x+1/2, -y, z+1/2'
'-x, y+1/2, -z+1/2'
'x+1/2, -y+1/2, -z'
'-x, -y, -z'
'x-1/2, y, -z-1/2'
'x, -y-1/2, z-1/2'
'-x-1/2, y-1/2, z'
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 0.02670(7) 1.16558(5) 0.117718(15) 0.0590(2) Uani 1 1 d .
O2 O 0.24040(17) 1.08685(11) -0.01676(3) 0.0537(4) Uani 1 1 d .
O1 O 0.20366(17) 0.81738(11) 0.04596(4) 0.0550(4) Uani 1 1 d .
N1 N 0.1548(2) 1.03199(15) 0.05845(4) 0.0471(4) Uani 1 1 d .
N2 N 0.0940(2) 0.91335(16) 0.11372(5) 0.0515(4) Uani 1 1 d .
C5 C 0.2058(2) 0.93071(17) 0.03529(5) 0.0438(4) Uani 1 1 d .
C2 C 0.3862(2) 0.97653(19) -0.06209(5) 0.0556(5) Uani 1 1 d .
H2 H 0.4444 0.9555 -0.0851 0.067 Uiso 1 1 calc R
C3 C 0.3548(2) 0.89394(18) -0.03036(6) 0.0524(5) Uani 1 1 d .
H3 H 0.3890 0.8077 -0.0283 0.063 Uiso 1 1 calc R
C1 C 0.3163(3) 1.0904(2) -0.05260(6) 0.0585(5) Uani 1 1 d .
H1 H 0.3189 1.1632 -0.0684 0.070 Uiso 1 1 calc R
C6 C 0.0932(2) 1.02818(17) 0.09689(5) 0.0459(5) Uani 1 1 d .
C4 C 0.2658(2) 0.96375(16) -0.00361(5) 0.0431(4) Uani 1 1 d .
C8 C -0.0369(3) 0.7473(2) 0.15462(5) 0.0587(5) Uani 1 1 d .
H8A H 0.0645 0.6907 0.1491 0.070 Uiso 1 1 calc R
H8B H -0.1292 0.7321 0.1352 0.070 Uiso 1 1 calc R
C7 C 0.0248(2) 0.88704(18) 0.15256(5) 0.0511(5) Uani 1 1 d .
H7 H -0.0803 0.9427 0.1570 0.061 Uiso 1 1 calc R
C10 C 0.0213(3) 0.7479(2) 0.22645(6) 0.0773(7) Uani 1 1 d .
H10A H -0.0352 0.7340 0.2515 0.093 Uiso 1 1 calc R
H10B H 0.1248 0.6907 0.2245 0.093 Uiso 1 1 calc R
C12 C 0.1643(3) 0.9153(2) 0.18380(6) 0.0628(6) Uani 1 1 d .
H12A H 0.2006 1.0053 0.1824 0.075 Uiso 1 1 calc R
H12B H 0.2706 0.8621 0.1797 0.075 Uiso 1 1 calc R
C11 C 0.0842(3) 0.8868(2) 0.22354(6) 0.0729(6) Uani 1 1 d .
H11A H 0.1745 0.9032 0.2433 0.088 Uiso 1 1 calc R
H11B H -0.0173 0.9441 0.2282 0.088 Uiso 1 1 calc R
C9 C -0.1126(3) 0.7158(2) 0.19460(6) 0.0732(6) Uani 1 1 d .
H9A H -0.2230 0.7644 0.1987 0.088 Uiso 1 1 calc R
H9B H -0.1422 0.6245 0.1958 0.088 Uiso 1 1 calc R
H13 H 0.138(3) 0.854(2) 0.1006(6) 0.070(7) Uiso 1 1 d .
H14 H 0.169(2) 1.1070(19) 0.0487(5) 0.053(6) Uiso 1 1 d .
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
C1 O2 C4 105.74(14)
C5 N1 C6 128.26(16)
C6 N2 C7 124.68(17)
O1 C5 N1 123.42(17)
O1 C5 C4 120.29(16)
N1 C5 C4 116.28(15)
C1 C2 C3 106.38(17)
C4 C3 C2 106.82(17)
C2 C1 O2 111.18(17)
N2 C6 N1 116.05(16)
N2 C6 S1 125.29(14)
N1 C6 S1 118.66(13)
C3 C4 O2 109.87(16)
C3 C4 C5 131.10(16)
O2 C4 C5 118.95(16)
C7 C8 C9 110.89(17)
N2 C7 C8 109.01(15)
N2 C7 C12 112.19(16)
C8 C7 C12 110.71(16)
C11 C10 C9 111.15(18)
C7 C12 C11 109.74(16)
C10 C11 C12 111.29(18)
C10 C9 C8 111.71(17)
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
S1 C6 1.6672(18)
O2 C1 1.360(2)
O2 C4 1.365(2)
O1 C5 1.2288(19)
N1 C5 1.371(2)
N1 C6 1.404(2)
N2 C6 1.322(2)
N2 C7 1.461(2)
C5 C4 1.456(2)
C2 C1 1.328(3)
C2 C3 1.409(3)
C3 C4 1.345(2)
C8 C7 1.517(3)
C8 C9 1.525(3)
C7 C12 1.521(3)
C10 C11 1.513(3)
C10 C9 1.517(3)
C12 C11 1.524(3)
