#------------------------------------------------------------------------------
#$Date: 2016-02-16 22:30:59 +0200 (Tue, 16 Feb 2016) $
#$Revision: 176467 $
#$URL: svn://www.crystallography.net/cod/cif/4/32/17/4321761.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_4321761
loop_
_publ_author_name
'Shinzi Kato'
'Nobuyuki Kitaoka'
'Osamu Niyomura'
'Yuka Kitoh'
'Takahiro Kanda'
'Masahiro Ebihara'
_publ_section_title
;
 Heavy Alkali Metal Arenedithiocarboxylates: A Facile Synthesis, Dimeric
 Structure, and Nonbonding Interaction between the Metals and Aromatic
 Ring Carbons
;
_journal_name_full               'Inorganic Chemistry'
_journal_page_first              496
_journal_page_last               506
_journal_paper_doi               10.1021/ic9808089
_journal_volume                  38
_journal_year                    1999
_chemical_formula_sum            'C12 H19 N O S2'
_chemical_formula_weight         257.41
_space_group_IT_number           19
_symmetry_cell_setting           orthorhombic
_symmetry_Int_Tables_number      19
_symmetry_space_group_name_Hall  'P 2ac 2ab'
_symmetry_space_group_name_H-M   'P 21 21 21'
_audit_creation_date             'Sat Jun 27 15:41:58 1998'
_audit_creation_method           'from TEXRAY.INF file'
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   10.481(2)
_cell_length_b                   18.243(2)
_cell_length_c                   7.474(2)
_cell_measurement_reflns_used    25
_cell_measurement_temperature    296.2
_cell_measurement_theta_max      15.0
_cell_measurement_theta_min      14.4
_cell_volume                     1429.1(5)
_computing_cell_refinement       'Rigaku/AFC Diffractometer Control'
_computing_data_collection       'Rigaku/AFC Diffractometer Control'
_computing_data_reduction        teXsan
_computing_publication_material  teXsan
_computing_structure_refinement  teXsan
_computing_structure_solution    SHELXS86
_diffrn_ambient_temperature      296.2
_diffrn_measurement_device_type  'Rigaku AFC7R'
_diffrn_measurement_method       ω-2θ
_diffrn_orient_matrix_UB_11      -0.08880
_diffrn_orient_matrix_UB_12      -0.01867
_diffrn_orient_matrix_UB_13      -0.01821
_diffrn_orient_matrix_UB_21      0.03378
_diffrn_orient_matrix_UB_22      -0.05103
_diffrn_orient_matrix_UB_23      -0.01212
_diffrn_orient_matrix_UB_31      -0.00915
_diffrn_orient_matrix_UB_32      -0.00726
_diffrn_orient_matrix_UB_33      0.13200
_diffrn_radiation_detector       'scintillation counter'
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_source         'Rigaku rotating anode'
_diffrn_radiation_type           'Mo K\a'
_diffrn_radiation_wavelength     0.7107
_diffrn_reflns_av_R_equivalents  0.003
_diffrn_reflns_av_sigmaI/netI    0.101
_diffrn_reflns_limit_h_max       13
_diffrn_reflns_limit_h_min       0
_diffrn_reflns_limit_k_max       23
_diffrn_reflns_limit_k_min       0
_diffrn_reflns_limit_l_max       9
_diffrn_reflns_limit_l_min       0
_diffrn_reflns_number            1921
_diffrn_reflns_reduction_process 'Lp corrections applied'
_diffrn_reflns_theta_max         27.50
_diffrn_reflns_theta_min         2.23
_diffrn_standards_decay_%        -0.44
_diffrn_standards_interval_count 150
_diffrn_standards_number         3
_exptl_absorpt_coefficient_mu    0.354
_exptl_absorpt_correction_type   none
_exptl_crystal_colour            red
_exptl_crystal_density_diffrn    1.196
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       prismatic
_exptl_crystal_F_000             552.00
_exptl_crystal_size_max          0.230
_exptl_crystal_size_mid          0.200
_exptl_crystal_size_min          0.170
_refine_diff_density_max         0.21
_refine_diff_density_min         -0.16
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.339
_refine_ls_hydrogen_treatment    noref
_refine_ls_matrix_type           full
_refine_ls_number_constraints    0
_refine_ls_number_parameters     145
_refine_ls_number_reflns         1035
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0000
_refine_ls_R_factor_gt           0.0000
_refine_ls_shift/su_max          0.0010
_refine_ls_shift/su_mean         0.0000
_refine_ls_structure_factor_coef F
_refine_ls_weighting_details     'w = 1/[σ²(Fo) + 0.00010|Fo|²]'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0000
_refine_ls_wR_factor_ref         0.0365
_reflns_number_gt                0
_reflns_number_total             1920
_reflns_threshold_expression     >3.0sigma(I)
_cod_data_source_file            ic9808089_6.cif
_cod_data_source_block           2-CH3OC6H4CSS-+NMe4
_cod_original_cell_volume        1429.0(4)
_cod_original_sg_symbol_H-M      'P 21 21 21 '
_cod_original_formula_sum        'C12 H19 N O S2 '
_cod_database_code               4321761
loop_
_symmetry_equiv_pos_as_xyz
x,y,z
1/2-x,-y,1/2+z
1/2+x,1/2-y,-z
-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_calc_flag
_atom_site_refinement_flags
_atom_site_disorder_assembly
_atom_site_disorder_group
S(1) S 0.5227(1) 0.80561(6) 0.2332(2) 0.0607(4) Uani 1.00 d . . .
S(2) S 0.5704(1) 0.96572(7) 0.2035(2) 0.0626(4) Uani 1.00 d . . .
O(1) O 0.3411(3) 0.8557(2) -0.1059(5) 0.063(1) Uani 1.00 d . . .
N(1) N 0.7174(3) 0.8467(2) -0.2862(6) 0.046(1) Uani 1.00 d . . .
C(1) C 0.4749(4) 0.8924(2) 0.2035(6) 0.044(1) Uani 1.00 d . . .
C(2) C 0.3343(4) 0.9045(2) 0.1849(7) 0.041(1) Uani 1.00 d . . .
C(3) C 0.2691(5) 0.8830(3) 0.0312(7) 0.047(1) Uani 1.00 d . . .
C(4) C 0.1369(5) 0.8904(3) 0.0227(7) 0.059(2) Uani 1.00 d . . .
C(5) C 0.0715(5) 0.9201(3) 0.1645(9) 0.067(2) Uani 1.00 d . . .
C(6) C 0.1344(5) 0.9435(3) 0.3127(9) 0.066(2) Uani 1.00 d . . .
C(7) C 0.2658(5) 0.9366(2) 0.3207(7) 0.056(2) Uani 1.00 d . . .
C(8) C 0.2802(5) 0.8391(4) -0.2677(8) 0.091(2) Uani 1.00 d . . .
C(9) C 0.6270(5) 0.9098(2) -0.3017(8) 0.062(2) Uani 1.00 d . . .
C(10) C 0.7899(5) 0.8537(3) -0.1150(7) 0.064(2) Uani 1.00 d . . .
C(11) C 0.8080(6) 0.8480(3) -0.4399(7) 0.063(2) Uani 1.00 d . . .
C(12) C 0.6458(5) 0.7759(3) -0.2844(8) 0.072(2) Uani 1.00 d . . .
H(1) H 0.0928 0.8742 -0.0914 0.0659 Uiso 1.00 calc . . .
H(2) H -0.0215 0.9218 0.1579 0.0721 Uiso 1.00 calc . . .
H(3) H 0.0846 0.9667 0.4128 0.0776 Uiso 1.00 calc . . .
H(4) H 0.3125 0.9535 0.4287 0.0674 Uiso 1.00 calc . . .
H(5) H 0.2358 0.8769 -0.3243 0.1032 Uiso 1.00 calc . . .
H(6) H 0.3392 0.8177 -0.3594 0.1032 Uiso 1.00 calc . . .
H(7) H 0.2169 0.7977 -0.2534 0.1032 Uiso 1.00 calc . . .
H(8) H 0.6704 0.9533 -0.3033 0.0722 Uiso 1.00 calc . . .
H(9) H 0.5772 0.9026 -0.4069 0.0722 Uiso 1.00 calc . . .
H(10) H 0.5707 0.9069 -0.1998 0.0722 Uiso 1.00 calc . . .
H(11) H 0.8480 0.8142 -0.1055 0.0612 Uiso 1.00 calc . . .
H(12) H 0.8325 0.8987 -0.1127 0.0612 Uiso 1.00 calc . . .
H(13) H 0.7294 0.8511 -0.0197 0.0612 Uiso 1.00 calc . . .
H(14) H 0.8676 0.8076 -0.4312 0.0656 Uiso 1.00 calc . . .
H(15) H 0.7638 0.8437 -0.5501 0.0656 Uiso 1.00 calc . . .
H(16) H 0.8567 0.8923 -0.4405 0.0656 Uiso 1.00 calc . . .
H(17) H 0.5880 0.7771 -0.1826 0.0705 Uiso 1.00 calc . . .
H(18) H 0.5951 0.7725 -0.3896 0.0705 Uiso 1.00 calc . . .
H(19) H 0.7003 0.7362 -0.2736 0.0705 Uiso 1.00 calc . . .
loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.003 0.002
;International Tables for Crystallography
(1992, Vol. C, Tables 4.2.6.8 and 6.1.1.1)
;
H H 0.000 0.000
;International Tables for Crystallography
(1992, Vol. C, Table 6.1.1.2)
;
N N 0.006 0.003
;International Tables for Crystallography
(1992, Vol. C, Tables 4.2.6.8 and 6.1.1.1)
;
O O 0.011 0.006
;International Tables for Crystallography
(1992, Vol. C, Tables 4.2.6.8 and 6.1.1.1)
;
S S 0.125 0.123
;International Tables for Crystallography
(1992, Vol. C, Tables 4.2.6.8 and 6.1.1.1)
;
loop_
_diffrn_standard_refln_index_h
_diffrn_standard_refln_index_k
_diffrn_standard_refln_index_l
-1 -2 2
-1 0 1
-1 -1 1
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_2
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
C(3) O(1) C(8) 118.3(4) 1_555 1_555 1_555 yes
C(9) N(1) C(10) 108.9(4) 1_555 1_555 1_555 yes
C(9) N(1) C(11) 109.3(4) 1_555 1_555 1_555 yes
C(9) N(1) C(12) 110.3(3) 1_555 1_555 1_555 yes
C(10) N(1) C(11) 109.5(3) 1_555 1_555 1_555 yes
C(10) N(1) C(12) 108.8(4) 1_555 1_555 1_555 yes
C(11) N(1) C(12) 109.9(4) 1_555 1_555 1_555 yes
S(1) C(1) S(2) 125.2(3) 1_555 1_555 1_555 yes
S(1) C(1) C(2) 116.5(3) 1_555 1_555 1_555 yes
S(2) C(1) C(2) 118.1(3) 1_555 1_555 1_555 yes
C(1) C(2) C(3) 121.2(4) 1_555 1_555 1_555 yes
C(1) C(2) C(7) 120.6(4) 1_555 1_555 1_555 yes
C(3) C(2) C(7) 118.2(4) 1_555 1_555 1_555 yes
O(1) C(3) C(2) 116.7(4) 1_555 1_555 1_555 yes
O(1) C(3) C(4) 123.4(5) 1_555 1_555 1_555 yes
C(2) C(3) C(4) 119.8(5) 1_555 1_555 1_555 yes
C(3) C(4) C(5) 120.0(5) 1_555 1_555 1_555 yes
C(3) C(4) H(1) 117.6(6) 1_555 1_555 1_555 no
C(5) C(4) H(1) 122.4(5) 1_555 1_555 1_555 no
C(4) C(5) C(6) 120.7(5) 1_555 1_555 1_555 yes
C(4) C(5) H(2) 118.2(6) 1_555 1_555 1_555 no
C(6) C(5) H(2) 121.0(6) 1_555 1_555 1_555 no
C(5) C(6) C(7) 119.3(6) 1_555 1_555 1_555 yes
C(5) C(6) H(3) 119.1(5) 1_555 1_555 1_555 no
C(7) C(6) H(3) 121.6(6) 1_555 1_555 1_555 no
C(2) C(7) C(6) 121.8(5) 1_555 1_555 1_555 yes
C(2) C(7) H(4) 118.4(5) 1_555 1_555 1_555 no
C(6) C(7) H(4) 119.7(6) 1_555 1_555 1_555 no
O(1) C(8) H(5) 117.3(6) 1_555 1_555 1_555 no
O(1) C(8) H(6) 113.2(5) 1_555 1_555 1_555 no
O(1) C(8) H(7) 111.7(5) 1_555 1_555 1_555 no
H(5) C(8) H(6) 106.5(6) 1_555 1_555 1_555 no
H(5) C(8) H(7) 105.8(5) 1_555 1_555 1_555 no
H(6) C(8) H(7) 100.8(5) 1_555 1_555 1_555 no
N(1) C(9) H(8) 110.7(4) 1_555 1_555 1_555 no
N(1) C(9) H(9) 107.9(4) 1_555 1_555 1_555 no
N(1) C(9) H(10) 106.6(4) 1_555 1_555 1_555 no
H(8) C(9) H(9) 112.3(5) 1_555 1_555 1_555 no
H(8) C(9) H(10) 111.1(5) 1_555 1_555 1_555 no
H(9) C(9) H(10) 108.0(5) 1_555 1_555 1_555 no
N(1) C(10) H(11) 109.0(5) 1_555 1_555 1_555 no
N(1) C(10) H(12) 109.5(5) 1_555 1_555 1_555 no
N(1) C(10) H(13) 107.2(5) 1_555 1_555 1_555 no
H(11) C(10) H(12) 111.2(6) 1_555 1_555 1_555 no
H(11) C(10) H(13) 109.4(5) 1_555 1_555 1_555 no
H(12) C(10) H(13) 110.4(6) 1_555 1_555 1_555 no
N(1) C(11) H(14) 110.3(5) 1_555 1_555 1_555 no
N(1) C(11) H(15) 110.9(5) 1_555 1_555 1_555 no
N(1) C(11) H(16) 110.9(4) 1_555 1_555 1_555 no
H(14) C(11) H(15) 108.1(5) 1_555 1_555 1_555 no
H(14) C(11) H(16) 107.4(6) 1_555 1_555 1_555 no
H(15) C(11) H(16) 109.1(5) 1_555 1_555 1_555 no
N(1) C(12) H(17) 107.4(4) 1_555 1_555 1_555 no
N(1) C(12) H(18) 109.3(4) 1_555 1_555 1_555 no
N(1) C(12) H(19) 111.5(4) 1_555 1_555 1_555 no
H(17) C(12) H(18) 107.5(5) 1_555 1_555 1_555 no
H(17) C(12) H(19) 109.5(5) 1_555 1_555 1_555 no
H(18) C(12) H(19) 111.5(5) 1_555 1_555 1_555 no
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_1
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
S(1) C(1) 1.675(4) 1_555 1_555 yes
S(2) C(1) 1.671(4) 1_555 1_555 yes
O(1) C(3) 1.366(6) 1_555 1_555 yes
O(1) C(8) 1.400(6) 1_555 1_555 yes
N(1) C(9) 1.495(5) 1_555 1_555 yes
N(1) C(10) 1.494(6) 1_555 1_555 yes
N(1) C(11) 1.491(6) 1_555 1_555 yes
N(1) C(12) 1.494(5) 1_555 1_555 yes
C(1) C(2) 1.496(6) 1_555 1_555 yes
C(2) C(3) 1.393(6) 1_555 1_555 yes
C(2) C(7) 1.374(6) 1_555 1_555 yes
C(3) C(4) 1.393(7) 1_555 1_555 yes
C(4) C(5) 1.373(7) 1_555 1_555 yes
C(4) H(1) 1.015 1_555 1_555 no
C(5) C(6) 1.358(8) 1_555 1_555 yes
C(5) H(2) 0.976 1_555 1_555 no
C(6) C(7) 1.385(7) 1_555 1_555 yes
C(6) H(3) 1.005 1_555 1_555 no
C(7) H(4) 0.994 1_555 1_555 no
C(8) H(5) 0.933 1_555 1_555 no
C(8) H(6) 1.002 1_555 1_555 no
C(8) H(7) 1.012 1_555 1_555 no
C(9) H(8) 0.915 1_555 1_555 no
C(9) H(9) 0.952 1_555 1_555 no
C(9) H(10) 0.965 1_555 1_555 no
C(10) H(11) 0.946 1_555 1_555 no
C(10) H(12) 0.935 1_555 1_555 no
C(10) H(13) 0.955 1_555 1_555 no
C(11) H(14) 0.969 1_555 1_555 no
C(11) H(15) 0.948 1_555 1_555 no
C(11) H(16) 0.956 1_555 1_555 no
C(12) H(17) 0.973 1_555 1_555 no
C(12) H(18) 0.950 1_555 1_555 no
C(12) H(19) 0.927 1_555 1_555 no
loop_
_geom_contact_atom_site_label_1
_geom_contact_atom_site_label_2
_geom_contact_distance
_geom_contact_site_symmetry_1
_geom_contact_site_symmetry_2
_geom_contact_publ_flag
O(1) C(9) 3.478(6) 1_555 1_555 ?
C(7) C(8) 3.557(8) 1_555 1_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
_geom_torsion_site_symmetry_1
_geom_torsion_site_symmetry_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
_geom_torsion_publ_flag
S(1) C(1) C(2) C(3) -71.6(5) 1_555 1_555 1_555 1_555 yes
S(1) C(1) C(2) C(7) 107.6(4) 1_555 1_555 1_555 1_555 yes
S(2) C(1) C(2) C(3) 111.4(4) 1_555 1_555 1_555 1_555 yes
S(2) C(1) C(2) C(7) -69.4(5) 1_555 1_555 1_555 1_555 yes
O(1) C(3) C(2) C(1) -4.9(6) 1_555 1_555 1_555 1_555 yes
O(1) C(3) C(2) C(7) 175.9(4) 1_555 1_555 1_555 1_555 yes
O(1) C(3) C(4) C(5) -178.4(4) 1_555 1_555 1_555 1_555 yes
C(1) C(2) C(3) C(4) 175.6(4) 1_555 1_555 1_555 1_555 yes
C(1) C(2) C(7) C(6) -175.1(5) 1_555 1_555 1_555 1_555 yes
C(2) C(3) O(1) C(8) -174.8(5) 1_555 1_555 1_555 1_555 yes
C(2) C(3) C(4) C(5) 1.1(8) 1_555 1_555 1_555 1_555 yes
C(2) C(7) C(6) C(5) -2.0(9) 1_555 1_555 1_555 1_555 yes
C(3) C(2) C(7) C(6) 4.1(8) 1_555 1_555 1_555 1_555 yes
C(3) C(4) C(5) C(6) 1.1(9) 1_555 1_555 1_555 1_555 yes
C(4) C(3) O(1) C(8) 4.7(8) 1_555 1_555 1_555 1_555 yes
C(4) C(3) C(2) C(7) -3.6(7) 1_555 1_555 1_555 1_555 yes
C(4) C(5) C(6) C(7) -0.7(9) 1_555 1_555 1_555 1_555 yes
