#------------------------------------------------------------------------------
#$Date: 2016-02-16 02:10:39 +0100 (mar 16 de feb de 2016) $
#$Revision: 176453 $
#$URL: svn://www.crystallography.net/cod/cif/7/00/73/7007381.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_7007381
loop_
_publ_author_name
'Adams, Christopher J.'
'Crawford, Paul C.'
'Guy Orpen, A.'
'Podesta, Thomas J.'
_publ_section_title
;
 Cation and anion diversity in [M(dithiooxalate)2]2- salts: structure
 robustness in crystal synthesis.
;
_journal_issue                   34
_journal_name_full
'Dalton transactions (Cambridge, England : 2003)'
_journal_page_first              4078
_journal_page_last               4092
_journal_paper_doi               10.1039/b604319d
_journal_year                    2006
_chemical_formula_moiety         'C6 H12 N O2, 0.5(C4 Cu O4 S4)'
_chemical_formula_sum            'C8 H12 Cu0.5 N O4 S2'
_chemical_formula_weight         282.10
_chemical_name_systematic
;
?
;
_space_group_IT_number           15
_symmetry_cell_setting           monoclinic
_symmetry_space_group_name_Hall  '-C 2yc'
_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                 117.028(3)
_cell_angle_gamma                90.00
_cell_formula_units_Z            8
_cell_length_a                   23.276(4)
_cell_length_b                   9.1837(16)
_cell_length_c                   11.898(2)
_cell_measurement_reflns_used    1024
_cell_measurement_temperature    173(2)
_cell_measurement_theta_max      20.5655
_cell_measurement_theta_min      2.804
_cell_volume                     2265.5(7)
_computing_cell_refinement       'Bruker SMART'
_computing_data_collection       'Bruker SMART'
_computing_data_reduction        'Bruker SHELXTL'
_computing_molecular_graphics    'Bruker SHELXTL'
_computing_publication_material  'Bruker SHELXTL'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 1990)'
_diffrn_ambient_temperature      173(2)
_diffrn_measured_fraction_theta_full 1.000
_diffrn_measured_fraction_theta_max 1.000
_diffrn_measurement_device_type  'CCD area detector'
_diffrn_measurement_method       'phi and omega 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  0.1125
_diffrn_reflns_av_sigmaI/netI    0.1153
_diffrn_reflns_limit_h_max       27
_diffrn_reflns_limit_h_min       -27
_diffrn_reflns_limit_k_max       10
_diffrn_reflns_limit_k_min       -10
_diffrn_reflns_limit_l_max       14
_diffrn_reflns_limit_l_min       -14
_diffrn_reflns_number            9561
_diffrn_reflns_theta_full        25.00
_diffrn_reflns_theta_max         25.00
_diffrn_reflns_theta_min         1.96
_exptl_absorpt_coefficient_mu    1.378
_exptl_absorpt_correction_T_max  0.8138949
_exptl_absorpt_correction_T_min  0.6342609
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   'SADABS (Bruker, 1996)'
_exptl_crystal_colour            brown
_exptl_crystal_density_diffrn    1.654
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       prism
_exptl_crystal_F_000             1164
_exptl_crystal_size_max          0.30
_exptl_crystal_size_mid          0.25
_exptl_crystal_size_min          0.15
_refine_diff_density_max         0.369
_refine_diff_density_min         -0.409
_refine_diff_density_rms         0.096
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   0.906
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     143
_refine_ls_number_reflns         1992
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      0.906
_refine_ls_R_factor_all          0.1143
_refine_ls_R_factor_gt           0.0448
_refine_ls_shift/su_max          0.003
_refine_ls_shift/su_mean         0.001
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'calc w=1/[σ²(Fo²)+(0.0420P)²+0.0000P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0839
_refine_ls_wR_factor_ref         0.1034
_reflns_number_gt                1108
_reflns_number_total             1992
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            b604319d.txt
_cod_data_source_block           15
_cod_depositor_comments
;
The following automatic conversions were performed:
'_symmetry_cell_setting' value 'Monoclinic' changed to 'monoclinic'
according to '/home/saulius/struct/CIF-dictionaries/cif_core.dic'
dictionary named 'cif_core.dic' version 2.4.1 from 2010-06-29.

Automatic conversion script
Id: cif_fix_enum 1527 2010-12-29 10:47:43Z saulius 
;
_cod_original_cell_volume        2265.4(7)
_cod_original_sg_symbol_H-M      C2/c
_cod_original_formula_sum        'C8 H12 Cu0.50 N O4 S2'
_cod_database_code               7007381
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
_atom_site_disorder_assembly
_atom_site_disorder_group
Cu1 Cu 0.7500 0.7500 0.0000 0.0249(3) Uani 1 2 d S . .
S1 S 0.71662(7) 0.62723(16) -0.18688(12) 0.0338(4) Uani 1 1 d . . .
O1 O 0.76185(16) 0.6804(4) -0.3475(3) 0.0365(10) Uani 1 1 d . . .
C1 C 0.7705(2) 0.6868(6) -0.2385(5) 0.0257(13) Uani 1 1 d . . .
O4 O 0.47809(17) 0.6656(4) -0.1655(3) 0.0282(9) Uani 1 1 d . . .
H4C H 0.4924 0.6796 -0.2180 0.042 Uiso 0.55(5) 1 calc PR . .
O3 O 0.48186(18) 0.9080(4) -0.1610(3) 0.0363(10) Uani 1 1 d . . .
H3C H 0.4932 0.8934 -0.2177 0.054 Uiso 0.45(5) 1 calc PR . .
C8 C 0.4716(2) 0.7863(6) -0.1217(5) 0.0251(13) Uani 1 1 d . . .
C4 C 0.4402(2) 0.6376(5) 0.0204(4) 0.0268(13) Uani 1 1 d . . .
H4A H 0.4084 0.5853 -0.0550 0.032 Uiso 1 1 calc R . .
H4B H 0.4810 0.5817 0.0553 0.032 Uiso 1 1 calc R . .
C5 C 0.4518(2) 0.7897(5) -0.0180(4) 0.0219(12) Uani 1 1 d . . .
H5A H 0.4878 0.8352 0.0575 0.026 Uiso 1 1 calc R . .
N1 N 0.35635(19) 0.7350(5) 0.0702(3) 0.0268(11) Uani 1 1 d . . .
H1A H 0.3414 0.7372 0.1297 0.032 Uiso 1 1 calc R . .
H1B H 0.3250 0.6927 -0.0017 0.032 Uiso 1 1 calc R . .
C6 C 0.3923(2) 0.8863(5) -0.0566(4) 0.0264(13) Uani 1 1 d . . .
H6A H 0.4033 0.9872 -0.0690 0.032 Uiso 1 1 calc R . .
H6B H 0.3577 0.8514 -0.1380 0.032 Uiso 1 1 calc R . .
C3 C 0.4156(2) 0.6457(6) 0.1178(4) 0.0248(13) Uani 1 1 d . . .
H3A H 0.4062 0.5463 0.1374 0.030 Uiso 1 1 calc R . .
H3B H 0.4491 0.6890 0.1965 0.030 Uiso 1 1 calc R . .
C7 C 0.3677(3) 0.8862(6) 0.0411(5) 0.0321(14) Uani 1 1 d . . .
H7A H 0.3997 0.9340 0.1191 0.039 Uiso 1 1 calc R . .
H7B H 0.3270 0.9422 0.0091 0.039 Uiso 1 1 calc R . .
S2 S 0.84747(7) 0.79239(16) 0.00834(12) 0.0367(4) Uani 1 1 d . . .
O2 O 0.87790(16) 0.7657(4) -0.1765(3) 0.0322(9) Uani 1 1 d . . .
C2 C 0.8366(2) 0.7510(6) -0.1408(4) 0.0262(12) Uani 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'
Cu Cu 0.3201 1.2651 '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
S2 Cu1 S2 180.0 7_665 . ?
S2 Cu1 S1 91.05(5) 7_665 7_665 ?
S2 Cu1 S1 88.95(5) . 7_665 ?
S2 Cu1 S1 88.95(5) 7_665 . ?
S2 Cu1 S1 91.05(5) . . ?
S1 Cu1 S1 180.000(1) 7_665 . ?
C1 S1 Cu1 102.10(18) . . ?
O1 C1 C2 116.1(4) . . ?
O1 C1 S1 124.8(4) . . ?
C2 C1 S1 119.1(3) . . ?
C8 O4 H4C 109.5 . . ?
C8 O3 H3C 109.5 . . ?
O4 C8 O3 122.8(4) . . ?
O4 C8 C5 119.7(5) . . ?
O3 C8 C5 117.4(4) . . ?
C3 C4 C5 111.3(4) . . ?
C3 C4 H4A 109.4 . . ?
C5 C4 H4A 109.4 . . ?
C3 C4 H4B 109.4 . . ?
C5 C4 H4B 109.4 . . ?
H4A C4 H4B 108.0 . . ?
C8 C5 C6 109.9(4) . . ?
C8 C5 C4 112.8(4) . . ?
C6 C5 C4 111.1(4) . . ?
C8 C5 H5A 107.6 . . ?
C6 C5 H5A 107.6 . . ?
C4 C5 H5A 107.6 . . ?
C3 N1 C7 112.0(4) . . ?
C3 N1 H1A 109.2 . . ?
C7 N1 H1A 109.2 . . ?
C3 N1 H1B 109.2 . . ?
C7 N1 H1B 109.2 . . ?
H1A N1 H1B 107.9 . . ?
C7 C6 C5 112.1(4) . . ?
C7 C6 H6A 109.2 . . ?
C5 C6 H6A 109.2 . . ?
C7 C6 H6B 109.2 . . ?
C5 C6 H6B 109.2 . . ?
H6A C6 H6B 107.9 . . ?
N1 C3 C4 110.3(4) . . ?
N1 C3 H3A 109.6 . . ?
C4 C3 H3A 109.6 . . ?
N1 C3 H3B 109.6 . . ?
C4 C3 H3B 109.6 . . ?
H3A C3 H3B 108.1 . . ?
N1 C7 C6 110.5(4) . . ?
N1 C7 H7A 109.6 . . ?
C6 C7 H7A 109.6 . . ?
N1 C7 H7B 109.6 . . ?
C6 C7 H7B 109.6 . . ?
H7A C7 H7B 108.1 . . ?
C2 S2 Cu1 104.03(18) . . ?
O2 C2 C1 116.6(4) . . ?
O2 C2 S2 124.3(4) . . ?
C1 C2 S2 119.1(4) . . ?
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
Cu1 S2 2.2592(14) 7_665 ?
Cu1 S2 2.2592(14) . ?
Cu1 S1 2.2909(13) 7_665 ?
Cu1 S1 2.2910(13) . ?
S1 C1 1.716(5) . ?
O1 C1 1.221(5) . ?
C1 C2 1.562(7) . ?
O4 C8 1.262(6) . ?
O4 H4C 0.8400 . ?
O3 C8 1.275(6) . ?
O3 H3C 0.8400 . ?
C8 C5 1.502(6) . ?
C4 C3 1.510(6) . ?
C4 C5 1.532(6) . ?
C4 H4A 0.9900 . ?
C4 H4B 0.9900 . ?
C5 C6 1.529(6) . ?
C5 H5A 1.0000 . ?
N1 C3 1.478(6) . ?
N1 C7 1.483(6) . ?
N1 H1A 0.9200 . ?
N1 H1B 0.9200 . ?
C6 C7 1.511(6) . ?
C6 H6A 0.9900 . ?
C6 H6B 0.9900 . ?
C3 H3A 0.9900 . ?
C3 H3B 0.9900 . ?
C7 H7A 0.9900 . ?
C7 H7B 0.9900 . ?
S2 C2 1.717(5) . ?
O2 C2 1.223(6) . ?
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
S2 Cu1 S1 C1 161.09(19) 7_665 . . . ?
S2 Cu1 S1 C1 -18.91(19) . . . . ?
Cu1 S1 C1 O1 -160.1(4) . . . . ?
Cu1 S1 C1 C2 21.5(4) . . . . ?
O4 C8 C5 C6 -125.9(5) . . . . ?
O3 C8 C5 C6 54.8(6) . . . . ?
O4 C8 C5 C4 -1.2(7) . . . . ?
O3 C8 C5 C4 179.4(4) . . . . ?
C3 C4 C5 C8 -175.7(4) . . . . ?
C3 C4 C5 C6 -51.8(5) . . . . ?
C8 C5 C6 C7 176.4(4) . . . . ?
C4 C5 C6 C7 50.8(5) . . . . ?
C7 N1 C3 C4 -60.2(5) . . . . ?
C5 C4 C3 N1 56.1(6) . . . . ?
C3 N1 C7 C6 58.9(5) . . . . ?
C5 C6 C7 N1 -53.9(6) . . . . ?
S1 Cu1 S2 C2 -166.22(19) 7_665 . . . ?
S1 Cu1 S2 C2 13.79(19) . . . . ?
O1 C1 C2 O2 -12.2(7) . . . . ?
S1 C1 C2 O2 166.3(4) . . . . ?
O1 C1 C2 S2 169.2(4) . . . . ?
S1 C1 C2 S2 -12.3(6) . . . . ?
Cu1 S2 C2 O2 176.8(4) . . . . ?
Cu1 S2 C2 C1 -4.6(4) . . . . ?
