# Electronic Supplementary Material (ESI) for Dalton Transactions.
# This journal is © The Royal Society of Chemistry 2014

#######################################################################
#
#                 Cambridge Crystallographic Data Centre
#                                CCDC 
# 
#######################################################################
# 
#  This CIF contains data from an original supplementary publication
#  deposited with the CCDC, and may include chemical, crystal,
#  experimental, refinement, atomic coordinates,
#  anisotropic displacement parameters and molecular geometry data,
#  as required by the journal to which it was submitted.
#
#  This CIF is provided on the understanding that it is used for bona
#  fide research purposes only. It may contain copyright material
#  of the CCDC or of third parties, and may not be copied or further
#  disseminated in any form, whether machine-readable or not,
#  except for the purpose of generating routine backup copies
#  on your local computer system.
# 
#  For further information on the CCDC, data deposition and
#  data retrieval see:
#                         www.ccdc.cam.ac.uk
#
#  Bona fide researchers may freely download Mercury and enCIFer
#  from this site to visualise CIF-encoded structures and 
#  to carry out CIF format checking respectively.
#
data_1_353K

_audit_creation_method           SHELXL-97
_chemical_name_systematic        
; 
 ? 
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C12 H12 Cu N6 S2'
_chemical_formula_weight         367.94

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'
Cu Cu 0.3201 1.2651 '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'
S S 0.1246 0.1234 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_symmetry_cell_setting           Orthorhombic
_symmetry_space_group_name_H-M   Cmc21

loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'-x, -y, 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'
'-x+1/2, y+1/2, z'
'x+1/2, -y+1/2, z+1/2'

_cell_length_a                   15.835(2)
_cell_length_b                   15.794(2)
_cell_length_c                   6.3968(9)
_cell_angle_alpha                90.00
_cell_angle_beta                 90.00
_cell_angle_gamma                90.00
_cell_volume                     1599.8(4)
_cell_formula_units_Z            4
_cell_measurement_temperature    353(2)
_cell_measurement_reflns_used    ?
_cell_measurement_theta_min      ?
_cell_measurement_theta_max      ?

_exptl_crystal_description       prism
_exptl_crystal_colour            green
_exptl_crystal_size_max          0.26
_exptl_crystal_size_mid          0.20
_exptl_crystal_size_min          0.15
_exptl_crystal_density_meas      ?
_exptl_crystal_density_diffrn    1.528
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             748
_exptl_absorpt_coefficient_mu    1.627
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.6770
_exptl_absorpt_correction_T_max  0.7924
_exptl_absorpt_process_details   SADABS

_exptl_special_details           
; 
 ? 
;

_diffrn_ambient_temperature      353(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_radiation_source         'fine-focus sealed tube'
_diffrn_radiation_monochromator  graphite
_diffrn_measurement_device_type  'Bruker CCD'
_diffrn_measurement_method       '/w scan'
_diffrn_detector_area_resol_mean ?
_diffrn_standards_number         ?
_diffrn_standards_interval_count ?
_diffrn_standards_interval_time  ?
_diffrn_standards_decay_%        ?
_diffrn_reflns_number            2983
_diffrn_reflns_av_R_equivalents  0.0163
_diffrn_reflns_av_sigmaI/netI    0.0194
_diffrn_reflns_limit_h_min       -18
_diffrn_reflns_limit_h_max       19
_diffrn_reflns_limit_k_min       -18
_diffrn_reflns_limit_k_max       19
_diffrn_reflns_limit_l_min       -7
_diffrn_reflns_limit_l_max       2
_diffrn_reflns_theta_min         1.82
_diffrn_reflns_theta_max         25.99
_reflns_number_total             1057
_reflns_number_gt                1019
_reflns_threshold_expression     >2sigma(I)

_computing_data_collection       ?
_computing_cell_refinement       ?
_computing_data_reduction        ?
_computing_structure_solution    'SHELXS-97 (Sheldrick, 1990)'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_computing_molecular_graphics    ?
_computing_publication_material  ?

_refine_special_details          
; 
 Refinement of F² against ALL reflections.  The weighted R-factor wR and 
 goodness of fit S are based on F², conventional R-factors R are based 
 on F, with F set to zero for negative F². The threshold expression of 
 F² > 2sigma(F²) is used only for calculating R-factors(gt) etc. and is 
 not relevant to the choice of reflections for refinement.  R-factors based 
 on F² are statistically about twice as large as those based on F, and R- 
 factors based on ALL data will be even larger. 
;

_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'calc w=1/[σ²(Fo²)+(0.0531P)²+0.3040P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_atom_sites_solution_hydrogens   geom
_refine_ls_hydrogen_treatment    mixed
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       ?
_refine_ls_abs_structure_details 'Flack H D (1983), Acta Cryst. A39, 876-881'
_refine_ls_abs_structure_Flack   0.032(19)
_refine_ls_number_reflns         1057
_refine_ls_number_parameters     112
_refine_ls_number_restraints     1
_refine_ls_R_factor_all          0.0308
_refine_ls_R_factor_gt           0.0298
_refine_ls_wR_factor_ref         0.0757
_refine_ls_wR_factor_gt          0.0748
_refine_ls_goodness_of_fit_ref   1.054
_refine_ls_restrained_S_all      1.053
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000

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 0.5000 0.85773(2) 0.43385(10) 0.0591(2) Uani 1 2 d S . .
S1 S 0.5000 1.15504(7) 0.3828(2) 0.0708(4) Uani 1 2 d S . .
C2 C 0.4893(15) 0.6647(4) 0.3669(9) 0.046(4) Uani 0.50 1 d P A -1
S2 S 0.5196(2) 0.56672(11) 0.3027(4) 0.0868(12) Uani 0.50 1 d P A -1
N1 N 0.5000 0.9810(2) 0.4336(10) 0.0613(8) Uani 1 2 d S . .
N2 N 0.5000 0.7344(2) 0.4142(11) 0.0714(11) Uani 1 2 d S . .
N3 N 0.62762(17) 0.85973(12) 0.4100(7) 0.0614(7) Uani 1 1 d . . .
N4 N 0.8884(3) 0.8704(3) 0.3434(9) 0.1105(16) Uani 1 1 d . . .
H4A H 0.9226 0.9058 0.4439 0.133 Uiso 1 1 d R . .
H4B H 0.9186 0.8412 0.2246 0.133 Uiso 1 1 d R . .
C1 C 0.5000 1.0526(2) 0.4139(8) 0.0457(8) Uani 1 2 d S . .
C3 C 0.6753(2) 0.9084(2) 0.5330(7) 0.0715(10) Uani 1 1 d . A .
H3 H 0.6487 0.9401 0.6363 0.086 Uiso 1 1 calc R . .
C4 C 0.7615(2) 0.9142(2) 0.5156(8) 0.0760(11) Uani 1 1 d . . .
H4 H 0.7919 0.9488 0.6060 0.091 Uiso 1 1 calc R A .
C5 C 0.8030(3) 0.8683(2) 0.3627(7) 0.0711(10) Uani 1 1 d . A .
C6 C 0.7532(3) 0.8186(3) 0.2313(7) 0.0790(11) Uani 1 1 d . . .
H6 H 0.7780 0.7875 0.1242 0.095 Uiso 1 1 calc R A .
C7 C 0.6686(2) 0.8161(2) 0.2608(6) 0.0688(9) Uani 1 1 d . A .
H7 H 0.6368 0.7820 0.1722 0.083 Uiso 1 1 calc R . .

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
Cu1 0.0596(3) 0.0482(3) 0.0697(4) -0.0043(3) 0.000 0.000
S1 0.1037(9) 0.0471(5) 0.0615(10) -0.0050(5) 0.000 0.000
C2 0.034(12) 0.056(2) 0.048(3) 0.0029(19) -0.003(3) -0.002(3)
S2 0.114(3) 0.0474(6) 0.0986(14) -0.0022(9) 0.0177(14) 0.0033(9)
N1 0.078(2) 0.0501(17) 0.056(2) 0.006(3) 0.000 0.000
N2 0.076(2) 0.0557(19) 0.083(3) -0.011(3) 0.000 0.000
N3 0.0621(13) 0.0592(13) 0.0630(19) -0.0075(14) 0.0003(19) -0.0011(9)
N4 0.0673(19) 0.142(3) 0.122(4) -0.044(3) 0.025(2) -0.0233(19)
C1 0.0486(16) 0.0542(19) 0.0343(19) -0.001(2) 0.000 0.000
C3 0.0664(17) 0.0711(19) 0.077(3) -0.025(2) 0.0088(19) -0.0019(15)
C4 0.072(2) 0.0738(19) 0.083(3) -0.022(2) 0.0006(19) -0.0148(16)
C5 0.0663(19) 0.078(2) 0.069(3) -0.0047(17) 0.0120(16) -0.0117(15)
C6 0.077(2) 0.093(3) 0.067(2) -0.018(2) 0.0136(18) -0.0004(19)
C7 0.070(2) 0.077(2) 0.060(2) -0.0168(19) -0.0001(18) -0.0027(17)

_geom_special_details            
; 
 All esds (except the esd in the dihedral angle between two l.s. planes) 
 are estimated using the full covariance matrix.  The cell esds are taken 
 into account individually in the estimation of esds in distances, angles 
 and torsion angles; correlations between esds in cell parameters are only 
 used when they are defined by crystal symmetry.  An approximate (isotropic) 
 treatment of cell esds is used for estimating esds involving l.s. planes. 
;

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 N1 1.946(3) . ?
Cu1 N2 1.952(4) . ?
Cu1 N3 2.027(3) 3_655 ?
Cu1 N3 2.027(3) . ?
Cu1 S1 2.8787(16) 2_675 ?
S1 C1 1.630(4) . ?
C2 N2 1.154(8) . ?
C2 S2 1.672(9) . ?
N1 C1 1.138(5) . ?
N2 C2 1.154(8) 3_655 ?
N3 C3 1.334(5) . ?
N3 C7 1.344(5) . ?
N4 C5 1.359(6) . ?
N4 H4A 1.0092 . ?
N4 H4B 1.0090 . ?
C3 C4 1.373(5) . ?
C3 H3 0.9300 . ?
C4 C5 1.384(5) . ?
C4 H4 0.9300 . ?
C5 C6 1.394(6) . ?
C6 C7 1.354(5) . ?
C6 H6 0.9300 . ?
C7 H7 0.9300 . ?

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
N1 Cu1 N2 176.3(3) . . ?
N1 Cu1 N3 89.10(6) . 3_655 ?
N2 Cu1 N3 90.62(6) . 3_655 ?
N1 Cu1 N3 89.10(6) . . ?
N2 Cu1 N3 90.62(6) . . ?
N3 Cu1 N3 171.2(3) 3_655 . ?
N1 Cu1 S1 94.07(19) . 2_675 ?
N2 Cu1 S1 89.7(2) . 2_675 ?
N3 Cu1 S1 94.36(13) 3_655 2_675 ?
N3 Cu1 S1 94.36(13) . 2_675 ?
N2 C2 S2 155(2) . . ?
C1 N1 Cu1 173.7(6) . . ?
C2 N2 C2 17(2) 3_655 . ?
C2 N2 Cu1 165.6(9) 3_655 . ?
C2 N2 Cu1 165.6(9) . . ?
C3 N3 C7 116.2(3) . . ?
C3 N3 Cu1 121.9(3) . . ?
C7 N3 Cu1 121.8(3) . . ?
C5 N4 H4A 119.3 . . ?
C5 N4 H4B 121.9 . . ?
H4A N4 H4B 118.6 . . ?
N1 C1 S1 179.3(5) . . ?
N3 C3 C4 123.6(4) . . ?
N3 C3 H3 118.2 . . ?
C4 C3 H3 118.2 . . ?
C3 C4 C5 119.6(4) . . ?
C3 C4 H4 120.2 . . ?
C5 C4 H4 120.2 . . ?
N4 C5 C4 121.6(4) . . ?
N4 C5 C6 121.4(4) . . ?
C4 C5 C6 116.9(4) . . ?
C7 C6 C5 119.5(4) . . ?
C7 C6 H6 120.3 . . ?
C5 C6 H6 120.3 . . ?
N3 C7 C6 124.2(3) . . ?
N3 C7 H7 117.9 . . ?
C6 C7 H7 117.9 . . ?

_diffrn_measured_fraction_theta_max 0.989
_diffrn_reflns_theta_full        25.99
_diffrn_measured_fraction_theta_full 0.989
_refine_diff_density_max         0.193
_refine_diff_density_min         -0.277
_refine_diff_density_rms         0.070
_database_code_depnum_ccdc_archive 'CCDC 980360'
#######################################################################
#
#                 Cambridge Crystallographic Data Centre
#                                CCDC 
# 
#######################################################################
# 
#  This CIF contains data from an original supplementary publication
#  deposited with the CCDC, and may include chemical, crystal,
#  experimental, refinement, atomic coordinates,
#  anisotropic displacement parameters and molecular geometry data,
#  as required by the journal to which it was submitted.
#
#  This CIF is provided on the understanding that it is used for bona
#  fide research purposes only. It may contain copyright material
#  of the CCDC or of third parties, and may not be copied or further
#  disseminated in any form, whether machine-readable or not,
#  except for the purpose of generating routine backup copies
#  on your local computer system.
# 
#  For further information on the CCDC, data deposition and
#  data retrieval see:
#                         www.ccdc.cam.ac.uk
#
#  Bona fide researchers may freely download Mercury and enCIFer
#  from this site to visualise CIF-encoded structures and 
#  to carry out CIF format checking respectively.
#
data_1_103K

_audit_creation_method           SHELXL-97
_chemical_name_systematic        
; 
 ? 
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C12 H12 Cu N6 S2'
_chemical_formula_weight         367.94

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'
Cu Cu 0.3201 1.2651 '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'
S S 0.1246 0.1234 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_symmetry_cell_setting           Orthorhombic
_symmetry_space_group_name_H-M   Pbn21

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'

_cell_length_a                   15.6369(14)
_cell_length_b                   15.6322(14)
_cell_length_c                   6.3057(6)
_cell_angle_alpha                90.00
_cell_angle_beta                 90.00
_cell_angle_gamma                90.00
_cell_volume                     1541.4(2)
_cell_formula_units_Z            4
_cell_measurement_temperature    103(2)
_cell_measurement_reflns_used    ?
_cell_measurement_theta_min      ?
_cell_measurement_theta_max      ?

_exptl_crystal_description       prism
_exptl_crystal_colour            green
_exptl_crystal_size_max          0.26
_exptl_crystal_size_mid          0.20
_exptl_crystal_size_min          0.15
_exptl_crystal_density_meas      ?
_exptl_crystal_density_diffrn    1.586
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             748
_exptl_absorpt_coefficient_mu    1.689
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.6679
_exptl_absorpt_correction_T_max  0.7858
_exptl_absorpt_process_details   SADABS

_exptl_special_details           
; 
 ? 
;

_diffrn_ambient_temperature      103(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_radiation_source         'fine-focus sealed tube'
_diffrn_radiation_monochromator  graphite
_diffrn_measurement_device_type  'Bruker CCD'
_diffrn_measurement_method       '/w scan'
_diffrn_detector_area_resol_mean ?
_diffrn_standards_number         ?
_diffrn_standards_interval_count ?
_diffrn_standards_interval_time  ?
_diffrn_standards_decay_%        ?
_diffrn_reflns_number            5699
_diffrn_reflns_av_R_equivalents  0.0192
_diffrn_reflns_av_sigmaI/netI    0.0257
_diffrn_reflns_limit_h_min       -19
_diffrn_reflns_limit_h_max       17
_diffrn_reflns_limit_k_min       -19
_diffrn_reflns_limit_k_max       18
_diffrn_reflns_limit_l_min       -7
_diffrn_reflns_limit_l_max       2
_diffrn_reflns_theta_min         2.61
_diffrn_reflns_theta_max         25.99
_reflns_number_total             1981
_reflns_number_gt                1889
_reflns_threshold_expression     >2sigma(I)

_computing_data_collection       ?
_computing_cell_refinement       ?
_computing_data_reduction        ?
_computing_structure_solution    'SHELXS-97 (Sheldrick, 1990)'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_computing_molecular_graphics    ?
_computing_publication_material  ?

_refine_special_details          
; 
 Refinement of F² against ALL reflections.  The weighted R-factor wR and 
 goodness of fit S are based on F², conventional R-factors R are based 
 on F, with F set to zero for negative F². The threshold expression of 
 F² > 2sigma(F²) is used only for calculating R-factors(gt) etc. and is 
 not relevant to the choice of reflections for refinement.  R-factors based 
 on F² are statistically about twice as large as those based on F, and R- 
 factors based on ALL data will be even larger. 
;

_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'calc w=1/[σ²(Fo²)+(0.0356P)²+0.2073P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_atom_sites_solution_hydrogens   geom
_refine_ls_hydrogen_treatment    mixed
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       ?
_refine_ls_abs_structure_details 'Flack H D (1983), Acta Cryst. A39, 876-881'
_refine_ls_abs_structure_Flack   0.019(11)
_refine_ls_number_reflns         1981
_refine_ls_number_parameters     202
_refine_ls_number_restraints     2
_refine_ls_R_factor_all          0.0246
_refine_ls_R_factor_gt           0.0233
_refine_ls_wR_factor_ref         0.0603
_refine_ls_wR_factor_gt          0.0595
_refine_ls_goodness_of_fit_ref   1.070
_refine_ls_restrained_S_all      1.070
_refine_ls_shift/su_max          0.001
_refine_ls_shift/su_mean         0.000

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 0.519643(16) 0.858378(18) 0.62696(6) 0.01886(11) Uani 1 1 d . . .
S1 S 0.47569(4) 1.15422(4) 0.57511(12) 0.02197(19) Uani 1 1 d . . .
S2 S 0.52561(5) 0.56197(5) 0.48668(15) 0.0292(2) Uani 1 1 d . . .
N1 N 0.52178(11) 0.98359(13) 0.6348(5) 0.0191(5) Uani 1 1 d . . .
N2 N 0.51575(13) 0.73369(15) 0.6033(6) 0.0253(6) Uani 1 1 d . . .
N3 N 0.64822(13) 0.85678(12) 0.5972(5) 0.0198(5) Uani 1 1 d . . .
N4 N 0.39121(14) 0.86467(12) 0.6006(5) 0.0206(5) Uani 1 1 d . . .
N5 N 0.91354(16) 0.85427(16) 0.5444(5) 0.0272(6) Uani 1 1 d . . .
H5A H 0.937(2) 0.822(2) 0.477(7) 0.033 Uiso 1 1 d . . .
H5B H 0.936(2) 0.877(2) 0.624(8) 0.033 Uiso 1 1 d . . .
N6 N 0.12856(19) 0.8917(2) 0.5092(6) 0.0418(8) Uani 1 1 d D . .
H6A H 0.108(2) 0.922(2) 0.590(6) 0.050 Uiso 1 1 d D . .
H6B H 0.117(3) 0.882(3) 0.405(7) 0.050 Uiso 1 1 d . . .
C1 C 0.50247(15) 1.05382(16) 0.6116(6) 0.0177(5) Uani 1 1 d . . .
C2 C 0.51898(14) 0.6625(2) 0.5530(5) 0.0186(6) Uani 1 1 d . . .
C3 C 0.69777(17) 0.90604(18) 0.7220(5) 0.0235(6) Uani 1 1 d . . .
H3 H 0.6707 0.9417 0.8239 0.028 Uiso 1 1 calc R . .
C4 C 0.78607(18) 0.90742(18) 0.7096(5) 0.0234(6) Uani 1 1 d . . .
H4 H 0.8184 0.9430 0.8017 0.028 Uiso 1 1 calc R . .
C5 C 0.82709(18) 0.85595(15) 0.5602(5) 0.0205(7) Uani 1 1 d . . .
C6 C 0.77555(19) 0.80638(17) 0.4264(5) 0.0233(6) Uani 1 1 d . . .
H6C H 0.8006 0.7718 0.3192 0.028 Uiso 1 1 calc R . .
C7 C 0.68842(17) 0.80833(17) 0.4521(5) 0.0222(6) Uani 1 1 d . . .
H7 H 0.6545 0.7734 0.3619 0.027 Uiso 1 1 calc R . .
C8 C 0.34256(17) 0.91425(18) 0.7277(5) 0.0231(6) Uani 1 1 d . . .
H8 H 0.3701 0.9441 0.8399 0.028 Uiso 1 1 calc R . .
C9 C 0.25592(17) 0.92428(18) 0.7050(5) 0.0239(7) Uani 1 1 d . . .
H9 H 0.2249 0.9593 0.8012 0.029 Uiso 1 1 calc R . .
C10 C 0.21356(18) 0.8827(2) 0.5398(5) 0.0261(7) Uani 1 1 d . . .
C11 C 0.2631(2) 0.8316(2) 0.4066(5) 0.0308(8) Uani 1 1 d . . .
H11 H 0.2373 0.8024 0.2910 0.037 Uiso 1 1 calc R . .
C12 C 0.34942(18) 0.82364(18) 0.4432(5) 0.0237(6) Uani 1 1 d . . .
H12 H 0.3815 0.7872 0.3526 0.028 Uiso 1 1 calc R . .

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
Cu1 0.01629(17) 0.01686(17) 0.0234(2) -0.00054(16) -0.0006(2) -0.00022(10)
S1 0.0267(4) 0.0175(3) 0.0217(5) -0.0020(3) 0.0001(3) 0.0013(2)
S2 0.0414(5) 0.0169(3) 0.0293(5) 0.0000(4) 0.0056(4) -0.0003(3)
N1 0.0180(10) 0.0199(11) 0.0193(13) 0.0021(13) 0.0014(10) 0.0002(7)
N2 0.0224(11) 0.0204(12) 0.0330(17) -0.0023(15) -0.0013(12) -0.0017(8)
N3 0.0178(10) 0.0198(10) 0.0218(15) -0.0018(10) -0.0011(12) 0.0023(8)
N4 0.0224(11) 0.0202(10) 0.0193(14) -0.0008(11) -0.0009(13) -0.0015(8)
N5 0.0198(13) 0.0276(15) 0.0342(17) -0.0078(11) 0.0030(12) 0.0019(9)
N6 0.0194(14) 0.078(2) 0.0283(17) -0.0171(18) -0.0057(13) 0.0000(14)
C1 0.0173(10) 0.0230(13) 0.0128(14) -0.0008(15) 0.0009(13) -0.0050(10)
C2 0.0135(13) 0.0263(15) 0.0159(16) 0.0017(12) -0.0018(10) -0.0012(10)
C3 0.0211(13) 0.0226(14) 0.0268(17) -0.0042(13) 0.0006(13) 0.0024(12)
C4 0.0229(13) 0.0219(14) 0.0254(16) -0.0069(12) -0.0011(13) -0.0052(11)
C5 0.0203(13) 0.0178(13) 0.0233(17) 0.0037(11) 0.0011(12) 0.0007(9)
C6 0.0266(15) 0.0205(13) 0.0229(16) -0.0027(12) 0.0027(12) 0.0061(12)
C7 0.0233(14) 0.0219(13) 0.0214(15) -0.0045(12) -0.0047(13) 0.0008(11)
C8 0.0193(13) 0.0246(14) 0.0253(17) -0.0046(13) -0.0042(12) -0.0020(11)
C9 0.0191(13) 0.0256(14) 0.0271(17) -0.0040(13) -0.0001(12) 0.0021(11)
C10 0.0194(14) 0.0371(15) 0.0218(17) 0.0021(14) 0.0000(13) -0.0024(12)
C11 0.0233(16) 0.0450(19) 0.0241(19) -0.0090(14) -0.0019(12) -0.0078(14)
C12 0.0223(14) 0.0299(15) 0.0188(15) -0.0067(13) 0.0032(12) -0.0024(12)

_geom_special_details            
; 
 All esds (except the esd in the dihedral angle between two l.s. planes) 
 are estimated using the full covariance matrix.  The cell esds are taken 
 into account individually in the estimation of esds in distances, angles 
 and torsion angles; correlations between esds in cell parameters are only 
 used when they are defined by crystal symmetry.  An approximate (isotropic) 
 treatment of cell esds is used for estimating esds involving l.s. planes. 
;

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 N2 1.956(2) . ?
Cu1 N1 1.958(2) . ?
Cu1 N4 2.018(2) . ?
Cu1 N3 2.019(2) . ?
S1 C1 1.641(3) . ?
S2 C2 1.630(3) . ?
N1 C1 1.148(3) . ?
N2 C2 1.158(4) . ?
N3 C7 1.344(4) . ?
N3 C3 1.346(4) . ?
N4 C8 1.350(4) . ?
N4 C12 1.351(4) . ?
N5 C5 1.356(4) . ?
N5 H5A 0.75(4) . ?
N5 H5B 0.71(4) . ?
N6 C10 1.350(4) . ?
N6 H6A 0.767(19) . ?
N6 H6B 0.70(5) . ?
C3 C4 1.383(4) . ?
C3 H3 0.9500 . ?
C4 C5 1.395(4) . ?
C4 H4 0.9500 . ?
C5 C6 1.400(4) . ?
C6 C7 1.372(4) . ?
C6 H6C 0.9500 . ?
C7 H7 0.9500 . ?
C8 C9 1.371(4) . ?
C8 H8 0.9500 . ?
C9 C10 1.395(4) . ?
C9 H9 0.9500 . ?
C10 C11 1.394(4) . ?
C11 C12 1.375(4) . ?
C11 H11 0.9500 . ?
C12 H12 0.9500 . ?

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
N2 Cu1 N1 176.96(17) . . ?
N2 Cu1 N4 90.65(8) . . ?
N1 Cu1 N4 88.30(8) . . ?
N2 Cu1 N3 90.66(8) . . ?
N1 Cu1 N3 89.87(7) . . ?
N4 Cu1 N3 169.73(14) . . ?
C1 N1 Cu1 161.5(2) . . ?
C2 N2 Cu1 167.7(3) . . ?
C7 N3 C3 116.8(2) . . ?
C7 N3 Cu1 122.41(19) . . ?
C3 N3 Cu1 120.8(2) . . ?
C8 N4 C12 115.9(2) . . ?
C8 N4 Cu1 122.7(2) . . ?
C12 N4 Cu1 121.3(2) . . ?
C5 N5 H5A 122(3) . . ?
C5 N5 H5B 116(3) . . ?
H5A N5 H5B 119(4) . . ?
C10 N6 H6A 113(3) . . ?
C10 N6 H6B 112(4) . . ?
H6A N6 H6B 130(5) . . ?
N1 C1 S1 179.1(3) . . ?
N2 C2 S2 178.5(3) . . ?
N3 C3 C4 123.4(3) . . ?
N3 C3 H3 118.3 . . ?
C4 C3 H3 118.3 . . ?
C3 C4 C5 119.2(3) . . ?
C3 C4 H4 120.4 . . ?
C5 C4 H4 120.4 . . ?
N5 C5 C4 121.3(3) . . ?
N5 C5 C6 121.2(3) . . ?
C4 C5 C6 117.5(3) . . ?
C7 C6 C5 119.2(3) . . ?
C7 C6 H6C 120.4 . . ?
C5 C6 H6C 120.4 . . ?
N3 C7 C6 123.9(3) . . ?
N3 C7 H7 118.1 . . ?
C6 C7 H7 118.1 . . ?
N4 C8 C9 124.1(3) . . ?
N4 C8 H8 118.0 . . ?
C9 C8 H8 118.0 . . ?
C8 C9 C10 119.6(3) . . ?
C8 C9 H9 120.2 . . ?
C10 C9 H9 120.2 . . ?
N6 C10 C11 121.3(3) . . ?
N6 C10 C9 121.7(3) . . ?
C11 C10 C9 116.9(3) . . ?
C12 C11 C10 119.7(3) . . ?
C12 C11 H11 120.1 . . ?
C10 C11 H11 120.1 . . ?
N4 C12 C11 123.7(3) . . ?
N4 C12 H12 118.1 . . ?
C11 C12 H12 118.1 . . ?

_diffrn_measured_fraction_theta_max 0.992
_diffrn_reflns_theta_full        25.99
_diffrn_measured_fraction_theta_full 0.992
_refine_diff_density_max         0.530
_refine_diff_density_min         -0.288
_refine_diff_density_rms         0.059
_database_code_depnum_ccdc_archive 'CCDC 980361'
#######################################################################
#
#                 Cambridge Crystallographic Data Centre
#                                CCDC 
# 
#######################################################################
# 
#  This CIF contains data from an original supplementary publication
#  deposited with the CCDC, and may include chemical, crystal,
#  experimental, refinement, atomic coordinates,
#  anisotropic displacement parameters and molecular geometry data,
#  as required by the journal to which it was submitted.
#
#  This CIF is provided on the understanding that it is used for bona
#  fide research purposes only. It may contain copyright material
#  of the CCDC or of third parties, and may not be copied or further
#  disseminated in any form, whether machine-readable or not,
#  except for the purpose of generating routine backup copies
#  on your local computer system.
# 
#  For further information on the CCDC, data deposition and
#  data retrieval see:
#                         www.ccdc.cam.ac.uk
#
#  Bona fide researchers may freely download Mercury and enCIFer
#  from this site to visualise CIF-encoded structures and 
#  to carry out CIF format checking respectively.
#
data_2_353K

_audit_creation_method           SHELXL-97
_chemical_name_systematic        
; 
 ? 
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C14 H16 Cu N6 S2'
_chemical_formula_weight         395.99

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'
Cu Cu 0.3201 1.2651 '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'
S S 0.1246 0.1234 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_symmetry_cell_setting           orthorhombic
_symmetry_space_group_name_H-M   Cmc21

loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'-x, -y, z+1/2'
'x, -y, z+1/2'
'-x, y, z'
'x+1/2, y+1/2, z'
'-x+1/2, -y+1/2, z+1/2'
'x+1/2, -y+1/2, z+1/2'
'-x+1/2, y+1/2, z'

_cell_length_a                   18.0714(16)
_cell_length_b                   15.1311(14)
_cell_length_c                   6.5878(6)
_cell_angle_alpha                90.00
_cell_angle_beta                 90.00
_cell_angle_gamma                90.00
_cell_volume                     1801.4(3)
_cell_formula_units_Z            4
_cell_measurement_temperature    353(2)
_cell_measurement_reflns_used    ?
_cell_measurement_theta_min      ?
_cell_measurement_theta_max      ?

_exptl_crystal_description       prism
_exptl_crystal_colour            green
_exptl_crystal_size_max          0.17
_exptl_crystal_size_mid          0.14
_exptl_crystal_size_min          0.11
_exptl_crystal_density_meas      ?
_exptl_crystal_density_diffrn    1.460
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             812
_exptl_absorpt_coefficient_mu    1.451
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.7906
_exptl_absorpt_correction_T_max  0.8567
_exptl_absorpt_process_details   '(ABSCOR; Higashi, 1995)'

_exptl_special_details           
; 
 ? 
;

_diffrn_ambient_temperature      353(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_radiation_source         'fine-focus sealed tube'
_diffrn_radiation_monochromator  graphite
_diffrn_measurement_device_type  'Rigaku R-AXIS SPIDE IP'
_diffrn_measurement_method       'phi and omega scans'
_diffrn_detector_area_resol_mean ?
_diffrn_standards_number         ?
_diffrn_standards_interval_count ?
_diffrn_standards_interval_time  ?
_diffrn_standards_decay_%        ?
_diffrn_reflns_number            3843
_diffrn_reflns_av_R_equivalents  0.0323
_diffrn_reflns_av_sigmaI/netI    0.0422
_diffrn_reflns_limit_h_min       -22
_diffrn_reflns_limit_h_max       22
_diffrn_reflns_limit_k_min       -18
_diffrn_reflns_limit_k_max       13
_diffrn_reflns_limit_l_min       -7
_diffrn_reflns_limit_l_max       8
_diffrn_reflns_theta_min         3.51
_diffrn_reflns_theta_max         26.00
_reflns_number_total             1567
_reflns_number_gt                1347
_reflns_threshold_expression     >2sigma(I)

_computing_data_collection       ?
_computing_cell_refinement       ?
_computing_data_reduction        ?
_computing_structure_solution    'SHELXS-97 (Sheldrick, 1990)'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_computing_molecular_graphics    ?
_computing_publication_material  ?

_refine_special_details          
; 
 Refinement of F² against ALL reflections.  The weighted R-factor wR and 
 goodness of fit S are based on F², conventional R-factors R are based 
 on F, with F set to zero for negative F². The threshold expression of 
 F² > 2sigma(F²) is used only for calculating R-factors(gt) etc. and is 
 not relevant to the choice of reflections for refinement.  R-factors based 
 on F² are statistically about twice as large as those based on F, and R- 
 factors based on ALL data will be even larger. 
;

_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'calc w=1/[σ²(Fo²)+(0.0404P)²+0.0000P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_atom_sites_solution_hydrogens   geom
_refine_ls_hydrogen_treatment    mixed
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       ?
_refine_ls_abs_structure_details 'Flack H D (1983), Acta Cryst. A39, 876-881'
_refine_ls_abs_structure_Flack   0.00(2)
_refine_ls_number_reflns         1567
_refine_ls_number_parameters     119
_refine_ls_number_restraints     1
_refine_ls_R_factor_all          0.0418
_refine_ls_R_factor_gt           0.0340
_refine_ls_wR_factor_ref         0.0779
_refine_ls_wR_factor_gt          0.0724
_refine_ls_goodness_of_fit_ref   1.061
_refine_ls_restrained_S_all      1.060
_refine_ls_shift/su_max          0.001
_refine_ls_shift/su_mean         0.000

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 0.5000 0.86197(4) 0.45440(10) 0.05017(18) Uani 1 2 d S . .
S1 S 0.5000 1.16933(10) 0.5395(2) 0.0591(3) Uani 1 2 d S . .
S2 S 0.5000 0.57386(12) 0.7277(3) 0.0835(5) Uani 1 2 d S . .
N1 N 0.5000 0.9909(3) 0.4339(8) 0.0588(10) Uani 1 2 d S . .
N2 N 0.5000 0.7386(3) 0.5363(8) 0.0571(10) Uani 1 2 d S . .
N3 N 0.38795(14) 0.86615(18) 0.4764(7) 0.0551(7) Uani 1 1 d . . .
N4 N 0.15952(17) 0.8911(3) 0.5442(7) 0.0812(11) Uani 1 1 d . . .
H4 H 0.138(3) 0.909(3) 0.446(12) 0.097 Uiso 1 1 d . . .
C1 C 0.5000 1.0653(3) 0.4772(8) 0.0458(11) Uani 1 2 d S . .
C2 C 0.5000 0.6708(4) 0.6147(8) 0.0533(12) Uani 1 2 d S . .
C3 C 0.3455(2) 0.9096(3) 0.3399(6) 0.0643(10) Uani 1 1 d . . .
H3 H 0.3688 0.9358 0.2293 0.077 Uiso 1 1 calc R . .
C4 C 0.2707(2) 0.9170(3) 0.3551(6) 0.0667(11) Uani 1 1 d . . .
H4A H 0.2444 0.9465 0.2544 0.080 Uiso 1 1 calc R . .
C5 C 0.2333(2) 0.8809(3) 0.5204(6) 0.0567(10) Uani 1 1 d . . .
C6 C 0.2771(2) 0.8361(3) 0.6618(6) 0.0628(10) Uani 1 1 d . . .
H6 H 0.2554 0.8106 0.7756 0.075 Uiso 1 1 calc R . .
C7 C 0.3517(2) 0.8297(3) 0.6329(6) 0.0602(10) Uani 1 1 d . . .
H7 H 0.3791 0.7982 0.7279 0.072 Uiso 1 1 calc R . .
C8 C 0.1179(2) 0.8584(3) 0.7154(10) 0.0889(16) Uani 1 1 d . . .
H8A H 0.0676 0.8783 0.7054 0.107 Uiso 1 1 calc R . .
H8B H 0.1394 0.8803 0.8388 0.107 Uiso 1 1 calc R . .
H8C H 0.1190 0.7950 0.7157 0.107 Uiso 1 1 calc R . .

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
Cu1 0.0426(3) 0.0541(4) 0.0538(3) -0.0008(3) 0.000 0.000
S1 0.0789(8) 0.0484(8) 0.0501(6) 0.0031(6) 0.000 0.000
S2 0.0998(11) 0.0573(12) 0.0935(13) 0.0160(8) 0.000 0.000
N1 0.065(2) 0.055(3) 0.057(3) -0.009(3) 0.000 0.000
N2 0.049(2) 0.059(3) 0.064(2) 0.001(2) 0.000 0.000
N3 0.0452(13) 0.0634(18) 0.0567(18) 0.0036(15) 0.000(2) 0.0027(11)
N4 0.0414(17) 0.100(3) 0.102(3) 0.025(2) 0.0111(17) 0.0037(17)
C1 0.0370(19) 0.067(4) 0.034(2) 0.008(2) 0.000 0.000
C2 0.046(3) 0.062(4) 0.052(3) -0.011(3) 0.000 0.000
C3 0.055(2) 0.073(3) 0.065(2) 0.018(2) 0.0031(17) 0.0017(18)
C4 0.052(2) 0.078(3) 0.070(2) 0.022(2) 0.0024(16) 0.0116(19)
C5 0.0460(17) 0.060(2) 0.064(3) 0.0006(16) 0.0002(15) 0.0011(15)
C6 0.049(2) 0.072(3) 0.067(3) 0.009(2) 0.0063(17) -0.0017(16)
C7 0.052(2) 0.075(3) 0.054(2) 0.0084(18) -0.0039(17) 0.0039(18)
C8 0.053(2) 0.089(4) 0.125(4) 0.015(3) 0.014(3) -0.006(2)

_geom_special_details            
; 
 All esds (except the esd in the dihedral angle between two l.s. planes) 
 are estimated using the full covariance matrix.  The cell esds are taken 
 into account individually in the estimation of esds in distances, angles 
 and torsion angles; correlations between esds in cell parameters are only 
 used when they are defined by crystal symmetry.  An approximate (isotropic) 
 treatment of cell esds is used for estimating esds involving l.s. planes. 
;

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 N2 1.943(5) . ?
Cu1 N1 1.955(4) . ?
Cu1 N3 2.031(3) 4_655 ?
Cu1 N3 2.031(3) . ?
Cu1 S1 2.7741(16) 2_674 ?
S1 C1 1.627(5) . ?
S1 Cu1 2.7741(16) 2_675 ?
S2 C2 1.645(6) . ?
N1 C1 1.161(6) . ?
N2 C2 1.148(7) . ?
N3 C7 1.340(6) . ?
N3 C3 1.352(5) . ?
N4 C5 1.351(5) . ?
N4 C8 1.443(7) . ?
C3 C4 1.360(5) . ?
C4 C5 1.394(5) . ?
C5 C6 1.398(6) . ?
C6 C7 1.365(5) . ?

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
N2 Cu1 N1 167.8(2) . . ?
N2 Cu1 N3 90.58(9) . 4_655 ?
N1 Cu1 N3 88.50(8) . 4_655 ?
N2 Cu1 N3 90.58(9) . . ?
N1 Cu1 N3 88.50(8) . . ?
N3 Cu1 N3 171.1(2) 4_655 . ?
N2 Cu1 S1 96.28(15) . 2_674 ?
N1 Cu1 S1 95.87(17) . 2_674 ?
N3 Cu1 S1 94.34(13) 4_655 2_674 ?
N3 Cu1 S1 94.33(13) . 2_674 ?
C1 S1 Cu1 94.8(2) . 2_675 ?
C1 N1 Cu1 161.8(5) . . ?
C2 N2 Cu1 169.4(5) . . ?
C7 N3 C3 115.7(3) . . ?
C7 N3 Cu1 122.0(3) . . ?
C3 N3 Cu1 122.2(3) . . ?
C5 N4 C8 124.5(4) . . ?
N1 C1 S1 179.6(5) . . ?
N2 C2 S2 179.8(5) . . ?
N3 C3 C4 123.7(4) . . ?
C3 C4 C5 120.5(4) . . ?
N4 C5 C4 121.7(4) . . ?
N4 C5 C6 122.4(4) . . ?
C4 C5 C6 115.9(3) . . ?
C7 C6 C5 120.0(4) . . ?
N3 C7 C6 124.1(3) . . ?

_diffrn_measured_fraction_theta_max 0.990
_diffrn_reflns_theta_full        26.00
_diffrn_measured_fraction_theta_full 0.990
_refine_diff_density_max         0.642
_refine_diff_density_min         -0.225
_refine_diff_density_rms         0.065
_database_code_depnum_ccdc_archive 'CCDC 980362'
#######################################################################
#
#                 Cambridge Crystallographic Data Centre
#                                CCDC 
# 
#######################################################################
# 
#  This CIF contains data from an original supplementary publication
#  deposited with the CCDC, and may include chemical, crystal,
#  experimental, refinement, atomic coordinates,
#  anisotropic displacement parameters and molecular geometry data,
#  as required by the journal to which it was submitted.
#
#  This CIF is provided on the understanding that it is used for bona
#  fide research purposes only. It may contain copyright material
#  of the CCDC or of third parties, and may not be copied or further
#  disseminated in any form, whether machine-readable or not,
#  except for the purpose of generating routine backup copies
#  on your local computer system.
# 
#  For further information on the CCDC, data deposition and
#  data retrieval see:
#                         www.ccdc.cam.ac.uk
#
#  Bona fide researchers may freely download Mercury and enCIFer
#  from this site to visualise CIF-encoded structures and 
#  to carry out CIF format checking respectively.
#
data_2_103K

_audit_creation_method           SHELXL-97
_chemical_name_systematic        
; 
 ? 
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C14 H16 Cu N6 S2'
_chemical_formula_weight         395.99

loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0181 0.0091 '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'
Cu Cu -1.9646 0.5888 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
N N 0.0311 0.0180 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
S S 0.3331 0.5567 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_symmetry_cell_setting           Orthorhombic
_symmetry_space_group_name_H-M   Cmc21

loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'-x, -y, z+1/2'
'x, -y, z+1/2'
'-x, y, z'
'x+1/2, y+1/2, z'
'-x+1/2, -y+1/2, z+1/2'
'x+1/2, -y+1/2, z+1/2'
'-x+1/2, y+1/2, z'

_cell_length_a                   17.930(6)
_cell_length_b                   14.618(4)
_cell_length_c                   6.513(3)
_cell_angle_alpha                90.00
_cell_angle_beta                 90.00
_cell_angle_gamma                90.00
_cell_volume                     1707.1(10)
_cell_formula_units_Z            4
_cell_measurement_temperature    103(2)
_cell_measurement_reflns_used    ?
_cell_measurement_theta_min      ?
_cell_measurement_theta_max      ?

_exptl_crystal_description       prism
_exptl_crystal_colour            green
_exptl_crystal_size_max          0.25
_exptl_crystal_size_mid          0.12
_exptl_crystal_size_min          0.12
_exptl_crystal_density_meas      ?
_exptl_crystal_density_diffrn    1.541
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             812
_exptl_absorpt_coefficient_mu    4.151
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.4234
_exptl_absorpt_correction_T_max  0.6357
_exptl_absorpt_process_details   'REQAB; Jacobson, 1998'

_exptl_special_details           
; 
 ? 
;

_diffrn_ambient_temperature      103(2)
_diffrn_radiation_wavelength     1.54178
_diffrn_radiation_type           CuK\a
_diffrn_radiation_source         'fine-focus sealed tube'
_diffrn_radiation_monochromator  graphite
_diffrn_measurement_device_type  'XtaLAB P300DS'
_diffrn_measurement_method       '/w scan'
_diffrn_detector_area_resol_mean ?
_diffrn_standards_number         ?
_diffrn_standards_interval_count ?
_diffrn_standards_interval_time  ?
_diffrn_standards_decay_%        ?
_diffrn_reflns_number            7112
_diffrn_reflns_av_R_equivalents  0.1003
_diffrn_reflns_av_sigmaI/netI    0.0572
_diffrn_reflns_limit_h_min       -20
_diffrn_reflns_limit_h_max       21
_diffrn_reflns_limit_k_min       -17
_diffrn_reflns_limit_k_max       17
_diffrn_reflns_limit_l_min       -6
_diffrn_reflns_limit_l_max       7
_diffrn_reflns_theta_min         7.82
_diffrn_reflns_theta_max         68.12
_reflns_number_total             1322
_reflns_number_gt                1314
_reflns_threshold_expression     >2sigma(I)

_computing_data_collection       ?
_computing_cell_refinement       ?
_computing_data_reduction        ?
_computing_structure_solution    'SHELXS-97 (Sheldrick, 1990)'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_computing_molecular_graphics    ?
_computing_publication_material  ?

_refine_special_details          
; 
 Refinement of F² against ALL reflections.  The weighted R-factor wR and 
 goodness of fit S are based on F², conventional R-factors R are based 
 on F, with F set to zero for negative F². The threshold expression of 
 F² > 2sigma(F²) is used only for calculating R-factors(gt) etc. and is 
 not relevant to the choice of reflections for refinement.  R-factors based 
 on F² are statistically about twice as large as those based on F, and R- 
 factors based on ALL data will be even larger. 
;

_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'calc w=1/[σ²(Fo²)+(0.0584P)²+1.3380P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_atom_sites_solution_hydrogens   geom
_refine_ls_hydrogen_treatment    mixed
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       ?
_refine_ls_abs_structure_details 'Flack H D (1983), Acta Cryst. A39, 876-881'
_refine_ls_abs_structure_Flack   0.03(3)
_refine_ls_number_reflns         1322
_refine_ls_number_parameters     119
_refine_ls_number_restraints     1
_refine_ls_R_factor_all          0.0373
_refine_ls_R_factor_gt           0.0366
_refine_ls_wR_factor_ref         0.0923
_refine_ls_wR_factor_gt          0.0910
_refine_ls_goodness_of_fit_ref   1.036
_refine_ls_restrained_S_all      1.036
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000

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 0.5000 0.86476(4) 0.68020(11) 0.0118(2) Uani 1 2 d S . .
S1 S 0.5000 1.17975(8) 0.5787(2) 0.0143(3) Uani 1 2 d S . .
S2 S 0.5000 0.57095(9) 0.3739(2) 0.0194(3) Uani 1 2 d S . .
N1 N 0.5000 0.9987(3) 0.7168(7) 0.0145(10) Uani 1 2 d S . .
N2 N 0.5000 0.7383(3) 0.5821(8) 0.0140(9) Uani 1 2 d S . .
N3 N 0.38778(15) 0.86919(17) 0.6512(6) 0.0137(7) Uani 1 1 d . . .
N4 N 0.15813(16) 0.8931(2) 0.5735(6) 0.0200(7) Uani 1 1 d . . .
H4A H 0.130(2) 0.911(3) 0.671(10) 0.024 Uiso 1 1 d . . .
C1 C 0.5000 1.0736(3) 0.6601(10) 0.0126(11) Uani 1 2 d S . .
C2 C 0.5000 0.6687(3) 0.4955(9) 0.0145(11) Uani 1 2 d S . .
C3 C 0.34440(19) 0.9107(2) 0.7948(6) 0.0149(8) Uani 1 1 d . . .
H3 H 0.3677 0.9360 0.9128 0.018 Uiso 1 1 calc R . .
C4 C 0.2685(2) 0.9176(2) 0.7764(7) 0.0180(8) Uani 1 1 d . . .
H4 H 0.2402 0.9457 0.8824 0.022 Uiso 1 1 calc R . .
C5 C 0.2320(2) 0.8831(2) 0.6000(6) 0.0138(8) Uani 1 1 d . . .
C6 C 0.27787(19) 0.8393(2) 0.4539(6) 0.0150(8) Uani 1 1 d . . .
H6 H 0.2567 0.8137 0.3332 0.018 Uiso 1 1 calc R . .
C7 C 0.3532(2) 0.8339(2) 0.4873(6) 0.0153(8) Uani 1 1 d . . .
H7 H 0.3827 0.8032 0.3877 0.018 Uiso 1 1 calc R . .
C8 C 0.1190(2) 0.8603(2) 0.3933(8) 0.0218(9) Uani 1 1 d . . .
H8A H 0.1418 0.8866 0.2699 0.026 Uiso 1 1 calc R . .
H8B H 0.0665 0.8787 0.4008 0.026 Uiso 1 1 calc R . .
H8C H 0.1223 0.7935 0.3872 0.026 Uiso 1 1 calc R . .

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
Cu1 0.0090(3) 0.0130(4) 0.0132(4) -0.0009(4) 0.000 0.000
S1 0.0192(5) 0.0114(5) 0.0122(6) -0.0003(6) 0.000 0.000
S2 0.0218(6) 0.0132(7) 0.0233(7) -0.0039(6) 0.000 0.000
N1 0.0149(17) 0.018(2) 0.010(3) 0.0024(19) 0.000 0.000
N2 0.0108(16) 0.017(2) 0.014(2) 0.001(2) 0.000 0.000
N3 0.0120(13) 0.0137(13) 0.0154(19) -0.0020(13) 0.0018(14) 0.0018(10)
N4 0.0101(14) 0.0250(17) 0.0251(19) -0.0056(16) -0.0007(15) 0.0024(13)
C1 0.009(2) 0.020(3) 0.009(3) -0.006(3) 0.000 0.000
C2 0.010(2) 0.019(3) 0.014(3) 0.006(3) 0.000 0.000
C3 0.0156(17) 0.0157(17) 0.014(2) -0.0034(16) 0.0015(15) 0.0002(14)
C4 0.0135(18) 0.0207(19) 0.020(2) -0.0053(18) -0.0014(16) 0.0025(14)
C5 0.0124(16) 0.0118(16) 0.017(2) 0.0041(16) -0.0003(16) 0.0007(12)
C6 0.0123(16) 0.0163(16) 0.017(2) -0.0002(18) 0.0013(14) 0.0001(13)
C7 0.0171(17) 0.0160(18) 0.013(2) -0.0016(18) -0.0001(15) -0.0011(13)
C8 0.0119(17) 0.024(2) 0.029(2) -0.0071(18) -0.004(2) -0.0007(14)

_geom_special_details            
; 
 All esds (except the esd in the dihedral angle between two l.s. planes) 
 are estimated using the full covariance matrix.  The cell esds are taken 
 into account individually in the estimation of esds in distances, angles 
 and torsion angles; correlations between esds in cell parameters are only 
 used when they are defined by crystal symmetry.  An approximate (isotropic) 
 treatment of cell esds is used for estimating esds involving l.s. planes. 
;

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 N2 1.956(4) . ?
Cu1 N1 1.972(5) . ?
Cu1 N3 2.022(3) . ?
Cu1 N3 2.022(3) 4_655 ?
Cu1 S1 2.6756(18) 2_675 ?
S1 C1 1.639(5) . ?
S1 Cu1 2.6756(18) 2_674 ?
S2 C2 1.633(6) . ?
N1 C1 1.156(6) . ?
N2 C2 1.163(7) . ?
N3 C7 1.339(5) . ?
N3 C3 1.359(5) . ?
N4 C5 1.344(5) . ?
N4 C8 1.449(6) . ?
C3 C4 1.370(5) . ?
C4 C5 1.415(5) . ?
C5 C6 1.411(5) . ?
C6 C7 1.370(5) . ?

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
N2 Cu1 N1 167.9(2) . . ?
N2 Cu1 N3 89.99(8) . . ?
N1 Cu1 N3 88.82(7) . . ?
N2 Cu1 N3 89.99(8) . 4_655 ?
N1 Cu1 N3 88.82(7) . 4_655 ?
N3 Cu1 N3 168.7(2) . 4_655 ?
N2 Cu1 S1 94.98(16) . 2_675 ?
N1 Cu1 S1 97.13(14) . 2_675 ?
N3 Cu1 S1 95.64(11) . 2_675 ?
N3 Cu1 S1 95.64(11) 4_655 2_675 ?
C1 S1 Cu1 94.8(2) . 2_674 ?
C1 N1 Cu1 154.4(5) . . ?
C2 N2 Cu1 170.1(5) . . ?
C7 N3 C3 117.1(3) . . ?
C7 N3 Cu1 121.6(3) . . ?
C3 N3 Cu1 121.3(3) . . ?
C5 N4 C8 123.0(4) . . ?
N1 C1 S1 179.8(6) . . ?
N2 C2 S2 180.0(5) . . ?
N3 C3 C4 122.8(3) . . ?
C3 C4 C5 120.2(3) . . ?
N4 C5 C6 122.5(4) . . ?
N4 C5 C4 121.4(4) . . ?
C6 C5 C4 116.1(4) . . ?
C7 C6 C5 119.5(4) . . ?
N3 C7 C6 124.2(4) . . ?

_diffrn_measured_fraction_theta_max 0.995
_diffrn_reflns_theta_full        68.12
_diffrn_measured_fraction_theta_full 0.995
_refine_diff_density_max         0.478
_refine_diff_density_min         -0.453
_refine_diff_density_rms         0.083
_database_code_depnum_ccdc_archive 'CCDC 980363'
