data_s93
 
_audit_creation_method            SHELXL-97
_chemical_name_systematic
;
 Dr. S. S. Turner
;
_chemical_name_common             ?
_chemical_melting_point           ?
_chemical_formula_moiety          'C14 H8 Cu N4 S2'
_chemical_formula_sum
 'C14 H8 Cu N4 S2'
_chemical_formula_weight          359.90
 
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'
 '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'
 
_symmetry_cell_setting            orthorhombic
_symmetry_space_group_name_H-M    Pbcn
_symmetry_space_group_name_hall   '-P 2n 2ab'
 
loop_
 _symmetry_equiv_pos_as_xyz
 'x, y, z'
 '-x+1/2, -y+1/2, z+1/2'
 '-x, y, -z+1/2'
 'x+1/2, -y+1/2, -z'
 '-x, -y, -z'
 'x-1/2, y-1/2, -z-1/2'
 'x, -y, z-1/2'
 '-x-1/2, y-1/2, z'
 
_cell_length_a                    7.52250(10)
_cell_length_b                    24.7605(7)
_cell_length_c                    7.5372(2)
_cell_angle_alpha                 90.00
_cell_angle_beta                  90.00
_cell_angle_gamma                 90.00
_cell_volume                      1403.89(6)
_cell_formula_units_Z             4
_cell_measurement_temperature     120(2)
_cell_measurement_reflns_used     3321
_cell_measurement_theta_min       2.910
_cell_measurement_theta_max       27.485
 
_exptl_crystal_description        Needle
_exptl_crystal_colour             'Dark Brown'
_exptl_crystal_size_max           0.24
_exptl_crystal_size_mid           0.03
_exptl_crystal_size_min           0.02
_exptl_crystal_density_meas       ?
_exptl_crystal_density_diffrn     1.703
_exptl_crystal_density_method     'not measured'
_exptl_crystal_F_000              724
_exptl_absorpt_coefficient_mu     1.849
_exptl_absorpt_correction_type    multi-scan
_exptl_absorpt_correction_T_min   0.6653
_exptl_absorpt_correction_T_max   0.9640
_exptl_absorpt_process_details       'SADABS V2.10 (Sheldrick, G.M., 2003)'

_diffrn_ambient_temperature           120(2)
_diffrn_radiation_wavelength           0.71073
_diffrn_radiation_type                      MoK\a
_diffrn_radiation_source                  'Bruker-Nonius FR591 rotating anode'
_diffrn_radiation_monochromator    '10cm confocal mirrors'
_diffrn_measurement_device_type  'Bruker-Nonius 95mm CCD camera on κ-goniostat'
_diffrn_measurement_method          'φ & ω scans'
_diffrn_detector_area_resol_mean   9.091
_diffrn_standards_number          ?
_diffrn_standards_interval_count  ?
_diffrn_standards_interval_time   ?
_diffrn_standards_decay_%         ?
_diffrn_reflns_number             19394
_diffrn_reflns_av_R_equivalents   0.0395
_diffrn_reflns_av_sigmaI/netI     0.0193
_diffrn_reflns_limit_h_min        -9
_diffrn_reflns_limit_h_max        9
_diffrn_reflns_limit_k_min        -30
_diffrn_reflns_limit_k_max        32
_diffrn_reflns_limit_l_min        -9
_diffrn_reflns_limit_l_max        9
_diffrn_reflns_theta_min          3.16
_diffrn_reflns_theta_max          27.47
_reflns_number_total              1608
_reflns_number_gt                 1479
_reflns_threshold_expression      >2sigma(I)
 
_computing_data_collection        
'COLLECT (Hooft, R.W.W., 1998)'
_computing_cell_refinement        
'DENZO (Otwinowski & Minor, 1997) & COLLECT (Hooft, R.W.W., 1998)'
#Although determined using DirAx, the cell is refined in the HKL
#package during data reduction
_computing_data_reduction         
'DENZO (Otwinowski & Minor, 1997) & COLLECT (Hooft, R.W.W., 1998)' 
_computing_structure_solution     'SHELXS-97 (Sheldrick, 1997a)' 
_computing_structure_refinement   'SHELXL-97 (Sheldrick, 1997b)' 
_computing_molecular_graphics     'ORTEP3 for Windows (Farrugia, 1997)'
_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)+(0.0197P)²+2.1771P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary      direct
_atom_sites_solution_secondary    difmap
_atom_sites_solution_hydrogens    geom
_refine_ls_hydrogen_treatment     constr
_refine_ls_extinction_method      none
_refine_ls_extinction_coef        ?
_refine_ls_number_reflns          1608
_refine_ls_number_parameters      96
_refine_ls_number_restraints      0
_refine_ls_R_factor_all           0.0341
_refine_ls_R_factor_gt            0.0291
_refine_ls_wR_factor_ref          0.0717
_refine_ls_wR_factor_gt           0.0689
_refine_ls_goodness_of_fit_ref    1.200
_refine_ls_restrained_S_all       1.200
_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
C1 C -0.0779(3) -0.10410(8) 0.2036(3) 0.0170(4) Uani 1 1 d . . .
C2 C -0.1611(3) -0.15419(8) 0.1559(3) 0.0193(5) Uani 1 1 d . . .
C11 C 0.0879(3) 0.13047(8) 0.2946(3) 0.0166(4) Uani 1 1 d . . .
C12 C 0.1777(3) 0.17715(9) 0.3421(3) 0.0211(5) Uani 1 1 d . . .
H12 H 0.1285 0.2116 0.3162 0.025 Uiso 1 1 calc R . .
C13 C 0.3403(3) 0.17301(9) 0.4277(3) 0.0233(5) Uani 1 1 d . . .
H13 H 0.4043 0.2045 0.4608 0.028 Uiso 1 1 calc R . .
C14 C 0.4078(3) 0.12224(9) 0.4643(3) 0.0236(5) Uani 1 1 d . . .
H14 H 0.5182 0.1182 0.5240 0.028 Uiso 1 1 calc R . .
C15 C 0.3114(3) 0.07751(9) 0.4123(3) 0.0208(5) Uani 1 1 d . . .
H15 H 0.3585 0.0427 0.4368 0.025 Uiso 1 1 calc R . .
N1 N -0.2304(3) -0.19363(8) 0.1157(3) 0.0257(4) Uani 1 1 d . . .
N11 N 0.1553(2) 0.08089(7) 0.3293(2) 0.0170(4) Uani 1 1 d . . .
S1 S -0.18379(7) -0.04507(2) 0.13842(7) 0.01913(14) Uani 1 1 d . . .
Cu1 Cu 0.0000 0.018702(13) 0.2500 0.01644(12) Uani 1 2 d S . .
 
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
C1 0.0193(11) 0.0124(9) 0.0193(10) -0.0003(8) -0.0005(9) -0.0006(8)
C2 0.0186(11) 0.0155(10) 0.0238(11) 0.0012(8) -0.0021(9) 0.0027(9)
C11 0.0204(11) 0.0138(9) 0.0157(10) 0.0000(7) 0.0004(9) 0.0005(8)
C12 0.0253(12) 0.0125(10) 0.0255(11) 0.0003(8) -0.0011(10) -0.0011(9)
C13 0.0256(12) 0.0172(10) 0.0271(12) -0.0017(9) -0.0020(10) -0.0051(9)
C14 0.0197(12) 0.0211(10) 0.0301(12) -0.0011(9) -0.0051(10) -0.0017(9)
C15 0.0201(11) 0.0170(10) 0.0254(11) 0.0000(8) -0.0045(9) 0.0015(9)
N1 0.0273(11) 0.0174(9) 0.0324(11) -0.0001(8) -0.0062(9) -0.0015(8)
N11 0.0183(9) 0.0118(8) 0.0209(9) -0.0006(7) -0.0010(8) -0.0003(7)
S1 0.0195(3) 0.0116(2) 0.0263(3) 0.0002(2) -0.0058(2) -0.0003(2)
Cu1 0.0170(2) 0.00989(18) 0.0225(2) 0.000 -0.00368(16) 0.000
 
_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
C1 C1 1.365(4) 3 ?
C1 C2 1.435(3) . ?
C1 S1 1.736(2) . ?
C2 N1 1.147(3) . ?
C11 N11 1.354(3) . ?
C11 C12 1.386(3) . ?
C11 C11 1.484(4) 3 ?
C12 C13 1.386(3) . ?
C12 H12 0.9500 . ?
C13 C14 1.383(3) . ?
C13 H13 0.9500 . ?
C14 C15 1.380(3) . ?
C14 H14 0.9500 . ?
C15 N11 1.333(3) . ?
C15 H15 0.9500 . ?
N11 Cu1 2.0229(18) . ?
S1 Cu1 2.2609(6) . ?
Cu1 N11 2.0229(18) 3 ?
Cu1 S1 2.2609(6) 3 ?
 
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
C1 C1 C2 120.19(12) 3 . ?
C1 C1 S1 122.62(7) 3 . ?
C2 C1 S1 117.19(16) . . ?
N1 C2 C1 178.5(2) . . ?
N11 C11 C12 121.6(2) . . ?
N11 C11 C11 114.91(12) . 3 ?
C12 C11 C11 123.48(13) . 3 ?
C11 C12 C13 119.2(2) . . ?
C11 C12 H12 120.4 . . ?
C13 C12 H12 120.4 . . ?
C14 C13 C12 118.9(2) . . ?
C14 C13 H13 120.5 . . ?
C12 C13 H13 120.5 . . ?
C15 C14 C13 118.7(2) . . ?
C15 C14 H14 120.7 . . ?
C13 C14 H14 120.7 . . ?
N11 C15 C14 123.0(2) . . ?
N11 C15 H15 118.5 . . ?
C14 C15 H15 118.5 . . ?
C15 N11 C11 118.51(18) . . ?
C15 N11 Cu1 126.83(15) . . ?
C11 N11 Cu1 114.65(14) . . ?
C1 S1 Cu1 101.67(7) . . ?
N11 Cu1 N11 80.87(10) . 3 ?
N11 Cu1 S1 174.00(5) . . ?
N11 Cu1 S1 93.93(5) 3 . ?
N11 Cu1 S1 93.93(5) . 3 ?
N11 Cu1 S1 174.00(5) 3 3 ?
S1 Cu1 S1 91.41(3) . 3 ?
 
_diffrn_measured_fraction_theta_max    0.996
_diffrn_reflns_theta_full              27.47
_diffrn_measured_fraction_theta_full   0.996
_refine_diff_density_max    0.416
_refine_diff_density_min   -0.335
_refine_diff_density_rms    0.070
