data_s92
 
_audit_creation_method            SHELXL-97
_chemical_name_systematic
;
 Prof. D. Bruce
;
_chemical_name_common             ?
_chemical_melting_point           ?
_chemical_formula_moiety          'C9 H6 Cl3 Cu3 N Se'
_chemical_formula_sum
 'C9 H6 Cl3 Cu3 N Se'
_chemical_formula_weight          504.08
 
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'
 'Cl'  'Cl'   0.1484   0.1585
 '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'
 'Se'  'Se'  -0.0929   2.2259
 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
 
_symmetry_cell_setting            Monoclinic
_symmetry_space_group_name_H-M    P2(1)/c
_symmetry_space_group_name_hall   '-P 2ybc'
 
loop_
 _symmetry_equiv_pos_as_xyz
 'x, y, z'
 '-x, y+1/2, -z+1/2'
 '-x, -y, -z'
 'x, -y-1/2, z-1/2'
 
_cell_length_a                    3.7872(3)
_cell_length_b                    14.5657(11)
_cell_length_c                    22.444(2)
_cell_angle_alpha                 90.00
_cell_angle_beta                  91.700(3)
_cell_angle_gamma                 90.00
_cell_volume                      1237.51(18)
_cell_formula_units_Z             4
_cell_measurement_temperature     120(2)
_cell_measurement_reflns_used     2582
_cell_measurement_theta_min       2.910
_cell_measurement_theta_max       27.485
 
_exptl_crystal_description        Needle
_exptl_crystal_colour             'Light Brown'
_exptl_crystal_size_max           0.22
_exptl_crystal_size_mid           0.05
_exptl_crystal_size_min           0.02
_exptl_crystal_density_meas       ?
_exptl_crystal_density_diffrn     2.706
_exptl_crystal_density_method     'not measured'
_exptl_crystal_F_000              956
_exptl_absorpt_coefficient_mu     8.666
_exptl_absorpt_correction_type    multi-scan
_exptl_absorpt_correction_T_min   0.2515
_exptl_absorpt_correction_T_max   0.8458
_exptl_absorpt_process_details    'SORTAV Blessing (1997)'
 
_exptl_special_details
;
 PLEASE NOTE cell_measurement_ fields are not relevant to area detector data,
 the entire data set is used to refine the cell, which is indexed from all
 observed reflections in a 10 degree phi range.
;
 
_diffrn_ambient_temperature       120(2)
_diffrn_radiation_wavelength      0.71073
_diffrn_radiation_type            MoK\a
_diffrn_radiation_source          'Nonius FR591 rotating anode'
_diffrn_radiation_monochromator   graphite 
_diffrn_measurement_device_type   'Nonius KappaCCD Area Detector'
_diffrn_measurement_method        'φ and ω scans to fill Ewald Sphere'
_diffrn_detector_area_resol_mean  9.091
_diffrn_standards_number          ?
_diffrn_standards_interval_count  ?
_diffrn_standards_interval_time   ?
_diffrn_standards_decay_%         ?
_diffrn_reflns_number             11352
_diffrn_reflns_av_R_equivalents   0.0929
_diffrn_reflns_av_sigmaI/netI     0.1083
_diffrn_reflns_limit_h_min        -4
_diffrn_reflns_limit_h_max        4
_diffrn_reflns_limit_k_min        -18
_diffrn_reflns_limit_k_max        18
_diffrn_reflns_limit_l_min        -29
_diffrn_reflns_limit_l_max        29
_diffrn_reflns_theta_min          2.94
_diffrn_reflns_theta_max          27.42
_reflns_number_total              2739
_reflns_number_gt                 1838
_reflns_threshold_expression      >2sigma(I)
 
_computing_data_collection
' DENZO (Otwinowski and Minor, 1997)'
_computing_cell_refinement        
' DENZO (Otwinowski & Minor, 1997) and COLLECT (Hooft, 1998)'
_computing_data_reduction         
' DENZO (Otwinowski & Minor, 1997) and COLLECT (Hooft, 1998)'
_computing_structure_solution     'SHELXS-97 (Sheldrick, 1997a)' 
_computing_structure_refinement   'SHELXL-97 (Sheldrick, 1997b)' 
_computing_molecular_graphics     'PLATON (Spek, 1990)'
_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)+(0.0189P)²+27.2706P] 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          2739
_refine_ls_number_parameters      154
_refine_ls_number_restraints      0
_refine_ls_R_factor_all           0.1417
_refine_ls_R_factor_gt            0.0877
_refine_ls_wR_factor_ref          0.1764
_refine_ls_wR_factor_gt           0.1610
_refine_ls_goodness_of_fit_ref    1.154
_refine_ls_restrained_S_all       1.154
_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 0.203(3) 0.0812(9) 0.2863(5) 0.028(3) Uani 1 1 d . . .
C2 C 0.335(3) 0.0744(10) 0.2304(5) 0.031(3) Uani 1 1 d . . .
H2 H 0.3637 0.1278 0.2068 0.037 Uiso 1 1 calc R . .
C3 C 0.426(3) -0.0114(10) 0.2084(6) 0.034(3) Uani 1 1 d . . .
H3 H 0.5143 -0.0153 0.1693 0.041 Uiso 1 1 calc R . .
C4 C 0.396(3) -0.0890(9) 0.2401(5) 0.030(3) Uani 1 1 d . . .
H4 H 0.4773 -0.1456 0.2246 0.036 Uiso 1 1 calc R . .
C5 C 0.240(3) -0.0860(10) 0.2974(6) 0.034(3) Uani 1 1 d . . .
C6 C 0.147(3) 0.0015(10) 0.3217(5) 0.032(3) Uani 1 1 d . . .
C7 C -0.031(3) -0.0682(8) 0.4085(5) 0.024(3) Uani 1 1 d . . .
H7 H -0.1189 -0.0629 0.4476 0.029 Uiso 1 1 calc R . .
C8 C 0.043(4) -0.1560(9) 0.3870(6) 0.036(3) Uani 1 1 d . . .
H8 H -0.0059 -0.2089 0.4101 0.043 Uiso 1 1 calc R . .
C9 C 0.186(3) -0.1640(10) 0.3320(7) 0.036(3) Uani 1 1 d . . .
H9 H 0.2488 -0.2228 0.3173 0.043 Uiso 1 1 calc R . .
N1 N 0.016(3) 0.0075(7) 0.3775(4) 0.027(2) Uani 1 1 d . . .
Cl1 Cl -0.5058(8) 0.1687(2) 0.47121(13) 0.0297(7) Uani 1 1 d . . .
Cl2 Cl -0.4857(9) 0.3747(2) 0.57331(15) 0.0369(8) Uani 1 1 d . . .
Cl3 Cl -1.0007(9) 0.6125(2) 0.57623(16) 0.0408(9) Uani 1 1 d . . .
Cu1 Cu -0.0385(5) 0.12478(12) 0.42062(7) 0.0377(5) Uani 1 1 d . . .
Cu2 Cu -0.4890(5) 0.32722(14) 0.47202(9) 0.0507(5) Uani 1 1 d . . .
Cu3 Cu -0.9840(5) 0.46095(13) 0.56131(8) 0.0460(5) Uani 1 1 d . . .
Se1 Se 0.0692(4) 0.19748(9) 0.31629(6) 0.0287(3) Uani 1 1 d . . .
 
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 0.021(7) 0.035(7) 0.026(6) -0.010(6) -0.005(5) -0.007(6)
C2 0.020(7) 0.047(8) 0.024(6) -0.002(6) -0.005(5) 0.006(6)
C3 0.025(7) 0.058(9) 0.021(6) -0.004(6) 0.000(5) -0.008(7)
C4 0.019(7) 0.041(8) 0.030(7) -0.013(6) 0.001(5) 0.003(6)
C5 0.028(8) 0.040(8) 0.034(7) -0.007(6) -0.006(6) 0.001(7)
C6 0.019(7) 0.054(9) 0.021(6) -0.004(6) -0.009(5) -0.002(6)
C7 0.018(6) 0.029(7) 0.025(6) 0.005(5) -0.002(5) -0.002(5)
C8 0.045(9) 0.029(7) 0.034(8) 0.013(6) -0.015(7) -0.003(7)
C9 0.018(7) 0.036(8) 0.053(9) 0.000(7) -0.015(6) 0.001(6)
N1 0.029(6) 0.027(6) 0.024(5) -0.002(4) -0.001(4) -0.002(5)
Cl1 0.0254(16) 0.0368(17) 0.0268(15) 0.0016(13) 0.0022(12) -0.0013(14)
Cl2 0.0345(18) 0.0335(18) 0.0429(19) -0.0115(15) 0.0032(15) 0.0004(15)
Cl3 0.0320(19) 0.0356(19) 0.055(2) 0.0141(16) 0.0007(16) 0.0000(16)
Cu1 0.0443(11) 0.0381(10) 0.0311(9) -0.0018(7) 0.0068(7) 0.0031(8)
Cu2 0.0500(12) 0.0551(12) 0.0470(11) 0.0085(9) 0.0030(9) 0.0016(10)
Cu3 0.0413(11) 0.0488(12) 0.0480(11) 0.0077(9) 0.0046(9) 0.0028(9)
Se1 0.0310(7) 0.0283(7) 0.0271(6) 0.0026(6) 0.0046(5) 0.0006(6)
 
_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 C2 1.367(16) . ?
C1 C6 1.427(18) . ?
C1 Se1 1.897(13) . ?
C2 C3 1.392(19) . ?
C2 H2 0.9500 . ?
C3 C4 1.342(18) . ?
C3 H3 0.9500 . ?
C4 C5 1.431(18) . ?
C4 H4 0.9500 . ?
C5 C9 1.394(19) . ?
C5 C6 1.435(19) . ?
C6 N1 1.365(15) . ?
C7 N1 1.318(15) . ?
C7 C8 1.397(18) . ?
C7 H7 0.9500 . ?
C8 C9 1.369(19) . ?
C8 H8 0.9500 . ?
C9 H9 0.9500 . ?
N1 Cu1 1.977(10) . ?
Cl1 Cu1 2.225(3) . ?
Cl1 Cu2 2.310(4) . ?
Cl1 Cu1 2.373(3) 1_455 ?
Cl2 Cu3 2.276(4) . ?
Cl2 Cu3 2.300(4) 1_655 ?
Cl2 Cu2 2.376(4) . ?
Cl3 Cu3 2.234(4) . ?
Cl3 Cu2 2.345(4) 3_466 ?
Cl3 Cu2 2.356(4) 3_366 ?
Cu1 Cl1 2.373(3) 1_655 ?
Cu1 Se1 2.613(2) . ?
Cu2 Cl3 2.345(4) 3_466 ?
Cu2 Cl3 2.356(4) 3_366 ?
Cu3 Cl2 2.300(4) 1_455 ?
Cu3 Cu3 2.977(4) 3_366 ?
 
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
C2 C1 C6 121.1(12) . . ?
C2 C1 Se1 120.0(10) . . ?
C6 C1 Se1 118.9(9) . . ?
C1 C2 C3 119.5(13) . . ?
C1 C2 H2 120.3 . . ?
C3 C2 H2 120.3 . . ?
C4 C3 C2 122.8(12) . . ?
C4 C3 H3 118.6 . . ?
C2 C3 H3 118.6 . . ?
C3 C4 C5 119.7(12) . . ?
C3 C4 H4 120.1 . . ?
C5 C4 H4 120.1 . . ?
C9 C5 C4 123.2(13) . . ?
C9 C5 C6 118.1(12) . . ?
C4 C5 C6 118.7(12) . . ?
N1 C6 C1 121.6(12) . . ?
N1 C6 C5 120.4(12) . . ?
C1 C6 C5 118.0(11) . . ?
N1 C7 C8 123.5(11) . . ?
N1 C7 H7 118.2 . . ?
C8 C7 H7 118.2 . . ?
C9 C8 C7 118.6(12) . . ?
C9 C8 H8 120.7 . . ?
C7 C8 H8 120.7 . . ?
C8 C9 C5 120.1(13) . . ?
C8 C9 H9 119.9 . . ?
C5 C9 H9 119.9 . . ?
C7 N1 C6 119.3(11) . . ?
C7 N1 Cu1 116.6(8) . . ?
C6 N1 Cu1 123.4(9) . . ?
Cu1 Cl1 Cu2 105.63(14) . . ?
Cu1 Cl1 Cu1 110.86(14) . 1_455 ?
Cu2 Cl1 Cu1 107.22(14) . 1_455 ?
Cu3 Cl2 Cu3 111.69(16) . 1_655 ?
Cu3 Cl2 Cu2 93.82(14) . . ?
Cu3 Cl2 Cu2 91.59(14) 1_655 . ?
Cu3 Cl3 Cu2 105.91(16) . 3_466 ?
Cu3 Cl3 Cu2 109.00(16) . 3_366 ?
Cu2 Cl3 Cu2 107.31(15) 3_466 3_366 ?
N1 Cu1 Cl1 126.4(3) . . ?
N1 Cu1 Cl1 111.6(3) . 1_655 ?
Cl1 Cu1 Cl1 110.86(14) . 1_655 ?
N1 Cu1 Se1 83.7(3) . . ?
Cl1 Cu1 Se1 119.24(11) . . ?
Cl1 Cu1 Se1 99.58(10) 1_655 . ?
Cl1 Cu2 Cl3 113.09(14) . 3_466 ?
Cl1 Cu2 Cl3 110.28(14) . 3_366 ?
Cl3 Cu2 Cl3 107.31(15) 3_466 3_366 ?
Cl1 Cu2 Cl2 107.33(14) . . ?
Cl3 Cu2 Cl2 110.55(15) 3_466 . ?
Cl3 Cu2 Cl2 108.19(15) 3_366 . ?
Cl3 Cu3 Cl2 123.69(15) . . ?
Cl3 Cu3 Cl2 119.66(15) . 1_455 ?
Cl2 Cu3 Cl2 111.69(16) . 1_455 ?
Cl3 Cu3 Cu3 76.14(12) . 3_366 ?
Cl2 Cu3 Cu3 109.34(13) . 3_366 ?
Cl2 Cu3 Cu3 107.81(13) 1_455 3_366 ?
C1 Se1 Cu1 90.4(4) . . ?
 
_diffrn_measured_fraction_theta_max    0.977
_diffrn_reflns_theta_full              27.42
_diffrn_measured_fraction_theta_full   0.977
_refine_diff_density_max    1.939
_refine_diff_density_min   -0.880
_refine_diff_density_rms    0.215
