 
data_s92
 
_audit_creation_method            SHELXL-97
_chemical_name_systematic
;
 ?
;
_chemical_name_common             ?
_chemical_melting_point           ?
_chemical_formula_moiety          ?
_chemical_formula_sum
 'C19 H14 Cl N2 P S Se'
_chemical_formula_weight          447.76
 
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'
 'P'  'P'   0.1023   0.0942
 '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'
 'Cl'  'Cl'   0.1484   0.1585
 '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                    16.4884(2)
_cell_length_b                    10.8238(2)
_cell_length_c                    10.8189(3)
_cell_angle_alpha                 90.00
_cell_angle_beta                  108.8960(10)
_cell_angle_gamma                 90.00
_cell_volume                      1826.76(6)
_cell_formula_units_Z             4
_cell_measurement_temperature     150(2)
_cell_measurement_reflns_used     10967
_cell_measurement_theta_min       2.91
_cell_measurement_theta_max       43.11
 
_exptl_crystal_description        block
_exptl_crystal_colour             colourless
_exptl_crystal_size_max           0.20
_exptl_crystal_size_mid           0.20
_exptl_crystal_size_min           0.20
_exptl_crystal_density_meas       ?
_exptl_crystal_density_diffrn     1.628
_exptl_crystal_density_method     'not measured'
_exptl_crystal_F_000              896
_exptl_absorpt_coefficient_mu     2.408
_exptl_absorpt_correction_type    Empirical
_exptl_absorpt_correction_T_min   0.6445
_exptl_absorpt_correction_T_max   0.6445
_exptl_absorpt_process_details    'SORTAV (R.H. Blessing, 1995, 1997)'
 
_exptl_special_details
;
 ?
;
 
_diffrn_ambient_temperature       150(2)
_diffrn_radiation_wavelength      0.71073
_diffrn_radiation_type            MoK\a
_diffrn_radiation_source          'Enraf Nonius FR591 rotating anode'
_diffrn_radiation_monochromator   graphite 
_diffrn_measurement_device_type   'Enraf Nonius KappaCCD area detector'
_diffrn_measurement_method        'ω and φ scans to fill Ewald sphere'
_diffrn_detector_area_resol_mean  '9.091 pixels/mm'
_diffrn_standards_number          'n/a'
_diffrn_standards_interval_count  'n/a'
_diffrn_standards_interval_time   'n/a'
_diffrn_standards_decay_%         'n/a'
_diffrn_reflns_number             10396
_diffrn_reflns_av_R_equivalents   0.0467
_diffrn_reflns_av_sigmaI/netI     0.0507
_diffrn_reflns_limit_h_min        -18
_diffrn_reflns_limit_h_max        19
_diffrn_reflns_limit_k_min        -12
_diffrn_reflns_limit_k_max        12
_diffrn_reflns_limit_l_min        -12
_diffrn_reflns_limit_l_max        12
_diffrn_reflns_theta_min          3.22
_diffrn_reflns_theta_max          25.03
_reflns_number_total              3229
_reflns_number_gt                 2775
_reflns_threshold_expression      >2σ(I)
 
_computing_data_collection        
;
'DENZO (Otwinowski and Minor, 1997) & COLLECT (Hooft, 1998) '
;
_computing_cell_refinement        'DENZO and COLLECT'
_computing_data_reduction         'DENZO and COLLECT'
_computing_structure_solution     'SHELXS-97 (Sheldrick, 2008)' 
_computing_structure_refinement   'SHELXL-97 (Sheldrick, 2008)' 
_computing_molecular_graphics     ?
_computing_publication_material   SHELXL-97
 
_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 > 2σ(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)+(0.0230P)²+0.8654P] 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      SHELXL
_refine_ls_extinction_coef        0.0038(5)
_refine_ls_extinction_expression
 'Fc^*^=kFc[1+0.001xFc²λ³/sin(2θ)]^-1/4^'
_refine_ls_number_reflns          3229
_refine_ls_number_parameters      283
_refine_ls_number_restraints      0
_refine_ls_R_factor_all           0.0375
_refine_ls_R_factor_gt            0.0304
_refine_ls_wR_factor_ref          0.0772
_refine_ls_wR_factor_gt           0.0736
_refine_ls_goodness_of_fit_ref    1.081
_refine_ls_restrained_S_all       1.081
_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
Se1 Se 0.180468(17) 0.01119(2) 0.16762(2) 0.02420(12) Uani 1 1 d . . .
S1 S 0.06229(4) 0.01690(6) -0.17456(6) 0.02228(17) Uani 1 1 d . . .
P1 P 0.25180(4) 0.08013(6) 0.05110(6) 0.02012(18) Uani 1 1 d . . .
Cl1 Cl -0.21455(4) 0.00636(6) -0.62709(7) 0.03362(19) Uani 1 1 d . . .
N2 N 0.20222(13) 0.17105(19) -0.0717(2) 0.0224(5) Uani 1 1 d . . .
N1 N 0.09855(14) 0.2194(2) -0.2670(2) 0.0224(5) Uani 1 1 d . . .
C1 C -0.00552(15) 0.0691(2) -0.3264(2) 0.0199(5) Uani 1 1 d . . .
C7 C 0.13153(15) 0.1455(2) -0.1619(2) 0.0198(5) Uani 1 1 d . . .
C5 C -0.01959(16) 0.2384(2) -0.4774(2) 0.0239(6) Uani 1 1 d . . .
C3 C -0.12146(15) 0.0727(2) -0.5231(2) 0.0239(6) Uani 1 1 d . . .
C12 C 0.39325(18) -0.1142(3) -0.1282(3) 0.0290(6) Uani 1 1 d . . .
C2 C -0.07864(17) 0.0133(2) -0.4073(3) 0.0228(6) Uani 1 1 d . . .
C11 C 0.35876(18) -0.2311(3) -0.1373(3) 0.0313(7) Uani 1 1 d . . .
C15 C 0.36050(18) 0.2850(3) 0.0939(3) 0.0300(6) Uani 1 1 d . . .
C8 C 0.29791(15) -0.0452(2) -0.0151(2) 0.0206(5) Uani 1 1 d . . .
C13 C 0.36232(17) -0.0206(3) -0.0690(3) 0.0242(6) Uani 1 1 d . . .
C4 C -0.09281(17) 0.1835(2) -0.5591(3) 0.0255(6) Uani 1 1 d . . .
C10 C 0.29558(19) -0.2567(3) -0.0838(3) 0.0336(7) Uani 1 1 d . . .
C19 C 0.39310(18) 0.1332(3) 0.2653(3) 0.0344(7) Uani 1 1 d . . .
C14 C 0.34144(16) 0.1742(2) 0.1427(2) 0.0230(6) Uani 1 1 d . . .
C6 C 0.02416(15) 0.1800(2) -0.3604(2) 0.0215(5) Uani 1 1 d . . .
C18 C 0.4633(2) 0.2018(3) 0.3360(3) 0.0396(8) Uani 1 1 d . . .
C17 C 0.48151(19) 0.3115(3) 0.2870(3) 0.0392(8) Uani 1 1 d . . .
C9 C 0.26543(18) -0.1637(3) -0.0224(3) 0.0290(6) Uani 1 1 d . . .
C16 C 0.43075(19) 0.3530(3) 0.1667(3) 0.0386(8) Uani 1 1 d . . .
H13 H 0.3849(15) 0.061(2) -0.066(2) 0.018(6) Uiso 1 1 d . . .
H9 H 0.2267(17) -0.178(3) 0.019(3) 0.032(8) Uiso 1 1 d . . .
H5 H 0.0015(14) 0.318(3) -0.501(2) 0.028(8) Uiso 1 1 d . . .
H17 H 0.5287(18) 0.355(3) 0.336(3) 0.035(8) Uiso 1 1 d . . .
H4 H -0.1205(17) 0.222(3) -0.636(3) 0.029(7) Uiso 1 1 d . . .
H15 H 0.3252(17) 0.310(3) 0.016(3) 0.028(7) Uiso 1 1 d . . .
H12 H 0.4363(18) -0.097(3) -0.166(3) 0.036(8) Uiso 1 1 d . . .
H2 H -0.0981(17) -0.060(3) -0.386(3) 0.028(7) Uiso 1 1 d . . .
H19 H 0.375(2) 0.060(3) 0.302(3) 0.048(9) Uiso 1 1 d . . .
H18 H 0.496(2) 0.179(3) 0.419(3) 0.056(10) Uiso 1 1 d . . .
H6 H 0.1249(17) 0.275(3) -0.277(3) 0.020(8) Uiso 1 1 d . . .
H16 H 0.440(2) 0.426(3) 0.135(3) 0.047(10) Uiso 1 1 d . . .
H11 H 0.3782(17) -0.296(3) -0.177(3) 0.033(8) Uiso 1 1 d . . .
H10 H 0.2739(17) -0.336(3) -0.089(3) 0.036(8) Uiso 1 1 d . . .
 
 
_geom_special_details
;
 All s.u.'s (except the s.u. in the dihedral angle between two l.s. planes)
 are estimated using the full covariance matrix.  The cell s.u.'s are taken
 into account individually in the estimation of s.u.'s in distances, angles
 and torsion angles; correlations between s.u.'s in cell parameters are only
 used when they are defined by crystal symmetry.  An approximate (isotropic)
 treatment of cell s.u.'s is used for estimating s.u.'s 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
Se1 P1 2.1189(7) . ?
S1 C1 1.754(2) . ?
S1 C7 1.777(2) . ?
P1 N2 1.642(2) . ?
P1 C14 1.804(3) . ?
P1 C8 1.812(2) . ?
Cl1 C3 1.738(3) . ?
N2 C7 1.285(3) . ?
N1 C7 1.352(3) . ?
N1 C6 1.380(3) . ?
N1 H6 0.77(3) . ?
C1 C2 1.379(4) . ?
C1 C6 1.391(3) . ?
C5 C4 1.379(4) . ?
C5 C6 1.389(3) . ?
C5 H5 0.99(3) . ?
C3 C2 1.382(4) . ?
C3 C4 1.389(4) . ?
C12 C11 1.378(4) . ?
C12 C13 1.382(4) . ?
C12 H12 0.95(3) . ?
C2 H2 0.91(3) . ?
C11 C10 1.374(4) . ?
C11 H11 0.93(3) . ?
C15 C16 1.383(4) . ?
C15 C14 1.387(4) . ?
C15 H15 0.90(3) . ?
C8 C9 1.382(4) . ?
C8 C13 1.393(4) . ?
C13 H13 0.96(3) . ?
C4 H4 0.91(3) . ?
C10 C9 1.384(4) . ?
C10 H10 0.93(3) . ?
C19 C18 1.380(4) . ?
C19 C14 1.396(4) . ?
C19 H19 0.97(3) . ?
C18 C17 1.372(5) . ?
C18 H18 0.92(3) . ?
C17 C16 1.375(5) . ?
C17 H17 0.91(3) . ?
C9 H9 0.91(3) . ?
C16 H16 0.89(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
C1 S1 C7 91.09(11) . . ?
N2 P1 C14 102.16(11) . . ?
N2 P1 C8 106.95(11) . . ?
C14 P1 C8 105.42(11) . . ?
N2 P1 Se1 117.73(8) . . ?
C14 P1 Se1 112.68(8) . . ?
C8 P1 Se1 110.87(8) . . ?
C7 N2 P1 125.22(18) . . ?
C7 N1 C6 117.0(2) . . ?
C7 N1 H6 119(2) . . ?
C6 N1 H6 123(2) . . ?
C2 C1 C6 121.3(2) . . ?
C2 C1 S1 127.9(2) . . ?
C6 C1 S1 110.72(18) . . ?
N2 C7 N1 122.0(2) . . ?
N2 C7 S1 129.01(19) . . ?
N1 C7 S1 108.97(18) . . ?
C4 C5 C6 118.5(2) . . ?
C4 C5 H5 121.2(14) . . ?
C6 C5 H5 120.3(14) . . ?
C2 C3 C4 122.4(2) . . ?
C2 C3 Cl1 118.6(2) . . ?
C4 C3 Cl1 118.99(19) . . ?
C11 C12 C13 120.1(3) . . ?
C11 C12 H12 120.2(18) . . ?
C13 C12 H12 119.6(18) . . ?
C1 C2 C3 117.2(2) . . ?
C1 C2 H2 121.7(17) . . ?
C3 C2 H2 121.1(17) . . ?
C10 C11 C12 120.4(3) . . ?
C10 C11 H11 117.6(17) . . ?
C12 C11 H11 122.0(17) . . ?
C16 C15 C14 119.6(3) . . ?
C16 C15 H15 122.7(18) . . ?
C14 C15 H15 117.6(18) . . ?
C9 C8 C13 119.2(2) . . ?
C9 C8 P1 120.83(19) . . ?
C13 C8 P1 119.8(2) . . ?
C12 C13 C8 120.0(3) . . ?
C12 C13 H13 119.9(14) . . ?
C8 C13 H13 120.1(14) . . ?
C5 C4 C3 119.9(2) . . ?
C5 C4 H4 117.6(17) . . ?
C3 C4 H4 122.5(17) . . ?
C11 C10 C9 119.7(3) . . ?
C11 C10 H10 119.5(17) . . ?
C9 C10 H10 120.8(17) . . ?
C18 C19 C14 120.0(3) . . ?
C18 C19 H19 121.6(19) . . ?
C14 C19 H19 118.2(19) . . ?
C15 C14 C19 119.5(3) . . ?
C15 C14 P1 121.7(2) . . ?
C19 C14 P1 118.8(2) . . ?
N1 C6 C5 127.1(2) . . ?
N1 C6 C1 112.2(2) . . ?
C5 C6 C1 120.7(2) . . ?
C17 C18 C19 120.0(3) . . ?
C17 C18 H18 119(2) . . ?
C19 C18 H18 121(2) . . ?
C18 C17 C16 120.4(3) . . ?
C18 C17 H17 118.0(18) . . ?
C16 C17 H17 121.5(18) . . ?
C8 C9 C10 120.6(3) . . ?
C8 C9 H9 116.7(18) . . ?
C10 C9 H9 122.5(18) . . ?
C17 C16 C15 120.4(3) . . ?
C17 C16 H16 122(2) . . ?
C15 C16 H16 118(2) . . ?
 
_diffrn_measured_fraction_theta_max    0.998
_diffrn_reflns_theta_full              25.03
_diffrn_measured_fraction_theta_full   0.998
_refine_diff_density_max    0.424
_refine_diff_density_min   -0.520
_refine_diff_density_rms    0.077
