 
data_123
 
_audit_creation_method            SHELXL-2014
_chemical_name_systematic
;
 ?
;
_chemical_name_common             ?
_chemical_melting_point           ?
_chemical_formula_moiety          'C12 H15 N S Se2'
_chemical_formula_sum
 'C12 H15 N S Se2' 
_chemical_formula_weight          363.23

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'
 'Se'  'Se'  -0.0929   2.2259
 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
 
_space_group_crystal_system       monoclinic
_space_group_IT_number            15
_space_group_name_H-M_alt         'C 2/c'
_space_group_name_Hall            '-C 2yc'
 
_shelx_space_group_comment
;
The symmetry employed for this shelxl refinement is uniquely defined
by the following loop, which should always be used as a source of
symmetry information in preference to the above space-group names.
They are only intended as comments.
;
 
loop_
 _space_group_symop_operation_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'
 
_cell_length_a                    23.773(14)
_cell_length_b                    6.507(4)
_cell_length_c                    18.085(11)
_cell_angle_alpha                 90
_cell_angle_beta                  105.479(11)
_cell_angle_gamma                 90
_cell_volume                      2696(3)
_cell_formula_units_Z             8
_cell_measurement_temperature     296(2)
_cell_measurement_reflns_used     2124
_cell_measurement_theta_min       2.337 
_cell_measurement_theta_max       28.025 
 
_exptl_crystal_description        Plate 
_exptl_crystal_colour             Yellow 
_exptl_crystal_density_meas       ? 
_exptl_crystal_density_method     ?              
_exptl_crystal_density_diffrn     1.790          
_exptl_crystal_F_000              1424
_exptl_transmission_factor_min    ?                                             
_exptl_transmission_factor_max    ?                                             
_exptl_crystal_size_max           0.200
_exptl_crystal_size_mid           0.180
_exptl_crystal_size_min           0.100
_exptl_absorpt_coefficient_mu     5.614
_shelx_estimated_absorpt_T_min    0.400
_shelx_estimated_absorpt_T_max    0.604
_exptl_absorpt_correction_type    multi-scan 
_exptl_absorpt_correction_T_min   0.338
_exptl_absorpt_correction_T_max   0.570 
_exptl_absorpt_process_details    ? 
 
_exptl_special_details
;
 ?
;
 
_diffrn_ambient_temperature       296(2)
_diffrn_radiation_wavelength      0.71073
_diffrn_radiation_type            MoK\a
_diffrn_source                    ?                       
_diffrn_measurement_device_type   'CCD area detector'
_diffrn_measurement_method        'phi and omega scans'
_diffrn_detector_area_resol_mean  ? 
_diffrn_reflns_number             3865
_diffrn_reflns_av_unetI/netI      0.0603
_diffrn_reflns_av_R_equivalents   0.0315
_diffrn_reflns_limit_h_min        -23
_diffrn_reflns_limit_h_max        28
_diffrn_reflns_limit_k_min        -7
_diffrn_reflns_limit_k_max        7
_diffrn_reflns_limit_l_min        -21
_diffrn_reflns_limit_l_max        9
_diffrn_reflns_theta_min          2.337
_diffrn_reflns_theta_max          25.045
_diffrn_reflns_theta_full         25.242
_diffrn_measured_fraction_theta_max   0.962
_diffrn_measured_fraction_theta_full  0.947
_diffrn_reflns_Laue_measured_fraction_max    0.962
_diffrn_reflns_Laue_measured_fraction_full   0.947
_diffrn_reflns_point_group_measured_fraction_max   0.962
_diffrn_reflns_point_group_measured_fraction_full  0.947
_reflns_number_total              2306
_reflns_number_gt                 1906
_reflns_threshold_expression      'I > 2σ(I)'
_reflns_Friedel_coverage          0.000
_reflns_Friedel_fraction_max      .
_reflns_Friedel_fraction_full     .
 
_reflns_special_details
;
 Reflections were merged by SHELXL according to the crystal
 class for the calculation of statistics and refinement.
 
 _reflns_Friedel_fraction is defined as the number of unique
 Friedel pairs measured divided by the number that would be
 possible theoretically, ignoring centric projections and
 systematic absences.
;
 
_computing_data_collection         'Bruker SMART'
_computing_cell_refinement          'Bruker SMART'
_computing_data_reduction        'Bruker SAINT'
_computing_structure_solution     'Bruker SHELXTL'
_computing_structure_refinement 'SHELXL-2014/7 (Sheldrick, 2014)'
_computing_molecular_graphics     'Bruker SHELXTL'
_computing_publication_material   'Bruker SHELXTL'
 
_refine_special_details
;
 ?
;
_refine_ls_structure_factor_coef  Fsqd
_refine_ls_matrix_type            full
_refine_ls_weighting_scheme       calc
_refine_ls_weighting_details
'w=1/[σ²(Fo²)+(0.1566P)²+10.2212P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary      ?
_atom_sites_solution_secondary    ?
_atom_sites_solution_hydrogens    geom
_refine_ls_hydrogen_treatment     constr
_refine_ls_extinction_method      none
_refine_ls_extinction_coef        .
_refine_ls_number_reflns          2306
_refine_ls_number_parameters      145
_refine_ls_number_restraints      0
_refine_ls_R_factor_all           0.0780
_refine_ls_R_factor_gt            0.0621
_refine_ls_wR_factor_ref          0.2229
_refine_ls_wR_factor_gt           0.1861
_refine_ls_goodness_of_fit_ref    1.065
_refine_ls_restrained_S_all       1.065
_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_site_symmetry_order  
 _atom_site_calc_flag
 _atom_site_refinement_flags_posn
 _atom_site_refinement_flags_adp
 _atom_site_refinement_flags_occupancy
 _atom_site_disorder_assembly
 _atom_site_disorder_group
Se1 Se 0.66922(4) 0.33086(13) 0.63761(5) 0.0514(4) Uani 1 1 d . . . . .
Se2 Se 0.69477(3) -0.10945(13) 0.56321(5) 0.0477(4) Uani 1 1 d . . . . .
S1 S 0.89608(11) 0.1497(4) 0.72592(14) 0.0570(7) Uani 1 1 d . . . . .
N1 N 0.7738(3) 0.2063(10) 0.6062(3) 0.0394(14) Uani 1 1 d . . . . .
C1 C 0.7186(3) 0.1604(10) 0.6047(3) 0.0305(14) Uani 1 1 d . . . . .
C2 C 0.8158(3) 0.0607(14) 0.5893(4) 0.0433(18) Uani 1 1 d . . . . .
H2A H 0.8411 0.1324 0.5637 0.052 Uiso 1 1 calc R U . . .
H2B H 0.7950 -0.0449 0.5549 0.052 Uiso 1 1 calc R U . . .
C3 C 0.8533(4) -0.0403(14) 0.6632(5) 0.0486(19) Uani 1 1 d . . . . .
H3A H 0.8789 -0.1417 0.6501 0.058 Uiso 1 1 calc R U . . .
H3B H 0.8281 -0.1102 0.6894 0.058 Uiso 1 1 calc R U . . .
C4 C 0.8386(5) 0.3322(14) 0.7266(5) 0.057(2) Uani 1 1 d . . . . .
H4A H 0.8127 0.2728 0.7542 0.068 Uiso 1 1 calc R U . . .
H4B H 0.8558 0.4549 0.7539 0.068 Uiso 1 1 calc R U . . .
C5 C 0.8038(4) 0.3908(13) 0.6482(5) 0.048(2) Uani 1 1 d . . . . .
H5A H 0.8293 0.4506 0.6201 0.058 Uiso 1 1 calc R U . . .
H5B H 0.7749 0.4932 0.6518 0.058 Uiso 1 1 calc R U . . .
C6 C 0.6123(4) -0.1187(14) 0.5653(4) 0.047(2) Uani 1 1 d . . . . .
H6A H 0.6072 -0.2287 0.5991 0.056 Uiso 1 1 calc R U . . .
H6B H 0.6024 0.0096 0.5860 0.056 Uiso 1 1 calc R U . . .
C7 C 0.5726(3) -0.1515(12) 0.4890(4) 0.0375(17) Uani 1 1 d . . . . .
C8 C 0.5500(4) -0.3460(13) 0.4664(5) 0.047(2) Uani 1 1 d . . . . .
H8 H 0.5621 -0.4571 0.4991 0.056 Uiso 1 1 calc R U . . .
C9 C 0.5096(4) -0.3780(15) 0.3958(5) 0.055(2) Uani 1 1 d . . . . .
H9 H 0.4944 -0.5088 0.3827 0.066 Uiso 1 1 calc R U . . .
C10 C 0.4919(4) -0.2162(19) 0.3450(5) 0.064(3) Uani 1 1 d . . . . .
H10 H 0.4652 -0.2364 0.2976 0.077 Uiso 1 1 calc R U . . .
C11 C 0.5152(3) -0.0221(17) 0.3673(5) 0.060(3) Uani 1 1 d . . . . .
H11 H 0.5038 0.0884 0.3341 0.073 Uiso 1 1 calc R U . . .
C12 C 0.5545(4) 0.0097(14) 0.4368(5) 0.053(2) Uani 1 1 d . . . . .
H12 H 0.5695 0.1408 0.4497 0.064 Uiso 1 1 calc R U . . .
 
 
_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
Se1 C1 1.826(7) . ?
Se2 C1 1.934(7) . ?
Se2 C6 1.971(8) . ?
S1 C3 1.799(9) . ?
S1 C4 1.814(11) . ?
N1 C1 1.339(10) . ?
N1 C2 1.467(10) . ?
N1 C5 1.496(10) . ?
C2 C3 1.541(11) . ?
C4 C5 1.488(12) . ?
C6 C7 1.464(10) . ?
C7 C8 1.393(11) . ?
C7 C12 1.400(11) . ?
C8 C9 1.392(12) . ?
C9 C10 1.387(14) . ?
C10 C11 1.395(15) . ?
C11 C12 1.367(12) . ?
 
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 Se2 C6 102.1(3) . . ?
C3 S1 C4 98.8(4) . . ?
C1 N1 C2 124.8(6) . . ?
C1 N1 C5 121.4(7) . . ?
C2 N1 C5 111.4(7) . . ?
N1 C1 Se1 124.7(5) . . ?
N1 C1 Se2 113.2(5) . . ?
Se1 C1 Se2 122.1(4) . . ?
N1 C2 C3 111.2(6) . . ?
C2 C3 S1 110.6(6) . . ?
C5 C4 S1 112.9(7) . . ?
C4 C5 N1 110.2(7) . . ?
C7 C6 Se2 112.5(5) . . ?
C8 C7 C12 117.2(7) . . ?
C8 C7 C6 120.7(8) . . ?
C12 C7 C6 122.0(8) . . ?
C9 C8 C7 121.5(8) . . ?
C10 C9 C8 120.4(9) . . ?
C9 C10 C11 118.0(8) . . ?
C12 C11 C10 121.6(9) . . ?
C11 C12 C7 121.2(9) . . ?
 
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
C2 N1 C1 Se1 171.7(5) . . . . ?
C5 N1 C1 Se1 10.8(9) . . . . ?
C2 N1 C1 Se2 -8.5(8) . . . . ?
C5 N1 C1 Se2 -169.4(5) . . . . ?
C1 N1 C2 C3 -93.9(8) . . . . ?
C5 N1 C2 C3 68.6(8) . . . . ?
N1 C2 C3 S1 -62.7(8) . . . . ?
C4 S1 C3 C2 50.4(7) . . . . ?
C3 S1 C4 C5 -51.9(7) . . . . ?
S1 C4 C5 N1 62.0(9) . . . . ?
C1 N1 C5 C4 95.3(9) . . . . ?
C2 N1 C5 C4 -67.8(9) . . . . ?
Se2 C6 C7 C8 99.7(8) . . . . ?
Se2 C6 C7 C12 -81.9(9) . . . . ?
C12 C7 C8 C9 -2.1(12) . . . . ?
C6 C7 C8 C9 176.3(8) . . . . ?
C7 C8 C9 C10 1.7(14) . . . . ?
C8 C9 C10 C11 -0.7(14) . . . . ?
C9 C10 C11 C12 0.2(14) . . . . ?
C10 C11 C12 C7 -0.6(14) . . . . ?
C8 C7 C12 C11 1.6(12) . . . . ?
C6 C7 C12 C11 -176.9(8) . . . . ?
 
loop_
 _geom_hbond_atom_site_label_D 
 _geom_hbond_atom_site_label_H 
 _geom_hbond_atom_site_label_A 
 _geom_hbond_distance_DH 
 _geom_hbond_distance_HA 
 _geom_hbond_distance_DA 
 _geom_hbond_angle_DHA 
 _geom_hbond_site_symmetry_A 
C6 H6B Se1  0.97 2.64 3.339(8) 129.2 .
C5 H5B Se1  0.97 2.67 3.177(9) 112.6 .
C3 H3B Se1  0.97 3.14 3.872(9) 133.9 4_646
C2 H2B Se2  0.97 3.16 3.990(8) 145.2 7_646
C2 H2B Se2  0.97 2.46 3.001(8) 114.7 .
 
_refine_diff_density_max    0.926
_refine_diff_density_min   -1.123
_refine_diff_density_rms    0.206

_shelxl_version_number 2014-3



