# Electronic Supplementary Material (ESI) for New Journal of Chemistry.
# This journal is © The Royal Society of Chemistry and the Centre National de la Recherche Scientifique 2019

####################################################################### 
# 
# This file contains crystal structure data downloaded from the 
# Cambridge Structural Database (CSD) hosted by the Cambridge 
# Crystallographic Data Centre (CCDC).
# 
# Full information about CCDC data access policies and citation 
# guidelines are available at http://www.ccdc.cam.ac.uk/access/V1 
# 
# Audit and citation data items may have been added by the CCDC. 
# Please retain this information to preserve the provenance of 
# this file and to allow appropriate attribution of the data. 
# 
#######################################################################

data_mj_11
_database_code_depnum_ccdc_archive 'CCDC 1819893'
loop_
_audit_author_name
_audit_author_address
'Ewa Zeslawska' 'Pedagogical University of Cracow'
_audit_update_record             
;
2018-01-27 deposited with the CCDC.	2019-03-13 downloaded from the CCDC.
;

_audit_creation_date             2017-11-26T19:43:19-00:00
_audit_creation_method           'WinGX routine CIF_UPDATE'

#----------------------------------------------------------------------------#
#                   CHEMICAL INFORMATION                                     #
#----------------------------------------------------------------------------#

_chemical_name_systematic        
;
1-(selenocyanatomethyl)benzene
;
_chemical_name_common            selenocyanate
_chemical_formula_moiety         'C7 H15 N Se'
_chemical_formula_sum            'C8 H7 N Se'
_chemical_formula_weight         196.11

#----------------------------------------------------------------------------#
#                   UNIT CELL INFORMATION                                    #
#----------------------------------------------------------------------------#

_symmetry_cell_setting           monoclinic
_symmetry_space_group_name_H-M   'P 21/c'
_symmetry_space_group_name_Hall  '-P 2ybc'
_symmetry_Int_Tables_number      14
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                   5.98800(10)
_cell_length_b                   7.4440(2)
_cell_length_c                   17.4880(5)
_cell_angle_alpha                90
_cell_angle_beta                 96.277(2)
_cell_angle_gamma                90
_cell_volume                     774.85(3)
_cell_formula_units_Z            4
_cell_measurement_temperature    293(2)
_cell_measurement_reflns_used    3244
_cell_measurement_theta_min      0.998
_cell_measurement_theta_max      27.485

#----------------------------------------------------------------------------#
#                   CRYSTAL INFORMATION                                      #
#----------------------------------------------------------------------------#

_exptl_crystal_description       prism
_exptl_crystal_colour            ?
_exptl_crystal_size_max          0.455
_exptl_crystal_size_mid          0.164
_exptl_crystal_size_min          0.075
_exptl_crystal_density_diffrn    1.681
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             384
loop_
_exptl_crystal_face_index_h
_exptl_crystal_face_index_k
_exptl_crystal_face_index_l
_exptl_crystal_face_perp_dist
0 1 -2 0.027
0 -1 2 0.05
0 1 2 0.117
0 -1 -2 0.047
3 0 -1 0.192
-3 0 1 0.237
-1 1 -2 0.13
1 -1 2 0.135
1 3 -5 0.06

_exptl_special_details           
;
 ?
;

#----------------------------------------------------------------------------#
#                   ABSORPTION CORRECTION                                    #
#----------------------------------------------------------------------------#

_exptl_absorpt_coefficient_mu    4.763
_exptl_absorpt_correction_type   Multi-scan
_exptl_absorpt_process_details   '(DENZO-SMN; Otwinowski & Minor, 1997)'
_exptl_absorpt_correction_T_min  0.7182
_exptl_absorpt_correction_T_max  1.0000
#----------------------------------------------------------------------------#
#                   DATA COLLECTION                                          #
#----------------------------------------------------------------------------#

_diffrn_ambient_temperature      293(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_radiation_monochromator  'horizonally mounted graphite crystal'
_diffrn_detector_area_resol_mean 9
_diffrn_orient_matrix_type       'by Bruker AXS Collect from scalepack cell'
_diffrn_orient_matrix_ub_11      0.1671556
_diffrn_orient_matrix_ub_12      -0.0134583
_diffrn_orient_matrix_ub_13      0.0054149
_diffrn_orient_matrix_ub_21      -0.0031988
_diffrn_orient_matrix_ub_22      -0.0440657
_diffrn_orient_matrix_ub_23      0.0538874
_diffrn_orient_matrix_ub_31      -0.0167095
_diffrn_orient_matrix_ub_32      -0.1261954
_diffrn_orient_matrix_ub_33      -0.0193942
_diffrn_measurement_device       '95mm CCD camera on κ-goniostat'
_diffrn_measurement_device_type  KappaCCD
_diffrn_measurement_method       CCD
_diffrn_reflns_av_R_equivalents  0.0326
_diffrn_reflns_number            5844
_diffrn_reflns_limit_h_min       -7
_diffrn_reflns_limit_h_max       7
_diffrn_reflns_limit_k_min       -9
_diffrn_reflns_limit_k_max       9
_diffrn_reflns_limit_l_min       -22
_diffrn_reflns_limit_l_max       21
_diffrn_reflns_theta_min         2.977
_diffrn_reflns_theta_max         27.489
_diffrn_reflns_theta_full        25.242
_diffrn_measured_fraction_theta_full 0.999
_diffrn_measured_fraction_theta_max 0.999
_diffrn_reflns_Laue_measured_fraction_full 0.999
_diffrn_reflns_Laue_measured_fraction_max 0.999
_diffrn_reflns_point_group_measured_fraction_full 0.999
_diffrn_reflns_point_group_measured_fraction_max 0.999
_reflns_number_total             1786
_reflns_number_gt                1633
_reflns_threshold_expression     'I > 2σ(I)'

#----------------------------------------------------------------------------#
#                   COMPUTER PROGRAMS USED                                   #
#----------------------------------------------------------------------------#

_computing_data_collection       'Collect (Bruker AXS BV, 1997-2004)'
_computing_cell_refinement       'HKL Scalepack (Otwinowski & Minor 1997)'
_computing_data_reduction        
'HKL Denzo and Scalepack (Otwinowski & Minor 1997)'
_computing_structure_refinement  'SHELXL-2013 (Sheldrick, 2013)'
_computing_molecular_graphics    'Ortep (Johnson, 1976)'

#----------------------------------------------------------------------------#
#                   STRUCTURE SOLUTION
#----------------------------------------------------------------------------#

_atom_sites_solution_hydrogens   geom

#----------------------------------------------------------------------------#
#                   REFINEMENT INFORMATION                                   #
#----------------------------------------------------------------------------#

_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)+(0.0232P)²+0.5385P] where P=(Fo²+2Fc²)/3'
_refine_ls_hydrogen_treatment    constr
_refine_ls_extinction_method     none
_refine_ls_number_reflns         1786
_refine_ls_number_parameters     91
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0261
_refine_ls_R_factor_gt           0.0226
_refine_ls_wR_factor_ref         0.0536
_refine_ls_wR_factor_gt          0.0521
_refine_ls_goodness_of_fit_gt    18.73
_refine_ls_goodness_of_fit_ref   1.083
_refine_ls_restrained_S_all      1.083
_refine_ls_shift/su_max          0
_refine_ls_shift/su_mean         0
_refine_diff_density_max         0.317
_refine_diff_density_min         -0.704
_refine_diff_density_rms         0.087

#----------------------------------------------------------------------------#
#                   ATOMIC TYPES, COORDINATES AND THERMAL PARAMETERS         #
#----------------------------------------------------------------------------#

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 0 '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'
Se Se -0.0929 2.2259 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

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_calc_flag
_atom_site_disorder_assembly
_atom_site_disorder_group
Se1 Se 0.34684(3) 0.30029(2) 0.03577(2) 0.01470(8) Uani 1 d . .
N1 N -0.1546(3) 0.2711(3) 0.02536(11) 0.0221(4) Uani 1 d . .
C3 C 0.3279(3) 0.0748(2) 0.17255(11) 0.0133(4) Uani 1 d . .
C1 C 0.0376(3) 0.2796(2) 0.03053(12) 0.0154(4) Uani 1 d . .
C2 C 0.4112(3) 0.0740(3) 0.09480(11) 0.0158(4) Uani 1 d . .
H2A H 0.3422 -0.0256 0.0652 0.019 Uiso 1 calc . .
H2B H 0.5723 0.054 0.1011 0.019 Uiso 1 calc . .
C5 C 0.0502(3) -0.0123(3) 0.25614(12) 0.0183(4) Uani 1 d . .
H5 H -0.0861 -0.0665 0.2629 0.022 Uiso 1 calc . .
C4 C 0.1248(3) -0.0078(2) 0.18338(11) 0.0155(4) Uani 1 d . .
H4 H 0.0386 -0.0603 0.1418 0.019 Uiso 1 calc . .
C8 C 0.4555(3) 0.1525(3) 0.23530(12) 0.0160(4) Uani 1 d . .
H8 H 0.5907 0.2088 0.2286 0.019 Uiso 1 calc . .
C6 C 0.1796(4) 0.0642(3) 0.31836(12) 0.0203(4) Uani 1 d . .
H6 H 0.1306 0.0605 0.367 0.024 Uiso 1 calc . .
C7 C 0.3821(3) 0.1464(3) 0.30793(12) 0.0202(4) Uani 1 d . .
H7 H 0.4689 0.1975 0.3497 0.024 Uiso 1 calc . .



#----------------------------------------------------------------------------#
#                   MOLECULAR GEOMETRY                                       #
#----------------------------------------------------------------------------#

_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 1.8505(19) . ?
Se1 C2 1.9912(19) . ?
N1 C1 1.146(3) . ?
C3 C8 1.393(3) . ?
C3 C4 1.394(2) . ?
C3 C2 1.499(3) . ?
C2 H2A 0.97 . ?
C2 H2B 0.97 . ?
C5 C6 1.387(3) . ?
C5 C4 1.394(3) . ?
C5 H5 0.93 . ?
C4 H4 0.93 . ?
C8 C7 1.390(3) . ?
C8 H8 0.93 . ?
C6 C7 1.388(3) . ?
C6 H6 0.93 . ?
C7 H7 0.93 . ?

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 Se1 C2 95.24(8) . . ?
C8 C3 C4 119.21(18) . . ?
C8 C3 C2 120.53(17) . . ?
C4 C3 C2 120.22(17) . . ?
N1 C1 Se1 177.69(19) . . ?
C3 C2 Se1 113.71(12) . . ?
C3 C2 H2A 108.8 . . ?
Se1 C2 H2A 108.8 . . ?
C3 C2 H2B 108.8 . . ?
Se1 C2 H2B 108.8 . . ?
H2A C2 H2B 107.7 . . ?
C6 C5 C4 119.94(18) . . ?
C6 C5 H5 120 . . ?
C4 C5 H5 120 . . ?
C3 C4 C5 120.38(18) . . ?
C3 C4 H4 119.8 . . ?
C5 C4 H4 119.8 . . ?
C7 C8 C3 120.35(18) . . ?
C7 C8 H8 119.8 . . ?
C3 C8 H8 119.8 . . ?
C5 C6 C7 119.91(19) . . ?
C5 C6 H6 120 . . ?
C7 C6 H6 120 . . ?
C6 C7 C8 120.21(19) . . ?
C6 C7 H7 119.9 . . ?
C8 C7 H7 119.9 . . ?

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
C8 C3 C2 Se1 -83.55(19) . . . . ?
C4 C3 C2 Se1 98.65(17) . . . . ?
C8 C3 C4 C5 0.1(3) . . . . ?
C2 C3 C4 C5 177.97(17) . . . . ?
C6 C5 C4 C3 -0.7(3) . . . . ?
C4 C3 C8 C7 0.5(3) . . . . ?
C2 C3 C8 C7 -177.31(17) . . . . ?
C4 C5 C6 C7 0.6(3) . . . . ?
C5 C6 C7 C8 0.1(3) . . . . ?
C3 C8 C7 C6 -0.6(3) . . . . ?

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
C2 H2A N1 0.97 2.59 3.559(3) 174.4 3
_shelxl_version_number           2013-4

####################################################################### 
# 
# This file contains crystal structure data downloaded from the 
# Cambridge Structural Database (CSD) hosted by the Cambridge 
# Crystallographic Data Centre (CCDC).
# 
# Full information about CCDC data access policies and citation 
# guidelines are available at http://www.ccdc.cam.ac.uk/access/V1 
# 
# Audit and citation data items may have been added by the CCDC. 
# Please retain this information to preserve the provenance of 
# this file and to allow appropriate attribution of the data. 
# 
#######################################################################

data_mj_18
_database_code_depnum_ccdc_archive 'CCDC 1819894'
loop_
_audit_author_name
_audit_author_address
'Ewa Zeslawska' 'Pedagogical University of Cracow'
_audit_update_record             
;
2018-01-27 deposited with the CCDC.	2019-03-13 downloaded from the CCDC.
;

_audit_creation_date             2018-01-11T17:52:10-00:00
_audit_creation_method           'WinGX routine CIF_UPDATE'

#----------------------------------------------------------------------------#
#                   CHEMICAL INFORMATION                                     #
#----------------------------------------------------------------------------#

_chemical_name_systematic        
;
2-(selenocyanatomethyl)naphthalene
;
_chemical_name_common            selenocyanate
_chemical_formula_sum            'C12 H9 N Se'
_chemical_formula_weight         246.16
_chemical_absolute_configuration unk

#----------------------------------------------------------------------------#
#                   UNIT CELL INFORMATION                                    #
#----------------------------------------------------------------------------#

_symmetry_cell_setting           monoclinic
_symmetry_space_group_name_H-M   'I a'
_symmetry_space_group_name_Hall  'I -2ya'
_symmetry_Int_Tables_number      9
loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'x+1/2, -y, z'
'x+1/2, y+1/2, z+1/2'
'x+1, -y+1/2, z+1/2'

_cell_length_a                   8.2486(2)
_cell_length_b                   5.98390(10)
_cell_length_c                   20.4158(7)
_cell_angle_alpha                90
_cell_angle_beta                 93.097(3)
_cell_angle_gamma                90
_cell_volume                     1006.23(5)
_cell_formula_units_Z            4
_cell_measurement_temperature    293(2)
_cell_measurement_reflns_used    2270
_cell_measurement_theta_min      3.547
_cell_measurement_theta_max      28.066

#----------------------------------------------------------------------------#
#                   CRYSTAL INFORMATION                                      #
#----------------------------------------------------------------------------#

_exptl_crystal_description       irregular
_exptl_crystal_colour            colourless
_exptl_crystal_size_max          0.596
_exptl_crystal_size_mid          0.483
_exptl_crystal_size_min          0.253
_exptl_crystal_density_diffrn    1.625
_exptl_crystal_F_000             488
loop_
_exptl_crystal_face_index_h
_exptl_crystal_face_index_k
_exptl_crystal_face_index_l
_exptl_crystal_face_perp_dist
0 0 -2 0.0871
-1 0 1 0.2942
-3 4 9 0.1806
-5 -2 5 0.2907
-1 -3 -6 0.2214
-2 2 10 0.1631
1 5 -8 0.2355
-2 -5 7 0.2126
-3 4 -11 0.2259
0 0 2 0.1658
5 -4 -11 0.2336
1 3 6 0.18
5 1 -2 0.2429
1 -1 0 0.2299
-4 0 -6 0.3141
-1 -1 4 0.1869

_exptl_special_details           
;
 ?
;

#----------------------------------------------------------------------------#
#                   ABSORPTION CORRECTION                                    #
#----------------------------------------------------------------------------#

_exptl_absorpt_coefficient_mu    3.686
_exptl_absorpt_correction_type   gaussian
_exptl_absorpt_process_details   
;
        CrysAlisPro 1.171.38.43 (Rigaku Oxford Diffraction, 2015)
Numerical absorption correction based on gaussian integration over
                        a multifaceted crystal model
        Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_absorpt_correction_T_min  0.254
_exptl_absorpt_correction_T_max  0.477

#----------------------------------------------------------------------------#
#                   DATA COLLECTION                                          #
#----------------------------------------------------------------------------#

_diffrn_source                   'micro-focus sealed X-ray tube'
_diffrn_ambient_temperature      293(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_radiation_monochromator  mirror
_diffrn_radiation_probe          x-ray
_diffrn_detector                 'CCD plate'
_diffrn_detector_area_resol_mean 10.3756
_diffrn_orient_matrix_type       
'CrysAlisPro convention (1999,Acta A55,543-557)'
_diffrn_orient_matrix_ub_11      0.0273256
_diffrn_orient_matrix_ub_12      -0.0292738
_diffrn_orient_matrix_ub_13      -0.0312404
_diffrn_orient_matrix_ub_21      -0.0528873
_diffrn_orient_matrix_ub_22      0.0808175
_diffrn_orient_matrix_ub_23      -0.0149267
_diffrn_orient_matrix_ub_31      0.0621812
_diffrn_orient_matrix_ub_32      0.081608
_diffrn_orient_matrix_ub_33      0.0035865
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'SuperNova, Dual, Cu at zero, Atlas'
_diffrn_measurement_method       'ω scans'
_diffrn_reflns_av_R_equivalents  0.03
_diffrn_reflns_av_unetI/netI     0.0491
_diffrn_reflns_number            4415
_diffrn_reflns_limit_h_min       -9
_diffrn_reflns_limit_h_max       11
_diffrn_reflns_limit_k_min       -7
_diffrn_reflns_limit_k_max       7
_diffrn_reflns_limit_l_min       -27
_diffrn_reflns_limit_l_max       26
_diffrn_reflns_theta_min         3.548
_diffrn_reflns_theta_max         28.606
_diffrn_reflns_theta_full        25.242
_diffrn_measured_fraction_theta_full 0.994
_diffrn_measured_fraction_theta_max 0.931
_diffrn_reflns_Laue_measured_fraction_full 0.994
_diffrn_reflns_Laue_measured_fraction_max 0.931
_diffrn_reflns_point_group_measured_fraction_full 0.892
_diffrn_reflns_point_group_measured_fraction_max 0.798
_reflns_number_total             2048
_reflns_number_gt                1929
_reflns_threshold_expression     'I > 2σ(I)'

#----------------------------------------------------------------------------#
#                   COMPUTER PROGRAMS USED                                   #
#----------------------------------------------------------------------------#

_computing_data_collection       'CrysAlisPro 1.171.38.43 (Rigaku OD, 2015)'
_computing_cell_refinement       'CrysAlisPro 1.171.38.43 (Rigaku OD, 2015)'
_computing_data_reduction        'CrysAlisPro 1.171.38.43 (Rigaku OD, 2015)'
_computing_structure_refinement  'SHELXL-2013 (Sheldrick, 2013)'

#----------------------------------------------------------------------------#
#                   STRUCTURE SOLUTION
#----------------------------------------------------------------------------#

_atom_sites_solution_hydrogens   geom

#----------------------------------------------------------------------------#
#                   REFINEMENT INFORMATION                                   #
#----------------------------------------------------------------------------#

_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)+(0.0622P)²] where P=(Fo²+2Fc²)/3'
_refine_ls_hydrogen_treatment    constr
_refine_ls_extinction_method     none
_refine_ls_number_reflns         2048
_refine_ls_number_parameters     127
_refine_ls_number_restraints     2
_refine_ls_R_factor_all          0.0399
_refine_ls_R_factor_gt           0.037
_refine_ls_wR_factor_ref         0.0948
_refine_ls_wR_factor_gt          0.0923
_refine_ls_goodness_of_fit_ref   1.046
_refine_ls_restrained_S_all      1.045
_refine_ls_shift/su_max          0.001
_refine_ls_shift/su_mean         0
_refine_ls_abs_structure_details 
;
 Classical Flack method preferred over Parsons because s.u. lower.
;
_refine_ls_abs_structure_Flack   -0.01(2)
_refine_diff_density_max         0.602
_refine_diff_density_min         -0.624
_refine_diff_density_rms         0.094

#----------------------------------------------------------------------------#
#                   ATOMIC TYPES, COORDINATES AND THERMAL PARAMETERS         #
#----------------------------------------------------------------------------#

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 0 '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'
Se Se -0.0929 2.2259 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

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_calc_flag
_atom_site_disorder_assembly
_atom_site_disorder_group
Se1 Se 0.51941(4) 0.17695(6) 0.32751(3) 0.01952(18) Uani 1 d . .
C1 C 0.5225(15) 0.4855(8) 0.3255(6) 0.0210(11) Uani 1 d . .
C6 C 0.4436(7) 0.3556(9) 0.0624(3) 0.0165(12) Uani 1 d . .
N1 N 0.522(2) 0.6768(7) 0.3227(8) 0.0314(16) Uani 1 d . .
C3 C 0.5744(7) 0.2137(9) 0.1867(3) 0.0172(12) Uani 1 d . .
C4 C 0.6130(7) 0.4274(9) 0.1610(3) 0.0189(12) Uani 1 d . .
H4 H 0.6824 0.5219 0.1854 0.023 Uiso 1 calc . .
C7 C 0.3794(7) 0.4193(10) -0.0004(3) 0.0195(12) Uani 1 d . .
H7 H 0.4075 0.5566 -0.0179 0.023 Uiso 1 calc . .
C2 C 0.6540(8) 0.1362(10) 0.2503(3) 0.0210(12) Uani 1 d . .
H2A H 0.7551 0.2171 0.2581 0.025 Uiso 1 calc . .
H2B H 0.6805 -0.0211 0.2465 0.025 Uiso 1 calc . .
C8 C 0.2748(8) 0.2783(11) -0.0360(3) 0.0239(13) Uani 1 d . .
H8 H 0.2301 0.3232 -0.0767 0.029 Uiso 1 calc . .
C5 C 0.5498(7) 0.4959(9) 0.1010(3) 0.0188(11) Uani 1 d . .
H5 H 0.5767 0.6361 0.0852 0.023 Uiso 1 calc . .
C10 C 0.2973(7) 0.0006(9) 0.0493(3) 0.0181(11) Uani 1 d . .
H10 H 0.2702 -0.1393 0.0653 0.022 Uiso 1 calc . .
C9 C 0.2359(7) 0.0667(10) -0.0108(3) 0.0223(12) Uani 1 d . .
H9 H 0.1676 -0.0284 -0.0354 0.027 Uiso 1 calc . .
C11 C 0.4026(7) 0.1427(9) 0.0881(3) 0.0168(12) Uani 1 d . .
C12 C 0.4703(7) 0.0770(9) 0.1502(3) 0.0166(11) Uani 1 d . .
H12 H 0.4439 -0.0623 0.1668 0.02 Uiso 1 calc . .



#----------------------------------------------------------------------------#
#                   MOLECULAR GEOMETRY                                       #
#----------------------------------------------------------------------------#

_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 1.847(5) . ?
Se1 C2 1.991(7) . ?
C1 N1 1.146(7) . ?
C6 C7 1.413(8) . ?
C6 C5 1.421(8) . ?
C6 C11 1.425(7) . ?
C3 C12 1.375(8) . ?
C3 C4 1.425(8) . ?
C3 C2 1.498(9) . ?
C4 C5 1.368(8) . ?
C7 C8 1.384(9) . ?
C8 C9 1.410(10) . ?
C10 C9 1.361(8) . ?
C10 C11 1.425(8) . ?
C11 C12 1.412(8) . ?

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 Se1 C2 95.5(4) . . ?
N1 C1 Se1 178.2(15) . . ?
C7 C6 C5 122.2(5) . . ?
C7 C6 C11 119.4(5) . . ?
C5 C6 C11 118.4(5) . . ?
C12 C3 C4 118.6(5) . . ?
C12 C3 C2 121.2(5) . . ?
C4 C3 C2 120.1(5) . . ?
C5 C4 C3 121.1(5) . . ?
C8 C7 C6 120.3(5) . . ?
C3 C2 Se1 114.3(4) . . ?
C7 C8 C9 120.2(6) . . ?
C4 C5 C6 120.9(5) . . ?
C9 C10 C11 120.9(5) . . ?
C10 C9 C8 120.6(5) . . ?
C12 C11 C10 122.1(5) . . ?
C12 C11 C6 119.3(5) . . ?
C10 C11 C6 118.6(5) . . ?
C3 C12 C11 121.7(5) . . ?

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
C2 H2A N1 0.97 2.58 3.487(17) 155.2 2_565

_shelxl_version_number           2013-4

