# Electronic Supplementary Material (ESI) for RSC Advances.
# This journal is © The Royal Society of Chemistry 2016

####################################################################### 
# 
# 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_IMP7
_database_code_depnum_ccdc_archive 'CCDC 1496202'
_audit_update_record             
;
2016-07-26 deposited with the CCDC.
2016-11-11 downloaded from the CCDC.
;

_audit_creation_date             2015-05-13T10:20:05-00:00
_audit_creation_method           'WinGX routine CIF_UPDATE'
_audit_conform_dict_name         cif_core.dic
_audit_conform_dict_version      2.4.3
_audit_conform_dict_location     ftp://ftp.iucr.org/pub/cif_core.dic

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

_chemical_name_systematic        
;
 ?
;
_chemical_formula_moiety         'C13  H11  N3  Se1'
_chemical_formula_sum            'C13 H11 N3 Se'
_chemical_formula_weight         288.21

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

_symmetry_cell_setting           trigonal
_symmetry_space_group_name_H-M   'R -3 :H'
_symmetry_space_group_name_Hall  '-R 3'
_symmetry_Int_Tables_number      148
loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'-y, x-y, z'
'-x+y, -x, z'
'x+2/3, y+1/3, z+1/3'
'-y+2/3, x-y+1/3, z+1/3'
'-x+y+2/3, -x+1/3, z+1/3'
'x+1/3, y+2/3, z+2/3'
'-y+1/3, x-y+2/3, z+2/3'
'-x+y+1/3, -x+2/3, z+2/3'
'-x, -y, -z'
'y, -x+y, -z'
'x-y, x, -z'
'-x+2/3, -y+1/3, -z+1/3'
'y+2/3, -x+y+1/3, -z+1/3'
'x-y+2/3, x+1/3, -z+1/3'
'-x+1/3, -y+2/3, -z+2/3'
'y+1/3, -x+y+2/3, -z+2/3'
'x-y+1/3, x+2/3, -z+2/3'

_cell_length_a                   31.935(2)
_cell_length_b                   31.935(2)
_cell_length_c                   6.3894(5)
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                120
_cell_volume                     5643.3(9)
_cell_formula_units_Z            18
_cell_measurement_temperature    296(2)
_cell_measurement_reflns_used    24
_cell_measurement_theta_min      2.209
_cell_measurement_theta_max      26.053
_cell_measurement_wavelength     0.71073

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

_exptl_crystal_description       PLATE
_exptl_crystal_colour            COLOURLESS
_exptl_crystal_size_max          0.05
_exptl_crystal_size_mid          0.03
_exptl_crystal_size_min          0.01
_exptl_crystal_density_diffrn    1.526
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             2592
_exptl_special_details           
;
 ?
;

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

_exptl_absorpt_coefficient_mu    2.974
_exptl_absorpt_correction_type   none

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

_diffrn_ambient_temperature      296(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_radiation_probe          x-ray
_diffrn_measurement_device_type  'Bruker APEX-II CCD'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_standards_number         0
_diffrn_standards_interval_time  .
_diffrn_standards_interval_count .
_diffrn_standards_decay_%        ?
_diffrn_reflns_av_R_equivalents  0.0928
_diffrn_reflns_av_unetI/netI     0.0449
_diffrn_reflns_number            27802
_diffrn_reflns_limit_h_min       -39
_diffrn_reflns_limit_h_max       39
_diffrn_reflns_limit_k_min       -39
_diffrn_reflns_limit_k_max       39
_diffrn_reflns_limit_l_min       -7
_diffrn_reflns_limit_l_max       7
_diffrn_reflns_theta_min         2.209
_diffrn_reflns_theta_max         26.053
_diffrn_reflns_theta_full        25.242
_diffrn_measured_fraction_theta_full 0.995
_diffrn_measured_fraction_theta_max 0.995
_diffrn_reflns_Laue_measured_fraction_full 0.995
_diffrn_reflns_Laue_measured_fraction_max 0.995
_diffrn_reflns_point_group_measured_fraction_full 0.995
_diffrn_reflns_point_group_measured_fraction_max 0.995
_reflns_Friedel_coverage         0
_reflns_number_total             2467
_reflns_number_gt                1697
_reflns_threshold_expression     'I > 2σ(I)'

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

_computing_data_collection       'Bruker APEX2'
_computing_cell_refinement       'Bruker SAINT'
_computing_data_reduction        'Bruker SAINT'
_computing_structure_solution    'SHELXS-97 (Sheldrick 2008)'
_computing_structure_refinement  'SHELXL-2014 (Sheldrick, 2014)'
_computing_molecular_graphics    'Bruker SHELXTL'
_computing_publication_material  'Bruker SHELXTL'

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

_atom_sites_solution_hydrogens   geom

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

_refine_special_details          ', SQUEEZE'
_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0580P)²+1.3399P] where P=(Fo²+2Fc²)/3'
_refine_ls_hydrogen_treatment    constr
_refine_ls_extinction_method     none
_refine_ls_number_reflns         2467
_refine_ls_number_parameters     154
_refine_ls_number_restraints     0
_refine_ls_number_constraints    0
_refine_ls_R_factor_all          0.076
_refine_ls_R_factor_gt           0.0442
_refine_ls_wR_factor_ref         0.1186
_refine_ls_wR_factor_gt          0.1088
_refine_ls_goodness_of_fit_ref   1.102
_refine_ls_restrained_S_all      1.102
_refine_ls_shift/su_max          0
_refine_ls_shift/su_mean         0
_refine_diff_density_max         0.592
_refine_diff_density_min         -0.281
_refine_diff_density_rms         0.079

#----------------------------------------------------------------------------#
#                   CONSTRAINTS AND RESTRAINTS                               #
#----------------------------------------------------------------------------#


#----------------------------------------------------------------------------#
#                   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'
O O 0.0106 0.006 '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_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 0.56496(2) 0.68532(2) 0.87219(6) 0.0638(2) Uani 1 1 d . . . . .
N3 N 0.67518(10) 0.77462(11) 0.3219(4) 0.0433(7) Uani 1 1 d . . . . .
N1 N 0.67988(11) 0.76241(10) 0.6622(4) 0.0480(7) Uani 1 1 d . . . . .
N2 N 0.73556(11) 0.84010(11) 0.5241(5) 0.0533(8) Uani 1 1 d . . . . .
C2 C 0.64281(12) 0.72155(12) 0.5718(5) 0.0451(8) Uani 1 1 d . . . . .
C7 C 0.69890(12) 0.79422(13) 0.5099(5) 0.0433(8) Uani 1 1 d . . . . .
C8 C 0.52283(13) 0.68746(13) 0.6640(6) 0.0541(9) Uani 1 1 d . . . . .
C3 C 0.63976(13) 0.72804(13) 0.3638(6) 0.0507(9) Uani 1 1 d . . . . .
H3 H 0.6181 0.7055 0.269 0.061 Uiso 1 1 calc R U . . .
C6 C 0.74774(14) 0.86543(14) 0.3494(7) 0.0601(10) Uani 1 1 d . . . . .
H6 H 0.7729 0.8973 0.3547 0.072 Uiso 1 1 calc R U . . .
C5 C 0.72510(14) 0.84740(15) 0.1560(6) 0.0579(10) Uani 1 1 d . . . . .
H5 H 0.7354 0.867 0.0379 0.07 Uiso 1 1 calc R U . . .
C4 C 0.68860(14) 0.80179(15) 0.1422(6) 0.0543(9) Uani 1 1 d . . . . .
H4 H 0.6729 0.789 0.0158 0.065 Uiso 1 1 calc R U . . .
C13 C 0.50966(14) 0.65948(14) 0.4846(6) 0.0575(10) Uani 1 1 d . . . . .
H13 H 0.5219 0.6389 0.4594 0.069 Uiso 1 1 calc R U . . .
C1 C 0.61155(14) 0.67803(13) 0.6971(6) 0.0547(9) Uani 1 1 d . . . . .
H1A H 0.6317 0.6708 0.7864 0.066 Uiso 1 1 calc R U . . .
H1B H 0.594 0.6508 0.6034 0.066 Uiso 1 1 calc R U . . .
C9 C 0.50408(17) 0.71729(15) 0.7033(7) 0.0710(12) Uani 1 1 d . . . . .
H9 H 0.5126 0.7358 0.8247 0.085 Uiso 1 1 calc R U . . .
C12 C 0.47869(16) 0.66208(16) 0.3444(7) 0.0698(11) Uani 1 1 d . . . . .
H12 H 0.4703 0.6437 0.2227 0.084 Uiso 1 1 calc R U . . .
C11 C 0.45989(17) 0.69183(19) 0.3825(9) 0.0839(14) Uani 1 1 d . . . . .
H11 H 0.4386 0.6934 0.2879 0.101 Uiso 1 1 calc R U . . .
C10 C 0.47304(19) 0.71943(18) 0.5631(9) 0.0871(15) Uani 1 1 d . . . . .
H10 H 0.4605 0.7397 0.5891 0.105 Uiso 1 1 calc R U . . .



#----------------------------------------------------------------------------#
#                   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 C8 1.917(4) . ?
Se1 C1 1.966(4) . ?
N3 C3 1.371(4) . ?
N3 C4 1.372(4) . ?
N3 C7 1.391(4) . ?
N1 C7 1.316(4) . ?
N1 C2 1.376(4) . ?
N2 C6 1.318(5) . ?
N2 C7 1.346(5) . ?
C2 C3 1.356(5) . ?
C2 C1 1.477(5) . ?
C8 C9 1.378(5) . ?
C8 C13 1.383(5) . ?
C3 H3 0.93 . ?
C6 C5 1.402(6) . ?
C6 H6 0.93 . ?
C5 C4 1.338(5) . ?
C5 H5 0.93 . ?
C4 H4 0.93 . ?
C13 C12 1.368(6) . ?
C13 H13 0.93 . ?
C1 H1A 0.97 . ?
C1 H1B 0.97 . ?
C9 C10 1.363(7) . ?
C9 H9 0.93 . ?
C12 C11 1.376(6) . ?
C12 H12 0.93 . ?
C11 C10 1.384(7) . ?
C11 H11 0.93 . ?
C10 H10 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
C8 Se1 C1 101.28(15) . . ?
C3 N3 C4 132.6(3) . . ?
C3 N3 C7 106.7(3) . . ?
C4 N3 C7 120.7(3) . . ?
C7 N1 C2 105.5(3) . . ?
C6 N2 C7 116.1(3) . . ?
C3 C2 N1 111.1(3) . . ?
C3 C2 C1 127.5(3) . . ?
N1 C2 C1 121.4(3) . . ?
N1 C7 N2 127.3(3) . . ?
N1 C7 N3 110.7(3) . . ?
N2 C7 N3 122.0(3) . . ?
C9 C8 C13 120.0(4) . . ?
C9 C8 Se1 117.0(3) . . ?
C13 C8 Se1 123.0(3) . . ?
C2 C3 N3 105.9(3) . . ?
C2 C3 H3 127.1 . . ?
N3 C3 H3 127.1 . . ?
N2 C6 C5 124.2(4) . . ?
N2 C6 H6 117.9 . . ?
C5 C6 H6 117.9 . . ?
C4 C5 C6 119.7(4) . . ?
C4 C5 H5 120.2 . . ?
C6 C5 H5 120.2 . . ?
C5 C4 N3 117.4(3) . . ?
C5 C4 H4 121.3 . . ?
N3 C4 H4 121.3 . . ?
C12 C13 C8 120.0(4) . . ?
C12 C13 H13 120 . . ?
C8 C13 H13 120 . . ?
C2 C1 Se1 113.1(2) . . ?
C2 C1 H1A 109 . . ?
Se1 C1 H1A 109 . . ?
C2 C1 H1B 109 . . ?
Se1 C1 H1B 109 . . ?
H1A C1 H1B 107.8 . . ?
C10 C9 C8 119.6(4) . . ?
C10 C9 H9 120.2 . . ?
C8 C9 H9 120.2 . . ?
C13 C12 C11 120.3(4) . . ?
C13 C12 H12 119.8 . . ?
C11 C12 H12 119.8 . . ?
C12 C11 C10 119.3(5) . . ?
C12 C11 H11 120.4 . . ?
C10 C11 H11 120.4 . . ?
C9 C10 C11 120.9(5) . . ?
C9 C10 H10 119.6 . . ?
C11 C10 H10 119.6 . . ?

loop_
_platon_squeeze_void_nr
_platon_squeeze_void_average_x
_platon_squeeze_void_average_y
_platon_squeeze_void_average_z
_platon_squeeze_void_volume
_platon_squeeze_void_count_electrons
_platon_squeeze_void_content
1 0.000 0.000 -0.005 121 29 ' '
2 0.333 0.667 0.456 120 29 ' '
3 0.667 0.333 0.123 119 29 ' '
_platon_squeeze_void_probe_radius 1.20
_platon_squeeze_details          ?
# END of CIF
