# Electronic Supplementary Material (ESI) for RSC Advances.
# This journal is © The Royal Society of Chemistry 2015

####################################################################### 
# 
# 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_2e
_database_code_depnum_ccdc_archive 'CCDC 1400520'
_audit_update_record             
;
2015-09-06 deposited with the CCDC.
2015-09-08 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2013
_chemical_name_systematic        
;
 ?
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C12 H12 N2 Se'
_chemical_formula_weight         263.20

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'
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           14
_space_group_name_H-M_alt        'P 21/n'
_space_group_name_Hall           '-P 2yn'

_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+1/2, y+1/2, -z+1/2'
'-x, -y, -z'
'x-1/2, -y-1/2, z-1/2'

_cell_length_a                   7.5073(3)
_cell_length_b                   19.2645(9)
_cell_length_c                   7.5241(4)
_cell_angle_alpha                90
_cell_angle_beta                 92.684(2)
_cell_angle_gamma                90
_cell_volume                     1086.97(9)
_cell_formula_units_Z            4
_cell_measurement_temperature    180(2)
_cell_measurement_reflns_used    376
_cell_measurement_theta_min      283
_cell_measurement_theta_max      26.08

_exptl_crystal_description       block
_exptl_crystal_colour            yellow
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.608
_exptl_crystal_F_000             528
_exptl_transmission_factor_min   0.6558
_exptl_transmission_factor_max   0.7458
_exptl_crystal_size_max          0.260
_exptl_crystal_size_mid          0.240
_exptl_crystal_size_min          0.060
_exptl_absorpt_coefficient_mu    3.420
_shelx_estimated_absorpt_T_min   0.470
_shelx_estimated_absorpt_T_max   0.821
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  ?
_exptl_absorpt_correction_T_max  ?
_exptl_absorpt_process_details   ?

_exptl_special_details           
;
 ?
;

_diffrn_ambient_temperature      180(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_source                   'fine-focus sealed tube'
_diffrn_measurement_device_type  CCD
_diffrn_measurement_method       'omega and phi scans'
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            17964
_diffrn_reflns_av_unetI/netI     0.0395
_diffrn_reflns_av_R_equivalents  0.0501
_diffrn_reflns_limit_h_min       -10
_diffrn_reflns_limit_h_max       9
_diffrn_reflns_limit_k_min       -21
_diffrn_reflns_limit_k_max       26
_diffrn_reflns_limit_l_min       -10
_diffrn_reflns_limit_l_max       10
_diffrn_reflns_theta_min         2.114
_diffrn_reflns_theta_max         29.139
_diffrn_reflns_theta_full        25.242
_diffrn_measured_fraction_theta_max 0.997
_diffrn_measured_fraction_theta_full 1.000
_diffrn_reflns_Laue_measured_fraction_max 0.997
_diffrn_reflns_Laue_measured_fraction_full 1.000
_diffrn_reflns_point_group_measured_fraction_max 0.997
_diffrn_reflns_point_group_measured_fraction_full 1.000
_reflns_number_total             2930
_reflns_number_gt                2287
_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    'SHELXS-2013 (Sheldrick, 2013)'
_computing_structure_refinement  'SHELXL-2013 (Sheldrick, 2013)'
_computing_molecular_graphics    'OLEX2 (J. Appl. Cryst., 2009, 42, 339-341)'
_computing_publication_material  'SHELXL-2013 (Sheldrick, 2013)'

_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)+(0.0217P)²+0.6411P] 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         2930
_refine_ls_number_parameters     138
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0481
_refine_ls_R_factor_gt           0.0306
_refine_ls_wR_factor_ref         0.0640
_refine_ls_wR_factor_gt          0.0583
_refine_ls_goodness_of_fit_ref   1.020
_refine_ls_restrained_S_all      1.020
_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
Se Se 0.38266(3) 0.08644(2) 0.85225(3) 0.02693(8) Uani 1 1 d . . . . .
N1 N 0.2113(2) 0.11092(9) 0.5222(2) 0.0226(4) Uani 1 1 d . . . . .
C2 C 0.2768(3) 0.05928(11) 0.6235(3) 0.0193(4) Uani 1 1 d . . . . .
C3 C 0.2791(3) -0.01039(10) 0.5733(3) 0.0197(4) Uani 1 1 d . . . . .
C4 C 0.2072(3) -0.02519(11) 0.4035(3) 0.0244(5) Uani 1 1 d . . . . .
H4 H 0.2050 -0.0718 0.3619 0.029 Uiso 1 1 calc R U . . .
C5 C 0.1391(3) 0.02719(12) 0.2952(3) 0.0266(5) Uani 1 1 d . . . . .
H5 H 0.0914 0.0174 0.1788 0.032 Uiso 1 1 calc R U . . .
C6 C 0.1421(3) 0.09406(12) 0.3604(3) 0.0257(5) Uani 1 1 d . . . . .
H6 H 0.0928 0.1300 0.2870 0.031 Uiso 1 1 calc R U . . .
N7 N 0.0322(2) 0.12797(9) 0.8951(2) 0.0228(4) Uani 1 1 d . . . . .
C8 C 0.1990(3) 0.15029(10) 0.9198(3) 0.0194(4) Uani 1 1 d . . . . .
C9 C 0.2478(3) 0.21394(11) 0.9976(3) 0.0214(4) Uani 1 1 d . . . . .
C10 C 0.1080(3) 0.25582(11) 1.0475(3) 0.0246(5) Uani 1 1 d . . . . .
H10 H 0.1330 0.2998 1.1003 0.030 Uiso 1 1 calc R U . . .
C11 C -0.0670(3) 0.23440(12) 1.0214(3) 0.0269(5) Uani 1 1 d . . . . .
H11 H -0.1629 0.2630 1.0547 0.032 Uiso 1 1 calc R U . . .
C12 C -0.0980(3) 0.16998(12) 0.9451(3) 0.0261(5) Uani 1 1 d . . . . .
H12 H -0.2179 0.1548 0.9274 0.031 Uiso 1 1 calc R U . . .
C13 C 0.3495(3) -0.06703(11) 0.6948(3) 0.0299(5) Uani 1 1 d . . . . .
H13A H 0.4798 -0.0640 0.7066 0.036 Uiso 1 1 calc R U . . .
H13B H 0.3148 -0.1123 0.6449 0.036 Uiso 1 1 calc R U . . .
H13C H 0.2997 -0.0617 0.8121 0.036 Uiso 1 1 calc R U . . .
C14 C 0.4385(3) 0.23595(12) 1.0282(3) 0.0297(5) Uani 1 1 d . . . . .
H14A H 0.4429 0.2846 1.0663 0.036 Uiso 1 1 calc R U . . .
H14B H 0.5011 0.2309 0.9176 0.036 Uiso 1 1 calc R U . . .
H14C H 0.4962 0.2068 1.1208 0.036 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
Se C8 1.933(2) . ?
Se C2 1.934(2) . ?
N1 C2 1.333(3) . ?
N1 C6 1.341(3) . ?
C2 C3 1.395(3) . ?
C3 C4 1.393(3) . ?
C3 C13 1.504(3) . ?
C4 C5 1.380(3) . ?
C4 H4 0.9500 . ?
C5 C6 1.378(3) . ?
C5 H5 0.9500 . ?
C6 H6 0.9500 . ?
N7 C8 1.329(3) . ?
N7 C12 1.337(3) . ?
C8 C9 1.400(3) . ?
C9 C10 1.389(3) . ?
C9 C14 1.501(3) . ?
C10 C11 1.383(3) . ?
C10 H10 0.9500 . ?
C11 C12 1.382(3) . ?
C11 H11 0.9500 . ?
C12 H12 0.9500 . ?
C13 H13A 0.9800 . ?
C13 H13B 0.9800 . ?
C13 H13C 0.9800 . ?
C14 H14A 0.9800 . ?
C14 H14B 0.9800 . ?
C14 H14C 0.9800 . ?

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 Se C2 97.90(8) . . ?
C2 N1 C6 117.08(18) . . ?
N1 C2 C3 124.88(19) . . ?
N1 C2 Se 115.61(15) . . ?
C3 C2 Se 119.46(15) . . ?
C4 C3 C2 115.87(19) . . ?
C4 C3 C13 121.27(19) . . ?
C2 C3 C13 122.83(19) . . ?
C5 C4 C3 120.6(2) . . ?
C5 C4 H4 119.7 . . ?
C3 C4 H4 119.7 . . ?
C6 C5 C4 118.3(2) . . ?
C6 C5 H5 120.8 . . ?
C4 C5 H5 120.8 . . ?
N1 C6 C5 123.3(2) . . ?
N1 C6 H6 118.4 . . ?
C5 C6 H6 118.4 . . ?
C8 N7 C12 117.50(18) . . ?
N7 C8 C9 124.62(19) . . ?
N7 C8 Se 115.87(15) . . ?
C9 C8 Se 119.43(15) . . ?
C10 C9 C8 115.81(19) . . ?
C10 C9 C14 121.46(19) . . ?
C8 C9 C14 122.72(19) . . ?
C11 C10 C9 120.9(2) . . ?
C11 C10 H10 119.6 . . ?
C9 C10 H10 119.6 . . ?
C12 C11 C10 117.9(2) . . ?
C12 C11 H11 121.1 . . ?
C10 C11 H11 121.1 . . ?
N7 C12 C11 123.3(2) . . ?
N7 C12 H12 118.3 . . ?
C11 C12 H12 118.3 . . ?
C3 C13 H13A 109.5 . . ?
C3 C13 H13B 109.5 . . ?
H13A C13 H13B 109.5 . . ?
C3 C13 H13C 109.5 . . ?
H13A C13 H13C 109.5 . . ?
H13B C13 H13C 109.5 . . ?
C9 C14 H14A 109.5 . . ?
C9 C14 H14B 109.5 . . ?
H14A C14 H14B 109.5 . . ?
C9 C14 H14C 109.5 . . ?
H14A C14 H14C 109.5 . . ?
H14B C14 H14C 109.5 . . ?

_refine_diff_density_max         0.507
_refine_diff_density_min         -0.443
_refine_diff_density_rms         0.080

_shelxl_version_number           2013-4





