# Electronic Supplementary Material (ESI) for Dalton Transactions.
# 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_p1522b
_database_code_depnum_ccdc_archive 'CCDC 1402867'
_audit_update_record             
;
2015-05-26 deposited with the CCDC.
2015-07-28 downloaded from the CCDC.
;

#==============================================================================



_audit_creation_method           SHELXL-2014
_chemical_name_systematic        
;
 ?
;
_chemical_name_common            ?
_chemical_formula_moiety         'C9 H16 N2 Se'
_chemical_formula_sum            'C9 H16 N2 Se'
_chemical_formula_weight         231.20

loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
Se Se -0.0929 2.2259 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
C C 0.0033 0.0016 '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'
H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_space_group_crystal_system      orthorhombic
_space_group_IT_number           19
_space_group_name_H-M_alt        'P 21 21 21'
_space_group_name_Hall           'P 2ac 2ab'

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

_cell_length_a                   8.774(4)
_cell_length_b                   11.3185(5)
_cell_length_c                   11.3495(5)
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_volume                     1127.1(5)
_cell_formula_units_Z            4
_cell_measurement_temperature    208(2)
_cell_measurement_reflns_used    234
_cell_measurement_theta_min      1.5
_cell_measurement_theta_max      35

_exptl_crystal_description       block
_exptl_crystal_colour            transparent
_exptl_crystal_density_diffrn    1.362
_exptl_crystal_F_000             472
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.220
_exptl_crystal_size_mid          0.210
_exptl_crystal_size_min          0.170
_exptl_absorpt_coefficient_mu    3.287
_shelx_estimated_absorpt_T_min   0.532
_shelx_estimated_absorpt_T_max   0.605
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.67
_exptl_absorpt_correction_T_max  0.75
_exptl_absorpt_process_details   'SADABS multiscan (Sheldrick, 1996)'

_exptl_special_details           
;
 ?
;

_diffrn_ambient_temperature      208(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_radiation_source         'fine-focus sealed tube'
_diffrn_radiation_monochromator  graphite
_diffrn_measurement_device       'Nonius KappaCCD'
_diffrn_measurement_method       'area detector φ and ω scan'
_diffrn_detector_area_resol_mean 18.4
_diffrn_reflns_number            56721
_diffrn_reflns_av_unetI/netI     0.0273
_diffrn_reflns_av_R_equivalents  0.0531
_diffrn_reflns_limit_h_min       -13
_diffrn_reflns_limit_h_max       13
_diffrn_reflns_limit_k_min       -17
_diffrn_reflns_limit_k_max       17
_diffrn_reflns_limit_l_min       -17
_diffrn_reflns_limit_l_max       17
_diffrn_reflns_theta_min         2.541
_diffrn_reflns_theta_max         32.489
_diffrn_reflns_theta_full        25.242
_diffrn_measured_fraction_theta_max 1.000
_diffrn_measured_fraction_theta_full 1.000
_diffrn_reflns_Laue_measured_fraction_max 1.000
_diffrn_reflns_Laue_measured_fraction_full 1.000
_diffrn_reflns_point_group_measured_fraction_max 1.000
_diffrn_reflns_point_group_measured_fraction_full 1.000
_reflns_number_total             4097
_reflns_number_gt                3427
_reflns_threshold_expression     'I > 2σ(I)'
_reflns_Friedel_coverage         0.758
_reflns_Friedel_fraction_max     1.000
_reflns_Friedel_fraction_full    1.000

_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       
;
Nonius "Collect" program suite (Nonius, 1998)
;
_computing_cell_refinement       
;
Nonius "EvalCCD" program suite (Duisenberg, 1998)
;
_computing_data_reduction        
;
Nonius "EvalCCD" program suite (Duisenberg, 2003)
;
_computing_structure_solution    'SHELXL-2014 (Sheldrick, 2014)'
_computing_structure_refinement  'SHELXL-2014 (Sheldrick, 2014)'
_computing_molecular_graphics    
;
PLATON (Spek, 2003)
SHELXLe (Hübschle et al, 2011)
;
_computing_publication_material  ?

_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)+(0.0258P)²+0.0128P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_atom_sites_solution_hydrogens   geom
_refine_ls_hydrogen_treatment    constr
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       .
_refine_ls_abs_structure_details 
;
 Flack x determined using 1307 quotients [(I+)-(I-)]/[(I+)+(I-)]
 (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259).
;
_refine_ls_abs_structure_Flack   0.025(5)
_chemical_absolute_configuration ad
_refine_ls_number_reflns         4097
_refine_ls_number_parameters     113
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0409
_refine_ls_R_factor_gt           0.0275
_refine_ls_wR_factor_ref         0.0542
_refine_ls_wR_factor_gt          0.0505
_refine_ls_goodness_of_fit_ref   1.055
_refine_ls_restrained_S_all      1.055
_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 0.77720(3) -0.00745(2) 0.89167(2) 0.03628(7) Uani 1 1 d . . . . .
N2 N 0.9389(2) 0.19204(16) 0.98577(17) 0.0315(4) Uani 1 1 d . . . . .
N3 N 0.9262(2) 0.19748(16) 0.79610(16) 0.0325(4) Uani 1 1 d . . . . .
C4 C 1.0701(4) 0.0711(3) 1.1328(2) 0.0597(8) Uani 1 1 d . . . . .
H4A H 1.0692 0.0043 1.0794 0.090 Uiso 1 1 calc R U . . .
H4B H 1.0662 0.0430 1.2135 0.090 Uiso 1 1 calc R U . . .
H4C H 1.1626 0.1165 1.1210 0.090 Uiso 1 1 calc R U . . .
C5 C 0.8851(2) 0.13282(16) 0.8913(2) 0.0282(4) Uani 1 1 d . . . . .
C6 C 1.0148(3) 0.2924(2) 0.9494(2) 0.0371(5) Uani 1 1 d . . . . .
H6 H 1.0629 0.3482 0.9982 0.044 Uiso 1 1 calc R U . . .
C7 C 0.8994(3) 0.1637(2) 0.6723(2) 0.0380(5) Uani 1 1 d . . . . .
H7 H 0.8258 0.0975 0.6706 0.046 Uiso 1 1 calc R U . . .
C8 C 1.0071(3) 0.2953(2) 0.8313(2) 0.0402(6) Uani 1 1 d . . . . .
H8 H 1.0491 0.3535 0.7819 0.048 Uiso 1 1 calc R U . . .
C9 C 0.9326(3) 0.1490(2) 1.1087(2) 0.0367(5) Uani 1 1 d . . . . .
H9 H 0.8398 0.1000 1.1174 0.044 Uiso 1 1 calc R U . . .
C10 C 0.9206(4) 0.2522(2) 1.1936(2) 0.0515(7) Uani 1 1 d . . . . .
H10A H 0.9034 0.2227 1.2728 0.077 Uiso 1 1 calc R U . . .
H10B H 0.8361 0.3025 1.1706 0.077 Uiso 1 1 calc R U . . .
H10C H 1.0145 0.2974 1.1918 0.077 Uiso 1 1 calc R U . . .
C11 C 0.8318(4) 0.2669(3) 0.6046(3) 0.0666(9) Uani 1 1 d . . . . .
H11A H 0.7402 0.2940 0.6440 0.100 Uiso 1 1 calc R U . . .
H11B H 0.8068 0.2418 0.5252 0.100 Uiso 1 1 calc R U . . .
H11C H 0.9053 0.3308 0.6013 0.100 Uiso 1 1 calc R U . . .
C12 C 1.0470(3) 0.1223(3) 0.6189(3) 0.0591(8) Uani 1 1 d . . . . .
H12A H 1.0292 0.0966 0.5386 0.089 Uiso 1 1 calc R U . . .
H12B H 1.0870 0.0570 0.6647 0.089 Uiso 1 1 calc R U . . .
H12C H 1.1200 0.1867 0.6190 0.089 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 C5 1.8487(18) . ?
N2 C5 1.349(3) . ?
N2 C6 1.380(3) . ?
N2 C9 1.479(3) . ?
N3 C5 1.354(3) . ?
N3 C8 1.375(3) . ?
N3 C7 1.475(3) . ?
C4 C9 1.519(4) . ?
C4 H4A 0.9700 . ?
C4 H4B 0.9700 . ?
C4 H4C 0.9700 . ?
C6 C8 1.343(3) . ?
C6 H6 0.9400 . ?
C7 C12 1.505(4) . ?
C7 C11 1.518(4) . ?
C7 H7 0.9900 . ?
C8 H8 0.9400 . ?
C9 C10 1.519(3) . ?
C9 H9 0.9900 . ?
C10 H10A 0.9700 . ?
C10 H10B 0.9700 . ?
C10 H10C 0.9700 . ?
C11 H11A 0.9700 . ?
C11 H11B 0.9700 . ?
C11 H11C 0.9700 . ?
C12 H12A 0.9700 . ?
C12 H12B 0.9700 . ?
C12 H12C 0.9700 . ?

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
C5 N2 C6 109.89(19) . . ?
C5 N2 C9 124.92(18) . . ?
C6 N2 C9 124.9(2) . . ?
C5 N3 C8 109.91(19) . . ?
C5 N3 C7 125.34(19) . . ?
C8 N3 C7 124.6(2) . . ?
C9 C4 H4A 109.5 . . ?
C9 C4 H4B 109.5 . . ?
H4A C4 H4B 109.5 . . ?
C9 C4 H4C 109.5 . . ?
H4A C4 H4C 109.5 . . ?
H4B C4 H4C 109.5 . . ?
N2 C5 N3 105.82(16) . . ?
N2 C5 Se1 127.17(16) . . ?
N3 C5 Se1 127.01(16) . . ?
C8 C6 N2 107.1(2) . . ?
C8 C6 H6 126.4 . . ?
N2 C6 H6 126.4 . . ?
N3 C7 C12 109.1(2) . . ?
N3 C7 C11 110.2(2) . . ?
C12 C7 C11 111.8(2) . . ?
N3 C7 H7 108.5 . . ?
C12 C7 H7 108.5 . . ?
C11 C7 H7 108.5 . . ?
C6 C8 N3 107.2(2) . . ?
C6 C8 H8 126.4 . . ?
N3 C8 H8 126.4 . . ?
N2 C9 C10 110.36(19) . . ?
N2 C9 C4 109.4(2) . . ?
C10 C9 C4 112.8(2) . . ?
N2 C9 H9 108.1 . . ?
C10 C9 H9 108.1 . . ?
C4 C9 H9 108.1 . . ?
C9 C10 H10A 109.5 . . ?
C9 C10 H10B 109.5 . . ?
H10A C10 H10B 109.5 . . ?
C9 C10 H10C 109.5 . . ?
H10A C10 H10C 109.5 . . ?
H10B C10 H10C 109.5 . . ?
C7 C11 H11A 109.5 . . ?
C7 C11 H11B 109.5 . . ?
H11A C11 H11B 109.5 . . ?
C7 C11 H11C 109.5 . . ?
H11A C11 H11C 109.5 . . ?
H11B C11 H11C 109.5 . . ?
C7 C12 H12A 109.5 . . ?
C7 C12 H12B 109.5 . . ?
H12A C12 H12B 109.5 . . ?
C7 C12 H12C 109.5 . . ?
H12A C12 H12C 109.5 . . ?
H12B C12 H12C 109.5 . . ?

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
C6 N2 C5 N3 -0.8(2) . . . . ?
C9 N2 C5 N3 -174.4(2) . . . . ?
C6 N2 C5 Se1 179.40(17) . . . . ?
C9 N2 C5 Se1 5.7(3) . . . . ?
C8 N3 C5 N2 0.9(2) . . . . ?
C7 N3 C5 N2 176.3(2) . . . . ?
C8 N3 C5 Se1 -179.22(17) . . . . ?
C7 N3 C5 Se1 -3.8(3) . . . . ?
C5 N2 C6 C8 0.3(3) . . . . ?
C9 N2 C6 C8 174.0(2) . . . . ?
C5 N3 C7 C12 -104.5(3) . . . . ?
C8 N3 C7 C12 70.3(3) . . . . ?
C5 N3 C7 C11 132.4(3) . . . . ?
C8 N3 C7 C11 -52.9(3) . . . . ?
N2 C6 C8 N3 0.3(3) . . . . ?
C5 N3 C8 C6 -0.8(3) . . . . ?
C7 N3 C8 C6 -176.2(2) . . . . ?
C5 N2 C9 C10 -149.6(2) . . . . ?
C6 N2 C9 C10 37.7(3) . . . . ?
C5 N2 C9 C4 85.8(3) . . . . ?
C6 N2 C9 C4 -86.9(3) . . . . ?

_refine_diff_density_max         0.285
_refine_diff_density_min         -0.686
_refine_diff_density_rms         0.060

_shelxl_version_number           2014-1


_exptl_crystal_recrystallization_method 'Re-crystallisation from solvent: '
