# Electronic Supplementary Material (ESI) for CrystEngComm.
# This journal is © The Royal Society of Chemistry 2018

####################################################################### 
# 
# 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_shelx
_database_code_depnum_ccdc_archive 'CCDC 1849844'
_audit_update_record             
;
2018-08-08 deposited with the CCDC.
2018-09-12 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2018/3
_shelx_SHELXL_version_number     2018/3
_chemical_name_systematic        ?
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         'C16 H36 N, 0.5(C10 H8 N2 Se2), I'
_chemical_formula_sum            'C21 H40 I N2 Se'
_chemical_formula_weight         526.41

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'
I I -0.4742 1.8119 '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/c'
_space_group_name_Hall           '-P 2ybc'

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

_cell_length_a                   8.059(4)
_cell_length_b                   14.506(6)
_cell_length_c                   21.978(10)
_cell_angle_alpha                90
_cell_angle_beta                 90.494(11)
_cell_angle_gamma                90
_cell_volume                     2569(2)
_cell_formula_units_Z            4
_cell_measurement_reflns_used    3724
_cell_measurement_temperature    200
_cell_measurement_theta_max      24.999
_cell_measurement_theta_min      1.682

_exptl_crystal_description       plate
_exptl_crystal_colour            'clear light colourless'
_exptl_crystal_colour_lustre     clear
_exptl_crystal_colour_modifier   light
_exptl_crystal_colour_primary    colourless
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.361
_exptl_crystal_F_000             1068
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.260
_exptl_crystal_size_mid          0.200
_exptl_crystal_size_min          0.140
_exptl_absorpt_coefficient_mu    2.669
_shelx_estimated_absorpt_T_min   0.544
_shelx_estimated_absorpt_T_max   0.706
_exptl_absorpt_correction_T_max  0.706
_exptl_absorpt_correction_T_min  0.544
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
SADABS-2012/1 (Bruker,2012) was used for absorption correction.
wR2(int) was 0.0955 before and 0.0681 after correction.
The Ratio of minimum to maximum transmission is 0.9205.
The λ/2 correction factor is 0.0015.
;
_exptl_absorpt_special_details   ?
_diffrn_ambient_temperature      200(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_source                   ?
_diffrn_measurement_device       'three-circle diffractometer'
_diffrn_measurement_device_type  'Bruker APEX-II CCD'
_diffrn_measurement_method       'ω and φ scans'
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            26625
_diffrn_reflns_av_unetI/netI     0.0568
_diffrn_reflns_av_R_equivalents  0.1071
_diffrn_reflns_limit_h_min       -8
_diffrn_reflns_limit_h_max       10
_diffrn_reflns_limit_k_min       -17
_diffrn_reflns_limit_k_max       18
_diffrn_reflns_limit_l_min       -28
_diffrn_reflns_limit_l_max       28
_diffrn_reflns_theta_min         1.682
_diffrn_reflns_theta_max         26.998
_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             5612
_reflns_number_gt                4291
_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       'APEX II (Bruker, 2009)'
_computing_cell_refinement       'APEX II (Bruker, 2009)'
_computing_data_reduction        'SAINT (Bruker)'
_computing_structure_solution    'SHELXT 2014/5 (Sheldrick, 2014)'
_computing_structure_refinement  'SHELXL-2016/6 (Sheldrick, 2016)'
_computing_molecular_graphics    'Mercury (Macrae et al., 2008)'
_computing_publication_material  'CIFTAB (Sheldrick, 1997)'

_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)+(0.0348P)²] 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     'SHELXL-2018/3 (Sheldrick 2018)'
_refine_ls_extinction_coef       0.00051(19)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc²λ³/sin(2θ)]^-1/4^
_refine_ls_number_reflns         5612
_refine_ls_number_parameters     231
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0445
_refine_ls_R_factor_gt           0.0309
_refine_ls_wR_factor_ref         0.0773
_refine_ls_wR_factor_gt          0.0745
_refine_ls_goodness_of_fit_ref   0.945
_refine_ls_restrained_S_all      0.945
_refine_ls_shift/su_max          0.003
_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
I1 I 0.79282(2) 0.92952(2) 0.74951(2) 0.04962(9) Uani 1 1 d . . . . .
Se1 Se 1.34337(3) 1.13880(2) 0.39554(2) 0.04114(9) Uani 1 1 d . . . . .
N1 N 1.4781(3) 1.1828(2) 0.52014(13) 0.0654(7) Uani 1 1 d . . . . .
C4 C 1.1349(3) 1.00603(16) 0.46024(11) 0.0341(5) Uani 1 1 d . . . . .
N2 N 0.3007(2) 0.71635(13) 0.32341(9) 0.0327(4) Uani 1 1 d . . . . .
C10 C 1.4256(3) 1.1653(2) 0.47327(13) 0.0450(6) Uani 1 1 d . . . . .
C9 C 1.2774(3) 1.01106(17) 0.41673(12) 0.0414(6) Uani 1 1 d . . . . .
H9A H 1.246504 0.977922 0.378917 0.050 Uiso 1 1 calc R U . . .
H9B H 1.374148 0.978984 0.434993 0.050 Uiso 1 1 calc R U . . .
C6 C 0.9748(3) 1.02139(19) 0.43977(11) 0.0424(6) Uani 1 1 d . . . . .
H6 H 0.955720 1.036210 0.398190 0.051 Uiso 1 1 calc R U . . .
C5 C 1.1591(3) 0.98451(19) 0.52088(12) 0.0435(6) Uani 1 1 d . . . . .
H5 H 1.268224 0.973628 0.535884 0.052 Uiso 1 1 calc R U . . .
C18 C 0.3995(6) 0.3904(3) 0.4020(2) 0.0993(15) Uani 1 1 d . . . . .
H18A H 0.393470 0.362693 0.361335 0.149 Uiso 1 1 calc R U . . .
H18B H 0.289615 0.388530 0.420680 0.149 Uiso 1 1 calc R U . . .
H18C H 0.478543 0.355778 0.427239 0.149 Uiso 1 1 calc R U . . .
C17 C 0.4555(5) 0.4880(2) 0.39685(19) 0.0786(11) Uani 1 1 d . . . . .
H17A H 0.565122 0.489221 0.376860 0.094 Uiso 1 1 calc R U . . .
H17B H 0.469775 0.513801 0.438258 0.094 Uiso 1 1 calc R U . . .
C16 C 0.3355(4) 0.54905(19) 0.36094(14) 0.0530(7) Uani 1 1 d . . . . .
H16A H 0.317779 0.523244 0.319693 0.064 Uiso 1 1 calc R U . . .
H16B H 0.227079 0.551422 0.381690 0.064 Uiso 1 1 calc R U . . .
C15 C 0.4075(3) 0.64493(17) 0.35637(12) 0.0394(6) Uani 1 1 d . . . . .
H15A H 0.515266 0.640706 0.335238 0.047 Uiso 1 1 calc R U . . .
H15B H 0.430328 0.667644 0.398085 0.047 Uiso 1 1 calc R U . . .
C11 C 0.3855(3) 0.80929(17) 0.33006(11) 0.0365(6) Uani 1 1 d . . . . .
H11A H 0.397604 0.823202 0.373972 0.044 Uiso 1 1 calc R U . . .
H11B H 0.312154 0.856982 0.312095 0.044 Uiso 1 1 calc R U . . .
C12 C 0.5552(3) 0.8172(2) 0.30085(14) 0.0507(7) Uani 1 1 d . . . . .
H12A H 0.629480 0.768972 0.317618 0.061 Uiso 1 1 calc R U . . .
H12B H 0.544311 0.807023 0.256451 0.061 Uiso 1 1 calc R U . . .
C13 C 0.6308(4) 0.9114(2) 0.31251(15) 0.0546(8) Uani 1 1 d . . . . .
H13A H 0.559915 0.959214 0.293366 0.065 Uiso 1 1 calc R U . . .
H13B H 0.634103 0.923223 0.356869 0.065 Uiso 1 1 calc R U . . .
C14 C 0.8038(4) 0.9185(3) 0.28754(18) 0.0683(10) Uani 1 1 d . . . . .
H14A H 0.803181 0.899437 0.244762 0.102 Uiso 1 1 calc R U . . .
H14B H 0.878327 0.878270 0.310935 0.102 Uiso 1 1 calc R U . . .
H14C H 0.842408 0.982391 0.290681 0.102 Uiso 1 1 calc R U . . .
C26 C -0.1372(5) 0.6474(3) 0.44216(18) 0.0888(13) Uani 1 1 d . . . . .
H26A H -0.148957 0.623759 0.400573 0.133 Uiso 1 1 calc R U . . .
H26B H -0.246819 0.651516 0.460915 0.133 Uiso 1 1 calc R U . . .
H26C H -0.066740 0.605527 0.466011 0.133 Uiso 1 1 calc R U . . .
C25 C -0.0591(4) 0.7414(2) 0.44062(13) 0.0578(8) Uani 1 1 d . . . . .
H25A H -0.062421 0.768212 0.482003 0.069 Uiso 1 1 calc R U . . .
H25B H -0.125983 0.781521 0.413483 0.069 Uiso 1 1 calc R U . . .
C24 C 0.1197(3) 0.7416(2) 0.41885(12) 0.0456(7) Uani 1 1 d . . . . .
H24A H 0.170511 0.802420 0.427500 0.055 Uiso 1 1 calc R U . . .
H24B H 0.183823 0.694204 0.441312 0.055 Uiso 1 1 calc R U . . .
C23 C 0.1278(3) 0.72218(19) 0.35122(11) 0.0384(6) Uani 1 1 d . . . . .
H23A H 0.065178 0.771114 0.329611 0.046 Uiso 1 1 calc R U . . .
H23B H 0.069956 0.663161 0.343225 0.046 Uiso 1 1 calc R U . . .
C19 C 0.2819(3) 0.6897(2) 0.25683(11) 0.0402(6) Uani 1 1 d . . . . .
H19A H 0.393445 0.676668 0.240403 0.048 Uiso 1 1 calc R U . . .
H19B H 0.216775 0.631963 0.254342 0.048 Uiso 1 1 calc R U . . .
C20 C 0.1991(4) 0.7610(2) 0.21679(13) 0.0547(8) Uani 1 1 d . . . . .
H20A H 0.084974 0.772070 0.231380 0.066 Uiso 1 1 calc R U . . .
H20B H 0.261071 0.819809 0.219969 0.066 Uiso 1 1 calc R U . . .
C21 C 0.1921(5) 0.7316(3) 0.15176(14) 0.0760(11) Uani 1 1 d . . . . .
H21A H 0.129056 0.673166 0.149088 0.091 Uiso 1 1 calc R U . . .
H21B H 0.306562 0.718827 0.138070 0.091 Uiso 1 1 calc R U . . .
C22 C 0.1148(5) 0.7997(4) 0.10906(17) 0.1025(16) Uani 1 1 d . . . . .
H22A H 0.130728 0.779076 0.067043 0.154 Uiso 1 1 calc R U . . .
H22B H 0.167176 0.860051 0.114770 0.154 Uiso 1 1 calc R U . . .
H22C H -0.004143 0.804467 0.117364 0.154 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 C10 1.867(3) . ?
Se1 C9 1.984(3) . ?
N1 C10 1.139(4) . ?
C4 C5 1.381(3) . ?
C4 C6 1.381(4) . ?
C4 C9 1.502(4) . ?
N2 C11 1.518(3) . ?
N2 C19 1.520(3) . ?
N2 C15 1.526(3) . ?
N2 C23 1.528(3) . ?
C9 H9A 0.9900 . ?
C9 H9B 0.9900 . ?
C6 C5 1.391(4) 3_776 ?
C6 H6 0.9500 . ?
C5 H5 0.9500 . ?
C18 C17 1.490(5) . ?
C18 H18A 0.9800 . ?
C18 H18B 0.9800 . ?
C18 H18C 0.9800 . ?
C17 C16 1.527(4) . ?
C17 H17A 0.9900 . ?
C17 H17B 0.9900 . ?
C16 C15 1.511(4) . ?
C16 H16A 0.9900 . ?
C16 H16B 0.9900 . ?
C15 H15A 0.9900 . ?
C15 H15B 0.9900 . ?
C11 C12 1.520(4) . ?
C11 H11A 0.9900 . ?
C11 H11B 0.9900 . ?
C12 C13 1.517(4) . ?
C12 H12A 0.9900 . ?
C12 H12B 0.9900 . ?
C13 C14 1.506(4) . ?
C13 H13A 0.9900 . ?
C13 H13B 0.9900 . ?
C14 H14A 0.9800 . ?
C14 H14B 0.9800 . ?
C14 H14C 0.9800 . ?
C26 C25 1.502(5) . ?
C26 H26A 0.9800 . ?
C26 H26B 0.9800 . ?
C26 H26C 0.9800 . ?
C25 C24 1.522(4) . ?
C25 H25A 0.9900 . ?
C25 H25B 0.9900 . ?
C24 C23 1.515(3) . ?
C24 H24A 0.9900 . ?
C24 H24B 0.9900 . ?
C23 H23A 0.9900 . ?
C23 H23B 0.9900 . ?
C19 C20 1.510(4) . ?
C19 H19A 0.9900 . ?
C19 H19B 0.9900 . ?
C20 C21 1.492(4) . ?
C20 H20A 0.9900 . ?
C20 H20B 0.9900 . ?
C21 C22 1.495(5) . ?
C21 H21A 0.9900 . ?
C21 H21B 0.9900 . ?
C22 H22A 0.9800 . ?
C22 H22B 0.9800 . ?
C22 H22C 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
C10 Se1 C9 94.09(12) . . ?
C5 C4 C6 118.3(2) . . ?
C5 C4 C9 121.6(2) . . ?
C6 C4 C9 120.1(2) . . ?
C11 N2 C19 111.06(19) . . ?
C11 N2 C15 107.78(18) . . ?
C19 N2 C15 109.61(19) . . ?
C11 N2 C23 108.89(18) . . ?
C19 N2 C23 108.39(18) . . ?
C15 N2 C23 111.13(19) . . ?
N1 C10 Se1 178.5(3) . . ?
C4 C9 Se1 113.73(17) . . ?
C4 C9 H9A 108.8 . . ?
Se1 C9 H9A 108.8 . . ?
C4 C9 H9B 108.8 . . ?
Se1 C9 H9B 108.8 . . ?
H9A C9 H9B 107.7 . . ?
C4 C6 C5 121.0(2) . 3_776 ?
C4 C6 H6 119.5 . . ?
C5 C6 H6 119.5 3_776 . ?
C4 C5 C6 120.7(2) . 3_776 ?
C4 C5 H5 119.7 . . ?
C6 C5 H5 119.7 3_776 . ?
C17 C18 H18A 109.5 . . ?
C17 C18 H18B 109.5 . . ?
H18A C18 H18B 109.5 . . ?
C17 C18 H18C 109.5 . . ?
H18A C18 H18C 109.5 . . ?
H18B C18 H18C 109.5 . . ?
C18 C17 C16 113.5(3) . . ?
C18 C17 H17A 108.9 . . ?
C16 C17 H17A 108.9 . . ?
C18 C17 H17B 108.9 . . ?
C16 C17 H17B 108.9 . . ?
H17A C17 H17B 107.7 . . ?
C15 C16 C17 109.1(3) . . ?
C15 C16 H16A 109.9 . . ?
C17 C16 H16A 109.9 . . ?
C15 C16 H16B 109.9 . . ?
C17 C16 H16B 109.9 . . ?
H16A C16 H16B 108.3 . . ?
C16 C15 N2 116.2(2) . . ?
C16 C15 H15A 108.2 . . ?
N2 C15 H15A 108.2 . . ?
C16 C15 H15B 108.2 . . ?
N2 C15 H15B 108.2 . . ?
H15A C15 H15B 107.4 . . ?
N2 C11 C12 115.6(2) . . ?
N2 C11 H11A 108.4 . . ?
C12 C11 H11A 108.4 . . ?
N2 C11 H11B 108.4 . . ?
C12 C11 H11B 108.4 . . ?
H11A C11 H11B 107.4 . . ?
C13 C12 C11 111.0(2) . . ?
C13 C12 H12A 109.4 . . ?
C11 C12 H12A 109.4 . . ?
C13 C12 H12B 109.4 . . ?
C11 C12 H12B 109.4 . . ?
H12A C12 H12B 108.0 . . ?
C14 C13 C12 111.8(3) . . ?
C14 C13 H13A 109.3 . . ?
C12 C13 H13A 109.3 . . ?
C14 C13 H13B 109.3 . . ?
C12 C13 H13B 109.3 . . ?
H13A C13 H13B 107.9 . . ?
C13 C14 H14A 109.5 . . ?
C13 C14 H14B 109.5 . . ?
H14A C14 H14B 109.5 . . ?
C13 C14 H14C 109.5 . . ?
H14A C14 H14C 109.5 . . ?
H14B C14 H14C 109.5 . . ?
C25 C26 H26A 109.5 . . ?
C25 C26 H26B 109.5 . . ?
H26A C26 H26B 109.5 . . ?
C25 C26 H26C 109.5 . . ?
H26A C26 H26C 109.5 . . ?
H26B C26 H26C 109.5 . . ?
C26 C25 C24 114.0(3) . . ?
C26 C25 H25A 108.7 . . ?
C24 C25 H25A 108.7 . . ?
C26 C25 H25B 108.7 . . ?
C24 C25 H25B 108.7 . . ?
H25A C25 H25B 107.6 . . ?
C23 C24 C25 110.9(2) . . ?
C23 C24 H24A 109.5 . . ?
C25 C24 H24A 109.5 . . ?
C23 C24 H24B 109.5 . . ?
C25 C24 H24B 109.5 . . ?
H24A C24 H24B 108.0 . . ?
C24 C23 N2 116.7(2) . . ?
C24 C23 H23A 108.1 . . ?
N2 C23 H23A 108.1 . . ?
C24 C23 H23B 108.1 . . ?
N2 C23 H23B 108.1 . . ?
H23A C23 H23B 107.3 . . ?
C20 C19 N2 115.3(2) . . ?
C20 C19 H19A 108.5 . . ?
N2 C19 H19A 108.5 . . ?
C20 C19 H19B 108.5 . . ?
N2 C19 H19B 108.5 . . ?
H19A C19 H19B 107.5 . . ?
C21 C20 C19 112.0(3) . . ?
C21 C20 H20A 109.2 . . ?
C19 C20 H20A 109.2 . . ?
C21 C20 H20B 109.2 . . ?
C19 C20 H20B 109.2 . . ?
H20A C20 H20B 107.9 . . ?
C20 C21 C22 115.1(3) . . ?
C20 C21 H21A 108.5 . . ?
C22 C21 H21A 108.5 . . ?
C20 C21 H21B 108.5 . . ?
C22 C21 H21B 108.5 . . ?
H21A C21 H21B 107.5 . . ?
C21 C22 H22A 109.5 . . ?
C21 C22 H22B 109.5 . . ?
H22A C22 H22B 109.5 . . ?
C21 C22 H22C 109.5 . . ?
H22A C22 H22C 109.5 . . ?
H22B C22 H22C 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
C5 C4 C9 Se1 -104.2(2) . . . . ?
C6 C4 C9 Se1 77.0(3) . . . . ?
C5 C4 C6 C5 0.1(4) . . . 3_776 ?
C9 C4 C6 C5 178.9(2) . . . 3_776 ?
C6 C4 C5 C6 -0.1(4) . . . 3_776 ?
C9 C4 C5 C6 -178.9(2) . . . 3_776 ?
C18 C17 C16 C15 -177.7(3) . . . . ?
C17 C16 C15 N2 -178.1(3) . . . . ?
C11 N2 C15 C16 173.7(2) . . . . ?
C19 N2 C15 C16 -65.3(3) . . . . ?
C23 N2 C15 C16 54.5(3) . . . . ?
C19 N2 C11 C12 -56.8(3) . . . . ?
C15 N2 C11 C12 63.3(3) . . . . ?
C23 N2 C11 C12 -176.1(2) . . . . ?
N2 C11 C12 C13 -177.7(2) . . . . ?
C11 C12 C13 C14 176.2(3) . . . . ?
C26 C25 C24 C23 71.5(4) . . . . ?
C25 C24 C23 N2 -177.5(2) . . . . ?
C11 N2 C23 C24 -63.1(3) . . . . ?
C19 N2 C23 C24 176.0(2) . . . . ?
C15 N2 C23 C24 55.5(3) . . . . ?
C11 N2 C19 C20 -52.9(3) . . . . ?
C15 N2 C19 C20 -171.8(2) . . . . ?
C23 N2 C19 C20 66.7(3) . . . . ?
N2 C19 C20 C21 177.5(3) . . . . ?
C19 C20 C21 C22 -178.8(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
_geom_hbond_publ_flag
C9 H9A I1 0.99 3.14 3.792(3) 124.7 3_776 yes
C15 H15A I1 0.99 3.11 4.056(3) 160.6 4_575 yes
C11 H11A N1 0.99 2.53 3.464(4) 157.8 3_776 yes
C23 H23B I1 0.99 3.31 4.126(3) 140.9 4_475 yes
C9 H9A I1 0.99 3.14 3.792(3) 124.7 3_776 yes
C15 H15A I1 0.99 3.11 4.056(3) 160.6 4_575 yes
C11 H11A N1 0.99 2.53 3.464(4) 157.8 3_776 yes
C23 H23B I1 0.99 3.31 4.126(3) 140.9 4_475 yes

_refine_diff_density_max         0.579
_refine_diff_density_min         -0.850
_refine_diff_density_rms         0.076

####################################################################### 
# 
# 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_shelx_CCDC1
_database_code_depnum_ccdc_archive 'CCDC 1851129'
_audit_update_record             
;
2018-09-10 deposited with the CCDC.
2018-09-12 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2016/6
_shelx_SHELXL_version_number     2016/6
_chemical_name_systematic        ?
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         'C16 H36 N, C10 H8 N2 Se2,Cl'
_chemical_formula_sum            'C26 H44 Cl N3 Se2'
_chemical_formula_weight         592.01

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'
Cl Cl 0.1484 0.1585 '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           12
_space_group_name_H-M_alt        'I 2/m'
_space_group_name_Hall           '-I 2y'

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

_cell_length_a                   12.5130(13)
_cell_length_b                   14.1548(18)
_cell_length_c                   17.6517(18)
_cell_angle_alpha                90
_cell_angle_beta                 101.041(7)
_cell_angle_gamma                90
_cell_volume                     3068.6(6)
_cell_formula_units_Z            4
_cell_measurement_temperature    200(2)
_cell_measurement_reflns_used    8754
_cell_measurement_theta_max      27.45
_cell_measurement_theta_min      2.20

_exptl_crystal_colour            'clear light yellow'
_exptl_crystal_colour_lustre     clear
_exptl_crystal_colour_modifier   light
_exptl_crystal_colour_primary    yellow
_exptl_crystal_description       block
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.281
_exptl_crystal_F_000             1224
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.250
_exptl_crystal_size_mid          0.190
_exptl_crystal_size_min          0.120
_exptl_absorpt_coefficient_mu    2.514
_shelx_estimated_absorpt_T_min   0.572
_shelx_estimated_absorpt_T_max   0.752
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_max  0.7456
_exptl_absorpt_correction_T_min  0.4234
_exptl_absorpt_process_details   'SADABS, Bruker (2003)'
_exptl_absorpt_special_details   ?
_diffrn_ambient_temperature      200(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_source                   ?
_diffrn_measurement_device       'three-circle diffractometer'
_diffrn_measurement_device_type  'Bruker SMART CCD 6000 area detector'
_diffrn_measurement_method       'ω scans'
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            73740
_diffrn_reflns_av_unetI/netI     0.0500
_diffrn_reflns_av_R_equivalents  0.1727
_diffrn_reflns_limit_h_min       -15
_diffrn_reflns_limit_h_max       15
_diffrn_reflns_limit_k_min       -16
_diffrn_reflns_limit_k_max       16
_diffrn_reflns_limit_l_min       -21
_diffrn_reflns_limit_l_max       21
_diffrn_reflns_theta_min         1.840
_diffrn_reflns_theta_max         25.248
_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             2901
_reflns_number_gt                1713
_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       'APEX II (Bruker, 2009)'
_computing_cell_refinement       'APEX II (Bruker, 2009)'
_computing_data_reduction        'SAINT (Bruker)'
_computing_structure_solution    'SHELXT 2014/5 (Sheldrick, 2014)'
_computing_structure_refinement  'SHELXL-2016/6 (Sheldrick, 2016)'
_computing_molecular_graphics    
'Olex2 (Dolomanov et al., 2009), Mercury (Macrae et al., 2008)'
_computing_publication_material  'CIFTAB (Sheldrick, 1997)'

_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)+63.1347P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     ?
_atom_sites_solution_secondary   ?
_atom_sites_solution_hydrogens   mixed
_refine_ls_hydrogen_treatment    constr
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       .
_refine_ls_number_reflns         2901
_refine_ls_number_parameters     165
_refine_ls_number_restraints     21
_refine_ls_R_factor_all          0.1513
_refine_ls_R_factor_gt           0.0909
_refine_ls_wR_factor_ref         0.2367
_refine_ls_wR_factor_gt          0.1968
_refine_ls_goodness_of_fit_ref   1.176
_refine_ls_restrained_S_all      1.174
_refine_ls_shift/su_max          0.000
_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
N2 N 0.4546(9) 0.000000 0.3013(6) 0.062(3) Uani 1 2 d S T P . .
C6 C 0.4150(13) 0.000000 0.3797(7) 0.065(4) Uani 1 2 d S T P . .
H6A H 0.445025 -0.056420 0.409450 0.078 Uiso 0.5 1 d R U P . .
H6B H 0.445025 0.056420 0.409440 0.078 Uiso 0.5 1 d R U P . .
C7 C 0.2934(14) 0.000000 0.3725(9) 0.089(6) Uani 1 2 d DS T P . .
H7A H 0.261476 -0.056773 0.344108 0.107 Uiso 0.5 1 calc R U P . .
H7B H 0.261476 0.056773 0.344108 0.107 Uiso 0.5 1 calc R U P . .
C8 C 0.2696(13) 0.000000 0.4548(9) 0.083(5) Uani 1 2 d DS T P . .
H8A H 0.302445 -0.056654 0.482921 0.099 Uiso 0.5 1 calc R U P . .
H8B H 0.302445 0.056654 0.482921 0.099 Uiso 0.5 1 calc R U P . .
C9 C 0.1521(15) 0.000000 0.4515(13) 0.130(9) Uani 1 2 d DS T P . .
H9A H 0.137389 0.000000 0.504099 0.156 Uiso 1 2 calc R U P . .
H9B H 0.120066 0.056530 0.424163 0.156 Uiso 0.5 1 calc R U P . .
H9C H 0.120066 -0.056530 0.424163 0.156 Uiso 0.5 1 calc R U P . .
C10 C 0.4141(8) 0.0871(9) 0.2540(5) 0.071(3) Uani 1 1 d . . . . .
H10A H 0.440635 0.083895 0.204739 0.085 Uiso 1 1 calc R U . . .
H10B H 0.333549 0.084635 0.241383 0.085 Uiso 1 1 calc R U . . .
C11 C 0.4468(12) 0.1792(10) 0.2907(7) 0.097(4) Uani 1 1 d D . . . .
H11A H 0.422385 0.182237 0.340819 0.117 Uiso 1 1 calc R U . . .
H11B H 0.527234 0.183443 0.301395 0.117 Uiso 1 1 calc R U . . .
C12 C 0.4019(10) 0.2613(11) 0.2434(7) 0.093(4) Uani 1 1 d D . . . .
H12A H 0.429090 0.259699 0.194303 0.111 Uiso 1 1 calc R U . . .
H12B H 0.321656 0.255301 0.230650 0.111 Uiso 1 1 calc R U . . .
C13 C 0.4295(16) 0.3526(12) 0.2804(10) 0.140(7) Uani 1 1 d D . . . .
H13A H 0.396979 0.403240 0.245564 0.211 Uiso 1 1 calc R U . . .
H13B H 0.401194 0.355774 0.328369 0.211 Uiso 1 1 calc R U . . .
H13C H 0.508796 0.360180 0.291965 0.211 Uiso 1 1 calc R U . . .
C14 C 0.5797(11) 0.000000 0.3210(9) 0.076(5) Uani 1 2 d S T P A .
H14A H 0.604623 0.056490 0.352538 0.091 Uiso 0.5 1 calc R U P . .
H14B H 0.604623 -0.056490 0.352538 0.091 Uiso 0.5 1 calc R U P . .
C15 C 0.6311(13) 0.000000 0.2514(11) 0.098(6) Uani 1 2 d DS T P . .
H15A H 0.621589 0.062281 0.225455 0.117 Uiso 0.5 1 calc R U P A .
H15B H 0.597416 -0.048922 0.214316 0.117 Uiso 0.5 1 calc R U P . .
C16 C 0.7577(18) -0.022(3) 0.2808(16) 0.112(14) Uani 0.5 1 d D . P A -1
H16A H 0.782172 0.001670 0.334031 0.135 Uiso 0.5 1 calc R U P A -1
H16B H 0.771120 -0.090960 0.280353 0.135 Uiso 0.5 1 calc R U P A -1
C17 C 0.816(2) 0.026(4) 0.228(2) 0.20(2) Uani 0.5 1 d D U P A -1
H17A H 0.894148 0.014342 0.243758 0.304 Uiso 0.5 1 calc R U P A -1
H17B H 0.790750 0.001822 0.175469 0.304 Uiso 0.5 1 calc R U P A -1
H17C H 0.801748 0.094008 0.228889 0.304 Uiso 0.5 1 calc R U P A -1
Se1 Se 0.21383(10) 0.25357(11) -0.06965(7) 0.0832(5) Uani 1 1 d . . . . .
N1 N 0.4190(13) 0.2097(13) -0.1204(8) 0.158(7) Uani 1 1 d . . . . .
C1 C 0.1674(8) 0.0466(8) 0.0305(7) 0.081(4) Uani 1 1 d . . . . .
H1 H 0.100658 0.079679 0.027477 0.097 Uiso 1 1 calc R U . . .
C2 C 0.2653(8) 0.0979(9) 0.0349(5) 0.061(3) Uani 1 1 d . . . . .
C3 C 0.3615(7) 0.0479(7) 0.0402(5) 0.060(3) Uani 1 1 d . . . . .
H3 H 0.428257 0.081068 0.043856 0.073 Uiso 1 1 calc R U . . .
C4 C 0.2636(9) 0.2000(10) 0.0344(6) 0.077(3) Uani 1 1 d . . . . .
H4A H 0.337802 0.223718 0.055453 0.092 Uiso 1 1 calc R U . . .
H4B H 0.214897 0.222293 0.068723 0.092 Uiso 1 1 calc R U . . .
C5 C 0.3419(12) 0.2292(11) -0.0999(7) 0.096(4) Uani 1 1 d . . . . .
Cl1 Cl 0.500000 0.2109(3) 0.500000 0.0711(11) Uani 1 2 d S T P . .


_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
N2 C10 1.520(12) 6 ?
N2 C10 1.520(12) . ?
N2 C14 1.538(18) . ?
N2 C6 1.555(16) . ?
C6 C7 1.50(2) . ?
C6 H6A 0.9900 . ?
C6 H6B 0.9899 . ?
C7 C8 1.537(19) . ?
C7 H7A 0.9900 . ?
C7 H7B 0.9900 . ?
C8 C9 1.461(18) . ?
C8 H8A 0.9900 . ?
C8 H8B 0.9900 . ?
C9 H9A 0.9800 . ?
C9 H9B 0.9800 . ?
C9 H9C 0.9800 . ?
C10 C11 1.479(17) . ?
C10 H10A 0.9900 . ?
C10 H10B 0.9900 . ?
C11 C12 1.477(16) . ?
C11 H11A 0.9900 . ?
C11 H11B 0.9900 . ?
C12 C13 1.459(17) . ?
C12 H12A 0.9900 . ?
C12 H12B 0.9900 . ?
C13 H13A 0.9800 . ?
C13 H13B 0.9800 . ?
C13 H13C 0.9800 . ?
C14 C15 1.49(2) . ?
C14 H14A 0.9900 . ?
C14 H14B 0.9900 . ?
C15 C16 1.60(3) . ?
C15 H15A 0.9900 . ?
C15 H15B 0.9900 . ?
C15 H15A 0.9900 6 ?
C15 H15B 0.9900 6 ?
C16 C17 1.46(2) . ?
C16 H16A 0.9900 . ?
C16 H16B 0.9900 . ?
C17 H17A 0.9800 . ?
C17 H17B 0.9800 . ?
C17 H17C 0.9800 . ?
Se1 C5 1.816(14) . ?
Se1 C4 1.974(11) . ?
N1 C5 1.128(16) . ?
C1 C1 1.32(2) 6 ?
C1 C2 1.414(14) . ?
C1 H1 0.9500 . ?
C2 C3 1.383(13) . ?
C2 C4 1.446(16) . ?
C3 C3 1.36(2) 6 ?
C3 H3 0.9500 . ?
C4 H4A 0.9900 . ?
C4 H4B 0.9900 . ?

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
C10 N2 C10 108.3(11) 6 . ?
C10 N2 C14 110.0(7) 6 . ?
C10 N2 C14 110.0(7) . . ?
C10 N2 C6 111.0(7) 6 . ?
C10 N2 C6 111.0(7) . . ?
C14 N2 C6 106.5(11) . . ?
C7 C6 N2 114.5(11) . . ?
C7 C6 H6A 108.7 . . ?
N2 C6 H6A 108.6 . . ?
C7 C6 H6B 108.7 . . ?
N2 C6 H6B 108.6 . . ?
H6A C6 H6B 107.6 . . ?
C6 C7 C8 107.3(13) . . ?
C6 C7 H7A 110.3 . . ?
C8 C7 H7A 110.3 . . ?
C6 C7 H7B 110.3 . . ?
C8 C7 H7B 110.3 . . ?
H7A C7 H7B 108.5 . . ?
C9 C8 C7 109.8(15) . . ?
C9 C8 H8A 109.7 . . ?
C7 C8 H8A 109.7 . . ?
C9 C8 H8B 109.7 . . ?
C7 C8 H8B 109.7 . . ?
H8A C8 H8B 108.2 . . ?
C8 C9 H9A 109.5 . . ?
C8 C9 H9B 109.5 . . ?
H9A C9 H9B 109.5 . . ?
C8 C9 H9C 109.5 . . ?
H9A C9 H9C 109.5 . . ?
H9B C9 H9C 109.5 . . ?
C11 C10 N2 116.1(8) . . ?
C11 C10 H10A 108.3 . . ?
N2 C10 H10A 108.3 . . ?
C11 C10 H10B 108.3 . . ?
N2 C10 H10B 108.3 . . ?
H10A C10 H10B 107.4 . . ?
C12 C11 C10 113.7(11) . . ?
C12 C11 H11A 108.8 . . ?
C10 C11 H11A 108.8 . . ?
C12 C11 H11B 108.8 . . ?
C10 C11 H11B 108.8 . . ?
H11A C11 H11B 107.7 . . ?
C13 C12 C11 114.3(12) . . ?
C13 C12 H12A 108.7 . . ?
C11 C12 H12A 108.7 . . ?
C13 C12 H12B 108.7 . . ?
C11 C12 H12B 108.7 . . ?
H12A C12 H12B 107.6 . . ?
C12 C13 H13A 109.5 . . ?
C12 C13 H13B 109.5 . . ?
H13A C13 H13B 109.5 . . ?
C12 C13 H13C 109.5 . . ?
H13A C13 H13C 109.5 . . ?
H13B C13 H13C 109.5 . . ?
C15 C14 N2 113.3(12) . . ?
C15 C14 H14A 108.9 . . ?
N2 C14 H14A 108.9 . . ?
C15 C14 H14B 108.9 . . ?
N2 C14 H14B 108.9 . . ?
H14A C14 H14B 107.7 . . ?
C14 C15 C16 106.8(16) . . ?
C14 C15 H15A 110.4 . . ?
C16 C15 H15A 110.4 . . ?
C14 C15 H15B 110.4 . . ?
C16 C15 H15B 110.4 . . ?
H15A C15 H15B 108.6 . . ?
C14 C15 H15A 110.4(3) . 6 ?
C16 C15 H15A 90.0(15) . 6 ?
H15A C15 H15A 125.9 . 6 ?
H15B C15 H15A 22.0 . 6 ?
C14 C15 H15B 110.4(6) . 6 ?
C16 C15 H15B 128.4(13) . 6 ?
H15A C15 H15B 22.0 . 6 ?
H15B C15 H15B 88.8 . 6 ?
H15A C15 H15B 108.6 6 6 ?
C17 C16 C15 107(2) . . ?
C17 C16 H16A 110.4 . . ?
C15 C16 H16A 110.4 . . ?
C17 C16 H16B 110.4 . . ?
C15 C16 H16B 110.4 . . ?
H16A C16 H16B 108.6 . . ?
C16 C17 H17A 109.5 . . ?
C16 C17 H17B 109.5 . . ?
H17A C17 H17B 109.5 . . ?
C16 C17 H17C 109.5 . . ?
H17A C17 H17C 109.5 . . ?
H17B C17 H17C 109.5 . . ?
C5 Se1 C4 93.5(5) . . ?
C1 C1 C2 120.9(7) 6 . ?
C1 C1 H1 119.6 6 . ?
C2 C1 H1 119.6 . . ?
C3 C2 C1 118.4(11) . . ?
C3 C2 C4 121.6(10) . . ?
C1 C2 C4 120.1(10) . . ?
C3 C3 C2 120.8(7) 6 . ?
C3 C3 H3 119.6 6 . ?
C2 C3 H3 119.6 . . ?
C2 C4 Se1 113.1(8) . . ?
C2 C4 H4A 109.0 . . ?
Se1 C4 H4A 109.0 . . ?
C2 C4 H4B 109.0 . . ?
Se1 C4 H4B 109.0 . . ?
H4A C4 H4B 107.8 . . ?
N1 C5 Se1 176.3(17) . . ?

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
C10 N2 C6 C7 -60.3(7) 6 . . . ?
C10 N2 C6 C7 60.3(7) . . . . ?
C14 N2 C6 C7 180.000(2) . . . . ?
N2 C6 C7 C8 180.000(3) . . . . ?
C6 C7 C8 C9 180.000(4) . . . . ?
C10 N2 C10 C11 -179.4(8) 6 . . . ?
C14 N2 C10 C11 -59.1(13) . . . . ?
C6 N2 C10 C11 58.5(13) . . . . ?
N2 C10 C11 C12 -177.9(11) . . . . ?
C10 C11 C12 C13 177.4(14) . . . . ?
C10 N2 C14 C15 59.6(7) 6 . . . ?
C10 N2 C14 C15 -59.6(7) . . . . ?
C6 N2 C14 C15 180.000(2) . . . . ?
N2 C14 C15 C16 -168.2(16) . . . . ?
C14 C15 C16 C17 -150(3) . . . . ?
C1 C1 C2 C3 -0.8(11) 6 . . . ?
C1 C1 C2 C4 179.6(7) 6 . . . ?
C1 C2 C3 C3 0.8(11) . . . 6 ?
C4 C2 C3 C3 -179.7(7) . . . 6 ?
C3 C2 C4 Se1 102.5(10) . . . . ?
C1 C2 C4 Se1 -77.9(11) . . . . ?

_refine_diff_density_max         0.994
_refine_diff_density_min         -0.853
_refine_diff_density_rms         0.100











# start Validation Reply Form

_vrf_PLAT341_shelx               
;
PROBLEM: Low Bond Precision on  C-C Bonds ...............    0.01883 Ang.  
RESPONSE: One of the n-butyl chains is disordered
which causes high s.u.'s of its bond length values.
;

# end Validation Reply Form
####################################################################### 
# 
# 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_shelx_CCDC2
_database_code_depnum_ccdc_archive 'CCDC 1849845'
_audit_update_record             
;
2018-08-08 deposited with the CCDC.
2018-09-12 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2018/3
_shelx_SHELXL_version_number     2018/3
_chemical_name_systematic        ?
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         'C14 H10 N4 Se4, 2(C16 H36 N), 2(I)'
_chemical_formula_sum            'C46 H82 I2 N6 Se4'
_chemical_formula_weight         1288.81

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'
I I -0.4742 1.8119 '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/c'
_space_group_name_Hall           '-P 2ybc'

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

_cell_length_a                   12.145(4)
_cell_length_b                   8.651(2)
_cell_length_c                   26.550(8)
_cell_angle_alpha                90
_cell_angle_beta                 96.341(7)
_cell_angle_gamma                90
_cell_volume                     2772.5(15)
_cell_formula_units_Z            2
_cell_measurement_reflns_used    7389
_cell_measurement_temperature    200.0
_cell_measurement_theta_max      25.11
_cell_measurement_theta_min      2.16

_exptl_crystal_colour            'clear yellowish yellow'
_exptl_crystal_colour_lustre     clear
_exptl_crystal_colour_modifier   yellowish
_exptl_crystal_colour_primary    yellow
_exptl_crystal_description       plate

_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.544
_exptl_crystal_F_000             1284
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.240
_exptl_crystal_size_mid          0.180
_exptl_crystal_size_min          0.170
_exptl_absorpt_coefficient_mu    3.794
_shelx_estimated_absorpt_T_min   0.463
_shelx_estimated_absorpt_T_max   0.565
_exptl_absorpt_correction_T_max  0.7454
_exptl_absorpt_correction_T_min  0.6188
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   'SADABS, Bruker (2003)'
_exptl_absorpt_special_details   ?
_diffrn_ambient_temperature      200(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_source                   ?
_diffrn_measurement_device_type  'Bruker APEX-II CCD'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            29236
_diffrn_reflns_av_unetI/netI     0.0374
_diffrn_reflns_av_R_equivalents  0.0470
_diffrn_reflns_limit_h_min       -14
_diffrn_reflns_limit_h_max       14
_diffrn_reflns_limit_k_min       -10
_diffrn_reflns_limit_k_max       10
_diffrn_reflns_limit_l_min       -32
_diffrn_reflns_limit_l_max       32
_diffrn_reflns_theta_min         1.543
_diffrn_reflns_theta_max         25.999
_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             5450
_reflns_number_gt                3997
_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       'APEX II (Bruker, 2009)'
_computing_cell_refinement       'APEX II (Bruker, 2009)'
_computing_data_reduction        'SAINT (Bruker)'
_computing_structure_solution    'SHELXT 2014/5 (Sheldrick, 2014)'
_computing_structure_refinement  'SHELXL-2016/6 (Sheldrick, 2016)'
_computing_molecular_graphics    'Mercury (Macrae et al., 2008)'
_computing_publication_material  'CIFTAB (Sheldrick, 1997)'

_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)+(0.0369P)²+0.4769P] 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         5450
_refine_ls_number_parameters     266
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0554
_refine_ls_R_factor_gt           0.0322
_refine_ls_wR_factor_ref         0.0730
_refine_ls_wR_factor_gt          0.0679
_refine_ls_goodness_of_fit_ref   0.976
_refine_ls_restrained_S_all      0.976
_refine_ls_shift/su_max          0.002
_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
I1 I 0.39759(2) 0.47613(3) 0.66075(2) 0.04496(9) Uani 1 1 d . . . . .
Se1 Se 0.28652(3) 0.71817(4) 0.56499(2) 0.04409(11) Uani 1 1 d . . . . .
Se2 Se 0.16107(3) 0.25272(4) 0.62389(2) 0.04884(12) Uani 1 1 d . . . . .
N3 N 0.3608(2) 0.0099(3) 0.34600(9) 0.0275(6) Uani 1 1 d . . . . .
C2 C 0.0851(2) 0.4161(3) 0.52778(11) 0.0283(7) Uani 1 1 d . . . . .
C3 C 0.0689(2) 0.5729(3) 0.53868(12) 0.0285(7) Uani 1 1 d . . . . .
C12 C 0.2979(3) 0.1138(4) 0.37934(12) 0.0329(8) Uani 1 1 d . . . . .
H12A H 0.229506 0.059213 0.386299 0.040 Uiso 1 1 calc R U . . .
H12B H 0.343953 0.127690 0.412181 0.040 Uiso 1 1 calc R U . . .
C6 C 0.0151(3) 0.3473(4) 0.48940(11) 0.0295(7) Uani 1 1 d . . . . .
H6 H 0.025356 0.241093 0.482152 0.035 Uiso 1 1 calc R U . . .
C4 C 0.1372(3) 0.6547(4) 0.58124(12) 0.0320(7) Uani 1 1 d . . . . .
H4A H 0.145934 0.585717 0.611176 0.038 Uiso 1 1 calc R U . . .
H4B H 0.096537 0.747799 0.590517 0.038 Uiso 1 1 calc R U . . .
C17 C 0.5439(3) -0.0102(4) 0.30607(13) 0.0358(8) Uani 1 1 d . . . . .
H17A H 0.562451 -0.108059 0.324380 0.043 Uiso 1 1 calc R U . . .
H17B H 0.503243 -0.036327 0.272770 0.043 Uiso 1 1 calc R U . . .
C1 C 0.1782(3) 0.3229(4) 0.55422(12) 0.0357(8) Uani 1 1 d . . . . .
H1A H 0.246762 0.385300 0.555479 0.043 Uiso 1 1 calc R U . . .
H1B H 0.188905 0.230471 0.533306 0.043 Uiso 1 1 calc R U . . .
C20 C 0.2937(3) -0.0193(4) 0.29505(12) 0.0329(7) Uani 1 1 d . . . . .
H20A H 0.286840 0.079767 0.276299 0.039 Uiso 1 1 calc R U . . .
H20B H 0.336296 -0.090863 0.275486 0.039 Uiso 1 1 calc R U . . .
C16 C 0.4696(3) 0.0864(4) 0.33615(12) 0.0326(7) Uani 1 1 d . . . . .
H16A H 0.452305 0.184452 0.317710 0.039 Uiso 1 1 calc R U . . .
H16B H 0.511307 0.112815 0.369187 0.039 Uiso 1 1 calc R U . . .
C13 C 0.2655(3) 0.2726(4) 0.35833(12) 0.0353(8) Uani 1 1 d . . . . .
H13A H 0.332867 0.333316 0.353867 0.042 Uiso 1 1 calc R U . . .
H13B H 0.221333 0.262239 0.324864 0.042 Uiso 1 1 calc R U . . .
C8 C 0.3812(3) -0.1424(4) 0.37372(13) 0.0360(8) Uani 1 1 d . . . . .
H8A H 0.309397 -0.181274 0.382891 0.043 Uiso 1 1 calc R U . . .
H8B H 0.408621 -0.217945 0.350030 0.043 Uiso 1 1 calc R U . . .
C9 C 0.4619(3) -0.1377(4) 0.42103(13) 0.0393(8) Uani 1 1 d . . . . .
H9A H 0.442850 -0.050677 0.442670 0.047 Uiso 1 1 calc R U . . .
H9B H 0.537575 -0.119738 0.411689 0.047 Uiso 1 1 calc R U . . .
C10 C 0.4599(3) -0.2875(4) 0.45054(12) 0.0426(9) Uani 1 1 d . . . . .
H10A H 0.383236 -0.308692 0.457948 0.051 Uiso 1 1 calc R U . . .
H10B H 0.483356 -0.373561 0.429566 0.051 Uiso 1 1 calc R U . . .
C22 C 0.1261(3) -0.1142(4) 0.24281(14) 0.0476(9) Uani 1 1 d . . . . .
H22A H 0.177325 -0.176420 0.224497 0.057 Uiso 1 1 calc R U . . .
H22B H 0.114690 -0.013888 0.225022 0.057 Uiso 1 1 calc R U . . .
C21 C 0.1791(3) -0.0852(4) 0.29615(14) 0.0426(9) Uani 1 1 d . . . . .
H21A H 0.133105 -0.011976 0.313406 0.051 Uiso 1 1 calc R U . . .
H21B H 0.183606 -0.183400 0.315430 0.051 Uiso 1 1 calc R U . . .
C7 C 0.0512(4) 0.1081(5) 0.60659(16) 0.0561(11) Uani 1 1 d . . . . .
C5 C 0.2378(3) 0.8707(5) 0.51842(15) 0.0516(10) Uani 1 1 d . . . . .
N1 N 0.2201(4) 0.9693(4) 0.49042(15) 0.0746(11) Uani 1 1 d . . . . .
C14 C 0.1983(3) 0.3546(4) 0.39477(15) 0.0484(10) Uani 1 1 d . . . . .
H14A H 0.131298 0.292407 0.398562 0.058 Uiso 1 1 calc R U . . .
H14B H 0.242571 0.359377 0.428357 0.058 Uiso 1 1 calc R U . . .
N2 N -0.0127(4) 0.0106(4) 0.60131(18) 0.0840(13) Uani 1 1 d . . . . .
C19 C 0.7153(3) -0.0106(4) 0.26176(16) 0.0556(11) Uani 1 1 d . . . . .
H19A H 0.675570 -0.007453 0.227577 0.083 Uiso 1 1 calc R U . . .
H19B H 0.726227 -0.118394 0.272516 0.083 Uiso 1 1 calc R U . . .
H19C H 0.787455 0.039981 0.261632 0.083 Uiso 1 1 calc R U . . .
C18 C 0.6487(3) 0.0724(4) 0.29792(16) 0.0544(11) Uani 1 1 d . . . . .
H18A H 0.694455 0.084300 0.330926 0.065 Uiso 1 1 calc R U . . .
H18B H 0.630114 0.177152 0.284562 0.065 Uiso 1 1 calc R U . . .
C11 C 0.5356(3) -0.2809(4) 0.49980(14) 0.0519(10) Uani 1 1 d . . . . .
H11A H 0.611495 -0.259414 0.492617 0.078 Uiso 1 1 calc R U . . .
H11B H 0.533479 -0.380256 0.517394 0.078 Uiso 1 1 calc R U . . .
H11C H 0.510647 -0.198686 0.521277 0.078 Uiso 1 1 calc R U . . .
C15 C 0.1631(3) 0.5150(4) 0.37928(17) 0.0588(11) Uani 1 1 d . . . . .
H15A H 0.110012 0.510568 0.348725 0.088 Uiso 1 1 calc R U . . .
H15B H 0.228095 0.575127 0.372256 0.088 Uiso 1 1 calc R U . . .
H15C H 0.128273 0.564309 0.406723 0.088 Uiso 1 1 calc R U . . .
C23 C 0.0160(3) -0.1976(5) 0.24095(19) 0.0761(14) Uani 1 1 d . . . . .
H23A H -0.015800 -0.209269 0.205595 0.114 Uiso 1 1 calc R U . . .
H23B H -0.034779 -0.137524 0.259520 0.114 Uiso 1 1 calc R U . . .
H23C H 0.027374 -0.299839 0.256531 0.114 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 1.860(4) . ?
Se1 C4 1.988(3) . ?
Se2 C7 1.850(5) . ?
Se2 C1 1.979(3) . ?
N3 C8 1.516(4) . ?
N3 C20 1.521(4) . ?
N3 C12 1.525(4) . ?
N3 C16 1.526(4) . ?
C2 C6 1.387(4) . ?
C2 C3 1.405(4) . ?
C2 C1 1.499(4) . ?
C3 C6 1.380(4) 3_566 ?
C3 C4 1.503(4) . ?
C12 C13 1.519(4) . ?
C17 C18 1.496(5) . ?
C17 C16 1.520(4) . ?
C20 C21 1.507(5) . ?
C13 C14 1.510(5) . ?
C8 C9 1.506(4) . ?
C9 C10 1.516(4) . ?
C10 C11 1.514(5) . ?
C22 C21 1.510(5) . ?
C22 C23 1.516(5) . ?
C7 N2 1.145(5) . ?
C5 N1 1.136(5) . ?
C14 C15 1.496(5) . ?
C19 C18 1.505(5) . ?

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 Se1 C4 96.29(16) . . ?
C7 Se2 C1 97.05(16) . . ?
C8 N3 C20 109.3(2) . . ?
C8 N3 C12 107.2(2) . . ?
C20 N3 C12 111.1(2) . . ?
C8 N3 C16 111.2(2) . . ?
C20 N3 C16 108.0(2) . . ?
C12 N3 C16 110.0(2) . . ?
C6 C2 C3 118.5(3) . . ?
C6 C2 C1 118.9(3) . . ?
C3 C2 C1 122.6(3) . . ?
C6 C3 C2 118.9(3) 3_566 . ?
C6 C3 C4 119.0(3) 3_566 . ?
C2 C3 C4 122.1(3) . . ?
C13 C12 N3 116.5(2) . . ?
C3 C6 C2 122.6(3) 3_566 . ?
C3 C4 Se1 114.1(2) . . ?
C18 C17 C16 112.2(3) . . ?
C2 C1 Se2 116.8(2) . . ?
C21 C20 N3 116.8(3) . . ?
C17 C16 N3 115.3(3) . . ?
C14 C13 C12 109.0(3) . . ?
C9 C8 N3 116.0(3) . . ?
C8 C9 C10 111.2(3) . . ?
C11 C10 C9 111.8(3) . . ?
C21 C22 C23 113.1(3) . . ?
C20 C21 C22 110.1(3) . . ?
N2 C7 Se2 171.8(4) . . ?
N1 C5 Se1 172.3(4) . . ?
C15 C14 C13 114.7(3) . . ?
C17 C18 C19 113.0(3) . . ?

_refine_diff_density_max         1.000
_refine_diff_density_min         -0.401
_refine_diff_density_rms         0.078

####################################################################### 
# 
# 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_db252_red_a
_database_code_depnum_ccdc_archive 'CCDC 1849846'
_audit_update_record             
;
2018-08-08 deposited with the CCDC.
2018-09-12 downloaded from the CCDC.
;
_audit_creation_date             2018-06-19
_audit_creation_method           
;
Olex2 1.2
(compiled 2018.05.29 svn.r3508 for OlexSys, GUI svn.r5506)
;
_shelx_SHELXL_version_number     2018/3
_chemical_name_common            ?
_chemical_name_systematic        ?
_chemical_formula_moiety         'Br, C5 H4 N Se, C16 H36 N'
_chemical_formula_sum            'C21 H40 Br N2 Se'
_chemical_formula_weight         479.42
_chemical_melting_point          ?
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'
Br Br -0.2901 2.4595 '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'

_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.
;
_space_group_crystal_system      monoclinic
_space_group_IT_number           14
_space_group_name_H-M_alt        'P 1 21/c 1'
_space_group_name_Hall           '-P 2ybc'
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x, y+1/2, -z+1/2'
'-x, -y, -z'
'x, -y-1/2, z-1/2'

_cell_length_a                   7.8550(12)
_cell_length_b                   14.479(2)
_cell_length_c                   21.667(3)
_cell_angle_alpha                90
_cell_angle_beta                 90.775(3)
_cell_angle_gamma                90
_cell_volume                     2464.1(6)
_cell_formula_units_Z            4
_cell_measurement_reflns_used    5749
_cell_measurement_temperature    200.0
_cell_measurement_theta_max      21.19
_cell_measurement_theta_min      2.59
_shelx_estimated_absorpt_T_max   0.649
_shelx_estimated_absorpt_T_min   0.518
_exptl_absorpt_coefficient_mu    3.152
_exptl_absorpt_correction_T_max  0.7456
_exptl_absorpt_correction_T_min  0.5652
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
'SADABS-2016/2 (Bruker,2016/2) was used for absorption correction. wR2(int) was 0.1205 before and 0.0533 after correction. The Ratio of minimum to maximum transmission is 0.7580. The λ/2 correction factor is Not present.'
_exptl_absorpt_special_details   ?
_exptl_crystal_colour            'clear light yellow'
_exptl_crystal_colour_lustre     clear
_exptl_crystal_colour_modifier   light
_exptl_crystal_colour_primary    yellow
_exptl_crystal_density_diffrn    1.292
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       plate
_exptl_crystal_F_000             996
_exptl_crystal_preparation       cocrystallization
_exptl_crystal_recrystallization_method 'solvent evaporation'
_exptl_crystal_size_max          0.24
_exptl_crystal_size_mid          0.21
_exptl_crystal_size_min          0.15
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.1153
_diffrn_reflns_av_unetI/netI     0.0620
_diffrn_reflns_Laue_measured_fraction_full 1.000
_diffrn_reflns_Laue_measured_fraction_max 1.000
_diffrn_reflns_limit_h_max       9
_diffrn_reflns_limit_h_min       -9
_diffrn_reflns_limit_k_max       17
_diffrn_reflns_limit_k_min       -17
_diffrn_reflns_limit_l_max       25
_diffrn_reflns_limit_l_min       -25
_diffrn_reflns_number            35719
_diffrn_reflns_point_group_measured_fraction_full 1.000
_diffrn_reflns_point_group_measured_fraction_max 1.000
_diffrn_reflns_theta_full        25.000
_diffrn_reflns_theta_max         25.000
_diffrn_reflns_theta_min         1.692
_diffrn_ambient_temperature      200.0
_diffrn_detector_area_resol_mean 5.6
_diffrn_detector_type            'Bruker SMART CCD 6000 area detector'
_diffrn_measured_fraction_theta_full 1.000
_diffrn_measured_fraction_theta_max 1.000
_diffrn_measurement_device       'three-circle diffractometer'
_diffrn_measurement_device_type  'Bruker SMART CCD 6000 area detector'
_diffrn_measurement_method       'ω scans'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_source                   ?
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_full    .
_reflns_Friedel_fraction_max     .
_reflns_number_gt                2536
_reflns_number_total             4343
_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.
;
_reflns_threshold_expression     'I > 2σ(I)'
_computing_cell_refinement       'SAINT v8.37A (Bruker, 2015)'
_computing_data_collection       ?
_computing_data_reduction        'SAINT v8.37A (Bruker, 2015)'
_computing_molecular_graphics    'Olex2 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 (Dolomanov et al., 2009)'
_computing_structure_refinement  'ShelXL (Sheldrick, 2015)'
_computing_structure_solution    'ShelXS (Sheldrick, 2008)'
_refine_diff_density_max         1.206
_refine_diff_density_min         -0.538
_refine_diff_density_rms         0.101
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   0.901
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     230
_refine_ls_number_reflns         4343
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.1103
_refine_ls_R_factor_gt           0.0571
_refine_ls_restrained_S_all      0.901
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.1036P)²] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1463
_refine_ls_wR_factor_ref         0.1633
_refine_special_details          ?
_olex2_refinement_description    
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups, All C(H,H) groups
 At 1.5 times of:
  All C(H,H,H) groups
2.a Secondary CH2 refined with riding coordinates:
 C1(H1A,H1B), C10(H10A,H10B), C18(H18A,H18B), C14(H14A,H14B), C11(H11A,H11B),
 C6(H6A,H6B), C20(H20A,H20B), C7(H7A,H7B), C12(H12A,H12B), C16(H16A,H16B),
 C8(H8A,H8B), C19(H19A,H19B), C15(H15A,H15B)
2.b Aromatic/amide H refined with riding coordinates:
 C3(H3), C4(H4)
2.c Idealised Me refined as rotating group:
 C9(H9A,H9B,H9C), C17(H17A,H17B,H17C), C13(H13A,H13B,H13C), C21(H21A,H21B,H21C)
;
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   ?
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
Br1 Br 0.79349(8) 0.08707(5) 0.74665(3) 0.0712(3) Uani 1 1 d . . . . .
Se1 Se 0.66494(7) 0.14480(4) 0.60880(3) 0.0526(2) Uani 1 1 d . . . . .
N2 N 0.3107(5) 0.2781(3) 0.31958(19) 0.0444(11) Uani 1 1 d . . . . .
N1 N 0.5293(7) 0.1824(4) 0.4807(3) 0.0719(15) Uani 1 1 d . . . . .
C2 C 0.8690(7) 0.0094(4) 0.5435(2) 0.0451(13) Uani 1 1 d . . . . .
C1 C 0.7302(7) 0.0159(4) 0.5904(3) 0.0517(14) Uani 1 1 d . . . . .
H1A H 0.769058 -0.014479 0.629018 0.062 Uiso 1 1 calc R . . . .
H1B H 0.628862 -0.017950 0.574816 0.062 Uiso 1 1 calc R . . . .
C10 C 0.1338(6) 0.2736(4) 0.3472(2) 0.0487(14) Uani 1 1 d . . . . .
H10A H 0.068515 0.224516 0.325575 0.058 Uiso 1 1 calc R . . . .
H10B H 0.075240 0.332894 0.338813 0.058 Uiso 1 1 calc R . . . .
C18 C 0.3977(7) 0.1860(4) 0.3267(3) 0.0488(14) Uani 1 1 d . . . . .
H18A H 0.408992 0.172414 0.371358 0.059 Uiso 1 1 calc R . . . .
H18B H 0.322541 0.138178 0.308386 0.059 Uiso 1 1 calc R . . . .
C3 C 1.0376(7) 0.0259(4) 0.5597(2) 0.0530(15) Uani 1 1 d . . . . .
H3 H 1.065336 0.043354 0.600893 0.064 Uiso 1 1 calc R . . . .
C5 C 0.5815(7) 0.1664(4) 0.5290(3) 0.0552(15) Uani 1 1 d . . . . .
C14 C 0.2909(7) 0.3023(4) 0.2513(2) 0.0539(15) Uani 1 1 d . . . . .
H14A H 0.223039 0.359748 0.247647 0.065 Uiso 1 1 calc R . . . .
H14B H 0.404982 0.315144 0.234486 0.065 Uiso 1 1 calc R . . . .
C11 C 0.1277(7) 0.2548(4) 0.4163(2) 0.0571(15) Uani 1 1 d . . . . .
H11A H 0.178932 0.193710 0.425291 0.069 Uiso 1 1 calc R . . . .
H11B H 0.195101 0.302237 0.438703 0.069 Uiso 1 1 calc R . . . .
C6 C 0.4211(7) 0.3509(4) 0.3515(3) 0.0515(14) Uani 1 1 d . . . . .
H6A H 0.451204 0.328160 0.393345 0.062 Uiso 1 1 calc R . . . .
H6B H 0.528373 0.356838 0.328367 0.062 Uiso 1 1 calc R . . . .
C4 C 1.1659(7) 0.0175(4) 0.5172(3) 0.0528(15) Uani 1 1 d . . . . .
H4 H 1.280051 0.030361 0.529499 0.063 Uiso 1 1 calc R . . . .
C20 C 0.6426(8) 0.0805(4) 0.3093(3) 0.0594(16) Uani 1 1 d . . . . .
H20A H 0.642884 0.066727 0.354093 0.071 Uiso 1 1 calc R . . . .
H20B H 0.568740 0.034422 0.288381 0.071 Uiso 1 1 calc R . . . .
C7 C 0.3443(8) 0.4452(4) 0.3577(3) 0.0642(17) Uani 1 1 d . . . . .
H7A H 0.237565 0.441186 0.381335 0.077 Uiso 1 1 calc R . . . .
H7B H 0.316462 0.470293 0.316264 0.077 Uiso 1 1 calc R . . . .
C12 C -0.0551(8) 0.2564(5) 0.4386(3) 0.0670(18) Uani 1 1 d . . . . .
H12A H -0.124990 0.215585 0.411820 0.080 Uiso 1 1 calc R . . . .
H12B H -0.057952 0.231043 0.481038 0.080 Uiso 1 1 calc R . . . .
C9 C 0.4010(12) 0.6019(6) 0.4018(5) 0.118(3) Uani 1 1 d . . . . .
H9A H 0.373382 0.631222 0.362119 0.176 Uiso 1 1 calc GR . . . .
H9B H 0.486000 0.639212 0.423992 0.176 Uiso 1 1 calc GR . . . .
H9C H 0.297770 0.597202 0.426457 0.176 Uiso 1 1 calc GR . . . .
C16 C 0.1844(10) 0.2557(6) 0.1468(3) 0.094(3) Uani 1 1 d . . . . .
H16A H 0.297054 0.272748 0.130285 0.113 Uiso 1 1 calc R . . . .
H16B H 0.111063 0.311262 0.144799 0.113 Uiso 1 1 calc R . . . .
C17 C 0.1074(11) 0.1819(7) 0.1066(3) 0.117(3) Uani 1 1 d . . . . .
H17A H 0.176639 0.125777 0.109646 0.175 Uiso 1 1 calc GR . . . .
H17B H 0.103670 0.203217 0.063707 0.175 Uiso 1 1 calc GR . . . .
H17C H -0.008432 0.168628 0.120338 0.175 Uiso 1 1 calc GR . . . .
C8 C 0.4699(9) 0.5090(5) 0.3909(4) 0.096(3) Uani 1 1 d . . . . .
H8A H 0.502621 0.481053 0.431020 0.115 Uiso 1 1 calc R . . . .
H8B H 0.574168 0.514379 0.365946 0.115 Uiso 1 1 calc R . . . .
C13 C -0.1328(9) 0.3501(6) 0.4388(3) 0.089(3) Uani 1 1 d . . . . .
H13A H -0.065979 0.390816 0.465976 0.134 Uiso 1 1 calc GR . . . .
H13B H -0.249727 0.346165 0.453749 0.134 Uiso 1 1 calc GR . . . .
H13C H -0.133732 0.375185 0.396775 0.134 Uiso 1 1 calc GR . . . .
C21 C 0.8216(8) 0.0716(5) 0.2855(3) 0.074(2) Uani 1 1 d . . . . .
H21A H 0.824747 0.093116 0.242625 0.112 Uiso 1 1 calc GR . . . .
H21B H 0.857200 0.006811 0.287401 0.112 Uiso 1 1 calc GR . . . .
H21C H 0.898907 0.109210 0.310936 0.112 Uiso 1 1 calc GR . . . .
C19 C 0.5697(7) 0.1768(4) 0.2986(3) 0.0599(16) Uani 1 1 d . . . . .
H19A H 0.647626 0.223323 0.316912 0.072 Uiso 1 1 calc R . . . .
H19B H 0.560793 0.188805 0.253680 0.072 Uiso 1 1 calc R . . . .
C15 C 0.2058(9) 0.2276(5) 0.2120(3) 0.0714(19) Uani 1 1 d . . . . .
H15A H 0.275449 0.170711 0.214061 0.086 Uiso 1 1 calc R . . . .
H15B H 0.092690 0.213247 0.229225 0.086 Uiso 1 1 calc R . . . .


_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 1.978(6) . ?
Se1 C5 1.867(7) . ?
N2 C10 1.522(6) . ?
N2 C18 1.505(7) . ?
N2 C14 1.526(6) . ?
N2 C6 1.525(7) . ?
N1 C5 1.144(7) . ?
C2 C1 1.503(7) . ?
C2 C3 1.387(7) . ?
C2 C4 1.395(7) 3_756 ?
C1 H1A 0.9900 . ?
C1 H1B 0.9900 . ?
C10 H10A 0.9900 . ?
C10 H10B 0.9900 . ?
C10 C11 1.523(7) . ?
C18 H18A 0.9900 . ?
C18 H18B 0.9900 . ?
C18 C19 1.495(8) . ?
C3 H3 0.9500 . ?
C3 C4 1.379(7) . ?
C14 H14A 0.9900 . ?
C14 H14B 0.9900 . ?
C14 C15 1.526(9) . ?
C11 H11A 0.9900 . ?
C11 H11B 0.9900 . ?
C11 C12 1.522(8) . ?
C6 H6A 0.9900 . ?
C6 H6B 0.9900 . ?
C6 C7 1.499(8) . ?
C4 H4 0.9500 . ?
C20 H20A 0.9900 . ?
C20 H20B 0.9900 . ?
C20 C21 1.509(8) . ?
C20 C19 1.524(8) . ?
C7 H7A 0.9900 . ?
C7 H7B 0.9900 . ?
C7 C8 1.526(9) . ?
C12 H12A 0.9900 . ?
C12 H12B 0.9900 . ?
C12 C13 1.488(9) . ?
C9 H9A 0.9800 . ?
C9 H9B 0.9800 . ?
C9 H9C 0.9800 . ?
C9 C8 1.470(10) . ?
C16 H16A 0.9900 . ?
C16 H16B 0.9900 . ?
C16 C17 1.500(11) . ?
C16 C15 1.478(9) . ?
C17 H17A 0.9800 . ?
C17 H17B 0.9800 . ?
C17 H17C 0.9800 . ?
C8 H8A 0.9900 . ?
C8 H8B 0.9900 . ?
C13 H13A 0.9800 . ?
C13 H13B 0.9800 . ?
C13 H13C 0.9800 . ?
C21 H21A 0.9800 . ?
C21 H21B 0.9800 . ?
C21 H21C 0.9800 . ?
C19 H19A 0.9900 . ?
C19 H19B 0.9900 . ?
C15 H15A 0.9900 . ?
C15 H15B 0.9900 . ?

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 Se1 C1 93.4(2) . . ?
C10 N2 C14 108.0(4) . . ?
C10 N2 C6 111.6(4) . . ?
C18 N2 C10 109.7(4) . . ?
C18 N2 C14 110.1(4) . . ?
C18 N2 C6 108.1(4) . . ?
C6 N2 C14 109.3(4) . . ?
C3 C2 C1 121.1(5) . . ?
C3 C2 C4 117.5(5) . 3_756 ?
C4 C2 C1 121.3(5) 3_756 . ?
Se1 C1 H1A 109.0 . . ?
Se1 C1 H1B 109.0 . . ?
C2 C1 Se1 112.8(4) . . ?
C2 C1 H1A 109.0 . . ?
C2 C1 H1B 109.0 . . ?
H1A C1 H1B 107.8 . . ?
N2 C10 H10A 108.3 . . ?
N2 C10 H10B 108.3 . . ?
N2 C10 C11 115.8(4) . . ?
H10A C10 H10B 107.4 . . ?
C11 C10 H10A 108.3 . . ?
C11 C10 H10B 108.3 . . ?
N2 C18 H18A 108.1 . . ?
N2 C18 H18B 108.1 . . ?
H18A C18 H18B 107.3 . . ?
C19 C18 N2 116.7(5) . . ?
C19 C18 H18A 108.1 . . ?
C19 C18 H18B 108.1 . . ?
C2 C3 H3 119.3 . . ?
C4 C3 C2 121.3(5) . . ?
C4 C3 H3 119.3 . . ?
N1 C5 Se1 177.9(6) . . ?
N2 C14 H14A 108.6 . . ?
N2 C14 H14B 108.6 . . ?
H14A C14 H14B 107.6 . . ?
C15 C14 N2 114.6(5) . . ?
C15 C14 H14A 108.6 . . ?
C15 C14 H14B 108.6 . . ?
C10 C11 H11A 109.5 . . ?
C10 C11 H11B 109.5 . . ?
H11A C11 H11B 108.1 . . ?
C12 C11 C10 110.6(5) . . ?
C12 C11 H11A 109.5 . . ?
C12 C11 H11B 109.5 . . ?
N2 C6 H6A 108.2 . . ?
N2 C6 H6B 108.2 . . ?
H6A C6 H6B 107.4 . . ?
C7 C6 N2 116.3(5) . . ?
C7 C6 H6A 108.2 . . ?
C7 C6 H6B 108.2 . . ?
C2 C4 H4 119.4 3_756 . ?
C3 C4 C2 121.2(5) . 3_756 ?
C3 C4 H4 119.4 . . ?
H20A C20 H20B 107.9 . . ?
C21 C20 H20A 109.2 . . ?
C21 C20 H20B 109.2 . . ?
C21 C20 C19 112.0(5) . . ?
C19 C20 H20A 109.2 . . ?
C19 C20 H20B 109.2 . . ?
C6 C7 H7A 109.8 . . ?
C6 C7 H7B 109.8 . . ?
C6 C7 C8 109.6(5) . . ?
H7A C7 H7B 108.2 . . ?
C8 C7 H7A 109.8 . . ?
C8 C7 H7B 109.8 . . ?
C11 C12 H12A 108.8 . . ?
C11 C12 H12B 108.8 . . ?
H12A C12 H12B 107.7 . . ?
C13 C12 C11 113.8(6) . . ?
C13 C12 H12A 108.8 . . ?
C13 C12 H12B 108.8 . . ?
H9A C9 H9B 109.5 . . ?
H9A C9 H9C 109.5 . . ?
H9B C9 H9C 109.5 . . ?
C8 C9 H9A 109.5 . . ?
C8 C9 H9B 109.5 . . ?
C8 C9 H9C 109.5 . . ?
H16A C16 H16B 107.7 . . ?
C17 C16 H16A 108.9 . . ?
C17 C16 H16B 108.9 . . ?
C15 C16 H16A 108.9 . . ?
C15 C16 H16B 108.9 . . ?
C15 C16 C17 113.5(7) . . ?
C16 C17 H17A 109.5 . . ?
C16 C17 H17B 109.5 . . ?
C16 C17 H17C 109.5 . . ?
H17A C17 H17B 109.5 . . ?
H17A C17 H17C 109.5 . . ?
H17B C17 H17C 109.5 . . ?
C7 C8 H8A 109.0 . . ?
C7 C8 H8B 109.0 . . ?
C9 C8 C7 113.1(7) . . ?
C9 C8 H8A 109.0 . . ?
C9 C8 H8B 109.0 . . ?
H8A C8 H8B 107.8 . . ?
C12 C13 H13A 109.5 . . ?
C12 C13 H13B 109.5 . . ?
C12 C13 H13C 109.5 . . ?
H13A C13 H13B 109.5 . . ?
H13A C13 H13C 109.5 . . ?
H13B C13 H13C 109.5 . . ?
C20 C21 H21A 109.5 . . ?
C20 C21 H21B 109.5 . . ?
C20 C21 H21C 109.5 . . ?
H21A C21 H21B 109.5 . . ?
H21A C21 H21C 109.5 . . ?
H21B C21 H21C 109.5 . . ?
C18 C19 C20 111.1(5) . . ?
C18 C19 H19A 109.4 . . ?
C18 C19 H19B 109.4 . . ?
C20 C19 H19A 109.4 . . ?
C20 C19 H19B 109.4 . . ?
H19A C19 H19B 108.0 . . ?
C14 C15 H15A 109.1 . . ?
C14 C15 H15B 109.1 . . ?
C16 C15 C14 112.5(6) . . ?
C16 C15 H15A 109.1 . . ?
C16 C15 H15B 109.1 . . ?
H15A C15 H15B 107.8 . . ?

_olex2_submission_special_instructions 'No special instructions were received'
