# Electronic Supplementary Material (ESI) for Dalton Transactions.
# This journal is © The Royal Society of Chemistry 2014

#######################################################################
#
#                 Cambridge Crystallographic Data Centre
#                                CCDC 
# 
#######################################################################
# 
#  This CIF contains data from an original supplementary publication
#  deposited with the CCDC, and may include chemical, crystal,
#  experimental, refinement, atomic coordinates,
#  anisotropic displacement parameters and molecular geometry data,
#  as required by the journal to which it was submitted.
#
#  This CIF is provided on the understanding that it is used for bona
#  fide research purposes only. It may contain copyright material
#  of the CCDC or of third parties, and may not be copied or further
#  disseminated in any form, whether machine-readable or not,
#  except for the purpose of generating routine backup copies
#  on your local computer system.
# 
#  For further information on the CCDC, data deposition and
#  data retrieval see:
#                         www.ccdc.cam.ac.uk
#
#  Bona fide researchers may freely download Mercury and enCIFer
#  from this site to visualise CIF-encoded structures and 
#  to carry out CIF format checking respectively.
#
data_diisose2

_audit_creation_method           SHELXL-97
_chemical_name_systematic        
; 
 ? 
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         'C38 H44 N2 Se'
_chemical_formula_sum            'C38 H44 N2 Se'
_chemical_formula_weight         607.71

loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0181 0.0091 '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 0.0311 0.0180 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
Se Se -0.7943 1.1372 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_symmetry_cell_setting           triclinic
_symmetry_space_group_name_H-M   'P -1'

loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'-x, -y, -z'

_cell_length_a                   9.6138(3)
_cell_length_b                   11.1782(5)
_cell_length_c                   17.0830(7)
_cell_angle_alpha                89.666(3)
_cell_angle_beta                 75.815(3)
_cell_angle_gamma                65.343(3)
_cell_volume                     1607.85(11)
_cell_formula_units_Z            2
_cell_measurement_temperature    123(2)
_cell_measurement_reflns_used    7276
_cell_measurement_theta_min      2.6818
_cell_measurement_theta_max      75.4797

_exptl_crystal_description       prism
_exptl_crystal_colour            colorless
_exptl_crystal_size_max          0.35
_exptl_crystal_size_mid          0.17
_exptl_crystal_size_min          0.12
_exptl_crystal_density_meas      ?
_exptl_crystal_density_diffrn    1.255
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             640
_exptl_absorpt_coefficient_mu    1.778
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.96193
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_process_details   
;
CrysAlisPro, Agilent Technologies,
Version 1.171.35.11 (release 16-05-2011 CrysAlis171 .NET)
(compiled May 16 2011,17:55:39)
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;

_exptl_special_details           
; 
 ? 
;

_diffrn_ambient_temperature      123(2)
_diffrn_radiation_wavelength     1.54184
_diffrn_radiation_type           CuK\a
_diffrn_radiation_source         'Enhance (Cu) X-ray Source'
_diffrn_radiation_monochromator  graphite
_diffrn_measurement_device_type  'Xcalibur, Ruby, Gemini'
_diffrn_measurement_method       'ω scans'
_diffrn_detector_area_resol_mean 10.5081
_diffrn_standards_number         ?
_diffrn_standards_interval_count ?
_diffrn_standards_interval_time  ?
_diffrn_standards_decay_%        ?
_diffrn_reflns_number            11196
_diffrn_reflns_av_R_equivalents  0.0295
_diffrn_reflns_av_sigmaI/netI    0.0350
_diffrn_reflns_limit_h_min       -8
_diffrn_reflns_limit_h_max       12
_diffrn_reflns_limit_k_min       -14
_diffrn_reflns_limit_k_max       13
_diffrn_reflns_limit_l_min       -20
_diffrn_reflns_limit_l_max       21
_diffrn_reflns_theta_min         2.68
_diffrn_reflns_theta_max         75.66
_reflns_number_total             6460
_reflns_number_gt                6010
_reflns_threshold_expression     >2sigma(I)

_computing_data_collection       
;
CrysAlisPro, Agilent Technologies,
Version 1.171.35.11 (release 16-05-2011 CrysAlis171 .NET)
(compiled May 16 2011,17:55:39)
;
_computing_cell_refinement       
;
CrysAlisPro, Agilent Technologies,
Version 1.171.35.11 (release 16-05-2011 CrysAlis171 .NET)
(compiled May 16 2011,17:55:39)
;
_computing_data_reduction        
;
CrysAlisPro, Agilent Technologies,
Version 1.171.35.11 (release 16-05-2011 CrysAlis171 .NET)
(compiled May 16 2011,17:55:39)
;
_computing_structure_solution    'SHELXS-97 (Sheldrick, 2008)'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 2008)'
_computing_molecular_graphics    'SHELXTL (Sheldrick, 2008)'
_computing_publication_material  'SHELXTL (Sheldrick, 2008)'

_refine_special_details          
; 
 Refinement of F² against ALL reflections.  The weighted R-factor wR and 
 goodness of fit S are based on F², conventional R-factors R are based 
 on F, with F set to zero for negative F². The threshold expression of 
 F² > 2sigma(F²) is used only for calculating R-factors(gt) etc. and is 
 not relevant to the choice of reflections for refinement.  R-factors based 
 on F² are statistically about twice as large as those based on F, and R- 
 factors based on ALL data will be even larger. 
;

_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'calc w=1/[σ²(Fo²)+(0.0428P)²+0.5390P] 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_number_reflns         6460
_refine_ls_number_parameters     378
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0350
_refine_ls_R_factor_gt           0.0323
_refine_ls_wR_factor_ref         0.0834
_refine_ls_wR_factor_gt          0.0814
_refine_ls_goodness_of_fit_ref   1.039
_refine_ls_restrained_S_all      1.039
_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_symmetry_multiplicity
_atom_site_calc_flag
_atom_site_refinement_flags
_atom_site_disorder_assembly
_atom_site_disorder_group
Se Se 0.197558(19) 0.254791(17) 0.847419(10) 0.02340(7) Uani 1 1 d . . .
N1A N 0.44061(17) 0.48979(14) 0.89082(8) 0.0247(3) Uani 1 1 d . . .
C1A C 0.18225(18) 0.32571(16) 0.95341(9) 0.0217(3) Uani 1 1 d . . .
C2A C 0.0995(2) 0.29185(17) 1.02237(11) 0.0266(3) Uani 1 1 d . . .
H2AA H 0.0472 0.2379 1.0168 0.032 Uiso 1 1 calc R . .
C3A C 0.0938(2) 0.33715(19) 1.09917(11) 0.0303(4) Uani 1 1 d . . .
H3AA H 0.0345 0.3166 1.1460 0.036 Uiso 1 1 calc R . .
C4A C 0.1744(2) 0.41248(18) 1.10783(10) 0.0296(4) Uani 1 1 d . . .
H4AA H 0.1744 0.4397 1.1604 0.036 Uiso 1 1 calc R . .
C5A C 0.2549(2) 0.44774(17) 1.03956(10) 0.0253(3) Uani 1 1 d . . .
H5AA H 0.3091 0.4999 1.0455 0.030 Uiso 1 1 calc R . .
C6A C 0.25666(18) 0.40697(15) 0.96182(10) 0.0214(3) Uani 1 1 d . . .
C7A C 0.33085(19) 0.45529(16) 0.89034(10) 0.0228(3) Uani 1 1 d . . .
H7AA H 0.2953 0.4607 0.8427 0.027 Uiso 1 1 calc R . .
C8A C 0.4930(2) 0.55212(17) 0.82413(10) 0.0243(3) Uani 1 1 d . . .
C9A C 0.4223(2) 0.69123(18) 0.83098(11) 0.0271(3) Uani 1 1 d . . .
C10A C 0.4890(2) 0.75350(19) 0.77256(12) 0.0338(4) Uani 1 1 d . . .
H10A H 0.4449 0.8475 0.7769 0.041 Uiso 1 1 calc R . .
C11A C 0.6188(3) 0.6802(2) 0.70825(12) 0.0367(4) Uani 1 1 d . . .
H11A H 0.6652 0.7239 0.6699 0.044 Uiso 1 1 calc R . .
C12A C 0.6808(2) 0.5433(2) 0.69990(11) 0.0334(4) Uani 1 1 d . . .
H12A H 0.7669 0.4941 0.6543 0.040 Uiso 1 1 calc R . .
C13A C 0.6194(2) 0.47614(18) 0.75717(10) 0.0272(3) Uani 1 1 d . . .
C14A C 0.2789(2) 0.77203(18) 0.90144(11) 0.0308(4) Uani 1 1 d . . .
H14A H 0.2239 0.7145 0.9209 0.037 Uiso 1 1 calc R . .
C15A C 0.3309(3) 0.8059(3) 0.97155(15) 0.0602(7) Uani 1 1 d . . .
H15A H 0.2374 0.8543 1.0170 0.090 Uiso 1 1 calc R . .
H15B H 0.3872 0.8612 0.9544 0.090 Uiso 1 1 calc R . .
H15C H 0.4017 0.7242 0.9887 0.090 Uiso 1 1 calc R . .
C16A C 0.1591(3) 0.8952(2) 0.87597(16) 0.0510(6) Uani 1 1 d . . .
H16A H 0.0627 0.9361 0.9210 0.076 Uiso 1 1 calc R . .
H16B H 0.1324 0.8701 0.8287 0.076 Uiso 1 1 calc R . .
H16C H 0.2052 0.9584 0.8619 0.076 Uiso 1 1 calc R . .
C17A C 0.6897(2) 0.32564(18) 0.74752(11) 0.0307(4) Uani 1 1 d . . .
H17A H 0.6071 0.2988 0.7792 0.037 Uiso 1 1 calc R . .
C18A C 0.8334(3) 0.2670(2) 0.78240(16) 0.0499(6) Uani 1 1 d . . .
H18A H 0.8024 0.3034 0.8393 0.075 Uiso 1 1 calc R . .
H18B H 0.9176 0.2896 0.7512 0.075 Uiso 1 1 calc R . .
H18C H 0.8725 0.1705 0.7791 0.075 Uiso 1 1 calc R . .
C19A C 0.7347(3) 0.2698(2) 0.65853(13) 0.0410(5) Uani 1 1 d . . .
H19A H 0.6450 0.3159 0.6354 0.062 Uiso 1 1 calc R . .
H19B H 0.7609 0.1750 0.6556 0.062 Uiso 1 1 calc R . .
H19C H 0.8269 0.2827 0.6278 0.062 Uiso 1 1 calc R . .
N1B N 0.29347(17) 0.16505(14) 0.68160(8) 0.0244(3) Uani 1 1 d . . .
C1B C 0.41734(19) 0.12869(16) 0.82471(10) 0.0228(3) Uani 1 1 d . . .
C2B C 0.4908(2) 0.08879(18) 0.88741(11) 0.0287(3) Uani 1 1 d . . .
H2BA H 0.4319 0.1242 0.9419 0.034 Uiso 1 1 calc R . .
C3B C 0.6490(2) -0.00208(19) 0.87115(11) 0.0334(4) Uani 1 1 d . . .
H3BA H 0.6967 -0.0289 0.9147 0.040 Uiso 1 1 calc R . .
C4B C 0.7380(2) -0.05393(18) 0.79225(12) 0.0324(4) Uani 1 1 d . . .
H4BA H 0.8465 -0.1153 0.7812 0.039 Uiso 1 1 calc R . .
C5B C 0.6663(2) -0.01499(17) 0.72965(11) 0.0281(3) Uani 1 1 d . . .
H5BA H 0.7270 -0.0498 0.6753 0.034 Uiso 1 1 calc R . .
C6B C 0.5065(2) 0.07442(16) 0.74453(10) 0.0239(3) Uani 1 1 d . . .
C7B C 0.4408(2) 0.10356(17) 0.67441(10) 0.0254(3) Uani 1 1 d . . .
H7BA H 0.5114 0.0752 0.6215 0.031 Uiso 1 1 calc R . .
C8B C 0.23858(19) 0.18506(17) 0.61000(10) 0.0237(3) Uani 1 1 d . . .
C9B C 0.20743(19) 0.08551(17) 0.57845(10) 0.0246(3) Uani 1 1 d . . .
C10B C 0.1468(2) 0.10898(19) 0.51061(10) 0.0287(4) Uani 1 1 d . . .
H10B H 0.1261 0.0430 0.4876 0.034 Uiso 1 1 calc R . .
C11B C 0.1163(2) 0.22660(19) 0.47645(10) 0.0311(4) Uani 1 1 d . . .
H11B H 0.0731 0.2415 0.4310 0.037 Uiso 1 1 calc R . .
C12B C 0.1487(2) 0.32315(18) 0.50826(11) 0.0308(4) Uani 1 1 d . . .
H12B H 0.1282 0.4032 0.4838 0.037 Uiso 1 1 calc R . .
C13B C 0.2109(2) 0.30483(18) 0.57549(10) 0.0273(3) Uani 1 1 d . . .
C14B C 0.2439(2) -0.04541(18) 0.61495(11) 0.0279(3) Uani 1 1 d . . .
H14B H 0.2557 -0.0321 0.6704 0.033 Uiso 1 1 calc R . .
C15B C 0.1127(3) -0.0912(2) 0.62470(16) 0.0451(5) Uani 1 1 d . . .
H15D H 0.1367 -0.1691 0.6548 0.068 Uiso 1 1 calc R . .
H15E H 0.1057 -0.1142 0.5710 0.068 Uiso 1 1 calc R . .
H15F H 0.0112 -0.0198 0.6546 0.068 Uiso 1 1 calc R . .
C16B C 0.4004(3) -0.1518(2) 0.56536(15) 0.0456(5) Uani 1 1 d . . .
H16D H 0.4267 -0.2331 0.5922 0.068 Uiso 1 1 calc R . .
H16E H 0.4842 -0.1219 0.5607 0.068 Uiso 1 1 calc R . .
H16F H 0.3916 -0.1694 0.5111 0.068 Uiso 1 1 calc R . .
C17B C 0.2476(2) 0.41014(19) 0.61052(12) 0.0343(4) Uani 1 1 d . . .
H17B H 0.3384 0.3638 0.6348 0.041 Uiso 1 1 calc R . .
C18B C 0.2966(3) 0.4922(2) 0.54660(15) 0.0484(6) Uani 1 1 d . . .
H18D H 0.3831 0.4327 0.5014 0.073 Uiso 1 1 calc R . .
H18E H 0.3326 0.5492 0.5712 0.073 Uiso 1 1 calc R . .
H18F H 0.2054 0.5471 0.5264 0.073 Uiso 1 1 calc R . .
C19B C 0.1055(3) 0.5018(2) 0.67848(13) 0.0426(5) Uani 1 1 d . . .
H19D H 0.0775 0.4492 0.7203 0.064 Uiso 1 1 calc R . .
H19E H 0.0149 0.5495 0.6562 0.064 Uiso 1 1 calc R . .
H19F H 0.1330 0.5655 0.7026 0.064 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
Se C1A 1.9280(16) . ?
Se C1B 1.9291(16) . ?
N1A C7A 1.267(2) . ?
N1A C8A 1.428(2) . ?
C1A C2A 1.397(2) . ?
C1A C6A 1.397(2) . ?
C2A C3A 1.389(3) . ?
C2A H2AA 0.9500 . ?
C3A C4A 1.391(3) . ?
C3A H3AA 0.9500 . ?
C4A C5A 1.386(2) . ?
C4A H4AA 0.9500 . ?
C5A C6A 1.400(2) . ?
C5A H5AA 0.9500 . ?
C6A C7A 1.476(2) . ?
C7A H7AA 0.9500 . ?
C8A C9A 1.405(2) . ?
C8A C13A 1.406(2) . ?
C9A C10A 1.393(3) . ?
C9A C14A 1.525(2) . ?
C10A C11A 1.386(3) . ?
C10A H10A 0.9500 . ?
C11A C12A 1.384(3) . ?
C11A H11A 0.9500 . ?
C12A C13A 1.396(3) . ?
C12A H12A 0.9500 . ?
C13A C17A 1.521(2) . ?
C14A C15A 1.511(3) . ?
C14A C16A 1.525(3) . ?
C14A H14A 1.0000 . ?
C15A H15A 0.9800 . ?
C15A H15B 0.9800 . ?
C15A H15C 0.9800 . ?
C16A H16A 0.9800 . ?
C16A H16B 0.9800 . ?
C16A H16C 0.9800 . ?
C17A C18A 1.529(3) . ?
C17A C19A 1.534(3) . ?
C17A H17A 1.0000 . ?
C18A H18A 0.9800 . ?
C18A H18B 0.9800 . ?
C18A H18C 0.9800 . ?
C19A H19A 0.9800 . ?
C19A H19B 0.9800 . ?
C19A H19C 0.9800 . ?
N1B C7B 1.264(2) . ?
N1B C8B 1.428(2) . ?
C1B C2B 1.396(2) . ?
C1B C6B 1.407(2) . ?
C2B C3B 1.389(3) . ?
C2B H2BA 0.9500 . ?
C3B C4B 1.384(3) . ?
C3B H3BA 0.9500 . ?
C4B C5B 1.383(3) . ?
C4B H4BA 0.9500 . ?
C5B C6B 1.398(2) . ?
C5B H5BA 0.9500 . ?
C6B C7B 1.461(2) . ?
C7B H7BA 0.9500 . ?
C8B C13B 1.408(2) . ?
C8B C9B 1.408(2) . ?
C9B C10B 1.397(2) . ?
C9B C14B 1.524(2) . ?
C10B C11B 1.382(3) . ?
C10B H10B 0.9500 . ?
C11B C12B 1.388(3) . ?
C11B H11B 0.9500 . ?
C12B C13B 1.397(3) . ?
C12B H12B 0.9500 . ?
C13B C17B 1.525(3) . ?
C14B C16B 1.513(3) . ?
C14B C15B 1.521(3) . ?
C14B H14B 1.0000 . ?
C15B H15D 0.9800 . ?
C15B H15E 0.9800 . ?
C15B H15F 0.9800 . ?
C16B H16D 0.9800 . ?
C16B H16E 0.9800 . ?
C16B H16F 0.9800 . ?
C17B C19B 1.527(3) . ?
C17B C18B 1.534(3) . ?
C17B H17B 1.0000 . ?
C18B H18D 0.9800 . ?
C18B H18E 0.9800 . ?
C18B H18F 0.9800 . ?
C19B H19D 0.9800 . ?
C19B H19E 0.9800 . ?
C19B H19F 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
C1A Se C1B 96.34(7) . . ?
C7A N1A C8A 119.18(14) . . ?
C2A C1A C6A 119.92(15) . . ?
C2A C1A Se 119.27(13) . . ?
C6A C1A Se 120.78(12) . . ?
C3A C2A C1A 119.91(16) . . ?
C3A C2A H2AA 120.0 . . ?
C1A C2A H2AA 120.0 . . ?
C2A C3A C4A 120.36(16) . . ?
C2A C3A H3AA 119.8 . . ?
C4A C3A H3AA 119.8 . . ?
C5A C4A C3A 119.84(16) . . ?
C5A C4A H4AA 120.1 . . ?
C3A C4A H4AA 120.1 . . ?
C4A C5A C6A 120.40(16) . . ?
C4A C5A H5AA 119.8 . . ?
C6A C5A H5AA 119.8 . . ?
C1A C6A C5A 119.44(15) . . ?
C1A C6A C7A 121.00(14) . . ?
C5A C6A C7A 119.50(15) . . ?
N1A C7A C6A 121.83(15) . . ?
N1A C7A H7AA 119.1 . . ?
C6A C7A H7AA 119.1 . . ?
C9A C8A C13A 121.66(16) . . ?
C9A C8A N1A 117.65(15) . . ?
C13A C8A N1A 120.50(15) . . ?
C10A C9A C8A 118.18(16) . . ?
C10A C9A C14A 120.83(16) . . ?
C8A C9A C14A 120.98(16) . . ?
C11A C10A C9A 120.88(18) . . ?
C11A C10A H10A 119.6 . . ?
C9A C10A H10A 119.6 . . ?
C12A C11A C10A 120.06(17) . . ?
C12A C11A H11A 120.0 . . ?
C10A C11A H11A 120.0 . . ?
C11A C12A C13A 121.25(17) . . ?
C11A C12A H12A 119.4 . . ?
C13A C12A H12A 119.4 . . ?
C12A C13A C8A 117.76(16) . . ?
C12A C13A C17A 120.64(16) . . ?
C8A C13A C17A 121.59(16) . . ?
C15A C14A C9A 110.76(16) . . ?
C15A C14A C16A 111.7(2) . . ?
C9A C14A C16A 112.67(17) . . ?
C15A C14A H14A 107.1 . . ?
C9A C14A H14A 107.1 . . ?
C16A C14A H14A 107.1 . . ?
C14A C15A H15A 109.5 . . ?
C14A C15A H15B 109.5 . . ?
H15A C15A H15B 109.5 . . ?
C14A C15A H15C 109.5 . . ?
H15A C15A H15C 109.5 . . ?
H15B C15A H15C 109.5 . . ?
C14A C16A H16A 109.5 . . ?
C14A C16A H16B 109.5 . . ?
H16A C16A H16B 109.5 . . ?
C14A C16A H16C 109.5 . . ?
H16A C16A H16C 109.5 . . ?
H16B C16A H16C 109.5 . . ?
C13A C17A C18A 110.68(16) . . ?
C13A C17A C19A 111.64(16) . . ?
C18A C17A C19A 110.63(17) . . ?
C13A C17A H17A 107.9 . . ?
C18A C17A H17A 107.9 . . ?
C19A C17A H17A 107.9 . . ?
C17A C18A H18A 109.5 . . ?
C17A C18A H18B 109.5 . . ?
H18A C18A H18B 109.5 . . ?
C17A C18A H18C 109.5 . . ?
H18A C18A H18C 109.5 . . ?
H18B C18A H18C 109.5 . . ?
C17A C19A H19A 109.5 . . ?
C17A C19A H19B 109.5 . . ?
H19A C19A H19B 109.5 . . ?
C17A C19A H19C 109.5 . . ?
H19A C19A H19C 109.5 . . ?
H19B C19A H19C 109.5 . . ?
C7B N1B C8B 118.87(14) . . ?
C2B C1B C6B 118.65(15) . . ?
C2B C1B Se 120.76(13) . . ?
C6B C1B Se 120.58(12) . . ?
C3B C2B C1B 120.82(16) . . ?
C3B C2B H2BA 119.6 . . ?
C1B C2B H2BA 119.6 . . ?
C4B C3B C2B 120.73(17) . . ?
C4B C3B H3BA 119.6 . . ?
C2B C3B H3BA 119.6 . . ?
C5B C4B C3B 118.90(17) . . ?
C5B C4B H4BA 120.5 . . ?
C3B C4B H4BA 120.5 . . ?
C4B C5B C6B 121.48(16) . . ?
C4B C5B H5BA 119.3 . . ?
C6B C5B H5BA 119.3 . . ?
C5B C6B C1B 119.39(15) . . ?
C5B C6B C7B 116.92(15) . . ?
C1B C6B C7B 123.68(15) . . ?
N1B C7B C6B 122.43(15) . . ?
N1B C7B H7BA 118.8 . . ?
C6B C7B H7BA 118.8 . . ?
C13B C8B C9B 122.28(16) . . ?
C13B C8B N1B 119.40(15) . . ?
C9B C8B N1B 118.26(15) . . ?
C10B C9B C8B 117.69(16) . . ?
C10B C9B C14B 120.92(16) . . ?
C8B C9B C14B 121.35(15) . . ?
C11B C10B C9B 121.08(17) . . ?
C11B C10B H10B 119.5 . . ?
C9B C10B H10B 119.5 . . ?
C10B C11B C12B 120.27(16) . . ?
C10B C11B H11B 119.9 . . ?
C12B C11B H11B 119.9 . . ?
C11B C12B C13B 121.26(17) . . ?
C11B C12B H12B 119.4 . . ?
C13B C12B H12B 119.4 . . ?
C12B C13B C8B 117.41(17) . . ?
C12B C13B C17B 121.56(17) . . ?
C8B C13B C17B 121.03(16) . . ?
C16B C14B C15B 110.35(17) . . ?
C16B C14B C9B 110.49(15) . . ?
C15B C14B C9B 113.50(16) . . ?
C16B C14B H14B 107.4 . . ?
C15B C14B H14B 107.4 . . ?
C9B C14B H14B 107.4 . . ?
C14B C15B H15D 109.5 . . ?
C14B C15B H15E 109.5 . . ?
H15D C15B H15E 109.5 . . ?
C14B C15B H15F 109.5 . . ?
H15D C15B H15F 109.5 . . ?
H15E C15B H15F 109.5 . . ?
C14B C16B H16D 109.5 . . ?
C14B C16B H16E 109.5 . . ?
H16D C16B H16E 109.5 . . ?
C14B C16B H16F 109.5 . . ?
H16D C16B H16F 109.5 . . ?
H16E C16B H16F 109.5 . . ?
C13B C17B C19B 110.36(16) . . ?
C13B C17B C18B 113.40(18) . . ?
C19B C17B C18B 109.80(17) . . ?
C13B C17B H17B 107.7 . . ?
C19B C17B H17B 107.7 . . ?
C18B C17B H17B 107.7 . . ?
C17B C18B H18D 109.5 . . ?
C17B C18B H18E 109.5 . . ?
H18D C18B H18E 109.5 . . ?
C17B C18B H18F 109.5 . . ?
H18D C18B H18F 109.5 . . ?
H18E C18B H18F 109.5 . . ?
C17B C19B H19D 109.5 . . ?
C17B C19B H19E 109.5 . . ?
H19D C19B H19E 109.5 . . ?
C17B C19B H19F 109.5 . . ?
H19D C19B H19F 109.5 . . ?
H19E C19B H19F 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
C1B Se C1A C2A -106.10(13) . . . . ?
C1B Se C1A C6A 72.01(14) . . . . ?
C6A C1A C2A C3A -1.1(2) . . . . ?
Se C1A C2A C3A 176.98(13) . . . . ?
C1A C2A C3A C4A -2.1(3) . . . . ?
C2A C3A C4A C5A 3.0(3) . . . . ?
C3A C4A C5A C6A -0.6(3) . . . . ?
C2A C1A C6A C5A 3.5(2) . . . . ?
Se C1A C6A C5A -174.58(12) . . . . ?
C2A C1A C6A C7A -173.74(15) . . . . ?
Se C1A C6A C7A 8.2(2) . . . . ?
C4A C5A C6A C1A -2.7(2) . . . . ?
C4A C5A C6A C7A 174.63(15) . . . . ?
C8A N1A C7A C6A -171.70(14) . . . . ?
C1A C6A C7A N1A -156.16(16) . . . . ?
C5A C6A C7A N1A 26.6(2) . . . . ?
C7A N1A C8A C9A 93.5(2) . . . . ?
C7A N1A C8A C13A -91.3(2) . . . . ?
C13A C8A C9A C10A -5.1(3) . . . . ?
N1A C8A C9A C10A 170.05(16) . . . . ?
C13A C8A C9A C14A 176.31(16) . . . . ?
N1A C8A C9A C14A -8.6(2) . . . . ?
C8A C9A C10A C11A 1.7(3) . . . . ?
C14A C9A C10A C11A -179.66(19) . . . . ?
C9A C10A C11A C12A 2.1(3) . . . . ?
C10A C11A C12A C13A -2.7(3) . . . . ?
C11A C12A C13A C8A -0.5(3) . . . . ?
C11A C12A C13A C17A -179.49(19) . . . . ?
C9A C8A C13A C12A 4.5(3) . . . . ?
N1A C8A C13A C12A -170.51(16) . . . . ?
C9A C8A C13A C17A -176.56(16) . . . . ?
N1A C8A C13A C17A 8.5(3) . . . . ?
C10A C9A C14A C15A -87.1(2) . . . . ?
C8A C9A C14A C15A 91.5(2) . . . . ?
C10A C9A C14A C16A 38.9(3) . . . . ?
C8A C9A C14A C16A -142.52(19) . . . . ?
C12A C13A C17A C18A 84.7(2) . . . . ?
C8A C13A C17A C18A -94.2(2) . . . . ?
C12A C13A C17A C19A -39.0(2) . . . . ?
C8A C13A C17A C19A 142.07(18) . . . . ?
C1A Se C1B C2B 19.23(15) . . . . ?
C1A Se C1B C6B -161.19(14) . . . . ?
C6B C1B C2B C3B 0.4(3) . . . . ?
Se C1B C2B C3B 179.94(15) . . . . ?
C1B C2B C3B C4B 0.8(3) . . . . ?
C2B C3B C4B C5B -0.8(3) . . . . ?
C3B C4B C5B C6B -0.4(3) . . . . ?
C4B C5B C6B C1B 1.6(3) . . . . ?
C4B C5B C6B C7B -176.99(17) . . . . ?
C2B C1B C6B C5B -1.5(2) . . . . ?
Se C1B C6B C5B 178.90(13) . . . . ?
C2B C1B C6B C7B 176.95(16) . . . . ?
Se C1B C6B C7B -2.6(2) . . . . ?
C8B N1B C7B C6B -177.64(15) . . . . ?
C5B C6B C7B N1B 168.19(17) . . . . ?
C1B C6B C7B N1B -10.3(3) . . . . ?
C7B N1B C8B C13B -95.53(19) . . . . ?
C7B N1B C8B C9B 87.2(2) . . . . ?
C13B C8B C9B C10B -0.1(2) . . . . ?
N1B C8B C9B C10B 177.08(14) . . . . ?
C13B C8B C9B C14B 177.77(15) . . . . ?
N1B C8B C9B C14B -5.0(2) . . . . ?
C8B C9B C10B C11B -0.9(2) . . . . ?
C14B C9B C10B C11B -178.80(16) . . . . ?
C9B C10B C11B C12B 1.3(3) . . . . ?
C10B C11B C12B C13B -0.6(3) . . . . ?
C11B C12B C13B C8B -0.4(3) . . . . ?
C11B C12B C13B C17B 179.69(16) . . . . ?
C9B C8B C13B C12B 0.7(2) . . . . ?
N1B C8B C13B C12B -176.43(15) . . . . ?
C9B C8B C13B C17B -179.32(16) . . . . ?
N1B C8B C13B C17B 3.5(2) . . . . ?
C10B C9B C14B C16B 78.9(2) . . . . ?
C8B C9B C14B C16B -98.9(2) . . . . ?
C10B C9B C14B C15B -45.7(2) . . . . ?
C8B C9B C14B C15B 136.51(18) . . . . ?
C12B C13B C17B C19B 92.7(2) . . . . ?
C8B C13B C17B C19B -87.2(2) . . . . ?
C12B C13B C17B C18B -30.9(2) . . . . ?
C8B C13B C17B C18B 149.14(18) . . . . ?

_diffrn_measured_fraction_theta_max 0.969
_diffrn_reflns_theta_full        67.50
_diffrn_measured_fraction_theta_full 0.999
_refine_diff_density_max         0.434
_refine_diff_density_min         -0.396
_refine_diff_density_rms         0.056

_database_code_depnum_ccdc_archive 'CCDC 959142'
#######################################################################
#
#                 Cambridge Crystallographic Data Centre
#                                CCDC 
# 
#######################################################################
# 
#  This CIF contains data from an original supplementary publication
#  deposited with the CCDC, and may include chemical, crystal,
#  experimental, refinement, atomic coordinates,
#  anisotropic displacement parameters and molecular geometry data,
#  as required by the journal to which it was submitted.
#
#  This CIF is provided on the understanding that it is used for bona
#  fide research purposes only. It may contain copyright material
#  of the CCDC or of third parties, and may not be copied or further
#  disseminated in any form, whether machine-readable or not,
#  except for the purpose of generating routine backup copies
#  on your local computer system.
# 
#  For further information on the CCDC, data deposition and
#  data retrieval see:
#                         www.ccdc.cam.ac.uk
#
#  Bona fide researchers may freely download Mercury and enCIFer
#  from this site to visualise CIF-encoded structures and 
#  to carry out CIF format checking respectively.
#
data_hbs-14

_audit_creation_method           SHELXL-97
_chemical_name_systematic        
; 
 ? 
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         'C19 H22 Br N Se'
_chemical_formula_sum            'C19 H22 Br N Se'
_chemical_formula_weight         423.25

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'
Br Br -0.2901 2.4595 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_symmetry_cell_setting           orthorhombic
_symmetry_space_group_name_H-M   Pbca
_symmetry_space_group_name_Hall  '-P 2ac 2ab '

loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'-x+1/2, -y, z+1/2'
'-x, y+1/2, -z+1/2'
'x+1/2, -y+1/2, -z'
'-x, -y, -z'
'x-1/2, y, -z-1/2'
'x, -y-1/2, z-1/2'
'-x-1/2, y-1/2, z'

_cell_length_a                   9.5735(5)
_cell_length_b                   16.5118(9)
_cell_length_c                   23.4372(13)
_cell_angle_alpha                90.00
_cell_angle_beta                 90.00
_cell_angle_gamma                90.00
_cell_volume                     3704.9(3)
_cell_formula_units_Z            8
_cell_measurement_temperature    173(2)
_cell_measurement_reflns_used    8530
_cell_measurement_theta_min      3.01
_cell_measurement_theta_max      32.32

_exptl_crystal_description       block
_exptl_crystal_colour            'pale yellow'
_exptl_crystal_size_max          0.21
_exptl_crystal_size_mid          0.20
_exptl_crystal_size_min          0.12
_exptl_crystal_density_meas      ?
_exptl_crystal_density_diffrn    1.518
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             1696
_exptl_absorpt_coefficient_mu    4.181
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.4739
_exptl_absorpt_correction_T_max  0.6338
_exptl_absorpt_process_details   'CrysAlisRED; Oxford Diffraction, 2010.'

_exptl_special_details           
; 
 ? 
;

_diffrn_ambient_temperature      173(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_radiation_source         'Enhance (Mo) X-ray Source'
_diffrn_radiation_monochromator  graphite
_diffrn_measurement_device_type  'Xcalibur, Eos, Gemini'
_diffrn_detector_area_resol_mean 16.1500
_diffrn_measurement_method       ' ω scans'

_diffrn_reflns_number            45354
_diffrn_reflns_av_R_equivalents  0.0982
_diffrn_reflns_av_sigmaI/netI    0.0431
_diffrn_reflns_limit_h_min       -12
_diffrn_reflns_limit_h_max       12
_diffrn_reflns_limit_k_min       -21
_diffrn_reflns_limit_k_max       22
_diffrn_reflns_limit_l_min       -31
_diffrn_reflns_limit_l_max       31
_diffrn_reflns_theta_min         3.01
_diffrn_reflns_theta_max         28.28
_reflns_number_total             4597
_reflns_number_gt                3645
_reflns_threshold_expression     >2sigma(I)

_computing_data_collection       'CrysAlisPRO (Oxford Diffraction, 2010)'
_computing_cell_refinement       'CrysAlisPRO (Oxford Diffraction, 2010)'
_computing_data_reduction        'CrysAlisRED (Oxford Diffraction, 2010)'
_computing_structure_solution    'SHELXS97 (Sheldrick, 2008)'
_computing_structure_refinement  'SHELXL97 (Sheldrick, 2008)'
_computing_molecular_graphics    'SHELXTL (Bruker, 2000)'
_computing_publication_material  'SHELXTL (Bruker, 2000)'

_refine_special_details          
; 
Refinement of F² against ALL reflections. The weighted R-factor
wR and goodness of fit S are based on F², conventional
R-factors R are based on F, with F set to zero for
negative F². The threshold expression of F² >
σ(F²) is used only for calculating R-factors(gt) etc.
and is not relevant to the choice of reflections for refinement.
R-factors based on F² are statistically about twice as large
as those based on F, and R- factors based on ALL data will be
even larger. 
;

_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'calc w=1/[σ²(Fo²)+(0.0284P)²+3.2208P] 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_number_reflns         4597
_refine_ls_number_parameters     203
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0520
_refine_ls_R_factor_gt           0.0361
_refine_ls_wR_factor_ref         0.0834
_refine_ls_wR_factor_gt          0.0764
_refine_ls_goodness_of_fit_ref   1.028
_refine_ls_restrained_S_all      1.028
_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_symmetry_multiplicity
_atom_site_calc_flag
_atom_site_refinement_flags
_atom_site_disorder_assembly
_atom_site_disorder_group
Se1 Se 0.58322(3) 0.192776(16) 0.618180(11) 0.02217(8) Uani 1 1 d . . .
Br1 Br 0.56603(3) 0.032420(17) 0.639890(14) 0.03576(10) Uani 1 1 d . . .
N1 N 0.6088(2) 0.30931(13) 0.60075(9) 0.0214(5) Uani 1 1 d . . .
C1 C 0.7405(3) 0.21007(15) 0.66536(11) 0.0203(5) Uani 1 1 d . . .
C2 C 0.8061(3) 0.15425(17) 0.70098(12) 0.0274(6) Uani 1 1 d . . .
H2A H 0.7713 0.1006 0.7042 0.033 Uiso 1 1 calc R . .
C3 C 0.9214(3) 0.17790(19) 0.73137(13) 0.0325(7) Uani 1 1 d . . .
H3A H 0.9657 0.1400 0.7559 0.039 Uiso 1 1 calc R . .
C4 C 0.9753(3) 0.25577(18) 0.72724(12) 0.0319(7) Uani 1 1 d . . .
H4A H 1.0566 0.2701 0.7482 0.038 Uiso 1 1 calc R . .
C5 C 0.9115(3) 0.31188(18) 0.69313(12) 0.0273(6) Uani 1 1 d . . .
H5A H 0.9475 0.3654 0.6904 0.033 Uiso 1 1 calc R . .
C6 C 0.7924(3) 0.28946(15) 0.66227(11) 0.0209(5) Uani 1 1 d . . .
C7 C 0.7154(3) 0.34194(16) 0.62570(11) 0.0224(6) Uani 1 1 d . . .
H7A H 0.7405 0.3970 0.6200 0.027 Uiso 1 1 calc R . .
C8 C 0.5112(3) 0.35297(15) 0.56519(12) 0.0222(6) Uani 1 1 d . . .
C9 C 0.5161(3) 0.34116(17) 0.50638(12) 0.0273(6) Uani 1 1 d . . .
C10 C 0.4201(3) 0.38470(18) 0.47378(13) 0.0340(7) Uani 1 1 d . . .
H10A H 0.4208 0.3790 0.4335 0.041 Uiso 1 1 calc R . .
C11 C 0.3245(3) 0.43576(18) 0.49877(14) 0.0348(7) Uani 1 1 d . . .
H11A H 0.2609 0.4652 0.4755 0.042 Uiso 1 1 calc R . .
C12 C 0.3202(3) 0.44468(17) 0.55731(13) 0.0314(7) Uani 1 1 d . . .
H12A H 0.2528 0.4797 0.5740 0.038 Uiso 1 1 calc R . .
C13 C 0.4135(3) 0.40289(16) 0.59235(13) 0.0253(6) Uani 1 1 d . . .
C14 C 0.4045(3) 0.41135(18) 0.65686(12) 0.0279(6) Uani 1 1 d . . .
H14A H 0.4671 0.3693 0.6738 0.033 Uiso 1 1 calc R . .
C15 C 0.2583(4) 0.3953(3) 0.67876(15) 0.0524(10) Uani 1 1 d . . .
H15A H 0.2561 0.4029 0.7202 0.079 Uiso 1 1 calc R . .
H15B H 0.2313 0.3396 0.6695 0.079 Uiso 1 1 calc R . .
H15C H 0.1928 0.4331 0.6607 0.079 Uiso 1 1 calc R . .
C16 C 0.4582(6) 0.4929(3) 0.67612(17) 0.0718(14) Uani 1 1 d . . .
H16A H 0.5487 0.5037 0.6581 0.108 Uiso 1 1 calc R . .
H16B H 0.4691 0.4929 0.7177 0.108 Uiso 1 1 calc R . .
H16C H 0.3915 0.5351 0.6650 0.108 Uiso 1 1 calc R . .
C17 C 0.6155(3) 0.28144(18) 0.47822(13) 0.0324(7) Uani 1 1 d . . .
H17A H 0.6853 0.2641 0.5075 0.039 Uiso 1 1 calc R . .
C18 C 0.5337(4) 0.2060(2) 0.45948(16) 0.0468(9) Uani 1 1 d . . .
H18A H 0.5980 0.1667 0.4425 0.070 Uiso 1 1 calc R . .
H18B H 0.4630 0.2216 0.4313 0.070 Uiso 1 1 calc R . .
H18C H 0.4878 0.1818 0.4927 0.070 Uiso 1 1 calc R . .
C19 C 0.6952(4) 0.3177(2) 0.42854(17) 0.0584(11) Uani 1 1 d . . .
H19A H 0.7472 0.3653 0.4416 0.088 Uiso 1 1 calc R . .
H19B H 0.6293 0.3338 0.3986 0.088 Uiso 1 1 calc R . .
H19C H 0.7605 0.2775 0.4133 0.088 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 1.890(3) . ?
Se1 N1 1.982(2) . ?
Se1 Br1 2.7012(4) . ?
N1 C7 1.293(3) . ?
N1 C8 1.445(3) . ?
C1 C2 1.393(4) . ?
C1 C6 1.404(4) . ?
C2 C3 1.371(4) . ?
C2 H2A 0.9500 . ?
C3 C4 1.389(4) . ?
C3 H3A 0.9500 . ?
C4 C5 1.368(4) . ?
C4 H4A 0.9500 . ?
C5 C6 1.400(4) . ?
C5 H5A 0.9500 . ?
C6 C7 1.425(4) . ?
C7 H7A 0.9500 . ?
C8 C9 1.393(4) . ?
C8 C13 1.400(4) . ?
C9 C10 1.395(4) . ?
C9 C17 1.521(4) . ?
C10 C11 1.375(4) . ?
C10 H10A 0.9500 . ?
C11 C12 1.380(4) . ?
C11 H11A 0.9500 . ?
C12 C13 1.396(4) . ?
C12 H12A 0.9500 . ?
C13 C14 1.521(4) . ?
C14 C16 1.511(5) . ?
C14 C15 1.514(4) . ?
C14 H14A 1.0000 . ?
C15 H15A 0.9800 . ?
C15 H15B 0.9800 . ?
C15 H15C 0.9800 . ?
C16 H16A 0.9800 . ?
C16 H16B 0.9800 . ?
C16 H16C 0.9800 . ?
C17 C19 1.515(5) . ?
C17 C18 1.535(5) . ?
C17 H17A 1.0000 . ?
C18 H18A 0.9800 . ?
C18 H18B 0.9800 . ?
C18 H18C 0.9800 . ?
C19 H19A 0.9800 . ?
C19 H19B 0.9800 . ?
C19 H19C 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
C1 Se1 N1 82.85(10) . . ?
C1 Se1 Br1 94.96(8) . . ?
N1 Se1 Br1 176.23(7) . . ?
C7 N1 C8 124.3(2) . . ?
C7 N1 Se1 114.12(18) . . ?
C8 N1 Se1 121.56(17) . . ?
C2 C1 C6 119.3(3) . . ?
C2 C1 Se1 127.6(2) . . ?
C6 C1 Se1 113.13(19) . . ?
C3 C2 C1 119.1(3) . . ?
C3 C2 H2A 120.5 . . ?
C1 C2 H2A 120.5 . . ?
C2 C3 C4 121.8(3) . . ?
C2 C3 H3A 119.1 . . ?
C4 C3 H3A 119.1 . . ?
C5 C4 C3 120.2(3) . . ?
C5 C4 H4A 119.9 . . ?
C3 C4 H4A 119.9 . . ?
C4 C5 C6 119.1(3) . . ?
C4 C5 H5A 120.4 . . ?
C6 C5 H5A 120.4 . . ?
C5 C6 C1 120.6(2) . . ?
C5 C6 C7 124.9(3) . . ?
C1 C6 C7 114.6(2) . . ?
N1 C7 C6 115.3(2) . . ?
N1 C7 H7A 122.4 . . ?
C6 C7 H7A 122.4 . . ?
C9 C8 C13 123.7(2) . . ?
C9 C8 N1 118.6(2) . . ?
C13 C8 N1 117.6(2) . . ?
C8 C9 C10 116.6(3) . . ?
C8 C9 C17 122.8(2) . . ?
C10 C9 C17 120.6(3) . . ?
C11 C10 C9 121.4(3) . . ?
C11 C10 H10A 119.3 . . ?
C9 C10 H10A 119.3 . . ?
C10 C11 C12 120.6(3) . . ?
C10 C11 H11A 119.7 . . ?
C12 C11 H11A 119.7 . . ?
C11 C12 C13 120.8(3) . . ?
C11 C12 H12A 119.6 . . ?
C13 C12 H12A 119.6 . . ?
C12 C13 C8 116.8(3) . . ?
C12 C13 C14 120.2(3) . . ?
C8 C13 C14 123.0(2) . . ?
C16 C14 C15 111.7(3) . . ?
C16 C14 C13 111.1(3) . . ?
C15 C14 C13 111.9(3) . . ?
C16 C14 H14A 107.3 . . ?
C15 C14 H14A 107.3 . . ?
C13 C14 H14A 107.3 . . ?
C14 C15 H15A 109.5 . . ?
C14 C15 H15B 109.5 . . ?
H15A C15 H15B 109.5 . . ?
C14 C15 H15C 109.5 . . ?
H15A C15 H15C 109.5 . . ?
H15B C15 H15C 109.5 . . ?
C14 C16 H16A 109.5 . . ?
C14 C16 H16B 109.5 . . ?
H16A C16 H16B 109.5 . . ?
C14 C16 H16C 109.5 . . ?
H16A C16 H16C 109.5 . . ?
H16B C16 H16C 109.5 . . ?
C19 C17 C9 113.1(3) . . ?
C19 C17 C18 111.0(3) . . ?
C9 C17 C18 109.3(3) . . ?
C19 C17 H17A 107.8 . . ?
C9 C17 H17A 107.8 . . ?
C18 C17 H17A 107.8 . . ?
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 . . ?
C17 C19 H19A 109.5 . . ?
C17 C19 H19B 109.5 . . ?
H19A C19 H19B 109.5 . . ?
C17 C19 H19C 109.5 . . ?
H19A C19 H19C 109.5 . . ?
H19B C19 H19C 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


C1 Se1 N1 C7 2.1(2) . . . . ?
C1 Se1 N1 C8 -175.2(2) . . . . ?
N1 Se1 C1 C2 178.1(3) . . . . ?
Br1 Se1 C1 C2 -5.0(2) . . . . ?
N1 Se1 C1 C6 -1.88(19) . . . . ?
Br1 Se1 C1 C6 175.04(18) . . . . ?
C6 C1 C2 C3 -1.2(4) . . . . ?
Se1 C1 C2 C3 178.8(2) . . . . ?
C1 C2 C3 C4 -0.5(4) . . . . ?
C2 C3 C4 C5 1.4(5) . . . . ?
C3 C4 C5 C6 -0.5(4) . . . . ?
C4 C5 C6 C1 -1.2(4) . . . . ?
C4 C5 C6 C7 179.4(3) . . . . ?
C2 C1 C6 C5 2.1(4) . . . . ?
Se1 C1 C6 C5 -177.9(2) . . . . ?
C2 C1 C6 C7 -178.4(2) . . . . ?
Se1 C1 C6 C7 1.5(3) . . . . ?
C8 N1 C7 C6 175.5(2) . . . . ?
Se1 N1 C7 C6 -1.7(3) . . . . ?
C5 C6 C7 N1 179.6(3) . . . . ?
C1 C6 C7 N1 0.2(3) . . . . ?
C7 N1 C8 C9 106.8(3) . . . . ?
Se1 N1 C8 C9 -76.2(3) . . . . ?
C7 N1 C8 C13 -75.4(3) . . . . ?
Se1 N1 C8 C13 101.7(2) . . . . ?
C13 C8 C9 C10 2.4(4) . . . . ?
N1 C8 C9 C10 -179.9(2) . . . . ?
C13 C8 C9 C17 -174.9(3) . . . . ?
N1 C8 C9 C17 2.8(4) . . . . ?
C8 C9 C10 C11 -0.8(4) . . . . ?
C17 C9 C10 C11 176.5(3) . . . . ?
C9 C10 C11 C12 -0.7(5) . . . . ?
C10 C11 C12 C13 0.7(5) . . . . ?
C11 C12 C13 C8 0.7(4) . . . . ?
C11 C12 C13 C14 -178.1(3) . . . . ?
C9 C8 C13 C12 -2.3(4) . . . . ?
N1 C8 C13 C12 179.9(2) . . . . ?
C9 C8 C13 C14 176.4(3) . . . . ?
N1 C8 C13 C14 -1.3(4) . . . . ?
C12 C13 C14 C16 -73.6(4) . . . . ?
C8 C13 C14 C16 107.7(4) . . . . ?
C12 C13 C14 C15 52.0(4) . . . . ?
C8 C13 C14 C15 -126.7(3) . . . . ?
C8 C9 C17 C19 -131.3(3) . . . . ?
C10 C9 C17 C19 51.6(4) . . . . ?
C8 C9 C17 C18 104.6(3) . . . . ?
C10 C9 C17 C18 -72.6(4) . . . . ?

loop_
_geom_hbond_atom_site_label_D
_geom_hbond_atom_site_label_H
_geom_hbond_atom_site_label_A
_geom_hbond_distance_DH
_geom_hbond_distance_HA
_geom_hbond_distance_DA
_geom_hbond_angle_DHA
_geom_hbond_site_symmetry_A
C2 H2A Br1 0.95 2.72 3.373(3) 126.5 .

_diffrn_measured_fraction_theta_max 0.999
_diffrn_reflns_theta_full        25.00
_diffrn_measured_fraction_theta_full 0.998
_refine_diff_density_max         0.501
_refine_diff_density_min         -0.802
_refine_diff_density_rms         0.087
_database_code_depnum_ccdc_archive 'CCDC 959143'
#######################################################################
#
#                 Cambridge Crystallographic Data Centre
#                                CCDC 
# 
#######################################################################
# 
#  This CIF contains data from an original supplementary publication
#  deposited with the CCDC, and may include chemical, crystal,
#  experimental, refinement, atomic coordinates,
#  anisotropic displacement parameters and molecular geometry data,
#  as required by the journal to which it was submitted.
#
#  This CIF is provided on the understanding that it is used for bona
#  fide research purposes only. It may contain copyright material
#  of the CCDC or of third parties, and may not be copied or further
#  disseminated in any form, whether machine-readable or not,
#  except for the purpose of generating routine backup copies
#  on your local computer system.
# 
#  For further information on the CCDC, data deposition and
#  data retrieval see:
#                         www.ccdc.cam.ac.uk
#
#  Bona fide researchers may freely download Mercury and enCIFer
#  from this site to visualise CIF-encoded structures and 
#  to carry out CIF format checking respectively.
#
data_hbs-15

_audit_creation_method           SHELXL-97
_chemical_name_systematic        
; 
 ? 
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         'C19 H22 I N Se'
_chemical_formula_sum            'C19 H22 I N Se'
_chemical_formula_weight         470.24

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'

_symmetry_cell_setting           Orthorhombic
_symmetry_space_group_name_H-M   Pbca
_symmetry_space_group_name_Hall  '-P 2ac 2ab '

loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'-x+1/2, -y, z+1/2'
'-x, y+1/2, -z+1/2'
'x+1/2, -y+1/2, -z'
'-x, -y, -z'
'x-1/2, y, -z-1/2'
'x, -y-1/2, z-1/2'
'-x-1/2, y-1/2, z'

_cell_length_a                   9.5672(2)
_cell_length_b                   17.2716(2)
_cell_length_c                   23.5022(5)
_cell_angle_alpha                90.00
_cell_angle_beta                 90.00
_cell_angle_gamma                90.00
_cell_volume                     3883.52(12)
_cell_formula_units_Z            8
_cell_measurement_temperature    173(2)
_cell_measurement_reflns_used    12060
_cell_measurement_theta_min      2.98
_cell_measurement_theta_max      32.30

_exptl_crystal_description       block
_exptl_crystal_colour            yellow
_exptl_crystal_size_max          0.15
_exptl_crystal_size_mid          0.12
_exptl_crystal_size_min          0.08
_exptl_crystal_density_meas      ?
_exptl_crystal_density_diffrn    1.609
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             1840
_exptl_absorpt_coefficient_mu    3.521
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.6202
_exptl_absorpt_correction_T_max  0.7659
_exptl_absorpt_process_details   'CrysAlisRED; Oxford Diffraction, 2010.'

_exptl_special_details           
; 
 ? 
;

_diffrn_ambient_temperature      173(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_radiation_source         'Enhance (Mo) X-ray Source'
_diffrn_radiation_monochromator  graphite
_diffrn_measurement_device_type  'Xcalibur, Eos, Gemini'
_diffrn_detector_area_resol_mean 16.1500
_diffrn_measurement_method       ' ω scans'

_diffrn_reflns_number            42681
_diffrn_reflns_av_R_equivalents  0.0418
_diffrn_reflns_av_sigmaI/netI    0.0221
_diffrn_reflns_limit_h_min       -12
_diffrn_reflns_limit_h_max       12
_diffrn_reflns_limit_k_min       -23
_diffrn_reflns_limit_k_max       23
_diffrn_reflns_limit_l_min       -31
_diffrn_reflns_limit_l_max       30
_diffrn_reflns_theta_min         2.99
_diffrn_reflns_theta_max         28.70
_reflns_number_total             5007
_reflns_number_gt                4276
_reflns_threshold_expression     >2sigma(I)

_computing_data_collection       'CrysAlisPRO (Oxford Diffraction, 2010)'
_computing_cell_refinement       'CrysAlisPRO (Oxford Diffraction, 2010)'
_computing_data_reduction        'CrysAlisRED (Oxford Diffraction, 2010)'
_computing_structure_solution    'SHELXS97 (Sheldrick, 2008)'
_computing_structure_refinement  'SHELXL97 (Sheldrick, 2008)'
_computing_molecular_graphics    'SHELXTL (Bruker, 2000)'
_computing_publication_material  'SHELXTL (Bruker, 2000)'

_refine_special_details          
; 
Refinement of F² against ALL reflections. The weighted R-factor
wR and goodness of fit S are based on F², conventional
R-factors R are based on F, with F set to zero for
negative F². The threshold expression of F² >
σ(F²) is used only for calculating R-factors(gt) etc.
and is not relevant to the choice of reflections for refinement.
R-factors based on F² are statistically about twice as large
as those based on F, and R- factors based on ALL data will be
even larger. 
;

_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'calc w=1/[σ²(Fo²)+(0.0233P)²+3.3134P] 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_number_reflns         5007
_refine_ls_number_parameters     203
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0370
_refine_ls_R_factor_gt           0.0275
_refine_ls_wR_factor_ref         0.0593
_refine_ls_wR_factor_gt          0.0558
_refine_ls_goodness_of_fit_ref   1.057
_refine_ls_restrained_S_all      1.057
_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_symmetry_multiplicity
_atom_site_calc_flag
_atom_site_refinement_flags
_atom_site_disorder_assembly
_atom_site_disorder_group
Se1 Se 0.40800(2) 0.199541(12) 0.617844(10) 0.02237(6) Uani 1 1 d . . .
I1 I 0.442540(18) 0.034953(9) 0.638537(8) 0.03411(6) Uani 1 1 d . . .
N1 N 0.37900(19) 0.31185(10) 0.60095(8) 0.0213(4) Uani 1 1 d . . .
C1 C 0.2475(2) 0.21385(12) 0.66391(9) 0.0205(4) Uani 1 1 d . . .
C2 C 0.1812(3) 0.15947(13) 0.69813(11) 0.0281(5) Uani 1 1 d . . .
H2A H 0.2161 0.1081 0.7007 0.034 Uiso 1 1 calc R . .
C3 C 0.0638(3) 0.18119(15) 0.72830(12) 0.0342(6) Uani 1 1 d . . .
H3A H 0.0189 0.1442 0.7520 0.041 Uiso 1 1 calc R . .
C4 C 0.0096(3) 0.25555(15) 0.72505(11) 0.0335(6) Uani 1 1 d . . .
H4A H -0.0727 0.2685 0.7456 0.040 Uiso 1 1 calc R . .
C5 C 0.0748(2) 0.31052(14) 0.69218(11) 0.0273(5) Uani 1 1 d . . .
H5A H 0.0387 0.3617 0.6901 0.033 Uiso 1 1 calc R . .
C6 C 0.1954(2) 0.29008(12) 0.66169(10) 0.0212(4) Uani 1 1 d . . .
C7 C 0.2719(2) 0.34161(13) 0.62597(10) 0.0222(5) Uani 1 1 d . . .
H7A H 0.2457 0.3942 0.6210 0.027 Uiso 1 1 calc R . .
C8 C 0.4766(2) 0.35389(12) 0.56578(10) 0.0230(5) Uani 1 1 d . . .
C9 C 0.4722(2) 0.34295(14) 0.50706(11) 0.0278(5) Uani 1 1 d . . .
C10 C 0.5694(3) 0.38372(15) 0.47446(12) 0.0350(6) Uani 1 1 d . . .
H10A H 0.5692 0.3781 0.4343 0.042 Uiso 1 1 calc R . .
C11 C 0.6654(3) 0.43201(15) 0.49984(12) 0.0380(6) Uani 1 1 d . . .
H11A H 0.7308 0.4593 0.4770 0.046 Uiso 1 1 calc R . .
C12 C 0.6677(3) 0.44111(14) 0.55811(12) 0.0334(6) Uani 1 1 d . . .
H12A H 0.7344 0.4749 0.5748 0.040 Uiso 1 1 calc R . .
C13 C 0.5742(2) 0.40173(13) 0.59299(11) 0.0251(5) Uani 1 1 d . . .
C14 C 0.5813(3) 0.41091(14) 0.65719(11) 0.0301(5) Uani 1 1 d . . .
H14A H 0.5140 0.3731 0.6742 0.036 Uiso 1 1 calc R . .
C15 C 0.5349(5) 0.4915(2) 0.67499(17) 0.0740(12) Uani 1 1 d . . .
H15A H 0.4437 0.5030 0.6580 0.111 Uiso 1 1 calc R . .
H15B H 0.6037 0.5296 0.6619 0.111 Uiso 1 1 calc R . .
H15C H 0.5275 0.4938 0.7165 0.111 Uiso 1 1 calc R . .
C16 C 0.7248(3) 0.3918(2) 0.67994(15) 0.0561(9) Uani 1 1 d . . .
H16A H 0.7259 0.3989 0.7213 0.084 Uiso 1 1 calc R . .
H16B H 0.7941 0.4261 0.6624 0.084 Uiso 1 1 calc R . .
H16C H 0.7476 0.3378 0.6709 0.084 Uiso 1 1 calc R . .
C17 C 0.3699(3) 0.28778(16) 0.47866(12) 0.0358(6) Uani 1 1 d . . .
H17A H 0.3012 0.2706 0.5081 0.043 Uiso 1 1 calc R . .
C18 C 0.4480(4) 0.2156(2) 0.45721(17) 0.0615(10) Uani 1 1 d . . .
H18A H 0.4947 0.1901 0.4893 0.092 Uiso 1 1 calc R . .
H18B H 0.5178 0.2310 0.4289 0.092 Uiso 1 1 calc R . .
H18C H 0.3812 0.1797 0.4398 0.092 Uiso 1 1 calc R . .
C19 C 0.2891(4) 0.3254(3) 0.43090(18) 0.0763(13) Uani 1 1 d . . .
H19A H 0.2369 0.3699 0.4457 0.114 Uiso 1 1 calc R . .
H19B H 0.2236 0.2878 0.4146 0.114 Uiso 1 1 calc R . .
H19C H 0.3542 0.3429 0.4014 0.114 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 1.895(2) . ?
Se1 N1 1.9993(17) . ?
Se1 I1 2.9029(3) . ?
N1 C7 1.288(3) . ?
N1 C8 1.443(3) . ?
C1 C2 1.390(3) . ?
C1 C6 1.409(3) . ?
C2 C3 1.380(3) . ?
C2 H2A 0.9500 . ?
C3 C4 1.387(4) . ?
C3 H3A 0.9500 . ?
C4 C5 1.374(3) . ?
C4 H4A 0.9500 . ?
C5 C6 1.404(3) . ?
C5 H5A 0.9500 . ?
C6 C7 1.426(3) . ?
C7 H7A 0.9500 . ?
C8 C9 1.393(3) . ?
C8 C13 1.401(3) . ?
C9 C10 1.395(3) . ?
C9 C17 1.520(4) . ?
C10 C11 1.377(4) . ?
C10 H10A 0.9500 . ?
C11 C12 1.379(4) . ?
C11 H11A 0.9500 . ?
C12 C13 1.391(3) . ?
C12 H12A 0.9500 . ?
C13 C14 1.519(4) . ?
C14 C16 1.511(4) . ?
C14 C15 1.519(4) . ?
C14 H14A 1.0000 . ?
C15 H15A 0.9800 . ?
C15 H15B 0.9800 . ?
C15 H15C 0.9800 . ?
C16 H16A 0.9800 . ?
C16 H16B 0.9800 . ?
C16 H16C 0.9800 . ?
C17 C19 1.510(4) . ?
C17 C18 1.538(4) . ?
C17 H17A 1.0000 . ?
C18 H18A 0.9800 . ?
C18 H18B 0.9800 . ?
C18 H18C 0.9800 . ?
C19 H19A 0.9800 . ?
C19 H19B 0.9800 . ?
C19 H19C 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
C1 Se1 N1 82.79(8) . . ?
C1 Se1 I1 97.14(6) . . ?
N1 Se1 I1 177.66(6) . . ?
C7 N1 C8 125.12(18) . . ?
C7 N1 Se1 114.01(15) . . ?
C8 N1 Se1 120.81(13) . . ?
C2 C1 C6 119.5(2) . . ?
C2 C1 Se1 127.76(17) . . ?
C6 C1 Se1 112.78(15) . . ?
C3 C2 C1 119.0(2) . . ?
C3 C2 H2A 120.5 . . ?
C1 C2 H2A 120.5 . . ?
C2 C3 C4 121.9(2) . . ?
C2 C3 H3A 119.1 . . ?
C4 C3 H3A 119.1 . . ?
C5 C4 C3 120.1(2) . . ?
C5 C4 H4A 120.0 . . ?
C3 C4 H4A 120.0 . . ?
C4 C5 C6 119.1(2) . . ?
C4 C5 H5A 120.4 . . ?
C6 C5 H5A 120.4 . . ?
C5 C6 C1 120.5(2) . . ?
C5 C6 C7 124.5(2) . . ?
C1 C6 C7 115.1(2) . . ?
N1 C7 C6 115.3(2) . . ?
N1 C7 H7A 122.3 . . ?
C6 C7 H7A 122.3 . . ?
C9 C8 C13 123.5(2) . . ?
C9 C8 N1 118.7(2) . . ?
C13 C8 N1 117.8(2) . . ?
C8 C9 C10 117.1(2) . . ?
C8 C9 C17 122.6(2) . . ?
C10 C9 C17 120.3(2) . . ?
C11 C10 C9 120.8(3) . . ?
C11 C10 H10A 119.6 . . ?
C9 C10 H10A 119.6 . . ?
C10 C11 C12 120.7(2) . . ?
C10 C11 H11A 119.7 . . ?
C12 C11 H11A 119.7 . . ?
C11 C12 C13 121.3(2) . . ?
C11 C12 H12A 119.3 . . ?
C13 C12 H12A 119.3 . . ?
C12 C13 C8 116.6(2) . . ?
C12 C13 C14 120.4(2) . . ?
C8 C13 C14 123.0(2) . . ?
C16 C14 C15 111.6(3) . . ?
C16 C14 C13 111.7(2) . . ?
C15 C14 C13 110.9(2) . . ?
C16 C14 H14A 107.5 . . ?
C15 C14 H14A 107.5 . . ?
C13 C14 H14A 107.5 . . ?
C14 C15 H15A 109.5 . . ?
C14 C15 H15B 109.5 . . ?
H15A C15 H15B 109.5 . . ?
C14 C15 H15C 109.5 . . ?
H15A C15 H15C 109.5 . . ?
H15B C15 H15C 109.5 . . ?
C14 C16 H16A 109.5 . . ?
C14 C16 H16B 109.5 . . ?
H16A C16 H16B 109.5 . . ?
C14 C16 H16C 109.5 . . ?
H16A C16 H16C 109.5 . . ?
H16B C16 H16C 109.5 . . ?
C19 C17 C9 112.7(2) . . ?
C19 C17 C18 110.7(3) . . ?
C9 C17 C18 109.9(2) . . ?
C19 C17 H17A 107.8 . . ?
C9 C17 H17A 107.8 . . ?
C18 C17 H17A 107.8 . . ?
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 . . ?
C17 C19 H19A 109.5 . . ?
C17 C19 H19B 109.5 . . ?
H19A C19 H19B 109.5 . . ?
C17 C19 H19C 109.5 . . ?
H19A C19 H19C 109.5 . . ?
H19B C19 H19C 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


C1 Se1 N1 C7 -0.94(17) . . . . ?
C1 Se1 N1 C8 176.22(18) . . . . ?
N1 Se1 C1 C2 -178.7(2) . . . . ?
I1 Se1 C1 C2 3.6(2) . . . . ?
N1 Se1 C1 C6 0.56(16) . . . . ?
I1 Se1 C1 C6 -177.08(15) . . . . ?
C6 C1 C2 C3 1.3(4) . . . . ?
Se1 C1 C2 C3 -179.42(19) . . . . ?
C1 C2 C3 C4 0.5(4) . . . . ?
C2 C3 C4 C5 -1.6(4) . . . . ?
C3 C4 C5 C6 0.7(4) . . . . ?
C4 C5 C6 C1 1.2(4) . . . . ?
C4 C5 C6 C7 179.7(2) . . . . ?
C2 C1 C6 C5 -2.2(3) . . . . ?
Se1 C1 C6 C5 178.45(18) . . . . ?
C2 C1 C6 C7 179.2(2) . . . . ?
Se1 C1 C6 C7 -0.2(3) . . . . ?
C8 N1 C7 C6 -175.9(2) . . . . ?
Se1 N1 C7 C6 1.1(3) . . . . ?
C5 C6 C7 N1 -179.2(2) . . . . ?
C1 C6 C7 N1 -0.6(3) . . . . ?
C7 N1 C8 C9 -106.7(3) . . . . ?
Se1 N1 C8 C9 76.5(2) . . . . ?
C7 N1 C8 C13 75.4(3) . . . . ?
Se1 N1 C8 C13 -101.4(2) . . . . ?
C13 C8 C9 C10 -1.4(3) . . . . ?
N1 C8 C9 C10 -179.1(2) . . . . ?
C13 C8 C9 C17 177.0(2) . . . . ?
N1 C8 C9 C17 -0.8(3) . . . . ?
C8 C9 C10 C11 0.4(4) . . . . ?
C17 C9 C10 C11 -177.9(2) . . . . ?
C9 C10 C11 C12 0.0(4) . . . . ?
C10 C11 C12 C13 0.4(4) . . . . ?
C11 C12 C13 C8 -1.2(4) . . . . ?
C11 C12 C13 C14 178.3(2) . . . . ?
C9 C8 C13 C12 1.7(3) . . . . ?
N1 C8 C13 C12 179.5(2) . . . . ?
C9 C8 C13 C14 -177.7(2) . . . . ?
N1 C8 C13 C14 0.1(3) . . . . ?
C12 C13 C14 C16 -55.3(3) . . . . ?
C8 C13 C14 C16 124.1(3) . . . . ?
C12 C13 C14 C15 69.8(3) . . . . ?
C8 C13 C14 C15 -110.7(3) . . . . ?
C8 C9 C17 C19 128.6(3) . . . . ?
C10 C9 C17 C19 -53.1(4) . . . . ?
C8 C9 C17 C18 -107.4(3) . . . . ?
C10 C9 C17 C18 70.9(3) . . . . ?

loop_
_geom_hbond_atom_site_label_D
_geom_hbond_atom_site_label_H
_geom_hbond_atom_site_label_A
_geom_hbond_distance_DH
_geom_hbond_distance_HA
_geom_hbond_distance_DA
_geom_hbond_angle_DHA
_geom_hbond_site_symmetry_A
C2 H2A I1 0.95 2.90 3.583(2) 129.6 .

_diffrn_measured_fraction_theta_max 0.999
_diffrn_reflns_theta_full        25.00
_diffrn_measured_fraction_theta_full 0.998
_refine_diff_density_max         0.624
_refine_diff_density_min         -0.665
_refine_diff_density_rms         0.075
_database_code_depnum_ccdc_archive 'CCDC 959144'
#######################################################################
#
#                 Cambridge Crystallographic Data Centre
#                                CCDC 
# 
#######################################################################
# 
#  This CIF contains data from an original supplementary publication
#  deposited with the CCDC, and may include chemical, crystal,
#  experimental, refinement, atomic coordinates,
#  anisotropic displacement parameters and molecular geometry data,
#  as required by the journal to which it was submitted.
#
#  This CIF is provided on the understanding that it is used for bona
#  fide research purposes only. It may contain copyright material
#  of the CCDC or of third parties, and may not be copied or further
#  disseminated in any form, whether machine-readable or not,
#  except for the purpose of generating routine backup copies
#  on your local computer system.
# 
#  For further information on the CCDC, data deposition and
#  data retrieval see:
#                         www.ccdc.cam.ac.uk
#
#  Bona fide researchers may freely download Mercury and enCIFer
#  from this site to visualise CIF-encoded structures and 
#  to carry out CIF format checking respectively.
#
data_hbs-17

_audit_creation_method           SHELXL-97
_chemical_name_systematic        
; 
 ? 
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         'C20 H22 N2 Se2'
_chemical_formula_sum            'C20 H22 N2 Se2'
_chemical_formula_weight         448.32

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'

_symmetry_cell_setting           Monoclinic
_symmetry_space_group_name_H-M   P2(1)/c
_symmetry_space_group_name_Hall  '-P 2ybc'

loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'-x, y+1/2, -z+1/2'
'-x, -y, -z'
'x, -y-1/2, z-1/2'

_cell_length_a                   10.0205(6)
_cell_length_b                   11.4514(8)
_cell_length_c                   16.4769(12)
_cell_angle_alpha                90.00
_cell_angle_beta                 97.148(6)
_cell_angle_gamma                90.00
_cell_volume                     1876.0(2)
_cell_formula_units_Z            4
_cell_measurement_temperature    173(2)
_cell_measurement_reflns_used    5057
_cell_measurement_theta_min      3.02
_cell_measurement_theta_max      32.23

_exptl_crystal_description       block
_exptl_crystal_colour            yellow
_exptl_crystal_size_max          0.28
_exptl_crystal_size_mid          0.18
_exptl_crystal_size_min          0.08
_exptl_crystal_density_meas      ?
_exptl_crystal_density_diffrn    1.587
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             896
_exptl_absorpt_coefficient_mu    3.945
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.4046
_exptl_absorpt_correction_T_max  0.7431
_exptl_absorpt_process_details   'CrysAlisRED; Oxford Diffraction, 2010.'

_exptl_special_details           
; 
 ? 
;

_diffrn_ambient_temperature      173(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_radiation_source         'Enhance (Mo) X-ray Source'
_diffrn_radiation_monochromator  graphite
_diffrn_measurement_device_type  'Xcalibur, Eos, Gemini'
_diffrn_detector_area_resol_mean 16.1500
_diffrn_measurement_method       ' ω scans'

_diffrn_reflns_number            18873
_diffrn_reflns_av_R_equivalents  0.0511
_diffrn_reflns_av_sigmaI/netI    0.0459
_diffrn_reflns_limit_h_min       -13
_diffrn_reflns_limit_h_max       12
_diffrn_reflns_limit_k_min       -13
_diffrn_reflns_limit_k_max       15
_diffrn_reflns_limit_l_min       -22
_diffrn_reflns_limit_l_max       22
_diffrn_reflns_theta_min         3.02
_diffrn_reflns_theta_max         28.70
_reflns_number_total             4851
_reflns_number_gt                3938
_reflns_threshold_expression     >2sigma(I)

_computing_data_collection       'CrysAlisPRO (Oxford Diffraction, 2010)'
_computing_cell_refinement       'CrysAlisPRO (Oxford Diffraction, 2010)'
_computing_data_reduction        'CrysAlisRED (Oxford Diffraction, 2010)'
_computing_structure_solution    'SHELXS97 (Sheldrick, 2008)'
_computing_structure_refinement  'SHELXL97 (Sheldrick, 2008)'
_computing_molecular_graphics    'SHELXTL (Bruker, 2000)'
_computing_publication_material  'SHELXTL (Bruker, 2000)'

_refine_special_details          
; 
Refinement of F² against ALL reflections. The weighted R-factor
wR and goodness of fit S are based on F², conventional
R-factors R are based on F, with F set to zero for
negative F². The threshold expression of F² >
σ(F²) is used only for calculating R-factors(gt) etc.
and is not relevant to the choice of reflections for refinement.
R-factors based on F² are statistically about twice as large
as those based on F, and R- factors based on ALL data will be
even larger. 
;

_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'calc w=1/[σ²(Fo²)+(0.0362P)²+0.4115P] 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_number_reflns         4851
_refine_ls_number_parameters     221
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0493
_refine_ls_R_factor_gt           0.0344
_refine_ls_wR_factor_ref         0.0820
_refine_ls_wR_factor_gt          0.0754
_refine_ls_goodness_of_fit_ref   1.041
_refine_ls_restrained_S_all      1.041
_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_symmetry_multiplicity
_atom_site_calc_flag
_atom_site_refinement_flags
_atom_site_disorder_assembly
_atom_site_disorder_group
Se1 Se 0.49035(3) 0.69800(2) 0.557884(15) 0.02188(8) Uani 1 1 d . . .
Se2 Se 0.71165(3) 0.59381(2) 0.530405(16) 0.02630(8) Uani 1 1 d . . .
N1 N 0.2983(2) 0.76838(18) 0.56937(12) 0.0196(4) Uani 1 1 d . . .
N2 N 0.9105(3) 0.6721(2) 0.66889(16) 0.0400(6) Uani 1 1 d . . .
C1 C 0.4269(3) 0.5803(2) 0.62641(14) 0.0186(5) Uani 1 1 d . . .
C2 C 0.4933(3) 0.4774(2) 0.65208(15) 0.0233(5) Uani 1 1 d . . .
H2A H 0.5802 0.4612 0.6373 0.028 Uiso 1 1 calc R . .
C3 C 0.4315(3) 0.3990(2) 0.69922(16) 0.0283(6) Uani 1 1 d . . .
H3A H 0.4769 0.3288 0.7166 0.034 Uiso 1 1 calc R . .
C4 C 0.3051(3) 0.4205(2) 0.72170(16) 0.0295(6) Uani 1 1 d . . .
H4A H 0.2649 0.3658 0.7546 0.035 Uiso 1 1 calc R . .
C5 C 0.2378(3) 0.5216(2) 0.69615(15) 0.0259(6) Uani 1 1 d . . .
H5A H 0.1508 0.5367 0.7109 0.031 Uiso 1 1 calc R . .
C6 C 0.2987(3) 0.6019(2) 0.64827(14) 0.0206(5) Uani 1 1 d . . .
C7 C 0.2313(3) 0.7051(2) 0.61403(14) 0.0212(5) Uani 1 1 d . . .
H7A H 0.1427 0.7250 0.6240 0.025 Uiso 1 1 calc R . .
C8 C 0.2414(3) 0.8631(2) 0.51928(14) 0.0197(5) Uani 1 1 d . . .
C9 C 0.1703(3) 0.8343(2) 0.44288(15) 0.0214(5) Uani 1 1 d . . .
C10 C 0.1134(3) 0.9265(2) 0.39540(16) 0.0259(6) Uani 1 1 d . . .
H10A H 0.0619 0.9102 0.3443 0.031 Uiso 1 1 calc R . .
C11 C 0.1301(3) 1.0411(2) 0.42090(17) 0.0300(6) Uani 1 1 d . . .
H11A H 0.0897 1.1025 0.3877 0.036 Uiso 1 1 calc R . .
C12 C 0.2058(3) 1.0665(2) 0.49487(17) 0.0284(6) Uani 1 1 d . . .
H12A H 0.2186 1.1457 0.5112 0.034 Uiso 1 1 calc R . .
C13 C 0.2636(3) 0.9782(2) 0.54599(15) 0.0220(5) Uani 1 1 d . . .
C14 C 0.3480(3) 1.0085(2) 0.62619(16) 0.0250(6) Uani 1 1 d . . .
H14A H 0.3743 0.9337 0.6552 0.030 Uiso 1 1 calc R . .
C15 C 0.2678(4) 1.0802(3) 0.68103(18) 0.0436(8) Uani 1 1 d . . .
H15A H 0.1859 1.0377 0.6898 0.065 Uiso 1 1 calc R . .
H15B H 0.2433 1.1553 0.6548 0.065 Uiso 1 1 calc R . .
H15C H 0.3225 1.0938 0.7337 0.065 Uiso 1 1 calc R . .
C16 C 0.4762(4) 1.0718(3) 0.6120(2) 0.0439(8) Uani 1 1 d . . .
H16A H 0.5296 1.0219 0.5800 0.066 Uiso 1 1 calc R . .
H16B H 0.5284 1.0900 0.6648 0.066 Uiso 1 1 calc R . .
H16C H 0.4532 1.1444 0.5820 0.066 Uiso 1 1 calc R . .
C17 C 0.1533(3) 0.7094(2) 0.41334(15) 0.0238(5) Uani 1 1 d . . .
H17A H 0.2243 0.6617 0.4460 0.029 Uiso 1 1 calc R . .
C18 C 0.0174(3) 0.6604(3) 0.4290(2) 0.0414(8) Uani 1 1 d . . .
H18A H 0.0060 0.6711 0.4867 0.062 Uiso 1 1 calc R . .
H18B H 0.0135 0.5770 0.4156 0.062 Uiso 1 1 calc R . .
H18C H -0.0545 0.7016 0.3947 0.062 Uiso 1 1 calc R . .
C19 C 0.1731(4) 0.6961(3) 0.32355(17) 0.0404(8) Uani 1 1 d . . .
H19A H 0.2599 0.7298 0.3145 0.061 Uiso 1 1 calc R . .
H19B H 0.1006 0.7369 0.2894 0.061 Uiso 1 1 calc R . .
H19C H 0.1715 0.6131 0.3090 0.061 Uiso 1 1 calc R . .
C20 C 0.8303(3) 0.6436(2) 0.61688(17) 0.0267(6) Uani 1 1 d . . .


_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 1.917(2) . ?
Se1 N1 2.116(2) . ?
Se1 Se2 2.6069(4) . ?
Se2 C20 1.830(3) . ?
N1 C7 1.281(3) . ?
N1 C8 1.437(3) . ?
N2 C20 1.147(4) . ?
C1 C2 1.394(3) . ?
C1 C6 1.398(4) . ?
C2 C3 1.382(4) . ?
C2 H2A 0.9500 . ?
C3 C4 1.386(4) . ?
C3 H3A 0.9500 . ?
C4 C5 1.379(4) . ?
C4 H4A 0.9500 . ?
C5 C6 1.400(4) . ?
C5 H5A 0.9500 . ?
C6 C7 1.441(3) . ?
C7 H7A 0.9500 . ?
C8 C13 1.399(4) . ?
C8 C9 1.406(3) . ?
C9 C10 1.393(3) . ?
C9 C17 1.514(4) . ?
C10 C11 1.382(4) . ?
C10 H10A 0.9500 . ?
C11 C12 1.384(4) . ?
C11 H11A 0.9500 . ?
C12 C13 1.395(4) . ?
C12 H12A 0.9500 . ?
C13 C14 1.518(4) . ?
C14 C16 1.518(4) . ?
C14 C15 1.523(4) . ?
C14 H14A 1.0000 . ?
C15 H15A 0.9800 . ?
C15 H15B 0.9800 . ?
C15 H15C 0.9800 . ?
C16 H16A 0.9800 . ?
C16 H16B 0.9800 . ?
C16 H16C 0.9800 . ?
C17 C18 1.524(4) . ?
C17 C19 1.525(4) . ?
C17 H17A 1.0000 . ?
C18 H18A 0.9800 . ?
C18 H18B 0.9800 . ?
C18 H18C 0.9800 . ?
C19 H19A 0.9800 . ?
C19 H19B 0.9800 . ?
C19 H19C 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
C1 Se1 N1 80.97(9) . . ?
C1 Se1 Se2 97.60(8) . . ?
N1 Se1 Se2 172.93(6) . . ?
C20 Se2 Se1 101.93(9) . . ?
C7 N1 C8 123.9(2) . . ?
C7 N1 Se1 112.57(17) . . ?
C8 N1 Se1 122.44(16) . . ?
C2 C1 C6 119.4(2) . . ?
C2 C1 Se1 126.3(2) . . ?
C6 C1 Se1 114.21(17) . . ?
C3 C2 C1 119.2(3) . . ?
C3 C2 H2A 120.4 . . ?
C1 C2 H2A 120.4 . . ?
C2 C3 C4 121.6(2) . . ?
C2 C3 H3A 119.2 . . ?
C4 C3 H3A 119.2 . . ?
C5 C4 C3 119.7(3) . . ?
C5 C4 H4A 120.1 . . ?
C3 C4 H4A 120.1 . . ?
C4 C5 C6 119.5(3) . . ?
C4 C5 H5A 120.2 . . ?
C6 C5 H5A 120.2 . . ?
C1 C6 C5 120.5(2) . . ?
C1 C6 C7 116.4(2) . . ?
C5 C6 C7 122.9(2) . . ?
N1 C7 C6 115.8(2) . . ?
N1 C7 H7A 122.1 . . ?
C6 C7 H7A 122.1 . . ?
C13 C8 C9 123.0(2) . . ?
C13 C8 N1 119.6(2) . . ?
C9 C8 N1 117.3(2) . . ?
C10 C9 C8 116.8(2) . . ?
C10 C9 C17 120.9(2) . . ?
C8 C9 C17 122.2(2) . . ?
C11 C10 C9 121.6(2) . . ?
C11 C10 H10A 119.2 . . ?
C9 C10 H10A 119.2 . . ?
C10 C11 C12 120.0(2) . . ?
C10 C11 H11A 120.0 . . ?
C12 C11 H11A 120.0 . . ?
C11 C12 C13 121.4(3) . . ?
C11 C12 H12A 119.3 . . ?
C13 C12 H12A 119.3 . . ?
C12 C13 C8 117.1(2) . . ?
C12 C13 C14 120.4(2) . . ?
C8 C13 C14 122.6(2) . . ?
C13 C14 C16 111.4(2) . . ?
C13 C14 C15 111.2(2) . . ?
C16 C14 C15 110.7(3) . . ?
C13 C14 H14A 107.8 . . ?
C16 C14 H14A 107.8 . . ?
C15 C14 H14A 107.8 . . ?
C14 C15 H15A 109.5 . . ?
C14 C15 H15B 109.5 . . ?
H15A C15 H15B 109.5 . . ?
C14 C15 H15C 109.5 . . ?
H15A C15 H15C 109.5 . . ?
H15B C15 H15C 109.5 . . ?
C14 C16 H16A 109.5 . . ?
C14 C16 H16B 109.5 . . ?
H16A C16 H16B 109.5 . . ?
C14 C16 H16C 109.5 . . ?
H16A C16 H16C 109.5 . . ?
H16B C16 H16C 109.5 . . ?
C9 C17 C18 111.2(2) . . ?
C9 C17 C19 112.5(2) . . ?
C18 C17 C19 110.8(2) . . ?
C9 C17 H17A 107.4 . . ?
C18 C17 H17A 107.4 . . ?
C19 C17 H17A 107.4 . . ?
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 . . ?
C17 C19 H19A 109.5 . . ?
C17 C19 H19B 109.5 . . ?
H19A C19 H19B 109.5 . . ?
C17 C19 H19C 109.5 . . ?
H19A C19 H19C 109.5 . . ?
H19B C19 H19C 109.5 . . ?
N2 C20 Se2 176.1(3) . . ?

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



C1 Se1 Se2 C20 -87.89(11) . . . . ?
C1 Se1 N1 C7 0.20(17) . . . . ?
C1 Se1 N1 C8 -168.2(2) . . . . ?
N1 Se1 C1 C2 175.8(2) . . . . ?
Se2 Se1 C1 C2 2.8(2) . . . . ?
N1 Se1 C1 C6 -1.44(17) . . . . ?
Se2 Se1 C1 C6 -174.44(16) . . . . ?
C6 C1 C2 C3 -0.5(4) . . . . ?
Se1 C1 C2 C3 -177.65(19) . . . . ?
C1 C2 C3 C4 -0.1(4) . . . . ?
C2 C3 C4 C5 0.6(4) . . . . ?
C3 C4 C5 C6 -0.5(4) . . . . ?
C2 C1 C6 C5 0.6(3) . . . . ?
Se1 C1 C6 C5 178.09(19) . . . . ?
C2 C1 C6 C7 -175.0(2) . . . . ?
Se1 C1 C6 C7 2.5(3) . . . . ?
C4 C5 C6 C1 -0.1(4) . . . . ?
C4 C5 C6 C7 175.2(2) . . . . ?
C8 N1 C7 C6 169.2(2) . . . . ?
Se1 N1 C7 C6 1.1(3) . . . . ?
C1 C6 C7 N1 -2.3(3) . . . . ?
C5 C6 C7 N1 -177.8(2) . . . . ?
C7 N1 C8 C13 102.1(3) . . . . ?
Se1 N1 C8 C13 -90.9(3) . . . . ?
C7 N1 C8 C9 -80.9(3) . . . . ?
Se1 N1 C8 C9 86.2(3) . . . . ?
C13 C8 C9 C10 -4.2(4) . . . . ?
N1 C8 C9 C10 178.9(2) . . . . ?
C13 C8 C9 C17 176.9(2) . . . . ?
N1 C8 C9 C17 0.0(4) . . . . ?
C8 C9 C10 C11 2.3(4) . . . . ?
C17 C9 C10 C11 -178.8(3) . . . . ?
C9 C10 C11 C12 0.5(5) . . . . ?
C10 C11 C12 C13 -1.6(5) . . . . ?
C11 C12 C13 C8 -0.2(4) . . . . ?
C11 C12 C13 C14 179.0(3) . . . . ?
C9 C8 C13 C12 3.2(4) . . . . ?
N1 C8 C13 C12 -179.9(2) . . . . ?
C9 C8 C13 C14 -176.0(2) . . . . ?
N1 C8 C13 C14 0.9(4) . . . . ?
C12 C13 C14 C16 -65.9(4) . . . . ?
C8 C13 C14 C16 113.3(3) . . . . ?
C12 C13 C14 C15 58.0(4) . . . . ?
C8 C13 C14 C15 -122.8(3) . . . . ?
C10 C9 C17 C18 -81.1(3) . . . . ?
C8 C9 C17 C18 97.7(3) . . . . ?
C10 C9 C17 C19 43.8(4) . . . . ?
C8 C9 C17 C19 -137.4(3) . . . . ?


loop_
_geom_hbond_atom_site_label_D
_geom_hbond_atom_site_label_H
_geom_hbond_atom_site_label_A
_geom_hbond_distance_DH
_geom_hbond_distance_HA
_geom_hbond_distance_DA
_geom_hbond_angle_DHA
_geom_hbond_site_symmetry_A
C2 H2A Se2 0.95 2.78 3.417(3) 125.2 .
C7 H7A N2 0.95 2.60 3.467(4) 151.8 1_455

_diffrn_measured_fraction_theta_max 0.999
_diffrn_reflns_theta_full        25.00
_diffrn_measured_fraction_theta_full 0.998
_refine_diff_density_max         0.988
_refine_diff_density_min         -0.529
_refine_diff_density_rms         0.093
_database_code_depnum_ccdc_archive 'CCDC 959145'
