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

####################################################################### 
# 
# This file contains crystal structure data downloaded from the 
# Cambridge Structural Database (CSD) hosted by the Cambridge 
# Crystallographic Data Centre (CCDC).
# 
# Full information about CCDC data access policies and citation 
# guidelines are available at http://www.ccdc.cam.ac.uk/access/V1 
# 
# Audit and citation data items may have been added by the CCDC. 
# Please retain this information to preserve the provenance of 
# this file and to allow appropriate attribution of the data. 
# 
#######################################################################

data_ch13687
_audit_block_doi                 10.5517/ccyn5d4
_database_code_depnum_ccdc_archive 'CCDC 883326'
_audit_update_record             
;
2012-05-22 deposited with the CCDC.
2015-10-22 downloaded from the CCDC.
;
#TrackingRef '11436_web_deposit_cif_file_0_wong-jin-chang_1337660280.ch13687.cif'


_audit_creation_method           SHELXL-97
_chemical_name_systematic        
;
?
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         'C29 H24 N2 O2 Se'
_chemical_formula_sum            'C29 H24 N2 O2 Se'
_chemical_formula_weight         511.46

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'
O O 0.0106 0.0060 '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           orthorhombic
_symmetry_space_group_name_H-M   'P 21 21 21'

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'

_cell_length_a                   8.7794(3)
_cell_length_b                   14.6701(4)
_cell_length_c                   37.5122(10)
_cell_angle_alpha                90.00
_cell_angle_beta                 90.00
_cell_angle_gamma                90.00
_cell_volume                     4831.4(2)
_cell_formula_units_Z            8
_cell_measurement_temperature    200(2)
_cell_measurement_reflns_used    0
_cell_measurement_theta_min      0
_cell_measurement_theta_max      0

_exptl_crystal_description       prism
_exptl_crystal_colour            colorless
_exptl_crystal_size_max          0.78
_exptl_crystal_size_mid          0.74
_exptl_crystal_size_min          0.67
_exptl_crystal_density_meas      ?
_exptl_crystal_density_diffrn    1.406
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             2096
_exptl_absorpt_coefficient_mu    1.583
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.3714
_exptl_absorpt_correction_T_max  0.4168
_exptl_absorpt_process_details   ?

_exptl_special_details           
;
?
;

_diffrn_ambient_temperature      200(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_radiation_source         'fine-focus sealed tube'
_diffrn_radiation_monochromator  graphite
_diffrn_measurement_device_type  ?
_diffrn_measurement_method       ?
_diffrn_detector_area_resol_mean ?
_diffrn_standards_number         ?
_diffrn_standards_interval_count ?
_diffrn_standards_interval_time  ?
_diffrn_standards_decay_%        ?
_diffrn_reflns_number            19306
_diffrn_reflns_av_R_equivalents  0.0336
_diffrn_reflns_av_sigmaI/netI    0.0612
_diffrn_reflns_limit_h_min       -3
_diffrn_reflns_limit_h_max       9
_diffrn_reflns_limit_k_min       -17
_diffrn_reflns_limit_k_max       17
_diffrn_reflns_limit_l_min       -44
_diffrn_reflns_limit_l_max       44
_diffrn_reflns_theta_min         2.70
_diffrn_reflns_theta_max         25.00
_reflns_number_total             8037
_reflns_number_gt                6940
_reflns_threshold_expression     >2sigma(I)

_computing_data_collection       ?
_computing_cell_refinement       ?
_computing_data_reduction        ?
_computing_structure_solution    'SHELXS-86 (Sheldrick, 1986)'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_computing_molecular_graphics    'Ortep-3 for Windows (Farrugia, 1997)'
_computing_publication_material  'WinGX publication routines (Farrugia, 1999)'

_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)+(0.0193P)²+0.0000P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_atom_sites_solution_hydrogens   geom
_refine_ls_hydrogen_treatment    constr
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       ?
_refine_ls_abs_structure_details 'Flack H D (1983), Acta Cryst. A39, 876-881'
_refine_ls_abs_structure_Flack   0.023(7)
_refine_ls_number_reflns         8037
_refine_ls_number_parameters     613
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0453
_refine_ls_R_factor_gt           0.0350
_refine_ls_wR_factor_ref         0.0708
_refine_ls_wR_factor_gt          0.0679
_refine_ls_goodness_of_fit_ref   1.011
_refine_ls_restrained_S_all      1.011
_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
C1 C 0.7308(4) 0.0489(2) 0.97906(8) 0.0281(8) Uani 1 1 d . . .
C2 C 0.7920(4) 0.0018(2) 1.03729(8) 0.0298(8) Uani 1 1 d . . .
C3 C 0.6801(4) 0.0414(2) 1.05814(9) 0.0383(9) Uani 1 1 d . . .
H3 H 0.6247 0.0924 1.0494 0.046 Uiso 1 1 calc R . .
C4 C 0.6487(5) 0.0067(3) 1.09168(9) 0.0476(10) Uani 1 1 d . . .
H4 H 0.5709 0.0339 1.1057 0.057 Uiso 1 1 calc R . .
C5 C 0.7285(5) -0.0663(3) 1.10489(10) 0.0475(11) Uani 1 1 d . . .
H5 H 0.7054 -0.0902 1.1278 0.057 Uiso 1 1 calc R . .
C6 C 0.8414(5) -0.1043(2) 1.08469(9) 0.0451(10) Uani 1 1 d . . .
H6 H 0.8975 -0.1544 1.0939 0.054 Uiso 1 1 calc R . .
C7 C 0.8753(4) -0.0711(2) 1.05133(9) 0.0373(9) Uani 1 1 d . . .
H7 H 0.9553 -0.0977 1.0378 0.045 Uiso 1 1 calc R . .
C8 C 0.9257(4) 0.1037(2) 0.93748(8) 0.0267(8) Uani 1 1 d . . .
H8 H 0.9317 0.1135 0.9111 0.032 Uiso 1 1 calc R . .
C9 C 1.0458(4) 0.0327(2) 0.94641(8) 0.0323(8) Uani 1 1 d . . .
C10 C 1.1072(5) -0.1226(2) 0.94615(10) 0.0518(11) Uani 1 1 d . . .
H10A H 1.0639 -0.1817 0.9393 0.078 Uiso 1 1 calc R . .
H10B H 1.1295 -0.1226 0.9717 0.078 Uiso 1 1 calc R . .
H10C H 1.2014 -0.1121 0.9328 0.078 Uiso 1 1 calc R . .
C11 C 0.9619(4) 0.1958(2) 0.95469(8) 0.0355(9) Uani 1 1 d . . .
H11A H 0.9521 0.1905 0.9809 0.043 Uiso 1 1 calc R . .
H11B H 1.0684 0.2129 0.9492 0.043 Uiso 1 1 calc R . .
C12 C 0.8559(4) 0.2697(2) 0.94139(8) 0.0323(8) Uani 1 1 d . . .
C13 C 0.8632(5) 0.3001(2) 0.90638(9) 0.0442(10) Uani 1 1 d . . .
H13 H 0.9368 0.2749 0.8906 0.053 Uiso 1 1 calc R . .
C14 C 0.7650(5) 0.3666(3) 0.89415(11) 0.0541(11) Uani 1 1 d . . .
H14 H 0.7696 0.3859 0.8700 0.065 Uiso 1 1 calc R . .
C15 C 0.6603(6) 0.4049(3) 0.91698(12) 0.0582(12) Uani 1 1 d . . .
H15 H 0.5931 0.4510 0.9087 0.070 Uiso 1 1 calc R . .
C16 C 0.6534(5) 0.3765(3) 0.95179(12) 0.0629(12) Uani 1 1 d . . .
H16 H 0.5819 0.4033 0.9676 0.075 Uiso 1 1 calc R . .
C17 C 0.7502(5) 0.3090(3) 0.96381(10) 0.0473(10) Uani 1 1 d . . .
H17 H 0.7439 0.2894 0.9879 0.057 Uiso 1 1 calc R . .
C18 C 0.6551(4) 0.0741(2) 0.91945(8) 0.0288(8) Uani 1 1 d . . .
C19 C 0.6951(4) 0.0771(2) 0.88083(9) 0.0315(8) Uani 1 1 d . . .
C20 C 0.7774(4) 0.0021(2) 0.86634(9) 0.0360(9) Uani 1 1 d . . .
H20 H 0.8079 -0.0467 0.8814 0.043 Uiso 1 1 calc R . .
C21 C 0.8126(5) 0.0002(2) 0.83090(9) 0.0398(9) Uani 1 1 d . . .
H21 H 0.8660 -0.0506 0.8214 0.048 Uiso 1 1 calc R . .
C22 C 0.7709(4) 0.0721(2) 0.80845(9) 0.0346(9) Uani 1 1 d . . .
C23 C 0.6907(4) 0.1481(2) 0.82258(9) 0.0325(8) Uani 1 1 d . . .
C24 C 0.6524(4) 0.1473(2) 0.85964(9) 0.0357(8) Uani 1 1 d . . .
H24 H 0.5964 0.1967 0.8695 0.043 Uiso 1 1 calc R . .
C25 C 0.6564(5) 0.2214(2) 0.80026(10) 0.0445(10) Uani 1 1 d . . .
H25 H 0.6048 0.2729 0.8097 0.053 Uiso 1 1 calc R . .
C26 C 0.6961(5) 0.2201(3) 0.76515(9) 0.0458(10) Uani 1 1 d . . .
H26 H 0.6719 0.2708 0.7505 0.055 Uiso 1 1 calc R . .
C27 C 0.7718(5) 0.1452(3) 0.75036(10) 0.0468(11) Uani 1 1 d . . .
H27 H 0.7975 0.1450 0.7258 0.056 Uiso 1 1 calc R . .
C28 C 0.8084(4) 0.0730(2) 0.77118(9) 0.0415(10) Uani 1 1 d . . .
H28 H 0.8595 0.0223 0.7610 0.050 Uiso 1 1 calc R . .
C29 C 0.5154(4) 0.0621(2) 0.93244(7) 0.0322(8) Uani 1 1 d . . .
H29 H 0.4262 0.0629 0.9181 0.039 Uiso 1 1 calc R . .
C30 C 0.7617(4) 0.7512(2) 0.85363(8) 0.0285(7) Uani 1 1 d . . .
C31 C 0.7189(4) 0.7385(2) 0.91419(8) 0.0300(8) Uani 1 1 d . . .
C32 C 0.8126(5) 0.6678(2) 0.92533(10) 0.0437(10) Uani 1 1 d . . .
H32 H 0.8434 0.6224 0.9087 0.052 Uiso 1 1 calc R . .
C33 C 0.8614(5) 0.6625(3) 0.96006(10) 0.0517(11) Uani 1 1 d . . .
H33 H 0.9253 0.6137 0.9673 0.062 Uiso 1 1 calc R . .
C34 C 0.8178(5) 0.7282(3) 0.98451(9) 0.0480(10) Uani 1 1 d . . .
H34 H 0.8536 0.7253 1.0084 0.058 Uiso 1 1 calc R . .
C35 C 0.7227(5) 0.7975(3) 0.97416(9) 0.0430(10) Uani 1 1 d . . .
H35 H 0.6913 0.8420 0.9910 0.052 Uiso 1 1 calc R . .
C36 C 0.6724(4) 0.8030(2) 0.93933(9) 0.0357(9) Uani 1 1 d . . .
H36 H 0.6057 0.8508 0.9324 0.043 Uiso 1 1 calc R . .
C37 C 0.5638(4) 0.7206(2) 0.80934(8) 0.0296(8) Uani 1 1 d . . .
H37 H 0.5522 0.7269 0.7829 0.036 Uiso 1 1 calc R . .
C38 C 0.4427(4) 0.7803(2) 0.82635(8) 0.0300(8) Uani 1 1 d . . .
C39 C 0.3846(5) 0.9289(2) 0.84635(10) 0.0517(11) Uani 1 1 d . . .
H39A H 0.4262 0.9909 0.8455 0.078 Uiso 1 1 calc R . .
H39B H 0.3760 0.9092 0.8712 0.078 Uiso 1 1 calc R . .
H39C H 0.2837 0.9282 0.8352 0.078 Uiso 1 1 calc R . .
C40 C 0.5370(4) 0.6193(2) 0.81840(8) 0.0356(9) Uani 1 1 d . . .
H40A H 0.5414 0.6111 0.8446 0.043 Uiso 1 1 calc R . .
H40B H 0.4340 0.6012 0.8103 0.043 Uiso 1 1 calc R . .
C41 C 0.6532(4) 0.5584(2) 0.80111(9) 0.0365(9) Uani 1 1 d . . .
C42 C 0.6332(5) 0.5266(2) 0.76658(10) 0.0501(10) Uani 1 1 d . . .
H42 H 0.5450 0.5434 0.7535 0.060 Uiso 1 1 calc R . .
C43 C 0.7424(6) 0.4701(3) 0.75110(11) 0.0627(14) Uani 1 1 d . . .
H43 H 0.7290 0.4493 0.7273 0.075 Uiso 1 1 calc R . .
C44 C 0.8687(6) 0.4443(3) 0.76994(13) 0.0625(13) Uani 1 1 d . . .
H44 H 0.9409 0.4042 0.7595 0.075 Uiso 1 1 calc R . .
C45 C 0.8908(5) 0.4760(3) 0.80349(13) 0.0600(12) Uani 1 1 d . . .
H45 H 0.9800 0.4595 0.8163 0.072 Uiso 1 1 calc R . .
C46 C 0.7828(5) 0.5325(2) 0.81903(10) 0.0454(10) Uani 1 1 d . . .
H46 H 0.7988 0.5537 0.8427 0.054 Uiso 1 1 calc R . .
C47 C 0.8325(4) 0.76379(19) 0.79296(8) 0.0268(7) Uani 1 1 d . . .
C48 C 0.7896(4) 0.7742(2) 0.75441(8) 0.0295(8) Uani 1 1 d . . .
C49 C 0.8359(4) 0.7117(2) 0.72958(9) 0.0383(9) Uani 1 1 d . . .
H49 H 0.8927 0.6598 0.7369 0.046 Uiso 1 1 calc R . .
C50 C 0.7991(4) 0.7239(2) 0.69266(9) 0.0388(9) Uani 1 1 d . . .
C51 C 0.7206(5) 0.8027(3) 0.68237(10) 0.0449(10) Uani 1 1 d . . .
C52 C 0.6758(5) 0.8664(2) 0.70801(10) 0.0454(10) Uani 1 1 d . . .
H52 H 0.6238 0.9202 0.7008 0.055 Uiso 1 1 calc R . .
C53 C 0.7058(4) 0.8521(2) 0.74322(9) 0.0382(9) Uani 1 1 d . . .
H53 H 0.6704 0.8945 0.7605 0.046 Uiso 1 1 calc R . .
C54 C 0.6846(5) 0.8149(3) 0.64519(11) 0.0593(12) Uani 1 1 d . . .
H54 H 0.6366 0.8693 0.6373 0.071 Uiso 1 1 calc R . .
C55 C 0.7195(5) 0.7484(4) 0.62171(11) 0.0674(13) Uani 1 1 d . . .
H55 H 0.6924 0.7557 0.5974 0.081 Uiso 1 1 calc R . .
C56 C 0.7945(5) 0.6690(4) 0.63242(11) 0.0619(13) Uani 1 1 d . . .
H56 H 0.8172 0.6231 0.6154 0.074 Uiso 1 1 calc R . .
C57 C 0.8356(5) 0.6568(3) 0.66730(10) 0.0512(11) Uani 1 1 d . . .
H57 H 0.8886 0.6032 0.6743 0.061 Uiso 1 1 calc R . .
C58 C 0.9715(4) 0.77122(19) 0.80591(8) 0.0314(8) Uani 1 1 d . . .
H58 H 1.0591 0.7806 0.7915 0.038 Uiso 1 1 calc R . .
N1 N 0.7714(3) 0.07238(17) 0.94476(7) 0.0280(7) Uani 1 1 d . . .
N2 N 0.8332(3) 0.03217(18) 1.00265(7) 0.0331(7) Uani 1 1 d . . .
N3 N 0.7164(3) 0.75120(18) 0.81819(6) 0.0258(6) Uani 1 1 d . . .
N4 N 0.6649(3) 0.74430(18) 0.87872(6) 0.0302(6) Uani 1 1 d . . .
O1 O 1.1720(3) 0.05144(17) 0.95669(7) 0.0457(7) Uani 1 1 d . . .
O2 O 0.9994(3) -0.05135(13) 0.93823(5) 0.0385(5) Uani 1 1 d . . .
O3 O 0.3198(3) 0.75331(17) 0.83572(6) 0.0453(7) Uani 1 1 d . . .
O4 O 0.4852(3) 0.86767(13) 0.82729(5) 0.0382(6) Uani 1 1 d . . .
Se1 Se 0.51244(4) 0.04347(2) 0.981877(8) 0.03520(10) Uani 1 1 d . . .
Se2 Se 0.97900(4) 0.76140(2) 0.855786(8) 0.03354(10) 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
C1 N2 1.285(4) . ?
C1 N1 1.379(4) . ?
C1 Se1 1.922(3) . ?
C2 C3 1.383(5) . ?
C2 C7 1.399(4) . ?
C2 N2 1.420(4) . ?
C3 C4 1.385(5) . ?
C3 H3 0.9500 . ?
C4 C5 1.373(5) . ?
C4 H4 0.9500 . ?
C5 C6 1.366(5) . ?
C5 H5 0.9500 . ?
C6 C7 1.375(4) . ?
C6 H6 0.9500 . ?
C7 H7 0.9500 . ?
C8 N1 1.457(4) . ?
C8 C9 1.520(5) . ?
C8 C11 1.530(4) . ?
C8 H8 1.0000 . ?
C9 O1 1.205(4) . ?
C9 O2 1.335(4) . ?
C10 O2 1.442(4) . ?
C10 H10A 0.9800 . ?
C10 H10B 0.9800 . ?
C10 H10C 0.9800 . ?
C11 C12 1.513(5) . ?
C11 H11A 0.9900 . ?
C11 H11B 0.9900 . ?
C12 C17 1.379(5) . ?
C12 C13 1.389(4) . ?
C13 C14 1.380(5) . ?
C13 H13 0.9500 . ?
C14 C15 1.376(6) . ?
C14 H14 0.9500 . ?
C15 C16 1.372(5) . ?
C15 H15 0.9500 . ?
C16 C17 1.381(5) . ?
C16 H16 0.9500 . ?
C17 H17 0.9500 . ?
C18 C29 1.331(5) . ?
C18 N1 1.395(4) . ?
C18 C19 1.491(4) . ?
C19 C24 1.354(4) . ?
C19 C20 1.424(4) . ?
C20 C21 1.365(4) . ?
C20 H20 0.9500 . ?
C21 C22 1.399(4) . ?
C21 H21 0.9500 . ?
C22 C23 1.421(5) . ?
C22 C28 1.437(4) . ?
C23 C25 1.396(4) . ?
C23 C24 1.430(4) . ?
C24 H24 0.9500 . ?
C25 C26 1.362(5) . ?
C25 H25 0.9500 . ?
C26 C27 1.398(5) . ?
C26 H26 0.9500 . ?
C27 C28 1.355(5) . ?
C27 H27 0.9500 . ?
C28 H28 0.9500 . ?
C29 Se1 1.875(3) . ?
C29 H29 0.9500 . ?
C30 N4 1.272(4) . ?
C30 N3 1.388(4) . ?
C30 Se2 1.916(3) . ?
C31 C32 1.389(5) . ?
C31 C36 1.397(4) . ?
C31 N4 1.415(4) . ?
C32 C33 1.373(5) . ?
C32 H32 0.9500 . ?
C33 C34 1.384(5) . ?
C33 H33 0.9500 . ?
C34 C35 1.372(5) . ?
C34 H34 0.9500 . ?
C35 C36 1.381(5) . ?
C35 H35 0.9500 . ?
C36 H36 0.9500 . ?
C37 N3 1.451(4) . ?
C37 C38 1.518(4) . ?
C37 C40 1.543(4) . ?
C37 H37 1.0000 . ?
C38 O3 1.202(4) . ?
C38 O4 1.335(4) . ?
C39 O4 1.449(4) . ?
C39 H39A 0.9800 . ?
C39 H39B 0.9800 . ?
C39 H39C 0.9800 . ?
C40 C41 1.503(5) . ?
C40 H40A 0.9900 . ?
C40 H40B 0.9900 . ?
C41 C46 1.375(5) . ?
C41 C42 1.388(5) . ?
C42 C43 1.394(6) . ?
C42 H42 0.9500 . ?
C43 C44 1.368(6) . ?
C43 H43 0.9500 . ?
C44 C45 1.355(6) . ?
C44 H44 0.9500 . ?
C45 C46 1.388(5) . ?
C45 H45 0.9500 . ?
C46 H46 0.9500 . ?
C47 C58 1.318(5) . ?
C47 N3 1.404(4) . ?
C47 C48 1.502(4) . ?
C48 C49 1.369(4) . ?
C48 C53 1.422(5) . ?
C49 C50 1.433(5) . ?
C49 H49 0.9500 . ?
C50 C51 1.400(5) . ?
C50 C57 1.406(5) . ?
C51 C52 1.397(5) . ?
C51 C54 1.441(5) . ?
C52 C53 1.363(5) . ?
C52 H52 0.9500 . ?
C53 H53 0.9500 . ?
C54 C55 1.349(6) . ?
C54 H54 0.9500 . ?
C55 C56 1.397(6) . ?
C55 H55 0.9500 . ?
C56 C57 1.369(5) . ?
C56 H56 0.9500 . ?
C57 H57 0.9500 . ?
C58 Se2 1.878(3) . ?
C58 H58 0.9500 . ?

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
N2 C1 N1 120.6(3) . . ?
N2 C1 Se1 130.7(2) . . ?
N1 C1 Se1 108.6(2) . . ?
C3 C2 C7 118.6(3) . . ?
C3 C2 N2 124.5(3) . . ?
C7 C2 N2 116.8(3) . . ?
C2 C3 C4 120.1(3) . . ?
C2 C3 H3 120.0 . . ?
C4 C3 H3 120.0 . . ?
C5 C4 C3 120.8(4) . . ?
C5 C4 H4 119.6 . . ?
C3 C4 H4 119.6 . . ?
C6 C5 C4 119.2(4) . . ?
C6 C5 H5 120.4 . . ?
C4 C5 H5 120.4 . . ?
C5 C6 C7 121.2(4) . . ?
C5 C6 H6 119.4 . . ?
C7 C6 H6 119.4 . . ?
C6 C7 C2 120.0(3) . . ?
C6 C7 H7 120.0 . . ?
C2 C7 H7 120.0 . . ?
N1 C8 C9 112.8(3) . . ?
N1 C8 C11 113.1(3) . . ?
C9 C8 C11 111.6(3) . . ?
N1 C8 H8 106.2 . . ?
C9 C8 H8 106.2 . . ?
C11 C8 H8 106.2 . . ?
O1 C9 O2 124.4(3) . . ?
O1 C9 C8 123.5(3) . . ?
O2 C9 C8 111.8(3) . . ?
O2 C10 H10A 109.5 . . ?
O2 C10 H10B 109.5 . . ?
H10A C10 H10B 109.5 . . ?
O2 C10 H10C 109.5 . . ?
H10A C10 H10C 109.5 . . ?
H10B C10 H10C 109.5 . . ?
C12 C11 C8 111.4(3) . . ?
C12 C11 H11A 109.3 . . ?
C8 C11 H11A 109.3 . . ?
C12 C11 H11B 109.3 . . ?
C8 C11 H11B 109.3 . . ?
H11A C11 H11B 108.0 . . ?
C17 C12 C13 118.3(3) . . ?
C17 C12 C11 120.8(3) . . ?
C13 C12 C11 120.9(3) . . ?
C14 C13 C12 120.8(4) . . ?
C14 C13 H13 119.6 . . ?
C12 C13 H13 119.6 . . ?
C15 C14 C13 119.9(4) . . ?
C15 C14 H14 120.0 . . ?
C13 C14 H14 120.0 . . ?
C16 C15 C14 119.8(4) . . ?
C16 C15 H15 120.1 . . ?
C14 C15 H15 120.1 . . ?
C15 C16 C17 120.1(4) . . ?
C15 C16 H16 119.9 . . ?
C17 C16 H16 119.9 . . ?
C16 C17 C12 121.0(4) . . ?
C16 C17 H17 119.5 . . ?
C12 C17 H17 119.5 . . ?
C29 C18 N1 115.0(3) . . ?
C29 C18 C19 125.2(3) . . ?
N1 C18 C19 119.3(3) . . ?
C24 C19 C20 120.3(3) . . ?
C24 C19 C18 121.8(3) . . ?
C20 C19 C18 117.9(3) . . ?
C21 C20 C19 120.2(3) . . ?
C21 C20 H20 119.9 . . ?
C19 C20 H20 119.9 . . ?
C20 C21 C22 120.7(3) . . ?
C20 C21 H21 119.6 . . ?
C22 C21 H21 119.6 . . ?
C21 C22 C23 119.8(3) . . ?
C21 C22 C28 122.2(3) . . ?
C23 C22 C28 118.0(3) . . ?
C25 C23 C22 119.2(3) . . ?
C25 C23 C24 122.6(3) . . ?
C22 C23 C24 118.2(3) . . ?
C19 C24 C23 120.8(3) . . ?
C19 C24 H24 119.6 . . ?
C23 C24 H24 119.6 . . ?
C26 C25 C23 120.9(4) . . ?
C26 C25 H25 119.5 . . ?
C23 C25 H25 119.5 . . ?
C25 C26 C27 121.1(3) . . ?
C25 C26 H26 119.5 . . ?
C27 C26 H26 119.5 . . ?
C28 C27 C26 119.9(3) . . ?
C28 C27 H27 120.1 . . ?
C26 C27 H27 120.1 . . ?
C27 C28 C22 120.9(4) . . ?
C27 C28 H28 119.5 . . ?
C22 C28 H28 119.5 . . ?
C18 C29 Se1 113.2(3) . . ?
C18 C29 H29 123.4 . . ?
Se1 C29 H29 123.4 . . ?
N4 C30 N3 121.1(3) . . ?
N4 C30 Se2 129.8(2) . . ?
N3 C30 Se2 109.0(2) . . ?
C32 C31 C36 118.4(3) . . ?
C32 C31 N4 121.7(3) . . ?
C36 C31 N4 119.7(3) . . ?
C33 C32 C31 120.8(4) . . ?
C33 C32 H32 119.6 . . ?
C31 C32 H32 119.6 . . ?
C32 C33 C34 120.2(4) . . ?
C32 C33 H33 119.9 . . ?
C34 C33 H33 119.9 . . ?
C35 C34 C33 119.8(3) . . ?
C35 C34 H34 120.1 . . ?
C33 C34 H34 120.1 . . ?
C34 C35 C36 120.3(4) . . ?
C34 C35 H35 119.8 . . ?
C36 C35 H35 119.8 . . ?
C35 C36 C31 120.4(3) . . ?
C35 C36 H36 119.8 . . ?
C31 C36 H36 119.8 . . ?
N3 C37 C38 111.8(3) . . ?
N3 C37 C40 112.9(3) . . ?
C38 C37 C40 110.9(3) . . ?
N3 C37 H37 107.0 . . ?
C38 C37 H37 107.0 . . ?
C40 C37 H37 107.0 . . ?
O3 C38 O4 124.0(3) . . ?
O3 C38 C37 124.1(3) . . ?
O4 C38 C37 111.7(3) . . ?
O4 C39 H39A 109.5 . . ?
O4 C39 H39B 109.5 . . ?
H39A C39 H39B 109.5 . . ?
O4 C39 H39C 109.5 . . ?
H39A C39 H39C 109.5 . . ?
H39B C39 H39C 109.5 . . ?
C41 C40 C37 111.9(3) . . ?
C41 C40 H40A 109.2 . . ?
C37 C40 H40A 109.2 . . ?
C41 C40 H40B 109.2 . . ?
C37 C40 H40B 109.2 . . ?
H40A C40 H40B 107.9 . . ?
C46 C41 C42 117.9(4) . . ?
C46 C41 C40 121.0(3) . . ?
C42 C41 C40 121.1(4) . . ?
C41 C42 C43 120.1(4) . . ?
C41 C42 H42 119.9 . . ?
C43 C42 H42 119.9 . . ?
C44 C43 C42 120.4(4) . . ?
C44 C43 H43 119.8 . . ?
C42 C43 H43 119.8 . . ?
C45 C44 C43 120.1(4) . . ?
C45 C44 H44 120.0 . . ?
C43 C44 H44 120.0 . . ?
C44 C45 C46 119.8(4) . . ?
C44 C45 H45 120.1 . . ?
C46 C45 H45 120.1 . . ?
C41 C46 C45 121.7(4) . . ?
C41 C46 H46 119.2 . . ?
C45 C46 H46 119.2 . . ?
C58 C47 N3 115.8(3) . . ?
C58 C47 C48 125.3(3) . . ?
N3 C47 C48 118.7(3) . . ?
C49 C48 C53 119.4(3) . . ?
C49 C48 C47 120.8(3) . . ?
C53 C48 C47 119.7(3) . . ?
C48 C49 C50 120.5(3) . . ?
C48 C49 H49 119.8 . . ?
C50 C49 H49 119.8 . . ?
C51 C50 C57 120.3(4) . . ?
C51 C50 C49 118.7(3) . . ?
C57 C50 C49 121.0(4) . . ?
C52 C51 C50 120.1(3) . . ?
C52 C51 C54 121.4(4) . . ?
C50 C51 C54 118.5(4) . . ?
C53 C52 C51 120.6(4) . . ?
C53 C52 H52 119.7 . . ?
C51 C52 H52 119.7 . . ?
C52 C53 C48 120.7(3) . . ?
C52 C53 H53 119.7 . . ?
C48 C53 H53 119.7 . . ?
C55 C54 C51 119.5(4) . . ?
C55 C54 H54 120.3 . . ?
C51 C54 H54 120.3 . . ?
C54 C55 C56 121.5(4) . . ?
C54 C55 H55 119.3 . . ?
C56 C55 H55 119.3 . . ?
C57 C56 C55 120.5(4) . . ?
C57 C56 H56 119.7 . . ?
C55 C56 H56 119.7 . . ?
C56 C57 C50 119.7(4) . . ?
C56 C57 H57 120.2 . . ?
C50 C57 H57 120.2 . . ?
C47 C58 Se2 113.2(2) . . ?
C47 C58 H58 123.4 . . ?
Se2 C58 H58 123.4 . . ?
C1 N1 C18 116.8(3) . . ?
C1 N1 C8 119.6(3) . . ?
C18 N1 C8 123.2(3) . . ?
C1 N2 C2 120.8(3) . . ?
C30 N3 C47 115.9(3) . . ?
C30 N3 C37 118.9(3) . . ?
C47 N3 C37 123.9(3) . . ?
C30 N4 C31 118.5(3) . . ?
C9 O2 C10 115.0(3) . . ?
C38 O4 C39 116.0(3) . . ?
C29 Se1 C1 85.75(15) . . ?
C58 Se2 C30 85.94(15) . . ?

_diffrn_measured_fraction_theta_max 0.959
_diffrn_reflns_theta_full        25.00
_diffrn_measured_fraction_theta_full 0.959
_refine_diff_density_max         0.279
_refine_diff_density_min         -0.581
_refine_diff_density_rms         0.050
####################################################################### 
# 
# 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_ch13732
_audit_block_doi                 10.5517/ccyn5f5
_database_code_depnum_ccdc_archive 'CCDC 883327'
_audit_update_record             
;
2012-05-22 deposited with the CCDC.
2015-10-22 downloaded from the CCDC.
;
#TrackingRef '11437_web_deposit_cif_file_1_wong-jin-chang_1337660280.ch13732.cif'


_audit_creation_method           SHELXL-97
_chemical_name_systematic        
;
?
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         'C31 H28 N2 O3 Se'
_chemical_formula_sum            'C31 H28 N2 O3 Se'
_chemical_formula_weight         555.51

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'
O O 0.0106 0.0060 '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   'P 21'

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

_cell_length_a                   8.6504(3)
_cell_length_b                   9.7776(4)
_cell_length_c                   16.3783(6)
_cell_angle_alpha                90.00
_cell_angle_beta                 98.688(2)
_cell_angle_gamma                90.00
_cell_volume                     1369.38(9)
_cell_formula_units_Z            2
_cell_measurement_temperature    298(2)
_cell_measurement_reflns_used    0
_cell_measurement_theta_min      0
_cell_measurement_theta_max      0

_exptl_crystal_description       prism
_exptl_crystal_colour            colorless
_exptl_crystal_size_max          0.74
_exptl_crystal_size_mid          0.46
_exptl_crystal_size_min          0.33
_exptl_crystal_density_meas      ?
_exptl_crystal_density_diffrn    1.347
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             572
_exptl_absorpt_coefficient_mu    1.405
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.4228
_exptl_absorpt_correction_T_max  0.6542
_exptl_absorpt_process_details   ?

_exptl_special_details           
;
?
;

_diffrn_ambient_temperature      298(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_radiation_source         'fine-focus sealed tube'
_diffrn_radiation_monochromator  graphite
_diffrn_measurement_device_type  ?
_diffrn_measurement_method       ?
_diffrn_detector_area_resol_mean ?
_diffrn_standards_number         ?
_diffrn_standards_interval_count ?
_diffrn_standards_interval_time  ?
_diffrn_standards_decay_%        ?
_diffrn_reflns_number            9454
_diffrn_reflns_av_R_equivalents  0.0241
_diffrn_reflns_av_sigmaI/netI    0.0569
_diffrn_reflns_limit_h_min       -10
_diffrn_reflns_limit_h_max       10
_diffrn_reflns_limit_k_min       -11
_diffrn_reflns_limit_k_max       11
_diffrn_reflns_limit_l_min       -19
_diffrn_reflns_limit_l_max       17
_diffrn_reflns_theta_min         1.26
_diffrn_reflns_theta_max         25.19
_reflns_number_total             4712
_reflns_number_gt                4084
_reflns_threshold_expression     >2sigma(I)

_computing_data_collection       ?
_computing_cell_refinement       ?
_computing_data_reduction        ?
_computing_structure_solution    'SHELXS-86 (Sheldrick, 1986)'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_computing_molecular_graphics    'Ortep-3 for Windows (Farrugia, 1997)'
_computing_publication_material  'WinGX publication routines (Farrugia, 1999)'

_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)+(0.0164P)²+0.0263P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_atom_sites_solution_hydrogens   geom
_refine_ls_hydrogen_treatment    constr
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       ?
_refine_ls_abs_structure_details 'Flack H D (1983), Acta Cryst. A39, 876-881'
_refine_ls_abs_structure_Flack   0.014(8)
_refine_ls_number_reflns         4712
_refine_ls_number_parameters     334
_refine_ls_number_restraints     1
_refine_ls_R_factor_all          0.0392
_refine_ls_R_factor_gt           0.0304
_refine_ls_wR_factor_ref         0.0730
_refine_ls_wR_factor_gt          0.0683
_refine_ls_goodness_of_fit_ref   1.082
_refine_ls_restrained_S_all      1.081
_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_symmetry_multiplicity
_atom_site_calc_flag
_atom_site_refinement_flags
_atom_site_disorder_assembly
_atom_site_disorder_group
C1 C 0.7424(3) 1.0811(4) 0.79307(17) 0.0371(7) Uani 1 1 d . . .
C2 C 0.7870(3) 1.2648(4) 0.8819(2) 0.0484(9) Uani 1 1 d . . .
C3 C 0.8712(4) 1.3595(4) 0.8444(3) 0.0618(10) Uani 1 1 d . . .
H3 H 0.8643 1.3613 0.7872 0.074 Uiso 1 1 calc R . .
C4 C 0.9665(4) 1.4522(5) 0.8928(3) 0.0790(13) Uani 1 1 d . . .
H4 H 1.0229 1.5172 0.8681 0.095 Uiso 1 1 calc R . .
C5 C 0.9772(5) 1.4471(5) 0.9783(3) 0.0804(14) Uani 1 1 d . . .
H5 H 1.0438 1.5070 1.0109 0.096 Uiso 1 1 calc R . .
C6 C 0.8912(5) 1.3555(5) 1.0149(3) 0.0711(12) Uani 1 1 d . . .
H6 H 0.8980 1.3541 1.0721 0.085 Uiso 1 1 calc R . .
C7 C 0.7946(4) 1.2652(4) 0.9678(2) 0.0555(10) Uani 1 1 d . . .
H7 H 0.7341 1.2041 0.9930 0.067 Uiso 1 1 calc R . .
C8 C 0.4817(3) 0.9913(3) 0.7428(2) 0.0369(8) Uani 1 1 d . . .
H8 H 0.4374 0.9200 0.7042 0.044 Uiso 1 1 calc R . .
C9 C 0.4294(3) 1.1273(3) 0.7027(2) 0.0436(9) Uani 1 1 d . A .
C10 C 0.2393(7) 1.3042(6) 0.6969(4) 0.0473(15) Uiso 0.60 1 d P A 1
H10A H 0.1436 1.3233 0.7177 0.071 Uiso 0.60 1 calc PR A 1
H10B H 0.2204 1.3047 0.6376 0.071 Uiso 0.60 1 calc PR A 1
H10C H 0.3155 1.3728 0.7162 0.071 Uiso 0.60 1 calc PR A 1
C10' C 0.2196(11) 1.2797(11) 0.6596(6) 0.054(3) Uiso 0.40 1 d P A 2
H10D H 0.1237 1.3127 0.6753 0.082 Uiso 0.40 1 calc PR A 2
H10E H 0.1982 1.2368 0.6064 0.082 Uiso 0.40 1 calc PR A 2
H10F H 0.2900 1.3550 0.6571 0.082 Uiso 0.40 1 calc PR A 2
C11 C 0.4176(3) 0.9646(4) 0.8246(2) 0.0493(9) Uani 1 1 d . . .
H11A H 0.4538 1.0371 0.8632 0.059 Uiso 1 1 calc R . .
H11B H 0.3043 0.9693 0.8138 0.059 Uiso 1 1 calc R . .
C12 C 0.4640(3) 0.8306(4) 0.8642(2) 0.0449(8) Uani 1 1 d . . .
C13 C 0.3785(4) 0.7133(4) 0.8425(2) 0.0621(10) Uani 1 1 d . . .
H13 H 0.2897 0.7174 0.8028 0.075 Uiso 1 1 calc R . .
C14 C 0.4248(5) 0.5886(5) 0.8799(3) 0.0813(13) Uani 1 1 d . . .
H14 H 0.3667 0.5098 0.8655 0.098 Uiso 1 1 calc R . .
C15 C 0.5578(6) 0.5832(6) 0.9385(3) 0.0877(15) Uani 1 1 d . . .
H15 H 0.5903 0.5004 0.9632 0.105 Uiso 1 1 calc R . .
C16 C 0.6412(5) 0.6991(6) 0.9599(3) 0.0832(14) Uani 1 1 d . . .
H16 H 0.7295 0.6950 1.0000 0.100 Uiso 1 1 calc R . .
C17 C 0.5970(4) 0.8210(4) 0.9235(2) 0.0623(10) Uani 1 1 d . . .
H17 H 0.6564 0.8989 0.9385 0.075 Uiso 1 1 calc R . .
C18 C 0.7227(3) 0.9151(3) 0.68257(18) 0.0366(7) Uani 1 1 d . . .
C19 C 0.6556(3) 0.7753(3) 0.65788(19) 0.0370(7) Uani 1 1 d . . .
C20 C 0.6470(3) 0.6738(4) 0.7167(2) 0.0477(8) Uani 1 1 d . . .
H20 H 0.6739 0.6942 0.7725 0.057 Uiso 1 1 calc R . .
C21 C 0.5992(4) 0.5437(4) 0.6930(2) 0.0567(10) Uani 1 1 d . . .
H21 H 0.5925 0.4769 0.7327 0.068 Uiso 1 1 calc R . .
C22 C 0.5607(4) 0.5119(4) 0.6095(2) 0.0596(10) Uani 1 1 d . . .
H22 H 0.5295 0.4238 0.5931 0.072 Uiso 1 1 calc R . .
C23 C 0.5692(4) 0.6109(4) 0.5526(2) 0.0603(12) Uani 1 1 d . . .
H23 H 0.5427 0.5904 0.4968 0.072 Uiso 1 1 calc R . .
C24 C 0.6162(3) 0.7409(4) 0.57579(19) 0.0458(8) Uani 1 1 d . . .
H24 H 0.6216 0.8069 0.5355 0.055 Uiso 1 1 calc R . .
C25 C 0.8989(3) 0.8954(3) 0.71728(19) 0.0408(8) Uani 1 1 d . . .
H25 H 0.9069 0.8196 0.7568 0.049 Uiso 1 1 calc R . .
C26 C 1.0006(3) 0.8612(4) 0.6532(2) 0.0510(9) Uani 1 1 d . . .
C27 C 1.0528(4) 0.7292(5) 0.6464(3) 0.0712(12) Uani 1 1 d . . .
H27 H 1.0272 0.6623 0.6825 0.085 Uiso 1 1 calc R . .
C28 C 1.1436(6) 0.6951(7) 0.5860(4) 0.1015(18) Uani 1 1 d . . .
H28 H 1.1785 0.6057 0.5822 0.122 Uiso 1 1 calc R . .
C29 C 1.1811(6) 0.7909(8) 0.5331(4) 0.1028(19) Uani 1 1 d . . .
H29 H 1.2431 0.7677 0.4934 0.123 Uiso 1 1 calc R . .
C30 C 1.1287(5) 0.9206(7) 0.5375(3) 0.0915(15) Uani 1 1 d . . .
H30 H 1.1522 0.9854 0.4997 0.110 Uiso 1 1 calc R . .
C31 C 1.0406(4) 0.9580(5) 0.5978(2) 0.0658(11) Uani 1 1 d . . .
H31 H 1.0080 1.0481 0.6012 0.079 Uiso 1 1 calc R . .
N1 N 0.6856(3) 1.1687(3) 0.83577(17) 0.0478(7) Uani 1 1 d . . .
N2 N 0.6530(2) 0.9787(3) 0.74983(15) 0.0351(6) Uani 1 1 d . . .
O1 O 0.4955(3) 1.1861(3) 0.65390(15) 0.0592(7) Uani 1 1 d . . .
O2 O 0.2969(2) 1.1720(3) 0.72569(17) 0.0650(7) Uani 1 1 d . . .
O3 O 0.7089(2) 1.0015(2) 0.61352(12) 0.0446(5) Uani 1 1 d . . .
H3' H 0.6450 1.0663 0.6209 0.053 Uiso 1 1 d R . .
Se1 Se 0.95880(3) 1.06374(4) 0.779777(18) 0.04705(11) 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
C1 N1 1.252(4) . ?
C1 N2 1.391(4) . ?
C1 Se1 1.925(3) . ?
C2 C3 1.379(5) . ?
C2 C7 1.398(5) . ?
C2 N1 1.423(4) . ?
C3 C4 1.390(5) . ?
C3 H3 0.9300 . ?
C4 C5 1.391(6) . ?
C4 H4 0.9300 . ?
C5 C6 1.360(6) . ?
C5 H5 0.9300 . ?
C6 C7 1.370(5) . ?
C6 H6 0.9300 . ?
C7 H7 0.9300 . ?
C8 N2 1.474(3) . ?
C8 C9 1.522(4) . ?
C8 C11 1.547(5) . ?
C8 H8 0.9800 . ?
C9 O1 1.198(4) . ?
C9 O2 1.332(4) . ?
C10 O2 1.439(6) . ?
C10 H10A 0.9600 . ?
C10 H10B 0.9600 . ?
C10 H10C 0.9600 . ?
C10' O2 1.585(10) . ?
C10' H10D 0.9600 . ?
C10' H10E 0.9600 . ?
C10' H10F 0.9600 . ?
C11 C12 1.490(5) . ?
C11 H11A 0.9700 . ?
C11 H11B 0.9700 . ?
C12 C13 1.382(5) . ?
C12 C17 1.392(5) . ?
C13 C14 1.395(6) . ?
C13 H13 0.9300 . ?
C14 C15 1.384(6) . ?
C14 H14 0.9300 . ?
C15 C16 1.360(7) . ?
C15 H15 0.9300 . ?
C16 C17 1.362(6) . ?
C16 H16 0.9300 . ?
C17 H17 0.9300 . ?
C18 O3 1.402(3) . ?
C18 N2 1.471(4) . ?
C18 C19 1.517(4) . ?
C18 C25 1.556(4) . ?
C19 C24 1.378(4) . ?
C19 C20 1.393(5) . ?
C20 C21 1.376(6) . ?
C20 H20 0.9300 . ?
C21 C22 1.393(5) . ?
C21 H21 0.9300 . ?
C22 C23 1.354(5) . ?
C22 H22 0.9300 . ?
C23 C24 1.371(5) . ?
C23 H23 0.9300 . ?
C24 H24 0.9300 . ?
C25 C26 1.506(4) . ?
C25 Se1 1.966(3) . ?
C25 H25 0.9800 . ?
C26 C27 1.377(5) . ?
C26 C31 1.390(5) . ?
C27 C28 1.393(6) . ?
C27 H27 0.9300 . ?
C28 C29 1.349(7) . ?
C28 H28 0.9300 . ?
C29 C30 1.352(8) . ?
C29 H29 0.9300 . ?
C30 C31 1.384(6) . ?
C30 H30 0.9300 . ?
C31 H31 0.9300 . ?
O3 H3' 0.8608 . ?

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
N1 C1 N2 122.8(2) . . ?
N1 C1 Se1 126.4(2) . . ?
N2 C1 Se1 110.7(2) . . ?
C3 C2 C7 120.0(3) . . ?
C3 C2 N1 122.1(3) . . ?
C7 C2 N1 117.9(3) . . ?
C2 C3 C4 119.4(4) . . ?
C2 C3 H3 120.3 . . ?
C4 C3 H3 120.3 . . ?
C5 C4 C3 119.7(4) . . ?
C5 C4 H4 120.2 . . ?
C3 C4 H4 120.2 . . ?
C6 C5 C4 120.6(4) . . ?
C6 C5 H5 119.7 . . ?
C4 C5 H5 119.7 . . ?
C5 C6 C7 120.3(4) . . ?
C5 C6 H6 119.8 . . ?
C7 C6 H6 119.8 . . ?
C6 C7 C2 120.0(4) . . ?
C6 C7 H7 120.0 . . ?
C2 C7 H7 120.0 . . ?
N2 C8 C9 109.7(2) . . ?
N2 C8 C11 113.9(2) . . ?
C9 C8 C11 113.5(3) . . ?
N2 C8 H8 106.4 . . ?
C9 C8 H8 106.4 . . ?
C11 C8 H8 106.4 . . ?
O1 C9 O2 123.3(3) . . ?
O1 C9 C8 124.5(3) . . ?
O2 C9 C8 112.1(3) . . ?
O2 C10 H10A 109.5 . . ?
O2 C10 H10B 109.5 . . ?
H10A C10 H10B 109.5 . . ?
O2 C10 H10C 109.5 . . ?
H10A C10 H10C 109.5 . . ?
H10B C10 H10C 109.5 . . ?
O2 C10' H10D 109.5 . . ?
O2 C10' H10E 109.5 . . ?
H10D C10' H10E 109.5 . . ?
O2 C10' H10F 109.5 . . ?
H10D C10' H10F 109.5 . . ?
H10E C10' H10F 109.5 . . ?
C12 C11 C8 114.7(3) . . ?
C12 C11 H11A 108.6 . . ?
C8 C11 H11A 108.6 . . ?
C12 C11 H11B 108.6 . . ?
C8 C11 H11B 108.6 . . ?
H11A C11 H11B 107.6 . . ?
C13 C12 C17 118.5(4) . . ?
C13 C12 C11 121.3(3) . . ?
C17 C12 C11 120.2(3) . . ?
C12 C13 C14 120.4(4) . . ?
C12 C13 H13 119.8 . . ?
C14 C13 H13 119.8 . . ?
C15 C14 C13 119.4(5) . . ?
C15 C14 H14 120.3 . . ?
C13 C14 H14 120.3 . . ?
C16 C15 C14 120.0(5) . . ?
C16 C15 H15 120.0 . . ?
C14 C15 H15 120.0 . . ?
C15 C16 C17 120.9(4) . . ?
C15 C16 H16 119.5 . . ?
C17 C16 H16 119.5 . . ?
C16 C17 C12 120.8(4) . . ?
C16 C17 H17 119.6 . . ?
C12 C17 H17 119.6 . . ?
O3 C18 N2 110.8(2) . . ?
O3 C18 C19 110.2(2) . . ?
N2 C18 C19 113.4(2) . . ?
O3 C18 C25 109.2(2) . . ?
N2 C18 C25 105.6(2) . . ?
C19 C18 C25 107.5(2) . . ?
C24 C19 C20 118.1(3) . . ?
C24 C19 C18 120.6(3) . . ?
C20 C19 C18 121.1(3) . . ?
C21 C20 C19 120.5(3) . . ?
C21 C20 H20 119.7 . . ?
C19 C20 H20 119.7 . . ?
C20 C21 C22 120.1(4) . . ?
C20 C21 H21 120.0 . . ?
C22 C21 H21 120.0 . . ?
C23 C22 C21 119.1(3) . . ?
C23 C22 H22 120.4 . . ?
C21 C22 H22 120.4 . . ?
C22 C23 C24 121.1(3) . . ?
C22 C23 H23 119.4 . . ?
C24 C23 H23 119.4 . . ?
C23 C24 C19 121.1(3) . . ?
C23 C24 H24 119.5 . . ?
C19 C24 H24 119.5 . . ?
C26 C25 C18 114.6(3) . . ?
C26 C25 Se1 114.4(2) . . ?
C18 C25 Se1 104.7(2) . . ?
C26 C25 H25 107.6 . . ?
C18 C25 H25 107.6 . . ?
Se1 C25 H25 107.6 . . ?
C27 C26 C31 117.9(4) . . ?
C27 C26 C25 119.8(4) . . ?
C31 C26 C25 122.2(3) . . ?
C26 C27 C28 120.5(5) . . ?
C26 C27 H27 119.7 . . ?
C28 C27 H27 119.7 . . ?
C29 C28 C27 120.4(5) . . ?
C29 C28 H28 119.8 . . ?
C27 C28 H28 119.8 . . ?
C28 C29 C30 120.1(5) . . ?
C28 C29 H29 120.0 . . ?
C30 C29 H29 120.0 . . ?
C29 C30 C31 120.8(5) . . ?
C29 C30 H30 119.6 . . ?
C31 C30 H30 119.6 . . ?
C30 C31 C26 120.2(5) . . ?
C30 C31 H31 119.9 . . ?
C26 C31 H31 119.9 . . ?
C1 N1 C2 119.1(3) . . ?
C1 N2 C18 115.2(2) . . ?
C1 N2 C8 117.0(2) . . ?
C18 N2 C8 119.8(2) . . ?
C9 O2 C10 118.1(3) . . ?
C9 O2 C10' 108.5(4) . . ?
C10 O2 C10' 24.4(4) . . ?
C18 O3 H3' 108.0 . . ?
C1 Se1 C25 87.03(14) . . ?

_diffrn_measured_fraction_theta_max 0.983
_diffrn_reflns_theta_full        25.19
_diffrn_measured_fraction_theta_full 0.983
_refine_diff_density_max         0.286
_refine_diff_density_min         -0.289
_refine_diff_density_rms         0.074


####################################################################### 
# 
# 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_mo_111153lt_0m
_audit_block_doi                 10.5517/ccyqhpt
_database_code_depnum_ccdc_archive 'CCDC 885567'
_audit_update_record             
;
2012-06-07 deposited with the CCDC.
2015-10-22 downloaded from the CCDC.
;
#TrackingRef '11725_web_deposit_cif_file_0_wong-jin-chang_1339051891.mo_111153lt_0m.cif'


_audit_creation_method           SHELXL-97
_chemical_name_systematic        
;
?
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C22 H23 Br N2 O2 S Se'
_chemical_formula_weight         538.35

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'
O O 0.0106 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
S S 0.1246 0.1234 '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           monoclinic
_symmetry_space_group_name_H-M   'P 1 21 1'
_symmetry_space_group_name_hall  'P 2yb'

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

_cell_length_a                   11.244(2)
_cell_length_b                   7.6728(14)
_cell_length_c                   12.837(2)
_cell_angle_alpha                90.00
_cell_angle_beta                 98.983(4)
_cell_angle_gamma                90.00
_cell_volume                     1093.9(3)
_cell_formula_units_Z            2
_cell_measurement_temperature    100(2)
_cell_measurement_reflns_used    5089
_cell_measurement_theta_min      3.1032
_cell_measurement_theta_max      26.4284

_exptl_crystal_description       Columnar
_exptl_crystal_colour            Colorless
_exptl_crystal_size_max          0.25
_exptl_crystal_size_mid          0.12
_exptl_crystal_size_min          0.12
_exptl_crystal_density_meas      'not measured'
_exptl_crystal_density_diffrn    1.634
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             540
_exptl_absorpt_coefficient_mu    3.659
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.8045
_exptl_absorpt_correction_T_max  0.9486
_exptl_absorpt_process_details   'SADABS V2008/1 (Bruker AXS)'

_exptl_special_details           
;
?
;

_diffrn_ambient_temperature      100(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_radiation_source         'fine-focus sealed tube'
_diffrn_radiation_monochromator  graphite
_diffrn_measurement_device_type  'Bruker APEX-II CCD'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_detector_area_resol_mean 8.3333
_diffrn_reflns_number            8706
_diffrn_reflns_av_R_equivalents  0.0186
_diffrn_reflns_av_sigmaI/netI    0.0399
_diffrn_reflns_limit_h_min       -14
_diffrn_reflns_limit_h_max       14
_diffrn_reflns_limit_k_min       -9
_diffrn_reflns_limit_k_max       5
_diffrn_reflns_limit_l_min       -15
_diffrn_reflns_limit_l_max       16
_diffrn_reflns_theta_min         1.61
_diffrn_reflns_theta_max         26.52
_reflns_number_total             3751
_reflns_number_gt                3529
_reflns_threshold_expression     >2sigma(I)

_computing_data_collection       'APEX2 (Bruker AXS, 2010)'
_computing_cell_refinement       'SAINT V7.68A (Bruker AXS, 2009)'
_computing_data_reduction        'SAINT V7.68A (Bruker AXS, 2009)'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 2008)'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 2008)'
_computing_molecular_graphics    'SHELXTL (Sheldrick, 2008)'
_computing_publication_material  SHELXTL

_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)+(0.0000P)²+0.0000P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_atom_sites_solution_hydrogens   geom
_refine_ls_hydrogen_treatment    constr
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       ?
_refine_ls_abs_structure_details 'Flack H D (1983), Acta Cryst. A39, 876-881'
_refine_ls_abs_structure_Flack   0.007(6)
_refine_ls_number_reflns         3751
_refine_ls_number_parameters     265
_refine_ls_number_restraints     1
_refine_ls_R_factor_all          0.0201
_refine_ls_R_factor_gt           0.0177
_refine_ls_wR_factor_ref         0.0386
_refine_ls_wR_factor_gt          0.0381
_refine_ls_goodness_of_fit_ref   1.004
_refine_ls_restrained_S_all      1.004
_refine_ls_shift/su_max          0.002
_refine_ls_shift/su_mean         0.000
_chemical_absolute_configuration rm

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
Br1 Br 0.51396(2) 0.36699(3) 0.480298(17) 0.02536(7) Uani 1 1 d . . .
Se1 Se 1.042501(17) 0.39096(3) 1.064026(15) 0.01775(6) Uani 1 1 d . . .
S1 S 0.96496(7) 0.64826(9) 0.54364(5) 0.03141(17) Uani 1 1 d . . .
N2 N 1.22896(14) 0.3679(3) 0.92948(12) 0.0187(4) Uani 1 1 d . . .
O2 O 1.11533(17) 0.1075(2) 0.74899(13) 0.0234(4) Uani 1 1 d . . .
N1 N 1.02930(14) 0.3932(3) 0.85304(12) 0.0170(4) Uani 1 1 d . . .
O1 O 1.23262(15) 0.2973(2) 0.67938(13) 0.0248(4) Uani 1 1 d . . .
C1 C 0.63161(17) 0.3664(4) 0.60434(15) 0.0175(4) Uani 1 1 d . . .
C2 C 0.7196(2) 0.2395(3) 0.61755(18) 0.0190(5) Uani 1 1 d . . .
H2A H 0.7196 0.1491 0.5670 0.023 Uiso 1 1 calc R . .
C3 C 0.8078(2) 0.2457(3) 0.70539(17) 0.0173(5) Uani 1 1 d . . .
H3 H 0.8677 0.1574 0.7154 0.021 Uiso 1 1 calc R . .
C4 C 0.81079(16) 0.3785(4) 0.77939(14) 0.0147(4) Uani 1 1 d . . .
C5 C 0.90820(17) 0.3890(3) 0.87085(15) 0.0151(4) Uani 1 1 d . . .
C6 C 0.89310(17) 0.3877(4) 0.97252(15) 0.0161(4) Uani 1 1 d . . .
C7 C 1.11744(17) 0.3823(4) 0.93974(15) 0.0168(4) Uani 1 1 d . . .
C8 C 1.32151(17) 0.3553(3) 1.01666(16) 0.0163(5) Uani 1 1 d . . .
C9 C 1.4158(2) 0.2393(3) 1.00928(18) 0.0194(5) Uani 1 1 d . . .
H9 H 1.4160 0.1737 0.9465 0.023 Uiso 1 1 calc R . .
C10 C 1.5085(2) 0.2195(3) 1.09224(19) 0.0206(5) Uani 1 1 d . . .
H10 H 1.5705 0.1374 1.0868 0.025 Uiso 1 1 calc R . .
C11 C 1.5131(2) 0.3169(3) 1.18324(19) 0.0211(6) Uani 1 1 d . . .
H11 H 1.5775 0.3023 1.2400 0.025 Uiso 1 1 calc R . .
C12 C 1.4222(2) 0.4365(3) 1.19061(19) 0.0221(6) Uani 1 1 d . . .
H12 H 1.4249 0.5051 1.2526 0.026 Uiso 1 1 calc R . .
C13 C 1.3269(2) 0.4570(3) 1.10808(18) 0.0182(5) Uani 1 1 d . . .
H13 H 1.2655 0.5400 1.1137 0.022 Uiso 1 1 calc R . .
C14 C 1.06633(19) 0.4134(3) 0.74871(16) 0.0164(5) Uani 1 1 d . . .
H14 H 0.9909 0.4081 0.6960 0.020 Uiso 1 1 calc R . .
C15 C 1.1401(2) 0.2531(3) 0.72897(17) 0.0190(5) Uani 1 1 d . . .
C16 C 1.3065(3) 0.1513(3) 0.6577(2) 0.0372(7) Uani 1 1 d . . .
H16A H 1.2584 0.0711 0.6088 0.056 Uiso 1 1 calc R . .
H16B H 1.3363 0.0902 0.7237 0.056 Uiso 1 1 calc R . .
H16C H 1.3749 0.1938 0.6261 0.056 Uiso 1 1 calc R . .
C17 C 1.1219(3) 0.5914(3) 0.7353(2) 0.0219(6) Uani 1 1 d . . .
H17A H 1.2076 0.5888 0.7683 0.026 Uiso 1 1 calc R . .
H17B H 1.0805 0.6793 0.7733 0.026 Uiso 1 1 calc R . .
C18 C 1.1143(2) 0.6480(3) 0.62006(19) 0.0264(6) Uani 1 1 d . . .
H18A H 1.1659 0.5695 0.5852 0.032 Uiso 1 1 calc R . .
H18B H 1.1480 0.7670 0.6187 0.032 Uiso 1 1 calc R . .
C19 C 0.8921(3) 0.8126(3) 0.6116(2) 0.0331(7) Uani 1 1 d . . .
H19A H 0.9423 0.9176 0.6204 0.050 Uiso 1 1 calc R . .
H19B H 0.8807 0.7686 0.6810 0.050 Uiso 1 1 calc R . .
H19C H 0.8136 0.8410 0.5703 0.050 Uiso 1 1 calc R . .
C20 C 0.77924(17) 0.3735(4) 1.01900(15) 0.0197(4) Uani 1 1 d . . .
H20A H 0.7770 0.2606 1.0543 0.030 Uiso 1 1 calc R . .
H20B H 0.7098 0.3833 0.9628 0.030 Uiso 1 1 calc R . .
H20C H 0.7764 0.4674 1.0703 0.030 Uiso 1 1 calc R . .
C21 C 0.7189(2) 0.5028(3) 0.76537(18) 0.0180(5) Uani 1 1 d . . .
H21 H 0.7182 0.5929 0.8161 0.022 Uiso 1 1 calc R . .
C22 C 0.6288(2) 0.4967(3) 0.67851(18) 0.0218(5) Uani 1 1 d . . .
H22 H 0.5659 0.5806 0.6700 0.026 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
Br1 C1 1.905(2) . ?
Se1 C6 1.894(2) . ?
Se1 C7 1.9182(18) . ?
S1 C19 1.802(3) . ?
S1 C18 1.808(3) . ?
N2 C7 1.286(2) . ?
N2 C8 1.408(3) . ?
O2 C15 1.189(3) . ?
N1 C7 1.372(2) . ?
N1 C5 1.416(2) . ?
N1 C14 1.472(2) . ?
O1 C15 1.345(3) . ?
O1 C16 1.447(3) . ?
C1 C2 1.380(3) . ?
C1 C22 1.384(3) . ?
C2 C3 1.381(3) . ?
C2 H2A 0.9500 . ?
C3 C4 1.390(3) . ?
C3 H3 0.9500 . ?
C4 C21 1.397(3) . ?
C4 C5 1.477(3) . ?
C5 C6 1.342(3) . ?
C6 C20 1.499(2) . ?
C8 C9 1.399(3) . ?
C8 C13 1.403(3) . ?
C9 C10 1.377(3) . ?
C9 H9 0.9500 . ?
C10 C11 1.381(3) . ?
C10 H10 0.9500 . ?
C11 C12 1.388(3) . ?
C11 H11 0.9500 . ?
C12 C13 1.392(3) . ?
C12 H12 0.9500 . ?
C13 H13 0.9500 . ?
C14 C17 1.522(3) . ?
C14 C15 1.527(3) . ?
C14 H14 1.0000 . ?
C16 H16A 0.9800 . ?
C16 H16B 0.9800 . ?
C16 H16C 0.9800 . ?
C17 C18 1.532(3) . ?
C17 H17A 0.9900 . ?
C17 H17B 0.9900 . ?
C18 H18A 0.9900 . ?
C18 H18B 0.9900 . ?
C19 H19A 0.9800 . ?
C19 H19B 0.9800 . ?
C19 H19C 0.9800 . ?
C20 H20A 0.9800 . ?
C20 H20B 0.9800 . ?
C20 H20C 0.9800 . ?
C21 C22 1.386(3) . ?
C21 H21 0.9500 . ?
C22 H22 0.9500 . ?

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
C6 Se1 C7 86.90(8) . . ?
C19 S1 C18 101.08(13) . . ?
C7 N2 C8 122.42(16) . . ?
C7 N1 C5 117.30(15) . . ?
C7 N1 C14 118.26(15) . . ?
C5 N1 C14 124.42(16) . . ?
C15 O1 C16 113.91(19) . . ?
C2 C1 C22 121.2(2) . . ?
C2 C1 Br1 119.71(18) . . ?
C22 C1 Br1 119.06(18) . . ?
C1 C2 C3 119.0(2) . . ?
C1 C2 H2A 120.5 . . ?
C3 C2 H2A 120.5 . . ?
C2 C3 C4 121.4(2) . . ?
C2 C3 H3 119.3 . . ?
C4 C3 H3 119.3 . . ?
C3 C4 C21 118.30(19) . . ?
C3 C4 C5 121.3(2) . . ?
C21 C4 C5 120.4(2) . . ?
C6 C5 N1 115.34(17) . . ?
C6 C5 C4 125.57(16) . . ?
N1 C5 C4 119.03(15) . . ?
C5 C6 C20 129.30(18) . . ?
C5 C6 Se1 111.62(13) . . ?
C20 C6 Se1 118.96(13) . . ?
N2 C7 N1 120.96(16) . . ?
N2 C7 Se1 130.56(15) . . ?
N1 C7 Se1 108.48(12) . . ?
C9 C8 C13 118.4(2) . . ?
C9 C8 N2 117.6(2) . . ?
C13 C8 N2 123.9(2) . . ?
C10 C9 C8 120.5(2) . . ?
C10 C9 H9 119.7 . . ?
C8 C9 H9 119.7 . . ?
C9 C10 C11 121.2(2) . . ?
C9 C10 H10 119.4 . . ?
C11 C10 H10 119.4 . . ?
C10 C11 C12 119.0(2) . . ?
C10 C11 H11 120.5 . . ?
C12 C11 H11 120.5 . . ?
C11 C12 C13 120.6(2) . . ?
C11 C12 H12 119.7 . . ?
C13 C12 H12 119.7 . . ?
C12 C13 C8 120.1(2) . . ?
C12 C13 H13 119.9 . . ?
C8 C13 H13 119.9 . . ?
N1 C14 C17 112.12(19) . . ?
N1 C14 C15 107.72(18) . . ?
C17 C14 C15 117.43(19) . . ?
N1 C14 H14 106.3 . . ?
C17 C14 H14 106.3 . . ?
C15 C14 H14 106.3 . . ?
O2 C15 O1 124.3(2) . . ?
O2 C15 C14 124.7(2) . . ?
O1 C15 C14 110.8(2) . . ?
O1 C16 H16A 109.5 . . ?
O1 C16 H16B 109.5 . . ?
H16A C16 H16B 109.5 . . ?
O1 C16 H16C 109.5 . . ?
H16A C16 H16C 109.5 . . ?
H16B C16 H16C 109.5 . . ?
C14 C17 C18 113.7(2) . . ?
C14 C17 H17A 108.8 . . ?
C18 C17 H17A 108.8 . . ?
C14 C17 H17B 108.8 . . ?
C18 C17 H17B 108.8 . . ?
H17A C17 H17B 107.7 . . ?
C17 C18 S1 115.56(18) . . ?
C17 C18 H18A 108.4 . . ?
S1 C18 H18A 108.4 . . ?
C17 C18 H18B 108.4 . . ?
S1 C18 H18B 108.4 . . ?
H18A C18 H18B 107.5 . . ?
S1 C19 H19A 109.5 . . ?
S1 C19 H19B 109.5 . . ?
H19A C19 H19B 109.5 . . ?
S1 C19 H19C 109.5 . . ?
H19A C19 H19C 109.5 . . ?
H19B C19 H19C 109.5 . . ?
C6 C20 H20A 109.5 . . ?
C6 C20 H20B 109.5 . . ?
H20A C20 H20B 109.5 . . ?
C6 C20 H20C 109.5 . . ?
H20A C20 H20C 109.5 . . ?
H20B C20 H20C 109.5 . . ?
C22 C21 C4 120.9(2) . . ?
C22 C21 H21 119.5 . . ?
C4 C21 H21 119.5 . . ?
C1 C22 C21 119.1(2) . . ?
C1 C22 H22 120.5 . . ?
C21 C22 H22 120.5 . . ?

_diffrn_measured_fraction_theta_max 0.991
_diffrn_reflns_theta_full        26.52
_diffrn_measured_fraction_theta_full 0.991
_refine_diff_density_max         0.260
_refine_diff_density_min         -0.250
_refine_diff_density_rms         0.048
####################################################################### 
# 
# 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_mo_140308lt_0m
_database_code_depnum_ccdc_archive 'CCDC 1424392'
_audit_update_record             
;
2015-09-15 deposited with the CCDC.
2015-10-22 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2013
_chemical_name_systematic        
;
 ?
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C32 H30 N2 Se2'
_chemical_formula_weight         600.50

loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
N N 0.0061 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
Se Se -0.0929 2.2259 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

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

_shelx_space_group_comment       
;
The symmetry employed for this shelxl refinement is uniquely defined
by the following loop, which should always be used as a source of
symmetry information in preference to the above space-group names.
They are only intended as comments.
;

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

_cell_length_a                   14.8679(9)
_cell_length_b                   10.0040(6)
_cell_length_c                   18.5854(11)
_cell_angle_alpha                90
_cell_angle_beta                 98.871(2)
_cell_angle_gamma                90
_cell_volume                     2731.3(3)
_cell_formula_units_Z            4
_cell_measurement_temperature    100(2)
_cell_measurement_reflns_used    5625
_cell_measurement_theta_min      2.7880
_cell_measurement_theta_max      26.3484

_exptl_crystal_description       Tabullar
_exptl_crystal_colour            Yellow
_exptl_crystal_density_meas      'not measured'
_exptl_crystal_density_method    'not measured'
_exptl_crystal_density_diffrn    1.460
_exptl_crystal_F_000             1216
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.30
_exptl_crystal_size_mid          0.30
_exptl_crystal_size_min          0.10
_exptl_absorpt_coefficient_mu    2.731
_shelx_estimated_absorpt_T_min   ?
_shelx_estimated_absorpt_T_max   ?
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.7832
_exptl_absorpt_correction_T_max  0.9485
_exptl_absorpt_process_details   'SADABS V2012/1 (Bruker AXS Inc.)'

_exptl_special_details           
;
 ?
;

_diffrn_ambient_temperature      100(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 8.3333
_diffrn_reflns_number            19190
_diffrn_reflns_av_unetI/netI     0.0297
_diffrn_reflns_av_R_equivalents  0.0286
_diffrn_reflns_limit_h_min       -16
_diffrn_reflns_limit_h_max       18
_diffrn_reflns_limit_k_min       -12
_diffrn_reflns_limit_k_max       12
_diffrn_reflns_limit_l_min       -23
_diffrn_reflns_limit_l_max       23
_diffrn_reflns_theta_min         1.636
_diffrn_reflns_theta_max         26.381
_diffrn_reflns_theta_full        25.242
_diffrn_measured_fraction_theta_max 0.993
_diffrn_measured_fraction_theta_full 0.997
_diffrn_reflns_Laue_measured_fraction_max 0.993
_diffrn_reflns_Laue_measured_fraction_full 0.997
_diffrn_reflns_point_group_measured_fraction_max 0.993
_diffrn_reflns_point_group_measured_fraction_full 0.997
_reflns_number_total             5560
_reflns_number_gt                4523
_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       'APEX2 (Bruker AXS, 2010)'
_computing_cell_refinement       'SAINT V8.34A (Bruker AXS Inc., 2013)'
_computing_data_reduction        'SAINT V8.34A (Bruker AXS Inc., 2013)'
_computing_structure_solution    ?
_computing_structure_refinement  'SHELXL-2013 (Sheldrick, 2013)'
_computing_molecular_graphics    'SHELXTL (Sheldrick, 2008)'
_computing_publication_material  SHELXTL

_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)+(0.0268P)²+1.3738P] 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         5560
_refine_ls_number_parameters     325
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0409
_refine_ls_R_factor_gt           0.0272
_refine_ls_wR_factor_ref         0.0615
_refine_ls_wR_factor_gt          0.0575
_refine_ls_goodness_of_fit_ref   1.026
_refine_ls_restrained_S_all      1.026
_refine_ls_shift/su_max          0.001
_refine_ls_shift/su_mean         0.000

loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_site_symmetry_order
_atom_site_calc_flag
_atom_site_refinement_flags_posn
_atom_site_refinement_flags_adp
_atom_site_refinement_flags_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
Se1 Se 0.53413(2) 1.23664(2) 0.07990(2) 0.02899(7) Uani 1 1 d . . . . .
Se2 Se 0.40321(2) -0.47394(2) 0.09937(2) 0.02381(7) Uani 1 1 d . . . . .
N1 N 0.58442(14) 0.95707(18) 0.10292(10) 0.0281(4) Uani 1 1 d . . . . .
N2 N 0.35413(14) -0.19219(19) 0.09939(10) 0.0287(4) Uani 1 1 d . . . . .
C1 C 0.56444(15) 1.0679(2) 0.09400(11) 0.0216(5) Uani 1 1 d . . . . .
C2 C 0.61226(16) 0.8202(2) 0.11441(11) 0.0229(5) Uani 1 1 d . . . . .
H1 H 0.6675 0.8040 0.0920 0.028 Uiso 1 1 calc R U . . .
H15 H 0.5635 0.7607 0.0904 0.028 Uiso 1 1 calc R U . . .
C3 C 0.63219(15) 0.78713(19) 0.19545(11) 0.0194(4) Uani 1 1 d . . . . .
H3 H 0.5798 0.8142 0.2191 0.023 Uiso 1 1 calc R U . . .
H2 H 0.6862 0.8382 0.2183 0.023 Uiso 1 1 calc R U . . .
C4 C 0.65001(14) 0.63640(18) 0.20747(10) 0.0148(4) Uani 1 1 d . . . . .
H14 H 0.5957 0.5885 0.1811 0.018 Uiso 1 1 calc R U . . .
C5 C 0.73171(14) 0.59227(18) 0.17295(10) 0.0149(4) Uani 1 1 d . . . . .
C6 C 0.71837(15) 0.53907(19) 0.10282(11) 0.0210(5) Uani 1 1 d . . . . .
H8 H 0.6582 0.5253 0.0782 0.025 Uiso 1 1 calc R U . . .
C7 C 0.79169(16) 0.5061(2) 0.06854(12) 0.0244(5) Uani 1 1 d . . . . .
H4 H 0.7816 0.4716 0.0203 0.029 Uiso 1 1 calc R U . . .
C8 C 0.87986(16) 0.5232(2) 0.10442(12) 0.0240(5) Uani 1 1 d . . . . .
H5 H 0.9302 0.4997 0.0811 0.029 Uiso 1 1 calc R U . . .
C9 C 0.89420(15) 0.5748(2) 0.17448(12) 0.0225(5) Uani 1 1 d . . . . .
H6 H 0.9545 0.5866 0.1993 0.027 Uiso 1 1 calc R U . . .
C10 C 0.82046(15) 0.60921(19) 0.20839(11) 0.0187(4) Uani 1 1 d . . . . .
H7 H 0.8308 0.6447 0.2564 0.022 Uiso 1 1 calc R U . . .
C11 C 0.65885(14) 0.59552(19) 0.28698(11) 0.0163(4) Uani 1 1 d . . . . .
C12 C 0.63195(15) 0.46698(19) 0.30359(11) 0.0197(4) Uani 1 1 d . . . . .
H13 H 0.6084 0.4079 0.2652 0.024 Uiso 1 1 calc R U . . .
C13 C 0.63903(16) 0.4242(2) 0.37513(12) 0.0244(5) Uani 1 1 d . . . . .
H9 H 0.6199 0.3366 0.3855 0.029 Uiso 1 1 calc R U . . .
C14 C 0.67394(16) 0.5088(2) 0.43142(11) 0.0247(5) Uani 1 1 d . . . . .
H10 H 0.6787 0.4798 0.4805 0.030 Uiso 1 1 calc R U . . .
C15 C 0.70180(16) 0.6359(2) 0.41575(12) 0.0256(5) Uani 1 1 d . . . . .
H11 H 0.7263 0.6940 0.4543 0.031 Uiso 1 1 calc R U . . .
C16 C 0.69433(15) 0.6795(2) 0.34421(11) 0.0212(5) Uani 1 1 d . . . . .
H12 H 0.7135 0.7672 0.3342 0.025 Uiso 1 1 calc R U . . .
C17 C 0.37330(15) -0.3044(2) 0.09980(11) 0.0217(5) Uani 1 1 d . . . . .
C18 C 0.33119(16) -0.0533(2) 0.10729(12) 0.0243(5) Uani 1 1 d . . . . .
H29 H 0.2662 -0.0387 0.0876 0.029 Uiso 1 1 calc R U . . .
H30 H 0.3682 0.0032 0.0793 0.029 Uiso 1 1 calc R U . . .
C19 C 0.34920(15) -0.01345(19) 0.18757(11) 0.0192(4) Uani 1 1 d . . . . .
H17 H 0.4130 -0.0356 0.2079 0.023 Uiso 1 1 calc R U . . .
H16 H 0.3089 -0.0661 0.2146 0.023 Uiso 1 1 calc R U . . .
C20 C 0.33282(15) 0.13669(19) 0.19898(11) 0.0179(4) Uani 1 1 d . . . . .
H28 H 0.3723 0.1876 0.1696 0.021 Uiso 1 1 calc R U . . .
C21 C 0.23466(14) 0.17511(19) 0.17172(10) 0.0161(4) Uani 1 1 d . . . . .
C22 C 0.20964(16) 0.22723(19) 0.10146(11) 0.0225(5) Uani 1 1 d . . . . .
H22 H 0.2549 0.2420 0.0714 0.027 Uiso 1 1 calc R U . . .
C23 C 0.11870(17) 0.2576(2) 0.07510(12) 0.0260(5) Uani 1 1 d . . . . .
H18 H 0.1020 0.2918 0.0272 0.031 Uiso 1 1 calc R U . . .
C24 C 0.05310(16) 0.2373(2) 0.11969(12) 0.0267(5) Uani 1 1 d . . . . .
H19 H -0.0089 0.2570 0.1020 0.032 Uiso 1 1 calc R U . . .
C25 C 0.07725(16) 0.1890(2) 0.18920(12) 0.0256(5) Uani 1 1 d . . . . .
H20 H 0.0322 0.1767 0.2197 0.031 Uiso 1 1 calc R U . . .
C26 C 0.16710(15) 0.15832(19) 0.21471(11) 0.0208(5) Uani 1 1 d . . . . .
H21 H 0.1830 0.1249 0.2628 0.025 Uiso 1 1 calc R U . . .
C27 C 0.36030(14) 0.17694(19) 0.27866(11) 0.0176(4) Uani 1 1 d . . . . .
C28 C 0.38421(15) 0.3087(2) 0.29447(11) 0.0222(5) Uani 1 1 d . . . . .
H27 H 0.3842 0.3709 0.2558 0.027 Uiso 1 1 calc R U . . .
C29 C 0.40828(17) 0.3515(2) 0.36599(12) 0.0281(5) Uani 1 1 d . . . . .
H26 H 0.4240 0.4424 0.3760 0.034 Uiso 1 1 calc R U . . .
C30 C 0.40922(16) 0.2616(2) 0.42250(12) 0.0282(5) Uani 1 1 d . . . . .
H25 H 0.4258 0.2902 0.4715 0.034 Uiso 1 1 calc R U . . .
C31 C 0.38602(16) 0.1305(2) 0.40745(12) 0.0265(5) Uani 1 1 d . . . . .
H24 H 0.3867 0.0685 0.4463 0.032 Uiso 1 1 calc R U . . .
C32 C 0.36162(15) 0.0878(2) 0.33614(12) 0.0228(5) Uani 1 1 d . . . . .
H23 H 0.3457 -0.0031 0.3265 0.027 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 C1 1.756(2) . ?
Se2 C17 1.754(2) . ?
N1 C1 1.153(3) . ?
N1 C2 1.437(3) . ?
N2 C17 1.158(3) . ?
N2 C18 1.444(3) . ?
C2 C3 1.526(3) . ?
C2 H1 0.9900 . ?
C2 H15 0.9900 . ?
C3 C4 1.541(3) . ?
C3 H3 0.9900 . ?
C3 H2 0.9900 . ?
C4 C11 1.519(3) . ?
C4 C5 1.524(3) . ?
C4 H14 1.0000 . ?
C5 C10 1.391(3) . ?
C5 C6 1.393(3) . ?
C6 C7 1.385(3) . ?
C6 H8 0.9500 . ?
C7 C8 1.387(3) . ?
C7 H4 0.9500 . ?
C8 C9 1.386(3) . ?
C8 H5 0.9500 . ?
C9 C10 1.390(3) . ?
C9 H6 0.9500 . ?
C10 H7 0.9500 . ?
C11 C16 1.394(3) . ?
C11 C12 1.395(3) . ?
C12 C13 1.385(3) . ?
C12 H13 0.9500 . ?
C13 C14 1.383(3) . ?
C13 H9 0.9500 . ?
C14 C15 1.382(3) . ?
C14 H10 0.9500 . ?
C15 C16 1.387(3) . ?
C15 H11 0.9500 . ?
C16 H12 0.9500 . ?
C18 C19 1.528(3) . ?
C18 H29 0.9900 . ?
C18 H30 0.9900 . ?
C19 C20 1.542(3) . ?
C19 H17 0.9900 . ?
C19 H16 0.9900 . ?
C20 C21 1.519(3) . ?
C20 C27 1.528(3) . ?
C20 H28 1.0000 . ?
C21 C26 1.387(3) . ?
C21 C22 1.402(3) . ?
C22 C23 1.399(3) . ?
C22 H22 0.9500 . ?
C23 C24 1.389(3) . ?
C23 H18 0.9500 . ?
C24 C25 1.374(3) . ?
C24 H19 0.9500 . ?
C25 C26 1.381(3) . ?
C25 H20 0.9500 . ?
C26 H21 0.9500 . ?
C27 C28 1.385(3) . ?
C27 C32 1.389(3) . ?
C28 C29 1.390(3) . ?
C28 H27 0.9500 . ?
C29 C30 1.381(3) . ?
C29 H26 0.9500 . ?
C30 C31 1.374(3) . ?
C30 H25 0.9500 . ?
C31 C32 1.386(3) . ?
C31 H24 0.9500 . ?
C32 H23 0.9500 . ?

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 N1 C2 178.2(2) . . ?
C17 N2 C18 173.8(2) . . ?
N1 C1 Se1 179.7(2) . . ?
N1 C2 C3 111.16(17) . . ?
N1 C2 H1 109.4 . . ?
C3 C2 H1 109.4 . . ?
N1 C2 H15 109.4 . . ?
C3 C2 H15 109.4 . . ?
H1 C2 H15 108.0 . . ?
C2 C3 C4 110.99(16) . . ?
C2 C3 H3 109.4 . . ?
C4 C3 H3 109.4 . . ?
C2 C3 H2 109.4 . . ?
C4 C3 H2 109.4 . . ?
H3 C3 H2 108.0 . . ?
C11 C4 C5 112.11(16) . . ?
C11 C4 C3 113.05(16) . . ?
C5 C4 C3 110.65(16) . . ?
C11 C4 H14 106.9 . . ?
C5 C4 H14 106.9 . . ?
C3 C4 H14 106.9 . . ?
C10 C5 C6 118.5(2) . . ?
C10 C5 C4 121.66(18) . . ?
C6 C5 C4 119.79(18) . . ?
C7 C6 C5 120.9(2) . . ?
C7 C6 H8 119.6 . . ?
C5 C6 H8 119.6 . . ?
C6 C7 C8 120.1(2) . . ?
C6 C7 H4 119.9 . . ?
C8 C7 H4 119.9 . . ?
C9 C8 C7 119.7(2) . . ?
C9 C8 H5 120.2 . . ?
C7 C8 H5 120.2 . . ?
C8 C9 C10 120.0(2) . . ?
C8 C9 H6 120.0 . . ?
C10 C9 H6 120.0 . . ?
C9 C10 C5 120.82(19) . . ?
C9 C10 H7 119.6 . . ?
C5 C10 H7 119.6 . . ?
C16 C11 C12 118.32(18) . . ?
C16 C11 C4 123.08(18) . . ?
C12 C11 C4 118.59(17) . . ?
C13 C12 C11 121.02(19) . . ?
C13 C12 H13 119.5 . . ?
C11 C12 H13 119.5 . . ?
C14 C13 C12 120.0(2) . . ?
C14 C13 H9 120.0 . . ?
C12 C13 H9 120.0 . . ?
C15 C14 C13 119.6(2) . . ?
C15 C14 H10 120.2 . . ?
C13 C14 H10 120.2 . . ?
C14 C15 C16 120.6(2) . . ?
C14 C15 H11 119.7 . . ?
C16 C15 H11 119.7 . . ?
C15 C16 C11 120.47(19) . . ?
C15 C16 H12 119.8 . . ?
C11 C16 H12 119.8 . . ?
N2 C17 Se2 179.2(2) . . ?
N2 C18 C19 109.99(17) . . ?
N2 C18 H29 109.7 . . ?
C19 C18 H29 109.7 . . ?
N2 C18 H30 109.7 . . ?
C19 C18 H30 109.7 . . ?
H29 C18 H30 108.2 . . ?
C18 C19 C20 112.39(16) . . ?
C18 C19 H17 109.1 . . ?
C20 C19 H17 109.1 . . ?
C18 C19 H16 109.1 . . ?
C20 C19 H16 109.1 . . ?
H17 C19 H16 107.9 . . ?
C21 C20 C27 110.87(17) . . ?
C21 C20 C19 111.39(17) . . ?
C27 C20 C19 111.45(16) . . ?
C21 C20 H28 107.6 . . ?
C27 C20 H28 107.6 . . ?
C19 C20 H28 107.6 . . ?
C26 C21 C22 118.0(2) . . ?
C26 C21 C20 121.42(18) . . ?
C22 C21 C20 120.54(19) . . ?
C23 C22 C21 120.7(2) . . ?
C23 C22 H22 119.7 . . ?
C21 C22 H22 119.7 . . ?
C24 C23 C22 119.3(2) . . ?
C24 C23 H18 120.4 . . ?
C22 C23 H18 120.4 . . ?
C25 C24 C23 120.4(2) . . ?
C25 C24 H19 119.8 . . ?
C23 C24 H19 119.8 . . ?
C24 C25 C26 120.0(2) . . ?
C24 C25 H20 120.0 . . ?
C26 C25 H20 120.0 . . ?
C25 C26 C21 121.6(2) . . ?
C25 C26 H21 119.2 . . ?
C21 C26 H21 119.2 . . ?
C28 C27 C32 118.36(18) . . ?
C28 C27 C20 118.54(17) . . ?
C32 C27 C20 123.09(18) . . ?
C27 C28 C29 121.03(19) . . ?
C27 C28 H27 119.5 . . ?
C29 C28 H27 119.5 . . ?
C30 C29 C28 119.9(2) . . ?
C30 C29 H26 120.1 . . ?
C28 C29 H26 120.1 . . ?
C31 C30 C29 119.6(2) . . ?
C31 C30 H25 120.2 . . ?
C29 C30 H25 120.2 . . ?
C30 C31 C32 120.6(2) . . ?
C30 C31 H24 119.7 . . ?
C32 C31 H24 119.7 . . ?
C31 C32 C27 120.5(2) . . ?
C31 C32 H23 119.7 . . ?
C27 C32 H23 119.7 . . ?

_refine_diff_density_max         0.427
_refine_diff_density_min         -0.371
_refine_diff_density_rms         0.062

_shelxl_version_number           2013-4

