# Electronic Supplementary Material (ESI) for CrystEngComm.
# This journal is © The Royal Society of Chemistry 2016

####################################################################### 
# 
# 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_ee
_database_code_depnum_ccdc_archive 'CCDC 1474550'
_audit_update_record             
;
2016-04-17 deposited with the CCDC.
2016-08-22 downloaded from the CCDC.
;
_audit_creation_date             2015-10-23
_audit_creation_method           
;
Olex2 1.2
(compiled 2015.09.30 svn.r3233 for OlexSys, GUI svn.r5103)
;
_chemical_name_common            ?
_chemical_name_systematic        
;
 ? 
;
_chemical_formula_moiety         'I, C19 H20 N O2 Se, 0.5(C6 H6)'
_chemical_formula_sum            'C22 H23 I N O2 Se'
_chemical_formula_weight         539.27
_chemical_melting_point          ?
loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
I I -0.4742 1.8119 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
N N 0.0061 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
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'

_space_group_crystal_system      triclinic
_space_group_IT_number           2
_space_group_name_H-M_alt        'P -1'
_space_group_name_Hall           '-P 1'
loop_
_space_group_symop_id
_space_group_symop_operation_xyz
1 'x, y, z'
2 '-x, -y, -z'

_cell_length_a                   11.6009(7)
_cell_length_b                   13.0363(8)
_cell_length_c                   15.2941(9)
_cell_angle_alpha                106.333(2)
_cell_angle_beta                 96.656(2)
_cell_angle_gamma                106.040(2)
_cell_volume                     2085.7(2)
_cell_formula_units_Z            4
_cell_measurement_reflns_used    2054
_cell_measurement_temperature    120.15
_cell_measurement_theta_max      26
_cell_measurement_theta_min      2.8
_exptl_absorpt_coefficient_mu    3.297
_exptl_absorpt_correction_T_max  0.7463
_exptl_absorpt_correction_T_min  0.4935
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   ?
_exptl_crystal_colour            'dark red'
_exptl_crystal_colour_modifier   dark
_exptl_crystal_colour_primary    red
_exptl_crystal_density_diffrn    1.717
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       needle
_exptl_crystal_F_000             1060
_exptl_crystal_size_max          0.33
_exptl_crystal_size_mid          0.07
_exptl_crystal_size_min          0.06
_exptl_special_details           
;
 ? 
;
_diffrn_reflns_av_R_equivalents  0.0698
_diffrn_reflns_av_unetI/netI     0.0741
_diffrn_reflns_limit_h_max       15
_diffrn_reflns_limit_h_min       -15
_diffrn_reflns_limit_k_max       17
_diffrn_reflns_limit_k_min       -17
_diffrn_reflns_limit_l_max       20
_diffrn_reflns_limit_l_min       -20
_diffrn_reflns_number            31365
_diffrn_reflns_theta_full        29.00
_diffrn_reflns_theta_max         29.00
_diffrn_reflns_theta_min         2.43
_diffrn_ambient_temperature      120.15
_diffrn_detector_area_resol_mean ?
_diffrn_measured_fraction_theta_full 0.991
_diffrn_measured_fraction_theta_max 0.991
_diffrn_measurement_device_type  'CCD Bruker-8 Venture'
_diffrn_measurement_method       ?
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_source                   'fine-focus sealed tube'
_diffrn_standards_decay_%        ?
_diffrn_standards_interval_count ?
_diffrn_standards_interval_time  ?
_diffrn_standards_number         ?
_reflns_number_gt                9059
_reflns_number_total             10980
_reflns_threshold_expression     >2sigma(I)
_computing_cell_refinement       ?
_computing_data_collection       ?
_computing_data_reduction        ?
_computing_molecular_graphics    'Olex2 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 (Dolomanov et al., 2009)'
_computing_structure_refinement  'XH (Sheldrick, 2008)'
_computing_structure_solution    'ShelXS-1997 (Sheldrick, 2008)'
_refine_diff_density_max         2.098
_refine_diff_density_min         -0.952
_refine_diff_density_rms         0.241
_refine_ls_extinction_coef       ?
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.038
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     493
_refine_ls_number_reflns         10980
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0733
_refine_ls_R_factor_gt           0.0619
_refine_ls_restrained_S_all      1.038
_refine_ls_shift/su_max          0.001
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details     
'calc w=1/[σ²(Fo²)+(0.0994P)²+0.0000P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1524
_refine_ls_wR_factor_ref         0.1586
_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. 
;
_olex2_refinement_description    
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups, All C(H,H) groups
 At 1.5 times of:
  All C(H,H,H) groups
2.a Secondary CH2 refined with riding coordinates:
 C18(H18A,H18B), C18A(H18C,H18D)
2.b Aromatic/amide H refined with riding coordinates:
 C2(H2), C3(H3), C5(H5), C8(H8), C9(H9), C14(H14), C15(H15), C16(H16),
 C17(H17), C2A(H2A), C3A(H3A), C5A(H5A), C8A(H8A), C9A(H9A), C14A(H14A),
 C15A(H15A), C16A(H16A), C17A(H17A), C1S(H1S), C2S(H2S), C3S(H3S), C4S(H4S),
 C5S(H5S), C6S(H6S)
2.c Idealised Me refined as rotating group:
 C10(H10A,H10B,H10C), C11(H11A,H11B,H11C), C19(H19A,H19B,H19C), C10A(H10D,H10E,
 H10F), C11A(H11D,H11E,H11F), C19A(H19D,H19E,H19F)
;
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
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_calc_flag
_atom_site_disorder_assembly
_atom_site_disorder_group
_atom_site_refinement_flags_posn
I1 I 0.22672(3) 0.81505(2) 1.402655(18) 0.02794(10) Uani 1 d . . .
I2 I 0.28519(3) 0.70403(2) 0.960551(19) 0.02830(10) Uani 1 d . . .
Se1 Se 0.19061(4) 0.08878(4) 0.33923(3) 0.02277(11) Uani 1 d . . .
Se1A Se 0.42104(4) 0.33960(4) 1.16162(3) 0.02512(11) Uani 1 d . . .
O1 O 0.0557(3) 0.1740(3) 0.8580(2) 0.0288(6) Uani 1 d . . .
O2 O 0.2170(3) 0.0913(3) 0.90745(19) 0.0275(6) Uani 1 d . . .
N1 N 0.0119(3) 0.1815(3) 0.3556(2) 0.0199(6) Uani 1 d . . .
C1 C 0.0835(3) 0.1441(3) 0.4060(3) 0.0200(7) Uani 1 d . . .
C2 C 0.0798(4) 0.1468(3) 0.4992(3) 0.0209(8) Uani 1 d . . .
H2 H 0.0299 0.1834 0.5321 0.025 Uiso 1 calc . . R
C3 C 0.1475(3) 0.0972(3) 0.5414(3) 0.0212(8) Uani 1 d . . .
H3 H 0.1932 0.0597 0.5040 0.025 Uiso 1 calc . . R
C4 C 0.1592(4) 0.0940(3) 0.6361(3) 0.0217(8) Uani 1 d . . .
C5 C 0.0915(4) 0.1373(3) 0.7003(3) 0.0220(8) Uani 1 d . . .
H5 H 0.0317 0.1684 0.6817 0.026 Uiso 1 calc . . R
C6 C 0.1128(4) 0.1340(3) 0.7892(3) 0.0223(8) Uani 1 d . . .
C7 C 0.2003(4) 0.0862(3) 0.8168(3) 0.0217(8) Uani 1 d . . .
C8 C 0.2641(4) 0.0407(3) 0.7548(3) 0.0223(8) Uani 1 d . . .
H8 H 0.3219 0.0076 0.7735 0.027 Uiso 1 calc . . R
C9 C 0.2428(4) 0.0439(3) 0.6633(3) 0.0230(8) Uani 1 d . . .
H9 H 0.2856 0.0118 0.6197 0.028 Uiso 1 calc . . R
C10 C -0.0320(5) 0.2242(5) 0.8356(3) 0.0376(11) Uani 1 d . . .
H10A H -0.0958 0.1700 0.7822 0.056 Uiso 1 calc . . GR
H10B H 0.0082 0.2913 0.8198 0.056 Uiso 1 calc . . GR
H10C H -0.0693 0.2462 0.8892 0.056 Uiso 1 calc . . GR
C11 C 0.3084(4) 0.0480(5) 0.9398(3) 0.0354(11) Uani 1 d . . .
H11A H 0.2859 -0.0328 0.9054 0.053 Uiso 1 calc . . GR
H11B H 0.3137 0.0592 1.0065 0.053 Uiso 1 calc . . GR
H11C H 0.3880 0.0881 0.9298 0.053 Uiso 1 calc . . GR
C12 C 0.1189(3) 0.1249(3) 0.2402(3) 0.0204(7) Uani 1 d . . .
C13 C 0.0290(3) 0.1726(3) 0.2648(3) 0.0200(7) Uani 1 d . . .
C14 C -0.0366(4) 0.2043(4) 0.2004(3) 0.0251(8) Uani 1 d . . .
H14 H -0.0985 0.2367 0.2161 0.030 Uiso 1 calc . . R
C15 C -0.0088(4) 0.1873(4) 0.1128(3) 0.0270(9) Uani 1 d . . .
H15 H -0.0510 0.2102 0.0687 0.032 Uiso 1 calc . . R
C16 C 0.0788(4) 0.1378(4) 0.0881(3) 0.0293(9) Uani 1 d . . .
H16 H 0.0944 0.1255 0.0270 0.035 Uiso 1 calc . . R
C17 C 0.1449(4) 0.1059(4) 0.1520(3) 0.0263(9) Uani 1 d . . .
H17 H 0.2056 0.0722 0.1356 0.032 Uiso 1 calc . . R
C18 C -0.0818(4) 0.2273(4) 0.3929(3) 0.0233(8) Uani 1 d . . .
H18A H -0.1112 0.1920 0.4392 0.028 Uiso 1 calc . . R
H18B H -0.1526 0.2082 0.3416 0.028 Uiso 1 calc . . R
C19 C -0.0307(5) 0.3543(4) 0.4387(3) 0.0346(10) Uani 1 d . . .
H19A H -0.0023 0.3894 0.3929 0.052 Uiso 1 calc . . GR
H19B H 0.0382 0.3733 0.4904 0.052 Uiso 1 calc . . GR
H19C H -0.0949 0.3824 0.4624 0.052 Uiso 1 calc . . GR
O1A O 0.2696(3) 0.4251(3) 0.6656(2) 0.0354(7) Uani 1 d . . .
O2A O 0.4029(3) 0.3135(3) 0.5887(2) 0.0307(7) Uani 1 d . . .
N1A N 0.2813(3) 0.4732(3) 1.1714(2) 0.0221(7) Uani 1 d . . .
C1A C 0.3363(4) 0.4194(3) 1.1113(3) 0.0242(8) Uani 1 d . . .
C2A C 0.3312(4) 0.4186(3) 1.0170(3) 0.0235(8) Uani 1 d . . .
H2A H 0.2801 0.4537 0.9921 0.028 Uiso 1 calc . . R
C3A C 0.3975(4) 0.3689(3) 0.9632(3) 0.0229(8) Uani 1 d . . .
H3A H 0.4486 0.3368 0.9920 0.027 Uiso 1 calc . . R
C4A C 0.4005(4) 0.3585(3) 0.8671(3) 0.0242(8) Uani 1 d . . .
C5A C 0.3304(4) 0.4023(4) 0.8156(3) 0.0262(9) Uani 1 d . . .
H5A H 0.2801 0.4423 0.8442 0.031 Uiso 1 calc . . R
C6A C 0.3346(4) 0.3871(3) 0.7234(3) 0.0252(8) Uani 1 d . . .
C7A C 0.4097(4) 0.3285(3) 0.6808(3) 0.0241(8) Uani 1 d . . .
C8A C 0.4809(4) 0.2876(4) 0.7325(3) 0.0255(8) Uani 1 d . . .
H8A H 0.5327 0.2492 0.7045 0.031 Uiso 1 calc . . R
C9A C 0.4761(4) 0.3031(4) 0.8251(3) 0.0268(9) Uani 1 d . . .
H9A H 0.5253 0.2753 0.8605 0.032 Uiso 1 calc . . R
C10A C 0.1822(5) 0.4745(5) 0.7033(3) 0.0448(13) Uani 1 d . . .
H10D H 0.1444 0.5021 0.6578 0.067 Uiso 1 calc . . GR
H10E H 0.2240 0.5377 0.7608 0.067 Uiso 1 calc . . GR
H10F H 0.1186 0.4175 0.7169 0.067 Uiso 1 calc . . GR
C11A C 0.4665(4) 0.2436(4) 0.5420(3) 0.0320(10) Uani 1 d . . .
H11D H 0.4483 0.2325 0.4751 0.048 Uiso 1 calc . . GR
H11E H 0.4401 0.1703 0.5518 0.048 Uiso 1 calc . . GR
H11F H 0.5549 0.2798 0.5666 0.048 Uiso 1 calc . . GR
C12A C 0.3671(4) 0.3932(3) 1.2706(3) 0.0233(8) Uani 1 d . . .
C13A C 0.2954(4) 0.4610(3) 1.2599(3) 0.0216(8) Uani 1 d . . .
C14A C 0.2471(4) 0.5105(4) 1.3335(3) 0.0275(9) Uani 1 d . . .
H14A H 0.1976 0.5560 1.3267 0.033 Uiso 1 calc . . R
C15A C 0.2735(4) 0.4913(4) 1.4165(3) 0.0309(9) Uani 1 d . . .
H15A H 0.2423 0.5254 1.4677 0.037 Uiso 1 calc . . R
C16A C 0.3440(4) 0.4239(4) 1.4279(3) 0.0314(9) Uani 1 d . . .
H16A H 0.3587 0.4114 1.4859 0.038 Uiso 1 calc . . R
C17A C 0.3925(4) 0.3753(4) 1.3558(3) 0.0279(9) Uani 1 d . . .
H17A H 0.4423 0.3303 1.3635 0.033 Uiso 1 calc . . R
C18A C 0.2108(4) 0.5454(4) 1.1493(3) 0.0281(9) Uani 1 d . . .
H18C H 0.2435 0.5769 1.1020 0.034 Uiso 1 calc . . R
H18D H 0.2206 0.6092 1.2062 0.034 Uiso 1 calc . . R
C19A C 0.0763(4) 0.4778(4) 1.1127(4) 0.0376(11) Uani 1 d . . .
H19D H 0.0659 0.4190 1.0532 0.056 Uiso 1 calc . . GR
H19E H 0.0304 0.5281 1.1033 0.056 Uiso 1 calc . . GR
H19F H 0.0453 0.4426 1.1578 0.056 Uiso 1 calc . . GR
C1S C 0.4963(5) 0.0553(5) 1.3358(3) 0.0389(12) Uani 1 d . . .
H1S H 0.4899 0.0368 1.3913 0.047 Uiso 1 calc . . R
C2S C 0.4221(4) -0.0192(4) 1.2511(4) 0.0352(10) Uani 1 d . . .
H2S H 0.3646 -0.0883 1.2487 0.042 Uiso 1 calc . . R
C3S C 0.4320(4) 0.0075(4) 1.1705(3) 0.0345(10) Uani 1 d . . .
H3S H 0.3819 -0.0437 1.1126 0.041 Uiso 1 calc . . R
C4S C 0.5146(4) 0.1085(4) 1.1739(3) 0.0311(10) Uani 1 d . . .
H4S H 0.5217 0.1268 1.1184 0.037 Uiso 1 calc . . R
C5S C 0.5866(4) 0.1824(4) 1.2581(3) 0.0329(10) Uani 1 d . . .
H5S H 0.6422 0.2526 1.2607 0.040 Uiso 1 calc . . R
C6S C 0.5787(4) 0.1557(5) 1.3392(3) 0.0376(11) Uani 1 d . . .
H6S H 0.6301 0.2065 1.3968 0.045 Uiso 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 1.866(4) . ?
Se1 C12 1.880(4) . ?
Se1A C1A 1.867(4) . ?
Se1A C12A 1.868(4) . ?
O1 C6 1.365(5) . ?
O1 C10 1.412(5) . ?
O2 C7 1.357(5) . ?
O2 C11 1.432(5) . ?
N1 C1 1.345(5) . ?
N1 C13 1.403(5) . ?
N1 C18 1.475(5) . ?
C1 C2 1.421(5) . ?
C2 H2 0.9500 . ?
C2 C3 1.359(5) . ?
C3 H3 0.9500 . ?
C3 C4 1.452(5) . ?
C4 C5 1.418(5) . ?
C4 C9 1.396(6) . ?
C5 H5 0.9500 . ?
C5 C6 1.368(5) . ?
C6 C7 1.412(6) . ?
C7 C8 1.374(5) . ?
C8 H8 0.9500 . ?
C8 C9 1.407(5) . ?
C9 H9 0.9500 . ?
C10 H10A 0.9800 . ?
C10 H10B 0.9800 . ?
C10 H10C 0.9800 . ?
C11 H11A 0.9800 . ?
C11 H11B 0.9800 . ?
C11 H11C 0.9800 . ?
C12 C13 1.390(5) . ?
C12 C17 1.385(5) . ?
C13 C14 1.397(5) . ?
C14 H14 0.9500 . ?
C14 C15 1.385(6) . ?
C15 H15 0.9500 . ?
C15 C16 1.380(6) . ?
C16 H16 0.9500 . ?
C16 C17 1.396(6) . ?
C17 H17 0.9500 . ?
C18 H18A 0.9900 . ?
C18 H18B 0.9900 . ?
C18 C19 1.514(6) . ?
C19 H19A 0.9800 . ?
C19 H19B 0.9800 . ?
C19 H19C 0.9800 . ?
O1A C6A 1.375(5) . ?
O1A C10A 1.437(6) . ?
O2A C7A 1.356(5) . ?
O2A C11A 1.418(5) . ?
N1A C1A 1.327(5) . ?
N1A C13A 1.403(5) . ?
N1A C18A 1.486(5) . ?
C1A C2A 1.433(6) . ?
C2A H2A 0.9500 . ?
C2A C3A 1.345(6) . ?
C3A H3A 0.9500 . ?
C3A C4A 1.443(6) . ?
C4A C5A 1.402(6) . ?
C4A C9A 1.387(6) . ?
C5A H5A 0.9500 . ?
C5A C6A 1.376(6) . ?
C6A C7A 1.410(6) . ?
C7A C8A 1.386(6) . ?
C8A H8A 0.9500 . ?
C8A C9A 1.383(6) . ?
C9A H9A 0.9500 . ?
C10A H10D 0.9800 . ?
C10A H10E 0.9800 . ?
C10A H10F 0.9800 . ?
C11A H11D 0.9800 . ?
C11A H11E 0.9800 . ?
C11A H11F 0.9800 . ?
C12A C13A 1.398(6) . ?
C12A C17A 1.399(6) . ?
C13A C14A 1.391(6) . ?
C14A H14A 0.9500 . ?
C14A C15A 1.379(6) . ?
C15A H15A 0.9500 . ?
C15A C16A 1.385(6) . ?
C16A H16A 0.9500 . ?
C16A C17A 1.373(6) . ?
C17A H17A 0.9500 . ?
C18A H18C 0.9900 . ?
C18A H18D 0.9900 . ?
C18A C19A 1.512(6) . ?
C19A H19D 0.9800 . ?
C19A H19E 0.9800 . ?
C19A H19F 0.9800 . ?
C1S H1S 0.9500 . ?
C1S C2S 1.390(8) . ?
C1S C6S 1.375(8) . ?
C2S H2S 0.9500 . ?
C2S C3S 1.381(7) . ?
C3S H3S 0.9500 . ?
C3S C4S 1.381(7) . ?
C4S H4S 0.9500 . ?
C4S C5S 1.376(7) . ?
C5S H5S 0.9500 . ?
C5S C6S 1.385(7) . ?
C6S H6S 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 Se1 C12 86.64(17) . . ?
C1A Se1A C12A 86.27(18) . . ?
C6 O1 C10 117.0(3) . . ?
C7 O2 C11 117.4(3) . . ?
C1 N1 C13 116.6(3) . . ?
C1 N1 C18 121.9(3) . . ?
C13 N1 C18 121.5(3) . . ?
N1 C1 Se1 111.8(3) . . ?
N1 C1 C2 124.6(4) . . ?
C2 C1 Se1 123.6(3) . . ?
C1 C2 H2 119.9 . . ?
C3 C2 C1 120.3(4) . . ?
C3 C2 H2 119.9 . . ?
C2 C3 H3 115.7 . . ?
C2 C3 C4 128.5(4) . . ?
C4 C3 H3 115.7 . . ?
C5 C4 C3 124.4(4) . . ?
C9 C4 C3 116.3(4) . . ?
C9 C4 C5 119.4(4) . . ?
C4 C5 H5 120.1 . . ?
C6 C5 C4 119.8(4) . . ?
C6 C5 H5 120.1 . . ?
O1 C6 C5 125.7(4) . . ?
O1 C6 C7 114.0(4) . . ?
C5 C6 C7 120.4(4) . . ?
O2 C7 C6 115.3(3) . . ?
O2 C7 C8 123.9(4) . . ?
C8 C7 C6 120.8(4) . . ?
C7 C8 H8 120.4 . . ?
C7 C8 C9 119.1(4) . . ?
C9 C8 H8 120.4 . . ?
C4 C9 C8 120.5(4) . . ?
C4 C9 H9 119.7 . . ?
C8 C9 H9 119.7 . . ?
O1 C10 H10A 109.5 . . ?
O1 C10 H10B 109.5 . . ?
O1 C10 H10C 109.5 . . ?
H10A C10 H10B 109.5 . . ?
H10A C10 H10C 109.5 . . ?
H10B C10 H10C 109.5 . . ?
O2 C11 H11A 109.5 . . ?
O2 C11 H11B 109.5 . . ?
O2 C11 H11C 109.5 . . ?
H11A C11 H11B 109.5 . . ?
H11A C11 H11C 109.5 . . ?
H11B C11 H11C 109.5 . . ?
C13 C12 Se1 111.0(3) . . ?
C17 C12 Se1 127.2(3) . . ?
C17 C12 C13 121.8(4) . . ?
C12 C13 N1 113.9(3) . . ?
C12 C13 C14 120.0(3) . . ?
C14 C13 N1 126.1(4) . . ?
C13 C14 H14 120.9 . . ?
C15 C14 C13 118.1(4) . . ?
C15 C14 H14 120.9 . . ?
C14 C15 H15 119.2 . . ?
C16 C15 C14 121.6(4) . . ?
C16 C15 H15 119.2 . . ?
C15 C16 H16 119.7 . . ?
C15 C16 C17 120.6(4) . . ?
C17 C16 H16 119.7 . . ?
C12 C17 C16 117.8(4) . . ?
C12 C17 H17 121.1 . . ?
C16 C17 H17 121.1 . . ?
N1 C18 H18A 109.4 . . ?
N1 C18 H18B 109.4 . . ?
N1 C18 C19 111.3(3) . . ?
H18A C18 H18B 108.0 . . ?
C19 C18 H18A 109.4 . . ?
C19 C18 H18B 109.4 . . ?
C18 C19 H19A 109.5 . . ?
C18 C19 H19B 109.5 . . ?
C18 C19 H19C 109.5 . . ?
H19A C19 H19B 109.5 . . ?
H19A C19 H19C 109.5 . . ?
H19B C19 H19C 109.5 . . ?
C6A O1A C10A 116.2(3) . . ?
C7A O2A C11A 116.6(3) . . ?
C1A N1A C13A 116.3(3) . . ?
C1A N1A C18A 123.2(3) . . ?
C13A N1A C18A 120.5(3) . . ?
N1A C1A Se1A 112.6(3) . . ?
N1A C1A C2A 125.3(4) . . ?
C2A C1A Se1A 122.1(3) . . ?
C1A C2A H2A 119.4 . . ?
C3A C2A C1A 121.2(4) . . ?
C3A C2A H2A 119.4 . . ?
C2A C3A H3A 116.0 . . ?
C2A C3A C4A 128.0(4) . . ?
C4A C3A H3A 116.0 . . ?
C5A C4A C3A 122.5(4) . . ?
C9A C4A C3A 118.0(4) . . ?
C9A C4A C5A 119.5(4) . . ?
C4A C5A H5A 120.1 . . ?
C6A C5A C4A 119.8(4) . . ?
C6A C5A H5A 120.1 . . ?
O1A C6A C5A 125.3(4) . . ?
O1A C6A C7A 114.5(4) . . ?
C5A C6A C7A 120.2(4) . . ?
O2A C7A C6A 115.6(4) . . ?
O2A C7A C8A 124.6(4) . . ?
C8A C7A C6A 119.8(4) . . ?
C7A C8A H8A 120.2 . . ?
C9A C8A C7A 119.7(4) . . ?
C9A C8A H8A 120.2 . . ?
C4A C9A H9A 119.5 . . ?
C8A C9A C4A 121.0(4) . . ?
C8A C9A H9A 119.5 . . ?
O1A C10A H10D 109.5 . . ?
O1A C10A H10E 109.5 . . ?
O1A C10A H10F 109.5 . . ?
H10D C10A H10E 109.5 . . ?
H10D C10A H10F 109.5 . . ?
H10E C10A H10F 109.5 . . ?
O2A C11A H11D 109.5 . . ?
O2A C11A H11E 109.5 . . ?
O2A C11A H11F 109.5 . . ?
H11D C11A H11E 109.5 . . ?
H11D C11A H11F 109.5 . . ?
H11E C11A H11F 109.5 . . ?
C13A C12A Se1A 111.2(3) . . ?
C13A C12A C17A 120.6(4) . . ?
C17A C12A Se1A 128.2(3) . . ?
C12A C13A N1A 113.6(3) . . ?
C14A C13A N1A 126.0(4) . . ?
C14A C13A C12A 120.4(4) . . ?
C13A C14A H14A 121.1 . . ?
C15A C14A C13A 117.8(4) . . ?
C15A C14A H14A 121.1 . . ?
C14A C15A H15A 118.8 . . ?
C14A C15A C16A 122.4(4) . . ?
C16A C15A H15A 118.8 . . ?
C15A C16A H16A 119.9 . . ?
C17A C16A C15A 120.2(4) . . ?
C17A C16A H16A 119.9 . . ?
C12A C17A H17A 120.6 . . ?
C16A C17A C12A 118.7(4) . . ?
C16A C17A H17A 120.6 . . ?
N1A C18A H18C 109.5 . . ?
N1A C18A H18D 109.5 . . ?
N1A C18A C19A 110.7(4) . . ?
H18C C18A H18D 108.1 . . ?
C19A C18A H18C 109.5 . . ?
C19A C18A H18D 109.5 . . ?
C18A C19A H19D 109.5 . . ?
C18A C19A H19E 109.5 . . ?
C18A C19A H19F 109.5 . . ?
H19D C19A H19E 109.5 . . ?
H19D C19A H19F 109.5 . . ?
H19E C19A H19F 109.5 . . ?
C2S C1S H1S 120.1 . . ?
C6S C1S H1S 120.1 . . ?
C6S C1S C2S 119.9(4) . . ?
C1S C2S H2S 120.0 . . ?
C3S C2S C1S 120.0(5) . . ?
C3S C2S H2S 120.0 . . ?
C2S C3S H3S 119.9 . . ?
C2S C3S C4S 120.2(5) . . ?
C4S C3S H3S 119.9 . . ?
C3S C4S H4S 120.2 . . ?
C5S C4S C3S 119.6(4) . . ?
C5S C4S H4S 120.2 . . ?
C4S C5S H5S 119.6 . . ?
C4S C5S C6S 120.7(5) . . ?
C6S C5S H5S 119.6 . . ?
C1S C6S C5S 119.7(5) . . ?
C1S C6S H6S 120.2 . . ?
C5S C6S H6S 120.2 . . ?

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
Se1 C1 C2 C3 -6.9(5) . . . . ?
Se1 C12 C13 N1 -0.7(4) . . . . ?
Se1 C12 C13 C14 -179.2(3) . . . . ?
Se1 C12 C17 C16 178.9(3) . . . . ?
Se1A C1A C2A C3A -6.6(6) . . . . ?
Se1A C12A C13A N1A -0.2(4) . . . . ?
Se1A C12A C13A C14A -179.3(3) . . . . ?
Se1A C12A C17A C16A 179.3(3) . . . . ?
O1 C6 C7 O2 -2.3(5) . . . . ?
O1 C6 C7 C8 179.0(4) . . . . ?
O2 C7 C8 C9 -177.5(4) . . . . ?
N1 C1 C2 C3 173.7(4) . . . . ?
N1 C13 C14 C15 -178.7(4) . . . . ?
C1 Se1 C12 C13 0.6(3) . . . . ?
C1 Se1 C12 C17 -177.5(4) . . . . ?
C1 N1 C13 C12 0.4(5) . . . . ?
C1 N1 C13 C14 178.8(4) . . . . ?
C1 N1 C18 C19 92.4(4) . . . . ?
C1 C2 C3 C4 177.8(4) . . . . ?
C2 C3 C4 C5 5.0(6) . . . . ?
C2 C3 C4 C9 -175.4(4) . . . . ?
C3 C4 C5 C6 -177.5(4) . . . . ?
C3 C4 C9 C8 177.5(4) . . . . ?
C4 C5 C6 O1 179.0(4) . . . . ?
C4 C5 C6 C7 -1.0(6) . . . . ?
C5 C4 C9 C8 -2.9(6) . . . . ?
C5 C6 C7 O2 177.7(4) . . . . ?
C5 C6 C7 C8 -1.0(6) . . . . ?
C6 C7 C8 C9 1.0(6) . . . . ?
C7 C8 C9 C4 0.9(6) . . . . ?
C9 C4 C5 C6 2.9(6) . . . . ?
C10 O1 C6 C5 -0.7(6) . . . . ?
C10 O1 C6 C7 179.3(4) . . . . ?
C11 O2 C7 C6 -177.5(4) . . . . ?
C11 O2 C7 C8 1.1(6) . . . . ?
C12 Se1 C1 N1 -0.4(3) . . . . ?
C12 Se1 C1 C2 -179.9(3) . . . . ?
C12 C13 C14 C15 -0.3(6) . . . . ?
C13 N1 C1 Se1 0.1(4) . . . . ?
C13 N1 C1 C2 179.6(4) . . . . ?
C13 N1 C18 C19 -88.8(4) . . . . ?
C13 C12 C17 C16 0.9(6) . . . . ?
C13 C14 C15 C16 1.6(6) . . . . ?
C14 C15 C16 C17 -1.7(7) . . . . ?
C15 C16 C17 C12 0.3(6) . . . . ?
C17 C12 C13 N1 177.6(4) . . . . ?
C17 C12 C13 C14 -1.0(6) . . . . ?
C18 N1 C1 Se1 178.9(3) . . . . ?
C18 N1 C1 C2 -1.6(6) . . . . ?
C18 N1 C13 C12 -178.4(3) . . . . ?
C18 N1 C13 C14 0.0(6) . . . . ?
O1A C6A C7A O2A -2.9(5) . . . . ?
O1A C6A C7A C8A 179.1(4) . . . . ?
O2A C7A C8A C9A -176.8(4) . . . . ?
N1A C1A C2A C3A 174.8(4) . . . . ?
N1A C13A C14A C15A -178.3(4) . . . . ?
C1A Se1A C12A C13A 0.1(3) . . . . ?
C1A Se1A C12A C17A -178.3(4) . . . . ?
C1A N1A C13A C12A 0.3(5) . . . . ?
C1A N1A C13A C14A 179.3(4) . . . . ?
C1A N1A C18A C19A 93.1(5) . . . . ?
C1A C2A C3A C4A 178.5(4) . . . . ?
C2A C3A C4A C5A 0.3(7) . . . . ?
C2A C3A C4A C9A -179.8(4) . . . . ?
C3A C4A C5A C6A -178.3(4) . . . . ?
C3A C4A C9A C8A 178.3(4) . . . . ?
C4A C5A C6A O1A 179.5(4) . . . . ?
C4A C5A C6A C7A -0.4(6) . . . . ?
C5A C4A C9A C8A -1.8(6) . . . . ?
C5A C6A C7A O2A 177.0(4) . . . . ?
C5A C6A C7A C8A -1.0(6) . . . . ?
C6A C7A C8A C9A 1.0(6) . . . . ?
C7A C8A C9A C4A 0.3(6) . . . . ?
C9A C4A C5A C6A 1.8(6) . . . . ?
C10A O1A C6A C5A -6.3(6) . . . . ?
C10A O1A C6A C7A 173.6(4) . . . . ?
C11A O2A C7A C6A -172.9(4) . . . . ?
C11A O2A C7A C8A 5.0(6) . . . . ?
C12A Se1A C1A N1A 0.1(3) . . . . ?
C12A Se1A C1A C2A -178.7(4) . . . . ?
C12A C13A C14A C15A 0.7(6) . . . . ?
C13A N1A C1A Se1A -0.2(4) . . . . ?
C13A N1A C1A C2A 178.5(4) . . . . ?
C13A N1A C18A C19A -88.5(5) . . . . ?
C13A C12A C17A C16A 1.1(6) . . . . ?
C13A C14A C15A C16A -1.0(7) . . . . ?
C14A C15A C16A C17A 1.3(7) . . . . ?
C15A C16A C17A C12A -1.3(7) . . . . ?
C17A C12A C13A N1A 178.3(4) . . . . ?
C17A C12A C13A C14A -0.8(6) . . . . ?
C18A N1A C1A Se1A 178.2(3) . . . . ?
C18A N1A C1A C2A -3.1(6) . . . . ?
C18A N1A C13A C12A -178.2(4) . . . . ?
C18A N1A C13A C14A 0.8(6) . . . . ?
C1S C2S C3S C4S -0.6(7) . . . . ?
C2S C1S C6S C5S 0.6(7) . . . . ?
C2S C3S C4S C5S -0.2(7) . . . . ?
C3S C4S C5S C6S 1.3(7) . . . . ?
C4S C5S C6S C1S -1.5(7) . . . . ?
C6S C1S C2S C3S 0.4(7) . . . . ?

_olex2_submission_special_instructions 'No special instructions were received'
####################################################################### 
# 
# 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_p-1
_database_code_depnum_ccdc_archive 'CCDC 1474551'
_audit_update_record             
;
2016-04-17 deposited with the CCDC.
2016-08-22 downloaded from the CCDC.
;
_audit_creation_date             2015-12-02
_audit_creation_method           
;
Olex2 1.2
(compiled 2015.09.30 svn.r3233 for OlexSys, GUI svn.r5103)
;
_chemical_name_common            ?
_chemical_name_systematic        
;
 ? 
;
_chemical_formula_moiety         'I, C19 H20 N O2 Se, 0.5(C6 H6 O2)'
_chemical_formula_sum            'C22 H23 I N O3 Se'
_chemical_formula_weight         555.27
_chemical_melting_point          ?
loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
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'
I I -0.4742 1.8119 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_space_group_crystal_system      triclinic
_space_group_IT_number           2
_space_group_name_H-M_alt        'P -1'
_space_group_name_Hall           '-P 1'
loop_
_space_group_symop_id
_space_group_symop_operation_xyz
1 'x, y, z'
2 '-x, -y, -z'

_cell_length_a                   11.8766(3)
_cell_length_b                   12.7576(4)
_cell_length_c                   15.3353(4)
_cell_angle_alpha                105.4770(10)
_cell_angle_beta                 97.1060(10)
_cell_angle_gamma                105.1850(10)
_cell_volume                     2113.78(10)
_cell_formula_units_Z            4
_cell_measurement_reflns_used    5499
_cell_measurement_temperature    120
_cell_measurement_theta_max      2.40
_cell_measurement_theta_min      26.000
_exptl_absorpt_coefficient_mu    3.259
_exptl_absorpt_correction_T_max  0.7461
_exptl_absorpt_correction_T_min  0.4986
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   ?
_exptl_crystal_colour            red
_exptl_crystal_colour_primary    red
_exptl_crystal_density_diffrn    1.745
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       block
_exptl_crystal_F_000             1092
_exptl_crystal_size_max          0.38
_exptl_crystal_size_mid          0.32
_exptl_crystal_size_min          0.3
_exptl_special_details           
;
 The data collection nominally covered a full sphere of reciprocal space by
 a combination of 4 sets of ω scans each set at different φ and/or
 2θ angles and each scan (10 s exposure) covering -0.300° degrees in ω.
 The crystal to detector distance was 4.85 cm.
;
_diffrn_reflns_av_R_equivalents  0.0160
_diffrn_reflns_av_unetI/netI     0.0232
_diffrn_reflns_limit_h_max       16
_diffrn_reflns_limit_h_min       -16
_diffrn_reflns_limit_k_max       17
_diffrn_reflns_limit_k_min       -17
_diffrn_reflns_limit_l_max       20
_diffrn_reflns_limit_l_min       -20
_diffrn_reflns_number            25381
_diffrn_reflns_theta_full        26.00
_diffrn_reflns_theta_max         29.00
_diffrn_reflns_theta_min         1.41
_diffrn_ambient_temperature      120.15
_diffrn_detector_area_resol_mean ?
_diffrn_measured_fraction_theta_full 0.996
_diffrn_measured_fraction_theta_max 0.991
_diffrn_measurement_device_type  SMART-6K
_diffrn_measurement_method       'ω scans'
_diffrn_radiation_monochromator  Parallel,graphite
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_source                   'fine-focus sealed tube'
_diffrn_source_current           35.0
_diffrn_source_power             1.75
_diffrn_source_voltage           50.0
_diffrn_standards_decay_%        ?
_diffrn_standards_interval_count ?
_diffrn_standards_interval_time  ?
_diffrn_standards_number         ?
_reflns_number_gt                9573
_reflns_number_total             11152
_reflns_threshold_expression     >2sigma(I)
_computing_cell_refinement       'SAINT v7.46A (Bruker, 2008)'
_computing_data_collection       'SMART v5.625 (Bruker, 2001)'
_computing_data_reduction        'SAINT v7.46A (Bruker, 2008)'
_computing_molecular_graphics    'Olex2 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 (Dolomanov et al., 2009)'
_computing_structure_refinement  'XL (Sheldrick, 2008)'
_computing_structure_solution    'XS (Sheldrick, 2008)'
_refine_diff_density_max         1.297
_refine_diff_density_min         -1.000
_refine_diff_density_rms         0.078
_refine_ls_extinction_coef       ?
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.019
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     511
_refine_ls_number_reflns         11152
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0331
_refine_ls_R_factor_gt           0.0258
_refine_ls_restrained_S_all      1.019
_refine_ls_shift/su_max          0.001
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details     
'calc w=1/[σ²(Fo²)+(0.0314P)²+0.8519P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0594
_refine_ls_wR_factor_ref         0.0609
_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. 
;
_olex2_refinement_description    
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups, All C(H,H) groups
 At 1.5 times of:
  All C(H,H,H) groups, All O(H) groups
2. Others
 Fixed Sof: H1S(0.12) H2S(0.88) H4S(0.12) H5S(0.88) O3A(0.88) H3AA(0.88)
 O4A(0.88) H4A(0.88) O3B(0.12) O4B(0.12) H3B(0.12) H4B(0.12)
3.a Everything fixed:
 H3B, H4B
3.b Secondary CH2 refined with riding coordinates:
 C18(H18A,H18B), C18A(H18C,H18D)
3.c Aromatic/amide H refined with riding coordinates:
 C2(H2), C3(H3), C5(H5), C6(H6), C9(H9), C14(H14), C15(H15), C16(H16),
 C17(H17), C2A(H2A), C3A(H3A), C5A(H5A), C6A(H6A), C9A(H9A), C14A(H14A),
 C15A(H15A), C16A(H16A), C17A(H17A), C1S(H1S), C2S(H2S), C3S(H3S), C4S(H4S),
 C5S(H5S), C6S(H6S)
3.d Idealised Me refined as rotating group:
 C10(H10A,H10B,H10C), C11(H11A,H11B,H11C), C19(H19A,H19B,H19C), C10A(H10D,H10E,
 H10F), C11A(H11D,H11E,H11F), C19A(H19D,H19E,H19F)
3.e Idealised tetrahedral OH refined as rotating group:
 O3A(H3AA), O4A(H4A)
;
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
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_calc_flag
_atom_site_disorder_assembly
_atom_site_disorder_group
_atom_site_refinement_flags_posn
I1 I 0.277449(14) 0.695704(13) 0.449367(10) 0.02994(4) Uani 1 d . . .
I2 I -0.224581(14) 0.186874(14) 0.087740(11) 0.03154(4) Uani 1 d . . .
Se1 Se 0.191530(19) 0.092862(19) -0.158732(15) 0.02345(5) Uani 1 d . . .
O2 O 0.21664(14) 0.09790(14) 0.40734(10) 0.0274(3) Uani 1 d . . .
O1 O 0.05185(14) 0.17475(14) 0.35485(10) 0.0290(3) Uani 1 d . . .
N1 N 0.00880(15) 0.17864(14) -0.15011(11) 0.0187(3) Uani 1 d . . .
C1 C 0.08063(18) 0.14450(16) -0.09712(14) 0.0192(4) Uani 1 d . . .
C2 C 0.07539(18) 0.14687(17) -0.00402(14) 0.0204(4) Uani 1 d . . .
H2 H 0.0240 0.1803 0.0258 0.024 Uiso 1 calc . . R
C3 C 0.14460(18) 0.10082(17) 0.04075(14) 0.0206(4) Uani 1 d . . .
H3 H 0.1921 0.0669 0.0063 0.025 Uiso 1 calc . . R
C4 C 0.15546(18) 0.09668(16) 0.13493(14) 0.0195(4) Uani 1 d . . .
C5 C 0.24225(18) 0.05133(17) 0.16496(14) 0.0211(4) Uani 1 d . . .
H5 H 0.2857 0.0218 0.1236 0.025 Uiso 1 calc . . R
C6 C 0.26502(18) 0.04936(18) 0.25526(14) 0.0219(4) Uani 1 d . . .
H6 H 0.3236 0.0194 0.2744 0.026 Uiso 1 calc . . R
C7 C 0.19992(18) 0.09229(17) 0.31678(14) 0.0208(4) Uani 1 d . . .
C8 C 0.10936(18) 0.13615(17) 0.28740(14) 0.0215(4) Uani 1 d . . .
C9 C 0.08709(18) 0.13794(17) 0.19745(14) 0.0211(4) Uani 1 d . . .
H9 H 0.0272 0.1662 0.1779 0.025 Uiso 1 calc . . R
C10 C 0.3088(2) 0.0568(2) 0.44118(16) 0.0328(5) Uani 1 d . . .
H10A H 0.2902 -0.0233 0.4094 0.049 Uiso 1 calc . . GR
H10B H 0.3146 0.0688 0.5063 0.049 Uiso 1 calc . . GR
H10C H 0.3835 0.0975 0.4305 0.049 Uiso 1 calc . . GR
C11 C -0.0394(2) 0.2215(3) 0.33121(17) 0.0381(6) Uani 1 d . . .
H11A H -0.0991 0.1657 0.2802 0.057 Uiso 1 calc . . GR
H11B H -0.0057 0.2882 0.3140 0.057 Uiso 1 calc . . GR
H11C H -0.0752 0.2421 0.3834 0.057 Uiso 1 calc . . GR
C12 C 0.12099(18) 0.12536(18) -0.26073(14) 0.0217(4) Uani 1 d . . .
C13 C 0.02840(18) 0.16923(17) -0.24037(14) 0.0201(4) Uani 1 d . . .
C14 C -0.03748(19) 0.19847(18) -0.30718(15) 0.0246(4) Uani 1 d . . .
H14 H -0.0987 0.2291 -0.2941 0.030 Uiso 1 calc . . R
C15 C -0.0082(2) 0.18015(19) -0.39346(15) 0.0279(5) Uani 1 d . . .
H15 H -0.0515 0.1981 -0.4391 0.033 Uiso 1 calc . . R
C16 C 0.0841(2) 0.1358(2) -0.41392(16) 0.0291(5) Uani 1 d . . .
H16 H 0.1016 0.1246 -0.4725 0.035 Uiso 1 calc . . R
C17 C 0.1499(2) 0.1081(2) -0.34718(16) 0.0276(5) Uani 1 d . . .
H17 H 0.2120 0.0787 -0.3601 0.033 Uiso 1 calc . . R
C18 C -0.08572(19) 0.22436(18) -0.11759(14) 0.0220(4) Uani 1 d . . .
H18A H -0.1151 0.1899 -0.0723 0.026 Uiso 1 calc . . R
H18B H -0.1517 0.2041 -0.1693 0.026 Uiso 1 calc . . R
C19 C -0.0404(2) 0.3530(2) -0.07467(19) 0.0362(6) Uani 1 d . . .
H19A H -0.0125 0.3874 -0.1197 0.054 Uiso 1 calc . . GR
H19B H 0.0239 0.3732 -0.0227 0.054 Uiso 1 calc . . GR
H19C H -0.1040 0.3800 -0.0544 0.054 Uiso 1 calc . . GR
Se2 Se 0.43135(2) 0.34355(2) 0.665673(15) 0.02625(5) Uani 1 d . . .
O1A O 0.40000(15) 0.30393(14) 0.08970(11) 0.0298(3) Uani 1 d . . .
O2A O 0.25867(17) 0.40494(15) 0.16191(11) 0.0364(4) Uani 1 d . . .
N1A N 0.28260(16) 0.46929(15) 0.66893(12) 0.0231(4) Uani 1 d . . .
C1A C 0.34042(19) 0.41753(18) 0.61079(15) 0.0231(4) Uani 1 d . . .
C2A C 0.33439(19) 0.41533(18) 0.51692(15) 0.0237(4) Uani 1 d . . .
H2A H 0.2814 0.4462 0.4906 0.028 Uiso 1 calc . . R
C3A C 0.40410(19) 0.36936(18) 0.46534(15) 0.0239(4) Uani 1 d . . .
H3A H 0.4576 0.3420 0.4953 0.029 Uiso 1 calc . . R
C4A C 0.40538(19) 0.35765(17) 0.36907(14) 0.0233(4) Uani 1 d . . .
C5A C 0.48521(19) 0.30700(18) 0.32910(15) 0.0251(4) Uani 1 d . . .
H5A H 0.5373 0.2845 0.3652 0.030 Uiso 1 calc . . R
C6A C 0.48807(19) 0.28971(19) 0.23588(15) 0.0255(4) Uani 1 d . . .
H6A H 0.5422 0.2566 0.2100 0.031 Uiso 1 calc . . R
C7A C 0.4096(2) 0.32223(18) 0.18218(14) 0.0242(4) Uani 1 d . . .
C8A C 0.3298(2) 0.37556(18) 0.22216(15) 0.0259(4) Uani 1 d . . .
C9A C 0.3281(2) 0.39339(18) 0.31422(15) 0.0247(4) Uani 1 d . . .
H9A H 0.2760 0.4291 0.3405 0.030 Uiso 1 calc . . R
C10A C 0.4696(2) 0.2393(2) 0.04496(16) 0.0325(5) Uani 1 d . . .
H10D H 0.4529 0.2291 -0.0202 0.049 Uiso 1 calc . . GR
H10E H 0.4501 0.1660 0.0547 0.049 Uiso 1 calc . . GR
H10F H 0.5528 0.2794 0.0701 0.049 Uiso 1 calc . . GR
C11A C 0.1691(3) 0.4500(3) 0.19680(18) 0.0416(6) Uani 1 d . . .
H11D H 0.1241 0.4668 0.1487 0.062 Uiso 1 calc . . GR
H11E H 0.2064 0.5189 0.2477 0.062 Uiso 1 calc . . GR
H11F H 0.1167 0.3948 0.2174 0.062 Uiso 1 calc . . GR
C12A C 0.3737(2) 0.39519(18) 0.77235(15) 0.0250(4) Uani 1 d . . .
C13A C 0.29739(19) 0.45764(18) 0.75777(15) 0.0235(4) Uani 1 d . . .
C14A C 0.2450(2) 0.5043(2) 0.82859(16) 0.0297(5) Uani 1 d . . .
H14A H 0.1935 0.5459 0.8195 0.036 Uiso 1 calc . . R
C15A C 0.2721(2) 0.4868(2) 0.91322(17) 0.0332(5) Uani 1 d . . .
H15A H 0.2382 0.5177 0.9614 0.040 Uiso 1 calc . . R
C16A C 0.3481(2) 0.4246(2) 0.92787(17) 0.0328(5) Uani 1 d . . .
H16A H 0.3641 0.4139 0.9852 0.039 Uiso 1 calc . . R
C17A C 0.4003(2) 0.3783(2) 0.85756(16) 0.0310(5) Uani 1 d . . .
H17A H 0.4519 0.3368 0.8670 0.037 Uiso 1 calc . . R
C18A C 0.2106(2) 0.54012(19) 0.64401(16) 0.0273(5) Uani 1 d . . .
H18C H 0.2410 0.5709 0.5972 0.033 Uiso 1 calc . . R
H18D H 0.2182 0.6039 0.6981 0.033 Uiso 1 calc . . R
C19A C 0.0802(2) 0.4711(2) 0.6077(2) 0.0383(6) Uani 1 d . . .
H19D H 0.0719 0.4108 0.5519 0.057 Uiso 1 calc . . GR
H19E H 0.0355 0.5199 0.5950 0.057 Uiso 1 calc . . GR
H19F H 0.0505 0.4387 0.6533 0.057 Uiso 1 calc . . GR
C1S C 0.4138(2) -0.0310(2) -0.25726(17) 0.0295(5) Uani 1 d . . .
H1S H 0.3569 -0.0984 -0.2601 0.035 Uiso 0.12 calc A 2 R
C2S C 0.4840(2) 0.0421(2) -0.17284(16) 0.0310(5) Uani 1 d E . .
H2S H 0.4741 0.0235 -0.1190 0.037 Uiso 0.88 calc B 1 R
C3S C 0.5693(2) 0.1430(2) -0.16819(16) 0.0300(5) Uani 1 d . . .
H3S H 0.6165 0.1917 -0.1114 0.036 Uiso 1 calc E . R
C4S C 0.5838(2) 0.1707(2) -0.24853(17) 0.0289(5) Uani 1 d E . .
H4S H 0.6403 0.2383 -0.2456 0.035 Uiso 0.12 calc C 2 R
C5S C 0.5139(2) 0.0976(2) -0.33335(16) 0.0276(5) Uani 1 d . . .
H5S H 0.5239 0.1159 -0.3873 0.033 Uiso 0.88 calc D 1 R
C6S C 0.4287(2) -0.0032(2) -0.33735(16) 0.0293(5) Uani 1 d E . .
H6S H 0.3817 -0.0520 -0.3941 0.035 Uiso 1 calc . . R
O3A O 0.3287(3) -0.1342(2) -0.2698(2) 0.0613(7) Uiso 0.88 d E 1 .
H3AA H 0.3160 -0.1391 -0.2194 0.092 Uiso 0.88 calc E 1 GR
O4A O 0.6704(3) 0.2689(2) -0.2402(2) 0.0623(7) Uiso 0.88 d E 1 .
H4A H 0.6818 0.2703 -0.2915 0.094 Uiso 0.88 calc E 1 GR
O3B O 0.464(2) 0.015(2) -0.0997(17) 0.080(7) Uiso 0.12 d E 2 .
O4B O 0.520(2) 0.1067(19) -0.4194(16) 0.071(6) Uiso 0.12 d E 2 .
H3B H 0.5205 0.0566 -0.0561 0.070 Uiso 0.12 d F 2 .
H4B H 0.5015 0.0385 -0.4560 0.070 Uiso 0.12 d G 2 .


_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 1.869(2) . ?
Se1 C12 1.877(2) . ?
O2 C7 1.358(2) . ?
O2 C10 1.431(3) . ?
O1 C8 1.363(3) . ?
O1 C11 1.421(3) . ?
N1 C1 1.338(2) . ?
N1 C13 1.411(3) . ?
N1 C18 1.475(3) . ?
C1 C2 1.429(3) . ?
C2 H2 0.9300 . ?
C2 C3 1.349(3) . ?
C3 H3 0.9300 . ?
C3 C4 1.450(3) . ?
C4 C5 1.395(3) . ?
C4 C9 1.415(3) . ?
C5 H5 0.9300 . ?
C5 C6 1.386(3) . ?
C6 H6 0.9300 . ?
C6 C7 1.384(3) . ?
C7 C8 1.415(3) . ?
C8 C9 1.380(3) . ?
C9 H9 0.9300 . ?
C10 H10A 0.9600 . ?
C10 H10B 0.9600 . ?
C10 H10C 0.9600 . ?
C11 H11A 0.9600 . ?
C11 H11B 0.9600 . ?
C11 H11C 0.9600 . ?
C12 C13 1.391(3) . ?
C12 C17 1.386(3) . ?
C13 C14 1.400(3) . ?
C14 H14 0.9300 . ?
C14 C15 1.385(3) . ?
C15 H15 0.9300 . ?
C15 C16 1.391(3) . ?
C16 H16 0.9300 . ?
C16 C17 1.387(3) . ?
C17 H17 0.9300 . ?
C18 H18A 0.9700 . ?
C18 H18B 0.9700 . ?
C18 C19 1.513(3) . ?
C19 H19A 0.9600 . ?
C19 H19B 0.9600 . ?
C19 H19C 0.9600 . ?
Se2 C1A 1.870(2) . ?
Se2 C12A 1.875(2) . ?
O1A C7A 1.359(3) . ?
O1A C10A 1.424(3) . ?
O2A C8A 1.366(3) . ?
O2A C11A 1.430(3) . ?
N1A C1A 1.333(3) . ?
N1A C13A 1.404(3) . ?
N1A C18A 1.484(3) . ?
C1A C2A 1.425(3) . ?
C2A H2A 0.9300 . ?
C2A C3A 1.351(3) . ?
C3A H3A 0.9300 . ?
C3A C4A 1.446(3) . ?
C4A C5A 1.395(3) . ?
C4A C9A 1.411(3) . ?
C5A H5A 0.9300 . ?
C5A C6A 1.393(3) . ?
C6A H6A 0.9300 . ?
C6A C7A 1.383(3) . ?
C7A C8A 1.413(3) . ?
C8A C9A 1.372(3) . ?
C9A H9A 0.9300 . ?
C10A H10D 0.9600 . ?
C10A H10E 0.9600 . ?
C10A H10F 0.9600 . ?
C11A H11D 0.9600 . ?
C11A H11E 0.9600 . ?
C11A H11F 0.9600 . ?
C12A C13A 1.389(3) . ?
C12A C17A 1.392(3) . ?
C13A C14A 1.391(3) . ?
C14A H14A 0.9300 . ?
C14A C15A 1.388(3) . ?
C15A H15A 0.9300 . ?
C15A C16A 1.383(4) . ?
C16A H16A 0.9300 . ?
C16A C17A 1.384(3) . ?
C17A H17A 0.9300 . ?
C18A H18C 0.9700 . ?
C18A H18D 0.9700 . ?
C18A C19A 1.515(3) . ?
C19A H19D 0.9600 . ?
C19A H19E 0.9600 . ?
C19A H19F 0.9600 . ?
C1S H1S 0.9300 . ?
C1S C2S 1.386(4) . ?
C1S C6S 1.386(3) . ?
C1S O3A 1.383(4) . ?
C2S H2S 0.9300 . ?
C2S C3S 1.393(4) . ?
C2S O3B 1.29(3) . ?
C3S H3S 0.9300 . ?
C3S C4S 1.388(3) . ?
C4S H4S 0.9300 . ?
C4S C5S 1.390(3) . ?
C4S O4A 1.360(4) . ?
C5S H5S 0.9300 . ?
C5S C6S 1.393(3) . ?
C5S O4B 1.36(2) . ?
C6S H6S 0.9300 . ?
O3A H3AA 0.8200 . ?
O4A H4A 0.8200 . ?
O3B H3B 0.8309 . ?
O4B H4B 0.8537 . ?

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 C12 86.73(9) . . ?
C7 O2 C10 117.28(17) . . ?
C8 O1 C11 117.59(17) . . ?
C1 N1 C13 116.18(17) . . ?
C1 N1 C18 122.95(17) . . ?
C13 N1 C18 120.87(16) . . ?
N1 C1 Se1 112.10(14) . . ?
N1 C1 C2 124.94(19) . . ?
C2 C1 Se1 122.96(15) . . ?
C1 C2 H2 119.8 . . ?
C3 C2 C1 120.32(19) . . ?
C3 C2 H2 119.8 . . ?
C2 C3 H3 115.4 . . ?
C2 C3 C4 129.2(2) . . ?
C4 C3 H3 115.4 . . ?
C5 C4 C3 116.42(19) . . ?
C5 C4 C9 119.02(18) . . ?
C9 C4 C3 124.54(18) . . ?
C4 C5 H5 119.4 . . ?
C6 C5 C4 121.27(19) . . ?
C6 C5 H5 119.4 . . ?
C5 C6 H6 120.2 . . ?
C7 C6 C5 119.51(19) . . ?
C7 C6 H6 120.2 . . ?
O2 C7 C6 124.72(18) . . ?
O2 C7 C8 114.97(18) . . ?
C6 C7 C8 120.30(18) . . ?
O1 C8 C7 114.09(18) . . ?
O1 C8 C9 125.96(19) . . ?
C9 C8 C7 119.95(19) . . ?
C4 C9 H9 120.0 . . ?
C8 C9 C4 119.91(19) . . ?
C8 C9 H9 120.0 . . ?
O2 C10 H10A 109.5 . . ?
O2 C10 H10B 109.5 . . ?
O2 C10 H10C 109.5 . . ?
H10A C10 H10B 109.5 . . ?
H10A C10 H10C 109.5 . . ?
H10B C10 H10C 109.5 . . ?
O1 C11 H11A 109.5 . . ?
O1 C11 H11B 109.5 . . ?
O1 C11 H11C 109.5 . . ?
H11A C11 H11B 109.5 . . ?
H11A C11 H11C 109.5 . . ?
H11B C11 H11C 109.5 . . ?
C13 C12 Se1 110.78(15) . . ?
C17 C12 Se1 127.74(17) . . ?
C17 C12 C13 121.46(19) . . ?
C12 C13 N1 114.20(17) . . ?
C12 C13 C14 120.37(19) . . ?
C14 C13 N1 125.42(19) . . ?
C13 C14 H14 121.2 . . ?
C15 C14 C13 117.6(2) . . ?
C15 C14 H14 121.2 . . ?
C14 C15 H15 119.0 . . ?
C14 C15 C16 122.0(2) . . ?
C16 C15 H15 119.0 . . ?
C15 C16 H16 119.9 . . ?
C17 C16 C15 120.2(2) . . ?
C17 C16 H16 119.9 . . ?
C12 C17 C16 118.4(2) . . ?
C12 C17 H17 120.8 . . ?
C16 C17 H17 120.8 . . ?
N1 C18 H18A 109.3 . . ?
N1 C18 H18B 109.3 . . ?
N1 C18 C19 111.55(18) . . ?
H18A C18 H18B 108.0 . . ?
C19 C18 H18A 109.3 . . ?
C19 C18 H18B 109.3 . . ?
C18 C19 H19A 109.5 . . ?
C18 C19 H19B 109.5 . . ?
C18 C19 H19C 109.5 . . ?
H19A C19 H19B 109.5 . . ?
H19A C19 H19C 109.5 . . ?
H19B C19 H19C 109.5 . . ?
C1A Se2 C12A 86.36(10) . . ?
C7A O1A C10A 116.95(17) . . ?
C8A O2A C11A 116.60(19) . . ?
C1A N1A C13A 116.34(18) . . ?
C1A N1A C18A 122.67(18) . . ?
C13A N1A C18A 120.93(18) . . ?
N1A C1A Se2 112.20(15) . . ?
N1A C1A C2A 125.37(19) . . ?
C2A C1A Se2 122.42(16) . . ?
C1A C2A H2A 119.3 . . ?
C3A C2A C1A 121.3(2) . . ?
C3A C2A H2A 119.3 . . ?
C2A C3A H3A 116.2 . . ?
C2A C3A C4A 127.6(2) . . ?
C4A C3A H3A 116.2 . . ?
C5A C4A C3A 118.13(19) . . ?
C5A C4A C9A 119.2(2) . . ?
C9A C4A C3A 122.7(2) . . ?
C4A C5A H5A 119.5 . . ?
C6A C5A C4A 120.9(2) . . ?
C6A C5A H5A 119.5 . . ?
C5A C6A H6A 120.3 . . ?
C7A C6A C5A 119.4(2) . . ?
C7A C6A H6A 120.3 . . ?
O1A C7A C6A 124.4(2) . . ?
O1A C7A C8A 115.26(19) . . ?
C6A C7A C8A 120.3(2) . . ?
O2A C8A C7A 114.34(19) . . ?
O2A C8A C9A 125.6(2) . . ?
C9A C8A C7A 120.10(19) . . ?
C4A C9A H9A 119.9 . . ?
C8A C9A C4A 120.1(2) . . ?
C8A C9A H9A 119.9 . . ?
O1A C10A H10D 109.5 . . ?
O1A C10A H10E 109.5 . . ?
O1A C10A H10F 109.5 . . ?
H10D C10A H10E 109.5 . . ?
H10D C10A H10F 109.5 . . ?
H10E C10A H10F 109.5 . . ?
O2A C11A H11D 109.5 . . ?
O2A C11A H11E 109.5 . . ?
O2A C11A H11F 109.5 . . ?
H11D C11A H11E 109.5 . . ?
H11D C11A H11F 109.5 . . ?
H11E C11A H11F 109.5 . . ?
C13A C12A Se2 111.03(16) . . ?
C13A C12A C17A 121.2(2) . . ?
C17A C12A Se2 127.73(18) . . ?
C12A C13A N1A 114.05(19) . . ?
C12A C13A C14A 120.3(2) . . ?
C14A C13A N1A 125.6(2) . . ?
C13A C14A H14A 121.0 . . ?
C15A C14A C13A 118.0(2) . . ?
C15A C14A H14A 121.0 . . ?
C14A C15A H15A 119.1 . . ?
C16A C15A C14A 121.8(2) . . ?
C16A C15A H15A 119.1 . . ?
C15A C16A H16A 119.9 . . ?
C15A C16A C17A 120.3(2) . . ?
C17A C16A H16A 119.9 . . ?
C12A C17A H17A 120.8 . . ?
C16A C17A C12A 118.4(2) . . ?
C16A C17A H17A 120.8 . . ?
N1A C18A H18C 109.3 . . ?
N1A C18A H18D 109.3 . . ?
N1A C18A C19A 111.47(18) . . ?
H18C C18A H18D 108.0 . . ?
C19A C18A H18C 109.3 . . ?
C19A C18A H18D 109.3 . . ?
C18A C19A H19D 109.5 . . ?
C18A C19A H19E 109.5 . . ?
C18A C19A H19F 109.5 . . ?
H19D C19A H19E 109.5 . . ?
H19D C19A H19F 109.5 . . ?
H19E C19A H19F 109.5 . . ?
C2S C1S H1S 120.2 . . ?
C6S C1S H1S 120.2 . . ?
C6S C1S C2S 119.7(2) . . ?
O3A C1S H1S 5.0 . . ?
O3A C1S C2S 125.0(2) . . ?
O3A C1S C6S 115.3(2) . . ?
C1S C2S H2S 119.8 . . ?
C1S C2S C3S 120.4(2) . . ?
C3S C2S H2S 119.8 . . ?
O3B C2S C1S 117.6(11) . . ?
O3B C2S H2S 3.0 . . ?
O3B C2S C3S 122.0(11) . . ?
C2S C3S H3S 120.1 . . ?
C4S C3S C2S 119.8(2) . . ?
C4S C3S H3S 120.1 . . ?
C3S C4S H4S 120.0 . . ?
C3S C4S C5S 120.1(2) . . ?
C5S C4S H4S 120.0 . . ?
O4A C4S C3S 117.2(2) . . ?
O4A C4S H4S 3.2 . . ?
O4A C4S C5S 122.7(2) . . ?
C4S C5S H5S 120.1 . . ?
C4S C5S C6S 119.8(2) . . ?
C6S C5S H5S 120.1 . . ?
O4B C5S C4S 128.4(10) . . ?
O4B C5S H5S 8.9 . . ?
O4B C5S C6S 111.7(10) . . ?
C1S C6S C5S 120.3(2) . . ?
C1S C6S H6S 119.8 . . ?
C5S C6S H6S 119.8 . . ?
C1S O3A H3AA 109.5 . . ?
C4S O4A H4A 109.5 . . ?
C2S O3B H3B 107.9 . . ?
C5S O4B H4B 106.3 . . ?

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
Se1 C1 C2 C3 -6.4(3) . . . . ?
Se1 C12 C13 N1 -0.2(2) . . . . ?
Se1 C12 C13 C14 -179.40(16) . . . . ?
Se1 C12 C17 C16 178.46(17) . . . . ?
O2 C7 C8 O1 -1.3(3) . . . . ?
O2 C7 C8 C9 178.06(18) . . . . ?
O1 C8 C9 C4 178.86(19) . . . . ?
N1 C1 C2 C3 173.90(19) . . . . ?
N1 C13 C14 C15 -177.96(19) . . . . ?
C1 Se1 C12 C13 0.35(15) . . . . ?
C1 Se1 C12 C17 -178.2(2) . . . . ?
C1 N1 C13 C12 -0.1(3) . . . . ?
C1 N1 C13 C14 179.0(2) . . . . ?
C1 N1 C18 C19 90.9(2) . . . . ?
C1 C2 C3 C4 178.22(19) . . . . ?
C2 C3 C4 C5 -174.9(2) . . . . ?
C2 C3 C4 C9 3.3(3) . . . . ?
C3 C4 C5 C6 176.22(19) . . . . ?
C3 C4 C9 C8 -176.12(19) . . . . ?
C4 C5 C6 C7 0.5(3) . . . . ?
C5 C4 C9 C8 2.0(3) . . . . ?
C5 C6 C7 O2 -178.00(19) . . . . ?
C5 C6 C7 C8 1.1(3) . . . . ?
C6 C7 C8 O1 179.51(18) . . . . ?
C6 C7 C8 C9 -1.1(3) . . . . ?
C7 C8 C9 C4 -0.5(3) . . . . ?
C9 C4 C5 C6 -2.1(3) . . . . ?
C10 O2 C7 C6 0.3(3) . . . . ?
C10 O2 C7 C8 -178.8(2) . . . . ?
C11 O1 C8 C7 179.2(2) . . . . ?
C11 O1 C8 C9 -0.1(3) . . . . ?
C12 Se1 C1 N1 -0.40(15) . . . . ?
C12 Se1 C1 C2 179.86(18) . . . . ?
C12 C13 C14 C15 1.1(3) . . . . ?
C13 N1 C1 Se1 0.4(2) . . . . ?
C13 N1 C1 C2 -179.91(18) . . . . ?
C13 N1 C18 C19 -88.8(2) . . . . ?
C13 C12 C17 C16 0.0(3) . . . . ?
C13 C14 C15 C16 -0.8(3) . . . . ?
C14 C15 C16 C17 0.1(4) . . . . ?
C15 C16 C17 C12 0.3(3) . . . . ?
C17 C12 C13 N1 178.43(19) . . . . ?
C17 C12 C13 C14 -0.7(3) . . . . ?
C18 N1 C1 Se1 -179.32(14) . . . . ?
C18 N1 C1 C2 0.4(3) . . . . ?
C18 N1 C13 C12 179.61(17) . . . . ?
C18 N1 C13 C14 -1.3(3) . . . . ?
Se2 C1A C2A C3A -7.0(3) . . . . ?
Se2 C12A C13A N1A -1.0(2) . . . . ?
Se2 C12A C13A C14A -179.74(17) . . . . ?
Se2 C12A C17A C16A 179.67(18) . . . . ?
O1A C7A C8A O2A -2.7(3) . . . . ?
O1A C7A C8A C9A 177.0(2) . . . . ?
O2A C8A C9A C4A 179.2(2) . . . . ?
N1A C1A C2A C3A 174.1(2) . . . . ?
N1A C13A C14A C15A -178.2(2) . . . . ?
C1A Se2 C12A C13A 0.25(16) . . . . ?
C1A Se2 C12A C17A -179.1(2) . . . . ?
C1A N1A C13A C12A 1.5(3) . . . . ?
C1A N1A C13A C14A -179.8(2) . . . . ?
C1A N1A C18A C19A 94.6(3) . . . . ?
C1A C2A C3A C4A 177.8(2) . . . . ?
C2A C3A C4A C5A -179.9(2) . . . . ?
C2A C3A C4A C9A -1.1(3) . . . . ?
C3A C4A C5A C6A 177.8(2) . . . . ?
C3A C4A C9A C8A -177.1(2) . . . . ?
C4A C5A C6A C7A -0.7(3) . . . . ?
C5A C4A C9A C8A 1.7(3) . . . . ?
C5A C6A C7A O1A -176.3(2) . . . . ?
C5A C6A C7A C8A 1.9(3) . . . . ?
C6A C7A C8A O2A 179.0(2) . . . . ?
C6A C7A C8A C9A -1.3(3) . . . . ?
C7A C8A C9A C4A -0.5(3) . . . . ?
C9A C4A C5A C6A -1.1(3) . . . . ?
C10A O1A C7A C6A 4.9(3) . . . . ?
C10A O1A C7A C8A -173.4(2) . . . . ?
C11A O2A C8A C7A 174.7(2) . . . . ?
C11A O2A C8A C9A -5.0(3) . . . . ?
C12A Se2 C1A N1A 0.57(16) . . . . ?
C12A Se2 C1A C2A -178.50(18) . . . . ?
C12A C13A C14A C15A 0.3(3) . . . . ?
C13A N1A C1A Se2 -1.3(2) . . . . ?
C13A N1A C1A C2A 177.74(19) . . . . ?
C13A N1A C18A C19A -88.2(2) . . . . ?
C13A C12A C17A C16A 0.4(3) . . . . ?
C13A C14A C15A C16A -0.4(4) . . . . ?
C14A C15A C16A C17A 0.4(4) . . . . ?
C15A C16A C17A C12A -0.4(4) . . . . ?
C17A C12A C13A N1A 178.4(2) . . . . ?
C17A C12A C13A C14A -0.4(3) . . . . ?
C18A N1A C1A Se2 175.99(15) . . . . ?
C18A N1A C1A C2A -5.0(3) . . . . ?
C18A N1A C13A C12A -175.80(19) . . . . ?
C18A N1A C13A C14A 2.9(3) . . . . ?
C1S C2S C3S C4S 0.2(3) . . . . ?
C2S C1S C6S C5S 0.0(3) . . . . ?
C2S C3S C4S C5S -0.4(3) . . . . ?
C2S C3S C4S O4A -178.5(2) . . . . ?
C3S C4S C5S C6S 0.4(3) . . . . ?
C3S C4S C5S O4B -175.6(12) . . . . ?
C4S C5S C6S C1S -0.2(3) . . . . ?
C6S C1S C2S C3S 0.0(3) . . . . ?
C6S C1S C2S O3B 177.7(13) . . . . ?
O3A C1S C2S C3S 178.5(2) . . . . ?
O3A C1S C2S O3B -3.8(13) . . . . ?
O3A C1S C6S C5S -178.6(2) . . . . ?
O4A C4S C5S C6S 178.4(2) . . . . ?
O4A C4S C5S O4B 2.4(13) . . . . ?
O3B C2S C3S C4S -177.4(13) . . . . ?
O4B C5S C6S C1S 176.4(10) . . . . ?

_olex2_submission_special_instructions 'No special instructions were received'
####################################################################### 
# 
# 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_p-1
_database_code_depnum_ccdc_archive 'CCDC 1474552'
_audit_update_record             
;
2016-04-17 deposited with the CCDC.
2016-08-22 downloaded from the CCDC.
;
_audit_creation_date             2015-10-23
_audit_creation_method           
;
Olex2 1.2
(compiled 2015.09.30 svn.r3233 for OlexSys, GUI svn.r5103)
;
_chemical_formula_moiety         'I, C19 H20 N O2 Se, 0.5(C4 H8 O2), 0.3(O)'
_chemical_formula_sum            'C21 H24 I N O3.3 Se'
_chemical_formula_weight         549.09
loop_
_atom_type_symbol
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_Cromer_Mann_a1
_atom_type_scat_Cromer_Mann_a2
_atom_type_scat_Cromer_Mann_a3
_atom_type_scat_Cromer_Mann_a4
_atom_type_scat_Cromer_Mann_b1
_atom_type_scat_Cromer_Mann_b2
_atom_type_scat_Cromer_Mann_b3
_atom_type_scat_Cromer_Mann_b4
_atom_type_scat_Cromer_Mann_c
_atom_type_scat_source
_atom_type_scat_dispersion_source
C 0.00347 0.00161 2.31000 1.02000 1.58860 0.86500 20.84390 10.20750 0.56870
51.65120 0.215599998832
'International Tables Volume C Table 6.1.1.4 (pp. 500-502)'
'Henke, Gullikson and Davis, At. Data and Nucl. Data Tables, 1993, 54, 2'
I -0.41187 1.83264 20.14720 18.99490 7.51380 2.27350 4.34700 0.38140 27.76600
66.87760 4.07119989395
'International Tables Volume C Table 6.1.1.4 (pp. 500-502)'
'Henke, Gullikson and Davis, At. Data and Nucl. Data Tables, 1993, 54, 2'
H 0.00000 0.00000 0.49300 0.32291 0.14019 0.04081 10.51090 26.12570 3.14236
57.79970 0.0030380000826
'International Tables Volume C Table 6.1.1.4 (pp. 500-502)'
'Henke, Gullikson and Davis, At. Data and Nucl. Data Tables, 1993, 54, 2'
O 0.01158 0.00611 3.04850 2.28680 1.54630 0.86700 13.27710 5.70110 0.32390
32.90890 0.250800013542
'International Tables Volume C Table 6.1.1.4 (pp. 500-502)'
'Henke, Gullikson and Davis, At. Data and Nucl. Data Tables, 1993, 54, 2'
N 0.00653 0.00323 12.21260 3.13220 2.01250 1.16630 0.00570 9.89330 28.99750
0.58260 -11.5290002823
'International Tables Volume C Table 6.1.1.4 (pp. 500-502)'
'Henke, Gullikson and Davis, At. Data and Nucl. Data Tables, 1993, 54, 2'
Se -0.08110 2.30834 17.00060 5.81960 3.97310 4.35430 2.40980 0.27260 15.23720
43.81630 2.84089994431
'International Tables Volume C Table 6.1.1.4 (pp. 500-502)'
'Henke, Gullikson and Davis, At. Data and Nucl. Data Tables, 1993, 54, 2'

_space_group_crystal_system      triclinic
_space_group_IT_number           2
_space_group_name_H-M_alt        'P -1'
_space_group_name_Hall           '-P 1'
loop_
_space_group_symop_id
_space_group_symop_operation_xyz
1 x,y,z
2 -x,-y,-z

_symmetry_Int_Tables_number      2
_cell_length_a                   7.3704(4)
_cell_length_b                   10.8423(5)
_cell_length_c                   14.5069(7)
_cell_angle_alpha                107.977(2)
_cell_angle_beta                 100.703(2)
_cell_angle_gamma                93.136(2)
_cell_volume                     1075.69(9)
_cell_formula_units_Z            2
_cell_measurement_reflns_used    4054
_cell_measurement_temperature    120.15
_cell_measurement_theta_max      28.1
_cell_measurement_theta_min      2.15
_exptl_absorpt_coefficient_mu    3.202
_exptl_absorpt_correction_T_max  0.7454
_exptl_absorpt_correction_T_min  0.6933
_exptl_absorpt_correction_type   multi-scan
_exptl_crystal_colour            red
_exptl_crystal_colour_primary    red
_exptl_crystal_density_diffrn    1.6952
_exptl_crystal_description       prism
_exptl_crystal_F_000             540.0420
_exptl_crystal_size_max          0.08
_exptl_crystal_size_mid          0.07
_exptl_crystal_size_min          0.06
_diffrn_reflns_av_R_equivalents  0.0286
_diffrn_reflns_av_unetI/netI     0.0313
_diffrn_reflns_limit_h_max       9
_diffrn_reflns_limit_h_min       -9
_diffrn_reflns_limit_k_max       13
_diffrn_reflns_limit_k_min       -13
_diffrn_reflns_limit_l_max       18
_diffrn_reflns_limit_l_min       -18
_diffrn_reflns_number            15987
_diffrn_reflns_theta_full        26.2847
_diffrn_reflns_theta_max         26.28
_diffrn_reflns_theta_min         2.83
_diffrn_ambient_temperature      120.15
_diffrn_measured_fraction_theta_full 0.9959
_diffrn_measured_fraction_theta_max 0.9959
_diffrn_measurement_device_type  'Bruker Venture D8'
_diffrn_radiation_type           'Mo K\a'
_diffrn_radiation_wavelength     0.71073
_reflns_Friedel_coverage         0.0
_reflns_limit_h_max              9
_reflns_limit_h_min              -9
_reflns_limit_k_max              12
_reflns_limit_k_min              -13
_reflns_limit_l_max              18
_reflns_limit_l_min              0
_reflns_number_gt                3647
_reflns_number_total             4342
_reflns_threshold_expression     I>=2u(I)
_computing_molecular_graphics    'Olex2 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 (Dolomanov et al., 2009)'
_computing_structure_refinement  'olex2.refine (Bourhis et al., 2015)'
_computing_structure_solution    'ShelXS-1997 (Sheldrick, 2008)'
_refine_diff_density_max         0.6068
_refine_diff_density_min         -0.5624
_refine_diff_density_rms         0.1279
_refine_ls_d_res_high            0.8025
_refine_ls_d_res_low             7.1900
_refine_ls_goodness_of_fit_ref   1.0319
_refine_ls_hydrogen_treatment    refall
_refine_ls_matrix_type           full
_refine_ls_number_constraints    44
_refine_ls_number_parameters     279
_refine_ls_number_reflns         4342
_refine_ls_number_restraints     12
_refine_ls_R_factor_all          0.0342
_refine_ls_R_factor_gt           0.0234
_refine_ls_restrained_S_all      1.0303
_refine_ls_shift/su_max          0.0000
_refine_ls_shift/su_mean         0.0000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0117P)²+0.9016P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0433
_refine_ls_wR_factor_ref         0.0461
_olex2_refinement_description    
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups, All C(H,H) groups
 At 1.5 times of:
  All C(H,H,H) groups
2. Uiso/Uaniso restraints and constraints
Uanis(C2S) \\sim Ueq, Uanis(O1W) \\sim Ueq: with sigma of 0.01 and sigma for
terminal atoms of 0.02
3. Others
 Fixed Sof: O1S(0.5) O2S(0.5) C1S(0.5) C2S(0.5) H2Sa(0.5) H2Sb(0.5) H2Sc(0.5)
 C3S(0.5) H3Sa(0.5) H3Sb(0.5) C4S(0.5) H4Sa(0.5) H4Sb(0.5) H4Sc(0.5) O1W(0.3)
4.a Secondary CH2 refined with riding coordinates:
 C18(H18a,H18b), C3S(H3Sa,H3Sb)
4.b Me refined with riding coordinates:
 C10(H10a,H10b,H10c), C11(H11a,H11b,H11c), C19(H19a,H19b,H19c), C2S(H2Sa,H2Sb,
 H2Sc), C4S(H4Sa,H4Sb,H4Sc)
4.c Aromatic/amide H refined with riding coordinates:
 C2(H2), C3(H3), C5(H5), C8(H8), C9(H9), C14(H14), C15(H15), C16(H16), C17(H17)
;
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_refinement_flags_posn
_atom_site_refinement_flags_adp
_atom_site_disorder_group
I1 I 0.67725(3) 0.895320(16) 0.671965(13) 0.03074(6) Uani 1.000000 . . .
Se1 Se 0.05333(3) 0.41236(2) 0.301790(17) 0.01521(6) Uani 1.000000 . . .
O1 O 0.5984(3) 0.60419(17) 0.87373(12) 0.0258(4) Uani 1.000000 . . .
O2 O 0.5753(2) 0.37162(17) 0.88042(12) 0.0247(4) Uani 1.000000 . . .
N1 N 0.1802(3) 0.66725(18) 0.37513(14) 0.0147(4) Uani 1.000000 . . .
C1 C 0.1820(3) 0.5609(2) 0.40327(17) 0.0145(5) Uani 1.000000 . . .
C2 C 0.2686(3) 0.5587(2) 0.49893(17) 0.0156(5) Uani 1.000000 . . .
H2 H 0.3283(3) 0.6379(2) 0.54801(17) 0.0187(6) Uiso 1.000000 R . .
C3 C 0.2682(3) 0.4469(2) 0.52175(17) 0.0153(5) Uani 1.000000 . . .
H3 H 0.2078(3) 0.3701(2) 0.47013(17) 0.0184(6) Uiso 1.000000 R . .
C4 C 0.3486(3) 0.4300(2) 0.61523(17) 0.0150(5) Uani 1.000000 . . .
C5 C 0.4393(3) 0.5344(2) 0.70042(17) 0.0167(5) Uani 1.000000 . . .
H5 H 0.4508(3) 0.6209(2) 0.69764(17) 0.0201(6) Uiso 1.000000 R . .
C6 C 0.5109(3) 0.5112(2) 0.78720(17) 0.0181(5) Uani 1.000000 . . .
C7 C 0.4970(3) 0.3830(2) 0.79190(17) 0.0188(5) Uani 1.000000 . . .
C8 C 0.4076(3) 0.2810(2) 0.70937(18) 0.0198(5) Uani 1.000000 . . .
H8 H 0.3966(3) 0.1947(2) 0.71226(18) 0.0238(6) Uiso 1.000000 R . .
C9 C 0.3335(3) 0.3047(2) 0.62166(18) 0.0186(5) Uani 1.000000 . . .
H9 H 0.2714(3) 0.2340(2) 0.56526(18) 0.0223(6) Uiso 1.000000 R . .
C10 C 0.6017(4) 0.7364(3) 0.87606(19) 0.0317(7) Uani 1.000000 . . .
H10a H 0.6679(4) 0.7939(3) 0.94164(19) 0.0476(10) Uiso 1.000000 R . .
H10b H 0.6655(4) 0.7487(3) 0.82542(19) 0.0476(10) Uiso 1.000000 R . .
H10c H 0.4740(4) 0.7577(3) 0.86272(19) 0.0476(10) Uiso 1.000000 R . .
C11 C 0.5576(4) 0.2438(3) 0.8896(2) 0.0301(7) Uani 1.000000 . . .
H11a H 0.6195(4) 0.2480(3) 0.9566(2) 0.0452(10) Uiso 1.000000 R . .
H11b H 0.4256(4) 0.2118(3) 0.8777(2) 0.0452(10) Uiso 1.000000 R . .
H11c H 0.6156(4) 0.1843(3) 0.8409(2) 0.0452(10) Uiso 1.000000 R . .
C12 C 0.0004(3) 0.5235(2) 0.22596(17) 0.0144(5) Uani 1.000000 . . .
C13 C 0.0804(3) 0.6505(2) 0.27881(17) 0.0150(5) Uani 1.000000 . . .
C14 C 0.0577(3) 0.7487(2) 0.23592(19) 0.0211(6) Uani 1.000000 . . .
H14 H 0.1119(3) 0.8360(2) 0.27153(19) 0.0253(7) Uiso 1.000000 R . .
C15 C -0.0451(3) 0.7159(3) 0.14066(19) 0.0239(6) Uani 1.000000 . . .
H15 H -0.0616(3) 0.7820(3) 0.11051(19) 0.0287(7) Uiso 1.000000 R . .
C16 C -0.1257(3) 0.5887(3) 0.08710(18) 0.0229(6) Uani 1.000000 . . .
H16 H -0.1960(3) 0.5689(3) 0.02133(18) 0.0275(7) Uiso 1.000000 R . .
C17 C -0.1035(3) 0.4911(2) 0.12965(17) 0.0190(5) Uani 1.000000 . . .
H17 H -0.1581(3) 0.4039(2) 0.09389(17) 0.0227(6) Uiso 1.000000 R . .
C18 C 0.2738(3) 0.7970(2) 0.44150(18) 0.0194(5) Uani 1.000000 . . .
H18a H 0.3844(3) 0.7854(2) 0.48712(18) 0.0233(6) Uiso 1.000000 R . .
H18b H 0.3168(3) 0.8470(2) 0.40127(18) 0.0233(6) Uiso 1.000000 R . .
C19 C 0.1459(4) 0.8730(3) 0.5012(2) 0.0355(7) Uani 1.000000 . . .
H19a H 0.2121(4) 0.9581(3) 0.5442(2) 0.0533(11) Uiso 1.000000 R . .
H19b H 0.0374(4) 0.8860(3) 0.4562(2) 0.0533(11) Uiso 1.000000 R . .
H19c H 0.1050(4) 0.8245(3) 0.5420(2) 0.0533(11) Uiso 1.000000 R . .
O1S O 0.1436(6) -0.2011(4) 0.8786(3) 0.0373(10) Uani 0.500000 . . -1
O2S O 0.1137(6) 0.0100(4) 0.9338(3) 0.0336(9) Uani 0.500000 . . -1
C1S C 0.1520(7) -0.0962(5) 0.8686(4) 0.0249(12) Uani 0.500000 . . -1
C2S C 0.215(2) -0.0836(13) 0.7729(10) 0.052(3) Uani 0.500000 . U -1
H2Sa H 0.216(2) 0.0071(13) 0.7737(10) 0.078(5) Uiso 0.500000 R . -1
H2Sb H 0.340(2) -0.1097(13) 0.7725(10) 0.078(5) Uiso 0.500000 R . -1
H2Sc H 0.128(2) -0.1406(13) 0.7134(10) 0.078(5) Uiso 0.500000 R . -1
C3S C 0.0471(10) -0.0077(8) 1.0175(6) 0.0386(18) Uani 0.500000 . . -1
H3Sa H -0.0156(10) -0.0976(8) 0.9996(6) 0.046(2) Uiso 0.500000 R . -1
H3Sb H 0.1522(10) 0.0070(8) 1.0746(6) 0.046(2) Uiso 0.500000 R . -1
C4S C -0.0883(13) 0.0906(9) 1.0435(7) 0.078(3) Uani 0.500000 . . -1
H4Sa H -0.1364(13) 0.0816(9) 1.1000(7) 0.117(4) Uiso 0.500000 R . -1
H4Sb H -0.0245(13) 0.1791(9) 1.0611(7) 0.117(4) Uiso 0.500000 R . -1
H4Sc H -0.1916(13) 0.0750(9) 0.9864(7) 0.117(4) Uiso 0.500000 R . -1
O1W O -0.219(3) 0.0453(13) 1.2237(11) 0.063(5) Uani 0.300000 . U -2


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 1.874(2) . ?
Se1 C12 1.877(2) . ?
O1 C6 1.362(3) . ?
O1 C10 1.422(3) . ?
O2 C7 1.352(3) . ?
O2 C11 1.434(3) . ?
N1 C1 1.336(3) . ?
N1 C13 1.405(3) . ?
N1 C18 1.481(3) . ?
C1 C2 1.424(3) . ?
C2 C3 1.352(3) . ?
C3 C4 1.446(3) . ?
C4 C5 1.416(3) . ?
C4 C9 1.389(3) . ?
C5 C6 1.375(3) . ?
C6 C7 1.412(3) . ?
C7 C8 1.378(3) . ?
C8 C9 1.394(3) . ?
C12 C13 1.387(3) . ?
C12 C17 1.390(3) . ?
C13 C14 1.392(3) . ?
C14 C15 1.374(3) . ?
C15 C16 1.391(4) . ?
C16 C17 1.383(3) . ?
C18 C19 1.505(4) . ?
O1S C1S 1.190(6) . ?
O2S C1S 1.328(6) . ?
O2S C3S 1.450(9) . ?
C1S C2S 1.584(15) . ?
C3S C4S 1.511(11) . ?

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
C12 Se1 C1 86.36(10) . . ?
C10 O1 C6 116.90(19) . . ?
C11 O2 C7 117.0(2) . . ?
C13 N1 C1 116.32(19) . . ?
C18 N1 C1 122.6(2) . . ?
C18 N1 C13 121.08(19) . . ?
N1 C1 Se1 112.03(17) . . ?
C2 C1 Se1 123.08(17) . . ?
C2 C1 N1 124.9(2) . . ?
C3 C2 C1 121.7(2) . . ?
C4 C3 C2 127.8(2) . . ?
C5 C4 C3 123.4(2) . . ?
C9 C4 C3 118.0(2) . . ?
C9 C4 C5 118.6(2) . . ?
C6 C5 C4 120.2(2) . . ?
C5 C6 O1 125.1(2) . . ?
C7 C6 O1 114.4(2) . . ?
C7 C6 C5 120.5(2) . . ?
C6 C7 O2 115.2(2) . . ?
C8 C7 O2 125.2(2) . . ?
C8 C7 C6 119.6(2) . . ?
C9 C8 C7 120.0(2) . . ?
C8 C9 C4 121.2(2) . . ?
C13 C12 Se1 111.04(16) . . ?
C17 C12 Se1 127.75(18) . . ?
C17 C12 C13 121.2(2) . . ?
C12 C13 N1 114.2(2) . . ?
C14 C13 N1 125.5(2) . . ?
C14 C13 C12 120.3(2) . . ?
C15 C14 C13 118.2(2) . . ?
C16 C15 C14 121.9(2) . . ?
C17 C16 C15 120.0(2) . . ?
C16 C17 C12 118.4(2) . . ?
C19 C18 N1 111.6(2) . . ?
C3S O2S C1S 116.8(5) . . ?
O2S C1S O1S 123.4(5) . . ?
C2S C1S O1S 117.7(7) . . ?
C2S C1S O2S 118.9(6) . . ?
C4S C3S O2S 107.1(5) . . ?

_olex2_submission_special_instructions 'No special instructions were received'
loop_
_restr_U_iso_atom_site_label
_restr_U_iso_weight_param
C2S 0.0100
O1W 0.0200

####################################################################### 
# 
# 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_p21c
_database_code_depnum_ccdc_archive 'CCDC 1474553'
_audit_update_record             
;
2016-04-17 deposited with the CCDC.
2016-08-22 downloaded from the CCDC.
;
_audit_creation_date             2015-10-13
_audit_creation_method           
;
Olex2 1.2
(compiled 2015.09.30 svn.r3233 for OlexSys, GUI svn.r5103)
;
_chemical_formula_moiety         '2(I3), 2(C19 H20 N O2 Se)'
_chemical_formula_sum            'C38 H40 I6 N2 O4 Se2'
_chemical_formula_weight         1508.10
loop_
_atom_type_symbol
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_Cromer_Mann_a1
_atom_type_scat_Cromer_Mann_a2
_atom_type_scat_Cromer_Mann_a3
_atom_type_scat_Cromer_Mann_a4
_atom_type_scat_Cromer_Mann_b1
_atom_type_scat_Cromer_Mann_b2
_atom_type_scat_Cromer_Mann_b3
_atom_type_scat_Cromer_Mann_b4
_atom_type_scat_Cromer_Mann_c
_atom_type_scat_source
_atom_type_scat_dispersion_source
C 0.00347 0.00161 2.31000 1.02000 1.58860 0.86500 20.84390 10.20750 0.56870
51.65120 0.215599998832
'International Tables Volume C Table 6.1.1.4 (pp. 500-502)'
'Henke, Gullikson and Davis, At. Data and Nucl. Data Tables, 1993, 54, 2'
I -0.41187 1.83264 20.14720 18.99490 7.51380 2.27350 4.34700 0.38140 27.76600
66.87760 4.07119989395
'International Tables Volume C Table 6.1.1.4 (pp. 500-502)'
'Henke, Gullikson and Davis, At. Data and Nucl. Data Tables, 1993, 54, 2'
H 0.00000 0.00000 0.49300 0.32291 0.14019 0.04081 10.51090 26.12570 3.14236
57.79970 0.0030380000826
'International Tables Volume C Table 6.1.1.4 (pp. 500-502)'
'Henke, Gullikson and Davis, At. Data and Nucl. Data Tables, 1993, 54, 2'
O 0.01158 0.00611 3.04850 2.28680 1.54630 0.86700 13.27710 5.70110 0.32390
32.90890 0.250800013542
'International Tables Volume C Table 6.1.1.4 (pp. 500-502)'
'Henke, Gullikson and Davis, At. Data and Nucl. Data Tables, 1993, 54, 2'
N 0.00653 0.00323 12.21260 3.13220 2.01250 1.16630 0.00570 9.89330 28.99750
0.58260 -11.5290002823
'International Tables Volume C Table 6.1.1.4 (pp. 500-502)'
'Henke, Gullikson and Davis, At. Data and Nucl. Data Tables, 1993, 54, 2'
Se -0.08110 2.30834 17.00060 5.81960 3.97310 4.35430 2.40980 0.27260 15.23720
43.81630 2.84089994431
'International Tables Volume C Table 6.1.1.4 (pp. 500-502)'
'Henke, Gullikson and Davis, At. Data and Nucl. Data Tables, 1993, 54, 2'

_space_group_crystal_system      monoclinic
_space_group_IT_number           14
_space_group_name_H-M_alt        'P 1 21/c 1'
_space_group_name_Hall           '-P 2ybc'
loop_
_space_group_symop_id
_space_group_symop_operation_xyz
1 x,y,z
2 -x,y+1/2,-z+1/2
3 -x,-y,-z
4 x,-y-1/2,z-1/2

_symmetry_Int_Tables_number      14
_cell_length_a                   15.2110(3)
_cell_length_b                   14.7644(3)
_cell_length_c                   21.0641(4)
_cell_angle_alpha                90
_cell_angle_beta                 108.775(1)
_cell_angle_gamma                90
_cell_volume                     4478.89(16)
_cell_formula_units_Z            4
_cell_measurement_reflns_used    3254
_cell_measurement_temperature    120.0
_cell_measurement_theta_max      24
_cell_measurement_theta_min      2.3
_exptl_absorpt_coefficient_mu    5.825
_exptl_absorpt_correction_T_max  0.7594
_exptl_absorpt_correction_T_min  0.1389
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   SADABS
_exptl_crystal_colour            'dark violet'
_exptl_crystal_colour_modifier   dark
_exptl_crystal_colour_primary    violet
_exptl_crystal_density_diffrn    2.2363
_exptl_crystal_description       prism
_exptl_crystal_F_000             2790.6784
_exptl_crystal_size_max          0.56
_exptl_crystal_size_mid          0.14
_exptl_crystal_size_min          0.05
_exptl_special_details           
;
 ? 
;
_diffrn_reflns_av_R_equivalents  0.0481
_diffrn_reflns_av_unetI/netI     0.0462
_diffrn_reflns_limit_h_max       21
_diffrn_reflns_limit_h_min       -21
_diffrn_reflns_limit_k_max       20
_diffrn_reflns_limit_k_min       -20
_diffrn_reflns_limit_l_max       29
_diffrn_reflns_limit_l_min       -29
_diffrn_reflns_number            51154
_diffrn_reflns_theta_full        29.9987
_diffrn_reflns_theta_max         30.00
_diffrn_reflns_theta_min         1.41
_diffrn_ambient_temperature      120.15
_diffrn_measured_fraction_theta_full 0.9987
_diffrn_measured_fraction_theta_max 0.9987
_diffrn_measurement_device_type  'CCD SMART-6'
_diffrn_measurement_method       ?
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_type           'Mo K\a'
_diffrn_radiation_wavelength     0.71073
_reflns_Friedel_coverage         0.0
_reflns_limit_h_max              20
_reflns_limit_h_min              -21
_reflns_limit_k_max              20
_reflns_limit_k_min              0
_reflns_limit_l_max              29
_reflns_limit_l_min              0
_reflns_number_gt                9196
_reflns_number_total             13042
_reflns_threshold_expression     I>=2u(I)
_computing_molecular_graphics    'Olex2 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 (Dolomanov et al., 2009)'
_computing_structure_refinement  'olex2.refine (Bourhis et al., 2015)'
_computing_structure_solution    'ShelXS-1997 (Sheldrick, 2008)'
_refine_diff_density_max         1.5308
_refine_diff_density_min         -1.1671
_refine_diff_density_rms         0.2559
_refine_ls_d_res_high            0.7108
_refine_ls_d_res_low             14.4016
_refine_ls_goodness_of_fit_ref   0.8934
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_constraints    66
_refine_ls_number_parameters     474
_refine_ls_number_reflns         13042
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0537
_refine_ls_R_factor_gt           0.0283
_refine_ls_restrained_S_all      0.8934
_refine_ls_shift/su_max          0.0000
_refine_ls_shift/su_mean         0.0000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0229P)²] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0487
_refine_ls_wR_factor_ref         0.0543
_olex2_refinement_description    
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups, All C(H,H) groups
 At 1.5 times of:
  All C(H,H,H) groups
2.a Secondary CH2 refined with riding coordinates:
 C18(H18a,H18b), C18a(H18c,H18d)
2.b Aromatic/amide H refined with riding coordinates:
 C17(H17), C16(H16), C15(H15), C14(H14), C9(H9), C8(H8), C5(H5), C17a(H17a),
 C16a(H16a), C15a(H15a), C14a(H14a), C9a(H9a), C8a(H8a), C5a(H5a), C2(H2),
 C3(H3), C2a(H2a), C3a(H3a)
2.c Idealised Me refined as rotating group:
 C10(H10a,H10b,H10c), C11(H11a,H11b,H11c), C19(H19a,H19b,H19c), C10a(H10d,H10e,
 H10f), C11a(H11d,H11e,H11f), C19a(H19d,H19e,H19f)
;
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_refinement_flags_posn
I5 I 0.323376(16) 0.886986(15) 0.212573(10) 0.02660(5) Uani 1.000000 .
I2 I 0.228684(16) 1.048436(17) -0.232369(11) 0.02837(5) Uani 1.000000 .
I4 I 0.514349(16) 0.854728(16) 0.223239(11) 0.02862(5) Uani 1.000000 .
I6 I 0.124738(17) 0.916458(17) 0.200890(11) 0.03223(6) Uani 1.000000 .
I1 I 0.220884(17) 0.863304(17) -0.277295(11) 0.03339(6) Uani 1.000000 .
I3 I 0.245304(17) 1.246977(17) -0.203874(11) 0.03333(6) Uani 1.000000 .
Se1 Se 0.34768(2) 1.13453(2) -0.048662(15) 0.02073(7) Uani 1.000000 .
O1 O 0.39186(17) 0.60720(15) 0.05963(11) 0.0269(5) Uani 1.000000 .
O2 O 0.28788(16) 0.55161(15) -0.05301(11) 0.0259(5) Uani 1.000000 .
N1 N 0.47071(17) 1.12068(17) 0.07522(12) 0.0177(5) Uani 1.000000 .
C1 C 0.4136(2) 1.0687(2) 0.02812(15) 0.0196(7) Uani 1.000000 .
C12 C 0.4067(2) 1.2382(2) -0.00178(15) 0.0196(6) Uani 1.000000 .
C13 C 0.4682(2) 1.2140(2) 0.06110(15) 0.0195(6) Uani 1.000000 .
C14 C 0.5202(2) 1.2808(2) 0.10402(16) 0.0230(7) Uani 1.000000 .
C15 C 0.5082(2) 1.3695(2) 0.08282(17) 0.0266(7) Uani 1.000000 .
C16 C 0.4454(2) 1.3931(2) 0.02064(18) 0.0273(8) Uani 1.000000 .
C17 C 0.3948(2) 1.3276(2) -0.02201(16) 0.0247(7) Uani 1.000000 .
C2 C 0.4031(2) 0.9725(2) 0.03284(15) 0.0186(6) Uani 1.000000 .
C3 C 0.3463(2) 0.9254(2) -0.01875(15) 0.0195(6) Uani 1.000000 .
C4 C 0.3293(2) 0.8285(2) -0.02535(15) 0.0186(6) Uani 1.000000 .
C5 C 0.3718(2) 0.7653(2) 0.02599(15) 0.0189(6) Uani 1.000000 .
C6 C 0.3556(2) 0.6742(2) 0.01480(15) 0.0209(7) Uani 1.000000 .
C7 C 0.2963(2) 0.6432(2) -0.04847(16) 0.0217(7) Uani 1.000000 .
C8 C 0.2540(2) 0.7040(2) -0.09840(15) 0.0214(7) Uani 1.000000 .
C9 C 0.2704(2) 0.7960(2) -0.08639(15) 0.0213(7) Uani 1.000000 .
C10 C 0.4498(3) 0.6331(2) 0.12519(15) 0.0315(9) Uani 1.000000 .
C11 C 0.2331(3) 0.5147(2) -0.11682(17) 0.0337(9) Uani 1.000000 .
C18 C 0.5327(2) 1.0872(2) 0.14032(15) 0.0227(7) Uani 1.000000 .
C19 C 0.4909(3) 1.1016(2) 0.19580(16) 0.0302(8) Uani 1.000000 .
Se1a Se 0.14494(2) 0.78143(2) 0.043270(16) 0.02327(7) Uani 1.000000 .
O1a O 0.10385(16) 1.30956(16) -0.06653(11) 0.0280(5) Uani 1.000000 .
O2a O 0.21805(16) 1.36856(16) 0.04159(11) 0.0273(5) Uani 1.000000 .
N1a N 0.02417(18) 0.80481(18) -0.07987(12) 0.0207(6) Uani 1.000000 .
C1a C 0.0780(2) 0.8533(2) -0.02916(16) 0.0220(7) Uani 1.000000 .
C12a C 0.0912(2) 0.6821(2) -0.01064(16) 0.0237(7) Uani 1.000000 .
C13a C 0.0298(2) 0.7103(2) -0.07227(16) 0.0237(7) Uani 1.000000 .
C14a C -0.0170(2) 0.6470(2) -0.12006(18) 0.0291(8) Uani 1.000000 .
C15a C -0.0005(3) 0.5562(3) -0.1050(2) 0.0356(9) Uani 1.000000 .
C16a C 0.0629(3) 0.5281(3) -0.04344(19) 0.0335(9) Uani 1.000000 .
C17a C 0.1088(2) 0.5907(2) 0.00424(18) 0.0291(8) Uani 1.000000 .
C2a C 0.0860(2) 0.9500(2) -0.02966(16) 0.0226(7) Uani 1.000000 .
C3a C 0.1444(2) 0.9964(2) 0.02232(16) 0.0216(7) Uani 1.000000 .
C4a C 0.1606(2) 1.0932(2) 0.02709(16) 0.0219(7) Uani 1.000000 .
C5a C 0.1178(2) 1.1539(2) -0.02565(15) 0.0215(7) Uani 1.000000 .
C6a C 0.1385(2) 1.2444(2) -0.01913(15) 0.0218(7) Uani 1.000000 .
C7a C 0.2026(2) 1.2781(2) 0.04157(16) 0.0223(7) Uani 1.000000 .
C8a C 0.2440(2) 1.2196(2) 0.09388(16) 0.0245(7) Uani 1.000000 .
C9a C 0.2229(2) 1.1274(2) 0.08580(16) 0.0247(7) Uani 1.000000 .
C10a C 0.0396(2) 1.2808(3) -0.12872(16) 0.0283(8) Uani 1.000000 .
C11a C 0.2831(3) 1.4068(3) 0.10097(17) 0.0312(8) Uani 1.000000 .
C18a C -0.0350(2) 0.8458(2) -0.14344(16) 0.0259(7) Uani 1.000000 .
C19a C 0.0177(3) 0.8572(3) -0.19288(17) 0.0340(9) Uani 1.000000 .
H17 H 0.3526(2) 1.3436(2) -0.06461(16) 0.0296(9) Uiso 1.000000 R
H16 H 0.4375(2) 1.4550(2) 0.00766(18) 0.0328(9) Uiso 1.000000 R
H15 H 0.5435(2) 1.4156(2) 0.11118(17) 0.0319(9) Uiso 1.000000 R
H14 H 0.5627(2) 1.2654(2) 0.14666(16) 0.0276(8) Uiso 1.000000 R
H9 H 0.2407(2) 0.8380(2) -0.12076(15) 0.0255(8) Uiso 1.000000 R
H8 H 0.2141(2) 0.6835(2) -0.14056(15) 0.0257(8) Uiso 1.000000 R
H5 H 0.4116(2) 0.7859(2) 0.06819(15) 0.0227(8) Uiso 1.000000 R
H17a H 0.1513(2) 0.5720(2) 0.04604(18) 0.0349(9) Uiso 1.000000 R
H16a H 0.0742(3) 0.4654(3) -0.03466(19) 0.0402(10) Uiso 1.000000 R
H15a H -0.0326(3) 0.5120(3) -0.1368(2) 0.0427(11) Uiso 1.000000 R
H14a H -0.0593(2) 0.6656(2) -0.16195(18) 0.0350(9) Uiso 1.000000 R
H9a H 0.2519(2) 1.0870(2) 0.12146(16) 0.0296(9) Uiso 1.000000 R
H8a H 0.2861(2) 1.2418(2) 0.13470(16) 0.0294(9) Uiso 1.000000 R
H5a H 0.0743(2) 1.1318(2) -0.06591(15) 0.0257(8) Uiso 1.000000 R
H2 H 0.4367(2) 0.9417(2) 0.07293(15) 0.0223(8) Uiso 1.000000 R
H3 H 0.3122(2) 0.9607(2) -0.05637(15) 0.0234(8) Uiso 1.000000 R
H10a H 0.5033(9) 0.6673(15) 0.12165(18) 0.0473(13) Uiso 1.000000 GR
H10b H 0.4143(6) 0.6711(14) 0.1463(5) 0.0473(13) Uiso 1.000000 GR
H10c H 0.4716(14) 0.5788(3) 0.1525(4) 0.0473(13) Uiso 1.000000 GR
H11a H 0.2645(9) 0.5259(15) -0.1500(4) 0.0506(13) Uiso 1.000000 GR
H11b H 0.2257(15) 0.4493(4) -0.1124(3) 0.0506(13) Uiso 1.000000 GR
H11c H 0.1719(7) 0.5437(12) -0.1314(6) 0.0506(13) Uiso 1.000000 GR
H18a H 0.5445(2) 1.0218(2) 0.13656(15) 0.0272(8) Uiso 1.000000 R
H18b H 0.5930(2) 1.1192(2) 0.15177(15) 0.0272(8) Uiso 1.000000 R
H19a H 0.4316(8) 1.0694(14) 0.1848(6) 0.0453(12) Uiso 1.000000 GR
H19b H 0.5335(8) 1.0783(15) 0.2381(3) 0.0453(12) Uiso 1.000000 GR
H19c H 0.4806(16) 1.1664(3) 0.2004(8) 0.0453(12) Uiso 1.000000 GR
H2a H 0.0491(2) 0.9826(2) -0.06780(16) 0.0271(8) Uiso 1.000000 R
H3a H 0.1786(2) 0.9614(2) 0.06003(16) 0.0260(8) Uiso 1.000000 R
H10d H 0.0182(12) 1.3335(3) -0.1580(5) 0.0425(12) Uiso 1.000000 GR
H10e H 0.0700(5) 1.2378(12) -0.1503(6) 0.0425(12) Uiso 1.000000 GR
H10f H -0.0136(8) 1.2515(14) -0.1207(2) 0.0425(12) Uiso 1.000000 GR
H11d H 0.2949(13) 1.4702(5) 0.0926(4) 0.0468(12) Uiso 1.000000 GR
H11e H 0.2572(8) 1.4037(15) 0.1379(4) 0.0468(12) Uiso 1.000000 GR
H11f H 0.3414(6) 1.3727(10) 0.1129(7) 0.0468(12) Uiso 1.000000 GR
H18c H -0.0898(2) 0.8067(2) -0.16350(16) 0.0310(9) Uiso 1.000000 R
H18d H -0.0574(2) 0.9056(2) -0.13400(16) 0.0310(9) Uiso 1.000000 R
H19d H -0.0233(6) 0.8840(16) -0.2344(5) 0.0510(13) Uiso 1.000000 GR
H19e H 0.0712(10) 0.8971(14) -0.1735(5) 0.0510(13) Uiso 1.000000 GR
H19f H 0.0394(15) 0.7980(3) -0.2027(10) 0.0510(13) Uiso 1.000000 GR


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
I5 I4 2.8802(3) . ?
I5 I6 2.9834(3) . ?
I2 I1 2.8825(4) . ?
I2 I3 2.9865(4) . ?
Se1 C1 1.877(3) . ?
Se1 C12 1.885(3) . ?
O1 C6 1.357(4) . ?
O1 C10 1.431(4) . ?
O2 C7 1.358(4) . ?
O2 C11 1.441(4) . ?
N1 C1 1.331(4) . ?
N1 C13 1.407(4) . ?
N1 C18 1.477(4) . ?
C1 C2 1.437(4) . ?
C12 C13 1.400(4) . ?
C12 C17 1.381(4) . ?
C13 C14 1.399(4) . ?
C14 C15 1.376(5) . ?
C15 C16 1.394(5) . ?
C16 C17 1.374(5) . ?
C2 C3 1.344(4) . ?
C3 C4 1.453(4) . ?
C4 C5 1.417(4) . ?
C4 C9 1.394(4) . ?
C5 C6 1.374(4) . ?
C6 C7 1.423(4) . ?
C7 C8 1.376(4) . ?
C8 C9 1.389(4) . ?
C18 C19 1.515(4) . ?
Se1a C1a 1.868(3) . ?
Se1a C12a 1.874(3) . ?
O1a C6a 1.364(4) . ?
O1a C10a 1.424(4) . ?
O2a C7a 1.357(4) . ?
O2a C11a 1.437(4) . ?
N1a C1a 1.327(4) . ?
N1a C13a 1.403(4) . ?
N1a C18a 1.481(4) . ?
C1a C2a 1.433(5) . ?
C12a C13a 1.397(4) . ?
C12a C17a 1.391(5) . ?
C13a C14a 1.391(5) . ?
C14a C15a 1.381(5) . ?
C15a C16a 1.407(5) . ?
C16a C17a 1.378(5) . ?
C2a C3a 1.353(5) . ?
C3a C4a 1.449(5) . ?
C4a C5a 1.413(4) . ?
C4a C9a 1.388(4) . ?
C5a C6a 1.370(5) . ?
C6a C7a 1.425(4) . ?
C7a C8a 1.382(4) . ?
C8a C9a 1.396(5) . ?
C18a C19a 1.514(5) . ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
I6 I5 I4 178.845(11) . . ?
I3 I2 I1 171.345(11) . . ?
C12 Se1 C1 86.37(14) . . ?
C10 O1 C6 117.6(3) . . ?
C11 O2 C7 117.1(3) . . ?
C13 N1 C1 116.1(3) . . ?
C18 N1 C1 124.5(3) . . ?
C18 N1 C13 119.3(3) . . ?
N1 C1 Se1 112.5(2) . . ?
C2 C1 Se1 122.1(2) . . ?
C2 C1 N1 125.4(3) . . ?
C13 C12 Se1 110.4(2) . . ?
C17 C12 Se1 128.4(2) . . ?
C17 C12 C13 121.1(3) . . ?
C12 C13 N1 114.5(3) . . ?
C14 C13 N1 125.6(3) . . ?
C14 C13 C12 119.9(3) . . ?
C15 C14 C13 118.2(3) . . ?
C16 C15 C14 121.5(3) . . ?
C17 C16 C15 120.5(3) . . ?
C16 C17 C12 118.7(3) . . ?
C3 C2 C1 120.8(3) . . ?
C4 C3 C2 129.4(3) . . ?
C5 C4 C3 123.5(3) . . ?
C9 C4 C3 117.9(3) . . ?
C9 C4 C5 118.5(3) . . ?
C6 C5 C4 120.0(3) . . ?
C5 C6 O1 125.7(3) . . ?
C7 C6 O1 114.2(3) . . ?
C7 C6 C5 120.1(3) . . ?
C6 C7 O2 113.8(3) . . ?
C8 C7 O2 125.9(3) . . ?
C8 C7 C6 120.3(3) . . ?
C9 C8 C7 119.2(3) . . ?
C8 C9 C4 121.9(3) . . ?
C19 C18 N1 111.6(3) . . ?
C12a Se1a C1a 86.14(14) . . ?
C10a O1a C6a 116.9(3) . . ?
C11a O2a C7a 117.3(3) . . ?
C13a N1a C1a 116.4(3) . . ?
C18a N1a C1a 123.1(3) . . ?
C18a N1a C13a 120.4(3) . . ?
N1a C1a Se1a 112.6(2) . . ?
C2a C1a Se1a 123.1(2) . . ?
C2a C1a N1a 124.3(3) . . ?
C13a C12a Se1a 111.1(2) . . ?
C17a C12a Se1a 127.4(3) . . ?
C17a C12a C13a 121.5(3) . . ?
C12a C13a N1a 113.7(3) . . ?
C14a C13a N1a 126.0(3) . . ?
C14a C13a C12a 120.3(3) . . ?
C15a C14a C13a 118.2(3) . . ?
C16a C15a C14a 121.2(3) . . ?
C17a C16a C15a 120.7(3) . . ?
C16a C17a C12a 118.0(3) . . ?
C3a C2a C1a 122.2(3) . . ?
C4a C3a C2a 127.5(3) . . ?
C5a C4a C3a 123.1(3) . . ?
C9a C4a C3a 118.2(3) . . ?
C9a C4a C5a 118.7(3) . . ?
C6a C5a C4a 120.4(3) . . ?
C5a C6a O1a 126.3(3) . . ?
C7a C6a O1a 113.7(3) . . ?
C7a C6a C5a 119.9(3) . . ?
C6a C7a O2a 114.3(3) . . ?
C8a C7a O2a 125.5(3) . . ?
C8a C7a C6a 120.2(3) . . ?
C9a C8a C7a 118.9(3) . . ?
C8a C9a C4a 121.8(3) . . ?
C19a C18a N1a 111.4(3) . . ?

_olex2_submission_special_instructions 'No special instructions were received'
####################################################################### 
# 
# 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_p21n
_database_code_depnum_ccdc_archive 'CCDC 1474554'
_audit_update_record             
;
2016-04-17 deposited with the CCDC.
2016-08-22 downloaded from the CCDC.
;
_audit_creation_date             2015-10-23
_audit_creation_method           
;
Olex2 1.2
(compiled 2015.09.30 svn.r3233 for OlexSys, GUI svn.r5103)
;
_chemical_name_common            ?
_chemical_name_systematic        
;
 ? 
;
_chemical_formula_moiety         'C19 H20 N O2 Se, C7 H7 O3 S'
_chemical_formula_sum            'C26 H27 N O5 S Se'
_chemical_formula_weight         544.51
_chemical_melting_point          ?
loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
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'

_space_group_crystal_system      monoclinic
_space_group_IT_number           14
_space_group_name_H-M_alt        'P 1 21/n 1'
_space_group_name_Hall           '-P 2yn'
loop_
_space_group_symop_id
_space_group_symop_operation_xyz
1 'x, y, z'
2 '-x+1/2, y+1/2, -z+1/2'
3 '-x, -y, -z'
4 'x-1/2, -y-1/2, z-1/2'

_cell_length_a                   7.5216(4)
_cell_length_b                   29.2202(16)
_cell_length_c                   11.1130(6)
_cell_angle_alpha                90.00
_cell_angle_beta                 93.721(5)
_cell_angle_gamma                90.00
_cell_volume                     2437.3(2)
_cell_formula_units_Z            4
_cell_measurement_reflns_used    3826
_cell_measurement_temperature    120.15
_cell_measurement_theta_max      2.3
_cell_measurement_theta_min      27.0
_exptl_absorpt_coefficient_mu    1.664
_exptl_absorpt_correction_T_max  0.85371
_exptl_absorpt_correction_T_min  0.65382
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   ?
_exptl_crystal_colour            orange
_exptl_crystal_colour_primary    orange
_exptl_crystal_density_diffrn    1.484
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       prism
_exptl_crystal_F_000             1120
_exptl_crystal_size_max          0.46
_exptl_crystal_size_mid          0.12
_exptl_crystal_size_min          0.08
_exptl_special_details           
;
 ? 
;
_diffrn_reflns_av_R_equivalents  0.0661
_diffrn_reflns_av_unetI/netI     0.0836
_diffrn_reflns_limit_h_max       7
_diffrn_reflns_limit_h_min       -9
_diffrn_reflns_limit_k_max       37
_diffrn_reflns_limit_k_min       -36
_diffrn_reflns_limit_l_max       14
_diffrn_reflns_limit_l_min       -14
_diffrn_reflns_number            16092
_diffrn_reflns_theta_full        27.00
_diffrn_reflns_theta_max         27.00
_diffrn_reflns_theta_min         2.78
_diffrn_ambient_temperature      120.15
_diffrn_detector_area_resol_mean ?
_diffrn_measured_fraction_theta_full 0.995
_diffrn_measured_fraction_theta_max 0.995
_diffrn_measurement_device_type  SMART-6K
_diffrn_measurement_method       'phi and omega scans'
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_source                   'fine-focus sealed tube'
_diffrn_standards_decay_%        ?
_diffrn_standards_interval_count ?
_diffrn_standards_interval_time  ?
_diffrn_standards_number         ?
_reflns_number_gt                3763
_reflns_number_total             5302
_reflns_threshold_expression     >2sigma(I)
_computing_cell_refinement       ?
_computing_data_collection       ?
_computing_data_reduction        ?
_computing_molecular_graphics    'Olex2 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 (Dolomanov et al., 2009)'
_computing_structure_refinement  'XL (Sheldrick, 2008)'
_computing_structure_solution    'ShelXS-1997 (Sheldrick, 2008)'
_refine_diff_density_max         0.537
_refine_diff_density_min         -0.549
_refine_diff_density_rms         0.097
_refine_ls_extinction_coef       ?
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.034
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     316
_refine_ls_number_reflns         5302
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0870
_refine_ls_R_factor_gt           0.0520
_refine_ls_restrained_S_all      1.034
_refine_ls_shift/su_max          0.001
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details     
'calc w=1/[σ²(Fo²)+(0.0364P)²+0.1122P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0958
_refine_ls_wR_factor_ref         0.1078
_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. 
;
_olex2_refinement_description    
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups, All C(H,H) groups
 At 1.5 times of:
  All C(H,H,H) groups
2. Others
 Fixed Sof: O1A(0.52) O2A(0.52) O3A(0.52) O1B(0.4) O2B(0.4) O3B(0.4) O1C(0.08)
 O2C(0.08) O3C(0.08)
3.a Secondary CH2 refined with riding coordinates:
 C18(H18A,H18B)
3.b Me refined with riding coordinates:
 C10(H10A,H10B,H10C), C11(H11A,H11B,H11C), C19(H19A,H19B,H19C), C7A(H7AA,H7AB,
 H7AC)
3.c Aromatic/amide H refined with riding coordinates:
 C2(H2), C3(H3), C5(H5), C8(H8), C9(H9), C14(H14), C15(H15), C16(H16),
 C17(H17), C2A(H2A), C3A(H3A), C5A(H5A), C6A(H6A)
;
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
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_calc_flag
_atom_site_disorder_assembly
_atom_site_disorder_group
_atom_site_refinement_flags_posn
Se1 Se 0.35433(4) 0.091561(12) 0.50803(3) 0.02342(12) Uani 1 d . . .
O1 O 0.0999(3) -0.17548(8) 0.5641(2) 0.0295(6) Uani 1 d . . .
O2 O 0.1283(3) -0.17951(8) 0.7922(2) 0.0255(6) Uani 1 d . . .
N1 N 0.2539(3) 0.05523(9) 0.2922(2) 0.0175(6) Uani 1 d . . .
C1 C 0.2675(4) 0.04373(11) 0.4094(3) 0.0174(7) Uani 1 d . . .
C2 C 0.2258(4) -0.00047(12) 0.4548(3) 0.0197(8) Uani 1 d . . .
H2 H 0.1892 -0.0233 0.4005 0.024 Uiso 1 calc . . R
C3 C 0.2375(4) -0.01025(12) 0.5736(3) 0.0211(8) Uani 1 d . . .
H3 H 0.2696 0.0138 0.6253 0.025 Uiso 1 calc . . R
C4 C 0.2060(4) -0.05375(12) 0.6296(3) 0.0192(7) Uani 1 d . . .
C5 C 0.1607(4) -0.09348(12) 0.5628(3) 0.0208(7) Uani 1 d . . .
H5 H 0.1464 -0.0919 0.4791 0.025 Uiso 1 calc . . R
C6 C 0.1374(4) -0.13463(12) 0.6196(3) 0.0203(8) Uani 1 d . . .
C7 C 0.1545(4) -0.13700(12) 0.7473(3) 0.0182(7) Uani 1 d . . .
C8 C 0.1933(4) -0.09808(12) 0.8137(3) 0.0197(7) Uani 1 d . . .
H8 H 0.2012 -0.0994 0.8975 0.024 Uiso 1 calc . . R
C9 C 0.2206(4) -0.05689(12) 0.7552(3) 0.0213(8) Uani 1 d . . .
H9 H 0.2491 -0.0309 0.8007 0.026 Uiso 1 calc . . R
C10 C 0.0781(6) -0.17490(14) 0.4361(3) 0.0436(11) Uani 1 d . . .
H10A H 0.0524 -0.2053 0.4070 0.065 Uiso 1 calc . . R
H10B H 0.1858 -0.1641 0.4037 0.065 Uiso 1 calc . . R
H10C H -0.0185 -0.1549 0.4110 0.065 Uiso 1 calc . . R
C11 C 0.1422(5) -0.18495(13) 0.9203(3) 0.0303(9) Uani 1 d . . .
H11A H 0.1209 -0.2164 0.9402 0.045 Uiso 1 calc . . R
H11B H 0.0556 -0.1659 0.9555 0.045 Uiso 1 calc . . R
H11C H 0.2595 -0.1763 0.9512 0.045 Uiso 1 calc . . R
C12 C 0.3726(4) 0.12530(11) 0.3660(3) 0.0182(7) Uani 1 d . . .
C13 C 0.3117(4) 0.09960(11) 0.2655(3) 0.0174(7) Uani 1 d . . .
C14 C 0.3126(4) 0.11796(12) 0.1497(3) 0.0220(8) Uani 1 d . . .
H14 H 0.2715 0.1012 0.0824 0.026 Uiso 1 calc . . R
C15 C 0.3773(4) 0.16231(12) 0.1384(3) 0.0250(8) Uani 1 d . . .
H15 H 0.3795 0.1753 0.0622 0.030 Uiso 1 calc . . R
C16 C 0.4387(4) 0.18747(12) 0.2385(3) 0.0243(8) Uani 1 d . . .
H16 H 0.4819 0.2169 0.2282 0.029 Uiso 1 calc . . R
C17 C 0.4364(4) 0.16940(12) 0.3529(3) 0.0225(8) Uani 1 d . . .
H17 H 0.4768 0.1864 0.4199 0.027 Uiso 1 calc . . R
C18 C 0.1918(4) 0.02333(11) 0.1950(3) 0.0199(7) Uani 1 d . . .
H18A H 0.1319 0.0405 0.1296 0.024 Uiso 1 calc . . R
H18B H 0.1063 0.0022 0.2257 0.024 Uiso 1 calc . . R
C19 C 0.3433(4) -0.00323(13) 0.1474(4) 0.0335(10) Uani 1 d . . .
H19A H 0.2982 -0.0235 0.0846 0.050 Uiso 1 calc . . R
H19B H 0.4015 -0.0208 0.2115 0.050 Uiso 1 calc . . R
H19C H 0.4272 0.0176 0.1156 0.050 Uiso 1 calc . . R
S1 S 0.07497(11) 0.08527(3) 0.83335(8) 0.0192(2) Uani 1 d . . .
O1A O -0.0833(8) 0.1068(2) 0.8805(6) 0.0258(19) Uiso 0.52 d A 1 .
O2A O 0.0470(7) 0.06974(19) 0.7084(5) 0.0158(16) Uiso 0.52 d A 1 .
O3A O 0.1490(8) 0.0501(2) 0.9118(6) 0.0248(19) Uiso 0.52 d A 1 .
O1B O -0.0563(11) 0.1022(3) 0.9095(8) 0.022(2) Uiso 0.40 d A 2 .
O2B O 0.0016(11) 0.0759(3) 0.7126(7) 0.023(2) Uiso 0.40 d A 2 .
O3B O 0.1824(10) 0.0467(3) 0.8902(8) 0.021(2) Uiso 0.40 d A 2 .
O1C O -0.078(4) 0.1001(10) 0.740(3) 0.021(7) Uiso 0.08 d A 3 .
O2C O 0.022(4) 0.0868(10) 0.947(3) 0.017(6) Uiso 0.08 d A 3 .
O3C O 0.170(3) 0.0465(10) 0.797(3) 0.019(6) Uiso 0.08 d A 3 .
C1A C 0.2354(4) 0.12994(11) 0.8264(3) 0.0188(7) Uani 1 d A . .
C2A C 0.4147(4) 0.11819(12) 0.8236(3) 0.0229(8) Uani 1 d . . .
H2A H 0.4492 0.0876 0.8281 0.027 Uiso 1 calc A . R
C3A C 0.5414(4) 0.15224(13) 0.8142(3) 0.0241(8) Uani 1 d A . .
H3A H 0.6606 0.1441 0.8119 0.029 Uiso 1 calc . . R
C4A C 0.4946(4) 0.19804(12) 0.8081(3) 0.0236(8) Uani 1 d . . .
C5A C 0.3144(4) 0.20947(12) 0.8130(3) 0.0246(8) Uani 1 d A . .
H5A H 0.2800 0.2400 0.8108 0.029 Uiso 1 calc . . R
C6A C 0.1870(4) 0.17552(11) 0.8213(3) 0.0201(8) Uani 1 d . . .
H6A H 0.0676 0.1835 0.8234 0.024 Uiso 1 calc A . R
C7A C 0.6326(4) 0.23484(13) 0.7987(4) 0.0327(9) Uani 1 d A . .
H7AA H 0.7482 0.2211 0.7962 0.049 Uiso 1 calc . . R
H7AB H 0.6312 0.2547 0.8675 0.049 Uiso 1 calc . . R
H7AC H 0.6066 0.2523 0.7265 0.049 Uiso 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 1.868(3) . ?
Se1 C12 1.873(3) . ?
O1 C6 1.365(4) . ?
O1 C10 1.421(4) . ?
O2 C7 1.358(4) . ?
O2 C11 1.430(4) . ?
N1 C1 1.342(4) . ?
N1 C13 1.405(4) . ?
N1 C18 1.480(4) . ?
C1 C2 1.429(4) . ?
C2 H2 0.9300 . ?
C2 C3 1.348(4) . ?
C3 H3 0.9300 . ?
C3 C4 1.442(5) . ?
C4 C5 1.408(5) . ?
C4 C9 1.396(5) . ?
C5 H5 0.9300 . ?
C5 C6 1.375(5) . ?
C6 C7 1.419(5) . ?
C7 C8 1.376(5) . ?
C8 H8 0.9300 . ?
C8 C9 1.389(5) . ?
C9 H9 0.9300 . ?
C10 H10A 0.9600 . ?
C10 H10B 0.9600 . ?
C10 H10C 0.9600 . ?
C11 H11A 0.9600 . ?
C11 H11B 0.9600 . ?
C11 H11C 0.9600 . ?
C12 C13 1.399(4) . ?
C12 C17 1.386(5) . ?
C13 C14 1.394(5) . ?
C14 H14 0.9300 . ?
C14 C15 1.393(5) . ?
C15 H15 0.9300 . ?
C15 C16 1.387(5) . ?
C16 H16 0.9300 . ?
C16 C17 1.378(5) . ?
C17 H17 0.9300 . ?
C18 H18A 0.9700 . ?
C18 H18B 0.9700 . ?
C18 C19 1.503(4) . ?
C19 H19A 0.9600 . ?
C19 H19B 0.9600 . ?
C19 H19C 0.9600 . ?
S1 O1A 1.472(6) . ?
S1 O2A 1.463(5) . ?
S1 O3A 1.436(7) . ?
S1 O1B 1.430(8) . ?
S1 O2B 1.443(8) . ?
S1 O3B 1.503(8) . ?
S1 O1C 1.56(3) . ?
S1 O2C 1.35(3) . ?
S1 O3C 1.41(3) . ?
S1 C1A 1.783(3) . ?
C1A C2A 1.394(4) . ?
C1A C6A 1.381(4) . ?
C2A H2A 0.9300 . ?
C2A C3A 1.386(5) . ?
C3A H3A 0.9300 . ?
C3A C4A 1.385(5) . ?
C4A C5A 1.400(5) . ?
C4A C7A 1.503(5) . ?
C5A H5A 0.9300 . ?
C5A C6A 1.386(4) . ?
C6A H6A 0.9300 . ?
C7A H7AA 0.9600 . ?
C7A H7AB 0.9600 . ?
C7A H7AC 0.9600 . ?

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 C12 86.64(15) . . ?
C6 O1 C10 116.7(3) . . ?
C7 O2 C11 117.7(3) . . ?
C1 N1 C13 115.5(3) . . ?
C1 N1 C18 123.4(3) . . ?
C13 N1 C18 120.9(3) . . ?
N1 C1 Se1 112.6(2) . . ?
N1 C1 C2 124.4(3) . . ?
C2 C1 Se1 123.1(3) . . ?
C1 C2 H2 118.8 . . ?
C3 C2 C1 122.4(3) . . ?
C3 C2 H2 118.8 . . ?
C2 C3 H3 116.3 . . ?
C2 C3 C4 127.4(3) . . ?
C4 C3 H3 116.3 . . ?
C5 C4 C3 122.7(3) . . ?
C9 C4 C3 119.0(3) . . ?
C9 C4 C5 118.3(3) . . ?
C4 C5 H5 119.6 . . ?
C6 C5 C4 120.8(3) . . ?
C6 C5 H5 119.6 . . ?
O1 C6 C5 125.9(3) . . ?
O1 C6 C7 114.3(3) . . ?
C5 C6 C7 119.8(3) . . ?
O2 C7 C6 114.0(3) . . ?
O2 C7 C8 126.2(3) . . ?
C8 C7 C6 119.9(3) . . ?
C7 C8 H8 120.1 . . ?
C7 C8 C9 119.9(3) . . ?
C9 C8 H8 120.1 . . ?
C4 C9 H9 119.3 . . ?
C8 C9 C4 121.3(3) . . ?
C8 C9 H9 119.3 . . ?
O1 C10 H10A 109.5 . . ?
O1 C10 H10B 109.5 . . ?
O1 C10 H10C 109.5 . . ?
H10A C10 H10B 109.5 . . ?
H10A C10 H10C 109.5 . . ?
H10B C10 H10C 109.5 . . ?
O2 C11 H11A 109.5 . . ?
O2 C11 H11B 109.5 . . ?
O2 C11 H11C 109.5 . . ?
H11A C11 H11B 109.5 . . ?
H11A C11 H11C 109.5 . . ?
H11B C11 H11C 109.5 . . ?
C13 C12 Se1 110.6(2) . . ?
C17 C12 Se1 128.5(3) . . ?
C17 C12 C13 120.8(3) . . ?
C12 C13 N1 114.6(3) . . ?
C14 C13 N1 124.8(3) . . ?
C14 C13 C12 120.6(3) . . ?
C13 C14 H14 121.2 . . ?
C15 C14 C13 117.6(3) . . ?
C15 C14 H14 121.2 . . ?
C14 C15 H15 119.3 . . ?
C16 C15 C14 121.4(3) . . ?
C16 C15 H15 119.3 . . ?
C15 C16 H16 119.6 . . ?
C17 C16 C15 120.9(3) . . ?
C17 C16 H16 119.6 . . ?
C12 C17 H17 120.7 . . ?
C16 C17 C12 118.6(3) . . ?
C16 C17 H17 120.7 . . ?
N1 C18 H18A 109.3 . . ?
N1 C18 H18B 109.3 . . ?
N1 C18 C19 111.8(3) . . ?
H18A C18 H18B 107.9 . . ?
C19 C18 H18A 109.3 . . ?
C19 C18 H18B 109.3 . . ?
C18 C19 H19A 109.5 . . ?
C18 C19 H19B 109.5 . . ?
C18 C19 H19C 109.5 . . ?
H19A C19 H19B 109.5 . . ?
H19A C19 H19C 109.5 . . ?
H19B C19 H19C 109.5 . . ?
O1A S1 O3B 126.6(4) . . ?
O1A S1 O1C 62.5(11) . . ?
O1A S1 C1A 105.5(3) . . ?
O2A S1 O1A 113.6(3) . . ?
O2A S1 O3B 101.9(4) . . ?
O2A S1 O1C 53.2(12) . . ?
O2A S1 C1A 104.0(2) . . ?
O3A S1 O1A 112.3(4) . . ?
O3A S1 O2A 112.4(3) . . ?
O3A S1 O2B 122.6(4) . . ?
O3A S1 O3B 14.3(4) . . ?
O3A S1 O1C 147.5(11) . . ?
O3A S1 C1A 108.3(3) . . ?
O1B S1 O1A 15.5(4) . . ?
O1B S1 O2A 127.4(4) . . ?
O1B S1 O3A 98.3(5) . . ?
O1B S1 O2B 112.3(5) . . ?
O1B S1 O3B 112.6(5) . . ?
O1B S1 O1C 77.8(12) . . ?
O1B S1 C1A 105.5(3) . . ?
O2B S1 O1A 98.2(4) . . ?
O2B S1 O2A 15.5(4) . . ?
O2B S1 O3B 114.3(5) . . ?
O2B S1 O1C 38.2(11) . . ?
O2B S1 C1A 108.5(3) . . ?
O3B S1 O1C 147.4(12) . . ?
O3B S1 C1A 102.8(3) . . ?
O1C S1 C1A 103.8(11) . . ?
O2C S1 O1A 50.0(13) . . ?
O2C S1 O2A 149.9(11) . . ?
O2C S1 O3A 65.3(13) . . ?
O2C S1 O1B 34.6(11) . . ?
O2C S1 O2B 139.2(12) . . ?
O2C S1 O3B 79.3(13) . . ?
O2C S1 O1C 111.2(17) . . ?
O2C S1 O3C 118.8(17) . . ?
O2C S1 C1A 105.0(11) . . ?
O3C S1 O1A 151.6(11) . . ?
O3C S1 O2A 61.4(11) . . ?
O3C S1 O3A 54.5(12) . . ?
O3C S1 O1B 146.0(12) . . ?
O3C S1 O2B 75.4(12) . . ?
O3C S1 O3B 41.6(11) . . ?
O3C S1 O1C 113.3(16) . . ?
O3C S1 C1A 102.7(11) . . ?
C2A C1A S1 118.6(3) . . ?
C6A C1A S1 122.0(3) . . ?
C6A C1A C2A 119.3(3) . . ?
C1A C2A H2A 120.1 . . ?
C3A C2A C1A 119.7(3) . . ?
C3A C2A H2A 120.1 . . ?
C2A C3A H3A 119.2 . . ?
C4A C3A C2A 121.6(3) . . ?
C4A C3A H3A 119.2 . . ?
C3A C4A C5A 118.2(3) . . ?
C3A C4A C7A 121.4(3) . . ?
C5A C4A C7A 120.4(3) . . ?
C4A C5A H5A 119.8 . . ?
C6A C5A C4A 120.4(3) . . ?
C6A C5A H5A 119.8 . . ?
C1A C6A C5A 120.8(3) . . ?
C1A C6A H6A 119.6 . . ?
C5A C6A H6A 119.6 . . ?
C4A C7A H7AA 109.5 . . ?
C4A C7A H7AB 109.5 . . ?
C4A C7A H7AC 109.5 . . ?
H7AA C7A H7AB 109.5 . . ?
H7AA C7A H7AC 109.5 . . ?
H7AB C7A H7AC 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
Se1 C1 C2 C3 3.5(4) . . . . ?
Se1 C12 C13 N1 -0.7(3) . . . . ?
Se1 C12 C13 C14 179.9(2) . . . . ?
Se1 C12 C17 C16 179.5(2) . . . . ?
O1 C6 C7 O2 -0.8(4) . . . . ?
O1 C6 C7 C8 179.6(3) . . . . ?
O2 C7 C8 C9 178.6(3) . . . . ?
N1 C1 C2 C3 -178.5(3) . . . . ?
N1 C13 C14 C15 -178.8(3) . . . . ?
C1 Se1 C12 C13 1.4(2) . . . . ?
C1 Se1 C12 C17 -178.2(3) . . . . ?
C1 N1 C13 C12 -0.8(4) . . . . ?
C1 N1 C13 C14 178.6(3) . . . . ?
C1 N1 C18 C19 -89.7(4) . . . . ?
C1 C2 C3 C4 -177.3(3) . . . . ?
C2 C3 C4 C5 1.5(5) . . . . ?
C2 C3 C4 C9 -178.4(3) . . . . ?
C3 C4 C5 C6 177.9(3) . . . . ?
C3 C4 C9 C8 -179.4(3) . . . . ?
C4 C5 C6 O1 -177.5(3) . . . . ?
C4 C5 C6 C7 1.7(5) . . . . ?
C5 C4 C9 C8 0.7(5) . . . . ?
C5 C6 C7 O2 180.0(3) . . . . ?
C5 C6 C7 C8 0.4(5) . . . . ?
C6 C7 C8 C9 -1.8(5) . . . . ?
C7 C8 C9 C4 1.3(5) . . . . ?
C9 C4 C5 C6 -2.2(5) . . . . ?
C10 O1 C6 C5 -1.9(5) . . . . ?
C10 O1 C6 C7 178.9(3) . . . . ?
C11 O2 C7 C6 -179.7(3) . . . . ?
C11 O2 C7 C8 -0.1(5) . . . . ?
C12 Se1 C1 N1 -1.9(2) . . . . ?
C12 Se1 C1 C2 176.3(3) . . . . ?
C12 C13 C14 C15 0.5(5) . . . . ?
C13 N1 C1 Se1 1.9(3) . . . . ?
C13 N1 C1 C2 -176.3(3) . . . . ?
C13 N1 C18 C19 87.0(4) . . . . ?
C13 C12 C17 C16 0.0(5) . . . . ?
C13 C14 C15 C16 -0.1(5) . . . . ?
C14 C15 C16 C17 -0.4(5) . . . . ?
C15 C16 C17 C12 0.5(5) . . . . ?
C17 C12 C13 N1 178.9(3) . . . . ?
C17 C12 C13 C14 -0.5(5) . . . . ?
C18 N1 C1 Se1 178.9(2) . . . . ?
C18 N1 C1 C2 0.7(5) . . . . ?
C18 N1 C13 C12 -177.8(3) . . . . ?
C18 N1 C13 C14 1.6(5) . . . . ?
S1 C1A C2A C3A 177.9(3) . . . . ?
S1 C1A C6A C5A -178.5(3) . . . . ?
O1A S1 C1A C2A 159.2(4) . . . . ?
O1A S1 C1A C6A -22.1(4) . . . . ?
O2A S1 C1A C2A -81.0(4) . . . . ?
O2A S1 C1A C6A 97.7(4) . . . . ?
O3A S1 C1A C2A 38.7(4) . . . . ?
O3A S1 C1A C6A -142.6(4) . . . . ?
O1B S1 C1A C2A 143.1(5) . . . . ?
O1B S1 C1A C6A -38.2(5) . . . . ?
O2B S1 C1A C2A -96.4(5) . . . . ?
O2B S1 C1A C6A 82.3(5) . . . . ?
O3B S1 C1A C2A 25.0(4) . . . . ?
O3B S1 C1A C6A -156.3(4) . . . . ?
O1C S1 C1A C2A -136.0(12) . . . . ?
O1C S1 C1A C6A 42.7(12) . . . . ?
O2C S1 C1A C2A 107.1(14) . . . . ?
O2C S1 C1A C6A -74.1(14) . . . . ?
O3C S1 C1A C2A -17.7(12) . . . . ?
O3C S1 C1A C6A 161.0(12) . . . . ?
C1A C2A C3A C4A 0.4(5) . . . . ?
C2A C1A C6A C5A 0.2(5) . . . . ?
C2A C3A C4A C5A 0.7(5) . . . . ?
C2A C3A C4A C7A 179.6(3) . . . . ?
C3A C4A C5A C6A -1.3(5) . . . . ?
C4A C5A C6A C1A 0.9(5) . . . . ?
C6A C1A C2A C3A -0.9(5) . . . . ?
C7A C4A C5A C6A 179.8(3) . . . . ?

_olex2_submission_special_instructions 'No special instructions were received'
####################################################################### 
# 
# 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_p21n
_database_code_depnum_ccdc_archive 'CCDC 1474555'
_audit_update_record             
;
2016-04-17 deposited with the CCDC.
2016-08-22 downloaded from the CCDC.
;
_audit_creation_date             2015-07-17
_audit_creation_method           
;
Olex2 1.2-alpha
(compiled 2015.07.16 svn.r3196 for OlexSys, GUI svn.r5069)
;
_chemical_name_common            ?
_chemical_name_systematic        
;
 ? 
;
_chemical_formula_moiety         'C19 H20 N O2 Se, C7 H7 O3 S'
_chemical_formula_sum            'C26 H27 N O5 S Se'
_chemical_formula_weight         544.51
_chemical_melting_point          ?
loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
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'

_space_group_crystal_system      monoclinic
_space_group_IT_number           14
_space_group_name_H-M_alt        'P 1 21/n 1'
_space_group_name_Hall           '-P 2yn'
loop_
_space_group_symop_id
_space_group_symop_operation_xyz
1 'x, y, z'
2 '-x+1/2, y+1/2, -z+1/2'
3 '-x, -y, -z'
4 'x-1/2, -y-1/2, z-1/2'

_cell_length_a                   7.5964(7)
_cell_length_b                   29.113(3)
_cell_length_c                   10.9942(9)
_cell_angle_alpha                90.00
_cell_angle_beta                 96.454(4)
_cell_angle_gamma                90.00
_cell_volume                     2416.0(4)
_cell_formula_units_Z            4
_cell_measurement_reflns_used    1374
_cell_measurement_temperature    120(2)
_cell_measurement_theta_max      24.323
_cell_measurement_theta_min      2.788
_exptl_absorpt_coefficient_mu    1.679
_exptl_absorpt_correction_T_max  0.9514
_exptl_absorpt_correction_T_min  0.8636
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   SADABS
_exptl_crystal_colour            light-orange
_exptl_crystal_density_diffrn    1.497
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       prism
_exptl_crystal_F_000             1120
_exptl_crystal_size_max          0.46
_exptl_crystal_size_mid          0.12
_exptl_crystal_size_min          0.08
_exptl_special_details           
;
 ? 
;
_diffrn_reflns_av_R_equivalents  0.1449
_diffrn_reflns_av_unetI/netI     0.2362
_diffrn_reflns_limit_h_max       9
_diffrn_reflns_limit_h_min       -10
_diffrn_reflns_limit_k_max       39
_diffrn_reflns_limit_k_min       -39
_diffrn_reflns_limit_l_max       14
_diffrn_reflns_limit_l_min       -14
_diffrn_reflns_number            19914
_diffrn_reflns_theta_full        29.00
_diffrn_reflns_theta_max         29.00
_diffrn_reflns_theta_min         1.40
_diffrn_ambient_temperature      123.15
_diffrn_detector_area_resol_mean ?
_diffrn_measured_fraction_theta_full 0.997
_diffrn_measured_fraction_theta_max 0.997
_diffrn_measurement_device_type  'CCD SMART-6'
_diffrn_measurement_method       ?
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_source                   'fine-focus sealed tube'
_diffrn_standards_decay_%        ?
_diffrn_standards_interval_count ?
_diffrn_standards_interval_time  ?
_diffrn_standards_number         ?
_reflns_number_gt                2523
_reflns_number_total             6401
_reflns_threshold_expression     >2sigma(I)
_computing_cell_refinement       'SAINT v7.46A (Bruker, 2008)'
_computing_data_collection       ?
_computing_data_reduction        'SAINT v7.46A (Bruker, 2008)'
_computing_molecular_graphics    'Olex2 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 (Dolomanov et al., 2009)'
_computing_structure_refinement  'XL (Sheldrick, 2008)'
_computing_structure_solution    'ShelXS-1997 (Sheldrick, 2008)'
_refine_diff_density_max         0.552
_refine_diff_density_min         -0.481
_refine_diff_density_rms         0.086
_refine_ls_extinction_coef       ?
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   0.724
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     305
_refine_ls_number_reflns         6401
_refine_ls_number_restraints     36
_refine_ls_R_factor_all          0.1764
_refine_ls_R_factor_gt           0.0557
_refine_ls_restrained_S_all      0.794
_refine_ls_shift/su_max          0.001
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details     
'calc w=1/[σ²(Fo²)+(0.0146P)²+0.0000P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0661
_refine_ls_wR_factor_ref         0.0813
_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. 
;
_olex2_refinement_description    
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups, All C(H,H) groups
 At 1.5 times of:
  All C(H,H,H) groups
2. Restrained distances
 O1A-O2A \\sim O1A-O3A \\sim O2A-O3A \\sim O1B-O2B \\sim O1B-O3B \\sim O2B-O3B
 with sigma of 0.04
 S1-O1A \\sim S1-O2A \\sim S1-O3A \\sim S1-O1B \\sim S1-O2B \\sim S1-O3B \\sim
S1-C1A
 with sigma of 0.02
3. Others
 Sof(O1B)=Sof(O2B)=Sof(O3B)=1-FVAR(1)
 Sof(O1A)=Sof(O2A)=Sof(O3A)=FVAR(1)
4.a Ternary CH refined with riding coordinates:
 C2(H2), C3(H3)
4.b Secondary CH2 refined with riding coordinates:
 C18(H18A,H18B)
4.c Me refined with riding coordinates:
 C10(H10A,H10B,H10C), C11(H11A,H11B,H11C), C19(H19A,H19B,H19C), C7A(H7AA,H7AB,
 H7AC)
4.d Aromatic/amide H refined with riding coordinates:
 C5(H5), C8(H8), C9(H9), C14(H14), C15(H15), C16(H16), C17(H17), C2A(H2A),
 C3A(H3A), C5A(H5A), C6A(H6A)
;
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
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_calc_flag
_atom_site_disorder_assembly
_atom_site_disorder_group
_atom_site_refinement_flags_posn
Se1 Se 0.34533(7) 0.075172(16) 0.53394(5) 0.03395(14) Uani 1 d . . .
O1 O 0.0884(4) -0.18240(9) 0.5627(3) 0.0355(9) Uani 1 d . . .
O2 O 0.1739(4) -0.18692(9) 0.7934(3) 0.0395(9) Uani 1 d . . .
N1 N 0.2308(4) 0.05514(11) 0.3024(3) 0.0228(9) Uani 1 d . . .
C1 C 0.2259(6) 0.03816(13) 0.4127(4) 0.0245(11) Uani 1 d . . .
C2 C 0.1148(6) -0.00103(14) 0.4415(4) 0.0325(13) Uani 1 d . . .
H2 H 0.1423 -0.0293 0.3953 0.039 Uiso 1 calc . . R
C3 C 0.1035(7) -0.01146(14) 0.5783(4) 0.0370(14) Uani 1 d . . .
H3 H 0.1684 0.0128 0.6299 0.044 Uiso 1 calc . . R
C4 C 0.1538(6) -0.05833(13) 0.6299(4) 0.0234(11) Uani 1 d . . .
C5 C 0.1120(6) -0.09882(12) 0.5613(4) 0.0220(10) Uani 1 d . . .
H5 H 0.0776 -0.0972 0.4756 0.026 Uiso 1 calc . . R
C6 C 0.1219(6) -0.14071(13) 0.6208(4) 0.0256(11) Uani 1 d . . .
C7 C 0.1745(6) -0.14370(14) 0.7461(4) 0.0283(11) Uani 1 d . . .
C8 C 0.2224(6) -0.10448(14) 0.8113(4) 0.0306(12) Uani 1 d . . .
H8 H 0.2634 -0.1062 0.8960 0.037 Uiso 1 calc . . R
C9 C 0.2104(5) -0.06207(13) 0.7517(4) 0.0261(11) Uani 1 d . . .
H9 H 0.2426 -0.0350 0.7973 0.031 Uiso 1 calc . . R
C10 C 0.0135(7) -0.18156(14) 0.4389(4) 0.0428(14) Uani 1 d . . .
H10A H -0.0043 -0.2131 0.4088 0.064 Uiso 1 calc . . R
H10B H 0.0937 -0.1654 0.3895 0.064 Uiso 1 calc . . R
H10C H -0.1007 -0.1656 0.4325 0.064 Uiso 1 calc . . R
C11 C 0.2042(8) -0.19114(15) 0.9235(4) 0.0522(17) Uani 1 d . . .
H11A H 0.2018 -0.2237 0.9462 0.078 Uiso 1 calc . . R
H11B H 0.1114 -0.1746 0.9607 0.078 Uiso 1 calc . . R
H11C H 0.3201 -0.1781 0.9528 0.078 Uiso 1 calc . . R
C12 C 0.3806(6) 0.11591(14) 0.4066(4) 0.0274(12) Uani 1 d . . .
C13 C 0.3084(6) 0.09883(14) 0.2964(4) 0.0233(11) Uani 1 d . . .
C14 C 0.3043(6) 0.12495(14) 0.1880(5) 0.0329(13) Uani 1 d . . .
H14 H 0.2545 0.1133 0.1110 0.040 Uiso 1 calc . . R
C15 C 0.3768(6) 0.16844(15) 0.2003(5) 0.0405(14) Uani 1 d . . .
H15 H 0.3746 0.1874 0.1298 0.049 Uiso 1 calc . . R
C16 C 0.4529(6) 0.18539(15) 0.3119(5) 0.0397(14) Uani 1 d . . .
H16 H 0.5036 0.2153 0.3157 0.048 Uiso 1 calc . . R
C17 C 0.4562(6) 0.15966(15) 0.4175(5) 0.0374(13) Uani 1 d . . .
H17 H 0.5076 0.1712 0.4942 0.045 Uiso 1 calc . . R
C18 C 0.1699(6) 0.02840(13) 0.1895(4) 0.0262(11) Uani 1 d . . .
H18A H 0.1175 0.0496 0.1249 0.031 Uiso 1 calc . . R
H18B H 0.0771 0.0063 0.2075 0.031 Uiso 1 calc . . R
C19 C 0.3215(6) 0.00285(16) 0.1446(4) 0.0413(14) Uani 1 d . . .
H19A H 0.2788 -0.0145 0.0707 0.062 Uiso 1 calc . . R
H19B H 0.3723 -0.0184 0.2082 0.062 Uiso 1 calc . . R
H19C H 0.4124 0.0248 0.1255 0.062 Uiso 1 calc . . R
S1 S 0.08238(16) 0.08675(3) 0.85085(11) 0.0277(3) Uani 1 d . . D
O1A O -0.024(2) 0.1038(5) 0.9483(13) 0.037(3) Uiso 0.51(6) d A 1 D
O2A O -0.019(2) 0.0850(5) 0.7327(8) 0.030(3) Uiso 0.51(6) d A 1 D
O3A O 0.1733(12) 0.0433(3) 0.884(2) 0.030(3) Uiso 0.51(6) d A 1 D
O1B O 0.013(2) 0.0973(4) 0.9634(10) 0.024(3) Uiso 0.49(6) d A 2 D
O2B O -0.0488(19) 0.0929(5) 0.7419(9) 0.024(3) Uiso 0.49(6) d A 2 D
O3B O 0.1763(12) 0.0425(3) 0.850(2) 0.032(3) Uiso 0.49(6) d A 2 D
C1A C 0.2497(6) 0.12752(13) 0.8381(4) 0.0244(11) Uani 1 d A . D
C2A C 0.4208(6) 0.11465(14) 0.8235(4) 0.0285(12) Uani 1 d . . .
H2A H 0.4509 0.0830 0.8270 0.034 Uiso 1 calc A . R
C3A C 0.5504(6) 0.14662(15) 0.8040(4) 0.0331(12) Uani 1 d A . .
H3A H 0.6671 0.1366 0.7942 0.040 Uiso 1 calc . . R
C4A C 0.5102(7) 0.19304(15) 0.7987(4) 0.0338(13) Uani 1 d . . .
C5A C 0.3400(6) 0.20640(14) 0.8167(4) 0.0294(12) Uani 1 d A . .
H5A H 0.3109 0.2381 0.8155 0.035 Uiso 1 calc . . R
C6A C 0.2120(6) 0.17452(14) 0.8362(4) 0.0291(12) Uani 1 d . . .
H6A H 0.0964 0.1846 0.8486 0.035 Uiso 1 calc A . R
C7A C 0.6460(6) 0.22831(15) 0.7745(5) 0.0463(14) Uani 1 d A . .
H7AA H 0.5934 0.2590 0.7753 0.069 Uiso 1 calc . . R
H7AB H 0.6862 0.2226 0.6942 0.069 Uiso 1 calc . . R
H7AC H 0.7471 0.2264 0.8380 0.069 Uiso 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 1.868(4) . ?
Se1 C12 1.877(5) . ?
O1 C6 1.382(5) . ?
O1 C10 1.415(5) . ?
O2 C7 1.362(4) . ?
O2 C11 1.428(5) . ?
N1 C1 1.314(5) . ?
N1 C13 1.407(5) . ?
N1 C18 1.493(5) . ?
C1 C2 1.474(6) . ?
C2 H2 1.0000 . ?
C2 C3 1.546(6) . ?
C2 C3 1.688(6) 3_556 ?
C3 C2 1.688(6) 3_556 ?
C3 H3 1.0000 . ?
C3 C4 1.511(5) . ?
C4 C5 1.416(5) . ?
C4 C9 1.364(5) . ?
C5 H5 0.9500 . ?
C5 C6 1.382(5) . ?
C6 C7 1.393(6) . ?
C7 C8 1.375(6) . ?
C8 H8 0.9500 . ?
C8 C9 1.396(5) . ?
C9 H9 0.9500 . ?
C10 H10A 0.9800 . ?
C10 H10B 0.9800 . ?
C10 H10C 0.9800 . ?
C11 H11A 0.9800 . ?
C11 H11B 0.9800 . ?
C11 H11C 0.9800 . ?
C12 C13 1.366(6) . ?
C12 C17 1.397(6) . ?
C13 C14 1.411(6) . ?
C14 H14 0.9500 . ?
C14 C15 1.381(6) . ?
C15 H15 0.9500 . ?
C15 C16 1.387(6) . ?
C16 H16 0.9500 . ?
C16 C17 1.379(6) . ?
C17 H17 0.9500 . ?
C18 H18A 0.9900 . ?
C18 H18B 0.9900 . ?
C18 C19 1.500(6) . ?
C19 H19A 0.9800 . ?
C19 H19B 0.9800 . ?
C19 H19C 0.9800 . ?
S1 O1A 1.496(9) . ?
S1 O2A 1.436(7) . ?
S1 O3A 1.468(7) . ?
S1 O1B 1.433(8) . ?
S1 O2B 1.481(8) . ?
S1 O3B 1.474(7) . ?
S1 C1A 1.757(4) . ?
C1A C2A 1.379(6) . ?
C1A C6A 1.398(5) . ?
C2A H2A 0.9500 . ?
C2A C3A 1.389(6) . ?
C3A H3A 0.9500 . ?
C3A C4A 1.385(6) . ?
C4A C5A 1.385(6) . ?
C4A C7A 1.500(6) . ?
C5A H5A 0.9500 . ?
C5A C6A 1.378(6) . ?
C6A H6A 0.9500 . ?
C7A H7AA 0.9800 . ?
C7A H7AB 0.9800 . ?
C7A H7AC 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 C12 86.02(18) . . ?
C6 O1 C10 117.6(3) . . ?
C7 O2 C11 117.1(3) . . ?
C1 N1 C13 116.0(4) . . ?
C1 N1 C18 122.2(4) . . ?
C13 N1 C18 121.7(4) . . ?
N1 C1 Se1 112.3(3) . . ?
N1 C1 C2 124.4(4) . . ?
C2 C1 Se1 122.5(3) . . ?
C1 C2 H2 111.7 . . ?
C1 C2 C3 117.2(4) . . ?
C1 C2 C3 112.6(3) . 3_556 ?
C3 C2 H2 111.7 . . ?
C3 C2 H2 111.7 3_556 . ?
C3 C2 C3 90.3(4) . 3_556 ?
C2 C3 C2 89.7(4) . 3_556 ?
C2 C3 H3 109.6 3_556 . ?
C2 C3 H3 109.6 . . ?
C4 C3 C2 120.2(4) . . ?
C4 C3 C2 116.5(4) . 3_556 ?
C4 C3 H3 109.6 . . ?
C5 C4 C3 121.3(4) . . ?
C9 C4 C3 118.7(4) . . ?
C9 C4 C5 118.9(4) . . ?
C4 C5 H5 120.5 . . ?
C6 C5 C4 119.0(4) . . ?
C6 C5 H5 120.5 . . ?
O1 C6 C5 124.0(4) . . ?
O1 C6 C7 114.8(4) . . ?
C5 C6 C7 121.2(4) . . ?
O2 C7 C6 115.0(4) . . ?
O2 C7 C8 125.5(4) . . ?
C8 C7 C6 119.6(4) . . ?
C7 C8 H8 120.3 . . ?
C7 C8 C9 119.4(4) . . ?
C9 C8 H8 120.3 . . ?
C4 C9 C8 121.9(4) . . ?
C4 C9 H9 119.1 . . ?
C8 C9 H9 119.1 . . ?
O1 C10 H10A 109.5 . . ?
O1 C10 H10B 109.5 . . ?
O1 C10 H10C 109.5 . . ?
H10A C10 H10B 109.5 . . ?
H10A C10 H10C 109.5 . . ?
H10B C10 H10C 109.5 . . ?
O2 C11 H11A 109.5 . . ?
O2 C11 H11B 109.5 . . ?
O2 C11 H11C 109.5 . . ?
H11A C11 H11B 109.5 . . ?
H11A C11 H11C 109.5 . . ?
H11B C11 H11C 109.5 . . ?
C13 C12 Se1 110.8(3) . . ?
C13 C12 C17 121.9(4) . . ?
C17 C12 Se1 127.1(4) . . ?
N1 C13 C14 123.9(4) . . ?
C12 C13 N1 114.6(4) . . ?
C12 C13 C14 121.4(4) . . ?
C13 C14 H14 121.9 . . ?
C15 C14 C13 116.1(4) . . ?
C15 C14 H14 121.9 . . ?
C14 C15 H15 118.8 . . ?
C14 C15 C16 122.3(5) . . ?
C16 C15 H15 118.8 . . ?
C15 C16 H16 119.4 . . ?
C17 C16 C15 121.2(4) . . ?
C17 C16 H16 119.4 . . ?
C12 C17 H17 121.5 . . ?
C16 C17 C12 117.0(5) . . ?
C16 C17 H17 121.5 . . ?
N1 C18 H18A 109.5 . . ?
N1 C18 H18B 109.5 . . ?
N1 C18 C19 110.8(3) . . ?
H18A C18 H18B 108.1 . . ?
C19 C18 H18A 109.5 . . ?
C19 C18 H18B 109.5 . . ?
C18 C19 H19A 109.5 . . ?
C18 C19 H19B 109.5 . . ?
C18 C19 H19C 109.5 . . ?
H19A C19 H19B 109.5 . . ?
H19A C19 H19C 109.5 . . ?
H19B C19 H19C 109.5 . . ?
O1A S1 C1A 106.6(4) . . ?
O2A S1 O1A 112.4(5) . . ?
O2A S1 O3A 112.8(5) . . ?
O2A S1 O2B 13.4(6) . . ?
O2A S1 O3B 100.1(5) . . ?
O2A S1 C1A 105.8(4) . . ?
O3A S1 O1A 112.5(5) . . ?
O3A S1 O2B 124.2(5) . . ?
O3A S1 O3B 14.9(6) . . ?
O3A S1 C1A 106.1(4) . . ?
O1B S1 O1A 13.9(5) . . ?
O1B S1 O2A 125.1(5) . . ?
O1B S1 O3A 100.2(5) . . ?
O1B S1 O2B 113.1(5) . . ?
O1B S1 O3B 114.8(5) . . ?
O1B S1 C1A 105.4(4) . . ?
O2B S1 O1A 99.9(5) . . ?
O2B S1 C1A 106.3(4) . . ?
O3B S1 O1A 126.5(5) . . ?
O3B S1 O2B 112.5(5) . . ?
O3B S1 C1A 103.6(4) . . ?
C2A C1A S1 121.7(3) . . ?
C2A C1A C6A 117.3(4) . . ?
C6A C1A S1 120.9(4) . . ?
C1A C2A H2A 119.0 . . ?
C1A C2A C3A 122.0(4) . . ?
C3A C2A H2A 119.0 . . ?
C2A C3A H3A 119.9 . . ?
C4A C3A C2A 120.2(5) . . ?
C4A C3A H3A 119.9 . . ?
C3A C4A C7A 121.5(5) . . ?
C5A C4A C3A 118.2(4) . . ?
C5A C4A C7A 120.3(4) . . ?
C4A C5A H5A 119.4 . . ?
C6A C5A C4A 121.3(4) . . ?
C6A C5A H5A 119.4 . . ?
C1A C6A H6A 119.5 . . ?
C5A C6A C1A 121.0(4) . . ?
C5A C6A H6A 119.5 . . ?
C4A C7A H7AA 109.5 . . ?
C4A C7A H7AB 109.5 . . ?
C4A C7A H7AC 109.5 . . ?
H7AA C7A H7AB 109.5 . . ?
H7AA C7A H7AC 109.5 . . ?
H7AB C7A H7AC 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
Se1 C1 C2 C3 -1.4(6) . . . . ?
Se1 C1 C2 C3 101.3(4) . . . 3_556 ?
Se1 C12 C13 N1 -1.8(5) . . . . ?
Se1 C12 C13 C14 174.5(3) . . . . ?
Se1 C12 C17 C16 -173.8(3) . . . . ?
O1 C6 C7 O2 -4.0(6) . . . . ?
O1 C6 C7 C8 175.7(4) . . . . ?
O2 C7 C8 C9 -177.6(4) . . . . ?
N1 C1 C2 C3 -67.8(6) . . . 3_556 ?
N1 C1 C2 C3 -170.6(4) . . . . ?
N1 C13 C14 C15 175.8(4) . . . . ?
C1 Se1 C12 C13 -0.9(3) . . . . ?
C1 Se1 C12 C17 174.3(4) . . . . ?
C1 N1 C13 C12 4.9(5) . . . . ?
C1 N1 C13 C14 -171.3(4) . . . . ?
C1 N1 C18 C19 -92.3(5) . . . . ?
C1 C2 C3 C2 115.7(4) . . . 3_556 ?
C1 C2 C3 C4 -123.4(4) . . . . ?
C2 C3 C4 C5 68.5(6) 3_556 . . . ?
C2 C3 C4 C5 -37.9(7) . . . . ?
C2 C3 C4 C9 -99.3(5) 3_556 . . . ?
C2 C3 C4 C9 154.3(4) . . . . ?
C3 C2 C3 C2 0.0 3_556 . . 3_556 ?
C3 C2 C3 C4 120.9(5) 3_556 . . . ?
C3 C4 C5 C6 -164.8(4) . . . . ?
C3 C4 C9 C8 165.9(4) . . . . ?
C4 C5 C6 O1 -178.3(4) . . . . ?
C4 C5 C6 C7 -0.9(7) . . . . ?
C5 C4 C9 C8 -2.2(7) . . . . ?
C5 C6 C7 O2 178.4(4) . . . . ?
C5 C6 C7 C8 -2.0(7) . . . . ?
C6 C7 C8 C9 2.7(7) . . . . ?
C7 C8 C9 C4 -0.6(7) . . . . ?
C9 C4 C5 C6 3.0(7) . . . . ?
C10 O1 C6 C5 -10.1(7) . . . . ?
C10 O1 C6 C7 172.3(4) . . . . ?
C11 O2 C7 C6 -172.0(4) . . . . ?
C11 O2 C7 C8 8.3(7) . . . . ?
C12 Se1 C1 N1 3.6(3) . . . . ?
C12 Se1 C1 C2 -166.8(4) . . . . ?
C12 C13 C14 C15 -0.1(7) . . . . ?
C13 N1 C1 Se1 -5.5(5) . . . . ?
C13 N1 C1 C2 164.6(4) . . . . ?
C13 N1 C18 C19 83.2(5) . . . . ?
C13 C12 C17 C16 0.9(7) . . . . ?
C13 C14 C15 C16 1.3(7) . . . . ?
C14 C15 C16 C17 -1.4(8) . . . . ?
C15 C16 C17 C12 0.3(7) . . . . ?
C17 C12 C13 N1 -177.3(4) . . . . ?
C17 C12 C13 C14 -1.0(7) . . . . ?
C18 N1 C1 Se1 170.2(3) . . . . ?
C18 N1 C1 C2 -19.7(6) . . . . ?
C18 N1 C13 C12 -170.8(4) . . . . ?
C18 N1 C13 C14 13.0(6) . . . . ?
S1 C1A C2A C3A 175.0(3) . . . . ?
S1 C1A C6A C5A -174.9(3) . . . . ?
O1A S1 C1A C2A 138.8(9) . . . . ?
O1A S1 C1A C6A -44.4(9) . . . . ?
O2A S1 C1A C2A -101.4(9) . . . . ?
O2A S1 C1A C6A 75.4(9) . . . . ?
O3A S1 C1A C2A 18.6(10) . . . . ?
O3A S1 C1A C6A -164.5(9) . . . . ?
O1B S1 C1A C2A 124.4(9) . . . . ?
O1B S1 C1A C6A -58.8(9) . . . . ?
O2B S1 C1A C2A -115.3(9) . . . . ?
O2B S1 C1A C6A 61.5(9) . . . . ?
O3B S1 C1A C2A 3.5(10) . . . . ?
O3B S1 C1A C6A -179.7(10) . . . . ?
C1A C2A C3A C4A 0.1(7) . . . . ?
C2A C1A C6A C5A 2.0(6) . . . . ?
C2A C3A C4A C5A 1.7(7) . . . . ?
C2A C3A C4A C7A -178.4(4) . . . . ?
C3A C4A C5A C6A -1.6(7) . . . . ?
C4A C5A C6A C1A -0.3(7) . . . . ?
C6A C1A C2A C3A -1.9(6) . . . . ?
C7A C4A C5A C6A 178.5(4) . . . . ?

_olex2_submission_special_instructions 'No special instructions were received'
####################################################################### 
# 
# 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_p-1
_database_code_depnum_ccdc_archive 'CCDC 1474556'
_audit_update_record             
;
2016-04-17 deposited with the CCDC.
2016-08-22 downloaded from the CCDC.
;
_audit_creation_date             2015-07-17
_audit_creation_method           
;
Olex2 1.2-alpha
(compiled 2015.07.16 svn.r3196 for OlexSys, GUI svn.r5069)
;
_chemical_name_common            ?
_chemical_name_systematic        
;
 ? 
;
_chemical_formula_moiety         'C19 H20 N O2 Se, C7 H7 O3 S, C3 H3 O, H2 O'
_chemical_formula_sum            'C29 H32 N O7 S Se'
_chemical_formula_weight         617.58
_chemical_melting_point          ?
loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
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'

_space_group_crystal_system      triclinic
_space_group_IT_number           2
_space_group_name_H-M_alt        'P -1'
_space_group_name_Hall           '-P 1'
loop_
_space_group_symop_id
_space_group_symop_operation_xyz
1 'x, y, z'
2 '-x, -y, -z'

_cell_length_a                   7.2675(2)
_cell_length_b                   12.9365(6)
_cell_length_c                   15.3429(6)
_cell_angle_alpha                108.909(4)
_cell_angle_beta                 92.576(3)
_cell_angle_gamma                96.008(3)
_cell_volume                     1352.36(9)
_cell_formula_units_Z            2
_cell_measurement_reflns_used    7162
_cell_measurement_temperature    153.15
_cell_measurement_theta_max      32.4506
_cell_measurement_theta_min      2.7549
_exptl_absorpt_coefficient_mu    1.515
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.83885
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   ?
_exptl_crystal_colour            orange
_exptl_crystal_colour_primary    orange
_exptl_crystal_density_diffrn    1.517
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       prism
_exptl_crystal_F_000             638
_exptl_crystal_size_max          0.44
_exptl_crystal_size_mid          0.42
_exptl_crystal_size_min          0.14
_exptl_special_details           
;
CrysAlisPro, Agilent Technologies,
Version 1.171.35.15 (release 03-08-2011 CrysAlis171 .NET)
(compiled Aug  3 2011,13:03:54)
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm. 
;
_diffrn_reflns_av_R_equivalents  0.0692
_diffrn_reflns_av_unetI/netI     0.0638
_diffrn_reflns_limit_h_max       9
_diffrn_reflns_limit_h_min       -9
_diffrn_reflns_limit_k_max       16
_diffrn_reflns_limit_k_min       -16
_diffrn_reflns_limit_l_max       19
_diffrn_reflns_limit_l_min       -19
_diffrn_reflns_number            24708
_diffrn_reflns_theta_full        27.50
_diffrn_reflns_theta_max         27.50
_diffrn_reflns_theta_min         2.76
_diffrn_ambient_temperature      153.15
_diffrn_detector_area_resol_mean ?
_diffrn_measured_fraction_theta_full 0.999
_diffrn_measured_fraction_theta_max 0.999
_diffrn_measurement_device_type  'multiwire proportional'
_diffrn_measurement_method       'phi and omega scans'
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_source                   'fine-focus sealed tube'
_diffrn_standards_decay_%        ?
_diffrn_standards_interval_count ?
_diffrn_standards_interval_time  ?
_diffrn_standards_number         ?
_reflns_number_gt                5222
_reflns_number_total             6214
_reflns_threshold_expression     >2sigma(I)
_computing_cell_refinement       ?
_computing_data_collection       ?
_computing_data_reduction        ?
_computing_molecular_graphics    'Olex2 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 (Dolomanov et al., 2009)'
_computing_structure_refinement  'XL (Sheldrick, 2008)'
_computing_structure_solution    'ShelXS-1997 (Sheldrick, 2008)'
_refine_diff_density_max         1.436
_refine_diff_density_min         -1.700
_refine_diff_density_rms         0.097
_refine_ls_extinction_coef       ?
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.097
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     368
_refine_ls_number_reflns         6214
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0687
_refine_ls_R_factor_gt           0.0535
_refine_ls_restrained_S_all      1.097
_refine_ls_shift/su_max          0.001
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details     
'calc w=1/[σ²(Fo²)+(0.0287P)²+2.1371P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1073
_refine_ls_wR_factor_ref         0.1140
_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. 
;
_olex2_refinement_description    
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups, All C(H,H) groups
 At 1.5 times of:
  All C(H,H,H) groups
2. Others
 Fixed Sof: C1(0.75) C2(0.75) H2(0.75) C3(0.75) H3(0.75) C4(0.75) C1'(0.25)
 C2'(0.25) H2'(0.25) C3'(0.25) H3'(0.25) C4'(0.25) H5A(0.75) H5B(0.25)
 H9A(0.75) H9B(0.25)
3.a Everything fixed:
 H3B, H2B, H1B, H1WA, H1WB
3.b Ternary CH refined with riding coordinates:
 C2'(H2'), C3'(H3')
3.c Secondary CH2 refined with riding coordinates:
 C18(H18A,H18B)
3.d Me refined with riding coordinates:
 C10(H10A,H10B,H10C), C11(H11A,H11B,H11C), C19(H19A,H19B,H19C), C7A(H7AA,H7AB,
 H7AC)
3.e Aromatic/amide H refined with riding coordinates:
 C2(H2), C3(H3), C5(H5A), C5(H5B), C8(H8), C9(H9A), C9(H9B), C14(H14),
 C15(H15), C16(H16), C17(H17), C2A(H2A), C3A(H3A), C5A(H5AA), C6A(H6A)
;
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
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_calc_flag
_atom_site_disorder_assembly
_atom_site_disorder_group
_atom_site_refinement_flags_posn
Se1 Se 0.17768(5) 0.20264(3) 0.00532(2) 0.02481(11) Uani 1 d . . .
O1 O 0.3792(4) -0.3877(2) 0.02936(16) 0.0307(6) Uani 1 d . . .
O2 O 0.4039(4) -0.3369(2) 0.20502(17) 0.0383(7) Uani 1 d . . .
N1 N 0.2022(4) 0.0514(2) -0.16157(17) 0.0223(6) Uani 1 d . . .
C1 C 0.2115(9) 0.0670(5) -0.0705(4) 0.0145(11) Uani 0.75 d A 1 .
C2 C 0.2536(6) -0.0206(3) -0.0371(3) 0.0193(8) Uani 0.75 d A 1 .
H2 H 0.2667 -0.0903 -0.0806 0.023 Uiso 0.75 calc A 1 R
C3 C 0.2751(5) -0.0072(3) 0.0532(3) 0.0182(8) Uani 0.75 d A 1 .
H3 H 0.2630 0.0634 0.0956 0.022 Uiso 0.75 calc A 1 R
C4 C 0.3154(12) -0.0925(7) 0.0913(6) 0.0181(14) Uani 0.75 d A 1 .
C1' C 0.261(3) 0.0568(19) -0.0743(15) 0.018(5) Uiso 0.25 d A 2 .
C2' C 0.3723(18) -0.0200(10) -0.0459(8) 0.017(2) Uiso 0.25 d . 2 .
H2' H 0.3206 -0.0985 -0.0791 0.021 Uiso 0.25 calc . 2 R
C3' C 0.4155(17) 0.0002(10) 0.0579(8) 0.018(2) Uiso 0.25 d . 2 .
H3' H 0.3717 0.0707 0.0954 0.022 Uiso 0.25 calc . 2 R
C4' C 0.358(4) -0.091(3) 0.098(2) 0.024(8) Uiso 0.25 d A 2 .
C5 C 0.3390(4) -0.2007(2) 0.0368(2) 0.0179(6) Uani 1 d . . .
H5A H 0.3377 -0.2190 -0.0284 0.021 Uiso 0.75 calc A 1 R
H5B H 0.3109 -0.2185 -0.0278 0.021 Uiso 0.25 calc A 2 R
C6 C 0.3638(4) -0.2801(3) 0.0764(2) 0.0214(7) Uani 1 d A . .
C7 C 0.3765(5) -0.2519(3) 0.1737(2) 0.0234(7) Uani 1 d . . .
C8 C 0.3603(4) -0.1458(3) 0.2290(2) 0.0243(7) Uani 1 d A . .
H8 H 0.3660 -0.1276 0.2943 0.029 Uiso 1 calc . . R
C9 C 0.3354(4) -0.0656(3) 0.1884(2) 0.0230(7) Uani 1 d . . .
H9A H 0.3319 0.0083 0.2267 0.028 Uiso 0.75 calc A 1 R
H9B H 0.3037 0.0044 0.2236 0.028 Uiso 0.25 calc A 2 R
C10 C 0.3642(5) -0.4200(3) -0.0697(2) 0.0282(8) Uani 1 d . . .
H10A H 0.3774 -0.4984 -0.0960 0.042 Uiso 1 calc . . R
H10B H 0.4624 -0.3767 -0.0895 0.042 Uiso 1 calc . . R
H10C H 0.2427 -0.4069 -0.0913 0.042 Uiso 1 calc . . R
C11 C 0.4142(6) -0.3147(4) 0.3022(2) 0.0388(9) Uani 1 d . . .
H11A H 0.4340 -0.3819 0.3157 0.058 Uiso 1 calc A . R
H11B H 0.2979 -0.2898 0.3261 0.058 Uiso 1 calc . . R
H11C H 0.5178 -0.2572 0.3318 0.058 Uiso 1 calc . . R
C12 C 0.1316(4) 0.2339(3) -0.1043(2) 0.0211(6) Uani 1 d A . .
C13 C 0.1533(4) 0.1443(3) -0.1814(2) 0.0210(7) Uani 1 d A . .
C14 C 0.1303(5) 0.1519(3) -0.2703(2) 0.0272(7) Uani 1 d . . .
H14 H 0.1437 0.0911 -0.3236 0.033 Uiso 1 calc A . R
C15 C 0.0876(5) 0.2501(3) -0.2784(2) 0.0299(8) Uani 1 d A . .
H15 H 0.0724 0.2569 -0.3381 0.036 Uiso 1 calc . . R
C16 C 0.0663(5) 0.3394(3) -0.2006(3) 0.0317(8) Uani 1 d . . .
H16 H 0.0375 0.4061 -0.2081 0.038 Uiso 1 calc A . R
C17 C 0.0864(4) 0.3325(3) -0.1131(2) 0.0268(7) Uani 1 d A . .
H17 H 0.0700 0.3931 -0.0603 0.032 Uiso 1 calc . . R
C18 C 0.2280(5) -0.0502(3) -0.2350(2) 0.0273(7) Uani 1 d A . .
H18A H 0.3223 -0.0877 -0.2126 0.033 Uiso 1 calc . . R
H18B H 0.2738 -0.0321 -0.2888 0.033 Uiso 1 calc . . R
C19 C 0.0470(6) -0.1265(3) -0.2645(3) 0.0419(10) Uani 1 d . . .
H19A H 0.0671 -0.1940 -0.3136 0.063 Uiso 1 calc A . R
H19B H -0.0457 -0.0898 -0.2876 0.063 Uiso 1 calc . . R
H19C H 0.0025 -0.1452 -0.2114 0.063 Uiso 1 calc . . R
S1A S -0.53355(11) 0.29412(7) 0.26705(5) 0.02283(18) Uani 1 d . . .
O1A O -0.4616(3) 0.2299(2) 0.18231(15) 0.0293(5) Uani 1 d . . .
O2A O -0.6960(3) 0.3440(2) 0.25130(18) 0.0348(6) Uani 1 d . . .
O3A O -0.5608(4) 0.2337(2) 0.33175(17) 0.0359(6) Uani 1 d . . .
C1A C -0.3570(4) 0.4048(3) 0.3239(2) 0.0208(6) Uani 1 d . . .
C2A C -0.3993(5) 0.4910(3) 0.3990(2) 0.0248(7) Uani 1 d . . .
H2A H -0.5234 0.4929 0.4159 0.030 Uiso 1 calc . . R
C3A C -0.2610(5) 0.5743(3) 0.4495(2) 0.0274(7) Uani 1 d . . .
H3A H -0.2915 0.6328 0.5006 0.033 Uiso 1 calc . . R
C4A C -0.0785(5) 0.5729(3) 0.4258(2) 0.0253(7) Uani 1 d . . .
C5A C -0.0378(5) 0.4872(3) 0.3495(2) 0.0257(7) Uani 1 d . . .
H5AA H 0.0861 0.4856 0.3322 0.031 Uiso 1 calc . . R
C6A C -0.1762(5) 0.4040(3) 0.2982(2) 0.0233(7) Uani 1 d . . .
H6A H -0.1469 0.3468 0.2458 0.028 Uiso 1 calc . . R
C7A C 0.0725(5) 0.6606(3) 0.4828(2) 0.0346(9) Uani 1 d . . .
H7AA H 0.0270 0.7326 0.4992 0.052 Uiso 1 calc . . R
H7AB H 0.1806 0.6611 0.4469 0.052 Uiso 1 calc . . R
H7AC H 0.1081 0.6452 0.5392 0.052 Uiso 1 calc . . R
O1B O -0.7388(4) 0.1134(2) 0.43055(19) 0.0398(7) Uani 1 d . . .
C1B C -0.6177(5) 0.0584(3) 0.4646(2) 0.0268(7) Uani 1 d . . .
C2B C -0.6912(5) -0.0248(3) 0.4966(2) 0.0286(8) Uani 1 d . . .
C3B C -0.5736(5) -0.0828(3) 0.5322(2) 0.0280(7) Uani 1 d . . .
O1W O -0.8353(4) 0.4351(2) 0.11785(18) 0.0366(6) Uani 1 d . . .
H3B H -0.6168 -0.1441 0.5539 0.050 Uiso 1 d . . .
H2B H -0.8273 -0.0449 0.4844 0.050 Uiso 1 d . . .
H1B H -0.6773 0.1623 0.3956 0.050 Uiso 1 d . . .
H1WA H -0.7799 0.4031 0.1607 0.050 Uiso 1 d . . .
H1WB H -0.7447 0.5007 0.1228 0.050 Uiso 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 1.813(6) . ?
Se1 C1' 2.06(2) . ?
Se1 C12 1.877(3) . ?
O1 C6 1.363(4) . ?
O1 C10 1.435(4) . ?
O2 C7 1.364(4) . ?
O2 C11 1.421(4) . ?
N1 C1 1.343(6) . ?
N1 C1' 1.36(2) . ?
N1 C13 1.408(4) . ?
N1 C18 1.463(4) . ?
C1 C2 1.441(7) . ?
C2 H2 0.9500 . ?
C2 C3 1.338(6) . ?
C3 H3 0.9500 . ?
C3 C4 1.455(9) . ?
C4 C5 1.411(9) . ?
C4 C9 1.413(9) . ?
C1' C2' 1.50(2) . ?
C2' H2' 1.0000 . ?
C2' C3' 1.565(18) 2_655 ?
C2' C3' 1.541(16) . ?
C3' C2' 1.565(18) 2_655 ?
C3' H3' 1.0000 . ?
C3' C4' 1.53(4) . ?
C4' C5 1.42(3) . ?
C4' C9 1.34(3) . ?
C5 H5A 0.9500 . ?
C5 H5B 0.9500 . ?
C5 C6 1.375(4) . ?
C6 C7 1.414(4) . ?
C7 C8 1.379(5) . ?
C8 H8 0.9500 . ?
C8 C9 1.395(5) . ?
C9 H9A 0.9500 . ?
C9 H9B 0.9500 . ?
C10 H10A 0.9800 . ?
C10 H10B 0.9800 . ?
C10 H10C 0.9800 . ?
C11 H11A 0.9800 . ?
C11 H11B 0.9800 . ?
C11 H11C 0.9800 . ?
C12 C13 1.391(4) . ?
C12 C17 1.396(5) . ?
C13 C14 1.403(4) . ?
C14 H14 0.9500 . ?
C14 C15 1.381(5) . ?
C15 H15 0.9500 . ?
C15 C16 1.394(5) . ?
C16 H16 0.9500 . ?
C16 C17 1.376(5) . ?
C17 H17 0.9500 . ?
C18 H18A 0.9900 . ?
C18 H18B 0.9900 . ?
C18 C19 1.515(5) . ?
C19 H19A 0.9800 . ?
C19 H19B 0.9800 . ?
C19 H19C 0.9800 . ?
S1A O1A 1.451(2) . ?
S1A O2A 1.450(2) . ?
S1A O3A 1.457(3) . ?
S1A C1A 1.779(3) . ?
C1A C2A 1.391(4) . ?
C1A C6A 1.390(4) . ?
C2A H2A 0.9500 . ?
C2A C3A 1.391(5) . ?
C3A H3A 0.9500 . ?
C3A C4A 1.391(5) . ?
C4A C5A 1.395(5) . ?
C4A C7A 1.505(5) . ?
C5A H5AA 0.9500 . ?
C5A C6A 1.394(5) . ?
C6A H6A 0.9500 . ?
C7A H7AA 0.9800 . ?
C7A H7AB 0.9800 . ?
C7A H7AC 0.9800 . ?
O1B C1B 1.372(4) . ?
O1B H1B 1.0348 . ?
C1B C2B 1.391(5) . ?
C1B C3B 1.389(5) 2_456 ?
C2B C3B 1.395(5) . ?
C2B H2B 0.9892 . ?
C3B C1B 1.389(5) 2_456 ?
C3B H3B 0.9834 . ?
O1W H1WA 0.9761 . ?
O1W H1WB 0.9984 . ?

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 C1' 9.2(6) . . ?
C1 Se1 C12 85.1(2) . . ?
C12 Se1 C1' 87.7(6) . . ?
C6 O1 C10 116.6(3) . . ?
C7 O2 C11 117.3(3) . . ?
C1 N1 C1' 16.7(8) . . ?
C1 N1 C13 112.0(3) . . ?
C1 N1 C18 126.2(3) . . ?
C1' N1 C13 121.8(10) . . ?
C1' N1 C18 115.5(9) . . ?
C13 N1 C18 121.7(3) . . ?
N1 C1 Se1 116.8(4) . . ?
N1 C1 C2 120.0(5) . . ?
C2 C1 Se1 123.1(4) . . ?
C1 C2 H2 118.8 . . ?
C3 C2 C1 122.4(4) . . ?
C3 C2 H2 118.8 . . ?
C2 C3 H3 117.5 . . ?
C2 C3 C4 125.0(5) . . ?
C4 C3 H3 117.5 . . ?
C5 C4 C3 123.8(6) . . ?
C5 C4 C9 117.8(6) . . ?
C9 C4 C3 118.4(6) . . ?
N1 C1' Se1 102.3(11) . . ?
N1 C1' C2' 128.0(16) . . ?
C2' C1' Se1 129.5(14) . . ?
C1' C2' H2' 110.9 . . ?
C1' C2' C3' 118.7(13) . . ?
C1' C2' C3' 113.5(12) . 2_655 ?
C3' C2' H2' 110.9 . . ?
C3' C2' H2' 110.9 2_655 . ?
C3' C2' C3' 90.4(9) . 2_655 ?
C2' C3' C2' 89.6(9) . 2_655 ?
C2' C3' H3' 110.1 . . ?
C2' C3' H3' 110.1 2_655 . ?
C4' C3' C2' 119.9(15) . . ?
C4' C3' C2' 115.4(13) . 2_655 ?
C4' C3' H3' 110.1 . . ?
C5 C4' C3' 117(2) . . ?
C9 C4' C3' 120(2) . . ?
C9 C4' C5 123(3) . . ?
C4 C5 C4' 12.9(12) . . ?
C4 C5 H5A 119.4 . . ?
C4 C5 H5B 115.5 . . ?
C4' C5 H5A 123.2 . . ?
C4' C5 H5B 122.0 . . ?
H5A C5 H5B 11.9 . . ?
C6 C5 C4 121.2(4) . . ?
C6 C5 C4' 115.9(13) . . ?
C6 C5 H5A 119.4 . . ?
C6 C5 H5B 122.0 . . ?
O1 C6 C5 125.4(3) . . ?
O1 C6 C7 114.9(3) . . ?
C5 C6 C7 119.7(3) . . ?
O2 C7 C6 114.4(3) . . ?
O2 C7 C8 125.2(3) . . ?
C8 C7 C6 120.4(3) . . ?
C7 C8 H8 120.2 . . ?
C7 C8 C9 119.6(3) . . ?
C9 C8 H8 120.2 . . ?
C4 C9 H9A 119.5 . . ?
C4 C9 H9B 116.3 . . ?
C4' C9 C4 12.9(13) . . ?
C4' C9 C8 117.5(15) . . ?
C4' C9 H9A 121.4 . . ?
C4' C9 H9B 121.2 . . ?
C8 C9 C4 121.0(4) . . ?
C8 C9 H9A 119.5 . . ?
C8 C9 H9B 121.2 . . ?
H9A C9 H9B 12.4 . . ?
O1 C10 H10A 109.5 . . ?
O1 C10 H10B 109.5 . . ?
O1 C10 H10C 109.5 . . ?
H10A C10 H10B 109.5 . . ?
H10A C10 H10C 109.5 . . ?
H10B C10 H10C 109.5 . . ?
O2 C11 H11A 109.5 . . ?
O2 C11 H11B 109.5 . . ?
O2 C11 H11C 109.5 . . ?
H11A C11 H11B 109.5 . . ?
H11A C11 H11C 109.5 . . ?
H11B C11 H11C 109.5 . . ?
C13 C12 Se1 111.1(2) . . ?
C13 C12 C17 121.3(3) . . ?
C17 C12 Se1 127.6(2) . . ?
C12 C13 N1 114.8(3) . . ?
C12 C13 C14 120.1(3) . . ?
C14 C13 N1 125.1(3) . . ?
C13 C14 H14 120.9 . . ?
C15 C14 C13 118.3(3) . . ?
C15 C14 H14 120.9 . . ?
C14 C15 H15 119.4 . . ?
C14 C15 C16 121.1(3) . . ?
C16 C15 H15 119.4 . . ?
C15 C16 H16 119.4 . . ?
C17 C16 C15 121.1(3) . . ?
C17 C16 H16 119.4 . . ?
C12 C17 H17 121.0 . . ?
C16 C17 C12 118.1(3) . . ?
C16 C17 H17 121.0 . . ?
N1 C18 H18A 109.5 . . ?
N1 C18 H18B 109.5 . . ?
N1 C18 C19 110.7(3) . . ?
H18A C18 H18B 108.1 . . ?
C19 C18 H18A 109.5 . . ?
C19 C18 H18B 109.5 . . ?
C18 C19 H19A 109.5 . . ?
C18 C19 H19B 109.5 . . ?
C18 C19 H19C 109.5 . . ?
H19A C19 H19B 109.5 . . ?
H19A C19 H19C 109.5 . . ?
H19B C19 H19C 109.5 . . ?
O1A S1A O3A 112.72(16) . . ?
O1A S1A C1A 106.38(15) . . ?
O2A S1A O1A 113.32(15) . . ?
O2A S1A O3A 112.62(16) . . ?
O2A S1A C1A 106.21(15) . . ?
O3A S1A C1A 104.78(15) . . ?
C2A C1A S1A 119.0(3) . . ?
C6A C1A S1A 121.4(2) . . ?
C6A C1A C2A 119.5(3) . . ?
C1A C2A H2A 119.8 . . ?
C3A C2A C1A 120.4(3) . . ?
C3A C2A H2A 119.8 . . ?
C2A C3A H3A 119.7 . . ?
C2A C3A C4A 120.6(3) . . ?
C4A C3A H3A 119.7 . . ?
C3A C4A C5A 118.6(3) . . ?
C3A C4A C7A 120.6(3) . . ?
C5A C4A C7A 120.7(3) . . ?
C4A C5A H5AA 119.5 . . ?
C6A C5A C4A 120.9(3) . . ?
C6A C5A H5AA 119.5 . . ?
C1A C6A C5A 119.9(3) . . ?
C1A C6A H6A 120.1 . . ?
C5A C6A H6A 120.1 . . ?
C4A C7A H7AA 109.5 . . ?
C4A C7A H7AB 109.5 . . ?
C4A C7A H7AC 109.5 . . ?
H7AA C7A H7AB 109.5 . . ?
H7AA C7A H7AC 109.5 . . ?
H7AB C7A H7AC 109.5 . . ?
C1B O1B H1B 114.2 . . ?
O1B C1B C2B 118.2(3) . . ?
O1B C1B C3B 122.5(3) . 2_456 ?
C3B C1B C2B 119.3(3) 2_456 . ?
C1B C2B C3B 120.3(3) . . ?
C1B C2B H2B 115.0 . . ?
C3B C2B H2B 124.2 . . ?
C1B C3B C2B 120.4(3) 2_456 . ?
C1B C3B H3B 115.4 2_456 . ?
C2B C3B H3B 124.2 . . ?
H1WA O1W H1WB 103.9 . . ?

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
Se1 C1 C2 C3 -1.5(7) . . . . ?
Se1 C1' C2' C3' 9(2) . . . . ?
Se1 C1' C2' C3' -95.7(17) . . . 2_655 ?
Se1 C12 C13 N1 0.6(3) . . . . ?
Se1 C12 C13 C14 -178.2(2) . . . . ?
Se1 C12 C17 C16 177.1(3) . . . . ?
O1 C6 C7 O2 0.6(4) . . . . ?
O1 C6 C7 C8 -179.0(3) . . . . ?
O2 C7 C8 C9 179.0(3) . . . . ?
N1 C1 C2 C3 176.0(4) . . . . ?
N1 C1' C2' C3' 78(2) . . . 2_655 ?
N1 C1' C2' C3' -177.5(15) . . . . ?
N1 C13 C14 C15 -178.1(3) . . . . ?
C1 Se1 C1' N1 62(4) . . . . ?
C1 Se1 C1' C2' -123(6) . . . . ?
C1 Se1 C12 C13 -2.3(3) . . . . ?
C1 Se1 C12 C17 179.5(4) . . . . ?
C1 N1 C1' Se1 -41(3) . . . . ?
C1 N1 C1' C2' 143(6) . . . . ?
C1 N1 C13 C12 2.3(5) . . . . ?
C1 N1 C13 C14 -179.0(4) . . . . ?
C1 N1 C18 C19 86.3(5) . . . . ?
C1 C2 C3 C4 179.2(6) . . . . ?
C2 C3 C4 C5 0.7(10) . . . . ?
C2 C3 C4 C9 179.6(5) . . . . ?
C3 C4 C5 C4' 115(8) . . . . ?
C3 C4 C5 C6 -175.3(5) . . . . ?
C3 C4 C9 C4' -107(8) . . . . ?
C3 C4 C9 C8 175.2(5) . . . . ?
C4 C5 C6 O1 176.8(5) . . . . ?
C4 C5 C6 C7 -3.6(6) . . . . ?
C1' Se1 C1 N1 -102(5) . . . . ?
C1' Se1 C1 C2 76(5) . . . . ?
C1' Se1 C12 C13 6.6(6) . . . . ?
C1' Se1 C12 C17 -171.6(6) . . . . ?
C1' N1 C1 Se1 125(4) . . . . ?
C1' N1 C1 C2 -53(4) . . . . ?
C1' N1 C13 C12 -13.0(10) . . . . ?
C1' N1 C13 C14 165.7(10) . . . . ?
C1' N1 C18 C19 101.3(10) . . . . ?
C1' C2' C3' C2' -117.3(15) . . . 2_655 ?
C1' C2' C3' C4' 123.3(18) . . . . ?
C2' C3' C4' C5 26(2) . . . . ?
C2' C3' C4' C5 -80(2) 2_655 . . . ?
C2' C3' C4' C9 -157.2(16) . . . . ?
C2' C3' C4' C9 97(2) 2_655 . . . ?
C3' C2' C3' C2' 0.0 2_655 . . 2_655 ?
C3' C2' C3' C4' -119.4(17) 2_655 . . . ?
C3' C4' C5 C4 -89(7) . . . . ?
C3' C4' C5 C6 154.0(13) . . . . ?
C3' C4' C9 C4 97(8) . . . . ?
C3' C4' C9 C8 -153.7(14) . . . . ?
C4' C5 C6 O1 -169.7(13) . . . . ?
C4' C5 C6 C7 9.9(13) . . . . ?
C5 C4 C9 C4' 72(8) . . . . ?
C5 C4 C9 C8 -5.9(9) . . . . ?
C5 C4' C9 C4 -86(8) . . . . ?
C5 C4' C9 C8 23(2) . . . . ?
C5 C6 C7 O2 -179.0(3) . . . . ?
C5 C6 C7 C8 1.4(5) . . . . ?
C6 C7 C8 C9 -1.5(5) . . . . ?
C7 C8 C9 C4 3.8(6) . . . . ?
C7 C8 C9 C4' -10.4(14) . . . . ?
C9 C4 C5 C4' -64(7) . . . . ?
C9 C4 C5 C6 5.8(9) . . . . ?
C9 C4' C5 C4 94(8) . . . . ?
C9 C4' C5 C6 -23(2) . . . . ?
C10 O1 C6 C5 -1.3(5) . . . . ?
C10 O1 C6 C7 179.1(3) . . . . ?
C11 O2 C7 C6 -178.7(3) . . . . ?
C11 O2 C7 C8 0.8(5) . . . . ?
C12 Se1 C1 N1 3.8(4) . . . . ?
C12 Se1 C1 C2 -178.5(5) . . . . ?
C12 Se1 C1' N1 -12.0(10) . . . . ?
C12 Se1 C1' C2' 163.0(17) . . . . ?
C12 C13 C14 C15 0.6(5) . . . . ?
C13 N1 C1 Se1 -4.3(5) . . . . ?
C13 N1 C1 C2 178.0(4) . . . . ?
C13 N1 C1' Se1 16.4(13) . . . . ?
C13 N1 C1' C2' -158.7(15) . . . . ?
C13 N1 C18 C19 -90.2(4) . . . . ?
C13 C12 C17 C16 -0.9(5) . . . . ?
C13 C14 C15 C16 -0.5(5) . . . . ?
C14 C15 C16 C17 -0.3(6) . . . . ?
C15 C16 C17 C12 1.0(5) . . . . ?
C17 C12 C13 N1 178.9(3) . . . . ?
C17 C12 C13 C14 0.1(5) . . . . ?
C18 N1 C1 Se1 178.9(3) . . . . ?
C18 N1 C1 C2 1.2(7) . . . . ?
C18 N1 C1' Se1 -175.0(4) . . . . ?
C18 N1 C1' C2' 10(2) . . . . ?
C18 N1 C13 C12 179.2(3) . . . . ?
C18 N1 C13 C14 -2.1(5) . . . . ?
S1A C1A C2A C3A 174.9(3) . . . . ?
S1A C1A C6A C5A -174.3(2) . . . . ?
O1A S1A C1A C2A 168.7(2) . . . . ?
O1A S1A C1A C6A -14.8(3) . . . . ?
O2A S1A C1A C2A 47.7(3) . . . . ?
O2A S1A C1A C6A -135.8(3) . . . . ?
O3A S1A C1A C2A -71.7(3) . . . . ?
O3A S1A C1A C6A 104.8(3) . . . . ?
C1A C2A C3A C4A 0.0(5) . . . . ?
C2A C1A C6A C5A 2.1(5) . . . . ?
C2A C3A C4A C5A 1.2(5) . . . . ?
C2A C3A C4A C7A -177.5(3) . . . . ?
C3A C4A C5A C6A -0.6(5) . . . . ?
C4A C5A C6A C1A -1.0(5) . . . . ?
C6A C1A C2A C3A -1.6(5) . . . . ?
C7A C4A C5A C6A 178.1(3) . . . . ?
O1B C1B C2B C3B -179.8(3) . . . . ?
C1B C2B C3B C1B -0.3(6) . . . 2_456 ?
C3B C1B C2B C3B 0.3(6) 2_456 . . . ?

_olex2_submission_special_instructions 'No special instructions were received'
####################################################################### 
# 
# 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_se
_database_code_depnum_ccdc_archive 'CCDC 1474558'
_audit_update_record             
;
2016-04-17 deposited with the CCDC.
2016-08-22 downloaded from the CCDC.
;
_audit_creation_date             2015-10-14
_audit_creation_method           
;
Olex2 1.2
(compiled 2015.09.30 svn.r3233 for OlexSys, GUI svn.r5103)
;
_chemical_name_common            ?
_chemical_name_systematic        
;
 ? 
;
_chemical_formula_moiety         'C19 H20 N O2 Se, C7 H7 O3 S, C3 H3 O, H2 O'
_chemical_formula_sum            'C29 H32 N O7 S Se'
_chemical_formula_weight         617.58
_chemical_melting_point          ?
loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
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'

_space_group_crystal_system      triclinic
_space_group_IT_number           2
_space_group_name_H-M_alt        'P -1'
_space_group_name_Hall           '-P 1'
loop_
_space_group_symop_id
_space_group_symop_operation_xyz
1 'x, y, z'
2 '-x, -y, -z'

_cell_length_a                   7.2613(3)
_cell_length_b                   12.9355(7)
_cell_length_c                   15.3053(9)
_cell_angle_alpha                109.055(5)
_cell_angle_beta                 92.175(4)
_cell_angle_gamma                96.618(4)
_cell_volume                     1345.40(12)
_cell_formula_units_Z            2
_cell_measurement_reflns_used    5432
_cell_measurement_temperature    120.15
_cell_measurement_theta_max      2.6
_cell_measurement_theta_min      28.0
_exptl_absorpt_coefficient_mu    1.523
_exptl_absorpt_correction_T_max  1.0000
_exptl_absorpt_correction_T_min  0.8444
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   ?
_exptl_crystal_colour            orange
_exptl_crystal_colour_primary    orange
_exptl_crystal_density_diffrn    1.524
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       block
_exptl_crystal_F_000             638
_exptl_crystal_size_max          0.44
_exptl_crystal_size_mid          0.42
_exptl_crystal_size_min          0.14
_exptl_special_details           
;
 ? 
;
_diffrn_reflns_av_R_equivalents  0.0459
_diffrn_reflns_av_unetI/netI     0.0669
_diffrn_reflns_limit_h_max       9
_diffrn_reflns_limit_h_min       -9
_diffrn_reflns_limit_k_max       16
_diffrn_reflns_limit_k_min       -16
_diffrn_reflns_limit_l_max       19
_diffrn_reflns_limit_l_min       -20
_diffrn_reflns_number            11984
_diffrn_reflns_theta_full        28.00
_diffrn_reflns_theta_max         28.00
_diffrn_reflns_theta_min         2.53
_diffrn_ambient_temperature      120.15
_diffrn_detector_area_resol_mean ?
_diffrn_measured_fraction_theta_full 0.936
_diffrn_measured_fraction_theta_max 0.936
_diffrn_measurement_device_type  'CCD Bruker-8 Venture'
_diffrn_measurement_method       ?
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_source                   'fine-focus sealed tube'
_diffrn_standards_decay_%        ?
_diffrn_standards_interval_count ?
_diffrn_standards_interval_time  ?
_diffrn_standards_number         ?
_reflns_number_gt                5193
_reflns_number_total             6092
_reflns_threshold_expression     >2sigma(I)
_computing_cell_refinement       ?
_computing_data_collection       ?
_computing_data_reduction        ?
_computing_molecular_graphics    'Olex2 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 (Dolomanov et al., 2009)'
_computing_structure_refinement  'XH (Sheldrick, 2008)'
_computing_structure_solution    'ShelXS-1997 (Sheldrick, 2008)'
_refine_diff_density_max         1.408
_refine_diff_density_min         -0.417
_refine_diff_density_rms         0.098
_refine_ls_extinction_coef       ?
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.037
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     364
_refine_ls_number_reflns         6092
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0546
_refine_ls_R_factor_gt           0.0416
_refine_ls_restrained_S_all      1.037
_refine_ls_shift/su_max          0.003
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details     
'calc w=1/[σ²(Fo²)+(0.0391P)²+0.3822P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0909
_refine_ls_wR_factor_ref         0.0961
_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. 
;
_olex2_refinement_description    
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups, All C(H,H) groups
 At 1.5 times of:
  All C(H,H,H) groups
2.a Secondary CH2 refined with riding coordinates:
 C18(H18A,H18B)
2.b Me refined with riding coordinates:
 C11(H11A,H11B,H11C), C10(H10A,H10B,H10C), C19(H19A,H19B,H19C), C7T(H7TA,H7TB,
 H7TC)
2.c Aromatic/amide H refined with riding coordinates:
 C17(H17), C16(H16), C15(H15), C14(H14), C2(H2), C3(H3), C9(H9), C8(H8),
 C5(H5), C2T(H2T), C3T(H3T), C5T(H5T), C6T(H6T), C1S(H1SA), C3S(H3S)
;
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
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_calc_flag
_atom_site_disorder_assembly
_atom_site_disorder_group
_atom_site_refinement_flags_posn
Se1 Se 0.17355(3) 1.206436(19) 0.505078(17) 0.01396(8) Uani 1 d . . .
O1 O 0.4092(3) 0.66666(15) 0.70452(13) 0.0227(4) Uani 1 d . . .
O2 O 0.3872(3) 0.61599(14) 0.52883(12) 0.0191(4) Uani 1 d . . .
N1 N 0.2033(3) 1.05518(17) 0.33826(14) 0.0145(4) Uani 1 d . . .
C12 C 0.1345(3) 1.2378(2) 0.39452(17) 0.0138(5) Uani 1 d . . .
C17 C 0.0894(3) 1.3357(2) 0.38525(19) 0.0187(6) Uani 1 d . . .
H17 H 0.0715 1.3963 0.4380 0.022 Uiso 1 calc . . R
C16 C 0.0715(4) 1.3420(2) 0.29708(19) 0.0203(6) Uani 1 d . . .
H16 H 0.0423 1.4083 0.2891 0.024 Uiso 1 calc . . R
C15 C 0.0958(4) 1.2526(2) 0.2195(2) 0.0234(6) Uani 1 d . . .
H15 H 0.0834 1.2592 0.1596 0.028 Uiso 1 calc . . R
C14 C 0.1376(4) 1.1543(2) 0.22797(19) 0.0213(6) Uani 1 d . . .
H14 H 0.1519 1.0931 0.1750 0.026 Uiso 1 calc . . R
C13 C 0.1581(3) 1.1487(2) 0.31762(18) 0.0145(5) Uani 1 d . . .
C1 C 0.2151(3) 1.06693(19) 0.42884(17) 0.0128(5) Uani 1 d . . .
C2 C 0.2545(3) 0.9803(2) 0.46260(17) 0.0144(5) Uani 1 d . . .
H2 H 0.2690 0.9107 0.4189 0.017 Uiso 1 calc . . R
C3 C 0.2720(3) 0.9926(2) 0.55326(17) 0.0145(5) Uani 1 d . . .
H3 H 0.2585 1.0632 0.5957 0.017 Uiso 1 calc . . R
C4 C 0.3093(3) 0.9084(2) 0.59217(17) 0.0135(5) Uani 1 d . . .
C9 C 0.3212(3) 0.9346(2) 0.68849(18) 0.0179(5) Uani 1 d . . .
H9 H 0.3063 1.0069 0.7269 0.021 Uiso 1 calc . . R
C8 C 0.3547(4) 0.8557(2) 0.72879(18) 0.0191(6) Uani 1 d . . .
H8 H 0.3622 0.8744 0.7943 0.023 Uiso 1 calc . . R
C7 C 0.3770(3) 0.7505(2) 0.67368(18) 0.0156(5) Uani 1 d . . .
C6 C 0.3644(3) 0.7224(2) 0.57570(18) 0.0150(5) Uani 1 d . . .
C5 C 0.3324(3) 0.8004(2) 0.53591(17) 0.0138(5) Uani 1 d . . .
H5 H 0.3257 0.7817 0.4704 0.017 Uiso 1 calc . . R
C11 C 0.4135(4) 0.6875(3) 0.80229(19) 0.0296(7) Uani 1 d . . .
H11A H 0.4280 0.6193 0.8151 0.044 Uiso 1 calc . . R
H11B H 0.2971 0.7133 0.8252 0.044 Uiso 1 calc . . R
H11C H 0.5184 0.7441 0.8336 0.044 Uiso 1 calc . . R
C10 C 0.3686(4) 0.5824(2) 0.42896(17) 0.0204(6) Uani 1 d . . .
H10A H 0.3930 0.5058 0.4027 0.031 Uiso 1 calc . . R
H10B H 0.4581 0.6304 0.4082 0.031 Uiso 1 calc . . R
H10C H 0.2421 0.5882 0.4081 0.031 Uiso 1 calc . . R
C18 C 0.2343(4) 0.9545(2) 0.26522(18) 0.0189(6) Uani 1 d . . .
H18A H 0.3263 0.9176 0.2893 0.023 Uiso 1 calc . . R
H18B H 0.2861 0.9738 0.2128 0.023 Uiso 1 calc . . R
C19 C 0.0560(4) 0.8763(2) 0.2311(2) 0.0313(7) Uani 1 d . . .
H19A H 0.0815 0.8091 0.1831 0.047 Uiso 1 calc . . R
H19B H -0.0336 0.9117 0.2052 0.047 Uiso 1 calc . . R
H19C H 0.0044 0.8572 0.2830 0.047 Uiso 1 calc . . R
S1 S 0.46199(9) 0.29037(5) 0.76580(4) 0.01651(14) Uani 1 d . . .
O11 O 0.5347(3) 0.22365(15) 0.68151(13) 0.0221(4) Uani 1 d . . .
O12 O 0.3017(2) 0.34057(16) 0.74830(14) 0.0252(4) Uani 1 d . . .
O13 O 0.4294(3) 0.23182(16) 0.83165(14) 0.0293(5) Uani 1 d . . .
C1T C 0.6405(3) 0.4015(2) 0.82216(17) 0.0149(5) Uani 1 d . . .
C2T C 0.8218(4) 0.3994(2) 0.79681(17) 0.0174(5) Uani 1 d . . .
H2T H 0.8511 0.3410 0.7450 0.021 Uiso 1 calc . . R
C3T C 0.9608(4) 0.4835(2) 0.84777(17) 0.0185(5) Uani 1 d . . .
H3T H 1.0847 0.4820 0.8301 0.022 Uiso 1 calc . . R
C4T C 0.9214(4) 0.5696(2) 0.92400(17) 0.0184(6) Uani 1 d . . .
C5T C 0.7375(4) 0.5718(2) 0.94692(18) 0.0210(6) Uani 1 d . . .
H5T H 0.7073 0.6315 0.9974 0.025 Uiso 1 calc . . R
C6T C 0.5983(4) 0.4884(2) 0.89723(18) 0.0188(6) Uani 1 d . . .
H6T H 0.4741 0.4905 0.9143 0.023 Uiso 1 calc . . R
C7T C 1.0726(4) 0.6584(2) 0.98102(19) 0.0273(7) Uani 1 d . . .
H7TA H 1.1836 0.6565 0.9464 0.041 Uiso 1 calc . . R
H7TB H 1.1029 0.6457 1.0393 0.041 Uiso 1 calc . . R
H7TC H 1.0296 0.7306 0.9944 0.041 Uiso 1 calc . . R
O1S O 0.2575(3) 0.11278(19) 0.93392(16) 0.0308(5) Uani 1 d . . .
H1S H 0.312(5) 0.149(3) 0.909(3) 0.052(13) Uiso 1 d . . .
C1S C 0.3091(4) -0.0261(2) 0.99785(18) 0.0221(6) Uani 1 d . . .
H1SA H 0.1783 -0.0447 0.9962 0.027 Uiso 1 calc . . R
C2S C 0.3806(4) 0.0584(2) 0.96623(18) 0.0210(6) Uani 1 d . . .
C3S C 0.5724(4) 0.0839(2) 0.96805(18) 0.0219(6) Uani 1 d . . .
H3S H 0.6227 0.1409 0.9459 0.026 Uiso 1 calc . . R
O1W O 0.1638(3) 0.43908(19) 0.61854(17) 0.0285(5) Uani 1 d . . .
H1WA H 0.201(6) 0.419(4) 0.659(3) 0.066(15) Uiso 1 d . . .
H1WB H 0.230(5) 0.495(3) 0.621(3) 0.048(12) Uiso 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 C12 1.883(2) . ?
Se1 C1 1.867(2) . ?
O1 C7 1.356(3) . ?
O1 C11 1.430(3) . ?
O2 C6 1.361(3) . ?
O2 C10 1.442(3) . ?
N1 C13 1.416(3) . ?
N1 C1 1.343(3) . ?
N1 C18 1.460(3) . ?
C12 C17 1.393(3) . ?
C12 C13 1.385(3) . ?
C17 H17 0.9500 . ?
C17 C16 1.381(4) . ?
C16 H16 0.9500 . ?
C16 C15 1.395(4) . ?
C15 H15 0.9500 . ?
C15 C14 1.385(4) . ?
C14 H14 0.9500 . ?
C14 C13 1.401(3) . ?
C1 C2 1.431(3) . ?
C2 H2 0.9500 . ?
C2 C3 1.343(3) . ?
C3 H3 0.9500 . ?
C3 C4 1.447(3) . ?
C4 C9 1.398(4) . ?
C4 C5 1.415(3) . ?
C9 H9 0.9500 . ?
C9 C8 1.391(4) . ?
C8 H8 0.9500 . ?
C8 C7 1.379(4) . ?
C7 C6 1.420(4) . ?
C6 C5 1.374(3) . ?
C5 H5 0.9500 . ?
C11 H11A 0.9800 . ?
C11 H11B 0.9800 . ?
C11 H11C 0.9800 . ?
C10 H10A 0.9800 . ?
C10 H10B 0.9800 . ?
C10 H10C 0.9800 . ?
C18 H18A 0.9900 . ?
C18 H18B 0.9900 . ?
C18 C19 1.508(4) . ?
C19 H19A 0.9800 . ?
C19 H19B 0.9800 . ?
C19 H19C 0.9800 . ?
S1 O11 1.4550(19) . ?
S1 O12 1.4533(19) . ?
S1 O13 1.456(2) . ?
S1 C1T 1.779(3) . ?
C1T C2T 1.387(4) . ?
C1T C6T 1.393(3) . ?
C2T H2T 0.9500 . ?
C2T C3T 1.394(4) . ?
C3T H3T 0.9500 . ?
C3T C4T 1.390(4) . ?
C4T C5T 1.394(4) . ?
C4T C7T 1.506(4) . ?
C5T H5T 0.9500 . ?
C5T C6T 1.385(4) . ?
C6T H6T 0.9500 . ?
C7T H7TA 0.9800 . ?
C7T H7TB 0.9800 . ?
C7T H7TC 0.9800 . ?
O1S H1S 0.78(4) . ?
O1S C2S 1.370(3) . ?
C1S H1SA 0.9500 . ?
C1S C2S 1.391(4) . ?
C1S C3S 1.392(4) 2_657 ?
C2S C3S 1.390(4) . ?
C3S C1S 1.392(4) 2_657 ?
C3S H3S 0.9500 . ?
O1W H1WA 0.79(4) . ?
O1W H1WB 0.80(4) . ?

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 C12 85.95(11) . . ?
C7 O1 C11 117.4(2) . . ?
C6 O2 C10 116.51(19) . . ?
C13 N1 C18 121.5(2) . . ?
C1 N1 C13 114.9(2) . . ?
C1 N1 C18 123.5(2) . . ?
C17 C12 Se1 127.6(2) . . ?
C13 C12 Se1 111.31(17) . . ?
C13 C12 C17 121.1(2) . . ?
C12 C17 H17 121.0 . . ?
C16 C17 C12 118.0(3) . . ?
C16 C17 H17 121.0 . . ?
C17 C16 H16 119.5 . . ?
C17 C16 C15 121.0(2) . . ?
C15 C16 H16 119.5 . . ?
C16 C15 H15 119.3 . . ?
C14 C15 C16 121.4(3) . . ?
C14 C15 H15 119.3 . . ?
C15 C14 H14 121.2 . . ?
C15 C14 C13 117.5(3) . . ?
C13 C14 H14 121.2 . . ?
C12 C13 N1 114.5(2) . . ?
C12 C13 C14 121.0(2) . . ?
C14 C13 N1 124.5(2) . . ?
N1 C1 Se1 113.29(17) . . ?
N1 C1 C2 122.8(2) . . ?
C2 C1 Se1 123.88(19) . . ?
C1 C2 H2 118.5 . . ?
C3 C2 C1 123.1(2) . . ?
C3 C2 H2 118.5 . . ?
C2 C3 H3 117.0 . . ?
C2 C3 C4 126.0(2) . . ?
C4 C3 H3 117.0 . . ?
C9 C4 C3 118.8(2) . . ?
C9 C4 C5 119.0(2) . . ?
C5 C4 C3 122.2(2) . . ?
C4 C9 H9 119.6 . . ?
C8 C9 C4 120.7(2) . . ?
C8 C9 H9 119.6 . . ?
C9 C8 H8 120.0 . . ?
C7 C8 C9 120.1(2) . . ?
C7 C8 H8 120.0 . . ?
O1 C7 C8 125.6(2) . . ?
O1 C7 C6 114.4(2) . . ?
C8 C7 C6 120.0(2) . . ?
O2 C6 C7 114.5(2) . . ?
O2 C6 C5 125.5(2) . . ?
C5 C6 C7 119.9(2) . . ?
C4 C5 H5 119.9 . . ?
C6 C5 C4 120.3(2) . . ?
C6 C5 H5 119.9 . . ?
O1 C11 H11A 109.5 . . ?
O1 C11 H11B 109.5 . . ?
O1 C11 H11C 109.5 . . ?
H11A C11 H11B 109.5 . . ?
H11A C11 H11C 109.5 . . ?
H11B C11 H11C 109.5 . . ?
O2 C10 H10A 109.5 . . ?
O2 C10 H10B 109.5 . . ?
O2 C10 H10C 109.5 . . ?
H10A C10 H10B 109.5 . . ?
H10A C10 H10C 109.5 . . ?
H10B C10 H10C 109.5 . . ?
N1 C18 H18A 109.4 . . ?
N1 C18 H18B 109.4 . . ?
N1 C18 C19 111.3(2) . . ?
H18A C18 H18B 108.0 . . ?
C19 C18 H18A 109.4 . . ?
C19 C18 H18B 109.4 . . ?
C18 C19 H19A 109.5 . . ?
C18 C19 H19B 109.5 . . ?
C18 C19 H19C 109.5 . . ?
H19A C19 H19B 109.5 . . ?
H19A C19 H19C 109.5 . . ?
H19B C19 H19C 109.5 . . ?
O11 S1 O13 112.63(12) . . ?
O11 S1 C1T 106.45(12) . . ?
O12 S1 O11 113.35(11) . . ?
O12 S1 O13 112.45(12) . . ?
O12 S1 C1T 106.09(12) . . ?
O13 S1 C1T 105.08(11) . . ?
C2T C1T S1 121.37(19) . . ?
C2T C1T C6T 119.8(2) . . ?
C6T C1T S1 118.7(2) . . ?
C1T C2T H2T 120.2 . . ?
C1T C2T C3T 119.6(2) . . ?
C3T C2T H2T 120.2 . . ?
C2T C3T H3T 119.4 . . ?
C4T C3T C2T 121.2(2) . . ?
C4T C3T H3T 119.4 . . ?
C3T C4T C5T 118.3(2) . . ?
C3T C4T C7T 121.2(3) . . ?
C5T C4T C7T 120.4(2) . . ?
C4T C5T H5T 119.5 . . ?
C6T C5T C4T 121.0(2) . . ?
C6T C5T H5T 119.5 . . ?
C1T C6T H6T 120.0 . . ?
C5T C6T C1T 120.0(2) . . ?
C5T C6T H6T 120.0 . . ?
C4T C7T H7TA 109.5 . . ?
C4T C7T H7TB 109.5 . . ?
C4T C7T H7TC 109.5 . . ?
H7TA C7T H7TB 109.5 . . ?
H7TA C7T H7TC 109.5 . . ?
H7TB C7T H7TC 109.5 . . ?
C2S O1S H1S 108(3) . . ?
C2S C1S H1SA 119.7 . . ?
C2S C1S C3S 120.6(3) . 2_657 ?
C3S C1S H1SA 119.7 2_657 . ?
O1S C2S C1S 118.0(3) . . ?
O1S C2S C3S 122.8(2) . . ?
C3S C2S C1S 119.1(2) . . ?
C1S C3S H3S 119.9 2_657 . ?
C2S C3S C1S 120.3(3) . 2_657 ?
C2S C3S H3S 119.9 . . ?
H1WA O1W H1WB 107(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
O1S H1S O13 0.78(4) 2.00(4) 2.768(3) 173(4) .
O1W H1WA O12 0.79(4) 2.11(4) 2.893(3) 171(4) .
O1W H1WB O1 0.80(4) 2.37(4) 3.108(3) 152(4) .
O1W H1WB O2 0.80(4) 2.63(4) 3.334(3) 147(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
Se1 C12 C17 C16 178.36(19) . . . . ?
Se1 C12 C13 N1 0.7(3) . . . . ?
Se1 C12 C13 C14 -179.3(2) . . . . ?
Se1 C1 C2 C3 -2.5(4) . . . . ?
O1 C7 C6 O2 -0.1(3) . . . . ?
O1 C7 C6 C5 -179.9(2) . . . . ?
O2 C6 C5 C4 179.4(2) . . . . ?
N1 C1 C2 C3 177.9(2) . . . . ?
C12 Se1 C1 N1 1.39(18) . . . . ?
C12 Se1 C1 C2 -178.3(2) . . . . ?
C12 C17 C16 C15 0.7(4) . . . . ?
C17 C12 C13 N1 -179.9(2) . . . . ?
C17 C12 C13 C14 0.1(4) . . . . ?
C17 C16 C15 C14 0.3(4) . . . . ?
C16 C15 C14 C13 -1.1(4) . . . . ?
C15 C14 C13 N1 -179.0(2) . . . . ?
C15 C14 C13 C12 0.9(4) . . . . ?
C13 N1 C1 Se1 -1.4(3) . . . . ?
C13 N1 C1 C2 178.3(2) . . . . ?
C13 N1 C18 C19 -90.2(3) . . . . ?
C13 C12 C17 C16 -0.9(4) . . . . ?
C1 Se1 C12 C17 179.5(2) . . . . ?
C1 Se1 C12 C13 -1.12(18) . . . . ?
C1 N1 C13 C12 0.4(3) . . . . ?
C1 N1 C13 C14 -179.6(2) . . . . ?
C1 N1 C18 C19 89.8(3) . . . . ?
C1 C2 C3 C4 179.2(2) . . . . ?
C2 C3 C4 C9 -179.2(2) . . . . ?
C2 C3 C4 C5 0.1(4) . . . . ?
C3 C4 C9 C8 179.2(2) . . . . ?
C3 C4 C5 C6 -178.8(2) . . . . ?
C4 C9 C8 C7 0.1(4) . . . . ?
C9 C4 C5 C6 0.5(4) . . . . ?
C9 C8 C7 O1 -179.7(2) . . . . ?
C9 C8 C7 C6 -0.5(4) . . . . ?
C8 C7 C6 O2 -179.4(2) . . . . ?
C8 C7 C6 C5 0.8(4) . . . . ?
C7 C6 C5 C4 -0.9(4) . . . . ?
C5 C4 C9 C8 -0.2(4) . . . . ?
C11 O1 C7 C8 2.5(4) . . . . ?
C11 O1 C7 C6 -176.7(2) . . . . ?
C10 O2 C6 C7 177.8(2) . . . . ?
C10 O2 C6 C5 -2.5(4) . . . . ?
C18 N1 C13 C12 -179.5(2) . . . . ?
C18 N1 C13 C14 0.4(4) . . . . ?
C18 N1 C1 Se1 178.61(17) . . . . ?
C18 N1 C1 C2 -1.7(4) . . . . ?
S1 C1T C2T C3T -174.56(19) . . . . ?
S1 C1T C6T C5T 175.1(2) . . . . ?
O11 S1 C1T C2T -14.5(2) . . . . ?
O11 S1 C1T C6T 169.76(19) . . . . ?
O12 S1 C1T C2T -135.5(2) . . . . ?
O12 S1 C1T C6T 48.7(2) . . . . ?
O13 S1 C1T C2T 105.2(2) . . . . ?
O13 S1 C1T C6T -70.6(2) . . . . ?
C1T C2T C3T C4T 0.2(4) . . . . ?
C2T C1T C6T C5T -0.7(4) . . . . ?
C2T C3T C4T C5T -1.9(4) . . . . ?
C2T C3T C4T C7T 177.9(2) . . . . ?
C3T C4T C5T C6T 2.3(4) . . . . ?
C4T C5T C6T C1T -1.0(4) . . . . ?
C6T C1T C2T C3T 1.1(4) . . . . ?
C7T C4T C5T C6T -177.5(2) . . . . ?
O1S C2S C3S C1S 179.6(3) . . . 2_657 ?
C1S C2S C3S C1S -0.7(4) . . . 2_657 ?
C3S C1S C2S O1S -179.6(2) 2_657 . . . ?
C3S C1S C2S C3S 0.8(4) 2_657 . . . ?

_olex2_submission_special_instructions 'No special instructions were received'
