# Electronic Supplementary Material (ESI) for Organic & Biomolecular Chemistry.
# 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_ks156_2_02
_audit_block_doi                 10.5517/cc1jrdsg
_database_code_depnum_ccdc_archive 'CCDC 1422676'
_audit_update_record             
;
2015-09-07 deposited with the CCDC.
2016-10-07 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-97
_chemical_name_systematic        
;
 ?
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C35 H55 N O Se'
_chemical_formula_weight         584.76
_chemical_absolute_configuration rm

loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0181 0.0091 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
N N 0.0311 0.0180 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
Se Se -0.7943 1.1372 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0492 0.0322 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_symmetry_cell_setting           monoclinic
_symmetry_space_group_name_H-M   P21

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

_cell_length_a                   13.729(2)
_cell_length_b                   8.3619(9)
_cell_length_c                   14.594(3)
_cell_angle_alpha                90.00
_cell_angle_beta                 114.96(2)
_cell_angle_gamma                90.00
_cell_volume                     1518.9(4)
_cell_formula_units_Z            2
_cell_measurement_temperature    100(1)
_cell_measurement_reflns_used    ?
_cell_measurement_theta_min      ?
_cell_measurement_theta_max      ?

_exptl_crystal_description       needle
_exptl_crystal_colour            colorless
_exptl_crystal_size_max          0.3
_exptl_crystal_size_mid          0.03
_exptl_crystal_size_min          0.02
_exptl_crystal_density_meas      ?
_exptl_crystal_density_diffrn    1.279
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             628
_exptl_absorpt_coefficient_mu    1.864
_exptl_absorpt_correction_type   ?
_exptl_absorpt_correction_T_min  ?
_exptl_absorpt_correction_T_max  ?
_exptl_absorpt_process_details   ?

_exptl_special_details           
;
 ?
;

_diffrn_ambient_temperature      100(1)
_diffrn_radiation_wavelength     1.54184
_diffrn_radiation_type           CuK\a
_diffrn_radiation_source         'SuperNova (Cu) X-ray Source'
_diffrn_radiation_monochromator  mirror
_diffrn_measurement_device_type  'SuperNova, Dual, Cu at zero, Eos'
_diffrn_measurement_method       'ω scans'
_diffrn_detector_area_resol_mean ?
_diffrn_standards_number         ?
_diffrn_standards_interval_count ?
_diffrn_standards_interval_time  ?
_diffrn_standards_decay_%        ?
_diffrn_reflns_number            4160
_diffrn_reflns_av_R_equivalents  0.0580
_diffrn_reflns_av_sigmaI/netI    0.1181
_diffrn_reflns_limit_h_min       -14
_diffrn_reflns_limit_h_max       15
_diffrn_reflns_limit_k_min       -9
_diffrn_reflns_limit_k_max       5
_diffrn_reflns_limit_l_min       -16
_diffrn_reflns_limit_l_max       15
_diffrn_reflns_theta_min         3.34
_diffrn_reflns_theta_max         58.92
_reflns_number_total             2992
_reflns_number_gt                2177
_reflns_threshold_expression     >2σ(I)
_computing_cell_refinement       
;
CrysAlisPro, Agilent Technologies,
Version 1.171.35.21b (release 03-02-2012 CrysAlis171 .NET)
(compiled Feb  3 2012,10:37:01)
;
_computing_data_collection       
;
CrysAlisPro, Agilent Technologies,
Version 1.171.35.21b (release 03-02-2012 CrysAlis171 .NET)
(compiled Feb  3 2012,10:37:01)
;
_computing_data_reduction        
;
CrysAlisPro, Agilent Technologies,
Version 1.171.35.21b (release 03-02-2012 CrysAlis171 .NET)
(compiled Feb  3 2012,10:37:01)
;
_computing_structure_solution    
;
SHELXS, G.M. Sheldrick, Acta Cryst.
(2008). A64, 112-122
;
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 2008)'
_computing_molecular_graphics    ?
_computing_publication_material  ?

_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 > 2σ(F²) is used only for calculating R-factors(gt) etc. and is
 not relevant to the choice of reflections for refinement.  R-factors based
 on F² are statistically about twice as large as those based on F, and R-
 factors based on ALL data will be even larger.
;

_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'calc w=1/[σ²(Fo²)+(0.1461P)²+2.1096P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_atom_sites_solution_hydrogens   geom
_refine_ls_hydrogen_treatment    mixed
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       ?
_refine_ls_abs_structure_details 'Flack H D (1983), Acta Cryst. A39, 876-881'
_refine_ls_abs_structure_Flack   -0.10(7)
_refine_ls_number_reflns         2992
_refine_ls_number_parameters     349
_refine_ls_number_restraints     1
_refine_ls_R_factor_all          0.1157
_refine_ls_R_factor_gt           0.0895
_refine_ls_wR_factor_ref         0.2644
_refine_ls_wR_factor_gt          0.2280
_refine_ls_goodness_of_fit_ref   1.046
_refine_ls_restrained_S_all      1.045
_refine_ls_shift/su_max          0.001
_refine_ls_shift/su_mean         0.000

loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_symmetry_multiplicity
_atom_site_calc_flag
_atom_site_refinement_flags
_atom_site_disorder_assembly
_atom_site_disorder_group
Se1 Se -0.52043(12) -0.3487(2) -0.48953(13) 0.0571(6) Uani 1 1 d . . .
O1 O 0.0602(6) 0.5675(10) 0.2467(7) 0.031(2) Uani 1 1 d . . .
N1 N -0.3168(14) -0.160(2) -0.4026(14) 0.087(5) Uani 1 1 d . . .
C1 C -0.2135(8) 0.5403(14) 0.0241(9) 0.023(3) Uani 1 1 d . . .
H1A H -0.2454 0.6093 -0.0345 0.028 Uiso 1 1 calc R . .
H1B H -0.2601 0.5410 0.0589 0.028 Uiso 1 1 calc R . .
C2 C -0.1022(9) 0.6078(17) 0.0956(9) 0.034(3) Uani 1 1 d . . .
H2A H -0.0573 0.6156 0.0592 0.040 Uiso 1 1 calc R . .
H2B H -0.1111 0.7146 0.1169 0.040 Uiso 1 1 calc R . .
C3 C -0.0472(9) 0.5045(14) 0.1871(10) 0.026(3) Uani 1 1 d . . .
H3 H -0.0882 0.5093 0.2281 0.031 Uiso 1 1 calc R . .
C4 C -0.0346(9) 0.3298(16) 0.1648(10) 0.029(3) Uani 1 1 d . . .
C5 C -0.1459(9) 0.2647(16) 0.0835(10) 0.026(3) Uani 1 1 d . . .
H5 H -0.1929 0.2653 0.1187 0.031 Uiso 1 1 calc R . .
C6 C -0.1410(9) 0.0922(15) 0.0577(10) 0.026(3) Uani 1 1 d . . .
H6A H -0.1001 0.0326 0.1191 0.032 Uiso 1 1 calc R . .
H6B H -0.1043 0.0830 0.0139 0.032 Uiso 1 1 calc R . .
C7 C -0.2531(9) 0.0205(16) 0.0051(10) 0.028(3) Uani 1 1 d . . .
H7A H -0.2858 0.0188 0.0524 0.033 Uiso 1 1 calc R . .
H7B H -0.2465 -0.0894 -0.0128 0.033 Uiso 1 1 calc R . .
C8 C -0.3282(8) 0.1099(14) -0.0906(9) 0.023(3) Uani 1 1 d . . .
C9 C -0.3217(9) 0.2982(15) -0.0645(10) 0.028(3) Uani 1 1 d . . .
H9 H -0.3516 0.3084 -0.0145 0.034 Uiso 1 1 calc R . .
C10 C -0.2068(9) 0.3651(14) -0.0121(9) 0.023(3) Uani 1 1 d . . .
C11 C -0.3991(9) 0.3895(16) -0.1570(9) 0.028(3) Uani 1 1 d . . .
H11A H -0.3986 0.5013 -0.1391 0.034 Uiso 1 1 calc R . .
H11B H -0.3734 0.3830 -0.2094 0.034 Uiso 1 1 calc R . .
C12 C -0.5141(9) 0.3286(15) -0.1994(9) 0.024(3) Uani 1 1 d . . .
H12A H -0.5561 0.3853 -0.2617 0.029 Uiso 1 1 calc R . .
H12B H -0.5443 0.3529 -0.1518 0.029 Uiso 1 1 calc R . .
C13 C -0.5244(8) 0.1484(17) -0.2209(8) 0.022(2) Uani 1 1 d . . .
H13 H -0.4948 0.1292 -0.2703 0.026 Uiso 1 1 calc R . .
C14 C -0.4518(9) 0.0540(15) -0.1240(9) 0.022(3) Uani 1 1 d . . .
C15 C -0.4602(9) -0.1287(13) -0.1408(9) 0.023(3) Uani 1 1 d . . .
H15A H -0.4224 -0.1580 -0.1815 0.028 Uiso 1 1 calc R . .
H15B H -0.4248 -0.1818 -0.0760 0.028 Uiso 1 1 calc R . .
C16 C -0.5757(9) -0.1882(16) -0.1930(9) 0.029(3) Uani 1 1 d . . .
H16A H -0.6112 -0.1723 -0.1487 0.034 Uiso 1 1 calc R . .
H16B H -0.5757 -0.3018 -0.2064 0.034 Uiso 1 1 calc R . .
C17 C -0.6372(9) -0.0992(15) -0.2923(9) 0.023(3) Uani 1 1 d . . .
C18 C -0.6384(9) 0.0837(15) -0.2677(10) 0.028(3) Uani 1 1 d . . .
H18 H -0.6656 0.0914 -0.2156 0.033 Uiso 1 1 calc R . .
C19 C -0.7238(8) 0.1537(18) -0.3626(8) 0.025(3) Uani 1 1 d . . .
H19 H -0.6914 0.1747 -0.4097 0.030 Uiso 1 1 calc R . .
C20 C -0.8058(9) 0.0177(15) -0.4067(10) 0.029(3) Uani 1 1 d . . .
H20A H -0.8729 0.0456 -0.4034 0.034 Uiso 1 1 calc R . .
H20B H -0.8202 -0.0003 -0.4769 0.034 Uiso 1 1 calc R . .
C21 C -0.7593(9) -0.1307(15) -0.3458(10) 0.031(3) Uani 1 1 d . . .
H21A H -0.7745 -0.2238 -0.3893 0.037 Uiso 1 1 calc R . .
H21B H -0.7888 -0.1480 -0.2967 0.037 Uiso 1 1 calc R . .
C22 C -0.7799(10) 0.3078(16) -0.3528(11) 0.035(3) Uani 1 1 d . . .
C23 C -0.8423(14) 0.392(2) -0.4430(11) 0.060(5) Uani 1 1 d . . .
H23A H -0.8910 0.3191 -0.4918 0.090 Uiso 1 1 calc R . .
H23B H -0.7957 0.4388 -0.4696 0.090 Uiso 1 1 calc R . .
H23C H -0.8824 0.4746 -0.4288 0.090 Uiso 1 1 calc R . .
C24 C -0.7851(10) 0.3528(16) -0.2691(12) 0.045(4) Uani 1 1 d . . .
H24A H -0.8291 0.4380 -0.2699 0.054 Uiso 1 1 calc R . .
H24B H -0.7450 0.2997 -0.2089 0.054 Uiso 1 1 calc R . .
C25 C -0.5881(9) -0.1297(15) -0.3707(10) 0.026(3) Uani 1 1 d . . .
H25A H -0.6353 -0.0833 -0.4352 0.031 Uiso 1 1 calc R . .
H25B H -0.5193 -0.0758 -0.3477 0.031 Uiso 1 1 calc R . .
C26 C -0.5724(9) -0.3084(14) -0.3858(9) 0.029(3) Uani 1 1 d . . .
H26A H -0.6403 -0.3634 -0.4044 0.035 Uiso 1 1 calc R . .
H26B H -0.5215 -0.3530 -0.3222 0.035 Uiso 1 1 calc R . .
C27 C -0.3930(14) -0.236(2) -0.4289(16) 0.074(6) Uani 1 1 d . . .
C28 C -0.4881(9) 0.0875(16) -0.0399(9) 0.033(3) Uani 1 1 d . . .
H28A H -0.4824 0.1999 -0.0252 0.049 Uiso 1 1 calc R . .
H28B H -0.4432 0.0294 0.0198 0.049 Uiso 1 1 calc R . .
H28C H -0.5614 0.0542 -0.0615 0.049 Uiso 1 1 calc R . .
C29 C -0.2934(8) 0.0754(15) -0.1759(9) 0.026(3) Uani 1 1 d . . .
H29A H -0.2165 0.0799 -0.1495 0.039 Uiso 1 1 calc R . .
H29B H -0.3243 0.1539 -0.2283 0.039 Uiso 1 1 calc R . .
H29C H -0.3178 -0.0291 -0.2031 0.039 Uiso 1 1 calc R . .
C30 C -0.1493(9) 0.3775(15) -0.0833(9) 0.029(3) Uani 1 1 d . . .
H30A H -0.1312 0.2723 -0.0974 0.043 Uiso 1 1 calc R . .
H30B H -0.0849 0.4397 -0.0512 0.043 Uiso 1 1 calc R . .
H30C H -0.1961 0.4282 -0.1453 0.043 Uiso 1 1 calc R . .
C31 C -0.0009(9) 0.2351(16) 0.2654(9) 0.031(3) Uani 1 1 d . . .
H31A H -0.0595 0.2335 0.2848 0.046 Uiso 1 1 calc R . .
H31B H 0.0602 0.2859 0.3173 0.046 Uiso 1 1 calc R . .
H31C H 0.0175 0.1275 0.2559 0.046 Uiso 1 1 calc R . .
C32 C 0.0584(8) 0.3068(16) 0.1308(10) 0.031(3) Uani 1 1 d . . .
H32A H 0.1240 0.3486 0.1818 0.046 Uiso 1 1 calc R . .
H32B H 0.0411 0.3627 0.0684 0.046 Uiso 1 1 calc R . .
H32C H 0.0671 0.1950 0.1213 0.046 Uiso 1 1 calc R . .
C33 C 0.0662(9) 0.7033(16) 0.3046(10) 0.037(4) Uani 1 1 d . . .
H33A H 0.0394 0.6801 0.3549 0.044 Uiso 1 1 calc R . .
H33B H 0.0241 0.7898 0.2619 0.044 Uiso 1 1 calc R . .
C34 C 0.1845(10) 0.7487(18) 0.3553(9) 0.036(3) Uani 1 1 d . . .
H34 H 0.2336 0.6695 0.3906 0.043 Uiso 1 1 calc R . .
C35 C 0.2218(11) 0.8924(18) 0.3524(10) 0.037(3) Uani 1 1 d . . .
H35A H 0.1748 0.9742 0.3177 0.044 Uiso 1 1 calc R . .
H35B H 0.2952 0.9123 0.3851 0.044 Uiso 1 1 calc R . .


_geom_special_details            
;
 All s.u.'s (except the s.u. in the dihedral angle between two l.s. planes)
 are estimated using the full covariance matrix.  The cell s.u.'s are taken
 into account individually in the estimation of s.u.'s in distances, angles
 and torsion angles; correlations between s.u.'s in cell parameters are only
 used when they are defined by crystal symmetry.  An approximate (isotropic)
 treatment of cell s.u.'s is used for estimating s.u.'s 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 C27 1.850(19) . ?
Se1 C26 1.956(11) . ?
O1 C33 1.396(14) . ?
O1 C3 1.458(13) . ?
N1 C27 1.14(2) . ?
C1 C2 1.549(15) . ?
C1 C10 1.573(16) . ?
C2 C3 1.499(17) . ?
C3 C4 1.522(16) . ?
C4 C31 1.557(17) . ?
C4 C32 1.564(15) . ?
C4 C5 1.584(16) . ?
C5 C6 1.499(18) . ?
C5 C10 1.538(17) . ?
C6 C7 1.523(16) . ?
C7 C8 1.536(16) . ?
C8 C29 1.537(15) . ?
C8 C9 1.614(17) . ?
C8 C14 1.624(13) . ?
C9 C11 1.524(18) . ?
C9 C10 1.539(16) . ?
C10 C30 1.552(15) . ?
C11 C12 1.519(15) . ?
C12 C13 1.533(18) . ?
C13 C18 1.519(15) . ?
C13 C14 1.558(16) . ?
C14 C28 1.533(15) . ?
C14 C15 1.544(16) . ?
C15 C16 1.524(15) . ?
C16 C17 1.528(17) . ?
C17 C21 1.545(15) . ?
C17 C18 1.573(17) . ?
C17 C25 1.575(15) . ?
C18 C19 1.505(16) . ?
C19 C20 1.538(18) . ?
C19 C22 1.538(18) . ?
C20 C21 1.503(18) . ?
C22 C24 1.31(2) . ?
C22 C23 1.418(19) . ?
C25 C26 1.539(16) . ?
C33 C34 1.521(16) . ?
C34 C35 1.31(2) . ?

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
C27 Se1 C26 97.0(6) . . ?
C33 O1 C3 116.2(9) . . ?
C2 C1 C10 112.6(9) . . ?
C3 C2 C1 111.9(10) . . ?
O1 C3 C2 109.0(9) . . ?
O1 C3 C4 107.2(9) . . ?
C2 C3 C4 115.0(11) . . ?
C3 C4 C31 107.6(11) . . ?
C3 C4 C32 111.6(10) . . ?
C31 C4 C32 106.2(9) . . ?
C3 C4 C5 109.2(9) . . ?
C31 C4 C5 109.9(10) . . ?
C32 C4 C5 112.2(10) . . ?
C6 C5 C10 111.3(11) . . ?
C6 C5 C4 112.8(11) . . ?
C10 C5 C4 118.4(10) . . ?
C5 C6 C7 111.2(10) . . ?
C6 C7 C8 114.5(10) . . ?
C7 C8 C29 109.0(9) . . ?
C7 C8 C9 108.2(10) . . ?
C29 C8 C9 111.7(10) . . ?
C7 C8 C14 110.4(9) . . ?
C29 C8 C14 110.2(9) . . ?
C9 C8 C14 107.3(8) . . ?
C11 C9 C10 116.4(10) . . ?
C11 C9 C8 109.3(10) . . ?
C10 C9 C8 114.5(9) . . ?
C5 C10 C9 107.7(9) . . ?
C5 C10 C30 114.1(9) . . ?
C9 C10 C30 113.3(10) . . ?
C5 C10 C1 106.9(10) . . ?
C9 C10 C1 108.2(9) . . ?
C30 C10 C1 106.3(9) . . ?
C12 C11 C9 114.1(10) . . ?
C11 C12 C13 113.8(10) . . ?
C18 C13 C12 115.6(9) . . ?
C18 C13 C14 111.8(11) . . ?
C12 C13 C14 110.1(10) . . ?
C28 C14 C15 106.3(10) . . ?
C28 C14 C13 109.6(9) . . ?
C15 C14 C13 112.4(10) . . ?
C28 C14 C8 111.1(9) . . ?
C15 C14 C8 109.3(9) . . ?
C13 C14 C8 108.3(9) . . ?
C16 C15 C14 113.2(10) . . ?
C15 C16 C17 110.9(10) . . ?
C16 C17 C21 116.4(10) . . ?
C16 C17 C18 108.2(10) . . ?
C21 C17 C18 99.6(10) . . ?
C16 C17 C25 112.1(9) . . ?
C21 C17 C25 108.1(9) . . ?
C18 C17 C25 111.9(10) . . ?
C19 C18 C13 122.0(11) . . ?
C19 C18 C17 104.3(10) . . ?
C13 C18 C17 109.9(10) . . ?
C18 C19 C20 104.3(11) . . ?
C18 C19 C22 117.8(11) . . ?
C20 C19 C22 110.6(9) . . ?
C21 C20 C19 108.0(10) . . ?
C20 C21 C17 104.9(10) . . ?
C24 C22 C23 118.3(13) . . ?
C24 C22 C19 123.7(13) . . ?
C23 C22 C19 117.3(13) . . ?
C26 C25 C17 112.9(10) . . ?
C25 C26 Se1 113.4(8) . . ?
N1 C27 Se1 172(2) . . ?
O1 C33 C34 106.0(10) . . ?
C35 C34 C33 124.3(13) . . ?

_diffrn_measured_fraction_theta_max 0.980
_diffrn_reflns_theta_full        58.92
_diffrn_measured_fraction_theta_full 0.980
_refine_diff_density_max         0.491
_refine_diff_density_min         -0.888
_refine_diff_density_rms         0.110
