# Electronic Supplementary Material (ESI) for Organic & Biomolecular Chemistry.
# This journal is © The Royal Society of Chemistry 2015

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

data_javi07a
_database_code_depnum_ccdc_archive 'CCDC 1406521'
_audit_update_record             
;
2015-06-12 deposited with the CCDC.
2015-07-17 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-97
_chemical_name_systematic        
; 
 ? 
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C29 H41 N O2 Se'
_chemical_absolute_configuration rmad
_chemical_formula_weight         514.59

loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
N N 0.0061 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0106 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
Se Se -0.0929 2.2259 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_symmetry_cell_setting           Monoclinic
_symmetry_space_group_name_H-M   P2(1)

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

_cell_length_a                   10.412(3)
_cell_length_b                   7.850(3)
_cell_length_c                   17.427(6)
_cell_angle_alpha                90.00
_cell_angle_beta                 105.304(6)
_cell_angle_gamma                90.00
_cell_volume                     1373.8(8)
_cell_formula_units_Z            2
_cell_measurement_temperature    298(2)
_cell_measurement_reflns_used    ?
_cell_measurement_theta_min      ?
_cell_measurement_theta_max      ?

_exptl_crystal_description       prism
_exptl_crystal_colour            COLORLESS
_exptl_crystal_size_max          0.41
_exptl_crystal_size_mid          0.25
_exptl_crystal_size_min          0.17
_exptl_crystal_density_meas      ?
_exptl_crystal_density_diffrn    1.244
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             544
_exptl_absorpt_coefficient_mu    1.391
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.795640
_exptl_absorpt_correction_T_max  1.000000
_exptl_absorpt_process_details   
;
 G.M. Sheldrick. 
 SADABS: A program for absorption correction with the Siemens SMART system;  University of Göttingen, Germany, 1996. 
;

_exptl_special_details           
; 
 ? 
;

_diffrn_ambient_temperature      298(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_radiation_source         'fine-focus sealed tube'
_diffrn_radiation_monochromator  graphite
_diffrn_measurement_device_type  'Bruker P4'
_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            3959
_diffrn_reflns_av_R_equivalents  0.0000
_diffrn_reflns_av_sigmaI/netI    0.0269
_diffrn_reflns_limit_h_min       -11
_diffrn_reflns_limit_h_max       11
_diffrn_reflns_limit_k_min       -8
_diffrn_reflns_limit_k_max       8
_diffrn_reflns_limit_l_min       0
_diffrn_reflns_limit_l_max       19
_diffrn_reflns_theta_min         1.21
_diffrn_reflns_theta_max         23.30
_reflns_number_total             3959
_reflns_number_gt                3810
_reflns_threshold_expression     >2sigma(I)

_computing_data_collection       'Bruker XSCANS'
_computing_cell_refinement       'Bruker XSCANS'
_computing_data_reduction        'Bruker SHELXTL'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 1990)'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_computing_molecular_graphics    'Bruker SHELXTL'
_computing_publication_material  'Bruker SHELXTL'

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

_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'calc w=1/[σ²(Fo²)+(0.0643P)²+0.0000P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_atom_sites_solution_hydrogens   geom
_refine_ls_hydrogen_treatment    constr
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       ?
_refine_ls_abs_structure_details 'Flack H D (1983), Acta Cryst. A39, 876-881'
_refine_ls_abs_structure_Flack   -0.004(8)
_refine_ls_number_reflns         3959
_refine_ls_number_parameters     304
_refine_ls_number_restraints     1
_refine_ls_R_factor_all          0.0342
_refine_ls_R_factor_gt           0.0320
_refine_ls_wR_factor_ref         0.0902
_refine_ls_wR_factor_gt          0.0835
_refine_ls_goodness_of_fit_ref   1.146
_refine_ls_restrained_S_all      1.146
_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
O1 O 0.7579(2) 0.7156(3) 0.33273(14) 0.0585(6) Uani 1 1 d . . .
H1 H 0.7638 0.7784 0.2962 0.088 Uiso 1 1 calc R . .
Se1 Se 1.05710(3) 1.16574(5) 0.200963(17) 0.05696(14) Uani 1 1 d . . .
C12 C 0.6784(3) 0.7411(4) 0.10500(17) 0.0411(7) Uani 1 1 d . . .
C20 C 1.2134(3) 0.6603(8) 0.1187(2) 0.0731(10) Uani 1 1 d . . .
H20 H 1.2704 0.5790 0.1483 0.088 Uiso 1 1 calc R . .
C11 C 0.6211(3) 0.8983(4) 0.13587(17) 0.0409(7) Uani 1 1 d . . .
H11A H 0.6200 0.9912 0.0990 0.049 Uiso 1 1 calc R . .
H11B H 0.5294 0.8742 0.1351 0.049 Uiso 1 1 calc R . .
N1 N 0.6907(2) 0.9566(3) 0.21584(14) 0.0382(5) Uani 1 1 d . . .
O2 O 0.82232(18) 0.7368(2) 0.12993(12) 0.0400(4) Uani 1 1 d . . .
C21 C 1.2408(3) 0.7312(6) 0.0522(2) 0.0733(13) Uani 1 1 d . . .
H21 H 1.3168 0.6984 0.0376 0.088 Uiso 1 1 calc R . .
C29 C 1.0074(3) 1.3978(5) 0.3179(2) 0.0597(9) Uani 1 1 d . . .
H29 H 0.9707 1.4684 0.2749 0.072 Uiso 1 1 calc R . .
C24 C 1.0616(3) 1.2435(4) 0.30618(18) 0.0471(7) Uani 1 1 d . . .
C10 C 0.4919(3) 1.1401(5) 0.2158(2) 0.0557(8) Uani 1 1 d . . .
H10A H 0.5335 1.2252 0.1909 0.084 Uiso 1 1 calc R . .
H10B H 0.4455 1.1943 0.2500 0.084 Uiso 1 1 calc R . .
H10C H 0.4300 1.0758 0.1757 0.084 Uiso 1 1 calc R . .
C18 C 1.0169(3) 0.8324(4) 0.09708(17) 0.0403(7) Uani 1 1 d . . .
C19 C 1.1017(3) 0.7102(5) 0.14092(19) 0.0590(10) Uani 1 1 d . . .
H19 H 1.0830 0.6618 0.1855 0.071 Uiso 1 1 calc R . .
C15 C 0.8936(3) 0.8876(4) 0.12022(17) 0.0384(6) Uani 1 1 d . . .
H15 H 0.8380 0.9561 0.0771 0.046 Uiso 1 1 calc R . .
C7 C 0.5371(3) 0.8578(4) 0.29156(17) 0.0382(6) Uani 1 1 d . . .
H7 H 0.5062 0.7858 0.2443 0.046 Uiso 1 1 calc R . .
C13 C 0.6395(3) 0.5778(4) 0.1387(2) 0.0516(8) Uani 1 1 d . . .
H13A H 0.6773 0.4827 0.1177 0.077 Uiso 1 1 calc R . .
H13B H 0.5442 0.5676 0.1242 0.077 Uiso 1 1 calc R . .
H13C H 0.6722 0.5793 0.1956 0.077 Uiso 1 1 calc R . .
C8 C 0.5988(3) 1.0200(4) 0.26524(19) 0.0414(7) Uani 1 1 d . . .
C26 C 1.1146(3) 1.1925(6) 0.4460(2) 0.0661(10) Uani 1 1 d . . .
H26 H 1.1503 1.1220 0.4893 0.079 Uiso 1 1 calc R . .
C25 C 1.1171(3) 1.1411(5) 0.37094(19) 0.0550(8) Uani 1 1 d . . .
H25 H 1.1559 1.0377 0.3638 0.066 Uiso 1 1 calc R . .
C1 C 0.6381(3) 0.7519(4) 0.35414(18) 0.0454(7) Uani 1 1 d . . .
H1A H 0.6611 0.8163 0.4041 0.054 Uiso 1 1 calc R . .
C5 C 0.3568(3) 0.7253(5) 0.3451(2) 0.0590(9) Uani 1 1 d . . .
H5A H 0.2850 0.7522 0.3690 0.071 Uiso 1 1 calc R . .
H5B H 0.3186 0.6636 0.2962 0.071 Uiso 1 1 calc R . .
C17 C 0.7973(3) 1.0776(4) 0.2106(2) 0.0448(7) Uani 1 1 d . . .
H17A H 0.8231 1.1435 0.2594 0.054 Uiso 1 1 calc R . .
H17B H 0.7628 1.1562 0.1671 0.054 Uiso 1 1 calc R . .
C3 C 0.4547(3) 0.6112(4) 0.40081(19) 0.0555(9) Uani 1 1 d . . .
H3 H 0.4838 0.6696 0.4522 0.067 Uiso 1 1 calc R . .
C22 C 1.1573(4) 0.8485(6) 0.0082(2) 0.0712(11) Uani 1 1 d . . .
H22 H 1.1752 0.8944 -0.0371 0.085 Uiso 1 1 calc R . .
C9 C 0.6783(3) 1.1175(4) 0.33796(19) 0.0550(9) Uani 1 1 d . . .
H9A H 0.7610 1.0599 0.3604 0.083 Uiso 1 1 calc R . .
H9B H 0.6281 1.1233 0.3768 0.083 Uiso 1 1 calc R . .
H9C H 0.6958 1.2307 0.3225 0.083 Uiso 1 1 calc R . .
C6 C 0.4164(3) 0.8912(5) 0.3248(2) 0.0537(8) Uani 1 1 d . . .
H6A H 0.4438 0.9610 0.3723 0.064 Uiso 1 1 calc R . .
H6B H 0.3492 0.9535 0.2858 0.064 Uiso 1 1 calc R . .
C28 C 1.0078(4) 1.4474(5) 0.3940(2) 0.0705(11) Uani 1 1 d . . .
H28 H 0.9715 1.5522 0.4019 0.085 Uiso 1 1 calc R . .
C2 C 0.5772(3) 0.5856(4) 0.3690(2) 0.0514(8) Uani 1 1 d . . .
H2A H 0.6431 0.5194 0.4071 0.062 Uiso 1 1 calc R . .
H2B H 0.5517 0.5214 0.3197 0.062 Uiso 1 1 calc R . .
C14 C 0.6310(3) 0.7406(5) 0.01458(19) 0.0564(8) Uani 1 1 d . . .
H14A H 0.6717 0.8334 -0.0062 0.085 Uiso 1 1 calc R . .
H14B H 0.5359 0.7533 -0.0017 0.085 Uiso 1 1 calc R . .
H14C H 0.6554 0.6349 -0.0054 0.085 Uiso 1 1 calc R . .
C23 C 1.0463(4) 0.8995(5) 0.0305(2) 0.0580(8) Uani 1 1 d . . .
H23 H 0.9899 0.9807 0.0003 0.070 Uiso 1 1 calc R . .
C16 C 0.9200(3) 0.9887(4) 0.19757(18) 0.0420(7) Uani 1 1 d . . .
H16 H 0.9539 0.9099 0.2419 0.050 Uiso 1 1 calc R . .
C27 C 1.0607(4) 1.3451(6) 0.4578(2) 0.0738(12) Uani 1 1 d . . .
H27 H 1.0599 1.3792 0.5087 0.089 Uiso 1 1 calc R . .
C4 C 0.3924(5) 0.4435(6) 0.4144(3) 0.0887(14) Uani 1 1 d . . .
H4A H 0.3219 0.4642 0.4393 0.133 Uiso 1 1 calc R . .
H4B H 0.4588 0.3724 0.4483 0.133 Uiso 1 1 calc R . .
H4C H 0.3571 0.3874 0.3643 0.133 Uiso 1 1 calc R . .


_geom_special_details            
; 
 All esds (except the esd in the dihedral angle between two l.s. planes) 
 are estimated using the full covariance matrix.  The cell esds are taken 
 into account individually in the estimation of esds in distances, angles 
 and torsion angles; correlations between esds in cell parameters are only 
 used when they are defined by crystal symmetry.  An approximate (isotropic) 
 treatment of cell esds is used for estimating esds involving l.s. planes. 
;

loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
O1 C1 1.421(4) . ?
Se1 C24 1.921(3) . ?
Se1 C16 1.982(3) . ?
C12 O2 1.447(3) . ?
C12 C13 1.509(4) . ?
C12 C14 1.522(4) . ?
C12 C11 1.529(4) . ?
C20 C19 1.376(5) . ?
C20 C21 1.380(6) . ?
C11 N1 1.464(4) . ?
N1 C17 1.483(4) . ?
N1 C8 1.529(4) . ?
O2 C15 1.431(3) . ?
C21 C22 1.357(6) . ?
C29 C24 1.374(5) . ?
C29 C28 1.381(5) . ?
C24 C25 1.382(5) . ?
C10 C8 1.537(4) . ?
C18 C23 1.379(5) . ?
C18 C19 1.389(5) . ?
C18 C15 1.507(4) . ?
C15 C16 1.525(4) . ?
C7 C6 1.539(4) . ?
C7 C1 1.543(4) . ?
C7 C8 1.549(4) . ?
C8 C9 1.524(4) . ?
C26 C27 1.362(6) . ?
C26 C25 1.375(5) . ?
C1 C2 1.503(5) . ?
C5 C3 1.503(5) . ?
C5 C6 1.524(5) . ?
C17 C16 1.524(4) . ?
C3 C4 1.514(5) . ?
C3 C2 1.533(5) . ?
C22 C23 1.373(5) . ?
C28 C27 1.364(6) . ?

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
C24 Se1 C16 94.99(12) . . ?
O2 C12 C13 103.1(2) . . ?
O2 C12 C14 109.7(2) . . ?
C13 C12 C14 110.7(3) . . ?
O2 C12 C11 112.5(2) . . ?
C13 C12 C11 112.3(2) . . ?
C14 C12 C11 108.4(3) . . ?
C19 C20 C21 119.9(4) . . ?
N1 C11 C12 116.5(2) . . ?
C11 N1 C17 109.4(2) . . ?
C11 N1 C8 114.3(2) . . ?
C17 N1 C8 114.6(2) . . ?
C15 O2 C12 118.3(2) . . ?
C22 C21 C20 120.4(3) . . ?
C24 C29 C28 119.6(3) . . ?
C29 C24 C25 119.4(3) . . ?
C29 C24 Se1 121.0(3) . . ?
C25 C24 Se1 119.6(3) . . ?
C23 C18 C19 118.4(3) . . ?
C23 C18 C15 120.6(3) . . ?
C19 C18 C15 121.0(3) . . ?
C20 C19 C18 120.2(4) . . ?
O2 C15 C18 107.4(2) . . ?
O2 C15 C16 107.7(2) . . ?
C18 C15 C16 114.7(2) . . ?
C6 C7 C1 107.3(2) . . ?
C6 C7 C8 114.5(2) . . ?
C1 C7 C8 113.2(2) . . ?
C9 C8 N1 110.4(2) . . ?
C9 C8 C10 108.2(3) . . ?
N1 C8 C10 110.6(2) . . ?
C9 C8 C7 110.1(3) . . ?
N1 C8 C7 105.6(2) . . ?
C10 C8 C7 112.0(2) . . ?
C27 C26 C25 120.9(4) . . ?
C26 C25 C24 119.8(4) . . ?
O1 C1 C2 108.0(3) . . ?
O1 C1 C7 113.8(2) . . ?
C2 C1 C7 110.5(2) . . ?
C3 C5 C6 114.3(3) . . ?
N1 C17 C16 112.7(3) . . ?
C5 C3 C4 112.0(3) . . ?
C5 C3 C2 109.4(3) . . ?
C4 C3 C2 112.0(3) . . ?
C21 C22 C23 119.9(4) . . ?
C5 C6 C7 111.4(3) . . ?
C27 C28 C29 121.0(4) . . ?
C1 C2 C3 112.2(3) . . ?
C22 C23 C18 121.1(4) . . ?
C17 C16 C15 114.0(2) . . ?
C17 C16 Se1 107.4(2) . . ?
C15 C16 Se1 110.57(19) . . ?
C26 C27 C28 119.3(3) . . ?

_diffrn_measured_fraction_theta_max 0.997
_diffrn_reflns_theta_full        23.30
_diffrn_measured_fraction_theta_full 0.997
_refine_diff_density_max         0.594
_refine_diff_density_min         -0.463
_refine_diff_density_rms         0.064
####################################################################### 
# 
# 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_javi07b
_database_code_depnum_ccdc_archive 'CCDC 1406522'
_audit_update_record             
;
2015-06-12 deposited with the CCDC.
2015-07-17 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-97
_chemical_name_systematic        
; 
 ? 
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C25 H27 N O3 S'
_chemical_absolute_configuration rmad
_chemical_formula_weight         421.54

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'

_symmetry_cell_setting           Monoclinic
_symmetry_space_group_name_H-M   P2(1)

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

_cell_length_a                   5.8067(18)
_cell_length_b                   13.672(4)
_cell_length_c                   13.807(4)
_cell_angle_alpha                90.00
_cell_angle_beta                 90.852(6)
_cell_angle_gamma                90.00
_cell_volume                     1096.0(6)
_cell_formula_units_Z            2
_cell_measurement_temperature    298(2)
_cell_measurement_reflns_used    ?
_cell_measurement_theta_min      ?
_cell_measurement_theta_max      ?

_exptl_crystal_description       prism
_exptl_crystal_colour            COLORLESS
_exptl_crystal_size_max          0.43
_exptl_crystal_size_mid          0.28
_exptl_crystal_size_min          0.09
_exptl_crystal_density_meas      ?
_exptl_crystal_density_diffrn    1.277
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             448
_exptl_absorpt_coefficient_mu    0.174
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.894271
_exptl_absorpt_correction_T_max  1.000000
_exptl_absorpt_process_details   
;
 G.M. Sheldrick. 
 SADABS: A program for absorption correction with the Siemens SMART system;  University of Göttingen, Germany, 1996. 
;

_exptl_special_details           
; 
 ? 
;

_diffrn_ambient_temperature      298(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_radiation_source         'fine-focus sealed tube'
_diffrn_radiation_monochromator  graphite
_diffrn_measurement_device_type  'Bruker P4'
_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            3161
_diffrn_reflns_av_R_equivalents  0.0000
_diffrn_reflns_av_sigmaI/netI    0.0204
_diffrn_reflns_limit_h_min       -6
_diffrn_reflns_limit_h_max       6
_diffrn_reflns_limit_k_min       -15
_diffrn_reflns_limit_k_max       15
_diffrn_reflns_limit_l_min       0
_diffrn_reflns_limit_l_max       15
_diffrn_reflns_theta_min         1.47
_diffrn_reflns_theta_max         23.28
_reflns_number_total             3161
_reflns_number_gt                3036
_reflns_threshold_expression     >2sigma(I)

_computing_data_collection       'Bruker XSCANS'
_computing_cell_refinement       'Bruker XSCANS'
_computing_data_reduction        'Bruker SHELXTL'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 1990)'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_computing_molecular_graphics    'Bruker SHELXTL'
_computing_publication_material  'Bruker SHELXTL'

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

_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'calc w=1/[σ²(Fo²)+(0.0481P)²+0.1320P] 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     SHELXL
_refine_ls_extinction_coef       0.011(2)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc²λ³/sin(2θ)]^-1/4^
_refine_ls_abs_structure_details 'Flack H D (1983), Acta Cryst. A39, 876-881'
_refine_ls_abs_structure_Flack   0.00(6)
_refine_ls_number_reflns         3161
_refine_ls_number_parameters     274
_refine_ls_number_restraints     1
_refine_ls_R_factor_all          0.0302
_refine_ls_R_factor_gt           0.0281
_refine_ls_wR_factor_ref         0.0774
_refine_ls_wR_factor_gt          0.0747
_refine_ls_goodness_of_fit_ref   1.042
_refine_ls_restrained_S_all      1.042
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000

loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_symmetry_multiplicity
_atom_site_calc_flag
_atom_site_refinement_flags
_atom_site_disorder_assembly
_atom_site_disorder_group
S1 S 1.22283(8) 0.14333(4) -0.06308(3) 0.05056(17) Uani 1 1 d . . .
O1 O 0.8530(2) 0.21850(9) 0.20684(10) 0.0417(3) Uani 1 1 d . . .
O2 O 1.2576(3) 0.04081(13) -0.05078(11) 0.0675(5) Uani 1 1 d . . .
C12 C 1.0610(3) 0.33486(15) 0.30342(14) 0.0441(5) Uani 1 1 d . . .
C3 C 1.0069(3) 0.28513(15) 0.02969(14) 0.0443(5) Uani 1 1 d . . .
H3A H 0.8409 0.2927 0.0261 0.053 Uiso 1 1 calc R . .
H3B H 1.0710 0.3170 -0.0266 0.053 Uiso 1 1 calc R . .
C23 C 0.8597(4) 0.11249(16) -0.18818(16) 0.0538(6) Uani 1 1 d . . .
H23 H 0.8019 0.0712 -0.1409 0.065 Uiso 1 1 calc R . .
C18 C 1.0658(3) 0.16141(15) -0.17253(13) 0.0461(5) Uani 1 1 d . . .
C11 C 0.5951(4) 0.08698(18) 0.30620(15) 0.0591(6) Uani 1 1 d . . .
H11 H 0.6577 0.1403 0.3391 0.071 Uiso 1 1 calc R . .
N1 N 1.0633(3) 0.18020(12) 0.02629(11) 0.0445(4) Uani 1 1 d . . .
O3 O 1.4169(2) 0.20735(14) -0.06643(12) 0.0684(5) Uani 1 1 d . . .
C1 C 0.8770(3) 0.11998(13) 0.17414(14) 0.0412(5) Uani 1 1 d . . .
H1 H 1.0220 0.0938 0.2005 0.049 Uiso 1 1 calc R . .
C19 C 1.1504(4) 0.22333(18) -0.24278(17) 0.0597(6) Uani 1 1 d . . .
H19 H 1.2876 0.2570 -0.2322 0.072 Uiso 1 1 calc R . .
C14 C 1.2381(5) 0.3929(2) 0.45124(17) 0.0670(7) Uani 1 1 d . . .
H14 H 1.3624 0.3920 0.4945 0.080 Uiso 1 1 calc R . .
C4 C 1.0977(3) 0.33632(15) 0.12101(14) 0.0437(5) Uani 1 1 d . . .
H4 H 1.0084 0.3965 0.1291 0.052 Uiso 1 1 calc R . .
C6 C 0.6800(3) 0.06170(14) 0.21626(14) 0.0435(5) Uani 1 1 d . . .
C20 C 1.0294(5) 0.2345(2) -0.32852(17) 0.0658(7) Uani 1 1 d . . .
H20 H 1.0875 0.2756 -0.3759 0.079 Uiso 1 1 calc R . .
C5 C 1.0651(3) 0.27367(14) 0.21220(14) 0.0409(5) Uani 1 1 d . . .
H5 H 1.1938 0.2275 0.2174 0.049 Uiso 1 1 calc R . .
C2 C 0.8848(4) 0.11447(14) 0.06364(14) 0.0456(5) Uani 1 1 d . . .
H2A H 0.9173 0.0478 0.0440 0.055 Uiso 1 1 calc R . .
H2B H 0.7360 0.1328 0.0364 0.055 Uiso 1 1 calc R . .
C22 C 0.7412(4) 0.12543(18) -0.27420(16) 0.0610(6) Uani 1 1 d . . .
H22 H 0.6026 0.0926 -0.2843 0.073 Uiso 1 1 calc R . .
C17 C 0.8765(4) 0.39627(19) 0.32150(18) 0.0607(6) Uani 1 1 d . . .
H17 H 0.7535 0.3986 0.2777 0.073 Uiso 1 1 calc R . .
C9 C 0.3233(4) -0.04372(18) 0.30100(19) 0.0652(7) Uani 1 1 d . . .
H9 H 0.2052 -0.0790 0.3293 0.078 Uiso 1 1 calc R . .
C13 C 1.2408(4) 0.33368(18) 0.36915(16) 0.0568(6) Uani 1 1 d . . .
H13 H 1.3661 0.2928 0.3587 0.068 Uiso 1 1 calc R . .
C21 C 0.8237(5) 0.18625(18) -0.34621(16) 0.0607(6) Uani 1 1 d . . .
C15 C 1.0536(5) 0.45238(19) 0.46863(17) 0.0672(7) Uani 1 1 d . . .
H15 H 1.0508 0.4913 0.5238 0.081 Uiso 1 1 calc R . .
C16 C 0.8723(5) 0.4538(2) 0.40324(19) 0.0694(7) Uani 1 1 d . . .
H16 H 0.7461 0.4940 0.4144 0.083 Uiso 1 1 calc R . .
C8 C 0.4033(5) -0.06950(19) 0.2117(2) 0.0725(7) Uani 1 1 d . . .
H8 H 0.3392 -0.1228 0.1792 0.087 Uiso 1 1 calc R . .
C7 C 0.5782(5) -0.01703(18) 0.16963(19) 0.0695(7) Uani 1 1 d . . .
H7 H 0.6288 -0.0350 0.1086 0.083 Uiso 1 1 calc R . .
C10 C 0.4193(5) 0.0343(2) 0.34768(17) 0.0707(7) Uani 1 1 d . . .
H10 H 0.3658 0.0524 0.4083 0.085 Uiso 1 1 calc R . .
C24 C 0.6929(6) 0.2001(3) -0.4400(2) 0.0949(10) Uani 1 1 d . . .
H24A H 0.7895 0.2324 -0.4859 0.142 Uiso 1 1 calc R . .
H24B H 0.5586 0.2393 -0.4289 0.142 Uiso 1 1 calc R . .
H24C H 0.6469 0.1375 -0.4652 0.142 Uiso 1 1 calc R . .
C25 C 1.3516(4) 0.36516(19) 0.11431(17) 0.0616(6) Uani 1 1 d . . .
H25A H 1.3995 0.3971 0.1732 0.092 Uiso 1 1 calc R . .
H25B H 1.3713 0.4089 0.0607 0.092 Uiso 1 1 calc R . .
H25C H 1.4432 0.3076 0.1049 0.092 Uiso 1 1 calc R . .


_geom_special_details            
; 
 All esds (except the esd in the dihedral angle between two l.s. planes) 
 are estimated using the full covariance matrix.  The cell esds are taken 
 into account individually in the estimation of esds in distances, angles 
 and torsion angles; correlations between esds in cell parameters are only 
 used when they are defined by crystal symmetry.  An approximate (isotropic) 
 treatment of cell esds is used for estimating esds involving l.s. planes. 
;

loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
S1 O2 1.4259(19) . ?
S1 O3 1.4283(18) . ?
S1 N1 1.6337(17) . ?
S1 C18 1.771(2) . ?
O1 C1 1.428(2) . ?
O1 C5 1.445(2) . ?
C12 C13 1.373(3) . ?
C12 C17 1.387(3) . ?
C12 C5 1.512(3) . ?
C3 N1 1.472(3) . ?
C3 C4 1.529(3) . ?
C23 C22 1.375(3) . ?
C23 C18 1.385(3) . ?
C18 C19 1.383(3) . ?
C11 C10 1.380(3) . ?
C11 C6 1.387(3) . ?
N1 C2 1.471(3) . ?
C1 C6 1.517(3) . ?
C1 C2 1.529(3) . ?
C19 C20 1.376(3) . ?
C14 C15 1.370(4) . ?
C14 C13 1.393(4) . ?
C4 C25 1.530(3) . ?
C4 C5 1.537(3) . ?
C6 C7 1.382(3) . ?
C20 C21 1.383(4) . ?
C22 C21 1.387(4) . ?
C17 C16 1.376(3) . ?
C9 C10 1.362(4) . ?
C9 C8 1.370(4) . ?
C21 C24 1.504(3) . ?
C15 C16 1.377(4) . ?
C8 C7 1.379(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
O2 S1 O3 119.73(11) . . ?
O2 S1 N1 107.10(9) . . ?
O3 S1 N1 106.98(9) . . ?
O2 S1 C18 108.00(10) . . ?
O3 S1 C18 106.46(10) . . ?
N1 S1 C18 108.12(9) . . ?
C1 O1 C5 114.93(14) . . ?
C13 C12 C17 118.0(2) . . ?
C13 C12 C5 121.51(19) . . ?
C17 C12 C5 120.43(18) . . ?
N1 C3 C4 113.46(16) . . ?
C22 C23 C18 119.5(2) . . ?
C19 C18 C23 120.08(19) . . ?
C19 C18 S1 120.02(16) . . ?
C23 C18 S1 119.90(16) . . ?
C10 C11 C6 121.1(2) . . ?
C2 N1 C3 115.20(15) . . ?
C2 N1 S1 119.13(13) . . ?
C3 N1 S1 116.97(13) . . ?
O1 C1 C6 107.26(15) . . ?
O1 C1 C2 111.50(15) . . ?
C6 C1 C2 112.97(16) . . ?
C20 C19 C18 119.3(2) . . ?
C15 C14 C13 120.4(2) . . ?
C3 C4 C25 112.88(17) . . ?
C3 C4 C5 112.04(16) . . ?
C25 C4 C5 108.88(17) . . ?
C7 C6 C11 117.1(2) . . ?
C7 C6 C1 123.37(19) . . ?
C11 C6 C1 119.49(17) . . ?
C19 C20 C21 121.9(2) . . ?
O1 C5 C12 107.90(15) . . ?
O1 C5 C4 111.36(15) . . ?
C12 C5 C4 112.19(16) . . ?
N1 C2 C1 110.56(15) . . ?
C23 C22 C21 121.5(2) . . ?
C16 C17 C12 121.1(2) . . ?
C10 C9 C8 119.1(2) . . ?
C12 C13 C14 120.9(2) . . ?
C20 C21 C22 117.8(2) . . ?
C20 C21 C24 121.1(3) . . ?
C22 C21 C24 121.2(3) . . ?
C14 C15 C16 119.1(2) . . ?
C17 C16 C15 120.4(2) . . ?
C9 C8 C7 120.4(2) . . ?
C8 C7 C6 121.4(2) . . ?
C9 C10 C11 120.8(2) . . ?

_diffrn_measured_fraction_theta_max 0.996
_diffrn_reflns_theta_full        23.28
_diffrn_measured_fraction_theta_full 0.996
_refine_diff_density_max         0.181
_refine_diff_density_min         -0.173
_refine_diff_density_rms         0.025
####################################################################### 
# 
# 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_pil02a
_database_code_depnum_ccdc_archive 'CCDC 1406523'
_audit_update_record             
;
2015-06-12 deposited with the CCDC.
2015-07-17 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-97
_chemical_name_systematic        
; 
 ? 
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C28 H37 N O2 Se'
_chemical_absolute_configuration rmad
_chemical_formula_weight         498.55

loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
N N 0.0061 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0106 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
Se Se -0.0929 2.2259 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_symmetry_cell_setting           Orthorhombic
_symmetry_space_group_name_H-M   P2(1)2(1)2(1)

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

_cell_length_a                   8.5898(17)
_cell_length_b                   10.768(2)
_cell_length_c                   28.159(6)
_cell_angle_alpha                90.00
_cell_angle_beta                 90.00
_cell_angle_gamma                90.00
_cell_volume                     2604.6(9)
_cell_formula_units_Z            4
_cell_measurement_temperature    298(2)
_cell_measurement_reflns_used    ?
_cell_measurement_theta_min      ?
_cell_measurement_theta_max      ?

_exptl_crystal_description       prism
_exptl_crystal_colour            COLORLESS
_exptl_crystal_size_max          0.43
_exptl_crystal_size_mid          0.1
_exptl_crystal_size_min          0.09
_exptl_crystal_density_meas      ?
_exptl_crystal_density_diffrn    1.271
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             1048
_exptl_absorpt_coefficient_mu    1.465
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.797109
_exptl_absorpt_correction_T_max  1.000000
_exptl_absorpt_process_details   
;
 G.M. Sheldrick. 
 SADABS: A program for absorption correction with the Siemens SMART system;  University of Göttingen, Germany, 1996. 
;

_exptl_special_details           
; 
 ? 
;

_diffrn_ambient_temperature      298(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_radiation_source         'fine-focus sealed tube'
_diffrn_radiation_monochromator  graphite
_diffrn_measurement_device_type  'Bruker P4'
_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            3759
_diffrn_reflns_av_R_equivalents  0.0000
_diffrn_reflns_av_sigmaI/netI    0.0257
_diffrn_reflns_limit_h_min       -9
_diffrn_reflns_limit_h_max       9
_diffrn_reflns_limit_k_min       0
_diffrn_reflns_limit_k_max       11
_diffrn_reflns_limit_l_min       0
_diffrn_reflns_limit_l_max       31
_diffrn_reflns_theta_min         1.45
_diffrn_reflns_theta_max         23.28
_reflns_number_total             3759
_reflns_number_gt                3488
_reflns_threshold_expression     >2sigma(I)

_computing_data_collection       'Bruker XSCANS'
_computing_cell_refinement       'Bruker XSCANS'
_computing_data_reduction        'Bruker SHELXTL'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 1990)'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_computing_molecular_graphics    'Bruker SHELXTL'
_computing_publication_material  'Bruker SHELXTL'

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

_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'calc w=1/[σ²(Fo²)+(0.0679P)²+1.2034P] 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   0.016(12)
_refine_ls_number_reflns         3759
_refine_ls_number_parameters     293
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0440
_refine_ls_R_factor_gt           0.0394
_refine_ls_wR_factor_ref         0.1096
_refine_ls_wR_factor_gt          0.1064
_refine_ls_goodness_of_fit_ref   1.080
_refine_ls_restrained_S_all      1.080
_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 0.47513(5) 0.05219(4) 0.015372(16) 0.05421(17) Uani 1 1 d . . .
O1 O 0.9666(3) 0.2015(3) 0.16818(9) 0.0425(6) Uani 1 1 d . . .
O2 O 0.9057(3) 0.1816(3) 0.06097(9) 0.0421(7) Uani 1 1 d . . .
N1 N 0.7282(4) 0.1176(3) 0.14355(12) 0.0406(8) Uani 1 1 d . . .
C23 C 0.8415(5) 0.1009(4) -0.01508(15) 0.0431(9) Uani 1 1 d . . .
C14 C 0.7760(5) 0.1482(4) 0.03173(14) 0.0392(10) Uani 1 1 d . . .
H14 H 0.7180 0.2245 0.0249 0.047 Uiso 1 1 calc R . .
C28 C 0.9709(5) 0.0254(4) -0.01723(16) 0.0546(11) Uani 1 1 d . . .
H28 H 1.0202 0.0008 0.0106 0.066 Uiso 1 1 calc R . .
C17 C 0.3392(5) -0.0549(5) 0.05167(15) 0.0496(10) Uani 1 1 d . . .
C13 C 0.6644(4) 0.0593(4) 0.05825(14) 0.0413(9) Uani 1 1 d . . .
C2 C 0.9350(5) 0.1778(4) 0.21726(14) 0.0436(10) Uani 1 1 d . . .
H2 H 0.8890 0.2528 0.2311 0.052 Uiso 1 1 calc R . .
C24 C 0.7717(6) 0.1397(5) -0.05721(16) 0.0508(12) Uani 1 1 d . . .
H24 H 0.6862 0.1926 -0.0561 0.061 Uiso 1 1 calc R . .
C1 C 0.8259(5) 0.2268(4) 0.14391(14) 0.0389(9) Uani 1 1 d . . .
H1 H 0.7708 0.2927 0.1611 0.047 Uiso 1 1 calc R . .
C8 C 0.8216(5) 0.0728(4) 0.22347(15) 0.0470(11) Uani 1 1 d . . .
H8 H 0.8756 -0.0023 0.2127 0.056 Uiso 1 1 calc R . .
C9 C 0.6731(5) 0.0839(4) 0.19247(16) 0.0509(11) Uani 1 1 d . . .
C6 C 0.9435(7) 0.0331(5) 0.30328(17) 0.0682(15) Uani 1 1 d . . .
H6A H 0.9855 -0.0466 0.2936 0.082 Uiso 1 1 calc R . .
H6B H 0.9213 0.0283 0.3370 0.082 Uiso 1 1 calc R . .
C16 C 0.7265(5) -0.0687(4) 0.06559(16) 0.0505(11) Uani 1 1 d . . .
H16A H 0.8211 -0.0646 0.0837 0.076 Uiso 1 1 calc R . .
H16B H 0.7471 -0.1064 0.0353 0.076 Uiso 1 1 calc R . .
H16C H 0.6511 -0.1175 0.0825 0.076 Uiso 1 1 calc R . .
C15 C 0.8681(5) 0.2760(4) 0.09465(13) 0.0416(10) Uani 1 1 d . . .
H15A H 0.7812 0.3240 0.0826 0.050 Uiso 1 1 calc R . .
H15B H 0.9564 0.3316 0.0976 0.050 Uiso 1 1 calc R . .
C4 C 1.0664(6) 0.1325(5) 0.29514(15) 0.0551(12) Uani 1 1 d . . .
H4 H 1.0265 0.2100 0.3087 0.066 Uiso 1 1 calc R . .
C12 C 0.6087(5) 0.1190(4) 0.10534(14) 0.0429(10) Uani 1 1 d . . .
H12A H 0.5786 0.2044 0.0992 0.051 Uiso 1 1 calc R . .
H12B H 0.5170 0.0751 0.1164 0.051 Uiso 1 1 calc R . .
C10 C 0.5574(6) 0.1805(6) 0.21201(19) 0.0719(16) Uani 1 1 d . . .
H10A H 0.6100 0.2582 0.2166 0.108 Uiso 1 1 calc R . .
H10B H 0.5163 0.1520 0.2418 0.108 Uiso 1 1 calc R . .
H10C H 0.4738 0.1915 0.1898 0.108 Uiso 1 1 calc R . .
C26 C 0.9550(8) 0.0247(6) -0.10269(19) 0.0767(18) Uani 1 1 d . . .
H26 H 0.9926 -0.0010 -0.1321 0.092 Uiso 1 1 calc R . .
C25 C 0.8283(7) 0.1006(6) -0.10045(17) 0.0660(15) Uani 1 1 d . . .
H25 H 0.7796 0.1260 -0.1283 0.079 Uiso 1 1 calc R . .
C3 C 1.0879(6) 0.1536(5) 0.24172(16) 0.0516(11) Uani 1 1 d . . .
H3A H 1.1566 0.2238 0.2368 0.062 Uiso 1 1 calc R . .
H3B H 1.1365 0.0809 0.2278 0.062 Uiso 1 1 calc R . .
C27 C 1.0285(7) -0.0145(5) -0.0614(2) 0.0743(16) Uani 1 1 d . . .
H27 H 1.1148 -0.0665 -0.0629 0.089 Uiso 1 1 calc R . .
C19 C 0.2244(7) -0.2539(5) 0.0641(2) 0.0732(16) Uani 1 1 d . . .
H19 H 0.2179 -0.3379 0.0568 0.088 Uiso 1 1 calc R . .
C21 C 0.1404(6) -0.0808(6) 0.1105(2) 0.0737(17) Uani 1 1 d . . .
H21 H 0.0795 -0.0495 0.1351 0.088 Uiso 1 1 calc R . .
C7 C 0.7928(6) 0.0554(6) 0.27692(15) 0.0626(13) Uani 1 1 d . . .
H7A H 0.7424 0.1289 0.2896 0.075 Uiso 1 1 calc R . .
H7B H 0.7236 -0.0147 0.2818 0.075 Uiso 1 1 calc R . .
C20 C 0.1301(8) -0.2043(6) 0.0981(2) 0.0768(17) Uani 1 1 d . . .
H20 H 0.0574 -0.2547 0.1131 0.092 Uiso 1 1 calc R . .
C22 C 0.2416(5) -0.0037(5) 0.08638(17) 0.0547(12) Uani 1 1 d . . .
H22 H 0.2448 0.0808 0.0931 0.066 Uiso 1 1 calc R . .
C5 C 1.2176(8) 0.1034(6) 0.31996(19) 0.0839(19) Uani 1 1 d . . .
H5A H 1.1989 0.0932 0.3533 0.126 Uiso 1 1 calc R . .
H5B H 1.2897 0.1703 0.3151 0.126 Uiso 1 1 calc R . .
H5C H 1.2606 0.0281 0.3072 0.126 Uiso 1 1 calc R . .
C18 C 0.3305(6) -0.1785(5) 0.04049(19) 0.0596(13) Uani 1 1 d . . .
H18 H 0.3951 -0.2117 0.0172 0.072 Uiso 1 1 calc R . .
C11 C 0.5958(7) -0.0455(6) 0.19028(19) 0.0820(19) Uani 1 1 d . . .
H11A H 0.5026 -0.0409 0.1715 0.123 Uiso 1 1 calc R . .
H11B H 0.5702 -0.0723 0.2218 0.123 Uiso 1 1 calc R . .
H11C H 0.6666 -0.1037 0.1761 0.123 Uiso 1 1 calc R . .


_geom_special_details            
; 
 All esds (except the esd in the dihedral angle between two l.s. planes) 
 are estimated using the full covariance matrix.  The cell esds are taken 
 into account individually in the estimation of esds in distances, angles 
 and torsion angles; correlations between esds in cell parameters are only 
 used when they are defined by crystal symmetry.  An approximate (isotropic) 
 treatment of cell esds is used for estimating esds involving l.s. planes. 
;

loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
Se1 C17 1.933(5) . ?
Se1 C13 2.027(4) . ?
O1 C1 1.415(5) . ?
O1 C2 1.431(5) . ?
O2 C15 1.427(5) . ?
O2 C14 1.431(5) . ?
N1 C1 1.445(5) . ?
N1 C12 1.487(5) . ?
N1 C9 1.501(5) . ?
C23 C28 1.378(6) . ?
C23 C24 1.393(6) . ?
C23 C14 1.521(6) . ?
C14 C13 1.547(6) . ?
C28 C27 1.405(7) . ?
C17 C18 1.370(7) . ?
C17 C22 1.401(7) . ?
C13 C16 1.492(6) . ?
C13 C12 1.550(6) . ?
C2 C8 1.503(6) . ?
C2 C3 1.505(6) . ?
C24 C25 1.377(7) . ?
C1 C15 1.528(6) . ?
C8 C7 1.537(6) . ?
C8 C9 1.550(6) . ?
C9 C10 1.540(7) . ?
C9 C11 1.545(7) . ?
C6 C7 1.511(7) . ?
C6 C4 1.521(7) . ?
C4 C5 1.508(8) . ?
C4 C3 1.532(6) . ?
C26 C25 1.363(9) . ?
C26 C27 1.389(9) . ?
C19 C20 1.362(8) . ?
C19 C18 1.391(7) . ?
C21 C20 1.378(9) . ?
C21 C22 1.381(7) . ?

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
C17 Se1 C13 101.08(17) . . ?
C1 O1 C2 109.8(3) . . ?
C15 O2 C14 112.7(3) . . ?
C1 N1 C12 113.4(3) . . ?
C1 N1 C9 111.9(3) . . ?
C12 N1 C9 116.7(3) . . ?
C28 C23 C24 119.1(4) . . ?
C28 C23 C14 122.3(4) . . ?
C24 C23 C14 118.6(4) . . ?
O2 C14 C23 107.2(3) . . ?
O2 C14 C13 111.1(3) . . ?
C23 C14 C13 116.1(3) . . ?
C23 C28 C27 120.2(5) . . ?
C18 C17 C22 120.6(5) . . ?
C18 C17 Se1 119.4(4) . . ?
C22 C17 Se1 119.8(4) . . ?
C16 C13 C14 114.6(3) . . ?
C16 C13 C12 112.0(3) . . ?
C14 C13 C12 110.4(3) . . ?
C16 C13 Se1 109.5(3) . . ?
C14 C13 Se1 103.5(3) . . ?
C12 C13 Se1 106.1(3) . . ?
O1 C2 C8 111.7(3) . . ?
O1 C2 C3 107.9(3) . . ?
C8 C2 C3 112.4(4) . . ?
C25 C24 C23 120.6(5) . . ?
O1 C1 N1 110.0(3) . . ?
O1 C1 C15 107.6(3) . . ?
N1 C1 C15 114.4(3) . . ?
C2 C8 C7 108.1(4) . . ?
C2 C8 C9 114.2(4) . . ?
C7 C8 C9 115.4(4) . . ?
N1 C9 C10 111.6(4) . . ?
N1 C9 C11 108.5(4) . . ?
C10 C9 C11 110.2(4) . . ?
N1 C9 C8 106.0(3) . . ?
C10 C9 C8 112.5(4) . . ?
C11 C9 C8 107.8(4) . . ?
C7 C6 C4 114.1(4) . . ?
O2 C15 C1 114.2(3) . . ?
C5 C4 C6 112.5(4) . . ?
C5 C4 C3 112.5(4) . . ?
C6 C4 C3 109.6(4) . . ?
N1 C12 C13 113.7(3) . . ?
C25 C26 C27 120.4(5) . . ?
C26 C25 C24 120.4(5) . . ?
C2 C3 C4 111.7(4) . . ?
C26 C27 C28 119.2(5) . . ?
C20 C19 C18 119.8(5) . . ?
C20 C21 C22 119.7(5) . . ?
C6 C7 C8 111.2(4) . . ?
C19 C20 C21 121.2(5) . . ?
C21 C22 C17 119.0(5) . . ?
C17 C18 C19 119.5(5) . . ?

_diffrn_measured_fraction_theta_max 0.999
_diffrn_reflns_theta_full        23.28
_diffrn_measured_fraction_theta_full 0.999
_refine_diff_density_max         0.853
_refine_diff_density_min         -0.296
_refine_diff_density_rms         0.062
####################################################################### 
# 
# 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_pilf
_database_code_depnum_ccdc_archive 'CCDC 1406524'
_audit_update_record             
;
2015-06-12 deposited with the CCDC.
2015-07-17 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-97
_chemical_name_systematic        
; 
 ? 
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C26 H41 N O2 Se'
_chemical_absolute_configuration rmad
_chemical_formula_weight         478.56

loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
N N 0.0061 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0106 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
Se Se -0.0929 2.2259 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_symmetry_cell_setting           Orthorhombic
_symmetry_space_group_name_H-M   P2(1)2(1)2(1)

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

_cell_length_a                   12.295(2)
_cell_length_b                   13.5593(19)
_cell_length_c                   15.728(3)
_cell_angle_alpha                90.00
_cell_angle_beta                 90.00
_cell_angle_gamma                90.00
_cell_volume                     2622.0(8)
_cell_formula_units_Z            4
_cell_measurement_temperature    298(2)
_cell_measurement_reflns_used    ?
_cell_measurement_theta_min      ?
_cell_measurement_theta_max      ?

_exptl_crystal_description       prism
_exptl_crystal_colour            COLORLESS
_exptl_crystal_size_max          0.36
_exptl_crystal_size_mid          0.30
_exptl_crystal_size_min          0.15
_exptl_crystal_density_meas      ?
_exptl_crystal_density_diffrn    1.212
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             1016
_exptl_absorpt_coefficient_mu    1.452
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.806084
_exptl_absorpt_correction_T_max  1.000000
_exptl_absorpt_process_details   
;
 G.M. Sheldrick. 
 SADABS: A program for absorption correction with the Siemens SMART system;  University of Göttingen, Germany, 1996. 
;

_exptl_special_details           
; 
 ? 
;

_diffrn_ambient_temperature      298(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_radiation_source         'fine-focus sealed tube'
_diffrn_radiation_monochromator  graphite
_diffrn_measurement_device_type  'Bruker P4'
_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            3781
_diffrn_reflns_av_R_equivalents  0.0000
_diffrn_reflns_av_sigmaI/netI    0.0497
_diffrn_reflns_limit_h_min       -13
_diffrn_reflns_limit_h_max       13
_diffrn_reflns_limit_k_min       0
_diffrn_reflns_limit_k_max       15
_diffrn_reflns_limit_l_min       0
_diffrn_reflns_limit_l_max       17
_diffrn_reflns_theta_min         1.98
_diffrn_reflns_theta_max         23.32
_reflns_number_total             3781
_reflns_number_gt                3027
_reflns_threshold_expression     >2sigma(I)

_computing_data_collection       'Bruker XSCANS'
_computing_cell_refinement       'Bruker XSCANS'
_computing_data_reduction        'Bruker SHELXTL'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 1990)'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_computing_molecular_graphics    'Bruker SHELXTL'
_computing_publication_material  'Bruker SHELXTL'

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

_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'calc w=1/[σ²(Fo²)+(0.0330P)²+0.5697P] 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   -0.003(10)
_refine_ls_number_reflns         3781
_refine_ls_number_parameters     278
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0582
_refine_ls_R_factor_gt           0.0356
_refine_ls_wR_factor_ref         0.0800
_refine_ls_wR_factor_gt          0.0706
_refine_ls_goodness_of_fit_ref   1.023
_refine_ls_restrained_S_all      1.023
_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 0.84122(3) 0.29747(3) 0.85376(3) 0.05457(15) Uani 1 1 d . . .
C12 C 0.4990(3) 0.3027(3) 0.8230(2) 0.0482(11) Uani 1 1 d . . .
H12A H 0.4925 0.3373 0.7692 0.058 Uiso 1 1 calc R . .
H12B H 0.4794 0.2343 0.8136 0.058 Uiso 1 1 calc R . .
O2 O 0.64291(19) 0.40942(17) 0.86966(16) 0.0432(7) Uani 1 1 d . . .
O1 O 0.39051(19) 0.4946(2) 0.95956(18) 0.0451(7) Uani 1 1 d . . .
C3 C 0.2175(3) 0.5483(3) 1.0074(3) 0.0582(13) Uani 1 1 d . . .
H3A H 0.2422 0.6162 1.0080 0.070 Uiso 1 1 calc R . .
H3B H 0.2343 0.5195 1.0623 0.070 Uiso 1 1 calc R . .
C21 C 0.9364(3) 0.2035(4) 0.8009(3) 0.0478(10) Uani 1 1 d . . .
C14 C 0.5718(3) 0.4543(3) 0.9291(3) 0.0414(10) Uani 1 1 d . . .
H14 H 0.5762 0.4168 0.9823 0.050 Uiso 1 1 calc R . .
N1 N 0.4245(3) 0.3462(2) 0.88465(19) 0.0407(8) Uani 1 1 d . . .
C13 C 0.6160(3) 0.3084(3) 0.8541(3) 0.0414(9) Uani 1 1 d . . .
H13 H 0.6211 0.2724 0.9080 0.050 Uiso 1 1 calc R . .
C18 C 0.7014(3) 0.2668(3) 0.7932(3) 0.0456(12) Uani 1 1 d . . .
C2 C 0.2772(3) 0.4926(3) 0.9390(3) 0.0460(11) Uani 1 1 d . . .
H2 H 0.2663 0.5263 0.8845 0.055 Uiso 1 1 calc R . .
C9 C 0.3065(3) 0.3293(3) 0.8641(3) 0.0433(10) Uani 1 1 d . . .
C10 C 0.2778(4) 0.3602(3) 0.7728(3) 0.0573(12) Uani 1 1 d . . .
H10A H 0.2926 0.4292 0.7655 0.086 Uiso 1 1 calc R . .
H10B H 0.2021 0.3478 0.7624 0.086 Uiso 1 1 calc R . .
H10C H 0.3209 0.3228 0.7333 0.086 Uiso 1 1 calc R . .
C1 C 0.4548(3) 0.4491(3) 0.8976(3) 0.0406(10) Uani 1 1 d . . .
H1 H 0.4482 0.4852 0.8438 0.049 Uiso 1 1 calc R . .
C15 C 0.6132(3) 0.5583(3) 0.9467(3) 0.0574(13) Uani 1 1 d . . .
H15 H 0.5618 0.5902 0.9856 0.069 Uiso 1 1 calc R . .
C8 C 0.2399(3) 0.3867(3) 0.9304(3) 0.0434(10) Uani 1 1 d . . .
H8 H 0.2536 0.3550 0.9854 0.052 Uiso 1 1 calc R . .
C19 C 0.6887(4) 0.1556(3) 0.7842(3) 0.0646(14) Uani 1 1 d . . .
H19A H 0.6191 0.1410 0.7595 0.097 Uiso 1 1 calc R . .
H19B H 0.6937 0.1253 0.8392 0.097 Uiso 1 1 calc R . .
H19C H 0.7452 0.1304 0.7481 0.097 Uiso 1 1 calc R . .
C22 C 0.9547(3) 0.1145(4) 0.8394(4) 0.0657(14) Uani 1 1 d . . .
H22 H 0.9205 0.0988 0.8904 0.079 Uiso 1 1 calc R . .
C26 C 0.9894(4) 0.2266(4) 0.7266(3) 0.0635(13) Uani 1 1 d . . .
H26 H 0.9777 0.2873 0.7007 0.076 Uiso 1 1 calc R . .
C17 C 0.7227(4) 0.5539(4) 0.9907(3) 0.0782(16) Uani 1 1 d . . .
H17A H 0.7174 0.5128 1.0402 0.117 Uiso 1 1 calc R . .
H17B H 0.7443 0.6191 1.0073 0.117 Uiso 1 1 calc R . .
H17C H 0.7758 0.5269 0.9524 0.117 Uiso 1 1 calc R . .
C7 C 0.1164(3) 0.3847(4) 0.9168(3) 0.0613(13) Uani 1 1 d . . .
H7A H 0.0997 0.4126 0.8616 0.074 Uiso 1 1 calc R . .
H7B H 0.0916 0.3168 0.9170 0.074 Uiso 1 1 calc R . .
C4 C 0.0947(3) 0.5461(4) 0.9936(3) 0.0668(14) Uani 1 1 d . . .
H4 H 0.0796 0.5799 0.9398 0.080 Uiso 1 1 calc R . .
C24 C 1.0770(5) 0.0703(5) 0.7273(5) 0.088(2) Uani 1 1 d . . .
H24 H 1.1238 0.0250 0.7021 0.106 Uiso 1 1 calc R . .
C20 C 0.7021(4) 0.3164(4) 0.7077(3) 0.0736(15) Uani 1 1 d . . .
H20A H 0.6364 0.3004 0.6777 0.110 Uiso 1 1 calc R . .
H20B H 0.7637 0.2939 0.6756 0.110 Uiso 1 1 calc R . .
H20C H 0.7067 0.3865 0.7152 0.110 Uiso 1 1 calc R . .
C25 C 1.0601(4) 0.1594(5) 0.6904(4) 0.0795(17) Uani 1 1 d . . .
H25 H 1.0963 0.1755 0.6404 0.095 Uiso 1 1 calc R . .
C11 C 0.2838(3) 0.2182(3) 0.8755(3) 0.0636(13) Uani 1 1 d . . .
H11A H 0.3232 0.1816 0.8333 0.095 Uiso 1 1 calc R . .
H11B H 0.2073 0.2061 0.8691 0.095 Uiso 1 1 calc R . .
H11C H 0.3067 0.1979 0.9311 0.095 Uiso 1 1 calc R . .
C23 C 1.0259(5) 0.0472(4) 0.8007(5) 0.0883(18) Uani 1 1 d . . .
H23 H 1.0381 -0.0139 0.8258 0.106 Uiso 1 1 calc R . .
C6 C 0.0556(3) 0.4418(4) 0.9848(3) 0.0701(15) Uani 1 1 d . . .
H6A H -0.0213 0.4423 0.9709 0.084 Uiso 1 1 calc R . .
H6B H 0.0641 0.4083 1.0389 0.084 Uiso 1 1 calc R . .
C5 C 0.0342(4) 0.6005(5) 1.0629(4) 0.110(2) Uani 1 1 d . . .
H5A H -0.0419 0.6025 1.0494 0.165 Uiso 1 1 calc R . .
H5B H 0.0618 0.6665 1.0673 0.165 Uiso 1 1 calc R . .
H5C H 0.0443 0.5670 1.1161 0.165 Uiso 1 1 calc R . .
C16 C 0.6197(4) 0.6207(3) 0.8664(4) 0.0858(17) Uani 1 1 d . . .
H16A H 0.6593 0.5853 0.8235 0.129 Uiso 1 1 calc R . .
H16B H 0.6564 0.6815 0.8788 0.129 Uiso 1 1 calc R . .
H16C H 0.5476 0.6345 0.8463 0.129 Uiso 1 1 calc R . .


_geom_special_details            
; 
 All esds (except the esd in the dihedral angle between two l.s. planes) 
 are estimated using the full covariance matrix.  The cell esds are taken 
 into account individually in the estimation of esds in distances, angles 
 and torsion angles; correlations between esds in cell parameters are only 
 used when they are defined by crystal symmetry.  An approximate (isotropic) 
 treatment of cell esds is used for estimating esds involving l.s. planes. 
;

loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
Se1 C21 1.919(4) . ?
Se1 C18 2.009(4) . ?
C12 N1 1.459(5) . ?
C12 C13 1.521(5) . ?
O2 C14 1.418(4) . ?
O2 C13 1.430(4) . ?
O1 C1 1.397(4) . ?
O1 C2 1.430(4) . ?
C3 C2 1.507(5) . ?
C3 C4 1.526(5) . ?
C21 C22 1.369(6) . ?
C21 C26 1.374(6) . ?
C14 C1 1.523(5) . ?
C14 C15 1.525(6) . ?
N1 C1 1.459(5) . ?
N1 C9 1.503(5) . ?
C13 C18 1.529(5) . ?
C18 C20 1.503(6) . ?
C18 C19 1.523(5) . ?
C2 C8 1.513(6) . ?
C9 C8 1.537(5) . ?
C9 C10 1.538(6) . ?
C9 C11 1.543(5) . ?
C15 C17 1.514(6) . ?
C15 C16 1.523(7) . ?
C8 C7 1.534(6) . ?
C22 C23 1.403(7) . ?
C26 C25 1.381(7) . ?
C7 C6 1.517(6) . ?
C4 C6 1.500(6) . ?
C4 C5 1.512(7) . ?
C24 C23 1.350(8) . ?
C24 C25 1.358(8) . ?

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
C21 Se1 C18 100.31(16) . . ?
N1 C12 C13 111.1(3) . . ?
C14 O2 C13 112.4(3) . . ?
C1 O1 C2 112.6(3) . . ?
C2 C3 C4 111.7(4) . . ?
C22 C21 C26 119.9(4) . . ?
C22 C21 Se1 119.6(3) . . ?
C26 C21 Se1 120.4(4) . . ?
O2 C14 C1 110.4(3) . . ?
O2 C14 C15 108.1(3) . . ?
C1 C14 C15 114.6(3) . . ?
C1 N1 C12 108.6(3) . . ?
C1 N1 C9 115.0(3) . . ?
C12 N1 C9 113.7(3) . . ?
O2 C13 C12 108.8(3) . . ?
O2 C13 C18 107.5(3) . . ?
C12 C13 C18 115.5(3) . . ?
C20 C18 C19 111.1(4) . . ?
C20 C18 C13 113.5(3) . . ?
C19 C18 C13 110.6(4) . . ?
C20 C18 Se1 109.1(3) . . ?
C19 C18 Se1 109.7(3) . . ?
C13 C18 Se1 102.4(2) . . ?
O1 C2 C3 107.7(3) . . ?
O1 C2 C8 109.5(3) . . ?
C3 C2 C8 113.0(3) . . ?
N1 C9 C8 106.9(3) . . ?
N1 C9 C10 112.4(3) . . ?
C8 C9 C10 112.0(3) . . ?
N1 C9 C11 107.4(3) . . ?
C8 C9 C11 108.6(3) . . ?
C10 C9 C11 109.4(4) . . ?
O1 C1 N1 112.0(3) . . ?
O1 C1 C14 106.7(3) . . ?
N1 C1 C14 109.3(3) . . ?
C17 C15 C16 110.7(4) . . ?
C17 C15 C14 110.1(4) . . ?
C16 C15 C14 112.4(4) . . ?
C2 C8 C7 109.2(4) . . ?
C2 C8 C9 112.3(3) . . ?
C7 C8 C9 115.1(3) . . ?
C21 C22 C23 118.9(5) . . ?
C21 C26 C25 119.9(5) . . ?
C6 C7 C8 112.4(4) . . ?
C6 C4 C5 111.6(5) . . ?
C6 C4 C3 110.4(4) . . ?
C5 C4 C3 112.0(4) . . ?
C23 C24 C25 120.0(6) . . ?
C24 C25 C26 120.5(6) . . ?
C24 C23 C22 120.7(6) . . ?
C4 C6 C7 112.8(4) . . ?

_diffrn_measured_fraction_theta_max 0.996
_diffrn_reflns_theta_full        23.32
_diffrn_measured_fraction_theta_full 0.996
_refine_diff_density_max         0.212
_refine_diff_density_min         -0.212
_refine_diff_density_rms         0.044
####################################################################### 
# 
# 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_pilk
_database_code_depnum_ccdc_archive 'CCDC 1406525'
_audit_update_record             
;
2015-06-12 deposited with the CCDC.
2015-07-17 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-97
_chemical_name_systematic        
; 
 ? 
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C22 H35 N O2'
_chemical_absolute_configuration rmad
_chemical_formula_weight         345.51

loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
N N 0.0061 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0106 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_symmetry_cell_setting           Monoclinic
_symmetry_space_group_name_H-M   P2(1)

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

_cell_length_a                   6.517(3)
_cell_length_b                   12.303(5)
_cell_length_c                   12.943(5)
_cell_angle_alpha                90.00
_cell_angle_beta                 100.402(7)
_cell_angle_gamma                90.00
_cell_volume                     1020.7(7)
_cell_formula_units_Z            2
_cell_measurement_temperature    298(2)
_cell_measurement_reflns_used    ?
_cell_measurement_theta_min      ?
_cell_measurement_theta_max      ?

_exptl_crystal_description       prism
_exptl_crystal_colour            COLORLESS
_exptl_crystal_size_max          0.47
_exptl_crystal_size_mid          0.37
_exptl_crystal_size_min          0.14
_exptl_crystal_density_meas      ?
_exptl_crystal_density_diffrn    1.124
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             380
_exptl_absorpt_coefficient_mu    0.070
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.928015
_exptl_absorpt_correction_T_max  1.000000
_exptl_absorpt_process_details   
;
 G.M. Sheldrick. 
 SADABS: A program for absorption correction with the Siemens SMART system;  University of Göttingen, Germany, 1996. 
;

_exptl_special_details           
; 
 ? 
;

_diffrn_ambient_temperature      298(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_radiation_source         'fine-focus sealed tube'
_diffrn_radiation_monochromator  graphite
_diffrn_measurement_device_type  'Bruker P4'
_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            2926
_diffrn_reflns_av_R_equivalents  0.0000
_diffrn_reflns_av_sigmaI/netI    0.0162
_diffrn_reflns_limit_h_min       -7
_diffrn_reflns_limit_h_max       7
_diffrn_reflns_limit_k_min       -13
_diffrn_reflns_limit_k_max       13
_diffrn_reflns_limit_l_min       0
_diffrn_reflns_limit_l_max       14
_diffrn_reflns_theta_min         1.60
_diffrn_reflns_theta_max         23.27
_reflns_number_total             2926
_reflns_number_gt                2852
_reflns_threshold_expression     >2sigma(I)

_computing_data_collection       'Bruker XSCANS'
_computing_cell_refinement       'Bruker XSCANS'
_computing_data_reduction        'Bruker SHELXTL'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 1990)'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_computing_molecular_graphics    'Bruker SHELXTL'
_computing_publication_material  'Bruker SHELXTL'

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

_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'calc w=1/[σ²(Fo²)+(0.0445P)²+0.0795P] 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     SHELXL
_refine_ls_extinction_coef       0.036(4)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc²λ³/sin(2θ)]^-1/4^
_refine_ls_abs_structure_details 'Flack H D (1983), Acta Cryst. A39, 876-881'
_refine_ls_abs_structure_Flack   0.3(10)
_refine_ls_number_reflns         2926
_refine_ls_number_parameters     236
_refine_ls_number_restraints     1
_refine_ls_R_factor_all          0.0287
_refine_ls_R_factor_gt           0.0278
_refine_ls_wR_factor_ref         0.0739
_refine_ls_wR_factor_gt          0.0728
_refine_ls_goodness_of_fit_ref   1.044
_refine_ls_restrained_S_all      1.044
_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
O2 O 0.60700(16) 0.53548(8) 0.80203(7) 0.0520(3) Uani 1 1 d . . .
C10 C 0.7872(2) 0.52185(12) 0.39917(11) 0.0430(3) Uani 1 1 d . . .
N1 N 0.65243(17) 0.54186(10) 0.56536(9) 0.0436(3) Uani 1 1 d . . .
C7 C 0.6957(2) 0.60437(12) 0.47033(11) 0.0459(3) Uani 1 1 d . . .
O1 O 0.5294(2) 0.38165(10) 0.42145(9) 0.0692(4) Uani 1 1 d . . .
H1 H 0.5352 0.4190 0.4744 0.104 Uiso 1 1 calc R . .
C1 C 0.6304(2) 0.43686(12) 0.34797(11) 0.0469(3) Uani 1 1 d . . .
H1A H 0.5230 0.4744 0.2978 0.056 Uiso 1 1 calc R . .
C15 C 0.8444(2) 0.51507(13) 0.64083(11) 0.0468(4) Uani 1 1 d . . .
H15A H 0.8859 0.5779 0.6849 0.056 Uiso 1 1 calc R . .
H15B H 0.9554 0.4996 0.6022 0.056 Uiso 1 1 calc R . .
C2 C 0.7319(3) 0.35315(13) 0.28808(13) 0.0560(4) Uani 1 1 d . . .
H2A H 0.6256 0.3033 0.2540 0.067 Uiso 1 1 calc R . .
H2B H 0.8311 0.3116 0.3376 0.067 Uiso 1 1 calc R . .
C13 C 0.7509(2) 0.44649(12) 0.81528(11) 0.0455(3) Uani 1 1 d . . .
C6 C 0.8856(3) 0.57468(13) 0.31253(13) 0.0576(4) Uani 1 1 d . . .
H6A H 0.7785 0.6119 0.2634 0.069 Uiso 1 1 calc R . .
H6B H 0.9879 0.6282 0.3435 0.069 Uiso 1 1 calc R . .
C17 C 0.6561(2) 0.34891(13) 0.86285(11) 0.0471(4) Uani 1 1 d . . .
C11 C 0.5012(2) 0.59547(15) 0.62019(13) 0.0566(4) Uani 1 1 d . . .
H11A H 0.3741 0.6089 0.5700 0.068 Uiso 1 1 calc R . .
H11B H 0.5574 0.6654 0.6459 0.068 Uiso 1 1 calc R . .
C3 C 0.8440(3) 0.40093(14) 0.20582(12) 0.0579(4) Uani 1 1 d . . .
H3 H 0.7389 0.4337 0.1510 0.069 Uiso 1 1 calc R . .
C22 C 0.7406(3) 0.24566(13) 0.86242(12) 0.0569(4) Uani 1 1 d . . .
H22 H 0.8530 0.2341 0.8285 0.068 Uiso 1 1 calc R . .
C8 C 0.4928(3) 0.65204(14) 0.40982(13) 0.0589(4) Uani 1 1 d . . .
H8A H 0.3870 0.5968 0.3995 0.088 Uiso 1 1 calc R . .
H8B H 0.5152 0.6781 0.3428 0.088 Uiso 1 1 calc R . .
H8C H 0.4488 0.7111 0.4491 0.088 Uiso 1 1 calc R . .
C5 C 0.9904(3) 0.49021(16) 0.25419(14) 0.0663(5) Uani 1 1 d . . .
H5A H 1.0480 0.5260 0.1991 0.080 Uiso 1 1 calc R . .
H5B H 1.1052 0.4578 0.3025 0.080 Uiso 1 1 calc R . .
C12 C 0.4470(2) 0.53178(15) 0.71127(12) 0.0561(4) Uani 1 1 d . . .
H12A H 0.3192 0.5607 0.7289 0.067 Uiso 1 1 calc R . .
H12B H 0.4216 0.4566 0.6901 0.067 Uiso 1 1 calc R . .
C19 C 0.4105(3) 0.27529(19) 0.96229(19) 0.0843(6) Uani 1 1 d . . .
H19 H 0.2978 0.2858 0.9961 0.101 Uiso 1 1 calc R . .
C9 C 0.8451(3) 0.69961(13) 0.50383(14) 0.0604(4) Uani 1 1 d . . .
H9A H 0.8473 0.7465 0.4447 0.091 Uiso 1 1 calc R . .
H9B H 0.9829 0.6721 0.5289 0.091 Uiso 1 1 calc R . .
H9C H 0.7984 0.7398 0.5588 0.091 Uiso 1 1 calc R . .
C4 C 0.9577(4) 0.31401(19) 0.15476(16) 0.0856(6) Uani 1 1 d . . .
H4A H 1.0655 0.2826 0.2065 0.128 Uiso 1 1 calc R . .
H4B H 1.0186 0.3460 0.0998 0.128 Uiso 1 1 calc R . .
H4C H 0.8607 0.2585 0.1257 0.128 Uiso 1 1 calc R . .
C16 C 0.9342(3) 0.48954(15) 0.89466(12) 0.0597(4) Uani 1 1 d . . .
H16A H 0.9943 0.5510 0.8654 0.089 Uiso 1 1 calc R . .
H16B H 1.0375 0.4335 0.9111 0.089 Uiso 1 1 calc R . .
H16C H 0.8864 0.5112 0.9575 0.089 Uiso 1 1 calc R . .
C14 C 0.8189(2) 0.41826(12) 0.71056(11) 0.0474(4) Uani 1 1 d . . .
H14A H 0.9506 0.3796 0.7257 0.057 Uiso 1 1 calc R . .
H14B H 0.7165 0.3693 0.6716 0.057 Uiso 1 1 calc R . .
C18 C 0.4888(3) 0.36248(16) 0.91356(15) 0.0688(5) Uani 1 1 d . . .
H18 H 0.4280 0.4307 0.9151 0.083 Uiso 1 1 calc R . .
C21 C 0.6616(3) 0.15962(15) 0.91127(13) 0.0669(5) Uani 1 1 d . . .
H21 H 0.7213 0.0911 0.9101 0.080 Uiso 1 1 calc R . .
C20 C 0.4966(3) 0.17443(16) 0.96120(16) 0.0740(5) Uani 1 1 d . . .
H20 H 0.4433 0.1164 0.9941 0.089 Uiso 1 1 calc R . .
H10 H 0.904(2) 0.4842(13) 0.4461(11) 0.047(4) Uiso 1 1 d . . .


_geom_special_details            
; 
 All esds (except the esd in the dihedral angle between two l.s. planes) 
 are estimated using the full covariance matrix.  The cell esds are taken 
 into account individually in the estimation of esds in distances, angles 
 and torsion angles; correlations between esds in cell parameters are only 
 used when they are defined by crystal symmetry.  An approximate (isotropic) 
 treatment of cell esds is used for estimating esds involving l.s. planes. 
;

loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
O2 C12 1.4238(19) . ?
O2 C13 1.4315(18) . ?
C10 C1 1.527(2) . ?
C10 C6 1.533(2) . ?
C10 C7 1.560(2) . ?
N1 C11 1.4705(19) . ?
N1 C15 1.4786(18) . ?
N1 C7 1.5195(19) . ?
C7 C8 1.527(2) . ?
C7 C9 1.535(2) . ?
O1 C1 1.4230(18) . ?
C1 C2 1.511(2) . ?
C15 C14 1.521(2) . ?
C2 C3 1.514(2) . ?
C13 C16 1.523(2) . ?
C13 C17 1.530(2) . ?
C13 C14 1.540(2) . ?
C6 C5 1.517(2) . ?
C17 C18 1.380(2) . ?
C17 C22 1.385(2) . ?
C11 C12 1.510(2) . ?
C3 C5 1.514(3) . ?
C3 C4 1.519(3) . ?
C22 C21 1.380(2) . ?
C19 C20 1.363(3) . ?
C19 C18 1.387(3) . ?
C21 C20 1.363(3) . ?

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 O2 C13 116.15(11) . . ?
C1 C10 C6 107.97(12) . . ?
C1 C10 C7 113.88(12) . . ?
C6 C10 C7 114.26(13) . . ?
C11 N1 C15 109.99(11) . . ?
C11 N1 C7 113.70(11) . . ?
C15 N1 C7 112.90(11) . . ?
N1 C7 C8 109.85(12) . . ?
N1 C7 C9 111.02(12) . . ?
C8 C7 C9 107.33(13) . . ?
N1 C7 C10 107.16(11) . . ?
C8 C7 C10 109.57(12) . . ?
C9 C7 C10 111.91(12) . . ?
O1 C1 C2 108.40(12) . . ?
O1 C1 C10 113.01(12) . . ?
C2 C1 C10 111.62(13) . . ?
N1 C15 C14 113.35(12) . . ?
C1 C2 C3 114.04(13) . . ?
O2 C13 C16 103.41(12) . . ?
O2 C13 C17 110.19(11) . . ?
C16 C13 C17 109.02(13) . . ?
O2 C13 C14 110.70(12) . . ?
C16 C13 C14 110.91(12) . . ?
C17 C13 C14 112.24(12) . . ?
C5 C6 C10 111.03(13) . . ?
C18 C17 C22 117.50(15) . . ?
C18 C17 C13 120.49(14) . . ?
C22 C17 C13 121.90(13) . . ?
N1 C11 C12 114.57(13) . . ?
C5 C3 C2 109.80(13) . . ?
C5 C3 C4 111.73(16) . . ?
C2 C3 C4 111.57(15) . . ?
C21 C22 C17 121.35(15) . . ?
C3 C5 C6 113.34(14) . . ?
O2 C12 C11 112.82(13) . . ?
C20 C19 C18 120.90(18) . . ?
C15 C14 C13 115.16(12) . . ?
C17 C18 C19 120.63(17) . . ?
C20 C21 C22 120.43(17) . . ?
C19 C20 C21 119.20(18) . . ?

_diffrn_measured_fraction_theta_max 0.998
_diffrn_reflns_theta_full        23.27
_diffrn_measured_fraction_theta_full 0.998
_refine_diff_density_max         0.094
_refine_diff_density_min         -0.090
_refine_diff_density_rms         0.021
####################################################################### 
# 
# 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_pill
_database_code_depnum_ccdc_archive 'CCDC 1406526'
_audit_update_record             
;
2015-06-12 deposited with the CCDC.
2015-07-17 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-97
_chemical_name_systematic        
; 
 ? 
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C22 H32 Cl N O2'
_chemical_absolute_configuration rmad
_chemical_formula_weight         377.94

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'
Cl Cl 0.1484 0.1585 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_symmetry_cell_setting           Orthorhombic
_symmetry_space_group_name_H-M   P2(1)2(1)2(1)

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

_cell_length_a                   8.8571(8)
_cell_length_b                   15.0597(14)
_cell_length_c                   15.5921(14)
_cell_angle_alpha                90.00
_cell_angle_beta                 90.00
_cell_angle_gamma                90.00
_cell_volume                     2079.8(3)
_cell_formula_units_Z            4
_cell_measurement_temperature    298(2)
_cell_measurement_reflns_used    ?
_cell_measurement_theta_min      ?
_cell_measurement_theta_max      ?

_exptl_crystal_description       prism
_exptl_crystal_colour            COLORLESS
_exptl_crystal_size_max          0.38
_exptl_crystal_size_mid          0.37
_exptl_crystal_size_min          0.27
_exptl_crystal_density_meas      ?
_exptl_crystal_density_diffrn    1.207
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             816
_exptl_absorpt_coefficient_mu    0.199
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.878404
_exptl_absorpt_correction_T_max  1.000000
_exptl_absorpt_process_details   
;
 G.M. Sheldrick. 
 SADABS: A program for absorption correction with the Siemens SMART system;  University of Göttingen, Germany, 1996. 
;

_exptl_special_details           
; 
 ? 
;

_diffrn_ambient_temperature      298(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_radiation_source         'fine-focus sealed tube'
_diffrn_radiation_monochromator  graphite
_diffrn_measurement_device_type  'CCD area detector'
_diffrn_measurement_method       'phi and omega scans'
_diffrn_detector_area_resol_mean ?
_diffrn_standards_number         ?
_diffrn_standards_interval_count ?
_diffrn_standards_interval_time  ?
_diffrn_standards_decay_%        ?
_diffrn_reflns_number            2995
_diffrn_reflns_av_R_equivalents  0.0000
_diffrn_reflns_av_sigmaI/netI    0.0090
_diffrn_reflns_limit_h_min       -9
_diffrn_reflns_limit_h_max       9
_diffrn_reflns_limit_k_min       0
_diffrn_reflns_limit_k_max       16
_diffrn_reflns_limit_l_min       0
_diffrn_reflns_limit_l_max       17
_diffrn_reflns_theta_min         1.88
_diffrn_reflns_theta_max         23.32
_reflns_number_total             2995
_reflns_number_gt                2838
_reflns_threshold_expression     >2sigma(I)

_computing_data_collection       'Bruker SMART'
_computing_cell_refinement       'Bruker SMART'
_computing_data_reduction        'Bruker SHELXTL'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 1990)'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_computing_molecular_graphics    'Bruker SHELXTL'
_computing_publication_material  'Bruker SHELXTL'

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

_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'calc w=1/[σ²(Fo²)+(0.0363P)²+0.2069P] 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     SHELXL
_refine_ls_extinction_coef       0.0070(9)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc²λ³/sin(2θ)]^-1/4^
_refine_ls_abs_structure_details 'Flack H D (1983), Acta Cryst. A39, 876-881'
_refine_ls_abs_structure_Flack   -0.06(5)
_refine_ls_number_reflns         2995
_refine_ls_number_parameters     240
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0268
_refine_ls_R_factor_gt           0.0249
_refine_ls_wR_factor_ref         0.0649
_refine_ls_wR_factor_gt          0.0633
_refine_ls_goodness_of_fit_ref   1.064
_refine_ls_restrained_S_all      1.064
_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
Cl1 Cl 0.83062(6) 0.50417(3) 0.61213(3) 0.07382(17) Uani 1 1 d . . .
O1 O 0.67445(13) 0.84259(6) 0.75970(6) 0.0489(3) Uani 1 1 d . . .
N1 N 0.61134(13) 0.69507(8) 0.80605(8) 0.0407(3) Uani 1 1 d . . .
O2 O 0.82530(13) 0.69365(7) 0.66954(6) 0.0549(3) Uani 1 1 d . . .
C14 C 0.6758(2) 0.72564(11) 0.65701(10) 0.0533(4) Uani 1 1 d . . .
H14A H 0.6142 0.6779 0.6342 0.064 Uiso 1 1 calc R . .
H14B H 0.6780 0.7729 0.6147 0.064 Uiso 1 1 calc R . .
C13 C 0.84030(18) 0.63116(10) 0.73806(9) 0.0459(4) Uani 1 1 d . . .
C8 C 0.59877(17) 0.82056(9) 0.90881(9) 0.0417(3) Uani 1 1 d . . .
H8 H 0.7041 0.8105 0.9254 0.050 Uiso 1 1 calc R . .
C9 C 0.53259(16) 0.72860(10) 0.88501(10) 0.0434(3) Uani 1 1 d . . .
C12 C 0.76966(16) 0.66958(10) 0.81934(9) 0.0421(3) Uani 1 1 d . . .
H12A H 0.7752 0.6258 0.8649 0.051 Uiso 1 1 calc R . .
H12B H 0.8268 0.7213 0.8373 0.051 Uiso 1 1 calc R . .
C1 C 0.60355(18) 0.76018(10) 0.73766(9) 0.0458(4) Uani 1 1 d . . .
H1 H 0.4969 0.7720 0.7255 0.055 Uiso 1 1 calc R . .
C2 C 0.60213(18) 0.88280(10) 0.83189(10) 0.0451(4) Uani 1 1 d . . .
H2 H 0.4979 0.8971 0.8160 0.054 Uiso 1 1 calc R . .
C7 C 0.5235(2) 0.86808(11) 0.98408(11) 0.0541(4) Uani 1 1 d . . .
H7A H 0.4192 0.8809 0.9698 0.065 Uiso 1 1 calc R . .
H7B H 0.5242 0.8295 1.0339 0.065 Uiso 1 1 calc R . .
C4 C 0.61407(19) 1.01606(10) 0.92883(11) 0.0563(4) Uani 1 1 d . . .
H4 H 0.5107 1.0328 0.9133 0.068 Uiso 1 1 calc R . .
C17 C 0.7742(2) 0.47006(10) 0.78027(10) 0.0520(4) Uani 1 1 d . . .
C15 C 1.00976(19) 0.62143(12) 0.75146(13) 0.0607(4) Uani 1 1 d . . .
H15A H 1.0555 0.6000 0.6996 0.091 Uiso 1 1 calc R . .
H15B H 1.0284 0.5801 0.7971 0.091 Uiso 1 1 calc R . .
H15C H 1.0522 0.6781 0.7661 0.091 Uiso 1 1 calc R . .
C16 C 0.76246(19) 0.54244(10) 0.71442(10) 0.0493(4) Uani 1 1 d . . .
H16 H 0.6548 0.5554 0.7073 0.059 Uiso 1 1 calc R . .
C10 C 0.5541(2) 0.66310(11) 0.95839(10) 0.0522(4) Uani 1 1 d . . .
H10A H 0.5262 0.6046 0.9397 0.078 Uiso 1 1 calc R . .
H10B H 0.4916 0.6803 1.0059 0.078 Uiso 1 1 calc R . .
H10C H 0.6580 0.6631 0.9759 0.078 Uiso 1 1 calc R . .
C11 C 0.36274(18) 0.73240(13) 0.86554(12) 0.0590(4) Uani 1 1 d . . .
H11A H 0.3432 0.7791 0.8251 0.088 Uiso 1 1 calc R . .
H11B H 0.3081 0.7438 0.9176 0.088 Uiso 1 1 calc R . .
H11C H 0.3307 0.6767 0.8418 0.088 Uiso 1 1 calc R . .
C3 C 0.6832(2) 0.96801(11) 0.85196(11) 0.0543(4) Uani 1 1 d . . .
H3A H 0.6793 1.0066 0.8022 0.065 Uiso 1 1 calc R . .
H3B H 0.7884 0.9552 0.8639 0.065 Uiso 1 1 calc R . .
C18 C 0.8990(3) 0.41530(12) 0.78846(14) 0.0739(6) Uani 1 1 d . . .
H18 H 0.9796 0.4209 0.7506 0.089 Uiso 1 1 calc R . .
C6 C 0.6047(2) 0.95393(11) 1.00533(12) 0.0603(5) Uani 1 1 d . . .
H6A H 0.7060 0.9403 1.0250 0.072 Uiso 1 1 calc R . .
H6B H 0.5520 0.9836 1.0517 0.072 Uiso 1 1 calc R . .
C21 C 0.6610(4) 0.39530(14) 0.90084(13) 0.0877(7) Uani 1 1 d . . .
H21 H 0.5806 0.3887 0.9386 0.105 Uiso 1 1 calc R . .
C22 C 0.6549(2) 0.45787(11) 0.83576(11) 0.0633(5) Uani 1 1 d . . .
H22 H 0.5685 0.4923 0.8294 0.076 Uiso 1 1 calc R . .
C5 C 0.7000(3) 1.10097(12) 0.94919(15) 0.0820(6) Uani 1 1 d . . .
H5A H 0.6512 1.1315 0.9956 0.123 Uiso 1 1 calc R . .
H5B H 0.7015 1.1385 0.8994 0.123 Uiso 1 1 calc R . .
H5C H 0.8017 1.0865 0.9654 0.123 Uiso 1 1 calc R . .
C19 C 0.9039(4) 0.35240(15) 0.85289(19) 0.0990(9) Uani 1 1 d . . .
H19 H 0.9879 0.3158 0.8581 0.119 Uiso 1 1 calc R . .
C20 C 0.7870(5) 0.34347(16) 0.90873(18) 0.1075(10) Uani 1 1 d . . .
H20 H 0.7928 0.3018 0.9526 0.129 Uiso 1 1 calc R . .


_geom_special_details            
; 
 All esds (except the esd in the dihedral angle between two l.s. planes) 
 are estimated using the full covariance matrix.  The cell esds are taken 
 into account individually in the estimation of esds in distances, angles 
 and torsion angles; correlations between esds in cell parameters are only 
 used when they are defined by crystal symmetry.  An approximate (isotropic) 
 treatment of cell esds is used for estimating esds involving l.s. planes. 
;

loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
Cl1 C16 1.8001(15) . ?
O1 C2 1.4297(18) . ?
O1 C1 1.4328(18) . ?
N1 C1 1.4503(18) . ?
N1 C12 1.4686(18) . ?
N1 C9 1.5023(19) . ?
O2 C14 1.422(2) . ?
O2 C13 1.4301(18) . ?
C14 C1 1.504(2) . ?
C13 C15 1.522(2) . ?
C13 C12 1.527(2) . ?
C13 C16 1.548(2) . ?
C8 C2 1.522(2) . ?
C8 C7 1.527(2) . ?
C8 C9 1.549(2) . ?
C9 C10 1.522(2) . ?
C9 C11 1.536(2) . ?
C2 C3 1.503(2) . ?
C7 C6 1.516(2) . ?
C4 C6 1.518(2) . ?
C4 C5 1.522(2) . ?
C4 C3 1.528(2) . ?
C17 C22 1.378(3) . ?
C17 C18 1.386(3) . ?
C17 C16 1.501(2) . ?
C18 C19 1.381(3) . ?
C21 C20 1.368(4) . ?
C21 C22 1.386(3) . ?
C19 C20 1.359(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
C2 O1 C1 111.06(11) . . ?
C1 N1 C12 109.02(11) . . ?
C1 N1 C9 110.69(11) . . ?
C12 N1 C9 114.55(11) . . ?
C14 O2 C13 114.34(12) . . ?
O2 C14 C1 113.48(12) . . ?
O2 C13 C15 104.92(13) . . ?
O2 C13 C12 109.42(12) . . ?
C15 C13 C12 109.06(13) . . ?
O2 C13 C16 110.41(12) . . ?
C15 C13 C16 112.88(13) . . ?
C12 C13 C16 110.01(12) . . ?
C2 C8 C7 108.99(12) . . ?
C2 C8 C9 111.66(12) . . ?
C7 C8 C9 115.96(12) . . ?
N1 C9 C10 109.89(12) . . ?
N1 C9 C11 107.78(13) . . ?
C10 C9 C11 107.16(13) . . ?
N1 C9 C8 108.73(11) . . ?
C10 C9 C8 110.61(12) . . ?
C11 C9 C8 112.63(13) . . ?
N1 C12 C13 111.91(12) . . ?
O1 C1 N1 112.86(11) . . ?
O1 C1 C14 108.27(13) . . ?
N1 C1 C14 111.15(12) . . ?
O1 C2 C3 108.14(12) . . ?
O1 C2 C8 111.61(11) . . ?
C3 C2 C8 111.76(13) . . ?
C6 C7 C8 111.13(13) . . ?
C6 C4 C5 112.41(16) . . ?
C6 C4 C3 110.26(13) . . ?
C5 C4 C3 111.17(15) . . ?
C22 C17 C18 118.36(17) . . ?
C22 C17 C16 118.25(15) . . ?
C18 C17 C16 123.39(17) . . ?
C17 C16 C13 115.66(12) . . ?
C17 C16 Cl1 110.51(10) . . ?
C13 C16 Cl1 109.76(11) . . ?
C2 C3 C4 112.09(14) . . ?
C19 C18 C17 120.0(2) . . ?
C7 C6 C4 112.32(14) . . ?
C20 C21 C22 119.1(3) . . ?
C17 C22 C21 121.3(2) . . ?
C20 C19 C18 120.7(2) . . ?
C19 C20 C21 120.5(2) . . ?

_diffrn_measured_fraction_theta_max 0.999
_diffrn_reflns_theta_full        23.32
_diffrn_measured_fraction_theta_full 0.999
_refine_diff_density_max         0.109
_refine_diff_density_min         -0.114
_refine_diff_density_rms         0.024


#===END


