# Electronic Supplementary Material (ESI) for Dalton Transactions.
# This journal is © The Royal Society of Chemistry 2017

####################################################################### 
# 
# 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_liu_a
_database_code_depnum_ccdc_archive 'CCDC 1515484'
_audit_update_record             
;
2017-01-13 deposited with the CCDC.
2017-01-26 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2014/7
_shelx_SHELXL_version_number     2014/7
_chemical_name_systematic        ?
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C22 H27 F3 N2 O3 S Se'
_chemical_formula_weight         535.47

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'
F F 0.0171 0.0103 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
S S 0.1246 0.1234 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
Se Se -0.0929 2.2259 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_space_group_crystal_system      monoclinic
_space_group_IT_number           15
_space_group_name_H-M_alt        'C 2/c'
_space_group_name_Hall           '-C 2yc'

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

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

_cell_length_a                   33.690(4)
_cell_length_b                   8.5921(9)
_cell_length_c                   18.017(2)
_cell_angle_alpha                90
_cell_angle_beta                 110.240(7)
_cell_angle_gamma                90
_cell_volume                     4893.2(10)
_cell_formula_units_Z            8
_cell_measurement_temperature    150(2)
_cell_measurement_reflns_used    9558
_cell_measurement_theta_min      2.58
_cell_measurement_theta_max      27.14

_exptl_crystal_description       block
_exptl_crystal_colour            colorless
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.454
_exptl_crystal_F_000             2192
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.200
_exptl_crystal_size_mid          0.120
_exptl_crystal_size_min          0.100
_exptl_absorpt_coefficient_mu    1.668
_shelx_estimated_absorpt_T_min   ?
_shelx_estimated_absorpt_T_max   ?
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.6702
_exptl_absorpt_correction_T_max  0.7456
_exptl_absorpt_process_details   ?
_exptl_absorpt_special_details   ?
_diffrn_ambient_temperature      150(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_source                   ?
_diffrn_measurement_device_type  'Bruker APEX-II CCD'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            40631
_diffrn_reflns_av_unetI/netI     0.0302
_diffrn_reflns_av_R_equivalents  0.0436
_diffrn_reflns_limit_h_min       -43
_diffrn_reflns_limit_h_max       43
_diffrn_reflns_limit_k_min       -11
_diffrn_reflns_limit_k_max       11
_diffrn_reflns_limit_l_min       -23
_diffrn_reflns_limit_l_max       23
_diffrn_reflns_theta_min         2.306
_diffrn_reflns_theta_max         27.482
_diffrn_reflns_theta_full        25.242
_diffrn_measured_fraction_theta_max 1.000
_diffrn_measured_fraction_theta_full 1.000
_diffrn_reflns_Laue_measured_fraction_max 1.000
_diffrn_reflns_Laue_measured_fraction_full 1.000
_diffrn_reflns_point_group_measured_fraction_max 1.000
_diffrn_reflns_point_group_measured_fraction_full 1.000
_reflns_number_total             5615
_reflns_number_gt                4162
_reflns_threshold_expression     'I > 2σ(I)'
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_max     .
_reflns_Friedel_fraction_full    .

_reflns_special_details          
;
 Reflections were merged by SHELXL according to the crystal
 class for the calculation of statistics and refinement.
 
 _reflns_Friedel_fraction is defined as the number of unique
 Friedel pairs measured divided by the number that would be
 possible theoretically, ignoring centric projections and
 systematic absences.
;

_computing_data_collection       ?
_computing_cell_refinement       ?
_computing_data_reduction        ?
_computing_structure_solution    ?
_computing_structure_refinement  'SHELXL-2014/7 (Sheldrick, 2014)'
_computing_molecular_graphics    ?
_computing_publication_material  ?
_refine_special_details          ?
_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0518P)²+11.7948P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     ?
_atom_sites_solution_secondary   ?
_atom_sites_solution_hydrogens   mixed
_refine_ls_hydrogen_treatment    mixed
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       .
_refine_ls_number_reflns         5615
_refine_ls_number_parameters     292
_refine_ls_number_restraints     1
_refine_ls_R_factor_all          0.0686
_refine_ls_R_factor_gt           0.0455
_refine_ls_wR_factor_ref         0.1305
_refine_ls_wR_factor_gt          0.1187
_refine_ls_goodness_of_fit_ref   1.199
_refine_ls_restrained_S_all      1.200
_refine_ls_shift/su_max          0.001
_refine_ls_shift/su_mean         0.000

loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_site_symmetry_order
_atom_site_calc_flag
_atom_site_refinement_flags_posn
_atom_site_refinement_flags_adp
_atom_site_refinement_flags_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
S002 S 0.37994(2) 0.20498(9) 0.20920(4) 0.02307(18) Uani 1 1 d . . . . .
F003 F 0.31673(6) 0.1947(2) 0.26366(12) 0.0381(5) Uani 1 1 d . . . . .
F004 F 0.33435(7) 0.4254(2) 0.24186(14) 0.0451(6) Uani 1 1 d . . . . .
F005 F 0.29935(7) 0.2791(3) 0.14412(14) 0.0531(6) Uani 1 1 d . . . . .
O006 O 0.40922(8) 0.2289(3) 0.28828(14) 0.0368(6) Uani 1 1 d . . . . .
O007 O 0.38668(8) 0.3022(3) 0.15005(15) 0.0372(6) Uani 1 1 d . . . . .
N008 N 0.42406(8) 0.2881(3) 0.60473(15) 0.0229(5) Uani 1 1 d . . . . .
N009 N 0.35556(8) 0.2898(3) 0.53866(14) 0.0213(5) Uani 1 1 d . . . . .
O00A O 0.37019(8) 0.0452(3) 0.18765(16) 0.0392(6) Uani 1 1 d . . . . .
C00B C 0.46841(9) 0.2696(3) 0.61634(18) 0.0222(6) Uani 1 1 d . . . . .
C00C C 0.39382(10) 0.2765(3) 0.53485(17) 0.0215(6) Uani 1 1 d . . . . .
C00D C 0.31687(9) 0.2961(4) 0.47125(17) 0.0217(6) Uani 1 1 d . . . . .
C00E C 0.25754(10) 0.1695(4) 0.37886(19) 0.0276(7) Uani 1 1 d . . . . .
H00D H 0.2409 0.0785 0.3612 0.033 Uiso 1 1 calc R U . . .
C00F C 0.49217(10) 0.4015(4) 0.61415(19) 0.0275(7) Uani 1 1 d . . . . .
C00G C 0.30487(10) 0.4385(4) 0.43227(18) 0.0239(6) Uani 1 1 d . . . . .
C00H C 0.26887(10) 0.4400(4) 0.36463(19) 0.0254(7) Uani 1 1 d . . . . .
H00E H 0.2602 0.5353 0.3371 0.031 Uiso 1 1 calc R U . . .
C00I C 0.24518(9) 0.3063(4) 0.33604(18) 0.0248(6) Uani 1 1 d . . . . .
C00J C 0.29320(10) 0.1608(4) 0.44644(19) 0.0264(7) Uani 1 1 d . . . . .
C00K C 0.52774(10) 0.1046(4) 0.6336(2) 0.0314(7) Uani 1 1 d . . . . .
H00F H 0.5401 0.0038 0.6409 0.038 Uiso 1 1 calc R U . . .
C00L C 0.40576(10) 0.3096(4) 0.66774(17) 0.0255(7) Uani 1 1 d . . . . .
H00G H 0.4159 0.4072 0.6974 0.031 Uiso 1 1 calc R U . . .
H00H H 0.4128 0.2209 0.7051 0.031 Uiso 1 1 calc R U . . .
C00M C 0.48561(10) 0.1209(4) 0.6274(2) 0.0282(7) Uani 1 1 d . . . . .
C00N C 0.35825(10) 0.3169(4) 0.62135(17) 0.0259(7) Uani 1 1 d . . . . .
H00I H 0.3429 0.2352 0.6392 0.031 Uiso 1 1 calc R U . . .
H00J H 0.3465 0.4199 0.6272 0.031 Uiso 1 1 calc R U . . .
C00O C 0.55209(10) 0.2317(4) 0.62932(19) 0.0283(7) Uani 1 1 d . . . . .
C00P C 0.53415(11) 0.3785(4) 0.6211(2) 0.0317(8) Uani 1 1 d . . . . .
H00K H 0.5511 0.4664 0.6201 0.038 Uiso 1 1 calc R U . . .
C00R C 0.33037(11) 0.2794(4) 0.2150(2) 0.0293(7) Uani 1 1 d . . . . .
C00S C 0.33021(12) 0.5842(4) 0.4607(2) 0.0383(9) Uani 1 1 d . . . . .
H00O H 0.3543 0.5613 0.5088 0.057 Uiso 1 1 calc R U . . .
H00P H 0.3406 0.6227 0.4196 0.057 Uiso 1 1 calc R U . . .
H00Q H 0.3123 0.6636 0.4723 0.057 Uiso 1 1 calc R U . . .
C00T C 0.59763(11) 0.2112(5) 0.6351(2) 0.0428(9) Uani 1 1 d . . . . .
H00R H 0.6098 0.3129 0.6309 0.064 Uiso 1 1 calc R U . . .
H00S H 0.6138 0.1635 0.6860 0.064 Uiso 1 1 calc R U . . .
H00T H 0.5988 0.1438 0.5920 0.064 Uiso 1 1 calc R U . . .
C00U C 0.47342(14) 0.5620(4) 0.6032(3) 0.0503(11) Uani 1 1 d . . . . .
H00U H 0.4437 0.5559 0.5995 0.075 Uiso 1 1 calc R U . . .
H00V H 0.4892 0.6271 0.6485 0.075 Uiso 1 1 calc R U . . .
H00W H 0.4751 0.6077 0.5545 0.075 Uiso 1 1 calc R U . . .
C00V C 0.30646(13) 0.0098(4) 0.4908(3) 0.0474(11) Uani 1 1 d . . . . .
H00X H 0.3322 0.0266 0.5366 0.071 Uiso 1 1 calc R U . . .
H00Y H 0.2838 -0.0273 0.5087 0.071 Uiso 1 1 calc R U . . .
H00Z H 0.3120 -0.0680 0.4557 0.071 Uiso 1 1 calc R U . . .
C00W C 0.45971(13) -0.0197(4) 0.6309(3) 0.0523(12) Uani 1 1 d . . . . .
H01A H 0.4774 -0.1132 0.6390 0.078 Uiso 1 1 calc R U . . .
H01B H 0.4491 -0.0083 0.6749 0.078 Uiso 1 1 calc R U . . .
H01C H 0.4358 -0.0291 0.5812 0.078 Uiso 1 1 calc R U . . .
Se1 Se 0.40686(2) 0.24504(4) 0.44249(2) 0.03511(13) Uani 1 1 d D . . . .
H1 H 0.3782(6) 0.251(4) 0.414(2) 0.035 Uiso 1 1 d D U . . .
C00Q C 0.20809(10) 0.3110(4) 0.2601(2) 0.0328(8) Uani 1 1 d . . . . .
H2 H 0.2044 0.4172 0.2389 0.049 Uiso 1 1 calc R U . . .
H3 H 0.2131 0.2401 0.2218 0.049 Uiso 1 1 calc R U . . .
H4 H 0.1825 0.2789 0.2701 0.049 Uiso 1 1 calc R U . . .


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

loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
S002 O007 1.433(2) . ?
S002 O00A 1.434(2) . ?
S002 O006 1.440(2) . ?
S002 C00R 1.825(3) . ?
F003 C00R 1.337(4) . ?
F004 C00R 1.335(4) . ?
F005 C00R 1.342(4) . ?
N008 C00C 1.321(4) . ?
N008 C00B 1.444(4) . ?
N008 C00L 1.479(4) . ?
N009 C00C 1.319(4) . ?
N009 C00D 1.443(4) . ?
N009 C00N 1.479(4) . ?
C00B C00M 1.389(4) . ?
C00B C00F 1.396(4) . ?
C00C Se1 1.882(3) . ?
C00D C00J 1.393(4) . ?
C00D C00G 1.399(4) . ?
C00E C00J 1.385(4) . ?
C00E C00I 1.389(5) . ?
C00E H00D 0.9500 . ?
C00F C00P 1.390(5) . ?
C00F C00U 1.501(5) . ?
C00G C00H 1.391(4) . ?
C00G C00S 1.502(4) . ?
C00H C00I 1.391(4) . ?
C00H H00E 0.9500 . ?
C00I C00Q 1.500(4) . ?
C00J C00V 1.508(5) . ?
C00K C00O 1.384(5) . ?
C00K C00M 1.392(5) . ?
C00K H00F 0.9500 . ?
C00L C00N 1.529(4) . ?
C00L H00G 0.9900 . ?
C00L H00H 0.9900 . ?
C00M C00W 1.504(5) . ?
C00N H00I 0.9900 . ?
C00N H00J 0.9900 . ?
C00O C00P 1.384(5) . ?
C00O C00T 1.512(5) . ?
C00P H00K 0.9500 . ?
C00S H00O 0.9800 . ?
C00S H00P 0.9800 . ?
C00S H00Q 0.9800 . ?
C00T H00R 0.9800 . ?
C00T H00S 0.9800 . ?
C00T H00T 0.9800 . ?
C00U H00U 0.9800 . ?
C00U H00V 0.9800 . ?
C00U H00W 0.9800 . ?
C00V H00X 0.9800 . ?
C00V H00Y 0.9800 . ?
C00V H00Z 0.9800 . ?
C00W H01A 0.9800 . ?
C00W H01B 0.9800 . ?
C00W H01C 0.9800 . ?
Se1 H1 0.925(19) . ?
C00Q H2 0.9800 . ?
C00Q H3 0.9800 . ?
C00Q H4 0.9800 . ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
O007 S002 O00A 115.94(16) . . ?
O007 S002 O006 114.98(16) . . ?
O00A S002 O006 114.75(16) . . ?
O007 S002 C00R 102.84(15) . . ?
O00A S002 C00R 102.86(16) . . ?
O006 S002 C00R 102.75(15) . . ?
C00C N008 C00B 123.2(3) . . ?
C00C N008 C00L 110.6(2) . . ?
C00B N008 C00L 126.0(2) . . ?
C00C N009 C00D 125.0(3) . . ?
C00C N009 C00N 110.2(2) . . ?
C00D N009 C00N 124.4(2) . . ?
C00M C00B C00F 122.4(3) . . ?
C00M C00B N008 118.8(3) . . ?
C00F C00B N008 118.8(3) . . ?
N009 C00C N008 112.9(3) . . ?
N009 C00C Se1 126.1(2) . . ?
N008 C00C Se1 121.0(2) . . ?
C00J C00D C00G 122.3(3) . . ?
C00J C00D N009 119.3(3) . . ?
C00G C00D N009 118.4(3) . . ?
C00J C00E C00I 122.4(3) . . ?
C00J C00E H00D 118.8 . . ?
C00I C00E H00D 118.8 . . ?
C00P C00F C00B 117.2(3) . . ?
C00P C00F C00U 120.8(3) . . ?
C00B C00F C00U 122.0(3) . . ?
C00H C00G C00D 117.4(3) . . ?
C00H C00G C00S 120.8(3) . . ?
C00D C00G C00S 121.8(3) . . ?
C00G C00H C00I 122.1(3) . . ?
C00G C00H H00E 118.9 . . ?
C00I C00H H00E 118.9 . . ?
C00E C00I C00H 118.0(3) . . ?
C00E C00I C00Q 121.6(3) . . ?
C00H C00I C00Q 120.4(3) . . ?
C00E C00J C00D 117.6(3) . . ?
C00E C00J C00V 121.3(3) . . ?
C00D C00J C00V 121.1(3) . . ?
C00O C00K C00M 121.6(3) . . ?
C00O C00K H00F 119.2 . . ?
C00M C00K H00F 119.2 . . ?
N008 C00L C00N 102.8(2) . . ?
N008 C00L H00G 111.2 . . ?
C00N C00L H00G 111.2 . . ?
N008 C00L H00H 111.2 . . ?
C00N C00L H00H 111.2 . . ?
H00G C00L H00H 109.1 . . ?
C00B C00M C00K 117.9(3) . . ?
C00B C00M C00W 121.7(3) . . ?
C00K C00M C00W 120.4(3) . . ?
N009 C00N C00L 103.4(2) . . ?
N009 C00N H00I 111.1 . . ?
C00L C00N H00I 111.1 . . ?
N009 C00N H00J 111.1 . . ?
C00L C00N H00J 111.1 . . ?
H00I C00N H00J 109.0 . . ?
C00K C00O C00P 118.7(3) . . ?
C00K C00O C00T 120.7(3) . . ?
C00P C00O C00T 120.6(3) . . ?
C00O C00P C00F 122.1(3) . . ?
C00O C00P H00K 118.9 . . ?
C00F C00P H00K 118.9 . . ?
F004 C00R F003 106.8(3) . . ?
F004 C00R F005 107.1(3) . . ?
F003 C00R F005 107.0(3) . . ?
F004 C00R S002 111.8(2) . . ?
F003 C00R S002 112.1(2) . . ?
F005 C00R S002 111.8(2) . . ?
C00G C00S H00O 109.5 . . ?
C00G C00S H00P 109.5 . . ?
H00O C00S H00P 109.5 . . ?
C00G C00S H00Q 109.5 . . ?
H00O C00S H00Q 109.5 . . ?
H00P C00S H00Q 109.5 . . ?
C00O C00T H00R 109.5 . . ?
C00O C00T H00S 109.5 . . ?
H00R C00T H00S 109.5 . . ?
C00O C00T H00T 109.5 . . ?
H00R C00T H00T 109.5 . . ?
H00S C00T H00T 109.5 . . ?
C00F C00U H00U 109.5 . . ?
C00F C00U H00V 109.5 . . ?
H00U C00U H00V 109.5 . . ?
C00F C00U H00W 109.5 . . ?
H00U C00U H00W 109.5 . . ?
H00V C00U H00W 109.5 . . ?
C00J C00V H00X 109.5 . . ?
C00J C00V H00Y 109.5 . . ?
H00X C00V H00Y 109.5 . . ?
C00J C00V H00Z 109.5 . . ?
H00X C00V H00Z 109.5 . . ?
H00Y C00V H00Z 109.5 . . ?
C00M C00W H01A 109.5 . . ?
C00M C00W H01B 109.5 . . ?
H01A C00W H01B 109.5 . . ?
C00M C00W H01C 109.5 . . ?
H01A C00W H01C 109.5 . . ?
H01B C00W H01C 109.5 . . ?
C00C Se1 H1 88(2) . . ?
C00I C00Q H2 109.5 . . ?
C00I C00Q H3 109.5 . . ?
H2 C00Q H3 109.5 . . ?
C00I C00Q H4 109.5 . . ?
H2 C00Q H4 109.5 . . ?
H3 C00Q H4 109.5 . . ?

_refine_diff_density_max         1.856
_refine_diff_density_min         -1.507
_refine_diff_density_rms         0.086

####################################################################### 
# 
# 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_liu_a
_database_code_depnum_ccdc_archive 'CCDC 1515485'
_audit_update_record             
;
2017-01-13 deposited with the CCDC.
2017-01-26 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2014/7
_shelx_SHELXL_version_number     2014/7
_chemical_name_systematic        ?
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C22 H27 F3 N2 O3 S2'
_chemical_formula_weight         488.57

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'
F F 0.0171 0.0103 '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'

_space_group_crystal_system      triclinic
_space_group_IT_number           2
_space_group_name_H-M_alt        'P -1'
_space_group_name_Hall           '-P 1'

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

loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x, -y, -z'

_cell_length_a                   8.783(13)
_cell_length_b                   16.48(2)
_cell_length_c                   17.56(2)
_cell_angle_alpha                73.04(6)
_cell_angle_beta                 89.36(5)
_cell_angle_gamma                78.37(4)
_cell_volume                     2378(6)
_cell_formula_units_Z            4
_cell_measurement_temperature    150(2)
_cell_measurement_reflns_used    201
_cell_measurement_theta_min      5.277
_cell_measurement_theta_max      48.217

_exptl_crystal_description       block
_exptl_crystal_colour            colorless
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.365
_exptl_crystal_F_000             1024
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.210
_exptl_crystal_size_mid          0.130
_exptl_crystal_size_min          0.110
_exptl_absorpt_coefficient_mu    0.273
_shelx_estimated_absorpt_T_min   ?
_shelx_estimated_absorpt_T_max   ?
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.6952
_exptl_absorpt_correction_T_max  0.7456
_exptl_absorpt_process_details   ?
_exptl_absorpt_special_details   ?
_diffrn_ambient_temperature      150(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_source                   ?
_diffrn_measurement_device_type  'Bruker APEX-II CCD'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            34133
_diffrn_reflns_av_unetI/netI     0.0644
_diffrn_reflns_av_R_equivalents  0.0479
_diffrn_reflns_limit_h_min       -11
_diffrn_reflns_limit_h_max       11
_diffrn_reflns_limit_k_min       -21
_diffrn_reflns_limit_k_max       21
_diffrn_reflns_limit_l_min       -22
_diffrn_reflns_limit_l_max       20
_diffrn_reflns_theta_min         1.214
_diffrn_reflns_theta_max         27.796
_diffrn_reflns_theta_full        25.242
_diffrn_measured_fraction_theta_max 0.966
_diffrn_measured_fraction_theta_full 0.993
_diffrn_reflns_Laue_measured_fraction_max 0.966
_diffrn_reflns_Laue_measured_fraction_full 0.993
_diffrn_reflns_point_group_measured_fraction_max 0.966
_diffrn_reflns_point_group_measured_fraction_full 0.993
_reflns_number_total             10900
_reflns_number_gt                7313
_reflns_threshold_expression     'I > 2σ(I)'
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_max     .
_reflns_Friedel_fraction_full    .

_reflns_special_details          
;
 Reflections were merged by SHELXL according to the crystal
 class for the calculation of statistics and refinement.
 
 _reflns_Friedel_fraction is defined as the number of unique
 Friedel pairs measured divided by the number that would be
 possible theoretically, ignoring centric projections and
 systematic absences.
;

_computing_data_collection       ?
_computing_cell_refinement       ?
_computing_data_reduction        ?
_computing_structure_solution    ?
_computing_structure_refinement  'SHELXL-2014/7 (Sheldrick, 2014)'
_computing_molecular_graphics    ?
_computing_publication_material  ?
_refine_special_details          ?
_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0656P)²+5.8739P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     ?
_atom_sites_solution_secondary   ?
_atom_sites_solution_hydrogens   mixed
_refine_ls_hydrogen_treatment    mixed
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       .
_refine_ls_number_reflns         10900
_refine_ls_number_parameters     585
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.1027
_refine_ls_R_factor_gt           0.0639
_refine_ls_wR_factor_ref         0.1885
_refine_ls_wR_factor_gt          0.1693
_refine_ls_goodness_of_fit_ref   1.058
_refine_ls_restrained_S_all      1.058
_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_site_symmetry_order
_atom_site_calc_flag
_atom_site_refinement_flags_posn
_atom_site_refinement_flags_adp
_atom_site_refinement_flags_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
S001 S 0.52547(11) 0.82713(6) 0.73028(5) 0.0231(2) Uani 1 1 d . . . . .
S002 S 0.22033(11) 0.73309(6) 0.23140(5) 0.0242(2) Uani 1 1 d . . . . .
S003 S 0.18663(12) 0.68442(6) 0.44395(6) 0.0284(2) Uani 1 1 d . . . . .
S004 S 0.65554(13) 0.68244(6) 0.94457(6) 0.0307(2) Uani 1 1 d . . . . .
F005 F -0.0641(3) 0.80072(18) 0.16838(16) 0.0487(7) Uani 1 1 d . . . . .
F006 F 0.6948(3) 0.67223(16) 0.74801(16) 0.0502(7) Uani 1 1 d . . . . .
F007 F 0.5863(4) 0.73423(17) 0.63052(16) 0.0511(7) Uani 1 1 d . . . . .
O008 O 0.6299(3) 0.83916(18) 0.78762(16) 0.0305(6) Uani 1 1 d . . . . .
F009 F 0.7839(3) 0.77417(19) 0.66810(17) 0.0504(7) Uani 1 1 d . . . . .
O00A O 0.4766(4) 0.89989(18) 0.66140(17) 0.0381(7) Uani 1 1 d . . . . .
O00B O 0.2643(4) 0.71537(19) 0.15815(16) 0.0368(7) Uani 1 1 d . . . . .
O00C O 0.3277(3) 0.76906(19) 0.26698(17) 0.0354(7) Uani 1 1 d . . . . .
O00D O 0.1582(4) 0.66706(19) 0.28672(17) 0.0382(7) Uani 1 1 d . . . . .
O00E O 0.4062(3) 0.7819(2) 0.76384(18) 0.0375(7) Uani 1 1 d . . . . .
N00F N 0.5867(3) 0.79453(18) 1.03329(17) 0.0189(6) Uani 1 1 d . . . . .
F00G F 0.0007(3) 0.8497(2) 0.26210(18) 0.0589(8) Uani 1 1 d . . . . .
F00H F 0.0879(4) 0.89031(17) 0.14617(19) 0.0598(8) Uani 1 1 d . . . . .
N00I N 0.1533(4) 0.79782(19) 0.53267(17) 0.0219(6) Uani 1 1 d . . . . .
N00J N 0.6645(3) 0.65673(18) 1.10029(17) 0.0212(6) Uani 1 1 d . . . . .
N00K N 0.2052(4) 0.65907(18) 0.59971(17) 0.0221(6) Uani 1 1 d . . . . .
C00L C 0.5396(4) 0.8705(2) 0.9660(2) 0.0189(7) Uani 1 1 d . . . . .
C00M C 0.4566(4) 1.0102(2) 0.8303(2) 0.0207(7) Uani 1 1 d . . . . .
C00N C 0.2268(4) 0.5672(2) 0.6113(2) 0.0205(7) Uani 1 1 d . . . . .
C00O C 0.7311(4) 0.5664(2) 1.1125(2) 0.0212(7) Uani 1 1 d . . . . .
C00P C 0.0501(4) 1.0129(2) 0.3280(2) 0.0221(7) Uani 1 1 d . . . . .
C00Q C 0.6327(4) 0.7145(2) 1.0297(2) 0.0199(7) Uani 1 1 d . . . . .
C00R C 0.6026(4) 0.9911(2) 0.8687(2) 0.0229(7) Uani 1 1 d . . . . .
H00G H 0.6742 1.0272 0.8476 0.027 Uiso 1 1 calc R U . . .
C00S C 0.1810(4) 0.7170(2) 0.5294(2) 0.0208(7) Uani 1 1 d . . . . .
C00T C 0.6481(4) 0.9214(2) 0.9366(2) 0.0214(7) Uani 1 1 d . . . . .
C00U C -0.0371(4) 0.9089(2) 0.4376(2) 0.0232(7) Uani 1 1 d . . . . .
C00V C 0.2027(4) 0.9791(2) 0.3593(2) 0.0261(8) Uani 1 1 d . . . . .
H00H H 0.2840 1.0046 0.3328 0.031 Uiso 1 1 calc R U . . .
C00W C -0.0677(4) 0.9784(2) 0.3686(2) 0.0247(8) Uani 1 1 d . . . . .
H00I H -0.1724 1.0026 0.3491 0.030 Uiso 1 1 calc R U . . .
C00X C 0.1174(4) 0.8741(2) 0.4648(2) 0.0210(7) Uani 1 1 d . . . . .
C00Y C 0.1574(5) 0.7984(2) 0.6170(2) 0.0245(8) Uani 1 1 d . . . . .
H00J H 0.0563 0.8286 0.6306 0.029 Uiso 1 1 calc R U . . .
H00K H 0.2405 0.8268 0.6277 0.029 Uiso 1 1 calc R U . . .
C00Z C 0.5788(4) 0.7948(2) 1.1178(2) 0.0218(7) Uani 1 1 d . . . . .
H00L H 0.4703 0.8141 1.1311 0.026 Uiso 1 1 calc R U . . .
H00M H 0.6438 0.8329 1.1291 0.026 Uiso 1 1 calc R U . . .
C010 C 0.3498(4) 0.9605(2) 0.8640(2) 0.0247(8) Uani 1 1 d . . . . .
H01A H 0.2475 0.9751 0.8402 0.030 Uiso 1 1 calc R U . . .
C011 C 0.6431(4) 0.6995(2) 1.1641(2) 0.0240(8) Uani 1 1 d . . . . .
H01B H 0.7431 0.6925 1.1931 0.029 Uiso 1 1 calc R U . . .
H01C H 0.5682 0.6759 1.2026 0.029 Uiso 1 1 calc R U . . .
C012 C 0.2653(5) 0.3931(2) 0.6229(2) 0.0273(8) Uani 1 1 d . . . . .
C013 C 0.6996(5) 0.4234(2) 1.1246(2) 0.0276(8) Uani 1 1 d . . . . .
H01D H 0.6343 0.3831 1.1280 0.033 Uiso 1 1 calc R U . . .
C014 C 0.1912(5) 0.7020(2) 0.6636(2) 0.0279(8) Uani 1 1 d . . . . .
H01E H 0.2892 0.6856 0.6969 0.033 Uiso 1 1 calc R U . . .
H01F H 0.1050 0.6870 0.6982 0.033 Uiso 1 1 calc R U . . .
C015 C 0.6541(5) 0.7481(2) 0.6928(2) 0.0277(8) Uani 1 1 d . . . . .
C016 C 0.6328(4) 0.5095(2) 1.1165(2) 0.0261(8) Uani 1 1 d . . . . .
C017 C 0.3917(5) 0.4309(2) 0.6199(2) 0.0303(9) Uani 1 1 d . . . . .
H01G H 0.4930 0.3962 0.6219 0.036 Uiso 1 1 calc R U . . .
C018 C 0.8608(5) 0.3947(2) 1.1280(2) 0.0262(8) Uani 1 1 d . . . . .
C019 C 0.2394(4) 0.9095(2) 0.4279(2) 0.0250(8) Uani 1 1 d . . . . .
C01A C 0.0953(4) 0.5308(2) 0.6155(2) 0.0283(8) Uani 1 1 d . . . . .
C01B C 0.3768(4) 0.5180(2) 0.6141(2) 0.0292(8) Uani 1 1 d . . . . .
C01C C 0.8940(4) 0.5402(2) 1.1166(2) 0.0273(8) Uani 1 1 d . . . . .
C01D C 0.9546(4) 0.4535(2) 1.1250(2) 0.0293(8) Uani 1 1 d . . . . .
H01H H 1.0644 0.4338 1.1288 0.035 Uiso 1 1 calc R U . . .
C01E C 0.3882(4) 0.8896(2) 0.9318(2) 0.0231(7) Uani 1 1 d . . . . .
C01F C 0.1182(5) 0.4433(3) 0.6220(2) 0.0314(9) Uani 1 1 d . . . . .
H01I H 0.0304 0.4171 0.6260 0.038 Uiso 1 1 calc R U . . .
C01G C 0.0159(5) 1.0829(3) 0.2494(2) 0.0314(9) Uani 1 1 d . . . . .
H01J H 0.1130 1.0996 0.2291 0.047 Uiso 1 1 calc R U . . .
H01K H -0.0314 1.0612 0.2111 0.047 Uiso 1 1 calc R U . . .
H01L H -0.0561 1.1335 0.2568 0.047 Uiso 1 1 calc R U . . .
C01H C 0.4165(5) 1.0798(2) 0.7523(2) 0.0283(8) Uani 1 1 d . . . . .
H01M H 0.5045 1.1085 0.7372 0.042 Uiso 1 1 calc R U . . .
H01N H 0.3941 1.0539 0.7112 0.042 Uiso 1 1 calc R U . . .
H01O H 0.3248 1.1225 0.7576 0.042 Uiso 1 1 calc R U . . .
C01I C 0.0543(5) 0.8231(3) 0.2002(3) 0.0330(9) Uani 1 1 d . . . . .
C01J C 0.9314(5) 0.3011(2) 1.1345(3) 0.0372(10) Uani 1 1 d . . . . .
H01P H 0.8482 0.2691 1.1358 0.056 Uiso 1 1 calc R U . . .
H01Q H 0.9939 0.2986 1.0883 0.056 Uiso 1 1 calc R U . . .
H01R H 0.9979 0.2750 1.1834 0.056 Uiso 1 1 calc R U . . .
C01K C 0.2729(5) 0.8341(3) 0.9642(3) 0.0386(10) Uani 1 1 d . . . . .
H01S H 0.3194 0.7875 1.0118 0.058 Uiso 1 1 calc R U . . .
H01T H 0.1798 0.8695 0.9783 0.058 Uiso 1 1 calc R U . . .
H01U H 0.2443 0.8088 0.9237 0.058 Uiso 1 1 calc R U . . .
C01L C 0.8096(5) 0.9005(3) 0.9749(3) 0.0366(10) Uani 1 1 d . . . . .
H01V H 0.8200 0.8495 1.0219 0.055 Uiso 1 1 calc R U . . .
H01W H 0.8864 0.8884 0.9366 0.055 Uiso 1 1 calc R U . . .
H01X H 0.8275 0.9501 0.9911 0.055 Uiso 1 1 calc R U . . .
C01M C 0.2862(6) 0.2989(3) 0.6262(3) 0.0462(12) Uani 1 1 d . . . . .
H01Y H 0.1842 0.2831 0.6280 0.069 Uiso 1 1 calc R U . . .
H01Z H 0.3378 0.2899 0.5787 0.069 Uiso 1 1 calc R U . . .
H02A H 0.3502 0.2627 0.6740 0.069 Uiso 1 1 calc R U . . .
C01N C 0.9997(5) 0.6023(3) 1.1135(3) 0.0454(12) Uani 1 1 d . . . . .
H02B H 0.9369 0.6604 1.1075 0.068 Uiso 1 1 calc R U . . .
H02C H 1.0649 0.5831 1.1630 0.068 Uiso 1 1 calc R U . . .
H02D H 1.0661 0.6040 1.0681 0.068 Uiso 1 1 calc R U . . .
C01O C -0.1691(5) 0.8726(3) 0.4802(3) 0.0394(11) Uani 1 1 d . . . . .
H02E H -0.1276 0.8242 0.5274 0.059 Uiso 1 1 calc R U . . .
H02F H -0.2397 0.9180 0.4966 0.059 Uiso 1 1 calc R U . . .
H02G H -0.2260 0.8520 0.4443 0.059 Uiso 1 1 calc R U . . .
C01P C 0.4056(5) 0.8746(3) 0.4602(3) 0.0455(12) Uani 1 1 d . . . . .
H02H H 0.4737 0.9083 0.4258 0.068 Uiso 1 1 calc R U . . .
H02I H 0.4146 0.8793 0.5143 0.068 Uiso 1 1 calc R U . . .
H02J H 0.4367 0.8136 0.4616 0.068 Uiso 1 1 calc R U . . .
C01Q C 0.4578(5) 0.5387(3) 1.1106(3) 0.0434(11) Uani 1 1 d . . . . .
H02K H 0.4098 0.4889 1.1147 0.065 Uiso 1 1 calc R U . . .
H02L H 0.4245 0.5634 1.1540 0.065 Uiso 1 1 calc R U . . .
H02M H 0.4255 0.5827 1.0592 0.065 Uiso 1 1 calc R U . . .
C01R C -0.0657(5) 0.5841(3) 0.6129(4) 0.0589(16) Uani 1 1 d . . . . .
H02N H -0.0596 0.6441 0.6082 0.088 Uiso 1 1 calc R U . . .
H02O H -0.1264 0.5829 0.5669 0.088 Uiso 1 1 calc R U . . .
H02P H -0.1164 0.5601 0.6620 0.088 Uiso 1 1 calc R U . . .
C01S C 0.5184(5) 0.5575(3) 0.6100(4) 0.0565(15) Uani 1 1 d . . . . .
H02Q H 0.4859 0.6191 0.6061 0.085 Uiso 1 1 calc R U . . .
H02R H 0.5858 0.5277 0.6583 0.085 Uiso 1 1 calc R U . . .
H02S H 0.5757 0.5514 0.5631 0.085 Uiso 1 1 calc R U . . .
H1 H 0.162(4) 0.760(2) 0.405(2) 0.016(9) Uiso 1 1 d . . . . .
H2 H 0.610(5) 0.755(3) 0.904(2) 0.029(11) 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
S001 O00A 1.429(3) . ?
S001 O00E 1.430(3) . ?
S001 O008 1.451(3) . ?
S001 C015 1.816(4) . ?
S002 O00D 1.427(3) . ?
S002 O00B 1.432(3) . ?
S002 O00C 1.444(3) . ?
S002 C01I 1.816(5) . ?
S003 C00S 1.732(4) . ?
S003 H1 1.21(3) . ?
S004 C00Q 1.723(4) . ?
S004 H2 1.19(4) . ?
F005 C01I 1.349(5) . ?
F006 C015 1.323(5) . ?
F007 C015 1.348(5) . ?
F009 C015 1.324(5) . ?
N00F C00Q 1.319(5) . ?
N00F C00L 1.439(5) . ?
N00F C00Z 1.486(5) . ?
F00G C01I 1.333(5) . ?
F00H C01I 1.314(5) . ?
N00I C00S 1.323(5) . ?
N00I C00X 1.440(5) . ?
N00I C00Y 1.484(5) . ?
N00J C00Q 1.316(5) . ?
N00J C00O 1.438(5) . ?
N00J C011 1.480(5) . ?
N00K C00S 1.311(5) . ?
N00K C00N 1.440(5) . ?
N00K C014 1.484(5) . ?
C00L C00T 1.393(5) . ?
C00L C01E 1.403(5) . ?
C00M C010 1.385(5) . ?
C00M C00R 1.389(5) . ?
C00M C01H 1.499(5) . ?
C00N C01B 1.395(5) . ?
C00N C01A 1.396(5) . ?
C00O C016 1.385(5) . ?
C00O C01C 1.405(5) . ?
C00P C00W 1.374(5) . ?
C00P C00V 1.395(5) . ?
C00P C01G 1.506(5) . ?
C00R C00T 1.389(5) . ?
C00R H00G 0.9500 . ?
C00T C01L 1.507(5) . ?
C00U C00W 1.387(5) . ?
C00U C00X 1.393(5) . ?
C00U C01O 1.503(6) . ?
C00V C019 1.387(5) . ?
C00V H00H 0.9500 . ?
C00W H00I 0.9500 . ?
C00X C019 1.387(5) . ?
C00Y C014 1.529(5) . ?
C00Y H00J 0.9900 . ?
C00Y H00K 0.9900 . ?
C00Z C011 1.534(5) . ?
C00Z H00L 0.9900 . ?
C00Z H00M 0.9900 . ?
C010 C01E 1.390(5) . ?
C010 H01A 0.9500 . ?
C011 H01B 0.9900 . ?
C011 H01C 0.9900 . ?
C012 C017 1.372(6) . ?
C012 C01F 1.385(6) . ?
C012 C01M 1.509(6) . ?
C013 C016 1.388(5) . ?
C013 C018 1.395(6) . ?
C013 H01D 0.9500 . ?
C014 H01E 0.9900 . ?
C014 H01F 0.9900 . ?
C016 C01Q 1.511(6) . ?
C017 C01B 1.388(6) . ?
C017 H01G 0.9500 . ?
C018 C01D 1.383(6) . ?
C018 C01J 1.513(5) . ?
C019 C01P 1.509(6) . ?
C01A C01F 1.385(6) . ?
C01A C01R 1.500(6) . ?
C01B C01S 1.508(6) . ?
C01C C01D 1.384(6) . ?
C01C C01N 1.505(6) . ?
C01D H01H 0.9500 . ?
C01E C01K 1.498(6) . ?
C01F H01I 0.9500 . ?
C01G H01J 0.9800 . ?
C01G H01K 0.9800 . ?
C01G H01L 0.9800 . ?
C01H H01M 0.9800 . ?
C01H H01N 0.9800 . ?
C01H H01O 0.9800 . ?
C01J H01P 0.9800 . ?
C01J H01Q 0.9800 . ?
C01J H01R 0.9800 . ?
C01K H01S 0.9800 . ?
C01K H01T 0.9800 . ?
C01K H01U 0.9800 . ?
C01L H01V 0.9800 . ?
C01L H01W 0.9800 . ?
C01L H01X 0.9800 . ?
C01M H01Y 0.9800 . ?
C01M H01Z 0.9800 . ?
C01M H02A 0.9800 . ?
C01N H02B 0.9800 . ?
C01N H02C 0.9800 . ?
C01N H02D 0.9800 . ?
C01O H02E 0.9800 . ?
C01O H02F 0.9800 . ?
C01O H02G 0.9800 . ?
C01P H02H 0.9800 . ?
C01P H02I 0.9800 . ?
C01P H02J 0.9800 . ?
C01Q H02K 0.9800 . ?
C01Q H02L 0.9800 . ?
C01Q H02M 0.9800 . ?
C01R H02N 0.9800 . ?
C01R H02O 0.9800 . ?
C01R H02P 0.9800 . ?
C01S H02Q 0.9800 . ?
C01S H02R 0.9800 . ?
C01S H02S 0.9800 . ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
O00A S001 O00E 115.0(2) . . ?
O00A S001 O008 115.86(19) . . ?
O00E S001 O008 115.25(19) . . ?
O00A S001 C015 104.5(2) . . ?
O00E S001 C015 102.5(2) . . ?
O008 S001 C015 100.85(19) . . ?
O00D S002 O00B 114.8(2) . . ?
O00D S002 O00C 114.3(2) . . ?
O00B S002 O00C 116.1(2) . . ?
O00D S002 C01I 103.7(2) . . ?
O00B S002 C01I 102.9(2) . . ?
O00C S002 C01I 102.5(2) . . ?
C00S S003 H1 88.7(17) . . ?
C00Q S004 H2 90.7(19) . . ?
C00Q N00F C00L 125.6(3) . . ?
C00Q N00F C00Z 110.0(3) . . ?
C00L N00F C00Z 124.2(3) . . ?
C00S N00I C00X 125.1(3) . . ?
C00S N00I C00Y 109.9(3) . . ?
C00X N00I C00Y 124.9(3) . . ?
C00Q N00J C00O 124.1(3) . . ?
C00Q N00J C011 110.6(3) . . ?
C00O N00J C011 124.8(3) . . ?
C00S N00K C00N 123.4(3) . . ?
C00S N00K C014 110.5(3) . . ?
C00N N00K C014 125.9(3) . . ?
C00T C00L C01E 122.5(3) . . ?
C00T C00L N00F 118.3(3) . . ?
C01E C00L N00F 119.2(3) . . ?
C010 C00M C00R 118.3(3) . . ?
C010 C00M C01H 120.1(3) . . ?
C00R C00M C01H 121.5(3) . . ?
C01B C00N C01A 121.8(3) . . ?
C01B C00N N00K 119.5(3) . . ?
C01A C00N N00K 118.6(3) . . ?
C016 C00O C01C 122.6(3) . . ?
C016 C00O N00J 118.9(3) . . ?
C01C C00O N00J 118.4(3) . . ?
C00W C00P C00V 118.7(3) . . ?
C00W C00P C01G 120.6(3) . . ?
C00V C00P C01G 120.7(3) . . ?
N00J C00Q N00F 113.3(3) . . ?
N00J C00Q S004 120.2(3) . . ?
N00F C00Q S004 126.5(3) . . ?
C00T C00R C00M 122.7(3) . . ?
C00T C00R H00G 118.7 . . ?
C00M C00R H00G 118.7 . . ?
N00K C00S N00I 113.4(3) . . ?
N00K C00S S003 120.1(3) . . ?
N00I C00S S003 126.5(3) . . ?
C00R C00T C00L 117.0(3) . . ?
C00R C00T C01L 121.3(3) . . ?
C00L C00T C01L 121.8(3) . . ?
C00W C00U C00X 118.2(3) . . ?
C00W C00U C01O 119.9(3) . . ?
C00X C00U C01O 121.9(3) . . ?
C019 C00V C00P 122.0(4) . . ?
C019 C00V H00H 119.0 . . ?
C00P C00V H00H 119.0 . . ?
C00P C00W C00U 121.5(3) . . ?
C00P C00W H00I 119.3 . . ?
C00U C00W H00I 119.3 . . ?
C019 C00X C00U 122.2(3) . . ?
C019 C00X N00I 118.4(3) . . ?
C00U C00X N00I 119.4(3) . . ?
N00I C00Y C014 103.3(3) . . ?
N00I C00Y H00J 111.1 . . ?
C014 C00Y H00J 111.1 . . ?
N00I C00Y H00K 111.1 . . ?
C014 C00Y H00K 111.1 . . ?
H00J C00Y H00K 109.1 . . ?
N00F C00Z C011 103.0(3) . . ?
N00F C00Z H00L 111.2 . . ?
C011 C00Z H00L 111.2 . . ?
N00F C00Z H00M 111.2 . . ?
C011 C00Z H00M 111.2 . . ?
H00L C00Z H00M 109.1 . . ?
C00M C010 C01E 121.8(3) . . ?
C00M C010 H01A 119.1 . . ?
C01E C010 H01A 119.1 . . ?
N00J C011 C00Z 102.8(3) . . ?
N00J C011 H01B 111.2 . . ?
C00Z C011 H01B 111.2 . . ?
N00J C011 H01C 111.2 . . ?
C00Z C011 H01C 111.2 . . ?
H01B C011 H01C 109.1 . . ?
C017 C012 C01F 118.7(4) . . ?
C017 C012 C01M 120.6(4) . . ?
C01F C012 C01M 120.7(4) . . ?
C016 C013 C018 121.3(4) . . ?
C016 C013 H01D 119.3 . . ?
C018 C013 H01D 119.3 . . ?
N00K C014 C00Y 102.9(3) . . ?
N00K C014 H01E 111.2 . . ?
C00Y C014 H01E 111.2 . . ?
N00K C014 H01F 111.2 . . ?
C00Y C014 H01F 111.2 . . ?
H01E C014 H01F 109.1 . . ?
F006 C015 F009 107.1(3) . . ?
F006 C015 F007 107.4(3) . . ?
F009 C015 F007 107.2(3) . . ?
F006 C015 S001 111.9(3) . . ?
F009 C015 S001 111.5(3) . . ?
F007 C015 S001 111.5(3) . . ?
C00O C016 C013 118.0(4) . . ?
C00O C016 C01Q 122.2(3) . . ?
C013 C016 C01Q 119.8(4) . . ?
C012 C017 C01B 122.3(4) . . ?
C012 C017 H01G 118.9 . . ?
C01B C017 H01G 118.9 . . ?
C01D C018 C013 118.8(3) . . ?
C01D C018 C01J 120.7(4) . . ?
C013 C018 C01J 120.6(4) . . ?
C00X C019 C00V 117.3(3) . . ?
C00X C019 C01P 122.1(3) . . ?
C00V C019 C01P 120.7(4) . . ?
C01F C01A C00N 117.7(3) . . ?
C01F C01A C01R 120.7(4) . . ?
C00N C01A C01R 121.5(4) . . ?
C017 C01B C00N 117.6(4) . . ?
C017 C01B C01S 120.8(4) . . ?
C00N C01B C01S 121.6(4) . . ?
C01D C01C C00O 117.1(3) . . ?
C01D C01C C01N 120.8(4) . . ?
C00O C01C C01N 122.1(3) . . ?
C018 C01D C01C 122.2(4) . . ?
C018 C01D H01H 118.9 . . ?
C01C C01D H01H 118.9 . . ?
C010 C01E C00L 117.6(3) . . ?
C010 C01E C01K 120.5(3) . . ?
C00L C01E C01K 121.8(3) . . ?
C012 C01F C01A 121.9(4) . . ?
C012 C01F H01I 119.1 . . ?
C01A C01F H01I 119.1 . . ?
C00P C01G H01J 109.5 . . ?
C00P C01G H01K 109.5 . . ?
H01J C01G H01K 109.5 . . ?
C00P C01G H01L 109.5 . . ?
H01J C01G H01L 109.5 . . ?
H01K C01G H01L 109.5 . . ?
C00M C01H H01M 109.5 . . ?
C00M C01H H01N 109.5 . . ?
H01M C01H H01N 109.5 . . ?
C00M C01H H01O 109.5 . . ?
H01M C01H H01O 109.5 . . ?
H01N C01H H01O 109.5 . . ?
F00H C01I F00G 107.5(4) . . ?
F00H C01I F005 106.7(3) . . ?
F00G C01I F005 107.3(3) . . ?
F00H C01I S002 112.7(3) . . ?
F00G C01I S002 110.7(3) . . ?
F005 C01I S002 111.7(3) . . ?
C018 C01J H01P 109.5 . . ?
C018 C01J H01Q 109.5 . . ?
H01P C01J H01Q 109.5 . . ?
C018 C01J H01R 109.5 . . ?
H01P C01J H01R 109.5 . . ?
H01Q C01J H01R 109.5 . . ?
C01E C01K H01S 109.5 . . ?
C01E C01K H01T 109.5 . . ?
H01S C01K H01T 109.5 . . ?
C01E C01K H01U 109.5 . . ?
H01S C01K H01U 109.5 . . ?
H01T C01K H01U 109.5 . . ?
C00T C01L H01V 109.5 . . ?
C00T C01L H01W 109.5 . . ?
H01V C01L H01W 109.5 . . ?
C00T C01L H01X 109.5 . . ?
H01V C01L H01X 109.5 . . ?
H01W C01L H01X 109.5 . . ?
C012 C01M H01Y 109.5 . . ?
C012 C01M H01Z 109.5 . . ?
H01Y C01M H01Z 109.5 . . ?
C012 C01M H02A 109.5 . . ?
H01Y C01M H02A 109.5 . . ?
H01Z C01M H02A 109.5 . . ?
C01C C01N H02B 109.5 . . ?
C01C C01N H02C 109.5 . . ?
H02B C01N H02C 109.5 . . ?
C01C C01N H02D 109.5 . . ?
H02B C01N H02D 109.5 . . ?
H02C C01N H02D 109.5 . . ?
C00U C01O H02E 109.5 . . ?
C00U C01O H02F 109.5 . . ?
H02E C01O H02F 109.5 . . ?
C00U C01O H02G 109.5 . . ?
H02E C01O H02G 109.5 . . ?
H02F C01O H02G 109.5 . . ?
C019 C01P H02H 109.5 . . ?
C019 C01P H02I 109.5 . . ?
H02H C01P H02I 109.5 . . ?
C019 C01P H02J 109.5 . . ?
H02H C01P H02J 109.5 . . ?
H02I C01P H02J 109.5 . . ?
C016 C01Q H02K 109.5 . . ?
C016 C01Q H02L 109.5 . . ?
H02K C01Q H02L 109.5 . . ?
C016 C01Q H02M 109.5 . . ?
H02K C01Q H02M 109.5 . . ?
H02L C01Q H02M 109.5 . . ?
C01A C01R H02N 109.5 . . ?
C01A C01R H02O 109.5 . . ?
H02N C01R H02O 109.5 . . ?
C01A C01R H02P 109.5 . . ?
H02N C01R H02P 109.5 . . ?
H02O C01R H02P 109.5 . . ?
C01B C01S H02Q 109.5 . . ?
C01B C01S H02R 109.5 . . ?
H02Q C01S H02R 109.5 . . ?
C01B C01S H02S 109.5 . . ?
H02Q C01S H02S 109.5 . . ?
H02R C01S H02S 109.5 . . ?

_refine_diff_density_max         0.538
_refine_diff_density_min         -0.554
_refine_diff_density_rms         0.085

####################################################################### 
# 
# 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_liu_a
_database_code_depnum_ccdc_archive 'CCDC 1515488'
_audit_update_record             
;
2017-01-13 deposited with the CCDC.
2017-01-26 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2014/7
_shelx_SHELXL_version_number     2014/7
_chemical_name_systematic        ?
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C29 H39 F3 N2 O3 S Te'
_chemical_formula_weight         680.28

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'
F F 0.0171 0.0103 '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'
Te Te -0.5308 1.6751 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_space_group_crystal_system      orthorhombic
_space_group_IT_number           61
_space_group_name_H-M_alt        'P b c a'
_space_group_name_Hall           '-P 2ac 2ab'

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

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

_cell_length_a                   16.234(2)
_cell_length_b                   17.579(3)
_cell_length_c                   21.880(3)
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_volume                     6244.1(16)
_cell_formula_units_Z            8
_cell_measurement_temperature    150(2)
_cell_measurement_reflns_used    8162
_cell_measurement_theta_min      2.50
_cell_measurement_theta_max      20.86

_exptl_crystal_description       block
_exptl_crystal_colour            colorless
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.447
_exptl_crystal_F_000             2768
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.240
_exptl_crystal_size_mid          0.122
_exptl_crystal_size_min          0.100
_exptl_absorpt_coefficient_mu    1.069
_shelx_estimated_absorpt_T_min   ?
_shelx_estimated_absorpt_T_max   ?
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.6988
_exptl_absorpt_correction_T_max  0.7452
_exptl_absorpt_process_details   ?
_exptl_absorpt_special_details   ?
_diffrn_ambient_temperature      150(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_source                   ?
_diffrn_measurement_device_type  'Bruker APEXX-II CCD'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            121842
_diffrn_reflns_av_unetI/netI     0.0588
_diffrn_reflns_av_R_equivalents  0.1423
_diffrn_reflns_limit_h_min       -19
_diffrn_reflns_limit_h_max       19
_diffrn_reflns_limit_k_min       -18
_diffrn_reflns_limit_k_max       21
_diffrn_reflns_limit_l_min       -26
_diffrn_reflns_limit_l_max       26
_diffrn_reflns_theta_min         1.945
_diffrn_reflns_theta_max         25.590
_diffrn_reflns_theta_full        25.242
_diffrn_measured_fraction_theta_max 0.989
_diffrn_measured_fraction_theta_full 1.000
_diffrn_reflns_Laue_measured_fraction_max 0.989
_diffrn_reflns_Laue_measured_fraction_full 1.000
_diffrn_reflns_point_group_measured_fraction_max 0.989
_diffrn_reflns_point_group_measured_fraction_full 1.000
_reflns_number_total             5806
_reflns_number_gt                3781
_reflns_threshold_expression     'I > 2σ(I)'
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_max     .
_reflns_Friedel_fraction_full    .

_reflns_special_details          
;
 Reflections were merged by SHELXL according to the crystal
 class for the calculation of statistics and refinement.
 
 _reflns_Friedel_fraction is defined as the number of unique
 Friedel pairs measured divided by the number that would be
 possible theoretically, ignoring centric projections and
 systematic absences.
;

_computing_data_collection       ?
_computing_cell_refinement       ?
_computing_data_reduction        ?
_computing_structure_solution    ?
_computing_structure_refinement  'SHELXL-2014/7 (Sheldrick, 2014)'
_computing_molecular_graphics    ?
_computing_publication_material  ?
_refine_special_details          ?
_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0198P)²+29.9043P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     ?
_atom_sites_solution_secondary   ?
_atom_sites_solution_hydrogens   geom
_refine_ls_hydrogen_treatment    constr
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       .
_refine_ls_number_reflns         5806
_refine_ls_number_parameters     352
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0997
_refine_ls_R_factor_gt           0.0511
_refine_ls_wR_factor_ref         0.1037
_refine_ls_wR_factor_gt          0.0887
_refine_ls_goodness_of_fit_ref   1.056
_refine_ls_restrained_S_all      1.056
_refine_ls_shift/su_max          0.001
_refine_ls_shift/su_mean         0.000

loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_site_symmetry_order
_atom_site_calc_flag
_atom_site_refinement_flags_posn
_atom_site_refinement_flags_adp
_atom_site_refinement_flags_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
Te1 Te 0.32365(2) 0.30414(2) 0.26287(2) 0.02816(11) Uani 1 1 d . . . . .
N2 N 0.3950(2) 0.2552(2) 0.39243(18) 0.0180(9) Uani 1 1 d . . . . .
N4 N 0.3046(3) 0.1768(2) 0.35696(18) 0.0212(10) Uani 1 1 d . . . . .
C3 C 0.4446(3) 0.3231(3) 0.4018(2) 0.0174(11) Uani 1 1 d . . . . .
C4 C 0.3453(3) 0.2422(3) 0.3443(2) 0.0186(11) Uani 1 1 d . . . . .
C10 C 0.5736(3) 0.3863(3) 0.3981(2) 0.0282(13) Uani 1 1 d . . . . .
H10A H 0.6298 0.3873 0.3900 0.034 Uiso 1 1 calc R U . . .
C11 C 0.5288(3) 0.3202(3) 0.3874(2) 0.0214(12) Uani 1 1 d . . . . .
C12 C 0.2365(3) 0.1446(3) 0.3219(2) 0.0232(12) Uani 1 1 d . . . . .
C13 C 0.4047(3) 0.3872(3) 0.4254(2) 0.0206(12) Uani 1 1 d . . . . .
C14 C 0.4533(4) 0.4512(3) 0.4338(2) 0.0296(14) Uani 1 1 d . . . . .
H14A H 0.4295 0.4955 0.4487 0.036 Uiso 1 1 calc R U . . .
C15 C 0.5354(4) 0.4503(3) 0.4205(2) 0.0303(14) Uani 1 1 d . . . . .
H15A H 0.5663 0.4942 0.4267 0.036 Uiso 1 1 calc R U . . .
C17 C 0.3839(3) 0.1993(3) 0.4360(2) 0.0282(13) Uani 1 1 d . . . . .
H17A H 0.4105 0.1961 0.4736 0.034 Uiso 1 1 calc R U . . .
C18 C 0.2548(3) 0.0943(3) 0.2739(2) 0.0261(13) Uani 1 1 d . . . . .
C20 C 0.1564(3) 0.1633(3) 0.3402(2) 0.0288(13) Uani 1 1 d . . . . .
C23 C 0.1082(4) 0.0794(4) 0.2606(3) 0.0441(16) Uani 1 1 d . . . . .
H23A H 0.0647 0.0577 0.2392 0.053 Uiso 1 1 calc R U . . .
C24 C 0.3150(3) 0.3869(3) 0.4433(3) 0.0304(13) Uani 1 1 d . . . . .
H24A H 0.2879 0.3460 0.4204 0.036 Uiso 1 1 calc R U . . .
C25 C 0.1372(4) 0.2178(3) 0.3930(3) 0.0346(15) Uani 1 1 d . . . . .
H25A H 0.1891 0.2295 0.4138 0.042 Uiso 1 1 calc R U . . .
C26 C 0.1876(4) 0.0622(3) 0.2450(3) 0.0389(15) Uani 1 1 d . . . . .
H26A H 0.1967 0.0274 0.2136 0.047 Uiso 1 1 calc R U . . .
C30 C 0.0928(4) 0.1292(4) 0.3083(3) 0.0412(16) Uani 1 1 d . . . . .
H30A H 0.0386 0.1399 0.3190 0.049 Uiso 1 1 calc R U . . .
C32 C 0.3281(4) 0.1509(3) 0.4145(2) 0.0287(13) Uani 1 1 d . . . . .
H32A H 0.3084 0.1077 0.4342 0.034 Uiso 1 1 calc R U . . .
C33 C 0.5689(3) 0.2499(3) 0.3619(3) 0.0325(14) Uani 1 1 d . . . . .
H33A H 0.5265 0.2187 0.3421 0.039 Uiso 1 1 calc R U . . .
C38 C 0.6351(4) 0.2696(4) 0.3144(3) 0.0536(19) Uani 1 1 d . . . . .
H38A H 0.6593 0.2236 0.2991 0.080 Uiso 1 1 calc R U . . .
H38B H 0.6104 0.2972 0.2813 0.080 Uiso 1 1 calc R U . . .
H38C H 0.6769 0.3003 0.3332 0.080 Uiso 1 1 calc R U . . .
C42 C 0.3056(4) 0.3695(4) 0.5114(3) 0.057(2) Uani 1 1 d . . . . .
H42A H 0.2483 0.3695 0.5220 0.086 Uiso 1 1 calc R U . . .
H42B H 0.3289 0.3204 0.5200 0.086 Uiso 1 1 calc R U . . .
H42C H 0.3339 0.4075 0.5348 0.086 Uiso 1 1 calc R U . . .
C43 C 0.2716(4) 0.4613(4) 0.4273(3) 0.055(2) Uani 1 1 d . . . . .
H43A H 0.2149 0.4584 0.4395 0.083 Uiso 1 1 calc R U . . .
H43B H 0.2979 0.5026 0.4483 0.083 Uiso 1 1 calc R U . . .
H43C H 0.2748 0.4697 0.3840 0.083 Uiso 1 1 calc R U . . .
C44 C 0.3413(3) 0.0741(3) 0.2549(3) 0.0336(15) Uani 1 1 d . . . . .
H44A H 0.3790 0.1098 0.2749 0.040 Uiso 1 1 calc R U . . .
C45 C 0.3640(4) -0.0060(4) 0.2752(4) 0.061(2) Uani 1 1 d . . . . .
H45A H 0.4192 -0.0173 0.2625 0.092 Uiso 1 1 calc R U . . .
H45B H 0.3603 -0.0093 0.3189 0.092 Uiso 1 1 calc R U . . .
H45C H 0.3267 -0.0418 0.2570 0.092 Uiso 1 1 calc R U . . .
C46 C 0.3525(4) 0.0823(4) 0.1861(3) 0.057(2) Uani 1 1 d . . . . .
H46A H 0.4080 0.0691 0.1752 0.086 Uiso 1 1 calc R U . . .
H46B H 0.3148 0.0490 0.1654 0.086 Uiso 1 1 calc R U . . .
H46C H 0.3416 0.1339 0.1742 0.086 Uiso 1 1 calc R U . . .
C50 C 0.4358(4) 0.3639(6) 0.2597(4) 0.090(3) Uani 1 1 d . . . . .
H50A H 0.4366 0.3961 0.2243 0.135 Uiso 1 1 calc R U . . .
H50B H 0.4413 0.3946 0.2958 0.135 Uiso 1 1 calc R U . . .
H50C H 0.4807 0.3285 0.2576 0.135 Uiso 1 1 calc R U . . .
C53 C 0.6085(5) 0.2037(4) 0.4123(4) 0.072(2) Uani 1 1 d . . . . .
H53A H 0.6337 0.1591 0.3951 0.109 Uiso 1 1 calc R U . . .
H53B H 0.6496 0.2338 0.4325 0.109 Uiso 1 1 calc R U . . .
H53C H 0.5672 0.1887 0.4414 0.109 Uiso 1 1 calc R U . . .
C54 C 0.1013(5) 0.2918(4) 0.3697(3) 0.061(2) Uani 1 1 d . . . . .
H54A H 0.1383 0.3142 0.3406 0.091 Uiso 1 1 calc R U . . .
H54B H 0.0492 0.2820 0.3504 0.091 Uiso 1 1 calc R U . . .
H54C H 0.0935 0.3261 0.4034 0.091 Uiso 1 1 calc R U . . .
C58 C 0.0796(6) 0.1811(4) 0.4392(3) 0.081(3) Uani 1 1 d . . . . .
H58A H 0.1032 0.1343 0.4535 0.121 Uiso 1 1 calc R U . . .
H58B H 0.0717 0.2150 0.4731 0.121 Uiso 1 1 calc R U . . .
H58C H 0.0275 0.1709 0.4202 0.121 Uiso 1 1 calc R U . . .
S1 S 0.33175(9) 0.37921(8) 0.09375(6) 0.0299(3) Uani 1 1 d . . . . .
F2 F 0.4594(3) 0.4642(3) 0.1170(2) 0.0917(17) Uani 1 1 d . . . . .
F3 F 0.4343(3) 0.4483(3) 0.0217(2) 0.103(2) Uani 1 1 d . . . . .
F4 F 0.3612(5) 0.5220(3) 0.0755(3) 0.127(2) Uani 1 1 d . . . . .
O1 O 0.3028(2) 0.3969(2) 0.15439(16) 0.0406(11) Uani 1 1 d . . . . .
O4 O 0.3848(3) 0.3142(2) 0.0903(2) 0.0558(13) Uani 1 1 d . . . . .
O5 O 0.2710(3) 0.3837(3) 0.04632(18) 0.0585(14) Uani 1 1 d . . . . .
C40 C 0.4007(5) 0.4562(4) 0.0764(3) 0.056(2) Uani 1 1 d . . . . .


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

loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
Te1 C50 2.104(7) . ?
Te1 C4 2.118(5) . ?
N2 C4 1.346(6) . ?
N2 C17 1.382(6) . ?
N2 C3 1.453(6) . ?
N4 C4 1.355(6) . ?
N4 C32 1.392(6) . ?
N4 C12 1.460(6) . ?
C3 C13 1.398(7) . ?
C3 C11 1.403(7) . ?
C10 C15 1.375(8) . ?
C10 C11 1.391(7) . ?
C10 H10A 0.9300 . ?
C11 C33 1.505(7) . ?
C12 C20 1.400(7) . ?
C12 C18 1.405(7) . ?
C13 C14 1.386(7) . ?
C13 C24 1.507(7) . ?
C14 C15 1.363(8) . ?
C14 H14A 0.9300 . ?
C15 H15A 0.9300 . ?
C17 C32 1.328(7) . ?
C17 H17A 0.9300 . ?
C18 C26 1.382(7) . ?
C18 C44 1.506(7) . ?
C20 C30 1.384(8) . ?
C20 C25 1.531(7) . ?
C23 C26 1.367(8) . ?
C23 C30 1.385(8) . ?
C23 H23A 0.9300 . ?
C24 C43 1.526(8) . ?
C24 C42 1.529(8) . ?
C24 H24A 0.9800 . ?
C25 C54 1.514(8) . ?
C25 C58 1.521(8) . ?
C25 H25A 0.9800 . ?
C26 H26A 0.9300 . ?
C30 H30A 0.9300 . ?
C32 H32A 0.9300 . ?
C33 C53 1.513(9) . ?
C33 C38 1.534(8) . ?
C33 H33A 0.9800 . ?
C38 H38A 0.9600 . ?
C38 H38B 0.9600 . ?
C38 H38C 0.9600 . ?
C42 H42A 0.9600 . ?
C42 H42B 0.9600 . ?
C42 H42C 0.9600 . ?
C43 H43A 0.9600 . ?
C43 H43B 0.9600 . ?
C43 H43C 0.9600 . ?
C44 C45 1.522(8) . ?
C44 C46 1.523(8) . ?
C44 H44A 0.9800 . ?
C45 H45A 0.9600 . ?
C45 H45B 0.9600 . ?
C45 H45C 0.9600 . ?
C46 H46A 0.9600 . ?
C46 H46B 0.9600 . ?
C46 H46C 0.9600 . ?
C50 H50A 0.9600 . ?
C50 H50B 0.9600 . ?
C50 H50C 0.9600 . ?
C53 H53A 0.9600 . ?
C53 H53B 0.9600 . ?
C53 H53C 0.9600 . ?
C54 H54A 0.9600 . ?
C54 H54B 0.9600 . ?
C54 H54C 0.9600 . ?
C58 H58A 0.9600 . ?
C58 H58B 0.9600 . ?
C58 H58C 0.9600 . ?
S1 O4 1.432(4) . ?
S1 O5 1.433(4) . ?
S1 O1 1.441(4) . ?
S1 C40 1.797(7) . ?
F2 C40 1.311(8) . ?
F3 C40 1.322(8) . ?
F4 C40 1.322(9) . ?

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
C50 Te1 C4 98.1(2) . . ?
C4 N2 C17 109.9(4) . . ?
C4 N2 C3 125.6(4) . . ?
C17 N2 C3 124.0(4) . . ?
C4 N4 C32 109.2(4) . . ?
C4 N4 C12 126.2(4) . . ?
C32 N4 C12 123.8(4) . . ?
C13 C3 C11 124.2(4) . . ?
C13 C3 N2 117.2(4) . . ?
C11 C3 N2 118.5(4) . . ?
N2 C4 N4 106.1(4) . . ?
N2 C4 Te1 132.1(4) . . ?
N4 C4 Te1 121.8(3) . . ?
C15 C10 C11 120.5(5) . . ?
C15 C10 H10A 119.8 . . ?
C11 C10 H10A 119.8 . . ?
C10 C11 C3 116.2(5) . . ?
C10 C11 C33 121.5(5) . . ?
C3 C11 C33 122.3(5) . . ?
C20 C12 C18 123.9(5) . . ?
C20 C12 N4 117.5(4) . . ?
C18 C12 N4 118.5(5) . . ?
C14 C13 C3 116.0(5) . . ?
C14 C13 C24 121.2(5) . . ?
C3 C13 C24 122.7(4) . . ?
C15 C14 C13 121.3(5) . . ?
C15 C14 H14A 119.4 . . ?
C13 C14 H14A 119.4 . . ?
C14 C15 C10 121.7(5) . . ?
C14 C15 H15A 119.1 . . ?
C10 C15 H15A 119.1 . . ?
C32 C17 N2 107.5(4) . . ?
C32 C17 H17A 126.3 . . ?
N2 C17 H17A 126.3 . . ?
C26 C18 C12 115.6(5) . . ?
C26 C18 C44 120.9(5) . . ?
C12 C18 C44 123.5(5) . . ?
C30 C20 C12 116.5(5) . . ?
C30 C20 C25 120.0(5) . . ?
C12 C20 C25 123.4(5) . . ?
C26 C23 C30 119.9(5) . . ?
C26 C23 H23A 120.0 . . ?
C30 C23 H23A 120.0 . . ?
C13 C24 C43 112.6(5) . . ?
C13 C24 C42 110.5(5) . . ?
C43 C24 C42 110.5(5) . . ?
C13 C24 H24A 107.7 . . ?
C43 C24 H24A 107.7 . . ?
C42 C24 H24A 107.7 . . ?
C54 C25 C58 110.5(6) . . ?
C54 C25 C20 111.3(5) . . ?
C58 C25 C20 111.2(5) . . ?
C54 C25 H25A 107.9 . . ?
C58 C25 H25A 107.9 . . ?
C20 C25 H25A 107.9 . . ?
C23 C26 C18 122.7(5) . . ?
C23 C26 H26A 118.7 . . ?
C18 C26 H26A 118.7 . . ?
C20 C30 C23 121.3(6) . . ?
C20 C30 H30A 119.4 . . ?
C23 C30 H30A 119.4 . . ?
C17 C32 N4 107.3(4) . . ?
C17 C32 H32A 126.3 . . ?
N4 C32 H32A 126.3 . . ?
C11 C33 C53 110.7(5) . . ?
C11 C33 C38 111.7(5) . . ?
C53 C33 C38 108.5(5) . . ?
C11 C33 H33A 108.6 . . ?
C53 C33 H33A 108.6 . . ?
C38 C33 H33A 108.6 . . ?
C33 C38 H38A 109.5 . . ?
C33 C38 H38B 109.5 . . ?
H38A C38 H38B 109.5 . . ?
C33 C38 H38C 109.5 . . ?
H38A C38 H38C 109.5 . . ?
H38B C38 H38C 109.5 . . ?
C24 C42 H42A 109.5 . . ?
C24 C42 H42B 109.5 . . ?
H42A C42 H42B 109.5 . . ?
C24 C42 H42C 109.5 . . ?
H42A C42 H42C 109.5 . . ?
H42B C42 H42C 109.5 . . ?
C24 C43 H43A 109.5 . . ?
C24 C43 H43B 109.5 . . ?
H43A C43 H43B 109.5 . . ?
C24 C43 H43C 109.5 . . ?
H43A C43 H43C 109.5 . . ?
H43B C43 H43C 109.5 . . ?
C18 C44 C45 111.2(5) . . ?
C18 C44 C46 111.2(5) . . ?
C45 C44 C46 110.3(5) . . ?
C18 C44 H44A 108.0 . . ?
C45 C44 H44A 108.0 . . ?
C46 C44 H44A 108.0 . . ?
C44 C45 H45A 109.5 . . ?
C44 C45 H45B 109.5 . . ?
H45A C45 H45B 109.5 . . ?
C44 C45 H45C 109.5 . . ?
H45A C45 H45C 109.5 . . ?
H45B C45 H45C 109.5 . . ?
C44 C46 H46A 109.5 . . ?
C44 C46 H46B 109.5 . . ?
H46A C46 H46B 109.5 . . ?
C44 C46 H46C 109.5 . . ?
H46A C46 H46C 109.5 . . ?
H46B C46 H46C 109.5 . . ?
Te1 C50 H50A 109.5 . . ?
Te1 C50 H50B 109.5 . . ?
H50A C50 H50B 109.5 . . ?
Te1 C50 H50C 109.5 . . ?
H50A C50 H50C 109.5 . . ?
H50B C50 H50C 109.5 . . ?
C33 C53 H53A 109.5 . . ?
C33 C53 H53B 109.5 . . ?
H53A C53 H53B 109.5 . . ?
C33 C53 H53C 109.5 . . ?
H53A C53 H53C 109.5 . . ?
H53B C53 H53C 109.5 . . ?
C25 C54 H54A 109.5 . . ?
C25 C54 H54B 109.5 . . ?
H54A C54 H54B 109.5 . . ?
C25 C54 H54C 109.5 . . ?
H54A C54 H54C 109.5 . . ?
H54B C54 H54C 109.5 . . ?
C25 C58 H58A 109.5 . . ?
C25 C58 H58B 109.5 . . ?
H58A C58 H58B 109.5 . . ?
C25 C58 H58C 109.5 . . ?
H58A C58 H58C 109.5 . . ?
H58B C58 H58C 109.5 . . ?
O4 S1 O5 114.8(3) . . ?
O4 S1 O1 114.6(3) . . ?
O5 S1 O1 115.5(3) . . ?
O4 S1 C40 102.4(3) . . ?
O5 S1 C40 103.5(3) . . ?
O1 S1 C40 103.6(3) . . ?
F2 C40 F3 109.0(7) . . ?
F2 C40 F4 105.6(6) . . ?
F3 C40 F4 106.2(6) . . ?
F2 C40 S1 113.0(5) . . ?
F3 C40 S1 111.7(5) . . ?
F4 C40 S1 111.0(6) . . ?

loop_
_geom_torsion_atom_site_label_1
_geom_torsion_atom_site_label_2
_geom_torsion_atom_site_label_3
_geom_torsion_atom_site_label_4
_geom_torsion
_geom_torsion_site_symmetry_1
_geom_torsion_site_symmetry_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
_geom_torsion_publ_flag
C4 N2 C3 C13 80.6(6) . . . . ?
C17 N2 C3 C13 -90.1(6) . . . . ?
C4 N2 C3 C11 -100.1(6) . . . . ?
C17 N2 C3 C11 89.2(6) . . . . ?
C17 N2 C4 N4 -1.8(5) . . . . ?
C3 N2 C4 N4 -173.6(4) . . . . ?
C17 N2 C4 Te1 177.0(4) . . . . ?
C3 N2 C4 Te1 5.1(7) . . . . ?
C32 N4 C4 N2 1.9(5) . . . . ?
C12 N4 C4 N2 171.9(4) . . . . ?
C32 N4 C4 Te1 -177.0(3) . . . . ?
C12 N4 C4 Te1 -7.0(6) . . . . ?
C15 C10 C11 C3 -1.0(7) . . . . ?
C15 C10 C11 C33 178.9(5) . . . . ?
C13 C3 C11 C10 0.1(7) . . . . ?
N2 C3 C11 C10 -179.1(4) . . . . ?
C13 C3 C11 C33 -179.8(5) . . . . ?
N2 C3 C11 C33 0.9(7) . . . . ?
C4 N4 C12 C20 -93.1(6) . . . . ?
C32 N4 C12 C20 75.5(6) . . . . ?
C4 N4 C12 C18 89.7(6) . . . . ?
C32 N4 C12 C18 -101.7(6) . . . . ?
C11 C3 C13 C14 0.9(7) . . . . ?
N2 C3 C13 C14 -179.9(4) . . . . ?
C11 C3 C13 C24 -176.8(5) . . . . ?
N2 C3 C13 C24 2.4(7) . . . . ?
C3 C13 C14 C15 -1.1(8) . . . . ?
C24 C13 C14 C15 176.7(5) . . . . ?
C13 C14 C15 C10 0.2(9) . . . . ?
C11 C10 C15 C14 0.9(8) . . . . ?
C4 N2 C17 C32 1.0(6) . . . . ?
C3 N2 C17 C32 173.0(5) . . . . ?
C20 C12 C18 C26 -0.8(8) . . . . ?
N4 C12 C18 C26 176.1(5) . . . . ?
C20 C12 C18 C44 -179.5(5) . . . . ?
N4 C12 C18 C44 -2.5(8) . . . . ?
C18 C12 C20 C30 0.1(8) . . . . ?
N4 C12 C20 C30 -176.9(5) . . . . ?
C18 C12 C20 C25 179.6(5) . . . . ?
N4 C12 C20 C25 2.6(8) . . . . ?
C14 C13 C24 C43 40.4(7) . . . . ?
C3 C13 C24 C43 -142.0(5) . . . . ?
C14 C13 C24 C42 -83.5(6) . . . . ?
C3 C13 C24 C42 94.1(6) . . . . ?
C30 C20 C25 C54 -70.7(7) . . . . ?
C12 C20 C25 C54 109.8(6) . . . . ?
C30 C20 C25 C58 52.9(8) . . . . ?
C12 C20 C25 C58 -126.5(7) . . . . ?
C30 C23 C26 C18 -1.9(10) . . . . ?
C12 C18 C26 C23 1.8(9) . . . . ?
C44 C18 C26 C23 -179.5(6) . . . . ?
C12 C20 C30 C23 -0.2(9) . . . . ?
C25 C20 C30 C23 -179.7(6) . . . . ?
C26 C23 C30 C20 1.1(10) . . . . ?
N2 C17 C32 N4 0.2(6) . . . . ?
C4 N4 C32 C17 -1.3(6) . . . . ?
C12 N4 C32 C17 -171.6(5) . . . . ?
C10 C11 C33 C53 84.2(7) . . . . ?
C3 C11 C33 C53 -95.8(7) . . . . ?
C10 C11 C33 C38 -36.8(7) . . . . ?
C3 C11 C33 C38 143.1(5) . . . . ?
C26 C18 C44 C45 -72.6(7) . . . . ?
C12 C18 C44 C45 106.0(6) . . . . ?
C26 C18 C44 C46 50.8(7) . . . . ?
C12 C18 C44 C46 -130.6(6) . . . . ?
O4 S1 C40 F2 -63.6(6) . . . . ?
O5 S1 C40 F2 176.8(6) . . . . ?
O1 S1 C40 F2 55.8(6) . . . . ?
O4 S1 C40 F3 59.7(6) . . . . ?
O5 S1 C40 F3 -60.0(7) . . . . ?
O1 S1 C40 F3 179.1(6) . . . . ?
O4 S1 C40 F4 177.9(5) . . . . ?
O5 S1 C40 F4 58.3(6) . . . . ?
O1 S1 C40 F4 -62.6(5) . . . . ?

_refine_diff_density_max         1.460
_refine_diff_density_min         -1.003
_refine_diff_density_rms         0.104

####################################################################### 
# 
# 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_LIU001_a
_database_code_depnum_ccdc_archive 'CCDC 1515486'
_audit_update_record             
;
2017-01-13 deposited with the CCDC.
2017-01-26 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2014/7
_shelx_SHELXL_version_number     2014/7
_chemical_name_systematic        ?
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C29 H39 F3 N2 O3 S2'
_chemical_formula_weight         584.74

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'
O O 0.0106 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
F F 0.0171 0.0103 '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'
N N 0.0061 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_space_group_crystal_system      orthorhombic
_space_group_IT_number           61
_space_group_name_H-M_alt        'P b c a'
_space_group_name_Hall           '-P 2ac 2ab'

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

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

_cell_length_a                   15.9377(14)
_cell_length_b                   17.3130(13)
_cell_length_c                   21.9697(18)
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_volume                     6062.1(9)
_cell_formula_units_Z            8
_cell_measurement_temperature    150(2)
_cell_measurement_reflns_used    9822
_cell_measurement_theta_min      2.25
_cell_measurement_theta_max      27.41

_exptl_crystal_description       shard
_exptl_crystal_colour            colorless
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.281
_exptl_crystal_F_000             2480
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.200
_exptl_crystal_size_mid          0.100
_exptl_crystal_size_min          0.100
_exptl_absorpt_coefficient_mu    0.226
_shelx_estimated_absorpt_T_min   0.956
_shelx_estimated_absorpt_T_max   0.978
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.6839
_exptl_absorpt_correction_T_max  0.7457
_exptl_absorpt_process_details   ?
_exptl_absorpt_special_details   ?
_diffrn_ambient_temperature      150(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_source                   ?
_diffrn_measurement_device_type  'Bruker APEX-II CCD'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            92925
_diffrn_reflns_av_unetI/netI     0.0766
_diffrn_reflns_av_R_equivalents  0.1115
_diffrn_reflns_limit_h_min       -21
_diffrn_reflns_limit_h_max       21
_diffrn_reflns_limit_k_min       -23
_diffrn_reflns_limit_k_max       23
_diffrn_reflns_limit_l_min       -29
_diffrn_reflns_limit_l_max       25
_diffrn_reflns_theta_min         1.854
_diffrn_reflns_theta_max         28.738
_diffrn_reflns_theta_full        25.242
_diffrn_measured_fraction_theta_max 0.987
_diffrn_measured_fraction_theta_full 1.000
_diffrn_reflns_Laue_measured_fraction_max 0.987
_diffrn_reflns_Laue_measured_fraction_full 1.000
_diffrn_reflns_point_group_measured_fraction_max 0.987
_diffrn_reflns_point_group_measured_fraction_full 1.000
_reflns_number_total             7765
_reflns_number_gt                4175
_reflns_threshold_expression     'I > 2σ(I)'
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_max     .
_reflns_Friedel_fraction_full    .

_reflns_special_details          
;
 Reflections were merged by SHELXL according to the crystal
 class for the calculation of statistics and refinement.
 
 _reflns_Friedel_fraction is defined as the number of unique
 Friedel pairs measured divided by the number that would be
 possible theoretically, ignoring centric projections and
 systematic absences.
;

_computing_data_collection       ?
_computing_cell_refinement       ?
_computing_data_reduction        ?
_computing_structure_solution    ?
_computing_structure_refinement  'SHELXL-2014/7 (Sheldrick, 2014)'
_computing_molecular_graphics    ?
_computing_publication_material  ?
_refine_special_details          ?
_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.1000P)²] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     ?
_atom_sites_solution_secondary   ?
_atom_sites_solution_hydrogens   geom
_refine_ls_hydrogen_treatment    constr
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       .
_refine_ls_number_reflns         7765
_refine_ls_number_parameters     380
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.1334
_refine_ls_R_factor_gt           0.0537
_refine_ls_wR_factor_ref         0.1767
_refine_ls_wR_factor_gt          0.1365
_refine_ls_goodness_of_fit_ref   0.971
_refine_ls_restrained_S_all      0.971
_refine_ls_shift/su_max          0.014
_refine_ls_shift/su_mean         0.001

loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_site_symmetry_order
_atom_site_calc_flag
_atom_site_refinement_flags_posn
_atom_site_refinement_flags_adp
_atom_site_refinement_flags_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
S001 S 0.31862(4) 0.20817(4) 0.28492(3) 0.03124(19) Uani 1 1 d . . . . .
S002 S 0.33495(5) 0.38706(5) 0.59374(3) 0.0426(2) Uani 1 1 d . . . . .
N1 N 0.40148(12) 0.25205(10) 0.39066(8) 0.0195(4) Uani 1 1 d . . . . .
N2 N 0.30453(12) 0.33143(10) 0.36186(9) 0.0219(4) Uani 1 1 d . . . . .
O005 O 0.29840(13) 0.40245(13) 0.65174(9) 0.0501(6) Uani 1 1 d . . . . .
O006 O 0.37747(15) 0.31515(12) 0.58773(10) 0.0605(7) Uani 1 1 d . . . . .
C007 C 0.45108(14) 0.18184(12) 0.39726(10) 0.0200(5) Uani 1 1 d . . . . .
C008 C 0.34436(14) 0.26540(12) 0.34712(10) 0.0200(5) Uani 1 1 d . . . . .
C009 C 0.23247(14) 0.36467(12) 0.33073(10) 0.0225(5) Uani 1 1 d . . . . .
C00A C 0.53460(14) 0.18303(13) 0.37905(10) 0.0222(5) Uani 1 1 d . . . . .
C00B C 0.39768(16) 0.31011(12) 0.43347(11) 0.0252(5) Uani 1 1 d . . . . .
H00C H 0.4316 0.3147 0.4688 0.030 Uiso 1 1 calc R U . . .
C00C C 0.33716(16) 0.35895(13) 0.41583(11) 0.0274(6) Uani 1 1 d . . . . .
H00D H 0.3199 0.4043 0.4367 0.033 Uiso 1 1 calc R U . . .
C00D C 0.41116(15) 0.11795(12) 0.42366(10) 0.0231(5) Uani 1 1 d . . . . .
C00E C 0.15303(15) 0.34579(13) 0.35319(11) 0.0253(5) Uani 1 1 d . . . . .
C00F C 0.58046(16) 0.11491(14) 0.38808(11) 0.0289(6) Uani 1 1 d . . . . .
H00E H 0.6379 0.1128 0.3766 0.035 Uiso 1 1 calc R U . . .
C00G C 0.57745(16) 0.25369(13) 0.35247(12) 0.0290(6) Uani 1 1 d . . . . .
H00F H 0.5331 0.2904 0.3385 0.035 Uiso 1 1 calc R U . . .
C00H C 0.24637(16) 0.41518(13) 0.28210(11) 0.0250(5) Uani 1 1 d . . . . .
C00J C 0.54290(17) 0.05091(14) 0.41355(12) 0.0321(6) Uani 1 1 d . . . . .
H00G H 0.5748 0.0051 0.4192 0.038 Uiso 1 1 calc R U . . .
C00K C 0.46025(16) 0.05220(13) 0.43087(11) 0.0293(6) Uani 1 1 d . . . . .
H00H H 0.4360 0.0072 0.4482 0.035 Uiso 1 1 calc R U . . .
C00L C 0.32066(16) 0.11966(13) 0.44467(12) 0.0286(6) Uani 1 1 d . . . . .
H00I H 0.2922 0.1638 0.4238 0.034 Uiso 1 1 calc R U . . .
C00M C 0.13865(17) 0.28954(14) 0.40551(12) 0.0301(6) Uani 1 1 d . . . . .
H00J H 0.1938 0.2809 0.4261 0.036 Uiso 1 1 calc R U . . .
C00N C 0.17551(16) 0.44926(15) 0.25593(12) 0.0325(6) Uani 1 1 d . . . . .
H00K H 0.1820 0.4846 0.2232 0.039 Uiso 1 1 calc R U . . .
C00O C 0.33262(16) 0.43380(14) 0.25736(12) 0.0308(6) Uani 1 1 d . . . . .
H00L H 0.3746 0.4022 0.2802 0.037 Uiso 1 1 calc R U . . .
C00P C 0.08538(16) 0.38089(14) 0.32492(12) 0.0337(6) Uani 1 1 d . . . . .
H00M H 0.0302 0.3696 0.3386 0.040 Uiso 1 1 calc R U . . .
C00R C 0.09642(17) 0.43197(15) 0.27720(12) 0.0369(7) Uani 1 1 d . . . . .
H00N H 0.0488 0.4554 0.2589 0.044 Uiso 1 1 calc R U . . .
O00S O 0.28383(19) 0.4077(2) 0.54340(11) 0.1090(12) Uani 1 1 d . . . . .
C00T C 0.63255(18) 0.23353(17) 0.29814(13) 0.0420(7) Uani 1 1 d . . . . .
H00P H 0.6589 0.2806 0.2824 0.063 Uiso 1 1 calc R U . . .
H00Q H 0.6761 0.1970 0.3109 0.063 Uiso 1 1 calc R U . . .
H00R H 0.5981 0.2100 0.2662 0.063 Uiso 1 1 calc R U . . .
C00U C 0.63059(19) 0.29437(16) 0.40092(14) 0.0432(7) Uani 1 1 d . . . . .
H00S H 0.6577 0.3398 0.3830 0.065 Uiso 1 1 calc R U . . .
H00T H 0.5945 0.3106 0.4347 0.065 Uiso 1 1 calc R U . . .
H00U H 0.6736 0.2587 0.4161 0.065 Uiso 1 1 calc R U . . .
C00V C 0.33836(19) 0.41207(18) 0.18968(14) 0.0461(8) Uani 1 1 d . . . . .
H00V H 0.3945 0.4245 0.1743 0.069 Uiso 1 1 calc R U . . .
H00W H 0.3279 0.3566 0.1849 0.069 Uiso 1 1 calc R U . . .
H00X H 0.2963 0.4413 0.1666 0.069 Uiso 1 1 calc R U . . .
C00W C 0.35399(19) 0.51956(16) 0.26691(15) 0.0470(8) Uani 1 1 d . . . . .
H00Y H 0.4100 0.5302 0.2506 0.071 Uiso 1 1 calc R U . . .
H00Z H 0.3126 0.5516 0.2458 0.071 Uiso 1 1 calc R U . . .
H01A H 0.3530 0.5315 0.3105 0.071 Uiso 1 1 calc R U . . .
C00X C 0.3162(2) 0.13405(19) 0.51284(15) 0.0538(9) Uani 1 1 d . . . . .
H01B H 0.2573 0.1350 0.5258 0.081 Uiso 1 1 calc R U . . .
H01C H 0.3458 0.0927 0.5344 0.081 Uiso 1 1 calc R U . . .
H01D H 0.3425 0.1838 0.5223 0.081 Uiso 1 1 calc R U . . .
C00Y C 0.1081(2) 0.21205(17) 0.38194(15) 0.0522(9) Uani 1 1 d . . . . .
H01E H 0.1477 0.1923 0.3516 0.078 Uiso 1 1 calc R U . . .
H01F H 0.1042 0.1754 0.4158 0.078 Uiso 1 1 calc R U . . .
H01G H 0.0527 0.2184 0.3632 0.078 Uiso 1 1 calc R U . . .
C00Z C 0.2740(2) 0.04594(17) 0.42768(17) 0.0555(9) Uani 1 1 d . . . . .
H01H H 0.2159 0.0493 0.4420 0.083 Uiso 1 1 calc R U . . .
H01I H 0.2745 0.0396 0.3834 0.083 Uiso 1 1 calc R U . . .
H01J H 0.3016 0.0015 0.4467 0.083 Uiso 1 1 calc R U . . .
C011 C 0.4172(2) 0.2016(2) 0.24599(15) 0.0675(11) Uani 1 1 d . . . . .
H01K H 0.4106 0.1700 0.2093 0.101 Uiso 1 1 calc R U . . .
H01L H 0.4361 0.2535 0.2345 0.101 Uiso 1 1 calc R U . . .
H01M H 0.4589 0.1777 0.2729 0.101 Uiso 1 1 calc R U . . .
C012 C 0.4194(4) 0.4532(2) 0.5896(2) 0.0770(14) Uani 1 1 d . . . . .
C013 C 0.0785(3) 0.3209(2) 0.45234(16) 0.0788(13) Uani 1 1 d . . . . .
H01N H 0.0989 0.3708 0.4672 0.118 Uiso 1 1 calc R U . . .
H01O H 0.0230 0.3275 0.4338 0.118 Uiso 1 1 calc R U . . .
H01P H 0.0745 0.2846 0.4865 0.118 Uiso 1 1 calc R U . . .
F1 F 0.3797(16) 0.5240(8) 0.5771(10) 0.137(6) Uani 0.47(3) 1 d . . P A 1
F2 F 0.4647(13) 0.4590(14) 0.6260(10) 0.096(6) Uani 0.47(3) 1 d . . P A 1
F3 F 0.4800(12) 0.4441(9) 0.5487(10) 0.098(5) Uani 0.47(3) 1 d . . P A 1
F1A F 0.4086(9) 0.5277(6) 0.6028(10) 0.101(4) Uani 0.53(3) 1 d . . P A 2
F2A F 0.4759(6) 0.4371(8) 0.6453(7) 0.062(3) Uani 0.53(3) 1 d . . P A 2
F3A F 0.4537(12) 0.4444(9) 0.5333(8) 0.111(5) Uani 0.53(3) 1 d . . P A 2


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

loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
S001 C008 1.737(2) . ?
S001 C011 1.793(3) . ?
S002 O00S 1.419(3) . ?
S002 O006 1.424(2) . ?
S002 O005 1.426(2) . ?
S002 C012 1.770(5) . ?
N1 C008 1.341(3) . ?
N1 C00B 1.378(3) . ?
N1 C007 1.457(3) . ?
N2 C008 1.347(3) . ?
N2 C00C 1.380(3) . ?
N2 C009 1.455(3) . ?
C007 C00A 1.390(3) . ?
C007 C00D 1.402(3) . ?
C009 C00E 1.398(3) . ?
C009 C00H 1.398(3) . ?
C00A C00F 1.402(3) . ?
C00A C00G 1.518(3) . ?
C00B C00C 1.340(3) . ?
C00B H00C 0.9500 . ?
C00C H00D 0.9500 . ?
C00D C00K 1.390(3) . ?
C00D C00L 1.515(3) . ?
C00E C00P 1.385(3) . ?
C00E C00M 1.524(3) . ?
C00F C00J 1.378(4) . ?
C00F H00E 0.9500 . ?
C00G C00T 1.522(4) . ?
C00G C00U 1.532(4) . ?
C00G H00F 1.0000 . ?
C00H C00N 1.398(3) . ?
C00H C00O 1.513(3) . ?
C00J C00K 1.371(4) . ?
C00J H00G 0.9500 . ?
C00K H00H 0.9500 . ?
C00L C00X 1.520(4) . ?
C00L C00Z 1.524(4) . ?
C00L H00I 1.0000 . ?
C00M C013 1.507(4) . ?
C00M C00Y 1.518(4) . ?
C00M H00J 1.0000 . ?
C00N C00R 1.377(4) . ?
C00N H00K 0.9500 . ?
C00O C00V 1.537(4) . ?
C00O C00W 1.538(4) . ?
C00O H00L 1.0000 . ?
C00P C00R 1.383(3) . ?
C00P H00M 0.9500 . ?
C00R H00N 0.9500 . ?
C00T H00P 0.9800 . ?
C00T H00Q 0.9800 . ?
C00T H00R 0.9800 . ?
C00U H00S 0.9800 . ?
C00U H00T 0.9800 . ?
C00U H00U 0.9800 . ?
C00V H00V 0.9800 . ?
C00V H00W 0.9800 . ?
C00V H00X 0.9800 . ?
C00W H00Y 0.9800 . ?
C00W H00Z 0.9800 . ?
C00W H01A 0.9800 . ?
C00X H01B 0.9800 . ?
C00X H01C 0.9800 . ?
C00X H01D 0.9800 . ?
C00Y H01E 0.9800 . ?
C00Y H01F 0.9800 . ?
C00Y H01G 0.9800 . ?
C00Z H01H 0.9800 . ?
C00Z H01I 0.9800 . ?
C00Z H01J 0.9800 . ?
C011 H01K 0.9800 . ?
C011 H01L 0.9800 . ?
C011 H01M 0.9800 . ?
C012 F2 1.08(2) . ?
C012 F3 1.327(15) . ?
C012 F1A 1.333(12) . ?
C012 F3A 1.361(16) . ?
C012 F1 1.407(18) . ?
C012 F2A 1.545(15) . ?
C013 H01N 0.9800 . ?
C013 H01O 0.9800 . ?
C013 H01P 0.9800 . ?
F2 F3 1.73(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
C008 S001 C011 101.79(13) . . ?
O00S S002 O006 114.92(16) . . ?
O00S S002 O005 114.49(15) . . ?
O006 S002 O005 116.15(14) . . ?
O00S S002 C012 103.5(3) . . ?
O006 S002 C012 101.46(18) . . ?
O005 S002 C012 103.65(18) . . ?
C008 N1 C00B 109.35(18) . . ?
C008 N1 C007 125.68(18) . . ?
C00B N1 C007 124.36(18) . . ?
C008 N2 C00C 108.78(19) . . ?
C008 N2 C009 126.47(19) . . ?
C00C N2 C009 124.40(19) . . ?
C00A C007 C00D 124.4(2) . . ?
C00A C007 N1 118.59(19) . . ?
C00D C007 N1 116.9(2) . . ?
N1 C008 N2 107.15(19) . . ?
N1 C008 S001 128.56(17) . . ?
N2 C008 S001 124.19(17) . . ?
C00E C009 C00H 124.0(2) . . ?
C00E C009 N2 117.2(2) . . ?
C00H C009 N2 118.8(2) . . ?
C007 C00A C00F 116.5(2) . . ?
C007 C00A C00G 123.6(2) . . ?
C00F C00A C00G 119.9(2) . . ?
C00C C00B N1 107.1(2) . . ?
C00C C00B H00C 126.4 . . ?
N1 C00B H00C 126.4 . . ?
C00B C00C N2 107.6(2) . . ?
C00B C00C H00D 126.2 . . ?
N2 C00C H00D 126.2 . . ?
C00K C00D C007 116.0(2) . . ?
C00K C00D C00L 121.1(2) . . ?
C007 C00D C00L 122.89(19) . . ?
C00P C00E C009 116.4(2) . . ?
C00P C00E C00M 120.1(2) . . ?
C009 C00E C00M 123.5(2) . . ?
C00J C00F C00A 120.5(2) . . ?
C00J C00F H00E 119.8 . . ?
C00A C00F H00E 119.8 . . ?
C00A C00G C00T 112.1(2) . . ?
C00A C00G C00U 110.6(2) . . ?
C00T C00G C00U 109.3(2) . . ?
C00A C00G H00F 108.2 . . ?
C00T C00G H00F 108.2 . . ?
C00U C00G H00F 108.2 . . ?
C00N C00H C009 116.8(2) . . ?
C00N C00H C00O 119.8(2) . . ?
C009 C00H C00O 123.5(2) . . ?
C00K C00J C00F 121.1(2) . . ?
C00K C00J H00G 119.4 . . ?
C00F C00J H00G 119.4 . . ?
C00J C00K C00D 121.5(2) . . ?
C00J C00K H00H 119.3 . . ?
C00D C00K H00H 119.3 . . ?
C00D C00L C00X 110.4(2) . . ?
C00D C00L C00Z 112.0(2) . . ?
C00X C00L C00Z 110.8(2) . . ?
C00D C00L H00I 107.8 . . ?
C00X C00L H00I 107.8 . . ?
C00Z C00L H00I 107.8 . . ?
C013 C00M C00Y 110.3(3) . . ?
C013 C00M C00E 112.4(2) . . ?
C00Y C00M C00E 110.8(2) . . ?
C013 C00M H00J 107.7 . . ?
C00Y C00M H00J 107.7 . . ?
C00E C00M H00J 107.7 . . ?
C00R C00N C00H 120.5(2) . . ?
C00R C00N H00K 119.7 . . ?
C00H C00N H00K 119.7 . . ?
C00H C00O C00V 110.5(2) . . ?
C00H C00O C00W 111.0(2) . . ?
C00V C00O C00W 110.8(2) . . ?
C00H C00O H00L 108.2 . . ?
C00V C00O H00L 108.2 . . ?
C00W C00O H00L 108.2 . . ?
C00R C00P C00E 121.4(2) . . ?
C00R C00P H00M 119.3 . . ?
C00E C00P H00M 119.3 . . ?
C00N C00R C00P 120.8(2) . . ?
C00N C00R H00N 119.6 . . ?
C00P C00R H00N 119.6 . . ?
C00G C00T H00P 109.5 . . ?
C00G C00T H00Q 109.5 . . ?
H00P C00T H00Q 109.5 . . ?
C00G C00T H00R 109.5 . . ?
H00P C00T H00R 109.5 . . ?
H00Q C00T H00R 109.5 . . ?
C00G C00U H00S 109.5 . . ?
C00G C00U H00T 109.5 . . ?
H00S C00U H00T 109.5 . . ?
C00G C00U H00U 109.5 . . ?
H00S C00U H00U 109.5 . . ?
H00T C00U H00U 109.5 . . ?
C00O C00V H00V 109.5 . . ?
C00O C00V H00W 109.5 . . ?
H00V C00V H00W 109.5 . . ?
C00O C00V H00X 109.5 . . ?
H00V C00V H00X 109.5 . . ?
H00W C00V H00X 109.5 . . ?
C00O C00W H00Y 109.5 . . ?
C00O C00W H00Z 109.5 . . ?
H00Y C00W H00Z 109.5 . . ?
C00O C00W H01A 109.5 . . ?
H00Y C00W H01A 109.5 . . ?
H00Z C00W H01A 109.5 . . ?
C00L C00X H01B 109.5 . . ?
C00L C00X H01C 109.5 . . ?
H01B C00X H01C 109.5 . . ?
C00L C00X H01D 109.5 . . ?
H01B C00X H01D 109.5 . . ?
H01C C00X H01D 109.5 . . ?
C00M C00Y H01E 109.5 . . ?
C00M C00Y H01F 109.5 . . ?
H01E C00Y H01F 109.5 . . ?
C00M C00Y H01G 109.5 . . ?
H01E C00Y H01G 109.5 . . ?
H01F C00Y H01G 109.5 . . ?
C00L C00Z H01H 109.5 . . ?
C00L C00Z H01I 109.5 . . ?
H01H C00Z H01I 109.5 . . ?
C00L C00Z H01J 109.5 . . ?
H01H C00Z H01J 109.5 . . ?
H01I C00Z H01J 109.5 . . ?
S001 C011 H01K 109.5 . . ?
S001 C011 H01L 109.5 . . ?
H01K C011 H01L 109.5 . . ?
S001 C011 H01M 109.5 . . ?
H01K C011 H01M 109.5 . . ?
H01L C011 H01M 109.5 . . ?
F2 C012 F3 91.5(13) . . ?
F1A C012 F3A 111.0(8) . . ?
F2 C012 F1 111.3(11) . . ?
F3 C012 F1 107.4(10) . . ?
F1A C012 F2A 94.4(11) . . ?
F3A C012 F2A 117.8(13) . . ?
F2 C012 S002 122.0(11) . . ?
F3 C012 S002 120.8(10) . . ?
F1A C012 S002 121.0(7) . . ?
F3A C012 S002 106.3(7) . . ?
F1 C012 S002 103.3(11) . . ?
F2A C012 S002 106.6(5) . . ?
C00M C013 H01N 109.5 . . ?
C00M C013 H01O 109.5 . . ?
H01N C013 H01O 109.5 . . ?
C00M C013 H01P 109.5 . . ?
H01N C013 H01P 109.5 . . ?
H01O C013 H01P 109.5 . . ?
C012 F2 F3 49.9(12) . . ?
C012 F3 F2 38.6(7) . . ?

_refine_diff_density_max         0.478
_refine_diff_density_min         -0.626
_refine_diff_density_rms         0.061


_chemical_properties_physical    
', Air-sensitive,Moisture-sensitive,Oxygen-sensitive'
####################################################################### 
# 
# 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_LIU002_0m_a
_database_code_depnum_ccdc_archive 'CCDC 1515487'
_audit_update_record             
;
2017-01-13 deposited with the CCDC.
2017-01-26 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2014/7
_shelx_SHELXL_version_number     2014/7
_chemical_name_systematic        ?
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C29 H39 F3 N2 O3 S Se'
_chemical_formula_weight         631.64

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'
F F 0.0171 0.0103 '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'
S S 0.1246 0.1234 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_space_group_crystal_system      orthorhombic
_space_group_IT_number           61
_space_group_name_H-M_alt        'P b c a'
_space_group_name_Hall           '-P 2ac 2ab'

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

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

_cell_length_a                   16.1430(16)
_cell_length_b                   17.3306(17)
_cell_length_c                   21.714(2)
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_volume                     6075.0(10)
_cell_formula_units_Z            8
_cell_measurement_temperature    150(2)
_cell_measurement_reflns_used    9813
_cell_measurement_theta_min      2.26
_cell_measurement_theta_max      26.70

_exptl_crystal_description       block
_exptl_crystal_colour            colorless
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.381
_exptl_crystal_F_000             2624
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.240
_exptl_crystal_size_mid          0.190
_exptl_crystal_size_min          0.170
_exptl_absorpt_coefficient_mu    1.355
_shelx_estimated_absorpt_T_min   0.737
_shelx_estimated_absorpt_T_max   0.802
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.7059
_exptl_absorpt_correction_T_max  0.7456
_exptl_absorpt_process_details   ?
_exptl_absorpt_special_details   ?
_diffrn_ambient_temperature      150(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_source                   ?
_diffrn_measurement_device_type  'Bruker APEX-II CCD'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            53460
_diffrn_reflns_av_unetI/netI     0.0363
_diffrn_reflns_av_R_equivalents  0.0538
_diffrn_reflns_limit_h_min       -15
_diffrn_reflns_limit_h_max       21
_diffrn_reflns_limit_k_min       -22
_diffrn_reflns_limit_k_max       21
_diffrn_reflns_limit_l_min       -25
_diffrn_reflns_limit_l_max       28
_diffrn_reflns_theta_min         1.963
_diffrn_reflns_theta_max         27.614
_diffrn_reflns_theta_full        25.242
_diffrn_measured_fraction_theta_max 0.997
_diffrn_measured_fraction_theta_full 1.000
_diffrn_reflns_Laue_measured_fraction_max 0.997
_diffrn_reflns_Laue_measured_fraction_full 1.000
_diffrn_reflns_point_group_measured_fraction_max 0.997
_diffrn_reflns_point_group_measured_fraction_full 1.000
_reflns_number_total             7045
_reflns_number_gt                5236
_reflns_threshold_expression     'I > 2σ(I)'
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_max     .
_reflns_Friedel_fraction_full    .

_reflns_special_details          
;
 Reflections were merged by SHELXL according to the crystal
 class for the calculation of statistics and refinement.
 
 _reflns_Friedel_fraction is defined as the number of unique
 Friedel pairs measured divided by the number that would be
 possible theoretically, ignoring centric projections and
 systematic absences.
;

_computing_data_collection       ?
_computing_cell_refinement       ?
_computing_data_reduction        ?
_computing_structure_solution    ?
_computing_structure_refinement  'SHELXL-2014/7 (Sheldrick, 2014)'
_computing_molecular_graphics    ?
_computing_publication_material  ?
_refine_special_details          ?
_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0481P)²+6.0730P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     ?
_atom_sites_solution_secondary   ?
_atom_sites_solution_hydrogens   geom
_refine_ls_hydrogen_treatment    constr
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       .
_refine_ls_number_reflns         7045
_refine_ls_number_parameters     380
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0650
_refine_ls_R_factor_gt           0.0412
_refine_ls_wR_factor_ref         0.1057
_refine_ls_wR_factor_gt          0.0954
_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_site_symmetry_order
_atom_site_calc_flag
_atom_site_refinement_flags_posn
_atom_site_refinement_flags_adp
_atom_site_refinement_flags_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
S01 S 0.33042(4) 0.37932(4) 0.40435(3) 0.02958(16) Uani 1 1 d . . . . .
N003 N 0.39793(11) 0.24916(11) 0.60900(9) 0.0150(4) Uani 1 1 d . . . . .
O2 O 0.29850(13) 0.39300(13) 0.34364(9) 0.0392(5) Uani 1 1 d . . . . .
N005 N 0.30235(12) 0.32749(11) 0.63916(9) 0.0176(4) Uani 1 1 d . . . . .
O3 O 0.38000(15) 0.31196(12) 0.41090(11) 0.0497(6) Uani 1 1 d . . . . .
C007 C 0.34300(14) 0.26264(13) 0.65409(10) 0.0155(5) Uani 1 1 d . . . . .
C008 C 0.44734(14) 0.17970(13) 0.60180(10) 0.0157(5) Uani 1 1 d . . . . .
C009 C 0.33247(15) 0.35412(14) 0.58289(11) 0.0223(5) Uani 1 1 d . . . . .
H00A H 0.3139 0.3986 0.5613 0.027 Uiso 1 1 calc R U . . .
C00A C 0.39144(16) 0.30629(14) 0.56511(11) 0.0230(5) Uani 1 1 d . . . . .
H00B H 0.4236 0.3105 0.5286 0.028 Uiso 1 1 calc R U . . .
C00B C 0.40845(14) 0.11527(13) 0.57661(11) 0.0177(5) Uani 1 1 d . . . . .
C00C C 0.15387(15) 0.34456(15) 0.65010(11) 0.0223(5) Uani 1 1 d . . . . .
C00D C 0.53079(14) 0.18181(14) 0.61863(11) 0.0183(5) Uani 1 1 d . . . . .
C00E C 0.23303(14) 0.36159(14) 0.67172(11) 0.0190(5) Uani 1 1 d . . . . .
C00F C 0.45708(16) 0.05014(14) 0.56859(12) 0.0240(5) Uani 1 1 d . . . . .
H00C H 0.4330 0.0048 0.5517 0.029 Uiso 1 1 calc R U . . .
C00G C 0.24890(15) 0.41229(15) 0.71998(11) 0.0216(5) Uani 1 1 d . . . . .
C00H C 0.31889(15) 0.11634(14) 0.55577(12) 0.0230(5) Uani 1 1 d . . . . .
H00D H 0.2905 0.1595 0.5778 0.028 Uiso 1 1 calc R U . . .
O1 O 0.27265(16) 0.3914(2) 0.45296(11) 0.0781(10) Uani 1 1 d . . . . .
C00J C 0.53938(16) 0.04988(15) 0.58460(12) 0.0262(6) Uani 1 1 d . . . . .
H00E H 0.5714 0.0045 0.5787 0.031 Uiso 1 1 calc R U . . .
C00L C 0.08860(16) 0.38115(17) 0.67934(13) 0.0323(6) Uani 1 1 d . . . . .
H00F H 0.0335 0.3710 0.6662 0.039 Uiso 1 1 calc R U . . .
C00M C 0.13731(16) 0.28857(15) 0.59775(12) 0.0269(6) Uani 1 1 d . . . . .
H00G H 0.1897 0.2832 0.5735 0.032 Uiso 1 1 calc R U . . .
C00N C 0.57592(15) 0.11472(15) 0.60904(12) 0.0248(6) Uani 1 1 d . . . . .
H00H H 0.6330 0.1136 0.6195 0.030 Uiso 1 1 calc R U . . .
C00P C 0.10188(17) 0.43211(18) 0.72711(13) 0.0350(7) Uani 1 1 d . . . . .
H00I H 0.0561 0.4567 0.7463 0.042 Uiso 1 1 calc R U . . .
C00Q C 0.57240(16) 0.25334(16) 0.64398(12) 0.0267(6) Uani 1 1 d . . . . .
H00J H 0.5285 0.2889 0.6599 0.032 Uiso 1 1 calc R U . . .
C00R C 0.33491(16) 0.42996(16) 0.74363(13) 0.0287(6) Uani 1 1 d . . . . .
H00K H 0.3751 0.3966 0.7208 0.034 Uiso 1 1 calc R U . . .
C00T C 0.63155(18) 0.23472(19) 0.69658(15) 0.0398(7) Uani 1 1 d . . . . .
H00L H 0.6570 0.2825 0.7116 0.060 Uiso 1 1 calc R U . . .
H00M H 0.6008 0.2101 0.7302 0.060 Uiso 1 1 calc R U . . .
H00N H 0.6748 0.1996 0.6818 0.060 Uiso 1 1 calc R U . . .
C00U C 0.6205(2) 0.29529(18) 0.59342(16) 0.0450(8) Uani 1 1 d . . . . .
H00O H 0.6470 0.3413 0.6107 0.067 Uiso 1 1 calc R U . . .
H00P H 0.6631 0.2608 0.5767 0.067 Uiso 1 1 calc R U . . .
H00Q H 0.5824 0.3106 0.5605 0.067 Uiso 1 1 calc R U . . .
C00V C 0.31268(19) 0.1323(2) 0.48734(15) 0.0439(8) Uani 1 1 d . . . . .
H00R H 0.2543 0.1327 0.4750 0.066 Uiso 1 1 calc R U . . .
H00S H 0.3376 0.1825 0.4782 0.066 Uiso 1 1 calc R U . . .
H00T H 0.3421 0.0919 0.4645 0.066 Uiso 1 1 calc R U . . .
C00W C 0.3580(2) 0.51428(19) 0.73165(17) 0.0481(9) Uani 1 1 d . . . . .
H00U H 0.4139 0.5243 0.7474 0.072 Uiso 1 1 calc R U . . .
H00V H 0.3565 0.5245 0.6873 0.072 Uiso 1 1 calc R U . . .
H00W H 0.3184 0.5481 0.7526 0.072 Uiso 1 1 calc R U . . .
C00X C 0.27392(19) 0.04166(18) 0.57224(17) 0.0466(8) Uani 1 1 d . . . . .
H00X H 0.2786 0.0323 0.6166 0.070 Uiso 1 1 calc R U . . .
H00Y H 0.2153 0.0461 0.5610 0.070 Uiso 1 1 calc R U . . .
H00Z H 0.2989 -0.0014 0.5497 0.070 Uiso 1 1 calc R U . . .
C00Y C 0.1144(2) 0.20922(17) 0.62189(15) 0.0433(8) Uani 1 1 d . . . . .
H01A H 0.1577 0.1910 0.6500 0.065 Uiso 1 1 calc R U . . .
H01B H 0.0615 0.2122 0.6440 0.065 Uiso 1 1 calc R U . . .
H01C H 0.1091 0.1732 0.5873 0.065 Uiso 1 1 calc R U . . .
C00Z C 0.34155(19) 0.4106(2) 0.81213(14) 0.0451(8) Uani 1 1 d . . . . .
H01D H 0.3976 0.4224 0.8267 0.068 Uiso 1 1 calc R U . . .
H01E H 0.3013 0.4414 0.8353 0.068 Uiso 1 1 calc R U . . .
H01F H 0.3300 0.3556 0.8183 0.068 Uiso 1 1 calc R U . . .
C011 C 0.0706(3) 0.3172(2) 0.55429(18) 0.0742(14) Uani 1 1 d . . . . .
H01G H 0.0857 0.3684 0.5388 0.111 Uiso 1 1 calc R U . . .
H01H H 0.0653 0.2813 0.5196 0.111 Uiso 1 1 calc R U . . .
H01I H 0.0177 0.3203 0.5763 0.111 Uiso 1 1 calc R U . . .
C013 C 0.4051(3) 0.4543(2) 0.4151(2) 0.0686(13) Uani 1 1 d . . . . .
F01A F 0.4551(14) 0.4432(11) 0.4618(10) 0.106(5) Uani 0.54(4) 1 d . . P A 1
F02A F 0.4504(12) 0.4653(12) 0.3766(5) 0.078(5) Uani 0.54(4) 1 d . . P A 1
F03A F 0.3889(12) 0.5212(6) 0.4084(9) 0.114(4) Uani 0.54(4) 1 d . . P A 1
F01B F 0.4301(13) 0.4537(11) 0.4748(7) 0.085(5) Uani 0.46(4) 1 d . . P A 2
F02B F 0.4726(8) 0.4424(11) 0.3644(11) 0.078(4) Uani 0.46(4) 1 d . . P A 2
F03B F 0.345(2) 0.5240(7) 0.4172(6) 0.104(6) Uani 0.46(4) 1 d . . P A 2
Se1 Se 0.31966(2) 0.20196(2) 0.72422(2) 0.02260(8) Uani 1 1 d . . . . .
C1 C 0.18090(16) 0.44761(16) 0.74720(13) 0.0292(6) Uani 1 1 d . . . . .
H1B H 0.1891 0.4829 0.7801 0.035 Uiso 1 1 calc R U . . .
C2 C 0.4297(2) 0.1979(3) 0.75778(17) 0.0755(16) Uani 1 1 d . . . . .
H2B H 0.4293 0.1675 0.7958 0.113 Uiso 1 1 calc R U . . .
H2C H 0.4670 0.1737 0.7279 0.113 Uiso 1 1 calc R U . . .
H2D H 0.4489 0.2503 0.7668 0.113 Uiso 1 1 calc R U . . .


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

loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
S01 O3 1.423(2) . ?
S01 O1 1.424(2) . ?
S01 O2 1.435(2) . ?
S01 C013 1.788(4) . ?
N003 C007 1.341(3) . ?
N003 C00A 1.378(3) . ?
N003 C008 1.452(3) . ?
N005 C007 1.341(3) . ?
N005 C009 1.394(3) . ?
N005 C00E 1.450(3) . ?
C007 Se1 1.889(2) . ?
C008 C00B 1.393(3) . ?
C008 C00D 1.396(3) . ?
C009 C00A 1.320(3) . ?
C009 H00A 0.9500 . ?
C00A H00B 0.9500 . ?
C00B C00F 1.386(3) . ?
C00B C00H 1.515(3) . ?
C00C C00L 1.384(3) . ?
C00C C00E 1.393(3) . ?
C00C C00M 1.518(3) . ?
C00D C00N 1.388(3) . ?
C00D C00Q 1.514(3) . ?
C00E C00G 1.391(3) . ?
C00F C00J 1.373(4) . ?
C00F H00C 0.9500 . ?
C00G C1 1.389(3) . ?
C00G C00R 1.512(3) . ?
C00H C00V 1.515(4) . ?
C00H C00X 1.526(4) . ?
C00H H00D 1.0000 . ?
C00J C00N 1.376(4) . ?
C00J H00E 0.9500 . ?
C00L C00P 1.379(4) . ?
C00L H00F 0.9500 . ?
C00M C011 1.515(4) . ?
C00M C00Y 1.518(4) . ?
C00M H00G 1.0000 . ?
C00N H00H 0.9500 . ?
C00P C1 1.375(4) . ?
C00P H00I 0.9500 . ?
C00Q C00T 1.523(4) . ?
C00Q C00U 1.529(4) . ?
C00Q H00J 1.0000 . ?
C00R C00Z 1.529(4) . ?
C00R C00W 1.530(4) . ?
C00R H00K 1.0000 . ?
C00T H00L 0.9800 . ?
C00T H00M 0.9800 . ?
C00T H00N 0.9800 . ?
C00U H00O 0.9800 . ?
C00U H00P 0.9800 . ?
C00U H00Q 0.9800 . ?
C00V H00R 0.9800 . ?
C00V H00S 0.9800 . ?
C00V H00T 0.9800 . ?
C00W H00U 0.9800 . ?
C00W H00V 0.9800 . ?
C00W H00W 0.9800 . ?
C00X H00X 0.9800 . ?
C00X H00Y 0.9800 . ?
C00X H00Z 0.9800 . ?
C00Y H01A 0.9800 . ?
C00Y H01B 0.9800 . ?
C00Y H01C 0.9800 . ?
C00Z H01D 0.9800 . ?
C00Z H01E 0.9800 . ?
C00Z H01F 0.9800 . ?
C011 H01G 0.9800 . ?
C011 H01H 0.9800 . ?
C011 H01I 0.9800 . ?
C013 F02A 1.127(16) . ?
C013 F03A 1.197(12) . ?
C013 F01A 1.310(15) . ?
C013 F01B 1.357(16) . ?
C013 F03B 1.55(2) . ?
C013 F02B 1.56(2) . ?
F02A F03A 1.55(5) . ?
Se1 C2 1.921(3) . ?
C1 H1B 0.9500 . ?
C2 H2B 0.9800 . ?
C2 H2C 0.9800 . ?
C2 H2D 0.9800 . ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
O3 S01 O1 114.51(17) . . ?
O3 S01 O2 115.43(14) . . ?
O1 S01 O2 114.94(14) . . ?
O3 S01 C013 101.78(19) . . ?
O1 S01 C013 103.7(2) . . ?
O2 S01 C013 104.02(17) . . ?
C007 N003 C00A 109.22(19) . . ?
C007 N003 C008 125.87(19) . . ?
C00A N003 C008 124.24(19) . . ?
C007 N005 C009 108.58(19) . . ?
C007 N005 C00E 126.97(19) . . ?
C009 N005 C00E 124.19(19) . . ?
N005 C007 N003 107.04(19) . . ?
N005 C007 Se1 124.32(16) . . ?
N003 C007 Se1 128.56(17) . . ?
C00B C008 C00D 124.0(2) . . ?
C00B C008 N003 117.33(19) . . ?
C00D C008 N003 118.7(2) . . ?
C00A C009 N005 107.5(2) . . ?
C00A C009 H00A 126.3 . . ?
N005 C009 H00A 126.3 . . ?
C009 C00A N003 107.7(2) . . ?
C009 C00A H00B 126.2 . . ?
N003 C00A H00B 126.2 . . ?
C00F C00B C008 116.5(2) . . ?
C00F C00B C00H 120.9(2) . . ?
C008 C00B C00H 122.5(2) . . ?
C00L C00C C00E 116.5(2) . . ?
C00L C00C C00M 120.1(2) . . ?
C00E C00C C00M 123.3(2) . . ?
C00N C00D C008 116.4(2) . . ?
C00N C00D C00Q 120.5(2) . . ?
C008 C00D C00Q 123.0(2) . . ?
C00G C00E C00C 123.8(2) . . ?
C00G C00E N005 118.9(2) . . ?
C00C C00E N005 117.2(2) . . ?
C00J C00F C00B 121.3(2) . . ?
C00J C00F H00C 119.4 . . ?
C00B C00F H00C 119.4 . . ?
C1 C00G C00E 117.0(2) . . ?
C1 C00G C00R 119.5(2) . . ?
C00E C00G C00R 123.6(2) . . ?
C00V C00H C00B 111.0(2) . . ?
C00V C00H C00X 110.7(2) . . ?
C00B C00H C00X 111.9(2) . . ?
C00V C00H H00D 107.7 . . ?
C00B C00H H00D 107.7 . . ?
C00X C00H H00D 107.7 . . ?
C00F C00J C00N 120.7(2) . . ?
C00F C00J H00E 119.7 . . ?
C00N C00J H00E 119.7 . . ?
C00P C00L C00C 121.3(2) . . ?
C00P C00L H00F 119.3 . . ?
C00C C00L H00F 119.3 . . ?
C011 C00M C00Y 109.8(3) . . ?
C011 C00M C00C 112.5(2) . . ?
C00Y C00M C00C 111.3(2) . . ?
C011 C00M H00G 107.7 . . ?
C00Y C00M H00G 107.7 . . ?
C00C C00M H00G 107.7 . . ?
C00J C00N C00D 121.1(2) . . ?
C00J C00N H00H 119.4 . . ?
C00D C00N H00H 119.4 . . ?
C1 C00P C00L 120.5(2) . . ?
C1 C00P H00I 119.7 . . ?
C00L C00P H00I 119.7 . . ?
C00D C00Q C00T 112.2(2) . . ?
C00D C00Q C00U 110.7(2) . . ?
C00T C00Q C00U 108.7(2) . . ?
C00D C00Q H00J 108.4 . . ?
C00T C00Q H00J 108.4 . . ?
C00U C00Q H00J 108.4 . . ?
C00G C00R C00Z 110.5(2) . . ?
C00G C00R C00W 111.0(2) . . ?
C00Z C00R C00W 111.0(3) . . ?
C00G C00R H00K 108.1 . . ?
C00Z C00R H00K 108.1 . . ?
C00W C00R H00K 108.1 . . ?
C00Q C00T H00L 109.5 . . ?
C00Q C00T H00M 109.5 . . ?
H00L C00T H00M 109.5 . . ?
C00Q C00T H00N 109.5 . . ?
H00L C00T H00N 109.5 . . ?
H00M C00T H00N 109.5 . . ?
C00Q C00U H00O 109.5 . . ?
C00Q C00U H00P 109.5 . . ?
H00O C00U H00P 109.5 . . ?
C00Q C00U H00Q 109.5 . . ?
H00O C00U H00Q 109.5 . . ?
H00P C00U H00Q 109.5 . . ?
C00H C00V H00R 109.5 . . ?
C00H C00V H00S 109.5 . . ?
H00R C00V H00S 109.5 . . ?
C00H C00V H00T 109.5 . . ?
H00R C00V H00T 109.5 . . ?
H00S C00V H00T 109.5 . . ?
C00R C00W H00U 109.5 . . ?
C00R C00W H00V 109.5 . . ?
H00U C00W H00V 109.5 . . ?
C00R C00W H00W 109.5 . . ?
H00U C00W H00W 109.5 . . ?
H00V C00W H00W 109.5 . . ?
C00H C00X H00X 109.5 . . ?
C00H C00X H00Y 109.5 . . ?
H00X C00X H00Y 109.5 . . ?
C00H C00X H00Z 109.5 . . ?
H00X C00X H00Z 109.5 . . ?
H00Y C00X H00Z 109.5 . . ?
C00M C00Y H01A 109.5 . . ?
C00M C00Y H01B 109.5 . . ?
H01A C00Y H01B 109.5 . . ?
C00M C00Y H01C 109.5 . . ?
H01A C00Y H01C 109.5 . . ?
H01B C00Y H01C 109.5 . . ?
C00R C00Z H01D 109.5 . . ?
C00R C00Z H01E 109.5 . . ?
H01D C00Z H01E 109.5 . . ?
C00R C00Z H01F 109.5 . . ?
H01D C00Z H01F 109.5 . . ?
H01E C00Z H01F 109.5 . . ?
C00M C011 H01G 109.5 . . ?
C00M C011 H01H 109.5 . . ?
H01G C011 H01H 109.5 . . ?
C00M C011 H01I 109.5 . . ?
H01G C011 H01I 109.5 . . ?
H01H C011 H01I 109.5 . . ?
F02A C013 F03A 84(2) . . ?
F02A C013 F01A 101.5(10) . . ?
F03A C013 F01A 111.8(11) . . ?
F01B C013 F03B 99.5(11) . . ?
F01B C013 F02B 117.6(13) . . ?
F03B C013 F02B 124.1(10) . . ?
F02A C013 S01 117.5(8) . . ?
F03A C013 S01 122.8(8) . . ?
F01A C013 S01 114.2(8) . . ?
F01B C013 S01 108.7(6) . . ?
F03B C013 S01 98.5(12) . . ?
F02B C013 S01 106.3(8) . . ?
C013 F02A F03A 50.1(14) . . ?
C013 F03A F02A 46.3(10) . . ?
C007 Se1 C2 98.16(12) . . ?
C00P C1 C00G 120.8(2) . . ?
C00P C1 H1B 119.6 . . ?
C00G C1 H1B 119.6 . . ?
Se1 C2 H2B 109.5 . . ?
Se1 C2 H2C 109.5 . . ?
H2B C2 H2C 109.5 . . ?
Se1 C2 H2D 109.5 . . ?
H2B C2 H2D 109.5 . . ?
H2C C2 H2D 109.5 . . ?

_refine_diff_density_max         1.623
_refine_diff_density_min         -0.553
_refine_diff_density_rms         0.072

