# Electronic Supplementary Material (ESI) for New Journal of Chemistry.
# This journal is © The Royal Society of Chemistry and the Centre National de la Recherche Scientifique 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_160607d
_database_code_depnum_ccdc_archive 'CCDC 1509287'
_audit_update_record             
;
2017-05-10 deposited with the CCDC.
2017-05-18 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            'C24 H30 F2 N0 O4 S2 Sn'
_chemical_formula_weight         603.29

loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
N N 0.0061 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0106 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
S S 0.1246 0.1234 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
Sn Sn -0.6537 1.4246 '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'

_space_group_crystal_system      monoclinic
_space_group_IT_number           5
_space_group_name_H-M_alt        'C 2'
_space_group_name_Hall           'C 2y'

_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'
'x+1/2, y+1/2, z'
'-x+1/2, y+1/2, -z'

_cell_length_a                   18.6301(16)
_cell_length_b                   5.1010(5)
_cell_length_c                   16.2579(14)
_cell_angle_alpha                90
_cell_angle_beta                 119.173(3)
_cell_angle_gamma                90
_cell_volume                     1349.0(2)
_cell_formula_units_Z            2
_cell_measurement_temperature    298(2)
_cell_measurement_reflns_used    1680
_cell_measurement_theta_min      2.741
_cell_measurement_theta_max      22.1035

_exptl_crystal_description       block
_exptl_crystal_colour            colourless
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.485
_exptl_crystal_F_000             612
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.420
_exptl_crystal_size_mid          0.160
_exptl_crystal_size_min          0.150
_exptl_absorpt_coefficient_mu    1.142
_shelx_estimated_absorpt_T_min   0.646
_shelx_estimated_absorpt_T_max   0.847
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.6456
_exptl_absorpt_correction_T_max  0.8474
_exptl_absorpt_process_details   sadabs
_exptl_absorpt_special_details   ?
_diffrn_ambient_temperature      298(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_source                   ?
_diffrn_measurement_device_type  'CCD area detector'
_diffrn_measurement_method       'phi and omega scans'
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            3404
_diffrn_reflns_av_unetI/netI     0.0573
_diffrn_reflns_av_R_equivalents  0.0365
_diffrn_reflns_limit_h_min       -19
_diffrn_reflns_limit_h_max       22
_diffrn_reflns_limit_k_min       -6
_diffrn_reflns_limit_k_max       5
_diffrn_reflns_limit_l_min       -19
_diffrn_reflns_limit_l_max       19
_diffrn_reflns_theta_min         2.739
_diffrn_reflns_theta_max         24.997
_diffrn_reflns_theta_full        24.997
_diffrn_measured_fraction_theta_max 0.994
_diffrn_measured_fraction_theta_full 0.994
_diffrn_reflns_Laue_measured_fraction_max 0.994
_diffrn_reflns_Laue_measured_fraction_full 0.994
_diffrn_reflns_point_group_measured_fraction_max 0.926
_diffrn_reflns_point_group_measured_fraction_full 0.926
_reflns_number_total             2198
_reflns_number_gt                2108
_reflns_threshold_expression     'I > 2σ(I)'
_reflns_Friedel_coverage         0.659
_reflns_Friedel_fraction_max     0.839
_reflns_Friedel_fraction_full    0.839

_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       'Bruker SMART'
_computing_cell_refinement       'Bruker SMART'
_computing_data_reduction        'Bruker SAINT'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 1990)'
_computing_structure_refinement  'SHELXL-2014/7 (Sheldrick, 2014)'
_computing_molecular_graphics    'Bruker SHELXTL'
_computing_publication_material  'Bruker SHELXTL'
_refine_special_details          ?
_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.1299P)²+1.0895P] 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_abs_structure_details 
;
 Flack x determined using 759 quotients [(I+)-(I-)]/[(I+)+(I-)]
 (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259).
;
_refine_ls_abs_structure_Flack   0.07(7)
_chemical_absolute_configuration ?
_refine_ls_number_reflns         2198
_refine_ls_number_parameters     176
_refine_ls_number_restraints     137
_refine_ls_R_factor_all          0.0667
_refine_ls_R_factor_gt           0.0641
_refine_ls_wR_factor_ref         0.1722
_refine_ls_wR_factor_gt          0.1684
_refine_ls_goodness_of_fit_ref   1.038
_refine_ls_restrained_S_all      1.074
_refine_ls_shift/su_max          0.076
_refine_ls_shift/su_mean         0.009

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
Sn1 Sn 1.0000 0.485(3) 1.0000 0.0484(4) Uani 1 2 d S T P . .
S1 S 0.6829(2) 0.736(4) 0.8497(3) 0.0706(10) Uani 1 1 d . . . . .
F1 F 0.685(4) 0.617(8) 0.491(3) 0.20(4) Uani 0.55(2) 1 d . . P A 1
F1' F 0.719(3) 0.691(18) 0.517(3) 0.20(3) Uani 0.45(2) 1 d . . P A 2
O1 O 0.8493(6) 0.453(5) 0.9593(9) 0.070(4) Uani 1 1 d . . . . .
O2 O 0.9189(5) 0.806(4) 0.9753(6) 0.053(2) Uani 1 1 d . U . . .
C1 C 0.7561(12) 0.815(3) 0.7337(15) 0.090(6) Uani 0.55(2) 1 d D U P A 1
H1 H 0.7997 0.9029 0.7828 0.108 Uiso 0.55(2) 1 calc R U P A 1
C2 C 0.7555(15) 0.785(3) 0.6493(16) 0.098(6) Uani 0.55(2) 1 d D U P A 1
H2 H 0.7983 0.8523 0.6419 0.117 Uiso 0.55(2) 1 calc R U P A 1
C3 C 0.6916(16) 0.656(4) 0.5760(16) 0.109(6) Uani 0.55(2) 1 d D U P A 1
C4 C 0.6292(17) 0.558(7) 0.5883(15) 0.111(7) Uani 0.55(2) 1 d D U P A 1
H4 H 0.5858 0.4702 0.5391 0.134 Uiso 0.55(2) 1 calc R U P A 1
C5 C 0.6298(13) 0.588(7) 0.6725(14) 0.104(7) Uani 0.55(2) 1 d D U P A 1
H5 H 0.5869 0.5202 0.6796 0.125 Uiso 0.55(2) 1 calc R U P A 1
C6 C 0.6934(7) 0.719(3) 0.7469(8) 0.077(4) Uani 1 1 d D U . . .
C7 C 0.7816(8) 0.857(5) 0.9383(10) 0.054(3) Uani 1 1 d . . . . .
H7A H 0.7910 1.0269 0.9184 0.064 Uiso 1 1 calc R U . . .
H7B H 0.7799 0.8829 0.9964 0.064 Uiso 1 1 calc R U . . .
C8 C 0.8521(7) 0.684(5) 0.9578(9) 0.044(2) Uani 1 1 d . U . . .
C9 C 0.9650(12) 0.634(5) 0.8656(10) 0.079(5) Uani 1 1 d D . . . .
H9A H 0.9075 0.6840 0.8360 0.095 Uiso 1 1 calc R U . . .
H9B H 0.9967 0.7912 0.8723 0.095 Uiso 1 1 calc R U . . .
C10 C 0.9763(9) 0.450(7) 0.8031(8) 0.082(6) Uani 1 1 d D . . . .
H10A H 1.0354 0.4516 0.8281 0.098 Uiso 1 1 calc R U . . .
H10B H 0.9646 0.2817 0.8217 0.098 Uiso 1 1 calc R U . . .
C11 C 0.9454(13) 0.417(5) 0.7029(9) 0.102(9) Uani 1 1 d D U . . .
H11A H 0.8859 0.4141 0.6742 0.123 Uiso 1 1 calc R U . . .
H11B H 0.9617 0.2424 0.6950 0.123 Uiso 1 1 calc R U . . .
C12 C 0.965(2) 0.595(7) 0.6425(16) 0.162(16) Uani 1 1 d D U . . .
H12A H 0.9211 0.7199 0.6111 0.242 Uiso 1 1 calc R U . . .
H12B H 0.9706 0.4932 0.5965 0.242 Uiso 1 1 calc R U . . .
H12C H 1.0153 0.6870 0.6814 0.242 Uiso 1 1 calc R U . . .
C1' C 0.7257(15) 0.934(4) 0.7257(17) 0.090(6) Uani 0.45(2) 1 d D . P A 2
H1' H 0.7410 1.0819 0.7640 0.108 Uiso 0.45(2) 1 calc R U P A 2
C2' C 0.7350(17) 0.927(6) 0.6466(18) 0.098(6) Uani 0.45(2) 1 d D . P A 2
H2' H 0.7565 1.0713 0.6308 0.117 Uiso 0.45(2) 1 calc R U P A 2
C3' C 0.7124(16) 0.707(7) 0.5915(17) 0.109(6) Uani 0.45(2) 1 d D . P A 2
C5' C 0.6715(18) 0.497(5) 0.6923(18) 0.104(7) Uani 0.45(2) 1 d D . P A 2
H5' H 0.6508 0.3520 0.7086 0.125 Uiso 0.45(2) 1 calc R U P A 2
C4' C 0.680(2) 0.492(7) 0.6131(18) 0.111(7) Uani 0.45(2) 1 d D . P A 2
H4' H 0.6649 0.3446 0.5746 0.134 Uiso 0.45(2) 1 calc R U 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
Sn1 C9 2.094(13) . ?
Sn1 C9 2.094(13) 2_757 ?
Sn1 O2 2.130(10) 2_757 ?
Sn1 O2 2.130(10) . ?
Sn1 O1 2.557(10) 2_757 ?
Sn1 O1 2.557(10) . ?
S1 C6 1.778(12) . ?
S1 C7 1.804(14) . ?
F1 C3 1.34(6) . ?
F1' C3' 1.28(7) . ?
O1 C8 1.18(3) . ?
O2 C8 1.294(15) . ?
C1 C6 1.378(12) . ?
C1 C2 1.374(12) . ?
C1 H1 0.9300 . ?
C2 C3 1.375(13) . ?
C2 H2 0.9300 . ?
C3 C4 1.367(13) . ?
C4 C5 1.371(12) . ?
C4 H4 0.9300 . ?
C5 C6 1.383(12) . ?
C5 H5 0.9300 . ?
C6 C5' 1.371(13) . ?
C6 C1' 1.375(13) . ?
C7 C8 1.482(19) . ?
C7 H7A 0.9700 . ?
C7 H7B 0.9700 . ?
C9 C10 1.472(13) . ?
C9 H9A 0.9700 . ?
C9 H9B 0.9700 . ?
C10 C11 1.449(11) . ?
C10 H10A 0.9700 . ?
C10 H10B 0.9700 . ?
C11 C12 1.508(13) . ?
C11 H11A 0.9700 . ?
C11 H11B 0.9700 . ?
C12 H12A 0.9600 . ?
C12 H12B 0.9600 . ?
C12 H12C 0.9600 . ?
C1' C2' 1.380(12) . ?
C1' H1' 0.9300 . ?
C2' C3' 1.370(13) . ?
C2' H2' 0.9300 . ?
C3' C4' 1.372(13) . ?
C5' C4' 1.377(13) . ?
C5' H5' 0.9300 . ?
C4' H4' 0.9300 . ?

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
C9 Sn1 C9 137.5(9) . 2_757 ?
C9 Sn1 O2 75.5(6) . 2_757 ?
C9 Sn1 O2 72.1(5) 2_757 2_757 ?
C9 Sn1 O2 72.1(5) . . ?
C9 Sn1 O2 75.5(6) 2_757 . ?
O2 Sn1 O2 79.4(5) 2_757 . ?
C9 Sn1 O1 92.2(6) . 2_757 ?
C9 Sn1 O1 90.5(6) 2_757 2_757 ?
O2 Sn1 O1 54.0(5) 2_757 2_757 ?
O2 Sn1 O1 133.4(6) . 2_757 ?
C9 Sn1 O1 90.5(6) . . ?
C9 Sn1 O1 92.2(6) 2_757 . ?
O2 Sn1 O1 133.4(6) 2_757 . ?
O2 Sn1 O1 54.0(5) . . ?
O1 Sn1 O1 172.6(10) 2_757 . ?
C6 S1 C7 103.3(6) . . ?
C8 O1 Sn1 83.5(10) . . ?
C8 O2 Sn1 100.9(8) . . ?
C6 C1 C2 121.3(15) . . ?
C6 C1 H1 119.3 . . ?
C2 C1 H1 119.4 . . ?
C3 C2 C1 120.2(16) . . ?
C3 C2 H2 119.9 . . ?
C1 C2 H2 119.9 . . ?
F1 C3 C4 116(4) . . ?
F1 C3 C2 125(4) . . ?
C4 C3 C2 119.1(16) . . ?
C3 C4 C5 120.7(16) . . ?
C3 C4 H4 119.6 . . ?
C5 C4 H4 119.7 . . ?
C4 C5 C6 121.0(15) . . ?
C4 C5 H5 119.5 . . ?
C6 C5 H5 119.5 . . ?
C5' C6 C1' 121.7(14) . . ?
C1 C6 C5 117.7(14) . . ?
C1 C6 S1 128.2(11) . . ?
C5' C6 S1 121.1(13) . . ?
C1' C6 S1 117.2(12) . . ?
C5 C6 S1 114.1(12) . . ?
C8 C7 S1 114.8(10) . . ?
C8 C7 H7A 108.6 . . ?
S1 C7 H7A 108.6 . . ?
C8 C7 H7B 108.6 . . ?
S1 C7 H7B 108.6 . . ?
H7A C7 H7B 107.5 . . ?
O1 C8 O2 121.6(13) . . ?
O1 C8 C7 123.8(13) . . ?
O2 C8 C7 114.6(13) . . ?
C10 C9 Sn1 114.4(11) . . ?
C10 C9 H9A 108.7 . . ?
Sn1 C9 H9A 108.7 . . ?
C10 C9 H9B 108.7 . . ?
Sn1 C9 H9B 108.7 . . ?
H9A C9 H9B 107.6 . . ?
C11 C10 C9 137.6(18) . . ?
C11 C10 H10A 102.7 . . ?
C9 C10 H10A 102.7 . . ?
C11 C10 H10B 102.7 . . ?
C9 C10 H10B 102.7 . . ?
H10A C10 H10B 105.0 . . ?
C10 C11 C12 124.9(17) . . ?
C10 C11 H11A 106.1 . . ?
C12 C11 H11A 106.1 . . ?
C10 C11 H11B 106.1 . . ?
C12 C11 H11B 106.1 . . ?
H11A C11 H11B 106.3 . . ?
C11 C12 H12A 109.5 . . ?
C11 C12 H12B 109.5 . . ?
H12A C12 H12B 109.5 . . ?
C11 C12 H12C 109.5 . . ?
H12A C12 H12C 109.5 . . ?
H12B C12 H12C 109.5 . . ?
C6 C1' C2' 118.9(15) . . ?
C6 C1' H1' 120.6 . . ?
C2' C1' H1' 120.5 . . ?
C3' C2' C1' 119.5(16) . . ?
C3' C2' H2' 120.2 . . ?
C1' C2' H2' 120.3 . . ?
F1' C3' C2' 122(5) . . ?
F1' C3' C4' 117(5) . . ?
C2' C3' C4' 121.4(17) . . ?
C6 C5' C4' 119.2(16) . . ?
C6 C5' H5' 120.4 . . ?
C4' C5' H5' 120.5 . . ?
C3' C4' C5' 119.4(17) . . ?
C3' C4' H4' 120.4 . . ?
C5' C4' H4' 120.3 . . ?

_refine_diff_density_max         0.953
_refine_diff_density_min         -0.586
_refine_diff_density_rms         0.119

####################################################################### 
# 
# 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_170503j
_database_code_depnum_ccdc_archive 'CCDC 1489807'
_audit_update_record             
;
2017-05-10 deposited with the CCDC.
2017-05-18 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            'C24 H30 F2 O4 Se2 Sn'
_chemical_formula_weight         697.09

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'
O O 0.0106 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
Se Se -0.0929 2.2259 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
Sn Sn -0.6537 1.4246 '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                   29.260(3)
_cell_length_b                   5.2170(5)
_cell_length_c                   20.7101(18)
_cell_angle_alpha                90
_cell_angle_beta                 121.175(2)
_cell_angle_gamma                90
_cell_volume                     2704.9(4)
_cell_formula_units_Z            4
_cell_measurement_temperature    298(2)
_cell_measurement_reflns_used    1427
_cell_measurement_theta_min      3.265
_cell_measurement_theta_max      22.139

_exptl_crystal_description       block
_exptl_crystal_colour            colourless
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.712
_exptl_crystal_F_000             1368
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.430
_exptl_crystal_size_mid          0.200
_exptl_crystal_size_min          0.140
_exptl_absorpt_coefficient_mu    3.676
_shelx_estimated_absorpt_T_min   0.301
_shelx_estimated_absorpt_T_max   0.627
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.3009
_exptl_absorpt_correction_T_max  0.6271
_exptl_absorpt_process_details   sadabs
_exptl_absorpt_special_details   ?
_diffrn_ambient_temperature      298(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_source                   ?
_diffrn_measurement_device_type  'CCD area detector'
_diffrn_measurement_method       'phi and omega scans'
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            6413
_diffrn_reflns_av_unetI/netI     0.0970
_diffrn_reflns_av_R_equivalents  0.1065
_diffrn_reflns_limit_h_min       -34
_diffrn_reflns_limit_h_max       34
_diffrn_reflns_limit_k_min       -6
_diffrn_reflns_limit_k_max       6
_diffrn_reflns_limit_l_min       -24
_diffrn_reflns_limit_l_max       20
_diffrn_reflns_theta_min         2.852
_diffrn_reflns_theta_max         25.018
_diffrn_reflns_theta_full        25.018
_diffrn_measured_fraction_theta_max 0.995
_diffrn_measured_fraction_theta_full 0.995
_diffrn_reflns_Laue_measured_fraction_max 0.995
_diffrn_reflns_Laue_measured_fraction_full 0.995
_diffrn_reflns_point_group_measured_fraction_max 0.995
_diffrn_reflns_point_group_measured_fraction_full 0.995
_reflns_number_total             2381
_reflns_number_gt                1428
_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       'Bruker SMART'
_computing_cell_refinement       'Bruker SMART'
_computing_data_reduction        'Bruker SAINT'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 1990)'
_computing_structure_refinement  'SHELXL-2014/7 (Sheldrick, 2014)'
_computing_molecular_graphics    'Bruker SHELXTL'
_computing_publication_material  'Bruker SHELXTL'
_refine_special_details          ?
_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0759P)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         2381
_refine_ls_number_parameters     165
_refine_ls_number_restraints     42
_refine_ls_R_factor_all          0.1128
_refine_ls_R_factor_gt           0.0697
_refine_ls_wR_factor_ref         0.1795
_refine_ls_wR_factor_gt          0.1632
_refine_ls_goodness_of_fit_ref   1.078
_refine_ls_restrained_S_all      1.079
_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
Sn1 Sn 0.5000 0.59635(18) 0.7500 0.0543(4) Uani 1 2 d S T P . .
Se1 Se 0.58141(4) 0.0540(2) 0.62838(6) 0.0632(4) Uani 1 1 d . . . . .
F1 F 0.7186(3) 0.9001(15) 0.6215(5) 0.119(3) Uani 1 1 d . . . . .
O1 O 0.5030(3) 0.2856(13) 0.6870(4) 0.0683(19) Uani 1 1 d . . . . .
O2 O 0.5046(3) 0.6264(13) 0.6278(4) 0.0716(19) Uani 1 1 d . . . . .
C1 C 0.5059(3) 0.3909(18) 0.6339(5) 0.048(2) Uani 1 1 d . . . . .
C2 C 0.5111(3) 0.2168(19) 0.5810(5) 0.057(2) Uani 1 1 d . . . . .
H2A H 0.5052 0.3139 0.5374 0.069 Uiso 1 1 calc R U . . .
H2B H 0.4838 0.0851 0.5636 0.069 Uiso 1 1 calc R U . . .
C3 C 0.6225(3) 0.333(2) 0.6228(5) 0.057(2) Uani 1 1 d . . . . .
C4 C 0.6620(4) 0.439(2) 0.6903(6) 0.072(3) Uani 1 1 d . . . . .
H4 H 0.6666 0.3820 0.7357 0.087 Uiso 1 1 calc R U . . .
C5 C 0.6952(4) 0.633(2) 0.6904(7) 0.081(3) Uani 1 1 d . . . . .
H5 H 0.7223 0.7028 0.7353 0.097 Uiso 1 1 calc R U . . .
C6 C 0.6868(5) 0.714(2) 0.6237(8) 0.080(3) Uani 1 1 d . . . . .
C7 C 0.6488(5) 0.609(2) 0.5562(7) 0.085(4) Uani 1 1 d . . . . .
H7 H 0.6448 0.6656 0.5110 0.102 Uiso 1 1 calc R U . . .
C8 C 0.6161(4) 0.414(2) 0.5573(6) 0.068(3) Uani 1 1 d . . . . .
H8 H 0.5899 0.3406 0.5122 0.082 Uiso 1 1 calc R U . . .
C9 C 0.4267(6) 0.792(4) 0.6907(12) 0.069(5) Uani 0.587(11) 1 d D U P A 1
H9A H 0.4230 0.9029 0.7254 0.083 Uiso 0.587(11) 1 calc R U P A 1
H9B H 0.4266 0.8997 0.6525 0.083 Uiso 0.587(11) 1 calc R U P A 1
C10 C 0.3794(6) 0.612(4) 0.6534(14) 0.121(7) Uani 0.587(11) 1 d D U P A 1
H10A H 0.3766 0.5280 0.6930 0.146 Uiso 0.587(11) 1 calc R U P A 1
H10B H 0.3875 0.4797 0.6278 0.146 Uiso 0.587(11) 1 calc R U P A 1
C11 C 0.3244(8) 0.721(5) 0.5965(15) 0.114(7) Uani 0.587(11) 1 d D U P A 1
H11A H 0.3225 0.7334 0.5484 0.137 Uiso 0.587(11) 1 calc R U P A 1
H11B H 0.2981 0.5949 0.5904 0.137 Uiso 0.587(11) 1 calc R U P A 1
C12 C 0.3063(14) 0.977(5) 0.610(2) 0.140(9) Uani 0.587(11) 1 d D U P A 1
H12A H 0.3266 1.0170 0.6631 0.209 Uiso 0.587(11) 1 calc R U P A 1
H12B H 0.2690 0.9687 0.5937 0.209 Uiso 0.587(11) 1 calc R U P A 1
H12C H 0.3118 1.1088 0.5825 0.209 Uiso 0.587(11) 1 calc R U P A 1
C9' C 0.4139(12) 0.657(5) 0.6947(16) 0.069(5) Uani 0.413(11) 1 d D . P A 2
H9'1 H 0.3964 0.4912 0.6791 0.083 Uiso 0.413(11) 1 calc R U P A 2
H9'2 H 0.4063 0.7265 0.7315 0.083 Uiso 0.413(11) 1 calc R U P A 2
C10' C 0.3892(10) 0.833(6) 0.6264(17) 0.121(7) Uani 0.413(11) 1 d D . P A 2
H10C H 0.3982 0.7582 0.5914 0.146 Uiso 0.413(11) 1 calc R U P A 2
H10D H 0.4089 0.9923 0.6436 0.146 Uiso 0.413(11) 1 calc R U P A 2
C11' C 0.3301(10) 0.908(9) 0.579(2) 0.114(7) Uani 0.413(11) 1 d D . P A 2
H11C H 0.3259 1.0907 0.5679 0.137 Uiso 0.413(11) 1 calc R U P A 2
H11D H 0.3118 0.8134 0.5317 0.137 Uiso 0.413(11) 1 calc R U P A 2
C12' C 0.310(2) 0.833(9) 0.631(3) 0.140(9) Uani 0.413(11) 1 d D . P A 2
H12D H 0.2888 0.6814 0.6124 0.209 Uiso 0.413(11) 1 calc R U P A 2
H12E H 0.2893 0.9703 0.6336 0.209 Uiso 0.413(11) 1 calc R U P A 2
H12F H 0.3403 0.8005 0.6809 0.209 Uiso 0.413(11) 1 calc R U 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
Sn1 C9 2.104(19) 2_656 ?
Sn1 C9 2.104(19) . ?
Sn1 O1 2.111(6) . ?
Sn1 O1 2.111(6) 2_656 ?
Sn1 C9' 2.18(3) . ?
Sn1 C9' 2.18(3) 2_656 ?
Sn1 O2 2.607(7) . ?
Se1 C3 1.928(10) . ?
Se1 C2 1.956(9) . ?
F1 C6 1.363(12) . ?
O1 C1 1.272(10) . ?
O2 C1 1.234(10) . ?
C1 C2 1.490(12) . ?
C2 H2A 0.9700 . ?
C2 H2B 0.9700 . ?
C3 C8 1.339(13) . ?
C3 C4 1.388(13) . ?
C4 C5 1.399(15) . ?
C4 H4 0.9300 . ?
C5 C6 1.338(15) . ?
C5 H5 0.9300 . ?
C6 C7 1.371(16) . ?
C7 C8 1.405(15) . ?
C7 H7 0.9300 . ?
C8 H8 0.9300 . ?
C9 C10 1.514(10) . ?
C9 H9A 0.9700 . ?
C9 H9B 0.9700 . ?
C10 C11 1.530(10) . ?
C10 H10A 0.9700 . ?
C10 H10B 0.9700 . ?
C11 C12 1.518(10) . ?
C11 H11A 0.9700 . ?
C11 H11B 0.9700 . ?
C12 H12A 0.9600 . ?
C12 H12B 0.9600 . ?
C12 H12C 0.9600 . ?
C9' C10' 1.518(10) . ?
C9' H9'1 0.9700 . ?
C9' H9'2 0.9700 . ?
C10' C11' 1.536(10) . ?
C10' H10C 0.9700 . ?
C10' H10D 0.9700 . ?
C11' C12' 1.526(10) . ?
C11' H11C 0.9700 . ?
C11' H11D 0.9700 . ?
C12' H12D 0.9600 . ?
C12' H12E 0.9600 . ?
C12' H12F 0.9600 . ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
C9 Sn1 C9 121.9(10) 2_656 . ?
C9 Sn1 O1 112.2(6) 2_656 . ?
C9 Sn1 O1 111.6(6) . . ?
C9 Sn1 O1 111.6(6) 2_656 2_656 ?
C9 Sn1 O1 112.2(6) . 2_656 ?
O1 Sn1 O1 79.7(4) . 2_656 ?
O1 Sn1 C9' 101.1(9) . . ?
O1 Sn1 C9' 91.7(7) 2_656 . ?
O1 Sn1 C9' 91.7(7) . 2_656 ?
O1 Sn1 C9' 101.1(9) 2_656 2_656 ?
C9' Sn1 C9' 163.4(15) . 2_656 ?
C9 Sn1 O2 89.3(7) 2_656 . ?
C9 Sn1 O2 87.4(7) . . ?
O1 Sn1 O2 53.6(2) . . ?
O1 Sn1 O2 133.3(2) 2_656 . ?
C9' Sn1 O2 96.2(8) . . ?
C9' Sn1 O2 82.8(8) 2_656 . ?
C3 Se1 C2 99.7(4) . . ?
C1 O1 Sn1 104.2(6) . . ?
C1 O2 Sn1 81.7(6) . . ?
O2 C1 O1 120.4(9) . . ?
O2 C1 C2 122.8(9) . . ?
O1 C1 C2 116.8(8) . . ?
C1 C2 Se1 112.1(6) . . ?
C1 C2 H2A 109.2 . . ?
Se1 C2 H2A 109.2 . . ?
C1 C2 H2B 109.2 . . ?
Se1 C2 H2B 109.2 . . ?
H2A C2 H2B 107.9 . . ?
C8 C3 C4 119.9(10) . . ?
C8 C3 Se1 122.3(8) . . ?
C4 C3 Se1 117.6(7) . . ?
C3 C4 C5 120.5(10) . . ?
C3 C4 H4 119.8 . . ?
C5 C4 H4 119.8 . . ?
C6 C5 C4 118.0(11) . . ?
C6 C5 H5 121.0 . . ?
C4 C5 H5 121.0 . . ?
C5 C6 F1 119.7(12) . . ?
C5 C6 C7 123.0(12) . . ?
F1 C6 C7 117.2(12) . . ?
C6 C7 C8 118.2(11) . . ?
C6 C7 H7 120.9 . . ?
C8 C7 H7 120.9 . . ?
C3 C8 C7 120.4(11) . . ?
C3 C8 H8 119.8 . . ?
C7 C8 H8 119.8 . . ?
C10 C9 Sn1 112.5(13) . . ?
C10 C9 H9A 109.1 . . ?
Sn1 C9 H9A 109.1 . . ?
C10 C9 H9B 109.1 . . ?
Sn1 C9 H9B 109.1 . . ?
H9A C9 H9B 107.8 . . ?
C9 C10 C11 118.7(18) . . ?
C9 C10 H10A 107.6 . . ?
C11 C10 H10A 107.6 . . ?
C9 C10 H10B 107.6 . . ?
C11 C10 H10B 107.6 . . ?
H10A C10 H10B 107.1 . . ?
C12 C11 C10 121(2) . . ?
C12 C11 H11A 107.1 . . ?
C10 C11 H11A 107.1 . . ?
C12 C11 H11B 107.1 . . ?
C10 C11 H11B 107.1 . . ?
H11A C11 H11B 106.8 . . ?
C11 C12 H12A 109.5 . . ?
C11 C12 H12B 109.5 . . ?
H12A C12 H12B 109.5 . . ?
C11 C12 H12C 109.5 . . ?
H12A C12 H12C 109.5 . . ?
H12B C12 H12C 109.5 . . ?
C10' C9' Sn1 116(2) . . ?
C10' C9' H9'1 108.3 . . ?
Sn1 C9' H9'1 108.3 . . ?
C10' C9' H9'2 108.3 . . ?
Sn1 C9' H9'2 108.3 . . ?
H9'1 C9' H9'2 107.4 . . ?
C9' C10' C11' 126(3) . . ?
C9' C10' H10C 105.8 . . ?
C11' C10' H10C 105.8 . . ?
C9' C10' H10D 105.8 . . ?
C11' C10' H10D 105.8 . . ?
H10C C10' H10D 106.2 . . ?
C12' C11' C10' 101(3) . . ?
C12' C11' H11C 111.6 . . ?
C10' C11' H11C 111.6 . . ?
C12' C11' H11D 111.6 . . ?
C10' C11' H11D 111.6 . . ?
H11C C11' H11D 109.4 . . ?
C11' C12' H12D 109.5 . . ?
C11' C12' H12E 109.5 . . ?
H12D C12' H12E 109.5 . . ?
C11' C12' H12F 109.5 . . ?
H12D C12' H12F 109.5 . . ?
H12E C12' H12F 109.5 . . ?

_refine_diff_density_max         1.206
_refine_diff_density_min         -1.074
_refine_diff_density_rms         0.165

####################################################################### 
# 
# 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_160417b
_database_code_depnum_ccdc_archive 'CCDC 1509288'
_audit_update_record             
;
2017-05-10 deposited with the CCDC.
2017-05-18 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            'C40 H48 F4 O10 S4 Sn4'
_chemical_formula_weight         1367.78

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'
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'
Sn Sn -0.6537 1.4246 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

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

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

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

_cell_length_a                   11.6817(9)
_cell_length_b                   11.9698(10)
_cell_length_c                   17.8333(15)
_cell_angle_alpha                90
_cell_angle_beta                 94.4010(10)
_cell_angle_gamma                90
_cell_volume                     2486.2(4)
_cell_formula_units_Z            2
_cell_measurement_temperature    298(2)
_cell_measurement_reflns_used    2571
_cell_measurement_theta_min      2.4405
_cell_measurement_theta_max      25.8095

_exptl_crystal_description       block
_exptl_crystal_colour            clourless
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.827
_exptl_crystal_F_000             1336
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.310
_exptl_crystal_size_mid          0.180
_exptl_crystal_size_min          0.100
_exptl_absorpt_coefficient_mu    2.219
_shelx_estimated_absorpt_T_min   0.546
_shelx_estimated_absorpt_T_max   0.809
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.5462
_exptl_absorpt_correction_T_max  0.8086
_exptl_absorpt_process_details   sadabs
_exptl_absorpt_special_details   ?
_diffrn_ambient_temperature      298(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_source                   ?
_diffrn_measurement_device_type  'CCD area detector'
_diffrn_measurement_method       'phi and omega scans'
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            12195
_diffrn_reflns_av_unetI/netI     0.0806
_diffrn_reflns_av_R_equivalents  0.0624
_diffrn_reflns_limit_h_min       -13
_diffrn_reflns_limit_h_max       13
_diffrn_reflns_limit_k_min       -13
_diffrn_reflns_limit_k_max       14
_diffrn_reflns_limit_l_min       -21
_diffrn_reflns_limit_l_max       16
_diffrn_reflns_theta_min         2.440
_diffrn_reflns_theta_max         25.020
_diffrn_reflns_theta_full        25.020
_diffrn_measured_fraction_theta_max 0.996
_diffrn_measured_fraction_theta_full 0.996
_diffrn_reflns_Laue_measured_fraction_max 0.996
_diffrn_reflns_Laue_measured_fraction_full 0.996
_diffrn_reflns_point_group_measured_fraction_max 0.996
_diffrn_reflns_point_group_measured_fraction_full 0.996
_reflns_number_total             4368
_reflns_number_gt                2624
_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       'Bruker SMART'
_computing_cell_refinement       'Bruker SMART'
_computing_data_reduction        'Bruker SAINT'
_computing_structure_solution    'SHELXL-2014/7 (Sheldrick, 1990)'
_computing_structure_refinement  'SHELXL-2014/7 (Sheldrick, 2014)'
_computing_molecular_graphics    Diamond
_computing_publication_material  'Bruker SHELXTL'
_refine_special_details          ?
_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0356P)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         4368
_refine_ls_number_parameters     284
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0874
_refine_ls_R_factor_gt           0.0437
_refine_ls_wR_factor_ref         0.0930
_refine_ls_wR_factor_gt          0.0779
_refine_ls_goodness_of_fit_ref   0.962
_refine_ls_restrained_S_all      0.962
_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
Sn1 Sn 0.11852(3) 0.06034(4) 0.03845(2) 0.03196(15) Uani 1 1 d . . . . .
Sn2 Sn -0.11635(4) 0.04993(4) 0.15870(2) 0.03656(16) Uani 1 1 d . . . . .
S1 S 0.52431(15) 0.18688(17) -0.00345(11) 0.0533(6) Uani 1 1 d . . . . .
S2 S 0.29030(19) 0.2357(2) 0.18961(15) 0.0867(9) Uani 1 1 d . . . . .
F1 F 0.5661(5) -0.0657(5) 0.3868(4) 0.122(2) Uani 1 1 d . . . . .
F2 F 0.2657(4) 0.6060(4) 0.0005(3) 0.0890(16) Uani 1 1 d . . . . .
O1 O 0.0082(5) 0.1849(6) 0.2838(3) 0.089(2) Uani 1 1 d . . . . .
O2 O 0.0469(4) 0.1382(4) 0.1691(3) 0.0457(13) Uani 1 1 d . . . . .
O3 O -0.0575(3) 0.0213(4) 0.0580(2) 0.0344(11) Uani 1 1 d . . . . .
O4 O 0.2980(3) 0.0625(4) -0.0065(3) 0.0469(13) Uani 1 1 d . . . . .
O5 O 0.2760(4) 0.0517(4) -0.1304(3) 0.0581(15) Uani 1 1 d . . . . .
C1 C 0.3390(7) 0.1210(7) 0.3231(5) 0.064(2) Uani 1 1 d . . . . .
H1 H 0.2738 0.1530 0.3410 0.077 Uiso 1 1 calc R U . . .
C2 C 0.4071(8) 0.0505(8) 0.3691(5) 0.071(3) Uani 1 1 d . . . . .
H2 H 0.3873 0.0340 0.4174 0.086 Uiso 1 1 calc R U . . .
C3 C 0.5013(8) 0.0068(8) 0.3431(7) 0.074(3) Uani 1 1 d . . . . .
C4 C 0.5303(8) 0.0279(9) 0.2721(7) 0.084(3) Uani 1 1 d . . . . .
H4 H 0.5949 -0.0052 0.2543 0.101 Uiso 1 1 calc R U . . .
C5 C 0.4639(8) 0.0979(9) 0.2275(5) 0.080(3) Uani 1 1 d . . . . .
H5 H 0.4846 0.1151 0.1795 0.096 Uiso 1 1 calc R U . . .
C6 C 0.3660(6) 0.1436(7) 0.2531(5) 0.053(2) Uani 1 1 d . . . . .
C7 C 0.1669(6) 0.2723(7) 0.2344(5) 0.071(3) Uani 1 1 d . . . . .
H7A H 0.1902 0.2861 0.2869 0.085 Uiso 1 1 calc R U . . .
H7B H 0.1389 0.3426 0.2130 0.085 Uiso 1 1 calc R U . . .
C8 C 0.0664(7) 0.1912(7) 0.2312(5) 0.055(2) Uani 1 1 d . . . . .
C9 C -0.0696(7) -0.0768(7) 0.2363(4) 0.067(3) Uani 1 1 d . . . . .
H9A H -0.0709 -0.1476 0.2109 0.100 Uiso 1 1 calc R U . . .
H9B H -0.1229 -0.0783 0.2747 0.100 Uiso 1 1 calc R U . . .
H9C H 0.0062 -0.0626 0.2588 0.100 Uiso 1 1 calc R U . . .
C10 C -0.2198(6) 0.1937(7) 0.1587(4) 0.064(2) Uani 1 1 d . . . . .
H10A H -0.1734 0.2587 0.1523 0.097 Uiso 1 1 calc R U . . .
H10B H -0.2546 0.1988 0.2057 0.097 Uiso 1 1 calc R U . . .
H10C H -0.2787 0.1893 0.1182 0.097 Uiso 1 1 calc R U . . .
C11 C 0.1944(6) -0.0602(6) 0.1113(4) 0.049(2) Uani 1 1 d . . . . .
H11A H 0.1356 -0.1048 0.1313 0.074 Uiso 1 1 calc R U . . .
H11B H 0.2387 -0.0238 0.1518 0.074 Uiso 1 1 calc R U . . .
H11C H 0.2436 -0.1071 0.0843 0.074 Uiso 1 1 calc R U . . .
C12 C 0.0995(6) 0.2302(6) 0.0100(4) 0.054(2) Uani 1 1 d . . . . .
H12A H 0.1017 0.2389 -0.0434 0.081 Uiso 1 1 calc R U . . .
H12B H 0.1609 0.2723 0.0352 0.081 Uiso 1 1 calc R U . . .
H12C H 0.0273 0.2570 0.0251 0.081 Uiso 1 1 calc R U . . .
C13 C 0.3356(5) 0.0698(5) -0.0711(4) 0.0325(16) Uani 1 1 d . . . . .
C14 C 0.4574(5) 0.1038(6) -0.0783(4) 0.0417(18) Uani 1 1 d . . . . .
H14A H 0.4605 0.1451 -0.1249 0.050 Uiso 1 1 calc R U . . .
H14B H 0.5028 0.0365 -0.0827 0.050 Uiso 1 1 calc R U . . .
C15 C 0.4398(6) 0.3079(6) -0.0051(4) 0.0408(18) Uani 1 1 d . . . . .
C16 C 0.4474(7) 0.3739(7) 0.0585(4) 0.054(2) Uani 1 1 d . . . . .
H16 H 0.4932 0.3506 0.1006 0.065 Uiso 1 1 calc R U . . .
C17 C 0.3885(7) 0.4744(7) 0.0612(5) 0.064(2) Uani 1 1 d . . . . .
H17 H 0.3944 0.5185 0.1042 0.077 Uiso 1 1 calc R U . . .
C18 C 0.3215(7) 0.5064(7) -0.0015(6) 0.056(2) Uani 1 1 d . . . . .
C19 C 0.3099(6) 0.4426(7) -0.0650(5) 0.055(2) Uani 1 1 d . . . . .
H19 H 0.2622 0.4655 -0.1063 0.066 Uiso 1 1 calc R U . . .
C20 C 0.3696(6) 0.3441(7) -0.0669(4) 0.051(2) Uani 1 1 d . . . . .
H20 H 0.3631 0.3007 -0.1103 0.061 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
Sn1 O3 2.057(4) 3 ?
Sn1 C11 2.092(6) . ?
Sn1 C12 2.103(7) . ?
Sn1 O3 2.163(4) . ?
Sn1 O4 2.302(4) . ?
Sn2 O3 2.001(4) . ?
Sn2 C9 2.097(7) . ?
Sn2 C10 2.103(7) . ?
Sn2 O2 2.175(4) . ?
Sn2 O5 2.251(5) 3 ?
S1 C15 1.752(7) . ?
S1 C14 1.795(6) . ?
S2 C7 1.756(8) . ?
S2 C6 1.768(8) . ?
F1 C3 1.357(10) . ?
F2 C18 1.361(9) . ?
O1 C8 1.202(8) . ?
O2 C8 1.281(8) . ?
O3 Sn1 2.057(4) 3 ?
O4 C13 1.266(7) . ?
O5 C13 1.241(7) . ?
O5 Sn2 2.251(5) 3 ?
C1 C6 1.338(10) . ?
C1 C2 1.385(11) . ?
C2 C3 1.334(12) . ?
C3 C4 1.360(12) . ?
C4 C5 1.357(13) . ?
C5 C6 1.378(10) . ?
C7 C8 1.521(10) . ?
C13 C14 1.495(8) . ?
C15 C16 1.380(9) . ?
C15 C20 1.392(9) . ?
C16 C17 1.388(10) . ?
C17 C18 1.369(11) . ?
C18 C19 1.364(10) . ?
C19 C20 1.372(10) . ?

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 Sn1 C11 107.2(2) 3 . ?
O3 Sn1 C12 103.5(2) 3 . ?
C11 Sn1 C12 148.0(3) . . ?
O3 Sn1 O3 76.09(16) 3 . ?
C11 Sn1 O3 96.5(2) . . ?
C12 Sn1 O3 99.4(2) . . ?
O3 Sn1 O4 88.87(15) 3 . ?
C11 Sn1 O4 82.6(2) . . ?
C12 Sn1 O4 89.3(2) . . ?
O3 Sn1 O4 163.99(16) . . ?
O3 Sn2 C9 112.2(3) . . ?
O3 Sn2 C10 112.2(2) . . ?
C9 Sn2 C10 135.4(3) . . ?
O3 Sn2 O2 78.50(16) . . ?
C9 Sn2 O2 96.5(2) . . ?
C10 Sn2 O2 95.9(2) . . ?
O3 Sn2 O5 92.40(16) . 3 ?
C9 Sn2 O5 85.8(3) . 3 ?
C10 Sn2 O5 88.6(3) . 3 ?
O2 Sn2 O5 170.82(17) . 3 ?
C15 S1 C14 103.5(3) . . ?
C7 S2 C6 104.6(4) . . ?
C8 O2 Sn2 114.3(5) . . ?
Sn2 O3 Sn1 135.3(2) . 3 ?
Sn2 O3 Sn1 120.26(19) . . ?
Sn1 O3 Sn1 103.91(16) 3 . ?
C13 O4 Sn1 134.9(4) . . ?
C13 O5 Sn2 133.4(4) . 3 ?
C6 C1 C2 120.7(8) . . ?
C3 C2 C1 119.1(9) . . ?
C2 C3 F1 119.4(10) . . ?
C2 C3 C4 121.4(10) . . ?
F1 C3 C4 119.1(10) . . ?
C5 C4 C3 119.3(9) . . ?
C4 C5 C6 120.2(9) . . ?
C1 C6 C5 119.4(9) . . ?
C1 C6 S2 125.5(7) . . ?
C5 C6 S2 115.0(7) . . ?
C8 C7 S2 118.8(6) . . ?
O1 C8 O2 124.7(8) . . ?
O1 C8 C7 119.5(8) . . ?
O2 C8 C7 115.7(7) . . ?
O5 C13 O4 123.5(6) . . ?
O5 C13 C14 116.7(6) . . ?
O4 C13 C14 119.7(6) . . ?
C13 C14 S1 116.7(5) . . ?
C16 C15 C20 118.0(7) . . ?
C16 C15 S1 117.3(6) . . ?
C20 C15 S1 124.6(6) . . ?
C15 C16 C17 121.6(8) . . ?
C18 C17 C16 117.9(8) . . ?
F2 C18 C19 119.7(9) . . ?
F2 C18 C17 117.9(8) . . ?
C19 C18 C17 122.4(8) . . ?
C18 C19 C20 118.9(8) . . ?
C19 C20 C15 121.2(7) . . ?

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
C6 C1 C2 C3 1.1(14) . . . . ?
C1 C2 C3 F1 -177.5(8) . . . . ?
C1 C2 C3 C4 -1.5(15) . . . . ?
C2 C3 C4 C5 2.1(16) . . . . ?
F1 C3 C4 C5 178.2(9) . . . . ?
C3 C4 C5 C6 -2.4(15) . . . . ?
C2 C1 C6 C5 -1.4(13) . . . . ?
C2 C1 C6 S2 -177.6(7) . . . . ?
C4 C5 C6 C1 2.0(14) . . . . ?
C4 C5 C6 S2 178.6(7) . . . . ?
C7 S2 C6 C1 -7.5(8) . . . . ?
C7 S2 C6 C5 176.2(6) . . . . ?
C6 S2 C7 C8 -79.9(7) . . . . ?
Sn2 O2 C8 O1 8.1(11) . . . . ?
Sn2 O2 C8 C7 -168.1(5) . . . . ?
S2 C7 C8 O1 146.3(7) . . . . ?
S2 C7 C8 O2 -37.3(10) . . . . ?
Sn2 O5 C13 O4 -24.3(11) 3 . . . ?
Sn2 O5 C13 C14 156.7(5) 3 . . . ?
Sn1 O4 C13 O5 -17.9(11) . . . . ?
Sn1 O4 C13 C14 161.0(5) . . . . ?
O5 C13 C14 S1 153.3(5) . . . . ?
O4 C13 C14 S1 -25.7(9) . . . . ?
C15 S1 C14 C13 -61.3(6) . . . . ?
C14 S1 C15 C16 161.4(5) . . . . ?
C14 S1 C15 C20 -21.4(7) . . . . ?
C20 C15 C16 C17 -0.8(10) . . . . ?
S1 C15 C16 C17 176.6(5) . . . . ?
C15 C16 C17 C18 0.2(11) . . . . ?
C16 C17 C18 F2 -178.6(6) . . . . ?
C16 C17 C18 C19 1.0(12) . . . . ?
F2 C18 C19 C20 178.0(6) . . . . ?
C17 C18 C19 C20 -1.7(12) . . . . ?
C18 C19 C20 C15 1.0(11) . . . . ?
C16 C15 C20 C19 0.2(10) . . . . ?
S1 C15 C20 C19 -177.0(5) . . . . ?

_refine_diff_density_max         0.880
_refine_diff_density_min         -0.678
_refine_diff_density_rms         0.135

####################################################################### 
# 
# 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_151025b
_database_code_depnum_ccdc_archive 'CCDC 1490057'
_audit_update_record             
;
2017-05-10 deposited with the CCDC.
2017-05-18 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            'C11 H15 F O2 Se Sn'
_chemical_formula_weight         395.88

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'
Se Se -0.0929 2.2259 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
Sn Sn -0.6537 1.4246 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_space_group_crystal_system      orthorhombic
_space_group_IT_number           19
_space_group_name_H-M_alt        'P 21 21 21'
_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'

_cell_length_a                   9.6149(8)
_cell_length_b                   12.9348(11)
_cell_length_c                   22.7853(19)
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_volume                     2833.7(4)
_cell_formula_units_Z            8
_cell_measurement_temperature    298(2)
_cell_measurement_reflns_used    2958
_cell_measurement_theta_min      2.744
_cell_measurement_theta_max      20.664

_exptl_crystal_description       block
_exptl_crystal_colour            colourless
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.856
_exptl_crystal_F_000             1520
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.470
_exptl_crystal_size_mid          0.310
_exptl_crystal_size_min          0.200
_exptl_absorpt_coefficient_mu    4.368
_shelx_estimated_absorpt_T_min   0.233
_shelx_estimated_absorpt_T_max   0.475
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.2333
_exptl_absorpt_correction_T_max  0.4754
_exptl_absorpt_process_details   sadabs
_exptl_absorpt_special_details   ?
_diffrn_ambient_temperature      298(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_source                   ?
_diffrn_measurement_device_type  'CCD area detector'
_diffrn_measurement_method       'phi and omega scans'
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            14159
_diffrn_reflns_av_unetI/netI     0.1489
_diffrn_reflns_av_R_equivalents  0.1268
_diffrn_reflns_limit_h_min       -11
_diffrn_reflns_limit_h_max       11
_diffrn_reflns_limit_k_min       -14
_diffrn_reflns_limit_k_max       15
_diffrn_reflns_limit_l_min       -25
_diffrn_reflns_limit_l_max       27
_diffrn_reflns_theta_min         2.299
_diffrn_reflns_theta_max         25.020
_diffrn_reflns_theta_full        25.020
_diffrn_measured_fraction_theta_max 0.997
_diffrn_measured_fraction_theta_full 0.997
_diffrn_reflns_Laue_measured_fraction_max 0.997
_diffrn_reflns_Laue_measured_fraction_full 0.997
_diffrn_reflns_point_group_measured_fraction_max 0.996
_diffrn_reflns_point_group_measured_fraction_full 0.996
_reflns_number_total             4998
_reflns_number_gt                2867
_reflns_threshold_expression     'I > 2σ(I)'
_reflns_Friedel_coverage         0.757
_reflns_Friedel_fraction_max     0.994
_reflns_Friedel_fraction_full    0.994

_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       'Bruker SMART'
_computing_cell_refinement       'Bruker SMART'
_computing_data_reduction        'Bruker SAINT'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 1990)'
_computing_structure_refinement  'SHELXL-2014/7 (Sheldrick, 2014)'
_computing_molecular_graphics    'Bruker SHELXTL'
_computing_publication_material  'Bruker SHELXTL'
_refine_special_details          ?
_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.1031P)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_abs_structure_details 
;
 Flack x determined using 830 quotients [(I+)-(I-)]/[(I+)+(I-)]
 (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259).
;
_refine_ls_abs_structure_Flack   0.05(3)
_chemical_absolute_configuration ?
_refine_ls_number_reflns         4998
_refine_ls_number_parameters     289
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.1378
_refine_ls_R_factor_gt           0.0751
_refine_ls_wR_factor_ref         0.2055
_refine_ls_wR_factor_gt          0.1801
_refine_ls_goodness_of_fit_ref   0.965
_refine_ls_restrained_S_all      0.965
_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
Sn1 Sn 1.10508(16) 0.77928(12) 1.03110(6) 0.0418(5) Uani 1 1 d . . . . .
Sn2 Sn 0.12032(16) 0.73408(14) 0.46569(7) 0.0465(5) Uani 1 1 d . . . . .
Se1 Se 0.1726(3) 0.8104(3) 0.67378(12) 0.0725(10) Uani 1 1 d . . . . .
Se2 Se 1.0534(3) 0.6714(3) 0.82902(12) 0.0763(11) Uani 1 1 d . . . . .
F1 F 0.670(3) 0.5178(19) 0.6413(7) 0.129(8) Uani 1 1 d . . . . .
F2 F 0.703(2) 0.9563(19) 0.7883(9) 0.119(8) Uani 1 1 d . . . . .
O1 O 0.7605(17) 0.6398(13) 0.9159(6) 0.048(4) Uani 1 1 d . . . . .
O2 O 0.9182(17) 0.6975(15) 0.9746(6) 0.057(5) Uani 1 1 d . . . . .
O3 O 0.4699(19) 0.7338(16) 0.6031(6) 0.063(5) Uani 1 1 d . . . . .
O4 O 0.3084(16) 0.7100(12) 0.5357(7) 0.050(4) Uani 1 1 d . . . . .
C1 C 0.964(4) 0.534(3) 0.7393(13) 0.089(12) Uani 1 1 d . . . . .
H1 H 1.0464 0.4993 0.7475 0.107 Uiso 1 1 calc R U . . .
C2 C 0.875(4) 0.498(3) 0.6950(12) 0.084(10) Uani 1 1 d . . . . .
H2 H 0.8972 0.4389 0.6736 0.101 Uiso 1 1 calc R U . . .
C3 C 0.758(4) 0.551(3) 0.6843(11) 0.081(10) Uani 1 1 d . . . . .
C4 C 0.716(4) 0.636(3) 0.7135(12) 0.080(11) Uani 1 1 d . . . . .
H4 H 0.6336 0.6705 0.7036 0.096 Uiso 1 1 calc R U . . .
C5 C 0.798(3) 0.670(3) 0.7579(13) 0.080(10) Uani 1 1 d . . . . .
H5 H 0.7699 0.7269 0.7803 0.096 Uiso 1 1 calc R U . . .
C6 C 0.926(4) 0.620(3) 0.7703(11) 0.071(10) Uani 1 1 d . . . . .
C7 C 0.995(3) 0.589(2) 0.8971(10) 0.057(7) Uani 1 1 d . . . . .
H7A H 0.9569 0.5234 0.8840 0.068 Uiso 1 1 calc R U . . .
H7B H 1.0745 0.5748 0.9220 0.068 Uiso 1 1 calc R U . . .
C8 C 0.887(2) 0.6479(18) 0.9308(9) 0.040(6) Uani 1 1 d . . . . .
C9 C 1.146(3) 0.859(2) 0.9518(9) 0.056(7) Uani 1 1 d . . . . .
H9A H 1.2203 0.8255 0.9312 0.083 Uiso 1 1 calc R U . . .
H9B H 1.0638 0.8590 0.9278 0.083 Uiso 1 1 calc R U . . .
H9C H 1.1720 0.9292 0.9605 0.083 Uiso 1 1 calc R U . . .
C10 C 1.173(3) 0.625(2) 1.0537(10) 0.056(7) Uani 1 1 d . . . . .
H10A H 1.2462 0.6037 1.0275 0.083 Uiso 1 1 calc R U . . .
H10B H 1.2076 0.6242 1.0933 0.083 Uiso 1 1 calc R U . . .
H10C H 1.0966 0.5776 1.0505 0.083 Uiso 1 1 calc R U . . .
C11 C 0.946(3) 0.839(2) 1.0837(11) 0.064(8) Uani 1 1 d . . . . .
H11A H 0.9362 0.7971 1.1183 0.096 Uiso 1 1 calc R U . . .
H11B H 0.9682 0.9085 1.0948 0.096 Uiso 1 1 calc R U . . .
H11C H 0.8601 0.8384 1.0621 0.096 Uiso 1 1 calc R U . . .
C12 C 0.413(3) 0.942(2) 0.6880(11) 0.064(8) Uani 1 1 d . . . . .
H12 H 0.3756 0.9783 0.6566 0.077 Uiso 1 1 calc R U . . .
C13 C 0.532(4) 0.972(3) 0.7125(12) 0.078(10) Uani 1 1 d . . . . .
H13 H 0.5819 1.0267 0.6967 0.093 Uiso 1 1 calc R U . . .
C14 C 0.580(4) 0.920(3) 0.7627(12) 0.080(10) Uani 1 1 d . . . . .
C15 C 0.508(4) 0.841(3) 0.7864(14) 0.095(12) Uani 1 1 d . . . . .
H15 H 0.5394 0.8099 0.8207 0.114 Uiso 1 1 calc R U . . .
C16 C 0.387(3) 0.808(3) 0.7595(11) 0.074(9) Uani 1 1 d . . . . .
H16 H 0.3358 0.7538 0.7751 0.089 Uiso 1 1 calc R U . . .
C17 C 0.346(3) 0.857(2) 0.7091(10) 0.058(8) Uani 1 1 d . . . . .
C18 C 0.245(3) 0.686(2) 0.6384(10) 0.067(8) Uani 1 1 d . . . . .
H18A H 0.2957 0.6467 0.6678 0.080 Uiso 1 1 calc R U . . .
H18B H 0.1684 0.6435 0.6249 0.080 Uiso 1 1 calc R U . . .
C19 C 0.341(2) 0.7078(17) 0.5873(11) 0.044(6) Uani 1 1 d . . . . .
C20 C 0.024(4) 0.607(2) 0.5059(13) 0.090(11) Uani 1 1 d . . . . .
H20A H -0.0445 0.6310 0.5333 0.135 Uiso 1 1 calc R U . . .
H20B H -0.0197 0.5650 0.4766 0.135 Uiso 1 1 calc R U . . .
H20C H 0.0928 0.5668 0.5263 0.135 Uiso 1 1 calc R U . . .
C21 C 0.115(4) 0.888(2) 0.4985(11) 0.076(9) Uani 1 1 d . . . . .
H21A H 0.1660 0.9330 0.4726 0.114 Uiso 1 1 calc R U . . .
H21B H 0.0199 0.9115 0.5007 0.114 Uiso 1 1 calc R U . . .
H21C H 0.1557 0.8904 0.5369 0.114 Uiso 1 1 calc R U . . .
C22 C 0.274(4) 0.687(3) 0.4043(11) 0.086(11) Uani 1 1 d . . . . .
H22A H 0.3159 0.7468 0.3868 0.129 Uiso 1 1 calc R U . . .
H22B H 0.3442 0.6472 0.4241 0.129 Uiso 1 1 calc R U . . .
H22C H 0.2316 0.6453 0.3744 0.129 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
Sn1 C11 2.09(3) . ?
Sn1 C9 2.12(2) . ?
Sn1 C10 2.17(3) . ?
Sn1 O1 2.189(16) 4_567 ?
Sn1 O2 2.450(15) . ?
Sn2 C20 2.10(3) . ?
Sn2 C22 2.12(3) . ?
Sn2 C21 2.13(3) . ?
Sn2 O3 2.172(16) 4_466 ?
Sn2 O4 2.432(15) . ?
Se1 C18 1.93(3) . ?
Se1 C17 1.95(3) . ?
Se2 C6 1.93(3) . ?
Se2 C7 1.96(3) . ?
F1 C3 1.37(3) . ?
F2 C14 1.39(4) . ?
O1 C8 1.27(3) . ?
O1 Sn1 2.189(15) 4_467 ?
O2 C8 1.22(2) . ?
O3 C19 1.33(3) . ?
O3 Sn2 2.172(16) 4_566 ?
O4 C19 1.22(3) . ?
C1 C6 1.37(4) . ?
C1 C2 1.40(5) . ?
C2 C3 1.35(4) . ?
C3 C4 1.35(4) . ?
C4 C5 1.36(4) . ?
C5 C6 1.43(4) . ?
C7 C8 1.50(3) . ?
C12 C13 1.33(4) . ?
C12 C17 1.36(4) . ?
C13 C14 1.40(4) . ?
C14 C15 1.34(4) . ?
C15 C16 1.38(4) . ?
C16 C17 1.37(3) . ?
C18 C19 1.51(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
C11 Sn1 C9 116.4(12) . . ?
C11 Sn1 C10 115.2(11) . . ?
C9 Sn1 C10 126.7(10) . . ?
C11 Sn1 O1 90.4(8) . 4_567 ?
C9 Sn1 O1 96.4(8) . 4_567 ?
C10 Sn1 O1 95.9(8) . 4_567 ?
C11 Sn1 O2 85.6(8) . . ?
C9 Sn1 O2 84.2(8) . . ?
C10 Sn1 O2 87.1(8) . . ?
O1 Sn1 O2 175.8(6) 4_567 . ?
C20 Sn2 C22 111.7(13) . . ?
C20 Sn2 C21 124.7(13) . . ?
C22 Sn2 C21 121.1(14) . . ?
C20 Sn2 O3 99.9(10) . 4_466 ?
C22 Sn2 O3 92.5(9) . 4_466 ?
C21 Sn2 O3 93.2(10) . 4_466 ?
C20 Sn2 O4 86.6(9) . . ?
C22 Sn2 O4 83.0(9) . . ?
C21 Sn2 O4 84.8(9) . . ?
O3 Sn2 O4 173.1(6) 4_466 . ?
C18 Se1 C17 97.1(12) . . ?
C6 Se2 C7 100.3(12) . . ?
C8 O1 Sn1 117.8(14) . 4_467 ?
C8 O2 Sn1 146.6(15) . . ?
C19 O3 Sn2 118.1(14) . 4_566 ?
C19 O4 Sn2 146.1(15) . . ?
C6 C1 C2 119(4) . . ?
C3 C2 C1 118(3) . . ?
C4 C3 C2 126(3) . . ?
C4 C3 F1 115(4) . . ?
C2 C3 F1 119(3) . . ?
C3 C4 C5 117(3) . . ?
C4 C5 C6 120(3) . . ?
C1 C6 C5 120(3) . . ?
C1 C6 Se2 118(3) . . ?
C5 C6 Se2 122(2) . . ?
C8 C7 Se2 109.0(18) . . ?
O2 C8 O1 120(2) . . ?
O2 C8 C7 121(2) . . ?
O1 C8 C7 119(2) . . ?
C13 C12 C17 120(3) . . ?
C12 C13 C14 119(3) . . ?
C15 C14 F2 121(3) . . ?
C15 C14 C13 121(3) . . ?
F2 C14 C13 117(3) . . ?
C14 C15 C16 119(3) . . ?
C17 C16 C15 118(3) . . ?
C12 C17 C16 122(3) . . ?
C12 C17 Se1 121(2) . . ?
C16 C17 Se1 117(2) . . ?
C19 C18 Se1 112.6(18) . . ?
O4 C19 O3 120(2) . . ?
O4 C19 C18 126(2) . . ?
O3 C19 C18 114(2) . . ?

loop_
_geom_torsion_atom_site_label_1
_geom_torsion_atom_site_label_2
_geom_torsion_atom_site_label_3
_geom_torsion_atom_site_label_4
_geom_torsion
_geom_torsion_site_symmetry_1
_geom_torsion_site_symmetry_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
_geom_torsion_publ_flag
C6 C1 C2 C3 1(5) . . . . ?
C1 C2 C3 C4 -1(6) . . . . ?
C1 C2 C3 F1 180(3) . . . . ?
C2 C3 C4 C5 -1(6) . . . . ?
F1 C3 C4 C5 178(3) . . . . ?
C3 C4 C5 C6 3(5) . . . . ?
C2 C1 C6 C5 1(5) . . . . ?
C2 C1 C6 Se2 -178(2) . . . . ?
C4 C5 C6 C1 -3(5) . . . . ?
C4 C5 C6 Se2 175(3) . . . . ?
Sn1 O2 C8 O1 -167(2) . . . . ?
Sn1 O2 C8 C7 18(4) . . . . ?
Sn1 O1 C8 O2 2(3) 4_467 . . . ?
Sn1 O1 C8 C7 176.9(17) 4_467 . . . ?
Se2 C7 C8 O2 -99(2) . . . . ?
Se2 C7 C8 O1 87(3) . . . . ?
C17 C12 C13 C14 -5(5) . . . . ?
C12 C13 C14 C15 -1(5) . . . . ?
C12 C13 C14 F2 -178(3) . . . . ?
F2 C14 C15 C16 180(3) . . . . ?
C13 C14 C15 C16 3(6) . . . . ?
C14 C15 C16 C17 0(5) . . . . ?
C13 C12 C17 C16 8(5) . . . . ?
C13 C12 C17 Se1 -179(2) . . . . ?
C15 C16 C17 C12 -5(5) . . . . ?
C15 C16 C17 Se1 -178(3) . . . . ?
Sn2 O4 C19 O3 -151.1(19) . . . . ?
Sn2 O4 C19 C18 24(4) . . . . ?
Sn2 O3 C19 O4 -5(3) 4_566 . . . ?
Sn2 O3 C19 C18 179.3(16) 4_566 . . . ?
Se1 C18 C19 O4 -95(3) . . . . ?
Se1 C18 C19 O3 80(2) . . . . ?

_refine_diff_density_max         1.679
_refine_diff_density_min         -1.591
_refine_diff_density_rms         0.213

####################################################################### 
# 
# 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_160525c
_database_code_depnum_ccdc_archive 'CCDC 1490058'
_audit_update_record             
;
2017-05-10 deposited with the CCDC.
2017-05-18 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            'C40 H48 F4 O10 Se4 Sn4'
_chemical_formula_weight         1555.38

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'
Se Se -0.0929 2.2259 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
Sn Sn -0.6537 1.4246 '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'

_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                   17.0682(14)
_cell_length_b                   15.0174(13)
_cell_length_c                   20.0535(17)
_cell_angle_alpha                90
_cell_angle_beta                 93.6930(10)
_cell_angle_gamma                90
_cell_volume                     5129.4(8)
_cell_formula_units_Z            4
_cell_measurement_temperature    298(2)
_cell_measurement_reflns_used    03658
_cell_measurement_theta_min      2.664
_cell_measurement_theta_max      23.844

_exptl_crystal_description       block
_exptl_crystal_colour            colourless
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    2.014
_exptl_crystal_F_000             2960
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.370
_exptl_crystal_size_mid          0.170
_exptl_crystal_size_min          0.120
_exptl_absorpt_coefficient_mu    4.827
_shelx_estimated_absorpt_T_min   0.268
_shelx_estimated_absorpt_T_max   0.595
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.2682
_exptl_absorpt_correction_T_max  0.5950
_exptl_absorpt_process_details   sadabs
_exptl_absorpt_special_details   ?
_diffrn_ambient_temperature      298(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_source                   ?
_diffrn_measurement_device_type  'CCD area detector'
_diffrn_measurement_method       'phi and omega scans'
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            12619
_diffrn_reflns_av_unetI/netI     0.0724
_diffrn_reflns_av_R_equivalents  0.0617
_diffrn_reflns_limit_h_min       -20
_diffrn_reflns_limit_h_max       15
_diffrn_reflns_limit_k_min       -17
_diffrn_reflns_limit_k_max       17
_diffrn_reflns_limit_l_min       -23
_diffrn_reflns_limit_l_max       23
_diffrn_reflns_theta_min         2.665
_diffrn_reflns_theta_max         25.020
_diffrn_reflns_theta_full        25.020
_diffrn_measured_fraction_theta_max 0.995
_diffrn_measured_fraction_theta_full 0.995
_diffrn_reflns_Laue_measured_fraction_max 0.995
_diffrn_reflns_Laue_measured_fraction_full 0.995
_diffrn_reflns_point_group_measured_fraction_max 0.995
_diffrn_reflns_point_group_measured_fraction_full 0.995
_reflns_number_total             4501
_reflns_number_gt                3102
_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       'Bruker SMART'
_computing_cell_refinement       'Bruker SMART'
_computing_data_reduction        'Bruker SAINT'
_computing_structure_solution    'SHELXL-2014/7 (Sheldrick, 1990)'
_computing_structure_refinement  'SHELXL-2014/7 (Sheldrick, 2014)'
_computing_molecular_graphics    'Bruker SHELXTL'
_computing_publication_material  'Bruker SHELXTL'
_refine_special_details          ?
_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0410P)²+34.2754P] 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         4501
_refine_ls_number_parameters     322
_refine_ls_number_restraints     198
_refine_ls_R_factor_all          0.0813
_refine_ls_R_factor_gt           0.0480
_refine_ls_wR_factor_ref         0.1259
_refine_ls_wR_factor_gt          0.1088
_refine_ls_goodness_of_fit_ref   1.050
_refine_ls_restrained_S_all      1.405
_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
Sn1 Sn 0.11558(3) 0.90436(4) 0.02876(3) 0.04389(19) Uani 1 1 d . . . . .
Sn2 Sn 0.28959(3) 0.75938(4) 0.07587(3) 0.04267(19) Uani 1 1 d . . . . .
Se1 Se 0.12834(7) 0.93936(8) 0.28892(6) 0.0793(4) Uani 1 1 d . . . . .
Se2 Se -0.12164(7) 0.83122(10) -0.16345(8) 0.1025(5) Uani 1 1 d . . . . .
F1 F -0.0602(14) 0.4537(14) -0.0699(13) 0.150(6) Uani 0.529(15) 1 d . U P A 1
F2 F 0.1616(12) 0.5575(12) 0.3737(11) 0.134(5) Uani 0.579(15) 1 d . U P B 1
F1' F -0.0518(16) 0.4448(17) -0.1217(15) 0.150(6) Uani 0.471(15) 1 d . . P A 2
F2' F 0.1256(16) 0.5477(17) 0.3312(15) 0.134(5) Uani 0.421(15) 1 d . . P B 2
O1 O -0.0088(4) 0.9569(5) -0.0630(3) 0.079(2) Uani 1 1 d . . . . .
O2 O 0.0783(3) 0.8529(4) -0.0731(3) 0.0540(15) Uani 1 1 d . . . . .
O3 O 0.1987(3) 0.8082(4) 0.0170(2) 0.0416(13) Uani 1 1 d . . . . .
O4 O 0.1699(5) 0.9449(6) 0.1300(3) 0.093(3) Uani 1 1 d . . . . .
O5 O 0.2521(5) 0.8420(5) 0.1662(3) 0.091(3) Uani 1 1 d . . . . .
C1 C -0.078(2) 0.6358(12) -0.1831(9) 0.096(5) Uani 0.529(15) 1 d D U P A 1
H1 H -0.0674 0.6454 -0.2275 0.115 Uiso 0.529(15) 1 calc R U P A 1
C2 C -0.0744(19) 0.5509(12) -0.1568(12) 0.099(5) Uani 0.529(15) 1 d D U P A 1
H2 H -0.0721 0.5018 -0.1850 0.118 Uiso 0.529(15) 1 calc R U P A 1
C3 C -0.074(2) 0.5393(12) -0.0889(12) 0.100(5) Uani 0.529(15) 1 d D U P A 1
C4 C -0.088(2) 0.6092(14) -0.0472(10) 0.102(5) Uani 0.529(15) 1 d D U P A 1
H4 H -0.0940 0.5989 -0.0021 0.122 Uiso 0.529(15) 1 calc R U P A 1
C5 C -0.093(2) 0.6939(13) -0.0720(6) 0.080(7) Uani 0.529(15) 1 d D . P A 1
H5 H -0.0931 0.7405 -0.0414 0.096 Uiso 0.529(15) 1 calc R U P A 1
C1' C -0.092(2) 0.6544(14) -0.1998(8) 0.096(5) Uani 0.471(15) 1 d D . P A 2
H1' H -0.1053 0.6744 -0.2428 0.115 Uiso 0.471(15) 1 calc R U P A 2
C2' C -0.0638(18) 0.5691(16) -0.1881(12) 0.099(5) Uani 0.471(15) 1 d D . P A 2
H2' H -0.0398 0.5379 -0.2213 0.118 Uiso 0.471(15) 1 calc R U P A 2
C3' C -0.072(2) 0.5308(13) -0.1268(15) 0.100(5) Uani 0.471(15) 1 d D . P A 2
C4' C -0.092(2) 0.5804(14) -0.0728(12) 0.102(5) Uani 0.471(15) 1 d D . P A 2
H4' H -0.0916 0.5545 -0.0307 0.122 Uiso 0.471(15) 1 calc R U P A 2
C5' C -0.112(2) 0.6685(14) -0.0815(8) 0.080(7) Uani 0.471(15) 1 d D . P A 2
H5' H -0.1349 0.6979 -0.0470 0.096 Uiso 0.471(15) 1 calc R U P A 2
C6 C -0.0986(6) 0.7151(7) -0.1383(5) 0.078(3) Uani 1 1 d D . . . .
C7 C -0.0150(6) 0.8764(8) -0.1640(4) 0.070(3) Uani 1 1 d . . . . .
H7A H 0.0174 0.8328 -0.1849 0.084 Uiso 1 1 calc R U . . .
H7B H -0.0151 0.9303 -0.1906 0.084 Uiso 1 1 calc R U . . .
C8 C 0.0196(5) 0.8960(6) -0.0966(4) 0.051(2) Uani 1 1 d . . . . .
C9 C 0.1672(5) 1.0197(6) -0.0049(5) 0.061(3) Uani 1 1 d . . . . .
H9A H 0.2233 1.0149 0.0015 0.091 Uiso 1 1 calc R U . . .
H9B H 0.1496 1.0699 0.0197 0.091 Uiso 1 1 calc R U . . .
H9C H 0.1526 1.0278 -0.0516 0.091 Uiso 1 1 calc R U . . .
C10 C 0.0277(6) 0.8362(7) 0.0765(5) 0.073(3) Uani 1 1 d . . . . .
H10A H -0.0144 0.8215 0.0444 0.110 Uiso 1 1 calc R U . . .
H10B H 0.0082 0.8734 0.1107 0.110 Uiso 1 1 calc R U . . .
H10C H 0.0492 0.7826 0.0963 0.110 Uiso 1 1 calc R U . . .
C11 C 0.3830(6) 0.8499(7) 0.0725(7) 0.085(4) Uani 1 1 d . . . . .
H11A H 0.4071 0.8436 0.0308 0.128 Uiso 1 1 calc R U . . .
H11B H 0.4211 0.8381 0.1087 0.128 Uiso 1 1 calc R U . . .
H11C H 0.3635 0.9096 0.0763 0.128 Uiso 1 1 calc R U . . .
C12 C 0.2511(6) 0.6528(6) 0.1331(4) 0.064(3) Uani 1 1 d . . . . .
H12A H 0.2042 0.6697 0.1538 0.097 Uiso 1 1 calc R U . . .
H12B H 0.2913 0.6377 0.1670 0.097 Uiso 1 1 calc R U . . .
H12C H 0.2404 0.6022 0.1047 0.097 Uiso 1 1 calc R U . . .
C13 C 0.2130(5) 0.9093(6) 0.1733(4) 0.048(2) Uani 1 1 d . . . . .
C14 C 0.2216(5) 0.9544(6) 0.2395(4) 0.055(2) Uani 1 1 d . . . . .
H14A H 0.2311 1.0174 0.2330 0.066 Uiso 1 1 calc R U . . .
H14B H 0.2666 0.9299 0.2653 0.066 Uiso 1 1 calc R U . . .
C15 C 0.1383(6) 0.8155(6) 0.3096(5) 0.071(3) Uani 1 1 d D . . . .
C16 C 0.1848(17) 0.7966(11) 0.3666(10) 0.090(4) Uani 0.579(15) 1 d D U P B 1
H16 H 0.2153 0.8411 0.3875 0.108 Uiso 0.579(15) 1 calc R U P B 1
C17 C 0.1859(16) 0.7116(12) 0.3927(10) 0.096(4) Uani 0.579(15) 1 d D U P B 1
H17 H 0.2059 0.7012 0.4362 0.115 Uiso 0.579(15) 1 calc R U P B 1
C18 C 0.1569(16) 0.6426(10) 0.3534(11) 0.090(4) Uani 0.579(15) 1 d D U P B 1
C19 C 0.1238(16) 0.6595(9) 0.2904(11) 0.103(5) Uani 0.579(15) 1 d D U P B 1
H19 H 0.1068 0.6125 0.2629 0.123 Uiso 0.579(15) 1 calc R U P B 1
C20 C 0.1157(13) 0.7456(10) 0.2679(8) 0.092(4) Uani 0.579(15) 1 d D U P B 1
H20 H 0.0951 0.7568 0.2247 0.110 Uiso 0.579(15) 1 calc R U P B 1
C16' C 0.169(2) 0.7768(14) 0.3676(13) 0.090(4) Uani 0.421(15) 1 d D . P B 2
H16' H 0.1864 0.8115 0.4041 0.108 Uiso 0.421(15) 1 calc R U P B 2
C17' C 0.175(2) 0.6851(14) 0.3703(15) 0.096(4) Uani 0.421(15) 1 d D . P B 2
H17' H 0.2089 0.6571 0.4015 0.115 Uiso 0.421(15) 1 calc R U P B 2
C18' C 0.128(2) 0.6363(12) 0.3256(18) 0.090(4) Uani 0.421(15) 1 d D . P B 2
C19' C 0.0831(19) 0.6775(13) 0.2751(14) 0.103(5) Uani 0.421(15) 1 d D . P B 2
H19' H 0.0507 0.6438 0.2459 0.123 Uiso 0.421(15) 1 calc R U P B 2
C20' C 0.0863(16) 0.7685(13) 0.2675(11) 0.092(4) Uani 0.421(15) 1 d D . P B 2
H20' H 0.0544 0.7974 0.2350 0.110 Uiso 0.421(15) 1 calc R U P B 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
Sn1 O3 2.049(4) . ?
Sn1 C9 2.076(9) . ?
Sn1 C10 2.097(9) . ?
Sn1 O2 2.237(6) . ?
Sn1 O4 2.260(7) . ?
Sn1 O1 2.831(7) . ?
Sn2 O3 2.025(5) . ?
Sn2 C12 2.100(9) . ?
Sn2 C11 2.100(9) . ?
Sn2 O3 2.141(5) 7_565 ?
Sn2 O5 2.320(6) . ?
Sn2 Sn2 3.2611(11) 7_565 ?
Se1 C15 1.912(9) . ?
Se1 C14 1.941(9) . ?
Se2 C6 1.850(10) . ?
Se2 C7 1.943(10) . ?
F1 C3 1.36(3) . ?
F2 C18 1.34(2) . ?
F1' C3' 1.34(3) . ?
F2' C18' 1.34(3) . ?
O1 C8 1.252(10) . ?
O2 C8 1.259(10) . ?
O3 Sn2 2.141(5) 7_565 ?
O4 C13 1.225(10) . ?
O5 C13 1.225(10) . ?
C1 C2 1.380(10) . ?
C1 C6 1.546(9) . ?
C2 C3 1.373(9) . ?
C3 C4 1.371(9) . ?
C4 C5 1.367(9) . ?
C5 C6 1.365(9) . ?
C1' C2' 1.380(10) . ?
C1' C6 1.544(9) . ?
C2' C3' 1.372(9) . ?
C3' C4' 1.374(9) . ?
C4' C5' 1.374(10) . ?
C5' C6 1.368(9) . ?
C7 C8 1.469(12) . ?
C13 C14 1.490(11) . ?
C15 C16' 1.376(9) . ?
C15 C16 1.378(9) . ?
C15 C20' 1.379(9) . ?
C15 C20 1.381(9) . ?
C16 C17 1.379(9) . ?
C17 C18 1.374(9) . ?
C18 C19 1.374(9) . ?
C19 C20 1.373(9) . ?
C16' C17' 1.381(10) . ?
C17' C18' 1.375(10) . ?
C18' C19' 1.373(9) . ?
C19' C20' 1.376(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
O3 Sn1 C9 103.8(3) . . ?
O3 Sn1 C10 103.3(3) . . ?
C9 Sn1 C10 152.5(4) . . ?
O3 Sn1 O2 79.0(2) . . ?
C9 Sn1 O2 95.3(3) . . ?
C10 Sn1 O2 94.5(3) . . ?
O3 Sn1 O4 92.7(2) . . ?
C9 Sn1 O4 84.8(4) . . ?
C10 Sn1 O4 89.2(4) . . ?
O2 Sn1 O4 171.5(2) . . ?
O3 Sn1 O1 128.1(2) . . ?
C9 Sn1 O1 82.6(3) . . ?
C10 Sn1 O1 84.5(3) . . ?
O2 Sn1 O1 49.1(2) . . ?
O4 Sn1 O1 139.1(2) . . ?
O3 Sn2 C12 109.9(3) . . ?
O3 Sn2 C11 107.5(4) . . ?
C12 Sn2 C11 140.9(4) . . ?
O3 Sn2 O3 77.00(19) . 7_565 ?
C12 Sn2 O3 99.4(3) . 7_565 ?
C11 Sn2 O3 99.5(4) . 7_565 ?
O3 Sn2 O5 91.3(2) . . ?
C12 Sn2 O5 82.5(3) . . ?
C11 Sn2 O5 85.8(4) . . ?
O3 Sn2 O5 168.1(2) 7_565 . ?
O3 Sn2 Sn2 39.78(14) . 7_565 ?
C12 Sn2 Sn2 108.6(3) . 7_565 ?
C11 Sn2 Sn2 107.2(4) . 7_565 ?
O3 Sn2 Sn2 37.23(12) 7_565 7_565 ?
O5 Sn2 Sn2 131.04(18) . 7_565 ?
C15 Se1 C14 99.2(4) . . ?
C6 Se2 C7 98.5(5) . . ?
C8 O1 Sn1 81.1(5) . . ?
C8 O2 Sn1 109.7(5) . . ?
Sn2 O3 Sn1 134.3(3) . . ?
Sn2 O3 Sn2 103.00(19) . 7_565 ?
Sn1 O3 Sn2 122.6(2) . 7_565 ?
C13 O4 Sn1 135.4(7) . . ?
C13 O5 Sn2 135.3(6) . . ?
C2 C1 C6 119.8(14) . . ?
C3 C2 C1 119.5(13) . . ?
F1 C3 C4 126.0(19) . . ?
F1 C3 C2 112.7(19) . . ?
C4 C3 C2 121.3(12) . . ?
C5 C4 C3 120.0(13) . . ?
C6 C5 C4 124.7(12) . . ?
C2' C1' C6 117.2(15) . . ?
C3' C2' C1' 119.0(15) . . ?
F1' C3' C2' 115(2) . . ?
F1' C3' C4' 123(2) . . ?
C2' C3' C4' 121.6(13) . . ?
C3' C4' C5' 119.5(13) . . ?
C6 C5' C4' 123.1(13) . . ?
C5' C6 C1' 112.8(11) . . ?
C5 C6 C1 112.5(11) . . ?
C5 C6 Se2 119.0(10) . . ?
C5' C6 Se2 131.8(11) . . ?
C1' C6 Se2 111.4(10) . . ?
C1 C6 Se2 128.3(10) . . ?
C8 C7 Se2 112.7(6) . . ?
O1 C8 O2 120.0(8) . . ?
O1 C8 C7 119.6(9) . . ?
O2 C8 C7 120.4(9) . . ?
O5 C13 O4 125.9(8) . . ?
O5 C13 C14 117.1(8) . . ?
O4 C13 C14 117.0(9) . . ?
C13 C14 Se1 111.4(6) . . ?
C16' C15 C20' 120.0(12) . . ?
C16 C15 C20 118.0(10) . . ?
C16' C15 Se1 128.2(11) . . ?
C16 C15 Se1 114.7(9) . . ?
C20' C15 Se1 108.7(10) . . ?
C20 C15 Se1 126.3(9) . . ?
C15 C16 C17 119.8(11) . . ?
C18 C17 C16 119.0(12) . . ?
F2 C18 C19 117.8(16) . . ?
F2 C18 C17 122.2(16) . . ?
C19 C18 C17 119.9(11) . . ?
C20 C19 C18 120.1(11) . . ?
C19 C20 C15 119.9(11) . . ?
C15 C16' C17' 118.3(13) . . ?
C18' C17' C16' 118.2(13) . . ?
F2' C18' C19' 120(2) . . ?
F2' C18' C17' 120(2) . . ?
C19' C18' C17' 120.8(12) . . ?
C18' C19' C20' 120.3(12) . . ?
C19' C20' C15 117.9(12) . . ?

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
C6 C1 C2 C3 -13(5) . . . . ?
C1 C2 C3 F1 -172(3) . . . . ?
C1 C2 C3 C4 9(5) . . . . ?
F1 C3 C4 C5 173(3) . . . . ?
C2 C3 C4 C5 -7(5) . . . . ?
C3 C4 C5 C6 11(5) . . . . ?
C6 C1' C2' C3' 25(5) . . . . ?
C1' C2' C3' F1' 173(3) . . . . ?
C1' C2' C3' C4' -14(5) . . . . ?
F1' C3' C4' C5' 180(4) . . . . ?
C2' C3' C4' C5' 7(6) . . . . ?
C3' C4' C5' C6 -13(6) . . . . ?
C4 C5 C6 C1 -14(4) . . . . ?
C4 C5 C6 Se2 170(2) . . . . ?
C4' C5' C6 C1' 23(4) . . . . ?
C4' C5' C6 Se2 178(2) . . . . ?
C2' C1' C6 C5' -28(4) . . . . ?
C2' C1' C6 Se2 171(2) . . . . ?
C2 C1 C6 C5 15(4) . . . . ?
C2 C1 C6 Se2 -170(2) . . . . ?
C7 Se2 C6 C5 90.7(18) . . . . ?
C7 Se2 C6 C5' 113(2) . . . . ?
C7 Se2 C6 C1' -91.6(17) . . . . ?
C7 Se2 C6 C1 -84.3(19) . . . . ?
Sn1 O1 C8 O2 0.2(8) . . . . ?
Sn1 O1 C8 C7 -178.5(8) . . . . ?
Sn1 O2 C8 O1 -0.3(10) . . . . ?
Sn1 O2 C8 C7 178.4(7) . . . . ?
Se2 C7 C8 O1 -65.5(11) . . . . ?
Se2 C7 C8 O2 115.8(9) . . . . ?
Sn2 O5 C13 O4 13.5(17) . . . . ?
Sn2 O5 C13 C14 -163.3(7) . . . . ?
Sn1 O4 C13 O5 15.4(17) . . . . ?
Sn1 O4 C13 C14 -167.7(7) . . . . ?
O5 C13 C14 Se1 -108.8(9) . . . . ?
O4 C13 C14 Se1 74.1(10) . . . . ?
C20 C15 C16 C17 -22(4) . . . . ?
Se1 C15 C16 C17 169(2) . . . . ?
C15 C16 C17 C18 16(4) . . . . ?
C16 C17 C18 F2 175(3) . . . . ?
C16 C17 C18 C19 -3(4) . . . . ?
F2 C18 C19 C20 178(2) . . . . ?
C17 C18 C19 C20 -4(4) . . . . ?
C18 C19 C20 C15 -2(4) . . . . ?
C16 C15 C20 C19 15(3) . . . . ?
Se1 C15 C20 C19 -177.6(16) . . . . ?
C20' C15 C16' C17' 26(5) . . . . ?
Se1 C15 C16' C17' -177(3) . . . . ?
C15 C16' C17' C18' -20(6) . . . . ?
C16' C17' C18' F2' -173(4) . . . . ?
C16' C17' C18' C19' 7(6) . . . . ?
F2' C18' C19' C20' -178(3) . . . . ?
C17' C18' C19' C20' 2(5) . . . . ?
C18' C19' C20' C15 3(5) . . . . ?
C16' C15 C20' C19' -17(4) . . . . ?
Se1 C15 C20' C19' -179(2) . . . . ?

_refine_diff_density_max         1.654
_refine_diff_density_min         -1.614
_refine_diff_density_rms         0.148

####################################################################### 
# 
# 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_160921a
_database_code_depnum_ccdc_archive 'CCDC 1509284'
_audit_update_record             
;
2017-05-10 deposited with the CCDC.
2017-05-18 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            'C40 H66 F2 O4 S2 Sn2'
_chemical_formula_weight         950.42

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'
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'
Sn Sn -0.6537 1.4246 '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                   10.5943(9)
_cell_length_b                   14.4760(13)
_cell_length_c                   16.9105(14)
_cell_angle_alpha                87.2930(10)
_cell_angle_beta                 90.023(2)
_cell_angle_gamma                68.535(11)
_cell_volume                     2410.4(4)
_cell_formula_units_Z            2
_cell_measurement_temperature    298(2)
_cell_measurement_reflns_used    2324
_cell_measurement_theta_min      2.3715
_cell_measurement_theta_max      28.1865

_exptl_crystal_description       block
_exptl_crystal_colour            colourless
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.309
_exptl_crystal_F_000             976
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.370
_exptl_crystal_size_mid          0.110
_exptl_crystal_size_min          0.100
_exptl_absorpt_coefficient_mu    1.163
_shelx_estimated_absorpt_T_min   0.673
_shelx_estimated_absorpt_T_max   0.893
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.6728
_exptl_absorpt_correction_T_max  0.8926
_exptl_absorpt_process_details   sadabs
_exptl_absorpt_special_details   ?
_diffrn_ambient_temperature      298(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_source                   ?
_diffrn_measurement_device_type  'CCD area detector'
_diffrn_measurement_method       'phi and omega scans'
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            11635
_diffrn_reflns_av_unetI/netI     0.1836
_diffrn_reflns_av_R_equivalents  0.0667
_diffrn_reflns_limit_h_min       -11
_diffrn_reflns_limit_h_max       12
_diffrn_reflns_limit_k_min       -17
_diffrn_reflns_limit_k_max       17
_diffrn_reflns_limit_l_min       -20
_diffrn_reflns_limit_l_max       18
_diffrn_reflns_theta_min         2.372
_diffrn_reflns_theta_max         25.019
_diffrn_reflns_theta_full        25.019
_diffrn_measured_fraction_theta_max 0.972
_diffrn_measured_fraction_theta_full 0.972
_diffrn_reflns_Laue_measured_fraction_max 0.972
_diffrn_reflns_Laue_measured_fraction_full 0.972
_diffrn_reflns_point_group_measured_fraction_max 0.972
_diffrn_reflns_point_group_measured_fraction_full 0.972
_reflns_number_total             8277
_reflns_number_gt                3006
_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       'Bruker SMART'
_computing_cell_refinement       'Bruker SMART'
_computing_data_reduction        'Bruker SAINT'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 1990)'
_computing_structure_refinement  'SHELXL-2014/7 (Sheldrick, 2014)'
_computing_molecular_graphics    'Bruker SHELXTL'
_computing_publication_material  'Bruker SHELXTL'
_refine_special_details          ?
_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0998P)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         8277
_refine_ls_number_parameters     451
_refine_ls_number_restraints     1070
_refine_ls_R_factor_all          0.2374
_refine_ls_R_factor_gt           0.1224
_refine_ls_wR_factor_ref         0.3180
_refine_ls_wR_factor_gt          0.2919
_refine_ls_goodness_of_fit_ref   1.237
_refine_ls_restrained_S_all      1.261
_refine_ls_shift/su_max          0.009
_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
Sn1 Sn 0.77808(13) 0.40217(10) 0.21540(8) 0.0866(6) Uani 1 1 d . U . . .
Sn2 Sn 0.27961(12) 0.40009(10) 0.29772(8) 0.0836(5) Uani 1 1 d . U . . .
F1 F 0.817(2) -0.0554(14) 0.0394(10) 0.277(8) Uani 1 1 d D U . . .
F2 F 0.352(2) -0.0440(14) 0.5065(11) 0.276(8) Uani 1 1 d D U . . .
O1 O 0.6273(15) 0.4032(11) 0.1271(8) 0.121(3) Uani 1 1 d . U . . .
O2 O 0.4699(13) 0.3990(10) 0.2112(9) 0.111(3) Uani 1 1 d . U . . .
O3 O 0.1268(15) 0.4001(11) 0.3842(8) 0.124(3) Uani 1 1 d . U . . .
O4 O -0.0289(13) 0.4017(10) 0.3025(9) 0.109(3) Uani 1 1 d . U . . .
S1 S 0.4875(8) 0.3678(6) -0.0184(4) 0.155(2) Uani 1 1 d . U . . .
S2 S -0.0106(8) 0.3675(6) 0.5336(4) 0.148(2) Uani 1 1 d . U . . .
C1 C 0.805(2) 0.2657(15) 0.2708(13) 0.130(4) Uani 1 1 d D U . . .
H1A H 0.8937 0.2432 0.2968 0.156 Uiso 1 1 calc R U . . .
H1B H 0.7392 0.2787 0.3126 0.156 Uiso 1 1 calc R U . . .
C2 C 0.798(3) 0.1761(15) 0.2290(13) 0.148(5) Uani 1 1 d D U . . .
H2A H 0.8664 0.1572 0.1887 0.178 Uiso 1 1 calc R U . . .
H2B H 0.7097 0.1943 0.2031 0.178 Uiso 1 1 calc R U . . .
C3 C 0.820(3) 0.0864(17) 0.2886(15) 0.189(8) Uani 1 1 d D U . . .
H3A H 0.9025 0.0730 0.3198 0.227 Uiso 1 1 calc R U . . .
H3B H 0.7446 0.1008 0.3243 0.227 Uiso 1 1 calc R U . . .
C4 C 0.832(4) -0.0025(19) 0.2416(19) 0.249(11) Uani 1 1 d D U . . .
H4A H 0.8461 -0.0592 0.2771 0.374 Uiso 1 1 calc R U . . .
H4B H 0.7501 0.0114 0.2111 0.374 Uiso 1 1 calc R U . . .
H4C H 0.9074 -0.0163 0.2066 0.374 Uiso 1 1 calc R U . . .
C5 C 0.899(2) 0.4158(17) 0.1161(14) 0.143(5) Uani 1 1 d D U . . .
H5A H 0.8406 0.4625 0.0764 0.172 Uiso 1 1 calc R U . . .
H5B H 0.9655 0.4422 0.1336 0.172 Uiso 1 1 calc R U . . .
C6 C 0.970(2) 0.3177(17) 0.0796(14) 0.160(6) Uani 1 1 d D U . . .
H6A H 0.9059 0.3019 0.0474 0.192 Uiso 1 1 calc R U . . .
H6B H 1.0041 0.2660 0.1214 0.192 Uiso 1 1 calc R U . . .
C7 C 1.091(2) 0.318(2) 0.0271(16) 0.197(8) Uani 1 1 d D U . . .
H7A H 1.1145 0.3761 0.0354 0.237 Uiso 1 1 calc R U . . .
H7B H 1.1711 0.2586 0.0375 0.237 Uiso 1 1 calc R U . . .
C8 C 1.038(3) 0.322(3) -0.0504(16) 0.243(12) Uani 1 1 d D U . . .
H8A H 1.1042 0.3222 -0.0887 0.364 Uiso 1 1 calc R U . . .
H8B H 1.0141 0.2642 -0.0564 0.364 Uiso 1 1 calc R U . . .
H8C H 0.9580 0.3806 -0.0584 0.364 Uiso 1 1 calc R U . . .
C9 C 0.663(2) 0.5371(14) 0.2676(13) 0.126(4) Uani 1 1 d D U . . .
H9A H 0.5668 0.5519 0.2590 0.151 Uiso 1 1 calc R U . . .
H9B H 0.6812 0.5313 0.3242 0.151 Uiso 1 1 calc R U . . .
C10 C 0.703(2) 0.6205(15) 0.2291(15) 0.149(6) Uani 1 1 d D U . . .
H10A H 0.7944 0.6102 0.2468 0.179 Uiso 1 1 calc R U . . .
H10B H 0.7054 0.6138 0.1722 0.179 Uiso 1 1 calc R U . . .
C11 C 0.613(3) 0.7258(16) 0.2450(18) 0.178(8) Uani 1 1 d D U . . .
H11A H 0.5804 0.7280 0.2987 0.214 Uiso 1 1 calc R U . . .
H11B H 0.5354 0.7472 0.2091 0.214 Uiso 1 1 calc R U . . .
C12 C 0.689(3) 0.797(2) 0.2345(17) 0.203(11) Uani 1 1 d D U . . .
H12A H 0.6299 0.8627 0.2450 0.305 Uiso 1 1 calc R U . . .
H12B H 0.7657 0.7761 0.2707 0.305 Uiso 1 1 calc R U . . .
H12C H 0.7207 0.7954 0.1812 0.305 Uiso 1 1 calc R U . . .
C13 C 0.410(2) 0.4147(16) 0.3928(12) 0.131(4) Uani 1 1 d D U . . .
H13A H 0.4861 0.4275 0.3692 0.157 Uiso 1 1 calc R U . . .
H13B H 0.3593 0.4720 0.4223 0.157 Uiso 1 1 calc R U . . .
C14 C 0.465(2) 0.3252(16) 0.4498(13) 0.153(6) Uani 1 1 d D U . . .
H14A H 0.5200 0.2682 0.4210 0.184 Uiso 1 1 calc R U . . .
H14B H 0.3901 0.3106 0.4723 0.184 Uiso 1 1 calc R U . . .
C15 C 0.552(3) 0.3404(18) 0.5175(15) 0.176(7) Uani 1 1 d D U . . .
H15A H 0.6067 0.3769 0.4968 0.211 Uiso 1 1 calc R U . . .
H15B H 0.4932 0.3795 0.5572 0.211 Uiso 1 1 calc R U . . .
C16 C 0.643(3) 0.243(2) 0.5548(19) 0.245(13) Uani 1 1 d D U . . .
H16A H 0.6958 0.2547 0.5966 0.368 Uiso 1 1 calc R U . . .
H16B H 0.5890 0.2074 0.5760 0.368 Uiso 1 1 calc R U . . .
H16C H 0.7024 0.2048 0.5157 0.368 Uiso 1 1 calc R U . . .
C17 C 0.161(2) 0.5360(14) 0.2382(13) 0.121(4) Uani 1 1 d D U . . .
H17A H 0.1656 0.5269 0.1817 0.145 Uiso 1 1 calc R U . . .
H17B H 0.0670 0.5525 0.2531 0.145 Uiso 1 1 calc R U . . .
C18 C 0.203(2) 0.6247(14) 0.2549(15) 0.140(5) Uani 1 1 d D U . . .
H18A H 0.2245 0.6203 0.3110 0.168 Uiso 1 1 calc R U . . .
H18B H 0.2863 0.6150 0.2270 0.168 Uiso 1 1 calc R U . . .
C19 C 0.110(2) 0.7269(15) 0.2353(17) 0.172(7) Uani 1 1 d D U . . .
H19A H 0.0381 0.7442 0.2734 0.206 Uiso 1 1 calc R U . . .
H19B H 0.0693 0.7285 0.1837 0.206 Uiso 1 1 calc R U . . .
C20 C 0.173(3) 0.8070(19) 0.234(2) 0.236(12) Uani 1 1 d D U . . .
H20A H 0.1034 0.8706 0.2202 0.354 Uiso 1 1 calc R U . . .
H20B H 0.2109 0.8083 0.2848 0.354 Uiso 1 1 calc R U . . .
H20C H 0.2423 0.7925 0.1948 0.354 Uiso 1 1 calc R U . . .
C21 C 0.312(2) 0.2613(14) 0.2516(13) 0.132(4) Uani 1 1 d D U . . .
H21A H 0.2531 0.2733 0.2055 0.158 Uiso 1 1 calc R U . . .
H21B H 0.4047 0.2364 0.2327 0.158 Uiso 1 1 calc R U . . .
C22 C 0.294(2) 0.1785(14) 0.3011(13) 0.147(5) Uani 1 1 d D U . . .
H22A H 0.2015 0.1993 0.3190 0.176 Uiso 1 1 calc R U . . .
H22B H 0.3539 0.1629 0.3473 0.176 Uiso 1 1 calc R U . . .
C23 C 0.328(3) 0.0823(15) 0.2506(14) 0.178(8) Uani 1 1 d D U . . .
H23A H 0.2485 0.0827 0.2218 0.213 Uiso 1 1 calc R U . . .
H23B H 0.4002 0.0765 0.2137 0.213 Uiso 1 1 calc R U . . .
C24 C 0.373(3) -0.0013(18) 0.3164(18) 0.226(10) Uani 1 1 d D U . . .
H24A H 0.3968 -0.0646 0.2931 0.339 Uiso 1 1 calc R U . . .
H24B H 0.4505 0.0012 0.3444 0.339 Uiso 1 1 calc R U . . .
H24C H 0.3003 0.0074 0.3525 0.339 Uiso 1 1 calc R U . . .
C25 C 0.507(2) 0.4048(17) 0.1466(15) 0.114(4) Uani 1 1 d . U . . .
C26 C 0.412(2) 0.4055(19) 0.0691(14) 0.144(5) Uani 1 1 d . U . . .
H26A H 0.3472 0.4728 0.0600 0.172 Uiso 1 1 calc R U . . .
H26B H 0.3608 0.3640 0.0834 0.172 Uiso 1 1 calc R U . . .
C27 C 0.574(2) 0.2506(17) -0.0014(7) 0.161(5) Uani 1 1 d D U . . .
C28 C 0.524(2) 0.1803(17) 0.0334(11) 0.187(6) Uani 1 1 d D U . . .
H28 H 0.4330 0.2027 0.0476 0.225 Uiso 1 1 calc R U . . .
C29 C 0.603(2) 0.0778(17) 0.0479(12) 0.201(6) Uani 1 1 d D U . . .
H29 H 0.5647 0.0352 0.0718 0.242 Uiso 1 1 calc R U . . .
C30 C 0.738(2) 0.0423(16) 0.0259(11) 0.202(7) Uani 1 1 d D U . . .
C31 C 0.797(2) 0.1081(16) -0.0094(13) 0.209(7) Uani 1 1 d D U . . .
H31 H 0.8868 0.0852 -0.0243 0.251 Uiso 1 1 calc R U . . .
C32 C 0.712(3) 0.2107(17) -0.0210(12) 0.184(5) Uani 1 1 d D U . . .
H32 H 0.7503 0.2539 -0.0430 0.221 Uiso 1 1 calc R U . . .
C33 C 0.008(3) 0.4016(18) 0.3661(17) 0.124(4) Uani 1 1 d . U . . .
C34 C -0.081(2) 0.4067(18) 0.4370(13) 0.136(5) Uani 1 1 d . U . . .
H34A H -0.1365 0.3682 0.4257 0.163 Uiso 1 1 calc R U . . .
H34B H -0.1423 0.4753 0.4393 0.163 Uiso 1 1 calc R U . . .
C35 C 0.085(2) 0.2440(16) 0.5213(8) 0.148(5) Uani 1 1 d D U . . .
C36 C 0.214(2) 0.2136(17) 0.5524(10) 0.172(5) Uani 1 1 d D U . . .
H36 H 0.2429 0.2583 0.5776 0.207 Uiso 1 1 calc R U . . .
C37 C 0.299(2) 0.1187(16) 0.5461(11) 0.189(6) Uani 1 1 d D U . . .
H37 H 0.3873 0.0995 0.5659 0.227 Uiso 1 1 calc R U . . .
C38 C 0.260(2) 0.0496(15) 0.5115(11) 0.184(6) Uani 1 1 d D U . . .
C39 C 0.133(2) 0.0744(16) 0.4774(12) 0.182(6) Uani 1 1 d D U . . .
H39 H 0.1061 0.0288 0.4518 0.218 Uiso 1 1 calc R U . . .
C40 C 0.047(2) 0.1735(17) 0.4842(12) 0.166(5) Uani 1 1 d D U . . .
H40 H -0.0407 0.1937 0.4629 0.199 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
Sn1 C1 2.07(2) . ?
Sn1 C9 2.12(2) . ?
Sn1 C5 2.16(2) . ?
Sn1 O1 2.181(14) . ?
Sn1 O4 2.518(14) 1_655 ?
Sn2 C21 2.10(2) . ?
Sn2 C17 2.114(19) . ?
Sn2 O3 2.182(15) . ?
Sn2 C13 2.19(2) . ?
Sn2 O2 2.487(15) . ?
F1 C30 1.363(16) . ?
F2 C38 1.356(16) . ?
O1 C25 1.31(2) . ?
O2 C25 1.17(2) . ?
O3 C33 1.29(3) . ?
O4 C33 1.14(2) . ?
O4 Sn1 2.518(14) 1_455 ?
S1 C27 1.62(2) . ?
S1 C26 1.70(2) . ?
S2 C35 1.72(2) . ?
S2 C34 1.77(2) . ?
C1 C2 1.532(16) . ?
C2 C3 1.552(17) . ?
C3 C4 1.512(18) . ?
C5 C6 1.506(17) . ?
C6 C7 1.562(17) . ?
C7 C8 1.421(18) . ?
C9 C10 1.538(16) . ?
C10 C11 1.509(17) . ?
C11 C12 1.523(18) . ?
C13 C14 1.510(16) . ?
C14 C15 1.541(17) . ?
C15 C16 1.493(17) . ?
C17 C18 1.541(16) . ?
C18 C19 1.466(16) . ?
C19 C20 1.528(18) . ?
C21 C22 1.499(16) . ?
C22 C23 1.595(17) . ?
C23 C24 1.543(17) . ?
C25 C26 1.65(3) . ?
C27 C32 1.398(17) . ?
C27 C28 1.421(17) . ?
C28 C29 1.421(17) . ?
C29 C30 1.389(17) . ?
C30 C31 1.425(17) . ?
C31 C32 1.432(17) . ?
C33 C34 1.52(3) . ?
C35 C36 1.370(16) . ?
C35 C40 1.400(17) . ?
C36 C37 1.348(16) . ?
C37 C38 1.371(17) . ?
C38 C39 1.376(17) . ?
C39 C40 1.400(16) . ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
C1 Sn1 C9 121.5(9) . . ?
C1 Sn1 C5 121.6(9) . . ?
C9 Sn1 C5 115.6(8) . . ?
C1 Sn1 O1 97.5(7) . . ?
C9 Sn1 O1 97.7(7) . . ?
C5 Sn1 O1 85.8(8) . . ?
C1 Sn1 O4 86.0(7) . 1_655 ?
C9 Sn1 O4 85.8(7) . 1_655 ?
C5 Sn1 O4 86.8(7) . 1_655 ?
O1 Sn1 O4 172.6(5) . 1_655 ?
C21 Sn2 C17 122.9(8) . . ?
C21 Sn2 O3 98.2(7) . . ?
C17 Sn2 O3 95.8(7) . . ?
C21 Sn2 C13 120.7(8) . . ?
C17 Sn2 C13 114.3(8) . . ?
O3 Sn2 C13 90.0(7) . . ?
C21 Sn2 O2 84.2(7) . . ?
C17 Sn2 O2 87.5(7) . . ?
O3 Sn2 O2 173.9(5) . . ?
C13 Sn2 O2 84.0(7) . . ?
C25 O1 Sn1 122.2(14) . . ?
C25 O2 Sn2 147.2(15) . . ?
C33 O3 Sn2 124.1(16) . . ?
C33 O4 Sn1 145.8(18) . 1_455 ?
C27 S1 C26 104.1(11) . . ?
C35 S2 C34 101.3(10) . . ?
C2 C1 Sn1 124.8(15) . . ?
C1 C2 C3 111.2(17) . . ?
C4 C3 C2 107.8(19) . . ?
C6 C5 Sn1 112.2(15) . . ?
C5 C6 C7 112.7(19) . . ?
C8 C7 C6 102(2) . . ?
C10 C9 Sn1 108.2(14) . . ?
C11 C10 C9 116.8(18) . . ?
C10 C11 C12 111(2) . . ?
C14 C13 Sn2 114.7(14) . . ?
C13 C14 C15 112.9(18) . . ?
C16 C15 C14 111.2(19) . . ?
C18 C17 Sn2 115.0(14) . . ?
C19 C18 C17 120.6(18) . . ?
C18 C19 C20 117(2) . . ?
C22 C21 Sn2 121.5(15) . . ?
C21 C22 C23 110.1(17) . . ?
C24 C23 C22 101.3(17) . . ?
O2 C25 O1 126(2) . . ?
O2 C25 C26 121(2) . . ?
O1 C25 C26 113(2) . . ?
C25 C26 S1 119.2(17) . . ?
C32 C27 C28 114.2(19) . . ?
C32 C27 S1 120.4(19) . . ?
C28 C27 S1 125.3(19) . . ?
C29 C28 C27 124(2) . . ?
C30 C29 C28 119.0(19) . . ?
F1 C30 C29 120.6(17) . . ?
F1 C30 C31 118.9(17) . . ?
C29 C30 C31 120.5(18) . . ?
C30 C31 C32 117.6(19) . . ?
C27 C32 C31 125(2) . . ?
O4 C33 O3 124(3) . . ?
O4 C33 C34 123(3) . . ?
O3 C33 C34 114(2) . . ?
C33 C34 S2 121.4(18) . . ?
C36 C35 C40 117.7(19) . . ?
C36 C35 S2 114.0(18) . . ?
C40 C35 S2 128.2(18) . . ?
C37 C36 C35 119.7(19) . . ?
C36 C37 C38 122(2) . . ?
F2 C38 C37 118.5(17) . . ?
F2 C38 C39 119.6(17) . . ?
C37 C38 C39 121.8(18) . . ?
C38 C39 C40 114.9(18) . . ?
C35 C40 C39 123.7(19) . . ?

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
Sn1 C1 C2 C3 -178.9(18) . . . . ?
C1 C2 C3 C4 -172(3) . . . . ?
Sn1 C5 C6 C7 -161.6(17) . . . . ?
C5 C6 C7 C8 -106(3) . . . . ?
Sn1 C9 C10 C11 167.7(18) . . . . ?
C9 C10 C11 C12 157(2) . . . . ?
Sn2 C13 C14 C15 -177.8(18) . . . . ?
C13 C14 C15 C16 -160(3) . . . . ?
Sn2 C17 C18 C19 -164(2) . . . . ?
C17 C18 C19 C20 -165(2) . . . . ?
Sn2 C21 C22 C23 -179.3(16) . . . . ?
C21 C22 C23 C24 153(2) . . . . ?
Sn2 O2 C25 O1 177.4(14) . . . . ?
Sn2 O2 C25 C26 -9(4) . . . . ?
Sn1 O1 C25 O2 -6(3) . . . . ?
Sn1 O1 C25 C26 179.9(12) . . . . ?
O2 C25 C26 S1 -156(2) . . . . ?
O1 C25 C26 S1 19(3) . . . . ?
C27 S1 C26 C25 66(2) . . . . ?
C26 S1 C27 C32 -129.4(13) . . . . ?
C26 S1 C27 C28 50.2(12) . . . . ?
C32 C27 C28 C29 0.0(10) . . . . ?
S1 C27 C28 C29 -179.7(7) . . . . ?
C27 C28 C29 C30 -1.1(16) . . . . ?
C28 C29 C30 F1 179.5(12) . . . . ?
C28 C29 C30 C31 1(2) . . . . ?
F1 C30 C31 C32 -178.5(14) . . . . ?
C29 C30 C31 C32 0(2) . . . . ?
C28 C27 C32 C31 1.2(16) . . . . ?
S1 C27 C32 C31 -179.1(11) . . . . ?
C30 C31 C32 C27 -1(2) . . . . ?
Sn1 O4 C33 O3 179.1(13) 1_455 . . . ?
Sn1 O4 C33 C34 -3(5) 1_455 . . . ?
Sn2 O3 C33 O4 1(4) . . . . ?
Sn2 O3 C33 C34 -176.9(14) . . . . ?
O4 C33 C34 S2 160(2) . . . . ?
O3 C33 C34 S2 -22(3) . . . . ?
C35 S2 C34 C33 -61(2) . . . . ?
C34 S2 C35 C36 132.9(11) . . . . ?
C34 S2 C35 C40 -46.9(12) . . . . ?
C40 C35 C36 C37 0.2(9) . . . . ?
S2 C35 C36 C37 -179.6(7) . . . . ?
C35 C36 C37 C38 -2.0(15) . . . . ?
C36 C37 C38 F2 179.1(11) . . . . ?
C36 C37 C38 C39 3(2) . . . . ?
F2 C38 C39 C40 -178.4(12) . . . . ?
C37 C38 C39 C40 -2.8(19) . . . . ?
C36 C35 C40 C39 0.2(14) . . . . ?
S2 C35 C40 C39 180.0(9) . . . . ?
C38 C39 C40 C35 1.1(18) . . . . ?

_refine_diff_density_max         0.763
_refine_diff_density_min         -1.161
_refine_diff_density_rms         0.144

####################################################################### 
# 
# 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_160416c
_database_code_depnum_ccdc_archive 'CCDC 1509289'
_audit_update_record             
;
2017-05-10 deposited with the CCDC.
2017-05-18 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            'C11 H15 F O2 S Sn'
_chemical_formula_weight         348.98

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'
Sn Sn -0.6537 1.4246 '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'
F F 0.0171 0.0103 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_space_group_crystal_system      monoclinic
_space_group_IT_number           14
_space_group_name_H-M_alt        'P 21/c'
_space_group_name_Hall           '-P 2ybc'

_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+1/2, -z+1/2'
'-x, -y, -z'
'x, -y-1/2, z-1/2'

_cell_length_a                   11.0008(11)
_cell_length_b                   10.2461(9)
_cell_length_c                   13.0833(12)
_cell_angle_alpha                90
_cell_angle_beta                 107.192(2)
_cell_angle_gamma                90
_cell_volume                     1408.8(2)
_cell_formula_units_Z            4
_cell_measurement_temperature    298(2)
_cell_measurement_reflns_used    2495
_cell_measurement_theta_min      2.569
_cell_measurement_theta_max      24.193

_exptl_crystal_description       block
_exptl_crystal_colour            colourless
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.645
_exptl_crystal_F_000             688
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.460
_exptl_crystal_size_mid          0.380
_exptl_crystal_size_min          0.220
_exptl_absorpt_coefficient_mu    1.958
_shelx_estimated_absorpt_T_min   0.466
_shelx_estimated_absorpt_T_max   0.673
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.4662
_exptl_absorpt_correction_T_max  0.6727
_exptl_absorpt_process_details   sadabs
_exptl_absorpt_special_details   ?
_diffrn_ambient_temperature      298(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_source                   ?
_diffrn_measurement_device_type  'CCD area detector'
_diffrn_measurement_method       'phi and omega scans'
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            6851
_diffrn_reflns_av_unetI/netI     0.0565
_diffrn_reflns_av_R_equivalents  0.0598
_diffrn_reflns_limit_h_min       -9
_diffrn_reflns_limit_h_max       13
_diffrn_reflns_limit_k_min       -12
_diffrn_reflns_limit_k_max       11
_diffrn_reflns_limit_l_min       -15
_diffrn_reflns_limit_l_max       13
_diffrn_reflns_theta_min         2.570
_diffrn_reflns_theta_max         25.019
_diffrn_reflns_theta_full        25.019
_diffrn_measured_fraction_theta_max 0.998
_diffrn_measured_fraction_theta_full 0.998
_diffrn_reflns_Laue_measured_fraction_max 0.998
_diffrn_reflns_Laue_measured_fraction_full 0.998
_diffrn_reflns_point_group_measured_fraction_max 0.998
_diffrn_reflns_point_group_measured_fraction_full 0.998
_reflns_number_total             2475
_reflns_number_gt                1713
_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       'Bruker SMART'
_computing_cell_refinement       'Bruker SMART'
_computing_data_reduction        'Bruker SAINT'
_computing_structure_solution    'SHELXL-2014/7 (Sheldrick, 1990)'
_computing_structure_refinement  'SHELXL-2014/7 (Sheldrick, 2014)'
_computing_molecular_graphics    'Bruker SHELXTL'
_computing_publication_material  'Bruker SHELXTL'
_refine_special_details          ?
_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0282P)²+1.3861P] 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         2475
_refine_ls_number_parameters     206
_refine_ls_number_restraints     37
_refine_ls_R_factor_all          0.0681
_refine_ls_R_factor_gt           0.0388
_refine_ls_wR_factor_ref         0.0975
_refine_ls_wR_factor_gt          0.0821
_refine_ls_goodness_of_fit_ref   1.073
_refine_ls_restrained_S_all      1.083
_refine_ls_shift/su_max          0.008
_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
Sn1 Sn 1.04536(4) 0.08764(4) 0.21904(3) 0.05747(18) Uani 1 1 d . . . . .
S1 S 0.6646(3) 0.2327(3) 0.3749(2) 0.0989(9) Uani 0.703(3) 1 d D . P A 1
F1 F 0.3774(12) 0.217(3) -0.0792(9) 0.210(7) Uani 0.703(3) 1 d D . P A 1
S1' S 0.7280(7) 0.0947(7) 0.3363(6) 0.0989(9) Uani 0.297(3) 1 d D . P A 2
F1' F 0.338(3) 0.242(10) -0.049(2) 0.210(7) Uani 0.297(3) 1 d D . P A 2
O1 O 0.9553(4) 0.2743(4) 0.2783(3) 0.0807(12) Uani 1 1 d . . . . .
O2 O 0.8608(4) 0.4309(4) 0.3436(3) 0.0695(11) Uani 1 1 d . . . . .
C1 C 0.5814(8) 0.2285(13) 0.2386(9) 0.087(5) Uani 0.703(3) 1 d D . P A 1
C2 C 0.5737(14) 0.3295(13) 0.1691(13) 0.127(8) Uani 0.703(3) 1 d D . P A 1
H2 H 0.6162 0.4071 0.1938 0.152 Uiso 0.703(3) 1 calc R U P A 1
C3 C 0.5043(16) 0.3186(14) 0.0634(13) 0.146(9) Uani 0.703(3) 1 d D . P A 1
H3 H 0.5002 0.3883 0.0170 0.175 Uiso 0.703(3) 1 calc R U P A 1
C4 C 0.4408(12) 0.2045(16) 0.0264(10) 0.119(5) Uani 0.703(3) 1 d D . P A 1
C5 C 0.4492(16) 0.1026(16) 0.0954(14) 0.132(9) Uani 0.703(3) 1 d D . P A 1
H5 H 0.4071 0.0249 0.0709 0.159 Uiso 0.703(3) 1 calc R U P A 1
C6 C 0.5193(15) 0.1143(13) 0.2005(12) 0.127(7) Uani 0.703(3) 1 d D . P A 1
H6 H 0.5249 0.0441 0.2467 0.152 Uiso 0.703(3) 1 calc R U P A 1
C7 C 0.8293(14) 0.2037(13) 0.3753(12) 0.075(3) Uani 0.703(3) 1 d . . P A 1
H7A H 0.8816 0.1901 0.4485 0.091 Uiso 0.703(3) 1 calc R U P A 1
H7B H 0.8323 0.1245 0.3355 0.091 Uiso 0.703(3) 1 calc R U P A 1
C7' C 0.797(4) 0.240(4) 0.397(3) 0.075(3) Uani 0.297(3) 1 d . . P A 2
H7'A H 0.7306 0.2997 0.4020 0.091 Uiso 0.297(3) 1 calc R U P A 2
H7'B H 0.8507 0.2219 0.4687 0.091 Uiso 0.297(3) 1 calc R U P A 2
C8 C 0.8831(6) 0.3111(7) 0.3288(5) 0.0693(17) Uani 1 1 d . . . . .
C9 C 1.1493(7) 0.2257(7) 0.1569(7) 0.104(2) Uani 1 1 d . . . . .
H9A H 1.1392 0.2065 0.0830 0.156 Uiso 1 1 calc R U . . .
H9B H 1.2378 0.2211 0.1967 0.156 Uiso 1 1 calc R U . . .
H9C H 1.1178 0.3119 0.1629 0.156 Uiso 1 1 calc R U . . .
C10 C 1.1176(7) 0.0318(7) 0.3814(5) 0.089(2) Uani 1 1 d . . . . .
H10A H 1.0490 0.0020 0.4068 0.133 Uiso 1 1 calc R U . . .
H10B H 1.1582 0.1053 0.4232 0.133 Uiso 1 1 calc R U . . .
H10C H 1.1784 -0.0373 0.3879 0.133 Uiso 1 1 calc R U . . .
C11 C 0.8622(6) 0.0367(7) 0.1220(5) 0.0823(19) Uani 1 1 d . . . . .
H11A H 0.8235 -0.0219 0.1605 0.124 Uiso 1 1 calc R U . . .
H11B H 0.8685 -0.0051 0.0582 0.124 Uiso 1 1 calc R U . . .
H11C H 0.8111 0.1140 0.1033 0.124 Uiso 1 1 calc R U . . .
C1' C 0.6134(13) 0.162(2) 0.2236(12) 0.074(8) Uani 0.297(3) 1 d D . P A 2
C2' C 0.599(2) 0.293(2) 0.203(2) 0.080(12) Uani 0.297(3) 1 d D . P A 2
H2' H 0.6508 0.3523 0.2503 0.096 Uiso 0.297(3) 1 calc R U P A 2
C3' C 0.509(3) 0.338(2) 0.113(3) 0.121(17) Uani 0.297(3) 1 d D . P A 2
H3' H 0.4996 0.4270 0.0991 0.145 Uiso 0.297(3) 1 calc R U P A 2
C4' C 0.434(2) 0.250(4) 0.0434(19) 0.119(5) Uani 0.297(3) 1 d D . P A 2
C5' C 0.448(2) 0.118(3) 0.064(2) 0.11(2) Uani 0.297(3) 1 d D . P A 2
H5' H 0.3972 0.0593 0.0158 0.136 Uiso 0.297(3) 1 calc R U P A 2
C6' C 0.537(2) 0.074(2) 0.155(2) 0.093(11) Uani 0.297(3) 1 d D . P A 2
H6' H 0.5455 -0.0149 0.1691 0.112 Uiso 0.297(3) 1 calc R U 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
Sn1 C11 2.105(6) . ?
Sn1 C10 2.116(6) . ?
Sn1 C9 2.126(7) . ?
Sn1 O2 2.194(4) 2_745 ?
Sn1 O1 2.386(5) . ?
S1 C1 1.748(11) . ?
S1 C7 1.835(13) . ?
F1 C4 1.358(9) . ?
S1' C7' 1.75(4) . ?
S1' C1' 1.772(15) . ?
F1' C4' 1.350(10) . ?
O1 C8 1.232(7) . ?
O2 C8 1.278(7) . ?
O2 Sn1 2.194(4) 2_755 ?
C1 C2 1.363(9) . ?
C1 C6 1.371(9) . ?
C2 C3 1.373(9) . ?
C3 C4 1.375(9) . ?
C4 C5 1.365(9) . ?
C5 C6 1.369(9) . ?
C7 C8 1.464(15) . ?
C7' C8 1.64(4) . ?
C1' C2' 1.371(9) . ?
C1' C6' 1.373(9) . ?
C2' C3' 1.375(10) . ?
C3' C4' 1.375(10) . ?
C4' C5' 1.369(10) . ?
C5' C6' 1.376(10) . ?

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
C11 Sn1 C10 123.2(3) . . ?
C11 Sn1 C9 117.5(3) . . ?
C10 Sn1 C9 118.6(3) . . ?
C11 Sn1 O2 93.8(2) . 2_745 ?
C10 Sn1 O2 95.6(2) . 2_745 ?
C9 Sn1 O2 88.8(2) . 2_745 ?
C11 Sn1 O1 88.8(2) . . ?
C10 Sn1 O1 87.7(2) . . ?
C9 Sn1 O1 85.0(2) . . ?
O2 Sn1 O1 173.77(14) 2_745 . ?
C1 S1 C7 102.6(5) . . ?
C7' S1' C1' 98.7(17) . . ?
C8 O1 Sn1 144.6(4) . . ?
C8 O2 Sn1 120.9(4) . 2_755 ?
C2 C1 C6 118.7(10) . . ?
C2 C1 S1 124.9(11) . . ?
C6 C1 S1 116.5(12) . . ?
C1 C2 C3 121.1(11) . . ?
C2 C3 C4 119.8(11) . . ?
F1 C4 C5 131(2) . . ?
F1 C4 C3 109.5(19) . . ?
C5 C4 C3 119.3(10) . . ?
C4 C5 C6 120.4(10) . . ?
C5 C6 C1 120.8(10) . . ?
C8 C7 S1 113.4(8) . . ?
C8 C7' S1' 111.9(19) . . ?
O1 C8 O2 123.9(6) . . ?
O1 C8 C7 113.3(7) . . ?
O2 C8 C7 122.6(7) . . ?
O1 C8 C7' 136.0(12) . . ?
O2 C8 C7' 100.0(12) . . ?
C2' C1' C6' 120.2(12) . . ?
C2' C1' S1' 123.8(17) . . ?
C6' C1' S1' 116.0(18) . . ?
C1' C2' C3' 120.5(12) . . ?
C2' C3' C4' 119.3(12) . . ?
F1' C4' C5' 98(5) . . ?
F1' C4' C3' 142(5) . . ?
C5' C4' C3' 120.4(13) . . ?
C4' C5' C6' 120.3(13) . . ?
C1' C6' C5' 119.5(12) . . ?

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
C7 S1 C1 C2 -80.4(8) . . . . ?
C7 S1 C1 C6 100.0(8) . . . . ?
C6 C1 C2 C3 0.8(5) . . . . ?
S1 C1 C2 C3 -178.8(4) . . . . ?
C1 C2 C3 C4 0.2(5) . . . . ?
C2 C3 C4 F1 179.0(6) . . . . ?
C2 C3 C4 C5 -0.8(12) . . . . ?
F1 C4 C5 C6 -179.3(11) . . . . ?
C3 C4 C5 C6 0.5(16) . . . . ?
C4 C5 C6 C1 0.5(16) . . . . ?
C2 C1 C6 C5 -1.1(12) . . . . ?
S1 C1 C6 C5 178.5(9) . . . . ?
C1 S1 C7 C8 67.8(10) . . . . ?
C1' S1' C7' C8 -71(2) . . . . ?
Sn1 O1 C8 O2 179.1(4) . . . . ?
Sn1 O1 C8 C7 1.9(12) . . . . ?
Sn1 O1 C8 C7' 2(3) . . . . ?
Sn1 O2 C8 O1 -1.2(9) 2_755 . . . ?
Sn1 O2 C8 C7 175.7(8) 2_755 . . . ?
Sn1 O2 C8 C7' 176.7(16) 2_755 . . . ?
S1 C7 C8 O1 -144.1(7) . . . . ?
S1 C7 C8 O2 38.7(13) . . . . ?
S1' C7' C8 O1 -38(4) . . . . ?
S1' C7' C8 O2 144.5(18) . . . . ?
C7' S1' C1' C2' 0.8(16) . . . . ?
C7' S1' C1' C6' -179.7(16) . . . . ?
C6' C1' C2' C3' -0.5(6) . . . . ?
S1' C1' C2' C3' 179.0(5) . . . . ?
C1' C2' C3' C4' -0.1(6) . . . . ?
C2' C3' C4' F1' -179.9(15) . . . . ?
C2' C3' C4' C5' 0.0(14) . . . . ?
F1' C4' C5' C6' -179.2(12) . . . . ?
C3' C4' C5' C6' 0.8(18) . . . . ?
C2' C1' C6' C5' 1.2(13) . . . . ?
S1' C1' C6' C5' -178.3(10) . . . . ?
C4' C5' C6' C1' -1.4(18) . . . . ?

_refine_diff_density_max         1.134
_refine_diff_density_min         -0.716
_refine_diff_density_rms         0.089

####################################################################### 
# 
# 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_160928a
_database_code_depnum_ccdc_archive 'CCDC 1509286'
_audit_update_record             
;
2017-05-10 deposited with the CCDC.
2017-05-18 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            'C40 H66 F2 O4 Se2 Sn2'
_chemical_formula_weight         1044.22

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'
O O 0.0106 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
Se Se -0.0929 2.2259 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
Sn Sn -0.6537 1.4246 '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                   10.3868(8)
_cell_length_b                   13.7639(11)
_cell_length_c                   18.2950(16)
_cell_angle_alpha                111.926(3)
_cell_angle_beta                 97.549(2)
_cell_angle_gamma                90.5060(10)
_cell_volume                     2400.5(3)
_cell_formula_units_Z            2
_cell_measurement_temperature    298(2)
_cell_measurement_reflns_used    2536
_cell_measurement_theta_min      2.483
_cell_measurement_theta_max      28.205

_exptl_crystal_description       block
_exptl_crystal_colour            colourless
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.445
_exptl_crystal_F_000             1048
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.370
_exptl_crystal_size_mid          0.100
_exptl_crystal_size_min          0.050
_exptl_absorpt_coefficient_mu    2.597
_shelx_estimated_absorpt_T_min   0.447
_shelx_estimated_absorpt_T_max   0.881
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.4466
_exptl_absorpt_correction_T_max  0.8811
_exptl_absorpt_process_details   sadabs
_exptl_absorpt_special_details   ?
_diffrn_ambient_temperature      298(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_source                   ?
_diffrn_measurement_device_type  'CCD area detector'
_diffrn_measurement_method       'phi and omega scans'
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            12233
_diffrn_reflns_av_unetI/netI     0.1074
_diffrn_reflns_av_R_equivalents  0.0545
_diffrn_reflns_limit_h_min       -12
_diffrn_reflns_limit_h_max       11
_diffrn_reflns_limit_k_min       -11
_diffrn_reflns_limit_k_max       16
_diffrn_reflns_limit_l_min       -21
_diffrn_reflns_limit_l_max       21
_diffrn_reflns_theta_min         2.347
_diffrn_reflns_theta_max         25.020
_diffrn_reflns_theta_full        25.020
_diffrn_measured_fraction_theta_max 0.982
_diffrn_measured_fraction_theta_full 0.982
_diffrn_reflns_Laue_measured_fraction_max 0.982
_diffrn_reflns_Laue_measured_fraction_full 0.982
_diffrn_reflns_point_group_measured_fraction_max 0.982
_diffrn_reflns_point_group_measured_fraction_full 0.982
_reflns_number_total             8343
_reflns_number_gt                3828
_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       'Bruker SMART'
_computing_cell_refinement       'Bruker SMART'
_computing_data_reduction        'Bruker SHELXTL'
_computing_structure_solution    'SHELXL-2014/7 (Sheldrick, 1990)'
_computing_structure_refinement  'SHELXL-2014/7 (Sheldrick, 2014)'
_computing_molecular_graphics    'Bruker SHELXTL'
_computing_publication_material  'Bruker SHELXTL'
_refine_special_details          ?
_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0388P)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         8343
_refine_ls_number_parameters     457
_refine_ls_number_restraints     109
_refine_ls_R_factor_all          0.1386
_refine_ls_R_factor_gt           0.0666
_refine_ls_wR_factor_ref         0.1450
_refine_ls_wR_factor_gt          0.1317
_refine_ls_goodness_of_fit_ref   1.110
_refine_ls_restrained_S_all      1.151
_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
Sn1 Sn 1.28130(6) 0.32218(5) 0.19149(4) 0.0754(2) Uani 1 1 d . . . . .
Sn2 Sn 0.77467(6) 0.40225(5) 0.14905(4) 0.0733(2) Uani 1 1 d . U . . .
Se1 Se 1.10765(13) 0.65218(9) 0.09314(7) 0.1131(4) Uani 1 1 d . . . . .
Se2 Se 0.72000(13) 0.25056(11) 0.35258(8) 0.1325(5) Uani 1 1 d . . . . .
F1 F 0.5192(9) -0.1174(7) 0.4174(5) 0.199(4) Uani 1 1 d . . . . .
F2 F 1.0328(9) 0.8960(6) 0.4326(5) 0.189(4) Uani 1 1 d . . . . .
O1 O 0.4486(6) 0.2450(4) 0.2278(4) 0.0812(17) Uani 1 1 d . . . . .
O2 O 0.5870(5) 0.3290(5) 0.1857(4) 0.0904(19) Uani 1 1 d . . . . .
O3 O 1.0814(6) 0.3988(5) 0.1525(4) 0.0841(18) Uani 1 1 d . . . . .
O4 O 0.9261(6) 0.4825(4) 0.1128(3) 0.0808(17) Uani 1 1 d . . . . .
C1 C 0.565(2) -0.0325(12) 0.4012(9) 0.143(6) Uani 1 1 d . U . . .
C2 C 0.4807(15) 0.0102(14) 0.3579(9) 0.157(6) Uani 1 1 d . . . . .
H2 H 0.3944 -0.0152 0.3396 0.189 Uiso 1 1 calc R U . . .
C3 C 0.5336(14) 0.0939(10) 0.3434(7) 0.130(4) Uani 1 1 d . . . . .
H3 H 0.4809 0.1255 0.3146 0.156 Uiso 1 1 calc R U . . .
C4 C 0.6575(13) 0.1300(8) 0.3696(7) 0.099(3) Uani 1 1 d . . . . .
C5 C 0.7337(14) 0.0847(11) 0.4107(7) 0.134(5) Uani 1 1 d . . . . .
H5 H 0.8201 0.1101 0.4278 0.161 Uiso 1 1 calc R U . . .
C6 C 0.6929(18) 0.0048(11) 0.4289(8) 0.145(5) Uani 1 1 d . U . . .
H6 H 0.7480 -0.0240 0.4587 0.174 Uiso 1 1 calc R U . . .
C7 C 1.0520(19) 0.8409(11) 0.3564(9) 0.132(5) Uani 1 1 d . . . . .
C8 C 1.1721(16) 0.8050(12) 0.3410(10) 0.140(5) Uani 1 1 d . . . . .
H8 H 1.2411 0.8198 0.3822 0.168 Uiso 1 1 calc R U . . .
C9 C 1.1898(13) 0.7462(9) 0.2629(9) 0.117(4) Uani 1 1 d . . . . .
H9 H 1.2706 0.7213 0.2514 0.141 Uiso 1 1 calc R U . . .
C10 C 1.0862(13) 0.7255(8) 0.2028(7) 0.093(3) Uani 1 1 d . . . . .
C11 C 0.9662(15) 0.7636(11) 0.2211(9) 0.139(5) Uani 1 1 d . . . . .
H11 H 0.8950 0.7490 0.1813 0.166 Uiso 1 1 calc R U . . .
C12 C 0.9542(16) 0.8250(11) 0.3012(10) 0.166(6) Uani 1 1 d . . . . .
H12 H 0.8757 0.8538 0.3140 0.199 Uiso 1 1 calc R U . . .
C13 C 0.5422(17) 0.7639(11) 0.2003(9) 0.221(8) Uani 1 1 d D U . . .
H13A H 0.5485 0.7554 0.2504 0.331 Uiso 1 1 calc R U . . .
H13B H 0.4664 0.8007 0.1936 0.331 Uiso 1 1 calc R U . . .
H13C H 0.6184 0.8033 0.1994 0.331 Uiso 1 1 calc R U . . .
C14 C 0.5322(15) 0.6595(11) 0.1348(9) 0.190(4) Uani 1 1 d D U . . .
H14A H 0.4461 0.6260 0.1265 0.228 Uiso 1 1 calc R U . . .
H14B H 0.5470 0.6667 0.0857 0.228 Uiso 1 1 calc R U . . .
C15 C 0.6317(14) 0.5954(9) 0.1572(8) 0.182(4) Uani 1 1 d D U . . .
H15A H 0.6202 0.5960 0.2091 0.219 Uiso 1 1 calc R U . . .
H15B H 0.7168 0.6292 0.1626 0.219 Uiso 1 1 calc R U . . .
C16 C 0.6318(12) 0.4812(9) 0.1000(7) 0.141(3) Uani 1 1 d D U . . .
H16A H 0.6514 0.4786 0.0489 0.169 Uiso 1 1 calc R U . . .
H16B H 0.5464 0.4464 0.0916 0.169 Uiso 1 1 calc R U . . .
C17 C 1.0665(16) 0.5872(13) 0.4325(10) 0.239(6) Uani 1 1 d D U . . .
H17A H 1.0923 0.5168 0.4211 0.358 Uiso 1 1 calc R U . . .
H17B H 1.0887 0.6276 0.4885 0.358 Uiso 1 1 calc R U . . .
H17C H 1.1107 0.6184 0.4031 0.358 Uiso 1 1 calc R U . . .
C18 C 0.9252(15) 0.5851(13) 0.4095(9) 0.202(4) Uani 1 1 d D U . . .
H18A H 0.8907 0.6527 0.4356 0.243 Uiso 1 1 calc R U . . .
H18B H 0.8788 0.5314 0.4202 0.243 Uiso 1 1 calc R U . . .
C19 C 0.9220(15) 0.5555(11) 0.3119(8) 0.198(4) Uani 1 1 d D U . . .
H19A H 0.8826 0.6097 0.2962 0.237 Uiso 1 1 calc R U . . .
H19B H 1.0092 0.5475 0.2978 0.237 Uiso 1 1 calc R U . . .
C20 C 0.8442(13) 0.4574(10) 0.2741(6) 0.153(3) Uani 1 1 d D U . . .
H20A H 0.7690 0.4633 0.3015 0.184 Uiso 1 1 calc R U . . .
H20B H 0.8950 0.4033 0.2835 0.184 Uiso 1 1 calc R U . . .
C21 C 0.5995(14) 0.0275(10) -0.1038(9) 0.190(7) Uani 1 1 d . . . . .
H21A H 0.5453 0.0077 -0.0724 0.285 Uiso 1 1 calc R U . . .
H21B H 0.6276 -0.0344 -0.1425 0.285 Uiso 1 1 calc R U . . .
H21C H 0.5511 0.0668 -0.1305 0.285 Uiso 1 1 calc R U . . .
C22 C 0.7119(13) 0.0914(9) -0.0526(8) 0.143(5) Uani 1 1 d . . . . .
H22A H 0.7641 0.1120 -0.0852 0.172 Uiso 1 1 calc R U . . .
H22B H 0.7639 0.0482 -0.0302 0.172 Uiso 1 1 calc R U . . .
C23 C 0.6859(11) 0.1858(8) 0.0128(7) 0.123(4) Uani 1 1 d . . . . .
H23A H 0.6275 0.1664 0.0430 0.148 Uiso 1 1 calc R U . . .
H23B H 0.6412 0.2324 -0.0094 0.148 Uiso 1 1 calc R U . . .
C24 C 0.8092(9) 0.2472(7) 0.0709(6) 0.096(3) Uani 1 1 d . U . . .
H24A H 0.8760 0.2521 0.0399 0.115 Uiso 1 1 calc R U . . .
H24B H 0.8420 0.2076 0.1028 0.115 Uiso 1 1 calc R U . . .
C25 C 1.539(2) 0.6274(14) 0.4668(12) 0.283(12) Uani 1 1 d . . . . .
H25A H 1.4984 0.5998 0.4999 0.425 Uiso 1 1 calc R U . . .
H25B H 1.5578 0.7015 0.4944 0.425 Uiso 1 1 calc R U . . .
H25C H 1.6179 0.5936 0.4544 0.425 Uiso 1 1 calc R U . . .
C26 C 1.4565(19) 0.6094(12) 0.3982(9) 0.219(9) Uani 1 1 d . . . . .
H26A H 1.4970 0.6391 0.3658 0.263 Uiso 1 1 calc R U . . .
H26B H 1.3776 0.6451 0.4112 0.263 Uiso 1 1 calc R U . . .
C27 C 1.4208(12) 0.4946(9) 0.3504(7) 0.139(5) Uani 1 1 d . . . . .
H27A H 1.4995 0.4568 0.3434 0.167 Uiso 1 1 calc R U . . .
H27B H 1.3688 0.4668 0.3793 0.167 Uiso 1 1 calc R U . . .
C28 C 1.3469(10) 0.4781(7) 0.2715(6) 0.098(3) Uani 1 1 d . . . . .
H28A H 1.4007 0.5075 0.2444 0.118 Uiso 1 1 calc R U . . .
H28B H 1.2710 0.5192 0.2803 0.118 Uiso 1 1 calc R U . . .
C29 C 1.1001(15) 0.0398(11) -0.1179(8) 0.184(6) Uani 1 1 d . . . . .
H29A H 1.0890 -0.0097 -0.0934 0.275 Uiso 1 1 calc R U . . .
H29B H 1.1219 0.0038 -0.1704 0.275 Uiso 1 1 calc R U . . .
H29C H 1.0208 0.0740 -0.1215 0.275 Uiso 1 1 calc R U . . .
C30 C 1.2097(13) 0.1216(11) -0.0678(8) 0.157(5) Uani 1 1 d . . . . .
H30A H 1.2903 0.0866 -0.0674 0.189 Uiso 1 1 calc R U . . .
H30B H 1.2198 0.1712 -0.0932 0.189 Uiso 1 1 calc R U . . .
C31 C 1.1893(12) 0.1793(9) 0.0140(7) 0.123(4) Uani 1 1 d . . . . .
H31A H 1.1741 0.1292 0.0382 0.148 Uiso 1 1 calc R U . . .
H31B H 1.1110 0.2170 0.0133 0.148 Uiso 1 1 calc R U . . .
C32 C 1.3028(9) 0.2594(8) 0.0681(5) 0.096(3) Uani 1 1 d . . . . .
H32A H 1.3082 0.3168 0.0499 0.115 Uiso 1 1 calc R U . . .
H32B H 1.3840 0.2250 0.0622 0.115 Uiso 1 1 calc R U . . .
C33 C 1.1412(16) 0.1412(13) 0.4005(10) 0.215(6) Uani 1 1 d . U . . .
H33A H 1.2337 0.1379 0.4110 0.322 Uiso 1 1 calc R U . . .
H33B H 1.0986 0.0782 0.3990 0.322 Uiso 1 1 calc R U . . .
H33C H 1.1137 0.2007 0.4418 0.322 Uiso 1 1 calc R U . . .
C34 C 1.1077(14) 0.1514(12) 0.3256(9) 0.170(4) Uani 1 1 d . U . . .
H34A H 1.0186 0.1718 0.3226 0.204 Uiso 1 1 calc R U . . .
H34B H 1.1087 0.0823 0.2843 0.204 Uiso 1 1 calc R U . . .
C35 C 1.1872(13) 0.2251(11) 0.3052(8) 0.162(4) Uani 1 1 d . U . . .
H35A H 1.1826 0.2950 0.3447 0.195 Uiso 1 1 calc R U . . .
H35B H 1.2771 0.2071 0.3104 0.195 Uiso 1 1 calc R U . . .
C36 C 1.1544(10) 0.2298(8) 0.2281(7) 0.110(4) Uani 1 1 d . . . . .
H36A H 1.0684 0.2562 0.2256 0.132 Uiso 1 1 calc R U . . .
H36B H 1.1479 0.1585 0.1891 0.132 Uiso 1 1 calc R U . . .
C37 C 0.6724(10) 0.2017(8) 0.2384(6) 0.105(3) Uani 1 1 d . . . . .
H37A H 0.7479 0.2099 0.2147 0.126 Uiso 1 1 calc R U . . .
H37B H 0.6456 0.1275 0.2178 0.126 Uiso 1 1 calc R U . . .
C38 C 0.5640(10) 0.2604(8) 0.2148(6) 0.080(3) Uani 1 1 d . . . . .
C39 C 1.1403(9) 0.5149(7) 0.0931(5) 0.088(3) Uani 1 1 d . . . . .
H39A H 1.1482 0.4688 0.0390 0.106 Uiso 1 1 calc R U . . .
H39B H 1.2239 0.5196 0.1253 0.106 Uiso 1 1 calc R U . . .
C40 C 1.0427(10) 0.4639(7) 0.1225(5) 0.069(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
Sn1 C32 2.137(9) . ?
Sn1 C28 2.140(9) . ?
Sn1 C36 2.155(9) . ?
Sn1 O1 2.201(6) 1_655 ?
Sn1 O3 2.479(6) . ?
Sn2 C16 2.144(10) . ?
Sn2 C20 2.143(10) . ?
Sn2 C24 2.144(9) . ?
Sn2 O4 2.219(6) . ?
Sn2 O2 2.466(6) . ?
Se1 C39 1.923(9) . ?
Se1 C10 1.925(12) . ?
Se2 C4 1.921(11) . ?
Se2 C37 1.932(10) . ?
F1 C1 1.403(14) . ?
F2 C7 1.357(15) . ?
O1 C38 1.282(10) . ?
O1 Sn1 2.201(6) 1_455 ?
O2 C38 1.280(10) . ?
O3 C40 1.257(9) . ?
O4 C40 1.244(10) . ?
C1 C6 1.377(18) . ?
C1 C2 1.384(19) . ?
C2 C3 1.399(16) . ?
C3 C4 1.335(14) . ?
C4 C5 1.336(14) . ?
C5 C6 1.343(16) . ?
C7 C12 1.289(16) . ?
C7 C8 1.371(17) . ?
C8 C9 1.392(16) . ?
C9 C10 1.377(13) . ?
C10 C11 1.389(15) . ?
C11 C12 1.415(17) . ?
C13 C14 1.481(9) . ?
C14 C15 1.479(9) . ?
C15 C16 1.529(8) . ?
C17 C18 1.469(9) . ?
C18 C19 1.673(18) . ?
C19 C20 1.446(9) . ?
C21 C22 1.446(14) . ?
C22 C23 1.456(14) . ?
C23 C24 1.561(12) . ?
C25 C26 1.36(2) . ?
C26 C27 1.506(15) . ?
C27 C28 1.479(12) . ?
C29 C30 1.528(15) . ?
C30 C31 1.455(14) . ?
C31 C32 1.562(12) . ?
C33 C34 1.428(16) . ?
C34 C35 1.483(15) . ?
C35 C36 1.432(13) . ?
C37 C38 1.502(12) . ?
C39 C40 1.490(11) . ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
C32 Sn1 C28 124.1(4) . . ?
C32 Sn1 C36 115.5(4) . . ?
C28 Sn1 C36 119.4(4) . . ?
C32 Sn1 O1 94.4(3) . 1_655 ?
C28 Sn1 O1 96.0(3) . 1_655 ?
C36 Sn1 O1 89.3(3) . 1_655 ?
C32 Sn1 O3 86.9(3) . . ?
C28 Sn1 O3 86.8(3) . . ?
C36 Sn1 O3 86.1(3) . . ?
O1 Sn1 O3 175.4(2) 1_655 . ?
C16 Sn2 C20 122.1(5) . . ?
C16 Sn2 C24 115.4(4) . . ?
C20 Sn2 C24 121.0(5) . . ?
C16 Sn2 O4 88.1(4) . . ?
C20 Sn2 O4 98.8(4) . . ?
C24 Sn2 O4 95.2(3) . . ?
C16 Sn2 O2 84.6(4) . . ?
C20 Sn2 O2 83.7(4) . . ?
C24 Sn2 O2 89.4(3) . . ?
O4 Sn2 O2 172.6(2) . . ?
C39 Se1 C10 100.3(4) . . ?
C4 Se2 C37 99.3(5) . . ?
C38 O1 Sn1 122.4(6) . 1_455 ?
C38 O2 Sn2 138.2(6) . . ?
C40 O3 Sn1 142.1(6) . . ?
C40 O4 Sn2 121.2(6) . . ?
C6 C1 C2 122.7(15) . . ?
C6 C1 F1 118.5(17) . . ?
C2 C1 F1 118.8(18) . . ?
C1 C2 C3 115.6(15) . . ?
C4 C3 C2 122.0(12) . . ?
C3 C4 C5 119.2(12) . . ?
C3 C4 Se2 119.4(10) . . ?
C5 C4 Se2 121.3(11) . . ?
C4 C5 C6 123.9(14) . . ?
C5 C6 C1 116.6(14) . . ?
C12 C7 F2 117.4(18) . . ?
C12 C7 C8 122.8(16) . . ?
F2 C7 C8 119.8(15) . . ?
C7 C8 C9 119.3(13) . . ?
C10 C9 C8 119.2(13) . . ?
C9 C10 C11 119.6(12) . . ?
C9 C10 Se1 121.0(11) . . ?
C11 C10 Se1 119.3(10) . . ?
C10 C11 C12 118.9(12) . . ?
C7 C12 C11 120.1(16) . . ?
C15 C14 C13 107.9(12) . . ?
C14 C15 C16 116.5(11) . . ?
C15 C16 Sn2 109.6(7) . . ?
C17 C18 C19 98.9(13) . . ?
C20 C19 C18 104.6(12) . . ?
C19 C20 Sn2 119.3(10) . . ?
C21 C22 C23 116.5(12) . . ?
C22 C23 C24 114.8(10) . . ?
C23 C24 Sn2 113.9(7) . . ?
C25 C26 C27 113.4(16) . . ?
C28 C27 C26 111.4(11) . . ?
C27 C28 Sn1 119.3(7) . . ?
C31 C30 C29 114.5(13) . . ?
C30 C31 C32 115.8(10) . . ?
C31 C32 Sn1 113.8(7) . . ?
C33 C34 C35 119.4(14) . . ?
C36 C35 C34 117.8(12) . . ?
C35 C36 Sn1 118.7(8) . . ?
C38 C37 Se2 112.2(7) . . ?
O2 C38 O1 119.9(9) . . ?
O2 C38 C37 120.6(9) . . ?
O1 C38 C37 119.3(9) . . ?
C40 C39 Se1 117.5(7) . . ?
O4 C40 O3 122.5(9) . . ?
O4 C40 C39 119.5(9) . . ?
O3 C40 C39 118.0(9) . . ?

loop_
_geom_torsion_atom_site_label_1
_geom_torsion_atom_site_label_2
_geom_torsion_atom_site_label_3
_geom_torsion_atom_site_label_4
_geom_torsion
_geom_torsion_site_symmetry_1
_geom_torsion_site_symmetry_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
_geom_torsion_publ_flag
C6 C1 C2 C3 0(2) . . . . ?
F1 C1 C2 C3 -179.5(12) . . . . ?
C1 C2 C3 C4 0(2) . . . . ?
C2 C3 C4 C5 0(2) . . . . ?
C2 C3 C4 Se2 -176.4(10) . . . . ?
C3 C4 C5 C6 -1(2) . . . . ?
Se2 C4 C5 C6 175.5(11) . . . . ?
C4 C5 C6 C1 1(2) . . . . ?
C2 C1 C6 C5 -1(2) . . . . ?
F1 C1 C6 C5 178.7(12) . . . . ?
C12 C7 C8 C9 -2(2) . . . . ?
F2 C7 C8 C9 178.3(11) . . . . ?
C7 C8 C9 C10 0.1(19) . . . . ?
C8 C9 C10 C11 0.1(17) . . . . ?
C8 C9 C10 Se1 176.1(9) . . . . ?
C9 C10 C11 C12 1.3(18) . . . . ?
Se1 C10 C11 C12 -174.8(10) . . . . ?
F2 C7 C12 C11 -176.9(13) . . . . ?
C8 C7 C12 C11 3(2) . . . . ?
C10 C11 C12 C7 -3(2) . . . . ?
C13 C14 C15 C16 175.7(14) . . . . ?
C14 C15 C16 Sn2 -176.0(12) . . . . ?
C17 C18 C19 C20 120.1(15) . . . . ?
C18 C19 C20 Sn2 166.5(9) . . . . ?
C21 C22 C23 C24 174.9(12) . . . . ?
C22 C23 C24 Sn2 166.4(9) . . . . ?
C25 C26 C27 C28 -171.9(17) . . . . ?
C26 C27 C28 Sn1 -179.2(11) . . . . ?
C29 C30 C31 C32 176.9(11) . . . . ?
C30 C31 C32 Sn1 -170.2(9) . . . . ?
C33 C34 C35 C36 177.2(14) . . . . ?
C34 C35 C36 Sn1 -172.9(10) . . . . ?
Sn2 O2 C38 O1 178.3(5) . . . . ?
Sn2 O2 C38 C37 1.8(15) . . . . ?
Sn1 O1 C38 O2 5.9(12) 1_455 . . . ?
Sn1 O1 C38 C37 -177.6(6) 1_455 . . . ?
Se2 C37 C38 O2 105.3(9) . . . . ?
Se2 C37 C38 O1 -71.2(10) . . . . ?
Sn2 O4 C40 O3 0.4(12) . . . . ?
Sn2 O4 C40 C39 176.5(6) . . . . ?
Sn1 O3 C40 O4 -179.0(5) . . . . ?
Sn1 O3 C40 C39 4.8(14) . . . . ?
Se1 C39 C40 O4 31.4(11) . . . . ?
Se1 C39 C40 O3 -152.3(7) . . . . ?

_refine_diff_density_max         0.847
_refine_diff_density_min         -0.606
_refine_diff_density_rms         0.100

