# Electronic Supplementary Material (ESI) for Dalton Transactions.
# This journal is © The Royal Society of Chemistry 2015

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

data_shelx
_database_code_depnum_ccdc_archive 'CCDC 980449'
_audit_update_record             
;
2015-05-15 deposited with the CCDC.
2015-05-27 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2014/6
_chemical_name_systematic        CES
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         'C22 H22 O6 S'
_chemical_formula_sum            'C22 H22 O6 S'
_chemical_formula_weight         414.45

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'
S S 0.1246 0.1234 '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                   14.3298(15)
_cell_length_b                   8.1440(8)
_cell_length_c                   16.8072(17)
_cell_angle_alpha                90
_cell_angle_beta                 104.2090(10)
_cell_angle_gamma                90
_cell_volume                     1901.4(3)
_cell_formula_units_Z            4
_cell_measurement_temperature    100(2)
_cell_measurement_reflns_used    5998
_cell_measurement_theta_min      2.50
_cell_measurement_theta_max      25.30


_exptl_crystal_description       block
_exptl_crystal_colour            'pale yellow'

_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.448
_exptl_crystal_F_000             872
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.500
_exptl_crystal_size_mid          0.420
_exptl_crystal_size_min          0.300
_exptl_absorpt_coefficient_mu    0.209
_shelx_estimated_absorpt_T_min   0.903
_shelx_estimated_absorpt_T_max   0.940
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.901
_exptl_absorpt_correction_T_max  0.939
_exptl_absorpt_process_details   SADABS

_exptl_absorpt_special_details   ?
_diffrn_ambient_temperature      100(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_radiation_source         'sealed tube'
_diffrn_radiation_monochromator  graphite
_diffrn_measurement_device_type  'CCD area detector'
_diffrn_measurement_method       'phi and omega scans'

_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            18441
_diffrn_reflns_av_unetI/netI     0.0360
_diffrn_reflns_av_R_equivalents  0.0490
_diffrn_reflns_limit_h_min       -17
_diffrn_reflns_limit_h_max       17
_diffrn_reflns_limit_k_min       -9
_diffrn_reflns_limit_k_max       9
_diffrn_reflns_limit_l_min       -20
_diffrn_reflns_limit_l_max       20
_diffrn_reflns_theta_min         1.677
_diffrn_reflns_theta_max         25.347
_diffrn_reflns_theta_full        25.242
_diffrn_measured_fraction_theta_max 0.999
_diffrn_measured_fraction_theta_full 1.000
_diffrn_reflns_Laue_measured_fraction_max 0.999
_diffrn_reflns_Laue_measured_fraction_full 1.000
_diffrn_reflns_point_group_measured_fraction_max 0.999
_diffrn_reflns_point_group_measured_fraction_full 1.000
_reflns_number_total             3473
_reflns_number_gt                2517
_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    'Bruker SHELXTL'
_computing_structure_refinement  'Bruker SHELXTL'
_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)+(0.0469P)²+0.9891P] 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         3473
_refine_ls_number_parameters     319
_refine_ls_number_restraints     180
_refine_ls_R_factor_all          0.0654
_refine_ls_R_factor_gt           0.0423
_refine_ls_wR_factor_ref         0.1097
_refine_ls_wR_factor_gt          0.0980
_refine_ls_goodness_of_fit_ref   1.031
_refine_ls_restrained_S_all      1.024
_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
O2 O -0.13636(9) 0.20241(17) 0.04403(8) 0.0234(3) Uani 1 1 d . . . . .
O1 O 0.08960(10) 0.52044(18) 0.25545(8) 0.0266(4) Uani 1 1 d D . . . .
O6 O 0.01454(11) 0.2663(2) 0.16580(9) 0.0324(4) Uani 1 1 d . . . . .
O5 O 0.23408(11) 0.3614(2) -0.03853(10) 0.0439(5) Uani 1 1 d . . . . .
C9 C 0.07954(14) 0.2840(2) -0.02597(12) 0.0212(4) Uani 1 1 d . . . . .
C14 C -0.07451(14) 0.1979(2) -0.00520(12) 0.0180(4) Uani 1 1 d . . . . .
C11 C 0.05589(15) 0.2160(3) -0.10445(13) 0.0257(5) Uani 1 1 d . . . . .
H11 H 0.0984 0.2241 -0.1382 0.031 Uiso 1 1 calc R U . . .
C13 C -0.09611(15) 0.1286(2) -0.08305(12) 0.0221(5) Uani 1 1 d . . . . .
H13 H -0.1549 0.0762 -0.1027 0.027 Uiso 1 1 calc R U . . .
C5 C 0.13398(14) 0.4372(2) 0.13539(12) 0.0186(4) Uani 1 1 d . . . . .
C8 C 0.04926(14) 0.3246(2) 0.11299(12) 0.0195(4) Uani 1 1 d . . . . .
C22 C -0.22927(14) 0.1256(3) 0.01767(12) 0.0231(5) Uani 1 1 d . . . . .
H22A H -0.2222 0.0072 0.0174 0.028 Uiso 1 1 calc R U . . .
H22B H -0.2608 0.1610 -0.0375 0.028 Uiso 1 1 calc R U . . .
C10 C 0.01619(14) 0.2733(2) 0.02541(12) 0.0183(4) Uani 1 1 d . . . . .
C21 C -0.28828(15) 0.1750(3) 0.07661(13) 0.0305(5) Uani 1 1 d . . . . .
H21A H -0.2768 0.2903 0.0898 0.037 Uiso 1 1 calc R U . . .
H21B H -0.3559 0.1628 0.0493 0.037 Uiso 1 1 calc R U . . .
C7 C 0.17563(15) 0.3632(3) 0.00342(13) 0.0256(5) Uani 1 1 d . . . . .
C12 C -0.03106(15) 0.1365(3) -0.13164(13) 0.0256(5) Uani 1 1 d . . . . .
H12 H -0.0462 0.0877 -0.1832 0.031 Uiso 1 1 calc R U . . .
C2 C 0.30616(15) 0.6132(3) 0.18386(14) 0.0291(5) Uani 1 1 d . . . . .
H2 H 0.3640 0.6698 0.2007 0.035 Uiso 1 1 calc R U . . .
C4 C 0.15585(14) 0.5243(2) 0.21052(12) 0.0213(5) Uani 1 1 d . . . . .
C20 C -0.17707(15) 0.1124(3) 0.20488(12) 0.0298(5) Uani 1 1 d D . . . .
H20A H -0.1716 0.2258 0.2230 0.036 Uiso 0.4877 1 calc R U P A 1
H20B H -0.1269 0.0904 0.1767 0.036 Uiso 0.4877 1 calc R U P A 1
H20C H -0.1629 0.2289 0.2099 0.036 Uiso 0.5123 1 calc R U P B 2
H20D H -0.1272 0.0578 0.1848 0.036 Uiso 0.5123 1 calc R U P B 2
C6 C 0.19817(14) 0.4466(2) 0.08486(13) 0.0212(5) Uani 1 1 d . . . . .
C3 C 0.24192(15) 0.6113(3) 0.23323(13) 0.0258(5) Uani 1 1 d . . . . .
H3 H 0.2565 0.6691 0.2825 0.031 Uiso 1 1 calc R U . . .
C1 C 0.28466(15) 0.5315(3) 0.10980(14) 0.0259(5) Uani 1 1 d . . . . .
H1 H 0.3279 0.5331 0.0766 0.031 Uiso 1 1 calc R U . . .
C15 C 0.1045(7) 0.5919(12) 0.3356(4) 0.0301(14) Uani 0.4877 1 d D U P C 1
H15A H 0.1065 0.7107 0.3321 0.036 Uiso 0.4877 1 calc R U P C 1
H15B H 0.1649 0.5541 0.3707 0.036 Uiso 0.4877 1 calc R U P C 1
C19 C -0.1663(4) -0.0032(7) 0.2790(3) 0.0268(15) Uani 0.4877 1 d D U P C 1
H19A H -0.1862 -0.1125 0.2589 0.032 Uiso 0.4877 1 calc R U P C 1
H19B H -0.2099 0.0332 0.3114 0.032 Uiso 0.4877 1 calc R U P C 1
O4 O -0.26927(11) 0.0842(2) 0.15119(9) 0.0380(4) Uani 1 1 d . . . . .
C16 C 0.0218(4) 0.5391(7) 0.3699(4) 0.0296(13) Uani 0.4877 1 d D U P C 1
H16A H 0.0228 0.5996 0.4198 0.036 Uiso 0.4877 1 calc R U P C 1
H16B H -0.0387 0.5618 0.3305 0.036 Uiso 0.4877 1 calc R U P C 1
C17 C -0.0567(4) 0.3088(7) 0.4056(4) 0.0310(12) Uani 0.4877 1 d D U P C 1
H17A H -0.1107 0.3254 0.3586 0.037 Uiso 0.4877 1 calc R U P C 1
H17B H -0.0690 0.3701 0.4515 0.037 Uiso 0.4877 1 calc R U P C 1
S1 S -0.0462(2) -0.0156(4) 0.3454(2) 0.0328(6) Uani 0.4877 1 d D . P C 1
C18 C -0.0469(4) 0.1287(7) 0.4269(3) 0.0302(12) Uani 0.4877 1 d D U P C 1
H18A H -0.0993 0.0989 0.4512 0.036 Uiso 0.4877 1 calc R U P C 1
H18B H 0.0125 0.1141 0.4688 0.036 Uiso 0.4877 1 calc R U P C 1
O3 O 0.0300(2) 0.3671(5) 0.3871(2) 0.0274(7) Uani 0.4877 1 d D U P C 1
S1' S -0.0674(3) 0.0237(4) 0.3562(2) 0.0427(8) Uani 0.5123 1 d D . P C 2
C18' C -0.0509(4) 0.2171(7) 0.4082(3) 0.0334(13) Uani 0.5123 1 d D U P C 2
H18C H -0.1090 0.2452 0.4251 0.040 Uiso 0.5123 1 calc R U P C 2
H18D H 0.0013 0.2082 0.4572 0.040 Uiso 0.5123 1 calc R U P C 2
O3' O 0.0201(3) 0.4786(5) 0.4069(2) 0.0342(8) Uani 0.5123 1 d D U P C 2
C17' C -0.0285(4) 0.3510(5) 0.3543(3) 0.0331(11) Uani 0.5123 1 d D U P C 2
H17C H 0.0122 0.3091 0.3205 0.040 Uiso 0.5123 1 calc R U P C 2
H17D H -0.0874 0.3928 0.3186 0.040 Uiso 0.5123 1 calc R U P C 2
C16' C 0.0268(4) 0.6273(7) 0.3641(3) 0.0336(12) Uani 0.5123 1 d D U P C 2
H16C H 0.0329 0.7185 0.4022 0.040 Uiso 0.5123 1 calc R U P C 2
H16D H -0.0322 0.6427 0.3219 0.040 Uiso 0.5123 1 calc R U P C 2
C19' C -0.1836(4) 0.0416(8) 0.2860(3) 0.0293(15) Uani 0.5123 1 d D U P C 2
H19C H -0.2133 -0.0660 0.2771 0.035 Uiso 0.5123 1 calc R U P C 2
H19D H -0.2242 0.1115 0.3100 0.035 Uiso 0.5123 1 calc R U P C 2
C15' C 0.1104(7) 0.6300(11) 0.3251(4) 0.0301(14) Uani 0.5123 1 d D U P C 2
H15C H 0.1204 0.7406 0.3074 0.036 Uiso 0.5123 1 calc R U P C 2
H15D H 0.1685 0.5950 0.3644 0.036 Uiso 0.5123 1 calc R U P C 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
O2 C14 1.353(2) . ?
O2 C22 1.439(2) . ?
O1 C4 1.351(2) . ?
O1 C15 1.435(6) . ?
O1 C15' 1.444(6) . ?
O6 C8 1.216(2) . ?
O5 C7 1.220(2) . ?
C9 C11 1.394(3) . ?
C9 C10 1.401(3) . ?
C9 C7 1.491(3) . ?
C14 C13 1.388(3) . ?
C14 C10 1.415(3) . ?
C11 C12 1.379(3) . ?
C11 H11 0.9300 . ?
C13 C12 1.383(3) . ?
C13 H13 0.9300 . ?
C5 C6 1.399(3) . ?
C5 C4 1.415(3) . ?
C5 C8 1.494(3) . ?
C8 C10 1.491(3) . ?
C22 C21 1.506(3) . ?
C22 H22A 0.9700 . ?
C22 H22B 0.9700 . ?
C21 O4 1.423(3) . ?
C21 H21A 0.9700 . ?
C21 H21B 0.9700 . ?
C7 C6 1.491(3) . ?
C12 H12 0.9300 . ?
C2 C1 1.378(3) . ?
C2 C3 1.382(3) . ?
C2 H2 0.9300 . ?
C4 C3 1.392(3) . ?
C20 O4 1.424(2) . ?
C20 C19' 1.503(5) . ?
C20 C19 1.538(5) . ?
C20 H20A 0.9700 . ?
C20 H20B 0.9700 . ?
C20 H20C 0.9700 . ?
C20 H20D 0.9700 . ?
C6 C1 1.391(3) . ?
C3 H3 0.9300 . ?
C1 H1 0.9300 . ?
C15 C16 1.502(6) . ?
C15 H15A 0.9700 . ?
C15 H15B 0.9700 . ?
C19 S1 1.809(5) . ?
C19 H19A 0.9700 . ?
C19 H19B 0.9700 . ?
C16 O3 1.430(5) . ?
C16 H16A 0.9700 . ?
C16 H16B 0.9700 . ?
C17 O3 1.434(5) . ?
C17 C18 1.508(6) . ?
C17 H17A 0.9700 . ?
C17 H17B 0.9700 . ?
S1 C18 1.806(5) . ?
C18 H18A 0.9700 . ?
C18 H18B 0.9700 . ?
S1' C18' 1.789(6) . ?
S1' C19' 1.795(5) . ?
C18' C17' 1.502(6) . ?
C18' H18C 0.9700 . ?
C18' H18D 0.9700 . ?
O3' C16' 1.423(5) . ?
O3' C17' 1.429(5) . ?
C17' H17C 0.9700 . ?
C17' H17D 0.9700 . ?
C16' C15' 1.501(6) . ?
C16' H16C 0.9700 . ?
C16' H16D 0.9700 . ?
C19' H19C 0.9700 . ?
C19' H19D 0.9700 . ?
C15' H15C 0.9700 . ?
C15' H15D 0.9700 . ?

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
C14 O2 C22 119.68(15) . . ?
C4 O1 C15 123.5(3) . . ?
C4 O1 C15' 113.9(3) . . ?
C11 C9 C10 121.01(19) . . ?
C11 C9 C7 118.41(18) . . ?
C10 C9 C7 120.54(18) . . ?
O2 C14 C13 124.01(18) . . ?
O2 C14 C10 116.53(17) . . ?
C13 C14 C10 119.44(18) . . ?
C12 C11 C9 119.36(19) . . ?
C12 C11 H11 120.3 . . ?
C9 C11 H11 120.3 . . ?
C12 C13 C14 120.70(19) . . ?
C12 C13 H13 119.6 . . ?
C14 C13 H13 119.6 . . ?
C6 C5 C4 118.68(18) . . ?
C6 C5 C8 119.69(18) . . ?
C4 C5 C8 121.39(18) . . ?
O6 C8 C10 121.57(18) . . ?
O6 C8 C5 120.58(18) . . ?
C10 C8 C5 117.53(17) . . ?
O2 C22 C21 107.93(16) . . ?
O2 C22 H22A 110.1 . . ?
C21 C22 H22A 110.1 . . ?
O2 C22 H22B 110.1 . . ?
C21 C22 H22B 110.1 . . ?
H22A C22 H22B 108.4 . . ?
C9 C10 C14 118.61(18) . . ?
C9 C10 C8 119.62(17) . . ?
C14 C10 C8 121.43(17) . . ?
O4 C21 C22 115.06(18) . . ?
O4 C21 H21A 108.5 . . ?
C22 C21 H21A 108.5 . . ?
O4 C21 H21B 108.5 . . ?
C22 C21 H21B 108.5 . . ?
H21A C21 H21B 107.5 . . ?
O5 C7 C9 120.8(2) . . ?
O5 C7 C6 120.74(19) . . ?
C9 C7 C6 118.41(18) . . ?
C11 C12 C13 120.76(19) . . ?
C11 C12 H12 119.6 . . ?
C13 C12 H12 119.6 . . ?
C1 C2 C3 120.17(19) . . ?
C1 C2 H2 119.9 . . ?
C3 C2 H2 119.9 . . ?
O1 C4 C3 123.77(19) . . ?
O1 C4 C5 117.07(17) . . ?
C3 C4 C5 119.14(19) . . ?
O4 C20 C19' 105.0(2) . . ?
O4 C20 C19 107.9(2) . . ?
O4 C20 H20A 110.1 . . ?
C19 C20 H20A 110.1 . . ?
O4 C20 H20B 110.1 . . ?
C19 C20 H20B 110.1 . . ?
H20A C20 H20B 108.4 . . ?
O4 C20 H20C 110.8 . . ?
C19' C20 H20C 110.8 . . ?
O4 C20 H20D 110.8 . . ?
C19' C20 H20D 110.8 . . ?
H20C C20 H20D 108.8 . . ?
C1 C6 C5 120.9(2) . . ?
C1 C6 C7 118.65(19) . . ?
C5 C6 C7 120.39(18) . . ?
C2 C3 C4 121.1(2) . . ?
C2 C3 H3 119.4 . . ?
C4 C3 H3 119.4 . . ?
C2 C1 C6 119.8(2) . . ?
C2 C1 H1 120.1 . . ?
C6 C1 H1 120.1 . . ?
O1 C15 C16 107.1(5) . . ?
O1 C15 H15A 110.3 . . ?
C16 C15 H15A 110.3 . . ?
O1 C15 H15B 110.3 . . ?
C16 C15 H15B 110.3 . . ?
H15A C15 H15B 108.5 . . ?
C20 C19 S1 115.2(4) . . ?
C20 C19 H19A 108.5 . . ?
S1 C19 H19A 108.5 . . ?
C20 C19 H19B 108.5 . . ?
S1 C19 H19B 108.5 . . ?
H19A C19 H19B 107.5 . . ?
C21 O4 C20 114.94(16) . . ?
O3 C16 C15 108.9(6) . . ?
O3 C16 H16A 109.9 . . ?
C15 C16 H16A 109.9 . . ?
O3 C16 H16B 109.9 . . ?
C15 C16 H16B 109.9 . . ?
H16A C16 H16B 108.3 . . ?
O3 C17 C18 109.7(4) . . ?
O3 C17 H17A 109.7 . . ?
C18 C17 H17A 109.7 . . ?
O3 C17 H17B 109.7 . . ?
C18 C17 H17B 109.7 . . ?
H17A C17 H17B 108.2 . . ?
C18 S1 C19 104.5(3) . . ?
C17 C18 S1 118.1(4) . . ?
C17 C18 H18A 107.8 . . ?
S1 C18 H18A 107.8 . . ?
C17 C18 H18B 107.8 . . ?
S1 C18 H18B 107.8 . . ?
H18A C18 H18B 107.1 . . ?
C16 O3 C17 109.6(4) . . ?
C18' S1' C19' 103.8(3) . . ?
C17' C18' S1' 111.5(4) . . ?
C17' C18' H18C 109.3 . . ?
S1' C18' H18C 109.3 . . ?
C17' C18' H18D 109.3 . . ?
S1' C18' H18D 109.3 . . ?
H18C C18' H18D 108.0 . . ?
C16' O3' C17' 113.0(4) . . ?
O3' C17' C18' 107.4(4) . . ?
O3' C17' H17C 110.2 . . ?
C18' C17' H17C 110.2 . . ?
O3' C17' H17D 110.2 . . ?
C18' C17' H17D 110.2 . . ?
H17C C17' H17D 108.5 . . ?
O3' C16' C15' 113.1(5) . . ?
O3' C16' H16C 109.0 . . ?
C15' C16' H16C 109.0 . . ?
O3' C16' H16D 109.0 . . ?
C15' C16' H16D 109.0 . . ?
H16C C16' H16D 107.8 . . ?
C20 C19' S1' 111.9(4) . . ?
C20 C19' H19C 109.2 . . ?
S1' C19' H19C 109.2 . . ?
C20 C19' H19D 109.2 . . ?
S1' C19' H19D 109.2 . . ?
H19C C19' H19D 107.9 . . ?
O1 C15' C16' 108.5(5) . . ?
O1 C15' H15C 110.0 . . ?
C16' C15' H15C 110.0 . . ?
O1 C15' H15D 110.0 . . ?
C16' C15' H15D 110.0 . . ?
H15C C15' H15D 108.4 . . ?

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
C22 O2 C14 C13 2.9(3) . . . . ?
C22 O2 C14 C10 -178.87(17) . . . . ?
C10 C9 C11 C12 -0.3(3) . . . . ?
C7 C9 C11 C12 177.49(19) . . . . ?
O2 C14 C13 C12 176.43(18) . . . . ?
C10 C14 C13 C12 -1.8(3) . . . . ?
C6 C5 C8 O6 152.05(19) . . . . ?
C4 C5 C8 O6 -22.3(3) . . . . ?
C6 C5 C8 C10 -21.6(3) . . . . ?
C4 C5 C8 C10 164.04(18) . . . . ?
C14 O2 C22 C21 -170.18(17) . . . . ?
C11 C9 C10 C14 -2.6(3) . . . . ?
C7 C9 C10 C14 179.67(18) . . . . ?
C11 C9 C10 C8 170.85(18) . . . . ?
C7 C9 C10 C8 -6.9(3) . . . . ?
O2 C14 C10 C9 -174.73(17) . . . . ?
C13 C14 C10 C9 3.6(3) . . . . ?
O2 C14 C10 C8 11.9(3) . . . . ?
C13 C14 C10 C8 -169.74(18) . . . . ?
O6 C8 C10 C9 -152.81(19) . . . . ?
C5 C8 C10 C9 20.8(3) . . . . ?
O6 C8 C10 C14 20.5(3) . . . . ?
C5 C8 C10 C14 -165.93(17) . . . . ?
O2 C22 C21 O4 -80.8(2) . . . . ?
C11 C9 C7 O5 -3.6(3) . . . . ?
C10 C9 C7 O5 174.2(2) . . . . ?
C11 C9 C7 C6 175.61(18) . . . . ?
C10 C9 C7 C6 -6.6(3) . . . . ?
C9 C11 C12 C13 2.2(3) . . . . ?
C14 C13 C12 C11 -1.2(3) . . . . ?
C15 O1 C4 C3 -6.5(6) . . . . ?
C15' O1 C4 C3 6.8(5) . . . . ?
C15 O1 C4 C5 175.0(6) . . . . ?
C15' O1 C4 C5 -171.8(5) . . . . ?
C6 C5 C4 O1 176.17(17) . . . . ?
C8 C5 C4 O1 -9.4(3) . . . . ?
C6 C5 C4 C3 -2.4(3) . . . . ?
C8 C5 C4 C3 171.97(18) . . . . ?
C4 C5 C6 C1 3.8(3) . . . . ?
C8 C5 C6 C1 -170.64(18) . . . . ?
C4 C5 C6 C7 -177.10(18) . . . . ?
C8 C5 C6 C7 8.4(3) . . . . ?
O5 C7 C6 C1 4.1(3) . . . . ?
C9 C7 C6 C1 -175.12(18) . . . . ?
O5 C7 C6 C5 -175.0(2) . . . . ?
C9 C7 C6 C5 5.8(3) . . . . ?
C1 C2 C3 C4 1.6(3) . . . . ?
O1 C4 C3 C2 -178.73(19) . . . . ?
C5 C4 C3 C2 -0.2(3) . . . . ?
C3 C2 C1 C6 -0.2(3) . . . . ?
C5 C6 C1 C2 -2.6(3) . . . . ?
C7 C6 C1 C2 178.35(19) . . . . ?
C4 O1 C15 C16 -171.3(4) . . . . ?
O4 C20 C19 S1 168.9(3) . . . . ?
C22 C21 O4 C20 68.4(2) . . . . ?
C19' C20 O4 C21 165.4(3) . . . . ?
C19 C20 O4 C21 -176.3(3) . . . . ?
O1 C15 C16 O3 69.5(8) . . . . ?
C20 C19 S1 C18 96.0(5) . . . . ?
O3 C17 C18 S1 -70.7(6) . . . . ?
C19 S1 C18 C17 -66.7(5) . . . . ?
C15 C16 O3 C17 -169.6(5) . . . . ?
C18 C17 O3 C16 -178.0(5) . . . . ?
C19' S1' C18' C17' -74.5(5) . . . . ?
C16' O3' C17' C18' -167.1(4) . . . . ?
S1' C18' C17' O3' -157.2(4) . . . . ?
C17' O3' C16' C15' -83.8(6) . . . . ?
O4 C20 C19' S1' 167.2(3) . . . . ?
C18' S1' C19' C20 89.1(4) . . . . ?
C4 O1 C15' C16' 174.0(4) . . . . ?
O3' C16' C15' O1 72.1(7) . . . . ?

_refine_diff_density_max         0.482
_refine_diff_density_min         -0.233
_refine_diff_density_rms         0.047

_shelxl_version_number           2014/6

####################################################################### 
# 
# 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_shelx
_database_code_depnum_ccdc_archive 'CCDC 980450'
_audit_update_record             
;
2015-05-06 deposited with the CCDC.
2015-05-27 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2014
_chemical_name_systematic        
;
 ?
;
_chemical_name_common            CES.PB
_chemical_melting_point          ?
_chemical_formula_moiety         'C22 H22 Cl2 O14 Pb S'
_chemical_formula_sum            'C22 H22 Cl2 O14 Pb S'
_chemical_formula_weight         820.54

loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
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'
Cl Cl 0.1484 0.1585 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
Pb Pb -3.3944 10.1111 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

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

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

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

_cell_length_a                   8.0605(6)
_cell_length_b                   12.1558(10)
_cell_length_c                   13.1591(10)
_cell_angle_alpha                80.0900(10)
_cell_angle_beta                 82.6810(10)
_cell_angle_gamma                85.4590(10)
_cell_volume                     1257.60(17)
_cell_formula_units_Z            2
_cell_measurement_temperature    100(2)
_cell_measurement_reflns_used    9993
_cell_measurement_theta_min      2.51
_cell_measurement_theta_max      25.46

_exptl_crystal_description       NEEDLE
_exptl_crystal_colour            YELLOW
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    2.167
_exptl_crystal_F_000             796
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.200
_exptl_crystal_size_mid          0.150
_exptl_crystal_size_min          0.100
_exptl_absorpt_coefficient_mu    7.079
_shelx_estimated_absorpt_T_min   0.332
_shelx_estimated_absorpt_T_max   0.538
_exptl_absorpt_correction_type   MULTI-SCAN
_exptl_absorpt_correction_T_min  0.233
_exptl_absorpt_correction_T_max  0.493
_exptl_absorpt_process_details   SADABS

_exptl_special_details           
;
 ?
;

_diffrn_ambient_temperature      100(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_source                   ?
_diffrn_measurement_device_type  'Bruker APEX-II CCD'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            12675
_diffrn_reflns_av_unetI/netI     0.0298
_diffrn_reflns_av_R_equivalents  0.0263
_diffrn_reflns_limit_h_min       -9
_diffrn_reflns_limit_h_max       9
_diffrn_reflns_limit_k_min       -14
_diffrn_reflns_limit_k_max       14
_diffrn_reflns_limit_l_min       -15
_diffrn_reflns_limit_l_max       15
_diffrn_reflns_theta_min         1.582
_diffrn_reflns_theta_max         25.464
_diffrn_reflns_theta_full        25.242
_diffrn_measured_fraction_theta_max 0.996
_diffrn_measured_fraction_theta_full 0.998
_diffrn_reflns_Laue_measured_fraction_max 0.996
_diffrn_reflns_Laue_measured_fraction_full 0.998
_diffrn_reflns_point_group_measured_fraction_max 0.996
_diffrn_reflns_point_group_measured_fraction_full 0.998
_reflns_number_total             4662
_reflns_number_gt                4575
_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 APEX2'
_computing_cell_refinement       'Bruker SAINT'
_computing_data_reduction        'Bruker SAINT'
_computing_structure_solution    'SHELXS-97 (Sheldrick 2008)'
_computing_structure_refinement  'SHELXL-2013 (Sheldrick 2013)'
_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)+(0.0102P)²+1.1525P] 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         4662
_refine_ls_number_parameters     361
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0162
_refine_ls_R_factor_gt           0.0158
_refine_ls_wR_factor_ref         0.0401
_refine_ls_wR_factor_gt          0.0398
_refine_ls_goodness_of_fit_ref   1.067
_refine_ls_restrained_S_all      1.067
_refine_ls_shift/su_max          0.001
_refine_ls_shift/su_mean         0.000

loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_site_symmetry_order
_atom_site_calc_flag
_atom_site_refinement_flags_posn
_atom_site_refinement_flags_adp
_atom_site_refinement_flags_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
C1 C 0.0500(3) 0.2651(2) -0.1423(2) 0.0153(6) Uani 1 1 d . . . . .
H1 H 0.0568 0.2380 -0.2047 0.018 Uiso 1 1 calc R U . . .
C2 C -0.0989(3) 0.3154(2) -0.1024(2) 0.0160(6) Uani 1 1 d . . . . .
H2 H -0.1918 0.3228 -0.1389 0.019 Uiso 1 1 calc R U . . .
C3 C -0.1108(3) 0.3548(2) -0.0089(2) 0.0145(5) Uani 1 1 d . . . . .
H3 H -0.2116 0.3882 0.0169 0.017 Uiso 1 1 calc R U . . .
C4 C 0.0276(3) 0.3447(2) 0.0471(2) 0.0120(5) Uani 1 1 d . . . . .
C5 C 0.1816(3) 0.2966(2) 0.0059(2) 0.0111(5) Uani 1 1 d . . . . .
C6 C 0.1890(3) 0.2557(2) -0.0880(2) 0.0124(5) Uani 1 1 d . . . . .
C7 C 0.3479(3) 0.2004(2) -0.1322(2) 0.0135(5) Uani 1 1 d . . . . .
C8 C 0.3376(3) 0.2918(2) 0.05698(19) 0.0100(5) Uani 1 1 d . . . . .
C9 C 0.4844(3) 0.1702(2) -0.0644(2) 0.0117(5) Uani 1 1 d . . . . .
C10 C 0.4727(3) 0.2079(2) 0.03145(19) 0.0108(5) Uani 1 1 d . . . . .
C11 C 0.6163(3) 0.0985(2) -0.0954(2) 0.0147(5) Uani 1 1 d . . . . .
H11 H 0.6255 0.0771 -0.1606 0.018 Uiso 1 1 calc R U . . .
C12 C 0.7342(3) 0.0591(2) -0.0279(2) 0.0156(6) Uani 1 1 d . . . . .
H12 H 0.8236 0.0116 -0.0484 0.019 Uiso 1 1 calc R U . . .
C13 C 0.7213(3) 0.0894(2) 0.0696(2) 0.0133(5) Uani 1 1 d . . . . .
H13 H 0.7988 0.0594 0.1150 0.016 Uiso 1 1 calc R U . . .
C14 C 0.5922(3) 0.1647(2) 0.10005(19) 0.0098(5) Uani 1 1 d . . . . .
C15 C -0.1396(3) 0.4288(2) 0.1813(2) 0.0120(5) Uani 1 1 d . . . . .
H15A H -0.2250 0.3746 0.1940 0.014 Uiso 1 1 calc R U . . .
H15B H -0.1749 0.4920 0.1315 0.014 Uiso 1 1 calc R U . . .
C16 C -0.1146(3) 0.4665(2) 0.2807(2) 0.0120(5) Uani 1 1 d . . . . .
H16A H -0.0252 0.5178 0.2683 0.014 Uiso 1 1 calc R U . . .
H16B H -0.2164 0.5050 0.3076 0.014 Uiso 1 1 calc R U . . .
C17 C -0.1381(3) 0.3812(2) 0.4597(2) 0.0130(5) Uani 1 1 d . . . . .
H17A H -0.2593 0.3803 0.4679 0.016 Uiso 1 1 calc R U . . .
H17B H -0.1082 0.4519 0.4750 0.016 Uiso 1 1 calc R U . . .
C18 C -0.0654(3) 0.2852(2) 0.5334(2) 0.0133(5) Uani 1 1 d . . . . .
H18A H -0.0832 0.2146 0.5127 0.016 Uiso 1 1 calc R U . . .
H18B H -0.1206 0.2853 0.6034 0.016 Uiso 1 1 calc R U . . .
C19 C 0.2436(3) 0.1583(2) 0.5657(2) 0.0128(5) Uani 1 1 d . . . . .
H19A H 0.2261 0.1357 0.6405 0.015 Uiso 1 1 calc R U . . .
H19B H 0.1874 0.1077 0.5338 0.015 Uiso 1 1 calc R U . . .
C20 C 0.4282(3) 0.1538(2) 0.52835(19) 0.0125(5) Uani 1 1 d . . . . .
H20A H 0.4800 0.2152 0.5480 0.015 Uiso 1 1 calc R U . . .
H20B H 0.4814 0.0842 0.5600 0.015 Uiso 1 1 calc R U . . .
C21 C 0.6251(3) 0.1636(2) 0.3761(2) 0.0128(5) Uani 1 1 d . . . . .
H21A H 0.6910 0.1174 0.4258 0.015 Uiso 1 1 calc R U . . .
H21B H 0.6604 0.2396 0.3667 0.015 Uiso 1 1 calc R U . . .
C22 C 0.6566(3) 0.1216(2) 0.2747(2) 0.0141(5) Uani 1 1 d . . . . .
H22A H 0.7762 0.1158 0.2531 0.017 Uiso 1 1 calc R U . . .
H22B H 0.6143 0.0477 0.2826 0.017 Uiso 1 1 calc R U . . .
O1 O 0.0193(2) 0.37861(16) 0.14137(14) 0.0131(4) Uani 1 1 d . . . . .
O2 O 0.5745(2) 0.19710(15) 0.19650(13) 0.0106(4) Uani 1 1 d . . . . .
O3 O -0.0722(2) 0.36934(15) 0.35507(13) 0.0113(4) Uani 1 1 d . . . . .
O4 O 0.4503(2) 0.16183(15) 0.41630(13) 0.0111(4) Uani 1 1 d . . . . .
O5 O 0.3602(3) 0.17396(17) -0.21826(15) 0.0212(4) Uani 1 1 d . . . . .
O6 O 0.3553(2) 0.35693(15) 0.11608(14) 0.0115(4) Uani 1 1 d . . . . .
O7 O 0.4939(2) 0.41385(15) 0.32887(15) 0.0172(4) Uani 1 1 d . . . . .
O8 O 0.4910(2) 0.57739(17) 0.20166(15) 0.0207(4) Uani 1 1 d . . . . .
O9 O 0.2460(2) 0.52595(16) 0.31389(15) 0.0180(4) Uani 1 1 d . . . . .
O10 O 0.4733(3) 0.59260(18) 0.37873(16) 0.0227(5) Uani 1 1 d . . . . .
O11 O 0.0218(2) -0.01869(17) 0.25719(16) 0.0192(4) Uani 1 1 d . . . . .
O12 O 0.2305(3) -0.04405(17) 0.36931(18) 0.0287(5) Uani 1 1 d . . . . .
O13 O 0.0404(2) 0.11341(17) 0.36745(15) 0.0200(4) Uani 1 1 d . . . . .
O14 O 0.2441(3) 0.10231(17) 0.22655(16) 0.0224(5) Uani 1 1 d . . . . .
S1 S 0.15865(8) 0.30111(5) 0.53029(5) 0.01186(13) Uani 1 1 d . . . . .
Cl1 Cl 0.42757(7) 0.53021(5) 0.30524(5) 0.01267(13) Uani 1 1 d . . . . .
Cl2 Cl 0.13399(7) 0.03609(5) 0.30544(5) 0.01156(13) Uani 1 1 d . . . . .
Pb1 Pb 0.24115(2) 0.29766(2) 0.31017(2) 0.00885(4) 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
C1 C2 1.387(4) . ?
C1 C6 1.391(4) . ?
C1 H1 0.9300 . ?
C2 C3 1.385(4) . ?
C2 H2 0.9300 . ?
C3 C4 1.399(4) . ?
C3 H3 0.9300 . ?
C4 O1 1.366(3) . ?
C4 C5 1.414(4) . ?
C5 C6 1.403(4) . ?
C5 C8 1.493(3) . ?
C6 C7 1.496(4) . ?
C7 O5 1.219(3) . ?
C7 C9 1.488(4) . ?
C8 O6 1.229(3) . ?
C8 C10 1.479(4) . ?
C9 C11 1.386(4) . ?
C9 C10 1.404(4) . ?
C10 C14 1.413(3) . ?
C11 C12 1.386(4) . ?
C11 H11 0.9300 . ?
C12 C13 1.383(4) . ?
C12 H12 0.9300 . ?
C13 C14 1.397(4) . ?
C13 H13 0.9300 . ?
C14 O2 1.379(3) . ?
C15 O1 1.450(3) . ?
C15 C16 1.500(4) . ?
C15 H15A 0.9700 . ?
C15 H15B 0.9700 . ?
C16 O3 1.446(3) . ?
C16 H16A 0.9700 . ?
C16 H16B 0.9700 . ?
C17 O3 1.439(3) . ?
C17 C18 1.515(4) . ?
C17 H17A 0.9700 . ?
C17 H17B 0.9700 . ?
C18 S1 1.826(3) . ?
C18 H18A 0.9700 . ?
C18 H18B 0.9700 . ?
C19 C20 1.507(4) . ?
C19 S1 1.820(3) . ?
C19 H19A 0.9700 . ?
C19 H19B 0.9700 . ?
C20 O4 1.450(3) . ?
C20 H20A 0.9700 . ?
C20 H20B 0.9700 . ?
C21 O4 1.441(3) . ?
C21 C22 1.495(4) . ?
C21 H21A 0.9700 . ?
C21 H21B 0.9700 . ?
C22 O2 1.446(3) . ?
C22 H22A 0.9700 . ?
C22 H22B 0.9700 . ?
O3 Pb1 2.6334(17) . ?
O4 Pb1 2.6239(17) . ?
O6 Pb1 2.6003(17) . ?
O7 Cl1 1.4678(19) . ?
O7 Pb1 2.6284(18) . ?
O8 Cl1 1.431(2) . ?
O9 Cl1 1.4581(19) . ?
O10 Cl1 1.426(2) . ?
O11 Cl2 1.432(2) . ?
O12 Cl2 1.423(2) . ?
O13 Cl2 1.454(2) . ?
O14 Cl2 1.450(2) . ?
S1 Pb1 2.8950(7) . ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
C2 C1 C6 119.3(3) . . ?
C2 C1 H1 120.3 . . ?
C6 C1 H1 120.3 . . ?
C3 C2 C1 120.7(2) . . ?
C3 C2 H2 119.6 . . ?
C1 C2 H2 119.6 . . ?
C2 C3 C4 120.5(3) . . ?
C2 C3 H3 119.7 . . ?
C4 C3 H3 119.7 . . ?
O1 C4 C3 122.3(2) . . ?
O1 C4 C5 118.3(2) . . ?
C3 C4 C5 119.4(2) . . ?
C6 C5 C4 118.8(2) . . ?
C6 C5 C8 119.0(2) . . ?
C4 C5 C8 122.2(2) . . ?
C1 C6 C5 121.2(2) . . ?
C1 C6 C7 118.3(2) . . ?
C5 C6 C7 120.5(2) . . ?
O5 C7 C9 121.2(2) . . ?
O5 C7 C6 120.8(2) . . ?
C9 C7 C6 117.8(2) . . ?
O6 C8 C10 121.1(2) . . ?
O6 C8 C5 121.4(2) . . ?
C10 C8 C5 117.5(2) . . ?
C11 C9 C10 121.4(2) . . ?
C11 C9 C7 118.2(2) . . ?
C10 C9 C7 120.3(2) . . ?
C9 C10 C14 118.6(2) . . ?
C9 C10 C8 119.3(2) . . ?
C14 C10 C8 122.2(2) . . ?
C12 C11 C9 119.0(2) . . ?
C12 C11 H11 120.5 . . ?
C9 C11 H11 120.5 . . ?
C13 C12 C11 121.2(2) . . ?
C13 C12 H12 119.4 . . ?
C11 C12 H12 119.4 . . ?
C12 C13 C14 120.2(2) . . ?
C12 C13 H13 119.9 . . ?
C14 C13 H13 119.9 . . ?
O2 C14 C13 122.2(2) . . ?
O2 C14 C10 118.3(2) . . ?
C13 C14 C10 119.5(2) . . ?
O1 C15 C16 107.4(2) . . ?
O1 C15 H15A 110.2 . . ?
C16 C15 H15A 110.2 . . ?
O1 C15 H15B 110.2 . . ?
C16 C15 H15B 110.2 . . ?
H15A C15 H15B 108.5 . . ?
O3 C16 C15 108.7(2) . . ?
O3 C16 H16A 109.9 . . ?
C15 C16 H16A 109.9 . . ?
O3 C16 H16B 109.9 . . ?
C15 C16 H16B 109.9 . . ?
H16A C16 H16B 108.3 . . ?
O3 C17 C18 108.6(2) . . ?
O3 C17 H17A 110.0 . . ?
C18 C17 H17A 110.0 . . ?
O3 C17 H17B 110.0 . . ?
C18 C17 H17B 110.0 . . ?
H17A C17 H17B 108.3 . . ?
C17 C18 S1 108.86(18) . . ?
C17 C18 H18A 109.9 . . ?
S1 C18 H18A 109.9 . . ?
C17 C18 H18B 109.9 . . ?
S1 C18 H18B 109.9 . . ?
H18A C18 H18B 108.3 . . ?
C20 C19 S1 108.38(18) . . ?
C20 C19 H19A 110.0 . . ?
S1 C19 H19A 110.0 . . ?
C20 C19 H19B 110.0 . . ?
S1 C19 H19B 110.0 . . ?
H19A C19 H19B 108.4 . . ?
O4 C20 C19 109.0(2) . . ?
O4 C20 H20A 109.9 . . ?
C19 C20 H20A 109.9 . . ?
O4 C20 H20B 109.9 . . ?
C19 C20 H20B 109.9 . . ?
H20A C20 H20B 108.3 . . ?
O4 C21 C22 111.3(2) . . ?
O4 C21 H21A 109.4 . . ?
C22 C21 H21A 109.4 . . ?
O4 C21 H21B 109.4 . . ?
C22 C21 H21B 109.4 . . ?
H21A C21 H21B 108.0 . . ?
O2 C22 C21 110.0(2) . . ?
O2 C22 H22A 109.7 . . ?
C21 C22 H22A 109.7 . . ?
O2 C22 H22B 109.7 . . ?
C21 C22 H22B 109.7 . . ?
H22A C22 H22B 108.2 . . ?
C4 O1 C15 117.21(19) . . ?
C14 O2 C22 114.88(19) . . ?
C17 O3 C16 112.22(19) . . ?
C17 O3 Pb1 121.06(14) . . ?
C16 O3 Pb1 110.24(13) . . ?
C21 O4 C20 111.15(18) . . ?
C21 O4 Pb1 116.91(13) . . ?
C20 O4 Pb1 117.77(14) . . ?
C8 O6 Pb1 116.50(15) . . ?
Cl1 O7 Pb1 103.30(9) . . ?
C19 S1 C18 103.46(12) . . ?
C19 S1 Pb1 92.90(9) . . ?
C18 S1 Pb1 95.98(9) . . ?
O10 Cl1 O8 110.97(12) . . ?
O10 Cl1 O9 110.47(12) . . ?
O8 Cl1 O9 110.11(12) . . ?
O10 Cl1 O7 109.49(12) . . ?
O8 Cl1 O7 109.60(12) . . ?
O9 Cl1 O7 106.08(11) . . ?
O12 Cl2 O11 110.37(13) . . ?
O12 Cl2 O14 109.90(13) . . ?
O11 Cl2 O14 109.84(12) . . ?
O12 Cl2 O13 109.81(13) . . ?
O11 Cl2 O13 110.19(12) . . ?
O14 Cl2 O13 106.67(12) . . ?
O6 Pb1 O4 113.45(5) . . ?
O6 Pb1 O7 79.39(6) . . ?
O4 Pb1 O7 72.68(6) . . ?
O6 Pb1 O3 113.26(5) . . ?
O4 Pb1 O3 132.92(5) . . ?
O7 Pb1 O3 121.88(6) . . ?
O6 Pb1 S1 161.00(4) . . ?
O4 Pb1 S1 69.68(4) . . ?
O7 Pb1 S1 84.06(5) . . ?
O3 Pb1 S1 68.21(4) . . ?

_refine_diff_density_max         0.889
_refine_diff_density_min         -0.727
_refine_diff_density_rms         0.095

_shelxl_version_number           2014-1

####################################################################### 
# 
# 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_shelx
_database_code_depnum_ccdc_archive 'CCDC 980451'
_audit_update_record             
;
2015-05-15 deposited with the CCDC.
2015-05-27 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2013
_chemical_name_systematic        
;
 ?
;
_chemical_name_common            CESe
_chemical_melting_point          ?
_chemical_formula_moiety         'C22 H22 O6 Se'
_chemical_formula_sum            'C22 H22 O6 Se'
_chemical_formula_weight         461.35

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'

_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                   7.4979(8)
_cell_length_b                   16.0574(17)
_cell_length_c                   16.3759(17)
_cell_angle_alpha                90
_cell_angle_beta                 100.5730(10)
_cell_angle_gamma                90
_cell_volume                     1938.1(4)
_cell_formula_units_Z            4
_cell_measurement_temperature    100(2)
_cell_measurement_reflns_used    7093
_cell_measurement_theta_min      2.53
_cell_measurement_theta_max      25.30

_exptl_crystal_description       needle
_exptl_crystal_colour            yellow
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.581
_exptl_crystal_F_000             944
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.500
_exptl_crystal_size_mid          0.450
_exptl_crystal_size_min          0.200
_exptl_absorpt_coefficient_mu    1.975
_shelx_estimated_absorpt_T_min   0.438
_shelx_estimated_absorpt_T_max   0.693
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.358
_exptl_absorpt_correction_T_max  0.674
_exptl_absorpt_process_details   SADBAS

_exptl_special_details           
;
 ?
;

_diffrn_ambient_temperature      100(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_radiation_source         'sealed tube'
_diffrn_radiation_monochromator  graphite
_diffrn_measurement_device_type  'CCD area detector'
_diffrn_measurement_method       'phi and omega scans'
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            18948
_diffrn_reflns_av_unetI/netI     0.0386
_diffrn_reflns_av_R_equivalents  0.0498
_diffrn_reflns_limit_h_min       -9
_diffrn_reflns_limit_h_max       9
_diffrn_reflns_limit_k_min       -19
_diffrn_reflns_limit_k_max       19
_diffrn_reflns_limit_l_min       -19
_diffrn_reflns_limit_l_max       19
_diffrn_reflns_theta_min         1.791
_diffrn_reflns_theta_max         25.357
_diffrn_reflns_theta_full        25.242
_diffrn_measured_fraction_theta_max 0.997
_diffrn_measured_fraction_theta_full 0.999
_diffrn_reflns_Laue_measured_fraction_max 0.997
_diffrn_reflns_Laue_measured_fraction_full 0.999
_diffrn_reflns_point_group_measured_fraction_max 0.997
_diffrn_reflns_point_group_measured_fraction_full 0.999
_reflns_number_total             3535
_reflns_number_gt                2578
_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    'Bruker SHELXTL'
_computing_structure_refinement  'SHELXL-2013 (Sheldrick, 2013)'
_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)+(0.0374P)²+2.9314P] 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         3535
_refine_ls_number_parameters     274
_refine_ls_number_restraints     67
_refine_ls_R_factor_all          0.0671
_refine_ls_R_factor_gt           0.0395
_refine_ls_wR_factor_ref         0.1013
_refine_ls_wR_factor_gt          0.0886
_refine_ls_goodness_of_fit_ref   1.061
_refine_ls_restrained_S_all      1.061
_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
Se1 Se 0.51812(5) 0.38863(3) 0.43369(3) 0.03887(15) Uani 1 1 d . . . . .
O1 O 0.7073(3) 0.07850(17) 0.35924(14) 0.0358(6) Uani 1 1 d . . . . .
O2 O 1.0470(3) 0.21499(15) 0.61989(14) 0.0307(6) Uani 1 1 d . . . . .
O4 O 1.0404(3) 0.39410(15) 0.56921(15) 0.0361(6) Uani 1 1 d . . . . .
O3 O 0.6224(3) 0.23159(18) 0.24734(15) 0.0397(7) Uani 1 1 d . . . . .
C10 C 0.9168(5) 0.0817(2) 0.6227(2) 0.0291(7) Uani 1 1 d D U . . .
C22 C 1.1658(5) 0.2787(2) 0.6586(2) 0.0310(8) Uani 1 1 d . . . . .
H22A H 1.2818 0.2550 0.6839 0.037 Uiso 1 1 calc R U . . .
H22B H 1.1137 0.3062 0.7015 0.037 Uiso 1 1 calc R U . . .
C14 C 1.0114(4) 0.1490(2) 0.6655(2) 0.0277(8) Uani 1 1 d . . . . .
O5 O 0.7778(4) -0.12693(19) 0.66486(18) 0.0527(8) Uani 1 1 d . . . . .
C1 C 0.6318(5) -0.1295(2) 0.4979(3) 0.0374(9) Uani 1 1 d . . . . .
H1 H 0.6187 -0.1769 0.5289 0.045 Uiso 1 1 calc R U . . .
C13 C 1.0646(5) 0.1457(2) 0.7512(2) 0.0300(8) Uani 1 1 d . . . . .
H13 H 1.1244 0.1908 0.7796 0.036 Uiso 1 1 calc R U . . .
C20 C 0.8867(5) 0.3575(2) 0.5170(2) 0.0313(8) Uani 1 1 d . . . . .
H20A H 0.8300 0.3168 0.5478 0.038 Uiso 1 1 calc R U . . .
H20B H 0.9234 0.3298 0.4701 0.038 Uiso 1 1 calc R U . . .
C4 C 0.6778(5) 0.0108(2) 0.4036(2) 0.0319(9) Uani 1 1 d . . . . .
C12 C 1.0291(5) 0.0757(2) 0.7944(2) 0.0321(9) Uani 1 1 d . . . . .
H12 H 1.0645 0.0743 0.8519 0.039 Uiso 1 1 calc R U . . .
C6 C 0.7261(5) -0.0606(2) 0.5350(2) 0.0320(8) Uani 1 1 d . . . . .
C5 C 0.7513(4) 0.0106(2) 0.4897(2) 0.0299(7) Uani 1 1 d D U . . .
C15 C 0.6403(5) 0.0801(3) 0.2714(2) 0.0396(10) Uani 1 1 d . . . . .
H15A H 0.5087 0.0816 0.2603 0.048 Uiso 1 1 calc R U . . .
H15B H 0.6794 0.0307 0.2455 0.048 Uiso 1 1 calc R U . . .
C18 C 0.5724(5) 0.3462(3) 0.3298(2) 0.0377(9) Uani 1 1 d . . . . .
H18A H 0.4654 0.3526 0.2869 0.045 Uiso 1 1 calc R U . . .
H18B H 0.6678 0.3801 0.3141 0.045 Uiso 1 1 calc R U . . .
C9 C 0.8867(4) 0.0109(2) 0.6679(2) 0.0289(8) Uani 1 1 d . . . . .
C3 C 0.5800(5) -0.0571(3) 0.3686(2) 0.0395(10) Uani 1 1 d . . . . .
H3 H 0.5277 -0.0558 0.3125 0.047 Uiso 1 1 calc R U . . .
C11 C 0.9424(5) 0.0082(2) 0.7540(2) 0.0333(9) Uani 1 1 d . . . . .
H11 H 0.9209 -0.0390 0.7836 0.040 Uiso 1 1 calc R U . . .
C21 C 1.1903(5) 0.3396(2) 0.5923(2) 0.0341(9) Uani 1 1 d . . . . .
H21A H 1.2982 0.3725 0.6118 0.041 Uiso 1 1 calc R U . . .
H21B H 1.2097 0.3090 0.5436 0.041 Uiso 1 1 calc R U . . .
C16 C 0.7147(5) 0.1564(3) 0.2377(2) 0.0437(11) Uani 1 1 d . . . . .
H16A H 0.8404 0.1627 0.2647 0.052 Uiso 1 1 calc R U . . .
H16B H 0.7133 0.1479 0.1789 0.052 Uiso 1 1 calc R U . . .
C2 C 0.5584(5) -0.1263(3) 0.4145(3) 0.0429(11) Uani 1 1 d . . . . .
H2 H 0.4935 -0.1717 0.3891 0.051 Uiso 1 1 calc R U . . .
C17 C 0.6307(5) 0.2569(2) 0.3321(2) 0.0355(9) Uani 1 1 d . . . . .
H17A H 0.7533 0.2512 0.3631 0.043 Uiso 1 1 calc R U . . .
H17B H 0.5504 0.2229 0.3584 0.043 Uiso 1 1 calc R U . . .
C19 C 0.7571(5) 0.4269(2) 0.4876(2) 0.0366(9) Uani 1 1 d . . . . .
H19A H 0.8081 0.4613 0.4489 0.044 Uiso 1 1 calc R U . . .
H19B H 0.7441 0.4614 0.5348 0.044 Uiso 1 1 calc R U . . .
C8 C 0.8288(11) 0.0892(4) 0.5328(4) 0.0316(8) Uani 0.5285 1 d D U P A 1
O6 O 0.8165(8) 0.1580(4) 0.4988(4) 0.0411(14) Uani 0.5285 1 d . U P A 1
O6' O 0.8945(9) 0.1396(4) 0.4885(5) 0.0414(15) Uani 0.4715 1 d D U P A 2
C7 C 0.7958(5) -0.0636(3) 0.6259(2) 0.0366(9) Uani 1 1 d . . . . .
C8' C 0.8605(13) 0.0822(5) 0.5302(4) 0.0316(8) Uani 0.4715 1 d D 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
Se1 C18 1.944(4) . ?
Se1 C19 1.946(4) . ?
O1 C4 1.348(5) . ?
O1 C15 1.434(4) . ?
O2 C14 1.351(4) . ?
O2 C22 1.427(4) . ?
O4 C21 1.420(4) . ?
O4 C20 1.430(4) . ?
O3 C16 1.414(5) . ?
O3 C17 1.437(4) . ?
C10 C9 1.397(5) . ?
C10 C14 1.407(5) . ?
C10 C8' 1.496(6) . ?
C10 C8 1.503(6) . ?
C22 C21 1.497(5) . ?
C22 H22A 0.9700 . ?
C22 H22B 0.9700 . ?
C14 C13 1.388(5) . ?
O5 C7 1.221(5) . ?
C1 C2 1.377(6) . ?
C1 C6 1.391(5) . ?
C1 H1 0.9300 . ?
C13 C12 1.380(5) . ?
C13 H13 0.9300 . ?
C20 C19 1.499(5) . ?
C20 H20A 0.9700 . ?
C20 H20B 0.9700 . ?
C4 C3 1.379(5) . ?
C4 C5 1.416(5) . ?
C12 C11 1.370(5) . ?
C12 H12 0.9300 . ?
C6 C5 1.394(5) . ?
C6 C7 1.486(5) . ?
C5 C8' 1.495(6) . ?
C5 C8 1.509(6) . ?
C15 C16 1.494(6) . ?
C15 H15A 0.9700 . ?
C15 H15B 0.9700 . ?
C18 C17 1.497(5) . ?
C18 H18A 0.9700 . ?
C18 H18B 0.9700 . ?
C9 C11 1.396(5) . ?
C9 C7 1.482(5) . ?
C3 C2 1.368(6) . ?
C3 H3 0.9300 . ?
C11 H11 0.9300 . ?
C21 H21A 0.9700 . ?
C21 H21B 0.9700 . ?
C16 H16A 0.9700 . ?
C16 H16B 0.9700 . ?
C2 H2 0.9300 . ?
C17 H17A 0.9700 . ?
C17 H17B 0.9700 . ?
C19 H19A 0.9700 . ?
C19 H19B 0.9700 . ?
C8 O6 1.233(9) . ?
O6' C8' 1.202(7) . ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
C18 Se1 C19 100.63(16) . . ?
C4 O1 C15 119.5(3) . . ?
C14 O2 C22 119.2(3) . . ?
C21 O4 C20 114.7(3) . . ?
C16 O3 C17 114.5(3) . . ?
C9 C10 C14 118.4(3) . . ?
C9 C10 C8' 119.9(4) . . ?
C14 C10 C8' 121.6(4) . . ?
C9 C10 C8 120.0(4) . . ?
C14 C10 C8 121.2(4) . . ?
O2 C22 C21 107.2(3) . . ?
O2 C22 H22A 110.3 . . ?
C21 C22 H22A 110.3 . . ?
O2 C22 H22B 110.3 . . ?
C21 C22 H22B 110.3 . . ?
H22A C22 H22B 108.5 . . ?
O2 C14 C13 122.7(3) . . ?
O2 C14 C10 117.3(3) . . ?
C13 C14 C10 120.0(3) . . ?
C2 C1 C6 118.9(4) . . ?
C2 C1 H1 120.6 . . ?
C6 C1 H1 120.6 . . ?
C12 C13 C14 120.2(4) . . ?
C12 C13 H13 119.9 . . ?
C14 C13 H13 119.9 . . ?
O4 C20 C19 106.8(3) . . ?
O4 C20 H20A 110.4 . . ?
C19 C20 H20A 110.4 . . ?
O4 C20 H20B 110.4 . . ?
C19 C20 H20B 110.4 . . ?
H20A C20 H20B 108.6 . . ?
O1 C4 C3 122.7(3) . . ?
O1 C4 C5 117.8(3) . . ?
C3 C4 C5 119.5(4) . . ?
C11 C12 C13 121.0(3) . . ?
C11 C12 H12 119.5 . . ?
C13 C12 H12 119.5 . . ?
C1 C6 C5 121.8(3) . . ?
C1 C6 C7 118.0(4) . . ?
C5 C6 C7 120.2(3) . . ?
C6 C5 C4 117.7(3) . . ?
C6 C5 C8' 120.8(4) . . ?
C4 C5 C8' 121.4(4) . . ?
C6 C5 C8 121.0(4) . . ?
C4 C5 C8 120.6(4) . . ?
O1 C15 C16 107.4(3) . . ?
O1 C15 H15A 110.2 . . ?
C16 C15 H15A 110.2 . . ?
O1 C15 H15B 110.2 . . ?
C16 C15 H15B 110.2 . . ?
H15A C15 H15B 108.5 . . ?
C17 C18 Se1 114.9(2) . . ?
C17 C18 H18A 108.6 . . ?
Se1 C18 H18A 108.6 . . ?
C17 C18 H18B 108.6 . . ?
Se1 C18 H18B 108.6 . . ?
H18A C18 H18B 107.5 . . ?
C11 C9 C10 120.8(3) . . ?
C11 C9 C7 118.0(3) . . ?
C10 C9 C7 121.1(3) . . ?
C2 C3 C4 121.5(4) . . ?
C2 C3 H3 119.3 . . ?
C4 C3 H3 119.3 . . ?
C12 C11 C9 119.5(3) . . ?
C12 C11 H11 120.3 . . ?
C9 C11 H11 120.3 . . ?
O4 C21 C22 113.6(3) . . ?
O4 C21 H21A 108.9 . . ?
C22 C21 H21A 108.9 . . ?
O4 C21 H21B 108.9 . . ?
C22 C21 H21B 108.9 . . ?
H21A C21 H21B 107.7 . . ?
O3 C16 C15 115.8(3) . . ?
O3 C16 H16A 108.3 . . ?
C15 C16 H16A 108.3 . . ?
O3 C16 H16B 108.3 . . ?
C15 C16 H16B 108.3 . . ?
H16A C16 H16B 107.4 . . ?
C3 C2 C1 120.6(4) . . ?
C3 C2 H2 119.7 . . ?
C1 C2 H2 119.7 . . ?
O3 C17 C18 106.6(3) . . ?
O3 C17 H17A 110.4 . . ?
C18 C17 H17A 110.4 . . ?
O3 C17 H17B 110.4 . . ?
C18 C17 H17B 110.4 . . ?
H17A C17 H17B 108.6 . . ?
C20 C19 Se1 113.5(3) . . ?
C20 C19 H19A 108.9 . . ?
Se1 C19 H19A 108.9 . . ?
C20 C19 H19B 108.9 . . ?
Se1 C19 H19B 108.9 . . ?
H19A C19 H19B 107.7 . . ?
O6 C8 C10 119.7(5) . . ?
O6 C8 C5 123.3(5) . . ?
C10 C8 C5 116.9(5) . . ?
O5 C7 C9 121.0(3) . . ?
O5 C7 C6 119.9(4) . . ?
C9 C7 C6 119.0(3) . . ?
O6' C8' C5 119.6(6) . . ?
O6' C8' C10 122.0(6) . . ?
C5 C8' C10 118.4(5) . . ?

loop_
_geom_torsion_atom_site_label_1
_geom_torsion_atom_site_label_2
_geom_torsion_atom_site_label_3
_geom_torsion_atom_site_label_4
_geom_torsion
_geom_torsion_site_symmetry_1
_geom_torsion_site_symmetry_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
_geom_torsion_publ_flag
C14 O2 C22 C21 175.9(3) . . . . ?
C22 O2 C14 C13 9.3(5) . . . . ?
C22 O2 C14 C10 -170.5(3) . . . . ?
C9 C10 C14 O2 176.6(3) . . . . ?
C8' C10 C14 O2 1.1(7) . . . . ?
C8 C10 C14 O2 -11.1(6) . . . . ?
C9 C10 C14 C13 -3.2(5) . . . . ?
C8' C10 C14 C13 -178.7(6) . . . . ?
C8 C10 C14 C13 169.0(5) . . . . ?
O2 C14 C13 C12 -178.2(3) . . . . ?
C10 C14 C13 C12 1.6(5) . . . . ?
C21 O4 C20 C19 -170.5(3) . . . . ?
C15 O1 C4 C3 -2.0(5) . . . . ?
C15 O1 C4 C5 178.0(3) . . . . ?
C14 C13 C12 C11 0.5(5) . . . . ?
C2 C1 C6 C5 -1.4(5) . . . . ?
C2 C1 C6 C7 176.8(3) . . . . ?
C1 C6 C5 C4 -0.2(5) . . . . ?
C7 C6 C5 C4 -178.4(3) . . . . ?
C1 C6 C5 C8' -177.1(6) . . . . ?
C7 C6 C5 C8' 4.7(7) . . . . ?
C1 C6 C5 C8 170.8(5) . . . . ?
C7 C6 C5 C8 -7.4(6) . . . . ?
O1 C4 C5 C6 -177.8(3) . . . . ?
C3 C4 C5 C6 2.2(5) . . . . ?
O1 C4 C5 C8' -0.9(7) . . . . ?
C3 C4 C5 C8' 179.1(6) . . . . ?
O1 C4 C5 C8 11.2(6) . . . . ?
C3 C4 C5 C8 -168.8(5) . . . . ?
C4 O1 C15 C16 -172.3(3) . . . . ?
C14 C10 C9 C11 2.7(5) . . . . ?
C8' C10 C9 C11 178.3(5) . . . . ?
C8 C10 C9 C11 -169.6(5) . . . . ?
C14 C10 C9 C7 -177.0(3) . . . . ?
C8' C10 C9 C7 -1.4(7) . . . . ?
C8 C10 C9 C7 10.7(6) . . . . ?
O1 C4 C3 C2 177.3(3) . . . . ?
C5 C4 C3 C2 -2.7(5) . . . . ?
C13 C12 C11 C9 -1.0(5) . . . . ?
C10 C9 C11 C12 -0.6(5) . . . . ?
C7 C9 C11 C12 179.1(3) . . . . ?
C20 O4 C21 C22 -76.5(4) . . . . ?
O2 C22 C21 O4 77.2(4) . . . . ?
C17 O3 C16 C15 64.6(4) . . . . ?
O1 C15 C16 O3 -80.7(4) . . . . ?
C4 C3 C2 C1 1.1(6) . . . . ?
C6 C1 C2 C3 1.0(5) . . . . ?
C16 O3 C17 C18 164.9(3) . . . . ?
Se1 C18 C17 O3 166.6(2) . . . . ?
O4 C20 C19 Se1 -168.4(2) . . . . ?
C9 C10 C8 O6 161.8(7) . . . . ?
C14 C10 C8 O6 -10.3(10) . . . . ?
C9 C10 C8 C5 -15.4(9) . . . . ?
C14 C10 C8 C5 172.5(5) . . . . ?
C6 C5 C8 O6 -163.2(7) . . . . ?
C4 C5 C8 O6 7.5(11) . . . . ?
C6 C5 C8 C10 13.9(9) . . . . ?
C4 C5 C8 C10 -175.4(5) . . . . ?
C11 C9 C7 O5 -3.4(5) . . . . ?
C10 C9 C7 O5 176.3(4) . . . . ?
C11 C9 C7 C6 176.6(3) . . . . ?
C10 C9 C7 C6 -3.7(5) . . . . ?
C1 C6 C7 O5 3.8(5) . . . . ?
C5 C6 C7 O5 -178.0(3) . . . . ?
C1 C6 C7 C9 -176.3(3) . . . . ?
C5 C6 C7 C9 2.0(5) . . . . ?
C6 C5 C8' O6' 173.2(7) . . . . ?
C4 C5 C8' O6' -3.6(12) . . . . ?
C6 C5 C8' C10 -9.7(10) . . . . ?
C4 C5 C8' C10 173.5(5) . . . . ?
C9 C10 C8' O6' -175.0(8) . . . . ?
C14 C10 C8' O6' 0.5(12) . . . . ?
C9 C10 C8' C5 7.9(10) . . . . ?
C14 C10 C8' C5 -176.6(5) . . . . ?

_refine_diff_density_max         0.925
_refine_diff_density_min         -0.426
_refine_diff_density_rms         0.075

_shelxl_version_number           2014/6

####################################################################### 
# 
# 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_13066
_database_code_depnum_ccdc_archive 'CCDC 980452'
_audit_update_record             
;
2014-01-07 deposited with the CCDC.
2015-05-27 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-97
_chemical_name_systematic        
;
 CE-Se
;
_chemical_name_common            CE-Se
_chemical_melting_point          ?
_chemical_formula_moiety         'C22 H24 O5 Se'
_chemical_formula_sum            'C22 H24 O5 Se'
_chemical_formula_weight         447.37

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'

_symmetry_cell_setting           Monoclinic
_symmetry_space_group_name_H-M   'P 21/n'
_symmetry_space_group_name_Hall  '-P 2yn'
loop_
_symmetry_equiv_pos_as_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                   14.6414(8)
_cell_length_b                   8.0187(4)
_cell_length_c                   16.9048(9)
_cell_angle_alpha                90.00
_cell_angle_beta                 104.1850(10)
_cell_angle_gamma                90.00
_cell_volume                     1924.19(18)
_cell_formula_units_Z            4
_cell_measurement_temperature    100(2)
_cell_measurement_reflns_used    9921
_cell_measurement_theta_min      2.49
_cell_measurement_theta_max      25.38

_exptl_crystal_description       needle
_exptl_crystal_colour            'pale yellow'
_exptl_crystal_size_max          0.6
_exptl_crystal_size_mid          0.55
_exptl_crystal_size_min          0.30
_exptl_crystal_density_meas      1.544
_exptl_crystal_density_diffrn    1.544
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             920
_exptl_absorpt_coefficient_mu    1.983
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.3374
_exptl_absorpt_correction_T_max  0.5876
_exptl_absorpt_process_details   SADABS

_exptl_special_details           
;
 ?
;

_diffrn_ambient_temperature      100(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_radiation_source         'fine-focus sealed tube'
_diffrn_radiation_monochromator  graphite
_diffrn_measurement_device_type  'CCD area detector'
_diffrn_measurement_method       'phi and omega scans'
_diffrn_detector_area_resol_mean ?
_diffrn_standards_number         ?
_diffrn_standards_interval_count ?
_diffrn_standards_interval_time  ?
_diffrn_standards_decay_%        ?
_diffrn_reflns_number            18815
_diffrn_reflns_av_R_equivalents  0.0331
_diffrn_reflns_av_sigmaI/netI    0.0235
_diffrn_reflns_limit_h_min       -17
_diffrn_reflns_limit_h_max       17
_diffrn_reflns_limit_k_min       -9
_diffrn_reflns_limit_k_max       9
_diffrn_reflns_limit_l_min       -20
_diffrn_reflns_limit_l_max       20
_diffrn_reflns_theta_min         1.65
_diffrn_reflns_theta_max         25.38
_reflns_number_total             3538
_reflns_number_gt                3107
_reflns_threshold_expression     >2sigma(I)

_computing_data_collection       'Bruker SMART'
_computing_cell_refinement       'Bruker SMART'
_computing_data_reduction        'Bruker SAINT'
_computing_structure_solution    'Bruker SHELXTL'
_computing_structure_refinement  'Bruker SHELXTL'
_computing_molecular_graphics    'Bruker SHELXTL'
_computing_publication_material  'Bruker SHELXTL'



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

_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'calc w=1/[σ²(Fo²)+(0.0248P)²+1.3315P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_atom_sites_solution_hydrogens   geom
_refine_ls_hydrogen_treatment    constr
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       ?
_refine_ls_number_reflns         3538
_refine_ls_number_parameters     253
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0297
_refine_ls_R_factor_gt           0.0237
_refine_ls_wR_factor_ref         0.0594
_refine_ls_wR_factor_gt          0.0566
_refine_ls_goodness_of_fit_ref   1.056
_refine_ls_restrained_S_all      1.056
_refine_ls_shift/su_max          0.001
_refine_ls_shift/su_mean         0.000

loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_symmetry_multiplicity
_atom_site_calc_flag
_atom_site_refinement_flags
_atom_site_disorder_assembly
_atom_site_disorder_group
Se1 Se 0.453503(13) 0.48767(2) 0.346837(11) 0.01685(7) Uani 1 1 d . . .
O2 O 0.58946(9) -0.00497(16) 0.25047(8) 0.0171(3) Uani 1 1 d . . .
O4 O 0.52517(9) 0.10098(16) 0.38795(8) 0.0179(3) Uani 1 1 d . . .
O3 O 0.23184(9) 0.37279(17) 0.15222(8) 0.0190(3) Uani 1 1 d . . .
O1 O 0.36813(9) 0.28445(16) 0.04355(7) 0.0163(3) Uani 1 1 d . . .
C11 C 0.78419(14) -0.0140(2) 0.10972(12) 0.0190(4) Uani 1 1 d . . .
H11 H 0.8276 -0.0118 0.0777 0.023 Uiso 1 1 calc R . .
C5 C 0.51609(13) 0.2271(2) 0.02241(11) 0.0137(4) Uani 1 1 d . . .
C14 C 0.65657(13) -0.0145(2) 0.20707(11) 0.0151(4) Uani 1 1 d . . .
C12 C 0.80490(13) -0.0988(2) 0.18264(12) 0.0204(4) Uani 1 1 d . . .
H12 H 0.8617 -0.1557 0.1992 0.024 Uiso 1 1 calc R . .
C8 C 0.53893(13) 0.1533(2) 0.10643(11) 0.0142(4) Uani 1 1 d . . .
H8A H 0.5365 0.2412 0.1453 0.017 Uiso 1 1 calc R . .
H8B H 0.4905 0.0726 0.1094 0.017 Uiso 1 1 calc R . .
C6 C 0.57999(13) 0.2292(2) -0.02646(11) 0.0156(4) Uani 1 1 d . . .
C7 C 0.67493(13) 0.1538(2) 0.00267(12) 0.0181(4) Uani 1 1 d . . .
C17 C 0.32445(13) 0.3612(2) 0.20415(11) 0.0161(4) Uani 1 1 d . . .
H17A H 0.3704 0.4043 0.1766 0.019 Uiso 1 1 calc R . .
H17B H 0.3399 0.2459 0.2190 0.019 Uiso 1 1 calc R . .
C10 C 0.63291(13) 0.0694(2) 0.13178(11) 0.0138(4) Uani 1 1 d . . .
C15 C 0.27446(12) 0.3522(2) 0.01955(11) 0.0165(4) Uani 1 1 d . . .
H15A H 0.2446 0.3198 -0.0361 0.020 Uiso 1 1 calc R . .
H15B H 0.2767 0.4730 0.0224 0.020 Uiso 1 1 calc R . .
C4 C 0.42654(13) 0.2987(2) -0.00800(11) 0.0144(4) Uani 1 1 d . . .
C3 C 0.40319(13) 0.3728(2) -0.08418(11) 0.0166(4) Uani 1 1 d . . .
H3 H 0.3444 0.4220 -0.1033 0.020 Uiso 1 1 calc R . .
C13 C 0.74114(14) -0.1000(2) 0.23200(11) 0.0181(4) Uani 1 1 d . . .
H13 H 0.7553 -0.1578 0.2812 0.022 Uiso 1 1 calc R . .
C22 C 0.60393(14) -0.0976(2) 0.32493(11) 0.0181(4) Uani 1 1 d . . .
H22A H 0.6612 -0.0614 0.3632 0.022 Uiso 1 1 calc R . .
H22B H 0.6093 -0.2157 0.3145 0.022 Uiso 1 1 calc R . .
C16 C 0.21937(13) 0.2846(2) 0.07717(11) 0.0169(4) Uani 1 1 d . . .
H16A H 0.1530 0.2859 0.0496 0.020 Uiso 1 1 calc R . .
H16B H 0.2374 0.1692 0.0892 0.020 Uiso 1 1 calc R . .
C1 C 0.55548(14) 0.3016(2) -0.10438(11) 0.0178(4) Uani 1 1 d . . .
H1 H 0.5981 0.3011 -0.1371 0.021 Uiso 1 1 calc R . .
C21 C 0.52028(14) -0.0655(2) 0.35897(12) 0.0188(4) Uani 1 1 d . . .
H21A H 0.4626 -0.0819 0.3169 0.023 Uiso 1 1 calc R . .
H21B H 0.5203 -0.1424 0.4033 0.023 Uiso 1 1 calc R . .
C9 C 0.69758(13) 0.0693(2) 0.08350(11) 0.0157(4) Uani 1 1 d . . .
C2 C 0.46819(14) 0.3733(2) -0.13225(11) 0.0180(4) Uani 1 1 d . . .
H2 H 0.4523 0.4225 -0.1836 0.022 Uiso 1 1 calc R . .
C20 C 0.44013(13) 0.1497(2) 0.40791(11) 0.0176(4) Uani 1 1 d . . .
H19A H 0.4296 0.0809 0.4520 0.021 Uiso 1 1 calc R . .
H19B H 0.3874 0.1347 0.3610 0.021 Uiso 1 1 calc R . .
C18 C 0.32512(13) 0.4633(2) 0.27905(12) 0.0185(4) Uani 1 1 d . . .
H18A H 0.2862 0.4094 0.3104 0.022 Uiso 1 1 calc R . .
H18B H 0.2988 0.5726 0.2628 0.022 Uiso 1 1 calc R . .
O5 O 0.73279(10) 0.1604(2) -0.03868(9) 0.0295(4) Uani 1 1 d . . .
C19 C 0.44758(13) 0.3301(2) 0.43339(11) 0.0170(4) Uani 1 1 d . . .
H99A H 0.5036 0.3439 0.4775 0.020 Uiso 1 1 calc R . .
H99B H 0.3936 0.3579 0.4546 0.020 Uiso 1 1 calc R . .


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

loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
Se1 C19 1.9511(19) . ?
Se1 C18 1.9567(19) . ?
O2 C14 1.365(2) . ?
O2 C22 1.432(2) . ?
O4 C21 1.418(2) . ?
O4 C20 1.422(2) . ?
O3 C16 1.425(2) . ?
O3 C17 1.426(2) . ?
O1 C4 1.367(2) . ?
O1 C15 1.438(2) . ?
C11 C12 1.375(3) . ?
C11 C9 1.406(3) . ?
C11 H11 0.9300 . ?
C5 C6 1.392(3) . ?
C5 C4 1.408(3) . ?
C5 C8 1.499(2) . ?
C14 C13 1.388(3) . ?
C14 C10 1.406(3) . ?
C12 C13 1.396(3) . ?
C12 H12 0.9300 . ?
C8 C10 1.497(3) . ?
C8 H8A 0.9700 . ?
C8 H8B 0.9700 . ?
C6 C1 1.403(3) . ?
C6 C7 1.485(3) . ?
C7 O5 1.224(2) . ?
C7 C9 1.488(3) . ?
C17 C18 1.506(3) . ?
C17 H17A 0.9700 . ?
C17 H17B 0.9700 . ?
C10 C9 1.393(3) . ?
C15 C16 1.509(3) . ?
C15 H15A 0.9700 . ?
C15 H15B 0.9700 . ?
C4 C3 1.383(3) . ?
C3 C2 1.395(3) . ?
C3 H3 0.9300 . ?
C13 H13 0.9300 . ?
C22 C21 1.498(3) . ?
C22 H22A 0.9700 . ?
C22 H22B 0.9700 . ?
C16 H16A 0.9700 . ?
C16 H16B 0.9700 . ?
C1 C2 1.375(3) . ?
C1 H1 0.9300 . ?
C21 H21A 0.9700 . ?
C21 H21B 0.9700 . ?
C2 H2 0.9300 . ?
C20 C19 1.506(3) . ?
C20 H19A 0.9700 . ?
C20 H19B 0.9700 . ?
C18 H18A 0.9700 . ?
C18 H18B 0.9700 . ?
C19 H99A 0.9700 . ?
C19 H99B 0.9700 . ?

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
C19 Se1 C18 99.30(8) . . ?
C14 O2 C22 118.19(14) . . ?
C21 O4 C20 111.56(14) . . ?
C16 O3 C17 114.26(14) . . ?
C4 O1 C15 119.40(14) . . ?
C12 C11 C9 120.09(18) . . ?
C12 C11 H11 120.0 . . ?
C9 C11 H11 120.0 . . ?
C6 C5 C4 118.66(17) . . ?
C6 C5 C8 122.75(17) . . ?
C4 C5 C8 118.59(16) . . ?
O2 C14 C13 124.82(17) . . ?
O2 C14 C10 114.18(16) . . ?
C13 C14 C10 121.00(18) . . ?
C11 C12 C13 120.44(18) . . ?
C11 C12 H12 119.8 . . ?
C13 C12 H12 119.8 . . ?
C10 C8 C5 115.13(15) . . ?
C10 C8 H8A 108.5 . . ?
C5 C8 H8A 108.5 . . ?
C10 C8 H8B 108.5 . . ?
C5 C8 H8B 108.5 . . ?
H8A C8 H8B 107.5 . . ?
C5 C6 C1 120.51(17) . . ?
C5 C6 C7 120.60(17) . . ?
C1 C6 C7 118.88(17) . . ?
O5 C7 C6 121.04(18) . . ?
O5 C7 C9 120.94(18) . . ?
C6 C7 C9 118.02(16) . . ?
O3 C17 C18 106.95(15) . . ?
O3 C17 H17A 110.3 . . ?
C18 C17 H17A 110.3 . . ?
O3 C17 H17B 110.3 . . ?
C18 C17 H17B 110.3 . . ?
H17A C17 H17B 108.6 . . ?
C9 C10 C14 118.56(17) . . ?
C9 C10 C8 122.79(16) . . ?
C14 C10 C8 118.65(16) . . ?
O1 C15 C16 107.81(15) . . ?
O1 C15 H15A 110.1 . . ?
C16 C15 H15A 110.1 . . ?
O1 C15 H15B 110.1 . . ?
C16 C15 H15B 110.1 . . ?
H15A C15 H15B 108.5 . . ?
O1 C4 C3 125.39(17) . . ?
O1 C4 C5 113.89(16) . . ?
C3 C4 C5 120.71(17) . . ?
C4 C3 C2 119.71(18) . . ?
C4 C3 H3 120.1 . . ?
C2 C3 H3 120.1 . . ?
C14 C13 C12 119.51(18) . . ?
C14 C13 H13 120.2 . . ?
C12 C13 H13 120.2 . . ?
O2 C22 C21 106.84(15) . . ?
O2 C22 H22A 110.4 . . ?
C21 C22 H22A 110.4 . . ?
O2 C22 H22B 110.4 . . ?
C21 C22 H22B 110.4 . . ?
H22A C22 H22B 108.6 . . ?
O3 C16 C15 115.09(15) . . ?
O3 C16 H16A 108.5 . . ?
C15 C16 H16A 108.5 . . ?
O3 C16 H16B 108.5 . . ?
C15 C16 H16B 108.5 . . ?
H16A C16 H16B 107.5 . . ?
C2 C1 C6 119.79(18) . . ?
C2 C1 H1 120.1 . . ?
C6 C1 H1 120.1 . . ?
O4 C21 C22 108.54(15) . . ?
O4 C21 H21A 110.0 . . ?
C22 C21 H21A 110.0 . . ?
O4 C21 H21B 110.0 . . ?
C22 C21 H21B 110.0 . . ?
H21A C21 H21B 108.4 . . ?
C10 C9 C11 120.37(17) . . ?
C10 C9 C7 120.48(17) . . ?
C11 C9 C7 119.13(17) . . ?
C1 C2 C3 120.59(18) . . ?
C1 C2 H2 119.7 . . ?
C3 C2 H2 119.7 . . ?
O4 C20 C19 108.99(15) . . ?
O4 C20 H19A 109.9 . . ?
C19 C20 H19A 109.9 . . ?
O4 C20 H19B 109.9 . . ?
C19 C20 H19B 109.9 . . ?
H19A C20 H19B 108.3 . . ?
C17 C18 Se1 110.74(12) . . ?
C17 C18 H18A 109.5 . . ?
Se1 C18 H18A 109.5 . . ?
C17 C18 H18B 109.5 . . ?
Se1 C18 H18B 109.5 . . ?
H18A C18 H18B 108.1 . . ?
C20 C19 Se1 114.91(12) . . ?
C20 C19 H99A 108.5 . . ?
Se1 C19 H99A 108.5 . . ?
C20 C19 H99B 108.5 . . ?
Se1 C19 H99B 108.5 . . ?
H99A C19 H99B 107.5 . . ?

_diffrn_measured_fraction_theta_max 0.998
_diffrn_reflns_theta_full        25.38
_diffrn_measured_fraction_theta_full 0.998
_refine_diff_density_max         0.459
_refine_diff_density_min         -0.307
_refine_diff_density_rms         0.054
####################################################################### 
# 
# 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_13067
_database_code_depnum_ccdc_archive 'CCDC 980453'
_audit_update_record             
;
2015-05-06 deposited with the CCDC.
2015-05-27 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-97
_chemical_name_systematic        
;
 ?
;
_chemical_name_common            CESE-anthone
_chemical_melting_point          ?
_chemical_formula_moiety         'C22 H24 O6 Se'
_chemical_formula_sum            'C22 H24 O6 Se'
_chemical_formula_weight         463.37

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'

_symmetry_cell_setting           Monoclinic
_symmetry_space_group_name_H-M   P21/c
_symmetry_space_group_name_Hall  '-P 2ybc'
loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'-x, y+1/2, -z+1/2'
'-x, -y, -z'
'x, -y-1/2, z-1/2'

_cell_length_a                   12.3365(8)
_cell_length_b                   11.5354(8)
_cell_length_c                   14.4592(9)
_cell_angle_alpha                90.00
_cell_angle_beta                 99.2400(10)
_cell_angle_gamma                90.00
_cell_volume                     2030.9(2)
_cell_formula_units_Z            4
_cell_measurement_temperature    100(2)
_cell_measurement_reflns_used    9901
_cell_measurement_theta_min      2.43
_cell_measurement_theta_max      25.39

_exptl_crystal_description       needle
_exptl_crystal_colour            colorless
_exptl_crystal_size_max          0.60
_exptl_crystal_size_mid          0.55
_exptl_crystal_size_min          0.50
_exptl_crystal_density_meas      ?
_exptl_crystal_density_diffrn    1.515
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             952
_exptl_absorpt_coefficient_mu    1.885
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.3975
_exptl_absorpt_correction_T_max  0.4524
_exptl_absorpt_process_details   SADABS

_exptl_special_details           
;
 ?
;

_diffrn_ambient_temperature      100(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_radiation_source         'fine-focus sealed tube'
_diffrn_radiation_monochromator  graphite
_diffrn_measurement_device_type  'CCD area detector'
_diffrn_measurement_method       'phi and omega scans'
_diffrn_detector_area_resol_mean ?
_diffrn_standards_number         ?
_diffrn_standards_interval_count ?
_diffrn_standards_interval_time  ?
_diffrn_standards_decay_%        ?
_diffrn_reflns_number            19801
_diffrn_reflns_av_R_equivalents  0.0266
_diffrn_reflns_av_sigmaI/netI    0.0189
_diffrn_reflns_limit_h_min       -14
_diffrn_reflns_limit_h_max       14
_diffrn_reflns_limit_k_min       -13
_diffrn_reflns_limit_k_max       13
_diffrn_reflns_limit_l_min       -17
_diffrn_reflns_limit_l_max       17
_diffrn_reflns_theta_min         1.67
_diffrn_reflns_theta_max         25.39
_reflns_number_total             3738
_reflns_number_gt                3339
_reflns_threshold_expression     >2sigma(I)

_computing_data_collection       'Bruker SMART'
_computing_cell_refinement       'Bruker SMART'
_computing_data_reduction        'Bruker SAINT'
_computing_structure_solution    'Bruker SHELXTL'
_computing_structure_refinement  'Bruker SHELXTL'
_computing_molecular_graphics    'Bruker SHELXTL'
_computing_publication_material  'Bruker SHELXTL'


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

_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'calc w=1/[σ²(Fo²)+(0.0317P)²+1.3900P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_atom_sites_solution_hydrogens   geom
_refine_ls_hydrogen_treatment    constr
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       ?
_refine_ls_number_reflns         3738
_refine_ls_number_parameters     262
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0293
_refine_ls_R_factor_gt           0.0242
_refine_ls_wR_factor_ref         0.0647
_refine_ls_wR_factor_gt          0.0618
_refine_ls_goodness_of_fit_ref   1.045
_refine_ls_restrained_S_all      1.045
_refine_ls_shift/su_max          0.001
_refine_ls_shift/su_mean         0.000

loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_symmetry_multiplicity
_atom_site_calc_flag
_atom_site_refinement_flags
_atom_site_disorder_assembly
_atom_site_disorder_group
Se1 Se 0.586136(16) 0.232017(17) -0.186202(14) 0.02445(8) Uani 1 1 d . . .
O2 O 0.86892(10) 0.18749(11) 0.05801(9) 0.0195(3) Uani 1 1 d . . .
O4 O 0.64963(11) 0.11559(11) 0.02040(9) 0.0224(3) Uani 1 1 d . . .
O6 O 0.86859(11) 0.27805(11) -0.13403(9) 0.0213(3) Uani 1 1 d . . .
H6 H 0.8335 0.2300 -0.1093 0.032 Uiso 1 1 calc R . .
O1 O 0.85050(11) 0.53018(11) -0.13379(9) 0.0234(3) Uani 1 1 d . . .
O3 O 0.62330(11) 0.50680(12) -0.19124(9) 0.0252(3) Uani 1 1 d . . .
O5 O 1.27213(13) 0.27728(13) -0.10458(12) 0.0362(4) Uani 1 1 d . . .
C8 C 0.94887(15) 0.33213(15) -0.06338(12) 0.0175(4) Uani 1 1 d . . .
H8 H 0.9101 0.3728 -0.0189 0.021 Uiso 1 1 calc R . .
C9 C 1.12903(16) 0.22102(15) -0.02418(13) 0.0194(4) Uani 1 1 d . . .
C5 C 1.01109(15) 0.41994(15) -0.11132(12) 0.0184(4) Uani 1 1 d . . .
C10 C 1.02030(15) 0.23946(15) -0.01120(12) 0.0174(4) Uani 1 1 d . . .
C14 C 0.97579(15) 0.16636(15) 0.05058(12) 0.0182(4) Uani 1 1 d . . .
C12 C 1.14654(16) 0.06149(16) 0.08393(14) 0.0246(4) Uani 1 1 d . . .
H3 H 1.1881 0.0021 0.1154 0.030 Uiso 1 1 calc R . .
C11 C 1.19181(16) 0.13084(16) 0.02275(13) 0.0227(4) Uani 1 1 d . . .
H4 H 1.2634 0.1181 0.0125 0.027 Uiso 1 1 calc R . .
C6 C 1.12056(16) 0.40483(16) -0.12208(12) 0.0206(4) Uani 1 1 d . . .
C7 C 1.18081(16) 0.29880(17) -0.08576(13) 0.0232(4) Uani 1 1 d . . .
C16 C 0.67379(17) 0.60931(16) -0.15021(14) 0.0265(4) Uani 1 1 d . . .
H21A H 0.6821 0.6045 -0.0825 0.032 Uiso 1 1 calc R . .
H21B H 0.6285 0.6762 -0.1707 0.032 Uiso 1 1 calc R . .
C4 C 0.95621(16) 0.52088(16) -0.14865(13) 0.0203(4) Uani 1 1 d . . .
C22 C 0.81943(16) 0.12014(16) 0.12353(13) 0.0207(4) Uani 1 1 d . . .
H15A H 0.8545 0.1366 0.1871 0.025 Uiso 1 1 calc R . .
H15B H 0.8272 0.0380 0.1116 0.025 Uiso 1 1 calc R . .
C2 C 1.11990(17) 0.58606(17) -0.20375(13) 0.0253(4) Uani 1 1 d . . .
H12 H 1.1562 0.6416 -0.2340 0.030 Uiso 1 1 calc R . .
C1 C 1.17530(17) 0.48842(17) -0.16776(13) 0.0250(4) Uani 1 1 d . . .
H11 H 1.2486 0.4779 -0.1737 0.030 Uiso 1 1 calc R . .
C21 C 0.70033(16) 0.15297(17) 0.11074(13) 0.0228(4) Uani 1 1 d . . .
H16A H 0.6652 0.1163 0.1586 0.027 Uiso 1 1 calc R . .
H16B H 0.6930 0.2363 0.1162 0.027 Uiso 1 1 calc R . .
C15 C 0.78368(16) 0.62153(16) -0.17983(14) 0.0241(4) Uani 1 1 d . . .
H22A H 0.7773 0.6142 -0.2473 0.029 Uiso 1 1 calc R . .
H22B H 0.8155 0.6965 -0.1613 0.029 Uiso 1 1 calc R . .
C3 C 1.01018(17) 0.60260(16) -0.19546(13) 0.0232(4) Uani 1 1 d . . .
H13 H 0.9730 0.6681 -0.2212 0.028 Uiso 1 1 calc R . .
C20 C 0.54057(16) 0.15621(17) -0.00532(14) 0.0241(4) Uani 1 1 d . . .
H17A H 0.5368 0.2385 0.0078 0.029 Uiso 1 1 calc R . .
H17B H 0.4918 0.1156 0.0300 0.029 Uiso 1 1 calc R . .
C13 C 1.03936(16) 0.07931(16) 0.09923(13) 0.0221(4) Uani 1 1 d . . .
H2 H 1.0101 0.0332 0.1419 0.026 Uiso 1 1 calc R . .
C19 C 0.50687(16) 0.13411(17) -0.10880(14) 0.0242(4) Uani 1 1 d . . .
H18A H 0.4287 0.1482 -0.1257 0.029 Uiso 1 1 calc R . .
H18B H 0.5203 0.0533 -0.1218 0.029 Uiso 1 1 calc R . .
C17 C 0.53165(18) 0.47107(19) -0.15060(16) 0.0327(5) Uani 1 1 d . . .
H20A H 0.4769 0.5321 -0.1564 0.039 Uiso 1 1 calc R . .
H20B H 0.5542 0.4542 -0.0846 0.039 Uiso 1 1 calc R . .
C18 C 0.48471(17) 0.36410(18) -0.20155(16) 0.0316(5) Uani 1 1 d . . .
H19A H 0.4656 0.3818 -0.2677 0.038 Uiso 1 1 calc R . .
H19B H 0.4178 0.3425 -0.1786 0.038 Uiso 1 1 calc R . .


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

loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
Se1 C19 1.9585(19) . ?
Se1 C18 1.961(2) . ?
O2 C14 1.362(2) . ?
O2 C22 1.435(2) . ?
O4 C20 1.417(2) . ?
O4 C21 1.422(2) . ?
O6 C8 1.445(2) . ?
O6 H6 0.8200 . ?
O1 C4 1.360(2) . ?
O1 C15 1.434(2) . ?
O3 C17 1.417(2) . ?
O3 C16 1.421(2) . ?
O5 C7 1.226(2) . ?
C8 C5 1.506(2) . ?
C8 C10 1.508(2) . ?
C8 H8 0.9800 . ?
C9 C10 1.400(3) . ?
C9 C11 1.405(3) . ?
C9 C7 1.479(3) . ?
C5 C6 1.395(3) . ?
C5 C4 1.410(3) . ?
C10 C14 1.403(3) . ?
C14 C13 1.393(3) . ?
C12 C11 1.376(3) . ?
C12 C13 1.390(3) . ?
C12 H3 0.9300 . ?
C11 H4 0.9300 . ?
C6 C1 1.402(3) . ?
C6 C7 1.483(3) . ?
C16 C15 1.493(3) . ?
C16 H21A 0.9700 . ?
C16 H21B 0.9700 . ?
C4 C3 1.391(3) . ?
C22 C21 1.500(3) . ?
C22 H15A 0.9700 . ?
C22 H15B 0.9700 . ?
C2 C1 1.376(3) . ?
C2 C3 1.391(3) . ?
C2 H12 0.9300 . ?
C1 H11 0.9300 . ?
C21 H16A 0.9700 . ?
C21 H16B 0.9700 . ?
C15 H22A 0.9700 . ?
C15 H22B 0.9700 . ?
C3 H13 0.9300 . ?
C20 C19 1.509(3) . ?
C20 H17A 0.9700 . ?
C20 H17B 0.9700 . ?
C13 H2 0.9300 . ?
C19 H18A 0.9700 . ?
C19 H18B 0.9700 . ?
C17 C18 1.505(3) . ?
C17 H20A 0.9700 . ?
C17 H20B 0.9700 . ?
C18 H19A 0.9700 . ?
C18 H19B 0.9700 . ?

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
C19 Se1 C18 98.31(8) . . ?
C14 O2 C22 118.36(14) . . ?
C20 O4 C21 113.58(14) . . ?
C8 O6 H6 109.5 . . ?
C4 O1 C15 118.62(15) . . ?
C17 O3 C16 113.23(16) . . ?
O6 C8 C5 107.89(14) . . ?
O6 C8 C10 109.07(14) . . ?
C5 C8 C10 114.01(15) . . ?
O6 C8 H8 108.6 . . ?
C5 C8 H8 108.6 . . ?
C10 C8 H8 108.6 . . ?
C10 C9 C11 120.89(17) . . ?
C10 C9 C7 120.27(17) . . ?
C11 C9 C7 118.81(17) . . ?
C6 C5 C4 118.32(17) . . ?
C6 C5 C8 122.80(16) . . ?
C4 C5 C8 118.87(16) . . ?
C9 C10 C14 118.38(16) . . ?
C9 C10 C8 122.41(16) . . ?
C14 C10 C8 119.18(16) . . ?
O2 C14 C13 124.25(17) . . ?
O2 C14 C10 115.18(15) . . ?
C13 C14 C10 120.57(17) . . ?
C11 C12 C13 120.73(17) . . ?
C11 C12 H3 119.6 . . ?
C13 C12 H3 119.6 . . ?
C12 C11 C9 119.46(18) . . ?
C12 C11 H4 120.3 . . ?
C9 C11 H4 120.3 . . ?
C5 C6 C1 120.99(18) . . ?
C5 C6 C7 120.18(16) . . ?
C1 C6 C7 118.83(17) . . ?
O5 C7 C9 120.78(18) . . ?
O5 C7 C6 120.97(18) . . ?
C9 C7 C6 118.23(17) . . ?
O3 C16 C15 108.43(16) . . ?
O3 C16 H21A 110.0 . . ?
C15 C16 H21A 110.0 . . ?
O3 C16 H21B 110.0 . . ?
C15 C16 H21B 110.0 . . ?
H21A C16 H21B 108.4 . . ?
O1 C4 C3 124.73(17) . . ?
O1 C4 C5 114.74(16) . . ?
C3 C4 C5 120.53(18) . . ?
O2 C22 C21 107.10(15) . . ?
O2 C22 H15A 110.3 . . ?
C21 C22 H15A 110.3 . . ?
O2 C22 H15B 110.3 . . ?
C21 C22 H15B 110.3 . . ?
H15A C22 H15B 108.5 . . ?
C1 C2 C3 120.73(18) . . ?
C1 C2 H12 119.6 . . ?
C3 C2 H12 119.6 . . ?
C2 C1 C6 119.59(19) . . ?
C2 C1 H11 120.2 . . ?
C6 C1 H11 120.2 . . ?
O4 C21 C22 108.32(15) . . ?
O4 C21 H16A 110.0 . . ?
C22 C21 H16A 110.0 . . ?
O4 C21 H16B 110.0 . . ?
C22 C21 H16B 110.0 . . ?
H16A C21 H16B 108.4 . . ?
O1 C15 C16 106.15(15) . . ?
O1 C15 H22A 110.5 . . ?
C16 C15 H22A 110.5 . . ?
O1 C15 H22B 110.5 . . ?
C16 C15 H22B 110.5 . . ?
H22A C15 H22B 108.7 . . ?
C2 C3 C4 119.83(18) . . ?
C2 C3 H13 120.1 . . ?
C4 C3 H13 120.1 . . ?
O4 C20 C19 107.65(15) . . ?
O4 C20 H17A 110.2 . . ?
C19 C20 H17A 110.2 . . ?
O4 C20 H17B 110.2 . . ?
C19 C20 H17B 110.2 . . ?
H17A C20 H17B 108.5 . . ?
C12 C13 C14 119.92(17) . . ?
C12 C13 H2 120.0 . . ?
C14 C13 H2 120.0 . . ?
C20 C19 Se1 112.70(13) . . ?
C20 C19 H18A 109.1 . . ?
Se1 C19 H18A 109.1 . . ?
C20 C19 H18B 109.1 . . ?
Se1 C19 H18B 109.1 . . ?
H18A C19 H18B 107.8 . . ?
O3 C17 C18 107.79(17) . . ?
O3 C17 H20A 110.1 . . ?
C18 C17 H20A 110.1 . . ?
O3 C17 H20B 110.1 . . ?
C18 C17 H20B 110.1 . . ?
H20A C17 H20B 108.5 . . ?
C17 C18 Se1 113.16(14) . . ?
C17 C18 H19A 108.9 . . ?
Se1 C18 H19A 108.9 . . ?
C17 C18 H19B 108.9 . . ?
Se1 C18 H19B 108.9 . . ?
H19A C18 H19B 107.8 . . ?

_diffrn_measured_fraction_theta_max 1.000
_diffrn_reflns_theta_full        25.39
_diffrn_measured_fraction_theta_full 1.000
_refine_diff_density_max         0.508
_refine_diff_density_min         -0.573
_refine_diff_density_rms         0.052
####################################################################### 
# 
# 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_shelx
_database_code_depnum_ccdc_archive 'CCDC 980454'
_audit_update_record             
;
2014-01-09 deposited with the CCDC.
2015-05-27 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2013
_chemical_name_systematic        
;
 ?
;
_chemical_name_common            'CESe+Pb complex'
_chemical_melting_point          ?
_chemical_formula_moiety         'C22 H22 Cl2 O14 Pb Se'
_chemical_formula_sum            'C22 H22 Cl2 O14 Pb Se'
_chemical_formula_weight         867.44

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'
Cl Cl 0.1484 0.1585 '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'
Pb Pb -3.3944 10.1111 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

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

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

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

_cell_length_a                   8.0759(6)
_cell_length_b                   12.2739(9)
_cell_length_c                   13.1224(9)
_cell_angle_alpha                80.0990(10)
_cell_angle_beta                 82.5590(10)
_cell_angle_gamma                85.9020(10)
_cell_volume                     1268.95(16)
_cell_formula_units_Z            2
_cell_measurement_temperature    100(2)

_cell_measurement_reflns_used    8360
_cell_measurement_theta_min      2.50
_cell_measurement_theta_max      25.44

_exptl_crystal_description       slab
_exptl_crystal_colour            'light orange'
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    2.270
_exptl_crystal_F_000             832
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.500
_exptl_crystal_size_mid          0.250
_exptl_crystal_size_min          0.200
_exptl_absorpt_coefficient_mu    8.367
_shelx_estimated_absorpt_T_min   0.103
_shelx_estimated_absorpt_T_max   0.285
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.013
_exptl_absorpt_correction_T_max  0.188
_exptl_absorpt_process_details   SADABS

_exptl_special_details           
;
 ?
;

_diffrn_ambient_temperature      100(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_radiation_source         'sealed tube'
_diffrn_radiation_monochromator  graphite
_diffrn_measurement_device_type  'CCD area detector'
_diffrn_measurement_method       'phi and omega scans'
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            13047
_diffrn_reflns_av_unetI/netI     0.0293
_diffrn_reflns_av_R_equivalents  0.0260
_diffrn_reflns_limit_h_min       -9
_diffrn_reflns_limit_h_max       9
_diffrn_reflns_limit_k_min       -14
_diffrn_reflns_limit_k_max       14
_diffrn_reflns_limit_l_min       -15
_diffrn_reflns_limit_l_max       15
_diffrn_reflns_theta_min         1.587
_diffrn_reflns_theta_max         25.450
_diffrn_reflns_theta_full        25.242
_diffrn_measured_fraction_theta_max 0.997
_diffrn_measured_fraction_theta_full 0.998
_diffrn_reflns_Laue_measured_fraction_max 0.997
_diffrn_reflns_Laue_measured_fraction_full 0.998
_diffrn_reflns_point_group_measured_fraction_max 0.997
_diffrn_reflns_point_group_measured_fraction_full 0.998
_reflns_number_total             4691
_reflns_number_gt                4439
_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 APEX2'
_computing_cell_refinement       'Bruker SAINT'
_computing_data_reduction        'Bruker SAINT'
_computing_structure_solution    'SHELXS-97 (Sheldrick 2008)'
_computing_structure_refinement  'SHELXL-2013 (Sheldrick 2013)'
_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)+(0.0425P)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         4691
_refine_ls_number_parameters     361
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0242
_refine_ls_R_factor_gt           0.0220
_refine_ls_wR_factor_ref         0.0671
_refine_ls_wR_factor_gt          0.0580
_refine_ls_goodness_of_fit_ref   1.127
_refine_ls_restrained_S_all      1.127
_refine_ls_shift/su_max          0.002
_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
C1 C 0.3857(5) 0.4011(4) 1.0969(3) 0.0156(9) Uani 1 1 d . . . . .
H1 H 0.3770 0.4224 1.1621 0.019 Uiso 1 1 calc R U . . .
C2 C 0.2685(5) 0.4397(4) 1.0299(3) 0.0169(9) Uani 1 1 d . . . . .
H2 H 0.1798 0.4868 1.0505 0.020 Uiso 1 1 calc R U . . .
C3 C 0.2812(5) 0.4091(3) 0.9326(3) 0.0137(9) Uani 1 1 d . . . . .
H3 H 0.2043 0.4389 0.8871 0.016 Uiso 1 1 calc R U . . .
C4 C 0.4078(5) 0.3342(3) 0.9018(3) 0.0106(8) Uani 1 1 d . . . . .
C5 C 0.5262(5) 0.2918(3) 0.9704(3) 0.0116(8) Uani 1 1 d . . . . .
C6 C 0.5175(5) 0.3297(3) 1.0655(3) 0.0127(9) Uani 1 1 d . . . . .
C7 C 0.6528(5) 0.3001(3) 1.1338(3) 0.0138(9) Uani 1 1 d . . . . .
C8 C 0.6612(5) 0.2097(3) 0.9437(3) 0.0113(9) Uani 1 1 d . . . . .
C9 C 0.8101(5) 0.2449(3) 1.0890(3) 0.0133(9) Uani 1 1 d . . . . .
C10 C 0.8175(5) 0.2040(3) 0.9947(3) 0.0111(8) Uani 1 1 d . . . . .
C11 C 0.9494(6) 0.2355(4) 1.1429(3) 0.0164(9) Uani 1 1 d . . . . .
H11 H 0.9434 0.2626 1.2054 0.020 Uiso 1 1 calc R U . . .
C12 C 1.0967(5) 0.1858(4) 1.1028(3) 0.0164(9) Uani 1 1 d . . . . .
H12 H 1.1894 0.1787 1.1392 0.020 Uiso 1 1 calc R U . . .
C13 C 1.1083(5) 0.1465(4) 1.0095(3) 0.0159(9) Uani 1 1 d . . . . .
H13 H 1.2088 0.1137 0.9835 0.019 Uiso 1 1 calc R U . . .
C14 C 0.9709(5) 0.1554(3) 0.9538(3) 0.0119(8) Uani 1 1 d . . . . .
C15 C 0.3409(5) 0.3752(4) 0.7280(3) 0.0136(9) Uani 1 1 d . . . . .
H15A H 0.3821 0.4488 0.7201 0.016 Uiso 1 1 calc R U . . .
H15B H 0.2217 0.3796 0.7502 0.016 Uiso 1 1 calc R U . . .
C16 C 0.3722(5) 0.3344(4) 0.6259(3) 0.0131(9) Uani 1 1 d . . . . .
H16A H 0.3382 0.2588 0.6351 0.016 Uiso 1 1 calc R U . . .
H16B H 0.3052 0.3796 0.5767 0.016 Uiso 1 1 calc R U . . .
C17 C 0.5670(5) 0.3536(4) 0.4714(3) 0.0138(9) Uani 1 1 d . . . . .
H17A H 0.5146 0.4241 0.4434 0.017 Uiso 1 1 calc R U . . .
H17B H 0.5139 0.2953 0.4484 0.017 Uiso 1 1 calc R U . . .
C18 C 0.7512(5) 0.3506(3) 0.4324(3) 0.0131(9) Uani 1 1 d . . . . .
H18A H 0.8094 0.3964 0.4680 0.016 Uiso 1 1 calc R U . . .
H18B H 0.7681 0.3786 0.3583 0.016 Uiso 1 1 calc R U . . .
C19 C 1.0760(5) 0.2158(4) 0.4654(3) 0.0147(9) Uani 1 1 d . . . . .
H19A H 1.1373 0.2175 0.3965 0.018 Uiso 1 1 calc R U . . .
H19B H 1.0893 0.2854 0.4883 0.018 Uiso 1 1 calc R U . . .
C20 C 1.1437(5) 0.1204(4) 0.5406(3) 0.0136(9) Uani 1 1 d . . . . .
H20A H 1.1155 0.0505 0.5238 0.016 Uiso 1 1 calc R U . . .
H20B H 1.2645 0.1216 0.5352 0.016 Uiso 1 1 calc R U . . .
C21 C 1.1115(5) 0.0347(3) 0.7204(3) 0.0121(9) Uani 1 1 d . . . . .
H21A H 1.2127 -0.0039 0.6940 0.014 Uiso 1 1 calc R U . . .
H21B H 1.0214 -0.0159 0.7330 0.014 Uiso 1 1 calc R U . . .
C22 C 1.1360(5) 0.0727(4) 0.8198(3) 0.0133(9) Uani 1 1 d . . . . .
H22A H 1.1705 0.0104 0.8701 0.016 Uiso 1 1 calc R U . . .
H22B H 1.2219 0.1265 0.8068 0.016 Uiso 1 1 calc R U . . .
O5 O 0.6409(4) 0.3255(3) 1.2196(2) 0.0223(7) Uani 1 1 d . . . . .
O6 O 0.6442(3) 0.1449(2) 0.8839(2) 0.0116(6) Uani 1 1 d . . . . .
O2 O 0.9787(3) 0.1221(2) 0.8592(2) 0.0133(6) Uani 1 1 d . . . . .
O1 O 0.4235(3) 0.3017(2) 0.8058(2) 0.0116(6) Uani 1 1 d . . . . .
O4 O 1.0712(4) 0.1310(2) 0.6449(2) 0.0122(6) Uani 1 1 d . . . . .
O3 O 0.5460(3) 0.3386(2) 0.5845(2) 0.0120(6) Uani 1 1 d . . . . .
O7 O 0.9783(4) 0.5147(3) 0.7439(3) 0.0207(7) Uani 1 1 d . . . . .
O8 O 0.7526(4) 0.3972(3) 0.7730(3) 0.0239(7) Uani 1 1 d . . . . .
O9 O 0.7736(4) 0.5412(3) 0.6294(3) 0.0287(8) Uani 1 1 d . . . . .
O10 O 0.9594(4) 0.3837(3) 0.6336(2) 0.0195(7) Uani 1 1 d . . . . .
O11 O 0.5035(4) 0.0855(2) 0.6731(2) 0.0178(7) Uani 1 1 d . . . . .
O12 O 0.7514(4) -0.0247(3) 0.6874(3) 0.0191(7) Uani 1 1 d . . . . .
O13 O 0.5055(4) -0.0776(3) 0.7994(3) 0.0240(8) Uani 1 1 d . . . . .
O14 O 0.5253(4) -0.0909(3) 0.6213(3) 0.0232(7) Uani 1 1 d . . . . .
Cl1 Cl 0.86646(12) 0.46142(8) 0.69448(8) 0.0122(2) Uani 1 1 d . . . . .
Cl2 Cl 0.56962(12) -0.02977(8) 0.69604(8) 0.0142(2) Uani 1 1 d . . . . .
Se1 Se 0.83785(5) 0.19640(3) 0.46013(3) 0.01248(10) Uani 1 1 d . . . . .
Pb1 Pb 0.75710(2) 0.20186(2) 0.68818(2) 0.01010(7) 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
C1 C2 1.379(6) . ?
C1 C6 1.396(6) . ?
C1 H1 0.9300 . ?
C2 C3 1.380(6) . ?
C2 H2 0.9300 . ?
C3 C4 1.393(6) . ?
C3 H3 0.9300 . ?
C4 O1 1.374(5) . ?
C4 C5 1.409(6) . ?
C5 C6 1.398(6) . ?
C5 C8 1.481(6) . ?
C6 C7 1.487(6) . ?
C7 O5 1.209(5) . ?
C7 C9 1.497(6) . ?
C8 O6 1.236(5) . ?
C8 C10 1.495(6) . ?
C9 C11 1.393(6) . ?
C9 C10 1.407(6) . ?
C10 C14 1.418(6) . ?
C11 C12 1.382(6) . ?
C11 H11 0.9300 . ?
C12 C13 1.382(6) . ?
C12 H12 0.9300 . ?
C13 C14 1.394(6) . ?
C13 H13 0.9300 . ?
C14 O2 1.365(5) . ?
C15 O1 1.439(5) . ?
C15 C16 1.495(6) . ?
C15 H15A 0.9700 . ?
C15 H15B 0.9700 . ?
C16 O3 1.439(5) . ?
C16 H16A 0.9700 . ?
C16 H16B 0.9700 . ?
C17 O3 1.453(5) . ?
C17 C18 1.509(6) . ?
C17 H17A 0.9700 . ?
C17 H17B 0.9700 . ?
C18 Se1 1.961(4) . ?
C18 H18A 0.9700 . ?
C18 H18B 0.9700 . ?
C19 C20 1.515(6) . ?
C19 Se1 1.966(4) . ?
C19 H19A 0.9700 . ?
C19 H19B 0.9700 . ?
C20 O4 1.441(5) . ?
C20 H20A 0.9700 . ?
C20 H20B 0.9700 . ?
C21 O4 1.454(5) . ?
C21 C22 1.498(6) . ?
C21 H21A 0.9700 . ?
C21 H21B 0.9700 . ?
C22 O2 1.441(5) . ?
C22 H22A 0.9700 . ?
C22 H22B 0.9700 . ?
O6 Pb1 2.604(3) . ?
O4 Pb1 2.645(3) . ?
O3 Pb1 2.642(3) . ?
O7 Cl1 1.430(3) . ?
O8 Cl1 1.452(3) . ?
O9 Cl1 1.422(3) . ?
O10 Cl1 1.455(3) . ?
O11 Cl2 1.471(3) . ?
O11 Pb1 2.625(3) . ?
O12 Cl2 1.462(3) . ?
O13 Cl2 1.429(3) . ?
O14 Cl2 1.426(3) . ?
Se1 Pb1 2.9904(5) . ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
C2 C1 C6 119.1(4) . . ?
C2 C1 H1 120.4 . . ?
C6 C1 H1 120.4 . . ?
C1 C2 C3 120.8(4) . . ?
C1 C2 H2 119.6 . . ?
C3 C2 H2 119.6 . . ?
C2 C3 C4 120.8(4) . . ?
C2 C3 H3 119.6 . . ?
C4 C3 H3 119.6 . . ?
O1 C4 C3 122.3(4) . . ?
O1 C4 C5 118.6(3) . . ?
C3 C4 C5 119.1(4) . . ?
C6 C5 C4 119.0(4) . . ?
C6 C5 C8 119.1(4) . . ?
C4 C5 C8 121.9(4) . . ?
C1 C6 C5 120.9(4) . . ?
C1 C6 C7 117.9(4) . . ?
C5 C6 C7 121.1(4) . . ?
O5 C7 C6 121.6(4) . . ?
O5 C7 C9 121.0(4) . . ?
C6 C7 C9 117.3(4) . . ?
O6 C8 C5 121.4(4) . . ?
O6 C8 C10 120.5(4) . . ?
C5 C8 C10 118.1(4) . . ?
C11 C9 C10 120.8(4) . . ?
C11 C9 C7 118.3(4) . . ?
C10 C9 C7 120.9(4) . . ?
C9 C10 C14 118.8(4) . . ?
C9 C10 C8 118.5(4) . . ?
C14 C10 C8 122.7(4) . . ?
C12 C11 C9 119.4(4) . . ?
C12 C11 H11 120.3 . . ?
C9 C11 H11 120.3 . . ?
C11 C12 C13 121.0(4) . . ?
C11 C12 H12 119.5 . . ?
C13 C12 H12 119.5 . . ?
C12 C13 C14 120.6(4) . . ?
C12 C13 H13 119.7 . . ?
C14 C13 H13 119.7 . . ?
O2 C14 C13 122.6(4) . . ?
O2 C14 C10 118.1(4) . . ?
C13 C14 C10 119.3(4) . . ?
O1 C15 C16 110.4(3) . . ?
O1 C15 H15A 109.6 . . ?
C16 C15 H15A 109.6 . . ?
O1 C15 H15B 109.6 . . ?
C16 C15 H15B 109.6 . . ?
H15A C15 H15B 108.1 . . ?
O3 C16 C15 111.3(3) . . ?
O3 C16 H16A 109.4 . . ?
C15 C16 H16A 109.4 . . ?
O3 C16 H16B 109.4 . . ?
C15 C16 H16B 109.4 . . ?
H16A C16 H16B 108.0 . . ?
O3 C17 C18 109.2(3) . . ?
O3 C17 H17A 109.8 . . ?
C18 C17 H17A 109.8 . . ?
O3 C17 H17B 109.8 . . ?
C18 C17 H17B 109.8 . . ?
H17A C17 H17B 108.3 . . ?
C17 C18 Se1 107.9(3) . . ?
C17 C18 H18A 110.1 . . ?
Se1 C18 H18A 110.1 . . ?
C17 C18 H18B 110.1 . . ?
Se1 C18 H18B 110.1 . . ?
H18A C18 H18B 108.4 . . ?
C20 C19 Se1 108.9(3) . . ?
C20 C19 H19A 109.9 . . ?
Se1 C19 H19A 109.9 . . ?
C20 C19 H19B 109.9 . . ?
Se1 C19 H19B 109.9 . . ?
H19A C19 H19B 108.3 . . ?
O4 C20 C19 108.7(3) . . ?
O4 C20 H20A 110.0 . . ?
C19 C20 H20A 110.0 . . ?
O4 C20 H20B 110.0 . . ?
C19 C20 H20B 110.0 . . ?
H20A C20 H20B 108.3 . . ?
O4 C21 C22 108.6(3) . . ?
O4 C21 H21A 110.0 . . ?
C22 C21 H21A 110.0 . . ?
O4 C21 H21B 110.0 . . ?
C22 C21 H21B 110.0 . . ?
H21A C21 H21B 108.4 . . ?
O2 C22 C21 107.5(3) . . ?
O2 C22 H22A 110.2 . . ?
C21 C22 H22A 110.2 . . ?
O2 C22 H22B 110.2 . . ?
C21 C22 H22B 110.2 . . ?
H22A C22 H22B 108.5 . . ?
C8 O6 Pb1 117.5(3) . . ?
C14 O2 C22 116.8(3) . . ?
C4 O1 C15 115.0(3) . . ?
C20 O4 C21 112.2(3) . . ?
C20 O4 Pb1 122.4(2) . . ?
C21 O4 Pb1 110.2(2) . . ?
C16 O3 C17 111.3(3) . . ?
C16 O3 Pb1 116.6(2) . . ?
C17 O3 Pb1 119.0(2) . . ?
Cl2 O11 Pb1 103.51(14) . . ?
O9 Cl1 O7 110.5(2) . . ?
O9 Cl1 O8 109.6(2) . . ?
O7 Cl1 O8 109.7(2) . . ?
O9 Cl1 O10 110.1(2) . . ?
O7 Cl1 O10 110.15(18) . . ?
O8 Cl1 O10 106.66(19) . . ?
O14 Cl2 O13 111.1(2) . . ?
O14 Cl2 O12 110.14(19) . . ?
O13 Cl2 O12 110.3(2) . . ?
O14 Cl2 O11 109.5(2) . . ?
O13 Cl2 O11 109.61(19) . . ?
O12 Cl2 O11 106.05(18) . . ?
C18 Se1 C19 101.38(18) . . ?
C18 Se1 Pb1 88.71(12) . . ?
C19 Se1 Pb1 91.67(13) . . ?
O6 Pb1 O11 79.12(9) . . ?
O6 Pb1 O3 112.54(9) . . ?
O11 Pb1 O3 73.47(9) . . ?
O6 Pb1 O4 112.54(9) . . ?
O11 Pb1 O4 122.37(9) . . ?
O3 Pb1 O4 134.33(9) . . ?
O6 Pb1 Se1 160.92(6) . . ?
O11 Pb1 Se1 84.09(7) . . ?
O3 Pb1 Se1 70.55(6) . . ?
O4 Pb1 Se1 69.39(6) . . ?

_refine_diff_density_max         2.121
_refine_diff_density_min         -1.132
_refine_diff_density_rms         0.168

_shelxl_version_number           2013-4

