# Electronic Supplementary Material (ESI) for Chemical Communications
# This journal is © The Royal Society of Chemistry 2013


#######################################################################
#
#                 Cambridge Crystallographic Data Centre
#                                CCDC 
# 
#######################################################################
# 
#  This CIF contains data from an original supplementary publication 
#  deposited with the CCDC, and may include chemical, crystal,   
#  experimental, refinement, atomic coordinates, 
#  anisotropic displacement parameters and molecular geometry data,
#  as required by the journal to which it was submitted. 
# 
#  This CIF is provided on the understanding that it is used for bona
#  fide research purposes only. It may contain copyright material 
#  of the CCDC or of third parties, and may not be copied or further 
#  disseminated in any form, whether machine-readable or not,  
#  except for the purpose of generating routine backup copies 
#  on your local computer system.
# 
#  For further information on the CCDC, data deposition and 
#  data retrieval see:
#                         www.ccdc.cam.ac.uk 
#
#  Bona fide researchers may freely download Mercury and enCIFer
#  from this site to visualise CIF-encoded structures and 
#  to carry out CIF format checking respectively. 
#
####################################################################### 

data_p21n
_database_code_depnum_ccdc_archive 'CCDC 904644'
#TrackingRef 'DK_B1CS1_49_p21n_final.cif'


_audit_creation_method           SHELXL-2012
_chemical_name_systematic        
;
?
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         'C20 H14 S2'
_chemical_formula_sum            'C20 H14 S2'
_chemical_formula_weight         318.43

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'
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                   5.968(3)
_cell_length_b                   7.465(2)
_cell_length_c                   33.815(12)
_cell_angle_alpha                90
_cell_angle_beta                 94.026(9)
_cell_angle_gamma                90
_cell_volume                     1502.6(11)
_cell_formula_units_Z            4
_cell_measurement_temperature    100(2)
_cell_measurement_reflns_used    6297
_cell_measurement_theta_min      2.415
_cell_measurement_theta_max      25.747

_exptl_crystal_description       plate
_exptl_crystal_colour            yellow
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.408
_exptl_crystal_F_000             664
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.300
_exptl_crystal_size_mid          0.200
_exptl_crystal_size_min          0.001
_exptl_absorpt_coefficient_mu    0.347
_shelx_estimated_absorpt_T_min   0.903
_shelx_estimated_absorpt_T_max   1.000
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.8787
_exptl_absorpt_correction_T_max  0.9422
_exptl_absorpt_process_details   'SADABS-2008/1, Sheldrick, Goettingen'

_exptl_special_details           
;
?
;

_diffrn_ambient_temperature      100(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_radiation_source         'rotating anode (TXS)'
_diffrn_radiation_monochromator  mirror
_diffrn_measurement_device_type  'Bruker Smart APEX II Ultra'
_diffrn_measurement_method       'omega scans'
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            30910
_diffrn_reflns_sigmaI/netI       0.0234
_diffrn_reflns_av_R_equivalents  0.0433
_diffrn_reflns_limit_h_min       -7
_diffrn_reflns_limit_h_max       7
_diffrn_reflns_limit_k_min       -9
_diffrn_reflns_limit_k_max       9
_diffrn_reflns_limit_l_min       -41
_diffrn_reflns_limit_l_max       41
_diffrn_reflns_theta_min         1.207
_diffrn_reflns_theta_max         25.770
_diffrn_reflns_theta_full        25.242
_diffrn_measured_fraction_theta_max 0.995
_diffrn_measured_fraction_theta_full 1.000
_diffrn_reflns_Laue_measured_fraction_max 0.995
_diffrn_reflns_Laue_measured_fraction_full 1.000
_diffrn_reflns_point_group_measured_fraction_max 0.995
_diffrn_reflns_point_group_measured_fraction_full 1.000
_reflns_number_total             2873
_reflns_number_gt                2379
_reflns_threshold_expression     'I > 2\s(I)'
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_max     .
_reflns_Friedel_fraction_full    .

_reflns_special_details          
;
The reflections were merged according to the crystal class
for structure refinement and the calculation of statistics.
_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       'APEX2 v2011.2'
_computing_cell_refinement       'SAINT V7.68A'
_computing_data_reduction        'SAINT V7.68A'
_computing_structure_solution    'SHELXS in SHELXTL Version 2008/3'
_computing_structure_refinement  'SHELXL-2012 (Sheldrick, 2012)'
_computing_molecular_graphics    'XP Version 5.1'
_computing_publication_material  'XP Version 5.1'

_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/[\s^2^(Fo^2^)+(0.0456P)^2^+1.9104P]
where P=(Fo^2^+2Fc^2^)/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         2873
_refine_ls_number_parameters     199
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0652
_refine_ls_R_factor_gt           0.0508
_refine_ls_wR_factor_ref         0.1221
_refine_ls_wR_factor_gt          0.1156
_refine_ls_goodness_of_fit_ref   1.139
_refine_ls_restrained_S_all      1.139
_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
_atom_site_disorder_assembly
_atom_site_disorder_group
S1 S 0.71144(11) 0.51726(10) 0.32553(2) 0.0258(2) Uani 1 1 d D . .
S2 S 1.27645(11) 0.34140(10) 0.17108(2) 0.0256(2) Uani 1 1 d D . .
C1 C 0.7478(4) 0.5059(4) 0.27612(8) 0.0241(6) Uani 1 1 d D . .
H1 H 0.6367 0.5413 0.2561 0.029 Uiso 1 1 calc RD . .
C2 C 0.9544(4) 0.4402(3) 0.26824(7) 0.0189(5) Uani 1 1 d D . .
C3 C 1.0855(4) 0.3970(3) 0.30415(7) 0.0193(5) Uani 1 1 d D . .
H3 H 1.2320 0.3468 0.3046 0.023 Uiso 1 1 calc RD . .
C4 C 0.9799(4) 0.4348(3) 0.33765(7) 0.0184(5) Uani 1 1 d D . .
C5 C 1.2380(4) 0.3496(4) 0.22047(8) 0.0244(6) Uani 1 1 d D . .
H5 H 1.3462 0.3089 0.2404 0.029 Uiso 1 1 calc RD . .
C6 C 1.0340(4) 0.4214(3) 0.22841(7) 0.0190(5) Uani 1 1 d D . .
C7 C 0.9075(4) 0.4704(3) 0.19262(7) 0.0195(5) Uani 1 1 d D . .
H7 H 0.7633 0.5245 0.1922 0.023 Uiso 1 1 calc RD . .
C8 C 1.0127(4) 0.4323(3) 0.15912(7) 0.0179(5) Uani 1 1 d D . .
C9 C 1.0704(4) 0.4319(3) 0.37918(7) 0.0180(5) Uani 1 1 d D . .
C10 C 0.9616(4) 0.5213(4) 0.40875(8) 0.0216(6) Uani 1 1 d D . .
H10 H 0.8234 0.5810 0.4022 0.026 Uiso 1 1 calc RD . .
C11 C 1.0533(5) 0.5236(4) 0.44748(8) 0.0238(6) Uani 1 1 d D . .
H11 H 0.9779 0.5847 0.4673 0.029 Uiso 1 1 calc RD . .
C12 C 1.2557(4) 0.4367(4) 0.45753(8) 0.0232(6) Uani 1 1 d D . .
H12 H 1.3184 0.4383 0.4841 0.028 Uiso 1 1 calc RD . .
C13 C 1.3648(4) 0.3481(4) 0.42862(8) 0.0225(6) Uani 1 1 d D . .
H13 H 1.5032 0.2890 0.4354 0.027 Uiso 1 1 calc RD . .
C14 C 1.2732(4) 0.3451(3) 0.38980(8) 0.0202(6) Uani 1 1 d D . .
H14 H 1.3494 0.2833 0.3702 0.024 Uiso 1 1 calc RD . .
C15 C 0.9261(4) 0.4428(3) 0.11732(7) 0.0175(5) Uani 1 1 d D . .
C16 C 1.0422(4) 0.3640(4) 0.08720(8) 0.0212(6) Uani 1 1 d D . .
H16 H 1.1813 0.3055 0.0937 0.025 Uiso 1 1 calc RD . .
C17 C 0.9569(4) 0.3704(4) 0.04823(8) 0.0236(6) Uani 1 1 d D . .
H17 H 1.0381 0.3172 0.0281 0.028 Uiso 1 1 calc RD . .
C18 C 0.7525(4) 0.4544(4) 0.03820(8) 0.0238(6) Uani 1 1 d D . .
H18 H 0.6938 0.4583 0.0114 0.029 Uiso 1 1 calc RD . .
C19 C 0.6353(4) 0.5325(4) 0.06778(8) 0.0228(6) Uani 1 1 d D . .
H19 H 0.4956 0.5898 0.0611 0.027 Uiso 1 1 calc RD . .
C20 C 0.7211(4) 0.5273(3) 0.10697(8) 0.0201(6) Uani 1 1 d D . .
H20 H 0.6399 0.5817 0.1270 0.024 Uiso 1 1 calc RD . .

loop_
_atom_site_aniso_label
_atom_site_aniso_U_11
_atom_site_aniso_U_22
_atom_site_aniso_U_33
_atom_site_aniso_U_23
_atom_site_aniso_U_13
_atom_site_aniso_U_12
S1 0.0204(4) 0.0340(4) 0.0228(4) 0.0001(3) 0.0007(3) 0.0081(3)
S2 0.0204(4) 0.0344(4) 0.0219(4) 0.0003(3) 0.0005(3) 0.0071(3)
C1 0.0234(14) 0.0265(15) 0.0220(13) 0.0024(11) -0.0009(11) 0.0045(11)
C2 0.0193(12) 0.0173(13) 0.0197(13) 0.0010(10) -0.0007(10) -0.0010(10)
C3 0.0162(12) 0.0210(13) 0.0206(13) 0.0006(11) 0.0001(10) 0.0008(10)
C4 0.0158(12) 0.0170(13) 0.0222(13) 0.0017(10) -0.0005(10) 0.0014(10)
C5 0.0234(14) 0.0282(16) 0.0213(13) 0.0016(11) -0.0015(11) 0.0041(11)
C6 0.0188(12) 0.0180(13) 0.0196(13) -0.0007(10) -0.0022(10) -0.0009(10)
C7 0.0163(12) 0.0206(14) 0.0212(13) 0.0009(11) -0.0013(10) -0.0012(10)
C8 0.0165(12) 0.0160(13) 0.0209(13) 0.0008(10) -0.0019(10) -0.0005(10)
C9 0.0171(12) 0.0174(13) 0.0196(13) 0.0018(10) 0.0020(10) -0.0015(10)
C10 0.0190(13) 0.0216(14) 0.0245(13) 0.0040(11) 0.0030(10) 0.0031(11)
C11 0.0280(14) 0.0228(14) 0.0213(13) -0.0003(11) 0.0063(11) 0.0010(11)
C12 0.0250(14) 0.0270(15) 0.0174(13) 0.0042(11) -0.0003(11) -0.0031(11)
C13 0.0177(13) 0.0237(14) 0.0257(14) 0.0059(11) 0.0000(11) 0.0015(11)
C14 0.0192(13) 0.0202(14) 0.0217(13) 0.0024(11) 0.0060(10) 0.0023(10)
C15 0.0169(12) 0.0163(13) 0.0195(12) 0.0010(10) 0.0025(10) -0.0042(10)
C16 0.0177(13) 0.0215(14) 0.0245(14) -0.0011(11) 0.0018(10) 0.0008(10)
C17 0.0251(14) 0.0245(14) 0.0216(13) -0.0038(11) 0.0046(11) -0.0021(11)
C18 0.0251(14) 0.0278(15) 0.0179(13) -0.0001(11) -0.0030(11) -0.0044(11)
C19 0.0171(13) 0.0263(15) 0.0247(14) 0.0036(11) -0.0017(10) 0.0000(11)
C20 0.0182(13) 0.0193(13) 0.0230(13) -0.0007(11) 0.0026(10) 0.0000(10)

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

loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
S1 C1 1.702(3) . ?
S1 C4 1.738(3) . ?
S2 C5 1.703(3) . ?
S2 C8 1.735(3) . ?
C1 C2 1.370(4) . ?
C1 H1 0.9500 . ?
C2 C3 1.435(3) . ?
C2 C6 1.466(4) . ?
C3 C4 1.364(4) . ?
C3 H3 0.9500 . ?
C4 C9 1.469(3) . ?
C5 C6 1.374(4) . ?
C5 H5 0.9500 . ?
C6 C7 1.428(3) . ?
C7 C8 1.363(4) . ?
C7 H7 0.9500 . ?
C8 C15 1.473(3) . ?
C9 C14 1.397(4) . ?
C9 C10 1.399(4) . ?
C10 C11 1.384(4) . ?
C10 H10 0.9500 . ?
C11 C12 1.392(4) . ?
C11 H11 0.9500 . ?
C12 C13 1.381(4) . ?
C12 H12 0.9500 . ?
C13 C14 1.386(4) . ?
C13 H13 0.9500 . ?
C14 H14 0.9500 . ?
C15 C20 1.399(4) . ?
C15 C16 1.401(4) . ?
C16 C17 1.380(4) . ?
C16 H16 0.9500 . ?
C17 C18 1.392(4) . ?
C17 H17 0.9500 . ?
C18 C19 1.388(4) . ?
C18 H18 0.9500 . ?
C19 C20 1.388(4) . ?
C19 H19 0.9500 . ?
C20 H20 0.9500 . ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
C1 S1 C4 92.00(13) . . ?
C5 S2 C8 91.85(13) . . ?
C2 C1 S1 112.8(2) . . ?
C2 C1 H1 123.6 . . ?
S1 C1 H1 123.6 . . ?
C1 C2 C3 111.1(2) . . ?
C1 C2 C6 124.5(2) . . ?
C3 C2 C6 124.3(2) . . ?
C4 C3 C2 113.6(2) . . ?
C4 C3 H3 123.2 . . ?
C2 C3 H3 123.2 . . ?
C3 C4 C9 129.1(2) . . ?
C3 C4 S1 110.45(19) . . ?
C9 C4 S1 120.10(19) . . ?
C6 C5 S2 112.81(19) . . ?
C6 C5 H5 123.6 . . ?
S2 C5 H5 123.6 . . ?
C5 C6 C7 110.9(2) . . ?
C5 C6 C2 124.4(2) . . ?
C7 C6 C2 124.6(2) . . ?
C8 C7 C6 113.8(2) . . ?
C8 C7 H7 123.1 . . ?
C6 C7 H7 123.1 . . ?
C7 C8 C15 129.4(2) . . ?
C7 C8 S2 110.54(18) . . ?
C15 C8 S2 119.75(19) . . ?
C14 C9 C10 118.3(2) . . ?
C14 C9 C4 120.4(2) . . ?
C10 C9 C4 121.2(2) . . ?
C11 C10 C9 120.6(2) . . ?
C11 C10 H10 119.7 . . ?
C9 C10 H10 119.7 . . ?
C10 C11 C12 120.3(2) . . ?
C10 C11 H11 119.9 . . ?
C12 C11 H11 119.9 . . ?
C13 C12 C11 119.7(2) . . ?
C13 C12 H12 120.2 . . ?
C11 C12 H12 120.2 . . ?
C12 C13 C14 120.3(2) . . ?
C12 C13 H13 119.9 . . ?
C14 C13 H13 119.9 . . ?
C13 C14 C9 120.8(2) . . ?
C13 C14 H14 119.6 . . ?
C9 C14 H14 119.6 . . ?
C20 C15 C16 118.4(2) . . ?
C20 C15 C8 120.4(2) . . ?
C16 C15 C8 121.2(2) . . ?
C17 C16 C15 120.8(2) . . ?
C17 C16 H16 119.6 . . ?
C15 C16 H16 119.6 . . ?
C16 C17 C18 120.4(2) . . ?
C16 C17 H17 119.8 . . ?
C18 C17 H17 119.8 . . ?
C19 C18 C17 119.4(2) . . ?
C19 C18 H18 120.3 . . ?
C17 C18 H18 120.3 . . ?
C20 C19 C18 120.4(2) . . ?
C20 C19 H19 119.8 . . ?
C18 C19 H19 119.8 . . ?
C19 C20 C15 120.6(2) . . ?
C19 C20 H20 119.7 . . ?
C15 C20 H20 119.7 . . ?

loop_
_geom_torsion_atom_site_label_1
_geom_torsion_atom_site_label_2
_geom_torsion_atom_site_label_3
_geom_torsion_atom_site_label_4
_geom_torsion
_geom_torsion_site_symmetry_1
_geom_torsion_site_symmetry_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
_geom_torsion_publ_flag
C4 S1 C1 C2 0.7(2) . . . . ?
S1 C1 C2 C3 0.4(3) . . . . ?
S1 C1 C2 C6 -177.9(2) . . . . ?
C1 C2 C3 C4 -1.7(3) . . . . ?
C6 C2 C3 C4 176.7(2) . . . . ?
C2 C3 C4 C9 -170.9(2) . . . . ?
C2 C3 C4 S1 2.2(3) . . . . ?
C1 S1 C4 C3 -1.6(2) . . . . ?
C1 S1 C4 C9 172.2(2) . . . . ?
C8 S2 C5 C6 -1.0(2) . . . . ?
S2 C5 C6 C7 0.0(3) . . . . ?
S2 C5 C6 C2 178.4(2) . . . . ?
C1 C2 C6 C5 -177.6(3) . . . . ?
C3 C2 C6 C5 4.3(4) . . . . ?
C1 C2 C6 C7 0.6(4) . . . . ?
C3 C2 C6 C7 -177.6(2) . . . . ?
C5 C6 C7 C8 1.4(3) . . . . ?
C2 C6 C7 C8 -177.0(2) . . . . ?
C6 C7 C8 C15 171.9(2) . . . . ?
C6 C7 C8 S2 -2.1(3) . . . . ?
C5 S2 C8 C7 1.7(2) . . . . ?
C5 S2 C8 C15 -172.9(2) . . . . ?
C3 C4 C9 C14 -15.8(4) . . . . ?
S1 C4 C9 C14 171.7(2) . . . . ?
C3 C4 C9 C10 161.7(3) . . . . ?
S1 C4 C9 C10 -10.9(3) . . . . ?
C14 C9 C10 C11 0.1(4) . . . . ?
C4 C9 C10 C11 -177.4(2) . . . . ?
C9 C10 C11 C12 0.0(4) . . . . ?
C10 C11 C12 C13 0.0(4) . . . . ?
C11 C12 C13 C14 -0.2(4) . . . . ?
C12 C13 C14 C9 0.3(4) . . . . ?
C10 C9 C14 C13 -0.2(4) . . . . ?
C4 C9 C14 C13 177.3(2) . . . . ?
C7 C8 C15 C20 11.2(4) . . . . ?
S2 C8 C15 C20 -175.35(19) . . . . ?
C7 C8 C15 C16 -166.8(3) . . . . ?
S2 C8 C15 C16 6.7(3) . . . . ?
C20 C15 C16 C17 0.3(4) . . . . ?
C8 C15 C16 C17 178.3(2) . . . . ?
C15 C16 C17 C18 -0.5(4) . . . . ?
C16 C17 C18 C19 0.2(4) . . . . ?
C17 C18 C19 C20 0.1(4) . . . . ?
C18 C19 C20 C15 -0.3(4) . . . . ?
C16 C15 C20 C19 0.1(4) . . . . ?
C8 C15 C20 C19 -177.9(2) . . . . ?

_refine_diff_density_max         0.463
_refine_diff_density_min         -0.448
_refine_diff_density_rms         0.062


data_p21n_a
_database_code_depnum_ccdc_archive 'CCDC 904645'
#TrackingRef 'DK_B1CS1_66_p21n_final.cif'


_audit_creation_method           SHELXL-2012
_chemical_name_systematic        
;
?
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         'C22 H16 F6 O3 S'
_chemical_formula_sum            'C22 H16 F6 O3 S'
_chemical_formula_weight         474.41

_vrf_PLAT_213_global             
;
213_ALERT_2_B Atom Fxx has ADP max/min Ratio ..... 4.2 prola
RESPONSE:
All flourine atoms where found to be disordered; see
_refine_special_details
;



loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
F F 0.0171 0.0103 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
S S 0.1246 0.1234 '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'

_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                   17.201(6)
_cell_length_b                   6.588(3)
_cell_length_c                   17.859(6)
_cell_angle_alpha                90
_cell_angle_beta                 98.49(2)
_cell_angle_gamma                90
_cell_volume                     2001.6(13)
_cell_formula_units_Z            4
_cell_measurement_temperature    100(2)
_cell_measurement_reflns_used    8411
_cell_measurement_theta_min      2.306
_cell_measurement_theta_max      26.873

_exptl_crystal_description       plate
_exptl_crystal_colour            colourless
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.574
_exptl_crystal_F_000             968
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.146
_exptl_crystal_size_mid          0.122
_exptl_crystal_size_min          0.037
_exptl_absorpt_coefficient_mu    0.240
_shelx_estimated_absorpt_T_min   0.966
_shelx_estimated_absorpt_T_max   0.991
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.8007
_exptl_absorpt_correction_T_max  0.8621
_exptl_absorpt_process_details   SADABS-2008/1

_exptl_special_details           
;
?
;

_diffrn_ambient_temperature      100(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_radiation_source         'INCOATEC Mo Microsource'
_diffrn_radiation_monochromator  mirror
_diffrn_measurement_device_type  'Bruker Smart Apex II Quazar'
_diffrn_measurement_method       'omega scans'
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            41361
_diffrn_reflns_sigmaI/netI       0.0244
_diffrn_reflns_av_R_equivalents  0.0423
_diffrn_reflns_limit_h_min       -21
_diffrn_reflns_limit_h_max       21
_diffrn_reflns_limit_k_min       -8
_diffrn_reflns_limit_k_max       8
_diffrn_reflns_limit_l_min       -22
_diffrn_reflns_limit_l_max       22
_diffrn_reflns_theta_min         1.534
_diffrn_reflns_theta_max         26.728
_diffrn_reflns_theta_full        25.242
_diffrn_measured_fraction_theta_max 0.999
_diffrn_measured_fraction_theta_full 0.999
_diffrn_reflns_Laue_measured_fraction_max 0.999
_diffrn_reflns_Laue_measured_fraction_full 0.999
_diffrn_reflns_point_group_measured_fraction_max 0.999
_diffrn_reflns_point_group_measured_fraction_full 0.999
_reflns_number_total             4254
_reflns_number_gt                3554
_reflns_threshold_expression     'I > 2\s(I)'
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_max     .
_reflns_Friedel_fraction_full    .

_reflns_special_details          
;
The reflections were merged according to the crystal class
for structure refinement and the calculation of statistics.
_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       'APEX2 v2011.2'
_computing_cell_refinement       'SAINT V7.68A'
_computing_data_reduction        'SAINT V7.68A'
_computing_structure_solution    'SHELXS in SHELXTL Version 2008/3'
_computing_structure_refinement  'SHELXL-2012 (Sheldrick, 2012)'
_computing_molecular_graphics    'XP Version 5.1'
_computing_publication_material  'XP Version 5.1'

_refine_special_details          
;
Both CF_3 groups on C1 and C22 turned out to be highly rotational
disordered. Same distance restraints for ideal symmetry of the CF_3
groups where applied and the occupancy was set to one. Opposite ADPs
where set equal.
;
_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
;
w=1/[\s^2^(Fo^2^)+(0.0659P)^2^+4.3059P]
where P=(Fo^2^+2Fc^2^)/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         4254
_refine_ls_number_parameters     331
_refine_ls_number_restraints     464
_refine_ls_R_factor_all          0.0751
_refine_ls_R_factor_gt           0.0643
_refine_ls_wR_factor_ref         0.1659
_refine_ls_wR_factor_gt          0.1591
_refine_ls_goodness_of_fit_ref   1.095
_refine_ls_restrained_S_all      1.495
_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
_atom_site_disorder_assembly
_atom_site_disorder_group
S1 S 0.35845(4) 1.02576(10) 0.31015(4) 0.02217(19) Uani 1 1 d D B .
C22 C 0.67301(16) 1.5325(4) 0.26938(15) 0.0412(8) Uani 1 1 d DU . .
F1 F 0.7144(5) 1.4954(14) 0.2142(4) 0.0465(11) Uani 0.255(3) 1 d PDU A 1
F2 F 0.7266(5) 1.5493(19) 0.3305(3) 0.120(3) Uani 0.255(3) 1 d PDU A 1
F3 F 0.6458(5) 1.7177(8) 0.2565(7) 0.092(2) Uani 0.255(3) 1 d PDU A 1
F1' F 0.6503(3) 1.7053(5) 0.2967(3) 0.0465(11) Uani 0.466(3) 1 d PDU A 2
F2' F 0.6844(5) 1.5701(9) 0.2005(2) 0.120(3) Uani 0.466(3) 1 d PDU A 2
F3' F 0.7432(2) 1.5011(7) 0.3090(4) 0.092(2) Uani 0.466(3) 1 d PDU A 2
F1" F 0.7007(6) 1.6488(14) 0.3265(3) 0.120(3) Uani 0.279(3) 1 d PDU A 3
F2" F 0.6338(4) 1.6593(12) 0.2188(5) 0.092(2) Uani 0.279(3) 1 d PDU A 3
F3" F 0.7343(4) 1.4790(11) 0.2374(5) 0.0465(11) Uani 0.279(3) 1 d PDU A 3
C1 C 0.09123(16) -0.3053(4) 0.51444(13) 0.0400(8) Uani 1 1 d DU . .
F4 F 0.1284(2) -0.4674(4) 0.5451(2) 0.0510(10) Uani 0.675(3) 1 d PDU B 1
F5 F 0.0450(3) -0.3701(7) 0.45430(17) 0.0933(19) Uani 0.675(3) 1 d PDU B 1
F6 F 0.0455(2) -0.2499(6) 0.5637(2) 0.0592(13) Uani 0.675(3) 1 d PDU B 1
F4' F 0.0216(5) -0.274(2) 0.4730(9) 0.0510(10) Uani 0.123(3) 1 d PDU B 2
F5' F 0.0770(10) -0.286(3) 0.5849(4) 0.0933(19) Uani 0.123(3) 1 d PDU B 2
F6' F 0.1116(8) -0.4882(11) 0.4951(12) 0.0592(13) Uani 0.123(3) 1 d PDU B 2
F4" F 0.0241(4) -0.251(2) 0.5349(8) 0.0592(13) Uani 0.202(3) 1 d PDU B 3
F5" F 0.0723(7) -0.4214(18) 0.4541(5) 0.0510(10) Uani 0.202(3) 1 d PDU B 3
F6" F 0.1237(8) -0.4307(19) 0.5676(7) 0.0933(19) Uani 0.202(3) 1 d PDU B 3
O1 O 0.35611(13) 0.3818(3) 0.50255(11) 0.0319(5) Uani 1 1 d D . .
O2 O 0.31736(11) 0.6566(3) 0.25520(11) 0.0230(4) Uani 1 1 d D B .
O3 O 0.44860(11) 0.7440(3) 0.25560(11) 0.0229(4) Uani 1 1 d D B .
C2 C 0.14491(18) -0.1371(4) 0.49809(17) 0.0298(7) Uani 1 1 d D B .
C3 C 0.21565(19) -0.1099(5) 0.54481(17) 0.0310(7) Uani 1 1 d D . .
H3 H 0.2310 -0.2003 0.5858 0.037 Uiso 1 1 calc RD B .
C4 C 0.26409(18) 0.0507(5) 0.53134(16) 0.0274(6) Uani 1 1 d D B .
H4 H 0.3127 0.0709 0.5634 0.033 Uiso 1 1 calc RD . .
C5 C 0.24168(16) 0.1823(4) 0.47094(15) 0.0224(6) Uani 1 1 d D . .
C6 C 0.17026(17) 0.1523(5) 0.42384(16) 0.0258(6) Uani 1 1 d D B .
H6 H 0.1549 0.2417 0.3826 0.031 Uiso 1 1 calc RD . .
C7 C 0.12168(18) -0.0077(5) 0.43721(17) 0.0300(7) Uani 1 1 d D . .
H7 H 0.0731 -0.0288 0.4052 0.036 Uiso 1 1 calc RD B .
C8 C 0.29528(16) 0.3554(4) 0.45899(15) 0.0230(6) Uani 1 1 d D B .
C9 C 0.27148(16) 0.4940(4) 0.39256(15) 0.0216(6) Uani 1 1 d D . .
H9A H 0.2194 0.5531 0.3969 0.026 Uiso 1 1 calc RD B .
H9B H 0.2657 0.4123 0.3455 0.026 Uiso 1 1 calc RD . .
C10 C 0.32926(15) 0.6667(4) 0.38553(15) 0.0205(5) Uani 1 1 d D B .
H10 H 0.3357 0.7549 0.4316 0.025 Uiso 1 1 calc RD . .
C11 C 0.40963(16) 0.5958(4) 0.36691(15) 0.0215(6) Uani 1 1 d D . .
H11 H 0.4265 0.4614 0.3898 0.026 Uiso 1 1 calc RD B .
C12 C 0.39654(16) 0.5940(4) 0.27869(16) 0.0230(6) Uani 1 1 d D B .
H12 H 0.4068 0.4567 0.2584 0.028 Uiso 1 1 calc RD . .
C13 C 0.30160(16) 0.7903(4) 0.31416(15) 0.0216(6) Uani 1 1 d D . .
H13 H 0.2441 0.8203 0.3096 0.026 Uiso 1 1 calc RD B .
C14 C 0.47192(16) 0.7633(4) 0.38540(16) 0.0232(6) Uani 1 1 d D B .
H14A H 0.4641 0.8401 0.4314 0.028 Uiso 1 1 calc RD . .
H14B H 0.5259 0.7074 0.3919 0.028 Uiso 1 1 calc RD . .
C15 C 0.45477(15) 0.8945(4) 0.31399(15) 0.0207(6) Uani 1 1 d D . .
C16 C 0.51376(15) 1.0544(4) 0.30134(16) 0.0209(5) Uani 1 1 d D A .
C17 C 0.54726(16) 1.1739(4) 0.36213(16) 0.0242(6) Uani 1 1 d D . .
H17 H 0.5345 1.1494 0.4113 0.029 Uiso 1 1 calc RD B .
C18 C 0.59920(17) 1.3288(4) 0.35105(17) 0.0274(6) Uani 1 1 d D A .
H18 H 0.6218 1.4102 0.3925 0.033 Uiso 1 1 calc RD . .
C19 C 0.61791(17) 1.3641(4) 0.27936(18) 0.0298(7) Uani 1 1 d D A .
C20 C 0.58560(19) 1.2438(5) 0.21876(19) 0.0337(7) Uani 1 1 d D . .
H20 H 0.5993 1.2670 0.1699 0.040 Uiso 1 1 calc RD A .
C21 C 0.53333(18) 1.0898(5) 0.22954(17) 0.0287(6) Uani 1 1 d D A .
H21 H 0.5109 1.0085 0.1879 0.034 Uiso 1 1 calc RD . .

loop_
_atom_site_aniso_label
_atom_site_aniso_U_11
_atom_site_aniso_U_22
_atom_site_aniso_U_33
_atom_site_aniso_U_23
_atom_site_aniso_U_13
_atom_site_aniso_U_12
S1 0.0204(3) 0.0169(3) 0.0285(4) 0.0015(3) 0.0013(3) 0.0012(3)
C22 0.0412(19) 0.0303(17) 0.056(2) -0.0081(15) 0.0205(16) -0.0082(14)
F1 0.051(2) 0.0242(16) 0.070(3) 0.0097(18) 0.028(2) -0.0050(15)
F2 0.224(7) 0.103(5) 0.041(2) -0.025(2) 0.050(3) -0.131(5)
F3 0.0214(19) 0.030(2) 0.224(7) 0.029(3) 0.011(3) -0.0088(16)
F1' 0.051(2) 0.0242(16) 0.070(3) 0.0097(18) 0.028(2) -0.0050(15)
F2' 0.224(7) 0.103(5) 0.041(2) -0.025(2) 0.050(3) -0.131(5)
F3' 0.0214(19) 0.030(2) 0.224(7) 0.029(3) 0.011(3) -0.0088(16)
F1" 0.224(7) 0.103(5) 0.041(2) -0.025(2) 0.050(3) -0.131(5)
F2" 0.0214(19) 0.030(2) 0.224(7) 0.029(3) 0.011(3) -0.0088(16)
F3" 0.051(2) 0.0242(16) 0.070(3) 0.0097(18) 0.028(2) -0.0050(15)
C1 0.047(2) 0.0376(18) 0.0374(18) 0.0014(14) 0.0127(15) -0.0130(15)
F4 0.0555(19) 0.0205(14) 0.082(3) 0.0092(16) 0.0272(18) -0.0026(14)
F5 0.143(5) 0.089(4) 0.0363(18) 0.0183(19) -0.026(2) -0.090(3)
F6 0.050(2) 0.0469(16) 0.092(3) 0.000(2) 0.045(2) -0.0116(18)
F4' 0.0555(19) 0.0205(14) 0.082(3) 0.0092(16) 0.0272(18) -0.0026(14)
F5' 0.143(5) 0.089(4) 0.0363(18) 0.0183(19) -0.026(2) -0.090(3)
F6' 0.050(2) 0.0469(16) 0.092(3) 0.000(2) 0.045(2) -0.0116(18)
F4" 0.050(2) 0.0469(16) 0.092(3) 0.000(2) 0.045(2) -0.0116(18)
F5" 0.0555(19) 0.0205(14) 0.082(3) 0.0092(16) 0.0272(18) -0.0026(14)
F6" 0.143(5) 0.089(4) 0.0363(18) 0.0183(19) -0.026(2) -0.090(3)
O1 0.0336(11) 0.0370(12) 0.0226(10) 0.0036(9) -0.0044(9) -0.0105(10)
O2 0.0232(10) 0.0226(10) 0.0219(10) -0.0009(8) -0.0011(8) -0.0028(8)
O3 0.0267(10) 0.0179(9) 0.0248(10) -0.0049(8) 0.0064(8) -0.0044(8)
C2 0.0373(17) 0.0253(15) 0.0294(15) -0.0020(12) 0.0136(13) -0.0064(13)
C3 0.0420(17) 0.0263(15) 0.0257(15) 0.0044(12) 0.0084(13) -0.0008(13)
C4 0.0311(15) 0.0275(15) 0.0230(14) 0.0019(12) 0.0018(12) -0.0017(12)
C5 0.0264(14) 0.0208(13) 0.0204(13) -0.0019(11) 0.0048(11) -0.0014(11)
C6 0.0277(14) 0.0270(14) 0.0227(14) 0.0015(12) 0.0037(11) -0.0023(12)
C7 0.0311(15) 0.0323(16) 0.0272(15) -0.0019(13) 0.0060(12) -0.0083(13)
C8 0.0271(14) 0.0246(14) 0.0173(13) -0.0032(11) 0.0032(11) -0.0006(11)
C9 0.0217(13) 0.0209(13) 0.0218(13) -0.0011(11) 0.0019(10) -0.0012(10)
C10 0.0222(13) 0.0175(12) 0.0210(13) -0.0017(10) 0.0008(10) -0.0009(10)
C11 0.0226(13) 0.0180(13) 0.0228(14) 0.0008(10) -0.0001(10) 0.0007(10)
C12 0.0252(14) 0.0180(13) 0.0259(14) -0.0011(11) 0.0038(11) 0.0006(11)
C13 0.0192(13) 0.0183(12) 0.0267(14) 0.0007(11) 0.0012(10) 0.0009(10)
C14 0.0203(13) 0.0230(13) 0.0242(14) 0.0023(11) -0.0034(10) 0.0000(11)
C15 0.0197(13) 0.0206(13) 0.0205(13) -0.0026(10) -0.0011(10) 0.0009(10)
C16 0.0187(12) 0.0192(13) 0.0242(14) -0.0003(11) 0.0015(10) 0.0015(10)
C17 0.0240(14) 0.0237(14) 0.0250(14) -0.0010(11) 0.0035(11) 0.0009(11)
C18 0.0258(14) 0.0243(14) 0.0314(15) -0.0058(12) 0.0014(12) -0.0023(11)
C19 0.0287(15) 0.0245(15) 0.0380(17) -0.0029(13) 0.0113(13) -0.0025(12)
C20 0.0389(17) 0.0310(16) 0.0338(17) -0.0020(13) 0.0142(14) -0.0049(14)
C21 0.0331(16) 0.0266(15) 0.0267(15) -0.0022(12) 0.0054(12) -0.0042(12)

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

loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
S1 C13 1.840(3) . ?
S1 C15 1.861(3) . ?
C22 F2' 1.298(3) . ?
C22 F1" 1.308(3) . ?
C22 F3 1.315(3) . ?
C22 F3" 1.319(3) . ?
C22 F1' 1.320(3) . ?
C22 F1 1.322(3) . ?
C22 F3' 1.322(3) . ?
C22 F2 1.326(3) . ?
C22 F2" 1.338(3) . ?
C22 C19 1.487(4) . ?
C1 F5 1.310(3) . ?
C1 F4" 1.311(3) . ?
C1 F6 1.315(3) . ?
C1 F6' 1.316(3) . ?
C1 F6" 1.319(3) . ?
C1 F4 1.321(3) . ?
C1 F5" 1.322(3) . ?
C1 F5' 1.324(3) . ?
C1 F4' 1.329(3) . ?
C1 C2 1.499(4) . ?
O1 C8 1.221(3) . ?
O2 C12 1.426(3) . ?
O2 C13 1.429(3) . ?
O3 C15 1.432(3) . ?
O3 C12 1.434(3) . ?
C2 C3 1.382(4) . ?
C2 C7 1.393(4) . ?
C3 C4 1.390(4) . ?
C3 H3 0.9500 . ?
C4 C5 1.393(4) . ?
C4 H4 0.9500 . ?
C5 C6 1.397(4) . ?
C5 C8 1.502(4) . ?
C6 C7 1.388(4) . ?
C6 H6 0.9500 . ?
C7 H7 0.9500 . ?
C8 C9 1.505(4) . ?
C9 C10 1.528(4) . ?
C9 H9A 0.9900 . ?
C9 H9B 0.9900 . ?
C10 C13 1.528(4) . ?
C10 C11 1.541(4) . ?
C10 H10 1.0000 . ?
C11 C14 1.540(4) . ?
C11 C12 1.558(4) . ?
C11 H11 1.0000 . ?
C12 H12 1.0000 . ?
C13 H13 1.0000 . ?
C14 C15 1.533(4) . ?
C14 H14A 0.9900 . ?
C14 H14B 0.9900 . ?
C15 C16 1.502(4) . ?
C16 C21 1.393(4) . ?
C16 C17 1.395(4) . ?
C17 C18 1.389(4) . ?
C17 H17 0.9500 . ?
C18 C19 1.385(4) . ?
C18 H18 0.9500 . ?
C19 C20 1.389(4) . ?
C20 C21 1.388(4) . ?
C20 H20 0.9500 . ?
C21 H21 0.9500 . ?

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
C13 S1 C15 94.73(12) . . ?
F1" C22 F3" 105.7(3) . . ?
F2' C22 F1' 106.2(3) . . ?
F3 C22 F1 104.9(3) . . ?
F2' C22 F3' 106.5(3) . . ?
F1' C22 F3' 103.5(3) . . ?
F3 C22 F2 104.6(3) . . ?
F1 C22 F2 104.1(3) . . ?
F1" C22 F2" 104.5(3) . . ?
F3" C22 F2" 103.3(3) . . ?
F2' C22 C19 116.4(3) . . ?
F1" C22 C19 120.6(4) . . ?
F3 C22 C19 119.8(4) . . ?
F3" C22 C19 114.7(4) . . ?
F1' C22 C19 111.8(3) . . ?
F1 C22 C19 112.0(5) . . ?
F3' C22 C19 111.5(3) . . ?
F2 C22 C19 110.0(5) . . ?
F2" C22 C19 106.3(4) . . ?
F5 C1 F6 106.8(3) . . ?
F4" C1 F6" 105.5(3) . . ?
F5 C1 F4 105.9(2) . . ?
F6 C1 F4 104.4(2) . . ?
F4" C1 F5" 105.4(3) . . ?
F6" C1 F5" 104.6(9) . . ?
F6' C1 F5' 115.6(12) . . ?
F6' C1 F4' 104.5(3) . . ?
F5' C1 F4' 103.7(3) . . ?
F5 C1 C2 113.4(3) . . ?
F4" C1 C2 116.4(6) . . ?
F6 C1 C2 111.8(3) . . ?
F6' C1 C2 115.5(6) . . ?
F6" C1 C2 113.3(6) . . ?
F4 C1 C2 113.8(3) . . ?
F5" C1 C2 110.7(6) . . ?
F5' C1 C2 108.6(8) . . ?
F4' C1 C2 107.8(6) . . ?
C12 O2 C13 103.80(19) . . ?
C15 O3 C12 104.5(2) . . ?
C3 C2 C7 121.2(3) . . ?
C3 C2 C1 119.4(3) . . ?
C7 C2 C1 119.4(3) . . ?
C2 C3 C4 119.4(3) . . ?
C2 C3 H3 120.3 . . ?
C4 C3 H3 120.3 . . ?
C3 C4 C5 120.2(3) . . ?
C3 C4 H4 119.9 . . ?
C5 C4 H4 119.9 . . ?
C4 C5 C6 119.8(3) . . ?
C4 C5 C8 118.5(3) . . ?
C6 C5 C8 121.7(2) . . ?
C7 C6 C5 120.1(3) . . ?
C7 C6 H6 119.9 . . ?
C5 C6 H6 119.9 . . ?
C6 C7 C2 119.3(3) . . ?
C6 C7 H7 120.4 . . ?
C2 C7 H7 120.4 . . ?
O1 C8 C5 120.3(3) . . ?
O1 C8 C9 121.6(3) . . ?
C5 C8 C9 118.1(2) . . ?
C8 C9 C10 114.3(2) . . ?
C8 C9 H9A 108.7 . . ?
C10 C9 H9A 108.7 . . ?
C8 C9 H9B 108.7 . . ?
C10 C9 H9B 108.7 . . ?
H9A C9 H9B 107.6 . . ?
C9 C10 C13 109.8(2) . . ?
C9 C10 C11 114.0(2) . . ?
C13 C10 C11 99.2(2) . . ?
C9 C10 H10 111.1 . . ?
C13 C10 H10 111.1 . . ?
C11 C10 H10 111.1 . . ?
C14 C11 C10 110.7(2) . . ?
C14 C11 C12 102.4(2) . . ?
C10 C11 C12 102.7(2) . . ?
C14 C11 H11 113.3 . . ?
C10 C11 H11 113.3 . . ?
C12 C11 H11 113.3 . . ?
O2 C12 O3 109.0(2) . . ?
O2 C12 C11 106.5(2) . . ?
O3 C12 C11 106.4(2) . . ?
O2 C12 H12 111.5 . . ?
O3 C12 H12 111.5 . . ?
C11 C12 H12 111.5 . . ?
O2 C13 C10 102.5(2) . . ?
O2 C13 S1 109.34(18) . . ?
C10 C13 S1 112.32(19) . . ?
O2 C13 H13 110.8 . . ?
C10 C13 H13 110.8 . . ?
S1 C13 H13 110.8 . . ?
C15 C14 C11 100.6(2) . . ?
C15 C14 H14A 111.7 . . ?
C11 C14 H14A 111.7 . . ?
C15 C14 H14B 111.7 . . ?
C11 C14 H14B 111.7 . . ?
H14A C14 H14B 109.4 . . ?
O3 C15 C16 110.8(2) . . ?
O3 C15 C14 101.5(2) . . ?
C16 C15 C14 118.0(2) . . ?
O3 C15 S1 108.98(17) . . ?
C16 C15 S1 106.64(18) . . ?
C14 C15 S1 110.70(19) . . ?
C21 C16 C17 119.6(3) . . ?
C21 C16 C15 121.1(2) . . ?
C17 C16 C15 119.3(2) . . ?
C18 C17 C16 120.3(3) . . ?
C18 C17 H17 119.9 . . ?
C16 C17 H17 119.9 . . ?
C19 C18 C17 119.8(3) . . ?
C19 C18 H18 120.1 . . ?
C17 C18 H18 120.1 . . ?
C18 C19 C20 120.2(3) . . ?
C18 C19 C22 118.4(3) . . ?
C20 C19 C22 121.4(3) . . ?
C21 C20 C19 120.1(3) . . ?
C21 C20 H20 119.9 . . ?
C19 C20 H20 119.9 . . ?
C20 C21 C16 120.0(3) . . ?
C20 C21 H21 120.0 . . ?
C16 C21 H21 120.0 . . ?

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
F5 C1 C2 C3 -153.6(4) . . . . ?
F4" C1 C2 C3 113.5(7) . . . . ?
F6 C1 C2 C3 85.6(4) . . . . ?
F6' C1 C2 C3 -76.8(10) . . . . ?
F6" C1 C2 C3 -9.1(9) . . . . ?
F4 C1 C2 C3 -32.4(4) . . . . ?
F5" C1 C2 C3 -126.3(7) . . . . ?
F5' C1 C2 C3 54.9(11) . . . . ?
F4' C1 C2 C3 166.7(8) . . . . ?
F5 C1 C2 C7 28.1(4) . . . . ?
F4" C1 C2 C7 -64.9(7) . . . . ?
F6 C1 C2 C7 -92.8(4) . . . . ?
F6' C1 C2 C7 104.8(10) . . . . ?
F6" C1 C2 C7 172.5(9) . . . . ?
F4 C1 C2 C7 149.3(3) . . . . ?
F5" C1 C2 C7 55.4(7) . . . . ?
F5' C1 C2 C7 -123.4(11) . . . . ?
F4' C1 C2 C7 -11.6(9) . . . . ?
C7 C2 C3 C4 0.7(5) . . . . ?
C1 C2 C3 C4 -177.6(3) . . . . ?
C2 C3 C4 C5 -0.4(5) . . . . ?
C3 C4 C5 C6 0.0(4) . . . . ?
C3 C4 C5 C8 179.2(3) . . . . ?
C4 C5 C6 C7 0.1(4) . . . . ?
C8 C5 C6 C7 -179.1(3) . . . . ?
C5 C6 C7 C2 0.2(4) . . . . ?
C3 C2 C7 C6 -0.6(5) . . . . ?
C1 C2 C7 C6 177.7(3) . . . . ?
C4 C5 C8 O1 -1.7(4) . . . . ?
C6 C5 C8 O1 177.6(3) . . . . ?
C4 C5 C8 C9 178.6(3) . . . . ?
C6 C5 C8 C9 -2.2(4) . . . . ?
O1 C8 C9 C10 -0.3(4) . . . . ?
C5 C8 C9 C10 179.4(2) . . . . ?
C8 C9 C10 C13 177.0(2) . . . . ?
C8 C9 C10 C11 66.7(3) . . . . ?
C9 C10 C11 C14 -162.0(2) . . . . ?
C13 C10 C11 C14 81.3(2) . . . . ?
C9 C10 C11 C12 89.3(3) . . . . ?
C13 C10 C11 C12 -27.3(2) . . . . ?
C13 O2 C12 O3 -84.0(2) . . . . ?
C13 O2 C12 C11 30.5(3) . . . . ?
C15 O3 C12 O2 83.5(2) . . . . ?
C15 O3 C12 C11 -31.0(3) . . . . ?
C14 C11 C12 O2 -115.2(2) . . . . ?
C10 C11 C12 O2 -0.3(3) . . . . ?
C14 C11 C12 O3 1.0(3) . . . . ?
C10 C11 C12 O3 115.9(2) . . . . ?
C12 O2 C13 C10 -49.4(2) . . . . ?
C12 O2 C13 S1 70.0(2) . . . . ?
C9 C10 C13 O2 -72.5(3) . . . . ?
C11 C10 C13 O2 47.2(2) . . . . ?
C9 C10 C13 S1 170.22(18) . . . . ?
C11 C10 C13 S1 -70.0(2) . . . . ?
C15 S1 C13 O2 -54.11(19) . . . . ?
C15 S1 C13 C10 59.0(2) . . . . ?
C10 C11 C14 C15 -82.2(3) . . . . ?
C12 C11 C14 C15 26.7(3) . . . . ?
C12 O3 C15 C16 174.8(2) . . . . ?
C12 O3 C15 C14 48.7(2) . . . . ?
C12 O3 C15 S1 -68.1(2) . . . . ?
C11 C14 C15 O3 -46.4(2) . . . . ?
C11 C14 C15 C16 -167.7(2) . . . . ?
C11 C14 C15 S1 69.2(2) . . . . ?
C13 S1 C15 O3 53.2(2) . . . . ?
C13 S1 C15 C16 172.81(18) . . . . ?
C13 S1 C15 C14 -57.7(2) . . . . ?
O3 C15 C16 C21 23.2(3) . . . . ?
C14 C15 C16 C21 139.5(3) . . . . ?
S1 C15 C16 C21 -95.3(3) . . . . ?
O3 C15 C16 C17 -159.1(2) . . . . ?
C14 C15 C16 C17 -42.8(4) . . . . ?
S1 C15 C16 C17 82.4(3) . . . . ?
C21 C16 C17 C18 0.7(4) . . . . ?
C15 C16 C17 C18 -177.0(3) . . . . ?
C16 C17 C18 C19 -0.2(4) . . . . ?
C17 C18 C19 C20 -0.7(5) . . . . ?
C17 C18 C19 C22 179.3(2) . . . . ?
F2' C22 C19 C18 -175.0(5) . . . . ?
F1" C22 C19 C18 -2.5(7) . . . . ?
F3 C22 C19 C18 -86.7(7) . . . . ?
F3" C22 C19 C18 125.7(5) . . . . ?
F1' C22 C19 C18 -52.8(4) . . . . ?
F1 C22 C19 C18 149.8(5) . . . . ?
F3' C22 C19 C18 62.6(4) . . . . ?
F2 C22 C19 C18 34.5(6) . . . . ?
F2" C22 C19 C18 -120.8(6) . . . . ?
F2' C22 C19 C20 5.0(5) . . . . ?
F1" C22 C19 C20 177.6(7) . . . . ?
F3 C22 C19 C20 93.3(7) . . . . ?
F3" C22 C19 C20 -54.3(6) . . . . ?
F1' C22 C19 C20 127.3(4) . . . . ?
F1 C22 C19 C20 -30.2(6) . . . . ?
F3' C22 C19 C20 -117.4(4) . . . . ?
F2 C22 C19 C20 -145.4(6) . . . . ?
F2" C22 C19 C20 59.2(6) . . . . ?
C18 C19 C20 C21 1.1(5) . . . . ?
C22 C19 C20 C21 -179.0(3) . . . . ?
C19 C20 C21 C16 -0.6(5) . . . . ?
C17 C16 C21 C20 -0.3(4) . . . . ?
C15 C16 C21 C20 177.4(3) . . . . ?

_refine_diff_density_max         1.120
_refine_diff_density_min         -0.883
_refine_diff_density_rms         0.077


data_p21nb
_database_code_depnum_ccdc_archive 'CCDC 904646'
#TrackingRef 'DK_JKD25A_p21n-final.cif'


_audit_creation_method           SHELXL-97
_chemical_name_systematic        
;
?
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         'C10 H10 S2'
_chemical_formula_sum            'C10 H10 S2'
_chemical_formula_weight         194.30

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'
S S 0.1246 0.1234 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_symmetry_cell_setting           monoclinic
_symmetry_space_group_name_H-M   '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                   5.955(2)
_cell_length_b                   7.649(3)
_cell_length_c                   20.480(7)
_cell_angle_alpha                90.00
_cell_angle_beta                 95.301(9)
_cell_angle_gamma                90.00
_cell_volume                     928.9(6)
_cell_formula_units_Z            4
_cell_measurement_temperature    100(2)
_cell_measurement_reflns_used    6971
_cell_measurement_theta_min      2.8430
_cell_measurement_theta_max      26.9195

_exptl_crystal_description       plate
_exptl_crystal_colour            colorless
_exptl_crystal_size_max          0.16
_exptl_crystal_size_mid          0.09
_exptl_crystal_size_min          0.06
_exptl_crystal_density_meas      ?
_exptl_crystal_density_diffrn    1.389
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             408
_exptl_absorpt_coefficient_mu    0.510
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.7510
_exptl_absorpt_correction_T_max  0.8620
_exptl_absorpt_process_details   SADABS-2008/2

_exptl_special_details           
;
?
;

_diffrn_ambient_temperature      100(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_radiation_source         'Bruker TXS-Mo rotating anode'
_diffrn_radiation_monochromator  'INCOATEC Helios mirror optics'
_diffrn_measurement_device_type  'Bruker Apex II ultra with D8-Goniometer'
_diffrn_measurement_method       'omega scans'
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            18476
_diffrn_reflns_av_R_equivalents  0.0410
_diffrn_reflns_av_sigmaI/netI    0.0206
_diffrn_reflns_limit_h_min       -7
_diffrn_reflns_limit_h_max       7
_diffrn_reflns_limit_k_min       -9
_diffrn_reflns_limit_k_max       9
_diffrn_reflns_limit_l_min       -26
_diffrn_reflns_limit_l_max       26
_diffrn_reflns_theta_min         2.00
_diffrn_reflns_theta_max         26.95
_reflns_number_total             2006
_reflns_number_gt                1750
_reflns_threshold_expression     >2sigma(I)

_computing_data_collection       'APEX2 v2010.7'
_computing_cell_refinement       'SAINT V7.68A'
_computing_data_reduction        'SAINT V7.68A'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 2008)'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 2008)'
_computing_molecular_graphics    'XP Version 5.1'
_computing_publication_material  'XP Version 5.1'

_refine_special_details          
;
Refinement of F^2^ against ALL reflections. The weighted R-factor wR and
goodness of fit S are based on F^2^, conventional R-factors R are based
on F, with F set to zero for negative F^2^. The threshold expression of
F^2^ > 2sigma(F^2^) is used only for calculating R-factors(gt) etc. and is
not relevant to the choice of reflections for refinement. R-factors based
on F^2^ 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/[\s^2^(Fo^2^)+(0.0262P)^2^+1.0157P] where P=(Fo^2^+2Fc^2^)/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         2006
_refine_ls_number_parameters     111
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0405
_refine_ls_R_factor_gt           0.0341
_refine_ls_wR_factor_ref         0.0846
_refine_ls_wR_factor_gt          0.0813
_refine_ls_goodness_of_fit_ref   1.132
_refine_ls_restrained_S_all      1.132
_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
S1 S 0.47012(8) -0.00477(6) 0.59149(2) 0.01805(14) Uani 1 1 d . . .
S2 S 0.53458(8) 0.17987(6) 0.90453(2) 0.01715(13) Uani 1 1 d . . .
C1 C 0.8702(3) 0.1723(3) 0.57138(9) 0.0198(4) Uani 1 1 d . . .
H1A H 0.7994 0.2603 0.5414 0.030 Uiso 1 1 calc R . .
H1B H 0.9144 0.0711 0.5462 0.030 Uiso 1 1 calc R . .
H1C H 1.0041 0.2226 0.5958 0.030 Uiso 1 1 calc R . .
C2 C 0.7066(3) 0.1161(2) 0.61830(9) 0.0161(4) Uani 1 1 d . . .
C3 C 0.7099(3) 0.1498(2) 0.68339(9) 0.0160(4) Uani 1 1 d . . .
H3 H 0.8267 0.2146 0.7071 0.019 Uiso 1 1 calc R . .
C4 C 0.5213(3) 0.0789(2) 0.71320(9) 0.0152(4) Uani 1 1 d . . .
C5 C 0.4847(3) 0.0972(2) 0.78265(9) 0.0148(4) Uani 1 1 d . . .
C6 C 0.2974(3) 0.0242(2) 0.81239(9) 0.0166(4) Uani 1 1 d . . .
H6 H 0.1816 -0.0414 0.7886 0.020 Uiso 1 1 calc R . .
C7 C 0.2997(3) 0.0570(2) 0.87761(9) 0.0160(4) Uani 1 1 d . . .
C8 C 0.1354(3) 0.0004(3) 0.92417(10) 0.0202(4) Uani 1 1 d . . .
H8C H 0.0165 -0.0702 0.9007 0.030 Uiso 1 1 calc R . .
H8A H 0.0681 0.1036 0.9430 0.030 Uiso 1 1 calc R . .
H8B H 0.2136 -0.0693 0.9594 0.030 Uiso 1 1 calc R . .
C9 C 0.3779(3) -0.0086(2) 0.66842(9) 0.0175(4) Uani 1 1 d . . .
H9 H 0.2433 -0.0648 0.6787 0.021 Uiso 1 1 calc R . .
C10 C 0.6271(3) 0.1855(2) 0.82755(9) 0.0168(4) Uani 1 1 d . . .
H10 H 0.7609 0.2430 0.8173 0.020 Uiso 1 1 calc R . .

loop_
_atom_site_aniso_label
_atom_site_aniso_U_11
_atom_site_aniso_U_22
_atom_site_aniso_U_33
_atom_site_aniso_U_23
_atom_site_aniso_U_13
_atom_site_aniso_U_12
S1 0.0177(2) 0.0195(3) 0.0167(2) -0.00209(18) -0.00003(17) -0.00166(18)
S2 0.0165(2) 0.0185(2) 0.0161(2) -0.00112(18) -0.00002(17) -0.00139(18)
C1 0.0198(10) 0.0191(10) 0.0210(9) 0.0012(8) 0.0051(7) -0.0013(8)
C2 0.0148(9) 0.0124(8) 0.0208(9) 0.0009(7) 0.0006(7) 0.0007(7)
C3 0.0155(9) 0.0119(8) 0.0202(9) -0.0002(7) 0.0002(7) -0.0005(7)
C4 0.0147(9) 0.0119(8) 0.0187(9) 0.0001(7) 0.0007(7) 0.0022(7)
C5 0.0143(9) 0.0107(8) 0.0195(9) 0.0000(7) 0.0007(7) 0.0016(7)
C6 0.0143(9) 0.0146(9) 0.0205(9) -0.0006(7) 0.0003(7) -0.0010(7)
C7 0.0143(9) 0.0121(9) 0.0213(9) 0.0008(7) 0.0001(7) 0.0014(7)
C8 0.0195(10) 0.0205(10) 0.0210(10) 0.0012(7) 0.0043(7) -0.0023(8)
C9 0.0164(9) 0.0175(9) 0.0187(9) -0.0005(7) 0.0028(7) -0.0007(7)
C10 0.0161(9) 0.0165(9) 0.0180(9) 0.0002(7) 0.0024(7) -0.0019(7)

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

loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
S1 C9 1.716(2) . ?
S1 C2 1.7307(19) . ?
S2 C10 1.7179(19) . ?
S2 C7 1.7322(19) . ?
C1 C2 1.494(3) . ?
C1 H1A 0.9800 . ?
C1 H1B 0.9800 . ?
C1 H1C 0.9800 . ?
C2 C3 1.356(3) . ?
C3 C4 1.434(3) . ?
C3 H3 0.9500 . ?
C4 C9 1.368(3) . ?
C4 C5 1.465(3) . ?
C5 C10 1.370(3) . ?
C5 C6 1.433(3) . ?
C6 C7 1.358(3) . ?
C6 H6 0.9500 . ?
C7 C8 1.492(3) . ?
C8 H8C 0.9800 . ?
C8 H8A 0.9800 . ?
C8 H8B 0.9800 . ?
C9 H9 0.9500 . ?
C10 H10 0.9500 . ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
C9 S1 C2 92.15(9) . . ?
C10 S2 C7 92.27(9) . . ?
C2 C1 H1A 109.5 . . ?
C2 C1 H1B 109.5 . . ?
H1A C1 H1B 109.5 . . ?
C2 C1 H1C 109.5 . . ?
H1A C1 H1C 109.5 . . ?
H1B C1 H1C 109.5 . . ?
C3 C2 C1 128.78(17) . . ?
C3 C2 S1 110.56(14) . . ?
C1 C2 S1 120.64(14) . . ?
C2 C3 C4 113.93(17) . . ?
C2 C3 H3 123.0 . . ?
C4 C3 H3 123.0 . . ?
C9 C4 C3 111.36(16) . . ?
C9 C4 C5 123.90(17) . . ?
C3 C4 C5 124.74(16) . . ?
C10 C5 C6 111.40(17) . . ?
C10 C5 C4 124.06(17) . . ?
C6 C5 C4 124.54(16) . . ?
C7 C6 C5 114.11(17) . . ?
C7 C6 H6 122.9 . . ?
C5 C6 H6 122.9 . . ?
C6 C7 C8 128.84(18) . . ?
C6 C7 S2 110.37(14) . . ?
C8 C7 S2 120.79(14) . . ?
C7 C8 H8C 109.5 . . ?
C7 C8 H8A 109.5 . . ?
H8C C8 H8A 109.5 . . ?
C7 C8 H8B 109.5 . . ?
H8C C8 H8B 109.5 . . ?
H8A C8 H8B 109.5 . . ?
C4 C9 S1 111.99(14) . . ?
C4 C9 H9 124.0 . . ?
S1 C9 H9 124.0 . . ?
C5 C10 S2 111.85(14) . . ?
C5 C10 H10 124.1 . . ?
S2 C10 H10 124.1 . . ?

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
C9 S1 C2 C3 0.01(15) . . . . ?
C9 S1 C2 C1 -178.53(16) . . . . ?
C1 C2 C3 C4 178.36(18) . . . . ?
S1 C2 C3 C4 0.0(2) . . . . ?
C2 C3 C4 C9 0.0(2) . . . . ?
C2 C3 C4 C5 -179.84(17) . . . . ?
C9 C4 C5 C10 -179.59(18) . . . . ?
C3 C4 C5 C10 0.3(3) . . . . ?
C9 C4 C5 C6 0.9(3) . . . . ?
C3 C4 C5 C6 -179.18(18) . . . . ?
C10 C5 C6 C7 0.0(2) . . . . ?
C4 C5 C6 C7 179.51(17) . . . . ?
C5 C6 C7 C8 -179.22(18) . . . . ?
C5 C6 C7 S2 0.0(2) . . . . ?
C10 S2 C7 C6 -0.03(15) . . . . ?
C10 S2 C7 C8 179.28(16) . . . . ?
C3 C4 C9 S1 0.0(2) . . . . ?
C5 C4 C9 S1 179.85(14) . . . . ?
C2 S1 C9 C4 0.02(15) . . . . ?
C6 C5 C10 S2 0.0(2) . . . . ?
C4 C5 C10 S2 -179.54(14) . . . . ?
C7 S2 C10 C5 0.03(15) . . . . ?

_diffrn_measured_fraction_theta_max 0.999
_diffrn_reflns_theta_full        26.95
_diffrn_measured_fraction_theta_full 0.999
_refine_diff_density_max         0.413
_refine_diff_density_min         -0.246
_refine_diff_density_rms         0.058


data_p-1
_database_code_depnum_ccdc_archive 'CCDC 904647'
#TrackingRef 'DK_JKEX06_final.cif'


_audit_creation_method           SHELXL-97
_chemical_name_systematic        
;
?
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         'C10 H14 O3 Se'
_chemical_formula_sum            'C10 H14 O3 Se'
_chemical_formula_weight         261.17

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           triclinic
_symmetry_space_group_name_H-M   'P -1'
_symmetry_space_group_name_Hall  '-P 1'

loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'-x, -y, -z'

_cell_length_a                   6.388(3)
_cell_length_b                   9.236(5)
_cell_length_c                   9.469(5)
_cell_angle_alpha                73.414(2)
_cell_angle_beta                 74.033(3)
_cell_angle_gamma                81.773(3)
_cell_volume                     513.6(5)
_cell_formula_units_Z            2
_cell_measurement_temperature    100(2)
_cell_measurement_reflns_used    9877
_cell_measurement_theta_min      2.3065
_cell_measurement_theta_max      26.75

_exptl_crystal_description       block
_exptl_crystal_colour            colorless
_exptl_crystal_size_max          0.18
_exptl_crystal_size_mid          0.17
_exptl_crystal_size_min          0.09
_exptl_crystal_density_meas      ?
_exptl_crystal_density_diffrn    1.689
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             264
_exptl_absorpt_coefficient_mu    3.634
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.5608
_exptl_absorpt_correction_T_max  0.7357
_exptl_absorpt_process_details   'SADABS-2008/2, Sheldrick, Goettingen'

_exptl_special_details           
;
?
;

_diffrn_ambient_temperature      100(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_radiation_source         'rotating anode (TXS)'
_diffrn_radiation_monochromator  mirror
_diffrn_measurement_device_type  'Bruker Smart APEX II Ultra'
_diffrn_measurement_method       'omega scans'
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            26279
_diffrn_reflns_av_R_equivalents  0.0312
_diffrn_reflns_av_sigmaI/netI    0.0121
_diffrn_reflns_limit_h_min       -8
_diffrn_reflns_limit_h_max       8
_diffrn_reflns_limit_k_min       -11
_diffrn_reflns_limit_k_max       11
_diffrn_reflns_limit_l_min       -11
_diffrn_reflns_limit_l_max       11
_diffrn_reflns_theta_min         2.31
_diffrn_reflns_theta_max         26.75
_reflns_number_total             2185
_reflns_number_gt                2159
_reflns_threshold_expression     >2sigma(I)

_computing_data_collection       'APEX2 v2011.2'
_computing_cell_refinement       'SAINT V7.68A'
_computing_data_reduction        'SAINT V7.68A'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 2008)'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 2008)'
_computing_molecular_graphics    'XP Version 5.1'
_computing_publication_material  'XP Version 5.1'

_refine_special_details          
;
Refinement of F^2^ against ALL reflections. The weighted R-factor wR and
goodness of fit S are based on F^2^, conventional R-factors R are based
on F, with F set to zero for negative F^2^. The threshold expression of
F^2^ > 2sigma(F^2^) is used only for calculating R-factors(gt) etc. and is
not relevant to the choice of reflections for refinement. R-factors based
on F^2^ 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/[\s^2^(Fo^2^)+(0.0222P)^2^+0.2228P] where P=(Fo^2^+2Fc^2^)/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     SHELXL
_refine_ls_extinction_coef       0.043(2)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc^2^\l^3^/sin(2\q)]^-1/4^
_refine_ls_number_reflns         2185
_refine_ls_number_parameters     130
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0162
_refine_ls_R_factor_gt           0.0160
_refine_ls_wR_factor_ref         0.0428
_refine_ls_wR_factor_gt          0.0427
_refine_ls_goodness_of_fit_ref   1.158
_refine_ls_restrained_S_all      1.158
_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 0.72584(2) 0.147458(14) 0.402334(14) 0.01357(7) Uani 1 1 d . . .
O1 O 1.22588(18) 0.41397(12) 0.47519(12) 0.0216(2) Uani 1 1 d . . .
O2 O 0.88364(16) 0.38795(10) 0.15311(11) 0.01413(19) Uani 1 1 d . . .
O3 O 0.83229(16) 0.17299(11) 0.08838(11) 0.0142(2) Uani 1 1 d . . .
C1 C 1.4181(3) 0.61577(18) 0.2885(2) 0.0270(3) Uani 1 1 d . . .
H1A H 1.5551 0.6051 0.2128 0.040 Uiso 1 1 calc R . .
H1B H 1.4491 0.6386 0.3754 0.040 Uiso 1 1 calc R . .
H1C H 1.3232 0.6983 0.2428 0.040 Uiso 1 1 calc R . .
C2 C 1.3054(2) 0.47003(16) 0.34172(17) 0.0175(3) Uani 1 1 d . . .
C3 C 1.3020(2) 0.39770(16) 0.21791(16) 0.0158(3) Uani 1 1 d . . .
H3A H 1.4529 0.3616 0.1741 0.019 Uiso 1 1 calc R . .
H3B H 1.2512 0.4758 0.1360 0.019 Uiso 1 1 calc R . .
C4 C 0.9158(2) 0.32079(15) 0.30253(15) 0.0138(3) Uani 1 1 d . . .
H4 H 0.8842 0.3967 0.3641 0.017 Uiso 1 1 calc R . .
C5 C 1.1568(2) 0.26533(15) 0.27117(15) 0.0133(3) Uani 1 1 d . . .
H5 H 1.1914 0.1892 0.3622 0.016 Uiso 1 1 calc R . .
C6 C 1.1715(2) 0.19127(15) 0.14216(15) 0.0135(3) Uani 1 1 d . . .
H6 H 1.3177 0.1979 0.0681 0.016 Uiso 1 1 calc R . .
C7 C 0.9842(2) 0.28042(15) 0.06852(15) 0.0135(3) Uani 1 1 d . . .
H7 H 1.0419 0.3312 -0.0415 0.016 Uiso 1 1 calc R . .
C8 C 1.0967(2) 0.02925(15) 0.20224(15) 0.0141(3) Uani 1 1 d . . .
H8A H 1.1605 -0.0310 0.1274 0.017 Uiso 1 1 calc R . .
H8B H 1.1356 -0.0232 0.2994 0.017 Uiso 1 1 calc R . .
C9 C 0.8511(2) 0.05772(15) 0.22426(15) 0.0138(3) Uani 1 1 d . . .
C10 C 0.7253(2) -0.07461(16) 0.24150(16) 0.0181(3) Uani 1 1 d . . .
H10A H 0.7864 -0.1184 0.1546 0.027 Uiso 1 1 calc R . .
H10B H 0.5718 -0.0403 0.2454 0.027 Uiso 1 1 calc R . .
H10C H 0.7355 -0.1514 0.3357 0.027 Uiso 1 1 calc R . .

loop_
_atom_site_aniso_label
_atom_site_aniso_U_11
_atom_site_aniso_U_22
_atom_site_aniso_U_33
_atom_site_aniso_U_23
_atom_site_aniso_U_13
_atom_site_aniso_U_12
Se1 0.01410(9) 0.01399(9) 0.01152(9) -0.00333(5) -0.00084(5) -0.00202(5)
O1 0.0234(5) 0.0212(5) 0.0221(6) -0.0087(4) -0.0056(4) -0.0011(4)
O2 0.0168(5) 0.0109(4) 0.0141(5) -0.0027(4) -0.0044(4) 0.0009(4)
O3 0.0171(5) 0.0129(5) 0.0125(5) -0.0015(4) -0.0042(4) -0.0036(4)
C1 0.0293(8) 0.0196(7) 0.0351(9) -0.0091(7) -0.0078(7) -0.0075(6)
C2 0.0142(6) 0.0145(6) 0.0261(8) -0.0074(6) -0.0077(6) 0.0017(5)
C3 0.0152(6) 0.0143(6) 0.0180(7) -0.0032(5) -0.0048(5) -0.0020(5)
C4 0.0150(6) 0.0122(6) 0.0143(6) -0.0034(5) -0.0037(5) -0.0012(5)
C5 0.0140(6) 0.0123(6) 0.0140(6) -0.0036(5) -0.0041(5) -0.0004(5)
C6 0.0139(6) 0.0122(6) 0.0132(6) -0.0029(5) -0.0020(5) -0.0006(5)
C7 0.0151(6) 0.0116(6) 0.0131(6) -0.0029(5) -0.0026(5) -0.0016(5)
C8 0.0165(6) 0.0115(6) 0.0138(6) -0.0035(5) -0.0029(5) -0.0001(5)
C9 0.0175(6) 0.0123(6) 0.0113(6) -0.0029(5) -0.0030(5) -0.0010(5)
C10 0.0221(7) 0.0159(7) 0.0161(7) -0.0040(5) -0.0022(5) -0.0062(5)

_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 C4 1.9977(13) . ?
Se1 C9 2.0092(13) . ?
O1 C2 1.2134(19) . ?
O2 C7 1.4245(16) . ?
O2 C4 1.4324(16) . ?
O3 C7 1.4251(16) . ?
O3 C9 1.4388(16) . ?
C1 C2 1.508(2) . ?
C1 H1A 0.9800 . ?
C1 H1B 0.9800 . ?
C1 H1C 0.9800 . ?
C2 C3 1.5122(19) . ?
C3 C5 1.5246(19) . ?
C3 H3A 0.9900 . ?
C3 H3B 0.9900 . ?
C4 C5 1.5268(18) . ?
C4 H4 1.0000 . ?
C5 C6 1.5380(18) . ?
C5 H5 1.0000 . ?
C6 C8 1.5362(18) . ?
C6 C7 1.5635(18) . ?
C6 H6 1.0000 . ?
C7 H7 1.0000 . ?
C8 C9 1.5191(19) . ?
C8 H8A 0.9900 . ?
C8 H8B 0.9900 . ?
C9 C10 1.5041(19) . ?
C10 H10A 0.9800 . ?
C10 H10B 0.9800 . ?
C10 H10C 0.9800 . ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
C4 Se1 C9 90.58(6) . . ?
C7 O2 C4 104.94(10) . . ?
C7 O3 C9 105.66(10) . . ?
C2 C1 H1A 109.5 . . ?
C2 C1 H1B 109.5 . . ?
H1A C1 H1B 109.5 . . ?
C2 C1 H1C 109.5 . . ?
H1A C1 H1C 109.5 . . ?
H1B C1 H1C 109.5 . . ?
O1 C2 C1 122.01(14) . . ?
O1 C2 C3 122.51(13) . . ?
C1 C2 C3 115.48(13) . . ?
C2 C3 C5 114.26(12) . . ?
C2 C3 H3A 108.7 . . ?
C5 C3 H3A 108.7 . . ?
C2 C3 H3B 108.7 . . ?
C5 C3 H3B 108.7 . . ?
H3A C3 H3B 107.6 . . ?
O2 C4 C5 102.96(10) . . ?
O2 C4 Se1 108.51(8) . . ?
C5 C4 Se1 111.06(9) . . ?
O2 C4 H4 111.3 . . ?
C5 C4 H4 111.3 . . ?
Se1 C4 H4 111.3 . . ?
C3 C5 C4 110.98(11) . . ?
C3 C5 C6 111.53(11) . . ?
C4 C5 C6 100.08(10) . . ?
C3 C5 H5 111.3 . . ?
C4 C5 H5 111.3 . . ?
C6 C5 H5 111.3 . . ?
C8 C6 C5 112.30(11) . . ?
C8 C6 C7 102.56(10) . . ?
C5 C6 C7 102.93(10) . . ?
C8 C6 H6 112.7 . . ?
C5 C6 H6 112.7 . . ?
C7 C6 H6 112.7 . . ?
O2 C7 O3 109.53(10) . . ?
O2 C7 C6 106.50(10) . . ?
O3 C7 C6 106.54(10) . . ?
O2 C7 H7 111.3 . . ?
O3 C7 H7 111.3 . . ?
C6 C7 H7 111.3 . . ?
C9 C8 C6 101.69(10) . . ?
C9 C8 H8A 111.4 . . ?
C6 C8 H8A 111.4 . . ?
C9 C8 H8B 111.4 . . ?
C6 C8 H8B 111.4 . . ?
H8A C8 H8B 109.3 . . ?
O3 C9 C10 109.95(11) . . ?
O3 C9 C8 102.48(10) . . ?
C10 C9 C8 117.12(12) . . ?
O3 C9 Se1 107.97(8) . . ?
C10 C9 Se1 109.49(9) . . ?
C8 C9 Se1 109.35(9) . . ?
C9 C10 H10A 109.5 . . ?
C9 C10 H10B 109.5 . . ?
H10A C10 H10B 109.5 . . ?
C9 C10 H10C 109.5 . . ?
H10A C10 H10C 109.5 . . ?
H10B C10 H10C 109.5 . . ?

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
O1 C2 C3 C5 10.30(19) . . . . ?
C1 C2 C3 C5 -170.69(12) . . . . ?
C7 O2 C4 C5 46.66(12) . . . . ?
C7 O2 C4 Se1 -71.11(10) . . . . ?
C9 Se1 C4 O2 53.27(9) . . . . ?
C9 Se1 C4 C5 -59.22(10) . . . . ?
C2 C3 C5 C4 72.71(15) . . . . ?
C2 C3 C5 C6 -176.63(11) . . . . ?
O2 C4 C5 C3 72.80(13) . . . . ?
Se1 C4 C5 C3 -171.24(9) . . . . ?
O2 C4 C5 C6 -45.06(12) . . . . ?
Se1 C4 C5 C6 70.90(11) . . . . ?
C3 C5 C6 C8 159.64(11) . . . . ?
C4 C5 C6 C8 -82.90(12) . . . . ?
C3 C5 C6 C7 -90.77(12) . . . . ?
C4 C5 C6 C7 26.69(12) . . . . ?
C4 O2 C7 O3 86.49(12) . . . . ?
C4 O2 C7 C6 -28.35(13) . . . . ?
C9 O3 C7 O2 -86.42(12) . . . . ?
C9 O3 C7 C6 28.40(13) . . . . ?
C8 C6 C7 O2 116.24(11) . . . . ?
C5 C6 C7 O2 -0.50(13) . . . . ?
C8 C6 C7 O3 -0.61(13) . . . . ?
C5 C6 C7 O3 -117.35(11) . . . . ?
C5 C6 C8 C9 84.49(12) . . . . ?
C7 C6 C8 C9 -25.33(12) . . . . ?
C7 O3 C9 C10 -170.52(11) . . . . ?
C7 O3 C9 C8 -45.29(12) . . . . ?
C7 O3 C9 Se1 70.09(10) . . . . ?
C6 C8 C9 O3 43.26(12) . . . . ?
C6 C8 C9 C10 163.65(11) . . . . ?
C6 C8 C9 Se1 -71.10(11) . . . . ?
C4 Se1 C9 O3 -52.42(9) . . . . ?
C4 Se1 C9 C10 -172.11(10) . . . . ?
C4 Se1 C9 C8 58.35(9) . . . . ?

_diffrn_measured_fraction_theta_max 0.998
_diffrn_reflns_theta_full        26.75
_diffrn_measured_fraction_theta_full 0.998
_refine_diff_density_max         0.437
_refine_diff_density_min         -0.271
_refine_diff_density_rms         0.060