 
data_2009src0172
 
_audit_creation_method            SHELXL-97
_chemical_name_systematic
;
 ?
;
_chemical_name_common             ?
_chemical_melting_point           ?
_chemical_formula_moiety          ?
_chemical_formula_sum
 'C20 H26 O4 S2 Se2'
_chemical_formula_weight          552.45
 
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'
 '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/n
 
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                    13.0885(2)
_cell_length_b                    12.5754(3)
_cell_length_c                    14.4854(3)
_cell_angle_alpha                 90.00
_cell_angle_beta                  110.7530(10)
_cell_angle_gamma                 90.00
_cell_volume                      2229.50(8)
_cell_formula_units_Z             4
_cell_measurement_temperature     120(2)
_cell_measurement_reflns_used     23819
_cell_measurement_theta_min       2.91
_cell_measurement_theta_max       27.48
 
_exptl_crystal_description        block
_exptl_crystal_colour             colourless
_exptl_crystal_size_max           0.33
_exptl_crystal_size_mid           0.23
_exptl_crystal_size_min           0.09
_exptl_crystal_density_meas       ?
_exptl_crystal_density_diffrn     1.646
_exptl_crystal_density_method     'not measured'
_exptl_crystal_F_000              1112
_exptl_absorpt_coefficient_mu     3.527
_exptl_absorpt_correction_type    multi-scan
_exptl_absorpt_correction_T_min   0.3890
_exptl_absorpt_correction_T_max   0.7419
_exptl_absorpt_process_details    'SADABS 2007/2 (Sheldrick, G.M., 2007)' 
 
_exptl_special_details
;
 ?
;
 
_diffrn_ambient_temperature           120(2)
_diffrn_radiation_wavelength           0.71073
_diffrn_radiation_type                      MoK\a
_diffrn_radiation_source                  'Bruker-Nonius FR591 rotating anode'
_diffrn_radiation_monochromator    'graphite'
_diffrn_measurement_device_type   
'Bruker-Nonius Roper CCD camera on κ-goniostat'
_diffrn_measurement_method          'φ & ω scans'
_diffrn_detector_area_resol_mean   '9.091'
_diffrn_standards_number          ?
_diffrn_standards_interval_count  ?
_diffrn_standards_interval_time   ?
_diffrn_standards_decay_%         ?
_diffrn_reflns_number             35179
_diffrn_reflns_av_R_equivalents   0.0752
_diffrn_reflns_av_sigmaI/netI     0.0518
_diffrn_reflns_limit_h_min        -16
_diffrn_reflns_limit_h_max        16
_diffrn_reflns_limit_k_min        -16
_diffrn_reflns_limit_k_max        16
_diffrn_reflns_limit_l_min        -18
_diffrn_reflns_limit_l_max        18
_diffrn_reflns_theta_min          3.01
_diffrn_reflns_theta_max          27.48
_reflns_number_total              5099
_reflns_number_gt                 3980
_reflns_threshold_expression      >2σ(I)
 
_computing_data_collection        
'COLLECT (Hooft, R.W.W., 1998)'
_computing_cell_refinement        
'DENZO (Otwinowski & Minor, 1997) & COLLECT (Hooft, R.W.W., 1998)'
#Although determined using DirAx, the cell is refined in the HKL
#package during data reduction
_computing_data_reduction         
'DENZO (Otwinowski & Minor, 1997) & COLLECT (Hooft, R.W.W., 1998)'  
_computing_structure_solution     ?
_computing_structure_refinement   'SHELXL-97 (Sheldrick, 2008)'
_computing_molecular_graphics     ?
_computing_publication_material   ?
 
_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 > 2σ(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)+(0.0178P)²+3.1282P] 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          5099
_refine_ls_number_parameters      259
_refine_ls_number_restraints      0
_refine_ls_R_factor_all           0.0565
_refine_ls_R_factor_gt            0.0366
_refine_ls_wR_factor_ref          0.0758
_refine_ls_wR_factor_gt           0.0695
_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
C1 C 0.8001(2) 0.1746(2) 0.1653(2) 0.0173(6) Uani 1 1 d . . .
C2 C 0.7854(2) 0.1027(2) 0.0872(2) 0.0199(7) Uani 1 1 d . . .
C3 C 0.8785(3) 0.0560(3) 0.0787(2) 0.0230(7) Uani 1 1 d . . .
H3 H 0.8708 0.0069 0.0268 0.028 Uiso 1 1 calc R . .
C4 C 0.9820(3) 0.0802(3) 0.1449(3) 0.0268(8) Uani 1 1 d . . .
H4 H 1.0443 0.0481 0.1373 0.032 Uiso 1 1 calc R . .
C5 C 0.9954(3) 0.1505(3) 0.2217(3) 0.0288(8) Uani 1 1 d . . .
H5 H 1.0665 0.1666 0.2668 0.035 Uiso 1 1 calc R . .
C6 C 0.9047(3) 0.1974(3) 0.2326(2) 0.0246(7) Uani 1 1 d . . .
H6 H 0.9134 0.2450 0.2857 0.030 Uiso 1 1 calc R . .
C7 C 0.6715(3) 0.3679(2) 0.1331(2) 0.0221(7) Uani 1 1 d . . .
C8 C 0.6345(3) 0.3557(3) 0.0218(2) 0.0306(8) Uani 1 1 d . . .
H8A H 0.5682 0.3120 -0.0015 0.046 Uiso 1 1 calc R . .
H8B H 0.6923 0.3212 0.0043 0.046 Uiso 1 1 calc R . .
H8C H 0.6189 0.4259 -0.0093 0.046 Uiso 1 1 calc R . .
C9 C 0.5822(3) 0.4196(3) 0.1632(3) 0.0321(8) Uani 1 1 d . . .
H9A H 0.5659 0.4906 0.1338 0.048 Uiso 1 1 calc R . .
H9B H 0.6074 0.4255 0.2353 0.048 Uiso 1 1 calc R . .
H9C H 0.5160 0.3758 0.1398 0.048 Uiso 1 1 calc R . .
C10 C 0.7779(3) 0.4312(3) 0.1747(3) 0.0312(8) Uani 1 1 d . . .
H10A H 0.8340 0.3979 0.1541 0.047 Uiso 1 1 calc R . .
H10B H 0.8023 0.4321 0.2469 0.047 Uiso 1 1 calc R . .
H10C H 0.7654 0.5043 0.1497 0.047 Uiso 1 1 calc R . .
C21 C 0.6904(2) -0.1485(2) -0.1201(2) 0.0177(6) Uani 1 1 d . . .
C22 C 0.6975(2) -0.2181(2) -0.1936(2) 0.0164(6) Uani 1 1 d . . .
C23 C 0.7110(2) -0.3273(2) -0.1761(2) 0.0188(6) Uani 1 1 d . . .
H23 H 0.7183 -0.3729 -0.2257 0.023 Uiso 1 1 calc R . .
C24 C 0.7137(2) -0.3696(2) -0.0872(2) 0.0212(7) Uani 1 1 d . . .
H24 H 0.7231 -0.4439 -0.0752 0.025 Uiso 1 1 calc R . .
C25 C 0.7025(3) -0.3017(3) -0.0156(2) 0.0234(7) Uani 1 1 d . . .
H25 H 0.7016 -0.3303 0.0447 0.028 Uiso 1 1 calc R . .
C26 C 0.6928(2) -0.1931(3) -0.0311(2) 0.0219(7) Uani 1 1 d . . .
H26 H 0.6876 -0.1481 0.0197 0.026 Uiso 1 1 calc R . .
C27 C 0.5487(2) -0.1842(2) -0.3935(2) 0.0177(6) Uani 1 1 d . . .
C28 C 0.5490(3) -0.1505(3) -0.4949(2) 0.0242(7) Uani 1 1 d . . .
H28A H 0.5907 -0.2022 -0.5179 0.036 Uiso 1 1 calc R . .
H28B H 0.5828 -0.0801 -0.4899 0.036 Uiso 1 1 calc R . .
H28C H 0.4737 -0.1476 -0.5419 0.036 Uiso 1 1 calc R . .
C29 C 0.5087(3) -0.2980(3) -0.3957(2) 0.0247(7) Uani 1 1 d . . .
H29A H 0.4349 -0.3042 -0.4451 0.037 Uiso 1 1 calc R . .
H29B H 0.5072 -0.3170 -0.3305 0.037 Uiso 1 1 calc R . .
H29C H 0.5581 -0.3461 -0.4128 0.037 Uiso 1 1 calc R . .
C30 C 0.4822(2) -0.1067(3) -0.3557(2) 0.0231(7) Uani 1 1 d . . .
H30A H 0.4064 -0.1054 -0.4018 0.035 Uiso 1 1 calc R . .
H30B H 0.5137 -0.0353 -0.3505 0.035 Uiso 1 1 calc R . .
H30C H 0.4838 -0.1299 -0.2906 0.035 Uiso 1 1 calc R . .
O1 O 0.59323(17) 0.17432(18) 0.14210(16) 0.0246(5) Uani 1 1 d . . .
O2 O 0.72566(19) 0.25244(19) 0.29501(16) 0.0297(5) Uani 1 1 d . . .
O21 O 0.75141(17) -0.25227(17) -0.34840(16) 0.0217(5) Uani 1 1 d . . .
O22 O 0.72584(17) -0.06653(17) -0.30454(16) 0.0218(5) Uani 1 1 d . . .
S3 S 0.69121(6) -0.17655(6) -0.31243(5) 0.01659(16) Uani 1 1 d . . .
S4 S 0.69040(6) 0.23662(6) 0.18942(5) 0.01922(17) Uani 1 1 d . . .
Se1 Se 0.64071(2) 0.06601(3) -0.00542(2) 0.02112(9) Uani 1 1 d . . .
Se2 Se 0.68259(3) 0.00504(2) -0.13931(2) 0.02194(9) Uani 1 1 d . . .
 
 
_geom_special_details
;
 All s.u.'s (except the s.u. in the dihedral angle between two l.s. planes)
 are estimated using the full covariance matrix.  The cell s.u.'s are taken
 into account individually in the estimation of s.u.'s in distances, angles
 and torsion angles; correlations between s.u.'s in cell parameters are only
 used when they are defined by crystal symmetry.  An approximate (isotropic)
 treatment of cell s.u.'s is used for estimating s.u.'s 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 C6 1.400(4) . ?
C1 C2 1.407(4) . ?
C1 S4 1.775(3) . ?
C2 C3 1.397(4) . ?
C2 Se1 1.949(3) . ?
C3 C4 1.388(4) . ?
C3 H3 0.9500 . ?
C4 C5 1.384(5) . ?
C4 H4 0.9500 . ?
C5 C6 1.383(5) . ?
C5 H5 0.9500 . ?
C6 H6 0.9500 . ?
C7 C8 1.518(4) . ?
C7 C10 1.530(4) . ?
C7 C9 1.531(4) . ?
C7 S4 1.820(3) . ?
C8 H8A 0.9800 . ?
C8 H8B 0.9800 . ?
C8 H8C 0.9800 . ?
C9 H9A 0.9800 . ?
C9 H9B 0.9800 . ?
C9 H9C 0.9800 . ?
C10 H10A 0.9800 . ?
C10 H10B 0.9800 . ?
C10 H10C 0.9800 . ?
C21 C26 1.396(4) . ?
C21 C22 1.408(4) . ?
C21 Se2 1.948(3) . ?
C22 C23 1.396(4) . ?
C22 S3 1.773(3) . ?
C23 C24 1.382(4) . ?
C23 H23 0.9500 . ?
C24 C25 1.390(4) . ?
C24 H24 0.9500 . ?
C25 C26 1.382(4) . ?
C25 H25 0.9500 . ?
C26 H26 0.9500 . ?
C27 C29 1.521(4) . ?
C27 C28 1.531(4) . ?
C27 C30 1.531(4) . ?
C27 S3 1.820(3) . ?
C28 H28A 0.9800 . ?
C28 H28B 0.9800 . ?
C28 H28C 0.9800 . ?
C29 H29A 0.9800 . ?
C29 H29B 0.9800 . ?
C29 H29C 0.9800 . ?
C30 H30A 0.9800 . ?
C30 H30B 0.9800 . ?
C30 H30C 0.9800 . ?
O1 S4 1.443(2) . ?
O2 S4 1.446(2) . ?
O21 S3 1.446(2) . ?
O22 S3 1.448(2) . ?
Se1 Se2 2.3245(4) . ?
 
loop_
 _geom_angle_atom_site_label_1
 _geom_angle_atom_site_label_2
 _geom_angle_atom_site_label_3
 _geom_angle
 _geom_angle_site_symmetry_1
 _geom_angle_site_symmetry_3
 _geom_angle_publ_flag
C6 C1 C2 120.9(3) . . ?
C6 C1 S4 115.7(2) . . ?
C2 C1 S4 123.4(2) . . ?
C3 C2 C1 117.7(3) . . ?
C3 C2 Se1 120.3(2) . . ?
C1 C2 Se1 121.9(2) . . ?
C4 C3 C2 121.1(3) . . ?
C4 C3 H3 119.5 . . ?
C2 C3 H3 119.5 . . ?
C5 C4 C3 120.6(3) . . ?
C5 C4 H4 119.7 . . ?
C3 C4 H4 119.7 . . ?
C6 C5 C4 119.7(3) . . ?
C6 C5 H5 120.2 . . ?
C4 C5 H5 120.2 . . ?
C5 C6 C1 120.1(3) . . ?
C5 C6 H6 120.0 . . ?
C1 C6 H6 120.0 . . ?
C8 C7 C10 112.0(3) . . ?
C8 C7 C9 110.9(3) . . ?
C10 C7 C9 110.3(3) . . ?
C8 C7 S4 109.0(2) . . ?
C10 C7 S4 109.6(2) . . ?
C9 C7 S4 104.7(2) . . ?
C7 C8 H8A 109.5 . . ?
C7 C8 H8B 109.5 . . ?
H8A C8 H8B 109.5 . . ?
C7 C8 H8C 109.5 . . ?
H8A C8 H8C 109.5 . . ?
H8B C8 H8C 109.5 . . ?
C7 C9 H9A 109.5 . . ?
C7 C9 H9B 109.5 . . ?
H9A C9 H9B 109.5 . . ?
C7 C9 H9C 109.5 . . ?
H9A C9 H9C 109.5 . . ?
H9B C9 H9C 109.5 . . ?
C7 C10 H10A 109.5 . . ?
C7 C10 H10B 109.5 . . ?
H10A C10 H10B 109.5 . . ?
C7 C10 H10C 109.5 . . ?
H10A C10 H10C 109.5 . . ?
H10B C10 H10C 109.5 . . ?
C26 C21 C22 117.5(3) . . ?
C26 C21 Se2 120.9(2) . . ?
C22 C21 Se2 121.5(2) . . ?
C23 C22 C21 120.8(3) . . ?
C23 C22 S3 115.2(2) . . ?
C21 C22 S3 124.0(2) . . ?
C24 C23 C22 120.5(3) . . ?
C24 C23 H23 119.7 . . ?
C22 C23 H23 119.7 . . ?
C23 C24 C25 118.9(3) . . ?
C23 C24 H24 120.5 . . ?
C25 C24 H24 120.5 . . ?
C26 C25 C24 120.9(3) . . ?
C26 C25 H25 119.5 . . ?
C24 C25 H25 119.5 . . ?
C25 C26 C21 121.2(3) . . ?
C25 C26 H26 119.4 . . ?
C21 C26 H26 119.4 . . ?
C29 C27 C28 111.0(3) . . ?
C29 C27 C30 111.8(3) . . ?
C28 C27 C30 111.3(3) . . ?
C29 C27 S3 109.2(2) . . ?
C28 C27 S3 104.7(2) . . ?
C30 C27 S3 108.6(2) . . ?
C27 C28 H28A 109.5 . . ?
C27 C28 H28B 109.5 . . ?
H28A C28 H28B 109.5 . . ?
C27 C28 H28C 109.5 . . ?
H28A C28 H28C 109.5 . . ?
H28B C28 H28C 109.5 . . ?
C27 C29 H29A 109.5 . . ?
C27 C29 H29B 109.5 . . ?
H29A C29 H29B 109.5 . . ?
C27 C29 H29C 109.5 . . ?
H29A C29 H29C 109.5 . . ?
H29B C29 H29C 109.5 . . ?
C27 C30 H30A 109.5 . . ?
C27 C30 H30B 109.5 . . ?
H30A C30 H30B 109.5 . . ?
C27 C30 H30C 109.5 . . ?
H30A C30 H30C 109.5 . . ?
H30B C30 H30C 109.5 . . ?
O21 S3 O22 117.55(13) . . ?
O21 S3 C22 108.17(13) . . ?
O22 S3 C22 107.43(13) . . ?
O21 S3 C27 107.32(13) . . ?
O22 S3 C27 108.77(13) . . ?
C22 S3 C27 107.17(13) . . ?
O1 S4 O2 118.30(13) . . ?
O1 S4 C1 107.85(14) . . ?
O2 S4 C1 106.96(14) . . ?
O1 S4 C7 108.83(14) . . ?
O2 S4 C7 106.94(15) . . ?
C1 S4 C7 107.51(14) . . ?
C2 Se1 Se2 101.18(9) . . ?
C21 Se2 Se1 102.90(9) . . ?
 
_diffrn_measured_fraction_theta_max    0.999
_diffrn_reflns_theta_full              27.48
_diffrn_measured_fraction_theta_full   0.999
_refine_diff_density_max    0.445
_refine_diff_density_min   -0.649
_refine_diff_density_rms    0.109
