data_s92
 
_audit_creation_method            SHELXL-97
_chemical_name_systematic
;
 Bricklebank
;
_chemical_name_common             ?
_chemical_melting_point           ?
_chemical_formula_moiety          ?
_chemical_formula_sum
 'C17 H10 Br2 O2 S5'
_chemical_formula_weight          566.37
 
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'
 'S'  'S'   0.1246   0.1234
 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
 'Br'  'Br'  -0.2901   2.4595
 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
 
_symmetry_cell_setting            Monoclinic
_symmetry_space_group_name_H-M    Cc
_symmetry_space_group_name_hall   'C -2yc'
 
loop_
 _symmetry_equiv_pos_as_xyz
 'x, y, z'
 'x, -y, z+1/2'
 'x+1/2, y+1/2, z'
 'x+1/2, -y+1/2, z+1/2'
 
_cell_length_a                    20.9579(5)
_cell_length_b                    13.8067(4)
_cell_length_c                    15.1219(5)
_cell_angle_alpha                 90.00
_cell_angle_beta                  116.4930(10)
_cell_angle_gamma                 90.00
_cell_volume                      3916.2(2)
_cell_formula_units_Z             8
_cell_measurement_temperature     120(2)
_cell_measurement_reflns_used     6040
_cell_measurement_theta_min       2.91
_cell_measurement_theta_max       27.48
 
_exptl_crystal_description        block
_exptl_crystal_colour             yellow
_exptl_crystal_size_max           0.40
_exptl_crystal_size_mid           0.28
_exptl_crystal_size_min           0.18
_exptl_crystal_density_meas       ?
_exptl_crystal_density_diffrn     1.921
_exptl_crystal_density_method     'not measured'
_exptl_crystal_F_000              2224
_exptl_absorpt_coefficient_mu     4.684
_exptl_absorpt_correction_type    multi-scan
_exptl_absorpt_correction_T_min   0.2559
_exptl_absorpt_correction_T_max   0.4861
_exptl_absorpt_process_details    'SORTAV Blessing (1997)'
 
_exptl_special_details
;
 ?
;
 
_diffrn_ambient_temperature       120(2)
_diffrn_radiation_wavelength      0.71073
_diffrn_radiation_type            MoK\a
_diffrn_radiation_source          'Enraf Nonius FR591 rotating anode'
_diffrn_radiation_monochromator   graphite 
_diffrn_measurement_device_type   'Enraf Nonius KappaCCD area detector'
_diffrn_measurement_method        'ω and φ scans to fill Ewald sphere'
_diffrn_detector_area_resol_mean  '9.091 pixels/mm'
_diffrn_standards_number          'n/a'
_diffrn_standards_interval_count  'n/a'
_diffrn_standards_interval_time   'n/a'
_diffrn_standards_decay_%         'n/a'
_diffrn_reflns_number             8839
_diffrn_reflns_av_R_equivalents   0.0675
_diffrn_reflns_av_sigmaI/netI     0.0722
_diffrn_reflns_limit_h_min        -26
_diffrn_reflns_limit_h_max        27
_diffrn_reflns_limit_k_min        -17
_diffrn_reflns_limit_k_max        17
_diffrn_reflns_limit_l_min        -18
_diffrn_reflns_limit_l_max        19
_diffrn_reflns_theta_min          2.95
_diffrn_reflns_theta_max          27.50
_reflns_number_total              5227
_reflns_number_gt                 4669
_reflns_threshold_expression      >2sigma(I)
 
_computing_data_collection        
;
'DENZO (Otwinowski and Minor, 1997) & COLLECT (Hooft, 1998) '
;
_computing_cell_refinement        'DENZO and COLLECT'
_computing_data_reduction         'DENZO and COLLECT'
_computing_structure_solution     'SHELXS-97 (Sheldrick, 2008)' 
_computing_structure_refinement   'SHELXL-97 (Sheldrick, 2008)' 
_computing_molecular_graphics     ?
_computing_publication_material   SHELXL-97
 
_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)+(0.1046P)²+21.0144P] 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_number_reflns          5227
_refine_ls_number_parameters      471
_refine_ls_number_restraints      2
_refine_ls_R_factor_all           0.0665
_refine_ls_R_factor_gt            0.0570
_refine_ls_wR_factor_ref          0.1557
_refine_ls_wR_factor_gt           0.1449
_refine_ls_goodness_of_fit_ref    1.020
_refine_ls_restrained_S_all       1.020
_refine_ls_shift/su_max           0.015
_refine_ls_shift/su_mean          0.002
 
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
C11 C 0.7071(6) 0.5048(8) 0.9927(9) 0.025(3) Uani 1 1 d . . .
C12 C 0.7818(6) 0.4887(8) 1.0661(9) 0.027(3) Uani 1 1 d . . .
C13 C 0.8093(7) 0.3948(9) 1.0873(11) 0.034(3) Uani 1 1 d . . .
H13 H 0.7811 0.3411 1.0520 0.041 Uiso 1 1 calc R . .
C14 C 0.8774(7) 0.3811(9) 1.1598(12) 0.043(4) Uani 1 1 d . . .
H14 H 0.8950 0.3169 1.1771 0.051 Uiso 1 1 calc R . .
C15 C 0.9204(7) 0.4566(9) 1.2075(10) 0.034(3) Uani 1 1 d . . .
H15 H 0.9678 0.4447 1.2559 0.041 Uiso 1 1 calc R . .
C16 C 0.8955(6) 0.5519(9) 1.1863(10) 0.030(3) Uani 1 1 d . . .
H16 H 0.9253 0.6048 1.2205 0.036 Uiso 1 1 calc R . .
C17 C 0.8261(6) 0.5675(8) 1.1141(11) 0.028(3) Uani 1 1 d . . .
H17 H 0.8087 0.6318 1.0971 0.034 Uiso 1 1 calc R . .
C18 C 0.1348(6) 0.6553(7) 0.2205(9) 0.022(3) Uani 1 1 d . . .
C19 C 0.0935(6) 0.6482(7) 0.0337(8) 0.019(2) Uani 1 1 d . . .
C20 C 0.0350(6) 0.6268(7) 0.0498(10) 0.023(3) Uani 1 1 d . . .
C21 C -0.0674(5) 0.4894(8) -0.0318(9) 0.023(3) Uani 1 1 d . . .
C22 C -0.1373(6) 0.4525(8) -0.1047(10) 0.027(3) Uani 1 1 d . . .
C23 C -0.1457(7) 0.3523(9) -0.1124(13) 0.043(4) Uani 1 1 d . . .
H23 H -0.1082 0.3101 -0.0719 0.051 Uiso 1 1 calc R . .
C24 C -0.2113(9) 0.3161(10) -0.1822(13) 0.055(5) Uani 1 1 d . . .
H24 H -0.2177 0.2480 -0.1899 0.066 Uiso 1 1 calc R . .
C25 C -0.2661(8) 0.3754(11) -0.2394(12) 0.043(4) Uani 1 1 d . . .
H25 H -0.3103 0.3488 -0.2854 0.052 Uiso 1 1 calc R . .
C26 C -0.2571(7) 0.4740(10) -0.2302(10) 0.035(3) Uani 1 1 d . . .
H26 H -0.2954 0.5150 -0.2710 0.042 Uiso 1 1 calc R . .
C27 C -0.1938(7) 0.5154(8) -0.1630(10) 0.027(3) Uani 1 1 d . . .
H27 H -0.1885 0.5837 -0.1562 0.032 Uiso 1 1 calc R . .
C28 C 0.1685(6) 0.6082(7) -0.0694(10) 0.024(3) Uani 1 1 d . . .
C29 C 0.1749(6) 0.6010(8) -0.1645(10) 0.023(3) Uani 1 1 d . . .
C30 C 0.2380(6) 0.5599(7) -0.1586(10) 0.025(3) Uani 1 1 d . . .
H30 H 0.2743 0.5385 -0.0969 0.030 Uiso 1 1 calc R . .
C31 C 0.2468(6) 0.5510(8) -0.2432(10) 0.028(3) Uani 1 1 d . . .
H31 H 0.2892 0.5231 -0.2402 0.033 Uiso 1 1 calc R . .
C32 C 0.1933(6) 0.5830(8) -0.3333(10) 0.028(3) Uani 1 1 d . . .
H32 H 0.1994 0.5772 -0.3917 0.033 Uiso 1 1 calc R . .
C33 C 0.1312(7) 0.6231(9) -0.3382(11) 0.031(3) Uani 1 1 d . . .
H33 H 0.0953 0.6451 -0.3999 0.037 Uiso 1 1 calc R . .
C34 C 0.1208(6) 0.6317(8) -0.2556(9) 0.023(3) Uani 1 1 d . . .
H34 H 0.0776 0.6579 -0.2597 0.028 Uiso 1 1 calc R . .
O2 O 0.6685(5) 0.4450(6) 0.9384(8) 0.042(3) Uani 1 1 d . . .
O3 O -0.0227(5) 0.4407(6) 0.0320(8) 0.043(3) Uani 1 1 d . . .
O4 O 0.2125(5) 0.5809(6) 0.0092(7) 0.032(2) Uani 1 1 d . . .
C1 C 0.4890(6) 0.6348(7) 0.7208(9) 0.023(3) Uani 1 1 d . . .
C2 C 0.5904(6) 0.6213(7) 0.8954(10) 0.024(3) Uani 1 1 d . . .
C3 C 0.5326(6) 0.6360(8) 0.9086(9) 0.025(3) Uani 1 1 d . . .
C4 C 0.4569(6) 0.6169(8) 1.0174(10) 0.024(3) Uani 1 1 d . . .
C5 C 0.4525(6) 0.6195(7) 1.1103(9) 0.021(3) Uani 1 1 d . . .
C6 C 0.5106(6) 0.6216(8) 1.2020(10) 0.027(3) Uani 1 1 d . . .
H6 H 0.5572 0.6249 1.2065 0.033 Uiso 1 1 calc R . .
C7 C 0.5023(7) 0.6192(7) 1.2876(10) 0.029(3) Uani 1 1 d . . .
H7 H 0.5431 0.6210 1.3500 0.035 Uiso 1 1 calc R . .
C8 C 0.4341(6) 0.6139(7) 1.2828(10) 0.025(3) Uani 1 1 d . . .
H8 H 0.4286 0.6116 1.3418 0.030 Uiso 1 1 calc R . .
C9 C 0.3740(6) 0.6122(7) 1.1903(10) 0.025(3) Uani 1 1 d . . .
H9 H 0.3272 0.6096 1.1851 0.030 Uiso 1 1 calc R . .
C10 C 0.3852(6) 0.6145(8) 1.1086(8) 0.022(3) Uani 1 1 d . . .
H10 H 0.3447 0.6126 1.0459 0.026 Uiso 1 1 calc R . .
O1 O 0.4090(4) 0.5917(6) 0.9386(7) 0.033(2) Uani 1 1 d . . .
S1 S 0.43762(15) 0.6358(2) 0.5934(2) 0.0245(7) Uani 1 1 d . . .
S2 S 0.45214(15) 0.6450(2) 0.8005(2) 0.0231(6) Uani 1 1 d . . .
S3 S 0.57845(14) 0.61646(19) 0.7736(2) 0.0237(7) Uani 1 1 d . . .
S4 S 0.53926(16) 0.6629(2) 1.0249(2) 0.0274(7) Uani 1 1 d . . .
S5 S 0.67832(15) 0.6295(2) 0.9885(2) 0.0261(7) Uani 1 1 d . . .
S6 S 0.18601(14) 0.66616(18) 0.3484(2) 0.0205(6) Uani 1 1 d . . .
S7 S 0.17061(14) 0.67214(19) 0.1408(2) 0.0216(6) Uani 1 1 d . . .
S8 S 0.04796(14) 0.62560(19) 0.1701(2) 0.0225(7) Uani 1 1 d . . .
S9 S -0.05228(15) 0.61710(19) -0.0452(2) 0.0253(7) Uani 1 1 d . . .
S10 S 0.08777(15) 0.6679(2) -0.0830(2) 0.0259(7) Uani 1 1 d . . .
Br1 Br 0.32694(6) 0.65703(8) 0.60100(9) 0.0290(3) Uani 1 1 d . . .
Br2 Br 0.54481(6) 0.61009(8) 0.55972(9) 0.0275(3) Uani 1 1 d . . .
Br3 Br 0.29374(6) 0.71084(8) 0.33954(10) 0.0287(3) Uani 1 1 d . . .
Br4 Br 0.08368(5) 0.62098(8) 0.38581(8) 0.0256(3) 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
C11 O2 1.190(14) . ?
C11 C12 1.477(16) . ?
C11 S5 1.816(12) . ?
C12 C13 1.397(16) . ?
C12 C17 1.405(18) . ?
C13 C14 1.371(19) . ?
C13 H13 0.9500 . ?
C14 C15 1.356(19) . ?
C14 H14 0.9500 . ?
C15 C16 1.399(17) . ?
C15 H15 0.9500 . ?
C16 C17 1.391(18) . ?
C16 H16 0.9500 . ?
C17 H17 0.9500 . ?
C18 S8 1.681(11) . ?
C18 S7 1.696(14) . ?
C18 S6 1.750(12) . ?
C19 C20 1.384(17) . ?
C19 S7 1.735(11) . ?
C19 S10 1.736(12) . ?
C20 S8 1.716(14) . ?
C20 S9 1.756(11) . ?
C21 O3 1.206(14) . ?
C21 C22 1.476(15) . ?
C21 S9 1.818(11) . ?
C22 C23 1.392(17) . ?
C22 C27 1.415(17) . ?
C23 C24 1.40(2) . ?
C23 H23 0.9500 . ?
C24 C25 1.36(2) . ?
C24 H24 0.9500 . ?
C25 C26 1.372(19) . ?
C25 H25 0.9500 . ?
C26 C27 1.384(17) . ?
C26 H26 0.9500 . ?
C27 H27 0.9500 . ?
C28 O4 1.194(16) . ?
C28 C29 1.506(19) . ?
C28 S10 1.810(12) . ?
C29 C34 1.403(17) . ?
C29 C30 1.405(16) . ?
C30 C31 1.377(19) . ?
C30 H30 0.9500 . ?
C31 C32 1.395(18) . ?
C31 H31 0.9500 . ?
C32 C33 1.386(19) . ?
C32 H32 0.9500 . ?
C33 C34 1.37(2) . ?
C33 H33 0.9500 . ?
C34 H34 0.9500 . ?
C1 S3 1.697(11) . ?
C1 S2 1.704(14) . ?
C1 S1 1.738(12) . ?
C2 C3 1.327(18) . ?
C2 S5 1.754(12) . ?
C2 S3 1.747(15) . ?
C3 S4 1.741(14) . ?
C3 S2 1.753(11) . ?
C4 O1 1.218(15) . ?
C4 C5 1.449(19) . ?
C4 S4 1.794(12) . ?
C5 C6 1.379(17) . ?
C5 C10 1.400(17) . ?
C6 C7 1.38(2) . ?
C6 H6 0.9500 . ?
C7 C8 1.400(19) . ?
C7 H7 0.9500 . ?
C8 C9 1.405(18) . ?
C8 H8 0.9500 . ?
C9 C10 1.357(19) . ?
C9 H9 0.9500 . ?
C10 H10 0.9500 . ?
S1 Br1 2.391(3) . ?
S1 Br2 2.540(4) . ?
S6 Br3 2.401(3) . ?
S6 Br4 2.528(3) . ?
 
loop_
 _geom_angle_atom_site_label_1
 _geom_angle_atom_site_label_2
 _geom_angle_atom_site_label_3
 _geom_angle
 _geom_angle_site_symmetry_1
 _geom_angle_site_symmetry_3
 _geom_angle_publ_flag
O2 C11 C12 125.4(11) . . ?
O2 C11 S5 121.4(9) . . ?
C12 C11 S5 113.1(8) . . ?
C13 C12 C17 119.4(11) . . ?
C13 C12 C11 120.2(11) . . ?
C17 C12 C11 120.5(10) . . ?
C14 C13 C12 119.2(12) . . ?
C14 C13 H13 120.4 . . ?
C12 C13 H13 120.4 . . ?
C15 C14 C13 121.8(11) . . ?
C15 C14 H14 119.1 . . ?
C13 C14 H14 119.1 . . ?
C14 C15 C16 120.7(11) . . ?
C14 C15 H15 119.7 . . ?
C16 C15 H15 119.7 . . ?
C17 C16 C15 118.6(12) . . ?
C17 C16 H16 120.7 . . ?
C15 C16 H16 120.7 . . ?
C16 C17 C12 120.3(11) . . ?
C16 C17 H17 119.9 . . ?
C12 C17 H17 119.9 . . ?
S8 C18 S7 116.4(7) . . ?
S8 C18 S6 121.9(8) . . ?
S7 C18 S6 121.7(7) . . ?
C20 C19 S7 114.0(9) . . ?
C20 C19 S10 123.2(9) . . ?
S7 C19 S10 122.2(7) . . ?
C19 C20 S8 117.0(9) . . ?
C19 C20 S9 123.6(10) . . ?
S8 C20 S9 118.8(8) . . ?
O3 C21 C22 124.3(10) . . ?
O3 C21 S9 121.2(8) . . ?
C22 C21 S9 114.6(8) . . ?
C23 C22 C27 121.2(11) . . ?
C23 C22 C21 116.8(11) . . ?
C27 C22 C21 122.0(10) . . ?
C22 C23 C24 117.6(13) . . ?
C22 C23 H23 121.2 . . ?
C24 C23 H23 121.2 . . ?
C25 C24 C23 122.0(12) . . ?
C25 C24 H24 119.0 . . ?
C23 C24 H24 119.0 . . ?
C24 C25 C26 119.6(12) . . ?
C24 C25 H25 120.2 . . ?
C26 C25 H25 120.2 . . ?
C25 C26 C27 121.8(13) . . ?
C25 C26 H26 119.1 . . ?
C27 C26 H26 119.1 . . ?
C26 C27 C22 117.8(11) . . ?
C26 C27 H27 121.1 . . ?
C22 C27 H27 121.1 . . ?
O4 C28 C29 124.9(11) . . ?
O4 C28 S10 121.6(11) . . ?
C29 C28 S10 113.5(8) . . ?
C34 C29 C30 120.6(12) . . ?
C34 C29 C28 122.7(10) . . ?
C30 C29 C28 116.6(10) . . ?
C31 C30 C29 119.3(11) . . ?
C31 C30 H30 120.3 . . ?
C29 C30 H30 120.3 . . ?
C30 C31 C32 119.8(11) . . ?
C30 C31 H31 120.1 . . ?
C32 C31 H31 120.1 . . ?
C33 C32 C31 120.3(13) . . ?
C33 C32 H32 119.8 . . ?
C31 C32 H32 119.8 . . ?
C34 C33 C32 121.0(13) . . ?
C34 C33 H33 119.5 . . ?
C32 C33 H33 119.5 . . ?
C33 C34 C29 118.9(11) . . ?
C33 C34 H34 120.6 . . ?
C29 C34 H34 120.6 . . ?
S3 C1 S2 115.7(7) . . ?
S3 C1 S1 122.0(8) . . ?
S2 C1 S1 122.1(7) . . ?
C3 C2 S5 124.8(11) . . ?
C3 C2 S3 117.0(9) . . ?
S5 C2 S3 117.0(8) . . ?
C2 C3 S4 121.2(9) . . ?
C2 C3 S2 115.7(10) . . ?
S4 C3 S2 122.4(8) . . ?
O1 C4 C5 125.0(11) . . ?
O1 C4 S4 120.9(11) . . ?
C5 C4 S4 114.0(8) . . ?
C6 C5 C10 116.7(12) . . ?
C6 C5 C4 124.5(11) . . ?
C10 C5 C4 118.7(10) . . ?
C7 C6 C5 121.3(12) . . ?
C7 C6 H6 119.4 . . ?
C5 C6 H6 119.4 . . ?
C6 C7 C8 120.3(12) . . ?
C6 C7 H7 119.8 . . ?
C8 C7 H7 119.8 . . ?
C7 C8 C9 119.6(13) . . ?
C7 C8 H8 120.2 . . ?
C9 C8 H8 120.2 . . ?
C10 C9 C8 117.6(10) . . ?
C10 C9 H9 121.2 . . ?
C8 C9 H9 121.2 . . ?
C9 C10 C5 124.5(11) . . ?
C9 C10 H10 117.7 . . ?
C5 C10 H10 117.7 . . ?
C1 S1 Br1 94.7(4) . . ?
C1 S1 Br2 93.2(4) . . ?
Br1 S1 Br2 172.06(14) . . ?
C1 S2 C3 95.9(6) . . ?
C1 S3 C2 95.7(6) . . ?
C3 S4 C4 102.7(6) . . ?
C2 S5 C11 100.4(5) . . ?
C18 S6 Br3 95.1(4) . . ?
C18 S6 Br4 93.6(4) . . ?
Br3 S6 Br4 171.29(14) . . ?
C18 S7 C19 96.6(5) . . ?
C18 S8 C20 96.1(6) . . ?
C20 S9 C21 98.8(5) . . ?
C19 S10 C28 100.1(6) . . ?
 
_diffrn_measured_fraction_theta_max    0.748
_diffrn_reflns_theta_full              27.50
_diffrn_measured_fraction_theta_full   0.748
_refine_diff_density_max    1.313
_refine_diff_density_min   -1.543
_refine_diff_density_rms    0.237
