data_global
 
_audit_creation_method            'manual editing of form.cif' 

_publ_contact_author_phone        '049 228 73-3495'
_publ_contact_author_fax          '049 228 73-5662'
_publ_contact_author_email        'hoeger@uni-bonn.de'
_publ_requested_journal           
'Organometallics'

_publ_contact_author_name            'Höger, Sigurd'
_publ_contact_author_address
;      Kekule-Institut für Organische Chemie und Biochemie
       Rheinische Friedrich-Wilhelms-Universität Bonn
       Gerhard-Domagk-Str. 1
       D-53121 Bonn
       Germany
;

_publ_section_title
;
Synthesis and Properties of Dithienophenazines
;        

loop_
_publ_author_name
_publ_author_address

       'Meyer, Annemarie'
;      Kekule-Institut für Organische Chemie und Biochemie
       Rheinische Friedrich-Wilhelms-Universität Bonn
       Gerhard-Domagk-Str. 1
       D-53121 Bonn
       Germany
;
       'Sigmund, Eva'
;      Kekule-Institut für Organische Chemie und Biochemie
       Rheinische Friedrich-Wilhelms-Universität Bonn
       Gerhard-Domagk-Str. 1
       D-53121 Bonn
       Germany
;
       'Luppertz, Friedhelm'
;      Kekule-Institut für Organische Chemie und Biochemie
       Rheinische Friedrich-Wilhelms-Universität Bonn
       Gerhard-Domagk-Str. 1
       D-53121 Bonn
       Germany
;
       'Schnakenburg, Gregor'
;      Institut für Anorganische Chemie
       Rheinische Friedrich-Wilhelms-Universität Bonn
       Gerhard-Domagk-Str. 1
       D-53121 Bonn
       Germany
;
       'Jester, Stefan-S.'
;      Kekule-Institut für Organische Chemie und Biochemie
       Rheinische Friedrich-Wilhelms-Universität Bonn
       Gerhard-Domagk-Str. 1
       D-53121 Bonn
       Germany
;
       'Höger, Sigurd'
;      Kekule-Institut für Organische Chemie und Biochemie
       Rheinische Friedrich-Wilhelms-Universität Bonn
       Gerhard-Domagk-Str. 1
       D-53121 Bonn
       Germany
;

#------------------------------------------------------------------------------
 
data_Greg706
 
_audit_creation_method            SHELXL-97 
_chemical_name_systematic 
; 
 ? 
; 
_chemical_name_common             ? 
_chemical_melting_point           ? 
_chemical_formula_moiety          
 '2(C10 H2 Br2 O2 S2), C H2 Cl2'
_chemical_formula_sum 
 'C21 H6 Br4 Cl2 O4 S4' 
_chemical_formula_weight          841.04 
 
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' 
 'Br'  'Br'  -0.2901   2.4595 
 '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' 
 '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' 
 
_symmetry_cell_setting            'Monoclinic' 
_symmetry_space_group_name_H-M    'P 21/c'
 
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                    7.5928(8) 
_cell_length_b                    20.9792(11) 
_cell_length_c                    15.9792(13) 
_cell_angle_alpha                 90.00 
_cell_angle_beta                  94.236(8) 
_cell_angle_gamma                 90.00 
_cell_volume                      2538.4(4) 
_cell_formula_units_Z             4 
_cell_measurement_temperature     123(2) 
_cell_measurement_reflns_used     2557
_cell_measurement_theta_min       2.32
_cell_measurement_theta_max       28.47
_exptl_crystal_description       'needle'
_exptl_crystal_colour            'orange'

_exptl_crystal_size_max           0.3 
_exptl_crystal_size_mid           0.02
_exptl_crystal_size_min           0.02
_exptl_crystal_density_meas       ? 
_exptl_crystal_density_diffrn     2.201 
_exptl_crystal_density_method     'not measured' 
_exptl_crystal_F_000              1608 
_exptl_absorpt_coefficient_mu     6.911 
_exptl_absorpt_correction_type    'Multi-Scan' 
_exptl_absorpt_correction_T_min   0.83152
_exptl_absorpt_correction_T_max   0.87431
_exptl_absorpt_process_details     
;
R.H. Blessing, Acta Cryst. (1995), A51, 33-38
;
 
_exptl_special_details 
; 
 ? 
; 
 
_diffrn_ambient_temperature       123(2) 
_diffrn_measurement_device         '2-circle goniometer'
_diffrn_measurement_device_type    'STOE IPDS 2T'
_diffrn_detector                   'image plate (34 cm diameter)'
_diffrn_detector_type              'STOE'
_diffrn_detector_area_resol_mean   6.67
_diffrn_source           'sealed X-ray tube, 12 x 0.4 mm long-fine focus'
_diffrn_source_voltage             50
_diffrn_source_current             45
_diffrn_source_power               2.25
_diffrn_radiation_type             'Mo K\a'
_diffrn_radiation_wavelength       0.71073
_diffrn_radiation_monochromator    'plane graphite'
_diffrn_radiation_polarisn_norm    0
_diffrn_radiation_collimation      '0.5 mm diameter, monocapillary'
_diffrn_measurement_method         'rotation method'
_diffrn_measurement_details
; 226 frames, detector distance = 100 mm
;
_diffrn_reflns_number             19770 
_diffrn_reflns_av_R_equivalents   0.1351 
_diffrn_reflns_av_sigmaI/netI     0.1667 
_diffrn_reflns_limit_h_min        -10 
_diffrn_reflns_limit_h_max        9 
_diffrn_reflns_limit_k_min        -27 
_diffrn_reflns_limit_k_max        27 
_diffrn_reflns_limit_l_min        -18 
_diffrn_reflns_limit_l_max        21 
_diffrn_reflns_theta_min          2.32 
_diffrn_reflns_theta_max          28.00 
_reflns_number_total              5987 
_reflns_number_gt                 2830 
_reflns_threshold_expression      >2sigma(I) 
 
_computing_data_collection        'STOE X-AREA'
_computing_cell_refinement        'STOE X-AREA'
_computing_data_reduction         'STOE X-RED' 
_computing_structure_solution     'SHELXS-97 (Sheldrick, 1990)' 
_computing_structure_refinement   'SHELXL-97 (Sheldrick, 1997)' 
_computing_molecular_graphics     'DIAMOND (Brandenburg, 1999)' 
_computing_publication_material   'SHELXL97 (Sheldrick, 1997)'
 
_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)+(0.0468P)²+0.0000P] 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          5987 
_refine_ls_number_parameters      316 
_refine_ls_number_restraints      0 
_refine_ls_R_factor_all           0.1545 
_refine_ls_R_factor_gt            0.0672 
_refine_ls_wR_factor_ref          0.1478 
_refine_ls_wR_factor_gt           0.1211 
_refine_ls_goodness_of_fit_ref    0.895 
_refine_ls_restrained_S_all       0.895 
_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_symmetry_multiplicity 
 _atom_site_calc_flag 
 _atom_site_refinement_flags 
 _atom_site_disorder_assembly 
 _atom_site_disorder_group 
C1 C 0.7133(15) 0.2480(5) -0.4627(7) 0.033(2) Uani 1 1 d . . . 
C2 C 0.6497(15) 0.2617(5) -0.3877(8) 0.036(3) Uani 1 1 d . . . 
H2A H 0.6380 0.3037 -0.3668 0.043 Uiso 1 1 calc R . . 
C3 C 0.6029(14) 0.2066(5) -0.3443(7) 0.031(2) Uani 1 1 d . . . 
C4 C 0.6364(14) 0.1506(6) -0.3868(7) 0.032(2) Uani 1 1 d . . . 
C5 C 0.5229(15) 0.2038(5) -0.2634(7) 0.032(3) Uani 1 1 d . . . 
C6 C 0.4771(15) 0.1373(5) -0.2285(7) 0.031(2) Uani 1 1 d . . . 
C7 C 0.5325(15) 0.0811(5) -0.2742(7) 0.031(2) Uani 1 1 d . . . 
C8 C 0.6038(14) 0.0899(5) -0.3512(7) 0.026(2) Uani 1 1 d . . . 
C9 C 0.5128(15) 0.0170(5) -0.2511(7) 0.029(2) Uani 1 1 d . . . 
H9A H 0.4685 0.0038 -0.1998 0.035 Uiso 1 1 calc R . . 
C10 C 0.5652(14) -0.0243(5) -0.3116(7) 0.030(2) Uani 1 1 d . . . 
C11 C 0.0658(15) 0.5580(4) 0.1959(7) 0.028(2) Uani 1 1 d . . . 
C12 C 0.0234(16) 0.5188(5) 0.2535(8) 0.037(3) Uani 1 1 d . . . 
H12A H -0.0148 0.5313 0.3063 0.045 Uiso 1 1 calc R . . 
C13 C 0.0419(14) 0.4541(5) 0.2268(7) 0.025(2) Uani 1 1 d . . . 
C14 C 0.1013(15) 0.4491(5) 0.1479(7) 0.031(2) Uani 1 1 d . . . 
C15 C -0.0040(15) 0.3975(5) 0.2737(7) 0.028(2) Uani 1 1 d . . . 
C16 C 0.0306(15) 0.3306(5) 0.2332(7) 0.031(2) Uani 1 1 d . . . 
C17 C 0.1059(14) 0.3309(5) 0.1516(7) 0.027(2) Uani 1 1 d . . . 
C18 C 0.1375(14) 0.3879(4) 0.1115(7) 0.028(2) Uani 1 1 d . . . 
C19 C 0.1479(14) 0.2757(4) 0.1041(7) 0.026(2) Uani 1 1 d . . . 
H19A H 0.1371 0.2331 0.1229 0.032 Uiso 1 1 calc R . . 
C20 C 0.2064(15) 0.2928(5) 0.0269(7) 0.030(2) Uani 1 1 d . . . 
C21 C 0.761(3) -0.0659(7) 0.0069(10) 0.070(5) Uani 1 1 d . . . 
H21A H 0.8798 -0.0803 0.0283 0.084 Uiso 1 1 calc R . . 
H21B H 0.6738 -0.0849 0.0429 0.084 Uiso 1 1 calc R . . 
Br1 Br 0.79525(16) 0.30346(5) -0.54257(8) 0.0366(3) Uani 1 1 d . . . 
Br2 Br 0.55864(16) -0.11261(5) -0.30897(8) 0.0338(3) Uani 1 1 d . . . 
Br3 Br 0.05861(16) 0.64900(5) 0.20045(8) 0.0339(3) Uani 1 1 d . . . 
Br4 Br 0.27892(15) 0.24172(5) -0.05801(7) 0.0307(3) Uani 1 1 d . . . 
Cl1 Cl 0.7492(6) 0.0192(2) 0.0134(3) 0.0691(11) Uani 1 1 d . . . 
Cl2 Cl 0.7177(5) -0.09275(16) -0.0952(2) 0.0563(9) Uani 1 1 d . . . 
O1 O 0.4878(11) 0.2520(4) -0.2241(5) 0.042(2) Uani 1 1 d . . . 
O2 O 0.3902(11) 0.1344(3) -0.1687(5) 0.0346(18) Uani 1 1 d . . . 
O3 O -0.0641(11) 0.3981(4) 0.3403(5) 0.0392(19) Uani 1 1 d . . . 
O4 O -0.0137(11) 0.2838(4) 0.2695(5) 0.0361(19) Uani 1 1 d . . . 
S1 S 0.7205(4) 0.16634(13) -0.48213(18) 0.0315(6) Uani 1 1 d . . . 
S2 S 0.6413(4) 0.01555(13) -0.39652(18) 0.0306(6) Uani 1 1 d . . . 
S3 S 0.1328(4) 0.52279(12) 0.10529(18) 0.0288(6) Uani 1 1 d . . . 
S4 S 0.2104(4) 0.37575(12) 0.01355(17) 0.0278(6) 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 1.356(16) . ? 
C1 S1 1.742(11) . ? 
C1 Br1 1.868(12) . ? 
C2 C3 1.407(15) . ? 
C2 H2A 0.9500 . ? 
C3 C4 1.389(15) . ? 
C3 C5 1.470(16) . ? 
C4 C8 1.424(15) . ? 
C4 S1 1.727(13) . ? 
C5 O1 1.228(13) . ? 
C5 C6 1.553(15) . ? 
C6 O2 1.202(13) . ? 
C6 C7 1.464(15) . ? 
C7 C8 1.392(16) . ? 
C7 C9 1.405(14) . ? 
C8 S2 1.752(11) . ? 
C9 C10 1.380(14) . ? 
C9 H9A 0.9500 . ? 
C10 S2 1.730(12) . ? 
C10 Br2 1.853(10) . ? 
C11 C12 1.292(16) . ? 
C11 S3 1.734(12) . ? 
C11 Br3 1.912(9) . ? 
C12 C13 1.433(14) . ? 
C12 H12A 0.9500 . ? 
C13 C14 1.373(15) . ? 
C13 C15 1.461(14) . ? 
C14 C18 1.445(14) . ? 
C14 S3 1.713(11) . ? 
C15 O3 1.189(13) . ? 
C15 C16 1.576(14) . ? 
C16 O4 1.201(13) . ? 
C16 C17 1.461(15) . ? 
C17 C18 1.387(14) . ? 
C17 C19 1.434(13) . ? 
C18 S4 1.717(12) . ? 
C19 C20 1.388(16) . ? 
C19 H19A 0.9500 . ? 
C20 S4 1.754(10) . ? 
C20 Br4 1.844(11) . ? 
C21 Cl2 1.735(17) . ? 
C21 Cl1 1.791(15) . ? 
C21 H21A 0.9900 . ? 
C21 H21B 0.9900 . ? 
 
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 S1 112.6(9) . . ? 
C2 C1 Br1 129.1(9) . . ? 
S1 C1 Br1 118.3(6) . . ? 
C1 C2 C3 112.3(11) . . ? 
C1 C2 H2A 123.8 . . ? 
C3 C2 H2A 123.8 . . ? 
C4 C3 C2 113.1(12) . . ? 
C4 C3 C5 120.0(11) . . ? 
C2 C3 C5 126.9(11) . . ? 
C3 C4 C8 121.2(11) . . ? 
C3 C4 S1 111.2(9) . . ? 
C8 C4 S1 127.6(9) . . ? 
O1 C5 C3 122.5(11) . . ? 
O1 C5 C6 119.5(11) . . ? 
C3 C5 C6 118.0(10) . . ? 
O2 C6 C7 123.5(11) . . ? 
O2 C6 C5 118.7(10) . . ? 
C7 C6 C5 117.6(11) . . ? 
C8 C7 C9 114.5(10) . . ? 
C8 C7 C6 118.6(10) . . ? 
C9 C7 C6 126.7(11) . . ? 
C7 C8 C4 124.2(10) . . ? 
C7 C8 S2 109.5(8) . . ? 
C4 C8 S2 126.3(9) . . ? 
C10 C9 C7 112.0(10) . . ? 
C10 C9 H9A 124.0 . . ? 
C7 C9 H9A 124.0 . . ? 
C9 C10 S2 112.1(8) . . ? 
C9 C10 Br2 127.1(9) . . ? 
S2 C10 Br2 120.8(6) . . ? 
C12 C11 S3 115.3(8) . . ? 
C12 C11 Br3 126.7(9) . . ? 
S3 C11 Br3 117.9(6) . . ? 
C11 C12 C13 110.8(11) . . ? 
C11 C12 H12A 124.6 . . ? 
C13 C12 H12A 124.6 . . ? 
C14 C13 C12 113.0(10) . . ? 
C14 C13 C15 121.1(10) . . ? 
C12 C13 C15 125.9(10) . . ? 
C13 C14 C18 121.5(11) . . ? 
C13 C14 S3 111.2(9) . . ? 
C18 C14 S3 127.2(10) . . ? 
O3 C15 C13 125.0(10) . . ? 
O3 C15 C16 117.6(10) . . ? 
C13 C15 C16 117.4(10) . . ? 
O4 C16 C17 125.3(10) . . ? 
O4 C16 C15 117.9(10) . . ? 
C17 C16 C15 116.8(10) . . ? 
C18 C17 C19 113.5(10) . . ? 
C18 C17 C16 120.6(10) . . ? 
C19 C17 C16 125.9(10) . . ? 
C17 C18 C14 122.4(11) . . ? 
C17 C18 S4 111.8(8) . . ? 
C14 C18 S4 125.7(9) . . ? 
C20 C19 C17 111.2(9) . . ? 
C20 C19 H19A 124.4 . . ? 
C17 C19 H19A 124.4 . . ? 
C19 C20 S4 111.9(8) . . ? 
C19 C20 Br4 129.5(8) . . ? 
S4 C20 Br4 118.6(7) . . ? 
Cl2 C21 Cl1 111.8(8) . . ? 
Cl2 C21 H21A 109.3 . . ? 
Cl1 C21 H21A 109.3 . . ? 
Cl2 C21 H21B 109.3 . . ? 
Cl1 C21 H21B 109.3 . . ? 
H21A C21 H21B 107.9 . . ? 
C4 S1 C1 90.7(6) . . ? 
C10 S2 C8 91.8(5) . . ? 
C14 S3 C11 89.7(5) . . ? 
C18 S4 C20 91.6(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 
S1 C1 C2 C3 -0.7(13) . . . . ? 
Br1 C1 C2 C3 -179.2(8) . . . . ? 
C1 C2 C3 C4 1.6(15) . . . . ? 
C1 C2 C3 C5 -177.1(11) . . . . ? 
C2 C3 C4 C8 177.7(10) . . . . ? 
C5 C3 C4 C8 -3.5(16) . . . . ? 
C2 C3 C4 S1 -1.7(12) . . . . ? 
C5 C3 C4 S1 177.1(8) . . . . ? 
C4 C3 C5 O1 -178.7(10) . . . . ? 
C2 C3 C5 O1 -0.1(18) . . . . ? 
C4 C3 C5 C6 -0.4(15) . . . . ? 
C2 C3 C5 C6 178.2(10) . . . . ? 
O1 C5 C6 O2 8.3(16) . . . . ? 
C3 C5 C6 O2 -169.9(11) . . . . ? 
O1 C5 C6 C7 -175.8(11) . . . . ? 
C3 C5 C6 C7 5.9(15) . . . . ? 
O2 C6 C7 C8 168.2(11) . . . . ? 
C5 C6 C7 C8 -7.5(15) . . . . ? 
O2 C6 C7 C9 -8.0(18) . . . . ? 
C5 C6 C7 C9 176.4(10) . . . . ? 
C9 C7 C8 C4 -179.6(10) . . . . ? 
C6 C7 C8 C4 3.9(16) . . . . ? 
C9 C7 C8 S2 1.5(11) . . . . ? 
C6 C7 C8 S2 -175.0(8) . . . . ? 
C3 C4 C8 C7 2.0(16) . . . . ? 
S1 C4 C8 C7 -178.8(9) . . . . ? 
C3 C4 C8 S2 -179.3(8) . . . . ? 
S1 C4 C8 S2 -0.1(15) . . . . ? 
C8 C7 C9 C10 -1.5(13) . . . . ? 
C6 C7 C9 C10 174.8(11) . . . . ? 
C7 C9 C10 S2 0.7(12) . . . . ? 
C7 C9 C10 Br2 -178.8(8) . . . . ? 
S3 C11 C12 C13 -0.5(14) . . . . ? 
Br3 C11 C12 C13 178.6(8) . . . . ? 
C11 C12 C13 C14 0.7(14) . . . . ? 
C11 C12 C13 C15 -176.3(11) . . . . ? 
C12 C13 C14 C18 176.7(10) . . . . ? 
C15 C13 C14 C18 -6.1(16) . . . . ? 
C12 C13 C14 S3 -0.7(12) . . . . ? 
C15 C13 C14 S3 176.5(8) . . . . ? 
C14 C13 C15 O3 -176.2(12) . . . . ? 
C12 C13 C15 O3 0.6(19) . . . . ? 
C14 C13 C15 C16 4.3(15) . . . . ? 
C12 C13 C15 C16 -178.9(10) . . . . ? 
O3 C15 C16 O4 3.7(16) . . . . ? 
C13 C15 C16 O4 -176.9(10) . . . . ? 
O3 C15 C16 C17 -179.5(11) . . . . ? 
C13 C15 C16 C17 0.0(14) . . . . ? 
O4 C16 C17 C18 174.0(11) . . . . ? 
C15 C16 C17 C18 -2.6(15) . . . . ? 
O4 C16 C17 C19 -3.6(19) . . . . ? 
C15 C16 C17 C19 179.9(10) . . . . ? 
C19 C17 C18 C14 179.0(10) . . . . ? 
C16 C17 C18 C14 1.1(16) . . . . ? 
C19 C17 C18 S4 2.4(12) . . . . ? 
C16 C17 C18 S4 -175.4(8) . . . . ? 
C13 C14 C18 C17 3.4(17) . . . . ? 
S3 C14 C18 C17 -179.7(9) . . . . ? 
C13 C14 C18 S4 179.5(9) . . . . ? 
S3 C14 C18 S4 -3.6(16) . . . . ? 
C18 C17 C19 C20 -1.7(14) . . . . ? 
C16 C17 C19 C20 176.0(10) . . . . ? 
C17 C19 C20 S4 0.3(12) . . . . ? 
C17 C19 C20 Br4 179.5(8) . . . . ? 
C3 C4 S1 C1 1.1(8) . . . . ? 
C8 C4 S1 C1 -178.2(10) . . . . ? 
C2 C1 S1 C4 -0.2(9) . . . . ? 
Br1 C1 S1 C4 178.4(7) . . . . ? 
C9 C10 S2 C8 0.1(9) . . . . ? 
Br2 C10 S2 C8 179.6(7) . . . . ? 
C7 C8 S2 C10 -0.9(8) . . . . ? 
C4 C8 S2 C10 -179.8(10) . . . . ? 
C13 C14 S3 C11 0.4(9) . . . . ? 
C18 C14 S3 C11 -176.8(11) . . . . ? 
C12 C11 S3 C14 0.1(10) . . . . ? 
Br3 C11 S3 C14 -179.1(7) . . . . ? 
C17 C18 S4 C20 -1.8(9) . . . . ? 
C14 C18 S4 C20 -178.3(10) . . . . ? 
C19 C20 S4 C18 0.9(9) . . . . ? 
Br4 C20 S4 C18 -178.4(7) . . . . ? 
 
_diffrn_measured_fraction_theta_max    0.980 
_diffrn_reflns_theta_full              28.00 
_diffrn_measured_fraction_theta_full   0.980 
_refine_diff_density_max    0.889 
_refine_diff_density_min   -1.138 
_refine_diff_density_rms    0.168 
 
#------------------------------------------------------------------------------
#===END
 
data_Greg1219 
 
_audit_creation_method            SHELXL-97 
_chemical_name_systematic 
; 
 ? 
; 
_chemical_name_common             ? 
_chemical_melting_point           ? 
_chemical_formula_moiety          
 'C10 H4 O2 S2' 
_chemical_formula_sum 
 'C10 H4 O2 S2' 
_chemical_formula_weight          220.27 
 
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' 
 
_symmetry_cell_setting            'Monoclinic'
_symmetry_space_group_name_H-M    'P 21/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                    8.9233(4) 
_cell_length_b                    14.8008(8) 
_cell_length_c                    6.6258(2) 
_cell_angle_alpha                 90.00 
_cell_angle_beta                  102.935(3) 
_cell_angle_gamma                 90.00 
_cell_volume                      852.88(7) 
_cell_formula_units_Z             4 
_cell_measurement_temperature     123(2) 
_cell_measurement_reflns_used     2113
_cell_measurement_theta_min       1.00
_cell_measurement_theta_max       29.13
 
_exptl_crystal_description        plate
_exptl_crystal_colour             red
_exptl_crystal_size_max           0.6
_exptl_crystal_size_mid           0.429
_exptl_crystal_size_min           0.161
_exptl_crystal_density_meas       ? 
_exptl_crystal_density_diffrn     1.715 
_exptl_crystal_density_method     'not measured' 
_exptl_crystal_F_000              448 
_exptl_absorpt_coefficient_mu     0.585 
_exptl_absorpt_correction_type    'Multi-Scan'
_exptl_absorpt_correction_T_min   0.79308 
_exptl_absorpt_correction_T_max   0.91287
_exptl_absorpt_process_details    
;
R.H. Blessing, Acta Cryst. (1995), A51, 33-38
;
 

_diffrn_ambient_temperature       123(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   'Nonius KappaCCD' 
_diffrn_measurement_method        'CCD rotation images, thick slices'
_diffrn_detector_area_resol_mean  9  
_diffrn_standards_number          ? 
_diffrn_standards_interval_count  ? 
_diffrn_standards_interval_time   ? 
_diffrn_standards_decay_%         ? 
_diffrn_reflns_number             7685 
_diffrn_reflns_av_R_equivalents   0.0424 
_diffrn_reflns_av_sigmaI/netI     0.0383 
_diffrn_reflns_limit_h_min        -11 
_diffrn_reflns_limit_h_max        10 
_diffrn_reflns_limit_k_min        -17 
_diffrn_reflns_limit_k_max        19 
_diffrn_reflns_limit_l_min        -8 
_diffrn_reflns_limit_l_max        7 
_diffrn_reflns_theta_min          2.75 
_diffrn_reflns_theta_max          27.99 
_reflns_number_total              2029 
_reflns_number_gt                 1666 
_reflns_threshold_expression      >2sigma(I) 
 
_computing_data_collection 'HKL Denzo and Scalepack (Otwinowski & Minor 1997)' 
_computing_cell_refinement 'HKL Scalepack (Otwinowski & Minor 1997)'
_computing_data_reduction  'HKL Denzo and Scalepack (Otwinowski & Minor 1997)'
_computing_structure_solution     'SHELXS-97 (Sheldrick, 1990)' 
_computing_structure_refinement   'SHELXL-97 (Sheldrick, 1997)' 
_computing_molecular_graphics     'DIAMOND (Brandenburg, 1999)' 
_computing_publication_material   'SHELXL97 (Sheldrick, 1997)' 
 
_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)+(0.0369P)²+0.0998P] 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      SHELXL 
_refine_ls_extinction_coef        0.0068(13) 
_refine_ls_extinction_expression 
 'Fc^*^=kFc[1+0.001xFc²λ³/sin(2θ)]^-1/4^' 
_refine_ls_number_reflns          2029 
_refine_ls_number_parameters      128 
_refine_ls_number_restraints      0 
_refine_ls_R_factor_all           0.0376 
_refine_ls_R_factor_gt            0.0272 
_refine_ls_wR_factor_ref          0.0736 
_refine_ls_wR_factor_gt           0.0699 
_refine_ls_goodness_of_fit_ref    1.044 
_refine_ls_restrained_S_all       1.044 
_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_symmetry_multiplicity 
 _atom_site_calc_flag 
 _atom_site_refinement_flags 
 _atom_site_disorder_assembly 
 _atom_site_disorder_group 
S1 S -1.49471(4) -0.89734(3) -0.23340(5) 0.01673(12) Uani 1 1 d . . . 
S2 S -0.96222(4) -0.61493(3) -0.08233(5) 0.01649(12) Uani 1 1 d . . . 
O1 O -1.54678(12) -0.68845(7) -0.25206(15) 0.0192(3) Uani 1 1 d . . . 
O2 O -1.31233(12) -0.56330(7) -0.18320(15) 0.0193(3) Uani 1 1 d . . . 
C1 C -1.34757(18) -0.97329(10) -0.1961(2) 0.0175(3) Uani 1 1 d . . . 
H1 H -1.3624 -1.0369 -0.2026 0.021 Uiso 1 1 calc R . . 
C2 C -1.20535(18) -0.93307(10) -0.1557(2) 0.0156(3) Uani 1 1 d . . . 
H2 H -1.1112 -0.9655 -0.1308 0.019 Uiso 1 1 calc R . . 
C3 C -1.21534(16) -0.83754(9) -0.15533(19) 0.0123(3) Uani 1 1 d . . . 
C4 C -1.36746(17) -0.80857(9) -0.1964(2) 0.0135(3) Uani 1 1 d . . . 
C5 C -1.41305(17) -0.71436(10) -0.2110(2) 0.0137(3) Uani 1 1 d . . . 
C6 C -1.28056(17) -0.64378(10) -0.1734(2) 0.0135(3) Uani 1 1 d . . . 
C7 C -1.12571(16) -0.68020(10) -0.12866(19) 0.0126(3) Uani 1 1 d . . . 
C8 C -1.09130(16) -0.77184(10) -0.12092(18) 0.0120(3) Uani 1 1 d . . . 
C9 C -0.93105(17) -0.78777(11) -0.07770(19) 0.0149(3) Uani 1 1 d . . . 
H9 H -0.8859 -0.8462 -0.0663 0.018 Uiso 1 1 calc R . . 
C10 C -0.84867(17) -0.70882(11) -0.0542(2) 0.0177(3) Uani 1 1 d . . . 
H10 H -0.7395 -0.7066 -0.0253 0.021 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 
S1 C1 1.7039(16) . ? 
S1 C4 1.7179(14) . ? 
S2 C10 1.7054(16) . ? 
S2 C7 1.7192(15) . ? 
O1 C5 1.2246(18) . ? 
O2 C6 1.2228(18) . ? 
C1 C2 1.373(2) . ? 
C1 H1 0.9500 . ? 
C2 C3 1.417(2) . ? 
C2 H2 0.9500 . ? 
C3 C4 1.391(2) . ? 
C3 C8 1.452(2) . ? 
C4 C5 1.450(2) . ? 
C5 C6 1.555(2) . ? 
C6 C7 1.451(2) . ? 
C7 C8 1.389(2) . ? 
C8 C9 1.414(2) . ? 
C9 C10 1.371(2) . ? 
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 
C1 S1 C4 91.18(7) . . ? 
C10 S2 C7 91.22(7) . . ? 
C2 C1 S1 113.02(11) . . ? 
C2 C1 H1 123.5 . . ? 
S1 C1 H1 123.5 . . ? 
C1 C2 C3 112.16(13) . . ? 
C1 C2 H2 123.9 . . ? 
C3 C2 H2 123.9 . . ? 
C4 C3 C2 111.49(13) . . ? 
C4 C3 C8 120.02(13) . . ? 
C2 C3 C8 128.49(13) . . ? 
C3 C4 C5 123.81(13) . . ? 
C3 C4 S1 112.15(11) . . ? 
C5 C4 S1 124.02(11) . . ? 
O1 C5 C4 124.13(14) . . ? 
O1 C5 C6 119.55(13) . . ? 
C4 C5 C6 116.32(12) . . ? 
O2 C6 C7 124.88(13) . . ? 
O2 C6 C5 119.13(13) . . ? 
C7 C6 C5 115.99(12) . . ? 
C8 C7 C6 124.26(13) . . ? 
C8 C7 S2 111.74(11) . . ? 
C6 C7 S2 123.99(11) . . ? 
C7 C8 C9 112.06(13) . . ? 
C7 C8 C3 119.57(13) . . ? 
C9 C8 C3 128.37(13) . . ? 
C10 C9 C8 111.91(14) . . ? 
C10 C9 H9 124.0 . . ? 
C8 C9 H9 124.0 . . ? 
C9 C10 S2 113.07(12) . . ? 
C9 C10 H10 123.5 . . ? 
S2 C10 H10 123.5 . . ? 
 
_diffrn_measured_fraction_theta_max    0.984 
_diffrn_reflns_theta_full              27.99 
_diffrn_measured_fraction_theta_full   0.984 
_refine_diff_density_max    0.292 
_refine_diff_density_min   -0.316 
_refine_diff_density_rms    0.061 

#===END