# Electronic Supplementary Material (ESI) for ChemComm.
# This journal is © The Royal Society of Chemistry 2014

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#                                CCDC 
# 
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#  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.
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#  fide research purposes only. It may contain copyright material
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data_cd28421

_audit_creation_method           SHELXL-97
_chemical_name_systematic        
; 
 ? 
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C18 H18 Br F2 N O3 S2'
_chemical_formula_weight         478.36

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'
N N 0.0061 0.0033 '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'
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'
Br Br -0.2901 2.4595 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_symmetry_cell_setting           Orthorhombic
_symmetry_space_group_name_H-M   P2(1)2(1)2(1)

loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'-x+1/2, -y, z+1/2'
'-x, y+1/2, -z+1/2'
'x+1/2, -y+1/2, -z'

_cell_length_a                   18.0666(13)
_cell_length_b                   21.1169(15)
_cell_length_c                   22.2584(15)
_cell_angle_alpha                90.00
_cell_angle_beta                 90.00
_cell_angle_gamma                90.00
_cell_volume                     8491.8(10)
_cell_formula_units_Z            16
_cell_measurement_temperature    293(2)
_cell_measurement_reflns_used    3351
_cell_measurement_theta_min      4.468
_cell_measurement_theta_max      33.932

_exptl_crystal_description       prismatic
_exptl_crystal_colour            yellow
_exptl_crystal_size_max          0.420
_exptl_crystal_size_mid          0.365
_exptl_crystal_size_min          0.123
_exptl_crystal_density_meas      ?
_exptl_crystal_density_diffrn    1.497
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             3872
_exptl_absorpt_coefficient_mu    2.167
_exptl_absorpt_correction_type   empirical
_exptl_absorpt_correction_T_min  0.7339
_exptl_absorpt_correction_T_max  1.0000
_exptl_absorpt_process_details   sadabs

_exptl_special_details           
; 
 ? 
;

_diffrn_ambient_temperature      293(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_radiation_source         'fine-focus sealed tube'
_diffrn_radiation_monochromator  graphite
_diffrn_measurement_device_type  'CCD area detector'
_diffrn_measurement_method       'phi and omega scans'
_diffrn_detector_area_resol_mean ?
_diffrn_standards_number         ?
_diffrn_standards_interval_count ?
_diffrn_standards_interval_time  ?
_diffrn_standards_decay_%        ?
_diffrn_reflns_number            50613
_diffrn_reflns_av_R_equivalents  0.1112
_diffrn_reflns_av_sigmaI/netI    0.2609
_diffrn_reflns_limit_h_min       -23
_diffrn_reflns_limit_h_max       19
_diffrn_reflns_limit_k_min       -23
_diffrn_reflns_limit_k_max       26
_diffrn_reflns_limit_l_min       -25
_diffrn_reflns_limit_l_max       28
_diffrn_reflns_theta_min         1.45
_diffrn_reflns_theta_max         27.00
_reflns_number_total             18491
_reflns_number_gt                7866
_reflns_threshold_expression     >2sigma(I)

_computing_data_collection       'Bruker SMART'
_computing_cell_refinement       'Bruker SMART'
_computing_data_reduction        'Bruker SHELXTL'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 1990)'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_computing_molecular_graphics    'Bruker SHELXTL'
_computing_publication_material  'Bruker SHELXTL'

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

_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
; calc 
 [0.00000+1.00000exp(3.00(sinθ/λ)²)]/ 
   [σ²(Fo²)+0.0000+0.0000*P+(0.0381P)²+0.0000sinθ/λ] 
 where P = 0.33333Fo² + 0.66667Fc² 
;
_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_abs_structure_details 'Flack H D (1983), Acta Cryst. A39, 876-881'
_refine_ls_abs_structure_Flack   0.026(9)
_refine_ls_number_reflns         18491
_refine_ls_number_parameters     970
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.2145
_refine_ls_R_factor_gt           0.0515
_refine_ls_wR_factor_ref         0.1397
_refine_ls_wR_factor_gt          0.0997
_refine_ls_goodness_of_fit_ref   0.864
_refine_ls_restrained_S_all      0.864
_refine_ls_shift/su_max          0.030
_refine_ls_shift/su_mean         0.042

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
Br1 Br 0.66345(8) 0.38657(7) 0.45631(5) 0.1391(5) Uani 1 1 d . . .
Br2 Br 0.16818(8) 0.72016(6) 0.47723(4) 0.1236(5) Uani 1 1 d . . .
Br3 Br 0.15978(8) 0.76213(6) 0.98154(4) 0.1185(5) Uani 1 1 d . . .
Br4 Br 0.33007(7) 0.59305(6) 0.53040(4) 0.1102(4) Uani 1 1 d . . .
S1 S 0.73093(15) 0.48732(13) 0.11896(13) 0.0824(8) Uani 1 1 d . . .
S2 S 0.48510(16) 0.48564(16) 0.18016(13) 0.1140(10) Uani 1 1 d . . .
S3 S 0.24075(14) 0.64709(12) 0.14085(12) 0.0703(7) Uani 1 1 d . . .
S4 S -0.00542(14) 0.72864(12) 0.18734(11) 0.0814(7) Uani 1 1 d . . .
S5 S 0.24690(14) 0.85643(11) 0.64727(11) 0.0661(7) Uani 1 1 d . . .
S6 S -0.00130(17) 0.8250(2) 0.71571(13) 0.1387(13) Uani 1 1 d . . .
S7 S 0.28249(16) 0.53324(13) 0.87240(14) 0.0850(8) Uani 1 1 d . . .
S8 S 0.52873(14) 0.59866(13) 0.81072(12) 0.0904(8) Uani 1 1 d . . .
F1 F 0.6709(3) 0.3781(3) 0.1061(3) 0.127(2) Uani 1 1 d . . .
F2 F 0.7370(3) 0.3879(2) 0.1862(3) 0.1068(19) Uani 1 1 d . . .
F3 F 0.2118(3) 0.7658(2) 0.1243(2) 0.0840(15) Uani 1 1 d . . .
F4 F 0.2679(3) 0.7445(2) 0.2071(2) 0.0839(15) Uani 1 1 d . . .
F5 F 0.1917(3) 0.7465(2) 0.6237(2) 0.1059(19) Uani 1 1 d . . .
F6 F 0.2558(3) 0.7509(2) 0.7052(2) 0.0929(17) Uani 1 1 d . . .
F7 F 0.3150(3) 0.6525(2) 0.8777(2) 0.0931(17) Uani 1 1 d . . .
F8 F 0.2564(3) 0.6240(2) 0.7980(2) 0.0815(15) Uani 1 1 d . . .
O1 O 0.6880(4) 0.5069(4) 0.0693(3) 0.130(3) Uani 1 1 d . . .
O2 O 0.7420(4) 0.5280(3) 0.1700(3) 0.116(3) Uani 1 1 d . . .
O3 O 0.4633(4) 0.4563(5) 0.2369(3) 0.183(4) Uani 1 1 d . . .
O4 O 0.1871(4) 0.6303(3) 0.0963(2) 0.094(2) Uani 1 1 d . . .
O5 O 0.2506(4) 0.6075(2) 0.1907(3) 0.0872(19) Uani 1 1 d . . .
O6 O -0.0205(3) 0.7137(4) 0.2500(3) 0.125(3) Uani 1 1 d . . .
O7 O 0.1962(4) 0.8843(3) 0.6047(3) 0.109(2) Uani 1 1 d . . .
O8 O 0.2664(3) 0.8891(2) 0.7022(2) 0.0789(18) Uani 1 1 d . . .
O9 O -0.0358(7) 0.7603(5) 0.7326(5) 0.233(5) Uiso 1 1 d . . .
O10 O 0.3293(4) 0.5256(4) 0.9240(3) 0.133(3) Uani 1 1 d . . .
O11 O 0.2818(4) 0.4873(3) 0.8262(3) 0.103(2) Uani 1 1 d . . .
O12 O 0.5373(4) 0.5635(4) 0.7545(3) 0.144(3) Uani 1 1 d . . .
N1 N 0.5676(4) 0.4579(4) 0.1543(3) 0.090(3) Uani 1 1 d . . .
N2 N 0.0855(4) 0.7247(3) 0.1672(3) 0.0597(19) Uani 1 1 d . . .
N3 N 0.0815(4) 0.8072(4) 0.6768(3) 0.100(3) Uani 1 1 d . . .
N4 N 0.4395(4) 0.6021(3) 0.8360(3) 0.073(2) Uani 1 1 d . . .
C1 C 0.6877(6) 0.4177(5) 0.1503(4) 0.076(3) Uani 1 1 d . . .
C2 C 0.6169(6) 0.4342(4) 0.1868(4) 0.074(3) Uani 1 1 d . . .
C3 C 0.6231(5) 0.4262(5) 0.2535(4) 0.063(3) Uani 1 1 d . . .
C4 C 0.6078(6) 0.3685(6) 0.2763(5) 0.092(3) Uani 1 1 d . . .
H4 H 0.5907 0.3369 0.2508 0.110 Uiso 1 1 calc R . .
C5 C 0.6170(6) 0.3547(5) 0.3379(6) 0.096(4) Uani 1 1 d . . .
H5 H 0.6070 0.3146 0.3531 0.115 Uiso 1 1 calc R . .
C6 C 0.6407(5) 0.4015(6) 0.3738(4) 0.077(3) Uani 1 1 d . . .
C7 C 0.6565(6) 0.4594(5) 0.3524(4) 0.082(3) Uani 1 1 d . . .
H7 H 0.6738 0.4909 0.3780 0.099 Uiso 1 1 calc R . .
C8 C 0.6466(5) 0.4718(4) 0.2915(5) 0.082(3) Uani 1 1 d . . .
H8 H 0.6563 0.5121 0.2767 0.098 Uiso 1 1 calc R . .
C9 C 0.8171(5) 0.4589(4) 0.0947(4) 0.069(3) Uani 1 1 d . . .
C10 C 0.8750(5) 0.4570(4) 0.1349(4) 0.069(3) Uani 1 1 d . . .
H10 H 0.8692 0.4687 0.1749 0.083 Uiso 1 1 calc R . .
C11 C 0.9445(5) 0.4360(4) 0.1113(5) 0.088(3) Uani 1 1 d . . .
H11 H 0.9854 0.4335 0.1367 0.106 Uiso 1 1 calc R . .
C12 C 0.9518(6) 0.4198(5) 0.0531(5) 0.112(4) Uani 1 1 d . . .
H12 H 0.9979 0.4072 0.0389 0.134 Uiso 1 1 calc R . .
C13 C 0.8932(7) 0.4213(6) 0.0147(5) 0.129(5) Uani 1 1 d . . .
H13 H 0.8986 0.4091 -0.0252 0.155 Uiso 1 1 calc R . .
C14 C 0.8258(6) 0.4414(4) 0.0361(4) 0.090(3) Uani 1 1 d . . .
H14 H 0.7854 0.4431 0.0103 0.108 Uiso 1 1 calc R . .
C15 C 0.4291(6) 0.4490(6) 0.1196(5) 0.104(4) Uani 1 1 d . . .
C16 C 0.4453(6) 0.3777(5) 0.1236(5) 0.149(5) Uani 1 1 d . . .
H16A H 0.4485 0.3654 0.1650 0.224 Uiso 1 1 calc R . .
H16B H 0.4914 0.3686 0.1039 0.224 Uiso 1 1 calc R . .
H16C H 0.4062 0.3545 0.1044 0.224 Uiso 1 1 calc R . .
C17 C 0.3495(6) 0.4633(6) 0.1408(5) 0.162(5) Uani 1 1 d . . .
H17A H 0.3403 0.5080 0.1382 0.244 Uiso 1 1 calc R . .
H17B H 0.3437 0.4496 0.1817 0.244 Uiso 1 1 calc R . .
H17C H 0.3149 0.4411 0.1158 0.244 Uiso 1 1 calc R . .
C18 C 0.4507(7) 0.4737(6) 0.0617(4) 0.183(7) Uani 1 1 d . . .
H18A H 0.4135 0.4635 0.0325 0.275 Uiso 1 1 calc R . .
H18B H 0.4970 0.4552 0.0498 0.275 Uiso 1 1 calc R . .
H18C H 0.4561 0.5189 0.0642 0.275 Uiso 1 1 calc R . .
C19 C 0.2146(5) 0.7229(4) 0.1698(4) 0.070(3) Uani 1 1 d . . .
C20 C 0.1385(5) 0.7224(3) 0.2039(4) 0.054(2) Uani 1 1 d . . .
C21 C 0.1411(5) 0.7208(5) 0.2704(4) 0.061(2) Uani 1 1 d . . .
C22 C 0.1354(5) 0.7764(4) 0.3009(4) 0.079(3) Uani 1 1 d . . .
H22 H 0.1259 0.8142 0.2809 0.094 Uiso 1 1 calc R . .
C23 C 0.1442(7) 0.7749(5) 0.3630(4) 0.095(4) Uani 1 1 d . . .
H23 H 0.1415 0.8124 0.3848 0.114 Uiso 1 1 calc R . .
C24 C 0.1565(5) 0.7208(6) 0.3917(4) 0.074(3) Uani 1 1 d . . .
C25 C 0.1614(6) 0.6653(5) 0.3623(5) 0.092(3) Uani 1 1 d . . .
H25 H 0.1698 0.6277 0.3829 0.111 Uiso 1 1 calc R . .
C26 C 0.1536(6) 0.6658(4) 0.3000(4) 0.082(3) Uani 1 1 d . . .
H26 H 0.1570 0.6281 0.2786 0.098 Uiso 1 1 calc R . .
C27 C 0.3259(5) 0.6604(4) 0.1060(4) 0.063(2) Uani 1 1 d . . .
C28 C 0.3291(6) 0.6696(4) 0.0433(4) 0.085(3) Uani 1 1 d . . .
H28 H 0.2862 0.6704 0.0203 0.102 Uiso 1 1 calc R . .
C29 C 0.3953(7) 0.6772(6) 0.0178(5) 0.129(5) Uani 1 1 d . . .
H29 H 0.3972 0.6801 -0.0238 0.155 Uiso 1 1 calc R . .
C30 C 0.4600(7) 0.6811(6) 0.0484(6) 0.134(5) Uani 1 1 d . . .
H30 H 0.5049 0.6894 0.0296 0.160 Uiso 1 1 calc R . .
C31 C 0.4539(7) 0.6715(5) 0.1112(6) 0.122(4) Uani 1 1 d . . .
H31 H 0.4970 0.6722 0.1340 0.146 Uiso 1 1 calc R . .
C32 C 0.3905(6) 0.6615(5) 0.1394(5) 0.094(3) Uani 1 1 d . . .
H32 H 0.3893 0.6554 0.1807 0.113 Uiso 1 1 calc R . .
C33 C -0.0375(5) 0.6619(5) 0.1446(4) 0.081(3) Uani 1 1 d . . .
C34 C -0.1214(5) 0.6594(5) 0.1554(5) 0.128(4) Uani 1 1 d . . .
H34A H -0.1440 0.6969 0.1392 0.192 Uiso 1 1 calc R . .
H34B H -0.1310 0.6571 0.1977 0.192 Uiso 1 1 calc R . .
H34C H -0.1417 0.6228 0.1359 0.192 Uiso 1 1 calc R . .
C35 C -0.0201(6) 0.6727(6) 0.0792(4) 0.151(5) Uani 1 1 d . . .
H35A H 0.0315 0.6647 0.0722 0.226 Uiso 1 1 calc R . .
H35B H -0.0314 0.7158 0.0688 0.226 Uiso 1 1 calc R . .
H35C H -0.0493 0.6446 0.0550 0.226 Uiso 1 1 calc R . .
C36 C 0.0020(6) 0.6026(4) 0.1696(6) 0.164(6) Uani 1 1 d . . .
H36A H -0.0087 0.5669 0.1445 0.247 Uiso 1 1 calc R . .
H36B H -0.0151 0.5944 0.2097 0.247 Uiso 1 1 calc R . .
H36C H 0.0545 0.6098 0.1702 0.247 Uiso 1 1 calc R . .
C37 C 0.2051(5) 0.7802(4) 0.6720(4) 0.060(2) Uani 1 1 d . . .
C38 C 0.1344(6) 0.7929(4) 0.7085(4) 0.073(3) Uani 1 1 d . . .
C39 C 0.1395(5) 0.7847(4) 0.7752(4) 0.057(2) Uani 1 1 d . . .
C40 C 0.1204(6) 0.7309(5) 0.8026(5) 0.089(3) Uani 1 1 d . . .
H40 H 0.1032 0.6975 0.7792 0.107 Uiso 1 1 calc R . .
C41 C 0.1250(7) 0.7220(5) 0.8651(5) 0.106(4) Uani 1 1 d . . .
H41 H 0.1125 0.6838 0.8833 0.128 Uiso 1 1 calc R . .
C42 C 0.1495(6) 0.7740(6) 0.8980(4) 0.076(3) Uani 1 1 d . . .
C43 C 0.1715(6) 0.8272(5) 0.8706(4) 0.091(3) Uani 1 1 d . . .
H43 H 0.1906 0.8603 0.8934 0.109 Uiso 1 1 calc R . .
C44 C 0.1663(6) 0.8336(5) 0.8096(4) 0.098(3) Uani 1 1 d . . .
H44 H 0.1810 0.8712 0.7913 0.118 Uiso 1 1 calc R . .
C45 C 0.3255(5) 0.8329(4) 0.6076(4) 0.055(2) Uani 1 1 d . . .
C46 C 0.3253(6) 0.8249(4) 0.5478(4) 0.087(3) Uani 1 1 d . . .
H46 H 0.2813 0.8296 0.5266 0.104 Uiso 1 1 calc R . .
C47 C 0.3881(7) 0.8102(5) 0.5178(5) 0.114(4) Uani 1 1 d . . .
H47 H 0.3881 0.8067 0.4762 0.137 Uiso 1 1 calc R . .
C48 C 0.4506(7) 0.8006(5) 0.5496(5) 0.111(4) Uani 1 1 d . . .
H48 H 0.4933 0.7888 0.5290 0.133 Uiso 1 1 calc R . .
C49 C 0.4540(6) 0.8071(5) 0.6091(5) 0.102(4) Uani 1 1 d . . .
H49 H 0.4979 0.7999 0.6298 0.122 Uiso 1 1 calc R . .
C50 C 0.3907(6) 0.8249(4) 0.6389(4) 0.069(3) Uani 1 1 d . . .
H50 H 0.3918 0.8316 0.6802 0.083 Uiso 1 1 calc R . .
C51 C -0.0555(6) 0.8404(5) 0.6510(4) 0.101(4) Uani 1 1 d . . .
C52 C -0.1297(5) 0.8621(5) 0.6709(4) 0.123(4) Uani 1 1 d . . .
H52A H -0.1581 0.8748 0.6365 0.184 Uiso 1 1 calc R . .
H52B H -0.1244 0.8973 0.6978 0.184 Uiso 1 1 calc R . .
H52C H -0.1546 0.8280 0.6911 0.184 Uiso 1 1 calc R . .
C53 C -0.0503(10) 0.7954(7) 0.6038(7) 0.186(8) Uiso 1 1 d . . .
H53A H -0.0649 0.7545 0.6184 0.353 Uiso 1 1 calc R . .
H53B H -0.0001 0.7935 0.5896 0.353 Uiso 1 1 calc R . .
H53C H -0.0823 0.8078 0.5714 0.353 Uiso 1 1 calc R . .
C54 C -0.0146(8) 0.8970(6) 0.6281(6) 0.192(6) Uiso 1 1 d . . .
H54A H 0.0330 0.8993 0.6472 0.289 Uiso 1 1 calc R . .
H54B H -0.0423 0.9346 0.6370 0.289 Uiso 1 1 calc R . .
H54C H -0.0081 0.8933 0.5854 0.289 Uiso 1 1 calc R . .
C55 C 0.3108(6) 0.6066(4) 0.8355(4) 0.073(3) Uani 1 1 d . . .
C56 C 0.3854(5) 0.5996(4) 0.7998(4) 0.066(3) Uani 1 1 d . . .
C57 C 0.3777(4) 0.5937(5) 0.7349(4) 0.061(2) Uani 1 1 d . . .
C58 C 0.3903(5) 0.6478(4) 0.7011(4) 0.070(3) Uani 1 1 d . . .
H58 H 0.4092 0.6840 0.7193 0.084 Uiso 1 1 calc R . .
C59 C 0.3751(6) 0.6477(4) 0.6416(4) 0.084(3) Uani 1 1 d . . .
H59 H 0.3791 0.6849 0.6194 0.101 Uiso 1 1 calc R . .
C60 C 0.3540(5) 0.5932(5) 0.6144(4) 0.065(2) Uani 1 1 d . . .
C61 C 0.3453(5) 0.5376(4) 0.6451(4) 0.073(3) Uani 1 1 d . . .
H61 H 0.3326 0.5003 0.6254 0.088 Uiso 1 1 calc R . .
C62 C 0.3563(5) 0.5387(4) 0.7075(5) 0.076(3) Uani 1 1 d . . .
H62 H 0.3491 0.5022 0.7302 0.091 Uiso 1 1 calc R . .
C63 C 0.1902(5) 0.5484(4) 0.8964(4) 0.061(2) Uani 1 1 d . . .
C64 C 0.1797(6) 0.5635(4) 0.9566(4) 0.080(3) Uani 1 1 d . . .
H64 H 0.2197 0.5676 0.9826 0.096 Uiso 1 1 calc R . .
C65 C 0.1105(6) 0.5720(5) 0.9758(4) 0.088(3) Uani 1 1 d . . .
H65 H 0.1019 0.5799 1.0163 0.106 Uiso 1 1 calc R . .
C66 C 0.0519(6) 0.5693(5) 0.9367(5) 0.094(3) Uani 1 1 d . . .
H66 H 0.0041 0.5761 0.9508 0.113 Uiso 1 1 calc R . .
C67 C 0.0630(6) 0.5567(5) 0.8779(5) 0.087(3) Uani 1 1 d . . .
H67 H 0.0229 0.5549 0.8517 0.104 Uiso 1 1 calc R . .
C68 C 0.1332(6) 0.5466(4) 0.8568(4) 0.080(3) Uani 1 1 d . . .
H68 H 0.1415 0.5387 0.8162 0.096 Uiso 1 1 calc R . .
C69 C 0.5630(6) 0.5449(5) 0.8703(4) 0.082(3) Uani 1 1 d . . .
C70 C 0.6438(6) 0.5357(5) 0.8542(5) 0.135(4) Uani 1 1 d . . .
H70A H 0.6685 0.5759 0.8542 0.202 Uiso 1 1 calc R . .
H70B H 0.6474 0.5169 0.8150 0.202 Uiso 1 1 calc R . .
H70C H 0.6667 0.5083 0.8831 0.202 Uiso 1 1 calc R . .
C71 C 0.5513(7) 0.5774(6) 0.9286(4) 0.166(6) Uani 1 1 d . . .
H71A H 0.5813 0.5577 0.9589 0.249 Uiso 1 1 calc R . .
H71B H 0.5001 0.5745 0.9398 0.249 Uiso 1 1 calc R . .
H71C H 0.5650 0.6212 0.9249 0.249 Uiso 1 1 calc R . .
C72 C 0.5215(6) 0.4854(5) 0.8686(5) 0.132(4) Uani 1 1 d . . .
H72A H 0.5363 0.4592 0.9017 0.198 Uiso 1 1 calc R . .
H72B H 0.5315 0.4639 0.8315 0.198 Uiso 1 1 calc R . .
H72C H 0.4695 0.4942 0.8715 0.198 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
Br1 C6 1.909(9) . ?
Br2 C24 1.916(8) . ?
Br3 C42 1.885(8) . ?
Br4 C60 1.919(8) . ?
S1 O1 1.412(6) . ?
S1 O2 1.437(6) . ?
S1 C9 1.754(9) . ?
S1 C1 1.804(10) . ?
S2 O3 1.462(8) . ?
S2 N1 1.701(7) . ?
S2 C15 1.855(11) . ?
S3 O5 1.400(5) . ?
S3 O4 1.431(6) . ?
S3 C27 1.746(9) . ?
S3 C19 1.788(9) . ?
S4 O6 1.456(6) . ?
S4 N2 1.705(7) . ?
S4 C33 1.797(9) . ?
S5 O7 1.443(6) . ?
S5 O8 1.448(5) . ?
S5 C45 1.744(8) . ?
S5 C37 1.860(8) . ?
S6 O9 1.549(11) . ?
S6 N3 1.769(8) . ?
S6 C51 1.771(9) . ?
S7 O11 1.413(6) . ?
S7 O10 1.436(7) . ?
S7 C63 1.780(9) . ?
S7 C55 1.826(9) . ?
S8 O12 1.463(7) . ?
S8 N4 1.710(7) . ?
S8 C69 1.852(9) . ?
F1 C1 1.328(9) . ?
F2 C1 1.352(9) . ?
F3 C19 1.360(9) . ?
F4 C19 1.351(9) . ?
F5 C37 1.311(8) . ?
F6 C37 1.330(9) . ?
F7 C55 1.351(9) . ?
F8 C55 1.340(9) . ?
N1 C2 1.251(10) . ?
N2 C20 1.258(9) . ?
N3 C38 1.227(10) . ?
N4 C56 1.267(10) . ?
C1 C2 1.555(12) . ?
C2 C3 1.498(12) . ?
C3 C4 1.349(11) . ?
C3 C8 1.350(10) . ?
C4 C5 1.411(12) . ?
C4 H4 0.9300 . ?
C5 C6 1.339(12) . ?
C5 H5 0.9300 . ?
C6 C7 1.343(11) . ?
C7 C8 1.392(10) . ?
C7 H7 0.9300 . ?
C8 H8 0.9300 . ?
C9 C14 1.363(10) . ?
C9 C10 1.377(11) . ?
C10 C11 1.432(12) . ?
C10 H10 0.9300 . ?
C11 C12 1.346(12) . ?
C11 H11 0.9300 . ?
C12 C13 1.363(14) . ?
C12 H12 0.9300 . ?
C13 C14 1.375(13) . ?
C13 H13 0.9300 . ?
C14 H14 0.9300 . ?
C15 C18 1.443(13) . ?
C15 C16 1.537(13) . ?
C15 C17 1.545(14) . ?
C16 H16A 0.9600 . ?
C16 H16B 0.9600 . ?
C16 H16C 0.9600 . ?
C17 H17A 0.9600 . ?
C17 H17B 0.9600 . ?
C17 H17C 0.9600 . ?
C18 H18A 0.9600 . ?
C18 H18B 0.9600 . ?
C18 H18C 0.9600 . ?
C19 C20 1.571(11) . ?
C20 C21 1.481(10) . ?
C21 C26 1.355(10) . ?
C21 C22 1.360(10) . ?
C22 C23 1.392(10) . ?
C22 H22 0.9300 . ?
C23 C24 1.327(11) . ?
C23 H23 0.9300 . ?
C24 C25 1.346(11) . ?
C25 C26 1.394(11) . ?
C25 H25 0.9300 . ?
C26 H26 0.9300 . ?
C27 C32 1.382(12) . ?
C27 C28 1.412(10) . ?
C28 C29 1.332(13) . ?
C28 H28 0.9300 . ?
C29 C30 1.354(14) . ?
C29 H29 0.9300 . ?
C30 C31 1.418(13) . ?
C30 H30 0.9300 . ?
C31 C32 1.323(13) . ?
C31 H31 0.9300 . ?
C32 H32 0.9300 . ?
C33 C35 1.507(11) . ?
C33 C34 1.535(12) . ?
C33 C36 1.545(13) . ?
C34 H34A 0.9600 . ?
C34 H34B 0.9600 . ?
C34 H34C 0.9600 . ?
C35 H35A 0.9600 . ?
C35 H35B 0.9600 . ?
C35 H35C 0.9600 . ?
C36 H36A 0.9600 . ?
C36 H36B 0.9600 . ?
C36 H36C 0.9600 . ?
C37 C38 1.538(11) . ?
C38 C39 1.497(11) . ?
C39 C40 1.335(11) . ?
C39 C44 1.373(10) . ?
C40 C41 1.406(11) . ?
C40 H40 0.9300 . ?
C41 C42 1.393(12) . ?
C41 H41 0.9300 . ?
C42 C43 1.338(11) . ?
C43 C44 1.368(10) . ?
C43 H43 0.9300 . ?
C44 H44 0.9300 . ?
C45 C46 1.342(9) . ?
C45 C50 1.378(11) . ?
C46 C47 1.352(12) . ?
C46 H46 0.9300 . ?
C47 C48 1.348(14) . ?
C47 H47 0.9300 . ?
C48 C49 1.333(13) . ?
C48 H48 0.9300 . ?
C49 C50 1.374(12) . ?
C49 H49 0.9300 . ?
C50 H50 0.9300 . ?
C51 C53 1.421(15) . ?
C51 C52 1.484(12) . ?
C51 C54 1.493(15) . ?
C52 H52A 0.9600 . ?
C52 H52B 0.9600 . ?
C52 H52C 0.9600 . ?
C53 H53A 0.9643 . ?
C53 H53B 0.9643 . ?
C53 H53C 0.9645 . ?
C54 H54A 0.9601 . ?
C54 H54B 0.9601 . ?
C54 H54C 0.9601 . ?
C55 C56 1.571(12) . ?
C56 C57 1.457(11) . ?
C57 C62 1.367(11) . ?
C57 C58 1.387(10) . ?
C58 C59 1.353(10) . ?
C58 H58 0.9300 . ?
C59 C60 1.356(10) . ?
C59 H59 0.9300 . ?
C60 C61 1.367(10) . ?
C61 C62 1.403(10) . ?
C61 H61 0.9300 . ?
C62 H62 0.9300 . ?
C63 C68 1.356(11) . ?
C63 C64 1.391(10) . ?
C64 C65 1.333(12) . ?
C64 H64 0.9300 . ?
C65 C66 1.373(12) . ?
C65 H65 0.9300 . ?
C66 C67 1.350(11) . ?
C66 H66 0.9300 . ?
C67 C68 1.369(12) . ?
C67 H67 0.9300 . ?
C68 H68 0.9300 . ?
C69 C72 1.462(12) . ?
C69 C71 1.484(12) . ?
C69 C70 1.516(13) . ?
C70 H70A 0.9600 . ?
C70 H70B 0.9600 . ?
C70 H70C 0.9600 . ?
C71 H71A 0.9600 . ?
C71 H71B 0.9600 . ?
C71 H71C 0.9600 . ?
C72 H72A 0.9600 . ?
C72 H72B 0.9600 . ?
C72 H72C 0.9600 . ?

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
O1 S1 O2 121.2(5) . . ?
O1 S1 C9 110.3(4) . . ?
O2 S1 C9 108.9(4) . . ?
O1 S1 C1 107.7(5) . . ?
O2 S1 C1 104.0(4) . . ?
C9 S1 C1 103.0(4) . . ?
O3 S2 N1 112.5(5) . . ?
O3 S2 C15 107.7(6) . . ?
N1 S2 C15 95.1(5) . . ?
O5 S3 O4 119.1(4) . . ?
O5 S3 C27 109.6(4) . . ?
O4 S3 C27 109.3(4) . . ?
O5 S3 C19 106.4(4) . . ?
O4 S3 C19 107.0(4) . . ?
C27 S3 C19 104.4(4) . . ?
O6 S4 N2 114.9(4) . . ?
O6 S4 C33 106.1(5) . . ?
N2 S4 C33 97.7(4) . . ?
O7 S5 O8 121.0(4) . . ?
O7 S5 C45 107.4(4) . . ?
O8 S5 C45 111.4(4) . . ?
O7 S5 C37 106.8(5) . . ?
O8 S5 C37 105.2(4) . . ?
C45 S5 C37 103.5(4) . . ?
O9 S6 N3 105.8(6) . . ?
O9 S6 C51 98.0(6) . . ?
N3 S6 C51 96.2(4) . . ?
O11 S7 O10 120.7(5) . . ?
O11 S7 C63 109.5(5) . . ?
O10 S7 C63 109.4(4) . . ?
O11 S7 C55 104.9(4) . . ?
O10 S7 C55 106.8(5) . . ?
C63 S7 C55 104.2(4) . . ?
O12 S8 N4 113.8(4) . . ?
O12 S8 C69 105.4(5) . . ?
N4 S8 C69 96.0(4) . . ?
C2 N1 S2 124.5(7) . . ?
C20 N2 S4 124.4(6) . . ?
C38 N3 S6 115.4(7) . . ?
C56 N4 S8 121.1(6) . . ?
F1 C1 F2 107.2(8) . . ?
F1 C1 C2 109.8(8) . . ?
F2 C1 C2 109.7(8) . . ?
F1 C1 S1 109.1(6) . . ?
F2 C1 S1 108.9(7) . . ?
C2 C1 S1 112.1(7) . . ?
N1 C2 C3 132.1(9) . . ?
N1 C2 C1 112.0(8) . . ?
C3 C2 C1 115.5(9) . . ?
C4 C3 C8 118.1(9) . . ?
C4 C3 C2 117.4(9) . . ?
C8 C3 C2 124.4(9) . . ?
C3 C4 C5 121.9(10) . . ?
C3 C4 H4 119.1 . . ?
C5 C4 H4 119.0 . . ?
C6 C5 C4 117.7(10) . . ?
C6 C5 H5 121.1 . . ?
C4 C5 H5 121.2 . . ?
C5 C6 C7 121.8(9) . . ?
C5 C6 Br1 121.4(10) . . ?
C7 C6 Br1 116.5(9) . . ?
C6 C7 C8 119.3(9) . . ?
C6 C7 H7 120.4 . . ?
C8 C7 H7 120.3 . . ?
C3 C8 C7 121.1(9) . . ?
C3 C8 H8 119.4 . . ?
C7 C8 H8 119.5 . . ?
C14 C9 C10 121.7(9) . . ?
C14 C9 S1 119.3(8) . . ?
C10 C9 S1 118.9(7) . . ?
C9 C10 C11 115.9(8) . . ?
C9 C10 H10 122.0 . . ?
C11 C10 H10 122.0 . . ?
C12 C11 C10 121.1(10) . . ?
C12 C11 H11 119.5 . . ?
C10 C11 H11 119.4 . . ?
C11 C12 C13 121.5(11) . . ?
C11 C12 H12 119.3 . . ?
C13 C12 H12 119.2 . . ?
C12 C13 C14 118.5(10) . . ?
C12 C13 H13 120.8 . . ?
C14 C13 H13 120.7 . . ?
C9 C14 C13 121.2(10) . . ?
C9 C14 H14 119.4 . . ?
C13 C14 H14 119.4 . . ?
C18 C15 C16 110.8(10) . . ?
C18 C15 C17 117.1(11) . . ?
C16 C15 C17 110.5(11) . . ?
C18 C15 S2 110.5(9) . . ?
C16 C15 S2 105.2(8) . . ?
C17 C15 S2 101.8(7) . . ?
C15 C16 H16A 109.5 . . ?
C15 C16 H16B 109.5 . . ?
H16A C16 H16B 109.5 . . ?
C15 C16 H16C 109.4 . . ?
H16A C16 H16C 109.5 . . ?
H16B C16 H16C 109.5 . . ?
C15 C17 H17A 109.4 . . ?
C15 C17 H17B 109.5 . . ?
H17A C17 H17B 109.5 . . ?
C15 C17 H17C 109.5 . . ?
H17A C17 H17C 109.5 . . ?
H17B C17 H17C 109.5 . . ?
C15 C18 H18A 109.4 . . ?
C15 C18 H18B 109.4 . . ?
H18A C18 H18B 109.5 . . ?
C15 C18 H18C 109.5 . . ?
H18A C18 H18C 109.5 . . ?
H18B C18 H18C 109.5 . . ?
F4 C19 F3 105.1(7) . . ?
F4 C19 C20 109.2(7) . . ?
F3 C19 C20 109.3(7) . . ?
F4 C19 S3 109.6(7) . . ?
F3 C19 S3 109.7(6) . . ?
C20 C19 S3 113.6(6) . . ?
N2 C20 C21 132.3(8) . . ?
N2 C20 C19 110.6(7) . . ?
C21 C20 C19 117.0(8) . . ?
C26 C21 C22 120.7(8) . . ?
C26 C21 C20 120.7(9) . . ?
C22 C21 C20 118.5(8) . . ?
C21 C22 C23 117.9(9) . . ?
C21 C22 H22 121.1 . . ?
C23 C22 H22 121.1 . . ?
C24 C23 C22 121.1(9) . . ?
C24 C23 H23 119.4 . . ?
C22 C23 H23 119.4 . . ?
C23 C24 C25 121.8(9) . . ?
C23 C24 Br2 120.2(9) . . ?
C25 C24 Br2 118.0(9) . . ?
C24 C25 C26 118.1(9) . . ?
C24 C25 H25 121.0 . . ?
C26 C25 H25 120.9 . . ?
C21 C26 C25 120.4(9) . . ?
C21 C26 H26 119.8 . . ?
C25 C26 H26 119.8 . . ?
C32 C27 C28 119.6(9) . . ?
C32 C27 S3 120.5(7) . . ?
C28 C27 S3 119.9(8) . . ?
C29 C28 C27 118.3(10) . . ?
C29 C28 H28 120.9 . . ?
C27 C28 H28 120.8 . . ?
C28 C29 C30 124.6(11) . . ?
C28 C29 H29 117.8 . . ?
C30 C29 H29 117.6 . . ?
C29 C30 C31 114.8(12) . . ?
C29 C30 H30 122.6 . . ?
C31 C30 H30 122.5 . . ?
C32 C31 C30 123.9(12) . . ?
C32 C31 H31 118.1 . . ?
C30 C31 H31 118.0 . . ?
C31 C32 C27 118.6(10) . . ?
C31 C32 H32 120.6 . . ?
C27 C32 H32 120.7 . . ?
C35 C33 C34 111.2(9) . . ?
C35 C33 C36 112.0(9) . . ?
C34 C33 C36 111.9(9) . . ?
C35 C33 S4 108.9(7) . . ?
C34 C33 S4 105.2(7) . . ?
C36 C33 S4 107.2(7) . . ?
C33 C34 H34A 109.4 . . ?
C33 C34 H34B 109.5 . . ?
H34A C34 H34B 109.5 . . ?
C33 C34 H34C 109.5 . . ?
H34A C34 H34C 109.5 . . ?
H34B C34 H34C 109.5 . . ?
C33 C35 H35A 109.5 . . ?
C33 C35 H35B 109.5 . . ?
H35A C35 H35B 109.5 . . ?
C33 C35 H35C 109.4 . . ?
H35A C35 H35C 109.5 . . ?
H35B C35 H35C 109.5 . . ?
C33 C36 H36A 109.5 . . ?
C33 C36 H36B 109.4 . . ?
H36A C36 H36B 109.5 . . ?
C33 C36 H36C 109.5 . . ?
H36A C36 H36C 109.5 . . ?
H36B C36 H36C 109.5 . . ?
F5 C37 F6 109.3(8) . . ?
F5 C37 C38 112.0(8) . . ?
F6 C37 C38 111.0(7) . . ?
F5 C37 S5 107.6(6) . . ?
F6 C37 S5 106.7(6) . . ?
C38 C37 S5 110.1(6) . . ?
N3 C38 C39 130.4(9) . . ?
N3 C38 C37 112.6(8) . . ?
C39 C38 C37 116.9(9) . . ?
C40 C39 C44 118.5(8) . . ?
C40 C39 C38 122.4(9) . . ?
C44 C39 C38 119.1(8) . . ?
C39 C40 C41 123.4(10) . . ?
C39 C40 H40 118.3 . . ?
C41 C40 H40 118.3 . . ?
C42 C41 C40 115.6(10) . . ?
C42 C41 H41 122.2 . . ?
C40 C41 H41 122.2 . . ?
C43 C42 C41 121.1(9) . . ?
C43 C42 Br3 122.2(9) . . ?
C41 C42 Br3 116.4(8) . . ?
C42 C43 C44 121.1(9) . . ?
C42 C43 H43 119.4 . . ?
C44 C43 H43 119.5 . . ?
C43 C44 C39 120.1(9) . . ?
C43 C44 H44 119.9 . . ?
C39 C44 H44 120.0 . . ?
C46 C45 C50 119.2(9) . . ?
C46 C45 S5 122.4(8) . . ?
C50 C45 S5 118.4(7) . . ?
C45 C46 C47 121.1(10) . . ?
C45 C46 H46 119.5 . . ?
C47 C46 H46 119.5 . . ?
C48 C47 C46 118.6(10) . . ?
C48 C47 H47 120.7 . . ?
C46 C47 H47 120.6 . . ?
C49 C48 C47 122.9(12) . . ?
C49 C48 H48 118.6 . . ?
C47 C48 H48 118.5 . . ?
C48 C49 C50 118.0(12) . . ?
C48 C49 H49 121.0 . . ?
C50 C49 H49 121.0 . . ?
C49 C50 C45 120.1(9) . . ?
C49 C50 H50 120.0 . . ?
C45 C50 H50 119.9 . . ?
C53 C51 C52 119.0(13) . . ?
C53 C51 C54 104.4(10) . . ?
C52 C51 C54 107.6(9) . . ?
C53 C51 S6 116.2(9) . . ?
C52 C51 S6 108.3(7) . . ?
C54 C51 S6 98.7(9) . . ?
C51 C52 H52A 109.5 . . ?
C51 C52 H52B 109.4 . . ?
H52A C52 H52B 109.5 . . ?
C51 C52 H52C 109.5 . . ?
H52A C52 H52C 109.5 . . ?
H52B C52 H52C 109.5 . . ?
C51 C53 H53A 109.9 . . ?
C51 C53 H53B 109.8 . . ?
H53A C53 H53B 109.0 . . ?
C51 C53 H53C 110.2 . . ?
H53A C53 H53C 109.0 . . ?
H53B C53 H53C 109.0 . . ?
C51 C54 H54A 109.5 . . ?
C51 C54 H54B 109.5 . . ?
H54A C54 H54B 109.5 . . ?
C51 C54 H54C 109.5 . . ?
H54A C54 H54C 109.5 . . ?
H54B C54 H54C 109.5 . . ?
F8 C55 F7 106.1(8) . . ?
F8 C55 C56 109.9(7) . . ?
F7 C55 C56 111.7(8) . . ?
F8 C55 S7 107.9(7) . . ?
F7 C55 S7 108.2(6) . . ?
C56 C55 S7 112.8(6) . . ?
N4 C56 C57 135.1(9) . . ?
N4 C56 C55 109.7(8) . . ?
C57 C56 C55 115.3(8) . . ?
C62 C57 C58 120.2(8) . . ?
C62 C57 C56 122.8(9) . . ?
C58 C57 C56 116.9(9) . . ?
C59 C58 C57 119.8(9) . . ?
C59 C58 H58 120.1 . . ?
C57 C58 H58 120.1 . . ?
C58 C59 C60 119.7(9) . . ?
C58 C59 H59 120.1 . . ?
C60 C59 H59 120.2 . . ?
C59 C60 C61 122.5(8) . . ?
C59 C60 Br4 119.9(8) . . ?
C61 C60 Br4 117.5(8) . . ?
C60 C61 C62 117.7(8) . . ?
C60 C61 H61 121.2 . . ?
C62 C61 H61 121.2 . . ?
C57 C62 C61 119.7(9) . . ?
C57 C62 H62 120.1 . . ?
C61 C62 H62 120.1 . . ?
C68 C63 C64 122.0(9) . . ?
C68 C63 S7 120.8(7) . . ?
C64 C63 S7 117.2(8) . . ?
C65 C64 C63 117.9(10) . . ?
C65 C64 H64 121.1 . . ?
C63 C64 H64 121.0 . . ?
C64 C65 C66 120.9(10) . . ?
C64 C65 H65 119.6 . . ?
C66 C65 H65 119.5 . . ?
C67 C66 C65 120.6(10) . . ?
C67 C66 H66 119.7 . . ?
C65 C66 H66 119.7 . . ?
C66 C67 C68 120.1(10) . . ?
C66 C67 H67 120.0 . . ?
C68 C67 H67 120.0 . . ?
C63 C68 C67 118.4(9) . . ?
C63 C68 H68 120.8 . . ?
C67 C68 H68 120.8 . . ?
C72 C69 C71 110.4(10) . . ?
C72 C69 C70 112.1(9) . . ?
C71 C69 C70 113.8(10) . . ?
C72 C69 S8 109.7(7) . . ?
C71 C69 S8 107.1(7) . . ?
C70 C69 S8 103.4(7) . . ?
C69 C70 H70A 109.4 . . ?
C69 C70 H70B 109.5 . . ?
H70A C70 H70B 109.5 . . ?
C69 C70 H70C 109.5 . . ?
H70A C70 H70C 109.5 . . ?
H70B C70 H70C 109.5 . . ?
C69 C71 H71A 109.5 . . ?
C69 C71 H71B 109.5 . . ?
H71A C71 H71B 109.5 . . ?
C69 C71 H71C 109.5 . . ?
H71A C71 H71C 109.5 . . ?
H71B C71 H71C 109.5 . . ?
C69 C72 H72A 109.4 . . ?
C69 C72 H72B 109.5 . . ?
H72A C72 H72B 109.5 . . ?
C69 C72 H72C 109.5 . . ?
H72A C72 H72C 109.5 . . ?
H72B C72 H72C 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
O3 S2 N1 C2 -24.4(11) . . . . ?
C15 S2 N1 C2 -136.0(10) . . . . ?
O6 S4 N2 C20 -14.5(9) . . . . ?
C33 S4 N2 C20 -126.3(8) . . . . ?
O9 S6 N3 C38 -79.4(10) . . . . ?
C51 S6 N3 C38 -179.5(9) . . . . ?
O12 S8 N4 C56 -28.3(9) . . . . ?
C69 S8 N4 C56 -138.0(8) . . . . ?
O1 S1 C1 F1 46.5(8) . . . . ?
O2 S1 C1 F1 176.3(7) . . . . ?
C9 S1 C1 F1 -70.1(8) . . . . ?
O1 S1 C1 F2 163.2(6) . . . . ?
O2 S1 C1 F2 -67.0(7) . . . . ?
C9 S1 C1 F2 46.6(7) . . . . ?
O1 S1 C1 C2 -75.3(8) . . . . ?
O2 S1 C1 C2 54.5(8) . . . . ?
C9 S1 C1 C2 168.1(7) . . . . ?
S2 N1 C2 C3 -4.4(17) . . . . ?
S2 N1 C2 C1 -176.0(6) . . . . ?
F1 C1 C2 N1 -57.8(12) . . . . ?
F2 C1 C2 N1 -175.4(8) . . . . ?
S1 C1 C2 N1 63.6(10) . . . . ?
F1 C1 C2 C3 129.1(9) . . . . ?
F2 C1 C2 C3 11.5(12) . . . . ?
S1 C1 C2 C3 -109.6(8) . . . . ?
N1 C2 C3 C4 101.0(14) . . . . ?
C1 C2 C3 C4 -87.6(11) . . . . ?
N1 C2 C3 C8 -82.6(15) . . . . ?
C1 C2 C3 C8 88.8(11) . . . . ?
C8 C3 C4 C5 -1.2(15) . . . . ?
C2 C3 C4 C5 175.4(9) . . . . ?
C3 C4 C5 C6 1.0(16) . . . . ?
C4 C5 C6 C7 -1.0(16) . . . . ?
C4 C5 C6 Br1 -174.5(7) . . . . ?
C5 C6 C7 C8 1.3(16) . . . . ?
Br1 C6 C7 C8 175.1(8) . . . . ?
C4 C3 C8 C7 1.5(15) . . . . ?
C2 C3 C8 C7 -174.9(10) . . . . ?
C6 C7 C8 C3 -1.6(16) . . . . ?
O1 S1 C9 C14 -18.7(9) . . . . ?
O2 S1 C9 C14 -154.1(7) . . . . ?
C1 S1 C9 C14 96.0(8) . . . . ?
O1 S1 C9 C10 159.1(8) . . . . ?
O2 S1 C9 C10 23.7(9) . . . . ?
C1 S1 C9 C10 -86.3(8) . . . . ?
C14 C9 C10 C11 0.4(14) . . . . ?
S1 C9 C10 C11 -177.3(7) . . . . ?
C9 C10 C11 C12 0.5(15) . . . . ?
C10 C11 C12 C13 -1.5(19) . . . . ?
C11 C12 C13 C14 2(2) . . . . ?
C10 C9 C14 C13 -0.3(16) . . . . ?
S1 C9 C14 C13 177.4(9) . . . . ?
C12 C13 C14 C9 -0.6(19) . . . . ?
O3 S2 C15 C18 -177.1(9) . . . . ?
N1 S2 C15 C18 -61.5(10) . . . . ?
O3 S2 C15 C16 -57.4(9) . . . . ?
N1 S2 C15 C16 58.1(8) . . . . ?
O3 S2 C15 C17 57.9(9) . . . . ?
N1 S2 C15 C17 173.4(8) . . . . ?
O5 S3 C19 F4 58.6(7) . . . . ?
O4 S3 C19 F4 -173.1(5) . . . . ?
C27 S3 C19 F4 -57.3(7) . . . . ?
O5 S3 C19 F3 173.5(6) . . . . ?
O4 S3 C19 F3 -58.2(7) . . . . ?
C27 S3 C19 F3 57.6(7) . . . . ?
O5 S3 C19 C20 -63.8(7) . . . . ?
O4 S3 C19 C20 64.5(7) . . . . ?
C27 S3 C19 C20 -179.7(6) . . . . ?
S4 N2 C20 C21 1.8(14) . . . . ?
S4 N2 C20 C19 -176.9(5) . . . . ?
F4 C19 C20 N2 156.8(7) . . . . ?
F3 C19 C20 N2 42.3(9) . . . . ?
S3 C19 C20 N2 -80.6(8) . . . . ?
F4 C19 C20 C21 -22.1(10) . . . . ?
F3 C19 C20 C21 -136.6(7) . . . . ?
S3 C19 C20 C21 100.5(8) . . . . ?
N2 C20 C21 C26 101.8(12) . . . . ?
C19 C20 C21 C26 -79.6(11) . . . . ?
N2 C20 C21 C22 -82.3(12) . . . . ?
C19 C20 C21 C22 96.3(10) . . . . ?
C26 C21 C22 C23 1.2(14) . . . . ?
C20 C21 C22 C23 -174.7(9) . . . . ?
C21 C22 C23 C24 -1.2(17) . . . . ?
C22 C23 C24 C25 0.5(17) . . . . ?
C22 C23 C24 Br2 -179.9(8) . . . . ?
C23 C24 C25 C26 0.3(17) . . . . ?
Br2 C24 C25 C26 -179.4(8) . . . . ?
C22 C21 C26 C25 -0.5(15) . . . . ?
C20 C21 C26 C25 175.3(9) . . . . ?
C24 C25 C26 C21 -0.2(16) . . . . ?
O5 S3 C27 C32 -31.4(9) . . . . ?
O4 S3 C27 C32 -163.6(8) . . . . ?
C19 S3 C27 C32 82.3(9) . . . . ?
O5 S3 C27 C28 148.2(7) . . . . ?
O4 S3 C27 C28 16.0(8) . . . . ?
C19 S3 C27 C28 -98.2(7) . . . . ?
C32 C27 C28 C29 2.1(15) . . . . ?
S3 C27 C28 C29 -177.4(9) . . . . ?
C27 C28 C29 C30 -5(2) . . . . ?
C28 C29 C30 C31 5(2) . . . . ?
C29 C30 C31 C32 -2(2) . . . . ?
C30 C31 C32 C27 -0.1(19) . . . . ?
C28 C27 C32 C31 0.2(16) . . . . ?
S3 C27 C32 C31 179.7(9) . . . . ?
O6 S4 C33 C35 -177.2(7) . . . . ?
N2 S4 C33 C35 -58.4(8) . . . . ?
O6 S4 C33 C34 63.5(8) . . . . ?
N2 S4 C33 C34 -177.8(7) . . . . ?
O6 S4 C33 C36 -55.8(8) . . . . ?
N2 S4 C33 C36 63.0(7) . . . . ?
O7 S5 C37 F5 55.1(7) . . . . ?
O8 S5 C37 F5 -175.1(6) . . . . ?
C45 S5 C37 F5 -58.1(7) . . . . ?
O7 S5 C37 F6 172.3(5) . . . . ?
O8 S5 C37 F6 -57.9(6) . . . . ?
C45 S5 C37 F6 59.1(6) . . . . ?
O7 S5 C37 C38 -67.1(7) . . . . ?
O8 S5 C37 C38 62.6(7) . . . . ?
C45 S5 C37 C38 179.6(7) . . . . ?
S6 N3 C38 C39 3.7(16) . . . . ?
S6 N3 C38 C37 -178.0(6) . . . . ?
F5 C37 C38 N3 -42.9(12) . . . . ?
F6 C37 C38 N3 -165.3(9) . . . . ?
S5 C37 C38 N3 76.8(10) . . . . ?
F5 C37 C38 C39 135.6(8) . . . . ?
F6 C37 C38 C39 13.2(11) . . . . ?
S5 C37 C38 C39 -104.7(8) . . . . ?
N3 C38 C39 C40 83.2(15) . . . . ?
C37 C38 C39 C40 -95.0(11) . . . . ?
N3 C38 C39 C44 -98.3(14) . . . . ?
C37 C38 C39 C44 83.5(11) . . . . ?
C44 C39 C40 C41 1.3(15) . . . . ?
C38 C39 C40 C41 179.7(9) . . . . ?
C39 C40 C41 C42 1.5(16) . . . . ?
C40 C41 C42 C43 -4.1(16) . . . . ?
C40 C41 C42 Br3 -177.6(7) . . . . ?
C41 C42 C43 C44 4.1(18) . . . . ?
Br3 C42 C43 C44 177.2(9) . . . . ?
C42 C43 C44 C39 -1.2(18) . . . . ?
C40 C39 C44 C43 -1.5(16) . . . . ?
C38 C39 C44 C43 180.0(10) . . . . ?
O7 S5 C45 C46 -18.7(9) . . . . ?
O8 S5 C45 C46 -153.4(7) . . . . ?
C37 S5 C45 C46 94.1(8) . . . . ?
O7 S5 C45 C50 158.5(7) . . . . ?
O8 S5 C45 C50 23.8(8) . . . . ?
C37 S5 C45 C50 -88.7(8) . . . . ?
C50 C45 C46 C47 -1.0(15) . . . . ?
S5 C45 C46 C47 176.2(8) . . . . ?
C45 C46 C47 C48 3.1(18) . . . . ?
C46 C47 C48 C49 -2(2) . . . . ?
C47 C48 C49 C50 -0.5(18) . . . . ?
C48 C49 C50 C45 2.7(15) . . . . ?
C46 C45 C50 C49 -1.9(14) . . . . ?
S5 C45 C50 C49 -179.3(7) . . . . ?
O9 S6 C51 C53 -59.9(12) . . . . ?
N3 S6 C51 C53 47.0(12) . . . . ?
O9 S6 C51 C52 77.2(10) . . . . ?
N3 S6 C51 C52 -175.9(9) . . . . ?
O9 S6 C51 C54 -170.9(8) . . . . ?
N3 S6 C51 C54 -63.9(8) . . . . ?
O11 S7 C55 F8 67.6(7) . . . . ?
O10 S7 C55 F8 -163.2(6) . . . . ?
C63 S7 C55 F8 -47.4(7) . . . . ?
O11 S7 C55 F7 -178.1(6) . . . . ?
O10 S7 C55 F7 -48.8(8) . . . . ?
C63 S7 C55 F7 66.9(7) . . . . ?
O11 S7 C55 C56 -53.9(8) . . . . ?
O10 S7 C55 C56 75.3(8) . . . . ?
C63 S7 C55 C56 -168.9(7) . . . . ?
S8 N4 C56 C57 0.4(16) . . . . ?
S8 N4 C56 C55 -177.7(5) . . . . ?
F8 C55 C56 N4 160.6(8) . . . . ?
F7 C55 C56 N4 43.2(11) . . . . ?
S7 C55 C56 N4 -79.0(9) . . . . ?
F8 C55 C56 C57 -17.9(11) . . . . ?
F7 C55 C56 C57 -135.3(8) . . . . ?
S7 C55 C56 C57 102.5(8) . . . . ?
N4 C56 C57 C62 104.8(13) . . . . ?
C55 C56 C57 C62 -77.2(11) . . . . ?
N4 C56 C57 C58 -77.6(14) . . . . ?
C55 C56 C57 C58 100.4(9) . . . . ?
C62 C57 C58 C59 5.9(14) . . . . ?
C56 C57 C58 C59 -171.7(9) . . . . ?
C57 C58 C59 C60 -5.9(15) . . . . ?
C58 C59 C60 C61 1.7(15) . . . . ?
C58 C59 C60 Br4 178.5(7) . . . . ?
C59 C60 C61 C62 2.5(15) . . . . ?
Br4 C60 C61 C62 -174.4(7) . . . . ?
C58 C57 C62 C61 -1.7(14) . . . . ?
C56 C57 C62 C61 175.8(9) . . . . ?
C60 C61 C62 C57 -2.4(15) . . . . ?
O11 S7 C63 C68 -34.3(9) . . . . ?
O10 S7 C63 C68 -168.6(8) . . . . ?
C55 S7 C63 C68 77.5(8) . . . . ?
O11 S7 C63 C64 147.2(7) . . . . ?
O10 S7 C63 C64 12.9(8) . . . . ?
C55 S7 C63 C64 -101.0(7) . . . . ?
C68 C63 C64 C65 4.7(14) . . . . ?
S7 C63 C64 C65 -176.8(7) . . . . ?
C63 C64 C65 C66 -3.5(16) . . . . ?
C64 C65 C66 C67 1.3(17) . . . . ?
C65 C66 C67 C68 -0.1(17) . . . . ?
C64 C63 C68 C67 -3.5(15) . . . . ?
S7 C63 C68 C67 178.0(7) . . . . ?
C66 C67 C68 C63 1.2(16) . . . . ?
O12 S8 C69 C72 -57.1(9) . . . . ?
N4 S8 C69 C72 59.6(8) . . . . ?
O12 S8 C69 C71 -176.9(9) . . . . ?
N4 S8 C69 C71 -60.2(9) . . . . ?
O12 S8 C69 C70 62.6(8) . . . . ?
N4 S8 C69 C70 179.3(7) . . . . ?

_diffrn_measured_fraction_theta_max 0.998
_diffrn_reflns_theta_full        27.00
_diffrn_measured_fraction_theta_full 0.998
_refine_diff_density_max         0.535
_refine_diff_density_min         -0.487
_refine_diff_density_rms         0.079


_database_code_depnum_ccdc_archive 'CCDC 1009678'
#######################################################################
#
#                 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_cd27130

_audit_creation_method           SHELXL-97
_chemical_name_systematic        
; 
 ? 
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C18 H18 F2 N O S'
_chemical_formula_weight         335.40

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'
N N 0.0061 0.0033 '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'
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'

_symmetry_cell_setting           Orthorhombic
_symmetry_space_group_name_H-M   P2(1)2(1)2(1)

loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'-x+1/2, -y, z+1/2'
'-x, y+1/2, -z+1/2'
'x+1/2, -y+1/2, -z'

_cell_length_a                   8.7675(12)
_cell_length_b                   10.5238(14)
_cell_length_c                   18.173(2)
_cell_angle_alpha                90.00
_cell_angle_beta                 90.00
_cell_angle_gamma                90.00
_cell_volume                     1676.8(4)
_cell_formula_units_Z            4
_cell_measurement_temperature    293(2)
_cell_measurement_reflns_used    1795
_cell_measurement_theta_min      4.473
_cell_measurement_theta_max      42.051

_exptl_crystal_description       prismatic
_exptl_crystal_colour            colorless
_exptl_crystal_size_max          0.421
_exptl_crystal_size_mid          0.140
_exptl_crystal_size_min          0.127
_exptl_crystal_density_meas      ?
_exptl_crystal_density_diffrn    1.329
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             704
_exptl_absorpt_coefficient_mu    0.216
_exptl_absorpt_correction_type   empirical
_exptl_absorpt_correction_T_min  0.7258
_exptl_absorpt_correction_T_max  1.0000
_exptl_absorpt_process_details   ?

_exptl_special_details           
; 
 ? 
;

_diffrn_ambient_temperature      293(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_radiation_source         'fine-focus sealed tube'
_diffrn_radiation_monochromator  graphite
_diffrn_measurement_device_type  'CCD area detector'
_diffrn_measurement_method       'phi and omega scans'
_diffrn_detector_area_resol_mean ?
_diffrn_standards_number         ?
_diffrn_standards_interval_count ?
_diffrn_standards_interval_time  ?
_diffrn_standards_decay_%        ?
_diffrn_reflns_number            10158
_diffrn_reflns_av_R_equivalents  0.1205
_diffrn_reflns_av_sigmaI/netI    0.1110
_diffrn_reflns_limit_h_min       -10
_diffrn_reflns_limit_h_max       11
_diffrn_reflns_limit_k_min       -13
_diffrn_reflns_limit_k_max       13
_diffrn_reflns_limit_l_min       -22
_diffrn_reflns_limit_l_max       23
_diffrn_reflns_theta_min         2.24
_diffrn_reflns_theta_max         27.50
_reflns_number_total             3793
_reflns_number_gt                2322
_reflns_threshold_expression     >2sigma(I)

_computing_data_collection       'Bruker SMART'
_computing_cell_refinement       'Bruker SMART'
_computing_data_reduction        'Bruker SHELXTL'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 1990)'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_computing_molecular_graphics    'Bruker SHELXTL'
_computing_publication_material  'Bruker SHELXTL'

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

_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'calc w=1/[σ²(Fo²)+(0.0342P)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     SHELXL
_refine_ls_extinction_coef       0.0218(19)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc²λ³/sin(2θ)]^-1/4^
_refine_ls_abs_structure_details 'Flack H D (1983), Acta Cryst. A39, 876-881'
_refine_ls_abs_structure_Flack   -0.18(10)
_chemical_absolute_configuration ad
_refine_ls_number_reflns         3793
_refine_ls_number_parameters     221
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0858
_refine_ls_R_factor_gt           0.0545
_refine_ls_wR_factor_ref         0.1171
_refine_ls_wR_factor_gt          0.1057
_refine_ls_goodness_of_fit_ref   0.859
_refine_ls_restrained_S_all      0.859
_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 0.20712(9) 0.13508(7) 0.89883(4) 0.0506(2) Uani 1 1 d . . .
F1 F 0.6303(3) 0.1580(3) 0.8155(2) 0.0904(11) Uani 0.65 1 d P . .
F2 F 0.6287(3) 0.3436(3) 0.82300(17) 0.0840(9) Uani 0.75 1 d P . .
F1' F 0.5556(4) 0.2401(4) 0.9082(2) 0.0805(10) Uani 0.60 1 d P . .
O1 O 0.2488(3) 0.0970(2) 0.97237(12) 0.0770(8) Uani 1 1 d . . .
N1 N 0.3223(3) 0.1180(2) 0.83626(14) 0.0498(6) Uani 1 1 d . . .
C1 C 0.1792(4) 0.3011(2) 0.89190(16) 0.0492(8) Uani 1 1 d . . .
C2 C 0.0790(4) 0.3785(4) 0.92977(18) 0.0647(9) Uani 1 1 d . . .
H2 H 0.0057 0.3457 0.9615 0.078 Uiso 1 1 calc R . .
C3 C 0.0943(5) 0.5086(4) 0.9177(2) 0.0788(11) Uani 1 1 d . . .
H3 H 0.0265 0.5643 0.9402 0.095 Uiso 1 1 calc R . .
C4 C 0.2070(5) 0.5563(3) 0.87346(19) 0.0748(11) Uani 1 1 d . . .
H4 H 0.2168 0.6438 0.8680 0.090 Uiso 1 1 calc R . .
C5 C 0.3069(4) 0.4761(3) 0.83667(17) 0.0585(8) Uani 1 1 d . . .
H5 H 0.3835 0.5091 0.8069 0.070 Uiso 1 1 calc R . .
C6 C 0.2904(4) 0.3454(3) 0.84519(15) 0.0465(7) Uani 1 1 d . . .
C7 C 0.3867(3) 0.2387(3) 0.81007(17) 0.0469(7) Uani 1 1 d . . .
C8 C 0.5484(4) 0.2438(4) 0.8402(2) 0.0671(10) Uani 1 1 d . . .
C9 C 0.3855(3) 0.2433(3) 0.72589(17) 0.0481(7) Uani 1 1 d . . .
C10 C 0.4501(4) 0.3437(3) 0.68689(19) 0.0631(9) Uani 1 1 d . . .
H10 H 0.4940 0.4107 0.7126 0.076 Uiso 1 1 calc R . .
C11 C 0.4507(5) 0.3461(4) 0.6118(2) 0.0798(11) Uani 1 1 d . . .
H11 H 0.4938 0.4146 0.5870 0.096 Uiso 1 1 calc R . .
C12 C 0.3882(5) 0.2481(4) 0.5731(2) 0.0802(11) Uani 1 1 d . . .
H12 H 0.3895 0.2494 0.5220 0.096 Uiso 1 1 calc R . .
C13 C 0.3234(4) 0.1478(3) 0.6096(2) 0.0763(11) Uani 1 1 d . . .
H13 H 0.2797 0.0814 0.5832 0.092 Uiso 1 1 calc R . .
C14 C 0.3231(3) 0.1452(3) 0.68501(19) 0.0560(8) Uani 1 1 d . . .
H14 H 0.2802 0.0761 0.7092 0.067 Uiso 1 1 calc R . .
C15 C 0.0348(4) 0.0491(3) 0.87602(19) 0.0631(9) Uani 1 1 d . . .
C16 C -0.0318(4) 0.1056(4) 0.8057(2) 0.0847(13) Uani 1 1 d . . .
H16A H -0.1196 0.0573 0.7910 0.127 Uiso 1 1 calc R . .
H16B H 0.0434 0.1030 0.7673 0.127 Uiso 1 1 calc R . .
H16C H -0.0613 0.1922 0.8144 0.127 Uiso 1 1 calc R . .
C17 C 0.0826(5) -0.0882(4) 0.8642(2) 0.0983(15) Uani 1 1 d . . .
H17A H 0.1335 -0.1190 0.9074 0.147 Uiso 1 1 calc R . .
H17B H 0.1506 -0.0932 0.8229 0.147 Uiso 1 1 calc R . .
H17C H -0.0061 -0.1392 0.8548 0.147 Uiso 1 1 calc R . .
C18 C -0.0777(4) 0.0597(4) 0.9405(2) 0.0900(13) Uani 1 1 d . . .
H18A H -0.1661 0.0088 0.9305 0.135 Uiso 1 1 calc R . .
H18B H -0.1077 0.1468 0.9466 0.135 Uiso 1 1 calc R . .
H18C H -0.0295 0.0302 0.9848 0.135 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 O1 1.442(2) . ?
S1 N1 1.531(2) . ?
S1 C1 1.768(3) . ?
S1 C15 1.809(4) . ?
F1 C8 1.238(4) . ?
F2 C8 1.303(4) . ?
F1' C8 1.239(5) . ?
N1 C7 1.470(4) . ?
C1 C6 1.374(4) . ?
C1 C2 1.382(4) . ?
C2 C3 1.393(5) . ?
C2 H2 0.9300 . ?
C3 C4 1.369(5) . ?
C3 H3 0.9300 . ?
C4 C5 1.388(4) . ?
C4 H4 0.9300 . ?
C5 C6 1.391(4) . ?
C5 H5 0.9300 . ?
C6 C7 1.544(4) . ?
C7 C8 1.520(5) . ?
C7 C9 1.531(4) . ?
C9 C14 1.385(4) . ?
C9 C10 1.393(4) . ?
C10 C11 1.365(5) . ?
C10 H10 0.9300 . ?
C11 C12 1.363(5) . ?
C11 H11 0.9300 . ?
C12 C13 1.370(5) . ?
C12 H12 0.9300 . ?
C13 C14 1.371(5) . ?
C13 H13 0.9300 . ?
C14 H14 0.9300 . ?
C15 C17 1.520(5) . ?
C15 C16 1.527(5) . ?
C15 C18 1.536(5) . ?
C16 H16A 0.9600 . ?
C16 H16B 0.9600 . ?
C16 H16C 0.9600 . ?
C17 H17A 0.9600 . ?
C17 H17B 0.9600 . ?
C17 H17C 0.9600 . ?
C18 H18A 0.9600 . ?
C18 H18B 0.9600 . ?
C18 H18C 0.9600 . ?

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
O1 S1 N1 119.23(14) . . ?
O1 S1 C1 112.07(13) . . ?
N1 S1 C1 98.88(13) . . ?
O1 S1 C15 106.55(15) . . ?
N1 S1 C15 108.76(15) . . ?
C1 S1 C15 111.23(15) . . ?
C7 N1 S1 113.09(18) . . ?
C6 C1 C2 123.9(3) . . ?
C6 C1 S1 106.4(2) . . ?
C2 C1 S1 129.4(3) . . ?
C1 C2 C3 116.1(3) . . ?
C1 C2 H2 122.0 . . ?
C3 C2 H2 122.0 . . ?
C4 C3 C2 121.5(3) . . ?
C4 C3 H3 119.2 . . ?
C2 C3 H3 119.2 . . ?
C3 C4 C5 121.0(3) . . ?
C3 C4 H4 119.5 . . ?
C5 C4 H4 119.5 . . ?
C4 C5 C6 118.8(3) . . ?
C4 C5 H5 120.6 . . ?
C6 C5 H5 120.6 . . ?
C1 C6 C5 118.6(3) . . ?
C1 C6 C7 113.4(2) . . ?
C5 C6 C7 128.0(3) . . ?
N1 C7 C8 105.8(3) . . ?
N1 C7 C9 110.4(2) . . ?
C8 C7 C9 111.4(3) . . ?
N1 C7 C6 106.5(2) . . ?
C8 C7 C6 109.6(3) . . ?
C9 C7 C6 112.7(2) . . ?
F1 C8 F1' 108.0(4) . . ?
F1 C8 F2 100.8(3) . . ?
F1' C8 F2 103.7(4) . . ?
F1 C8 C7 112.6(4) . . ?
F1' C8 C7 113.9(3) . . ?
F2 C8 C7 116.5(3) . . ?
C14 C9 C10 117.0(3) . . ?
C14 C9 C7 121.0(3) . . ?
C10 C9 C7 122.0(3) . . ?
C11 C10 C9 121.6(3) . . ?
C11 C10 H10 119.2 . . ?
C9 C10 H10 119.2 . . ?
C12 C11 C10 120.0(3) . . ?
C12 C11 H11 120.0 . . ?
C10 C11 H11 120.0 . . ?
C11 C12 C13 120.1(3) . . ?
C11 C12 H12 120.0 . . ?
C13 C12 H12 120.0 . . ?
C12 C13 C14 120.0(3) . . ?
C12 C13 H13 120.0 . . ?
C14 C13 H13 120.0 . . ?
C13 C14 C9 121.4(3) . . ?
C13 C14 H14 119.3 . . ?
C9 C14 H14 119.3 . . ?
C17 C15 C16 110.9(3) . . ?
C17 C15 C18 110.7(3) . . ?
C16 C15 C18 111.4(3) . . ?
C17 C15 S1 106.1(3) . . ?
C16 C15 S1 108.5(2) . . ?
C18 C15 S1 109.0(2) . . ?
C15 C16 H16A 109.5 . . ?
C15 C16 H16B 109.5 . . ?
H16A C16 H16B 109.5 . . ?
C15 C16 H16C 109.5 . . ?
H16A C16 H16C 109.5 . . ?
H16B C16 H16C 109.5 . . ?
C15 C17 H17A 109.5 . . ?
C15 C17 H17B 109.5 . . ?
H17A C17 H17B 109.5 . . ?
C15 C17 H17C 109.5 . . ?
H17A C17 H17C 109.5 . . ?
H17B C17 H17C 109.5 . . ?
C15 C18 H18A 109.5 . . ?
C15 C18 H18B 109.5 . . ?
H18A C18 H18B 109.5 . . ?
C15 C18 H18C 109.5 . . ?
H18A C18 H18C 109.5 . . ?
H18B C18 H18C 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 S1 N1 C7 -108.3(2) . . . . ?
C1 S1 N1 C7 13.3(2) . . . . ?
C15 S1 N1 C7 129.4(2) . . . . ?
O1 S1 C1 C6 115.4(2) . . . . ?
N1 S1 C1 C6 -11.2(2) . . . . ?
C15 S1 C1 C6 -125.4(2) . . . . ?
O1 S1 C1 C2 -58.4(3) . . . . ?
N1 S1 C1 C2 175.0(3) . . . . ?
C15 S1 C1 C2 60.7(3) . . . . ?
C6 C1 C2 C3 0.7(5) . . . . ?
S1 C1 C2 C3 173.6(3) . . . . ?
C1 C2 C3 C4 -2.9(5) . . . . ?
C2 C3 C4 C5 2.5(6) . . . . ?
C3 C4 C5 C6 0.3(5) . . . . ?
C2 C1 C6 C5 1.9(5) . . . . ?
S1 C1 C6 C5 -172.3(2) . . . . ?
C2 C1 C6 C7 179.9(3) . . . . ?
S1 C1 C6 C7 5.7(3) . . . . ?
C4 C5 C6 C1 -2.4(4) . . . . ?
C4 C5 C6 C7 179.9(3) . . . . ?
S1 N1 C7 C8 105.5(3) . . . . ?
S1 N1 C7 C9 -133.8(2) . . . . ?
S1 N1 C7 C6 -11.1(3) . . . . ?
C1 C6 C7 N1 2.5(3) . . . . ?
C5 C6 C7 N1 -179.7(3) . . . . ?
C1 C6 C7 C8 -111.5(3) . . . . ?
C5 C6 C7 C8 66.2(4) . . . . ?
C1 C6 C7 C9 123.7(3) . . . . ?
C5 C6 C7 C9 -58.5(4) . . . . ?
N1 C7 C8 F1 63.6(4) . . . . ?
C9 C7 C8 F1 -56.4(4) . . . . ?
C6 C7 C8 F1 178.1(3) . . . . ?
N1 C7 C8 F1' -59.9(4) . . . . ?
C9 C7 C8 F1' -179.9(3) . . . . ?
C6 C7 C8 F1' 54.6(4) . . . . ?
N1 C7 C8 F2 179.4(3) . . . . ?
C9 C7 C8 F2 59.4(4) . . . . ?
C6 C7 C8 F2 -66.1(4) . . . . ?
N1 C7 C9 C14 2.8(4) . . . . ?
C8 C7 C9 C14 120.0(3) . . . . ?
C6 C7 C9 C14 -116.3(3) . . . . ?
N1 C7 C9 C10 -175.4(3) . . . . ?
C8 C7 C9 C10 -58.1(4) . . . . ?
C6 C7 C9 C10 65.6(4) . . . . ?
C14 C9 C10 C11 0.7(5) . . . . ?
C7 C9 C10 C11 178.9(3) . . . . ?
C9 C10 C11 C12 -0.6(6) . . . . ?
C10 C11 C12 C13 0.6(6) . . . . ?
C11 C12 C13 C14 -0.8(6) . . . . ?
C12 C13 C14 C9 0.9(6) . . . . ?
C10 C9 C14 C13 -0.9(5) . . . . ?
C7 C9 C14 C13 -179.1(3) . . . . ?
O1 S1 C15 C17 -72.2(3) . . . . ?
N1 S1 C15 C17 57.5(3) . . . . ?
C1 S1 C15 C17 165.4(2) . . . . ?
O1 S1 C15 C16 168.6(2) . . . . ?
N1 S1 C15 C16 -61.7(3) . . . . ?
C1 S1 C15 C16 46.2(3) . . . . ?
O1 S1 C15 C18 47.1(3) . . . . ?
N1 S1 C15 C18 176.8(2) . . . . ?
C1 S1 C15 C18 -75.3(3) . . . . ?

_diffrn_measured_fraction_theta_max 0.999
_diffrn_reflns_theta_full        27.50
_diffrn_measured_fraction_theta_full 0.999
_refine_diff_density_max         0.393
_refine_diff_density_min         -0.205
_refine_diff_density_rms         0.047

_database_code_depnum_ccdc_archive 'CCDC 1009679'
#######################################################################
#
#                 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_cd2986

_audit_creation_method           SHELXL-97
_chemical_name_systematic        
; 
 ? 
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C24 H23 F2 N O3 S2'
_chemical_formula_weight         475.55

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'
N N 0.0061 0.0033 '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'
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'

_symmetry_cell_setting           Orthorhombic
_symmetry_space_group_name_H-M   P2(1)2(1)2(1)

loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'-x+1/2, -y, z+1/2'
'-x, y+1/2, -z+1/2'
'x+1/2, -y+1/2, -z'

_cell_length_a                   10.0872(9)
_cell_length_b                   14.0488(12)
_cell_length_c                   16.2483(14)
_cell_angle_alpha                90.00
_cell_angle_beta                 90.00
_cell_angle_gamma                90.00
_cell_volume                     2302.6(3)
_cell_formula_units_Z            4
_cell_measurement_temperature    293(2)
_cell_measurement_reflns_used    3987
_cell_measurement_theta_min      4.753
_cell_measurement_theta_max      46.367

_exptl_crystal_description       prismatic
_exptl_crystal_colour            colorless
_exptl_crystal_size_max          0.403
_exptl_crystal_size_mid          0.365
_exptl_crystal_size_min          0.286
_exptl_crystal_density_meas      ?
_exptl_crystal_density_diffrn    1.372
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             992
_exptl_absorpt_coefficient_mu    0.274
_exptl_absorpt_correction_type   empirical
_exptl_absorpt_correction_T_min  0.8204
_exptl_absorpt_correction_T_max  1.0000
_exptl_absorpt_process_details   sadabs

_exptl_special_details           
; 
 ? 
;

_diffrn_ambient_temperature      293(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_radiation_source         'fine-focus sealed tube'
_diffrn_radiation_monochromator  graphite
_diffrn_measurement_device_type  'CCD area detector'
_diffrn_measurement_method       'phi and omega scans'
_diffrn_detector_area_resol_mean ?
_diffrn_standards_number         ?
_diffrn_standards_interval_count ?
_diffrn_standards_interval_time  ?
_diffrn_standards_decay_%        ?
_diffrn_reflns_number            13675
_diffrn_reflns_av_R_equivalents  0.0366
_diffrn_reflns_av_sigmaI/netI    0.0486
_diffrn_reflns_limit_h_min       -11
_diffrn_reflns_limit_h_max       12
_diffrn_reflns_limit_k_min       -17
_diffrn_reflns_limit_k_max       17
_diffrn_reflns_limit_l_min       -19
_diffrn_reflns_limit_l_max       20
_diffrn_reflns_theta_min         1.92
_diffrn_reflns_theta_max         27.00
_reflns_number_total             5004
_reflns_number_gt                4088
_reflns_threshold_expression     >2sigma(I)

_computing_data_collection       'Bruker SMART'
_computing_cell_refinement       'Bruker SMART'
_computing_data_reduction        'Bruker SHELXTL'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 1990)'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_computing_molecular_graphics    'Bruker SHELXTL'
_computing_publication_material  'Bruker SHELXTL'

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

_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'calc w=1/[σ²(Fo²)+(0.0379P)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     SHELXL
_refine_ls_extinction_coef       0.0033(4)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc²λ³/sin(2θ)]^-1/4^
_refine_ls_abs_structure_details 'Flack H D (1983), Acta Cryst. A39, 876-881'
_refine_ls_abs_structure_Flack   0.01(6)
_chemical_absolute_configuration ad
_refine_ls_number_reflns         5004
_refine_ls_number_parameters     293
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0508
_refine_ls_R_factor_gt           0.0405
_refine_ls_wR_factor_ref         0.0824
_refine_ls_wR_factor_gt          0.0786
_refine_ls_goodness_of_fit_ref   0.937
_refine_ls_restrained_S_all      0.937
_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 0.00710(7) 0.92662(4) 0.69222(4) 0.05497(18) Uani 1 1 d . . .
S2 S -0.06954(5) 0.90308(3) 0.96622(3) 0.03756(14) Uani 1 1 d . . .
F1 F -0.17406(14) 1.00687(10) 0.77517(8) 0.0618(4) Uani 1 1 d . . .
F2 F -0.02048(17) 1.10281(9) 0.73637(8) 0.0666(4) Uani 1 1 d . . .
O1 O -0.0664(2) 0.84225(13) 0.70988(12) 0.0737(6) Uani 1 1 d . . .
O2 O -0.0141(2) 0.97529(15) 0.61655(10) 0.0800(6) Uani 1 1 d . . .
O3 O 0.00493(16) 0.87283(10) 1.03750(9) 0.0497(4) Uani 1 1 d . . .
N1 N 0.00058(18) 0.91184(11) 0.88281(10) 0.0385(4) Uani 1 1 d . . .
C1 C -0.0405(2) 1.01716(15) 0.77131(14) 0.0457(6) Uani 1 1 d . . .
C2 C 0.0207(2) 1.01095(13) 0.85785(12) 0.0381(5) Uani 1 1 d . . .
C3 C 0.1668(2) 1.04053(14) 0.86221(13) 0.0404(5) Uani 1 1 d . . .
C4 C 0.2188(3) 1.11956(19) 0.82350(18) 0.0710(8) Uani 1 1 d . . .
H4 H 0.1645 1.1574 0.7908 0.085 Uiso 1 1 calc R . .
C5 C 0.3512(4) 1.1430(2) 0.8330(2) 0.0955(12) Uani 1 1 d . . .
H5 H 0.3850 1.1954 0.8051 0.115 Uiso 1 1 calc R . .
C6 C 0.4333(3) 1.0908(2) 0.8823(2) 0.0822(9) Uani 1 1 d . . .
H6 H 0.5224 1.1068 0.8878 0.099 Uiso 1 1 calc R . .
C7 C 0.3823(3) 1.0158(2) 0.9228(2) 0.0772(9) Uani 1 1 d . . .
H7 H 0.4356 0.9810 0.9585 0.093 Uiso 1 1 calc R . .
C8 C 0.2517(3) 0.9901(2) 0.91193(17) 0.0598(7) Uani 1 1 d . . .
H8 H 0.2197 0.9366 0.9392 0.072 Uiso 1 1 calc R . .
C9 C 0.1764(2) 0.90382(17) 0.70249(13) 0.0491(6) Uani 1 1 d . . .
C10 C 0.2632(3) 0.9617(2) 0.66155(19) 0.0714(9) Uani 1 1 d . . .
H10 H 0.2320 1.0124 0.6302 0.086 Uiso 1 1 calc R . .
C11 C 0.3976(4) 0.9442(2) 0.6671(2) 0.0908(11) Uani 1 1 d . . .
H11 H 0.4575 0.9834 0.6398 0.109 Uiso 1 1 calc R . .
C12 C 0.4422(3) 0.8695(2) 0.7128(2) 0.0877(10) Uani 1 1 d . . .
H12 H 0.5328 0.8581 0.7169 0.105 Uiso 1 1 calc R . .
C13 C 0.3555(4) 0.8116(2) 0.75230(19) 0.0794(9) Uani 1 1 d . . .
H13 H 0.3871 0.7600 0.7823 0.095 Uiso 1 1 calc R . .
C14 C 0.2207(3) 0.82848(18) 0.74853(15) 0.0621(7) Uani 1 1 d . . .
H14 H 0.1614 0.7896 0.7766 0.075 Uiso 1 1 calc R . .
C15 C -0.0623(2) 1.07303(14) 0.91540(13) 0.0418(5) Uani 1 1 d . . .
C16 C -0.0795(3) 1.17089(15) 0.91434(16) 0.0577(7) Uani 1 1 d . . .
H16 H -0.0371 1.2079 0.8748 0.069 Uiso 1 1 calc R . .
C17 C -0.1592(3) 1.21233(17) 0.97180(18) 0.0704(8) Uani 1 1 d . . .
H17 H -0.1718 1.2779 0.9703 0.084 Uiso 1 1 calc R . .
C18 C -0.2218(3) 1.15959(18) 1.03229(18) 0.0679(8) Uani 1 1 d . . .
H18 H -0.2775 1.1893 1.0699 0.081 Uiso 1 1 calc R . .
C19 C -0.2012(3) 1.06294(16) 1.03648(16) 0.0539(6) Uani 1 1 d . . .
H19 H -0.2383 1.0267 1.0785 0.065 Uiso 1 1 calc R . .
C20 C -0.1242(2) 1.02166(14) 0.97690(14) 0.0401(5) Uani 1 1 d . . .
C21 C -0.2085(2) 0.82004(15) 0.95759(16) 0.0481(6) Uani 1 1 d . . .
C22 C -0.2743(3) 0.8126(2) 1.04064(18) 0.0773(9) Uani 1 1 d . . .
H22A H -0.3193 0.8712 1.0528 0.116 Uiso 1 1 calc R . .
H22B H -0.2084 0.8006 1.0820 0.116 Uiso 1 1 calc R . .
H22C H -0.3372 0.7613 1.0400 0.116 Uiso 1 1 calc R . .
C23 C -0.1466(3) 0.72534(17) 0.9330(2) 0.0789(9) Uani 1 1 d . . .
H23A H -0.2147 0.6779 0.9283 0.118 Uiso 1 1 calc R . .
H23B H -0.0837 0.7062 0.9742 0.118 Uiso 1 1 calc R . .
H23C H -0.1023 0.7322 0.8811 0.118 Uiso 1 1 calc R . .
C24 C -0.3027(3) 0.8541(2) 0.89204(19) 0.0766(9) Uani 1 1 d . . .
H24A H -0.3786 0.8128 0.8902 0.115 Uiso 1 1 calc R . .
H24B H -0.2589 0.8533 0.8396 0.115 Uiso 1 1 calc R . .
H24C H -0.3309 0.9177 0.9045 0.115 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 O2 1.4229(19) . ?
S1 O1 1.4271(19) . ?
S1 C9 1.745(3) . ?
S1 C1 1.871(2) . ?
S2 O3 1.4444(16) . ?
S2 N1 1.5338(17) . ?
S2 C20 1.763(2) . ?
S2 C21 1.829(2) . ?
F1 C1 1.357(3) . ?
F2 C1 1.346(2) . ?
N1 C2 1.464(2) . ?
C1 C2 1.538(3) . ?
C2 C15 1.528(3) . ?
C2 C3 1.533(3) . ?
C3 C8 1.374(3) . ?
C3 C4 1.380(3) . ?
C4 C5 1.383(5) . ?
C4 H4 0.9300 . ?
C5 C6 1.366(5) . ?
C5 H5 0.9300 . ?
C6 C7 1.345(4) . ?
C6 H6 0.9300 . ?
C7 C8 1.378(4) . ?
C7 H7 0.9300 . ?
C8 H8 0.9300 . ?
C9 C10 1.368(4) . ?
C9 C14 1.371(3) . ?
C10 C11 1.380(4) . ?
C10 H10 0.9300 . ?
C11 C12 1.362(4) . ?
C11 H11 0.9300 . ?
C12 C13 1.355(4) . ?
C12 H12 0.9300 . ?
C13 C14 1.382(4) . ?
C13 H13 0.9300 . ?
C14 H14 0.9300 . ?
C15 C20 1.382(3) . ?
C15 C16 1.386(3) . ?
C16 C17 1.363(4) . ?
C16 H16 0.9300 . ?
C17 C18 1.383(4) . ?
C17 H17 0.9300 . ?
C18 C19 1.375(3) . ?
C18 H18 0.9300 . ?
C19 C20 1.370(3) . ?
C19 H19 0.9300 . ?
C21 C24 1.505(4) . ?
C21 C22 1.508(3) . ?
C21 C23 1.523(3) . ?
C22 H22A 0.9600 . ?
C22 H22B 0.9600 . ?
C22 H22C 0.9600 . ?
C23 H23A 0.9600 . ?
C23 H23B 0.9600 . ?
C23 H23C 0.9600 . ?
C24 H24A 0.9600 . ?
C24 H24B 0.9600 . ?
C24 H24C 0.9600 . ?

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 S1 O1 119.66(13) . . ?
O2 S1 C9 108.53(12) . . ?
O1 S1 C9 109.67(12) . . ?
O2 S1 C1 103.19(11) . . ?
O1 S1 C1 107.05(11) . . ?
C9 S1 C1 108.06(11) . . ?
O3 S2 N1 119.49(10) . . ?
O3 S2 C20 111.20(10) . . ?
N1 S2 C20 98.93(10) . . ?
O3 S2 C21 105.81(10) . . ?
N1 S2 C21 109.68(11) . . ?
C20 S2 C21 111.76(11) . . ?
C2 N1 S2 112.63(13) . . ?
F2 C1 F1 105.28(18) . . ?
F2 C1 C2 112.11(17) . . ?
F1 C1 C2 110.49(18) . . ?
F2 C1 S1 106.24(15) . . ?
F1 C1 S1 102.36(15) . . ?
C2 C1 S1 119.12(15) . . ?
N1 C2 C15 107.30(17) . . ?
N1 C2 C3 112.21(17) . . ?
C15 C2 C3 110.10(17) . . ?
N1 C2 C1 104.58(16) . . ?
C15 C2 C1 107.90(17) . . ?
C3 C2 C1 114.36(18) . . ?
C8 C3 C4 116.5(2) . . ?
C8 C3 C2 119.09(19) . . ?
C4 C3 C2 124.2(2) . . ?
C3 C4 C5 120.5(3) . . ?
C3 C4 H4 119.8 . . ?
C5 C4 H4 119.8 . . ?
C6 C5 C4 121.6(3) . . ?
C6 C5 H5 119.2 . . ?
C4 C5 H5 119.2 . . ?
C7 C6 C5 118.3(3) . . ?
C7 C6 H6 120.8 . . ?
C5 C6 H6 120.8 . . ?
C6 C7 C8 120.6(3) . . ?
C6 C7 H7 119.7 . . ?
C8 C7 H7 119.7 . . ?
C3 C8 C7 122.4(3) . . ?
C3 C8 H8 118.8 . . ?
C7 C8 H8 118.8 . . ?
C10 C9 C14 121.0(3) . . ?
C10 C9 S1 118.1(2) . . ?
C14 C9 S1 120.9(2) . . ?
C9 C10 C11 119.4(3) . . ?
C9 C10 H10 120.3 . . ?
C11 C10 H10 120.3 . . ?
C12 C11 C10 119.8(3) . . ?
C12 C11 H11 120.1 . . ?
C10 C11 H11 120.1 . . ?
C13 C12 C11 120.5(3) . . ?
C13 C12 H12 119.8 . . ?
C11 C12 H12 119.8 . . ?
C12 C13 C14 120.7(3) . . ?
C12 C13 H13 119.6 . . ?
C14 C13 H13 119.6 . . ?
C9 C14 C13 118.5(3) . . ?
C9 C14 H14 120.7 . . ?
C13 C14 H14 120.7 . . ?
C20 C15 C16 118.1(2) . . ?
C20 C15 C2 113.06(18) . . ?
C16 C15 C2 128.8(2) . . ?
C17 C16 C15 119.3(2) . . ?
C17 C16 H16 120.4 . . ?
C15 C16 H16 120.4 . . ?
C16 C17 C18 121.8(2) . . ?
C16 C17 H17 119.1 . . ?
C18 C17 H17 119.1 . . ?
C19 C18 C17 119.7(3) . . ?
C19 C18 H18 120.2 . . ?
C17 C18 H18 120.2 . . ?
C20 C19 C18 117.9(2) . . ?
C20 C19 H19 121.0 . . ?
C18 C19 H19 121.0 . . ?
C19 C20 C15 123.1(2) . . ?
C19 C20 S2 130.29(18) . . ?
C15 C20 S2 106.34(16) . . ?
C24 C21 C22 112.1(2) . . ?
C24 C21 C23 110.5(2) . . ?
C22 C21 C23 110.8(2) . . ?
C24 C21 S2 109.62(16) . . ?
C22 C21 S2 108.24(18) . . ?
C23 C21 S2 105.26(18) . . ?
C21 C22 H22A 109.5 . . ?
C21 C22 H22B 109.5 . . ?
H22A C22 H22B 109.5 . . ?
C21 C22 H22C 109.5 . . ?
H22A C22 H22C 109.5 . . ?
H22B C22 H22C 109.5 . . ?
C21 C23 H23A 109.5 . . ?
C21 C23 H23B 109.5 . . ?
H23A C23 H23B 109.5 . . ?
C21 C23 H23C 109.5 . . ?
H23A C23 H23C 109.5 . . ?
H23B C23 H23C 109.5 . . ?
C21 C24 H24A 109.5 . . ?
C21 C24 H24B 109.5 . . ?
H24A C24 H24B 109.5 . . ?
C21 C24 H24C 109.5 . . ?
H24A C24 H24C 109.5 . . ?
H24B C24 H24C 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
O3 S2 N1 C2 -107.41(16) . . . . ?
C20 S2 N1 C2 13.21(17) . . . . ?
C21 S2 N1 C2 130.27(16) . . . . ?
O2 S1 C1 F2 -26.63(19) . . . . ?
O1 S1 C1 F2 -153.76(16) . . . . ?
C9 S1 C1 F2 88.19(18) . . . . ?
O2 S1 C1 F1 83.54(16) . . . . ?
O1 S1 C1 F1 -43.59(17) . . . . ?
C9 S1 C1 F1 -161.64(14) . . . . ?
O2 S1 C1 C2 -154.30(18) . . . . ?
O1 S1 C1 C2 78.58(19) . . . . ?
C9 S1 C1 C2 -39.5(2) . . . . ?
S2 N1 C2 C15 -12.0(2) . . . . ?
S2 N1 C2 C3 109.05(17) . . . . ?
S2 N1 C2 C1 -126.45(16) . . . . ?
F2 C1 C2 N1 -174.91(18) . . . . ?
F1 C1 C2 N1 68.0(2) . . . . ?
S1 C1 C2 N1 -50.0(2) . . . . ?
F2 C1 C2 C15 71.1(2) . . . . ?
F1 C1 C2 C15 -46.0(2) . . . . ?
S1 C1 C2 C15 -164.03(15) . . . . ?
F2 C1 C2 C3 -51.8(2) . . . . ?
F1 C1 C2 C3 -168.87(17) . . . . ?
S1 C1 C2 C3 73.1(2) . . . . ?
N1 C2 C3 C8 -21.8(3) . . . . ?
C15 C2 C3 C8 97.6(2) . . . . ?
C1 C2 C3 C8 -140.7(2) . . . . ?
N1 C2 C3 C4 162.9(2) . . . . ?
C15 C2 C3 C4 -77.7(3) . . . . ?
C1 C2 C3 C4 44.0(3) . . . . ?
C8 C3 C4 C5 2.3(4) . . . . ?
C2 C3 C4 C5 177.7(3) . . . . ?
C3 C4 C5 C6 -1.9(5) . . . . ?
C4 C5 C6 C7 -0.7(5) . . . . ?
C5 C6 C7 C8 2.7(5) . . . . ?
C4 C3 C8 C7 -0.4(4) . . . . ?
C2 C3 C8 C7 -176.0(3) . . . . ?
C6 C7 C8 C3 -2.2(5) . . . . ?
O2 S1 C9 C10 24.8(2) . . . . ?
O1 S1 C9 C10 157.2(2) . . . . ?
C1 S1 C9 C10 -86.5(2) . . . . ?
O2 S1 C9 C14 -153.5(2) . . . . ?
O1 S1 C9 C14 -21.1(2) . . . . ?
C1 S1 C9 C14 95.3(2) . . . . ?
C14 C9 C10 C11 -0.4(4) . . . . ?
S1 C9 C10 C11 -178.7(3) . . . . ?
C9 C10 C11 C12 0.4(5) . . . . ?
C10 C11 C12 C13 0.6(5) . . . . ?
C11 C12 C13 C14 -1.4(5) . . . . ?
C10 C9 C14 C13 -0.5(4) . . . . ?
S1 C9 C14 C13 177.8(2) . . . . ?
C12 C13 C14 C9 1.4(5) . . . . ?
N1 C2 C15 C20 4.2(3) . . . . ?
C3 C2 C15 C20 -118.2(2) . . . . ?
C1 C2 C15 C20 116.4(2) . . . . ?
N1 C2 C15 C16 -177.4(2) . . . . ?
C3 C2 C15 C16 60.2(3) . . . . ?
C1 C2 C15 C16 -65.2(3) . . . . ?
C20 C15 C16 C17 -2.0(4) . . . . ?
C2 C15 C16 C17 179.7(3) . . . . ?
C15 C16 C17 C18 1.2(5) . . . . ?
C16 C17 C18 C19 1.7(5) . . . . ?
C17 C18 C19 C20 -3.6(4) . . . . ?
C18 C19 C20 C15 2.8(4) . . . . ?
C18 C19 C20 S2 175.9(2) . . . . ?
C16 C15 C20 C19 0.0(4) . . . . ?
C2 C15 C20 C19 178.5(2) . . . . ?
C16 C15 C20 S2 -174.5(2) . . . . ?
C2 C15 C20 S2 4.0(2) . . . . ?
O3 S2 C20 C19 -57.6(3) . . . . ?
N1 S2 C20 C19 175.8(2) . . . . ?
C21 S2 C20 C19 60.4(3) . . . . ?
O3 S2 C20 C15 116.35(16) . . . . ?
N1 S2 C20 C15 -10.19(18) . . . . ?
C21 S2 C20 C15 -125.65(17) . . . . ?
O3 S2 C21 C24 172.04(18) . . . . ?
N1 S2 C21 C24 -57.8(2) . . . . ?
C20 S2 C21 C24 50.9(2) . . . . ?
O3 S2 C21 C22 49.4(2) . . . . ?
N1 S2 C21 C22 179.58(18) . . . . ?
C20 S2 C21 C22 -71.7(2) . . . . ?
O3 S2 C21 C23 -69.1(2) . . . . ?
N1 S2 C21 C23 61.1(2) . . . . ?
C20 S2 C21 C23 169.76(19) . . . . ?

_diffrn_measured_fraction_theta_max 1.000
_diffrn_reflns_theta_full        27.00
_diffrn_measured_fraction_theta_full 1.000
_refine_diff_density_max         0.289
_refine_diff_density_min         -0.246
_refine_diff_density_rms         0.037

_database_code_depnum_ccdc_archive 'CCDC 1009680'
#######################################################################
#
#                 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_mo_dm12080_0m

_audit_creation_method           SHELXL-97
_chemical_name_systematic        
; 
 ? 
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C13 H8 Br N O S'
_chemical_formula_weight         306.17

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'
N N 0.0061 0.0033 '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   P2(1)

loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'-x, y+1/2, -z'

_cell_length_a                   7.5255(18)
_cell_length_b                   3.9957(10)
_cell_length_c                   19.305(5)
_cell_angle_alpha                90.00
_cell_angle_beta                 95.045(4)
_cell_angle_gamma                90.00
_cell_volume                     578.2(2)
_cell_formula_units_Z            2
_cell_measurement_temperature    133(2)
_cell_measurement_reflns_used    3770
_cell_measurement_theta_min      5.434
_cell_measurement_theta_max      55.053

_exptl_crystal_description       prismatic
_exptl_crystal_colour            colorless
_exptl_crystal_size_max          0.256
_exptl_crystal_size_mid          0.187
_exptl_crystal_size_min          0.163
_exptl_crystal_density_meas      ?
_exptl_crystal_density_diffrn    1.758
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             304
_exptl_absorpt_coefficient_mu    3.714
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.3512
_exptl_absorpt_correction_T_max  0.7455
_exptl_absorpt_process_details   sadabs

_exptl_special_details           
; 
 ? 
;

_diffrn_ambient_temperature      133(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  'Bruker APEX-II CCD'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            3602
_diffrn_reflns_av_R_equivalents  0.0225
_diffrn_reflns_av_sigmaI/netI    0.0543
_diffrn_reflns_limit_h_min       -9
_diffrn_reflns_limit_h_max       9
_diffrn_reflns_limit_k_min       -4
_diffrn_reflns_limit_k_max       4
_diffrn_reflns_limit_l_min       -23
_diffrn_reflns_limit_l_max       23
_diffrn_reflns_theta_min         2.12
_diffrn_reflns_theta_max         26.00
_reflns_number_total             2058
_reflns_number_gt                2006
_reflns_threshold_expression     >2sigma(I)

_computing_data_collection       'Bruker APEX2'
_computing_cell_refinement       'Bruker SAINT'
_computing_data_reduction        'Bruker SAINT'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 2008)'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 2008)'
_computing_molecular_graphics    'Bruker SHELXTL'
_computing_publication_material  'Bruker SHELXTL'

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

_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'calc w=1/[σ²(Fo²)+(0.0000P)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     SHELXL
_refine_ls_extinction_coef       ?
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc²λ³/sin(2θ)]^-1/4^
_refine_ls_abs_structure_details 'Flack H D (1983), Acta Cryst. A39, 876-881'
_refine_ls_abs_structure_Flack   0.042(9)
_chemical_absolute_configuration ad
_refine_ls_number_reflns         2058
_refine_ls_number_parameters     155
_refine_ls_number_restraints     1
_refine_ls_R_factor_all          0.0254
_refine_ls_R_factor_gt           0.0245
_refine_ls_wR_factor_ref         0.0658
_refine_ls_wR_factor_gt          0.0654
_refine_ls_goodness_of_fit_ref   1.211
_refine_ls_restrained_S_all      1.211
_refine_ls_shift/su_max          0.002
_refine_ls_shift/su_mean         0.000

loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_symmetry_multiplicity
_atom_site_calc_flag
_atom_site_refinement_flags
_atom_site_disorder_assembly
_atom_site_disorder_group
Br1 Br 0.17222(4) 0.62858(11) 0.544905(14) 0.02510(12) Uani 1 1 d . . .
S1 S 1.04377(9) -0.0499(2) 0.81885(4) 0.01732(17) Uani 1 1 d . . .
N1 N 0.9021(3) 0.1547(9) 0.75882(12) 0.0183(5) Uani 1 1 d . . .
O1 O 1.1605(3) 0.1960(5) 0.85917(11) 0.0197(5) Uani 1 1 d . . .
C1 C 0.8664(4) -0.1757(8) 0.86806(15) 0.0150(6) Uani 1 1 d . . .
C2 C 0.8814(4) -0.3391(10) 0.93169(14) 0.0179(6) Uani 1 1 d . . .
H2 H 0.9944 -0.3831 0.9558 0.022 Uiso 1 1 calc R . .
C3 C 0.7226(4) -0.4365(8) 0.95885(15) 0.0200(8) Uani 1 1 d . . .
H3 H 0.7263 -0.5364 1.0036 0.024 Uiso 1 1 calc R . .
C4 C 0.5598(4) -0.3871(11) 0.92040(14) 0.0201(6) Uani 1 1 d . . .
H4 H 0.4540 -0.4660 0.9384 0.024 Uiso 1 1 calc R . .
C5 C 0.5474(4) -0.2259(9) 0.85653(15) 0.0187(6) Uani 1 1 d . . .
H5 H 0.4349 -0.1945 0.8309 0.022 Uiso 1 1 calc R . .
C6 C 0.7045(4) -0.1103(8) 0.83060(15) 0.0146(6) Uani 1 1 d . . .
C7 C 0.7357(4) 0.0818(8) 0.76606(14) 0.0147(6) Uani 1 1 d . . .
C8 C 0.5973(4) 0.1992(7) 0.71337(15) 0.0153(7) Uani 1 1 d . . .
C9 C 0.6421(4) 0.2640(9) 0.64544(15) 0.0197(6) Uani 1 1 d . . .
H9 H 0.7599 0.2201 0.6338 0.024 Uiso 1 1 calc R . .
C10 C 0.5177(4) 0.3904(9) 0.59548(16) 0.0223(7) Uani 1 1 d . . .
H10 H 0.5497 0.4346 0.5499 0.027 Uiso 1 1 calc R . .
C11 C 0.3447(4) 0.4526(9) 0.61251(15) 0.0189(6) Uani 1 1 d . . .
C12 C 0.2960(4) 0.3943(8) 0.67914(15) 0.0191(6) Uani 1 1 d . . .
H12 H 0.1781 0.4402 0.6905 0.023 Uiso 1 1 calc R . .
C13 C 0.4220(4) 0.2683(9) 0.72872(15) 0.0179(6) Uani 1 1 d . . .
H13 H 0.3893 0.2273 0.7744 0.022 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
Br1 C11 1.893(3) . ?
S1 O1 1.491(2) . ?
S1 N1 1.712(3) . ?
S1 C1 1.778(3) . ?
N1 C7 1.305(4) . ?
C1 C2 1.387(4) . ?
C1 C6 1.386(4) . ?
C2 C3 1.401(4) . ?
C2 H2 0.9500 . ?
C3 C4 1.390(5) . ?
C3 H3 0.9500 . ?
C4 C5 1.387(4) . ?
C4 H4 0.9500 . ?
C5 C6 1.402(4) . ?
C5 H5 0.9500 . ?
C6 C7 1.499(4) . ?
C7 C8 1.467(4) . ?
C8 C9 1.407(4) . ?
C8 C13 1.404(4) . ?
C9 C10 1.379(5) . ?
C9 H9 0.9500 . ?
C10 C11 1.393(4) . ?
C10 H10 0.9500 . ?
C11 C12 1.388(4) . ?
C12 C13 1.382(5) . ?
C12 H12 0.9500 . ?
C13 H13 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
O1 S1 N1 110.01(15) . . ?
O1 S1 C1 110.06(13) . . ?
N1 S1 C1 92.54(13) . . ?
C7 N1 S1 111.6(2) . . ?
C2 C1 C6 123.4(3) . . ?
C2 C1 S1 126.9(2) . . ?
C6 C1 S1 109.6(2) . . ?
C1 C2 C3 117.2(3) . . ?
C1 C2 H2 121.4 . . ?
C3 C2 H2 121.4 . . ?
C4 C3 C2 120.1(3) . . ?
C4 C3 H3 120.0 . . ?
C2 C3 H3 120.0 . . ?
C3 C4 C5 121.9(3) . . ?
C3 C4 H4 119.1 . . ?
C5 C4 H4 119.1 . . ?
C4 C5 C6 118.5(3) . . ?
C4 C5 H5 120.8 . . ?
C6 C5 H5 120.8 . . ?
C1 C6 C5 118.8(3) . . ?
C1 C6 C7 109.6(2) . . ?
C5 C6 C7 131.6(3) . . ?
N1 C7 C8 118.9(3) . . ?
N1 C7 C6 115.1(3) . . ?
C8 C7 C6 125.9(2) . . ?
C9 C8 C13 117.9(3) . . ?
C9 C8 C7 119.4(2) . . ?
C13 C8 C7 122.6(3) . . ?
C10 C9 C8 121.0(3) . . ?
C10 C9 H9 119.5 . . ?
C8 C9 H9 119.5 . . ?
C9 C10 C11 119.4(3) . . ?
C9 C10 H10 120.3 . . ?
C11 C10 H10 120.3 . . ?
C12 C11 C10 121.2(3) . . ?
C12 C11 Br1 118.7(2) . . ?
C10 C11 Br1 120.1(2) . . ?
C11 C12 C13 118.8(3) . . ?
C11 C12 H12 120.6 . . ?
C13 C12 H12 120.6 . . ?
C12 C13 C8 121.7(3) . . ?
C12 C13 H13 119.1 . . ?
C8 C13 H13 119.1 . . ?

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
O1 S1 N1 C7 -124.3(2) . . . . ?
C1 S1 N1 C7 -11.9(3) . . . . ?
O1 S1 C1 C2 -61.7(3) . . . . ?
N1 S1 C1 C2 -174.1(3) . . . . ?
O1 S1 C1 C6 123.2(2) . . . . ?
N1 S1 C1 C6 10.8(2) . . . . ?
C6 C1 C2 C3 -0.9(5) . . . . ?
S1 C1 C2 C3 -175.4(2) . . . . ?
C1 C2 C3 C4 3.9(5) . . . . ?
C2 C3 C4 C5 -3.6(6) . . . . ?
C3 C4 C5 C6 -0.1(5) . . . . ?
C2 C1 C6 C5 -2.6(5) . . . . ?
S1 C1 C6 C5 172.7(2) . . . . ?
C2 C1 C6 C7 177.6(3) . . . . ?
S1 C1 C6 C7 -7.1(3) . . . . ?
C4 C5 C6 C1 3.1(5) . . . . ?
C4 C5 C6 C7 -177.2(3) . . . . ?
S1 N1 C7 C8 -172.0(2) . . . . ?
S1 N1 C7 C6 9.9(4) . . . . ?
C1 C6 C7 N1 -1.6(4) . . . . ?
C5 C6 C7 N1 178.6(3) . . . . ?
C1 C6 C7 C8 -179.6(3) . . . . ?
C5 C6 C7 C8 0.7(5) . . . . ?
N1 C7 C8 C9 25.2(5) . . . . ?
C6 C7 C8 C9 -156.9(3) . . . . ?
N1 C7 C8 C13 -151.2(3) . . . . ?
C6 C7 C8 C13 26.7(5) . . . . ?
C13 C8 C9 C10 -0.2(5) . . . . ?
C7 C8 C9 C10 -176.8(3) . . . . ?
C8 C9 C10 C11 -0.4(5) . . . . ?
C9 C10 C11 C12 0.9(5) . . . . ?
C9 C10 C11 Br1 179.6(3) . . . . ?
C10 C11 C12 C13 -0.8(5) . . . . ?
Br1 C11 C12 C13 -179.5(3) . . . . ?
C11 C12 C13 C8 0.2(5) . . . . ?
C9 C8 C13 C12 0.3(5) . . . . ?
C7 C8 C13 C12 176.8(3) . . . . ?

loop_
_geom_hbond_atom_site_label_D
_geom_hbond_atom_site_label_H
_geom_hbond_atom_site_label_A
_geom_hbond_distance_DH
_geom_hbond_distance_HA
_geom_hbond_distance_DA
_geom_hbond_angle_DHA
_geom_hbond_site_symmetry_A
C5 H5 O1 0.95 2.68 3.368(4) 129.6 1_455
C13 H13 O1 0.95 2.48 3.342(3) 150.8 1_455

_diffrn_measured_fraction_theta_max 0.985
_diffrn_reflns_theta_full        26.00
_diffrn_measured_fraction_theta_full 0.985
_refine_diff_density_max         0.349
_refine_diff_density_min         -0.543
_refine_diff_density_rms         0.072
_database_code_depnum_ccdc_archive 'CCDC 1009681'
#######################################################################
#
#                 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_z

_audit_creation_method           SHELXL-97
_chemical_name_systematic        
; 
 ? 
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C16 H17 F2 N O S'
_chemical_formula_weight         309.37

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'
N N 0.0061 0.0033 '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'
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'

_symmetry_cell_setting           Orthorhombic
_symmetry_space_group_name_H-M   P2(1)2(1)2(1)

loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'-x+1/2, -y, z+1/2'
'-x, y+1/2, -z+1/2'
'x+1/2, -y+1/2, -z'

_cell_length_a                   9.9519(4)
_cell_length_b                   10.2705(4)
_cell_length_c                   15.1165(6)
_cell_angle_alpha                90.00
_cell_angle_beta                 90.00
_cell_angle_gamma                90.00
_cell_volume                     1545.07(11)
_cell_formula_units_Z            4
_cell_measurement_temperature    173(2)
_cell_measurement_reflns_used    ?
_cell_measurement_theta_min      ?
_cell_measurement_theta_max      ?

_exptl_crystal_description       block
_exptl_crystal_colour            colorless
_exptl_crystal_size_max          0.38
_exptl_crystal_size_mid          0.32
_exptl_crystal_size_min          0.26
_exptl_crystal_density_meas      ?
_exptl_crystal_density_diffrn    1.330
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             648
_exptl_absorpt_coefficient_mu    0.228
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.9183
_exptl_absorpt_correction_T_max  0.9430
_exptl_absorpt_process_details   ?

_exptl_special_details           
; 
 ? 
;

_diffrn_ambient_temperature      173(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  ?
_diffrn_measurement_method       ?
_diffrn_detector_area_resol_mean ?
_diffrn_standards_number         ?
_diffrn_standards_interval_count ?
_diffrn_standards_interval_time  ?
_diffrn_standards_decay_%        ?
_diffrn_reflns_number            17817
_diffrn_reflns_av_R_equivalents  0.0173
_diffrn_reflns_av_sigmaI/netI    0.0108
_diffrn_reflns_limit_h_min       -11
_diffrn_reflns_limit_h_max       11
_diffrn_reflns_limit_k_min       -12
_diffrn_reflns_limit_k_max       11
_diffrn_reflns_limit_l_min       -17
_diffrn_reflns_limit_l_max       17
_diffrn_reflns_theta_min         2.40
_diffrn_reflns_theta_max         25.01
_reflns_number_total             2721
_reflns_number_gt                2673
_reflns_threshold_expression     >2sigma(I)

_computing_data_collection       ?
_computing_cell_refinement       ?
_computing_data_reduction        ?
_computing_structure_solution    'SHELXS-97 (Sheldrick, 1990)'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_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 > 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)+(0.0363P)²+0.3502P] 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_abs_structure_details 'Flack H D (1983), Acta Cryst. A39, 876-881'
_refine_ls_abs_structure_Flack   0.00(6)
_refine_ls_number_reflns         2721
_refine_ls_number_parameters     190
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0241
_refine_ls_R_factor_gt           0.0237
_refine_ls_wR_factor_ref         0.0639
_refine_ls_wR_factor_gt          0.0636
_refine_ls_goodness_of_fit_ref   1.050
_refine_ls_restrained_S_all      1.050
_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 0.33836(4) 0.70238(3) 0.80462(2) 0.02785(10) Uani 1 1 d . . .
F1 F 0.22046(11) 0.33214(11) 0.71505(8) 0.0593(3) Uani 1 1 d . . .
F2 F 0.30057(10) 0.31768(11) 0.84950(9) 0.0610(3) Uani 1 1 d . . .
O1 O 0.46018(10) 0.61992(11) 0.81068(8) 0.0388(3) Uani 1 1 d . . .
N1 N 0.19417(11) 0.62265(12) 0.82297(8) 0.0280(3) Uani 1 1 d . . .
C1 C -0.16689(16) 0.17009(15) 0.90623(10) 0.0344(3) Uani 1 1 d . . .
H1A H -0.0989 0.1053 0.9092 0.041 Uiso 1 1 calc R . .
C2 C -0.29609(17) 0.13961(17) 0.92879(11) 0.0385(4) Uani 1 1 d . . .
H2A H -0.3170 0.0537 0.9476 0.046 Uiso 1 1 calc R . .
C3 C -0.39833(16) 0.23351(16) 0.92455(10) 0.0349(4) Uani 1 1 d . . .
H3A H -0.4877 0.2107 0.9403 0.042 Uiso 1 1 calc R . .
C4 C -0.36980(14) 0.35752(15) 0.89795(10) 0.0302(3) Uani 1 1 d . . .
H4A H -0.4395 0.4206 0.8956 0.036 Uiso 1 1 calc R . .
C5 C -0.23731(14) 0.39287(14) 0.87389(9) 0.0261(3) Uani 1 1 d . . .
C6 C -0.13379(13) 0.29786(15) 0.87844(9) 0.0265(3) Uani 1 1 d . . .
C7 C -0.00080(14) 0.33335(14) 0.85523(10) 0.0276(3) Uani 1 1 d . . .
H7A H 0.0685 0.2698 0.8573 0.033 Uiso 1 1 calc R . .
C8 C 0.02941(14) 0.45839(14) 0.82986(9) 0.0259(3) Uani 1 1 d . . .
C9 C -0.07522(14) 0.55178(14) 0.82333(10) 0.0287(3) Uani 1 1 d . . .
H9A H -0.0550 0.6377 0.8043 0.034 Uiso 1 1 calc R . .
C10 C -0.20411(14) 0.51977(14) 0.84404(10) 0.0294(3) Uani 1 1 d . . .
H10A H -0.2729 0.5834 0.8384 0.035 Uiso 1 1 calc R . .
C11 C 0.16984(15) 0.50153(13) 0.81273(8) 0.0268(3) Uani 1 1 d . . .
C12 C 0.27367(16) 0.40248(17) 0.78280(12) 0.0401(4) Uani 1 1 d . . .
H12A H 0.3578 0.4473 0.7633 0.048 Uiso 1 1 calc R . .
C13 C 0.32992(15) 0.79739(15) 0.90895(9) 0.0322(3) Uani 1 1 d . . .
C14 C 0.45545(18) 0.88274(19) 0.90630(14) 0.0488(5) Uani 1 1 d . . .
H14A H 0.4589 0.9369 0.9596 0.073 Uiso 1 1 calc R . .
H14B H 0.4525 0.9387 0.8538 0.073 Uiso 1 1 calc R . .
H14C H 0.5355 0.8274 0.9038 0.073 Uiso 1 1 calc R . .
C15 C 0.3333(2) 0.70335(18) 0.98648(11) 0.0467(4) Uani 1 1 d . . .
H15A H 0.3288 0.7524 1.0420 0.070 Uiso 1 1 calc R . .
H15B H 0.4169 0.6530 0.9847 0.070 Uiso 1 1 calc R . .
H15C H 0.2564 0.6440 0.9827 0.070 Uiso 1 1 calc R . .
C16 C 0.20417(18) 0.88046(18) 0.90653(13) 0.0455(4) Uani 1 1 d . . .
H16A H 0.1979 0.9315 0.9611 0.068 Uiso 1 1 calc R . .
H16B H 0.1251 0.8242 0.9013 0.068 Uiso 1 1 calc R . .
H16C H 0.2082 0.9394 0.8556 0.068 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 O1 1.4817(11) . ?
S1 N1 1.6753(12) . ?
S1 C13 1.8565(15) . ?
F1 C12 1.361(2) . ?
F2 C12 1.359(2) . ?
N1 C11 1.2768(18) . ?
C1 C2 1.366(2) . ?
C1 C6 1.417(2) . ?
C1 H1A 0.9500 . ?
C2 C3 1.403(2) . ?
C2 H2A 0.9500 . ?
C3 C4 1.365(2) . ?
C3 H3A 0.9500 . ?
C4 C5 1.415(2) . ?
C4 H4A 0.9500 . ?
C5 C10 1.418(2) . ?
C5 C6 1.421(2) . ?
C6 C7 1.417(2) . ?
C7 C8 1.374(2) . ?
C7 H7A 0.9500 . ?
C8 C9 1.419(2) . ?
C8 C11 1.4888(19) . ?
C9 C10 1.361(2) . ?
C9 H9A 0.9500 . ?
C10 H10A 0.9500 . ?
C11 C12 1.519(2) . ?
C12 H12A 1.0000 . ?
C13 C16 1.515(2) . ?
C13 C15 1.519(2) . ?
C13 C14 1.527(2) . ?
C14 H14A 0.9800 . ?
C14 H14B 0.9800 . ?
C14 H14C 0.9800 . ?
C15 H15A 0.9800 . ?
C15 H15B 0.9800 . ?
C15 H15C 0.9800 . ?
C16 H16A 0.9800 . ?
C16 H16B 0.9800 . ?
C16 H16C 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
O1 S1 N1 114.28(6) . . ?
O1 S1 C13 106.56(7) . . ?
N1 S1 C13 94.44(6) . . ?
C11 N1 S1 128.21(11) . . ?
C2 C1 C6 120.33(15) . . ?
C2 C1 H1A 119.8 . . ?
C6 C1 H1A 119.8 . . ?
C1 C2 C3 120.89(15) . . ?
C1 C2 H2A 119.6 . . ?
C3 C2 H2A 119.6 . . ?
C4 C3 C2 120.24(15) . . ?
C4 C3 H3A 119.9 . . ?
C2 C3 H3A 119.9 . . ?
C3 C4 C5 120.58(14) . . ?
C3 C4 H4A 119.7 . . ?
C5 C4 H4A 119.7 . . ?
C4 C5 C10 122.32(13) . . ?
C4 C5 C6 119.14(13) . . ?
C10 C5 C6 118.53(13) . . ?
C1 C6 C7 121.93(14) . . ?
C1 C6 C5 118.81(13) . . ?
C7 C6 C5 119.26(13) . . ?
C8 C7 C6 120.94(13) . . ?
C8 C7 H7A 119.5 . . ?
C6 C7 H7A 119.5 . . ?
C7 C8 C9 119.39(13) . . ?
C7 C8 C11 122.16(13) . . ?
C9 C8 C11 118.39(13) . . ?
C10 C9 C8 120.82(13) . . ?
C10 C9 H9A 119.6 . . ?
C8 C9 H9A 119.6 . . ?
C9 C10 C5 120.99(13) . . ?
C9 C10 H10A 119.5 . . ?
C5 C10 H10A 119.5 . . ?
N1 C11 C8 116.55(13) . . ?
N1 C11 C12 124.03(13) . . ?
C8 C11 C12 119.41(12) . . ?
F2 C12 F1 107.15(14) . . ?
F2 C12 C11 110.01(14) . . ?
F1 C12 C11 108.37(13) . . ?
F2 C12 H12A 110.4 . . ?
F1 C12 H12A 110.4 . . ?
C11 C12 H12A 110.4 . . ?
C16 C13 C15 113.27(14) . . ?
C16 C13 C14 110.60(13) . . ?
C15 C13 C14 111.54(15) . . ?
C16 C13 S1 108.23(11) . . ?
C15 C13 S1 108.68(11) . . ?
C14 C13 S1 104.03(11) . . ?
C13 C14 H14A 109.5 . . ?
C13 C14 H14B 109.5 . . ?
H14A C14 H14B 109.5 . . ?
C13 C14 H14C 109.5 . . ?
H14A C14 H14C 109.5 . . ?
H14B C14 H14C 109.5 . . ?
C13 C15 H15A 109.5 . . ?
C13 C15 H15B 109.5 . . ?
H15A C15 H15B 109.5 . . ?
C13 C15 H15C 109.5 . . ?
H15A C15 H15C 109.5 . . ?
H15B C15 H15C 109.5 . . ?
C13 C16 H16A 109.5 . . ?
C13 C16 H16B 109.5 . . ?
H16A C16 H16B 109.5 . . ?
C13 C16 H16C 109.5 . . ?
H16A C16 H16C 109.5 . . ?
H16B C16 H16C 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 S1 N1 C11 -25.08(15) . . . . ?
C13 S1 N1 C11 -135.48(14) . . . . ?
C6 C1 C2 C3 0.3(2) . . . . ?
C1 C2 C3 C4 -0.2(2) . . . . ?
C2 C3 C4 C5 0.3(2) . . . . ?
C3 C4 C5 C10 178.57(15) . . . . ?
C3 C4 C5 C6 -0.5(2) . . . . ?
C2 C1 C6 C7 179.48(15) . . . . ?
C2 C1 C6 C5 -0.5(2) . . . . ?
C4 C5 C6 C1 0.6(2) . . . . ?
C10 C5 C6 C1 -178.55(13) . . . . ?
C4 C5 C6 C7 -179.37(13) . . . . ?
C10 C5 C6 C7 1.5(2) . . . . ?
C1 C6 C7 C8 -178.92(14) . . . . ?
C5 C6 C7 C8 1.0(2) . . . . ?
C6 C7 C8 C9 -2.6(2) . . . . ?
C6 C7 C8 C11 174.52(12) . . . . ?
C7 C8 C9 C10 1.7(2) . . . . ?
C11 C8 C9 C10 -175.57(13) . . . . ?
C8 C9 C10 C5 0.9(2) . . . . ?
C4 C5 C10 C9 178.45(14) . . . . ?
C6 C5 C10 C9 -2.5(2) . . . . ?
S1 N1 C11 C8 -176.92(10) . . . . ?
S1 N1 C11 C12 1.7(2) . . . . ?
C7 C8 C11 N1 -154.01(14) . . . . ?
C9 C8 C11 N1 23.16(19) . . . . ?
C7 C8 C11 C12 27.3(2) . . . . ?
C9 C8 C11 C12 -155.54(14) . . . . ?
N1 C11 C12 F2 113.11(16) . . . . ?
C8 C11 C12 F2 -68.29(17) . . . . ?
N1 C11 C12 F1 -130.04(15) . . . . ?
C8 C11 C12 F1 48.56(19) . . . . ?
O1 S1 C13 C16 -178.41(10) . . . . ?
N1 S1 C13 C16 -61.46(11) . . . . ?
O1 S1 C13 C15 -55.02(13) . . . . ?
N1 S1 C13 C15 61.94(12) . . . . ?
O1 S1 C13 C14 63.92(13) . . . . ?
N1 S1 C13 C14 -179.12(12) . . . . ?

_diffrn_measured_fraction_theta_max 1.000
_diffrn_reflns_theta_full        25.01
_diffrn_measured_fraction_theta_full 1.000
_refine_diff_density_max         0.222
_refine_diff_density_min         -0.143
_refine_diff_density_rms         0.032
_database_code_depnum_ccdc_archive 'CCDC 1009682'
#######################################################################
#
#                 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_cd29410

_audit_creation_method           SHELXL-97
_chemical_name_systematic        
; 
 ? 
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C31 H22 Br F2 N O3 S2'
_chemical_formula_weight         638.53

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'
N N 0.0061 0.0033 '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'
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'
Br Br -0.2901 2.4595 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_symmetry_cell_setting           Orthorhombic
_symmetry_space_group_name_H-M   P2(1)2(1)2(1)

loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'-x+1/2, -y, z+1/2'
'-x, y+1/2, -z+1/2'
'x+1/2, -y+1/2, -z'

_cell_length_a                   8.5124(11)
_cell_length_b                   14.4301(19)
_cell_length_c                   22.503(3)
_cell_angle_alpha                90.00
_cell_angle_beta                 90.00
_cell_angle_gamma                90.00
_cell_volume                     2764.1(6)
_cell_formula_units_Z            4
_cell_measurement_temperature    293(2)
_cell_measurement_reflns_used    1450
_cell_measurement_theta_min      4.591
_cell_measurement_theta_max      47.542

_exptl_crystal_description       prismatic
_exptl_crystal_colour            colorless
_exptl_crystal_size_max          0.220
_exptl_crystal_size_mid          0.185
_exptl_crystal_size_min          0.128
_exptl_crystal_density_meas      ?
_exptl_crystal_density_diffrn    1.534
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             1296
_exptl_absorpt_coefficient_mu    1.687
_exptl_absorpt_correction_type   empirical
_exptl_absorpt_correction_T_min  0.7688
_exptl_absorpt_correction_T_max  1.0000
_exptl_absorpt_process_details   sadabs

_exptl_special_details           
; 
 ? 
;

_diffrn_ambient_temperature      293(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_radiation_source         'fine-focus sealed tube'
_diffrn_radiation_monochromator  graphite
_diffrn_measurement_device_type  'CCD area detector'
_diffrn_measurement_method       'phi and omega scans'
_diffrn_detector_area_resol_mean ?
_diffrn_standards_number         ?
_diffrn_standards_interval_count ?
_diffrn_standards_interval_time  ?
_diffrn_standards_decay_%        ?
_diffrn_reflns_number            16423
_diffrn_reflns_av_R_equivalents  0.0993
_diffrn_reflns_av_sigmaI/netI    0.2183
_diffrn_reflns_limit_h_min       -8
_diffrn_reflns_limit_h_max       11
_diffrn_reflns_limit_k_min       -18
_diffrn_reflns_limit_k_max       18
_diffrn_reflns_limit_l_min       -28
_diffrn_reflns_limit_l_max       28
_diffrn_reflns_theta_min         1.68
_diffrn_reflns_theta_max         27.50
_reflns_number_total             6165
_reflns_number_gt                2274
_reflns_threshold_expression     >2sigma(I)

_computing_data_collection       'Bruker SMART'
_computing_cell_refinement       'Bruker SMART'
_computing_data_reduction        'Bruker SHELXTL'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 1990)'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_computing_molecular_graphics    'Bruker SHELXTL'
_computing_publication_material  'Bruker SHELXTL'

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

_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
; calc 
 [0.00000+1.00000exp(2.00(sinθ/λ)²)]/ 
   [σ²(Fo²)+0.0000+0.0000*P+(0.0179P)²+0.0000sinθ/λ] 
 where P = 0.33333Fo² + 0.66667Fc² 
;
_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_abs_structure_details 'Flack H D (1983), Acta Cryst. A39, 876-881'
_refine_ls_abs_structure_Flack   0.058(11)
_chemical_absolute_configuration ad
_refine_ls_number_reflns         6165
_refine_ls_number_parameters     361
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.1596
_refine_ls_R_factor_gt           0.0470
_refine_ls_wR_factor_ref         0.0908
_refine_ls_wR_factor_gt          0.0677
_refine_ls_goodness_of_fit_ref   0.872
_refine_ls_restrained_S_all      0.872
_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
Br Br 0.82211(9) 0.98640(4) 0.06296(3) 0.0745(2) Uani 1 1 d . . .
S1 S 0.0587(2) 0.60291(10) 0.19735(7) 0.0490(4) Uani 1 1 d . . .
S2 S 0.3535(2) 0.38599(11) 0.19433(8) 0.0540(5) Uani 1 1 d . . .
F1 F 0.2658(4) 0.3770(2) 0.08544(15) 0.0629(10) Uani 1 1 d . . .
F2 F 0.1434(4) 0.2800(2) 0.14264(16) 0.0689(11) Uani 1 1 d . . .
O1 O -0.0776(5) 0.6607(2) 0.17906(17) 0.0586(12) Uani 1 1 d . . .
O2 O 0.4567(5) 0.4544(2) 0.1709(2) 0.0672(14) Uani 1 1 d . . .
O3 O 0.2803(5) 0.3991(3) 0.25121(19) 0.0754(14) Uani 1 1 d . . .
N1 N 0.1155(5) 0.5303(3) 0.14198(19) 0.0390(12) Uani 1 1 d . . .
C1 C 0.1913(7) 0.3713(4) 0.1389(3) 0.0468(15) Uani 1 1 d . . .
C2 C 0.0489(7) 0.4358(4) 0.1424(3) 0.0394(15) Uani 1 1 d . . .
C3 C -0.0297(7) 0.4276(4) 0.2030(3) 0.0478(17) Uani 1 1 d . . .
C4 C -0.0223(6) 0.5087(4) 0.2350(3) 0.0477(15) Uani 1 1 d . . .
C5 C -0.0899(7) 0.5139(5) 0.2913(3) 0.067(2) Uani 1 1 d . . .
H5 H -0.0856 0.5690 0.3128 0.081 Uiso 1 1 calc R . .
C6 C -0.1624(10) 0.4381(5) 0.3148(3) 0.086(2) Uani 1 1 d . . .
H6 H -0.2046 0.4411 0.3529 0.103 Uiso 1 1 calc R . .
C7 C -0.1738(9) 0.3558(5) 0.2824(3) 0.083(2) Uani 1 1 d . . .
H7 H -0.2283 0.3054 0.2979 0.100 Uiso 1 1 calc R . .
C8 C -0.1024(7) 0.3497(4) 0.2261(3) 0.064(2) Uani 1 1 d . . .
H8 H -0.1040 0.2945 0.2049 0.077 Uiso 1 1 calc R . .
C9 C -0.0710(7) 0.4171(4) 0.0913(3) 0.0433(16) Uani 1 1 d . . .
C10 C -0.2063(7) 0.4705(4) 0.0913(3) 0.0551(18) Uani 1 1 d . . .
H10 H -0.2215 0.5138 0.1213 0.066 Uiso 1 1 calc R . .
C11 C -0.3182(8) 0.4607(4) 0.0479(3) 0.0644(19) Uani 1 1 d . . .
H11 H -0.4073 0.4979 0.0483 0.077 Uiso 1 1 calc R . .
C12 C -0.2982(9) 0.3957(5) 0.0041(3) 0.077(2) Uani 1 1 d . . .
H12 H -0.3753 0.3877 -0.0247 0.093 Uiso 1 1 calc R . .
C13 C -0.1658(10) 0.3429(5) 0.0029(3) 0.089(3) Uani 1 1 d . . .
H13 H -0.1507 0.3005 -0.0278 0.107 Uiso 1 1 calc R . .
C14 C -0.0530(8) 0.3521(4) 0.0472(3) 0.070(2) Uani 1 1 d . . .
H14 H 0.0351 0.3139 0.0471 0.084 Uiso 1 1 calc R . .
C15 C 0.1238(7) 0.5788(4) 0.0841(2) 0.0570(19) Uani 1 1 d . . .
H15A H 0.0188 0.5983 0.0730 0.068 Uiso 1 1 calc R . .
H15B H 0.1603 0.5355 0.0542 0.068 Uiso 1 1 calc R . .
C16 C 0.2305(8) 0.6627(4) 0.0838(3) 0.0511(18) Uani 1 1 d . . .
C17 C 0.3798(8) 0.6578(4) 0.1031(3) 0.0582(19) Uani 1 1 d . . .
H17 H 0.4180 0.6041 0.1208 0.070 Uiso 1 1 calc R . .
C18 C 0.4815(8) 0.7400(4) 0.0955(3) 0.0542(18) Uani 1 1 d . . .
C19 C 0.6331(9) 0.7342(5) 0.1137(3) 0.076(2) Uani 1 1 d . . .
H19 H 0.6702 0.6810 0.1323 0.092 Uiso 1 1 calc R . .
C20 C 0.7336(9) 0.8105(5) 0.1038(3) 0.073(2) Uani 1 1 d . . .
H20 H 0.8387 0.8070 0.1148 0.087 Uiso 1 1 calc R . .
C21 C 0.6759(8) 0.8901(4) 0.0779(2) 0.0535(16) Uani 1 1 d . . .
C22 C 0.5221(8) 0.8991(4) 0.0614(3) 0.0628(19) Uani 1 1 d . . .
H22 H 0.4843 0.9543 0.0454 0.075 Uiso 1 1 calc R . .
C23 C 0.4187(8) 0.8187(4) 0.0697(3) 0.0506(17) Uani 1 1 d . . .
C24 C 0.2645(8) 0.8220(5) 0.0501(3) 0.064(2) Uani 1 1 d . . .
H24 H 0.2240 0.8754 0.0327 0.076 Uiso 1 1 calc R . .
C25 C 0.1731(9) 0.7444(4) 0.0571(3) 0.0609(18) Uani 1 1 d . . .
H25 H 0.0697 0.7457 0.0438 0.073 Uiso 1 1 calc R . .
C26 C 0.4436(7) 0.2783(4) 0.1918(3) 0.0487(16) Uani 1 1 d . . .
C27 C 0.5579(8) 0.2629(4) 0.1509(3) 0.065(2) Uani 1 1 d . . .
H27 H 0.5875 0.3096 0.1247 0.079 Uiso 1 1 calc R . .
C28 C 0.6309(8) 0.1758(5) 0.1485(3) 0.083(2) Uani 1 1 d . . .
H28 H 0.7089 0.1642 0.1206 0.100 Uiso 1 1 calc R . .
C29 C 0.5863(9) 0.1075(5) 0.1880(4) 0.083(2) Uani 1 1 d . . .
H29 H 0.6350 0.0499 0.1869 0.099 Uiso 1 1 calc R . .
C30 C 0.4711(9) 0.1247(5) 0.2284(4) 0.079(2) Uani 1 1 d . . .
H30 H 0.4415 0.0785 0.2549 0.095 Uiso 1 1 calc R . .
C31 C 0.3988(8) 0.2085(5) 0.2304(3) 0.074(2) Uani 1 1 d . . .
H31 H 0.3189 0.2190 0.2577 0.088 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
Br C21 1.896(6) . ?
S1 O1 1.487(4) . ?
S1 N1 1.698(4) . ?
S1 C4 1.745(6) . ?
S2 O2 1.423(4) . ?
S2 O3 1.436(4) . ?
S2 C26 1.734(6) . ?
S2 C1 1.872(6) . ?
F1 C1 1.363(6) . ?
F2 C1 1.382(6) . ?
N1 C2 1.477(6) . ?
N1 C15 1.480(6) . ?
C1 C2 1.530(7) . ?
C2 C3 1.524(8) . ?
C2 C9 1.562(7) . ?
C3 C4 1.375(7) . ?
C3 C8 1.384(7) . ?
C4 C5 1.393(7) . ?
C5 C6 1.364(8) . ?
C5 H5 0.9300 . ?
C6 C7 1.397(8) . ?
C6 H6 0.9300 . ?
C7 C8 1.407(8) . ?
C7 H7 0.9300 . ?
C8 H8 0.9300 . ?
C9 C14 1.373(7) . ?
C9 C10 1.385(7) . ?
C10 C11 1.371(8) . ?
C10 H10 0.9300 . ?
C11 C12 1.371(8) . ?
C11 H11 0.9300 . ?
C12 C13 1.361(9) . ?
C12 H12 0.9300 . ?
C13 C14 1.392(8) . ?
C13 H13 0.9300 . ?
C14 H14 0.9300 . ?
C15 C16 1.513(7) . ?
C15 H15A 0.9700 . ?
C15 H15B 0.9700 . ?
C16 C17 1.345(8) . ?
C16 C25 1.410(7) . ?
C17 C18 1.479(8) . ?
C17 H17 0.9300 . ?
C18 C19 1.356(8) . ?
C18 C23 1.383(8) . ?
C19 C20 1.411(8) . ?
C19 H19 0.9300 . ?
C20 C21 1.379(8) . ?
C20 H20 0.9300 . ?
C21 C22 1.367(8) . ?
C22 C23 1.469(7) . ?
C22 H22 0.9300 . ?
C23 C24 1.385(8) . ?
C24 C25 1.374(7) . ?
C24 H24 0.9300 . ?
C25 H25 0.9300 . ?
C26 C27 1.357(8) . ?
C26 C31 1.384(8) . ?
C27 C28 1.402(8) . ?
C27 H27 0.9300 . ?
C28 C29 1.379(8) . ?
C28 H28 0.9300 . ?
C29 C30 1.360(9) . ?
C29 H29 0.9300 . ?
C30 C31 1.357(8) . ?
C30 H30 0.9300 . ?
C31 H31 0.9300 . ?

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
O1 S1 N1 111.4(2) . . ?
O1 S1 C4 105.3(3) . . ?
N1 S1 C4 89.3(2) . . ?
O2 S2 O3 120.5(3) . . ?
O2 S2 C26 109.7(3) . . ?
O3 S2 C26 109.8(3) . . ?
O2 S2 C1 106.7(3) . . ?
O3 S2 C1 106.7(3) . . ?
C26 S2 C1 101.7(3) . . ?
C2 N1 C15 117.5(4) . . ?
C2 N1 S1 117.1(4) . . ?
C15 N1 S1 111.5(3) . . ?
F1 C1 F2 104.3(5) . . ?
F1 C1 C2 112.2(5) . . ?
F2 C1 C2 110.0(5) . . ?
F1 C1 S2 103.8(4) . . ?
F2 C1 S2 106.6(4) . . ?
C2 C1 S2 118.8(4) . . ?
N1 C2 C3 104.3(5) . . ?
N1 C2 C1 104.9(4) . . ?
C3 C2 C1 110.3(5) . . ?
N1 C2 C9 113.9(4) . . ?
C3 C2 C9 111.0(5) . . ?
C1 C2 C9 112.0(5) . . ?
C4 C3 C8 121.0(6) . . ?
C4 C3 C2 112.5(5) . . ?
C8 C3 C2 126.5(6) . . ?
C3 C4 C5 120.3(6) . . ?
C3 C4 S1 115.3(5) . . ?
C5 C4 S1 124.2(5) . . ?
C6 C5 C4 119.7(7) . . ?
C6 C5 H5 120.1 . . ?
C4 C5 H5 120.1 . . ?
C5 C6 C7 120.7(7) . . ?
C5 C6 H6 119.6 . . ?
C7 C6 H6 119.6 . . ?
C6 C7 C8 119.5(7) . . ?
C6 C7 H7 120.2 . . ?
C8 C7 H7 120.2 . . ?
C3 C8 C7 118.7(7) . . ?
C3 C8 H8 120.6 . . ?
C7 C8 H8 120.6 . . ?
C14 C9 C10 118.2(6) . . ?
C14 C9 C2 125.2(6) . . ?
C10 C9 C2 116.5(5) . . ?
C11 C10 C9 121.3(6) . . ?
C11 C10 H10 119.3 . . ?
C9 C10 H10 119.3 . . ?
C10 C11 C12 119.8(7) . . ?
C10 C11 H11 120.1 . . ?
C12 C11 H11 120.1 . . ?
C13 C12 C11 120.1(7) . . ?
C13 C12 H12 120.0 . . ?
C11 C12 H12 120.0 . . ?
C12 C13 C14 120.2(7) . . ?
C12 C13 H13 119.9 . . ?
C14 C13 H13 119.9 . . ?
C9 C14 C13 120.4(6) . . ?
C9 C14 H14 119.8 . . ?
C13 C14 H14 119.8 . . ?
N1 C15 C16 114.3(5) . . ?
N1 C15 H15A 108.7 . . ?
C16 C15 H15A 108.7 . . ?
N1 C15 H15B 108.7 . . ?
C16 C15 H15B 108.7 . . ?
H15A C15 H15B 107.6 . . ?
C17 C16 C25 120.6(6) . . ?
C17 C16 C15 121.5(6) . . ?
C25 C16 C15 117.6(6) . . ?
C16 C17 C18 118.3(6) . . ?
C16 C17 H17 120.9 . . ?
C18 C17 H17 120.9 . . ?
C19 C18 C23 123.0(7) . . ?
C19 C18 C17 118.2(7) . . ?
C23 C18 C17 118.7(6) . . ?
C18 C19 C20 118.8(7) . . ?
C18 C19 H19 120.6 . . ?
C20 C19 H19 120.6 . . ?
C21 C20 C19 120.0(7) . . ?
C21 C20 H20 120.0 . . ?
C19 C20 H20 120.0 . . ?
C22 C21 C20 122.4(6) . . ?
C22 C21 Br 120.7(5) . . ?
C20 C21 Br 116.9(6) . . ?
C21 C22 C23 117.6(6) . . ?
C21 C22 H22 121.2 . . ?
C23 C22 H22 121.2 . . ?
C18 C23 C24 121.9(7) . . ?
C18 C23 C22 118.1(6) . . ?
C24 C23 C22 120.0(7) . . ?
C25 C24 C23 118.2(7) . . ?
C25 C24 H24 120.9 . . ?
C23 C24 H24 120.9 . . ?
C24 C25 C16 122.3(7) . . ?
C24 C25 H25 118.8 . . ?
C16 C25 H25 118.8 . . ?
C27 C26 C31 120.3(6) . . ?
C27 C26 S2 119.1(5) . . ?
C31 C26 S2 120.6(6) . . ?
C26 C27 C28 119.3(7) . . ?
C26 C27 H27 120.3 . . ?
C28 C27 H27 120.3 . . ?
C29 C28 C27 119.6(7) . . ?
C29 C28 H28 120.2 . . ?
C27 C28 H28 120.2 . . ?
C30 C29 C28 119.9(7) . . ?
C30 C29 H29 120.0 . . ?
C28 C29 H29 120.0 . . ?
C31 C30 C29 120.7(7) . . ?
C31 C30 H30 119.6 . . ?
C29 C30 H30 119.6 . . ?
C30 C31 C26 120.2(7) . . ?
C30 C31 H31 119.9 . . ?
C26 C31 H31 119.9 . . ?

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 S1 N1 C2 -93.8(4) . . . . ?
C4 S1 N1 C2 12.4(4) . . . . ?
O1 S1 N1 C15 45.6(4) . . . . ?
C4 S1 N1 C15 151.8(4) . . . . ?
O2 S2 C1 F1 38.9(4) . . . . ?
O3 S2 C1 F1 168.9(4) . . . . ?
C26 S2 C1 F1 -76.0(4) . . . . ?
O2 S2 C1 F2 148.7(4) . . . . ?
O3 S2 C1 F2 -81.3(4) . . . . ?
C26 S2 C1 F2 33.8(5) . . . . ?
O2 S2 C1 C2 -86.4(5) . . . . ?
O3 S2 C1 C2 43.6(5) . . . . ?
C26 S2 C1 C2 158.7(5) . . . . ?
C15 N1 C2 C3 -148.2(5) . . . . ?
S1 N1 C2 C3 -11.3(5) . . . . ?
C15 N1 C2 C1 95.8(5) . . . . ?
S1 N1 C2 C1 -127.3(4) . . . . ?
C15 N1 C2 C9 -27.1(7) . . . . ?
S1 N1 C2 C9 109.9(5) . . . . ?
F1 C1 C2 N1 -67.9(6) . . . . ?
F2 C1 C2 N1 176.4(4) . . . . ?
S2 C1 C2 N1 53.3(6) . . . . ?
F1 C1 C2 C3 -179.6(5) . . . . ?
F2 C1 C2 C3 64.7(6) . . . . ?
S2 C1 C2 C3 -58.5(6) . . . . ?
F1 C1 C2 C9 56.2(6) . . . . ?
F2 C1 C2 C9 -59.5(6) . . . . ?
S2 C1 C2 C9 177.3(4) . . . . ?
N1 C2 C3 C4 3.5(7) . . . . ?
C1 C2 C3 C4 115.7(5) . . . . ?
C9 C2 C3 C4 -119.6(5) . . . . ?
N1 C2 C3 C8 -176.4(6) . . . . ?
C1 C2 C3 C8 -64.3(8) . . . . ?
C9 C2 C3 C8 60.5(7) . . . . ?
C8 C3 C4 C5 -0.7(9) . . . . ?
C2 C3 C4 C5 179.4(5) . . . . ?
C8 C3 C4 S1 -175.0(5) . . . . ?
C2 C3 C4 S1 5.1(7) . . . . ?
O1 S1 C4 C3 102.2(5) . . . . ?
N1 S1 C4 C3 -9.9(5) . . . . ?
O1 S1 C4 C5 -71.8(6) . . . . ?
N1 S1 C4 C5 176.2(5) . . . . ?
C3 C4 C5 C6 0.6(10) . . . . ?
S1 C4 C5 C6 174.3(6) . . . . ?
C4 C5 C6 C7 -1.9(12) . . . . ?
C5 C6 C7 C8 3.4(13) . . . . ?
C4 C3 C8 C7 2.2(10) . . . . ?
C2 C3 C8 C7 -177.9(6) . . . . ?
C6 C7 C8 C3 -3.5(11) . . . . ?
N1 C2 C9 C14 117.9(6) . . . . ?
C3 C2 C9 C14 -124.7(6) . . . . ?
C1 C2 C9 C14 -0.9(8) . . . . ?
N1 C2 C9 C10 -62.7(7) . . . . ?
C3 C2 C9 C10 54.6(7) . . . . ?
C1 C2 C9 C10 178.5(5) . . . . ?
C14 C9 C10 C11 -1.5(9) . . . . ?
C2 C9 C10 C11 179.1(5) . . . . ?
C9 C10 C11 C12 1.2(9) . . . . ?
C10 C11 C12 C13 -1.7(10) . . . . ?
C11 C12 C13 C14 2.5(12) . . . . ?
C10 C9 C14 C13 2.2(10) . . . . ?
C2 C9 C14 C13 -178.4(6) . . . . ?
C12 C13 C14 C9 -2.8(12) . . . . ?
C2 N1 C15 C16 -164.5(5) . . . . ?
S1 N1 C15 C16 56.3(6) . . . . ?
N1 C15 C16 C17 51.8(8) . . . . ?
N1 C15 C16 C25 -134.1(6) . . . . ?
C25 C16 C17 C18 -0.2(9) . . . . ?
C15 C16 C17 C18 173.7(5) . . . . ?
C16 C17 C18 C19 -178.4(6) . . . . ?
C16 C17 C18 C23 1.0(9) . . . . ?
C23 C18 C19 C20 -2.7(11) . . . . ?
C17 C18 C19 C20 176.7(6) . . . . ?
C18 C19 C20 C21 2.1(11) . . . . ?
C19 C20 C21 C22 0.6(10) . . . . ?
C19 C20 C21 Br -177.0(5) . . . . ?
C20 C21 C22 C23 -2.6(9) . . . . ?
Br C21 C22 C23 174.9(4) . . . . ?
C19 C18 C23 C24 178.3(7) . . . . ?
C17 C18 C23 C24 -1.1(10) . . . . ?
C19 C18 C23 C22 0.6(10) . . . . ?
C17 C18 C23 C22 -178.8(5) . . . . ?
C21 C22 C23 C18 2.0(9) . . . . ?
C21 C22 C23 C24 -175.7(6) . . . . ?
C18 C23 C24 C25 0.3(10) . . . . ?
C22 C23 C24 C25 178.0(6) . . . . ?
C23 C24 C25 C16 0.5(10) . . . . ?
C17 C16 C25 C24 -0.6(10) . . . . ?
C15 C16 C25 C24 -174.7(6) . . . . ?
O2 S2 C26 C27 -25.3(7) . . . . ?
O3 S2 C26 C27 -159.9(5) . . . . ?
C1 S2 C26 C27 87.4(6) . . . . ?
O2 S2 C26 C31 155.4(6) . . . . ?
O3 S2 C26 C31 20.8(7) . . . . ?
C1 S2 C26 C31 -92.0(6) . . . . ?
C31 C26 C27 C28 -0.6(11) . . . . ?
S2 C26 C27 C28 -179.9(5) . . . . ?
C26 C27 C28 C29 -0.4(11) . . . . ?
C27 C28 C29 C30 0.6(12) . . . . ?
C28 C29 C30 C31 0.1(12) . . . . ?
C29 C30 C31 C26 -1.1(12) . . . . ?
C27 C26 C31 C30 1.3(11) . . . . ?
S2 C26 C31 C30 -179.4(5) . . . . ?

_diffrn_measured_fraction_theta_max 0.994
_diffrn_reflns_theta_full        27.50
_diffrn_measured_fraction_theta_full 0.994
_refine_diff_density_max         0.355
_refine_diff_density_min         -0.358
_refine_diff_density_rms         0.059

_database_code_depnum_ccdc_archive 'CCDC 1009683'
#######################################################################
#
#                 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_040

_audit_creation_method           SHELXL-97
_chemical_name_systematic        
; 
 ? 
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         'C21 H16 Br N O3 S'
_chemical_formula_sum            'C21 H16 Br N O3 S'
_chemical_formula_weight         442.32

loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0181 0.0091 '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'
N N 0.0311 0.0180 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0492 0.0322 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
S S 0.3331 0.5567 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
Br Br -0.6763 1.2805 '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                   9.876(2)
_cell_length_b                   11.292(2)
_cell_length_c                   16.818(3)
_cell_angle_alpha                90.00
_cell_angle_beta                 92.78(3)
_cell_angle_gamma                90.00
_cell_volume                     1873.4(7)
_cell_formula_units_Z            4
_cell_measurement_temperature    296(2)
_cell_measurement_reflns_used    6898
_cell_measurement_theta_min      4.72
_cell_measurement_theta_max      66.94

_exptl_crystal_description       column
_exptl_crystal_colour            colorless
_exptl_crystal_size_max          0.46
_exptl_crystal_size_mid          0.10
_exptl_crystal_size_min          0.06
_exptl_crystal_density_meas      ?
_exptl_crystal_density_diffrn    1.568
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             896
_exptl_absorpt_coefficient_mu    4.218
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.2472
_exptl_absorpt_correction_T_max  0.7859
_exptl_absorpt_process_details   sadabs

_exptl_special_details           
; 
 ? 
;

_diffrn_ambient_temperature      296(2)
_diffrn_radiation_wavelength     1.54178
_diffrn_radiation_type           CuK\a
_diffrn_radiation_source         'fine-focus sealed tube'
_diffrn_radiation_monochromator  graphite
_diffrn_measurement_device_type  ?
_diffrn_measurement_method       ?
_diffrn_detector_area_resol_mean ?
_diffrn_standards_number         ?
_diffrn_standards_interval_count ?
_diffrn_standards_interval_time  ?
_diffrn_standards_decay_%        ?
_diffrn_reflns_number            12287
_diffrn_reflns_av_R_equivalents  0.0197
_diffrn_reflns_av_sigmaI/netI    0.0190
_diffrn_reflns_limit_h_min       -11
_diffrn_reflns_limit_h_max       10
_diffrn_reflns_limit_k_min       -12
_diffrn_reflns_limit_k_max       11
_diffrn_reflns_limit_l_min       -20
_diffrn_reflns_limit_l_max       19
_diffrn_reflns_theta_min         4.72
_diffrn_reflns_theta_max         67.33
_reflns_number_total             3191
_reflns_number_gt                2980
_reflns_threshold_expression     >2sigma(I)

_computing_data_collection       'Bruker APEX2'
_computing_cell_refinement       'Bruker SAINT'
_computing_data_reduction        'Bruker SAINT'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 2008)'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 2008)'
_computing_molecular_graphics    'Bruker SHELXTL'
_computing_publication_material  'Bruker SHELXTL'

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

_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'calc w=1/[σ²(Fo²)+(0.0423P)²+1.9087P] 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       0.00028(11)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc²λ³/sin(2θ)]^-1/4^
_refine_ls_number_reflns         3191
_refine_ls_number_parameters     245
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0419
_refine_ls_R_factor_gt           0.0398
_refine_ls_wR_factor_ref         0.1002
_refine_ls_wR_factor_gt          0.0985
_refine_ls_goodness_of_fit_ref   1.046
_refine_ls_restrained_S_all      1.046
_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
Br1 Br 0.28725(4) 0.22821(3) 0.09520(3) 0.0868(2) Uani 1 1 d . . .
S1 S 0.66955(6) -0.57872(6) 0.05531(4) 0.04652(19) Uani 1 1 d . . .
O1 O 0.6505(3) -0.7016(2) 0.04312(18) 0.0848(8) Uani 1 1 d . . .
O2 O 0.6539(2) -0.5063(2) -0.01537(11) 0.0683(7) Uani 1 1 d . . .
O3 O 0.38331(18) -0.35740(17) 0.18533(13) 0.0528(5) Uani 1 1 d . . .
N1 N 0.5797(2) -0.5300(2) 0.12679(12) 0.0406(5) Uani 1 1 d . . .
H1B H 0.4975 -0.5523 0.1326 0.049 Uiso 1 1 calc R . .
C1 C 0.8229(2) -0.5409(2) 0.10456(15) 0.0420(6) Uani 1 1 d . . .
C2 C 0.8000(2) -0.4656(2) 0.16677(14) 0.0380(5) Uani 1 1 d . . .
C3 C 0.9102(3) -0.4160(3) 0.20871(16) 0.0455(6) Uani 1 1 d . . .
H3A H 0.8975 -0.3662 0.2518 0.055 Uiso 1 1 calc R . .
C4 C 1.0395(3) -0.4418(3) 0.18536(18) 0.0548(7) Uani 1 1 d . . .
H4A H 1.1139 -0.4066 0.2119 0.066 Uiso 1 1 calc R . .
C5 C 1.0598(3) -0.5186(3) 0.12346(19) 0.0598(8) Uani 1 1 d . . .
H5A H 1.1476 -0.5356 0.1094 0.072 Uiso 1 1 calc R . .
C6 C 0.9518(3) -0.5707(3) 0.08207(17) 0.0546(7) Uani 1 1 d . . .
H6A H 0.9648 -0.6237 0.0408 0.065 Uiso 1 1 calc R . .
C7 C 0.6499(2) -0.4444(2) 0.18119(14) 0.0368(5) Uani 1 1 d . . .
C8 C 0.6128(2) -0.3172(2) 0.15686(16) 0.0418(6) Uani 1 1 d . . .
H8A H 0.6682 -0.2632 0.1893 0.050 Uiso 1 1 calc R . .
H8B H 0.6354 -0.3056 0.1019 0.050 Uiso 1 1 calc R . .
C9 C 0.4645(2) -0.2846(2) 0.16480(15) 0.0403(6) Uani 1 1 d . . .
C10 C 0.4236(2) -0.1600(2) 0.14606(14) 0.0391(5) Uani 1 1 d . . .
C11 C 0.5115(3) -0.0788(2) 0.11393(16) 0.0452(6) Uani 1 1 d . . .
H11A H 0.5991 -0.1021 0.1032 0.054 Uiso 1 1 calc R . .
C12 C 0.4707(3) 0.0361(3) 0.09770(17) 0.0503(7) Uani 1 1 d . . .
H12A H 0.5296 0.0899 0.0757 0.060 Uiso 1 1 calc R . .
C13 C 0.3411(3) 0.0691(2) 0.11473(18) 0.0506(7) Uani 1 1 d . . .
C14 C 0.2514(3) -0.0089(3) 0.14657(19) 0.0554(7) Uani 1 1 d . . .
H14A H 0.1643 0.0153 0.1576 0.066 Uiso 1 1 calc R . .
C15 C 0.2929(3) -0.1235(3) 0.16175(17) 0.0492(6) Uani 1 1 d . . .
H15A H 0.2328 -0.1772 0.1828 0.059 Uiso 1 1 calc R . .
C16 C 0.6253(2) -0.4753(2) 0.26796(14) 0.0373(5) Uani 1 1 d . . .
C17 C 0.6475(3) -0.3928(3) 0.32824(17) 0.0517(7) Uani 1 1 d . . .
H17A H 0.6673 -0.3147 0.3154 0.062 Uiso 1 1 calc R . .
C18 C 0.6406(3) -0.4255(3) 0.40753(17) 0.0601(8) Uani 1 1 d . . .
H18A H 0.6561 -0.3694 0.4474 0.072 Uiso 1 1 calc R . .
C19 C 0.6114(3) -0.5395(3) 0.42727(17) 0.0557(8) Uani 1 1 d . . .
H19A H 0.6081 -0.5613 0.4805 0.067 Uiso 1 1 calc R . .
C20 C 0.5868(3) -0.6216(3) 0.36851(17) 0.0521(7) Uani 1 1 d . . .
H20A H 0.5652 -0.6990 0.3819 0.062 Uiso 1 1 calc R . .
C21 C 0.5939(3) -0.5901(2) 0.28905(15) 0.0438(6) Uani 1 1 d . . .
H21A H 0.5774 -0.6468 0.2496 0.053 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
Br1 C13 1.898(3) . ?
S1 O1 1.414(3) . ?
S1 O2 1.445(2) . ?
S1 N1 1.624(2) . ?
S1 C1 1.743(3) . ?
O3 C9 1.211(3) . ?
N1 C7 1.480(3) . ?
N1 H1B 0.8600 . ?
C1 C2 1.375(4) . ?
C1 C6 1.388(4) . ?
C2 C3 1.387(4) . ?
C2 C7 1.533(3) . ?
C3 C4 1.385(4) . ?
C3 H3A 0.9300 . ?
C4 C5 1.377(5) . ?
C4 H4A 0.9300 . ?
C5 C6 1.377(5) . ?
C5 H5A 0.9300 . ?
C6 H6A 0.9300 . ?
C7 C16 1.531(3) . ?
C7 C8 1.533(4) . ?
C8 C9 1.522(3) . ?
C8 H8A 0.9700 . ?
C8 H8B 0.9700 . ?
C9 C10 1.493(4) . ?
C10 C11 1.390(4) . ?
C10 C15 1.393(3) . ?
C11 C12 1.381(4) . ?
C11 H11A 0.9300 . ?
C12 C13 1.377(4) . ?
C12 H12A 0.9300 . ?
C13 C14 1.376(4) . ?
C14 C15 1.377(4) . ?
C14 H14A 0.9300 . ?
C15 H15A 0.9300 . ?
C16 C21 1.383(4) . ?
C16 C17 1.387(4) . ?
C17 C18 1.389(4) . ?
C17 H17A 0.9300 . ?
C18 C19 1.364(5) . ?
C18 H18A 0.9300 . ?
C19 C20 1.368(4) . ?
C19 H19A 0.9300 . ?
C20 C21 1.388(4) . ?
C20 H20A 0.9300 . ?
C21 H21A 0.9300 . ?

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
O1 S1 O2 115.33(17) . . ?
O1 S1 N1 111.47(14) . . ?
O2 S1 N1 112.14(13) . . ?
O1 S1 C1 114.57(15) . . ?
O2 S1 C1 107.92(13) . . ?
N1 S1 C1 93.35(11) . . ?
C7 N1 S1 114.98(15) . . ?
C7 N1 H1B 122.5 . . ?
S1 N1 H1B 122.5 . . ?
C2 C1 C6 123.0(3) . . ?
C2 C1 S1 110.00(18) . . ?
C6 C1 S1 126.7(2) . . ?
C1 C2 C3 118.9(2) . . ?
C1 C2 C7 114.4(2) . . ?
C3 C2 C7 126.7(2) . . ?
C4 C3 C2 118.8(3) . . ?
C4 C3 H3A 120.6 . . ?
C2 C3 H3A 120.6 . . ?
C5 C4 C3 121.1(3) . . ?
C5 C4 H4A 119.4 . . ?
C3 C4 H4A 119.4 . . ?
C6 C5 C4 120.9(3) . . ?
C6 C5 H5A 119.5 . . ?
C4 C5 H5A 119.5 . . ?
C5 C6 C1 117.2(3) . . ?
C5 C6 H6A 121.4 . . ?
C1 C6 H6A 121.4 . . ?
N1 C7 C16 110.4(2) . . ?
N1 C7 C2 103.16(19) . . ?
C16 C7 C2 108.32(19) . . ?
N1 C7 C8 110.4(2) . . ?
C16 C7 C8 114.9(2) . . ?
C2 C7 C8 108.94(19) . . ?
C9 C8 C7 114.9(2) . . ?
C9 C8 H8A 108.5 . . ?
C7 C8 H8A 108.5 . . ?
C9 C8 H8B 108.5 . . ?
C7 C8 H8B 108.5 . . ?
H8A C8 H8B 107.5 . . ?
O3 C9 C10 121.6(2) . . ?
O3 C9 C8 120.9(2) . . ?
C10 C9 C8 117.5(2) . . ?
C11 C10 C15 118.7(2) . . ?
C11 C10 C9 122.4(2) . . ?
C15 C10 C9 118.9(2) . . ?
C12 C11 C10 121.0(2) . . ?
C12 C11 H11A 119.5 . . ?
C10 C11 H11A 119.5 . . ?
C13 C12 C11 118.6(3) . . ?
C13 C12 H12A 120.7 . . ?
C11 C12 H12A 120.7 . . ?
C14 C13 C12 122.0(3) . . ?
C14 C13 Br1 119.6(2) . . ?
C12 C13 Br1 118.4(2) . . ?
C13 C14 C15 118.8(3) . . ?
C13 C14 H14A 120.6 . . ?
C15 C14 H14A 120.6 . . ?
C14 C15 C10 120.9(3) . . ?
C14 C15 H15A 119.6 . . ?
C10 C15 H15A 119.6 . . ?
C21 C16 C17 118.2(2) . . ?
C21 C16 C7 120.4(2) . . ?
C17 C16 C7 121.1(2) . . ?
C16 C17 C18 120.6(3) . . ?
C16 C17 H17A 119.7 . . ?
C18 C17 H17A 119.7 . . ?
C19 C18 C17 120.4(3) . . ?
C19 C18 H18A 119.8 . . ?
C17 C18 H18A 119.8 . . ?
C18 C19 C20 119.7(3) . . ?
C18 C19 H19A 120.1 . . ?
C20 C19 H19A 120.1 . . ?
C19 C20 C21 120.5(3) . . ?
C19 C20 H20A 119.8 . . ?
C21 C20 H20A 119.8 . . ?
C16 C21 C20 120.6(3) . . ?
C16 C21 H21A 119.7 . . ?
C20 C21 H21A 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
O1 S1 N1 C7 138.4(2) . . . . ?
O2 S1 N1 C7 -90.5(2) . . . . ?
C1 S1 N1 C7 20.35(19) . . . . ?
O1 S1 C1 C2 -130.0(2) . . . . ?
O2 S1 C1 C2 100.1(2) . . . . ?
N1 S1 C1 C2 -14.5(2) . . . . ?
O1 S1 C1 C6 55.8(3) . . . . ?
O2 S1 C1 C6 -74.2(3) . . . . ?
N1 S1 C1 C6 171.3(3) . . . . ?
C6 C1 C2 C3 0.7(4) . . . . ?
S1 C1 C2 C3 -173.8(2) . . . . ?
C6 C1 C2 C7 179.8(2) . . . . ?
S1 C1 C2 C7 5.3(3) . . . . ?
C1 C2 C3 C4 1.5(4) . . . . ?
C7 C2 C3 C4 -177.5(2) . . . . ?
C2 C3 C4 C5 -2.3(4) . . . . ?
C3 C4 C5 C6 1.0(5) . . . . ?
C4 C5 C6 C1 1.1(5) . . . . ?
C2 C1 C6 C5 -1.9(4) . . . . ?
S1 C1 C6 C5 171.6(2) . . . . ?
S1 N1 C7 C16 -134.76(17) . . . . ?
S1 N1 C7 C2 -19.2(2) . . . . ?
S1 N1 C7 C8 97.1(2) . . . . ?
C1 C2 C7 N1 7.8(3) . . . . ?
C3 C2 C7 N1 -173.2(2) . . . . ?
C1 C2 C7 C16 124.8(2) . . . . ?
C3 C2 C7 C16 -56.1(3) . . . . ?
C1 C2 C7 C8 -109.5(2) . . . . ?
C3 C2 C7 C8 69.5(3) . . . . ?
N1 C7 C8 C9 65.1(3) . . . . ?
C16 C7 C8 C9 -60.6(3) . . . . ?
C2 C7 C8 C9 177.7(2) . . . . ?
C7 C8 C9 O3 -3.3(4) . . . . ?
C7 C8 C9 C10 176.9(2) . . . . ?
O3 C9 C10 C11 -172.6(3) . . . . ?
C8 C9 C10 C11 7.2(4) . . . . ?
O3 C9 C10 C15 7.8(4) . . . . ?
C8 C9 C10 C15 -172.4(2) . . . . ?
C15 C10 C11 C12 0.0(4) . . . . ?
C9 C10 C11 C12 -179.6(2) . . . . ?
C10 C11 C12 C13 0.6(4) . . . . ?
C11 C12 C13 C14 -0.6(4) . . . . ?
C11 C12 C13 Br1 178.2(2) . . . . ?
C12 C13 C14 C15 0.0(5) . . . . ?
Br1 C13 C14 C15 -178.8(2) . . . . ?
C13 C14 C15 C10 0.7(4) . . . . ?
C11 C10 C15 C14 -0.6(4) . . . . ?
C9 C10 C15 C14 179.0(3) . . . . ?
N1 C7 C16 C21 24.7(3) . . . . ?
C2 C7 C16 C21 -87.6(3) . . . . ?
C8 C7 C16 C21 150.3(2) . . . . ?
N1 C7 C16 C17 -162.1(2) . . . . ?
C2 C7 C16 C17 85.6(3) . . . . ?
C8 C7 C16 C17 -36.4(3) . . . . ?
C21 C16 C17 C18 1.1(4) . . . . ?
C7 C16 C17 C18 -172.3(2) . . . . ?
C16 C17 C18 C19 -0.2(5) . . . . ?
C17 C18 C19 C20 -0.9(5) . . . . ?
C18 C19 C20 C21 1.2(4) . . . . ?
C17 C16 C21 C20 -0.8(4) . . . . ?
C7 C16 C21 C20 172.6(2) . . . . ?
C19 C20 C21 C16 -0.3(4) . . . . ?

loop_
_geom_hbond_atom_site_label_D
_geom_hbond_atom_site_label_H
_geom_hbond_atom_site_label_A
_geom_hbond_distance_DH
_geom_hbond_distance_HA
_geom_hbond_distance_DA
_geom_hbond_angle_DHA
_geom_hbond_site_symmetry_A
N1 H1B O2 0.86 2.50 2.930(3) 111.4 3_645

_diffrn_measured_fraction_theta_max 0.947
_diffrn_reflns_theta_full        67.33
_diffrn_measured_fraction_theta_full 0.947
_refine_diff_density_max         0.609
_refine_diff_density_min         -0.634
_refine_diff_density_rms         0.053
_database_code_depnum_ccdc_archive 'CCDC 1009684'
