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

#######################################################################
#
#                 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_1a_sd

_audit_creation_method           SHELXL-97
_chemical_name_systematic        
;
 ?
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C18 H13 Br N2 O2 S'
_chemical_formula_weight         401.27

loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
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)/n  '

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

_cell_length_a                   13.675(4)
_cell_length_b                   8.025(2)
_cell_length_c                   15.703(4)
_cell_angle_alpha                90.00
_cell_angle_beta                 100.008(8)
_cell_angle_gamma                90.00
_cell_volume                     1697.2(8)
_cell_formula_units_Z            4
_cell_measurement_temperature    293(2)
_cell_measurement_reflns_used    ?
_cell_measurement_theta_min      ?
_cell_measurement_theta_max      ?

_exptl_crystal_description       ?
_exptl_crystal_colour            ?
_exptl_crystal_size_max          0.15
_exptl_crystal_size_mid          0.14
_exptl_crystal_size_min          0.11
_exptl_crystal_density_meas      ?
_exptl_crystal_density_diffrn    1.570
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             808
_exptl_absorpt_coefficient_mu    2.558
_exptl_absorpt_correction_type   none
_exptl_absorpt_correction_T_min  ?
_exptl_absorpt_correction_T_max  ?
_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  ?
_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            19731
_diffrn_reflns_av_R_equivalents  0.0773
_diffrn_reflns_av_sigmaI/netI    0.0526
_diffrn_reflns_limit_h_min       -14
_diffrn_reflns_limit_h_max       16
_diffrn_reflns_limit_k_min       -9
_diffrn_reflns_limit_k_max       9
_diffrn_reflns_limit_l_min       -18
_diffrn_reflns_limit_l_max       18
_diffrn_reflns_theta_min         1.82
_diffrn_reflns_theta_max         25.00
_reflns_number_total             2996
_reflns_number_gt                1806
_reflns_threshold_expression     >2σ(I)

_computing_data_collection       ?
_computing_cell_refinement       ?
_computing_data_reduction        ?
_computing_structure_solution    ?
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 2008)'
_computing_molecular_graphics    ?
_computing_publication_material  ?

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

_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'calc w=1/[σ²(Fo²)+(0.0548P)²+0.9671P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_atom_sites_solution_hydrogens   geom
_refine_ls_hydrogen_treatment    mixed
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       ?
_refine_ls_number_reflns         2996
_refine_ls_number_parameters     217
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0973
_refine_ls_R_factor_gt           0.0504
_refine_ls_wR_factor_ref         0.1352
_refine_ls_wR_factor_gt          0.1138
_refine_ls_goodness_of_fit_ref   1.061
_refine_ls_restrained_S_all      1.061
_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 0.83463(6) 0.99758(10) 0.20739(4) 0.1070(3) Uani 1 1 d . . .
S1 S 0.73436(8) 1.23536(14) -0.13122(7) 0.0478(3) Uani 1 1 d . . .
O2 O 0.7248(2) 1.2744(4) -0.22066(18) 0.0609(9) Uani 1 1 d . . .
O1 O 0.6973(2) 1.0823(4) -0.1049(2) 0.0605(9) Uani 1 1 d . . .
N2 N 0.8490(3) 1.1204(5) 0.0477(2) 0.0527(10) Uani 1 1 d . . .
C8 C 0.8996(3) 1.1913(5) -0.0077(3) 0.0455(11) Uani 1 1 d . . .
N1 N 0.8560(2) 1.2380(4) -0.0930(2) 0.0454(9) Uani 1 1 d . . .
C9 C 0.9985(3) 1.2353(5) 0.0076(3) 0.0454(11) Uani 1 1 d . . .
C10 C 1.0188(3) 1.3179(5) -0.0682(3) 0.0492(11) Uani 1 1 d . . .
C11 C 0.9313(3) 1.3233(5) -0.1294(3) 0.0458(11) Uani 1 1 d . . .
C6 C 0.6589(3) 1.3714(6) 0.0020(3) 0.0520(11) Uani 1 1 d . . .
H6 H 0.6625 1.2650 0.0258 0.062 Uiso 1 1 calc R . .
C5 C 0.6260(3) 1.5025(7) 0.0449(3) 0.0587(13) Uani 1 1 d . . .
H5 H 0.6065 1.4835 0.0980 0.070 Uiso 1 1 calc R . .
C15 C 1.1041(4) 1.3915(6) -0.0882(4) 0.0671(14) Uani 1 1 d . . .
H15 H 1.1634 1.3886 -0.0488 0.081 Uiso 1 1 calc R . .
C18 C 0.9045(4) 1.0892(6) 0.1239(3) 0.0602(13) Uani 1 1 d . . .
C13 C 1.0138(5) 1.4709(6) -0.2272(4) 0.0741(15) Uani 1 1 d . . .
H13 H 1.0137 1.5212 -0.2806 0.089 Uiso 1 1 calc R . .
C1 C 0.6868(3) 1.3992(5) -0.0773(3) 0.0443(10) Uani 1 1 d . . .
C4 C 0.6208(3) 1.6616(6) 0.0119(4) 0.0600(13) Uani 1 1 d . . .
C17 C 1.0049(4) 1.1175(6) 0.1466(3) 0.0654(14) Uani 1 1 d . . .
H17 H 1.0393 1.0859 0.2006 0.078 Uiso 1 1 calc R . .
C12 C 0.9265(4) 1.3983(6) -0.2092(3) 0.0615(13) Uani 1 1 d . . .
H12 H 0.8678 1.4005 -0.2492 0.074 Uiso 1 1 calc R . .
C2 C 0.6811(3) 1.5574(6) -0.1131(3) 0.0564(12) Uani 1 1 d . . .
H2 H 0.6994 1.5756 -0.1667 0.068 Uiso 1 1 calc R . .
C14 C 1.0996(5) 1.4687(7) -0.1671(4) 0.0810(17) Uani 1 1 d . . .
H14 H 1.1561 1.5207 -0.1799 0.097 Uiso 1 1 calc R . .
C16 C 1.0528(4) 1.1938(6) 0.0874(3) 0.0596(13) Uani 1 1 d . . .
H16 H 1.1204 1.2171 0.1006 0.072 Uiso 1 1 calc R . .
C3 C 0.6480(4) 1.6870(6) -0.0685(4) 0.0634(14) Uani 1 1 d . . .
H3 H 0.6436 1.7933 -0.0924 0.076 Uiso 1 1 calc R . .
C7 C 0.5874(4) 1.8075(7) 0.0608(4) 0.096(2) Uani 1 1 d . . .
H7A H 0.5710 1.7689 0.1145 0.144 Uiso 1 1 calc R . .
H7B H 0.5300 1.8580 0.0267 0.144 Uiso 1 1 calc R . .
H7C H 0.6400 1.8880 0.0723 0.144 Uiso 1 1 calc R . .

loop_
_atom_site_aniso_label
_atom_site_aniso_U_11
_atom_site_aniso_U_22
_atom_site_aniso_U_33
_atom_site_aniso_U_23
_atom_site_aniso_U_13
_atom_site_aniso_U_12
Br1 0.1127(6) 0.1565(7) 0.0523(4) 0.0203(4) 0.0155(4) -0.0228(5)
S1 0.0438(7) 0.0530(7) 0.0418(6) -0.0051(5) -0.0056(5) -0.0048(5)
O2 0.059(2) 0.083(2) 0.0346(17) -0.0053(15) -0.0077(15) -0.0019(17)
O1 0.060(2) 0.0490(18) 0.066(2) -0.0035(16) -0.0065(17) -0.0153(16)
N2 0.051(2) 0.062(2) 0.041(2) 0.0000(18) -0.0010(19) 0.0011(19)
C8 0.050(3) 0.044(2) 0.040(3) -0.0045(19) 0.001(2) 0.003(2)
N1 0.039(2) 0.055(2) 0.038(2) 0.0025(17) -0.0054(16) 0.0028(17)
C9 0.037(3) 0.049(3) 0.046(3) -0.006(2) -0.006(2) 0.003(2)
C10 0.041(3) 0.052(3) 0.053(3) -0.003(2) 0.004(2) 0.000(2)
C11 0.044(3) 0.045(2) 0.046(3) 0.003(2) 0.004(2) 0.000(2)
C6 0.043(3) 0.056(3) 0.054(3) 0.008(2) 0.001(2) -0.005(2)
C5 0.042(3) 0.082(4) 0.051(3) -0.003(3) 0.006(2) -0.001(3)
C15 0.045(3) 0.079(4) 0.075(4) -0.002(3) 0.006(3) -0.006(3)
C18 0.072(4) 0.065(3) 0.040(3) -0.002(2) 0.000(3) 0.001(3)
C13 0.078(4) 0.075(4) 0.071(4) 0.017(3) 0.016(3) -0.010(3)
C1 0.033(2) 0.053(3) 0.044(3) 0.001(2) -0.001(2) -0.010(2)
C4 0.038(3) 0.061(3) 0.076(4) -0.016(3) -0.005(3) 0.000(2)
C17 0.066(4) 0.082(4) 0.039(3) 0.001(3) -0.016(3) 0.003(3)
C12 0.060(3) 0.067(3) 0.055(3) 0.006(3) 0.002(2) -0.002(3)
C2 0.054(3) 0.058(3) 0.056(3) 0.008(2) 0.006(2) -0.008(2)
C14 0.062(4) 0.089(4) 0.096(5) 0.004(4) 0.027(4) -0.011(3)
C16 0.047(3) 0.073(3) 0.052(3) -0.006(3) -0.010(2) 0.002(2)
C3 0.066(3) 0.043(3) 0.077(4) 0.003(3) 0.001(3) 0.001(2)
C7 0.078(4) 0.089(4) 0.119(5) -0.035(4) 0.012(4) 0.006(3)

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

loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
Br1 C18 1.899(5) . ?
S1 O1 1.418(3) . ?
S1 O2 1.423(3) . ?
S1 N1 1.667(4) . ?
S1 C1 1.749(4) . ?
N2 C18 1.325(6) . ?
N2 C8 1.330(5) . ?
C8 C9 1.377(6) . ?
C8 N1 1.420(5) . ?
N1 C11 1.435(5) . ?
C9 C16 1.382(6) . ?
C9 C10 1.431(6) . ?
C10 C15 1.391(6) . ?
C10 C11 1.399(6) . ?
C11 C12 1.381(6) . ?
C6 C5 1.368(6) . ?
C6 C1 1.381(6) . ?
C5 C4 1.375(6) . ?
C15 C14 1.377(7) . ?
C18 C17 1.377(7) . ?
C13 C14 1.372(8) . ?
C13 C12 1.401(7) . ?
C1 C2 1.385(6) . ?
C4 C3 1.391(7) . ?
C4 C7 1.513(7) . ?
C17 C16 1.372(7) . ?
C2 C3 1.374(6) . ?

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 120.16(19) . . ?
O1 S1 N1 106.94(18) . . ?
O2 S1 N1 105.49(18) . . ?
O1 S1 C1 109.1(2) . . ?
O2 S1 C1 109.5(2) . . ?
N1 S1 C1 104.34(18) . . ?
C18 N2 C8 112.9(4) . . ?
N2 C8 C9 127.0(4) . . ?
N2 C8 N1 123.3(4) . . ?
C9 C8 N1 109.6(4) . . ?
C8 N1 C11 106.8(3) . . ?
C8 N1 S1 124.4(3) . . ?
C11 N1 S1 127.1(3) . . ?
C8 C9 C16 117.0(4) . . ?
C8 C9 C10 107.5(4) . . ?
C16 C9 C10 135.5(4) . . ?
C15 C10 C11 118.8(4) . . ?
C15 C10 C9 132.5(4) . . ?
C11 C10 C9 108.6(4) . . ?
C12 C11 C10 122.5(4) . . ?
C12 C11 N1 130.1(4) . . ?
C10 C11 N1 107.4(4) . . ?
C5 C6 C1 119.1(4) . . ?
C6 C5 C4 121.9(5) . . ?
C14 C15 C10 119.1(5) . . ?
N2 C18 C17 126.3(4) . . ?
N2 C18 Br1 114.7(4) . . ?
C17 C18 Br1 118.9(4) . . ?
C14 C13 C12 120.8(5) . . ?
C6 C1 C2 120.6(4) . . ?
C6 C1 S1 119.9(3) . . ?
C2 C1 S1 119.4(3) . . ?
C5 C4 C3 118.3(4) . . ?
C5 C4 C7 121.8(5) . . ?
C3 C4 C7 119.9(5) . . ?
C16 C17 C18 118.0(4) . . ?
C11 C12 C13 117.2(5) . . ?
C3 C2 C1 119.1(4) . . ?
C13 C14 C15 121.7(5) . . ?
C17 C16 C9 118.5(4) . . ?
C2 C3 C4 121.0(4) . . ?

_diffrn_measured_fraction_theta_max 1.000
_diffrn_reflns_theta_full        25.00
_diffrn_measured_fraction_theta_full 1.000
_refine_diff_density_max         0.580
_refine_diff_density_min         -0.942
_refine_diff_density_rms         0.065
_database_code_depnum_ccdc_archive 'CCDC 953972'
#######################################################################
#
#                 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_1b_sd

_audit_creation_method           SHELXL-97
_chemical_name_systematic        
;
 ?
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C18 H13 Br N2 O2 S'
_chemical_formula_weight         401.27

loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
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   'P 21/n '

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

_cell_length_a                   11.494(3)
_cell_length_b                   8.262(2)
_cell_length_c                   17.581(4)
_cell_angle_alpha                90.00
_cell_angle_beta                 103.742(8)
_cell_angle_gamma                90.00
_cell_volume                     1621.7(7)
_cell_formula_units_Z            4
_cell_measurement_temperature    293(2)
_cell_measurement_reflns_used    ?
_cell_measurement_theta_min      ?
_cell_measurement_theta_max      ?

_exptl_crystal_description       ?
_exptl_crystal_colour            ?
_exptl_crystal_size_max          0.23
_exptl_crystal_size_mid          0.15
_exptl_crystal_size_min          0.12
_exptl_crystal_density_meas      ?
_exptl_crystal_density_diffrn    1.644
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             808
_exptl_absorpt_coefficient_mu    2.677
_exptl_absorpt_correction_type   none
_exptl_absorpt_correction_T_min  ?
_exptl_absorpt_correction_T_max  ?
_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  ?
_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            18788
_diffrn_reflns_av_R_equivalents  0.0771
_diffrn_reflns_av_sigmaI/netI    0.0525
_diffrn_reflns_limit_h_min       -13
_diffrn_reflns_limit_h_max       13
_diffrn_reflns_limit_k_min       -9
_diffrn_reflns_limit_k_max       9
_diffrn_reflns_limit_l_min       -20
_diffrn_reflns_limit_l_max       20
_diffrn_reflns_theta_min         1.93
_diffrn_reflns_theta_max         25.00
_reflns_number_total             2845
_reflns_number_gt                1780
_reflns_threshold_expression     >2σ(I)

_computing_data_collection       ?
_computing_cell_refinement       ?
_computing_data_reduction        ?
_computing_structure_solution    ?
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 2008)'
_computing_molecular_graphics    ?
_computing_publication_material  ?

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

_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'calc w=1/[σ²(Fo²)+(0.1166P)²+24.7760P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_atom_sites_solution_hydrogens   geom
_refine_ls_hydrogen_treatment    mixed
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       ?
_refine_ls_number_reflns         2845
_refine_ls_number_parameters     217
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.1007
_refine_ls_R_factor_gt           0.0566
_refine_ls_wR_factor_ref         0.1971
_refine_ls_wR_factor_gt          0.1431
_refine_ls_goodness_of_fit_ref   0.635
_refine_ls_restrained_S_all      0.635
_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 0.37576(9) 0.05466(14) 0.21894(6) 0.0872(4) Uani 1 1 d . . .
S1 S 0.79214(14) 0.40519(19) 0.14626(10) 0.0441(4) Uani 1 1 d . . .
O1 O 0.7588(4) 0.3861(7) 0.2189(3) 0.0599(13) Uani 1 1 d . . .
O2 O 0.8419(4) 0.5531(5) 0.1280(3) 0.0605(13) Uani 1 1 d . . .
C8 C 0.5713(5) 0.2770(7) 0.0831(4) 0.0429(15) Uani 1 1 d . . .
N1 N 0.6665(4) 0.3756(6) 0.0763(3) 0.0421(12) Uani 1 1 d . . .
C6 C 0.8535(6) 0.0888(8) 0.1504(4) 0.0458(15) Uani 1 1 d . . .
H6 H 0.7858 0.0708 0.1695 0.055 Uiso 1 1 calc R . .
C1 C 0.8846(5) 0.2438(7) 0.1339(3) 0.0364(13) Uani 1 1 d . . .
C17 C 0.5369(6) 0.2177(8) 0.1485(4) 0.0484(16) Uani 1 1 d . . .
H17 H 0.5813 0.2353 0.1994 0.058 Uiso 1 1 calc R . .
C11 C 0.6603(5) 0.4003(8) -0.0054(4) 0.0440(15) Uani 1 1 d . . .
C10 C 0.5571(6) 0.3204(8) -0.0484(4) 0.0476(16) Uani 1 1 d . . .
C9 C 0.5009(6) 0.2445(7) 0.0074(4) 0.0449(15) Uani 1 1 d . . .
N2 N 0.3616(5) 0.0971(7) 0.0623(4) 0.0562(15) Uani 1 1 d . . .
C12 C 0.7337(6) 0.4886(8) -0.0418(4) 0.0516(17) Uani 1 1 d . . .
H12 H 0.8004 0.5434 -0.0130 0.062 Uiso 1 1 calc R . .
C5 C 0.9239(6) -0.0393(8) 0.1383(4) 0.0509(17) Uani 1 1 d . . .
H5 H 0.9023 -0.1439 0.1489 0.061 Uiso 1 1 calc R . .
C4 C 1.0263(6) -0.0159(8) 0.1107(4) 0.0460(16) Uani 1 1 d . . .
C13 C 0.7039(7) 0.4922(9) -0.1230(5) 0.063(2) Uani 1 1 d . . .
H13 H 0.7522 0.5492 -0.1493 0.076 Uiso 1 1 calc R . .
C3 C 1.0564(6) 0.1401(8) 0.0959(4) 0.0481(16) Uani 1 1 d . . .
H3 H 1.1255 0.1582 0.0783 0.058 Uiso 1 1 calc R . .
C2 C 0.9864(6) 0.2712(8) 0.1065(4) 0.0464(16) Uani 1 1 d . . .
H2 H 1.0075 0.3757 0.0955 0.056 Uiso 1 1 calc R . .
C18 C 0.4306(6) 0.1297(9) 0.1315(5) 0.0547(18) Uani 1 1 d . . .
C16 C 0.3970(6) 0.1542(8) 0.0009(5) 0.0531(17) Uani 1 1 d . . .
H16 H 0.3500 0.1326 -0.0489 0.064 Uiso 1 1 calc R . .
C15 C 0.5297(7) 0.3275(9) -0.1297(4) 0.0566(18) Uani 1 1 d . . .
H15 H 0.4624 0.2754 -0.1594 0.068 Uiso 1 1 calc R . .
C7 C 1.1032(7) -0.1583(9) 0.1002(5) 0.067(2) Uani 1 1 d . . .
H7A H 1.1697 -0.1211 0.0807 0.101 Uiso 1 1 calc R . .
H7B H 1.0564 -0.2332 0.0636 0.101 Uiso 1 1 calc R . .
H7C H 1.1324 -0.2113 0.1497 0.101 Uiso 1 1 calc R . .
C14 C 0.6044(8) 0.4131(10) -0.1650(5) 0.064(2) Uani 1 1 d . . .
H14 H 0.5871 0.4177 -0.2194 0.077 Uiso 1 1 calc R . .

loop_
_atom_site_aniso_label
_atom_site_aniso_U_11
_atom_site_aniso_U_22
_atom_site_aniso_U_33
_atom_site_aniso_U_23
_atom_site_aniso_U_13
_atom_site_aniso_U_12
Br1 0.0749(7) 0.1083(8) 0.0815(7) 0.0143(6) 0.0250(5) -0.0112(5)
S1 0.0370(8) 0.0437(9) 0.0499(10) -0.0125(7) 0.0071(7) 0.0004(7)
O1 0.052(3) 0.076(3) 0.050(3) -0.022(3) 0.010(2) 0.003(3)
O2 0.056(3) 0.040(3) 0.082(4) -0.011(2) 0.008(3) -0.006(2)
C8 0.035(3) 0.038(3) 0.053(4) -0.001(3) 0.006(3) 0.011(3)
N1 0.033(3) 0.047(3) 0.043(3) -0.006(2) 0.003(2) 0.003(2)
C6 0.038(3) 0.045(4) 0.052(4) 0.005(3) 0.007(3) -0.005(3)
C1 0.033(3) 0.039(3) 0.036(3) -0.004(3) 0.003(2) 0.001(2)
C17 0.040(3) 0.053(4) 0.051(4) -0.003(3) 0.007(3) 0.008(3)
C11 0.035(3) 0.039(3) 0.055(4) -0.002(3) 0.007(3) 0.016(3)
C10 0.041(3) 0.041(4) 0.058(4) 0.001(3) 0.007(3) 0.015(3)
C9 0.041(3) 0.037(3) 0.051(4) -0.005(3) 0.001(3) 0.007(3)
N2 0.044(3) 0.054(3) 0.069(4) -0.002(3) 0.009(3) 0.001(3)
C12 0.044(4) 0.049(4) 0.065(5) 0.005(3) 0.018(3) 0.012(3)
C5 0.053(4) 0.036(3) 0.057(4) 0.002(3) -0.001(3) -0.004(3)
C4 0.045(4) 0.048(4) 0.039(4) -0.005(3) -0.002(3) 0.009(3)
C13 0.061(5) 0.052(4) 0.081(6) 0.010(4) 0.024(4) 0.019(4)
C3 0.044(4) 0.057(4) 0.046(4) 0.004(3) 0.016(3) 0.009(3)
C2 0.045(4) 0.042(4) 0.053(4) 0.008(3) 0.013(3) -0.001(3)
C18 0.045(4) 0.053(4) 0.068(5) 0.004(4) 0.016(4) 0.008(3)
C16 0.045(4) 0.048(4) 0.064(5) -0.005(3) 0.008(3) 0.001(3)
C15 0.058(4) 0.059(4) 0.046(4) -0.002(3) -0.001(3) 0.014(4)
C7 0.068(5) 0.056(5) 0.070(5) -0.008(4) 0.002(4) 0.021(4)
C14 0.075(5) 0.073(5) 0.047(4) 0.010(4) 0.020(4) 0.022(4)

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

loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
Br1 C18 1.899(7) . ?
S1 O2 1.418(5) . ?
S1 O1 1.426(5) . ?
S1 N1 1.678(5) . ?
S1 C1 1.751(6) . ?
C8 C17 1.390(9) . ?
C8 N1 1.393(8) . ?
C8 C9 1.409(9) . ?
N1 C11 1.436(8) . ?
C6 C5 1.379(9) . ?
C6 C1 1.379(9) . ?
C1 C2 1.385(8) . ?
C17 C18 1.391(10) . ?
C11 C12 1.381(9) . ?
C11 C10 1.411(9) . ?
C10 C15 1.389(10) . ?
C10 C9 1.440(10) . ?
C9 C16 1.390(9) . ?
N2 C18 1.312(9) . ?
N2 C16 1.328(9) . ?
C12 C13 1.386(11) . ?
C5 C4 1.388(10) . ?
C4 C3 1.375(10) . ?
C4 C7 1.509(9) . ?
C13 C14 1.371(12) . ?
C3 C2 1.389(9) . ?
C15 C14 1.370(11) . ?

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 120.4(3) . . ?
O2 S1 N1 106.4(3) . . ?
O1 S1 N1 105.9(3) . . ?
O2 S1 C1 109.8(3) . . ?
O1 S1 C1 109.1(3) . . ?
N1 S1 C1 103.9(3) . . ?
C17 C8 N1 131.4(6) . . ?
C17 C8 C9 120.1(6) . . ?
N1 C8 C9 108.4(6) . . ?
C8 N1 C11 108.5(5) . . ?
C8 N1 S1 125.4(4) . . ?
C11 N1 S1 122.9(4) . . ?
C5 C6 C1 119.3(6) . . ?
C2 C1 C6 120.5(6) . . ?
C2 C1 S1 120.5(5) . . ?
C6 C1 S1 119.1(5) . . ?
C18 C17 C8 114.4(6) . . ?
C12 C11 C10 121.9(7) . . ?
C12 C11 N1 130.3(6) . . ?
C10 C11 N1 107.7(6) . . ?
C11 C10 C15 119.1(7) . . ?
C11 C10 C9 107.2(6) . . ?
C15 C10 C9 133.7(7) . . ?
C16 C9 C8 118.0(7) . . ?
C16 C9 C10 133.9(6) . . ?
C8 C9 C10 108.1(6) . . ?
C18 N2 C16 116.4(6) . . ?
C11 C12 C13 117.3(7) . . ?
C6 C5 C4 121.6(6) . . ?
C5 C4 C3 118.0(6) . . ?
C5 C4 C7 120.3(7) . . ?
C3 C4 C7 121.7(7) . . ?
C14 C13 C12 121.0(8) . . ?
C2 C3 C4 121.7(6) . . ?
C1 C2 C3 119.0(6) . . ?
N2 C18 C17 127.9(7) . . ?
N2 C18 Br1 116.0(5) . . ?
C17 C18 Br1 116.1(6) . . ?
N2 C16 C9 123.2(7) . . ?
C14 C15 C10 118.4(7) . . ?
C13 C14 C15 122.3(8) . . ?

_diffrn_measured_fraction_theta_max 1.000
_diffrn_reflns_theta_full        25.00
_diffrn_measured_fraction_theta_full 1.000
_refine_diff_density_max         0.763
_refine_diff_density_min         -0.726
_refine_diff_density_rms         0.096
_database_code_depnum_ccdc_archive 'CCDC 953973'
