# 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_a

_audit_creation_method           SHELXL-97
_chemical_name_systematic        
; 
 ? 
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         'C5 H3.60 Br0.20 N0.60 O0.80 S0.20'
_chemical_formula_sum            'C5 H3.60 Br0.20 N0.60 O0.80 S0.20'
_chemical_formula_weight         107.28

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           Triclinic
_symmetry_space_group_name_H-M   P-1

loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'-x, -y, -z'

_cell_length_a                   9.0285(3)
_cell_length_b                   9.3506(3)
_cell_length_c                   14.1171(5)
_cell_angle_alpha                107.993(2)
_cell_angle_beta                 99.488(2)
_cell_angle_gamma                93.745(2)
_cell_volume                     1109.38(6)
_cell_formula_units_Z            10
_cell_measurement_temperature    296(2)
_cell_measurement_reflns_used    ?
_cell_measurement_theta_min      ?
_cell_measurement_theta_max      ?

_exptl_crystal_description       block
_exptl_crystal_colour            colourless
_exptl_crystal_size_max          ?
_exptl_crystal_size_mid          ?
_exptl_crystal_size_min          ?
_exptl_crystal_density_meas      ?
_exptl_crystal_density_diffrn    1.606
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             544
_exptl_absorpt_coefficient_mu    1.987
_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      296(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 P4'
_diffrn_measurement_method       'ω scans'
_diffrn_detector_area_resol_mean ?
_diffrn_standards_number         ?
_diffrn_standards_interval_count ?
_diffrn_standards_interval_time  ?
_diffrn_standards_decay_%        ?
_diffrn_reflns_number            38048
_diffrn_reflns_av_R_equivalents  0.0398
_diffrn_reflns_av_sigmaI/netI    0.0256
_diffrn_reflns_limit_h_min       -11
_diffrn_reflns_limit_h_max       11
_diffrn_reflns_limit_k_min       -12
_diffrn_reflns_limit_k_max       12
_diffrn_reflns_limit_l_min       -18
_diffrn_reflns_limit_l_max       18
_diffrn_reflns_theta_min         1.55
_diffrn_reflns_theta_max         27.67
_reflns_number_total             5164
_reflns_number_gt                4001
_reflns_threshold_expression     >2sigma(I)

_computing_data_collection       'Bruker XSCANS'
_computing_cell_refinement       'Bruker XSCANS'
_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)+(0.0446P)²+0.9699P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_atom_sites_solution_hydrogens   .
_refine_ls_hydrogen_treatment    .
_refine_ls_extinction_method     SHELXL
_refine_ls_extinction_coef       0.0019(11)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc²λ³/sin(2θ)]^-1/4^
_refine_ls_number_reflns         5164
_refine_ls_number_parameters     308
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0600
_refine_ls_R_factor_gt           0.0418
_refine_ls_wR_factor_ref         0.1048
_refine_ls_wR_factor_gt          0.0954
_refine_ls_goodness_of_fit_ref   1.022
_refine_ls_restrained_S_all      1.022
_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
Br1 Br 0.84232(4) 0.85789(4) 0.03140(3) 0.07352(16) Uani 1 1 d . . .
O1 O 1.13601(17) 0.45800(17) -0.33458(11) 0.0308(3) Uani 1 1 d . . .
S1 S 1.39383(8) 0.77018(8) 0.00693(4) 0.04455(18) Uani 1 1 d . . .
N1 N 1.3945(2) 0.4910(2) -0.19094(14) 0.0318(4) Uani 1 1 d . . .
C1 C 1.1575(2) 0.5910(2) -0.24641(15) 0.0258(4) Uani 1 1 d . . .
H1A H 1.1242 0.6731 -0.2709 0.031 Uiso 1 1 calc R . .
N2 N 1.4186(2) 0.8843(2) -0.14123(14) 0.0314(4) Uani 1 1 d . . .
H2A H 1.4461 0.9740 -0.0986 0.038 Uiso 1 1 calc R . .
O2 O 1.5024(3) 0.4495(3) -0.2273(2) 0.0688(7) Uani 1 1 d . . .
C2 C 1.3307(2) 0.6308(2) -0.20711(15) 0.0249(4) Uani 1 1 d . . .
N3 N 1.3260(2) 1.0118(2) -0.34386(16) 0.0374(5) Uani 1 1 d . . .
C3 C 1.3986(2) 0.6772(2) -0.28787(15) 0.0242(4) Uani 1 1 d . . .
H3A H 1.5023 0.6509 -0.2829 0.029 Uiso 1 1 calc R . .
O3 O 1.3303(2) 0.4253(2) -0.14535(17) 0.0566(5) Uani 1 1 d . . .
O4 O 1.14230(19) 0.8975(2) -0.28857(16) 0.0475(5) Uani 1 1 d . . .
C4 C 1.4099(2) 0.8538(2) -0.24975(16) 0.0270(4) Uani 1 1 d . . .
C5 C 1.5412(3) 0.9329(2) -0.27566(17) 0.0303(5) Uani 1 1 d . . .
C6 C 1.6940(3) 0.9264(3) -0.2532(2) 0.0413(6) Uani 1 1 d . . .
H6A H 1.7324 0.8677 -0.2147 0.050 Uiso 1 1 calc R . .
C7 C 1.7901(3) 1.0108(3) -0.2899(2) 0.0525(7) Uani 1 1 d . . .
H7A H 1.8940 1.0079 -0.2761 0.063 Uiso 1 1 calc R . .
C8 C 1.7322(4) 1.0979(3) -0.3463(2) 0.0555(8) Uani 1 1 d . . .
H8A H 1.7982 1.1530 -0.3701 0.067 Uiso 1 1 calc R . .
C9 C 1.5792(4) 1.1058(3) -0.3687(2) 0.0490(7) Uani 1 1 d . . .
H9A H 1.5408 1.1651 -0.4068 0.059 Uiso 1 1 calc R . .
C10 C 1.4854(3) 1.0225(3) -0.33213(17) 0.0347(5) Uani 1 1 d . . .
C11 C 1.2733(3) 0.9202(2) -0.29575(18) 0.0318(5) Uani 1 1 d . . .
C12 C 1.3823(2) 0.7681(3) -0.11083(16) 0.0287(5) Uani 1 1 d . . .
C13 C 1.3157(2) 0.5940(2) -0.39487(15) 0.0265(4) Uani 1 1 d . . .
C14 C 1.3654(3) 0.6170(3) -0.47865(17) 0.0341(5) Uani 1 1 d . . .
H14A H 1.4444 0.6925 -0.4684 0.041 Uiso 1 1 calc R . .
C15 C 1.2977(3) 0.5282(3) -0.57676(18) 0.0402(6) Uani 1 1 d . . .
H15A H 1.3285 0.5467 -0.6320 0.048 Uiso 1 1 calc R . .
C16 C 1.1841(3) 0.4121(3) -0.59193(18) 0.0397(6) Uani 1 1 d . . .
H16A H 1.1418 0.3499 -0.6576 0.048 Uiso 1 1 calc R . .
C17 C 1.1330(3) 0.3876(3) -0.51095(17) 0.0356(5) Uani 1 1 d . . .
H17A H 1.0569 0.3091 -0.5215 0.043 Uiso 1 1 calc R . .
C18 C 1.1966(2) 0.4819(2) -0.41291(16) 0.0283(4) Uani 1 1 d . . .
C19 C 1.0515(2) 0.5695(2) -0.17813(16) 0.0280(4) Uani 1 1 d . . .
C20 C 0.9862(3) 0.4274(3) -0.18439(18) 0.0375(5) Uani 1 1 d . . .
H20A H 1.0162 0.3405 -0.2260 0.045 Uiso 1 1 calc R . .
C21 C 0.8760(3) 0.4155(3) -0.1283(2) 0.0451(6) Uani 1 1 d . . .
H21A H 0.8315 0.3202 -0.1336 0.054 Uiso 1 1 calc R . .
C22 C 0.8315(3) 0.5425(3) -0.0651(2) 0.0420(6) Uani 1 1 d . . .
H22A H 0.7578 0.5339 -0.0277 0.050 Uiso 1 1 calc R . .
C23 C 0.8984(3) 0.6821(3) -0.05865(19) 0.0374(5) Uani 1 1 d . . .
C24 C 1.0063(3) 0.6981(3) -0.11510(18) 0.0333(5) Uani 1 1 d . . .
H24A H 1.0481 0.7940 -0.1108 0.040 Uiso 1 1 calc R . .
C25 C 1.2307(4) 1.1004(3) -0.3901(3) 0.0574(8) Uani 1 1 d . . .
H25A H 1.1268 1.0722 -0.3895 0.086 Uiso 1 1 calc R . .
H25B H 1.2434 1.0818 -0.4589 0.086 Uiso 1 1 calc R . .
H25C H 1.2588 1.2062 -0.3525 0.086 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 C23 1.899(2) . ?
O1 C18 1.381(3) . ?
O1 C1 1.437(2) . ?
S1 C12 1.642(2) . ?
N1 O3 1.204(3) . ?
N1 O2 1.206(3) . ?
N1 C2 1.527(3) . ?
C1 C19 1.511(3) . ?
C1 C2 1.550(3) . ?
N2 C12 1.327(3) . ?
N2 C4 1.457(3) . ?
C2 C12 1.532(3) . ?
C2 C3 1.538(3) . ?
N3 C11 1.354(3) . ?
N3 C10 1.414(3) . ?
N3 C25 1.448(3) . ?
C3 C13 1.507(3) . ?
C3 C4 1.562(3) . ?
O4 C11 1.214(3) . ?
C4 C5 1.510(3) . ?
C4 C11 1.553(3) . ?
C5 C6 1.373(3) . ?
C5 C10 1.388(3) . ?
C6 C7 1.398(4) . ?
C7 C8 1.375(5) . ?
C8 C9 1.378(4) . ?
C9 C10 1.377(3) . ?
C13 C18 1.385(3) . ?
C13 C14 1.402(3) . ?
C14 C15 1.388(3) . ?
C15 C16 1.384(4) . ?
C16 C17 1.377(4) . ?
C17 C18 1.393(3) . ?
C19 C24 1.388(3) . ?
C19 C20 1.389(3) . ?
C20 C21 1.388(3) . ?
C21 C22 1.376(4) . ?
C22 C23 1.372(4) . ?
C23 C24 1.385(3) . ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
C18 O1 C1 113.08(16) . . ?
O3 N1 O2 123.7(2) . . ?
O3 N1 C2 117.67(19) . . ?
O2 N1 C2 118.59(19) . . ?
O1 C1 C19 109.30(16) . . ?
O1 C1 C2 106.43(16) . . ?
C19 C1 C2 121.69(17) . . ?
C12 N2 C4 117.33(17) . . ?
N1 C2 C12 109.90(17) . . ?
N1 C2 C3 111.06(17) . . ?
C12 C2 C3 103.53(16) . . ?
N1 C2 C1 108.39(16) . . ?
C12 C2 C1 116.20(17) . . ?
C3 C2 C1 107.67(16) . . ?
C11 N3 C10 111.4(2) . . ?
C11 N3 C25 123.0(2) . . ?
C10 N3 C25 125.2(2) . . ?
C13 C3 C2 113.34(17) . . ?
C13 C3 C4 117.73(17) . . ?
C2 C3 C4 103.75(16) . . ?
N2 C4 C5 114.00(17) . . ?
N2 C4 C11 111.02(18) . . ?
C5 C4 C11 101.89(18) . . ?
N2 C4 C3 100.92(16) . . ?
C5 C4 C3 114.46(17) . . ?
C11 C4 C3 115.07(17) . . ?
C6 C5 C10 120.4(2) . . ?
C6 C5 C4 130.8(2) . . ?
C10 C5 C4 108.8(2) . . ?
C5 C6 C7 118.1(3) . . ?
C8 C7 C6 120.5(3) . . ?
C7 C8 C9 121.8(3) . . ?
C10 C9 C8 117.2(3) . . ?
C9 C10 C5 121.9(2) . . ?
C9 C10 N3 128.3(2) . . ?
C5 C10 N3 109.8(2) . . ?
O4 C11 N3 125.4(2) . . ?
O4 C11 C4 126.6(2) . . ?
N3 C11 C4 107.99(19) . . ?
N2 C12 C2 106.50(17) . . ?
N2 C12 S1 126.74(17) . . ?
C2 C12 S1 126.75(17) . . ?
C18 C13 C14 118.2(2) . . ?
C18 C13 C3 120.18(19) . . ?
C14 C13 C3 121.3(2) . . ?
C15 C14 C13 120.6(2) . . ?
C16 C15 C14 119.7(2) . . ?
C17 C16 C15 120.8(2) . . ?
C16 C17 C18 119.1(2) . . ?
O1 C18 C13 121.56(18) . . ?
O1 C18 C17 117.0(2) . . ?
C13 C18 C17 121.5(2) . . ?
C24 C19 C20 119.4(2) . . ?
C24 C19 C1 117.82(19) . . ?
C20 C19 C1 122.4(2) . . ?
C21 C20 C19 119.8(2) . . ?
C22 C21 C20 121.1(2) . . ?
C23 C22 C21 118.5(2) . . ?
C22 C23 C24 121.9(2) . . ?
C22 C23 Br1 118.84(18) . . ?
C24 C23 Br1 119.27(18) . . ?
C23 C24 C19 119.3(2) . . ?

_diffrn_measured_fraction_theta_max 0.995
_diffrn_reflns_theta_full        27.67
_diffrn_measured_fraction_theta_full 0.995
_refine_diff_density_max         0.989
_refine_diff_density_min         -0.734
_refine_diff_density_rms         0.063

_database_code_depnum_ccdc_archive 'CCDC 1001582'
#######################################################################
#
#                 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_a

_audit_creation_method           SHELXL-97
_chemical_name_systematic        
; 
 ? 
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         'C4.76 H3.43 Br0.19 N0.57 O0.76 S0.19'
_chemical_formula_sum            'C4.76 H3.43 Br0.19 N0.57 O0.76 S0.19'
_chemical_formula_weight         102.17

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           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                   7.8034(10)
_cell_length_b                   9.5210(13)
_cell_length_c                   30.485(4)
_cell_angle_alpha                90.00
_cell_angle_beta                 90.00
_cell_angle_gamma                90.00
_cell_volume                     2264.9(5)
_cell_formula_units_Z            21
_cell_measurement_temperature    296(2)
_cell_measurement_reflns_used    ?
_cell_measurement_theta_min      ?
_cell_measurement_theta_max      ?

_exptl_crystal_description       ?
_exptl_crystal_colour            ?
_exptl_crystal_size_max          ?
_exptl_crystal_size_mid          ?
_exptl_crystal_size_min          ?
_exptl_crystal_density_meas      ?
_exptl_crystal_density_diffrn    1.573
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             1088
_exptl_absorpt_coefficient_mu    1.946
_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      296(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 P4'
_diffrn_measurement_method       'ω scans'
_diffrn_detector_area_resol_mean ?
_diffrn_standards_number         ?
_diffrn_standards_interval_count ?
_diffrn_standards_interval_time  ?
_diffrn_standards_decay_%        ?
_diffrn_reflns_number            11290
_diffrn_reflns_av_R_equivalents  0.0245
_diffrn_reflns_av_sigmaI/netI    0.0633
_diffrn_reflns_limit_h_min       -9
_diffrn_reflns_limit_h_max       9
_diffrn_reflns_limit_k_min       -11
_diffrn_reflns_limit_k_max       12
_diffrn_reflns_limit_l_min       -37
_diffrn_reflns_limit_l_max       39
_diffrn_reflns_theta_min         1.34
_diffrn_reflns_theta_max         27.51
_reflns_number_total             4963
_reflns_number_gt                3799
_reflns_threshold_expression     >2sigma(I)

_computing_data_collection       'Bruker XSCANS'
_computing_cell_refinement       'Bruker XSCANS'
_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)+(0.0227P)²+0.0000P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_atom_sites_solution_hydrogens   .
_refine_ls_hydrogen_treatment    .
_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   0.001(8)
_refine_ls_number_reflns         4963
_refine_ls_number_parameters     307
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0588
_refine_ls_R_factor_gt           0.0372
_refine_ls_wR_factor_ref         0.0798
_refine_ls_wR_factor_gt          0.0736
_refine_ls_goodness_of_fit_ref   1.004
_refine_ls_restrained_S_all      1.004
_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
Br1 Br 0.33099(5) 0.74996(4) 0.204714(10) 0.06854(14) Uani 1 1 d . . .
O1 O 0.1819(3) 0.32241(17) 0.30478(5) 0.0363(5) Uani 1 1 d . . .
N1 N -0.0415(3) 0.4677(2) 0.36385(7) 0.0324(5) Uani 1 1 d . . .
C1 C 0.2168(3) 0.2306(2) 0.43393(7) 0.0277(6) Uani 1 1 d . . .
S2 S 0.18510(13) 0.64635(7) 0.42867(2) 0.0482(2) Uani 1 1 d . . .
C2 C 0.0952(3) 0.2489(3) 0.39345(7) 0.0258(5) Uani 1 1 d . . .
H2A H -0.0227 0.2442 0.4044 0.031 Uiso 1 1 calc R . .
O2 O -0.1700(3) 0.4379(2) 0.38408(7) 0.0600(6) Uani 1 1 d . . .
N2 N 0.2428(3) 0.3770(2) 0.44705(7) 0.0331(6) Uani 1 1 d . . .
H2B H 0.2930 0.3982 0.4713 0.040 Uiso 1 1 calc R . .
O3 O -0.0376(3) 0.5501(2) 0.33362(7) 0.0515(6) Uani 1 1 d . . .
C3 C 0.1269(3) 0.4015(2) 0.37827(8) 0.0263(6) Uani 1 1 d . . .
N3 N 0.2124(3) 0.0381(2) 0.48203(7) 0.0375(6) Uani 1 1 d . . .
O4 O -0.0226(3) 0.1818(2) 0.48389(6) 0.0447(5) Uani 1 1 d . . .
C4 C 0.2569(4) 0.3995(3) 0.34017(8) 0.0296(6) Uani 1 1 d . . .
H4A H 0.3536 0.3426 0.3504 0.035 Uiso 1 1 calc R . .
C5 C 0.1428(4) 0.1840(2) 0.31463(8) 0.0297(6) Uani 1 1 d . . .
C6 C 0.1112(3) 0.1417(3) 0.35741(8) 0.0287(6) Uani 1 1 d . . .
C7 C 0.0768(4) 0.0006(3) 0.36493(9) 0.0357(7) Uani 1 1 d . . .
H7A H 0.0590 -0.0310 0.3934 0.043 Uiso 1 1 calc R . .
C8 C 0.0686(4) -0.0931(3) 0.33055(11) 0.0470(8) Uani 1 1 d . . .
H8A H 0.0458 -0.1874 0.3359 0.056 Uiso 1 1 calc R . .
C9 C 0.0942(4) -0.0468(3) 0.28815(10) 0.0479(8) Uani 1 1 d . . .
H9A H 0.0846 -0.1097 0.2649 0.058 Uiso 1 1 calc R . .
C10 C 0.1336(4) 0.0913(3) 0.27993(9) 0.0423(8) Uani 1 1 d . . .
H10A H 0.1539 0.1218 0.2514 0.051 Uiso 1 1 calc R . .
C11 C 0.1857(4) 0.4758(2) 0.41992(8) 0.0300(6) Uani 1 1 d . . .
C12 C 0.1173(4) 0.1509(3) 0.47037(8) 0.0331(7) Uani 1 1 d . . .
C13 C 0.3678(4) 0.0321(3) 0.45884(8) 0.0335(7) Uani 1 1 d . . .
C14 C 0.3783(4) 0.1464(3) 0.42993(8) 0.0314(6) Uani 1 1 d . . .
C15 C 0.5256(4) 0.1635(3) 0.40577(10) 0.0449(8) Uani 1 1 d . . .
H15A H 0.5389 0.2413 0.3877 0.054 Uiso 1 1 calc R . .
C16 C 0.6547(5) 0.0628(4) 0.40876(12) 0.0589(9) Uani 1 1 d . . .
H16A H 0.7527 0.0719 0.3916 0.071 Uiso 1 1 calc R . .
C17 C 0.6395(5) -0.0485(3) 0.43634(12) 0.0594(10) Uani 1 1 d . . .
H17A H 0.7272 -0.1145 0.4378 0.071 Uiso 1 1 calc R . .
C18 C 0.4958(5) -0.0654(3) 0.46227(11) 0.0496(8) Uani 1 1 d . . .
H18A H 0.4864 -0.1409 0.4815 0.059 Uiso 1 1 calc R . .
C19 C 0.1650(5) -0.0603(3) 0.51645(10) 0.0596(9) Uani 1 1 d . . .
H19A H 0.0544 -0.0357 0.5279 0.089 Uiso 1 1 calc R . .
H19B H 0.2484 -0.0566 0.5396 0.089 Uiso 1 1 calc R . .
H19C H 0.1609 -0.1537 0.5046 0.089 Uiso 1 1 calc R . .
C20 C 0.3346(4) 0.5330(3) 0.32200(8) 0.0301(6) Uani 1 1 d . . .
C21 C 0.4624(4) 0.6005(3) 0.34484(10) 0.0434(7) Uani 1 1 d . . .
H21A H 0.4933 0.5681 0.3725 0.052 Uiso 1 1 calc R . .
C22 C 0.5453(5) 0.7152(3) 0.32741(10) 0.0536(9) Uani 1 1 d . . .
H22A H 0.6289 0.7612 0.3437 0.064 Uiso 1 1 calc R . .
C23 C 0.5053(4) 0.7623(3) 0.28602(10) 0.0504(8) Uani 1 1 d . . .
H23A H 0.5606 0.8399 0.2741 0.060 Uiso 1 1 calc R . .
C24 C 0.3821(4) 0.6921(3) 0.26289(9) 0.0415(8) Uani 1 1 d . . .
C25 C 0.2931(4) 0.5791(3) 0.28004(8) 0.0341(7) Uani 1 1 d . . .
H25A H 0.2075 0.5350 0.2639 0.041 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 C24 1.899(3) . ?
O1 C5 1.386(3) . ?
O1 C4 1.430(3) . ?
N1 O3 1.211(3) . ?
N1 O2 1.211(3) . ?
N1 C3 1.522(3) . ?
C1 N2 1.464(3) . ?
C1 C14 1.499(4) . ?
C1 C12 1.553(3) . ?
C1 C2 1.566(3) . ?
S2 C11 1.645(2) . ?
C2 C6 1.505(3) . ?
C2 C3 1.545(3) . ?
N2 C11 1.330(3) . ?
C3 C11 1.524(3) . ?
C3 C4 1.542(3) . ?
N3 C12 1.353(3) . ?
N3 C13 1.405(4) . ?
N3 C19 1.455(3) . ?
O4 C12 1.203(3) . ?
C4 C20 1.513(3) . ?
C5 C10 1.380(3) . ?
C5 C6 1.387(4) . ?
C6 C7 1.390(4) . ?
C7 C8 1.377(4) . ?
C8 C9 1.380(4) . ?
C9 C10 1.373(4) . ?
C13 C18 1.368(4) . ?
C13 C14 1.403(3) . ?
C14 C15 1.375(4) . ?
C15 C16 1.394(4) . ?
C16 C17 1.358(4) . ?
C17 C18 1.381(5) . ?
C20 C21 1.376(4) . ?
C20 C25 1.391(3) . ?
C21 C22 1.376(4) . ?
C22 C23 1.375(4) . ?
C23 C24 1.367(4) . ?
C24 C25 1.383(4) . ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
C5 O1 C4 114.51(19) . . ?
O3 N1 O2 124.1(3) . . ?
O3 N1 C3 117.8(2) . . ?
O2 N1 C3 118.1(2) . . ?
N2 C1 C14 114.5(2) . . ?
N2 C1 C12 109.81(19) . . ?
C14 C1 C12 102.6(2) . . ?
N2 C1 C2 101.13(18) . . ?
C14 C1 C2 120.3(2) . . ?
C12 C1 C2 108.4(2) . . ?
C6 C2 C3 113.9(2) . . ?
C6 C2 C1 116.7(2) . . ?
C3 C2 C1 104.12(19) . . ?
C11 N2 C1 117.2(2) . . ?
N1 C3 C11 107.9(2) . . ?
N1 C3 C4 110.8(2) . . ?
C11 C3 C4 115.8(2) . . ?
N1 C3 C2 109.7(2) . . ?
C11 C3 C2 103.60(19) . . ?
C4 C3 C2 108.63(19) . . ?
C12 N3 C13 112.0(2) . . ?
C12 N3 C19 124.1(3) . . ?
C13 N3 C19 123.8(3) . . ?
O1 C4 C20 108.60(19) . . ?
O1 C4 C3 107.8(2) . . ?
C20 C4 C3 121.9(2) . . ?
C10 C5 O1 117.0(2) . . ?
C10 C5 C6 121.8(2) . . ?
O1 C5 C6 121.2(2) . . ?
C5 C6 C7 118.0(2) . . ?
C5 C6 C2 120.3(2) . . ?
C7 C6 C2 121.3(2) . . ?
C8 C7 C6 120.6(3) . . ?
C7 C8 C9 120.0(3) . . ?
C10 C9 C8 120.6(3) . . ?
C9 C10 C5 118.9(3) . . ?
N2 C11 C3 106.9(2) . . ?
N2 C11 S2 126.8(2) . . ?
C3 C11 S2 126.33(19) . . ?
O4 C12 N3 127.0(3) . . ?
O4 C12 C1 125.4(2) . . ?
N3 C12 C1 107.5(2) . . ?
C18 C13 C14 122.2(3) . . ?
C18 C13 N3 128.3(3) . . ?
C14 C13 N3 109.5(2) . . ?
C15 C14 C13 118.5(3) . . ?
C15 C14 C1 133.1(2) . . ?
C13 C14 C1 108.3(2) . . ?
C14 C15 C16 119.2(3) . . ?
C17 C16 C15 120.9(3) . . ?
C16 C17 C18 121.1(3) . . ?
C13 C18 C17 118.0(3) . . ?
C21 C20 C25 119.1(3) . . ?
C21 C20 C4 119.8(2) . . ?
C25 C20 C4 120.6(2) . . ?
C20 C21 C22 121.1(3) . . ?
C23 C22 C21 120.4(3) . . ?
C24 C23 C22 118.3(3) . . ?
C23 C24 C25 122.6(3) . . ?
C23 C24 Br1 119.2(2) . . ?
C25 C24 Br1 118.2(2) . . ?
C24 C25 C20 118.5(3) . . ?

_diffrn_measured_fraction_theta_max 0.965
_diffrn_reflns_theta_full        27.51
_diffrn_measured_fraction_theta_full 0.965
_refine_diff_density_max         0.463
_refine_diff_density_min         -0.478
_refine_diff_density_rms         0.047

_database_code_depnum_ccdc_archive 'CCDC 1001583'
