# Supplementary Information (SI) for ChemComm.
# This journal is © The Royal Society of Chemistry 2025

####################################################################### 
# 
# This file contains crystal structure data downloaded from the 
# Cambridge Structural Database (CSD) hosted by the Cambridge 
# Crystallographic Data Centre (CCDC).
# 
# Full information about CCDC data access policies and citation 
# guidelines are available at http://www.ccdc.cam.ac.uk/access/V1 
# 
# Audit and citation data items may have been added by the CCDC. 
# Please retain this information to preserve the provenance of 
# this file and to allow appropriate attribution of the data. 
# 
#######################################################################

data_1
_database_code_depnum_ccdc_archive 'CCDC 2353284'
loop_
_audit_author_name
_audit_author_address
'Feng Li'
;Zaozhuang University
China
;
_audit_update_record             
;
2024-05-06 deposited with the CCDC.	2025-01-23 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2018/3
_shelx_SHELXL_version_number     2018/3
_chemical_name_systematic        ?
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C11 H9 Br N O2'
_chemical_formula_weight         267.10

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

_space_group_crystal_system      triclinic
_space_group_IT_number           2
_space_group_name_H-M_alt        'P -1'
_space_group_name_Hall           '-P 1'

_shelx_space_group_comment       
;
The symmetry employed for this shelxl refinement is uniquely defined
by the following loop, which should always be used as a source of
symmetry information in preference to the above space-group names.
They are only intended as comments.
;

loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x, -y, -z'

_cell_length_a                   6.7614(19)
_cell_length_b                   7.298(2)
_cell_length_c                   11.361(3)
_cell_angle_alpha                82.509(18)
_cell_angle_beta                 89.624(18)
_cell_angle_gamma                84.148(19)
_cell_volume                     552.9(3)
_cell_formula_units_Z            2
_cell_measurement_temperature    295(2)
_cell_measurement_reflns_used    3978
_cell_measurement_theta_min      2.83
_cell_measurement_theta_max      26.19

_exptl_crystal_description       block
_exptl_crystal_colour            colorless
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.604
_exptl_crystal_F_000             266
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.312
_exptl_crystal_size_mid          0.213
_exptl_crystal_size_min          0.069
_exptl_absorpt_coefficient_mu    3.695
_shelx_estimated_absorpt_T_min   0.392
_shelx_estimated_absorpt_T_max   0.785
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.4645
_exptl_absorpt_correction_T_max  0.7456
_exptl_absorpt_process_details   'SADABS (Sheldrick,1996)'
_exptl_absorpt_special_details   ?
_diffrn_ambient_temperature      295(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_source                   ?
_diffrn_measurement_device_type  'Bruker APEX-II CCD'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            16439
_diffrn_reflns_av_unetI/netI     0.0480
_diffrn_reflns_av_R_equivalents  0.0759
_diffrn_reflns_limit_h_min       -8
_diffrn_reflns_limit_h_max       8
_diffrn_reflns_limit_k_min       -9
_diffrn_reflns_limit_k_max       9
_diffrn_reflns_limit_l_min       -14
_diffrn_reflns_limit_l_max       14
_diffrn_reflns_theta_min         2.830
_diffrn_reflns_theta_max         27.513
_diffrn_reflns_theta_full        25.242
_diffrn_measured_fraction_theta_max 0.993
_diffrn_measured_fraction_theta_full 0.997
_diffrn_reflns_Laue_measured_fraction_max 0.993
_diffrn_reflns_Laue_measured_fraction_full 0.997
_diffrn_reflns_point_group_measured_fraction_max 0.993
_diffrn_reflns_point_group_measured_fraction_full 0.997
_reflns_number_total             2529
_reflns_number_gt                1903
_reflns_threshold_expression     'I > 2σ(I)'
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_max     .
_reflns_Friedel_fraction_full    .

_reflns_special_details          
;
 Reflections were merged by SHELXL according to the crystal
 class for the calculation of statistics and refinement.
 
 _reflns_Friedel_fraction is defined as the number of unique
 Friedel pairs measured divided by the number that would be
 possible theoretically, ignoring centric projections and
 systematic absences.
;

_computing_data_collection       'Bruker APEX2'
_computing_cell_refinement       'Bruker SAINT'
_computing_data_reduction        'Bruker SAINT'
_computing_structure_solution    'SHELXT 2018/2 (Sheldrick, 2018)'
_computing_structure_refinement  'SHELXL-2018/3 (Sheldrick, 2018)'
_computing_molecular_graphics    'Bruker SHELXTL'
_computing_publication_material  'Bruker SHELXTL'
_refine_special_details          ?
_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0314P)²+0.5390P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     ?
_atom_sites_solution_secondary   ?
_atom_sites_solution_hydrogens   geom
_refine_ls_hydrogen_treatment    constr
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       .
_refine_ls_number_reflns         2529
_refine_ls_number_parameters     136
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0648
_refine_ls_R_factor_gt           0.0431
_refine_ls_wR_factor_ref         0.1045
_refine_ls_wR_factor_gt          0.0953
_refine_ls_goodness_of_fit_ref   1.058
_refine_ls_restrained_S_all      1.058
_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_site_symmetry_order
_atom_site_calc_flag
_atom_site_refinement_flags_posn
_atom_site_refinement_flags_adp
_atom_site_refinement_flags_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
Br1 Br 0.77893(7) 0.55971(6) 0.71673(3) 0.06707(18) Uani 1 1 d . . . . .
O1 O 0.1637(3) 0.9340(3) 0.3617(2) 0.0569(6) Uani 1 1 d . . . . .
O2 O 0.4318(4) 0.9349(4) 0.2045(2) 0.0575(6) Uani 1 1 d . . . . .
N1 N 0.7906(6) 0.3838(5) 0.0696(3) 0.0769(10) Uani 1 1 d . . . . .
C1 C 0.7495(6) 0.5378(6) 0.0481(3) 0.0596(10) Uani 1 1 d . . . . .
C2 C 0.6953(8) 0.7370(6) 0.0239(3) 0.0715(12) Uani 1 1 d . . . . .
H2 H 0.552814 0.762605 0.032941 0.086 Uiso 1 1 calc R U . . .
H3 H 0.727844 0.779406 -0.057747 0.086 Uiso 1 1 calc R U . . .
C3 C 0.8007(7) 0.8448(5) 0.1055(3) 0.0625(10) Uani 1 1 d . . . . .
H4 H 0.759732 0.976164 0.084226 0.075 Uiso 1 1 calc R U . . .
H5 H 0.942661 0.825214 0.092020 0.075 Uiso 1 1 calc R U . . .
C4 C 0.7619(5) 0.7928(5) 0.2371(3) 0.0463(8) Uani 1 1 d . . . . .
H6 H 0.789120 0.659221 0.256372 0.056 Uiso 1 1 calc R U . . .
H7 H 0.854652 0.849732 0.282127 0.056 Uiso 1 1 calc R U . . .
C5 C 0.5547(5) 0.8495(4) 0.2763(3) 0.0390(7) Uani 1 1 d . . . . .
C6 C 0.5008(4) 0.8022(4) 0.4016(3) 0.0344(6) Uani 1 1 d . . . . .
C7 C 0.3038(4) 0.8467(4) 0.4385(3) 0.0399(7) Uani 1 1 d . . . . .
C8 C 0.2533(5) 0.8017(5) 0.5562(3) 0.0491(8) Uani 1 1 d . . . . .
H8 H 0.122983 0.829132 0.579972 0.059 Uiso 1 1 calc R U . . .
C9 C 0.3921(6) 0.7175(4) 0.6379(3) 0.0507(8) Uani 1 1 d . . . . .
H1 H 0.356735 0.689161 0.716926 0.061 Uiso 1 1 calc R U . . .
C10 C 0.5869(5) 0.6742(4) 0.6022(3) 0.0425(7) Uani 1 1 d . . . . .
C11 C 0.6406(4) 0.7143(4) 0.4863(3) 0.0376(6) Uani 1 1 d . . . . .
H9 H 0.770799 0.683088 0.463617 0.045 Uiso 1 1 calc R U . . .


_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 C10 1.896(3) . ?
O1 C7 1.344(4) . ?
O2 C5 1.230(4) . ?
N1 C1 1.125(5) . ?
C1 C2 1.453(6) . ?
C2 C3 1.516(6) . ?
C2 H2 0.9700 . ?
C2 H3 0.9700 . ?
C3 C4 1.521(5) . ?
C3 H4 0.9700 . ?
C3 H5 0.9700 . ?
C4 C5 1.501(5) . ?
C4 H6 0.9700 . ?
C4 H7 0.9700 . ?
C5 C6 1.473(4) . ?
C6 C11 1.400(4) . ?
C6 C7 1.412(4) . ?
C7 C8 1.384(5) . ?
C8 C9 1.366(5) . ?
C8 H8 0.9300 . ?
C9 C10 1.393(5) . ?
C9 H1 0.9300 . ?
C10 C11 1.366(4) . ?
C11 H9 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
N1 C1 C2 178.4(4) . . ?
C1 C2 C3 112.6(3) . . ?
C1 C2 H2 109.1 . . ?
C3 C2 H2 109.1 . . ?
C1 C2 H3 109.1 . . ?
C3 C2 H3 109.1 . . ?
H2 C2 H3 107.8 . . ?
C2 C3 C4 114.7(3) . . ?
C2 C3 H4 108.6 . . ?
C4 C3 H4 108.6 . . ?
C2 C3 H5 108.6 . . ?
C4 C3 H5 108.6 . . ?
H4 C3 H5 107.6 . . ?
C5 C4 C3 115.0(3) . . ?
C5 C4 H6 108.5 . . ?
C3 C4 H6 108.5 . . ?
C5 C4 H7 108.5 . . ?
C3 C4 H7 108.5 . . ?
H6 C4 H7 107.5 . . ?
O2 C5 C6 120.5(3) . . ?
O2 C5 C4 120.3(3) . . ?
C6 C5 C4 119.2(3) . . ?
C11 C6 C7 118.6(3) . . ?
C11 C6 C5 121.7(3) . . ?
C7 C6 C5 119.8(3) . . ?
O1 C7 C8 118.9(3) . . ?
O1 C7 C6 121.4(3) . . ?
C8 C7 C6 119.7(3) . . ?
C9 C8 C7 121.0(3) . . ?
C9 C8 H8 119.5 . . ?
C7 C8 H8 119.5 . . ?
C8 C9 C10 119.6(3) . . ?
C8 C9 H1 120.2 . . ?
C10 C9 H1 120.2 . . ?
C11 C10 C9 120.8(3) . . ?
C11 C10 Br1 120.0(2) . . ?
C9 C10 Br1 119.3(2) . . ?
C10 C11 C6 120.4(3) . . ?
C10 C11 H9 119.8 . . ?
C6 C11 H9 119.8 . . ?

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
C1 C2 C3 C4 -59.1(5) . . . . ?
C2 C3 C4 C5 -69.6(4) . . . . ?
C3 C4 C5 O2 -1.4(5) . . . . ?
C3 C4 C5 C6 178.8(3) . . . . ?
O2 C5 C6 C11 -176.4(3) . . . . ?
C4 C5 C6 C11 3.4(4) . . . . ?
O2 C5 C6 C7 3.3(4) . . . . ?
C4 C5 C6 C7 -176.9(3) . . . . ?
C11 C6 C7 O1 178.8(3) . . . . ?
C5 C6 C7 O1 -0.9(4) . . . . ?
C11 C6 C7 C8 -0.5(4) . . . . ?
C5 C6 C7 C8 179.8(3) . . . . ?
O1 C7 C8 C9 -178.2(3) . . . . ?
C6 C7 C8 C9 1.1(5) . . . . ?
C7 C8 C9 C10 -0.7(5) . . . . ?
C8 C9 C10 C11 -0.3(5) . . . . ?
C8 C9 C10 Br1 179.3(2) . . . . ?
C9 C10 C11 C6 0.9(4) . . . . ?
Br1 C10 C11 C6 -178.7(2) . . . . ?
C7 C6 C11 C10 -0.5(4) . . . . ?
C5 C6 C11 C10 179.2(3) . . . . ?

_refine_diff_density_max         0.549
_refine_diff_density_min         -0.805
_refine_diff_density_rms         0.072

####################################################################### 
# 
# This file contains crystal structure data downloaded from the 
# Cambridge Structural Database (CSD) hosted by the Cambridge 
# Crystallographic Data Centre (CCDC).
# 
# Full information about CCDC data access policies and citation 
# guidelines are available at http://www.ccdc.cam.ac.uk/access/V1 
# 
# Audit and citation data items may have been added by the CCDC. 
# Please retain this information to preserve the provenance of 
# this file and to allow appropriate attribution of the data. 
# 
#######################################################################

data_1_CCDC1
_database_code_depnum_ccdc_archive 'CCDC 2353287'
loop_
_audit_author_name
_audit_author_address
'Feng Li'
;Zaozhuang University
China
;
_audit_update_record             
;
2024-05-06 deposited with the CCDC.	2025-01-23 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2018/3
_shelx_SHELXL_version_number     2018/3
_chemical_name_systematic        ?
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C12 H12 N2 O3 S'
_chemical_formula_weight         264.30

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'

_space_group_crystal_system      triclinic
_space_group_IT_number           2
_space_group_name_H-M_alt        'P -1'
_space_group_name_Hall           '-P 1'

_shelx_space_group_comment       
; 
The symmetry employed for this shelxl refinement is uniquely defined 
by the following loop, which should always be used as a source of 
symmetry information in preference to the above space-group names. 
They are only intended as comments. 
;

loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x, -y, -z'

_cell_length_a                   7.7907(5)
_cell_length_b                   9.2425(6)
_cell_length_c                   9.6790(5)
_cell_angle_alpha                106.943(2)
_cell_angle_beta                 105.014(2)
_cell_angle_gamma                96.858(3)
_cell_volume                     629.44(7)
_cell_formula_units_Z            2
_cell_measurement_temperature    300(2)
_cell_measurement_reflns_used    5723
_cell_measurement_theta_min      2.69
_cell_measurement_theta_max      31.87

_exptl_crystal_description       block
_exptl_crystal_colour            colorless
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.394
_exptl_crystal_F_000             276
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.241
_exptl_crystal_size_mid          0.212
_exptl_crystal_size_min          0.062
_exptl_absorpt_coefficient_mu    0.259
_shelx_estimated_absorpt_T_min   0.940
_shelx_estimated_absorpt_T_max   0.984
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.6815
_exptl_absorpt_correction_T_max  0.7466
_exptl_absorpt_process_details   'SADABS (Sheldrick,1996)'
_exptl_absorpt_special_details   ?
_diffrn_ambient_temperature      300(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_source                   ?
_diffrn_measurement_device_type  'Bruker APEX-II CCD'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            11872
_diffrn_reflns_av_unetI/netI     0.0200
_diffrn_reflns_av_R_equivalents  0.0287
_diffrn_reflns_limit_h_min       -9
_diffrn_reflns_limit_h_max       9
_diffrn_reflns_limit_k_min       -11
_diffrn_reflns_limit_k_max       11
_diffrn_reflns_limit_l_min       -11
_diffrn_reflns_limit_l_max       11
_diffrn_reflns_theta_min         2.691
_diffrn_reflns_theta_max         25.999
_diffrn_reflns_theta_full        25.242
_diffrn_measured_fraction_theta_max 0.990
_diffrn_measured_fraction_theta_full 0.989
_diffrn_reflns_Laue_measured_fraction_max 0.990
_diffrn_reflns_Laue_measured_fraction_full 0.989
_diffrn_reflns_point_group_measured_fraction_max 0.990
_diffrn_reflns_point_group_measured_fraction_full 0.989
_reflns_number_total             2441
_reflns_number_gt                2125
_reflns_threshold_expression     'I > 2σ(I)'
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_max     .
_reflns_Friedel_fraction_full    .

_reflns_special_details          
; 
 Reflections were merged by SHELXL according to the crystal 
 class for the calculation of statistics and refinement. 
  
 _reflns_Friedel_fraction is defined as the number of unique 
 Friedel pairs measured divided by the number that would be 
 possible theoretically, ignoring centric projections and 
 systematic absences. 
;

_computing_data_collection       'Bruker APEX2'
_computing_cell_refinement       'Bruker SAINT'
_computing_data_reduction        'Bruker SAINT'
_computing_structure_solution    'SHELXT 2018/2 (Sheldrick, 2018)'
_computing_structure_refinement  'SHELXL-2018/3 (Sheldrick, 2018)'
_computing_molecular_graphics    'Bruker SHELXTL'
_computing_publication_material  'Bruker SHELXTL'
_refine_special_details          ?
_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0453P)²+0.2823P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     ?
_atom_sites_solution_secondary   ?
_atom_sites_solution_hydrogens   geom
_refine_ls_hydrogen_treatment    constr
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       .
_refine_ls_number_reflns         2441
_refine_ls_number_parameters     164
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0503
_refine_ls_R_factor_gt           0.0432
_refine_ls_wR_factor_ref         0.1118
_refine_ls_wR_factor_gt          0.1072
_refine_ls_goodness_of_fit_ref   1.088
_refine_ls_restrained_S_all      1.088
_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_site_symmetry_order
_atom_site_calc_flag
_atom_site_refinement_flags_posn
_atom_site_refinement_flags_adp
_atom_site_refinement_flags_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
S1 S 0.18649(7) 0.23883(5) 0.01315(6) 0.04840(19) Uani 1 1 d . . . . .
O1 O 0.0659(2) 0.19319(16) 0.11012(16) 0.0541(4) Uani 1 1 d . . . . .
O2 O 0.0668(3) 0.18853(19) -0.13689(17) 0.0715(5) Uani 1 1 d . . . . .
O3 O 0.3467(2) 0.18160(17) 0.0436(2) 0.0662(5) Uani 1 1 d . . . . .
N1 N 0.6973(4) 1.0352(3) 0.4225(3) 0.0980(9) Uani 1 1 d . . . . .
N2 N 0.2395(2) 0.42654(17) 0.07619(18) 0.0446(4) Uani 1 1 d . . . . .
C1 C 0.5659(4) 0.9819(3) 0.3256(3) 0.0684(7) Uani 1 1 d . . . . .
C2 C 0.3977(4) 0.9129(3) 0.2019(3) 0.0667(7) Uani 1 1 d . . . . .
H12 H 0.405428 0.946464 0.117243 0.080 Uiso 1 1 calc R U . . .
H2 H 0.298794 0.950573 0.234623 0.080 Uiso 1 1 calc R U . . .
C3 C 0.3535(3) 0.7362(2) 0.1476(2) 0.0535(5) Uani 1 1 d . . . . .
H3 H 0.245587 0.697785 0.059467 0.064 Uiso 1 1 calc R U . . .
H4 H 0.453271 0.697873 0.116910 0.064 Uiso 1 1 calc R U . . .
C4 C 0.3219(3) 0.6746(2) 0.2700(2) 0.0445(4) Uani 1 1 d . . . . .
H11 H 0.434194 0.704583 0.353503 0.053 Uiso 1 1 calc R U . . .
H5 H 0.231847 0.722707 0.308409 0.053 Uiso 1 1 calc R U . . .
C5 C 0.2587(2) 0.5023(2) 0.2168(2) 0.0374(4) Uani 1 1 d . . . . .
C6 C 0.2182(2) 0.4281(2) 0.3223(2) 0.0376(4) Uani 1 1 d . . . . .
C7 C 0.2604(2) 0.5066(2) 0.4783(2) 0.0421(4) Uani 1 1 d . . . . .
H8 H 0.321669 0.609641 0.518407 0.051 Uiso 1 1 calc R U . . .
C8 C 0.2132(3) 0.4349(2) 0.5741(2) 0.0452(4) Uani 1 1 d . . . . .
C9 C 0.2570(3) 0.5224(3) 0.7407(2) 0.0615(6) Uani 1 1 d . . . . .
H7 H 0.293544 0.631018 0.759243 0.092 Uiso 1 1 calc R U . . .
H6 H 0.354116 0.487740 0.797473 0.092 Uiso 1 1 calc R U . . .
H1 H 0.151341 0.504312 0.771879 0.092 Uiso 1 1 calc R U . . .
C10 C 0.1258(3) 0.2743(2) 0.2667(2) 0.0427(4) Uani 1 1 d . . . . .
C11 C 0.0763(3) 0.2002(2) 0.3591(3) 0.0538(5) Uani 1 1 d . . . . .
H10 H 0.013658 0.097558 0.319334 0.065 Uiso 1 1 calc R U . . .
C12 C 0.1214(3) 0.2811(3) 0.5114(3) 0.0539(5) Uani 1 1 d . . . . .
H9 H 0.089418 0.231391 0.574711 0.065 Uiso 1 1 calc R U . . .


_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 O3 1.4078(17) . ?
S1 O2 1.4127(16) . ?
S1 O1 1.5921(14) . ?
S1 N2 1.6230(15) . ?
O1 C10 1.402(2) . ?
N1 C1 1.133(4) . ?
N2 C5 1.296(2) . ?
C1 C2 1.448(4) . ?
C2 C3 1.528(3) . ?
C2 H12 0.9700 . ?
C2 H2 0.9700 . ?
C3 C4 1.516(3) . ?
C3 H3 0.9700 . ?
C3 H4 0.9700 . ?
C4 C5 1.499(2) . ?
C4 H11 0.9700 . ?
C4 H5 0.9700 . ?
C5 C6 1.461(2) . ?
C6 C10 1.392(2) . ?
C6 C7 1.401(3) . ?
C7 C8 1.383(3) . ?
C7 H8 0.9300 . ?
C8 C12 1.389(3) . ?
C8 C9 1.503(3) . ?
C9 H7 0.9600 . ?
C9 H6 0.9600 . ?
C9 H1 0.9600 . ?
C10 C11 1.375(3) . ?
C11 C12 1.371(3) . ?
C11 H10 0.9300 . ?
C12 H9 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
O3 S1 O2 119.46(11) . . ?
O3 S1 O1 108.75(9) . . ?
O2 S1 O1 104.63(9) . . ?
O3 S1 N2 108.87(9) . . ?
O2 S1 N2 108.88(9) . . ?
O1 S1 N2 105.32(8) . . ?
C10 O1 S1 116.97(11) . . ?
C5 N2 S1 120.26(13) . . ?
N1 C1 C2 179.6(3) . . ?
C1 C2 C3 113.6(2) . . ?
C1 C2 H12 108.8 . . ?
C3 C2 H12 108.8 . . ?
C1 C2 H2 108.8 . . ?
C3 C2 H2 108.8 . . ?
H12 C2 H2 107.7 . . ?
C4 C3 C2 111.99(17) . . ?
C4 C3 H3 109.2 . . ?
C2 C3 H3 109.2 . . ?
C4 C3 H4 109.2 . . ?
C2 C3 H4 109.2 . . ?
H3 C3 H4 107.9 . . ?
C5 C4 C3 113.86(16) . . ?
C5 C4 H11 108.8 . . ?
C3 C4 H11 108.8 . . ?
C5 C4 H5 108.8 . . ?
C3 C4 H5 108.8 . . ?
H11 C4 H5 107.7 . . ?
N2 C5 C6 123.17(16) . . ?
N2 C5 C4 117.26(15) . . ?
C6 C5 C4 119.56(15) . . ?
C10 C6 C7 117.35(16) . . ?
C10 C6 C5 119.53(16) . . ?
C7 C6 C5 123.05(16) . . ?
C8 C7 C6 121.65(17) . . ?
C8 C7 H8 119.2 . . ?
C6 C7 H8 119.2 . . ?
C7 C8 C12 118.08(18) . . ?
C7 C8 C9 120.68(19) . . ?
C12 C8 C9 121.23(18) . . ?
C8 C9 H7 109.5 . . ?
C8 C9 H6 109.5 . . ?
H7 C9 H6 109.5 . . ?
C8 C9 H1 109.5 . . ?
H7 C9 H1 109.5 . . ?
H6 C9 H1 109.5 . . ?
C11 C10 C6 122.28(18) . . ?
C11 C10 O1 117.34(16) . . ?
C6 C10 O1 120.15(16) . . ?
C12 C11 C10 118.44(18) . . ?
C12 C11 H10 120.8 . . ?
C10 C11 H10 120.8 . . ?
C11 C12 C8 122.19(18) . . ?
C11 C12 H9 118.9 . . ?
C8 C12 H9 118.9 . . ?

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
O3 S1 O1 C10 73.21(16) . . . . ?
O2 S1 O1 C10 -158.08(14) . . . . ?
N2 S1 O1 C10 -43.36(16) . . . . ?
O3 S1 N2 C5 -85.44(17) . . . . ?
O2 S1 N2 C5 142.79(16) . . . . ?
O1 S1 N2 C5 31.05(18) . . . . ?
C1 C2 C3 C4 63.9(3) . . . . ?
C2 C3 C4 C5 173.84(19) . . . . ?
S1 N2 C5 C6 -6.1(3) . . . . ?
S1 N2 C5 C4 175.35(14) . . . . ?
C3 C4 C5 N2 0.3(3) . . . . ?
C3 C4 C5 C6 -178.29(18) . . . . ?
N2 C5 C6 C10 -11.4(3) . . . . ?
C4 C5 C6 C10 167.14(17) . . . . ?
N2 C5 C6 C7 171.71(18) . . . . ?
C4 C5 C6 C7 -9.7(3) . . . . ?
C10 C6 C7 C8 0.2(3) . . . . ?
C5 C6 C7 C8 177.19(17) . . . . ?
C6 C7 C8 C12 -0.1(3) . . . . ?
C6 C7 C8 C9 -178.89(18) . . . . ?
C7 C6 C10 C11 0.1(3) . . . . ?
C5 C6 C10 C11 -176.94(18) . . . . ?
C7 C6 C10 O1 174.56(17) . . . . ?
C5 C6 C10 O1 -2.5(3) . . . . ?
S1 O1 C10 C11 -153.22(16) . . . . ?
S1 O1 C10 C6 32.1(2) . . . . ?
C6 C10 C11 C12 -0.5(3) . . . . ?
O1 C10 C11 C12 -175.14(19) . . . . ?
C10 C11 C12 C8 0.6(3) . . . . ?
C7 C8 C12 C11 -0.3(3) . . . . ?
C9 C8 C12 C11 178.4(2) . . . . ?

_refine_diff_density_max         0.221
_refine_diff_density_min         -0.337
_refine_diff_density_rms         0.039

