# Electronic Supplementary Material (ESI) for CrystEngComm.
# This journal is © The Royal Society of Chemistry 2020

####################################################################### 
# 
# 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_shelx
_database_code_depnum_ccdc_archive 'CCDC 2006014'
loop_
_audit_author_name
_audit_author_address
'Doris Braun'
;University of Innsbruck
Austria
;
_audit_update_record             
;
2020-05-27 deposited with the CCDC.	2020-08-21 downloaded from the CCDC.
;

_audit_creation_date             2014-06-19T18:41:47-00:00
_audit_creation_method           'WinGX routine CIF_UPDATE'
_audit_conform_dict_name         cif_core.dic
_audit_conform_dict_version      2.4.3
_audit_conform_dict_location     ftp://ftp.iucr.org/pub/cif_core.dic

#----------------------------------------------------------------------------#
#                   CHEMICAL INFORMATION                                     #
#----------------------------------------------------------------------------#

_chemical_name_systematic        
;
 ?
;
_chemical_formula_moiety         'C7 H11 N2 O S, Br'
_chemical_formula_sum            'C7 H11 Br N2 O S'
_chemical_formula_weight         251.15

#----------------------------------------------------------------------------#
#                   UNIT CELL INFORMATION                                    #
#----------------------------------------------------------------------------#

_symmetry_cell_setting           monoclinic
_symmetry_space_group_name_H-M   'C 2/c'
_symmetry_space_group_name_Hall  '-C 2yc'
_symmetry_Int_Tables_number      15
loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'-x, y, -z+1/2'
'x+1/2, y+1/2, z'
'-x+1/2, y+1/2, -z+1/2'
'-x, -y, -z'
'x, -y, z-1/2'
'-x+1/2, -y+1/2, -z'
'x+1/2, -y+1/2, z-1/2'

_cell_length_a                   11.2359(2)
_cell_length_b                   14.9020(2)
_cell_length_c                   12.3361(3)
_cell_angle_alpha                90
_cell_angle_beta                 111.2210(10)
_cell_angle_gamma                90
_cell_volume                     1925.46(6)
_cell_formula_units_Z            8
_cell_measurement_temperature    233(2)
_cell_measurement_reflns_used    8910
_cell_measurement_theta_min      0.998
_cell_measurement_theta_max      27.485
_cell_measurement_wavelength     0.71073

#----------------------------------------------------------------------------#
#                   CRYSTAL INFORMATION                                      #
#----------------------------------------------------------------------------#

_exptl_crystal_description       prism
_exptl_crystal_colour            colorless
_exptl_crystal_size_max          0.4
_exptl_crystal_size_mid          0.4
_exptl_crystal_size_min          0.3
_exptl_crystal_density_diffrn    1.733
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             1008
_exptl_special_details           
;
 ?
;

#----------------------------------------------------------------------------#
#                   ABSORPTION CORRECTION                                    #
#----------------------------------------------------------------------------#

_exptl_absorpt_coefficient_mu    4.442
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.270
_exptl_absorpt_correction_T_max  0.349
_exptl_absorpt_process_details   
;
(SORTAV; Blessing, 1995)
;


#----------------------------------------------------------------------------#
#                   DATA COLLECTION                                          #
#----------------------------------------------------------------------------#

_diffrn_ambient_temperature      233(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_radiation_probe          x-ray
_diffrn_radiation_source         'fine-focus sealed tube'
_diffrn_radiation_monochromator  graphite
_diffrn_measurement_device_type  'Nonius Kappa CCD'
_diffrn_measurement_method       'phi and omega-scans'
_diffrn_reflns_av_R_equivalents  0.0854
_diffrn_reflns_number            6560
_diffrn_reflns_limit_h_min       -14
_diffrn_reflns_limit_h_max       14
_diffrn_reflns_limit_k_min       -19
_diffrn_reflns_limit_k_max       19
_diffrn_reflns_limit_l_min       -15
_diffrn_reflns_limit_l_max       13
_diffrn_reflns_theta_min         2.377
_diffrn_reflns_theta_max         27.468
_diffrn_reflns_theta_full        26
_diffrn_measured_fraction_theta_full 0.997
_diffrn_measured_fraction_theta_max 0.997
_diffrn_reflns_Laue_measured_fraction_full 0.997
_diffrn_reflns_Laue_measured_fraction_max 0.997
_diffrn_reflns_point_group_measured_fraction_full 0.997
_diffrn_reflns_point_group_measured_fraction_max 0.997
_reflns_number_total             2190
_reflns_number_gt                2006
_reflns_threshold_expression     'I > 2σ(I)'

#----------------------------------------------------------------------------#
#                   COMPUTER PROGRAMS USED                                   #
#----------------------------------------------------------------------------#

_computing_structure_refinement  'SHELXL-2013 (Sheldrick, 2013)'
_computing_molecular_graphics    'Ortep for Windows (Farrugia, 2012)'
_computing_publication_material  'WinGX publication routines (Farrugia, 2012)'

#----------------------------------------------------------------------------#
#                   STRUCTURE SOLUTION
#----------------------------------------------------------------------------#

_atom_sites_solution_hydrogens   mixed

#----------------------------------------------------------------------------#
#                   REFINEMENT INFORMATION                                   #
#----------------------------------------------------------------------------#

_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)+(0.0131P)²+1.4495P] where P=(Fo²+2Fc²)/3'
_refine_ls_hydrogen_treatment    mixed
_refine_ls_extinction_method     SHELXL
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc²λ³/sin(2θ)]^-1/4^
_refine_ls_extinction_coef       0.0033(3)
_refine_ls_number_reflns         2190
_refine_ls_number_parameters     115
_refine_ls_number_restraints     1
_refine_ls_number_constraints    0
_refine_ls_R_factor_all          0.032
_refine_ls_R_factor_gt           0.0289
_refine_ls_wR_factor_ref         0.0762
_refine_ls_wR_factor_gt          0.0737
_refine_ls_goodness_of_fit_ref   1.083
_refine_ls_restrained_S_all      1.083
_refine_ls_shift/su_max          0.001
_refine_ls_shift/su_mean         0
_refine_diff_density_max         0.381
_refine_diff_density_min         -0.551
_refine_diff_density_rms         0.074

#----------------------------------------------------------------------------#
#                   ATOMIC TYPES, COORDINATES AND THERMAL PARAMETERS         #
#----------------------------------------------------------------------------#

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 0 '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 0.006 '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'

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_calc_flag
_atom_site_disorder_assembly
_atom_site_disorder_group
C1 C 0.34548(18) 0.79597(16) 0.65568(18) 0.0323(5) Uani 1 d . .
H1 H 0.2999 0.821 0.6989 0.039 Uiso 1 calc . .
C2 C 0.36161(17) 0.70771(16) 0.64050(18) 0.0320(5) Uani 1 d . .
H2 H 0.3293 0.6598 0.6711 0.038 Uiso 1 calc . .
C3 C 0.47730(19) 0.61705(14) 0.5356(2) 0.0343(5) Uani 1 d . .
H3A H 0.4098 0.5937 0.4661 0.041 Uiso 1 calc . .
H3B H 0.4934 0.5725 0.5977 0.041 Uiso 1 calc . .
C4 C 0.5983(2) 0.63124(15) 0.50952(19) 0.0356(5) Uani 1 d . .
H4 H 0.6194 0.574 0.4798 0.043 Uiso 1 calc . .
C5 C 0.5799(2) 0.70222(16) 0.41755(19) 0.0379(5) Uani 1 d . .
H5A H 0.5064 0.6859 0.3482 0.045 Uiso 1 calc . .
H5B H 0.6555 0.7036 0.3957 0.045 Uiso 1 calc . .
C6 C 0.46173(17) 0.78443(14) 0.54483(17) 0.0261(4) Uani 1 d . .
C7 C 0.4155(2) 0.94062(14) 0.5876(2) 0.0358(5) Uani 1 d . .
H7A H 0.5042 0.9594 0.618 0.054 Uiso 1 calc . .
H7B H 0.3702 0.9684 0.6325 0.054 Uiso 1 calc . .
H7C H 0.3767 0.9588 0.5068 0.054 Uiso 1 calc . .
H10 H 0.720(3) 0.6116(15) 0.654(2) 0.063(10) Uiso 1 d . .
N1 N 0.40861(14) 0.84267(11) 0.59576(15) 0.0284(4) Uani 1 d . .
N2 N 0.43491(14) 0.70105(12) 0.57115(15) 0.0276(4) Uani 1 d . .
O1 O 0.70361(14) 0.65559(11) 0.61072(14) 0.0389(4) Uani 1 d . .
S1 S 0.55380(6) 0.81408(4) 0.46518(6) 0.03891(16) Uani 1 d . .
Br1 Br 0.71040(2) 0.47996(2) 0.77478(2) 0.03684(12) Uani 1 d . .



#----------------------------------------------------------------------------#
#                   MOLECULAR GEOMETRY                                       #
#----------------------------------------------------------------------------#

_geom_special_details            
;
 All esds (except the esd in the dihedral angle between two l.s. planes)
 are estimated using the full covariance matrix.  The cell esds are taken
 into account individually in the estimation of esds in distances, angles
 and torsion angles; correlations between esds in cell parameters are only
 used when they are defined by crystal symmetry.  An approximate (isotropic)
 treatment of cell esds is used for estimating esds involving l.s. planes.
;
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
C1 C2 1.350(3) . ?
C1 N1 1.383(3) . ?
C1 H1 0.94 . ?
C2 N2 1.389(3) . ?
C2 H2 0.94 . ?
C3 N2 1.462(3) . ?
C3 C4 1.521(3) . ?
C3 H3A 0.98 . ?
C3 H3B 0.98 . ?
C4 O1 1.421(2) . ?
C4 C5 1.510(3) . ?
C4 H4 0.99 . ?
C5 S1 1.826(2) . ?
C5 H5A 0.98 . ?
C5 H5B 0.98 . ?
C6 N1 1.333(3) . ?
C6 N2 1.346(3) . ?
C6 S1 1.722(2) . ?
C7 N1 1.467(3) . ?
C7 H7A 0.97 . ?
C7 H7B 0.97 . ?
C7 H7C 0.97 . ?
O1 H10 0.821(17) . ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
C2 C1 N1 107.2(2) . . ?
C2 C1 H1 126.4 . . ?
N1 C1 H1 126.4 . . ?
C1 C2 N2 107.1(2) . . ?
C1 C2 H2 126.4 . . ?
N2 C2 H2 126.4 . . ?
N2 C3 C4 110.95(17) . . ?
N2 C3 H3A 109.4 . . ?
C4 C3 H3A 109.4 . . ?
N2 C3 H3B 109.4 . . ?
C4 C3 H3B 109.4 . . ?
H3A C3 H3B 108 . . ?
O1 C4 C5 108.99(18) . . ?
O1 C4 C3 111.93(18) . . ?
C5 C4 C3 111.48(18) . . ?
O1 C4 H4 108.1 . . ?
C5 C4 H4 108.1 . . ?
C3 C4 H4 108.1 . . ?
C4 C5 S1 113.09(15) . . ?
C4 C5 H5A 109 . . ?
S1 C5 H5A 109 . . ?
C4 C5 H5B 109 . . ?
S1 C5 H5B 109 . . ?
H5A C5 H5B 107.8 . . ?
N1 C6 N2 108.06(18) . . ?
N1 C6 S1 124.46(16) . . ?
N2 C6 S1 127.42(17) . . ?
N1 C7 H7A 109.5 . . ?
N1 C7 H7B 109.5 . . ?
H7A C7 H7B 109.5 . . ?
N1 C7 H7C 109.5 . . ?
H7A C7 H7C 109.5 . . ?
H7B C7 H7C 109.5 . . ?
C6 N1 C1 109.15(18) . . ?
C6 N1 C7 124.9(2) . . ?
C1 N1 C7 126.0(2) . . ?
C6 N2 C2 108.48(19) . . ?
C6 N2 C3 126.32(18) . . ?
C2 N2 C3 125.18(19) . . ?
C4 O1 H10 107(2) . . ?
C6 S1 C5 98.56(11) . . ?


# END of CIF
_exptl_crystal_recrystallization_method 
'Re-crystallisation from solvent: methanol'
####################################################################### 
# 
# 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_shelx_CCDC1
_database_code_depnum_ccdc_archive 'CCDC 2006016'
loop_
_audit_author_name
_audit_author_address
'Doris Braun'
;University of Innsbruck
Austria
;
_audit_update_record             
;
2020-05-27 deposited with the CCDC.	2020-08-21 downloaded from the CCDC.
;

_audit_creation_date             2014-06-19T17:51:19-00:00
_audit_creation_method           'WinGX routine CIF_UPDATE'
_audit_conform_dict_name         cif_core.dic
_audit_conform_dict_version      2.4.3
_audit_conform_dict_location     ftp://ftp.iucr.org/pub/cif_core.dic

#----------------------------------------------------------------------------#
#                   CHEMICAL INFORMATION                                     #
#----------------------------------------------------------------------------#

_chemical_name_systematic        
;
 ?
;
_chemical_formula_moiety         'C7 H11 N2 O S, Cl '
_chemical_formula_sum            'C7 H11 Cl N2 O S '
_chemical_formula_weight         206.70

#----------------------------------------------------------------------------#
#                   UNIT CELL INFORMATION                                    #
#----------------------------------------------------------------------------#

_symmetry_cell_setting           monoclinic
_symmetry_space_group_name_H-M   'C 2/c'
_symmetry_space_group_name_Hall  '-C 2yc'
_symmetry_Int_Tables_number      15
loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'-x, y, -z+1/2'
'x+1/2, y+1/2, z'
'-x+1/2, y+1/2, -z+1/2'
'-x, -y, -z'
'x, -y, z-1/2'
'-x+1/2, -y+1/2, -z'
'x+1/2, -y+1/2, z-1/2'

_cell_length_a                   11.1116(2)
_cell_length_b                   14.6502(3)
_cell_length_c                   12.1138(4)
_cell_angle_alpha                90
_cell_angle_beta                 111.270(2)
_cell_angle_gamma                90
_cell_volume                     1837.64(8)
_cell_formula_units_Z            8
_cell_measurement_temperature    233(2)
_cell_measurement_reflns_used    8123
_cell_measurement_theta_min      0.998
_cell_measurement_theta_max      27.485
_cell_measurement_wavelength     0.71073

#----------------------------------------------------------------------------#
#                   CRYSTAL INFORMATION                                      #
#----------------------------------------------------------------------------#

_exptl_crystal_description       prism
_exptl_crystal_colour            colorless
_exptl_crystal_size_max          0.4
_exptl_crystal_size_mid          0.4
_exptl_crystal_size_min          0.25
_exptl_crystal_density_diffrn    1.494
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             864
_exptl_special_details           
;
 ?
;

#----------------------------------------------------------------------------#
#                   ABSORPTION CORRECTION                                    #
#----------------------------------------------------------------------------#

_exptl_absorpt_coefficient_mu    0.596
_exptl_absorpt_correction_type   none
_shelx_estimated_absorpt_T_min   0.797
_shelx_estimated_absorpt_T_max   0.865

#----------------------------------------------------------------------------#
#                   DATA COLLECTION                                          #
#----------------------------------------------------------------------------#

_diffrn_ambient_temperature      233(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_radiation_probe          x-ray
_diffrn_radiation_source         'fine-focus sealed tube'
_diffrn_radiation_monochromator  graphite
_diffrn_measurement_device_type  'Kappa CCD'
_diffrn_measurement_method       'phi- and omega-scans'
_diffrn_reflns_av_R_equivalents  0.0203
_diffrn_reflns_number            7134
_diffrn_reflns_limit_h_min       -14
_diffrn_reflns_limit_h_max       14
_diffrn_reflns_limit_k_min       -18
_diffrn_reflns_limit_k_max       18
_diffrn_reflns_limit_l_min       -15
_diffrn_reflns_limit_l_max       15
_diffrn_reflns_theta_min         2.409
_diffrn_reflns_theta_max         27.492
_diffrn_reflns_theta_full        26
_diffrn_measured_fraction_theta_full 0.993
_diffrn_measured_fraction_theta_max 0.994
_diffrn_reflns_Laue_measured_fraction_full 0.993
_diffrn_reflns_Laue_measured_fraction_max 0.994
_diffrn_reflns_point_group_measured_fraction_full 0.993
_diffrn_reflns_point_group_measured_fraction_max 0.994
_reflns_number_total             2099
_reflns_number_gt                1937
_reflns_threshold_expression     'I > 2σ(I)'

#----------------------------------------------------------------------------#
#                   COMPUTER PROGRAMS USED                                   #
#----------------------------------------------------------------------------#

_computing_structure_refinement  'SHELXL-2013 (Sheldrick, 2013)'
_computing_molecular_graphics    'Ortep for Windows (Farrugia, 2012)'
_computing_publication_material  'WinGX publication routines (Farrugia, 2012)'

#----------------------------------------------------------------------------#
#                   STRUCTURE SOLUTION
#----------------------------------------------------------------------------#

_atom_sites_solution_hydrogens   mixed

#----------------------------------------------------------------------------#
#                   REFINEMENT INFORMATION                                   #
#----------------------------------------------------------------------------#

_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)+(0.0327P)²+1.6045P] where P=(Fo²+2Fc²)/3'
_refine_ls_hydrogen_treatment    mixed
_refine_ls_extinction_method     SHELXL
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc²λ³/sin(2θ)]^-1/4^
_refine_ls_extinction_coef       0.0062(13)
_refine_ls_number_reflns         2099
_refine_ls_number_parameters     115
_refine_ls_number_restraints     1
_refine_ls_number_constraints    0
_refine_ls_R_factor_all          0.0311
_refine_ls_R_factor_gt           0.0287
_refine_ls_wR_factor_ref         0.0747
_refine_ls_wR_factor_gt          0.0731
_refine_ls_goodness_of_fit_ref   1.046
_refine_ls_restrained_S_all      1.046
_refine_ls_shift/su_max          0.001
_refine_ls_shift/su_mean         0
_refine_diff_density_max         0.253
_refine_diff_density_min         -0.247
_refine_diff_density_rms         0.041

#----------------------------------------------------------------------------#
#                   ATOMIC TYPES, COORDINATES AND THERMAL PARAMETERS         #
#----------------------------------------------------------------------------#

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 0 '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 0.006 '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'
Cl Cl 0.1484 0.1585 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

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_calc_flag
_atom_site_disorder_assembly
_atom_site_disorder_group
C1 C 0.34232(13) 0.79614(10) 0.65795(12) 0.0285(3) Uani 1 d . .
H1 H 0.2957 0.8212 0.7017 0.034 Uiso 1 calc . .
C2 C 0.35922(13) 0.70675(10) 0.64222(12) 0.0290(3) Uani 1 d . .
H2 H 0.3263 0.6578 0.6728 0.035 Uiso 1 calc . .
C3 C 0.47765(14) 0.61445(9) 0.53652(13) 0.0308(3) Uani 1 d . .
H3A H 0.4094 0.5905 0.4658 0.037 Uiso 1 calc . .
H3B H 0.4943 0.5692 0.6 0.037 Uiso 1 calc . .
C4 C 0.59965(15) 0.62897(9) 0.50996(13) 0.0329(3) Uani 1 d . .
H4 H 0.6205 0.571 0.4788 0.039 Uiso 1 calc . .
C5 C 0.58055(17) 0.70214(10) 0.41653(13) 0.0361(3) Uani 1 d . .
H5A H 0.5059 0.6859 0.346 0.043 Uiso 1 calc . .
H5B H 0.6567 0.7037 0.3939 0.043 Uiso 1 calc . .
C6 C 0.46151(12) 0.78457(9) 0.54635(11) 0.0239(3) Uani 1 d . .
C7 C 0.41370(15) 0.94385(9) 0.58828(13) 0.0332(3) Uani 1 d . .
H7A H 0.5035 0.9626 0.6145 0.05 Uiso 1 calc . .
H7B H 0.3726 0.9725 0.6377 0.05 Uiso 1 calc . .
H7C H 0.3697 0.9623 0.5066 0.05 Uiso 1 calc . .
H1O H 0.718(2) 0.6090(13) 0.6594(18) 0.063(7) Uiso 1 d . .
N1 N 0.40661(10) 0.84434(7) 0.59752(9) 0.0253(2) Uani 1 d . .
N2 N 0.43401(10) 0.70008(7) 0.57266(10) 0.0250(2) Uani 1 d . .
O1 O 0.70631(10) 0.65284(7) 0.61297(10) 0.0354(3) Uani 1 d . .
S1 S 0.55497(4) 0.81534(2) 0.46570(3) 0.03563(14) Uani 1 d . .
Cl1 Cl 0.71363(4) 0.48335(2) 0.77188(3) 0.03704(14) Uani 1 d . .



#----------------------------------------------------------------------------#
#                   MOLECULAR GEOMETRY                                       #
#----------------------------------------------------------------------------#

_geom_special_details            
;
 All esds (except the esd in the dihedral angle between two l.s. planes)
 are estimated using the full covariance matrix.  The cell esds are taken
 into account individually in the estimation of esds in distances, angles
 and torsion angles; correlations between esds in cell parameters are only
 used when they are defined by crystal symmetry.  An approximate (isotropic)
 treatment of cell esds is used for estimating esds involving l.s. planes.
;
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
C1 C2 1.346(2) . ?
C1 N1 1.3872(16) . ?
C1 H1 0.94 . ?
C2 N2 1.3850(17) . ?
C2 H2 0.94 . ?
C3 N2 1.4678(17) . ?
C3 C4 1.518(2) . ?
C3 H3A 0.98 . ?
C3 H3B 0.98 . ?
C4 O1 1.4181(18) . ?
C4 C5 1.517(2) . ?
C4 H4 0.99 . ?
C5 S1 1.8190(15) . ?
C5 H5A 0.98 . ?
C5 H5B 0.98 . ?
C6 N1 1.3407(16) . ?
C6 N2 1.3408(16) . ?
C6 S1 1.7241(13) . ?
C7 N1 1.4664(17) . ?
C7 H7A 0.97 . ?
C7 H7B 0.97 . ?
C7 H7C 0.97 . ?
O1 H1O 0.833(16) . ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
C2 C1 N1 107.19(12) . . ?
C2 C1 H1 126.4 . . ?
N1 C1 H1 126.4 . . ?
C1 C2 N2 107.46(11) . . ?
C1 C2 H2 126.3 . . ?
N2 C2 H2 126.3 . . ?
N2 C3 C4 111.14(11) . . ?
N2 C3 H3A 109.4 . . ?
C4 C3 H3A 109.4 . . ?
N2 C3 H3B 109.4 . . ?
C4 C3 H3B 109.4 . . ?
H3A C3 H3B 108 . . ?
O1 C4 C5 109.17(12) . . ?
O1 C4 C3 111.94(11) . . ?
C5 C4 C3 111.30(12) . . ?
O1 C4 H4 108.1 . . ?
C5 C4 H4 108.1 . . ?
C3 C4 H4 108.1 . . ?
C4 C5 S1 113.34(10) . . ?
C4 C5 H5A 108.9 . . ?
S1 C5 H5A 108.9 . . ?
C4 C5 H5B 108.9 . . ?
S1 C5 H5B 108.9 . . ?
H5A C5 H5B 107.7 . . ?
N1 C6 N2 108.17(11) . . ?
N1 C6 S1 124.05(10) . . ?
N2 C6 S1 127.75(10) . . ?
N1 C7 H7A 109.5 . . ?
N1 C7 H7B 109.5 . . ?
H7A C7 H7B 109.5 . . ?
N1 C7 H7C 109.5 . . ?
H7A C7 H7C 109.5 . . ?
H7B C7 H7C 109.5 . . ?
C6 N1 C1 108.62(11) . . ?
C6 N1 C7 124.61(11) . . ?
C1 N1 C7 126.77(11) . . ?
C6 N2 C2 108.56(11) . . ?
C6 N2 C3 126.13(11) . . ?
C2 N2 C3 125.30(11) . . ?
C4 O1 H1O 106.2(16) . . ?
C6 S1 C5 98.33(7) . . ?


# END of CIF
_exptl_crystal_recrystallization_method 
'Re-crystallisation from solvent: methanol'
####################################################################### 
# 
# 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_ml139_2
_database_code_depnum_ccdc_archive 'CCDC 2006017'
loop_
_audit_author_name
_audit_author_address
'Doris Braun'
;University of Innsbruck
Austria
;
_audit_update_record             
;
2020-05-27 deposited with the CCDC.	2020-08-21 downloaded from the CCDC.
;

_audit_creation_date             2014-08-15T12:16:29-00:00
_audit_creation_method           'WinGX routine CIF_UPDATE'
_audit_conform_dict_name         cif_core.dic
_audit_conform_dict_version      2.4
_audit_conform_dict_location     ftp://ftp.iucr.org/pub/cif_core.dic

#----------------------------------------------------------------------------#
#                   CHEMICAL INFORMATION                                     #
#----------------------------------------------------------------------------#

_chemical_name_systematic        
;
 ?
;
_chemical_formula_sum            'C6 H10 Br N3 O S'
_chemical_formula_moiety         'C6 H10 N3 O S, Br'
_chemical_formula_weight         252.14
_chemical_absolute_configuration ad

#----------------------------------------------------------------------------#
#                   UNIT CELL INFORMATION                                    #
#----------------------------------------------------------------------------#

_symmetry_cell_setting           orthorhombic
_symmetry_space_group_name_H-M   'P n a 21'
_symmetry_space_group_name_Hall  'P 2c -2n'
loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'-x, -y, z+1/2'
'-x+1/2, y+1/2, z+1/2'
'x+1/2, -y+1/2, z'

_cell_length_a                   15.1584(6)
_cell_length_b                   6.9422(3)
_cell_length_c                   8.7807(4)
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_volume                     924.02(7)
_cell_formula_units_Z            4
_cell_measurement_temperature    203(2)
_cell_measurement_reflns_used    2397
_cell_measurement_theta_min      3.547
_cell_measurement_theta_max      28.127

#----------------------------------------------------------------------------#
#                   CRYSTAL INFORMATION                                      #
#----------------------------------------------------------------------------#

_exptl_crystal_description       'prismatic fragment'
_exptl_crystal_colour            colourless
_exptl_crystal_size_max          0.12
_exptl_crystal_size_mid          0.08
_exptl_crystal_size_min          0.02
_exptl_crystal_density_diffrn    1.812
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             504
_exptl_special_details           
;
 ?
;

#----------------------------------------------------------------------------#
#                   ABSORPTION CORRECTION                                    #
#----------------------------------------------------------------------------#

_exptl_absorpt_coefficient_mu    4.631
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
        CrysAlisPro, Agilent Technologies,
        Version 1.171.37.31 (release 14-01-2014 CrysAlis171 .NET)
        (compiled Jan 14 2014,18:38:05)
        Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_absorpt_correction_T_min  0.7956
_exptl_absorpt_correction_T_max  1

#----------------------------------------------------------------------------#
#                   DATA COLLECTION                                          #
#----------------------------------------------------------------------------#

_diffrn_source                   'Enhance (Mo) X-ray Source'
_diffrn_ambient_temperature      203(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_probe          x-ray
_diffrn_detector                 'CCD plate'
_diffrn_detector_area_resol_mean 10.3575
_diffrn_orient_matrix_ub_11      -0.026899
_diffrn_orient_matrix_ub_12      0.0199978
_diffrn_orient_matrix_ub_13      0.064186
_diffrn_orient_matrix_ub_21      -0.0080298
_diffrn_orient_matrix_ub_22      -0.0999439
_diffrn_orient_matrix_ub_23      0.0094426
_diffrn_orient_matrix_ub_31      0.0374387
_diffrn_orient_matrix_ub_32      -0.0070701
_diffrn_orient_matrix_ub_33      0.0481274
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'Xcalibur, Ruby, Gemini ultra'
_diffrn_measurement_method       'ω scans'
_diffrn_reflns_av_R_equivalents  0.0302
_diffrn_reflns_av_unetI/netI     0.0319
_diffrn_reflns_number            5309
_diffrn_reflns_limit_h_min       -18
_diffrn_reflns_limit_h_max       15
_diffrn_reflns_limit_k_min       -8
_diffrn_reflns_limit_k_max       6
_diffrn_reflns_limit_l_min       -10
_diffrn_reflns_limit_l_max       10
_diffrn_reflns_theta_min         3.23
_diffrn_reflns_theta_max         25.34
_diffrn_reflns_theta_full        25.34
_diffrn_measured_fraction_theta_full 0.999
_diffrn_measured_fraction_theta_max 0.999
_reflns_number_total             1674
_reflns_number_gt                1527
_reflns_threshold_expression     >2sigma(I)

#----------------------------------------------------------------------------#
#                   COMPUTER PROGRAMS USED                                   #
#----------------------------------------------------------------------------#

_computing_data_collection       
;
        CrysAlisPro, Agilent Technologies,
        Version 1.171.37.31 (release 14-01-2014 CrysAlis171 .NET)
        (compiled Jan 14 2014,18:38:05)
;
_computing_cell_refinement       
;
        CrysAlisPro, Agilent Technologies,
        Version 1.171.37.31 (release 14-01-2014 CrysAlis171 .NET)
        (compiled Jan 14 2014,18:38:05)
;
_computing_data_reduction        
;
        CrysAlisPro, Agilent Technologies,
        Version 1.171.37.31 (release 14-01-2014 CrysAlis171 .NET)
        (compiled Jan 14 2014,18:38:05)
;
_computing_structure_solution    'SIR2002 (Burla et al., 2003)'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'

#----------------------------------------------------------------------------#
#                   STRUCTURE SOLUTION
#----------------------------------------------------------------------------#

_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_atom_sites_solution_hydrogens   geom

#----------------------------------------------------------------------------#
#                   REFINEMENT INFORMATION                                   #
#----------------------------------------------------------------------------#

_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)+(0.0133P)²+1.6419P] where P=(Fo²+2Fc²)/3'
_refine_ls_hydrogen_treatment    mixed
_refine_ls_extinction_method     none
_refine_ls_number_reflns         1674
_refine_ls_number_parameters     116
_refine_ls_number_restraints     3
_refine_ls_R_factor_all          0.0344
_refine_ls_R_factor_gt           0.0287
_refine_ls_wR_factor_ref         0.0606
_refine_ls_wR_factor_gt          0.0585
_refine_ls_goodness_of_fit_ref   1.067
_refine_ls_restrained_S_all      1.076
_refine_ls_shift/su_max          0
_refine_ls_shift/su_mean         0
_refine_ls_abs_structure_details 'Flack H D (1983), Acta Cryst. A39, 876-881'
_refine_ls_abs_structure_Flack   0.003(13)
_refine_diff_density_max         0.437
_refine_diff_density_min         -0.247
_refine_diff_density_rms         0.066

#----------------------------------------------------------------------------#
#                   ATOMIC TYPES, COORDINATES AND THERMAL PARAMETERS         #
#----------------------------------------------------------------------------#

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 0 '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 0.006 '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'

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 -0.11047(2) 0.25202(6) 0.04635(9) 0.02707(12) Uani 1 1 d . . .
S1 S 0.13239(7) 0.00537(15) 0.02523(16) 0.0236(3) Uani 1 1 d . . .
O10 O 0.0754(2) 0.1451(6) 0.3570(4) 0.0407(10) Uani 1 1 d D . .
H10 H 0.074(3) 0.030(5) 0.414(5) 0.049 Uiso 1 1 d D . .
N5 N 0.1401(2) 0.3832(5) 0.1057(4) 0.0186(8) Uani 1 1 d . . .
N8 N 0.0928(2) 0.3412(5) -0.1203(4) 0.0171(7) Uani 1 1 d . . .
N6 N 0.1204(2) 0.5650(4) 0.0503(6) 0.0250(8) Uani 1 1 d . . .
C11 C 0.0632(4) 0.2509(8) -0.2629(6) 0.0320(12) Uani 1 1 d . . .
H11A H 0.0973 0.135 -0.2815 0.048 Uiso 1 1 calc R . .
H11B H 0.0715 0.3402 -0.3467 0.048 Uiso 1 1 calc R . .
H11C H 0.0012 0.2179 -0.2547 0.048 Uiso 1 1 calc R . .
C2 C 0.1935(3) 0.0056(7) 0.2039(5) 0.0215(10) Uani 1 1 d . . .
H2A H 0.187 -0.121 0.252 0.026 Uiso 1 1 calc R . .
H2B H 0.2562 0.0243 0.1814 0.026 Uiso 1 1 calc R . .
C4 C 0.1794(3) 0.3597(7) 0.2559(5) 0.0247(10) Uani 1 1 d . . .
H4A H 0.1536 0.4538 0.3261 0.03 Uiso 1 1 calc R . .
H4B H 0.2429 0.3848 0.2497 0.03 Uiso 1 1 calc R . .
C3 C 0.1644(3) 0.1592(7) 0.3167(5) 0.0228(10) Uani 1 1 d D . .
H3 H 0.195(2) 0.137(7) 0.417(3) 0.027 Uiso 1 1 d D . .
C7 C 0.0916(3) 0.5316(6) -0.0863(5) 0.0246(10) Uani 1 1 d . . .
H7 H 0.0722 0.6279 -0.1537 0.03 Uiso 1 1 calc R . .
C9 C 0.1232(2) 0.2505(6) 0.0038(4) 0.0182(10) Uani 1 1 d . . .



#----------------------------------------------------------------------------#
#                   MOLECULAR GEOMETRY                                       #
#----------------------------------------------------------------------------#

_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 C9 1.718(4) . ?
S1 C2 1.822(4) . ?
O10 C3 1.399(5) . ?
O10 H10 0.94(2) . ?
N5 C9 1.309(5) . ?
N5 N6 1.385(5) . ?
N5 C4 1.456(5) . ?
N8 C9 1.341(5) . ?
N8 C7 1.354(5) . ?
N8 C11 1.471(6) . ?
N6 C7 1.298(7) . ?
C11 H11A 0.97 . ?
C11 H11B 0.97 . ?
C11 H11C 0.97 . ?
C2 C3 1.521(6) . ?
C2 H2A 0.98 . ?
C2 H2B 0.98 . ?
C4 C3 1.508(6) . ?
C4 H4A 0.98 . ?
C4 H4B 0.98 . ?
C3 H3 1.004(19) . ?
C7 H7 0.94 . ?

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
C9 S1 C2 97.7(2) . . ?
C3 O10 H10 102(3) . . ?
C9 N5 N6 111.1(4) . . ?
C9 N5 C4 128.3(4) . . ?
N6 N5 C4 120.5(4) . . ?
C9 N8 C7 106.5(4) . . ?
C9 N8 C11 126.6(4) . . ?
C7 N8 C11 126.8(4) . . ?
C7 N6 N5 103.5(3) . . ?
N8 C11 H11A 109.5 . . ?
N8 C11 H11B 109.5 . . ?
H11A C11 H11B 109.5 . . ?
N8 C11 H11C 109.5 . . ?
H11A C11 H11C 109.5 . . ?
H11B C11 H11C 109.5 . . ?
C3 C2 S1 114.5(3) . . ?
C3 C2 H2A 108.6 . . ?
S1 C2 H2A 108.6 . . ?
C3 C2 H2B 108.6 . . ?
S1 C2 H2B 108.6 . . ?
H2A C2 H2B 107.6 . . ?
N5 C4 C3 111.2(4) . . ?
N5 C4 H4A 109.4 . . ?
C3 C4 H4A 109.4 . . ?
N5 C4 H4B 109.4 . . ?
C3 C4 H4B 109.4 . . ?
H4A C4 H4B 108 . . ?
O10 C3 C4 107.4(4) . . ?
O10 C3 C2 113.3(4) . . ?
C4 C3 C2 111.9(4) . . ?
O10 C3 H3 102(2) . . ?
C4 C3 H3 113(3) . . ?
C2 C3 H3 109(3) . . ?
N6 C7 N8 111.9(4) . . ?
N6 C7 H7 124 . . ?
N8 C7 H7 124 . . ?
N5 C9 N8 107.0(4) . . ?
N5 C9 S1 127.3(3) . . ?
N8 C9 S1 125.6(3) . . ?

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
C9 N5 N6 C7 0.2(4) . . . . ?
C4 N5 N6 C7 176.7(4) . . . . ?
C9 S1 C2 C3 38.8(4) . . . . ?
C9 N5 C4 C3 -25.3(6) . . . . ?
N6 N5 C4 C3 158.9(4) . . . . ?
N5 C4 C3 O10 -72.5(5) . . . . ?
N5 C4 C3 C2 52.4(5) . . . . ?
S1 C2 C3 O10 58.5(5) . . . . ?
S1 C2 C3 C4 -63.1(4) . . . . ?
N5 N6 C7 N8 -0.6(5) . . . . ?
C9 N8 C7 N6 0.8(5) . . . . ?
C11 N8 C7 N6 178.6(4) . . . . ?
N6 N5 C9 N8 0.4(4) . . . . ?
C4 N5 C9 N8 -175.8(4) . . . . ?
N6 N5 C9 S1 -176.6(3) . . . . ?
C4 N5 C9 S1 7.2(6) . . . . ?
C7 N8 C9 N5 -0.7(4) . . . . ?
C11 N8 C9 N5 -178.4(4) . . . . ?
C7 N8 C9 S1 176.4(3) . . . . ?
C11 N8 C9 S1 -1.4(6) . . . . ?
C2 S1 C9 N5 -12.3(4) . . . . ?
C2 S1 C9 N8 171.3(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
O10 H10 Br 0.94(2) 2.34(2) 3.263(4) 165(4) 2

# END of CIF
_exptl_crystal_recrystallization_method 
'Re-crystallisation from solvent: methanol'
####################################################################### 
# 
# 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_ml160_1
_database_code_depnum_ccdc_archive 'CCDC 2006018'
loop_
_audit_author_name
_audit_author_address
'Doris Braun'
;University of Innsbruck
Austria
;
_audit_update_record             
;
2020-05-27 deposited with the CCDC.	2020-08-21 downloaded from the CCDC.
;

_audit_creation_date             2014-11-21T16:01:57-00:00
_audit_creation_method           'WinGX routine CIF_UPDATE'
_audit_conform_dict_name         cif_core.dic
_audit_conform_dict_version      2.4
_audit_conform_dict_location     ftp://ftp.iucr.org/pub/cif_core.dic

#----------------------------------------------------------------------------#
#                   CHEMICAL INFORMATION                                     #
#----------------------------------------------------------------------------#

_chemical_name_systematic        
;
 ?
;
_chemical_formula_sum            'C5 H9 Br N4 O S'
_chemical_formula_moiety         'C5 H9 N4 O S, Br'

_chemical_formula_weight         253.13

#----------------------------------------------------------------------------#
#                   UNIT CELL INFORMATION                                    #
#----------------------------------------------------------------------------#

_symmetry_cell_setting           monoclinic
_symmetry_space_group_name_H-M   'P 1 21/c 1'
_symmetry_space_group_name_Hall  '-P 2ybc'
loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'-x, y+1/2, -z+1/2'
'-x, -y, -z'
'x, -y-1/2, z-1/2'

_cell_length_a                   5.8057(3)
_cell_length_b                   19.4234(11)
_cell_length_c                   8.3009(5)
_cell_angle_alpha                90
_cell_angle_beta                 102.153(5)
_cell_angle_gamma                90
_cell_volume                     915.08(9)
_cell_formula_units_Z            4
_cell_measurement_temperature    173(2)
_cell_measurement_reflns_used    2548
_cell_measurement_theta_min      4.025
_cell_measurement_theta_max      28.762

#----------------------------------------------------------------------------#
#                   CRYSTAL INFORMATION                                      #
#----------------------------------------------------------------------------#

_exptl_crystal_description       prismatic
_exptl_crystal_colour            colourless
_exptl_crystal_size_max          0.36
_exptl_crystal_size_mid          0.08
_exptl_crystal_size_min          0.08
_exptl_crystal_density_diffrn    1.837
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             504
_exptl_special_details           
;
 ?
;

#----------------------------------------------------------------------------#
#                   ABSORPTION CORRECTION                                    #
#----------------------------------------------------------------------------#

_exptl_absorpt_coefficient_mu    4.68
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
        CrysAlisPro, Agilent Technologies,
        Version 1.171.37.31 (release 14-01-2014 CrysAlis171 .NET)
        (compiled Jan 14 2014,18:38:05)
        Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_absorpt_correction_T_min  0.43357
_exptl_absorpt_correction_T_max  1

#----------------------------------------------------------------------------#
#                   DATA COLLECTION                                          #
#----------------------------------------------------------------------------#

_diffrn_source                   'Enhance (Mo) X-ray Source'
_diffrn_ambient_temperature      173(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_probe          x-ray
_diffrn_detector                 'CCD plate'
_diffrn_detector_area_resol_mean 10.3575
_diffrn_orient_matrix_ub_11      -0.0932471
_diffrn_orient_matrix_ub_12      0.01209
_diffrn_orient_matrix_ub_13      -0.0631493
_diffrn_orient_matrix_ub_21      0.0787512
_diffrn_orient_matrix_ub_22      0.0024637
_diffrn_orient_matrix_ub_23      -0.0545185
_diffrn_orient_matrix_ub_31      -0.0270838
_diffrn_orient_matrix_ub_32      -0.0343596
_diffrn_orient_matrix_ub_33      -0.0260447
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'Xcalibur, Ruby, Gemini ultra'
_diffrn_measurement_method       'ω scans'
_diffrn_reflns_av_R_equivalents  0.0323
_diffrn_reflns_av_unetI/netI     0.0344
_diffrn_reflns_number            5419
_diffrn_reflns_limit_h_min       -6
_diffrn_reflns_limit_h_max       5
_diffrn_reflns_limit_k_min       -19
_diffrn_reflns_limit_k_max       23
_diffrn_reflns_limit_l_min       -9
_diffrn_reflns_limit_l_max       9
_diffrn_reflns_theta_min         3.27
_diffrn_reflns_theta_max         25.34
_diffrn_reflns_theta_full        25.34
_diffrn_measured_fraction_theta_full 0.998
_diffrn_measured_fraction_theta_max 0.998
_reflns_number_total             1658
_reflns_number_gt                1467
_reflns_threshold_expression     >2σ(I)

#----------------------------------------------------------------------------#
#                   COMPUTER PROGRAMS USED                                   #
#----------------------------------------------------------------------------#

_computing_data_collection       
;
        CrysAlisPro, Agilent Technologies,
        Version 1.171.37.31 (release 14-01-2014 CrysAlis171 .NET)
        (compiled Jan 14 2014,18:38:05)
;
_computing_cell_refinement       
;
        CrysAlisPro, Agilent Technologies,
        Version 1.171.37.31 (release 14-01-2014 CrysAlis171 .NET)
        (compiled Jan 14 2014,18:38:05)
;
_computing_data_reduction        
;
        CrysAlisPro, Agilent Technologies,
        Version 1.171.37.31 (release 14-01-2014 CrysAlis171 .NET)
        (compiled Jan 14 2014,18:38:05)
;
_computing_structure_solution    'SIR2002 (Burla et al., 2003)'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 2008)'

#----------------------------------------------------------------------------#
#                   STRUCTURE SOLUTION
#----------------------------------------------------------------------------#

_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_atom_sites_solution_hydrogens   geom

#----------------------------------------------------------------------------#
#                   REFINEMENT INFORMATION                                   #
#----------------------------------------------------------------------------#

_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)+(0.0430P)²+0.5734P] where P=(Fo²+2Fc²)/3'
_refine_ls_hydrogen_treatment    mixed
_refine_ls_extinction_method     none
_refine_ls_number_reflns         1658
_refine_ls_number_parameters     113
_refine_ls_number_restraints     1
_refine_ls_R_factor_all          0.0394
_refine_ls_R_factor_gt           0.0325
_refine_ls_wR_factor_ref         0.0883
_refine_ls_wR_factor_gt          0.0846
_refine_ls_goodness_of_fit_ref   1.146
_refine_ls_restrained_S_all      1.147
_refine_ls_shift/su_max          0
_refine_ls_shift/su_mean         0
_refine_diff_density_max         0.854
_refine_diff_density_min         -0.363
_refine_diff_density_rms         0.103

#----------------------------------------------------------------------------#
#                   ATOMIC TYPES, COORDINATES AND THERMAL PARAMETERS         #
#----------------------------------------------------------------------------#

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 0 '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 0.006 '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'

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 0.35723(6) 0.179018(19) -0.01150(4) 0.02357(17) Uani 1 1 d . . .
S S 0.97850(16) 0.17144(5) 0.40122(10) 0.0186(2) Uani 1 1 d . . .
O1 O 0.9427(5) 0.10056(13) 0.7346(3) 0.0226(6) Uani 1 1 d D . .
H1 H 1.062(5) 0.116(2) 0.798(4) 0.027 Uiso 1 1 d D . .
N3 N 0.4373(5) 0.05177(15) 0.3707(4) 0.0217(7) Uani 1 1 d . . .
N1 N 0.7136(5) 0.06700(16) 0.2396(3) 0.0189(7) Uani 1 1 d . . .
C4 C 0.7550(6) 0.11272(18) 0.3613(4) 0.0160(8) Uani 1 1 d . . .
N4 N 0.5834(5) 0.10268(14) 0.4432(3) 0.0160(6) Uani 1 1 d . . .
C1 C 0.5602(6) 0.13601(19) 0.5980(4) 0.0185(8) Uani 1 1 d . . .
H1A H 0.4927 0.1032 0.6667 0.022 Uiso 1 1 calc R . .
H1B H 0.4531 0.1761 0.5741 0.022 Uiso 1 1 calc R . .
C5 C 0.8444(7) 0.0558(2) 0.1096(4) 0.0277(9) Uani 1 1 d . . .
H5A H 0.9283 0.0981 0.0926 0.042 Uiso 1 1 calc R . .
H5B H 0.7345 0.0435 0.0071 0.042 Uiso 1 1 calc R . .
H5C H 0.9582 0.0185 0.1418 0.042 Uiso 1 1 calc R . .
N2 N 0.5163(6) 0.03027(16) 0.2460(4) 0.0238(7) Uani 1 1 d . . .
C3 C 0.9104(6) 0.20965(18) 0.5867(4) 0.0169(8) Uani 1 1 d . . .
H3A H 1.0573 0.2282 0.6558 0.02 Uiso 1 1 calc R . .
H3B H 0.8009 0.2487 0.5543 0.02 Uiso 1 1 calc R . .
C2 C 0.8001(6) 0.15922(18) 0.6890(4) 0.0168(7) Uani 1 1 d . . .
H2 H 0.7811 0.1833 0.7919 0.02 Uiso 1 1 calc R . .



#----------------------------------------------------------------------------#
#                   MOLECULAR GEOMETRY                                       #
#----------------------------------------------------------------------------#

_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
S C4 1.707(4) . ?
S C3 1.826(3) . ?
O1 C2 1.412(4) . ?
O1 H1 0.836(19) . ?
N3 N2 1.287(4) . ?
N3 N4 1.358(4) . ?
N1 C4 1.328(4) . ?
N1 N2 1.360(4) . ?
N1 C5 1.461(5) . ?
C4 N4 1.333(4) . ?
N4 C1 1.470(4) . ?
C1 C2 1.507(5) . ?
C1 H1A 0.99 . ?
C1 H1B 0.99 . ?
C5 H5A 0.98 . ?
C5 H5B 0.98 . ?
C5 H5C 0.98 . ?
C3 C2 1.523(5) . ?
C3 H3A 0.99 . ?
C3 H3B 0.99 . ?
C2 H2 1 . ?

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
C4 S C3 98.30(16) . . ?
C2 O1 H1 104(3) . . ?
N2 N3 N4 107.3(3) . . ?
C4 N1 N2 109.9(3) . . ?
C4 N1 C5 128.5(3) . . ?
N2 N1 C5 121.6(3) . . ?
N1 C4 N4 104.8(3) . . ?
N1 C4 S 127.1(3) . . ?
N4 C4 S 128.2(3) . . ?
C4 N4 N3 110.2(3) . . ?
C4 N4 C1 126.6(3) . . ?
N3 N4 C1 123.0(3) . . ?
N4 C1 C2 109.0(3) . . ?
N4 C1 H1A 109.9 . . ?
C2 C1 H1A 109.9 . . ?
N4 C1 H1B 109.9 . . ?
C2 C1 H1B 109.9 . . ?
H1A C1 H1B 108.3 . . ?
N1 C5 H5A 109.5 . . ?
N1 C5 H5B 109.5 . . ?
H5A C5 H5B 109.5 . . ?
N1 C5 H5C 109.5 . . ?
H5A C5 H5C 109.5 . . ?
H5B C5 H5C 109.5 . . ?
N3 N2 N1 107.9(3) . . ?
C2 C3 S 113.6(2) . . ?
C2 C3 H3A 108.8 . . ?
S C3 H3A 108.8 . . ?
C2 C3 H3B 108.8 . . ?
S C3 H3B 108.8 . . ?
H3A C3 H3B 107.7 . . ?
O1 C2 C1 108.7(3) . . ?
O1 C2 C3 112.1(3) . . ?
C1 C2 C3 111.5(3) . . ?
O1 C2 H2 108.1 . . ?
C1 C2 H2 108.1 . . ?
C3 C2 H2 108.1 . . ?

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
N2 N1 C4 N4 1.0(4) . . . . ?
C5 N1 C4 N4 178.8(3) . . . . ?
N2 N1 C4 S -178.6(2) . . . . ?
C5 N1 C4 S -0.8(5) . . . . ?
C3 S C4 N1 -178.3(3) . . . . ?
C3 S C4 N4 2.2(3) . . . . ?
N1 C4 N4 N3 -0.7(4) . . . . ?
S C4 N4 N3 178.9(2) . . . . ?
N1 C4 N4 C1 174.1(3) . . . . ?
S C4 N4 C1 -6.3(5) . . . . ?
N2 N3 N4 C4 0.1(4) . . . . ?
N2 N3 N4 C1 -174.9(3) . . . . ?
C4 N4 C1 C2 -24.0(5) . . . . ?
N3 N4 C1 C2 150.2(3) . . . . ?
N4 N3 N2 N1 0.5(4) . . . . ?
C4 N1 N2 N3 -0.9(4) . . . . ?
C5 N1 N2 N3 -178.9(3) . . . . ?
C4 S C3 C2 31.8(3) . . . . ?
N4 C1 C2 O1 -64.8(3) . . . . ?
N4 C1 C2 C3 59.3(4) . . . . ?
S C3 C2 O1 56.3(3) . . . . ?
S C3 C2 C1 -65.8(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
O1 H1 Br 0.836(19) 2.40(2) 3.228(2) 169(4) 1_656

# END of CIF
_exptl_crystal_recrystallization_method 
'Re-crystallisation from solvent: methanol'
####################################################################### 
# 
# 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_shelx_CCDC2
_database_code_depnum_ccdc_archive 'CCDC 2006015'
loop_
_audit_author_name
_audit_author_address
'Doris Braun'
;University of Innsbruck
Austria
;
_audit_update_record             
;
2020-05-27 deposited with the CCDC.	2020-08-21 downloaded from the CCDC.
;

_audit_creation_date             2014-06-14T14:10:30-00:00
_audit_creation_method           'WinGX routine CIF_UPDATE'
_audit_conform_dict_name         cif_core.dic
_audit_conform_dict_version      2.4.3
_audit_conform_dict_location     ftp://ftp.iucr.org/pub/cif_core.dic

#----------------------------------------------------------------------------#
#                   CHEMICAL INFORMATION                                     #
#----------------------------------------------------------------------------#

_chemical_name_systematic        
;
 ?
;
_chemical_formula_moiety         'C7 H11 N2 O S, Cl'
_chemical_formula_sum            'C7 H11 Cl N2 O S'
_chemical_formula_weight         206.70
_chemical_absolute_configuration R

#----------------------------------------------------------------------------#
#                   UNIT CELL INFORMATION                                    #
#----------------------------------------------------------------------------#

_symmetry_cell_setting           monoclinic
_symmetry_space_group_name_H-M   'C 2'
_symmetry_space_group_name_Hall  'C 2y'
_symmetry_Int_Tables_number      5
loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'-x, y, -z'
'x+1/2, y+1/2, z'
'-x+1/2, y+1/2, -z'

_cell_length_a                   17.1960(8)
_cell_length_b                   8.4197(5)
_cell_length_c                   6.6408(3)
_cell_angle_alpha                90
_cell_angle_beta                 95.281(4)
_cell_angle_gamma                90
_cell_volume                     957.41(8)
_cell_formula_units_Z            4
_cell_measurement_temperature    173(2)
_cell_measurement_reflns_used    3381
_cell_measurement_theta_min      4.0120
_cell_measurement_theta_max      28.6400
_cell_measurement_wavelength     0.71073

#----------------------------------------------------------------------------#
#                   CRYSTAL INFORMATION                                      #
#----------------------------------------------------------------------------#

_exptl_crystal_description       block
_exptl_crystal_colour            colorless
_exptl_crystal_size_max          0.3
_exptl_crystal_size_mid          0.2
_exptl_crystal_size_min          0.2
_exptl_crystal_density_diffrn    1.434
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             432
_exptl_special_details           
;
Crystal twinned.

Both parts of twin indexed in CrysAlisPro and raw data processed
to give an hklf 5 formated file.

BASF refined to 0.44046

;

#----------------------------------------------------------------------------#
#                   ABSORPTION CORRECTION                                    #
#----------------------------------------------------------------------------#

_exptl_absorpt_coefficient_mu    0.572
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.94378
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_process_details   
;
CrysAlisPro, Agilent Technologies,
Version 1.171.37.31 (release 14-01-2014 CrysAlis171 .NET)
(compiled Jan 14 2014,18:38:05)
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;

#----------------------------------------------------------------------------#
#                   DATA COLLECTION                                          #
#----------------------------------------------------------------------------#

_diffrn_ambient_temperature      173(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_radiation_probe          x-ray
_diffrn_radiation_monochromator  graphite
_diffrn_detector_area_resol_mean 10.3575
_diffrn_orient_matrix_UB_11      0.0179153000
_diffrn_orient_matrix_UB_12      0.0264125000
_diffrn_orient_matrix_UB_13      0.0944988000
_diffrn_orient_matrix_UB_21      0.0078196000
_diffrn_orient_matrix_UB_22      0.0745932000
_diffrn_orient_matrix_UB_23      -0.0435170000
_diffrn_orient_matrix_UB_31      -0.0365201000
_diffrn_orient_matrix_UB_32      0.0289365000
_diffrn_orient_matrix_UB_33      0.0260158000
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'Xcalibur, Ruby, Gemini ultra'
_diffrn_reflns_number            2255
_diffrn_reflns_limit_h_min       -22
_diffrn_reflns_limit_h_max       23
_diffrn_reflns_limit_k_min       -11
_diffrn_reflns_limit_k_max       11
_diffrn_reflns_limit_l_min       -8
_diffrn_reflns_limit_l_max       8
_diffrn_reflns_theta_min         3.081
_diffrn_reflns_theta_max         28.704
_diffrn_reflns_theta_full        26
_diffrn_measured_fraction_theta_full 0.997
_diffrn_measured_fraction_theta_max 0.96
_diffrn_reflns_Laue_measured_fraction_full 0.997
_diffrn_reflns_Laue_measured_fraction_max 0.96
_diffrn_reflns_point_group_measured_fraction_full 0.825
_diffrn_reflns_point_group_measured_fraction_max 0.769
_reflns_number_total             2255
_reflns_number_gt                2048
_reflns_threshold_expression     'I > 2σ(I)'

#----------------------------------------------------------------------------#
#                   COMPUTER PROGRAMS USED                                   #
#----------------------------------------------------------------------------#

_computing_structure_refinement  'SHELXL-2013 (Sheldrick, 2013)'
_computing_molecular_graphics    'Ortep for Windows (Farrugia, 2012)'
_computing_publication_material  'WinGX publication routines (Farrugia, 2012)'

#----------------------------------------------------------------------------#
#                   STRUCTURE SOLUTION
#----------------------------------------------------------------------------#

_atom_sites_solution_hydrogens   mixed

#----------------------------------------------------------------------------#
#                   REFINEMENT INFORMATION                                   #
#----------------------------------------------------------------------------#

_refine_special_details          'Refined as a 2-component twin.,Twin'
_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0552P)²] where P=(Fo²+2Fc²)/3'
_refine_ls_hydrogen_treatment    mixed
_refine_ls_extinction_method     none
_refine_ls_number_reflns         2255
_refine_ls_number_parameters     114
_refine_ls_number_restraints     2
_refine_ls_number_constraints    0
_refine_ls_R_factor_all          0.0319
_refine_ls_R_factor_gt           0.0287
_refine_ls_wR_factor_ref         0.0765
_refine_ls_wR_factor_gt          0.0757
_refine_ls_goodness_of_fit_ref   1.018
_refine_ls_restrained_S_all      1.018
_refine_ls_shift/su_max          0
_refine_ls_shift/su_mean         0
_refine_ls_abs_structure_details 
;
 Classical Flack method preferred over Parsons because s.u. lower.
;
_refine_ls_abs_structure_Flack   0.34(5)
_refine_diff_density_max         0.402
_refine_diff_density_min         -0.224
_refine_diff_density_rms         0.052

#----------------------------------------------------------------------------#
#                   ATOMIC TYPES, COORDINATES AND THERMAL PARAMETERS         #
#----------------------------------------------------------------------------#

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 0 '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 0.006 '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'
Cl Cl 0.1484 0.1585 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

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_calc_flag
_atom_site_disorder_assembly
_atom_site_disorder_group
Cl1 Cl 0.10923(3) 1.33017(8) 0.27028(8) 0.02755(17) Uani 1 d . .
S1 S 0.19456(3) 0.81828(10) 0.70813(9) 0.02591(16) Uani 1 d . .
N2 N 0.05060(15) 0.9545(3) 0.7421(4) 0.0190(6) Uani 1 d . .
N1 N 0.05087(16) 0.6966(3) 0.7437(4) 0.0223(6) Uani 1 d . .
C1 C -0.02553(19) 0.7455(4) 0.7567(5) 0.0253(7) Uani 1 d . .
H1 H -0.0695 0.6782 0.7641 0.03 Uiso 1 calc . .
C6 C 0.09567(12) 0.8265(4) 0.7333(3) 0.0186(4) Uani 1 d . .
C7 C 0.0796(2) 0.5336(3) 0.7455(6) 0.0308(8) Uani 1 d . .
H7A H 0.1046 0.5131 0.6214 0.046 Uiso 1 calc . .
H7B H 0.0357 0.4602 0.7534 0.046 Uiso 1 calc . .
H7C H 0.1176 0.5181 0.8631 0.046 Uiso 1 calc . .
C2 C -0.02622(18) 0.9046(4) 0.7571(5) 0.0234(7) Uani 1 d . .
H2 H -0.0705 0.9709 0.7658 0.028 Uiso 1 calc . .
C4 C 0.16405(15) 1.1275(3) 0.8178(4) 0.0280(6) Uani 1 d . .
H4 H 0.1814 1.2406 0.8118 0.034 Uiso 1 calc . .
C3 C 0.07719(17) 1.1198(3) 0.7463(5) 0.0253(7) Uani 1 d . .
H3A H 0.0471 1.1823 0.8389 0.03 Uiso 1 calc . .
H3B H 0.0681 1.1665 0.6093 0.03 Uiso 1 calc . .
O1 O 0.17944(13) 1.0734(3) 1.0184(3) 0.0345(5) Uani 1 d . .
H10 H 0.1647(19) 1.138(4) 1.097(5) 0.041 Uiso 1 d . .
C5 C 0.21200(15) 1.0297(4) 0.6833(5) 0.0314(6) Uani 1 d . .
H5A H 0.2681 1.0518 0.719 0.038 Uiso 1 calc . .
H5B H 0.199 1.0616 0.5408 0.038 Uiso 1 calc . .



#----------------------------------------------------------------------------#
#                   MOLECULAR GEOMETRY                                       #
#----------------------------------------------------------------------------#

_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 C6 1.725(2) . ?
S1 C5 1.815(3) . ?
N2 C6 1.332(4) . ?
N2 C2 1.398(4) . ?
N2 C3 1.464(3) . ?
N1 C6 1.344(4) . ?
N1 C1 1.387(4) . ?
N1 C7 1.458(4) . ?
C1 C2 1.339(4) . ?
C4 O1 1.410(3) . ?
C4 C5 1.513(4) . ?
C4 C3 1.527(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
C6 S1 C5 98.16(13) . . ?
C6 N2 C2 108.5(2) . . ?
C6 N2 C3 126.0(2) . . ?
C2 N2 C3 125.4(2) . . ?
C6 N1 C1 108.2(2) . . ?
C6 N1 C7 124.9(2) . . ?
C1 N1 C7 126.9(2) . . ?
C2 C1 N1 107.8(3) . . ?
N2 C6 N1 108.54(18) . . ?
N2 C6 S1 128.3(2) . . ?
N1 C6 S1 123.2(2) . . ?
C1 C2 N2 107.0(3) . . ?
O1 C4 C5 108.5(2) . . ?
O1 C4 C3 111.9(2) . . ?
C5 C4 C3 111.4(2) . . ?
N2 C3 C4 109.9(2) . . ?
C4 C5 S1 112.11(19) . . ?

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
C6 N1 C1 C2 -0.8(4) . . . . ?
C7 N1 C1 C2 177.8(4) . . . . ?
C2 N2 C6 N1 -0.5(3) . . . . ?
C3 N2 C6 N1 176.5(3) . . . . ?
C2 N2 C6 S1 178.4(2) . . . . ?
C3 N2 C6 S1 -4.7(4) . . . . ?
C1 N1 C6 N2 0.8(3) . . . . ?
C7 N1 C6 N2 -177.8(3) . . . . ?
C1 N1 C6 S1 -178.08(19) . . . . ?
C7 N1 C6 S1 3.3(4) . . . . ?
C5 S1 C6 N2 -3.3(3) . . . . ?
C5 S1 C6 N1 175.4(2) . . . . ?
N1 C1 C2 N2 0.6(5) . . . . ?
C6 N2 C2 C1 -0.1(4) . . . . ?
C3 N2 C2 C1 -177.1(4) . . . . ?
C6 N2 C3 C4 -21.1(4) . . . . ?
C2 N2 C3 C4 155.4(3) . . . . ?
O1 C4 C3 N2 -63.8(3) . . . . ?
C5 C4 C3 N2 57.8(3) . . . . ?
O1 C4 C5 S1 55.0(3) . . . . ?
C3 C4 C5 S1 -68.6(3) . . . . ?
C6 S1 C5 C4 37.5(2) . . . . ?

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
O1 H10 Cl1 0.81(2) 2.25(2) 3.050(2) 170(4) 1_556


# END of CIF
