# Electronic Supplementary Material (ESI) for Green Chemistry.
# This journal is © The Royal Society of Chemistry 2021

####################################################################### 
# 
# 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_mo_jd190421_0m_a
_database_code_depnum_ccdc_archive 'CCDC 2090344'
loop_
_audit_author_name
_audit_author_address
'Tirtha Mandal'
;INDIAN ASSOCIATION FOR THE CULTIVATION OF SCIENCE
India
;
_audit_update_record             
;
2021-06-16 deposited with the CCDC.	2021-12-08 downloaded from the CCDC.
;
_audit_creation_date             2021-04-30
_audit_creation_method           
;
Olex2 1.2
(compiled 2018.05.29 svn.r3508 for OlexSys, GUI svn.r5506)
;
_shelxl_version_number           2014-3
_chemical_name_common            ?
_chemical_name_systematic        
;
 ?
;
_chemical_formula_moiety         'C15 H12 Br N3 O2 S'
_chemical_formula_sum            'C15 H12 Br N3 O2 S'
_chemical_formula_weight         378.25
_chemical_absolute_configuration ?
_chemical_melting_point          ?
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'
Br Br -0.2901 2.4595 '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'

_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.
;
_space_group_crystal_system      orthorhombic
_space_group_IT_number           19
_space_group_name_H-M_alt        'P 21 21 21'
_space_group_name_Hall           'P 2ac 2ab'
loop_
_space_group_symop_operation_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                   4.8673(12)
_cell_length_b                   11.348(3)
_cell_length_c                   27.751(6)
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_volume                     1532.8(6)
_cell_formula_units_Z            4
_cell_measurement_reflns_used    5709
_cell_measurement_temperature    174(2)
_cell_measurement_theta_max      24.76
_cell_measurement_theta_min      2.32
_shelx_estimated_absorpt_T_max   ?
_shelx_estimated_absorpt_T_min   ?
_exptl_absorpt_coefficient_mu    2.828
_exptl_absorpt_correction_T_max  0.7452
_exptl_absorpt_correction_T_min  0.5854
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
SADABS-2016/2 (Bruker,2016/2) was used for absorption correction.
wR2(int) was 0.1231 before and 0.0619 after correction.
The Ratio of minimum to maximum transmission is 0.7856.
The λ/2 correction factor is Not present.
;
_exptl_crystal_colour            colorless
_exptl_crystal_density_diffrn    1.639
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       needle
_exptl_crystal_F_000             760
_exptl_crystal_size_max          ?
_exptl_crystal_size_mid          ?
_exptl_crystal_size_min          ?
_exptl_special_details           
;
 ?
;
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0500
_diffrn_reflns_av_unetI/netI     0.0446
_diffrn_reflns_Laue_measured_fraction_full 0.976
_diffrn_reflns_Laue_measured_fraction_max 0.995
_diffrn_reflns_limit_h_max       5
_diffrn_reflns_limit_h_min       -5
_diffrn_reflns_limit_k_max       13
_diffrn_reflns_limit_k_min       -13
_diffrn_reflns_limit_l_max       33
_diffrn_reflns_limit_l_min       -32
_diffrn_reflns_number            15737
_diffrn_reflns_point_group_measured_fraction_full 0.976
_diffrn_reflns_point_group_measured_fraction_max 0.997
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         25.000
_diffrn_reflns_theta_min         2.318
_diffrn_ambient_temperature      174.29
_diffrn_detector_area_resol_mean ?
_diffrn_measured_fraction_theta_full 0.976
_diffrn_measured_fraction_theta_max 0.995
_diffrn_measurement_device_type  'Bruker APEX-II CCD'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_source                   ?
_diffrn_standards_number         0
_reflns_Friedel_coverage         0.674
_reflns_Friedel_fraction_full    0.976
_reflns_Friedel_fraction_max     0.999
_reflns_number_gt                2378
_reflns_number_total             2691
_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.
;
_reflns_threshold_expression     'I > 2σ(I)'
_computing_cell_refinement       'SAINT V8.38A (?, 2016)'
_computing_data_collection       ?
_computing_data_reduction        'SAINT V8.38A (?, 2016)'
_computing_molecular_graphics    'Olex2 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 (Dolomanov et al., 2009)'
_computing_structure_refinement  'ShelXL (Sheldrick, 2015)'
_computing_structure_solution    'SHELXT 2014/5 (Sheldrick, 2014)'
_refine_diff_density_max         0.218
_refine_diff_density_min         -0.302
_refine_diff_density_rms         0.045
_refine_ls_abs_structure_details 
;
 Refined as an inversion twin.
;
_refine_ls_abs_structure_Flack   0.041(14)
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.060
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     200
_refine_ls_number_reflns         2691
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0392
_refine_ls_R_factor_gt           0.0317
_refine_ls_restrained_S_all      1.060
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0067P)²+0.6928P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0641
_refine_ls_wR_factor_ref         0.0665
_refine_special_details          
;
 Refined as a 2-component inversion twin.
;
_olex2_refinement_description    
;
1. Twinned data refinement
 Scales: 0.959(14)
 0.041(14)
2. Fixed Uiso
 At 1.2 times of:
  All C(H) groups, All C(H,H) groups
3.a Secondary CH2 refined with riding coordinates:
 C00K(H00A,H00C)
3.b Aromatic/amide H refined with riding coordinates:
 C009(H009), C00B(H00B), C00D(H00D), C00E(H00E), C00G(H00G), C00H(H00H),
 C00I(H00I), C00J(H00J), C00L(H00L), C00M(H00M)
;
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     ?
_atom_sites_solution_secondary   ?
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 0.25317(14) 0.30871(4) 0.39031(2) 0.0681(2) Uani 1 1 d . . . . .
S002 S 0.6971(2) 0.60180(9) 0.59502(3) 0.0335(2) Uani 1 1 d . . . . .
O003 O 0.9045(6) 0.6746(3) 0.57495(10) 0.0409(7) Uani 1 1 d . . . . .
O004 O 0.7571(8) 0.5134(2) 0.62977(9) 0.0456(7) Uani 1 1 d . . . . .
N005 N 0.4812(7) 0.6944(3) 0.62499(11) 0.0325(8) Uani 1 1 d . . . . .
N006 N 0.2492(9) 0.8515(3) 0.63634(11) 0.0399(8) Uani 1 1 d . . . . .
N007 N 0.4286(7) 0.8050(3) 0.60750(12) 0.0396(8) Uani 1 1 d . . . . .
C008 C 0.1801(8) 0.7730(3) 0.67197(13) 0.0319(10) Uani 1 1 d . . . . .
C009 C 0.3258(8) 0.6726(4) 0.66449(14) 0.0350(10) Uani 1 1 d . . . . .
H009 H 0.3200 0.6022 0.6830 0.042 Uiso 1 1 calc R . . . .
C00A C 0.1878(9) 0.4538(3) 0.47396(15) 0.0364(10) Uani 1 1 d . . . . .
C00B C 0.3570(9) 0.5499(4) 0.46644(16) 0.0411(11) Uani 1 1 d . . . . .
H00B H 0.3663 0.5846 0.4353 0.049 Uiso 1 1 calc R . . . .
C00C C -0.0232(8) 0.8018(4) 0.70902(14) 0.0360(10) Uani 1 1 d . . . . .
C00D C 0.1764(9) 0.4031(4) 0.51927(16) 0.0420(11) Uani 1 1 d . . . . .
H00D H 0.0611 0.3368 0.5245 0.050 Uiso 1 1 calc R . . . .
C00E C 0.3297(9) 0.4472(4) 0.55692(15) 0.0388(11) Uani 1 1 d . . . . .
H00E H 0.3212 0.4123 0.5880 0.047 Uiso 1 1 calc R . . . .
C00F C 0.4967(8) 0.5441(3) 0.54826(14) 0.0305(9) Uani 1 1 d . . . . .
C00G C 0.5122(9) 0.5960(4) 0.50340(14) 0.0372(10) Uani 1 1 d . . . . .
H00G H 0.6277 0.6622 0.4981 0.045 Uiso 1 1 calc R . . . .
C00H C -0.1762(9) 0.9041(4) 0.70642(16) 0.0443(11) Uani 1 1 d . . . . .
H00H H -0.1470 0.9573 0.6805 0.053 Uiso 1 1 calc R . . . .
C00I C -0.2604(13) 0.7520(5) 0.78219(16) 0.0607(13) Uani 1 1 d . . . . .
H00I H -0.2876 0.6998 0.8085 0.073 Uiso 1 1 calc R . . . .
C00J C -0.4132(11) 0.8534(5) 0.77918(19) 0.0576(15) Uani 1 1 d . . . . .
H00J H -0.5468 0.8709 0.8031 0.069 Uiso 1 1 calc R . . . .
C00K C 0.0231(11) 0.4055(4) 0.43297(17) 0.0538(13) Uani 1 1 d . . . . .
H00A H -0.0574 0.4714 0.4143 0.065 Uiso 1 1 calc R . . . .
H00C H -0.1295 0.3571 0.4458 0.065 Uiso 1 1 calc R . . . .
C00L C -0.0685(11) 0.7254(4) 0.74756(17) 0.0516(13) Uani 1 1 d . . . . .
H00L H 0.0341 0.6544 0.7499 0.062 Uiso 1 1 calc R . . . .
C00M C -0.3710(10) 0.9300(4) 0.74100(19) 0.0536(14) Uani 1 1 d . . . . .
H00M H -0.4761 1.0003 0.7386 0.064 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 C00K 1.965(5) . ?
S002 O003 1.418(3) . ?
S002 O004 1.422(3) . ?
S002 N005 1.703(3) . ?
S002 C00F 1.750(4) . ?
N005 N007 1.370(5) . ?
N005 C009 1.354(5) . ?
N006 N007 1.297(5) . ?
N006 C008 1.373(5) . ?
C008 C009 1.358(5) . ?
C008 C00C 1.464(5) . ?
C009 H009 0.9500 . ?
C00A C00B 1.382(6) . ?
C00A C00D 1.384(6) . ?
C00A C00K 1.496(6) . ?
C00B H00B 0.9500 . ?
C00B C00G 1.377(6) . ?
C00C C00H 1.381(6) . ?
C00C C00L 1.394(6) . ?
C00D H00D 0.9500 . ?
C00D C00E 1.378(6) . ?
C00E H00E 0.9500 . ?
C00E C00F 1.388(6) . ?
C00F C00G 1.379(5) . ?
C00G H00G 0.9500 . ?
C00H H00H 0.9500 . ?
C00H C00M 1.381(6) . ?
C00I H00I 0.9500 . ?
C00I C00J 1.372(7) . ?
C00I C00L 1.374(7) . ?
C00J H00J 0.9500 . ?
C00J C00M 1.386(7) . ?
C00K H00A 0.9900 . ?
C00K H00C 0.9900 . ?
C00L H00L 0.9500 . ?
C00M H00M 0.9500 . ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
O003 S002 O004 122.1(2) . . ?
O003 S002 N005 105.78(17) . . ?
O003 S002 C00F 108.85(19) . . ?
O004 S002 N005 103.35(17) . . ?
O004 S002 C00F 110.69(19) . . ?
N005 S002 C00F 104.43(18) . . ?
N007 N005 S002 120.5(3) . . ?
C009 N005 S002 128.8(3) . . ?
C009 N005 N007 110.5(3) . . ?
N007 N006 C008 110.2(3) . . ?
N006 N007 N005 106.3(3) . . ?
N006 C008 C00C 121.7(4) . . ?
C009 C008 N006 107.9(3) . . ?
C009 C008 C00C 130.4(4) . . ?
N005 C009 C008 105.2(3) . . ?
N005 C009 H009 127.4 . . ?
C008 C009 H009 127.4 . . ?
C00B C00A C00D 119.3(4) . . ?
C00B C00A C00K 119.6(4) . . ?
C00D C00A C00K 121.1(4) . . ?
C00A C00B H00B 119.5 . . ?
C00G C00B C00A 120.9(4) . . ?
C00G C00B H00B 119.5 . . ?
C00H C00C C008 121.0(4) . . ?
C00H C00C C00L 118.5(4) . . ?
C00L C00C C008 120.4(4) . . ?
C00A C00D H00D 119.5 . . ?
C00E C00D C00A 121.1(4) . . ?
C00E C00D H00D 119.5 . . ?
C00D C00E H00E 120.9 . . ?
C00D C00E C00F 118.3(4) . . ?
C00F C00E H00E 120.9 . . ?
C00E C00F S002 119.6(3) . . ?
C00G C00F S002 118.6(3) . . ?
C00G C00F C00E 121.8(4) . . ?
C00B C00G C00F 118.7(4) . . ?
C00B C00G H00G 120.7 . . ?
C00F C00G H00G 120.7 . . ?
C00C C00H H00H 119.6 . . ?
C00C C00H C00M 120.9(4) . . ?
C00M C00H H00H 119.6 . . ?
C00J C00I H00I 119.7 . . ?
C00J C00I C00L 120.7(5) . . ?
C00L C00I H00I 119.7 . . ?
C00I C00J H00J 120.3 . . ?
C00I C00J C00M 119.5(5) . . ?
C00M C00J H00J 120.3 . . ?
Br1 C00K H00A 109.4 . . ?
Br1 C00K H00C 109.4 . . ?
C00A C00K Br1 111.0(3) . . ?
C00A C00K H00A 109.4 . . ?
C00A C00K H00C 109.4 . . ?
H00A C00K H00C 108.0 . . ?
C00C C00L H00L 119.8 . . ?
C00I C00L C00C 120.5(5) . . ?
C00I C00L H00L 119.8 . . ?
C00H C00M C00J 120.0(5) . . ?
C00H C00M H00M 120.0 . . ?
C00J C00M H00M 120.0 . . ?

_olex2_submission_special_instructions 'No special instructions were received'
loop_
_twin_individual_id
_twin_individual_mass_fraction_refined
1 0.959(14)
2 0.041(14)

####################################################################### 
# 
# 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_mo_jdoc080221_0m_a
_database_code_depnum_ccdc_archive 'CCDC 2090346'
loop_
_audit_author_name
_audit_author_address
'Tirtha Mandal'
;INDIAN ASSOCIATION FOR THE CULTIVATION OF SCIENCE
India
;
_audit_update_record             
;
2021-06-16 deposited with the CCDC.	2021-12-08 downloaded from the CCDC.
;
_audit_creation_date             2021-03-24
_audit_creation_method           
;
Olex2 1.2
(compiled 2018.05.29 svn.r3508 for OlexSys, GUI svn.r5506)
;
_shelx_SHELXL_version_number     2018/3
_chemical_name_common            ?
_chemical_name_systematic        ?
_chemical_formula_moiety         'C11 H14 N4 O3 S'
_chemical_formula_sum            'C11 H14 N4 O3 S'
_chemical_formula_weight         282.32
_chemical_absolute_configuration ?
_chemical_melting_point          ?
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'

_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.
;
_space_group_crystal_system      orthorhombic
_space_group_IT_number           19
_space_group_name_H-M_alt        'P 21 21 21'
_space_group_name_Hall           'P 2ac 2ab'
loop_
_space_group_symop_operation_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                   5.3437(5)
_cell_length_b                   14.4207(16)
_cell_length_c                   16.6141(16)
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_volume                     1280.3(2)
_cell_formula_units_Z            4
_cell_measurement_reflns_used    7984
_cell_measurement_temperature    100(2)
_cell_measurement_theta_max      25.06
_cell_measurement_theta_min      2.45
_shelx_estimated_absorpt_T_max   ?
_shelx_estimated_absorpt_T_min   ?
_exptl_absorpt_coefficient_mu    0.263
_exptl_absorpt_correction_T_max  0.7452
_exptl_absorpt_correction_T_min  0.5890
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
SADABS-2016/2 (Bruker,2016/2) was used for absorption correction.
wR2(int) was 0.1085 before and 0.0719 after correction.
The Ratio of minimum to maximum transmission is 0.7904.
The λ/2 correction factor is Not present.
;
_exptl_absorpt_special_details   ?
_exptl_crystal_colour            colourless
_exptl_crystal_density_diffrn    1.465
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       needle
_exptl_crystal_F_000             592
_exptl_crystal_size_max          ?
_exptl_crystal_size_mid          ?
_exptl_crystal_size_min          ?
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.1207
_diffrn_reflns_av_unetI/netI     0.0656
_diffrn_reflns_Laue_measured_fraction_full 0.990
_diffrn_reflns_Laue_measured_fraction_max 0.990
_diffrn_reflns_limit_h_max       6
_diffrn_reflns_limit_h_min       -6
_diffrn_reflns_limit_k_max       17
_diffrn_reflns_limit_k_min       -17
_diffrn_reflns_limit_l_max       18
_diffrn_reflns_limit_l_min       -19
_diffrn_reflns_number            11636
_diffrn_reflns_point_group_measured_fraction_full 0.992
_diffrn_reflns_point_group_measured_fraction_max 0.992
_diffrn_reflns_theta_full        24.993
_diffrn_reflns_theta_max         24.993
_diffrn_reflns_theta_min         2.452
_diffrn_ambient_temperature      99.83
_diffrn_detector_area_resol_mean ?
_diffrn_measured_fraction_theta_full 0.990
_diffrn_measured_fraction_theta_max 0.990
_diffrn_measurement_device_type  'Bruker APEX-II CCD'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_source                   ?
_diffrn_standards_number         0
_reflns_Friedel_coverage         0.684
_reflns_Friedel_fraction_full    0.996
_reflns_Friedel_fraction_max     0.996
_reflns_number_gt                2156
_reflns_number_total             2241
_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. Completness statistics refer to single and
 composite reflections containing twin component 1 only.
;
_reflns_threshold_expression     'I > 2σ(I)'
_computing_cell_refinement       'SAINT V8.38A (?, 2016)'
_computing_data_collection       ?
_computing_data_reduction        'SAINT V8.38A (?, 2016)'
_computing_molecular_graphics    'Olex2 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 (Dolomanov et al., 2009)'
_computing_structure_refinement  'ShelXL (Sheldrick, 2015)'
_computing_structure_solution    'SHELXT 2014/5 (Sheldrick, 2014)'
_refine_diff_density_max         0.364
_refine_diff_density_min         -0.393
_refine_diff_density_rms         0.067
_refine_ls_abs_structure_details 
;
 Refined as an inversion twin.
;
_refine_ls_abs_structure_Flack   0.39(13)
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.070
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     176
_refine_ls_number_reflns         2241
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0450
_refine_ls_R_factor_gt           0.0424
_refine_ls_restrained_S_all      1.070
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0288P)²+0.8901P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0905
_refine_ls_wR_factor_ref         0.0923
_refine_special_details          
;
 Refined as a 2-component inversion twin.
;
_olex2_refinement_description    
;
1. Twinned data refinement
 Scales: 0.61(13)
 0.39(13)
2. Fixed Uiso
 At 1.2 times of:
  All C(H) groups
 At 1.5 times of:
  All C(H,H,H) groups
3.a Aromatic/amide H refined with riding coordinates:
 C00A(H00A), C00D(H00D), C00E(H00E), C00F(H00F), C00I(H00K)
3.b Idealised Me refined as rotating group:
 C00G(H00B,H00C,H00G), C00H(H00H,H00I,H00J), C00J(H00L,H00M,H00N)
;
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     ?
_atom_sites_solution_secondary   ?
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 0.86826(15) 0.28606(6) 0.35531(5) 0.0178(2) Uani 1 1 d . . . . .
O002 O 0.9432(4) 0.26621(18) 0.43537(13) 0.0244(6) Uani 1 1 d . . . . .
O003 O 1.0429(4) 0.31425(18) 0.29560(14) 0.0227(6) Uani 1 1 d . . . . .
O004 O 0.4116(4) 0.50699(17) 0.57030(13) 0.0207(6) Uani 1 1 d . . . . .
N005 N 0.4333(5) 0.48698(19) 0.32399(15) 0.0180(6) Uani 1 1 d . . . . .
N006 N 0.5984(5) 0.42807(19) 0.29935(15) 0.0180(6) Uani 1 1 d . . . . .
N007 N 0.6692(5) 0.37827(19) 0.36579(15) 0.0166(6) Uani 1 1 d . . . . .
N008 N 0.7031(5) 0.2025(2) 0.32119(16) 0.0215(7) Uani 1 1 d . . . . .
C009 C 0.2291(6) 0.5542(2) 0.5304(2) 0.0180(7) Uani 1 1 d . . . . .
C00A C 0.5432(6) 0.4070(2) 0.43213(18) 0.0175(7) Uani 1 1 d . . . . .
H00A H 0.556667 0.383578 0.485391 0.021 Uiso 1 1 calc R . . . .
C00B C 0.3928(6) 0.4770(2) 0.40545(18) 0.0157(7) Uani 1 1 d . . . . .
C00C C 0.2132(6) 0.5380(2) 0.44684(19) 0.0181(7) Uani 1 1 d . . . . .
C00D C 0.0275(7) 0.5830(2) 0.4032(2) 0.0196(7) Uani 1 1 d . . . . .
H00D H 0.013197 0.571863 0.347018 0.024 Uiso 1 1 calc R . . . .
C00E C 0.0617(7) 0.6149(3) 0.5672(2) 0.0229(8) Uani 1 1 d . . . . .
H00E H 0.070997 0.625469 0.623528 0.027 Uiso 1 1 calc R . . . .
C00F C -0.1183(7) 0.6599(3) 0.5217(2) 0.0251(8) Uani 1 1 d . . . . .
H00F H -0.229839 0.702135 0.546964 0.030 Uiso 1 1 calc R . . . .
C00G C 0.6075(7) 0.2123(3) 0.23823(19) 0.0267(8) Uani 1 1 d . . . . .
H00B H 0.570184 0.150785 0.216137 0.040 Uiso 1 1 calc GR . . . .
H00C H 0.734263 0.242693 0.204769 0.040 Uiso 1 1 calc GR . . . .
H00G H 0.454660 0.249809 0.238720 0.040 Uiso 1 1 calc GR . . . .
C00H C 0.4595(7) 0.5330(3) 0.6519(2) 0.0283(9) Uani 1 1 d . . . . .
H00H H 0.490408 0.599939 0.654670 0.043 Uiso 1 1 calc GR . . . .
H00I H 0.606690 0.499580 0.671744 0.043 Uiso 1 1 calc GR . . . .
H00J H 0.314086 0.517425 0.685208 0.043 Uiso 1 1 calc GR . . . .
C00I C -0.1369(7) 0.6438(3) 0.4401(2) 0.0250(8) Uani 1 1 d . . . . .
H00K H -0.262173 0.674244 0.409321 0.030 Uiso 1 1 calc R . . . .
C00J C 0.5263(7) 0.1582(3) 0.3777(2) 0.0273(9) Uani 1 1 d . . . . .
H00L H 0.375114 0.196304 0.382188 0.041 Uiso 1 1 calc GR . . . .
H00M H 0.605081 0.152378 0.430704 0.041 Uiso 1 1 calc GR . . . .
H00N H 0.481336 0.096476 0.357630 0.041 Uiso 1 1 calc GR . . . .


_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 O002 1.418(2) . ?
S1 O003 1.421(2) . ?
S1 N007 1.712(3) . ?
S1 N008 1.598(3) . ?
O004 C009 1.362(4) . ?
O004 C00H 1.430(4) . ?
N005 N006 1.291(4) . ?
N005 C00B 1.378(4) . ?
N006 N007 1.370(4) . ?
N007 C00A 1.356(4) . ?
N008 C00G 1.477(4) . ?
N008 C00J 1.477(4) . ?
C009 C00C 1.411(5) . ?
C009 C00E 1.393(5) . ?
C00A H00A 0.9500 . ?
C00A C00B 1.364(5) . ?
C00B C00C 1.472(5) . ?
C00C C00D 1.390(5) . ?
C00D H00D 0.9500 . ?
C00D C00I 1.384(5) . ?
C00E H00E 0.9500 . ?
C00E C00F 1.384(5) . ?
C00F H00F 0.9500 . ?
C00F C00I 1.380(5) . ?
C00G H00B 0.9800 . ?
C00G H00C 0.9800 . ?
C00G H00G 0.9800 . ?
C00H H00H 0.9800 . ?
C00H H00I 0.9800 . ?
C00H H00J 0.9800 . ?
C00I H00K 0.9500 . ?
C00J H00L 0.9800 . ?
C00J H00M 0.9800 . ?
C00J H00N 0.9800 . ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
O002 S1 O003 121.81(15) . . ?
O002 S1 N007 103.69(13) . . ?
O002 S1 N008 109.65(15) . . ?
O003 S1 N007 104.88(14) . . ?
O003 S1 N008 109.32(15) . . ?
N008 S1 N007 106.20(14) . . ?
C009 O004 C00H 117.3(3) . . ?
N006 N005 C00B 110.5(3) . . ?
N005 N006 N007 106.1(2) . . ?
N006 N007 S1 119.8(2) . . ?
C00A N007 S1 128.9(2) . . ?
C00A N007 N006 110.9(3) . . ?
C00G N008 S1 116.7(2) . . ?
C00G N008 C00J 114.4(3) . . ?
C00J N008 S1 117.0(2) . . ?
O004 C009 C00C 116.0(3) . . ?
O004 C009 C00E 124.1(3) . . ?
C00E C009 C00C 119.8(3) . . ?
N007 C00A H00A 127.6 . . ?
N007 C00A C00B 104.7(3) . . ?
C00B C00A H00A 127.6 . . ?
N005 C00B C00C 119.9(3) . . ?
C00A C00B N005 107.7(3) . . ?
C00A C00B C00C 132.4(3) . . ?
C009 C00C C00B 121.3(3) . . ?
C00D C00C C009 118.6(3) . . ?
C00D C00C C00B 120.0(3) . . ?
C00C C00D H00D 119.4 . . ?
C00I C00D C00C 121.2(3) . . ?
C00I C00D H00D 119.4 . . ?
C009 C00E H00E 119.9 . . ?
C00F C00E C009 120.1(3) . . ?
C00F C00E H00E 119.9 . . ?
C00E C00F H00F 119.8 . . ?
C00I C00F C00E 120.5(3) . . ?
C00I C00F H00F 119.8 . . ?
N008 C00G H00B 109.5 . . ?
N008 C00G H00C 109.5 . . ?
N008 C00G H00G 109.5 . . ?
H00B C00G H00C 109.5 . . ?
H00B C00G H00G 109.5 . . ?
H00C C00G H00G 109.5 . . ?
O004 C00H H00H 109.5 . . ?
O004 C00H H00I 109.5 . . ?
O004 C00H H00J 109.5 . . ?
H00H C00H H00I 109.5 . . ?
H00H C00H H00J 109.5 . . ?
H00I C00H H00J 109.5 . . ?
C00D C00I H00K 120.1 . . ?
C00F C00I C00D 119.7(3) . . ?
C00F C00I H00K 120.1 . . ?
N008 C00J H00L 109.5 . . ?
N008 C00J H00M 109.5 . . ?
N008 C00J H00N 109.5 . . ?
H00L C00J H00M 109.5 . . ?
H00L C00J H00N 109.5 . . ?
H00M C00J H00N 109.5 . . ?

_olex2_submission_special_instructions 'No special instructions were received'
loop_
_twin_individual_id
_twin_individual_mass_fraction_refined
1 0.61(13)
2 0.39(13)

