# Electronic Supplementary Material (ESI) for Organic & Biomolecular Chemistry.
# 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_YM671
_database_code_depnum_ccdc_archive 'CCDC 1828325'
loop_
_audit_author_name
_audit_author_address
'Daisuke Hashizume'
;RIKEN
Japan
;
_audit_update_record             
;
2018-03-08 deposited with the CCDC.	2020-11-27 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2014
_chemical_name_systematic        2-Toluenesulfonamide
_chemical_name_common            ?
_chemical_melting_point          429
_chemical_formula_moiety         'C7 H9 N O2 S'
_chemical_formula_sum            'C7 H9 N O2 S'
_chemical_formula_weight         171.21

loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
N N 0.0061 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0106 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
S S 0.1246 0.1234 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_space_group_crystal_system      tetragonal
_space_group_IT_number           88
_space_group_name_H-M_alt        'I 41/a'
_space_group_name_Hall           '-I 4ad'

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

loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x, -y+1/2, z'
'-y+3/4, x+1/4, z+1/4'
'y+1/4, -x+1/4, z+1/4'
'x+1/2, y+1/2, z+1/2'
'-x+1/2, -y+1, z+1/2'
'-y+5/4, x+3/4, z+3/4'
'y+3/4, -x+3/4, z+3/4'
'-x, -y, -z'
'x, y-1/2, -z'
'y-3/4, -x-1/4, -z-1/4'
'-y-1/4, x-1/4, -z-1/4'
'-x+1/2, -y+1/2, -z+1/2'
'x+1/2, y, -z+1/2'
'y-1/4, -x+1/4, -z+1/4'
'-y+1/4, x+1/4, -z+1/4'

_cell_length_a                   18.5210(4)
_cell_length_b                   18.5210(4)
_cell_length_c                   9.0228(2)
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_volume                     3095.07(15)
_cell_formula_units_Z            16
_cell_measurement_temperature    90
_cell_measurement_reflns_used    24659
_cell_measurement_theta_min      2.199
_cell_measurement_theta_max      30.924

_exptl_crystal_description       block
_exptl_crystal_colour            colourless
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.470
_exptl_crystal_F_000             1440
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.22
_exptl_crystal_size_mid          0.21
_exptl_crystal_size_min          0.18
_exptl_absorpt_coefficient_mu    0.363
_shelx_estimated_absorpt_T_min   0.924
_shelx_estimated_absorpt_T_max   0.937
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.88692
_exptl_absorpt_correction_T_max  0.90451
_exptl_absorpt_process_details   
;
 MULABS - Empirical Correction for Absorption Anisotropy.
 R.H. Blessing, Acta Cryst. (1995), A51, 33-38.
;

_exptl_special_details           
;
 ?
;

_diffrn_ambient_temperature      90
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_source                   'Fine-focus rotating anode'
_diffrn_measurement_device_type  'Rigaku AFC-8 with Saturn70 CCD'
_diffrn_measurement_method       ω-scan
_diffrn_detector_area_resol_mean 7.31
_diffrn_reflns_number            24659
_diffrn_reflns_av_unetI/netI     0.0215
_diffrn_reflns_av_R_equivalents  0.0461
_diffrn_reflns_limit_h_min       -26
_diffrn_reflns_limit_h_max       26
_diffrn_reflns_limit_k_min       -26
_diffrn_reflns_limit_k_max       26
_diffrn_reflns_limit_l_min       -13
_diffrn_reflns_limit_l_max       13
_diffrn_reflns_theta_min         2.199
_diffrn_reflns_theta_max         30.924
_diffrn_reflns_theta_full        25.242
_diffrn_measured_fraction_theta_max 0.998
_diffrn_measured_fraction_theta_full 0.999
_diffrn_reflns_Laue_measured_fraction_max 0.998
_diffrn_reflns_Laue_measured_fraction_full 0.999
_diffrn_reflns_point_group_measured_fraction_max 0.998
_diffrn_reflns_point_group_measured_fraction_full 0.999
_reflns_number_total             2444
_reflns_number_gt                2197
_reflns_threshold_expression     'I > 2σ(I)'
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_max     .
_reflns_Friedel_fraction_full    .

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

_computing_data_collection       CrystalClear
_computing_cell_refinement       HKL2000
_computing_data_reduction        HKL2000
_computing_structure_solution    SIR2011
_computing_structure_refinement  'SHELXL-2014 (Sheldrick, 2014)'
_computing_molecular_graphics    SV
_computing_publication_material  'SHELXL-2014 (Sheldrick, 2014)'

_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)+(0.0473P)²+2.5996P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_atom_sites_solution_hydrogens   difmap
_refine_ls_hydrogen_treatment    mixed
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       .
_refine_ls_number_reflns         2444
_refine_ls_number_parameters     109
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0360
_refine_ls_R_factor_gt           0.0324
_refine_ls_wR_factor_ref         0.0915
_refine_ls_wR_factor_gt          0.0887
_refine_ls_goodness_of_fit_ref   1.067
_refine_ls_restrained_S_all      1.067
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000

loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_site_symmetry_order
_atom_site_calc_flag
_atom_site_refinement_flags_posn
_atom_site_refinement_flags_adp
_atom_site_refinement_flags_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
S1 S 0.13358(2) 0.12510(2) 0.26295(3) 0.01647(9) Uani 1 1 d . . . . .
O1 O 0.12006(6) 0.20154(5) 0.25966(10) 0.0282(2) Uani 1 1 d . . . . .
O2 O 0.20725(5) 0.10051(5) 0.24946(9) 0.02385(19) Uani 1 1 d . . . . .
N1 N 0.09015(6) 0.08918(6) 0.12934(11) 0.0204(2) Uani 1 1 d . . . . .
H1A H 0.0471(10) 0.1063(10) 0.107(2) 0.034(5) Uiso 1 1 d . . . . .
H1B H 0.1066(10) 0.0478(10) 0.101(2) 0.035(5) Uiso 1 1 d . . . . .
C1 C 0.10064(6) 0.09123(5) 0.43403(12) 0.01583(19) Uani 1 1 d . . . . .
C2 C 0.02986(6) 0.10572(6) 0.48174(12) 0.0183(2) Uani 1 1 d . . . . .
C3 C 0.01010(7) 0.07829(7) 0.62015(13) 0.0229(2) Uani 1 1 d . . . . .
H3 H -0.0373 0.0871 0.6561 0.027 Uiso 1 1 calc R U . . .
C4 C 0.05770(7) 0.03854(7) 0.70674(13) 0.0246(2) Uani 1 1 d . . . . .
H4 H 0.0427 0.0210 0.8007 0.030 Uiso 1 1 calc R U . . .
C5 C 0.12700(7) 0.02434(7) 0.65678(13) 0.0230(2) Uani 1 1 d . . . . .
H5 H 0.1594 -0.0033 0.7157 0.028 Uiso 1 1 calc R U . . .
C6 C 0.14877(6) 0.05086(6) 0.51953(12) 0.0189(2) Uani 1 1 d . . . . .
H6 H 0.1962 0.0415 0.4842 0.023 Uiso 1 1 calc R U . . .
C7 C -0.02486(7) 0.14732(7) 0.39268(16) 0.0273(3) Uani 1 1 d . . . . .
H7A H -0.0382 0.1195 0.3045 0.041 Uiso 1 1 calc R U . . .
H7B H -0.0041 0.1937 0.3624 0.041 Uiso 1 1 calc R U . . .
H7C H -0.0679 0.1559 0.4532 0.041 Uiso 1 1 calc R U . . .


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

loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
S1 O1 1.4380(9) . ?
S1 O2 1.4435(9) . ?
S1 N1 1.5947(10) . ?
S1 C1 1.7745(11) . ?
N1 H1A 0.880(19) . ?
N1 H1B 0.863(19) . ?
C1 C6 1.3960(15) . ?
C1 C2 1.4056(15) . ?
C2 C3 1.3970(16) . ?
C2 C7 1.5055(17) . ?
C3 C4 1.3891(18) . ?
C3 H3 0.9500 . ?
C4 C5 1.3855(18) . ?
C4 H4 0.9500 . ?
C5 C6 1.3920(16) . ?
C5 H5 0.9500 . ?
C6 H6 0.9500 . ?
C7 H7A 0.9800 . ?
C7 H7B 0.9800 . ?
C7 H7C 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
O1 S1 O2 118.27(6) . . ?
O1 S1 N1 107.89(6) . . ?
O2 S1 N1 106.34(5) . . ?
O1 S1 C1 107.83(5) . . ?
O2 S1 C1 106.67(5) . . ?
N1 S1 C1 109.67(5) . . ?
S1 N1 H1A 118.5(12) . . ?
S1 N1 H1B 114.6(12) . . ?
H1A N1 H1B 124.9(17) . . ?
C6 C1 C2 121.91(10) . . ?
C6 C1 S1 116.77(8) . . ?
C2 C1 S1 121.31(8) . . ?
C3 C2 C1 116.66(10) . . ?
C3 C2 C7 119.14(11) . . ?
C1 C2 C7 124.20(11) . . ?
C4 C3 C2 121.96(11) . . ?
C4 C3 H3 119.0 . . ?
C2 C3 H3 119.0 . . ?
C5 C4 C3 120.37(11) . . ?
C5 C4 H4 119.8 . . ?
C3 C4 H4 119.8 . . ?
C4 C5 C6 119.40(11) . . ?
C4 C5 H5 120.3 . . ?
C6 C5 H5 120.3 . . ?
C5 C6 C1 119.71(11) . . ?
C5 C6 H6 120.1 . . ?
C1 C6 H6 120.1 . . ?
C2 C7 H7A 109.5 . . ?
C2 C7 H7B 109.5 . . ?
H7A C7 H7B 109.5 . . ?
C2 C7 H7C 109.5 . . ?
H7A C7 H7C 109.5 . . ?
H7B C7 H7C 109.5 . . ?

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
O1 S1 C1 C6 -127.04(9) . . . . ?
O2 S1 C1 C6 0.95(10) . . . . ?
N1 S1 C1 C6 115.72(9) . . . . ?
O1 S1 C1 C2 51.78(10) . . . . ?
O2 S1 C1 C2 179.77(9) . . . . ?
N1 S1 C1 C2 -65.46(10) . . . . ?
C6 C1 C2 C3 0.62(16) . . . . ?
S1 C1 C2 C3 -178.14(8) . . . . ?
C6 C1 C2 C7 -178.44(11) . . . . ?
S1 C1 C2 C7 2.80(15) . . . . ?
C1 C2 C3 C4 -0.10(17) . . . . ?
C7 C2 C3 C4 179.01(11) . . . . ?
C2 C3 C4 C5 -0.52(18) . . . . ?
C3 C4 C5 C6 0.62(18) . . . . ?
C4 C5 C6 C1 -0.10(17) . . . . ?
C2 C1 C6 C5 -0.53(16) . . . . ?
S1 C1 C6 C5 178.28(9) . . . . ?

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
N1 H1A O1 0.880(19) 2.107(19) 2.9552(13) 161.5(17) 15
N1 H1B O2 0.863(19) 2.07(2) 2.9244(13) 170.2(18) 7_444

_refine_diff_density_max         0.317
_refine_diff_density_min         -0.458
_refine_diff_density_rms         0.056

_shelxl_version_number           2014-3



_exptl_crystal_recrystallization_method 'Re-crystallisation from solvent'
####################################################################### 
# 
# 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_YM672
_database_code_depnum_ccdc_archive 'CCDC 1828326'
loop_
_audit_author_name
_audit_author_address
'Daisuke Hashizume'
;RIKEN
Japan
;
_audit_update_record             
;
2018-03-08 deposited with the CCDC.	2020-11-27 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2014
_chemical_name_systematic        4-Toluenesulfonamide
_chemical_name_common            ?
_chemical_melting_point          412
_chemical_formula_moiety         'C7 H9 N O2 S'
_chemical_formula_sum            'C7 H9 N O2 S'
_chemical_formula_weight         171.21

loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
N N 0.0061 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0106 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
S S 0.1246 0.1234 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_space_group_crystal_system      monoclinic
_space_group_IT_number           14
_space_group_name_H-M_alt        'P 21/n'
_space_group_name_Hall           '-P 2yn'

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

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

_cell_length_a                   6.6299(2)
_cell_length_b                   16.2473(4)
_cell_length_c                   7.5792(2)
_cell_angle_alpha                90
_cell_angle_beta                 91.6792(11)
_cell_angle_gamma                90
_cell_volume                     816.07(4)
_cell_formula_units_Z            4
_cell_measurement_temperature    90
_cell_measurement_reflns_used    21683
_cell_measurement_theta_min      2.967
_cell_measurement_theta_max      30.902

_exptl_crystal_description       plate
_exptl_crystal_colour            colourless
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.394
_exptl_crystal_F_000             360
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.11
_exptl_crystal_size_mid          0.10
_exptl_crystal_size_min          0.07
_exptl_absorpt_coefficient_mu    0.344
_shelx_estimated_absorpt_T_min   0.963
_shelx_estimated_absorpt_T_max   0.976
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.94854
_exptl_absorpt_correction_T_max  0.95879
_exptl_absorpt_process_details   
;
 MULABS - Empirical Correction for Absorption Anisotropy.
 R.H. Blessing, Acta Cryst. (1995), A51, 33-38.
;

_exptl_special_details           
;
 ?
;

_diffrn_ambient_temperature      90
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_source                   'Fine-focus rotating anode'
_diffrn_measurement_device_type  'Rigaku AFC-8 with Saturn70 CCD'
_diffrn_measurement_method       ω-scan
_diffrn_detector_area_resol_mean 7.31
_diffrn_reflns_number            21683
_diffrn_reflns_av_unetI/netI     0.0200
_diffrn_reflns_av_R_equivalents  0.0317
_diffrn_reflns_limit_h_min       -9
_diffrn_reflns_limit_h_max       9
_diffrn_reflns_limit_k_min       -23
_diffrn_reflns_limit_k_max       23
_diffrn_reflns_limit_l_min       -10
_diffrn_reflns_limit_l_max       10
_diffrn_reflns_theta_min         2.967
_diffrn_reflns_theta_max         30.902
_diffrn_reflns_theta_full        25.242
_diffrn_measured_fraction_theta_max 0.997
_diffrn_measured_fraction_theta_full 0.997
_diffrn_reflns_Laue_measured_fraction_max 0.997
_diffrn_reflns_Laue_measured_fraction_full 0.997
_diffrn_reflns_point_group_measured_fraction_max 0.997
_diffrn_reflns_point_group_measured_fraction_full 0.997
_reflns_number_total             2571
_reflns_number_gt                2322
_reflns_threshold_expression     'I > 2σ(I)'
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_max     .
_reflns_Friedel_fraction_full    .

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

_computing_data_collection       CrystalClear
_computing_cell_refinement       HKL2000
_computing_data_reduction        HKL2000
_computing_structure_solution    SIR2004
_computing_structure_refinement  'SHELXL-2014 (Sheldrick, 2014)'
_computing_molecular_graphics    SV
_computing_publication_material  'SHELXL-2014 (Sheldrick, 2014)'

_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)+(0.0445P)²+0.3841P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_atom_sites_solution_hydrogens   difmap
_refine_ls_hydrogen_treatment    mixed
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       .
_refine_ls_number_reflns         2571
_refine_ls_number_parameters     109
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0346
_refine_ls_R_factor_gt           0.0311
_refine_ls_wR_factor_ref         0.0893
_refine_ls_wR_factor_gt          0.0869
_refine_ls_goodness_of_fit_ref   1.043
_refine_ls_restrained_S_all      1.043
_refine_ls_shift/su_max          0.001
_refine_ls_shift/su_mean         0.000

loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_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 0.72298(4) 0.72402(2) 0.36042(3) 0.01674(9) Uani 1 1 d . . . . .
O1 O 0.58988(13) 0.77593(5) 0.45806(12) 0.02382(19) Uani 1 1 d . . . . .
O2 O 0.91834(13) 0.70372(6) 0.43640(11) 0.02414(18) Uani 1 1 d . . . . .
N1 N 0.76146(15) 0.77068(6) 0.17756(13) 0.01953(19) Uani 1 1 d . . . . .
H1A H 0.653(3) 0.7795(11) 0.113(3) 0.037(5) Uiso 1 1 d . . . . .
H1B H 0.853(3) 0.7508(13) 0.120(3) 0.043(5) Uiso 1 1 d . . . . .
C1 C 0.59439(16) 0.63117(7) 0.31472(13) 0.01730(19) Uani 1 1 d . . . . .
C2 C 0.39250(17) 0.63458(7) 0.25918(15) 0.0204(2) Uani 1 1 d . . . . .
H2 H 0.3232 0.6857 0.2538 0.025 Uiso 1 1 calc R U . . .
C3 C 0.29407(18) 0.56208(8) 0.21185(15) 0.0233(2) Uani 1 1 d . . . . .
H3 H 0.1567 0.5640 0.1726 0.028 Uiso 1 1 calc R U . . .
C4 C 0.39360(19) 0.48637(7) 0.22093(15) 0.0234(2) Uani 1 1 d . . . . .
C5 C 0.5952(2) 0.48453(7) 0.27837(16) 0.0248(2) Uani 1 1 d . . . . .
H5 H 0.6641 0.4333 0.2857 0.030 Uiso 1 1 calc R U . . .
C6 C 0.69712(17) 0.55653(7) 0.32520(15) 0.0216(2) Uani 1 1 d . . . . .
H6 H 0.8347 0.5548 0.3637 0.026 Uiso 1 1 calc R U . . .
C7 C 0.2846(2) 0.40818(8) 0.16959(18) 0.0324(3) Uani 1 1 d . . . . .
H7A H 0.2127 0.3870 0.2712 0.049 Uiso 1 1 calc R U . . .
H7B H 0.3825 0.3671 0.1317 0.049 Uiso 1 1 calc R U . . .
H7C H 0.1877 0.4196 0.0725 0.049 Uiso 1 1 calc R U . . .


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

loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
S1 O2 1.4402(8) . ?
S1 O1 1.4408(9) . ?
S1 N1 1.6067(10) . ?
S1 C1 1.7621(11) . ?
N1 H1A 0.87(2) . ?
N1 H1B 0.82(2) . ?
C1 C6 1.3920(15) . ?
C1 C2 1.3924(15) . ?
C2 C3 1.3887(16) . ?
C2 H2 0.9500 . ?
C3 C4 1.3966(17) . ?
C3 H3 0.9500 . ?
C4 C5 1.3937(18) . ?
C4 C7 1.5071(17) . ?
C5 C6 1.3918(17) . ?
C5 H5 0.9500 . ?
C6 H6 0.9500 . ?
C7 H7A 0.9800 . ?
C7 H7B 0.9800 . ?
C7 H7C 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
O2 S1 O1 119.07(5) . . ?
O2 S1 N1 106.81(5) . . ?
O1 S1 N1 106.38(6) . . ?
O2 S1 C1 107.87(5) . . ?
O1 S1 C1 107.58(5) . . ?
N1 S1 C1 108.82(5) . . ?
S1 N1 H1A 114.5(13) . . ?
S1 N1 H1B 114.2(15) . . ?
H1A N1 H1B 112.0(19) . . ?
C6 C1 C2 121.09(10) . . ?
C6 C1 S1 120.10(8) . . ?
C2 C1 S1 118.72(8) . . ?
C3 C2 C1 118.99(11) . . ?
C3 C2 H2 120.5 . . ?
C1 C2 H2 120.5 . . ?
C2 C3 C4 121.10(11) . . ?
C2 C3 H3 119.4 . . ?
C4 C3 H3 119.4 . . ?
C5 C4 C3 118.79(11) . . ?
C5 C4 C7 120.72(12) . . ?
C3 C4 C7 120.49(12) . . ?
C6 C5 C4 121.04(11) . . ?
C6 C5 H5 119.5 . . ?
C4 C5 H5 119.5 . . ?
C5 C6 C1 118.98(11) . . ?
C5 C6 H6 120.5 . . ?
C1 C6 H6 120.5 . . ?
C4 C7 H7A 109.5 . . ?
C4 C7 H7B 109.5 . . ?
H7A C7 H7B 109.5 . . ?
C4 C7 H7C 109.5 . . ?
H7A C7 H7C 109.5 . . ?
H7B C7 H7C 109.5 . . ?

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
O2 S1 C1 C6 -10.76(11) . . . . ?
O1 S1 C1 C6 -140.37(9) . . . . ?
N1 S1 C1 C6 104.77(10) . . . . ?
O2 S1 C1 C2 172.66(8) . . . . ?
O1 S1 C1 C2 43.04(10) . . . . ?
N1 S1 C1 C2 -71.82(10) . . . . ?
C6 C1 C2 C3 -0.74(17) . . . . ?
S1 C1 C2 C3 175.81(9) . . . . ?
C1 C2 C3 C4 0.66(17) . . . . ?
C2 C3 C4 C5 -0.12(17) . . . . ?
C2 C3 C4 C7 179.83(11) . . . . ?
C3 C4 C5 C6 -0.36(18) . . . . ?
C7 C4 C5 C6 179.69(11) . . . . ?
C4 C5 C6 C1 0.28(17) . . . . ?
C2 C1 C6 C5 0.27(17) . . . . ?
S1 C1 C6 C5 -176.23(9) . . . . ?

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
N1 H1A O2 0.87(2) 2.04(2) 2.9061(13) 173.2(18) 4_575
N1 H1B O1 0.82(2) 2.07(2) 2.8800(14) 169(2) 4_675

_refine_diff_density_max         0.322
_refine_diff_density_min         -0.440
_refine_diff_density_rms         0.056

_shelxl_version_number           2014-3



_exptl_crystal_recrystallization_method 'Re-crystallisation from solvent'
####################################################################### 
# 
# 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_YM674
_database_code_depnum_ccdc_archive 'CCDC 1828331'
loop_
_audit_author_name
_audit_author_address
'Daisuke Hashizume'
;RIKEN
Japan
;
_audit_update_record             
;
2018-03-08 deposited with the CCDC.	2020-11-27 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2014
_chemical_name_systematic        1,2-Phenylenediamine
_chemical_name_common            ?
_chemical_melting_point          374
_chemical_formula_moiety         'C6 H8 N2'
_chemical_formula_sum            'C6 H8 N2'
_chemical_formula_weight         108.14

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'

_space_group_crystal_system      monoclinic
_space_group_IT_number           14
_space_group_name_H-M_alt        'P 21/c'
_space_group_name_Hall           '-P 2ybc'

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

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

_cell_length_a                   10.1687(11)
_cell_length_b                   7.4132(13)
_cell_length_c                   7.6623(15)
_cell_angle_alpha                90
_cell_angle_beta                 100.344(5)
_cell_angle_gamma                90
_cell_volume                     568.22(16)
_cell_formula_units_Z            4
_cell_measurement_temperature    90
_cell_measurement_reflns_used    15333
_cell_measurement_theta_min      2.036
_cell_measurement_theta_max      31.179

_exptl_crystal_description       plate
_exptl_crystal_colour            colourless
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.264
_exptl_crystal_F_000             232
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.13
_exptl_crystal_size_mid          0.09
_exptl_crystal_size_min          0.03
_exptl_absorpt_coefficient_mu    0.080
_shelx_estimated_absorpt_T_min   0.990
_shelx_estimated_absorpt_T_max   0.998
_exptl_absorpt_correction_type   none
_exptl_absorpt_correction_T_min  ?
_exptl_absorpt_correction_T_max  ?
_exptl_absorpt_process_details   ?

_exptl_special_details           
;
 ?
;

_diffrn_ambient_temperature      90
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_source                   'Fine-focus rotating anode'
_diffrn_measurement_device_type  'Rigaku AFC-8 with Saturn70 CCD'
_diffrn_measurement_method       ω-scan
_diffrn_detector_area_resol_mean 7.31
_diffrn_reflns_number            14662
_diffrn_reflns_av_unetI/netI     0.0359
_diffrn_reflns_av_R_equivalents  0.0639
_diffrn_reflns_limit_h_min       -14
_diffrn_reflns_limit_h_max       14
_diffrn_reflns_limit_k_min       -10
_diffrn_reflns_limit_k_max       10
_diffrn_reflns_limit_l_min       -11
_diffrn_reflns_limit_l_max       11
_diffrn_reflns_theta_min         2.036
_diffrn_reflns_theta_max         31.179
_diffrn_reflns_theta_full        25.242
_diffrn_measured_fraction_theta_max 0.998
_diffrn_measured_fraction_theta_full 1.000
_diffrn_reflns_Laue_measured_fraction_max 0.998
_diffrn_reflns_Laue_measured_fraction_full 1.000
_diffrn_reflns_point_group_measured_fraction_max 0.998
_diffrn_reflns_point_group_measured_fraction_full 1.000
_reflns_number_total             1838
_reflns_number_gt                1323
_reflns_threshold_expression     'I > 2σ(I)'
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_max     .
_reflns_Friedel_fraction_full    .

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

_computing_data_collection       CrystalClear
_computing_cell_refinement       HKL2000
_computing_data_reduction        HKL2000
_computing_structure_solution    SIR2011
_computing_structure_refinement  'SHELXL-2014 (Sheldrick, 2014)'
_computing_molecular_graphics    SV
_computing_publication_material  'SHELXL-2014 (Sheldrick, 2014)'

_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)+(0.0744P)²+0.0414P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   direct
_atom_sites_solution_hydrogens   difmap
_refine_ls_hydrogen_treatment    mixed
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       .
_refine_ls_number_reflns         1838
_refine_ls_number_parameters     89
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0705
_refine_ls_R_factor_gt           0.0483
_refine_ls_wR_factor_ref         0.1347
_refine_ls_wR_factor_gt          0.1239
_refine_ls_goodness_of_fit_ref   1.049
_refine_ls_restrained_S_all      1.049
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000

loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_site_symmetry_order
_atom_site_calc_flag
_atom_site_refinement_flags_posn
_atom_site_refinement_flags_adp
_atom_site_refinement_flags_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
N1 N 0.00448(10) 0.45881(13) 0.26297(13) 0.0246(2) Uani 1 1 d . . . . .
H1A H -0.0501(15) 0.400(2) 0.173(2) 0.038(4) Uiso 1 1 d . . . . .
H1B H -0.0265(14) 0.572(2) 0.275(2) 0.039(4) Uiso 1 1 d . . . . .
N2 N 0.17867(10) 0.68688(13) 0.47481(13) 0.0255(2) Uani 1 1 d . . . . .
H2A H 0.1180(15) 0.635(2) 0.536(2) 0.040(4) Uiso 1 1 d . . . . .
H2B H 0.2443(16) 0.743(2) 0.548(2) 0.039(4) Uiso 1 1 d . . . . .
C1 C 0.13917(11) 0.46212(14) 0.24267(14) 0.0222(2) Uani 1 1 d . . . . .
C2 C 0.22866(11) 0.57414(13) 0.35477(14) 0.0225(2) Uani 1 1 d . . . . .
C3 C 0.36150(11) 0.57928(14) 0.33571(15) 0.0251(3) Uani 1 1 d . . . . .
H3 H 0.4220 0.6561 0.4102 0.030 Uiso 1 1 calc R U . . .
C4 C 0.40759(12) 0.47390(16) 0.20936(16) 0.0287(3) Uani 1 1 d . . . . .
H4 H 0.4988 0.4798 0.1968 0.034 Uiso 1 1 calc R U . . .
C5 C 0.32016(12) 0.36018(15) 0.10178(15) 0.0282(3) Uani 1 1 d . . . . .
H5 H 0.3515 0.2863 0.0166 0.034 Uiso 1 1 calc R U . . .
C6 C 0.18694(11) 0.35447(14) 0.11873(14) 0.0245(3) Uani 1 1 d . . . . .
H6 H 0.1273 0.2761 0.0449 0.029 Uiso 1 1 calc R U . . .


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

loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
N1 C1 1.4061(14) . ?
N1 H1A 0.911(15) . ?
N1 H1B 0.909(15) . ?
N2 C2 1.4038(14) . ?
N2 H2A 0.922(16) . ?
N2 H2B 0.893(16) . ?
C1 C6 1.3929(15) . ?
C1 C2 1.4052(15) . ?
C2 C3 1.3851(15) . ?
C3 C4 1.3893(16) . ?
C3 H3 0.9500 . ?
C4 C5 1.3847(17) . ?
C4 H4 0.9500 . ?
C5 C6 1.3845(16) . ?
C5 H5 0.9500 . ?
C6 H6 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
C1 N1 H1A 113.5(9) . . ?
C1 N1 H1B 111.0(9) . . ?
H1A N1 H1B 109.9(13) . . ?
C2 N2 H2A 115.8(9) . . ?
C2 N2 H2B 111.8(10) . . ?
H2A N2 H2B 111.7(14) . . ?
C6 C1 C2 119.24(10) . . ?
C6 C1 N1 122.09(10) . . ?
C2 C1 N1 118.65(10) . . ?
C3 C2 N2 121.83(10) . . ?
C3 C2 C1 119.25(10) . . ?
N2 C2 C1 118.78(10) . . ?
C2 C3 C4 121.03(10) . . ?
C2 C3 H3 119.5 . . ?
C4 C3 H3 119.5 . . ?
C5 C4 C3 119.75(11) . . ?
C5 C4 H4 120.1 . . ?
C3 C4 H4 120.1 . . ?
C6 C5 C4 119.82(11) . . ?
C6 C5 H5 120.1 . . ?
C4 C5 H5 120.1 . . ?
C5 C6 C1 120.88(10) . . ?
C5 C6 H6 119.6 . . ?
C1 C6 H6 119.6 . . ?

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 C1 C2 C3 2.04(15) . . . . ?
N1 C1 C2 C3 -179.73(9) . . . . ?
C6 C1 C2 N2 177.74(9) . . . . ?
N1 C1 C2 N2 -4.03(14) . . . . ?
N2 C2 C3 C4 -176.40(10) . . . . ?
C1 C2 C3 C4 -0.84(16) . . . . ?
C2 C3 C4 C5 -0.74(17) . . . . ?
C3 C4 C5 C6 1.10(17) . . . . ?
C4 C5 C6 C1 0.13(17) . . . . ?
C2 C1 C6 C5 -1.70(16) . . . . ?
N1 C1 C6 C5 -179.87(10) . . . . ?

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
N1 H1A N2 0.911(15) 2.230(16) 3.1037(14) 160.6(13) 2_545
N2 H2A N1 0.922(16) 2.259(16) 3.1648(15) 167.1(13) 3_566

_refine_diff_density_max         0.338
_refine_diff_density_min         -0.198
_refine_diff_density_rms         0.048

_shelxl_version_number           2014-3



_exptl_crystal_recrystallization_method 'Re-crystallisation from solvent'
_chemical_properties_physical    Light-sensitive
####################################################################### 
# 
# 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_YM673
_database_code_depnum_ccdc_archive 'CCDC 1828327'
loop_
_audit_author_name
_audit_author_address
'Daisuke Hashizume'
;RIKEN
Japan
;
_audit_update_record             
;
2018-03-08 deposited with the CCDC.	2020-11-27 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2014
_chemical_name_systematic        3-Toluenesulfonamide
_chemical_name_common            ?
_chemical_melting_point          379
_chemical_formula_moiety         'C7 H9 N O2 S'
_chemical_formula_sum            'C7 H9 N O2 S'
_chemical_formula_weight         171.21

loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
N N 0.0061 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0106 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
S S 0.1246 0.1234 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_space_group_crystal_system      monoclinic
_space_group_IT_number           14
_space_group_name_H-M_alt        'P 21/c'
_space_group_name_Hall           '-P 2ybc'

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

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

_cell_length_a                   6.9213(2)
_cell_length_b                   14.3941(4)
_cell_length_c                   15.9579(5)
_cell_angle_alpha                90
_cell_angle_beta                 90.6969(14)
_cell_angle_gamma                90
_cell_volume                     1589.70(8)
_cell_formula_units_Z            8
_cell_measurement_temperature    90
_cell_measurement_reflns_used    34304
_cell_measurement_theta_min      1.905
_cell_measurement_theta_max      25.242

_exptl_crystal_description       plate
_exptl_crystal_colour            colourless
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.431
_exptl_crystal_F_000             720
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.12
_exptl_crystal_size_mid          0.09
_exptl_crystal_size_min          0.03
_exptl_absorpt_coefficient_mu    0.354
_shelx_estimated_absorpt_T_min   0.959
_shelx_estimated_absorpt_T_max   0.989
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.94648
_exptl_absorpt_correction_T_max  0.96565
_exptl_absorpt_process_details   
;
 MULABS - Empirical Correction for Absorption Anisotropy.
 R.H. Blessing, Acta Cryst. (1995), A51, 33-38.
;

_exptl_special_details           
;
 ?
;

_diffrn_ambient_temperature      90
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_source                   'Fine-focus rotating anode'
_diffrn_measurement_device_type  'Rigaku AFC-8 with Saturn70 CCD'
_diffrn_measurement_method       ω-scan
_diffrn_detector_area_resol_mean 7.31
_diffrn_reflns_number            34304
_diffrn_reflns_av_unetI/netI     0.0448
_diffrn_reflns_av_R_equivalents  0.0580
_diffrn_reflns_limit_h_min       -10
_diffrn_reflns_limit_h_max       9
_diffrn_reflns_limit_k_min       -20
_diffrn_reflns_limit_k_max       20
_diffrn_reflns_limit_l_min       -23
_diffrn_reflns_limit_l_max       23
_diffrn_reflns_theta_min         1.905
_diffrn_reflns_theta_max         30.957
_diffrn_reflns_theta_full        25.242
_diffrn_measured_fraction_theta_max 0.993
_diffrn_measured_fraction_theta_full 1.000
_diffrn_reflns_Laue_measured_fraction_max 0.993
_diffrn_reflns_Laue_measured_fraction_full 1.000
_diffrn_reflns_point_group_measured_fraction_max 0.993
_diffrn_reflns_point_group_measured_fraction_full 1.000
_reflns_number_total             4999
_reflns_number_gt                3873
_reflns_threshold_expression     'I > 2σ(I)'
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_max     .
_reflns_Friedel_fraction_full    .

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

_computing_data_collection       CrystalClear
_computing_cell_refinement       HKL2000
_computing_data_reduction        HKL2000
_computing_structure_solution    SIR2011
_computing_structure_refinement  'SHELXL-2014 (Sheldrick, 2014)'
_computing_molecular_graphics    SV
_computing_publication_material  'SHELXL-2014 (Sheldrick, 2014)'

_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)+(0.0510P)²+0.2975P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_atom_sites_solution_hydrogens   difmap
_refine_ls_hydrogen_treatment    mixed
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       .
_refine_ls_number_reflns         4999
_refine_ls_number_parameters     217
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0570
_refine_ls_R_factor_gt           0.0394
_refine_ls_wR_factor_ref         0.1051
_refine_ls_wR_factor_gt          0.0970
_refine_ls_goodness_of_fit_ref   1.048
_refine_ls_restrained_S_all      1.048
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000

loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_site_symmetry_order
_atom_site_calc_flag
_atom_site_refinement_flags_posn
_atom_site_refinement_flags_adp
_atom_site_refinement_flags_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
S1A S 0.49029(5) 0.45280(2) 0.28229(2) 0.01670(9) Uani 1 1 d . . . . .
O1A O 0.30550(16) 0.49511(8) 0.29536(7) 0.0250(2) Uani 1 1 d . . . . .
O2A O 0.63537(16) 0.50384(8) 0.23794(7) 0.0242(2) Uani 1 1 d . . . . .
N1A N 0.4512(2) 0.35869(9) 0.23013(8) 0.0187(3) Uani 1 1 d . . . . .
H1A H 0.361(3) 0.3321(13) 0.2499(12) 0.027(5) Uiso 1 1 d . . . . .
H1B H 0.558(3) 0.3270(14) 0.2270(12) 0.028(5) Uiso 1 1 d . . . . .
C1A C 0.5877(2) 0.42175(10) 0.38140(9) 0.0171(3) Uani 1 1 d . . . . .
C2A C 0.4616(2) 0.38801(10) 0.44149(9) 0.0199(3) Uani 1 1 d . . . . .
H2A H 0.3268 0.3855 0.4299 0.024 Uiso 1 1 calc R U . . .
C3A C 0.5337(2) 0.35794(10) 0.51873(9) 0.0215(3) Uani 1 1 d . . . . .
C4A C 0.7323(2) 0.36250(11) 0.53341(10) 0.0239(3) Uani 1 1 d . . . . .
H4A H 0.7835 0.3420 0.5857 0.029 Uiso 1 1 calc R U . . .
C5A C 0.8562(2) 0.39625(11) 0.47345(10) 0.0249(3) Uani 1 1 d . . . . .
H5A H 0.9909 0.3993 0.4851 0.030 Uiso 1 1 calc R U . . .
C6A C 0.7849(2) 0.42587(11) 0.39595(10) 0.0218(3) Uani 1 1 d . . . . .
H6A H 0.8695 0.4483 0.3542 0.026 Uiso 1 1 calc R U . . .
C7A C 0.4007(3) 0.32017(13) 0.58444(11) 0.0305(4) Uani 1 1 d . . . . .
H7A H 0.4026 0.2521 0.5827 0.046 Uiso 1 1 calc R U . . .
H7B H 0.2690 0.3424 0.5735 0.046 Uiso 1 1 calc R U . . .
H7C H 0.4440 0.3414 0.6399 0.046 Uiso 1 1 calc R U . . .
S1B S 0.96020(5) 0.20581(2) 0.28904(2) 0.01699(9) Uani 1 1 d . . . . .
O1B O 1.13466(16) 0.25606(8) 0.30809(7) 0.0252(2) Uani 1 1 d . . . . .
O2B O 0.80760(16) 0.25114(8) 0.24305(7) 0.0243(2) Uani 1 1 d . . . . .
N1B N 1.02116(19) 0.11699(10) 0.23455(8) 0.0194(3) Uani 1 1 d . . . . .
H1C H 1.125(3) 0.0913(13) 0.2499(12) 0.028(5) Uiso 1 1 d . . . . .
H1D H 0.928(3) 0.0819(14) 0.2240(13) 0.034(6) Uiso 1 1 d . . . . .
C1B C 0.8633(2) 0.16666(10) 0.38483(9) 0.0174(3) Uani 1 1 d . . . . .
C2B C 0.9872(2) 0.15206(10) 0.45281(9) 0.0191(3) Uani 1 1 d . . . . .
H2B H 1.1207 0.1662 0.4482 0.023 Uiso 1 1 calc R U . . .
C3B C 0.9160(2) 0.11674(10) 0.52774(9) 0.0206(3) Uani 1 1 d . . . . .
C4B C 0.7187(2) 0.09714(11) 0.53185(10) 0.0233(3) Uani 1 1 d . . . . .
H4B H 0.6673 0.0733 0.5824 0.028 Uiso 1 1 calc R U . . .
C5B C 0.5962(2) 0.11170(11) 0.46368(10) 0.0241(3) Uani 1 1 d . . . . .
H5B H 0.4626 0.0977 0.4681 0.029 Uiso 1 1 calc R U . . .
C6B C 0.6674(2) 0.14665(11) 0.38912(10) 0.0210(3) Uani 1 1 d . . . . .
H6B H 0.5842 0.1566 0.3422 0.025 Uiso 1 1 calc R U . . .
C7B C 1.0473(3) 0.10106(12) 0.60203(10) 0.0272(3) Uani 1 1 d . . . . .
H7D H 1.1008 0.1606 0.6209 0.041 Uiso 1 1 calc R U . . .
H7E H 1.1529 0.0595 0.5861 0.041 Uiso 1 1 calc R U . . .
H7F H 0.9739 0.0728 0.6476 0.041 Uiso 1 1 calc R U . . .


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

loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
S1A O1A 1.4341(11) . ?
S1A O2A 1.4375(11) . ?
S1A N1A 1.6111(13) . ?
S1A C1A 1.7690(14) . ?
N1A H1A 0.80(2) . ?
N1A H1B 0.87(2) . ?
C1A C6A 1.383(2) . ?
C1A C2A 1.392(2) . ?
C2A C3A 1.393(2) . ?
C2A H2A 0.9500 . ?
C3A C4A 1.393(2) . ?
C3A C7A 1.505(2) . ?
C4A C5A 1.381(2) . ?
C4A H4A 0.9500 . ?
C5A C6A 1.393(2) . ?
C5A H5A 0.9500 . ?
C6A H6A 0.9500 . ?
C7A H7A 0.9800 . ?
C7A H7B 0.9800 . ?
C7A H7C 0.9800 . ?
S1B O2B 1.4357(11) . ?
S1B O1B 1.4369(11) . ?
S1B N1B 1.6055(14) . ?
S1B C1B 1.7690(15) . ?
N1B H1C 0.84(2) . ?
N1B H1D 0.84(2) . ?
C1B C6B 1.389(2) . ?
C1B C2B 1.391(2) . ?
C2B C3B 1.395(2) . ?
C2B H2B 0.9500 . ?
C3B C4B 1.397(2) . ?
C3B C7B 1.502(2) . ?
C4B C5B 1.387(2) . ?
C4B H4B 0.9500 . ?
C5B C6B 1.388(2) . ?
C5B H5B 0.9500 . ?
C6B H6B 0.9500 . ?
C7B H7D 0.9800 . ?
C7B H7E 0.9800 . ?
C7B H7F 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
O1A S1A O2A 118.96(7) . . ?
O1A S1A N1A 106.73(7) . . ?
O2A S1A N1A 106.80(7) . . ?
O1A S1A C1A 107.95(7) . . ?
O2A S1A C1A 107.97(7) . . ?
N1A S1A C1A 108.01(7) . . ?
S1A N1A H1A 109.0(14) . . ?
S1A N1A H1B 109.4(13) . . ?
H1A N1A H1B 116.0(19) . . ?
C6A C1A C2A 121.66(14) . . ?
C6A C1A S1A 120.26(12) . . ?
C2A C1A S1A 117.96(11) . . ?
C1A C2A C3A 119.82(14) . . ?
C1A C2A H2A 120.1 . . ?
C3A C2A H2A 120.1 . . ?
C2A C3A C4A 118.43(14) . . ?
C2A C3A C7A 120.87(15) . . ?
C4A C3A C7A 120.69(14) . . ?
C5A C4A C3A 121.32(14) . . ?
C5A C4A H4A 119.3 . . ?
C3A C4A H4A 119.3 . . ?
C4A C5A C6A 120.44(14) . . ?
C4A C5A H5A 119.8 . . ?
C6A C5A H5A 119.8 . . ?
C1A C6A C5A 118.32(15) . . ?
C1A C6A H6A 120.8 . . ?
C5A C6A H6A 120.8 . . ?
C3A C7A H7A 109.5 . . ?
C3A C7A H7B 109.5 . . ?
H7A C7A H7B 109.5 . . ?
C3A C7A H7C 109.5 . . ?
H7A C7A H7C 109.5 . . ?
H7B C7A H7C 109.5 . . ?
O2B S1B O1B 119.37(7) . . ?
O2B S1B N1B 106.35(7) . . ?
O1B S1B N1B 106.84(7) . . ?
O2B S1B C1B 107.58(7) . . ?
O1B S1B C1B 107.71(7) . . ?
N1B S1B C1B 108.62(7) . . ?
S1B N1B H1C 114.9(13) . . ?
S1B N1B H1D 112.4(14) . . ?
H1C N1B H1D 116.8(19) . . ?
C6B C1B C2B 121.56(14) . . ?
C6B C1B S1B 119.31(11) . . ?
C2B C1B S1B 119.04(11) . . ?
C1B C2B C3B 120.20(14) . . ?
C1B C2B H2B 119.9 . . ?
C3B C2B H2B 119.9 . . ?
C2B C3B C4B 118.01(14) . . ?
C2B C3B C7B 120.98(14) . . ?
C4B C3B C7B 121.01(14) . . ?
C5B C4B C3B 121.41(14) . . ?
C5B C4B H4B 119.3 . . ?
C3B C4B H4B 119.3 . . ?
C4B C5B C6B 120.50(14) . . ?
C4B C5B H5B 119.7 . . ?
C6B C5B H5B 119.7 . . ?
C5B C6B C1B 118.32(14) . . ?
C5B C6B H6B 120.8 . . ?
C1B C6B H6B 120.8 . . ?
C3B C7B H7D 109.5 . . ?
C3B C7B H7E 109.5 . . ?
H7D C7B H7E 109.5 . . ?
C3B C7B H7F 109.5 . . ?
H7D C7B H7F 109.5 . . ?
H7E C7B H7F 109.5 . . ?

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
O1A S1A C1A C6A -146.12(13) . . . . ?
O2A S1A C1A C6A -16.32(15) . . . . ?
N1A S1A C1A C6A 98.83(14) . . . . ?
O1A S1A C1A C2A 37.77(14) . . . . ?
O2A S1A C1A C2A 167.57(11) . . . . ?
N1A S1A C1A C2A -77.28(13) . . . . ?
C6A C1A C2A C3A 0.4(2) . . . . ?
S1A C1A C2A C3A 176.46(11) . . . . ?
C1A C2A C3A C4A -0.1(2) . . . . ?
C1A C2A C3A C7A -179.32(14) . . . . ?
C2A C3A C4A C5A 0.3(2) . . . . ?
C7A C3A C4A C5A 179.45(15) . . . . ?
C3A C4A C5A C6A -0.7(2) . . . . ?
C2A C1A C6A C5A -0.8(2) . . . . ?
S1A C1A C6A C5A -176.74(12) . . . . ?
C4A C5A C6A C1A 0.9(2) . . . . ?
O2B S1B C1B C6B 26.94(14) . . . . ?
O1B S1B C1B C6B 156.82(12) . . . . ?
N1B S1B C1B C6B -87.80(13) . . . . ?
O2B S1B C1B C2B -156.40(12) . . . . ?
O1B S1B C1B C2B -26.51(14) . . . . ?
N1B S1B C1B C2B 88.86(13) . . . . ?
C6B C1B C2B C3B -0.2(2) . . . . ?
S1B C1B C2B C3B -176.75(11) . . . . ?
C1B C2B C3B C4B -0.1(2) . . . . ?
C1B C2B C3B C7B -179.61(14) . . . . ?
C2B C3B C4B C5B 0.3(2) . . . . ?
C7B C3B C4B C5B 179.77(15) . . . . ?
C3B C4B C5B C6B -0.2(2) . . . . ?
C4B C5B C6B C1B -0.1(2) . . . . ?
C2B C1B C6B C5B 0.3(2) . . . . ?
S1B C1B C6B C5B 176.88(12) . . . . ?

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
N1A H1A O1B 0.80(2) 2.13(2) 2.9321(18) 176(2) 1_455
N1A H1B O2B 0.87(2) 2.06(2) 2.9174(17) 169.6(18) .
N1B H1C O2A 0.84(2) 2.09(2) 2.9106(17) 164.9(18) 2_745
N1B H1D O1A 0.84(2) 2.06(2) 2.8967(17) 177(2) 2_645

_refine_diff_density_max         0.380
_refine_diff_density_min         -0.522
_refine_diff_density_rms         0.071

_shelxl_version_number           2014-3



_exptl_crystal_recrystallization_method 'Re-crystallisation from solvent'
####################################################################### 
# 
# 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_CY011
_database_code_depnum_ccdc_archive 'CCDC 1828329'
loop_
_audit_author_name
_audit_author_address
'Daisuke Hashizume'
;RIKEN
Japan
;
_audit_update_record             
;
2018-03-08 deposited with the CCDC.	2020-11-27 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2014
_chemical_name_systematic        1,2-Bis(methanesulfonyl)benzene
_chemical_name_common            ?
_chemical_melting_point          502
_chemical_formula_moiety         'C8 H10 O4 S2'
_chemical_formula_sum            'C8 H10 O4 S2'
_chemical_formula_weight         234.28

loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0106 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
S S 0.1246 0.1234 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_space_group_crystal_system      orthorhombic
_space_group_IT_number           60
_space_group_name_H-M_alt        'P b c n'
_space_group_name_Hall           '-P 2n 2ab'

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

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

_cell_length_a                   10.1116(2)
_cell_length_b                   12.9234(3)
_cell_length_c                   7.4954(1)
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_volume                     979.47(3)
_cell_formula_units_Z            4
_cell_measurement_temperature    90
_cell_measurement_reflns_used    27584
_cell_measurement_theta_min      2.558
_cell_measurement_theta_max      30.998

_exptl_crystal_description       block
_exptl_crystal_colour            colourless
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.589
_exptl_crystal_F_000             488
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.130
_exptl_crystal_size_mid          0.090
_exptl_crystal_size_min          0.080
_exptl_absorpt_coefficient_mu    0.528
_shelx_estimated_absorpt_T_min   0.935
_shelx_estimated_absorpt_T_max   0.959
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.91478
_exptl_absorpt_correction_T_max  0.93102
_exptl_absorpt_process_details   
;
 MULABS - Empirical Correction for Absorption Anisotropy.
 R.H. Blessing, Acta Cryst. (1995), A51, 33-38.
;

_exptl_special_details           
;
 ?
;

_diffrn_ambient_temperature      90
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_source                   'Fine-focus rotating anode'
_diffrn_measurement_device_type  'Rigaku AFC-8 with Saturn70 CCD'
_diffrn_measurement_method       ω-scan
_diffrn_detector_area_resol_mean 7.31
_diffrn_reflns_number            25073
_diffrn_reflns_av_unetI/netI     0.0154
_diffrn_reflns_av_R_equivalents  0.0339
_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       -10
_diffrn_reflns_limit_l_max       10
_diffrn_reflns_theta_min         2.558
_diffrn_reflns_theta_max         30.998
_diffrn_reflns_theta_full        25.242
_diffrn_measured_fraction_theta_max 0.998
_diffrn_measured_fraction_theta_full 0.997
_diffrn_reflns_Laue_measured_fraction_max 0.998
_diffrn_reflns_Laue_measured_fraction_full 0.997
_diffrn_reflns_point_group_measured_fraction_max 0.998
_diffrn_reflns_point_group_measured_fraction_full 0.997
_reflns_number_total             1564
_reflns_number_gt                1449
_reflns_threshold_expression     'I > 2σ(I)'
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_max     .
_reflns_Friedel_fraction_full    .

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

_computing_data_collection       CrystalClear
_computing_cell_refinement       HKL2000
_computing_data_reduction        HKL2000
_computing_structure_solution    SIR2004
_computing_structure_refinement  'SHELXL-2014 (Sheldrick, 2014)'
_computing_molecular_graphics    SV
_computing_publication_material  'SHELXL-2014 (Sheldrick, 2014)'

_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)+(0.0501P)²+0.3128P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_atom_sites_solution_hydrogens   difmap
_refine_ls_hydrogen_treatment    refall
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       .
_refine_ls_number_reflns         1564
_refine_ls_number_parameters     84
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0296
_refine_ls_R_factor_gt           0.0279
_refine_ls_wR_factor_ref         0.0801
_refine_ls_wR_factor_gt          0.0788
_refine_ls_goodness_of_fit_ref   1.051
_refine_ls_restrained_S_all      1.051
_refine_ls_shift/su_max          0.001
_refine_ls_shift/su_mean         0.000

loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_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 0.34431(2) 0.17920(2) 0.64552(3) 0.01507(10) Uani 1 1 d . . . . .
O1 O 0.21197(7) 0.21477(6) 0.60600(11) 0.02086(16) Uani 1 1 d . . . . .
O2 O 0.35754(7) 0.10146(6) 0.78251(10) 0.02046(17) Uani 1 1 d . . . . .
C1 C 0.43898(8) 0.29102(7) 0.70484(12) 0.01417(17) Uani 1 1 d . . . . .
C2 C 0.38080(10) 0.38493(7) 0.65793(13) 0.01756(19) Uani 1 1 d . . . . .
H2 H 0.3006(15) 0.3863(11) 0.594(2) 0.024(3) Uiso 1 1 d . . . . .
C3 C 0.44093(9) 0.47830(7) 0.70295(14) 0.0200(2) Uani 1 1 d . . . . .
H3 H 0.3989(16) 0.5428(12) 0.669(2) 0.026(4) Uiso 1 1 d . . . . .
C4 C 0.41521(11) 0.13554(8) 0.44509(14) 0.0209(2) Uani 1 1 d . . . . .
H4A H 0.3664(16) 0.0713(15) 0.417(2) 0.036(4) Uiso 1 1 d . . . . .
H4B H 0.5077(16) 0.1238(11) 0.462(2) 0.030(4) Uiso 1 1 d . . . . .
H4C H 0.4046(19) 0.1907(13) 0.360(2) 0.032(4) Uiso 1 1 d . . . . .


_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 O2 1.4428(7) . ?
S1 O1 1.4456(7) . ?
S1 C4 1.7577(11) . ?
S1 C1 1.7896(9) . ?
C1 C2 1.3938(12) . ?
C1 C1 1.4075(17) 7_657 ?
C2 C3 1.3927(13) . ?
C2 H2 0.943(16) . ?
C3 C3 1.387(2) 7_657 ?
C3 H3 0.971(16) . ?
C4 H4A 0.987(18) . ?
C4 H4B 0.956(16) . ?
C4 H4C 0.963(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
O2 S1 O1 116.94(4) . . ?
O2 S1 C4 110.30(5) . . ?
O1 S1 C4 107.73(5) . . ?
O2 S1 C1 109.63(4) . . ?
O1 S1 C1 106.81(4) . . ?
C4 S1 C1 104.68(5) . . ?
C2 C1 C1 119.43(5) . 7_657 ?
C2 C1 S1 114.50(7) . . ?
C1 C1 S1 126.05(3) 7_657 . ?
C3 C2 C1 120.60(9) . . ?
C3 C2 H2 118.9(9) . . ?
C1 C2 H2 120.5(9) . . ?
C3 C3 C2 119.94(6) 7_657 . ?
C3 C3 H3 120.8(9) 7_657 . ?
C2 C3 H3 119.3(10) . . ?
S1 C4 H4A 104.2(10) . . ?
S1 C4 H4B 109.6(10) . . ?
H4A C4 H4B 112.6(13) . . ?
S1 C4 H4C 106.5(10) . . ?
H4A C4 H4C 115.3(15) . . ?
H4B C4 H4C 108.3(15) . . ?

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
O2 S1 C1 C2 -143.14(7) . . . . ?
O1 S1 C1 C2 -15.52(8) . . . . ?
C4 S1 C1 C2 98.56(8) . . . . ?
O2 S1 C1 C1 35.33(12) . . . 7_657 ?
O1 S1 C1 C1 162.94(10) . . . 7_657 ?
C4 S1 C1 C1 -82.98(12) . . . 7_657 ?
C1 C1 C2 C3 -1.37(16) 7_657 . . . ?
S1 C1 C2 C3 177.21(8) . . . . ?
C1 C2 C3 C3 -0.71(18) . . . 7_657 ?

_refine_diff_density_max         0.394
_refine_diff_density_min         -0.513
_refine_diff_density_rms         0.060

_shelxl_version_number           2014-3



_exptl_crystal_recrystallization_method 'Re-crystallisation from solvent'
####################################################################### 
# 
# 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_CY015
_database_code_depnum_ccdc_archive 'CCDC 1828336'
loop_
_audit_author_name
_audit_author_address
'Daisuke Hashizume'
;RIKEN
Japan
;
_audit_update_record             
;
2018-03-08 deposited with the CCDC.	2020-11-27 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2014
_chemical_name_systematic        3-Bromobenzonitrile
_chemical_name_common            ?
_chemical_melting_point          38
_chemical_formula_moiety         'C7 H4 Br N'
_chemical_formula_sum            'C7 H4 Br N'
_chemical_formula_weight         182.02

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'

_space_group_crystal_system      monoclinic
_space_group_IT_number           14
_space_group_name_H-M_alt        'P 21/n'
_space_group_name_Hall           '-P 2yn'

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

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

_cell_length_a                   7.5162(4)
_cell_length_b                   3.9503(2)
_cell_length_c                   22.2292(13)
_cell_angle_alpha                90
_cell_angle_beta                 93.257(3)
_cell_angle_gamma                90
_cell_volume                     658.95(6)
_cell_formula_units_Z            4
_cell_measurement_temperature    90
_cell_measurement_reflns_used    17150
_cell_measurement_theta_min      1.835
_cell_measurement_theta_max      31.020

_exptl_crystal_description       needle
_exptl_crystal_colour            colourless
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.835
_exptl_crystal_F_000             352
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.120
_exptl_crystal_size_mid          0.020
_exptl_crystal_size_min          0.020
_exptl_absorpt_coefficient_mu    6.133
_shelx_estimated_absorpt_T_min   0.527
_shelx_estimated_absorpt_T_max   0.887
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.56823
_exptl_absorpt_correction_T_max  0.65834
_exptl_absorpt_process_details   
;
 MULABS - Empirical Correction for Absorption Anisotropy.
 R.H. Blessing, Acta Cryst. (1995), A51, 33-38.
;

_exptl_special_details           
;
 ?
;

_diffrn_ambient_temperature      90
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_source                   'Fine-focus rotating anode'
_diffrn_measurement_device_type  'Rigaku AFC-8 with Saturn70 CCD'
_diffrn_measurement_method       ω-scan
_diffrn_detector_area_resol_mean 7.31
_diffrn_reflns_number            15786
_diffrn_reflns_av_unetI/netI     0.0299
_diffrn_reflns_av_R_equivalents  0.0654
_diffrn_reflns_limit_h_min       -10
_diffrn_reflns_limit_h_max       10
_diffrn_reflns_limit_k_min       -5
_diffrn_reflns_limit_k_max       5
_diffrn_reflns_limit_l_min       -32
_diffrn_reflns_limit_l_max       32
_diffrn_reflns_theta_min         1.835
_diffrn_reflns_theta_max         31.020
_diffrn_reflns_theta_full        25.242
_diffrn_measured_fraction_theta_max 0.999
_diffrn_measured_fraction_theta_full 1.000
_diffrn_reflns_Laue_measured_fraction_max 0.999
_diffrn_reflns_Laue_measured_fraction_full 1.000
_diffrn_reflns_point_group_measured_fraction_max 0.999
_diffrn_reflns_point_group_measured_fraction_full 1.000
_reflns_number_total             2107
_reflns_number_gt                1696
_reflns_threshold_expression     'I > 2σ(I)'
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_max     .
_reflns_Friedel_fraction_full    .

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

_computing_data_collection       CrystalClear
_computing_cell_refinement       HKL2000
_computing_data_reduction        HKL2000
_computing_structure_solution    SHELXS-97
_computing_structure_refinement  'SHELXL-2014 (Sheldrick, 2014)'
_computing_molecular_graphics    SV
_computing_publication_material  'SHELXL-2014 (Sheldrick, 2014)'

_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)+(0.0446P)²+0.5480P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_atom_sites_solution_hydrogens   difmap
_refine_ls_hydrogen_treatment    constr
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       .
_refine_ls_number_reflns         2107
_refine_ls_number_parameters     82
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0447
_refine_ls_R_factor_gt           0.0343
_refine_ls_wR_factor_ref         0.0918
_refine_ls_wR_factor_gt          0.0860
_refine_ls_goodness_of_fit_ref   1.058
_refine_ls_restrained_S_all      1.058
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000

loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_site_symmetry_order
_atom_site_calc_flag
_atom_site_refinement_flags_posn
_atom_site_refinement_flags_adp
_atom_site_refinement_flags_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
Br1 Br 0.57850(3) 0.73832(6) 0.20838(2) 0.02760(10) Uani 1 1 d . . . . .
N1 N 0.2877(3) 0.0473(6) -0.03388(10) 0.0325(5) Uani 1 1 d . . . . .
C1 C 0.2547(3) 0.3525(6) 0.06770(11) 0.0244(4) Uani 1 1 d . . . . .
C2 C 0.4052(3) 0.4407(6) 0.10450(11) 0.0238(4) Uani 1 1 d . . . . .
H2 H 0.5218 0.3867 0.0932 0.029 Uiso 1 1 calc R U . . .
C3 C 0.3784(3) 0.6087(6) 0.15775(11) 0.0235(4) Uani 1 1 d . . . . .
C4 C 0.2088(3) 0.6911(6) 0.17523(12) 0.0263(5) Uani 1 1 d . . . . .
H4 H 0.1939 0.8078 0.2120 0.032 Uiso 1 1 calc R U . . .
C5 C 0.0614(3) 0.6000(7) 0.13810(12) 0.0292(5) Uani 1 1 d . . . . .
H5 H -0.0550 0.6545 0.1496 0.035 Uiso 1 1 calc R U . . .
C6 C 0.0830(3) 0.4307(6) 0.08461(12) 0.0279(5) Uani 1 1 d . . . . .
H6 H -0.0180 0.3678 0.0595 0.033 Uiso 1 1 calc R U . . .
C7 C 0.2762(3) 0.1802(7) 0.01113(12) 0.0273(5) Uani 1 1 d . . . . .


_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 C3 1.897(2) . ?
N1 C7 1.137(3) . ?
C1 C6 1.399(3) . ?
C1 C2 1.402(3) . ?
C1 C7 1.447(4) . ?
C2 C3 1.382(3) . ?
C2 H2 0.9500 . ?
C3 C4 1.392(3) . ?
C4 C5 1.391(4) . ?
C4 H4 0.9500 . ?
C5 C6 1.382(4) . ?
C5 H5 0.9500 . ?
C6 H6 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
C6 C1 C2 121.0(2) . . ?
C6 C1 C7 119.2(2) . . ?
C2 C1 C7 119.8(2) . . ?
C3 C2 C1 117.8(2) . . ?
C3 C2 H2 121.1 . . ?
C1 C2 H2 121.1 . . ?
C2 C3 C4 122.1(2) . . ?
C2 C3 Br1 119.25(17) . . ?
C4 C3 Br1 118.63(19) . . ?
C5 C4 C3 119.0(2) . . ?
C5 C4 H4 120.5 . . ?
C3 C4 H4 120.5 . . ?
C6 C5 C4 120.5(2) . . ?
C6 C5 H5 119.8 . . ?
C4 C5 H5 119.8 . . ?
C5 C6 C1 119.6(2) . . ?
C5 C6 H6 120.2 . . ?
C1 C6 H6 120.2 . . ?
N1 C7 C1 177.8(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
C6 C1 C2 C3 -0.4(4) . . . . ?
C7 C1 C2 C3 179.2(2) . . . . ?
C1 C2 C3 C4 -0.1(4) . . . . ?
C1 C2 C3 Br1 -179.14(18) . . . . ?
C2 C3 C4 C5 0.3(4) . . . . ?
Br1 C3 C4 C5 179.38(19) . . . . ?
C3 C4 C5 C6 -0.1(4) . . . . ?
C4 C5 C6 C1 -0.4(4) . . . . ?
C2 C1 C6 C5 0.6(4) . . . . ?
C7 C1 C6 C5 -179.0(2) . . . . ?

_refine_diff_density_max         0.535
_refine_diff_density_min         -0.952
_refine_diff_density_rms         0.107

_shelxl_version_number           2014-3



_exptl_crystal_recrystallization_method 'Re-crystallisation from solvent'
####################################################################### 
# 
# 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_CY010
_database_code_depnum_ccdc_archive 'CCDC 1828328'
loop_
_audit_author_name
_audit_author_address
'Daisuke Hashizume'
;RIKEN
Japan
;
_audit_update_record             
;
2018-03-08 deposited with the CCDC.	2020-11-27 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2014
_chemical_name_systematic        1,3-Bis(methanesulfonyl)benzene
_chemical_name_common            ?
_chemical_melting_point          474
_chemical_formula_moiety         'C8 H10 O4 S2'
_chemical_formula_sum            'C8 H10 O4 S2'
_chemical_formula_weight         234.28

loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0106 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
S S 0.1246 0.1234 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_space_group_crystal_system      monoclinic
_space_group_IT_number           15
_space_group_name_H-M_alt        'C 2/c'
_space_group_name_Hall           '-C 2yc'

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

loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x, y, -z+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                   17.8295(5)
_cell_length_b                   6.9792(2)
_cell_length_c                   7.9202(2)
_cell_angle_alpha                90
_cell_angle_beta                 92.3238(12)
_cell_angle_gamma                90
_cell_volume                     984.74(5)
_cell_formula_units_Z            4
_cell_measurement_temperature    90
_cell_measurement_reflns_used    13083
_cell_measurement_theta_min      2.286
_cell_measurement_theta_max      30.404

_exptl_crystal_description       plate
_exptl_crystal_colour            colourless
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.580
_exptl_crystal_F_000             488
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.07
_exptl_crystal_size_mid          0.06
_exptl_crystal_size_min          0.02
_exptl_absorpt_coefficient_mu    0.525
_shelx_estimated_absorpt_T_min   0.964
_shelx_estimated_absorpt_T_max   0.990
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.95530
_exptl_absorpt_correction_T_max  0.96605
_exptl_absorpt_process_details   
;
 MULABS - Empirical Correction for Absorption Anisotropy.
 R.H. Blessing, Acta Cryst. (1995), A51, 33-38.
;

_exptl_special_details           
;
 ?
;

_diffrn_ambient_temperature      90
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_source                   'Fine-focus rotating anode'
_diffrn_measurement_device_type  'Rigaku AFC-8 with Saturn70 CCD'
_diffrn_measurement_method       ω-scan
_diffrn_detector_area_resol_mean 7.31
_diffrn_reflns_number            12525
_diffrn_reflns_av_unetI/netI     0.0269
_diffrn_reflns_av_R_equivalents  0.0385
_diffrn_reflns_limit_h_min       -25
_diffrn_reflns_limit_h_max       25
_diffrn_reflns_limit_k_min       -9
_diffrn_reflns_limit_k_max       9
_diffrn_reflns_limit_l_min       -11
_diffrn_reflns_limit_l_max       11
_diffrn_reflns_theta_min         2.286
_diffrn_reflns_theta_max         30.404
_diffrn_reflns_theta_full        25.242
_diffrn_measured_fraction_theta_max 0.995
_diffrn_measured_fraction_theta_full 1.000
_diffrn_reflns_Laue_measured_fraction_max 0.995
_diffrn_reflns_Laue_measured_fraction_full 1.000
_diffrn_reflns_point_group_measured_fraction_max 0.995
_diffrn_reflns_point_group_measured_fraction_full 1.000
_reflns_number_total             1479
_reflns_number_gt                1255
_reflns_threshold_expression     'I > 2σ(I)'
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_max     .
_reflns_Friedel_fraction_full    .

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

_computing_data_collection       CrystalClear
_computing_cell_refinement       HKL2000
_computing_data_reduction        HKL2000
_computing_structure_solution    SHELXS-97
_computing_structure_refinement  'SHELXL-2014 (Sheldrick, 2014)'
_computing_molecular_graphics    SV
_computing_publication_material  'SHELXL-2014 (Sheldrick, 2014)'

_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)+(0.0417P)²+0.6189P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_atom_sites_solution_hydrogens   difmap
_refine_ls_hydrogen_treatment    refall
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       .
_refine_ls_number_reflns         1479
_refine_ls_number_parameters     85
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0379
_refine_ls_R_factor_gt           0.0306
_refine_ls_wR_factor_ref         0.0825
_refine_ls_wR_factor_gt          0.0779
_refine_ls_goodness_of_fit_ref   1.058
_refine_ls_restrained_S_all      1.058
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000

loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_site_symmetry_order
_atom_site_calc_flag
_atom_site_refinement_flags_posn
_atom_site_refinement_flags_adp
_atom_site_refinement_flags_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
S1 S 0.36143(2) 0.74435(4) 0.88488(4) 0.01920(11) Uani 1 1 d . . . . .
O1 O 0.32391(6) 0.61769(16) 0.99803(13) 0.0268(2) Uani 1 1 d . . . . .
O2 O 0.38780(6) 0.92736(15) 0.94697(14) 0.0295(3) Uani 1 1 d . . . . .
C1 C 0.43958(7) 0.61771(18) 0.80906(15) 0.0171(2) Uani 1 1 d . . . . .
C2 C 0.5000 0.7200(3) 0.7500 0.0202(4) Uani 1 2 d S T P . .
H2 H 0.5000 0.858(4) 0.7500 0.038(7) Uiso 1 2 d S . P . .
C3 C 0.43916(7) 0.41871(18) 0.81071(17) 0.0190(3) Uani 1 1 d . . . . .
H3 H 0.3979(9) 0.353(3) 0.850(2) 0.021(4) Uiso 1 1 d . . . . .
C4 C 0.5000 0.3198(3) 0.7500 0.0226(4) Uani 1 2 d S T P . .
H4 H 0.5000 0.178(4) 0.7500 0.030(6) Uiso 1 2 d S . P . .
C5 C 0.30177(8) 0.7827(2) 0.70541(19) 0.0227(3) Uani 1 1 d . . . . .
H5A H 0.2583(12) 0.834(3) 0.747(3) 0.037(5) Uiso 1 1 d . . . . .
H5B H 0.2932(10) 0.667(3) 0.653(2) 0.026(4) Uiso 1 1 d . . . . .
H5C H 0.3248(11) 0.872(3) 0.634(2) 0.032(5) Uiso 1 1 d . . . . .


_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 O2 1.4407(11) . ?
S1 O1 1.4425(10) . ?
S1 C5 1.7610(15) . ?
S1 C1 1.7751(12) . ?
C1 C3 1.3889(17) . ?
C1 C2 1.3893(15) . ?
C2 C1 1.3893(15) 2_656 ?
C2 H2 0.96(3) . ?
C3 C4 1.3881(16) . ?
C3 H3 0.931(17) . ?
C4 C3 1.3881(16) 2_656 ?
C4 H4 0.99(3) . ?
C5 H5A 0.93(2) . ?
C5 H5B 0.918(19) . ?
C5 H5C 0.949(19) . ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
O2 S1 O1 118.97(7) . . ?
O2 S1 C5 108.59(7) . . ?
O1 S1 C5 108.33(7) . . ?
O2 S1 C1 107.89(6) . . ?
O1 S1 C1 107.17(6) . . ?
C5 S1 C1 105.03(6) . . ?
C3 C1 C2 121.45(12) . . ?
C3 C1 S1 119.35(10) . . ?
C2 C1 S1 119.20(10) . . ?
C1 C2 C1 118.12(17) . 2_656 ?
C1 C2 H2 120.94(8) . . ?
C1 C2 H2 120.94(8) 2_656 . ?
C4 C3 C1 119.31(13) . . ?
C4 C3 H3 120.6(11) . . ?
C1 C3 H3 120.0(11) . . ?
C3 C4 C3 120.34(17) . 2_656 ?
C3 C4 H4 119.83(8) . . ?
C3 C4 H4 119.83(8) 2_656 . ?
S1 C5 H5A 105.1(12) . . ?
S1 C5 H5B 108.3(11) . . ?
H5A C5 H5B 112.1(17) . . ?
S1 C5 H5C 108.7(11) . . ?
H5A C5 H5C 110.0(16) . . ?
H5B C5 H5C 112.2(16) . . ?

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
O2 S1 C1 C3 152.32(11) . . . . ?
O1 S1 C1 C3 23.08(13) . . . . ?
C5 S1 C1 C3 -91.99(12) . . . . ?
O2 S1 C1 C2 -27.41(10) . . . . ?
O1 S1 C1 C2 -156.64(8) . . . . ?
C5 S1 C1 C2 88.29(10) . . . . ?
C3 C1 C2 C1 0.43(9) . . . 2_656 ?
S1 C1 C2 C1 -179.85(10) . . . 2_656 ?
C2 C1 C3 C4 -0.85(18) . . . . ?
S1 C1 C3 C4 179.43(7) . . . . ?
C1 C3 C4 C3 0.42(9) . . . 2_656 ?

_refine_diff_density_max         0.350
_refine_diff_density_min         -0.480
_refine_diff_density_rms         0.063

_shelxl_version_number           2014-3



_exptl_crystal_recrystallization_method 'Re-crystallisation from solvent'
####################################################################### 
# 
# 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_YM676
_database_code_depnum_ccdc_archive 'CCDC 1828333'
loop_
_audit_author_name
_audit_author_address
'Daisuke Hashizume'
;RIKEN
Japan
;
_audit_update_record             
;
2018-03-08 deposited with the CCDC.	2020-11-27 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2014
_chemical_name_systematic        1,4-Phenylenediamine
_chemical_name_common            ?
_chemical_melting_point          415
_chemical_formula_moiety         'C6 H8 N2'
_chemical_formula_sum            'C6 H8 N2'
_chemical_formula_weight         108.14

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'

_space_group_crystal_system      monoclinic
_space_group_IT_number           14
_space_group_name_H-M_alt        'P 21/c'
_space_group_name_Hall           '-P 2ybc'

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

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

_cell_length_a                   8.3017(2)
_cell_length_b                   5.8957(1)
_cell_length_c                   22.7478(5)
_cell_angle_alpha                90
_cell_angle_beta                 93.5648(10)
_cell_angle_gamma                90
_cell_volume                     1111.22(4)
_cell_formula_units_Z            8
_cell_measurement_temperature    90
_cell_measurement_reflns_used    18722
_cell_measurement_theta_min      1.794
_cell_measurement_theta_max      30.993

_exptl_crystal_description       block
_exptl_crystal_colour            colourless
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.293
_exptl_crystal_F_000             464
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.12
_exptl_crystal_size_mid          0.11
_exptl_crystal_size_min          0.09
_exptl_absorpt_coefficient_mu    0.081
_shelx_estimated_absorpt_T_min   0.990
_shelx_estimated_absorpt_T_max   0.993
_exptl_absorpt_correction_type   none
_exptl_absorpt_correction_T_min  ?
_exptl_absorpt_correction_T_max  ?
_exptl_absorpt_process_details   ?

_exptl_special_details           
;
 ?
;

_diffrn_ambient_temperature      90
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_source                   'Fine-focus rotating anode'
_diffrn_measurement_device_type  'Rigaku AFC-8 with Saturn70 CCD'
_diffrn_measurement_method       ω-scan
_diffrn_detector_area_resol_mean 7.31
_diffrn_reflns_number            17683
_diffrn_reflns_av_unetI/netI     0.0358
_diffrn_reflns_av_R_equivalents  0.0394
_diffrn_reflns_limit_h_min       -11
_diffrn_reflns_limit_h_max       12
_diffrn_reflns_limit_k_min       -8
_diffrn_reflns_limit_k_max       8
_diffrn_reflns_limit_l_min       -32
_diffrn_reflns_limit_l_max       32
_diffrn_reflns_theta_min         1.794
_diffrn_reflns_theta_max         30.993
_diffrn_reflns_theta_full        25.242
_diffrn_measured_fraction_theta_max 0.996
_diffrn_measured_fraction_theta_full 0.999
_diffrn_reflns_Laue_measured_fraction_max 0.996
_diffrn_reflns_Laue_measured_fraction_full 0.999
_diffrn_reflns_point_group_measured_fraction_max 0.996
_diffrn_reflns_point_group_measured_fraction_full 0.999
_reflns_number_total             3525
_reflns_number_gt                2850
_reflns_threshold_expression     'I > 2σ(I)'
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_max     .
_reflns_Friedel_fraction_full    .

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

_computing_data_collection       CrystalClear
_computing_cell_refinement       HKL2000
_computing_data_reduction        HKL2000
_computing_structure_solution    SIR2011
_computing_structure_refinement  'SHELXL-2014 (Sheldrick, 2014)'
_computing_molecular_graphics    SV
_computing_publication_material  'SHELXL-2014 (Sheldrick, 2014)'

_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)+(0.0590P)²+0.1879P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   direct
_atom_sites_solution_hydrogens   difmap
_refine_ls_hydrogen_treatment    mixed
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       .
_refine_ls_number_reflns         3525
_refine_ls_number_parameters     177
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0510
_refine_ls_R_factor_gt           0.0400
_refine_ls_wR_factor_ref         0.1125
_refine_ls_wR_factor_gt          0.1058
_refine_ls_goodness_of_fit_ref   1.027
_refine_ls_restrained_S_all      1.027
_refine_ls_shift/su_max          0.001
_refine_ls_shift/su_mean         0.000

loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_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
N1A N 0.42473(10) 0.54173(14) 0.67355(4) 0.01905(17) Uani 1 1 d . . . . .
H1NA H 0.4839(17) 0.647(2) 0.6946(6) 0.030(3) Uiso 1 1 d . . . . .
H1NB H 0.4884(17) 0.470(2) 0.6475(6) 0.034(4) Uiso 1 1 d . . . . .
N2A N 0.08636(10) -0.05627(14) 0.81643(3) 0.01803(17) Uani 1 1 d . . . . .
H2NA H 0.0254(17) -0.158(2) 0.7951(6) 0.035(4) Uiso 1 1 d . . . . .
H2NB H 0.0255(17) 0.019(2) 0.8414(6) 0.030(3) Uiso 1 1 d . . . . .
C1A C 0.34460(10) 0.39023(15) 0.71006(4) 0.01579(18) Uani 1 1 d . . . . .
C2A C 0.30142(11) 0.17233(16) 0.69033(4) 0.01647(18) Uani 1 1 d . . . . .
H2A H 0.3325 0.1224 0.6530 0.020 Uiso 1 1 calc R U . . .
C3A C 0.21361(11) 0.02764(15) 0.72465(4) 0.01608(18) Uani 1 1 d . . . . .
H3A H 0.1852 -0.1191 0.7102 0.019 Uiso 1 1 calc R U . . .
C4A C 0.16650(10) 0.09475(15) 0.78013(4) 0.01534(18) Uani 1 1 d . . . . .
C5A C 0.20930(10) 0.31275(16) 0.79971(4) 0.01628(18) Uani 1 1 d . . . . .
H5A H 0.1777 0.3629 0.8370 0.020 Uiso 1 1 calc R U . . .
C6A C 0.29749(11) 0.45761(15) 0.76552(4) 0.01647(18) Uani 1 1 d . . . . .
H6A H 0.3261 0.6042 0.7800 0.020 Uiso 1 1 calc R U . . .
N1B N 0.65232(10) 0.31563(15) 0.57922(4) 0.02068(18) Uani 1 1 d . . . . .
H1NC H 0.7204(18) 0.255(3) 0.6084(7) 0.041(4) Uiso 1 1 d . . . . .
H1ND H 0.7031(16) 0.424(2) 0.5616(6) 0.031(3) Uiso 1 1 d . . . . .
C1B C 0.58039(11) 0.15526(16) 0.53940(4) 0.01658(18) Uani 1 1 d . . . . .
C2B C 0.54273(11) 0.21218(16) 0.48046(4) 0.01803(18) Uani 1 1 d . . . . .
H2B H 0.5713 0.3578 0.4666 0.022 Uiso 1 1 calc R U . . .
C3B C 0.46428(11) 0.05974(16) 0.44170(4) 0.01784(19) Uani 1 1 d . . . . .
H3B H 0.4408 0.1026 0.4018 0.021 Uiso 1 1 calc R U . . .
N1C N 0.11462(11) 0.74720(17) 0.60018(4) 0.02342(19) Uani 1 1 d . . . . .
H1NE H 0.2165(18) 0.706(2) 0.6136(6) 0.037(4) Uiso 1 1 d . . . . .
H1NF H 0.1025(17) 0.898(3) 0.5964(7) 0.040(4) Uiso 1 1 d . . . . .
C1C C 0.06073(11) 0.62716(16) 0.54919(4) 0.01837(19) Uani 1 1 d . . . . .
C2C C -0.06456(11) 0.71153(17) 0.51132(4) 0.01948(19) Uani 1 1 d . . . . .
H2C H -0.1098 0.8559 0.5188 0.023 Uiso 1 1 calc R U . . .
C3C C -0.12357(11) 0.58625(17) 0.46282(4) 0.01944(19) Uani 1 1 d . . . . .
H3C H -0.2080 0.6470 0.4375 0.023 Uiso 1 1 calc R U . . .


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

loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
N1A C1A 1.4138(12) . ?
N1A H1NA 0.911(14) . ?
N1A H1NB 0.920(14) . ?
N2A C4A 1.4091(12) . ?
N2A H2NA 0.905(15) . ?
N2A H2NB 0.900(14) . ?
C1A C2A 1.4002(13) . ?
C1A C6A 1.4012(12) . ?
C2A C3A 1.3927(13) . ?
C2A H2A 0.9500 . ?
C3A C4A 1.4012(12) . ?
C3A H3A 0.9500 . ?
C4A C5A 1.3989(13) . ?
C5A C6A 1.3933(13) . ?
C5A H5A 0.9500 . ?
C6A H6A 0.9500 . ?
N1B C1B 1.4155(12) . ?
N1B H1NC 0.916(15) . ?
N1B H1ND 0.875(14) . ?
C1B C3B 1.3960(13) 3_656 ?
C1B C2B 1.3986(12) . ?
C2B C3B 1.3920(13) . ?
C2B H2B 0.9500 . ?
C3B C1B 1.3961(13) 3_656 ?
C3B H3B 0.9500 . ?
N1C C1C 1.4078(12) . ?
N1C H1NE 0.914(15) . ?
N1C H1NF 0.899(16) . ?
C1C C3C 1.3956(14) 3_566 ?
C1C C2C 1.4000(13) . ?
C2C C3C 1.3912(13) . ?
C2C H2C 0.9500 . ?
C3C C1C 1.3956(14) 3_566 ?
C3C H3C 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
C1A N1A H1NA 112.4(8) . . ?
C1A N1A H1NB 113.5(9) . . ?
H1NA N1A H1NB 109.8(12) . . ?
C4A N2A H2NA 111.9(9) . . ?
C4A N2A H2NB 111.2(9) . . ?
H2NA N2A H2NB 110.3(13) . . ?
C2A C1A C6A 117.94(8) . . ?
C2A C1A N1A 120.78(8) . . ?
C6A C1A N1A 121.17(8) . . ?
C3A C2A C1A 120.98(8) . . ?
C3A C2A H2A 119.5 . . ?
C1A C2A H2A 119.5 . . ?
C2A C3A C4A 121.14(8) . . ?
C2A C3A H3A 119.4 . . ?
C4A C3A H3A 119.4 . . ?
C5A C4A C3A 117.82(8) . . ?
C5A C4A N2A 120.91(8) . . ?
C3A C4A N2A 121.19(8) . . ?
C6A C5A C4A 121.15(8) . . ?
C6A C5A H5A 119.4 . . ?
C4A C5A H5A 119.4 . . ?
C5A C6A C1A 120.97(8) . . ?
C5A C6A H6A 119.5 . . ?
C1A C6A H6A 119.5 . . ?
C1B N1B H1NC 114.9(10) . . ?
C1B N1B H1ND 112.9(9) . . ?
H1NC N1B H1ND 108.8(13) . . ?
C3B C1B C2B 117.72(8) 3_656 . ?
C3B C1B N1B 121.27(8) 3_656 . ?
C2B C1B N1B 120.89(9) . . ?
C3B C2B C1B 121.34(9) . . ?
C3B C2B H2B 119.3 . . ?
C1B C2B H2B 119.3 . . ?
C2B C3B C1B 120.93(8) . 3_656 ?
C2B C3B H3B 119.5 . . ?
C1B C3B H3B 119.5 3_656 . ?
C1C N1C H1NE 112.5(9) . . ?
C1C N1C H1NF 113.1(10) . . ?
H1NE N1C H1NF 112.9(13) . . ?
C3C C1C C2C 118.18(8) 3_566 . ?
C3C C1C N1C 120.73(9) 3_566 . ?
C2C C1C N1C 120.95(9) . . ?
C3C C2C C1C 120.72(9) . . ?
C3C C2C H2C 119.6 . . ?
C1C C2C H2C 119.6 . . ?
C2C C3C C1C 121.09(8) . 3_566 ?
C2C C3C H3C 119.5 . . ?
C1C C3C H3C 119.5 3_566 . ?

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
C6A C1A C2A C3A 0.34(13) . . . . ?
N1A C1A C2A C3A -175.94(8) . . . . ?
C1A C2A C3A C4A -0.38(13) . . . . ?
C2A C3A C4A C5A 0.57(13) . . . . ?
C2A C3A C4A N2A -176.05(8) . . . . ?
C3A C4A C5A C6A -0.73(13) . . . . ?
N2A C4A C5A C6A 175.89(8) . . . . ?
C4A C5A C6A C1A 0.72(13) . . . . ?
C2A C1A C6A C5A -0.50(13) . . . . ?
N1A C1A C6A C5A 175.76(8) . . . . ?
C3B C1B C2B C3B -0.39(15) 3_656 . . . ?
N1B C1B C2B C3B -176.57(9) . . . . ?
C1B C2B C3B C1B 0.40(15) . . . 3_656 ?
C3C C1C C2C C3C -0.50(15) 3_566 . . . ?
N1C C1C C2C C3C -176.32(9) . . . . ?
C1C C2C C3C C1C 0.51(15) . . . 3_566 ?

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
N1A H1NB N1B 0.920(14) 2.315(15) 3.2336(12) 175.9(12) .
N2A H2NB N1C 0.900(14) 2.263(14) 3.1586(12) 173.1(12) 2_546
N1B H1NC N2A 0.916(15) 2.528(15) 3.2048(12) 131.0(12) 2_656
N1C H1NE N1A 0.914(15) 2.344(15) 3.2166(13) 159.7(13) .

_refine_diff_density_max         0.364
_refine_diff_density_min         -0.219
_refine_diff_density_rms         0.046

_shelxl_version_number           2014-3



_exptl_crystal_recrystallization_method 'Re-crystallisation from solvent'
_chemical_properties_physical    Light-sensitive
####################################################################### 
# 
# 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_CY013
_database_code_depnum_ccdc_archive 'CCDC 1828334'
loop_
_audit_author_name
_audit_author_address
'Daisuke Hashizume'
;RIKEN
Japan
;
_audit_update_record             
;
2018-03-08 deposited with the CCDC.	2020-11-27 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2014
_chemical_name_systematic        4-Bromobenzonitrile
_chemical_name_common            ?
_chemical_melting_point          385
_chemical_formula_moiety         'C7 H4 Br N'
_chemical_formula_sum            'C7 H4 Br N'
_chemical_formula_weight         182.02

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

_space_group_crystal_system      monoclinic
_space_group_IT_number           8
_space_group_name_H-M_alt        'C m'
_space_group_name_Hall           'C -2y'

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

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

_cell_length_a                   9.4437(1)
_cell_length_b                   8.5227(1)
_cell_length_c                   4.0482(1)
_cell_angle_alpha                90
_cell_angle_beta                 91.2214(1)
_cell_angle_gamma                90
_cell_volume                     325.749(10)
_cell_formula_units_Z            2
_cell_measurement_temperature    90
_cell_measurement_reflns_used    4004
_cell_measurement_theta_min      3.220
_cell_measurement_theta_max      30.334

_exptl_crystal_description       needle
_exptl_crystal_colour            colourless
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.856
_exptl_crystal_F_000             176
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.07
_exptl_crystal_size_mid          0.04
_exptl_crystal_size_min          0.03
_exptl_absorpt_coefficient_mu    6.203
_shelx_estimated_absorpt_T_min   0.671
_shelx_estimated_absorpt_T_max   0.836
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.63685
_exptl_absorpt_correction_T_max  0.67326
_exptl_absorpt_process_details   
;
 MULABS - Empirical Correction for Absorption Anisotropy.
 R.H. Blessing, Acta Cryst. (1995), A51, 33-38.
;

_exptl_special_details           
;
 ?
;

_diffrn_ambient_temperature      90
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_source                   'Fine-focus rotating anode'
_diffrn_measurement_device_type  'Rigaku AFC-8 with Saturn70 CCD'
_diffrn_measurement_method       ω-scan
_diffrn_detector_area_resol_mean 7.31
_diffrn_reflns_number            4004
_diffrn_reflns_av_unetI/netI     0.0276
_diffrn_reflns_av_R_equivalents  0.0358
_diffrn_reflns_limit_h_min       -13
_diffrn_reflns_limit_h_max       13
_diffrn_reflns_limit_k_min       -12
_diffrn_reflns_limit_k_max       12
_diffrn_reflns_limit_l_min       -5
_diffrn_reflns_limit_l_max       5
_diffrn_reflns_theta_min         3.220
_diffrn_reflns_theta_max         30.334
_diffrn_reflns_theta_full        25.242
_diffrn_measured_fraction_theta_max 0.994
_diffrn_measured_fraction_theta_full 1.000
_diffrn_reflns_Laue_measured_fraction_max 0.994
_diffrn_reflns_Laue_measured_fraction_full 1.000
_diffrn_reflns_point_group_measured_fraction_max 0.994
_diffrn_reflns_point_group_measured_fraction_full 1.000
_reflns_number_total             1031
_reflns_number_gt                1031
_reflns_threshold_expression     'I > 2σ(I)'
_reflns_Friedel_coverage         0.988
_reflns_Friedel_fraction_max     0.994
_reflns_Friedel_fraction_full    1.000

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

_computing_data_collection       CrystalClear
_computing_cell_refinement       HKL2000
_computing_data_reduction        HKL2000
_computing_structure_solution    SIR2004
_computing_structure_refinement  'SHELXL-2014 (Sheldrick, 2014)'
_computing_molecular_graphics    SV
_computing_publication_material  'SHELXL-2014 (Sheldrick, 2014)'

_refine_special_details          
;
 Refined as a 2-component inversion 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)+(0.0300P)²+0.1262P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_atom_sites_solution_hydrogens   difmap
_refine_ls_hydrogen_treatment    refall
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       .
_refine_ls_abs_structure_details 
;
 Refined as an inversion twin.
;
_refine_ls_abs_structure_Flack   0.41(2)
_chemical_absolute_configuration ?
_refine_ls_number_reflns         1031
_refine_ls_number_parameters     58
_refine_ls_number_restraints     2
_refine_ls_R_factor_all          0.0209
_refine_ls_R_factor_gt           0.0209
_refine_ls_wR_factor_ref         0.0520
_refine_ls_wR_factor_gt          0.0520
_refine_ls_goodness_of_fit_ref   1.083
_refine_ls_restrained_S_all      1.082
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000

loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_site_symmetry_order
_atom_site_calc_flag
_atom_site_refinement_flags_posn
_atom_site_refinement_flags_adp
_atom_site_refinement_flags_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
Br1 Br 0.60183(2) 0.5000 0.41858(2) 0.02458(12) Uani 1 2 d S T P . .
N1 N -0.0756(6) 0.5000 1.2195(13) 0.0336(10) Uani 1 2 d S T P . .
C1 C 0.1669(5) 0.5000 0.9353(14) 0.0231(9) Uani 1 2 d S T P . .
C2 C 0.2309(4) 0.3574(4) 0.8553(9) 0.0236(6) Uani 1 1 d . . . . .
H2 H 0.189(5) 0.262(7) 0.940(13) 0.028(12) Uiso 1 1 d . . . . .
C3 C 0.3597(4) 0.3578(4) 0.6954(9) 0.0241(6) Uani 1 1 d . . . . .
H3 H 0.401(6) 0.265(7) 0.651(14) 0.033(13) Uiso 1 1 d . . . . .
C4 C 0.4217(5) 0.5000 0.6184(12) 0.0216(8) Uani 1 2 d S T P . .
C5 C 0.0318(6) 0.5000 1.0955(15) 0.0274(10) Uani 1 2 d S T P . .


_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 C4 1.899(5) . ?
N1 C5 1.141(8) . ?
C1 C2 1.399(4) . ?
C1 C2 1.399(4) 2_565 ?
C1 C5 1.444(8) . ?
C2 C3 1.390(5) . ?
C2 H2 0.97(6) . ?
C3 C4 1.384(4) . ?
C3 H3 0.90(6) . ?
C4 C3 1.384(4) 2_565 ?

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 C2 120.7(5) . 2_565 ?
C2 C1 C5 119.7(2) . . ?
C2 C1 C5 119.7(2) 2_565 . ?
C3 C2 C1 119.5(3) . . ?
C3 C2 H2 122(3) . . ?
C1 C2 H2 118(3) . . ?
C4 C3 C2 119.0(3) . . ?
C4 C3 H3 122(4) . . ?
C2 C3 H3 119(4) . . ?
C3 C4 C3 122.2(5) . 2_565 ?
C3 C4 Br1 118.9(2) . . ?
C3 C4 Br1 118.9(2) 2_565 . ?
N1 C5 C1 179.4(7) . . ?

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
C2 C1 C2 C3 0.2(8) 2_565 . . . ?
C5 C1 C2 C3 178.8(5) . . . . ?
C1 C2 C3 C4 -0.1(6) . . . . ?
C2 C3 C4 C3 0.0(7) . . . 2_565 ?
C2 C3 C4 Br1 177.1(3) . . . . ?

_refine_diff_density_max         0.340
_refine_diff_density_min         -0.602
_refine_diff_density_rms         0.071

_shelxl_version_number           2014-3



_exptl_crystal_recrystallization_method 'Re-crystallisation from solvent'
####################################################################### 
# 
# 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_CY012
_database_code_depnum_ccdc_archive 'CCDC 1828330'
loop_
_audit_author_name
_audit_author_address
'Daisuke Hashizume'
;RIKEN
Japan
;
_audit_update_record             
;
2018-03-08 deposited with the CCDC.	2020-11-27 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2014
_chemical_name_systematic        1,4-Bis(methaneslufonyl)benzene
_chemical_name_common            ?
_chemical_melting_point          537
_chemical_formula_moiety         'C8 H10 O4 S2'
_chemical_formula_sum            'C8 H10 O4 S2'
_chemical_formula_weight         234.28

loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0106 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
S S 0.1246 0.1234 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

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

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

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

_cell_length_a                   5.3453(1)
_cell_length_b                   6.6576(1)
_cell_length_c                   6.9904(1)
_cell_angle_alpha                86.1628(1)
_cell_angle_beta                 88.9324(1)
_cell_angle_gamma                82.6823(1)
_cell_volume                     246.174(7)
_cell_formula_units_Z            1
_cell_measurement_temperature    90
_cell_measurement_reflns_used    5393
_cell_measurement_theta_min      2.921
_cell_measurement_theta_max      30.034

_exptl_crystal_description       plate
_exptl_crystal_colour            colourless
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.580
_exptl_crystal_F_000             122
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.07
_exptl_crystal_size_mid          0.04
_exptl_crystal_size_min          0.03
_exptl_absorpt_coefficient_mu    0.525
_shelx_estimated_absorpt_T_min   0.964
_shelx_estimated_absorpt_T_max   0.984
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.95851
_exptl_absorpt_correction_T_max  0.96924
_exptl_absorpt_process_details   
;
 MULABS - Empirical Correction for Absorption Anisotropy.
 R.H. Blessing, Acta Cryst. (1995), A51, 33-38.
;

_exptl_special_details           
;
 ?
;

_diffrn_ambient_temperature      90
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_source                   'Fine-focus rotating anode'
_diffrn_measurement_device_type  'Rigaku AFC-8 with Saturn70 CCD'
_diffrn_measurement_method       ω-scan
_diffrn_detector_area_resol_mean 7.31
_diffrn_reflns_number            5392
_diffrn_reflns_av_unetI/netI     0.0403
_diffrn_reflns_av_R_equivalents  0.0335
_diffrn_reflns_limit_h_min       -7
_diffrn_reflns_limit_h_max       7
_diffrn_reflns_limit_k_min       -9
_diffrn_reflns_limit_k_max       9
_diffrn_reflns_limit_l_min       -9
_diffrn_reflns_limit_l_max       9
_diffrn_reflns_theta_min         2.921
_diffrn_reflns_theta_max         30.034
_diffrn_reflns_theta_full        25.242
_diffrn_measured_fraction_theta_max 0.999
_diffrn_measured_fraction_theta_full 1.000
_diffrn_reflns_Laue_measured_fraction_max 0.999
_diffrn_reflns_Laue_measured_fraction_full 1.000
_diffrn_reflns_point_group_measured_fraction_max 0.999
_diffrn_reflns_point_group_measured_fraction_full 1.000
_reflns_number_total             1447
_reflns_number_gt                1263
_reflns_threshold_expression     'I > 2σ(I)'
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_max     .
_reflns_Friedel_fraction_full    .

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

_computing_data_collection       CrystalClear
_computing_cell_refinement       HKL2000
_computing_data_reduction        HKL2000
_computing_structure_solution    SIR2004
_computing_structure_refinement  'SHELXL-2014 (Sheldrick, 2014)'
_computing_molecular_graphics    SV
_computing_publication_material  'SHELXL-2014 (Sheldrick, 2014)'

_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)+(0.0252P)²+0.1238P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_atom_sites_solution_hydrogens   difmap
_refine_ls_hydrogen_treatment    refall
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       .
_refine_ls_number_reflns         1447
_refine_ls_number_parameters     84
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0380
_refine_ls_R_factor_gt           0.0312
_refine_ls_wR_factor_ref         0.0754
_refine_ls_wR_factor_gt          0.0723
_refine_ls_goodness_of_fit_ref   1.050
_refine_ls_restrained_S_all      1.050
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000

loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_site_symmetry_order
_atom_site_calc_flag
_atom_site_refinement_flags_posn
_atom_site_refinement_flags_adp
_atom_site_refinement_flags_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
S1 S 0.16761(6) 0.82357(5) 0.22938(5) 0.01381(11) Uani 1 1 d . . . . .
O1 O 0.1896(2) 0.75568(17) 0.03627(15) 0.0206(2) Uani 1 1 d . . . . .
O2 O -0.08141(19) 0.86038(16) 0.31479(16) 0.0180(2) Uani 1 1 d . . . . .
C1 C 0.3541(3) 0.6397(2) 0.3820(2) 0.0134(3) Uani 1 1 d . . . . .
C2 C 0.5509(3) 0.5143(2) 0.3020(2) 0.0160(3) Uani 1 1 d . . . . .
H2 H 0.583(4) 0.523(3) 0.166(3) 0.023(5) Uiso 1 1 d . . . . .
C3 C 0.6992(3) 0.3717(2) 0.4212(2) 0.0161(3) Uani 1 1 d . . . . .
H3 H 0.836(4) 0.278(3) 0.369(3) 0.028(5) Uiso 1 1 d . . . . .
C4 C 0.3168(3) 1.0464(2) 0.2371(2) 0.0172(3) Uani 1 1 d . . . . .
H4A H 0.223(4) 1.145(3) 0.149(3) 0.025(5) Uiso 1 1 d . . . . .
H4B H 0.497(4) 1.016(3) 0.199(3) 0.027(5) Uiso 1 1 d . . . . .
H4C H 0.298(4) 1.090(3) 0.364(3) 0.026(5) Uiso 1 1 d . . . . .


_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 O2 1.4475(11) . ?
S1 O1 1.4500(11) . ?
S1 C4 1.7757(15) . ?
S1 C1 1.7845(14) . ?
C1 C2 1.3911(19) . ?
C1 C3 1.398(2) 2_666 ?
C2 C3 1.397(2) . ?
C2 H2 0.959(19) . ?
C3 C1 1.398(2) 2_666 ?
C3 H3 0.98(2) . ?
C4 H4A 0.96(2) . ?
C4 H4B 0.99(2) . ?
C4 H4C 0.95(2) . ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
O2 S1 O1 118.39(7) . . ?
O2 S1 C4 108.71(7) . . ?
O1 S1 C4 108.80(7) . . ?
O2 S1 C1 107.99(6) . . ?
O1 S1 C1 107.79(6) . . ?
C4 S1 C1 104.26(7) . . ?
C2 C1 C3 121.96(13) . 2_666 ?
C2 C1 S1 118.93(11) . . ?
C3 C1 S1 119.10(11) 2_666 . ?
C1 C2 C3 119.13(13) . . ?
C1 C2 H2 120.7(12) . . ?
C3 C2 H2 120.2(12) . . ?
C2 C3 C1 118.91(13) . 2_666 ?
C2 C3 H3 121.4(12) . . ?
C1 C3 H3 119.6(12) 2_666 . ?
S1 C4 H4A 105.0(11) . . ?
S1 C4 H4B 109.4(11) . . ?
H4A C4 H4B 112.5(16) . . ?
S1 C4 H4C 107.6(12) . . ?
H4A C4 H4C 110.1(16) . . ?
H4B C4 H4C 111.9(16) . . ?

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
O2 S1 C1 C2 152.09(11) . . . . ?
O1 S1 C1 C2 23.10(13) . . . . ?
C4 S1 C1 C2 -92.41(13) . . . . ?
O2 S1 C1 C3 -28.96(13) . . . 2_666 ?
O1 S1 C1 C3 -157.95(12) . . . 2_666 ?
C4 S1 C1 C3 86.54(13) . . . 2_666 ?
C3 C1 C2 C3 0.4(2) 2_666 . . . ?
S1 C1 C2 C3 179.28(11) . . . . ?
C1 C2 C3 C1 -0.4(2) . . . 2_666 ?

_refine_diff_density_max         0.380
_refine_diff_density_min         -0.481
_refine_diff_density_rms         0.065

_shelxl_version_number           2014-3



_exptl_crystal_recrystallization_method 'Re-crystallisation from solvent'
####################################################################### 
# 
# 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_YM675
_database_code_depnum_ccdc_archive 'CCDC 1828332'
loop_
_audit_author_name
_audit_author_address
'Daisuke Hashizume'
;RIKEN
Japan
;
_audit_update_record             
;
2018-03-08 deposited with the CCDC.	2020-11-27 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2014
_chemical_name_systematic        1,3-Phenylenediamine
_chemical_name_common            ?
_chemical_melting_point          334
_chemical_formula_moiety         'C6 H8 N2'
_chemical_formula_sum            'C6 H8 N2'
_chemical_formula_weight         108.14

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'

_space_group_crystal_system      monoclinic
_space_group_IT_number           14
_space_group_name_H-M_alt        'P 21/c'
_space_group_name_Hall           '-P 2ybc'

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

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

_cell_length_a                   8.0887(1)
_cell_length_b                   11.9923(2)
_cell_length_c                   23.8075(4)
_cell_angle_alpha                90
_cell_angle_beta                 90.9951(6)
_cell_angle_gamma                90
_cell_volume                     2309.03(6)
_cell_formula_units_Z            16
_cell_measurement_temperature    90
_cell_measurement_reflns_used    65112
_cell_measurement_theta_min      1.711
_cell_measurement_theta_max      31.136

_exptl_crystal_description       block
_exptl_crystal_colour            colourless
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.244
_exptl_crystal_F_000             928
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.08
_exptl_crystal_size_mid          0.07
_exptl_crystal_size_min          0.07
_exptl_absorpt_coefficient_mu    0.078
_shelx_estimated_absorpt_T_min   0.994
_shelx_estimated_absorpt_T_max   0.995
_exptl_absorpt_correction_type   none
_exptl_absorpt_correction_T_min  ?
_exptl_absorpt_correction_T_max  ?
_exptl_absorpt_process_details   ?

_exptl_special_details           
;
 ?
;

_diffrn_ambient_temperature      90
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_source                   'Fine-focus rotating anode'
_diffrn_measurement_device_type  'Rigaku AFC-8 with Saturn70 CCD'
_diffrn_measurement_method       ω-scan
_diffrn_detector_area_resol_mean 7.31
_diffrn_reflns_number            63438
_diffrn_reflns_av_unetI/netI     0.0315
_diffrn_reflns_av_R_equivalents  0.0445
_diffrn_reflns_limit_h_min       -11
_diffrn_reflns_limit_h_max       11
_diffrn_reflns_limit_k_min       -17
_diffrn_reflns_limit_k_max       17
_diffrn_reflns_limit_l_min       -34
_diffrn_reflns_limit_l_max       34
_diffrn_reflns_theta_min         1.711
_diffrn_reflns_theta_max         31.136
_diffrn_reflns_theta_full        25.242
_diffrn_measured_fraction_theta_max 0.996
_diffrn_measured_fraction_theta_full 0.999
_diffrn_reflns_Laue_measured_fraction_max 0.996
_diffrn_reflns_Laue_measured_fraction_full 0.999
_diffrn_reflns_point_group_measured_fraction_max 0.996
_diffrn_reflns_point_group_measured_fraction_full 0.999
_reflns_number_total             7429
_reflns_number_gt                5829
_reflns_threshold_expression     'I > 2σ(I)'
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_max     .
_reflns_Friedel_fraction_full    .

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

_computing_data_collection       CrystalClear
_computing_cell_refinement       HKL2000
_computing_data_reduction        HKL2000
_computing_structure_solution    SIR2011
_computing_structure_refinement  'SHELXL-2014 (Sheldrick, 2014)'
_computing_molecular_graphics    SV
_computing_publication_material  'SHELXL-2014 (Sheldrick, 2014)'

_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)+(0.0514P)²+0.4109P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   direct
_atom_sites_solution_hydrogens   difmap
_refine_ls_hydrogen_treatment    mixed
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       .
_refine_ls_number_reflns         7429
_refine_ls_number_parameters     353
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0532
_refine_ls_R_factor_gt           0.0383
_refine_ls_wR_factor_ref         0.1035
_refine_ls_wR_factor_gt          0.0958
_refine_ls_goodness_of_fit_ref   1.032
_refine_ls_restrained_S_all      1.032
_refine_ls_shift/su_max          0.001
_refine_ls_shift/su_mean         0.000

loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_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
N1A N 0.53927(10) 0.37392(7) 0.21724(4) 0.02097(16) Uani 1 1 d . . . . .
H1NA H 0.5949(17) 0.4309(12) 0.2024(6) 0.036(4) Uiso 1 1 d . . . . .
H1NB H 0.6070(19) 0.3318(13) 0.2396(6) 0.046(4) Uiso 1 1 d . . . . .
N2A N 0.27638(11) 0.02618(7) 0.16420(4) 0.02060(16) Uani 1 1 d . . . . .
H2NA H 0.2722(17) 0.0118(12) 0.2022(6) 0.039(4) Uiso 1 1 d . . . . .
H2NB H 0.1900(17) -0.0034(11) 0.1458(6) 0.033(3) Uiso 1 1 d . . . . .
C1A C 0.44825(11) 0.31143(7) 0.17742(4) 0.01729(17) Uani 1 1 d . . . . .
C2A C 0.40658(11) 0.20096(7) 0.18931(4) 0.01662(16) Uani 1 1 d . . . . .
H2A H 0.4460 0.1677 0.2232 0.020 Uiso 1 1 calc R U . . .
C3A C 0.30792(11) 0.13844(7) 0.15221(4) 0.01675(16) Uani 1 1 d . . . . .
C4A C 0.24953(11) 0.18813(8) 0.10236(4) 0.01953(17) Uani 1 1 d . . . . .
H4A H 0.1809 0.1473 0.0769 0.023 Uiso 1 1 calc R U . . .
C5A C 0.29307(12) 0.29790(8) 0.09044(4) 0.02100(18) Uani 1 1 d . . . . .
H5A H 0.2545 0.3310 0.0564 0.025 Uiso 1 1 calc R U . . .
C6A C 0.39151(11) 0.36005(8) 0.12712(4) 0.02010(18) Uani 1 1 d . . . . .
H6A H 0.4201 0.4347 0.1182 0.024 Uiso 1 1 calc R U . . .
N1B N 0.73309(11) 0.00491(7) 0.20807(4) 0.02124(16) Uani 1 1 d . . . . .
H1NC H 0.6448(16) -0.0249(11) 0.2250(5) 0.030(3) Uiso 1 1 d . . . . .
H1ND H 0.7157(16) 0.0119(11) 0.1697(6) 0.031(3) Uiso 1 1 d . . . . .
N2B N 1.03070(10) 0.35697(7) 0.19811(4) 0.02131(16) Uani 1 1 d . . . . .
H2NC H 1.0765(18) 0.3277(12) 0.1667(6) 0.041(4) Uiso 1 1 d . . . . .
H2ND H 1.1041(17) 0.3932(11) 0.2191(6) 0.032(3) Uiso 1 1 d . . . . .
C1B C 0.78748(10) 0.10394(7) 0.23329(4) 0.01654(16) Uani 1 1 d . . . . .
C2B C 0.88068(11) 0.18085(7) 0.20277(4) 0.01626(16) Uani 1 1 d . . . . .
H2B H 0.9012 0.1676 0.1642 0.020 Uiso 1 1 calc R U . . .
C3B C 0.94370(10) 0.27693(7) 0.22871(4) 0.01667(16) Uani 1 1 d . . . . .
C4B C 0.91364(11) 0.29603(8) 0.28571(4) 0.01959(18) Uani 1 1 d . . . . .
H4B H 0.9571 0.3606 0.3038 0.024 Uiso 1 1 calc R U . . .
C5B C 0.81988(12) 0.21996(8) 0.31560(4) 0.02140(18) Uani 1 1 d . . . . .
H5B H 0.7993 0.2333 0.3542 0.026 Uiso 1 1 calc R U . . .
C6B C 0.75576(11) 0.12477(8) 0.29007(4) 0.01990(18) Uani 1 1 d . . . . .
H6B H 0.6908 0.0741 0.3110 0.024 Uiso 1 1 calc R U . . .
N1C N 0.18934(10) 0.07705(7) 0.29705(3) 0.01807(15) Uani 1 1 d . . . . .
H1NE H 0.1117(16) 0.0213(11) 0.3013(5) 0.028(3) Uiso 1 1 d . . . . .
H1NF H 0.1487(16) 0.1317(12) 0.2775(6) 0.032(3) Uiso 1 1 d . . . . .
N2C N 0.50599(11) 0.34939(7) 0.40647(4) 0.02235(17) Uani 1 1 d . . . . .
H2NE H 0.5400(16) 0.3793(11) 0.3732(6) 0.032(3) Uiso 1 1 d . . . . .
H2NF H 0.5900(17) 0.3498(12) 0.4325(6) 0.034(3) Uiso 1 1 d . . . . .
C1C C 0.26167(10) 0.11244(7) 0.34799(4) 0.01567(16) Uani 1 1 d . . . . .
C2C C 0.34322(11) 0.21519(7) 0.35205(4) 0.01663(16) Uani 1 1 d . . . . .
H2C H 0.3405 0.2651 0.3211 0.020 Uiso 1 1 calc R U . . .
C3C C 0.42863(11) 0.24484(7) 0.40142(4) 0.01771(17) Uani 1 1 d . . . . .
C4C C 0.43124(12) 0.17126(8) 0.44718(4) 0.02086(18) Uani 1 1 d . . . . .
H4C H 0.4900 0.1902 0.4807 0.025 Uiso 1 1 calc R U . . .
C5C C 0.34757(12) 0.07066(8) 0.44315(4) 0.02168(18) Uani 1 1 d . . . . .
H5C H 0.3487 0.0213 0.4744 0.026 Uiso 1 1 calc R U . . .
C6C C 0.26211(11) 0.04060(7) 0.39432(4) 0.01852(17) Uani 1 1 d . . . . .
H6C H 0.2043 -0.0283 0.3924 0.022 Uiso 1 1 calc R U . . .
N1D N 0.65949(11) 0.41590(7) 0.57635(4) 0.02221(17) Uani 1 1 d . . . . .
H1NG H 0.5799(17) 0.3750(12) 0.5934(6) 0.035(4) Uiso 1 1 d . . . . .
H1NH H 0.6180(16) 0.4835(12) 0.5645(5) 0.032(3) Uiso 1 1 d . . . . .
N2D N 1.01372(11) 0.40817(7) 0.41354(3) 0.02129(16) Uani 1 1 d . . . . .
H2NG H 1.0503(17) 0.4777(12) 0.4215(6) 0.036(4) Uiso 1 1 d . . . . .
H2NH H 1.0979(17) 0.3671(12) 0.3984(6) 0.034(4) Uiso 1 1 d . . . . .
C1D C 0.75636(11) 0.35644(7) 0.53869(4) 0.01698(16) Uani 1 1 d . . . . .
C2D C 0.83420(11) 0.41074(7) 0.49431(4) 0.01647(16) Uani 1 1 d . . . . .
H2D H 0.8147 0.4879 0.4881 0.020 Uiso 1 1 calc R U . . .
C3D C 0.94065(11) 0.35252(8) 0.45887(4) 0.01702(16) Uani 1 1 d . . . . .
C4D C 0.96667(12) 0.23864(8) 0.46727(4) 0.02109(18) Uani 1 1 d . . . . .
H4D H 1.0378 0.1982 0.4433 0.025 Uiso 1 1 calc R U . . .
C5D C 0.88734(12) 0.18513(8) 0.51105(4) 0.02289(19) Uani 1 1 d . . . . .
H5D H 0.9047 0.1075 0.5166 0.027 Uiso 1 1 calc R U . . .
C6D C 0.78366(12) 0.24203(8) 0.54683(4) 0.02094(18) Uani 1 1 d . . . . .
H6D H 0.7314 0.2038 0.5767 0.025 Uiso 1 1 calc R U . . .


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

loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
N1A C1A 1.4065(12) . ?
N1A H1NA 0.894(15) . ?
N1A H1NB 0.910(16) . ?
N2A C3A 1.4006(12) . ?
N2A H2NA 0.921(15) . ?
N2A H2NB 0.892(14) . ?
C1A C2A 1.3972(12) . ?
C1A C6A 1.4019(13) . ?
C2A C3A 1.3981(12) . ?
C2A H2A 0.9500 . ?
C3A C4A 1.4026(13) . ?
C4A C5A 1.3932(13) . ?
C4A H4A 0.9500 . ?
C5A C6A 1.3884(14) . ?
C5A H5A 0.9500 . ?
C6A H6A 0.9500 . ?
N1B C1B 1.3983(12) . ?
N1B H1NC 0.901(13) . ?
N1B H1ND 0.925(14) . ?
N2B C3B 1.4017(12) . ?
N2B H2NC 0.912(15) . ?
N2B H2ND 0.884(14) . ?
C1B C2B 1.4021(12) . ?
C1B C6B 1.4026(12) . ?
C2B C3B 1.3992(12) . ?
C2B H2B 0.9500 . ?
C3B C4B 1.4018(12) . ?
C4B C5B 1.3902(14) . ?
C4B H4B 0.9500 . ?
C5B C6B 1.3895(13) . ?
C5B H5B 0.9500 . ?
C6B H6B 0.9500 . ?
N1C C1C 1.4031(11) . ?
N1C H1NE 0.924(13) . ?
N1C H1NF 0.865(14) . ?
N2C C3C 1.4054(12) . ?
N2C H2NE 0.915(14) . ?
N2C H2NF 0.912(14) . ?
C1C C6C 1.3995(12) . ?
C1C C2C 1.4002(12) . ?
C2C C3C 1.3989(12) . ?
C2C H2C 0.9500 . ?
C3C C4C 1.4017(13) . ?
C4C C5C 1.3858(14) . ?
C4C H4C 0.9500 . ?
C5C C6C 1.3898(13) . ?
C5C H5C 0.9500 . ?
C6C H6C 0.9500 . ?
N1D C1D 1.3966(12) . ?
N1D H1NG 0.910(14) . ?
N1D H1NH 0.920(14) . ?
N2D C3D 1.4078(12) . ?
N2D H2NG 0.904(15) . ?
N2D H2NH 0.919(14) . ?
C1D C2D 1.4000(12) . ?
C1D C6D 1.4026(13) . ?
C2D C3D 1.4021(12) . ?
C2D H2D 0.9500 . ?
C3D C4D 1.3957(13) . ?
C4D C5D 1.3905(14) . ?
C4D H4D 0.9500 . ?
C5D C6D 1.3854(14) . ?
C5D H5D 0.9500 . ?
C6D H6D 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
C1A N1A H1NA 113.7(9) . . ?
C1A N1A H1NB 113.7(10) . . ?
H1NA N1A H1NB 110.6(13) . . ?
C3A N2A H2NA 113.0(9) . . ?
C3A N2A H2NB 115.2(9) . . ?
H2NA N2A H2NB 111.4(12) . . ?
C2A C1A C6A 119.40(8) . . ?
C2A C1A N1A 119.60(8) . . ?
C6A C1A N1A 120.93(8) . . ?
C1A C2A C3A 121.16(8) . . ?
C1A C2A H2A 119.4 . . ?
C3A C2A H2A 119.4 . . ?
C2A C3A N2A 119.38(8) . . ?
C2A C3A C4A 119.14(8) . . ?
N2A C3A C4A 121.40(8) . . ?
C5A C4A C3A 119.42(8) . . ?
C5A C4A H4A 120.3 . . ?
C3A C4A H4A 120.3 . . ?
C6A C5A C4A 121.56(9) . . ?
C6A C5A H5A 119.2 . . ?
C4A C5A H5A 119.2 . . ?
C5A C6A C1A 119.32(8) . . ?
C5A C6A H6A 120.3 . . ?
C1A C6A H6A 120.3 . . ?
C1B N1B H1NC 113.0(8) . . ?
C1B N1B H1ND 112.8(9) . . ?
H1NC N1B H1ND 111.7(12) . . ?
C3B N2B H2NC 112.2(9) . . ?
C3B N2B H2ND 112.4(9) . . ?
H2NC N2B H2ND 112.1(12) . . ?
N1B C1B C2B 120.28(8) . . ?
N1B C1B C6B 120.24(8) . . ?
C2B C1B C6B 119.41(8) . . ?
C3B C2B C1B 120.54(8) . . ?
C3B C2B H2B 119.7 . . ?
C1B C2B H2B 119.7 . . ?
C2B C3B N2B 121.13(8) . . ?
C2B C3B C4B 119.59(8) . . ?
N2B C3B C4B 119.23(8) . . ?
C5B C4B C3B 119.59(8) . . ?
C5B C4B H4B 120.2 . . ?
C3B C4B H4B 120.2 . . ?
C6B C5B C4B 121.19(8) . . ?
C6B C5B H5B 119.4 . . ?
C4B C5B H5B 119.4 . . ?
C5B C6B C1B 119.66(9) . . ?
C5B C6B H6B 120.2 . . ?
C1B C6B H6B 120.2 . . ?
C1C N1C H1NE 113.4(8) . . ?
C1C N1C H1NF 112.7(9) . . ?
H1NE N1C H1NF 110.7(12) . . ?
C3C N2C H2NE 114.5(8) . . ?
C3C N2C H2NF 112.9(9) . . ?
H2NE N2C H2NF 110.8(12) . . ?
C6C C1C C2C 119.50(8) . . ?
C6C C1C N1C 119.37(8) . . ?
C2C C1C N1C 120.98(8) . . ?
C3C C2C C1C 120.46(8) . . ?
C3C C2C H2C 119.8 . . ?
C1C C2C H2C 119.8 . . ?
C2C C3C C4C 119.57(8) . . ?
C2C C3C N2C 120.75(8) . . ?
C4C C3C N2C 119.63(8) . . ?
C5C C4C C3C 119.57(8) . . ?
C5C C4C H4C 120.2 . . ?
C3C C4C H4C 120.2 . . ?
C4C C5C C6C 121.26(9) . . ?
C4C C5C H5C 119.4 . . ?
C6C C5C H5C 119.4 . . ?
C5C C6C C1C 119.61(8) . . ?
C5C C6C H6C 120.2 . . ?
C1C C6C H6C 120.2 . . ?
C1D N1D H1NG 114.8(9) . . ?
C1D N1D H1NH 117.4(8) . . ?
H1NG N1D H1NH 110.7(12) . . ?
C3D N2D H2NG 114.7(9) . . ?
C3D N2D H2NH 111.7(9) . . ?
H2NG N2D H2NH 109.6(12) . . ?
N1D C1D C2D 120.77(8) . . ?
N1D C1D C6D 119.97(8) . . ?
C2D C1D C6D 119.18(8) . . ?
C1D C2D C3D 120.76(8) . . ?
C1D C2D H2D 119.6 . . ?
C3D C2D H2D 119.6 . . ?
C4D C3D C2D 119.59(8) . . ?
C4D C3D N2D 120.62(8) . . ?
C2D C3D N2D 119.72(8) . . ?
C5D C4D C3D 119.25(9) . . ?
C5D C4D H4D 120.4 . . ?
C3D C4D H4D 120.4 . . ?
C6D C5D C4D 121.72(9) . . ?
C6D C5D H5D 119.1 . . ?
C4D C5D H5D 119.1 . . ?
C5D C6D C1D 119.50(8) . . ?
C5D C6D H6D 120.3 . . ?
C1D C6D H6D 120.3 . . ?

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
C6A C1A C2A C3A -0.66(13) . . . . ?
N1A C1A C2A C3A 176.15(8) . . . . ?
C1A C2A C3A N2A 176.56(8) . . . . ?
C1A C2A C3A C4A -0.29(13) . . . . ?
C2A C3A C4A C5A 1.01(13) . . . . ?
N2A C3A C4A C5A -175.77(8) . . . . ?
C3A C4A C5A C6A -0.80(14) . . . . ?
C4A C5A C6A C1A -0.15(14) . . . . ?
C2A C1A C6A C5A 0.88(13) . . . . ?
N1A C1A C6A C5A -175.89(8) . . . . ?
N1B C1B C2B C3B -176.22(8) . . . . ?
C6B C1B C2B C3B 0.86(13) . . . . ?
C1B C2B C3B N2B -177.10(8) . . . . ?
C1B C2B C3B C4B 0.21(13) . . . . ?
C2B C3B C4B C5B -0.79(13) . . . . ?
N2B C3B C4B C5B 176.57(8) . . . . ?
C3B C4B C5B C6B 0.29(14) . . . . ?
C4B C5B C6B C1B 0.78(14) . . . . ?
N1B C1B C6B C5B 175.73(8) . . . . ?
C2B C1B C6B C5B -1.35(13) . . . . ?
C6C C1C C2C C3C 1.81(13) . . . . ?
N1C C1C C2C C3C -173.74(8) . . . . ?
C1C C2C C3C C4C -0.47(13) . . . . ?
C1C C2C C3C N2C -177.82(8) . . . . ?
C2C C3C C4C C5C -0.74(14) . . . . ?
N2C C3C C4C C5C 176.64(8) . . . . ?
C3C C4C C5C C6C 0.62(14) . . . . ?
C4C C5C C6C C1C 0.73(14) . . . . ?
C2C C1C C6C C5C -1.93(13) . . . . ?
N1C C1C C6C C5C 173.70(8) . . . . ?
N1D C1D C2D C3D 175.52(8) . . . . ?
C6D C1D C2D C3D -1.15(13) . . . . ?
C1D C2D C3D C4D 1.29(13) . . . . ?
C1D C2D C3D N2D 178.16(8) . . . . ?
C2D C3D C4D C5D -0.53(13) . . . . ?
N2D C3D C4D C5D -177.37(8) . . . . ?
C3D C4D C5D C6D -0.36(15) . . . . ?
C4D C5D C6D C1D 0.50(15) . . . . ?
N1D C1D C6D C5D -176.44(9) . . . . ?
C2D C1D C6D C5D 0.25(13) . . . . ?

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
N1A H1NA N1C 0.894(15) 2.473(15) 3.3007(12) 154.1(12) 2_655
N2A H2NB N2D 0.892(14) 2.399(14) 3.2839(12) 171.7(12) 2_645
N1B H1NC N1A 0.901(13) 2.377(14) 3.2587(12) 166.3(11) 2_645
N1B H1ND N1D 0.925(14) 2.421(14) 3.3206(12) 164.0(12) 4_565
N2B H2ND N1B 0.884(14) 2.540(14) 3.4115(12) 168.7(12) 2_755
N1C H1NE N2B 0.924(13) 2.283(14) 3.1866(12) 165.7(11) 2_645
N2C H2NE N2A 0.915(14) 2.480(14) 3.2446(12) 141.2(11) 2_655
N1D H1NH N2C 0.920(14) 2.350(14) 3.1466(12) 144.8(11) 3_666
N2D H2NG N1D 0.904(15) 2.671(14) 3.3873(12) 136.8(11) 3_766

_refine_diff_density_max         0.386
_refine_diff_density_min         -0.180
_refine_diff_density_rms         0.042

_shelxl_version_number           2014-3



_exptl_crystal_recrystallization_method 'Re-crystallisation from solvent'
_chemical_properties_physical    Light-sensitive
####################################################################### 
# 
# 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_CY014
_database_code_depnum_ccdc_archive 'CCDC 1828335'
loop_
_audit_author_name
_audit_author_address
'Daisuke Hashizume'
;RIKEN
Japan
;
_audit_update_record             
;
2018-03-08 deposited with the CCDC.	2020-11-27 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2014
_chemical_name_systematic        2-Bromobenzonitrile
_chemical_name_common            ?
_chemical_melting_point          327
_chemical_formula_moiety         'C7 H4 Br N'
_chemical_formula_sum            'C7 H4 Br N'
_chemical_formula_weight         182.02

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'

_space_group_crystal_system      monoclinic
_space_group_IT_number           14
_space_group_name_H-M_alt        'P 21/c'
_space_group_name_Hall           '-P 2ybc'

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

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

_cell_length_a                   3.8910(2)
_cell_length_b                   10.2919(4)
_cell_length_c                   16.3686(7)
_cell_angle_alpha                90
_cell_angle_beta                 94.963(2)
_cell_angle_gamma                90
_cell_volume                     653.04(5)
_cell_formula_units_Z            4
_cell_measurement_temperature    90
_cell_measurement_reflns_used    18190
_cell_measurement_theta_min      2.340
_cell_measurement_theta_max      31.235

_exptl_crystal_description       needle
_exptl_crystal_colour            colourless
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.851
_exptl_crystal_F_000             352
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.11
_exptl_crystal_size_mid          0.09
_exptl_crystal_size_min          0.07
_exptl_absorpt_coefficient_mu    6.188
_shelx_estimated_absorpt_T_min   0.549
_shelx_estimated_absorpt_T_max   0.671
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.42999
_exptl_absorpt_correction_T_max  0.46982
_exptl_absorpt_process_details   
;
 MULABS - Empirical Correction for Absorption Anisotropy.
 R.H. Blessing, Acta Cryst. (1995), A51, 33-38.
;

_exptl_special_details           
;
 ?
;

_diffrn_ambient_temperature      90
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_source                   'Fine-focus rotating anode'
_diffrn_measurement_device_type  'Rigaku AFC-8 with Saturn70 CCD'
_diffrn_measurement_method       ω-scan
_diffrn_detector_area_resol_mean 7.31
_diffrn_reflns_number            17607
_diffrn_reflns_av_unetI/netI     0.0224
_diffrn_reflns_av_R_equivalents  0.0521
_diffrn_reflns_limit_h_min       -5
_diffrn_reflns_limit_h_max       5
_diffrn_reflns_limit_k_min       -14
_diffrn_reflns_limit_k_max       14
_diffrn_reflns_limit_l_min       -23
_diffrn_reflns_limit_l_max       23
_diffrn_reflns_theta_min         2.340
_diffrn_reflns_theta_max         31.235
_diffrn_reflns_theta_full        25.242
_diffrn_measured_fraction_theta_max 0.990
_diffrn_measured_fraction_theta_full 1.000
_diffrn_reflns_Laue_measured_fraction_max 0.990
_diffrn_reflns_Laue_measured_fraction_full 1.000
_diffrn_reflns_point_group_measured_fraction_max 0.990
_diffrn_reflns_point_group_measured_fraction_full 1.000
_reflns_number_total             2108
_reflns_number_gt                1868
_reflns_threshold_expression     'I > 2σ(I)'
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_max     .
_reflns_Friedel_fraction_full    .

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

_computing_data_collection       CrystalClear
_computing_cell_refinement       HKL2000
_computing_data_reduction        HKL2000
_computing_structure_solution    SHELXS-97
_computing_structure_refinement  'SHELXL-2014 (Sheldrick, 2014)'
_computing_molecular_graphics    SV
_computing_publication_material  'SHELXL-2014 (Sheldrick, 2014)'

_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)+(0.0682P)²+0.3366P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_atom_sites_solution_hydrogens   difmap
_refine_ls_hydrogen_treatment    constr
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       .
_refine_ls_number_reflns         2108
_refine_ls_number_parameters     82
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0448
_refine_ls_R_factor_gt           0.0405
_refine_ls_wR_factor_ref         0.1141
_refine_ls_wR_factor_gt          0.1115
_refine_ls_goodness_of_fit_ref   1.179
_refine_ls_restrained_S_all      1.179
_refine_ls_shift/su_max          0.001
_refine_ls_shift/su_mean         0.000

loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_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 0.09141(6) 0.50842(2) 0.36142(2) 0.02511(12) Uani 1 1 d . . . . .
N1 N 0.1403(7) 0.3140(2) 0.16950(15) 0.0382(5) Uani 1 1 d . . . . .
C1 C 0.3447(6) 0.2584(2) 0.31966(14) 0.0228(4) Uani 1 1 d . . . . .
C2 C 0.2987(6) 0.3442(2) 0.38390(14) 0.0220(4) Uani 1 1 d . . . . .
C3 C 0.4087(6) 0.3125(2) 0.46394(15) 0.0259(5) Uani 1 1 d . . . . .
H3 H 0.3724 0.3709 0.5073 0.031 Uiso 1 1 calc R U . . .
C4 C 0.5734(7) 0.1939(3) 0.48031(16) 0.0271(5) Uani 1 1 d . . . . .
H4 H 0.6536 0.1721 0.5351 0.032 Uiso 1 1 calc R U . . .
C5 C 0.6214(6) 0.1071(3) 0.41706(15) 0.0277(5) Uani 1 1 d . . . . .
H5 H 0.7328 0.0262 0.4288 0.033 Uiso 1 1 calc R U . . .
C6 C 0.5066(7) 0.1386(2) 0.33695(15) 0.0263(5) Uani 1 1 d . . . . .
H6 H 0.5376 0.0791 0.2938 0.032 Uiso 1 1 calc R U . . .
C7 C 0.2295(6) 0.2906(2) 0.23514(15) 0.0269(5) Uani 1 1 d . . . . .


_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 C2 1.895(2) . ?
N1 C7 1.126(3) . ?
C1 C2 1.396(3) . ?
C1 C6 1.403(3) . ?
C1 C7 1.455(3) . ?
C2 C3 1.382(3) . ?
C3 C4 1.394(3) . ?
C3 H3 0.9500 . ?
C4 C5 1.393(4) . ?
C4 H4 0.9500 . ?
C5 C6 1.387(3) . ?
C5 H5 0.9500 . ?
C6 H6 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
C2 C1 C6 119.2(2) . . ?
C2 C1 C7 121.6(2) . . ?
C6 C1 C7 119.2(2) . . ?
C3 C2 C1 121.0(2) . . ?
C3 C2 Br1 119.10(17) . . ?
C1 C2 Br1 119.85(17) . . ?
C2 C3 C4 119.3(2) . . ?
C2 C3 H3 120.4 . . ?
C4 C3 H3 120.4 . . ?
C5 C4 C3 120.5(2) . . ?
C5 C4 H4 119.7 . . ?
C3 C4 H4 119.7 . . ?
C6 C5 C4 120.0(2) . . ?
C6 C5 H5 120.0 . . ?
C4 C5 H5 120.0 . . ?
C5 C6 C1 119.9(2) . . ?
C5 C6 H6 120.0 . . ?
C1 C6 H6 120.0 . . ?
N1 C7 C1 179.2(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
C6 C1 C2 C3 -0.3(3) . . . . ?
C7 C1 C2 C3 179.9(2) . . . . ?
C6 C1 C2 Br1 178.34(18) . . . . ?
C7 C1 C2 Br1 -1.5(3) . . . . ?
C1 C2 C3 C4 1.1(4) . . . . ?
Br1 C2 C3 C4 -177.49(18) . . . . ?
C2 C3 C4 C5 -1.2(4) . . . . ?
C3 C4 C5 C6 0.4(4) . . . . ?
C4 C5 C6 C1 0.5(4) . . . . ?
C2 C1 C6 C5 -0.6(4) . . . . ?
C7 C1 C6 C5 179.3(2) . . . . ?

_refine_diff_density_max         1.024
_refine_diff_density_min         -1.585
_refine_diff_density_rms         0.158

_shelxl_version_number           2014-3



_exptl_crystal_recrystallization_method 'Re-crystallisation from solvent'
